# Patent

## Title
Bicyclic compound

## Abstract

A novel compound represented by the following formula (1) or a salt thereof:




wherein symbol “A” represents a saturated heterocyclic group, a 5-membered heteroaromatic group having two heteroatoms in the ring, a group represented by the formula A1 (R2, R3, and R4 represent hydrogen atom, hydroxyl group, etc.), etc., B represents a group represented by the formula B1 (R11 represents hydrogen atom, hydroxyl group, etc.), etc., R1 represents an alkyl group, and symbol “n” represents an integer of 2 to 6, which has a parathyroid hormone depressing action and showing low toxicity, and a medicament containing the compound or salt thereof as an active ingredient.

## Background
TECHNICAL FIELD
The present invention relates to a novel compound having a parathyroid hormone depressing activity and useful as an active ingredient of a medicament.
BACKGROUND ART
Parathyroid hormone (also abbreviated as “PTH” hereafter in the specification) is a peptide hormone produced by parathyroid chief cells and acts on multiple target organs to play a key role is maintenance of the blood calcium concentration (Furukawa, Y., “Dissection and Physiology of Parathyroid”, Saishin Naikagaku Taikei (Latest Internal Medicine System), 14, Endocrinologic Diseases 3 (edited by Inoue, H. et al), pp. 15-33, Nakayama Shoten, Tokyo, 1993).
Therefore, abnormalities in secretion of PTH bring about pathological conditions based on change of the blood calcium concentration and affections of target organs such as kidney and bone. In hyperparathyroidism characterized by unusual rise of PTH secretion, in particular, target organs are exposed to superfluous PTH, and therefore, in bones, for example, the bone metabolic turnover becomes unusual, and pathological changes of bones such as fibrous ostitis occur at the same time. Furthermore, because affections of organs include a wide range of affections such as hypercalcemia, renal calculus, ectopic calcification, pruritus, digestive ulcer, cardiac muscle abnormal contraction, brain wave abnormality and anemia, life prognosis and QOL (Quality of Life) of patients are seriously affected. As the curative medicaments for the diseases in which PTH secretion abnormally rises, activated type vitamin D and the like have already been clinically used. However, development of novel safe medicaments having further superior curative effect and being convenient for patients has been desired.
DISCLOSURE OF THE INVENTION
Object to be Achieved by the Invention
An object of the present invention is to provide a compound having a parathyroid hormone depressing activity and useful as an active ingredient of medicaments for prophylactic and/or therapeutic treatment of diseases such as hyperPTHemia.
Means to Achieve the Object
The inventors of the present invention intensively searched substances having a PTH depressing action to achieve the aforementioned object. As a result, we found that the compounds represented by the following formula (1) had a marked PTH depressing action and were useful as an active ingredient of medicaments for prophylactic and/or therapeutic treatment of diseases such as hyperPTHemia. The present invention was achieved on the basis of the aforementioned finding.
The present invention thus provides:

    (1) A compound represented by the following formula (1) or a salt thereof:






wherein:

symbol “A” represents a group selected from the group consisting of (1) a saturated heterocyclic group, (2) a 5-membered heteroaromatic group having two heteroatoms in the ring which may be substituted, (3) a group represented by the following formula A1, (4) a group represented by the following formula A2, and (5) a group represented by the following formula A3:




wherein R2, R3, and R4 may be the same or different, and independently represent hydrogen atom, hydroxyl group, a halogen atom, an alkyl group, phenyl group, a substituted phenyl group, benzyl group, a substituted benzyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, or N(R16)(R17) wherein R16 and R17 may be the same or different, and independently represent hydrogen atom, an alkyl group, an acyl group, or SO2R18 wherein R18 represents a lower alkyl group, or R16 and R17 together form a 3- to 7-membered ring to represent a cyclic amine as N(R16)(R17); R5, R6 and R7 may be the same or different, and independently represent hydrogen atom, hydroxyl group, a halogen atom, an alkyl group, phenyl group, a substituted phenyl group, benzyl group, a substituted benzyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, or N(R16)(R17) wherein R16 and R17 may be the same or different, and independently represent hydrogen atom, an alkyl group, an acyl group, or SO2R18 wherein R18 represents a lower alkyl group, or R16 and R17 together form a 3- to 7-membered ring to represent a cyclic amine as N(R16)(R17); R8, R9 and R10 independently represent hydrogen atom, hydroxyl group, a halogen atom, an alkyl group, phenyl group, a substituted phenyl group, benzyl group, a substituted benzyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, or N(R16)(R17) wherein R16 and R17 may be the same or different, and independently represent hydrogen atom, an alkyl group, an acyl group, or SO2R18 wherein R18 represents a lower alkyl group, or R16 and R17 together form a 3- to 7-membered ring to represent a cyclic amine as N(R16)(R17), or R8 and R9 may together form a benzene ring to represent a bicyclic heteroaromatic group as the group represented by the formula A3; and X1 represents oxygen atom, sulfur atom, or N—R19 wherein R19 represents hydrogen atom, an alkyl group, phenyl group, or a substituted phenyl group,

B represents a group selected from the group consisting of a group represented by the following formula B1, a group represented by the formula B2, a group represented by the formula B3, a group represented by the formula B4, and a group represented by the formula B5:




wherein R11 represents hydrogen atom, hydroxyl group, a halogen atom, an alkyl group, an alkoxyl group, a thioalkoxyl group, hydroxymethyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, or N(R20)(R21) wherein R20 and R21 may be the same or different, and independently represent hydrogen atom, an alkyl group, an acyl group, or SO2R22 wherein R22 represents a lower alkyl group, or R20 and R21 together form a 3- to 7-membered ring to represent a cyclic amine as N(R20)(R21), Y1 represents sulfur atom or oxygen atom; R12 represent hydrogen atom or an alkyl group, Y2 represents CH or nitrogen atom; R13 represents hydrogen atom, hydroxyl group, a halogen atom, an alkyl group, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, or N(R20)(R21) wherein R20 and R21 may be the same or different, and independently represent hydrogen atom, an alkyl group, an acyl group, or SO2R22 wherein R22 represents a lower alkyl group, or R20 and R21 together form a 3- to 7-membered ring to represent a cyclic amine as N(R20)(R21), Y4 represents sulfur atom or oxygen atom, and one of Y3, Y5, and Y6 represents nitrogen atom, and the remaining groups represent CH; R14 represents hydrogen atom, hydroxyl group, a halogen atom, an alkyl group, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, or N(R20)(R21) wherein R20 and R21 may be the same or different, and independently represent hydrogen atom, an alkyl group, an acyl group, or SO2R22 wherein R22 represents a lower alkyl group, or R20 and R21 together form a 3- to 7-membered ring to represent a cyclic amine as N(R20)(R21), Y7 represent CH or nitrogen atom; and R15 represents hydrogen atom, hydroxyl group, a halogen atom, an alkyl group, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, or N(R20)(R21) wherein R20 and R21 may be the same or different, and independently represent hydrogen atom, an alkyl group, an acyl group, or SO2R22 wherein R22 represents a lower alkyl group, or R16 and R17 together form a 3- to 7-membered ring to represent a cyclic amine as N(R20)(R21);

R1 represents an alkyl group, and symbol “n” represents an integer of 2 to 6,

    (2) The compound or salt thereof according to (1) mentioned above, wherein B is a group represented by the formula B1, B3, B4, or B5,
    (3) The compound or salt thereof according to (1) mentioned above, wherein B is a group represented by the formula B1,
    (4) The compound or salt thereof according to (1) mentioned above, wherein B is a group represented by the formula B2,
    (5) The compound or salt thereof according to (1), wherein A is a group selected from the group consisting of a group represented by the formula A2, a group represented by the formula A3, and a group represented by the following formula A4:






wherein R23 represents hydrogen atom, hydroxyl group, a halogen atom, an alkyl group, phenyl group, a substituted phenyl group, benzyl group, a substituted benzyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, or N(R16)(R17) wherein R16 and R17 may be the same or different, and independently represent hydrogen atom, an alkyl group, an acyl group, or SO2R18 wherein R18 represents a lower alkyl group, or R16 and R17 together form a 3- to 7-membered ring to represent a cyclic amine as N(R16)(R17); and X2 represents oxygen atom, sulfur atom, or N—R19 wherein R19 represents hydrogen atom, an alkyl group, phenyl group, or a substituted phenyl group,

    (6) The compound or salt thereof according to any one of (1) to (5), wherein A is a group represented by the formula A2,
    (7) The compound or salt thereof according to any one of (1), (4), and (6), wherein A is a group represented by the formula A2 wherein R6 and R7 are hydrogen atoms, R5 is phenyl group, a substituted phenyl group, benzyl group, a substituted benzyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, or an alkoxyl group arbitrarily substituted with one or more halogen atoms, and B is a group represented by the formula B2 wherein R12 is hydrogen atom, and Y2 is CH,
    (8) The compound or salt thereof according to (7), wherein R5 is a substituted phenyl group, a monocyclic heteroaromatic group which may be substituted, or a bicyclic heteroaromatic group which may be substituted,
    (9) The compound or salt thereof according to any one of (1) to (5), wherein A is a group represented by the formula A3,
    (10) The compound or salt thereof according to any one of (1), (4), and (9), wherein A is a group represented by the formula A3 wherein R8 and R10 are hydrogen atoms, and R9 is phenyl group, a substituted phenyl group, benzyl group, a substituted benzyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, or an alkoxyl group arbitrarily substituted with one or more halogen atoms, and B is a group represented by the formula B2 wherein R12 is hydrogen atom, and Y2 is CH,
    (11) The compound or salt thereof according to (10), wherein R9 is a substituted phenyl group, a monocyclic heteroaromatic group which may be substituted, or a bicyclic heteroaromatic group which may be substituted,
    (12) The compound or salt thereof according to any one of (1) to (5), wherein A is a group represented by the formula A4,
    (13) The compound or salt thereof according to any one of claims (1), (4), and (12), wherein A is a group represented by the formula A4 wherein R23 is phenyl group, a substituted phenyl group, benzyl group, a substituted benzyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, or an alkoxyl group arbitrarily substituted with one or more halogen atoms, and B is a group represented by the formula B2 wherein R12 is hydrogen atom, and Y2 is CH,
    (14) The compound or salt thereof according to (13), wherein R23 is a substituted phenyl group, a monocyclic heteroaromatic group which may be substituted, or a bicyclic heteroaromatic group which may be substituted, and
    (15) The compound or salt thereof according to any one of claims 1 to 4, wherein A is a group represented by the formula A2 or A3, or a 5-membered heteroaromatic group having two hetero atoms in the ring.


Further, from another aspect of the present invention, a medicament containing a compound represented by the aforementioned formula (1) or a physiologically acceptable salt thereof as an active ingredient is provided. The aforementioned medicament can be used as an agent for depressing parathyroid hormone. The medicament of the present invention can be used for hyperPTHemia and hyperparathyroidism (including, for example, primary hyperparathyroidism and secondary hyperparathyroidism), which is a major causative disease of hyperPTHemia. The medicament of the present invention can also be used for complications of hyperparathyroidism (for example, bone diseases accompanied by a bone metabolic disorder and the like). The medicament of the present invention can also be used for various kinds of bone diseases showing a bone metabolic disorder due to a relatively high blood parathyroid hormone concentration, even if the concentration is within a normal range (for example, osteoporosis and the like). Furthermore, the medicament of the present invention can be used for prophylactic and/or therapeutic treatment of hypercalcemia and the like resulting from a malignant tumor and the like on the basis on the action of depressing the blood PTH concentration.
From still further aspects of the present invention, there are provided use of a compound represented by the aforementioned formula (1) or a physiologically acceptable salt thereof for manufacture of the aforementioned medicament; a method for depressing parathyroid hormone, which comprises the step of administrating an effective amount of a compound represented by the aforementioned formula (1) or a physiologically acceptable salt thereof to a mammal including human; a method for prophylactic and/or therapeutic treatment of hyperparathormonemia, which comprises the step of administrating a prophylactically and/or therapeutically effective amount of a compound represented by the aforementioned formula (1) or a physiologically acceptable salt thereof to a mammal including human; a method for prophylactic and/or therapeutic treatment of hyperparathyroidism and/or complications thereof, which comprises the step of administrating a prophylactically and/or therapeutically effective amount of a compound represented by the aforementioned formula (1) or a physiologically acceptable salt thereof to a mammal including human; a method for prophylactic and/or therapeutic treatment of a bone disease accompanying increase in blood parathyroid hormone, which comprises the step of administrating a prophylactically and/or therapeutically effective amount of a compound represented by the aforementioned formula (1) or a physiologically acceptable salt thereof to a mammal including human; and a method for prophylactic and/or therapeutic treatment of hypercalcemia based on an action of depressing blood PTH concentration, which comprises the step of administrating a prophylactically and/or therapeutically effective amount of a compound represented by the aforementioned formula (1) or a physiologically acceptable salt thereof to a mammal including human.
EFFECT OF THE INVENTION
The compounds of the present invention have a potent PTH depressing action, when they are administered to a human or an animal in a free form or in a form of a salt, and they are suitable as active ingredients of medicaments for prophylactic and/or therapeutic treatment of diseases such as hyperPTHemia.


BEST MODE FOR CARRYING OUT THE INVENTION
Hereafter, the present invention will be specifically explained.
In this specification, a halogen atom may be, for example, fluorine atom, chlorine atom, bromine atom, or iodine atom, unless otherwise especially indicated. Further, as the alkyl group, examples include a saturated hydrocarbon group comprising a linear, cyclic, or branched chain or a combination thereof, and the alkyl group is usually preferably a lower alkyl group. The same shall apply to alkyl moieties of other substituents having an alkyl moiety (e.g., an alkoxyl group, an acyl group and the like). As the lower alkyl group, an alkyl group having 1 to 4 carbon atoms is generally preferred. Specific examples include methyl group, ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, cyclobutyl group, and cyclopropylmethyl group.
As the alkoxyl group, an example includes a saturated alkyl ether group, and the group is generally preferably a lower alkoxyl group. As the lower alkoxyl group, an alkoxyl group having 1 to 4 carbon atoms is generally preferred. Specific examples include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, cyclopropoxy group, n-butoxy group, isobutoxy group, s-butoxy group, t-butoxy group, cyclobutoxy group, and cyclopropylmethoxy group.
As alkyl group arbitrarily substituted with one or more halogen atoms, examples include the aforementioned alkyl group of which one or more hydrogen atoms are replaced with a halogen atom or atoms of an arbitrary type, and the group is generally preferably an alkyl group arbitrarily substituted with one or more halogen atoms and having 1 to 4 carbon atoms. When the group is substituted with two or more halogen atoms, the halogen atom may be the same or different. Specific examples include chloromethyl group, dichloromethyl group, trichloromethyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, chloroethyl group, fluoroethyl group, 1,1,1-trichloroethyl group, 1,1,1-trifluoroethyl group, and the like.
As the alkoxyl group arbitrarily substituted with one or more halogen atoms, examples include a saturated alkyl ether group comprising the aforementioned alkyl group of which one or more hydrogen atoms are replaced with a halogen atom or atoms of an arbitrary type, and the group is generally preferably an alkoxyl group arbitrarily substituted with one or more halogen atoms and having 1 to 4 carbon atoms. When the group is substituted with two or more halogen atoms, the halogen atom may be the same or different. Specific examples include trifluoromethoxy group and 1,1,1-trifluoroethoxy group.
As the acyl group, examples include an alkanoyl group (alkylcarbonyl group), an arylcarbonyl group and the like, and a lower alkanoyl group may be preferred. The alkyl moiety of the alkanoyl group may contain one or more unsaturated bonds. As the lower alkanoyl group, an acyl group having 2 to 5 carton atoms is generally preferred. Specifically, examples include acetyl group, propanoyl group, butanoyl group, 2-methylpropanoyl group, cyclopropylcarbonyl group, pentanoyl group, 3-methylbutanoyl group, 2,2-dimethylpropanoyl group, cyclobutylcarbonyl group and the like.
Examples of the substituent in the substituted phenyl group, substituted benzyl group, 5-membered heteroaromatic group having two hetero atoms in the ring which may be substituted, monocyclic heteroaromatic group which may be substituted, and bicyclic heteroaromatic group which may be substituted include hydrogen atom, hydroxyl group, a halogen atom, an alkyl group, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, cyano group, an acyl group, CON(R24)(R25) wherein R24 and R25 may be the same or different, and independently represent hydrogen atom, an alkyl group, or an alkoxy group, or R24 and R25 together form a 3- to 7-membered ring to represent a cyclic amine as N(R24)(R25), COOR26 wherein R26 represents an alkyl group, S(O)mR27 wherein m represents 0 or 1, and R27 represents an alkyl group, SO2R28 wherein R28 represents an alkyl group, amino group, aminomethyl group, or dimethylamino group, CH2OR29 wherein R29 represents hydrogen atom, an alkyl group, or an alkyl group arbitrarily substituted with one or more halogens, CH(OH)CH3, CH2N(R30)(R31) wherein R30 and R31 may be the same or different, and independently represent hydrogen atom, an alkyl group, an acyl group, or SO2R34 wherein R34 represents a lower alkyl group, or R30 and R31 together form a 3- to 7-membered ring to represent a cyclic amine as N(R30)(R31), and N(R32)(R33) wherein R32 and R33 may be the same or different, and independently represent hydrogen atom, an alkyl group, an acyl group, SO2R34 wherein R34 represents a lower alkyl group, COOR35 wherein R35 represents hydrogen atom, or a lower alkyl group, CSR36 wherein R36 represents a lower alkyl group, or an amino group which may be substituted with one or two lower alkyl groups, CH2COR37 wherein R37 represents a lower alkyl group, CH2CH(OR38)R39 wherein R38 and R39 may be the same or different, and independently represent hydrogen atom, or a lower alkyl group, or R32 and R33 together form a 3- to 7-membered ring to represent a cyclic amine as N(R32)(R33), and number of the substituent is 1 to 3. When two or more substituents exist, they may be the same or different.
Examples of the substituted phenyl group include, for example, 2-hydroxyphenyl group, 3-hydroxyphenyl group, 4-hydroxyphenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 3-chlorophenyl group, 3-tolyl group, 4-tolyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 4-amino-3-hydroxyphenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 3-aminophenyl group, 4-aminophenyl group, 3-nitrophenyl group, 4-nitrophenyl group, 4-hydroxymethylphenyl group, 4-methoxymethylphenyl group, 3,4-dimethoxyphenyl group, 2-trifluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 4-cyanophenyl group, 4-acetylphenyl group, 4-methoxycarbonylphenyl group, 4-carbamoylphenyl group, 4-acetamidophenyl group, 4-methanesulfonylphenyl group, 4-(1-hydroxyethyl)phenyl group, 4-methanesulfonylaminophenyl group, and 4-dimethylaminophenyl group.
Examples of the substituted benzyl group include, for example, 3-hydroxybenzyl group, 2-fluorobenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group, 4-methylbenzyl group, 3-methoxybenzyl group, 4-methoxybenzyl group, 2-methoxybenzyl group, 3-trifluoromethylbenzyl group, 4-trifluoromethylbenzyl group, and 4-nitrobenzyl group.
In the 5-membered heteroaromatic group having two heteroatoms in the ring which may be substituted, the heteroatom is preferably nitrogen atom, oxygen atom, or nitrogen atom. Specific examples of the 5-membered heteroaromatic group include a monovalent group formed by eliminating an arbitrary one hydrogen atom from oxazole, thiazole, isoxazole, isothiazole, imidazole, or pyrazole, and examples include, for example, oxazol-2-yl, thiazol-2-yl, imidazol-2-yl, 2-phenylthiazol-4-yl, and 1-phenylpyrazol-3-yl.
Examples of the monocyclic heteroaromatic group which may be substituted include a monocyclic heteroaromatic group having a 5-membered ring or 6-membered ring constituted by ring-constituting carbon atoms and one or two ring-constituting heteroatoms selected from nitrogen atom, oxygen atom, and sulfur atom. Examples include, specifically, a monovalent group formed by eliminating an arbitrary one hydrogen atom from a cyclic compound such as pyrrole, furan, thiophene, oxazole, thiazole, imidazole, pyrazole, pyridine, pyrimidine, or pyrazine, but not limited to these groups. More specifically, examples include 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-methoxypyridin-6-yl, 2-methoxypyridin-5-yl, 2-trifluoromethoxypyridin-5-yl, 2-trifluoromethylpyridin-5-yl, 2-morpholinopyridin-5-yl, 2-fluoropyridin-5-yl, furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, pyrrol-2-yl, N-methylpyrrol-2-yl, 5-chlorothiophen-2-yl, 5-nitrothiophen-2-yl, 5-methylthiophen-2-yl, 5-ethylthiophen-2-yl, 5-acetylthiophen-2-yl, oxazol-2-yl, oxazol-4-yl, 5-phenyloxazol-2-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, 1-methylpyrazol-4-yl, 2-aminopyrimidin-5-yl, 2-methylaminopyrimidin-5-yl, 2-dimethylaminopyrimidine-5-yl, pyrimidin-2-on-5-yl, 1-methylpyrimidin-2-on-5-yl, and 2-methoxypyrimidin-5-yl.
Examples of the bicyclic heteroaromatic group which may be substituted, include a bicyclic heteroaromatic group having a 5-membered ring or 6-membered ring constituted by ring-constituting carbon atoms and one to three ring-constituting heteroatoms selected from nitrogen atom, oxygen atom, and sulfur atom. Examples include, specifically, a monovalent group formed by eliminating an arbitrary one hydrogen atom from a bicyclic compound such as indole, isoindole, benzofuran, benzothiophene, indazole, benzothiazole, benzimidazole, benzoxazole, quinoline, isoquinoline, cinnoline, phthalazine, quinazoline, or quinoxaline, but not limited to these groups.
Examples include, for example, indol-3-yl, indol-5-yl, indol-6-yl, benzofuran-5-yl, isoindol-5-yl, indazol-5-yl, indazol-6-yl, N-methylindazol-5-yl, N-methylindazol-6-yl, quinolin-6-yl, benzo[b]isoxazol-5-yl, benzo[b]isothiazol-5-yl, isoquinolin-6-yl, benzothiazol-2-yl, benzothiazol-5-yl, benzothiazol-6-yl, benzoxazol-2-yl, benzoxazol-5-yl, and benzoxazol-6-yl.
Examples of the cyclic amine include a cyclic amine having a 3- to 7-membered ring and constituted by ring-constituting carbon atoms and zero to two ring-constituting heteroatoms selected from nitrogen atom, oxygen atom, and sulfur atom, and a substituent may exist on a ring-constituting nitrogen atom and/or ring-constituting carbon atom. Specific examples include cyclopropylamine, cyclobutylamine, pyrrolidine, piperidine, cyclopentylamine, morpholine, piperazine, and thiomorpholine, but not limited to these amines. Examples of the substituent of the cyclic amine include, for example, hydroxyl group, a halogen atom, an alkyl group, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, amino group, and cyano group. When a substituent exists, the number of substituent is 1 to 2.
Hereafter, each of various substituents in the compounds represented by the formula (1) will be specifically explained.
R2, R3, and R4 may be the same or different, and independently represent hydrogen atom, hydroxyl group, a halogen atom, an alkyl group, phenyl group, a substituted phenyl group, benzyl group, a substituted benzyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, or N(R16)(R17). As R2, R3, and R4, hydrogen atom, a halogen atom, an alkyl group, phenyl group, a substituted phenyl group, benzyl group, a substituted benzyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, and an alkoxyl group arbitrarily substituted with one or more halogen atoms are preferred. The halogen atom, alkyl group, alkoxyl group, alkyl group arbitrarily substituted with one or more halogen atoms, and alkoxyl group arbitrarily substituted with one or more halogen atoms have the same meanings as those defined above.
As the halogen atoms represented by R2, R3, and R4, halogen atoms independently selected from the group consisting of fluorine atom, chlorine atom, and bromine atom are preferred, and fluorine atom, and chlorine atom are more preferred. As the alkyl group represented by R2, R3, or R4, an alkyl group having 1 to 4 carbon atoms is preferred, methyl group and ethyl group are more preferred, and methyl group is most preferred. As R2, R3, or R4, phenyl group is also preferred. As the substituted phenyl group represented by R2, R3, or R4, 2-hydroxyphenyl group, 3-hydroxyphenyl group, 4-hydroxyphenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 3-chlorophenyl group, 3-tolyl group, 4-tolyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 4-amino-3-hydroxyphenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 3-aminophenyl group, 4-aminophenyl group, 3-nitrophenyl group, 4-nitrophenyl group, 4-hydroxymethylphenyl group, 4-methoxymethylphenyl group, 3,4-dimethoxyphenyl group, 2-trifluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 4-cyanophenyl group, 4-acetylphenyl group, 4-methoxycarbonylphenyl group, 4-carbamoylphenyl group, 4-acetamidophenyl group, 4-methanesulfonylaminophenyl group, 4-(1-hydroxyethyl)phenyl group, methanesulfonylphenyl group, 4-methylsulfinylphenyl group, 4-aminosulfonylphenyl group, 4-methylaminosulfonylphenyl group, 4-dimethylaminosulfonylphenyl group, and 4-dimethylaminophenyl group are preferred, 4-hydroxyphenyl group, 4-fluorophenyl group, 4-methoxyphenyl group, 4-trifluoromethylphenyl group, 4-hydroxymethylphenyl group, 4-methoxymethylphenyl group, 3,4-dimethoxyphenyl group, 4-trifluoromethoxyphenyl group, 4-cyanophenyl group, 4-acetylphenyl group, 4-methoxycarbonylphenyl group, 4-carbamoylphenyl group, 4-acetamidophenyl group, 4-methanesulfonylaminophenyl group, 4-(1-hydroxyethyl)phenyl group, 4-methanesulfonylphenyl group, 4-methylsulfinylphenyl group, 4-aminosulfonylphenyl group, 4-methylaminosulfonylphenyl group, 4-dimethylaminosulfonylphenyl group, and 4-dimethylaminophenyl group are more preferred, and 4-trifluoromethoxyphenyl group, 4-hydroxymethylphenyl group, 4-methoxymethylphenyl group, 4-cyanophenyl group, 4-acetylphenyl group, 4-methoxycarbonylphenyl group, 4-carbamoylphenyl group, 4-(1-hydroxyethyl)phenyl group, 4-methanesulfonylphenyl group, 4-methylsulfinylphenyl group, 4-aminosulfonylphenyl group, 4-methylaminosulfonylphenyl group, 4-dimethylaminosulfonylphenyl group, and 4-acetamidophenyl group are particularly preferred.
As R2, R3, or R4, benzyl group is also preferred. As the substituted benzyl group represented by R2, R3, or R4, 2-hydroxybenzyl group, 3-hydroxybenzyl group, 4-hydroxybenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, 3-chlorobenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 2-methoxybenzyl group, 3-methoxybenzyl group, 4-methoxybenzyl group, 4-amino-3-hydroxybenzyl group, 2-trifluoromethylbenzyl group, 3-trifluoromethylbenzyl group, 4-trifluoromethylbenzyl group, 3-aminobenzyl group, 4-aminobenzyl group, 3-nitrobenzyl group, 4-nitrobenzyl group, 3,4-dimethoxybenzyl group, 2-trifluoromethoxybenzyl group, 3-trifluoromethoxybenzyl group, 4-trifluoromethoxybenzyl group, 4-cyanobenzyl group, 4-acetylbenzyl group, 4-methoxycarbonylbenzyl group, 4-carbamoylbenzyl group, 4-acetamidobenzyl group, 4-methanesulfonylaminobenzyl group, and 4-dimethylaminobenzyl group are preferred, and 4-trifluoromethoxybenzyl group, 4-cyanobenzyl group, 4-acetylbenzyl group, 4-methoxycarbonylbenzyl group, 4-carbamoylbenzyl group, and 4-acetamidobenzyl group are more preferred.
As the monocyclic heteroaromatic group which may be substituted, represented by R2, R3, or R4, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-methoxypyridin-6-yl, 2-methoxypyridin-5-yl, 2-trifluoromethoxypyridin-5-yl, 2-trifluoromethylpyridin-5-yl, 2-morpholinopyridin-5-yl, 2-methoxypyrimidin-5-yl, furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, pyrrol-2-yl, N-methylpyrrol-2-yl, 5-chlorothiophen-2-yl, 5-nitrothiophen-2-yl, 5-methylthiophen-2-yl, 5-ethylthiophen-2-yl, oxazol-2-yl, oxazol-4-yl, 5-phenyloxazol-2-yl, 1-methylpyrazol-4-yl, 2-dimethylaminopyridin-5-yl, 5-acetylthiophen-2-yl, 2-cyanopyrimidin-5-yl, 2-methoxypyrimidin-5-yl, 2-dimethylaminopyrimidin-5-yl, 1-(2-oxopropyl)pyrazol-4-yl, 2-methoxythiazol-4-yl, 2-dimethylaminothiazol-4-yl, and thiazol-2-yl are preferred, and 3-pyridyl group, 2-methoxypyridin-5-yl, 2-trifluoromethoxypyridin-5-yl, 2-trifluoromethylpyridin-5-yl, 2-methoxypyrimidin-5-yl, thiophen-2-yl, thiophen-3-yl, N-methylpyrrol-2-yl, 5-chlorothiophen-2-yl, 5-methylthiophen-2-yl, oxazol-2-yl, oxazol-4-yl, 1-methylpyrazol-4-yl, 5-acetylthiophen-2-yl, 2-methoxypyrimidin-5-yl, 2-dimethylaminopyrimidin-5-yl, 2-methoxythiazol-4-yl, and thiazol-2-yl are more preferred. As the bicyclic heteroaromatic group which may be substituted, represented by R2, R3, or R4, indol-3-yl, indol-5-yl, indol-6-yl, benzofuran-5-yl, isoindol-5-yl, indazol-5-yl, indazol-6-yl, N-methylindazol-5-yl, N-methylindazol-6-yl, quinolin-6-yl, benzo[b]isoxazol-5-yl, benzo[b]isothiazol-5-yl, isoquinolin-6-yl, benzothiazol-2-yl, benzothiazol-5-yl, benzothiazol-6-yl, benzoxazol-2-yl, benzoxazol-5-yl, and benzoxazol-6-yl are preferred, and indol-3-yl, indol-5-yl, benzofuran-5-yl, isoindol-5-yl, indazol-5-yl, N-methylindazol-5-yl, quinolin-6-yl, benzo[b]isoxazol-5-yl, benzo[b]isothiazol-5-yl, isoquinolin-6-yl, benzothiazol-2-yl, benzothiazol-5-yl, and benzoxazol-5-yl are more preferred.
As the alkoxyl group represented by R2, R3, or R4, an alkoxyl group having 1 to 4 carbon atoms is preferred, methoxy group and ethoxy group are more preferred, and methoxy group is most preferred. As the alkyl group arbitrarily substituted with one or more halogen atoms represented by R2, R3, or R4, such an alkyl group having 1 to 4 carbon atoms is preferred, monofluoromethyl group, difluoromethyl group, and trifluoromethyl group are more preferred, and trifluoromethyl group is most preferred. As the alkoxyl group arbitrarily substituted with one or more halogen atoms represented by R2, R3, or R4, such an alkoxyl group having 1 to 4 carbon atoms is preferred, and trifluoromethoxy group is preferred.
It is preferred that any one of R2, R3, and R4 is hydrogen atom, and it is more preferred that any two of them are hydrogen atoms. Further, all of R2, R3, and R4 may be hydrogen atoms. When one or more of R2, R3, and R4 are substituents other than hydrogen atom, the substituting positions thereof are not particularly limited, and they may exist on arbitrary positions on the benzene ring. When one or more of R2, R3, and R4 are substituents other than hydrogen atom, the substituting positions thereof are preferably chosen from the para- and meta-positions relative to the aminoalkyl side chain, and the meta-position is particularly preferred. As another embodiment, the para-position is also extremely preferred.
R16 and R17 may be the same or different, and independently represent hydrogen atom, an alkyl group, an acyl group, or SO2R18 wherein R18 is a lower alkyl group, or R16 and R17 together form a 3- to 7-membered ring to represent a cyclic amine as N(R16)(R17). The alkyl group and acyl group have the same meanings as those defined above. As R16 and R17, hydrogen atom is preferred. As the alkyl group represented by R16 or R17, an alkyl group having 1 to 4 carton atoms is preferred, methyl group and ethyl group are more preferred, and methyl group is particularly preferred. As the acyl group represented by R16 or R17, an acyl group having 2 to 5 carton atoms is preferred, and acetyl group is particularly preferred. More specifically, examples of N(R16)(R17) include amino group, a monoalkylamino group, a dialkylamino group, a monoacylamino group, a diacylamino group, and an acylated monoalkylamino group, and preferred examples are amino group, a monoalkylamino group, a dialkylamino group, and monoacylamino group. Among them, amino group is preferred. As the monoalkylamino group represented by N(R16)(R17), an amino group substituted with an alkyl group having 1 to 4 carton atoms is preferred, and methylamino group and ethylamino group are more preferred. As the dialkylamino group represented by N(R16)(R17), an amino group substituted with alkyl groups independently having 1 to 4 carton atoms is preferred, and dimethylamino group is more preferred. As the monoacylamino group represented by N(R16)(R17), an amino group substituted with an acyl group having 2 to 5 carton atoms is preferred, and acetylamino group is more preferred. When R16 and R17 together form a 3- to 7-membered ring to represent a cyclic amine as N(R16)(R17), a 3- to 7-membered cyclic amine is preferred, and a 6-membered cyclic amine is more preferred. Specifically, morpholine, piperidine, and piperazine are preferred, and morpholine is more preferred.
R5, R6, and R7 may be the same or different, and independently represent hydrogen atom, hydroxyl group, a halogen atom, an alkyl group, phenyl group, a substituted phenyl group, benzyl group, a substituted benzyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, or N(R16)(R17). As R5, R6, and R7, hydrogen atom, a halogen atom, an alkyl group, phenyl group, a substituted phenyl group, benzyl group, a substituted benzyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, and an alkoxyl group arbitrarily substituted with one or more halogen atoms are preferred. The halogen atom, alkyl group, alkoxyl group, alkyl group arbitrarily substituted with one or more halogen atoms, and alkoxyl group arbitrarily substituted with one or more halogen atoms have the same meanings as those defined above.
As R5, R6, and R7, hydrogen atom is preferred. As the halogen atom represented by R5, R6, or R7, a halogen atom selected from the group consisting of fluorine atom, chlorine atom, and bromine atom is preferred, and fluorine atom, and chlorine atom are more preferred. As the alkyl group represented by R5, R6, or R7, an alkyl group having 1 to 4 carbon atoms is preferred, methyl group and ethyl group are more preferred, and methyl group is particularly preferred. As R5, R6, and R7, phenyl group is also preferred. As the substituted phenyl group represented by R5, R6, and R7, 2-hydroxyphenyl group, 3-hydroxyphenyl group, 4-hydroxyphenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 3-chlorophenyl group, 3-tolyl group, 4-tolyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 4-amino-3-hydroxyphenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 3-aminophenyl group, 4-aminophenyl group, 3-nitrophenyl group, 4-nitrophenyl group, 4-hydroxymethylphenyl group, 4-methoxymethylphenyl group, 3,4-dimethoxyphenyl group, 2-trifluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 4-cyanophenyl group, 4-acetylphenyl group, 4-methoxycarbonylphenyl group, 4-carbamoylphenyl group, 4-acetamidophenyl group, 4-methanesulfonylaminophenyl group, 4-(1-hydroxyethyl)phenyl group, 4-methanesulfonylphenyl group, 4-methylsulfinylphenyl group, 4-aminosulfonylphenyl group, 4-methylaminosulfonylphenyl group, 4-dimethylaminosulfonylphenyl group, and 4-dimethylaminophenyl group are preferred, 4-hydroxyphenyl group, 4-fluorophenyl group, 4-methoxyphenyl group, 4-trifluoromethylphenyl group, 4-hydroxymethylphenyl group, 4-methoxymethylphenyl group, 3,4-dimethoxyphenyl group, 4-trifluoromethoxyphenyl group, 4-cyanophenyl group, 4-acetylphenyl group, 4-methoxycarbonylphenyl group, 4-carbamoylphenyl group, 4-acetamidophenyl group, 4-methanesulfonylaminophenyl group, 4-(1-hydroxyethyl)phenyl group, 4-methanesulfonylphenyl group, 4-methylsulfinylphenyl group, 4-aminosulfonylphenyl group, 4-methylaminosulfonylphenyl group, 4-dimethylaminosulfonylphenyl group, and dimethylaminophenyl group are more preferred, and 4-trifluoromethoxyphenyl group, 4-hydroxymethylphenyl group, 4-methoxymethylphenyl group, 4-cyanophenyl group, 4-acetylphenyl group, 4-methoxycarbonylphenyl group, 4-carbamoylphenyl group, 4-(1-hydroxyethyl)phenyl group, 4-methanesulfonylphenyl group, 4-methylsulfinylphenyl group, 4-aminosulfonylphenyl group, 4-methylaminosulfonylphenyl group, 4-dimethylaminosulfonylphenyl group, and 4-acetamidophenyl group are particularly preferred.
As R5, R6, and R7, benzyl group is also preferred. As the substituted benzyl group represented by R5, R6, or R7, 2-hydroxybenzyl group, 3-hydroxybenzyl group, 4-hydroxybenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, 3-chlorobenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 2-methoxybenzyl group, 3-methoxybenzyl group, 4-methoxybenzyl group, 4-amino-3-hydroxybenzyl group, 2-trifluoromethylbenzyl group, 3-trifluoromethylbenzyl group, 4-trifluoromethylbenzyl group, 3-aminobenzyl group, 4-aminobenzyl group, 3-nitrobenzyl group, 4-nitrobenzyl group, 3,4-dimethoxybenzyl group, 2-trifluoromethoxybenzyl group, 3-trifluoromethoxybenzyl group, 4-trifluoromethoxybenzyl group, 4-cyanobenzyl group, 4-acetylbenzyl group, 4-methoxycarbonylbenzyl group, 4-carbamoylbenzyl group, 4-acetamidobenzyl group, 4-methanesulfonylaminobenzyl group, and 4-dimethylaminobenzyl group are preferred, and 4-trifluoromethoxybenzyl group, 4-cyanobenzyl group, 4-acetylbenzyl group, 4-methoxycarbonylbenzyl group, 4-carbamoylbenzyl group, and 4-acetamidobenzyl group are more preferred.
As the monocyclic heteroaromatic group which may be substituted, represented by R5, R6, or R7, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-methoxypyridin-6-yl, 2-methoxypyridin-5-yl, 2-trifluoromethoxypyridin-5-yl, 2-trifluoromethylpyridin-5-yl, 2-morpholinopyridin-5-yl, 2-methoxypyrimidin-5-yl, furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, pyrrol-2-yl, N-methylpyrrol-2-yl, 5-chlorothiophen-2-yl, 5-nitrothiophen-2-yl, 5-methylthiophen-2-yl, 5-ethylthiophen-2-yl, oxazol-2-yl, oxazol-4-yl, 5-phenyloxazol-2-yl, 1-methylpyrazol-4-yl, 2-dimethylaminopyridin-5-yl, 5-acetylthiophen-2-yl, 2-cyanopyrimidin-5-yl, 2-methoxypyrimidin-5-yl, 2-dimethylaminopyrimidin-5-yl, 1-(2-oxopropyl)pyrazol-4-yl, 2-methoxythiazol-4-yl, 2-dimethylaminothiazol-4-yl, and thiazol-2-yl are preferred, and 3-pyridyl group, 2-methoxypyridin-5-yl, 2-trifluoromethoxypyridin-5-yl, 2-trifluoromethylpyridin-5-yl, 2-methoxypyrimidin-5-yl, thiophen-2-yl, thiophen-3-yl, N-methylpyrrol-2-yl, 5-chlorothiophen-2-yl, 5-methylthiophen-2-yl, oxazol-2-yl, oxazol-4-yl, 1-methylpyrazol-4-yl, 5-acetylthiophen-2-yl, 2-methoxypyrimidin-5-yl, 2-dimethylaminopyrimidin-5-yl, 2-methoxythiazol-4-yl, and thiazol-2-yl are more preferred.
As the bicyclic heteroaromatic group which may be substituted, represented by R5, R6, or R7, indol-3-yl, indol-5-yl, indol-6-yl, benzofuran-5-yl, isoindol-5-yl, indazol-5-yl, indazol-6-yl, N-methylindazol-5-yl, N-methylindazol-6-yl, quinolin-6-yl, benzo[b]isoxazol-5-yl, benzo[b]isothiazol-5-yl, isoquinolin-6-yl, benzothiazol-2-yl, benzothiazol-5-yl, benzothiazol-6-yl, benzoxazol-2-yl, benzoxazol-5-yl, and benzoxazol-6-yl are preferred, and indol-3-yl, indol-5-yl, benzofuran-5-yl, isoindol-5-yl, indazol-5-yl, N-methylindazol-5-yl, quinolin-6-yl, benzo[b]isoxazol-5-yl, benzo[b]isothiazol-5-yl, isoquinolin-6-yl, benzothiazol-2-yl, benzothiazol-5-yl, and benzoxazol-5-yl are more preferred. As the alkoxyl group represented by R5, R6, and R7, an alkoxyl group having 1 to 4 carbon atoms is preferred, methoxy group and ethoxy group are more preferred, and methoxy group is particularly preferred. As the the alkyl group arbitrarily substituted with one or more halogen atoms represented by R5, R6, or R7, an alkyl group having 1 to 4 carbon atoms is preferred, monofluoromethyl group, difluoromethyl group, and trifluoromethyl group are more preferred, and trifluoromethyl group is particularly preferred. As the alkoxyl group arbitrarily substituted with one or more halogen atoms represented by R5, R6, or R7, an alkoxyl group having 1 to 4 carbon atoms is preferred, and trifluoromethoxy group is particularly preferred.
It is preferred that any one of R5, R6, and the R7 is hydrogen atom, and it is more preferred that any two of them are hydrogen atoms. Further, all of R5, R6, and R7 may be hydrogen atoms. When one or more of R5, R6, and R7 are substituents other than hydrogen atom, the substituting positions thereof are not particularly limited, and they may exist at arbitrary positions on the benzene ring. When one or more of R5, R6, and R7 are substituents other than hydrogen atom, the substituting positions thereof are preferably selected from the para- and meta-positions relative to the aminoalkyl side chain, and the meta-position is particularly preferred. As another embodiment, the para-position may also be extremely preferred.
R8, R9, and R10 may be the same or different, and independently represent hydrogen atom, hydroxyl group, a halogen atom, an alkyl group, phenyl group, a substituted phenyl group, benzyl group, a substituted benzyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, or N(R16)(R17), or R8 and R9 may together form a benzene ring to represent a bicyclic heteroaromatic group. As R8, R9, and R10, hydrogen atom, a halogen atom, an alkyl group, phenyl group, a substituted phenyl group, benzyl group, a substituted benzyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, and an alkoxyl group arbitrarily substituted with one or more halogen atoms are preferred. The halogen atom, alkyl group, alkoxyl group, alkyl group arbitrarily substituted with one or more halogen atoms, and alkoxyl group arbitrarily substituted with one or more halogen atoms have the same meanings as those defined above.
As R8, R9, and R10, hydrogen atom is preferred. As the halogen atom represented by R8, R9, or R10, halogen atoms independently selected from the group consisting of fluorine atom, chlorine atom, and bromine atom are preferred, and fluorine atom, and chlorine atom are more preferred. As the alkyl group represented by R8, R9, or R10, an alkyl group having 1 to 4 carbon atoms is preferred, methyl group, and ethyl group are more preferred, and methyl group is particularly preferred. As R8, R9, and R10, phenyl group is also preferred. As the substituted phenyl group represented by R8, R9, or R10, 2-hydroxyphenyl group, 3-hydroxyphenyl group, 4-hydroxyphenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 3-chlorophenyl group, 3-tolyl group, 4-tolyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 4-amino-3-hydroxyphenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 3-aminophenyl group, 4-aminophenyl group, 3-nitrophenyl group, 4-nitrophenyl group, 4-hydroxymethylphenyl group, 4-methoxymethylphenyl group, 3,4-dimethoxyphenyl group, 2-trifluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 4-cyanophenyl group, 4-acetylphenyl group, 4-methoxycarbonylphenyl group, 4-carbamoylphenyl group, 4-acetamidophenyl group, 4-methanesulfonylaminophenyl group, 4-(1-hydroxyethyl)phenyl group, 4-methanesulfonylphenyl group, 4-methylsulfinylphenyl group, 4-aminosulfonylphenyl group, 4-methylaminosulfonyl phenyl group, 4-dimethylaminosulfonylphenyl group, and 4-dimethylaminophenyl group are preferred, 4-hydroxyphenyl group, 4-fluorophenyl group, 4-methoxyphenyl group, 4-trifluoromethylphenyl group, 4-hydroxymethylphenyl group, 4-methoxymethylphenyl group, 3,4-dimethoxyphenyl group, 4-trifluoromethoxyphenyl group, 4-cyanophenyl group, 4-acetylphenyl group, 4-methoxycarbonylphenyl group, 4-carbamoylphenyl group, 4-acetamidophenyl group, 4-methanesulfonylaminophenyl group, 4-(1-hydroxyethyl)phenyl group, 4-methanesulfonylphenyl group, 4-methylsulfinylphenyl group, 4-aminosulfonylphenyl group, 4-methylaminosulfonylphenyl group, 4-dimethylaminosulfonylphenyl group, and dimethylaminophenyl group are more preferred, and 4-trifluoromethoxyphenyl group, 4-hydroxymethylphenyl group, 4-methoxymethylphenyl group, 4-cyanophenyl group, 4-acetylphenyl group, 4-methoxycarbonylphenyl group, 4-carbamoylphenyl group, 4-(1-hydroxyethyl)phenyl group, 4-methanesulfonylphenyl group, 4-methylsulfinylphenyl group, 4-aminosulfonylphenyl group, 4-methylaminosulfonylphenyl group, 4-dimethylaminosulfonylphenyl group, and 4-acetamidophenyl group are particularly preferred.
As R8, R9, and R10, benzyl group is also preferred. As the substituted benzyl group represented by R8, R9, or R10, 2-hydroxybenzyl group, 3-hydroxybenzyl group, 4-hydroxybenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, 3-chlorobenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 2-methoxybenzyl group, 3-methoxybenzyl group, 4-methoxybenzyl group, 4-amino-3-hydroxybenzyl group, 2-trifluoromethylbenzyl group, 3-trifluoromethylbenzyl group, 4-trifluoromethylbenzyl group, 3-aminobenzyl group, 4-aminobenzyl group, 3-nitrobenzyl group, 4-nitrobenzyl group, 3,4-dimethoxybenzyl group, 2-trifluoromethoxybenzyl group, 3-trifluoromethoxybenzyl group, 4-trifluoromethoxybenzyl group, 4-cyanobenzyl group, 4-acetylbenzyl group, 4-methoxycarbonylbenzyl group, 4-carbamoylbenzyl group, 4-acetamidobenzyl group, 4-methanesulfonylaminobenzyl group, and 4-dimethylaminobenzyl group are preferred, and 4-trifluoromethoxybenzyl group, 4-cyanobenzyl group, 4-acetylbenzyl group, 4-methoxycarbonylbenzyl group, 4-carbamoylbenzyl group, and 4-acetamidobenzyl group are more preferred.
As the monocyclic heteroaromatic group which may be substituted, represented by R8, R9, or R10, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-methoxypyridin-6-yl, 2-methoxypyridin-5-yl, 2-trifluoromethoxypyridin-5-yl, 2-trifluoromethylpyridin-5-yl, 2-morpholinopyridin-5-yl, 2-methoxypyrimidin-5-yl, furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, pyrrol-2-yl, N-methylpyrrol-2-yl, 5-chlorothiophen-2-yl, 5-nitrothiophen-2-yl, 5-methylthiophen-2-yl, 5-ethylthiophen-2-yl, oxazol-2-yl, oxazol-4-yl, 5-phenyloxazol-2-yl, 1-methylpyrazol-4-yl, 2-dimethylaminopyridin-5-yl, 5-acetylthiophen-2-yl, 2-cyanopyrimidin-5-yl, 2-methoxypyrimidin-5-yl, 2-dimethylaminopyrimidin-5-yl, 1-(2-oxopropyl)pyrazol-4-yl, 2-methoxythiazol-4-yl, 2-dimethylaminothiazol-4-yl, and thiazol-2-yl are preferred, and 3-pyridyl group, 2-methoxypyridin-5-yl, 2-trifluoromethoxypyridin-5-yl, 2-trifluoromethylpyridin-5-yl, 2-methoxypyrimidin-5-yl, thiophen-2-yl, thiophen-3-yl, N-methylpyrrol-2-yl, 5-chlorothiophen-2-yl, 5-methylthiophen-2-yl, oxazol-2-yl, oxazol-4-yl, 1-methylpyrazol-4-yl, 5-acetylthiophen-2-yl, 2-methoxypyrimidin-5-yl, 2-dimethylaminopyrimidin-5-yl, 2-methoxythiazol-4-yl, and thiazol-2-yl are more preferred.
As the bicyclic heteroaromatic group which may be substituted, represented by R8, R9, or R10, indol-3-yl, indol-5-yl, indol-6-yl, benzofuran-5-yl, isoindol-5-yl, indazol-5-yl, indazol-6-yl, N-methylindazol-5-yl, N-methylindazol-6-yl, quinolin-6-yl, benzo[b]isoxazol-5-yl, benzo[b]isothiazol-5-yl, isoquinolin-6-yl, benzothiazol-2-yl, benzothiazol-5-yl, benzothiazol-6-yl, benzoxazol-2-yl, benzoxazol-5-yl, and benzoxazol-6-yl are preferred, and indol-3-yl, indol-5-yl, benzofuran-5-yl, isoindol-5-yl, indazol-5-yl, N-methylindazol-5-yl, quinolin-6-yl, benzo[b]isoxazol-5-yl, benzo[b]isothiazol-5-yl, isoquinolin-6-yl, benzothiazol-2-yl, benzothiazol-5-yl, and benzoxazol-5-yl are more preferred. As the alkoxyl group represented by R8, R9, or R10, an alkoxyl group having 1 to 4 carbon atoms is preferred, methoxy group, and ethoxy group are more preferred, and methoxy group is particularly preferred. As the the alkyl group arbitrarily substituted with one or more halogen atoms represented by R8, R9, or R10, an alkyl group having 1 to 4 carbon atoms is preferred, monofluoromethyl group, difluoromethyl group, and trifluoromethyl group are more preferred, and trifluoromethyl group is particularly preferred. As the alkoxyl group arbitrarily substituted with one or more halogen atoms represented by R8, R9, or R10, an alkoxyl group having 1 to 4 carbon atoms is preferred, and trifluoromethoxy group is particularly preferred.
It is preferred that one of R8 and R10 is hydrogen atom, and it is more preferred that R8 and R10 are hydrogen atoms. It is preferred that R9 is hydrogen atom, hydroxyl group, a halogen atom, an alkyl group, phenyl group, a substituted phenyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, or an alkoxyl group, and it is more preferred that R9 is a substituted phenyl group, a monocyclic heteroaromatic group which may be substituted, or a bicyclic heteroaromatic group which may be substituted, and R8 and R10 are hydrogen atoms.
Further, R8 and R10 may together form a benzene ring and thereby form a bicyclic heteroaromatic group as A3, and as the heteroaromatic group, specifically, a monovalent group formed from benzothiophene, benzofuran, indazole, indole or the like by eliminating one arbitrary hydrogen atom is preferred.
X1 represents oxygen atom, sulfur atom, or N—R19 wherein R19 represents hydrogen atom, an alkyl group, phenyl group, or a substituted phenyl group. It is preferred that X1 is oxygen atom, and it is also preferred that X is sulfur atom. Further, it is also preferred that X1 is N—R19, and a lower alkyl group is preferred as R19. As the lower alkyl group, methyl group, and ethyl group are preferred, and methyl group is more preferred.
R23 is hydrogen atom, hydroxyl group, a halogen atom, an alkyl group, phenyl group, a substituted phenyl group, benzyl group, a substituted benzyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, or N(R16)(R17). As R23, hydrogen atom, a halogen atom, an alkyl group, phenyl group, a substituted phenyl group, benzyl group, a substituted benzyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, and an alkoxyl group arbitrarily substituted with one or more halogen atoms are preferred.
As R23, hydrogen atom is preferred. As the halogen atom represented by R23, a halogen atom selected from the group consisting of fluorine atom, chlorine atom, and bromine atom is preferred, and fluorine atom, and chlorine atom are more preferred. As the alkyl group represented by R23, an alkyl group having 1 to 4 carbon atoms is preferred, methyl group, and ethyl group are more preferred, and methyl group is particularly preferred. As R23, phenyl group is also preferred. As the substituted phenyl group represented by R23, 2-hydroxyphenyl group, 3-hydroxyphenyl group, 4-hydroxyphenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 3-chlorophenyl group, 3-tolyl group, 4-tolyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 4-amino-3-hydroxyphenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 3-aminophenyl group, 4-aminophenyl group, 3-nitrophenyl group, 4-nitrophenyl group, 4-hydroxymethylphenyl group, 4-methoxymethylphenyl group, 3,4-dimethoxyphenyl group, 2-trifluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 4-cyanophenyl group, 4-acetylphenyl group, 4-methoxycarbonylphenyl group, 4-carbamoylphenyl group, 4-acetamidophenyl group, 4-methanesulfonylaminophenyl group, 4-(1-hydroxyethyl)phenyl group, 4-methanesulfonylphenyl group, 4-methylsulfinylphenyl group, 4-aminosulfonylphenyl group, 4-methylaminosulfonylphenyl group, 4-dimethylaminosulfonylphenyl group, and 4-dimethylaminophenyl group are preferred, 4-hydroxyphenyl group, 4-fluorophenyl group, 4-methoxyphenyl group, 4-trifluoromethylphenyl group, 4-hydroxymethylphenyl group, 4-methoxymethylphenyl group, 3,4-dimethoxyphenyl group, 4-trifluoromethoxyphenyl group, 4-cyanophenyl group, 4-acetylphenyl group, 4-methoxycarbonylphenyl group, 4-carbamoylphenyl group, 4-acetamidophenyl group, 4-methanesulfonylaminophenyl group, 4-(1-hydroxyethyl)phenyl group, 4-methanesulfonylphenyl group, 4-methylsulfinylphenyl group, 4-aminosulfonylphenyl group, 4-methylaminosulfonylphenyl group, 4-dimethylaminosulfonylphenyl group, and 4-dimethylaminophenyl group are more preferred, and 4-trifluoromethoxyphenyl group, 4-hydroxymethylphenyl group, 4-methoxymethylphenyl group, 4-cyanophenyl group, 4-acetylphenyl group, 4-methoxycarbonylphenyl group, 4-carbamoylphenyl group, 4-(1-hydroxyethyl)phenyl group, 4-methanesulfonylphenyl group, 4-methylsulfinylphenyl group, 4-aminosulfonylphenyl group, 4-methylaminosulfonylphenyl group, 4-dimethylaminosulfonylphenyl group, and 4-acetamidophenyl group are particularly preferred.
As R23, benzyl group is also preferred. As the substituted benzyl group represented by R23, 2-hydroxybenzyl group, 3-hydroxybenzyl group, 4-hydroxybenzyl group, 3-fluorobenzyl group, 4-fluorobenzyl group, 3-chlorobenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 2-methoxybenzyl group, 3-methoxybenzyl group, 4-methoxybenzyl group, 4-amino-3-hydroxybenzyl group, 2-trifluoromethylbenzyl group, 3-trifluoromethylbenzyl group, 4-trifluoromethylbenzyl group, 3-aminobenzyl group, 4-aminobenzyl group, 3-nitrobenzyl group, 4-nitrobenzyl group, 3,4-dimethoxybenzyl group, 2-trifluoromethoxybenzyl group, 3-trifluoromethoxybenzyl group, 4-trifluoromethoxybenzyl group, 4-cyanobenzyl group, 4-acetylbenzyl group, 4-methoxycarbonylbenzyl group, 4-carbamoylbenzyl group, 4-acetamidobenzyl group, 4-methanesulfonylaminobenzyl group, and 4-dimethylaminobenzyl group are preferred, and 4-trifluoromethoxybenzyl group, 4-cyanobenzyl group, 4-acetylbenzyl group, 4-methoxycarbonylbenzyl group, 4-carbamoylbenzyl group, and 4-acetamidobenzyl group are more preferred.
As the monocyclic heteroaromatic group which may be substituted, represented by R23, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-methoxypyridin-6-yl, 2-methoxypyridin-5-yl, 2-trifluoromethoxypyridin-5-yl, 2-trifluoromethylpyridin-5-yl, 2-morpholinopyridin-5-yl, 2-methoxypyrimidin-5-yl, furan-2-yl, furan-3-yl, thiophen-2-yl, thiophen-3-yl, pyrrol-2-yl, N-methylpyrrol-2-yl, 5-chlorothiophen-2-yl, 5-nitrothiophen-2-yl, 5-methylthiophen-2-yl, 5-ethylthiophen-2-yl, oxazol-2-yl, oxazol-4-yl, 5-phenyloxazol-2-yl, 1-methylpyrazol-4-yl, 2-dimethylaminopyridin-5-yl, 5-acetylthiophen-2-yl, 2-cyanopyrimidin-5-yl, 2-methoxypyrimidin-5-yl, 2-dimethylaminopyrimidin-5-yl, 1-(2-oxopropyl)pyrazol-4-yl, 2-methoxythiazol-4-yl, 2-dimethylaminothiazol-4-yl, and thiazol-2-yl are preferred, and 3-pyridyl group, 2-methoxypyridin-5-yl, 2-trifluoromethoxypyridin-5-yl, 2-trifluoromethylpyridin-5-yl, 2-methoxypyrimidin-5-yl, thiophen-2-yl, thiophen-3-yl, N-methylpyrrol-2-yl, 5-chlorothiophen-2-yl, 5-methylthiophen-2-yl, oxazol-2-yl, oxazol-4-yl, 1-methylpyrazol-4-yl, 5-acetylthiophen-2-yl, 2-methoxypyrimidin-5-yl, 2-dimethylaminopyrimidin-5-yl, 2-methoxythiazol-4-yl, and thiazol-2-yl are more preferred. As the bicyclic heteroaromatic group which may be substituted, represented by R23, indol-3-yl, indol-5-yl, indol-6-yl, benzofuran-5-yl, isoindol-5-yl, indazol-5-yl, indazol-6-yl, N-methylindazol-5-yl, N-methylindazol-6-yl, quinolin-6-yl, benzo[b]isoxazol-5-yl, benzo[b]isothiazol-5-yl, isoquinolin-6-yl, benzothiazol-2-yl, benzothiazol-5-yl, benzothiazol-6-yl, benzoxazol-2-yl, benzoxazol-5-yl, and benzoxazol-6-yl are preferred, and indol-3-yl, indol-5-yl, benzofuran-5-yl, isoindol-5-yl, indazol-5-yl, N-methylindazol-5-yl, quinolin-6-yl, benzo[b]isoxazol-5-yl, benzo[b]isothiazol-5-yl, isoquinolin-6-yl, benzothiazol-2-yl, benzothiazol-5-yl, and benzoxazol-5-yl are more preferred. As the alkoxyl group represented by R23, an alkoxyl group having 1 to 4 carbon atoms is preferred, methoxy group, and ethoxy group are more preferred, and methoxy group is particularly preferred. As the alkyl group arbitrarily substituted with one or more halogen atoms represented by R23, an alkyl group having 1 to 4 carbon atoms is preferred, monofluoromethyl group, difluoromethyl group, and trifluoromethyl group are more preferred, and trifluoromethyl group is particularly preferred. As the alkoxyl group arbitrarily substituted with one or more halogen atoms represented by R23, an alkoxyl group having 1 to 4 carbon atoms is preferred, and trifluoromethoxy group is particularly preferred.
X2 represents oxygen atom, sulfur atom, or N—R19 wherein R19 represents hydrogen atom, an alkyl group, phenyl group, or a substituted phenyl group. It is preferred that X2 is oxygen atom, and it is also preferred that X2 is sulfur atom. Further, it is also preferred that X2 is N—R19, and hydrogen atom, and a lower alkyl group are preferred as R19. As the lower alkyl group, methyl group and ethyl group are preferred, and methyl group is more preferred.
R11 represents hydrogen atom, hydroxyl group, a halogen atom, an alkyl group, an alkoxyl group, a thioalkoxyl group, hydroxymethyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, or N(R20)(R21). As the R11, hydrogen atom, a halogen atom, an alkyl group, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, or N(R20)(R21) is preferred, and hydrogen atom, a halogen atom, an alkyl group, or an alkoxyl group is more preferred. The halogen atom, alkyl group, alkoxyl group, alkyl group arbitrarily substituted with one or more halogen atoms, and alkoxyl group arbitrarily substituted with one or more halogen atoms have the same meanings as those defined above. It is preferred that R11 is hydrogen atom. As the halogen atom represented by R11, fluorine atom, chlorine atom, or bromine atom is preferred, and chlorine atom is more preferred. As the alkyl group represented by R11, an alkyl group having 1 to 4 carton atoms is preferred, and methyl group and ethyl group are more preferred. As the alkoxyl group represented by R11, an alkoxyl group having 1 to 4 carton atoms is preferred, and methoxy group is more preferred. As the alkyl group arbitrarily substituted with one or more halogen atoms represented by R11, an alkyl group having 1 to 4 carton atoms and arbitrarily substituted with one or more halogen atoms is preferred, and trifluoromethyl group is more preferred. As the alkoxyl group arbitrarily substituted with one or more halogen atoms represented by R11, an alkoxyl group having 1 to 4 carton atoms and arbitrarily substituted with one or more halogen atoms is preferred.
R20 and R21 may be the same or different, and independently represent hydrogen atom, an alkyl group, an acyl group, or SO2R22 wherein R22 represents a lower alkyl group, or R20 and R21 together form a 3- to 7-membered ring to represent a cyclic amine as N(R20)(R21). The alkyl group and acyl group have the same meanings as those defined above. It is preferred that R20 and R21 are hydrogen atoms. As the alkyl group represented by R20 or R21, an alkyl group having 1 to 4 carton atoms is preferred, and methyl group and ethyl group are more preferred. As the acyl group represented by R20 or R21, an acyl group having 2 to 5 carton atoms is preferred, and acetyl group is more preferred. More specifically, examples of N(R20)(R21) include amino group, a monoalkylamino group, a dialkylamino group, a monoacylamino group, a diacylamino group, and an acylated monoalkylamino group, and preferred examples include amino group, a monoalkylamino group, a dialkylamino group, and a monoacylamino group. As N(R20)(R21), amino group is preferred. As the monoalkylamino group represented by N(R20)(R21), an amino group substituted with an alkyl group having 1 to 4 carton atoms is preferred, and methylamino group and ethylamino group are more preferred. As the dialkylamino group represented by N(R20)(R21), an amino group substituted with alkyl groups independently having 1 to 4 carton atoms is preferred, and dimethylamino group is more preferred. As the monoacylamino group represented by N(R20)(R21), an amino group substituted with an acyl group having 2 to 5 carton atoms is preferred, and acetylamino group is more preferred. When R20 and R21 together form a 3- to 7-membered ring and thereby form a cyclic amine as N(R20)(R21), a 3- to 7-membered cyclic amine is preferred, and a 6-membered cyclic amine is more preferred. Specifically, morpholine, piperidine, and piperazine are preferred, and morpholine is more preferred.
R12 represents hydrogen atom or an alkyl group, and it is preferred that R12 is hydrogen atom. As the alkyl group represented by R12, a lower alkyl group is preferred, an alkyl group having 1 to 4 carton atoms is more preferred, and methyl group is further preferred. Y2 represents CH or nitrogen atom, and it is preferred that Y2 is CH.
R13 represents hydrogen atom, hydroxyl group, a halogen atom, an alkyl group, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, or N(R20)(R21) (in the formula, R20 and R21 may be the same or different, and independently represents hydrogen atom, an alkyl group, an acyl group, or SO2R22 wherein R22 is a lower alkyl group). It is preferred that R13 is hydrogen atom. Y4 represents sulfur atom or oxygen atom. Any one of Y3, Y5, and Y6 is nitrogen atom, and the remaining group is CH. It is preferred that Y4 is sulfur atom, Y5 is nitrogen atom, and Y3 and Y6 represent CH.
R14 represents hydrogen atom, hydroxyl group, a halogen atom, an alkyl group, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, or N(R20)(R21) (in the formula, R20 and R21 may be the same or different, and independently represent hydrogen atom, an alkyl group, an acyl group, or SO2R22 wherein R22 is a lower alkyl group). It is preferred that R14 is hydrogen atom. Y7 represents CH or nitrogen atom, and is preferably CH.
R15 represents hydrogen atom, hydroxyl group, a halogen atom, an alkyl group, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, or N(R20)(R21) (in the formula, R20 and R21 may be the same or different, and independently represent hydrogen atom, an alkyl group, an acyl group, or SO2R22 wherein R22 is a lower alkyl group). It is preferred that R15 is hydrogen atom.
The substituent(s) in the substituted phenyl group, substituted benzyl group, 5-membered heteroaromatic group having two hetero atoms in the ring which may be substituted, monocyclic heteroaromatic group which may be substituted, and bicyclic heteroaromatic group which may be substituted is (are) selected from hydrogen atom, hydroxyl group, a halogen atom, an alkyl group, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, cyano group, an acyl group, CON(R24)(R25), COOR26, S(O)mR27, SO2R28, CH2OR29, CH(OH)CH3, CH2N(R30)(R31), and N(R32)(R33). Number of the substituent(s) is 1 to 3. The number of the substituent(s) is preferably 1 or 2, more preferably 1. The substituting positions thereof are not particularly limited, and they may exist on arbitrary positions on the phenyl group. However, the substituting positions thereof are preferably chosen from the para- and/or meta-positions relative to the aminoalkyl side chain, and the meta-position is particularly preferred. The para-position is also particularly preferred. As the substituent(s), hydrogen atom, hydroxyl group, a halogen atom, an alkyl group, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, cyano group, an acyl group, CON(R24)(R25), COOR26, S(O)mR27, SO2R28, CH2OR29, and CH(OH)CH3 are preferred, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, cyano group, an acyl group, CON(R24)(R25), S(O)mR27, SO2R28, CH2OR29, and CH(OH)CH3 are more preferred, and cyano group, an acyl group, CON(R24)(R25), S(O)mR27, SO2R28, CH2OR29, and CH(OH)CH3 are particularly preferred. As the halogen atom as the substituent, fluorine atom, chlorine atom, and bromine atom are preferred, and fluorine atom, and chlorine atom are particularly preferred. As the alkyl group as the substituent, an alkyl group having 1 to 4 carbon atoms is preferred, methyl group, and ethyl group are more preferred, and methyl group is particularly preferred. As the alkoxyl group as the substituent, an alkoxyl group having 1 to 4 carbon atoms is preferred, methoxy group, and ethoxy group are more preferred, and methoxy group is particularly preferred. As the alkyl group arbitrarily substituted with one or more halogen atoms as the substituent, an alkyl group having 1 to 4 carbon atoms and arbitrarily substituted with one or more halogen atoms is preferred, fluoromethyl group, difluoromethyl group, trifluoromethyl group, trichloromethyl group, 1-fluoroethyl group, and 1,1,1-trifluoroethyl group are more preferred, and trifluoromethyl group is particularly preferred. As the alkoxyl group arbitrarily substituted with one or more halogen atoms as the substituent, an alkoxyl group having 1 to 4 carbon atoms and arbitrarily substituted with one or more halogen atoms is preferred, fluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, trichloromethoxy group, 1-fluoroethoxy group, and 1,1,1-trifluoroethoxy group are more preferred, and trifluoromethoxy group is particularly preferred. As the substituent, cyano group is also preferred. As the acyl group as the substituent, an acyl group having 2 to 5 carbon atoms is preferred, acetyl group, and ethylcarbonyl group are more preferred, and acetyl group is particularly preferred. As CON(R24)(R25) as the substituent, CONH2, CONH(CH3), CON(CH3)2, and CONCH3(OCH3) are preferred. As COOR26 as the substituent, COOCH3 and COOC2H5 are preferred, and COOCH3 is particularly preferred. As S(O)mR27 as the substituent, SCH3, SC2H5, SOCH3, and SOC2H5 are preferred, and SCH3 and SOCH3 are more preferred. As SO2R28 as the substituent, SO2CH3, SO2C2H5, SO2NH2, SO2N(CH3)2, and SO2NHCH3 are preferred, and SO2CH3 is particularly preferred. As CH2OR29 as the substituent, CH2OH, and CH2OCH3 are preferred. As the substituent, CH(OH)CH3 is also preferred. As CH2N(R30)(R31) as the substituent, CH2NH2, CH2NHCH3, and CH2N(CH3)2 are preferred. As N(R32)(R33) as the substituent, NH2, NHCH3, N(CH3)2, morpholin-1-yl, piperazin-1-yl, NHCOCH3, NHCOOCH3, NHCONH2, NHCONH(CH3), NHCON(CH3)2, and NHSO2CH3 are preferred. As CSR36 as the substituent, CSCH3, CSC2H5, CSNH2, CSNHCH3, and CSN(CH3)2 are preferred. As CH2COR37 as the substituent, CH2COCH3 is preferred. As CH2CH(OR38)R39 as the substituent, CH2CH(OH)CH3 is preferred.
Symbol “A” represents a group represented by the formula A1, A2, or A3, a saturated heterocyclic group, or a 5-membered heteroaromatic group having two heteroatoms in the ring which may be substituted (preferably, a group represented by the formula A4). The saturated heterocyclic group is, specifically, a monovalent group formed by eliminating one arbitrary hydrogen atom form tetrahydrofuran, pyrrolidine, piperidine, morpholine, or the like.
It is preferred that A is a group represented by the formula A1. Further, A may be a group represented by the formula A2, and it is also extremely preferred that A is a group represented by the formula A3. Further, according to another embodiment, it is also preferred that A is a 5-membered heteroaromatic group having two heteroatoms, and it is also extremely preferred that A is a group represented by the formula A4.
Examples of A include a group represented by any of the following formulas (A-1) to (A-590).



































































































































































































































































Examples of the group represented by the formula A1 include those represented by the aforementioned formulas (A-1) to (A-60), (A-253) to (A-302), and (A-452) to (A-486), and those represented by the formulas (A-28), (A-34), (A-44), (A-54), (A-56), (A-57), (A-287), (A-452), (A-453), (A-460), (A-461), and (A-486) are preferred.
Examples of the group represented by the formula A2 include those represented by the aforementioned formulas (A-61) to (A-113), (A-303) to (A-360), and (A-487) to (A-521). Those represented by the formulas (A-83), (A-85), (A-86), (A-91), (A-94), (A-104), (A-106), (A-107), (A-108), (A-346), (A-495), (A-496), and (A-521) are preferred, and those represented by the formulas (A-86), (A-104), (A-107), and (A-496) are particularly preferred.
Examples of the group represented by the formula A3 include those represented by the aforementioned formulas (A-114) to (A-181), (A-361) to (A-400), and (A-522) to (A-556). Those represented by the formulas (A-114), (A-118), (A-135) to (A-142), (A-146), (A-153), (A-171), (A-177), (A-396), (A-398), (A-522), (A-523), (A-528), (A-530), (A-531), (A-532), and (A-556) are preferred, and those represented by the formulas (A-135), (A-139), (A-142), (A-153), (A-171), (A-396), (A-398), (A-522), (A-523), (A-531), and (A-556) are particularly preferred.
Examples of the group represented by the formula A4 include those represented by the formulas (A-182) to (A-236), (A-401) to (A-426), and (A-557) to (A-590). Those represented by the formulas (A-201), (A-204), (A-205), (A-206), (A-210), (A-219), (A-222), (A-229), (A-230), (A-233), (A-234), (A-411), (A-563), (A-566), and (A-569) are preferred, and those represented by the formulas (A-204), (A-205), (A-233), and (A-411) are particularly preferred.
Examples of the 5-membered heteroaromatic group having two hetero atoms in the ring include those represented by the formulas (A-237) to (A-252), and (A-427) to (A-445), and those represented by the formulas (A-245), (A-246), (A-251), and (A-252) are preferred.
In the groups represented by the formulas B1, B2, B3, B4, and B5, when each of R11, R12, R13, R14, and R15 represents a substituent other than hydrogen atom, the substituent can exist at an arbitrary substitutable position on the condensed ring. That is, R11 can substitute at any one of the 2-, 4-, 5-, 6-. and 7-positions, and the substituting position of R11 is preferably the 5-position. When Y2 is CH, R12 can substitute at any of the 2-, 3-, 4-, 5-, 6-, 7-, and 8-position, and the substituting position of R12 is preferably the 7-position. When Y2 is nitrogen atom, it can substitute at any one of the 2-, 4-, 5-, 6-, 7-, and 8-positions, and the substituting position of R12 is preferably the 5-position. R13 can substitute at the 5- or 6-position, and the substituting position of R13 is preferably the 5-position. R14 can substitute at any one of the 2-, 4-, 6-, and the 7-positions, and the substituting position of R14 is preferably the 5-position. R15 can substitute at any one of the 2-, 4-, 5-, 6-, and 7-positions, and the substituting position of R15 is preferably the 5-position. B is preferably a group represented by the formula B1. Further, it is also preferred that B is a group represented by the formula B2, and B may be a group represented by the formula B3. Further, B may be naphthalene-1-yl group which may be substituted with a substituent (hydroxyl group, halogen atom, alkyl group, alkoxy group). Y1 represents sulfur atom or oxygen atom, and it is preferred that Y1 is sulfur atom.
Examples of the group represented by the formula B1 include the groups represented by following formulas (B-1) to (B-4). The groups represented by the formulas (B-1), and (B-2) are preferred, and the group represented by the formula (B-1) is particularly preferred.




Examples of the group represented by the formula B2 include the groups represented by following formulas (B-5) to (B-8), and the group represented by the formula (B-5) is preferred.




Examples of the group represented by the formula B3 include the groups represented by following formulas (B-9) to (B-14), and the group represented by the formula (B-12) is preferred.




Examples of the group represented by the formula B4 include the groups represented by following formulas (B-15) to (B-17). The groups represented by the formulas (B-15), and (B-16) are preferred, and the group represented by the formula (B-15) is particularly preferred.




Examples of the group represented by the formula B5 include the groups represented by following formulas (B-18), and (B-19), and the group represented by the formula (B-18) is preferred.




R1 represents an alkyl group. As the alkyl group represented by R1, a lower alkyl group is preferred, an alkyl group having 1 to 4 carton atoms is more preferred, and methyl group and ethyl group are further preferred. Further, methyl group is particularly preferred.
Symbol “n” represents the number of carbon atoms in the alkylene group existing between A and —NH—CH(B)(R1). n represents an integer of 2 to 6, preferably 2 to 4, more preferably 2 or 3, most preferably 3.
A combination of the substituents in the formula (1) is not particularly limited. For example, preferred compounds include:

    (1) compounds wherein R2 is hydrogen atom, trifluoromethyl group, difluoromethyl group, fluoromethyl group, methyl group, trifluoromethoxy group, hydroxyl group, methoxy group, amino group, phenyl group, benzyl group, pyridyl group, furanyl group, fluorine atom, chlorine atom, or bromine atom, and R3 and R4 are hydrogen atoms;
    (2) compounds wherein R2 is 4-hydroxyphenyl group, 4-trifluoromethylphenyl group, 4-cyanophenyl group, 4-acetylphenyl group, 4-methoxycarbonylphenyl group, 4-carbamoylphenyl group, 4-hydroxymethylphenyl group, 4-methoxymethylphenyl group, 2-methoxypyrimidin-5-yl, 2-methoxypyridin-5-yl, 2-trifluoromethylpyridin-5-yl, 4-methanesulfonylphenyl group, 2-dimethylaminopyrimidin-5-yl, or 1-methylindazol-5-yl, and R3 and R4 are hydrogen atoms;
    (3) compounds wherein R2, R3, and R4 are hydrogen atoms;
    (4) compounds wherein R2 is trifluoromethyl group, and R3 and R4 are hydrogen atoms;
    (5) compounds wherein R5 is hydrogen atom, methyl group, methoxy group, amino group, phenyl group, benzyl group, furanyl group, thiofuranyl group, or indolyl group, and R6 and R7 are hydrogen atoms;
    (6) compounds wherein R5 is 4-hydroxyphenyl group, 4-trifluoromethylphenyl group, 4-cyanophenyl group, 4-acetylphenyl group, 4-methoxycarbonylphenyl group, 4-carbamoylphenyl group, 4-hydroxymethylphenyl group, 4-methoxymethylphenyl group, 2-methoxypyrimidin-5-yl, 2-methoxypyridin-5-yl, 2-trifluoromethylpyridin-5-yl, 4-methanesulfonylphenyl group, 2-dimethylaminopyrimidin-5-yl, or 1-methylindazol-5-yl, and R6 and R7 are hydrogen atoms;
    (7) compounds wherein R5, R6, and R7 are hydrogen atoms;
    (8) compounds wherein R8 and R10 are hydrogen atoms, and R9 is methyl group, phenyl group, m-chlorophenyl group, p-aminophenyl group, furanyl group, thiofuranyl group, amino group, or nitro group;
    (9) compounds wherein R8 and R10 are hydrogen atoms, and R9 is 4-hydroxyphenyl group, 4-trifluoromethylphenyl group, 4-cyanophenyl group, 4-acetylphenyl group, 4-methoxycarbonylphenyl group, 4-carbamoylphenyl group, 4-hydroxymethylphenyl group, 4-methoxymethylphenyl group, 2-methoxypyrimidin-5-yl, 2-methoxypyridin-5-yl, 2-trifluoromethylpyridin-5-yl, 4-methanesulfonylphenyl group, 2-dimethylaminopyrimidin-5-yl, or 1-methylindazol-5-yl;
    (10) compounds wherein R8 and R9 together form a benzene ring and thereby form benzothiophen-2-yl group, benzothiophen-3-yl group, indol-2-yl group, indol-3-yl group, benzofuran-2-yl group, or benzofuran-3-yl group as a bicyclic heterocyclic group as A3, and R10 is hydrogen atom;
    (11) compounds wherein R8, R9, and R10 are hydrogen atoms;
    (12) compounds wherein A is pyrrolidinyl group, piperidinyl group, or morphonyl group as a saturated heterocyclic group;
    (13) compounds wherein A is pyrazonyl group, thiazolidinyl group, or isoxazolyl group;
    (14) compounds wherein R23 is hydrogen atom, trifluoromethyl group, difluoromethyl group, fluoromethyl group, methyl group, trifluoromethoxy group, hydroxyl group, methoxy group, amino group, phenyl group, benzyl group, pyridyl group, furanyl group, fluorine atom, chlorine atom, or bromine atom;
    (15) compounds wherein R23 is 4-hydroxyphenyl group, 4-trifluoromethylphenyl group, 4-cyanophenyl group, 4-acetylphenyl group, 4-methoxycarbonylphenyl group, 4-carbamoylphenyl group, 4-hydroxymethylphenyl group, 4-methoxymethylphenyl group, 2-methoxypyrimidin-5-yl, 2-methoxypyridin-5-yl, 2-trifluoromethylpyridin-5-yl, 4-methanesulfonylphenyl group, 2-dimethylaminopyrimidin-5-yl, or 1-methylindazol-5-yl;
    (16) compounds of (14) or (15) wherein X2 is oxygen atom; and
    (17) compounds of (14) or (15) wherein X2 is sulfur atom.


More preferred compounds include:

    (18) compounds of (1) to (17) wherein R1 is methyl group or ethyl group; and
    (19) compounds of (1) to (18) wherein R1 is methyl group.


Preferred compounds further include:

    (20) compounds of (1) to (19) wherein B is a group represented by the formula B1;
    (21) compounds of (20) wherein Y1 is sulfur atom;
    (22) compounds of (21) wherein R11 is hydrogen atom, methyl group, methoxy group, fluorine atom, or chlorine atom;
    (23) compounds of (1) to (19) wherein B is a group represented by the formula B2;
    (24) compounds of (23) wherein R12 is hydrogen atom or methyl group;
    (25) compounds of (24) wherein R12 is hydrogen atom, and Y2 is CH;
    (26) compounds of (1) to (19) wherein B is a group represented by the formula B3;
    (27) compounds of (26) wherein R13 is hydrogen atom or methyl group;
    (28) compounds of (1) to (19) wherein B is a group represented by the formula B4;
    (29) compounds of (28) wherein R14 is hydrogen atom or methyl group;
    (30) compounds of (1) or (19) wherein B is a group represented by the formula B5; and
    (31) compounds of (30) wherein R15 is hydrogen atom.


Also preferred compounds include:

    (32) compounds of (1) to (19) wherein B is naphthalen-1-yl group which may be substituted; and
    (33) compounds of (32) wherein B is naphthalen-1-yl group.


Still more preferred compounds include:

    (34) compounds wherein A is a group represented by the formula A2, A3, or A4, or a 5-membered heteroaromatic group having two heteroatoms, B is a group represented by the formula B1, Y1 is sulfur atom, and R11 is hydrogen atom, methyl group, or methoxy group;
    (35) compounds wherein A is a group represented by the formula A2, A3, or A4, or a 5-membered heteroaromatic group having two heteroatoms, B is a group represented by the formula B2, Y1 is CH, and R12 is hydrogen atom; and
    (36) compounds of (35) wherein A is a group represented by the formula A3, or A4.


In the compounds represented by the aforementioned formula (1), the carbon atoms on which NH, B, and R1 substitute are asymmetric carbons. The steric configuration of these asymmetric carbons are not particularly limited, and the configuration may be S-configuration, or R-configuration. The compounds of the present invention may consist of an arbitrary mixture or racemate of pure optical isomers based on these asymmetric carbons. However, in view of the desired biological action, the steric configuration of the aforementioned asymmetric carbons is preferably R-configuration. Further, the compounds of the present invention may have one or more asymmetric carbons depending on the types of the substituents, and a steric configuration of the atoms other than the asymmetric carbons specified above is not particularly limited and the compounds may be in an arbitrary steric configuration. Pure stereoisomers including optical isomers and diastereoisomers based on one or more asymmetric carbons, any mixtures, racemates and the like of stereoisomers all fall within the scope of the present invention.
Types of salts of the compounds of the formula (1) are not particularly limited, and the salts may be either acid addition salts or base addition salts. The salts may also be in the form of a molecule having an intramolecular counter ion. Examples of the acid addition salts include, for example, hydrochlorides, hydrobromides, sulfates, hydrogensulfates, dihydrogenphosphates, citrates, maleates, tartrates, fumarates, gluconates, methanesulfonates, and addition salts with an optically active acid such as camphorsulfonic acid, mandelic, and a substituted mandelic acid. A base addition salt may be formed when any one or more of R2 to R15 are hydroxyl groups, and examples include, for example, metal salts such as sodium salts and potassium salts, ammonium salts and the like. However, the type of the salts is not limited to these examples, and those skilled in the art can appropriately choose a salt. Among them, physiologically acceptable salts are preferred. The compounds of the present invention and salts thereof may exist as hydrates or solvates, and such substances also fall within the scope of the present invention.
Preferred examples of the compounds of the present invention represented by the formula (1) include the following compounds:

    [1-(benzothiophen-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(3-methylphenyl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(3-difluoromethylphenyl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(3-monofluoromethylphenyl)propyl]amine;
    [1-(benzothiophen-3-yl)propyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(2-methylbenzothiophen-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(4-methylbenzothiophen-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(5-methylbenzothiophen-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(6-methylbenzothiophen-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(7-methylbenzothiophen-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(5-fluorobenzothiophen-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(5-chlorobenzothiophen-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(5-bromobenzothiophen-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(5-methoxybenzothiophen-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(5-thiomethoxybenzothiophen-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(5-hydroxybenzothiophen-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(5-hydroxymethylbenzothiophen-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]-amine;
    [1-(5-aminobenzothiophen-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(5-ethylaminobenzothiophen-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(5-acetylaminobenzothiophen-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(5-methylsulfonylaminobenzothiophen-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(2-fluorophenyl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(3-fluorophenyl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(4-fluorophenyl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(2-hydroxyphenyl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(3-hydroxyphenyl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(4-hydroxyphenyl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(3-bromophenyl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(3,5-difluorophenyl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(2-methoxyphenyl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(3-methoxyphenyl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(4-methoxyphenyl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(3-trifluoromethoxyphenyl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(2-aminophenyl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(3-aminophenyl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(4-aminophenyl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(4-amino-3-hydroxyphenyl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(phenyl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][5-(phenyl)pentyl]amine;
    [1-(benzothiophen-3-yl)ethyl][2-(4-fluorophenyl)ethyl]amine;
    [1-(2-methylbenzofuran-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(3-methoxyphenyl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(3-hydroxyphenyl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(4-hydroxyphenyl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(4-aminophenyl)propyl]amine;
    [1-(5-isopropylazulen-1-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(1-azaazulen-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(thieno[2,3-b]pyridin-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(thieno[3,2-b]pyridin-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(imidazopyidin-3-yl)ethyl][3-(3-methoxyphenyl)propyl]amine;
    [1-(imidazopyidin-3-yl)ethyl][3-(3-hydroxyphenyl)propyl]amine;
    [1-(imidazopyidin-3-yl)ethyl][3-(4-aminophenyl)propyl]amine;
    [1-(imidazopyidin-3-yl)ethyl][3-(4-hydroxyphenyl)propyl]amine;
    [1-(pyrazolopyridin-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine;
    [1-(pyrazolopyridin-3-yl)ethyl][3-(3-methoxyphenyl)propyl]amine;
    [1-(pyrazolopyridin-3-yl)ethyl][3-(3-hydroxyphenyl)propyl]amine;
    [1-(pyrazolopyridin-3-yl)ethyl][3-(4-hydroxyphenyl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(pyridin-2-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(pyridin-3-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(pyridin-4-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(pyridin-3-yl)propyl]amine;
    [1-(imidazopyidin-3-yl)ethyl][3-(pyridin-3-yl)propyl]amine;
    [1-(pyrazolopyridin-3-yl)ethyl][3-(pyridin-3-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(furan-2-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(furan-3-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(5-methylfuran-2-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(5-phenylfuran-2-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(5-(3-chlorophenyl)furan-2-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(5-(3-aminophenyl)furan-2-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(5-(2-aminophenyl)furan-2-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(5-(4-aminophenyl)furan-2-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(benzofuran-2-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(thiophen-2-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(thiophen-3-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][2-(thiophen-2-yl)ethyl]amine;
    [1-(benzothiophen-3-yl)ethyl][4-(thiophen-2-yl) butyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(5-nitrothiophen-2-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(5-aminothiophen-2-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(2-nitrothiophen-4-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(2-aminothiophen-4-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(benzothiophen-2-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(pyrrol-1-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][2-(pyrrol-1-yl)ethyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(1-methylpyrrol-2-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][2-(1-methylpyrrol-2-yl)ethyl]amine;
    [1-(benzothiophen-3-yl)ethyl][5-(1-methylpyrrol-2-yl) pentyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(1-methylpyrrol-3-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][4-(1-methylpyrrol-2-yl)butyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(indol-3-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(furan-2-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(furan-3-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(5-methylfuran-2-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(5-phenylfuran-2-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(5-(3-chlorophenyl)furan-2-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(5-(3-aminophenyl)furan-2-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(5-(2-aminophenyl)furan-2-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(5-(4-aminophenyl)furan-2-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-[5-(pyridin-2-yl)furan-2-yl]propyl]amine;
    [1-(azulen-1-yl)ethyl][3-[5-(pyridin-3-yl)furan-2-yl]propyl]amine;
    [1-(azulen-1-yl)ethyl][3-[5-(pyridin-4-yl)furan-2-yl]propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(benzofuran-2-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(thiophen-2-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(thiophen-3-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][2-(thiophen-2-yl)ethyl]amine;
    [1-(azulen-1-yl)ethyl][4-(thiophen-2-yl)butyl]amine;
    [1-(azulen-1-yl)ethyl][3-(5-nitrothiophen-2-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(5-aminothiophen-2-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(2-nitrothiophen-4-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(2-aminothiophen-4-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(benzothiophen-2-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(pyrrol-1-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][2-(pyrrol-1-yl)ethyl]amine;
    [1-(azulen-1-yl)ethyl][3-(1-methylpyrrol-2-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][2-(1-methylpyrrol-2-yl)ethyl]amine;
    [1-(azulen-1-yl)ethyl][5-(1-methylpyrrol-2-yl)pentyl]amine;
    [1-(azulen-1-yl)ethyl][3-(1-methylpyrrol-3-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][5-(1-phenylpyrrol-2-yl)pentyl]amine;
    [1-(azulen-1-yl)ethyl][3-(1-phenylpyrrol-3-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(indol-3-yl)propyl]amine;
    [1-(thieno[2,3-b]pyridin-3-yl)ethyl][3-(furan-2-yl)propyl]amine;
    [1-(thieno[3,2-b]pyridin-3-yl)ethyl][3-(furan-3-yl)propyl]amine;
    [1-(imidazopyidin-3-yl)ethyl][3-(furan-2-yl)propyl]amine;
    [1-(imidazopyidin-3-yl)ethyl][3-(furan-3-yl)propyl]amine;
    [1-(pyrazolopyridin-3-yl)ethyl][3-(furan-2-yl)propyl]amine;
    [1-(pyrazolopyridin-3-yl)ethyl][3-(furan-3-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(tetrahydrofuran-2-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(tetrahydrofuran-3-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(pyrrolidin-1-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(piperidin-1-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(morpholin-1-yl)propyl]amine;
    [1-(benzothiophen-3-yl)ethyl][3-(thiazol-2-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(tetrahydrofuran-2-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(tetrahydrofuran-3-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(pyrrolidin-1-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(piperidin-1-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(morpholin-1-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(thiazol-2-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(2-phenylthiazol-4-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(2,5-dimethyloxazol-4-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(3,5-dimethylisoxazol-4-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(5-(thiophen-2-yl)isoxazol-4-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(3,5-dimethylisoxazol-4-yl)propyl]amine;
    [1-(azulen-1-yl)ethyl][3-(1,3-dimethylpyrazol-5-yl)propyl]amine;
    [1-(naphthalen-1-yl)ethyl][3-(furan-2-yl)propyl]amine;
    [1-(naphthalen-1-yl)ethyl][3-(furan-3-yl)propyl]amine;
    [1-(naphthalen-1-yl)ethyl][3-(5-methylfuran-2-yl)propyl]amine;
    [1-(naphthalen-1-yl)ethyl][3-(5-phenylfuran-2-yl)propyl]amine;
    [1-(naphthalen-1-yl)ethyl][3-(5-(3-chlorophenyl)furan-2-yl)propyl]amine;
    [1-(naphthalen-1-yl)ethyl][3-(5-(4-aminophenyl)furan-2-yl)propyl]amine;
    [1-(naphthalen-1-yl)ethyl][3-(benzofuran-2-yl)propyl]amine;
    [1-(naphthalen-1-yl)ethyl][3-(thiophen-2-yl)propyl]amine;
    [1-(naphthalen-1-yl)ethyl][3-(thiophen-3-yl)propyl]amine;
    [1-(naphthalen-1-yl)ethyl][4-(thiophen-2-yl)butyl]amine;
    [1-(naphthalen-1-yl)ethyl][3-(5-nitrothiophen-2-yl)propyl]amine;
    [1-(naphthalen-1-yl)ethyl][3-(5-aminothiophen-2-yl)propyl]amine;
    [1-(naphthalen-1-yl)ethyl][3-(2-nitrothiophen-4-yl)propyl]amine;
    [1-(naphthalen-1-yl)ethyl][3-(2-aminothiophen-4-yl)propyl]amine;
    [1-(naphthalen-1-yl)ethyl][3-(benzothiophen-2-yl)propyl]amine;
    [1-(naphthalen-1-yl)ethyl][3-(pyrrol-1-yl)propyl]amine;
    [1-(naphthalen-1-yl)ethyl][2-(pyrrol-1-yl)ethyl]amine;
    [1-(naphthalen-1-yl)ethyl][3-(1-methylpyrrol-2-yl)propyl]amine;
    [1-(naphthalen-1-yl)ethyl][2-(1-methylpyrrol-2-yl)ethyl]amine;
    [1-(naphthalen-1-yl)ethyl][5-(1-methylpyrrol-2-yl) pentyl]amine;
    [1-(naphthalen-1-yl)ethyl][3-(1-methylpyrrol-3-yl)propyl]amine;
    [1-(naphthalen-1-yl)ethyl][3-(indol-3-yl)propyl]amine and the like. However, the compounds of the present invention are not limited to the aforementioned specific compounds.


Preferred examples of the compounds of the present invention represented by the formula (1) further include the compounds represented by the formula 24:




wherein A, B, and n are selected as in any of the combinations shown in Tables 1 and 2. In Tables 1 and 2, example numbers are mentioned in the columns of “epn”. Further, the compounds represented by the formula (1) wherein A and B are selected as in any of the combinations shown in Table 1, but n is 2 or 4 instead of 3 are also preferred compounds, and these compounds are also included in the disclosure of Tables 1 and 2 with example numbers n2-1 to n2-12390 and n4-1 to n4-12390. However, the scope of the present invention is not limited to these preferred compounds.











TABLE 1









n = 3












epn
A
B







n3-1
A-1
B-1



n3-2
A-2
B-1



n3-3
A-3
B-1



n3-4
A-4
B-1



n3-5
A-5
B-1



n3-6
A-6
B-1



n3-7
A-7
B-1



n3-8
A-8
B-1



n3-9
A-9
B-1



n3-10
A-10
B-1



n3-11
A-11
B-1



n3-12
A-12
B-1



n3-13
A-13
B-1



n3-14
A-14
B-1



n3-15
A-15
B-1



n3-16
A-16
B-1



n3-17
A-17
B-1



n3-18
A-18
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A-160
B-4



n3-1514
A-161
B-4



n3-1515
A-162
B-4



n3-1516
A-163
B-4



n3-1517
A-164
B-4



n3-1518
A-165
B-4



n3-1519
A-166
B-4



n3-1520
A-167
B-4



n3-1521
A-168
B-4



n3-1522
A-169
B-4



n3-1523
A-170
B-4



n3-1524
A-171
B-4



n3-1525
A-172
B-4



n3-1526
A-173
B-4



n3-1527
A-174
B-4



n3-1528
A-175
B-4



n3-1529
A-176
B-4



n3-1530
A-177
B-4



n3-1531
A-178
B-4



n3-1532
A-179
B-4



n3-1533
A-180
B-4



n3-1534
A-181
B-4



n3-1535
A-182
B-4



n3-1536
A-183
B-4



n3-1537
A-184
B-4



n3-1538
A-185
B-4



n3-1539
A-186
B-4



n3-1540
A-187
B-4



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A-188
B-4



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A-189
B-4



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A-190
B-4



n3-1544
A-191
B-4



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A-192
B-4



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A-193
B-4



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A-194
B-4



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A-195
B-4



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A-196
B-4



n3-1550
A-197
B-4



n3-1551
A-198
B-4



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A-199
B-4



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A-200
B-4



n3-1554
A-201
B-4



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A-202
B-4



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A-203
B-4



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A-204
B-4



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A-205
B-4



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A-206
B-4



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A-207
B-4



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A-208
B-4



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A-209
B-4



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A-210
B-4



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A-211
B-4



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A-212
B-4



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A-213
B-4



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A-214
B-4



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A-215
B-4



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A-216
B-4



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A-217
B-4



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A-218
B-4



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A-219
B-4



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A-220
B-4



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A-221
B-4



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A-222
B-4



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A-223
B-4



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A-224
B-4



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A-225
B-4



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A-226
B-4



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A-227
B-4



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A-228
B-4



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A-229
B-4



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A-230
B-4



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A-231
B-4



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A-232
B-4



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A-233
B-4



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A-234
B-4



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A-235
B-4



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A-236
B-4



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A-237
B-4



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A-238
B-4



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A-239
B-4



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A-240
B-4



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A-241
B-4



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A-242
B-4



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A-243
B-4



n3-1597
A-244
B-4



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A-245
B-4



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A-246
B-4



n3-1600
A-247
B-4



n3-1601
A-248
B-4



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A-249
B-4



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A-250
B-4



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A-251
B-4



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A-252
B-4



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A-253
B-4



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A-254
B-4



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A-255
B-4



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A-256
B-4



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A-257
B-4



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A-258
B-4



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A-259
B-4



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A-260
B-4



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A-261
B-4



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A-262
B-4



n3-1616
A-263
B-4



n3-1617
A-264
B-4



n3-1618
A-265
B-4



n3-1619
A-266
B-4



n3-1620
A-267
B-4



n3-1621
A-268
B-4



n3-1622
A-269
B-4



n3-1623
A-270
B-4



n3-1624
A-271
B-4



n3-1625
A-272
B-4



n3-1626
A-273
B-4



n3-1627
A-274
B-4



n3-1628
A-275
B-4



n3-1629
A-276
B-4



n3-1630
A-277
B-4



n3-1631
A-278
B-4



n3-1632
A-279
B-4



n3-1633
A-280
B-4



n3-1634
A-281
B-4



n3-1635
A-282
B-4



n3-1636
A-283
B-4



n3-1637
A-284
B-4



n3-1638
A-285
B-4



n3-1639
A-286
B-4



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A-287
B-4



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A-288
B-4



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A-289
B-4



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A-290
B-4



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A-291
B-4



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A-292
B-4



n3-1646
A-293
B-4



n3-1647
A-294
B-4



n3-1648
A-295
B-4



n3-1649
A-296
B-4



n3-1650
A-297
B-4



n3-1651
A-298
B-4



n3-1652
A-299
B-4



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A-300
B-4



n3-1654
A-301
B-4



n3-1655
A-302
B-4



n3-1656
A-303
B-4



n3-1657
A-304
B-4



n3-1658
A-305
B-4



n3-1659
A-306
B-4



n3-1660
A-307
B-4



n3-1661
A-308
B-4



n3-1662
A-309
B-4



n3-1663
A-310
B-4



n3-1664
A-311
B-4



n3-1665
A-312
B-4



n3-1666
A-313
B-4



n3-1667
A-314
B-4



n3-1668
A-315
B-4



n3-1669
A-316
B-4



n3-1670
A-317
B-4



n3-1671
A-318
B-4



n3-1672
A-319
B-4



n3-1673
A-320
B-4



n3-1674
A-321
B-4



n3-1675
A-322
B-4



n3-1676
A-323
B-4



n3-1677
A-324
B-4



n3-1678
A-325
B-4



n3-1679
A-326
B-4



n3-1680
A-327
B-4



n3-1681
A-328
B-4



n3-1682
A-329
B-4



n3-1683
A-330
B-4



n3-1684
A-331
B-4



n3-1685
A-332
B-4



n3-1686
A-333
B-4



n3-1687
A-334
B-4



n3-1688
A-335
B-4



n3-1689
A-336
B-4



n3-1690
A-337
B-4



n3-1691
A-338
B-4



n3-1692
A-339
B-4



n3-1693
A-340
B-4



n3-1694
A-341
B-4



n3-1695
A-342
B-4



n3-1696
A-343
B-4



n3-1697
A-344
B-4



n3-1698
A-345
B-4



n3-1699
A-346
B-4



n3-1700
A-347
B-4



n3-1701
A-348
B-4



n3-1702
A-349
B-4



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A-350
B-4



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A-351
B-4



n3-1705
A-352
B-4



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A-353
B-4



n3-1707
A-354
B-4



n3-1708
A-355
B-4



n3-1709
A-356
B-4



n3-1710
A-357
B-4



n3-1711
A-358
B-4



n3-1712
A-359
B-4



n3-1713
A-360
B-4



n3-1714
A-361
B-4



n3-1715
A-362
B-4



n3-1716
A-363
B-4



n3-1717
A-364
B-4



n3-1718
A-365
B-4



n3-1719
A-366
B-4



n3-1720
A-367
B-4



n3-1721
A-368
B-4



n3-1722
A-369
B-4



n3-1723
A-370
B-4



n3-1724
A-371
B-4



n3-1725
A-372
B-4



n3-1726
A-373
B-4



n3-1727
A-374
B-4



n3-1728
A-375
B-4



n3-1729
A-376
B-4



n3-1730
A-377
B-4



n3-1731
A-378
B-4



n3-1732
A-379
B-4



n3-1733
A-380
B-4



n3-1734
A-381
B-4



n3-1735
A-382
B-4



n3-1736
A-383
B-4



n3-1737
A-384
B-4



n3-1738
A-385
B-4



n3-1739
A-386
B-4



n3-1740
A-387
B-4



n3-1741
A-388
B-4



n3-1742
A-389
B-4



n3-1743
A-390
B-4



n3-1744
A-391
B-4



n3-1745
A-392
B-4



n3-1746
A-393
B-4



n3-1747
A-394
B-4



n3-1748
A-395
B-4



n3-1749
A-396
B-4



n3-1750
A-397
B-4



n3-1751
A-398
B-4



n3-1752
A-399
B-4



n3-1753
A-400
B-4



n3-1754
A-401
B-4



n3-1755
A-402
B-4



n3-1756
A-403
B-4



n3-1757
A-404
B-4



n3-1758
A-405
B-4



n3-1759
A-406
B-4



n3-1760
A-407
B-4



n3-1761
A-408
B-4



n3-1762
A-409
B-4



n3-1763
A-410
B-4



n3-1764
A-411
B-4



n3-1765
A-412
B-4



n3-1766
A-413
B-4



n3-1767
A-414
B-4



n3-1768
A-415
B-4



n3-1769
A-416
B-4



n3-1770
A-417
B-4



n3-1771
A-418
B-4



n3-1772
A-419
B-4



n3-1773
A-420
B-4



n3-1774
A-421
B-4



n3-1775
A-422
B-4



n3-1776
A-423
B-4



n3-1777
A-424
B-4



n3-1778
A-425
B-4



n3-1779
A-426
B-4



n3-1780
A-427
B-4



n3-1781
A-428
B-4



n3-1782
A-429
B-4



n3-1783
A-430
B-4



n3-1784
A-431
B-4



n3-1785
A-432
B-4



n3-1786
A-433
B-4



n3-1787
A-434
B-4



n3-1788
A-435
B-4



n3-1789
A-436
B-4



n3-1790
A-437
B-4



n3-1791
A-438
B-4



n3-1792
A-439
B-4



n3-1793
A-440
B-4



n3-1794
A-441
B-4



n3-1795
A-442
B-4



n3-1796
A-443
B-4



n3-1797
A-444
B-4



n3-1798
A-445
B-4



n3-1799
A-446
B-4



n3-1800
A-447
B-4



n3-1801
A-448
B-4



n3-1802
A-449
B-4



n3-1803
A-450
B-4



n3-1804
A-451
B-4



n3-1805
A-1
B-5



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A-2
B-5



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A-3
B-5



n3-1808
A-4
B-5



n3-1809
A-5
B-5



n3-1810
A-6
B-5



n3-1811
A-7
B-5



n3-1812
A-8
B-5



n3-1813
A-9
B-5



n3-1814
A-10
B-5



n3-1815
A-11
B-5



n3-1816
A-12
B-5



n3-1817
A-13
B-5



n3-1818
A-14
B-5



n3-1819
A-15
B-5



n3-1820
A-16
B-5



n3-1821
A-17
B-5



n3-1822
A-18
B-5



n3-1823
A-19
B-5



n3-1824
A-20
B-5



n3-1825
A-21
B-5



n3-1826
A-22
B-5



n3-1827
A-23
B-5



n3-1828
A-24
B-5



n3-1829
A-25
B-5



n3-1830
A-26
B-5



n3-1831
A-27
B-5



n3-1832
A-28
B-5



n3-1833
A-29
B-5



n3-1834
A-30
B-5



n3-1835
A-31
B-5



n3-1836
A-32
B-5



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A-33
B-5



n3-1838
A-34
B-5



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A-35
B-5



n3-1840
A-36
B-5



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A-37
B-5



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A-38
B-5



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A-39
B-5



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A-40
B-5



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A-41
B-5



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A-42
B-5



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A-43
B-5



n3-1848
A-44
B-5



n3-1849
A-45
B-5



n3-1850
A-46
B-5



n3-1851
A-47
B-5



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A-48
B-5



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A-49
B-5



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A-50
B-5



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A-51
B-5



n3-1856
A-52
B-5



n3-1857
A-53
B-5



n3-1858
A-54
B-5



n3-1859
A-55
B-5



n3-1860
A-56
B-5



n3-1861
A-57
B-5



n3-1862
A-58
B-5



n3-1863
A-59
B-5



n3-1864
A-60
B-5



n3-1865
A-61
B-5



n3-1866
A-62
B-5



n3-1867
A-63
B-5



n3-1868
A-64
B-5



n3-1869
A-65
B-5



n3-1870
A-66
B-5



n3-1871
A-67
B-5



n3-1872
A-68
B-5



n3-1873
A-69
B-5



n3-1874
A-70
B-5



n3-1875
A-71
B-5



n3-1876
A-72
B-5



n3-1877
A-73
B-5



n3-1878
A-74
B-5



n3-1879
A-75
B-5



n3-1880
A-76
B-5



n3-1881
A-77
B-5



n3-1882
A-78
B-5



n3-1883
A-79
B-5



n3-1884
A-80
B-5



n3-1885
A-81
B-5



n3-1886
A-82
B-5



n3-1887
A-83
B-5



n3-1888
A-84
B-5



n3-1889
A-85
B-5



n3-1890
A-86
B-5



n3-1891
A-87
B-5



n3-1892
A-88
B-5



n3-1893
A-89
B-5



n3-1894
A-90
B-5



n3-1895
A-91
B-5



n3-1896
A-92
B-5



n3-1897
A-93
B-5



n3-1898
A-94
B-5



n3-1899
A-95
B-5



n3-1900
A-96
B-5



n3-1901
A-97
B-5



n3-1902
A-98
B-5



n3-1903
A-99
B-5



n3-1904
A-100
B-5



n3-1905
A-101
B-5



n3-1906
A-102
B-5



n3-1907
A-103
B-5



n3-1908
A-104
B-5



n3-1909
A-105
B-5



n3-1910
A-106
B-5



n3-1911
A-107
B-5



n3-1912
A-108
B-5



n3-1913
A-109
B-5



n3-1914
A-110
B-5



n3-1915
A-111
B-5



n3-1916
A-112
B-5



n3-1917
A-113
B-5



n3-1918
A-114
B-5



n3-1919
A-115
B-5



n3-1920
A-116
B-5



n3-1921
A-117
B-5



n3-1922
A-118
B-5



n3-1923
A-119
B-5



n3-1924
A-120
B-5



n3-1925
A-121
B-5



n3-1926
A-122
B-5



n3-1927
A-123
B-5



n3-1928
A-124
B-5



n3-1929
A-125
B-5



n3-1930
A-126
B-5



n3-1931
A-127
B-5



n3-1932
A-128
B-5



n3-1933
A-129
B-5



n3-1934
A-130
B-5



n3-1935
A-131
B-5



n3-1936
A-132
B-5



n3-1937
A-133
B-5



n3-1938
A-134
B-5



n3-1939
A-135
B-5



n3-1940
A-136
B-5



n3-1941
A-137
B-5



n3-1942
A-138
B-5



n3-1943
A-139
B-5



n3-1944
A-140
B-5



n3-1945
A-141
B-5



n3-1946
A-142
B-5



n3-1947
A-143
B-5



n3-1948
A-144
B-5



n3-1949
A-145
B-5



n3-1950
A-146
B-5



n3-1951
A-147
B-5



n3-1952
A-148
B-5



n3-1953
A-149
B-5



n3-1954
A-150
B-5



n3-1955
A-151
B-5



n3-1956
A-152
B-5



n3-1957
A-153
B-5



n3-1958
A-154
B-5



n3-1959
A-155
B-5



n3-1960
A-156
B-5



n3-1961
A-157
B-5



n3-1962
A-158
B-5



n3-1963
A-159
B-5



n3-1964
A-160
B-5



n3-1965
A-161
B-5



n3-1966
A-162
B-5



n3-1967
A-163
B-5



n3-1968
A-164
B-5



n3-1969
A-165
B-5



n3-1970
A-166
B-5



n3-1971
A-167
B-5



n3-1972
A-168
B-5



n3-1973
A-169
B-5



n3-1974
A-170
B-5



n3-1975
A-171
B-5



n3-1976
A-172
B-5



n3-1977
A-173
B-5



n3-1978
A-174
B-5



n3-1979
A-175
B-5



n3-1980
A-176
B-5



n3-1981
A-177
B-5



n3-1982
A-178
B-5



n3-1983
A-179
B-5



n3-1984
A-180
B-5



n3-1985
A-181
B-5



n3-1986
A-182
B-5



n3-1987
A-183
B-5



n3-1988
A-184
B-5



n3-1989
A-185
B-5



n3-1990
A-186
B-5



n3-1991
A-187
B-5



n3-1992
A-188
B-5



n3-1993
A-189
B-5



n3-1994
A-190
B-5



n3-1995
A-191
B-5



n3-1996
A-192
B-5



n3-1997
A-193
B-5



n3-1998
A-194
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A-194
B-21



n3-9215
A-195
B-21



n3-9216
A-196
B-21



n3-9217
A-197
B-21



n3-9218
A-198
B-21



n3-9219
A-199
B-21



n3-9220
A-200
B-21



n3-9221
A-201
B-21



n3-9222
A-202
B-21



n3-9223
A-203
B-21



n3-9224
A-204
B-21



n3-9225
A-205
B-21



n3-9226
A-206
B-21



n3-9227
A-207
B-21



n3-9228
A-208
B-21



n3-9229
A-209
B-21



n3-9230
A-210
B-21



n3-9231
A-211
B-21



n3-9232
A-212
B-21



n3-9233
A-213
B-21



n3-9234
A-214
B-21



n3-9235
A-215
B-21



n3-9236
A-216
B-21



n3-9237
A-217
B-21



n3-9238
A-218
B-21



n3-9239
A-219
B-21



n3-9240
A-220
B-21



n3-9241
A-221
B-21



n3-9242
A-222
B-21



n3-9243
A-223
B-21



n3-9244
A-224
B-21



n3-9245
A-225
B-21



n3-9246
A-226
B-21



n3-9247
A-227
B-21



n3-9248
A-228
B-21



n3-9249
A-229
B-21



n3-9250
A-230
B-21



n3-9251
A-231
B-21



n3-9252
A-232
B-21



n3-9253
A-233
B-21



n3-9254
A-234
B-21



n3-9255
A-235
B-21



n3-9256
A-236
B-21



n3-9257
A-237
B-21



n3-9258
A-238
B-21



n3-9259
A-239
B-21



n3-9260
A-240
B-21



n3-9261
A-241
B-21



n3-9262
A-242
B-21



n3-9263
A-243
B-21



n3-9264
A-244
B-21



n3-9265
A-245
B-21



n3-9266
A-246
B-21



n3-9267
A-247
B-21



n3-9268
A-248
B-21



n3-9269
A-249
B-21



n3-9270
A-250
B-21



n3-9271
A-251
B-21



n3-9272
A-252
B-21



n3-9273
A-253
B-21



n3-9274
A-254
B-21



n3-9275
A-255
B-21



n3-9276
A-256
B-21



n3-9277
A-257
B-21



n3-9278
A-258
B-21



n3-9279
A-259
B-21



n3-9280
A-260
B-21



n3-9281
A-261
B-21



n3-9282
A-262
B-21



n3-9283
A-263
B-21



n3-9284
A-264
B-21



n3-9285
A-265
B-21



n3-9286
A-266
B-21



n3-9287
A-267
B-21



n3-9288
A-268
B-21



n3-9289
A-269
B-21



n3-9290
A-270
B-21



n3-9291
A-271
B-21



n3-9292
A-272
B-21



n3-9293
A-273
B-21



n3-9294
A-274
B-21



n3-9295
A-275
B-21



n3-9296
A-276
B-21



n3-9297
A-277
B-21



n3-9298
A-278
B-21



n3-9299
A-279
B-21



n3-9300
A-280
B-21



n3-9301
A-281
B-21



n3-9302
A-282
B-21



n3-9303
A-283
B-21



n3-9304
A-284
B-21



n3-9305
A-285
B-21



n3-9306
A-286
B-21



n3-9307
A-287
B-21



n3-9308
A-288
B-21



n3-9309
A-289
B-21



n3-9310
A-290
B-21



n3-9311
A-291
B-21



n3-9312
A-292
B-21



n3-9313
A-293
B-21



n3-9314
A-294
B-21



n3-9315
A-295
B-21



n3-9316
A-296
B-21



n3-9317
A-297
B-21



n3-9318
A-298
B-21



n3-9319
A-299
B-21



n3-9320
A-300
B-21



n3-9321
A-301
B-21



n3-9322
A-302
B-21



n3-9323
A-303
B-21



n3-9324
A-304
B-21



n3-9325
A-305
B-21



n3-9326
A-306
B-21



n3-9327
A-307
B-21



n3-9328
A-308
B-21



n3-9329
A-309
B-21



n3-9330
A-310
B-21



n3-9331
A-311
B-21



n3-9332
A-312
B-21



n3-9333
A-313
B-21



n3-9334
A-314
B-21



n3-9335
A-315
B-21



n3-9336
A-316
B-21



n3-9337
A-317
B-21



n3-9338
A-318
B-21



n3-9339
A-319
B-21



n3-9340
A-320
B-21



n3-9341
A-321
B-21



n3-9342
A-322
B-21



n3-9343
A-323
B-21



n3-9344
A-324
B-21



n3-9345
A-325
B-21



n3-9346
A-326
B-21



n3-9347
A-327
B-21



n3-9348
A-328
B-21



n3-9349
A-329
B-21



n3-9350
A-330
B-21



n3-9351
A-331
B-21



n3-9352
A-332
B-21



n3-9353
A-333
B-21



n3-9354
A-334
B-21



n3-9355
A-335
B-21



n3-9356
A-336
B-21



n3-9357
A-337
B-21



n3-9358
A-338
B-21



n3-9359
A-339
B-21



n3-9360
A-340
B-21



n3-9361
A-341
B-21



n3-9362
A-342
B-21



n3-9363
A-343
B-21



n3-9364
A-344
B-21



n3-9365
A-345
B-21



n3-9366
A-346
B-21



n3-9367
A-347
B-21



n3-9368
A-348
B-21



n3-9369
A-349
B-21



n3-9370
A-350
B-21



n3-9371
A-351
B-21



n3-9372
A-352
B-21



n3-9373
A-353
B-21



n3-9374
A-354
B-21



n3-9375
A-355
B-21



n3-9376
A-356
B-21



n3-9377
A-357
B-21



n3-9378
A-358
B-21



n3-9379
A-359
B-21



n3-9380
A-360
B-21



n3-9381
A-361
B-21



n3-9382
A-362
B-21



n3-9383
A-363
B-21



n3-9384
A-364
B-21



n3-9385
A-365
B-21



n3-9386
A-366
B-21



n3-9387
A-367
B-21



n3-9388
A-368
B-21



n3-9389
A-369
B-21



n3-9390
A-370
B-21



n3-9391
A-371
B-21



n3-9392
A-372
B-21



n3-9393
A-373
B-21



n3-9394
A-374
B-21



n3-9395
A-375
B-21



n3-9396
A-376
B-21



n3-9397
A-377
B-21



n3-9398
A-378
B-21



n3-9399
A-379
B-21



n3-9400
A-380
B-21



n3-9401
A-381
B-21



n3-9402
A-382
B-21



n3-9403
A-383
B-21



n3-9404
A-384
B-21



n3-9405
A-385
B-21



n3-9406
A-386
B-21



n3-9407
A-387
B-21



n3-9408
A-388
B-21



n3-9409
A-389
B-21



n3-9410
A-390
B-21



n3-9411
A-391
B-21



n3-9412
A-392
B-21



n3-9413
A-393
B-21



n3-9414
A-394
B-21



n3-9415
A-395
B-21



n3-9416
A-396
B-21



n3-9417
A-397
B-21



n3-9418
A-398
B-21



n3-9419
A-399
B-21



n3-9420
A-400
B-21



n3-9421
A-401
B-21



n3-9422
A-402
B-21



n3-9423
A-403
B-21



n3-9424
A-404
B-21



n3-9425
A-405
B-21



n3-9426
A-406
B-21



n3-9427
A-407
B-21



n3-9428
A-408
B-21



n3-9429
A-409
B-21



n3-9430
A-410
B-21



n3-9431
A-411
B-21



n3-9432
A-412
B-21



n3-9433
A-413
B-21



n3-9434
A-414
B-21



n3-9435
A-415
B-21



n3-9436
A-416
B-21



n3-9437
A-417
B-21



n3-9438
A-418
B-21



n3-9439
A-419
B-21



n3-9440
A-420
B-21



n3-9441
A-421
B-21



n3-9442
A-422
B-21



n3-9443
A-423
B-21



n3-9444
A-424
B-21



n3-9445
A-425
B-21



n3-9446
A-426
B-21



n3-9447
A-427
B-21



n3-9448
A-428
B-21



n3-9449
A-429
B-21



n3-9450
A-430
B-21



n3-9451
A-431
B-21



n3-9452
A-432
B-21



n3-9453
A-433
B-21



n3-9454
A-434
B-21



n3-9455
A-435
B-21



n3-9456
A-436
B-21



n3-9457
A-437
B-21



n3-9458
A-438
B-21



n3-9459
A-439
B-21



n3-9460
A-440
B-21



n3-9461
A-441
B-21



n3-9462
A-442
B-21



n3-9463
A-443
B-21



n3-9464
A-444
B-21



n3-9465
A-445
B-21



n3-9466
A-446
B-21



n3-9467
A-447
B-21



n3-9468
A-448
B-21



n3-9469
A-449
B-21



n3-9470
A-450
B-21



n3-9471
A-451
B-21




















TABLE 2









n = 3












epn
A
B







n3-9472
A-452
B-1



n3-9473
A-453
B-1



n3-9474
A-454
B-1



n3-9475
A-455
B-1



n3-9476
A-456
B-1



n3-9477
A-457
B-1



n3-9478
A-458
B-1



n3-9479
A-459
B-1



n3-9480
A-460
B-1



n3-9481
A-461
B-1



n3-9482
A-462
B-1



n3-9483
A-463
B-1



n3-9484
A-464
B-1



n3-9485
A-465
B-1



n3-9486
A-466
B-1



n3-9487
A-467
B-1



n3-9488
A-468
B-1



n3-9489
A-469
B-1



n3-9490
A-470
B-1



n3-9491
A-471
B-1



n3-9492
A-472
B-1



n3-9493
A-473
B-1



n3-9494
A-474
B-1



n3-9495
A-475
B-1



n3-9496
A-476
B-1



n3-9497
A-477
B-1



n3-9498
A-478
B-1



n3-9499
A-479
B-1



n3-9500
A-480
B-1



n3-9501
A-481
B-1



n3-9502
A-482
B-1



n3-9503
A-483
B-1



n3-9504
A-484
B-1



n3-9505
A-485
B-1



n3-9506
A-486
B-1



n3-9507
A-487
B-1



n3-9508
A-488
B-1



n3-9509
A-489
B-1



n3-9510
A-490
B-1



n3-9511
A-491
B-1



n3-9512
A-492
B-1



n3-9513
A-493
B-1



n3-9514
A-494
B-1



n3-9515
A-495
B-1



n3-9516
A-496
B-1



n3-9517
A-497
B-1



n3-9518
A-498
B-1



n3-9519
A-499
B-1



n3-9520
A-500
B-1



n3-9521
A-501
B-1



n3-9522
A-502
B-1



n3-9523
A-503
B-1



n3-9524
A-504
B-1



n3-9525
A-505
B-1



n3-9526
A-506
B-1



n3-9527
A-507
B-1



n3-9528
A-508
B-1



n3-9529
A-509
B-1



n3-9530
A-510
B-1



n3-9531
A-511
B-1



n3-9532
A-512
B-1



n3-9533
A-513
B-1



n3-9534
A-514
B-1



n3-9535
A-515
B-1



n3-9536
A-516
B-1



n3-9537
A-517
B-1



n3-9538
A-518
B-1



n3-9539
A-519
B-1



n3-9540
A-520
B-1



n3-9541
A-521
B-1



n3-9542
A-522
B-1



n3-9543
A-523
B-1



n3-9544
A-524
B-1



n3-9545
A-525
B-1



n3-9546
A-526
B-1



n3-9547
A-527
B-1



n3-9548
A-528
B-1



n3-9549
A-529
B-1



n3-9550
A-530
B-1



n3-9551
A-531
B-1



n3-9552
A-532
B-1



n3-9553
A-533
B-1



n3-9554
A-534
B-1



n3-9555
A-535
B-1



n3-9556
A-536
B-1



n3-9557
A-537
B-1



n3-9558
A-538
B-1



n3-9559
A-539
B-1



n3-9560
A-540
B-1



n3-9561
A-541
B-1



n3-9562
A-542
B-1



n3-9563
A-543
B-1



n3-9564
A-544
B-1



n3-9565
A-545
B-1



n3-9566
A-546
B-1



n3-9567
A-547
B-1



n3-9568
A-548
B-1



n3-9569
A-549
B-1



n3-9570
A-550
B-1



n3-9571
A-551
B-1



n3-9572
A-552
B-1



n3-9573
A-553
B-1



n3-9574
A-554
B-1



n3-9575
A-555
B-1



n3-9576
A-556
B-1



n3-9577
A-557
B-1



n3-9578
A-558
B-1



n3-9579
A-559
B-1



n3-9580
A-560
B-1



n3-9581
A-561
B-1



n3-9582
A-562
B-1



n3-9583
A-563
B-1



n3-9584
A-564
B-1



n3-9585
A-565
B-1



n3-9586
A-566
B-1



n3-9587
A-567
B-1



n3-9588
A-568
B-1



n3-9589
A-569
B-1



n3-9590
A-570
B-1



n3-9591
A-571
B-1



n3-9592
A-572
B-1



n3-9593
A-573
B-1



n3-9594
A-574
B-1



n3-9595
A-575
B-1



n3-9596
A-576
B-1



n3-9597
A-577
B-1



n3-9598
A-578
B-1



n3-9599
A-579
B-1



n3-9600
A-580
B-1



n3-9601
A-581
B-1



n3-9602
A-582
B-1



n3-9603
A-583
B-1



n3-9604
A-584
B-1



n3-9605
A-585
B-1



n3-9606
A-586
B-1



n3-9607
A-587
B-1



n3-9608
A-588
B-1



n3-9609
A-589
B-1



n3-9610
A-590
B-1



n3-9611
A-452
B-2



n3-9612
A-453
B-2



n3-9613
A-454
B-2



n3-9614
A-455
B-2



n3-9615
A-456
B-2



n3-9616
A-457
B-2



n3-9617
A-458
B-2



n3-9618
A-459
B-2



n3-9619
A-460
B-2



n3-9620
A-461
B-2



n3-9621
A-462
B-2



n3-9622
A-463
B-2



n3-9623
A-464
B-2



n3-9624
A-465
B-2



n3-9625
A-466
B-2



n3-9626
A-467
B-2



n3-9627
A-468
B-2



n3-9628
A-469
B-2



n3-9629
A-470
B-2



n3-9630
A-471
B-2



n3-9631
A-472
B-2



n3-9632
A-473
B-2



n3-9633
A-474
B-2



n3-9634
A-475
B-2



n3-9635
A-476
B-2



n3-9636
A-477
B-2



n3-9637
A-478
B-2



n3-9638
A-479
B-2



n3-9639
A-480
B-2



n3-9640
A-481
B-2



n3-9641
A-482
B-2



n3-9642
A-483
B-2



n3-9643
A-484
B-2



n3-9644
A-485
B-2



n3-9645
A-486
B-2



n3-9646
A-487
B-2



n3-9647
A-488
B-2



n3-9648
A-489
B-2



n3-9649
A-490
B-2



n3-9650
A-491
B-2



n3-9651
A-492
B-2



n3-9652
A-493
B-2



n3-9653
A-494
B-2



n3-9654
A-495
B-2



n3-9655
A-496
B-2



n3-9656
A-497
B-2



n3-9657
A-498
B-2



n3-9658
A-499
B-2



n3-9659
A-500
B-2



n3-9660
A-501
B-2



n3-9661
A-502
B-2



n3-9662
A-503
B-2



n3-9663
A-504
B-2



n3-9664
A-505
B-2



n3-9665
A-506
B-2



n3-9666
A-507
B-2



n3-9667
A-508
B-2



n3-9668
A-509
B-2



n3-9669
A-510
B-2



n3-9670
A-511
B-2



n3-9671
A-512
B-2



n3-9672
A-513
B-2



n3-9673
A-514
B-2



n3-9674
A-515
B-2



n3-9675
A-516
B-2



n3-9676
A-517
B-2



n3-9677
A-518
B-2



n3-9678
A-519
B-2



n3-9679
A-520
B-2



n3-9680
A-521
B-2



n3-9681
A-522
B-2



n3-9682
A-523
B-2



n3-9683
A-524
B-2



n3-9684
A-525
B-2



n3-9685
A-526
B-2



n3-9686
A-527
B-2



n3-9687
A-528
B-2



n3-9688
A-529
B-2



n3-9689
A-530
B-2



n3-9690
A-531
B-2



n3-9691
A-532
B-2



n3-9692
A-533
B-2



n3-9693
A-534
B-2



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A-567
B-19



n3-12090
A-568
B-19



n3-12091
A-569
B-19



n3-12092
A-570
B-19



n3-12093
A-571
B-19



n3-12094
A-572
B-19



n3-12095
A-573
B-19



n3-12096
A-574
B-19



n3-12097
A-575
B-19



n3-12098
A-576
B-19



n3-12099
A-577
B-19



n3-12100
A-578
B-19



n3-12101
A-579
B-19



n3-12102
A-580
B-19



n3-12103
A-581
B-19



n3-12104
A-582
B-19



n3-12105
A-583
B-19



n3-12106
A-584
B-19



n3-12107
A-585
B-19



n3-12108
A-586
B-19



n3-12109
A-587
B-19



n3-12110
A-588
B-19



n3-12111
A-589
B-19



n3-12112
A-590
B-19



n3-12113
A-452
B-20



n3-12114
A-453
B-20



n3-12115
A-454
B-20



n3-12116
A-455
B-20



n3-12117
A-456
B-20



n3-12118
A-457
B-20



n3-12119
A-458
B-20



n3-12120
A-459
B-20



n3-12121
A-460
B-20



n3-12122
A-461
B-20



n3-12123
A-462
B-20



n3-12124
A-463
B-20



n3-12125
A-464
B-20



n3-12126
A-465
B-20



n3-12127
A-466
B-20



n3-12128
A-467
B-20



n3-12129
A-468
B-20



n3-12130
A-469
B-20



n3-12131
A-470
B-20



n3-12132
A-471
B-20



n3-12133
A-472
B-20



n3-12134
A-473
B-20



n3-12135
A-474
B-20



n3-12136
A-475
B-20



n3-12137
A-476
B-20



n3-12138
A-477
B-20



n3-12139
A-478
B-20



n3-12140
A-479
B-20



n3-12141
A-480
B-20



n3-12142
A-481
B-20



n3-12143
A-482
B-20



n3-12144
A-483
B-20



n3-12145
A-484
B-20



n3-12146
A-485
B-20



n3-12147
A-486
B-20



n3-12148
A-487
B-20



n3-12149
A-488
B-20



n3-12150
A-489
B-20



n3-12151
A-490
B-20



n3-12152
A-491
B-20



n3-12153
A-492
B-20



n3-12154
A-493
B-20



n3-12155
A-494
B-20



n3-12156
A-495
B-20



n3-12157
A-496
B-20



n3-12158
A-497
B-20



n3-12159
A-498
B-20



n3-12160
A-499
B-20



n3-12161
A-500
B-20



n3-12162
A-501
B-20



n3-12163
A-502
B-20



n3-12164
A-503
B-20



n3-12165
A-504
B-20



n3-12166
A-505
B-20



n3-12167
A-506
B-20



n3-12168
A-507
B-20



n3-12169
A-508
B-20



n3-12170
A-509
B-20



n3-12171
A-510
B-20



n3-12172
A-511
B-20



n3-12173
A-512
B-20



n3-12174
A-513
B-20



n3-12175
A-514
B-20



n3-12176
A-515
B-20



n3-12177
A-516
B-20



n3-12178
A-517
B-20



n3-12179
A-518
B-20



n3-12180
A-519
B-20



n3-12181
A-520
B-20



n3-12182
A-521
B-20



n3-12183
A-522
B-20



n3-12184
A-523
B-20



n3-12185
A-524
B-20



n3-12186
A-525
B-20



n3-12187
A-526
B-20



n3-12188
A-527
B-20



n3-12189
A-528
B-20



n3-12190
A-529
B-20



n3-12191
A-530
B-20



n3-12192
A-531
B-20



n3-12193
A-532
B-20



n3-12194
A-533
B-20



n3-12195
A-534
B-20



n3-12196
A-535
B-20



n3-12197
A-536
B-20



n3-12198
A-537
B-20



n3-12199
A-538
B-20



n3-12200
A-539
B-20



n3-12201
A-540
B-20



n3-12202
A-541
B-20



n3-12203
A-542
B-20



n3-12204
A-543
B-20



n3-12205
A-544
B-20



n3-12206
A-545
B-20



n3-12207
A-546
B-20



n3-12208
A-547
B-20



n3-12209
A-548
B-20



n3-12210
A-549
B-20



n3-12211
A-550
B-20



n3-12212
A-551
B-20



n3-12213
A-552
B-20



n3-12214
A-553
B-20



n3-12215
A-554
B-20



n3-12216
A-555
B-20



n3-12217
A-556
B-20



n3-12218
A-557
B-20



n3-12219
A-558
B-20



n3-12220
A-559
B-20



n3-12221
A-560
B-20



n3-12222
A-561
B-20



n3-12223
A-562
B-20



n3-12224
A-563
B-20



n3-12225
A-564
B-20



n3-12226
A-565
B-20



n3-12227
A-566
B-20



n3-12228
A-567
B-20



n3-12229
A-568
B-20



n3-12230
A-569
B-20



n3-12231
A-570
B-20



n3-12232
A-571
B-20



n3-12233
A-572
B-20



n3-12234
A-573
B-20



n3-12235
A-574
B-20



n3-12236
A-575
B-20



n3-12237
A-576
B-20



n3-12238
A-577
B-20



n3-12239
A-578
B-20



n3-12240
A-579
B-20



n3-12241
A-580
B-20



n3-12242
A-581
B-20



n3-12243
A-582
B-20



n3-12244
A-583
B-20



n3-12245
A-584
B-20



n3-12246
A-585
B-20



n3-12247
A-586
B-20



n3-12248
A-587
B-20



n3-12249
A-588
B-20



n3-12250
A-589
B-20



n3-12251
A-590
B-20



n3-12252
A-452
B-21



n3-12253
A-453
B-21



n3-12254
A-454
B-21



n3-12255
A-455
B-21



n3-12256
A-456
B-21



n3-12257
A-457
B-21



n3-12258
A-458
B-21



n3-12259
A-459
B-21



n3-12260
A-460
B-21



n3-12261
A-461
B-21



n3-12262
A-462
B-21



n3-12263
A-463
B-21



n3-12264
A-464
B-21



n3-12265
A-465
B-21



n3-12266
A-466
B-21



n3-12267
A-467
B-21



n3-12268
A-468
B-21



n3-12269
A-469
B-21



n3-12270
A-470
B-21



n3-12271
A-471
B-21



n3-12272
A-472
B-21



n3-12273
A-473
B-21



n3-12274
A-474
B-21



n3-12275
A-475
B-21



n3-12276
A-476
B-21



n3-12277
A-477
B-21



n3-12278
A-478
B-21



n3-12279
A-479
B-21



n3-12280
A-480
B-21



n3-12281
A-481
B-21



n3-12282
A-482
B-21



n3-12283
A-483
B-21



n3-12284
A-484
B-21



n3-12285
A-485
B-21



n3-12286
A-486
B-21



n3-12287
A-487
B-21



n3-12288
A-488
B-21



n3-12289
A-489
B-21



n3-12290
A-490
B-21



n3-12291
A-491
B-21



n3-12292
A-492
B-21



n3-12293
A-493
B-21



n3-12294
A-494
B-21



n3-12295
A-495
B-21



n3-12296
A-496
B-21



n3-12297
A-497
B-21



n3-12298
A-498
B-21



n3-12299
A-499
B-21



n3-12300
A-500
B-21



n3-12301
A-501
B-21



n3-12302
A-502
B-21



n3-12303
A-503
B-21



n3-12304
A-504
B-21



n3-12305
A-505
B-21



n3-12306
A-506
B-21



n3-12307
A-507
B-21



n3-12308
A-508
B-21



n3-12309
A-509
B-21



n3-12310
A-510
B-21



n3-12311
A-511
B-21



n3-12312
A-512
B-21



n3-12313
A-513
B-21



n3-12314
A-514
B-21



n3-12315
A-515
B-21



n3-12316
A-516
B-21



n3-12317
A-517
B-21



n3-12318
A-518
B-21



n3-12319
A-519
B-21



n3-12320
A-520
B-21



n3-12321
A-521
B-21



n3-12322
A-522
B-21



n3-12323
A-523
B-21



n3-12324
A-524
B-21



n3-12325
A-525
B-21



n3-12326
A-526
B-21



n3-12327
A-527
B-21



n3-12328
A-528
B-21



n3-12329
A-529
B-21



n3-12330
A-530
B-21



n3-12331
A-531
B-21



n3-12332
A-532
B-21



n3-12333
A-533
B-21



n3-12334
A-534
B-21



n3-12335
A-535
B-21



n3-12336
A-536
B-21



n3-12337
A-537
B-21



n3-12338
A-538
B-21



n3-12339
A-539
B-21



n3-12340
A-540
B-21



n3-12341
A-541
B-21



n3-12342
A-542
B-21



n3-12343
A-543
B-21



n3-12344
A-544
B-21



n3-12345
A-545
B-21



n3-12346
A-546
B-21



n3-12347
A-547
B-21



n3-12348
A-548
B-21



n3-12349
A-549
B-21



n3-12350
A-550
B-21



n3-12351
A-551
B-21



n3-12352
A-552
B-21



n3-12353
A-553
B-21



n3-12354
A-554
B-21



n3-12355
A-555
B-21



n3-12356
A-556
B-21



n3-12357
A-557
B-21



n3-12358
A-558
B-21



n3-12359
A-559
B-21



n3-12360
A-560
B-21



n3-12361
A-561
B-21



n3-12362
A-562
B-21



n3-12363
A-563
B-21



n3-12364
A-564
B-21



n3-12365
A-565
B-21



n3-12366
A-566
B-21



n3-12367
A-567
B-21



n3-12368
A-568
B-21



n3-12369
A-569
B-21



n3-12370
A-570
B-21



n3-12371
A-571
B-21



n3-12372
A-572
B-21



n3-12373
A-573
B-21



n3-12374
A-574
B-21



n3-12375
A-575
B-21



n3-12376
A-576
B-21



n3-12377
A-577
B-21



n3-12378
A-578
B-21



n3-12379
A-579
B-21



n3-12380
A-580
B-21



n3-12381
A-581
B-21



n3-12382
A-582
B-21



n3-12383
A-583
B-21



n3-12384
A-584
B-21



n3-12385
A-585
B-21



n3-12386
A-586
B-21



n3-12387
A-587
B-21



n3-12388
A-588
B-21



n3-12389
A-589
B-21



n3-12390
A-590
B-21










The compounds of the present invention represented by the formula (1) can be prepared by, for example, the following methods. However, the synthetic methods are not limited to the following methods.
Synthetic Method A
For example, by reducing a compound represented by the formula (3):




wherein A′ represents a group selected from the group consisting of (1) a saturated heterocyclic group, (2) a 5-membered heteroaromatic group having two heteroatoms in the ring which may be substituted, (3) a group represented by the following formula A1′, (4) a group represented by the following formula A2′, (5) a group represented by the following formula A3′, and (6) a group represented by the following formula A4′:





wherein R2′, R3′, and R4′ may be the same or different, and independently represent hydrogen atom, a hydroxyl group which may have a protective group, a halogen atom, an alkyl group, phenyl group, a substituted phenyl group which may have a protective group in a substituent, benzyl group, a substituted benzyl group which may have a protective group in a substituent, a monocyclic heteroaromatic group which may be substituted with a substituent which may have a protective group, a bicyclic heteroaromatic group which may be substituted with a substituent which may have a protective group, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group or N(R16′)(R17′) wherein R16′ and R17′ may be the same or different, and independently represent hydrogen atom, an alkyl group, an acyl group, SO2R18, or a protective group for the nitrogen atom, wherein R18 represents a lower alkyl group, or R16′ and R17′ together form a 3- to 7-membered ring to represent a cyclic amine as N(R16′)(R17′); R5′, R6, and R7 may be the same or different, and independently represent hydrogen atom, hydroxyl group which may have a protective group, a halogen atom, an alkyl group, phenyl group, a substituted phenyl group which may have a protective group in a substituent, benzyl group, a substituted benzyl group which may have a protective group in a substituent, a monocyclic heteroaromatic group, a monocyclic heteroaromatic group which may be substituted with a substituent which may have a protective group, a bicyclic heteroaromatic group which may be substituted with a substituent which may have a protective group, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, or N(R16′)(R17′) wherein R16′ and R17′ may be the same or different, and independently represent hydrogen atom, an alkyl group, an acyl group, SO2R18, or a protective group of the nitrogen atom, wherein R18 represents a lower alkyl group, or R16′ and R17′ together form a 3- to 7-membered ring to represent a cyclic amine as N(R16′)(R17′); R8′, R9′, and R10′ may be the same or different, and independently represent hydrogen atom, hydroxyl group which may have a protective group, a halogen atom, an alkyl group, a phenyl group, a substituted phenyl group which may have a protective group in a substituent, benzyl group, a substituted benzyl group which may have a protective group in a substituent, a monocyclic heteroaromatic group which may be substituted with a substituent which may have a protective group, a bicyclic heteroaromatic group which may be substituted with a substituent which may have a protective group, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, or N(R16′)(R17′) wherein R16′ and R17′ may be the same or different, and independently represent hydrogen atom, an alkyl group, an acyl group, SO2R18, or a protective group of the nitrogen atom, wherein R18 represents a lower alkyl group, or R16′ and R17′ together form a 3- to 7-membered ring to represent a cyclic amine as N(R16′)(R17′), or R8 and R9 may together form a benzene ring and thus form a bicyclic heteroaromatic group as a group represented by the formula A3′; and X1 represent oxygen atom, sulfur atom, or N—R19 wherein R19 represents hydrogen atom, an alkyl group, phenyl group, or a substituted phenyl group; X2 represents oxygen atom, or sulfur atom, and R23′ represents a substituted phenyl group which may have a protective group in a substituent, a monocyclic heteroaromatic group which may be substituted with a substituent which may have a protective group, or a bicyclic heteroaromatic group which may be substituted with a substituent which may have a protective group,

B′ represents a group selected from the group consisting of a group represented by the following formula B1′, B2′, B3′, B4′, or B5′:




wherein R11′ represents hydrogen atom, hydroxyl group which may have a protective group, a halogen atom, an alkyl group, an alkoxyl group, a thioalkoxyl group, hydroxymethyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, or N(R20′)(R21′) wherein R20′ and R21′ may be the same or different, and independently represent hydrogen atom, an alkyl group, an acyl group, SO2R22, or a protective group of the nitrogen atom, wherein R22 represents a lower alkyl group, or R20′′ and R21′′ together form a 3- to 7-membered ring to represent a cyclic amine as N(R20′)(R21′), Y1′ represents sulfur atom or oxygen atom; R12 represent hydrogen atom or an alkyl group, Y2 represents CH or nitrogen atom; R13′ represents hydrogen atom, hydroxyl group which may have a protective group, a halogen atom, an alkyl group, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, or N(R20′)(R21′) wherein R20′ and R21′ may be the same or different, and independently represent hydrogen atom, an alkyl group, an acyl group, SO2R22, or a protective group of the nitrogen atom, wherein R22 represents a lower alkyl group, or R20′′ and R21′′ together form a 3- to 7-membered ring to represent a cyclic amine as N(R20′)(R21′), Y4 represents sulfur atom or oxygen atom, and one of Y3, Y5, and Y6 represents nitrogen atom, and the remaining groups represent CH; R14′ represents hydrogen atom, hydroxyl group which may have a protective group, a halogen atom, an alkyl group, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, or N(R20′)(R21′) wherein R20′ and R21′ may be the same or different, and independently represent hydrogen atom, an alkyl group, an acyl group, SO2R22, or a protective group of the nitrogen atom, wherein R22 represents a lower alkyl group, or R20′′ and R21′′ together form a 3- to 7-membered ring to represent a cyclic amine as N(R20′)(R21′), Y7 represent CH or nitrogen atom; and R15′ represents hydrogen atom, hydroxyl group which may have a protective group, a halogen atom, an alkyl group, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, nitro group, or N(R20′)(R21′) wherein R20′ and R21′ may be the same or different, and independently represent hydrogen atom, an alkyl group, an acyl group, SO2R22, or a protective group of the nitrogen atom, wherein R22 represents a lower alkyl group, or R20′′ and R21′′ together form a 3- to 7-membered ring to represent a cyclic amine as N(R20′)(R21′);

R1 represents an alkyl group, and symbol “n” represents an integer of 2 to 6, compounds represented by the following formula (2):




wherein A′, B′, R1, and n have the same meanings as those defined above, and * represents a carbon atom in S-configuration, R-configuration, or the both configurations, can be obtained, and when A′ or B′ has a protective group, by deprotecting such a compound, compounds represented by the formula (1) can be prepared.

The method of reducing a compound represented by the formula (3) to obtain a compound represented by the formula (2) can be performed, for example, according to known reduction amination reaction methods described in a publication (Jikken Kagaku Koza (Lecture of Experiment Chemistry), 4th-edition, Vol. 20, Chapter 6, Maruzen), literature (Robert M. B. et al., Tetrahedron Letters, Vol. 39, 1998, pp. 3451-3454), and the like.
Type of the reducing agent used for the reduction reaction is not particularly limited, and examples include, for example, hydrogen, lithium aluminum hydride, sodium borohydride, sodium cyanoborohydride, sodium triacetoxyborohydride, borane, formic acid-triethyl amine complex, and the like, and preferred example include hydrogen, sodium borohydride, sodium cyanoborohydride, sodium triacetoxyborohydride, borane, and formic acid-triethyl amine complex. Type of the solvent used for the reaction is not particularly limited so long as a solvent inert to the reduction reaction is chosen. Examples include an alcohol type solvent, a saturated hydrocarbon type solvent, a chlorinated hydrocarbon type solvent, an ether type solvent, an aromatic hydrocarbon type solvent, dimethylformamide, dimethyl sulfoxide, and the like, and individuals and mixed solvents at arbitrary ratios of these solvents are included. Examples of the alcohol type solvent include methanol, ethanol, and 2-propanol, examples of the saturated hydrocarbon type solvent include pentane, hexane, heptane, and cyclohexane, and examples of chlorinated hydrocarbon type solvent include methylene chloride, chloroform, and 1,2-dichloroethane. Examples of the ether type solvent include tetrahydrofuran, diethyl ether, and 1,4-dioxane, and examples of aromatic hydrocarbon type solvent include toluene, xylene, and the like. Preferred examples include 2-propanol, methylene chloride, tetrahydrofuran, toluene, dimethylformamide, and the like.
The reducing agent is preferably used in an amount of 0.1 mole or more, more preferably in an equimolar amount or more, based on the compound represented by the formula (3). Further, the agent is preferably used in an amount of 100 moles or less, more preferably 10 moles or less. Although the reaction temperature is not particularly limited, the reaction is preferably performed at a temperature of −20° C. or higher, more preferably 20° C. or higher. The reaction time is not particularly limited. Progress of the reaction can be easily monitored by an analysis method such as thin layer chromatography (TLC), high performance liquid chromatography (HPLC), and gas chromatography (GC), and therefore the reaction can be terminated when the maximum yield of objective substance is obtained.
The compounds represented by the formula (2) have asymmetric carbons indicated with *, and according to the aforementioned method, the objective substance is obtained as a racemate. In order to obtain an optically active substance, for example, asymmetric reduction can be performed as the reduction reaction with a hydrogen supplying compound in the presence of an asymmetric reduction catalyst. Examples of the asymmetric reduction catalyst include combinations of an optically active aminosulfonamide and arene chloride-ruthenium complex, optically active ruthenium complex and optically active titanium complex prepared from these complexes, and the like.
Examples of the optically active aminosulfonamide include, for example, (1R,2R)-N-(p-toluenesulfonyl)-1,2-diphenyl-1,2-ethanediamine, (1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenyl-1,2-ethanediamine, (1R,2R)-N-methanesulfonyl-1,2-diphenyl-1,2-ethanediamine, (1S,2S)-N-methanesulfonyl-1,2-diphenyl-1,2-ethanediamine, (1R,2R)-N-benzenesulfonyl-1,2-diphenyl-1,2-ethanediamine, (1S,2S)-N-benzenesulfonyl-1,2-diphenyl-1,2-ethanediamine, (1R,2R)-N-mesitylenesulfonyl-1,2-diphenyl-1,2-ethanediamine, (1S,2S)-N-mesitylenesulfonyl-1,2-diphenyl-1,2-ethanediamine, (1R,2R)-N-(p-toluenesulfonyl)-1,2-cyclohexyldiamine, (1S,2S)-N-(p-toluenesulfonyl)-1,2-cyclohexyldiamine, and the like. Examples of the arene chloride-ruthenium complex include, for example, dichlorobenzene ruthenium dimer, dichloro(p-cymene)ruthenium dimer, dichloromesitylene ruthenium dimer, and the like.
Examples of the optically active ruthenium catalyst include, for example, [(1R,2R)-N-(p-toluenesulfonyl)-1,2-diphenyl-1,2-ethanediamine](p-cymene)ruthenium, [(1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenyl-1,2-ethanediamine](p-cymene)ruthenium, [(1R,2R)-N-methanesulfonyl-1,2-diphenyl-1,2-ethanediamine](p-cymene)ruthenium, [(1S,2S)-N-methanesulfonyl-1,2-diphenyl-1,2-ethanediamine](p-cymene)ruthenium, [(1R,2R)-N-(p-toluenesulfonyl)-1,2-diphenyl-1,2-ethanediamine](benzene)ruthenium, [(1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenyl-1,2-ethanediamine](benzene)ruthenium, and the like. Examples of the optically active titanium complex include, for example, (R,R)-ethylene-1,2-bis(η5-4,5,6,7-tetrahydro-1-indenyl)titanium difluoride, (S,S)-ethylene-1,2-bis(η5-4,5,6,7-tetrahydro-1-indenyl)titanium difluoride, (R,R)-ethylene-1,2-bis(η5-4,5,6,7-tetrahydro-1-indenyl)titanium dichloride, (S,S)-ethylene-1,2-bis(η5-4,5,6,7-tetrahydro-1-indenyl)titanium dichloride, (R,R)-ethylene-1,2-bis(η5-4,5,6,7-tetrahydro-1-indenyl)titanium (R)-1,1′-binaphth-2,2′-diolate, and (S,S)-ethylene-1,2-bis(η5-4,5,6,7-tetrahydro-1-indenyl)titanium (S)-1,1′-binaphth-2,2′-diolate.
Examples of the hydrogen supplying compound include, for example, a formic acid-tertiary amine mixture, 2-propanol, and an alkylsilane, examples of the formic acid-tertiary amine mixture include a formic acid-triethylamine mixture, and examples of the alkylsilane include phenylsilane. Examples of the solvent for carrying out the asymmetric reduction include, for example, an alcohol type solvent, an ether type solvent, a chlorinated hydrocarbon type solvent, acetonitrile, dimethyl sulfoxide, dimethylformamide, acetone, and the like, and a single solvent and mixtures at arbitrary ratios of these solvents are included. Examples of the alcohol type solvent include methanol, ethanol, and 2-propanol, examples of the ether type solvent include diethyl ether, tetrahydrofuran, and 1,4-dioxane, and examples of the chlorinated hydrocarbon type solvent include dichloromethane, and 1,2-dichloroethane. Further, the asymmetric reduction reaction can also be performed without solvent.
The asymmetric reduction can be performed according to methods described in the literature, for example, Noyori et al., J. Am. Chem. Soc., Vol. 118, pp. 4916-4917, 1996; Johansson A., Contemp. Org. Synth., Vol. 2, pp. 393-407, 1995; Buchwald S. L. et al., Angew. Chem. Int. Ed., Vol. 37, pp. 1103-1107, 1998; Buchwald S. L. et al., Tetrahedron Letters, Vol. 3740, pp. 2033-2034, 1999 and the like. It is preferable to appropriately choose a method from those described in the aforementioned literature to prepare a compound of the formula (1) as the ultimate objective compound in which the carbon atom corresponding to the asymmetric carbon indicated with * in the aforementioned formula (2) is in the R-configuration. As the reduction reaction, asymmetric reduction is preferably performed.
Further, when a compound represented by the formula (2) is obtained as a racemate, the racemate can be converted into an addition salt with an optically active acid such as camphorsulfonic acid, mandelic acid, and tartaric acid, and then subjected to fractional recrystallization to separate an optically active substance. Further, the separation can also be performed by using a commercially available optically active column.
After a compound represented by the formula (2) is obtained, when a protective group exists in A′ or B′, the compound can be deprotected to obtain a compound represented by the formula (1). In addition, a compound represented by the formula (2) in which a protective group does not exist in A′ and B′ corresponds to the compound of the formula (1). Also for the aforementioned compound, an optically active substance can be obtained by the aforementioned method.
When the protective group contained in A′ or B′ is a protective group of hydroxyl group, the protective group of hydroxyl group is not limited so long as a protective group ordinarily used in the organic synthesis is chosen, and preferred examples include a trialkylsilyl group, a benzyl group which may be substituted, an n-alkyl group, an acyl group, and the like. Examples of the trialkylsilyl group include, for example, a trialkylsilyl group such as t-butyldimethylsilyl group, trimethylsilyl group, and triethylsilyl group, t-butyldiphenylsilyl group, and the like. Examples of the benzyl group which may be substituted include, for example, benzyl group, 4-methoxybenzyl group, 4-nitrobenzyl group, and the like. Examples of the n-alkyl group include, for example, methyl group. Examples of the acyl group include, for example, acetyl group, benzoyl group, and the like.
When the protective group contained in A′ or B′ is a protective group of amino group, the protective group of amino group is not limited so long as a protective group ordinarily used in the organic synthesis is chosen, and preferred examples include, for example, benzyl group which may be substituted, an alkyloxycarbonyl group, and an acyl group. Examples of the benzyl group which may be substituted include, for example, benzyl group, 4-methoxybenzyl group, and 4-nitrobenzyl group. Examples of the alkyloxycarbonyl group include, for example, t-butyloxycarbonyl group, benzyloxycarbonyl group, and the like. Examples of the acyl group include, for example, acetyl group, benzoyl group, and the like.
As for the deprotection, when two or more kinds of protective groups are removed, they may be removed sequentially or simultaneously. For example, it is preferable to first remove the protective group of hydroxyl group in A′ or B′, and then subsequently remove the protective group of amino group in A′ or B′. Further, it is also preferable to perform sequential deprotection under different deprotection conditions.
For example, when the protective group of hydroxyl group in A′ or B′ contains a benzyl group which may be substituted, or when the protective group of amino group contains a benzyl group which may be substituted or benzyloxycarbonyl group, a method of performing hydrogenolysis in an inert solvent in the presence of a metal catalyst may be used. Examples of the inert solvent include, an alcohol type solvent, an ester type solvent, and an ether type solvent. Examples of the alcohol type solvent include methanol, ethanol, and 2-propanol, examples of the ester type solvent include ethyl acetate and the like, and examples of the ether type solvent include tetrahydrofuran, 1,4-dioxane, and the like. The hydrogenolysis may be performed in a simple solvent or a mixed solvent at an arbitrary ratio of these solvents. Examples of the metal catalyst include, for example, a simple catalyst and a catalyst carried on carbon powder of palladium, nickel, and the like. Examples of the method of the hydrogenolysis include a method of using hydrogen gas, and a method of carrying out the reaction by generating active type hydrogen in a reaction system using formic acid, ammonium formate, or the like as in methods described in the literature (B. ElAmin et al., J. Org. Chem., Vol. 44, p. 3442, 1979; T. Bieg et al., Synthesis, p 76, 1978).
When the protective group of hydroxyl group in A′ or B′ contains benzyl group which may be substituted or n-alkyl group, the deprotection method may be, for example, a method of treating the compound with a dealkylation agent in a chlorinated hydrocarbon solvent. Examples of the chlorinated hydrocarbon include, for example, simple solvents and mixed solvents at an arbitrary ratio of 1,2-dichloroethane, methylene chloride, and the like. Examples of the dealkylation agent include a Lewis acid such as boron tribromide, hydrogen iodide, and the like.
When the hydroxyl group of A′ or B′ contains a hydroxyl group protected with an acyl group, or when the amino group of A′ and B′ contains an amino group protected with an acyl group, known conditions for hydrolysis of esters using an alkali or acid can be used. Examples of the solvent include a single solvent of an alcohol type solvent such as methanol and ethanol or water, and a mixed solvent thereof at an arbitrary ratio with a water-soluble ether type solvent such as tetrahydrofuran, and 1,4-dioxane. Examples of the alkali include sodium hydroxide, potassium hydroxide, and the like, and examples of the acid include a mineral acid such as hydrochloric acid, nitric acid, and sulfuric acid.
When the protective group of hydroxyl group of A′ or B′ contains a trialkylsilyl group, known conditions for removing a silyl group can be used. The method may be, for example, a reaction using acetic acid, and tetrabutylammonium fluoride in a water-soluble ether type solvent such as tetrahydrofuran. The amount of tetrabutylammonium fluoride is preferably 1 mole or more and 5 moles or less based on the protective group contained in the compound represented by the formula (2). The reaction time is not particularly limited. Progress of the reaction can be easily monitored by the aforementioned analysis methods, and therefore the reaction can be terminated when the maximum yield of the objective substance is obtained.
When the protective group of amine in A′ or B′ contains t-butyloxycarbonyl group, deprotection can be performed by a method of treating the compound with an acid in an inert solvent. Examples of the inert solvent include an ether type solvent, an ester type solvent, and an alcohol type solvent. Examples of the ether type solvent include diethyl ether and 1,4-dioxane, examples of the ester type solvent include ethyl acetate, examples of the alcohol type solvent include methanol, ethanol, and the like, and a single solvent and a mixed solvent at an arbitrary ratio of these solvents are included. Examples of the acid include hydrochloric acid, trifluoroacetic acid, and the like. Although the reaction temperature is not particularly limited, the reaction is preferably carried out at a temperature of 0° C. or higher, more preferably 20° C. or higher. It is also preferable to carry out the reaction with heating, and the upper limit of the temperature is, for example, the reflux temperature of the solvent.
The compounds represented by the formula (3) can be prepared by reacting an amine represented by the formula (4):




wherein A′ and n have the same meanings as those defined above, with a carbonyl compound represented by the formula (5):





wherein R1 and B′ have the same meanings as those defined above, in an inert solvent, or without solvent.

The amount of the compound represented by the formula (4) is preferably 0.8 mole or more, more preferably an equimolar amount or more, based on the compound represented by the formula (5). The amount is preferably 5 moles or less, more preferably 2 moles or less. Further, a dehydration agent may be added as a reagent for promoting generation of an imine. Examples of the dehydration agent include, for example, titanium tetraisopropoxide, potassium hydroxide, titanium tetrachloride, molecular sieves, and the like. The amount of the dehydration agent is preferably 0.8 mole or more, more preferably an equimolar amount or more, based on the compound represented by the formula (4). The amount is preferably 5 moles or less, more preferably 2 moles or less.
Examples of the inert solvent include, for example, an alcohol type solvent, a chlorinated hydrocarbon type solvent, an ether type solvent, a hydrocarbon type solvent, an aromatic hydrocarbon type solvent, dimethyl formamide, dimethyl sulfoxide, and the like. Examples of the alcohol type solvent include methanol, ethanol, 2-propanol, and the like, examples of the chlorinated hydrocarbon type solvent include methylene chloride, chloroform, 1,2-dichloroethane, and the like, and examples of the ether type solvent include tetrahydrofuran, diethyl ether, and the like. Examples of the hydrocarbon type solvent include pentane, hexane, and the like. Examples of the aromatic hydrocarbon type solvent include toluene, xylene, and the like. Preferred examples of the solvent include methanol, ethanol, 2-propanol, diethyl ether, and toluene. Further, this reaction can also be performed without solvent, and the reaction without solvent is also preferred. Although the reaction temperature is not particularly limited, the reaction is performed at a temperature of −20° C. or higher, preferably 0° C. or higher. Although the upper limit of the reaction temperature is not particularly limited so long as the compound is not decomposed, the reaction can be preferably performed at a temperature up to the boiling point of the solvent, and when the reaction is performed without solvent, the upper limit is, for example, 100° C. Although the reaction time is not particularly limited, the reaction is usually performed for 10 minutes to 48 hours. Further, progress of the reaction can be easily monitored by the aforementioned methods, and therefore the reaction can be terminated when the maximum yield of the objective substance is obtained.
Further, although the obtained compound of the formula (3) can be used for the subsequent reduction reaction without being isolated from a reaction mixture, the compound may be extracted, or purified as required, and then used for the reduction reaction. The reaction of the compound of the formula (4) and the compound of the formula (5) can be performed according to, for example, a known imine synthesis method described in a publication (Jikken Kagaku Koza (Lecture of Experiment Chemistry), 4th-edition, Vol. 20, Chapter 6, Maruzen, or WO93/04373), and the like.
The compounds represented by the formula (4) are known compounds, and can be obtained as commercial products, or easily synthesized by introducing a suitable protective group into commercially available or known corresponding various amidated compounds or nitrile compounds as required and then reducing the amide group or nitrile group into an amine according to a method described in the literature (Toson et al., Bioorg. Med. Chem., Vol. 5, pp. 1675-1684, 1997), or a publication (Jikken Kagaku Koza (Lecture of Experiment Chemistry), 4th-edition, Vol. 20, Chapter 6, Maruzen).
The compounds providing the groups represented by the formulas A1′, A2′, A3′, and A4′ can be obtained as commercial products, or can be synthesized from a corresponding alcohol according to methods described in the literature (Campi, E. M. et al., Tetrahedron; Vol. 50, pp. 2533-2542, 1994; Reddy, G. V. S. et al., Synth. Commun., Vol. 30, pp. 2233-2237, 2000), or by converting a corresponding carboxylic acid synthesized according to methods described in the literature (Toth, G. et al., Synth. Commun., Vol. 25, pp. 3067-3074, 1995; Uenishi, J. et al., J. Org. Chem., Vol. 62, pp. 1692-1701, 1997 and the like) into an amide and then reducing the amide into an amine.
The compounds represented by the formula (5) are also known compounds, and can be obtained as commercial products. Further, the compounds wherein B′ is a group represented by the formula B1′ can be synthesized by, for example, synthesizing a corresponding R11′-substituted benzoxazole or R11′-substituted benzothiazole according to methods described in the literature and publications (Robertson et al., Eur. J. Med. Chem. Chim. Ther., Vol. 21, pp 223-230, 1986; Yamanaka et al., Chemistry of Heterocyclic Compounds, Chapter 2, Kodansha, 1988 and the like) and then acylating the resultant according to the Friedel-Crafts reaction, Vilsmeier reaction, or the like described in the literature and publications (Shirley et al., J. Org. Chem., Vol. 23, 1024p, 1958; Jackson, J. Chem. Soc. Perkin Trans., 1, pp 681-687, 1990; Yamanaka et al., Chemistry of Heterocyclic Compounds, Chapter 6, Kodansha, 1988 and the like). The compounds of the formula (5) wherein B′ is a group represented by the formula B2′, and Y2 is CH can be synthesized, for example, according to methods described in the literature (Anderson et al., J. Am. Chem. Soc., Vol. 77, pp. 6321-6323, 1955; Gerdil et al., Helv. Chim. Acta, Vol. 40, pp. 141-155, 1957; Hafner et al., Justus Liebigs Ann. Chem., Vol. 625, pp. 108-122, 1959; Nozoe et al., Heterocycles, Vol. 31, pp. 17-22, 1990). The compounds of the formula (5) wherein B′ is a group represented by the formula B2′, and Y2 is nitrogen atom can be synthesized, for example, according to a method described in the literature (Nitta et al., Heterocycles, Vol. 32, pp. 23-28, 1991). The compounds of the formula (5) wherein B′ is a group represented by the formula B3′, Y2 is sulfur atom, and Y5 or Y6 is nitrogen atom can be synthesized, for example, according to methods described in the literature (Klemm, L. H. et al., J. Heterocycl. Chem., Vol. 11, pp. 205-209, 1974; Klemm, L. H. et al., J. Heterocycl. Chem., Vol. 11, pp. 355-361, 1974). The compounds of the formula (5) wherein B′ is a group represented by the formula B4′, and Y2 is CH can be synthesized, for example, according to a method described in the literature (Kawamoto T. et al., Tetrahedron. Lett., Vol. 41, pp. 3447-3451, 2000). The compounds of the formula (5) wherein B′ is a group represented by the formula B4′, and Y7 is nitrogen atom can be synthesized, for example, according to a method described in the literature (Lumma, W. C. Jr. et al., J. Org. Chem., Vol. 46, pp. 3735-3736, 1981). The compounds of the formula (5) wherein B′ is a group represented by the formula B5′ can be synthesized, for example, according to a method described in the literature (Tanji K. et al., Heterocycles, Vol. 35, pp. 915-924, 1993). Protective groups in the groups represented by the formulas B1′, B2′, B3′, B4′, and B5′ may be introduced at an appropriate stage as required.
Synthetic Method B
The compounds of the present invention represented by the formula (1) can also be produced by the following method, that is, a method of synthesizing a compound represented by the formula (6):




wherein A′, B′, R1, n, and * have the same meanings as those defined above, reducing the compound represented by the formula (6) to obtain a compound represented by the formula (2), and then obtaining a compound represented by the formula (1) from the compound represented by the formula (2) according to Synthetic method A.

The method of reducing a compound represented by the formula (6) to the compound of the formula (2) can be performed, for example, according to a known method for reducing to an amide into an amine described in a publication (Jikken Kagaku Koza (Lecture of Experiment Chemistry), 4th-edition, Vol. 20, Chapter 6, Maruzen) and the like.
A type of the reducing agent used for the reduction reaction is not particularly limited. Examples include lithium aluminum hydride, sodium borohydride, sodium cyanoborohydride, sodium triacetoxyborohydride, borane, and the like, and preferred examples include lithium aluminum hydride, sodium borohydride, sodium cyanoborohydride, sodium triacetoxyborohydride, and borane. Further, in order to enhance reactivity, a Lewis acid may be added. Examples include aluminum chloride, titanium tetrachloride, tin tetrachloride, triethyloxonium tetrafluoroborate, and the like, and preferred examples include titanium tetrachloride and triethyloxonium tetrafluoroborate. Type of the solvent used for the reaction is not particularly limited so long as a solvent inert to the reduction reaction is chosen. Examples include a saturated hydrocarbon type solvent, a chlorinated hydrocarbon type solvent, an ether type solvent, an aromatic hydrocarbon type solvent, dimethylformamide, dimethyl sulfoxide, and the like, and a single solvent and a mixed solvent at an arbitrary ratio of these solvents are included. Examples of the saturated hydrocarbon type solvent include pentane, hexane, heptane, and cyclohexane, and examples of chlorinated hydrocarbon type solvent include methylene chloride, chloroform, and 1,2-dichloroethane. Examples of the ether type solvent include tetrahydrofuran, diethyl ether, and 1,4-dioxane, and examples of the aromatic hydrocarbon type solvent include toluene, xylene, dimethylformamide, and the like. Preferred examples include methylene chloride, tetrahydrofuran, toluene, dimethylformamide, and the like. The reducing agent is preferably used in an amount of 0.1 mole or more, more preferably in an equimolar amount or more, based on the compound represented by the formula (6). Further, the agent is preferably used in an amount of 100 moles or less, more preferably 10 moles or less. When a Lewis acid is added, the acid is preferably used in an amount of 0.01 mole or more, more preferably in an equimolar amount or more, based on the reducing agent. Further, the acid is preferably used in an amount of 10 moles or less, more preferably 2 moles or less. Although the reaction temperature is not particularly limited, the reaction is preferably performed at a temperature of −20° C. or higher, more preferably 20° C. or higher. The reaction time is not particularly limited. Progress of the reaction can be easily monitored by an analysis method such as thin layer chromatography (TLC), high performance liquid chromatography (HPLC), and gas chromatography (GC), and therefore the reaction can be terminated when the maximum yield of objective substance is obtained.
The compounds represented by the formula (2) have an asymmetric carbon indicated with *, and according to the aforementioned method, the compound is usually obtained as a compound retaining the three-dimensional structure of the compound represented by the formula (6).
Further, when the compound represented by the formula (2) is obtained as a racemate, the racemate can be converted into an addition salt with an optically active acid such as camphorsulfonic acid, mandelic acid, and tartaric acid, and then subjected to fractional recrystallization to separate an optically active substance. Further, the separation can also be performed by using a commercially available optically active column as already described above.
After a compound represented by the formula (2) is obtained, when a protective group exists in A′ or B′, the compound can be deprotected to obtain a compound represented by the formula (1). In addition, a compound represented by the formula (2) in which a protective group does not exist in A′ and B′ corresponds to the compound of the formula (1). As described above, an optically active substance can be obtained by the aforementioned method also for this compound.
The compounds represented by the formula (6) can be synthesized by reacting a carboxylic acid represented by the formula (7):




wherein A′ and n are have the same meanings as those defined above, with an amine represented by the formula (8):





wherein B′, R1, and * have the same meanings as those defined above. Further, the compounds of the formula (6) can also be obtained by reacting an alkaline metal salt, active ester derivative, acid anhydride, or acid halide corresponding to a compound of the formula (7), which can be readily synthesized from the compound of the formula (7) by a known method, with an amine of the formula (8).

As for the method for obtaining the compounds of the formula (6) from compounds represented by the formulas (7) and (8), the compounds of the formula (6) can be readily synthesized by a known amidation reaction described in a publication (Jikken Kagaku Koza (Lecture of Experiment Chemistry), 4th-edition, Vol. 22, Chapters 1 and 2, Maruzen).
Examples of the condensing agent used for the amidation include dicyclohexylcarbodiimide, diisopropylcarbodiimide, N-ethyl-N′-3-dimethylaminopropylcarbodiimide, N-ethyl-N′-3-dimethylaminopropylcarbodiimide hydrochloride, benzotriazol-1-yl-tris (dimethylamino)phosphonium hexafluorophosphide salt, diphenylphosphorylazide, and the like. These agents may be used as a single agent, or used in combination with N-hydroxysuccinimide, 1-hydroxybenzotriazole, or 3-hydroxy-4-oxo-3,4-dihydro-1,2,3-benzotriazine as an additive. Further, a base may be added to neutralize the acid generated in the reaction system, and examples include a tertiary amine such as triethylamine, trimethylamine, and pyridine, carbonic acid salt such as potassium carbonate, sodium carbonate, potassium carbonate, and cesium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide, magnesium hydroxide, calcium hydroxide, and the like.
Type of the solvent used for the reaction is not particularly limited so long as a solvent inert to the reduction reaction is chosen. Examples include a saturated hydrocarbon type solvent, a chlorinated hydrocarbon type solvent, an ether type solvent, an aromatic hydrocarbon type solvent, acetonitrile, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, and the like, and a single solvent and a mixed solvent at an arbitrary ratio of these solvents are included. Examples of the saturated hydrocarbon type solvent include pentane, hexane, heptane, and cyclohexane, and examples of chlorinated hydrocarbon type solvents include methylene chloride, chloroform, and 1,2-dichloroethane. Examples of the ether type solvent include tetrahydrofuran, diethyl ether, and 1,4-dioxane, and examples of the aromatic hydrocarbon type solvent include toluene, xylene, and the like. Preferred examples include methylene chloride, tetrahydrofuran, toluene, dimethylformamide, acetonitrile, and the like. The condensing agent is preferably used in an amount of 0.8 mole or more, more preferably in an equimolar amount or more, based on the compound represented by the formula (7). Further, the agent is preferably used in an amount of 5 moles or less, more preferably 2 moles or less. The additive is preferably used in an amount of 0.8 mole or more, more preferably in an equimolar amount or more, based on the compound represented by the formula (7). Further, the additive is preferably used in an amount of 5 moles or less, more preferably 2 moles or less. When a base is added, the base is preferably added in an amount of 0.8 mole or more, more preferably in an equimolar amount or more, based on the acid generated in the reaction system. Further, the base is preferably added in an amount of 5 moles or less, more preferably 2 moles or less. Although the reaction temperature is not particularly limited, the reaction is preferably performed at a temperature of 0° C. or higher, more preferably 20° C. or higher. The reaction time is not particularly limited. Progress of the reaction can be easily monitored by an analysis method such as thin layer chromatography (TLC), high performance liquid chromatography (HPLC), and gas chromatography (GC), and therefore the reaction can be terminated when the maximum yield of objective substance is obtained.
When an alkaline metal salt or active ester of a compound represented by the formula (7) is used instead of the compound represented by the formula (7), the reaction can also be performed in a manner similar to that of the aforementioned amidation.
Further, when an acid anhydride or acid halide of a compound represented by the formula (7) is used instead of the compound represented by the formula (7), the agent can be reacted with a compound represented by the formula (8) in an inert solvent or without solvent in the presence of a base to synthesize the desired compound. Examples of the base include a tertiary amine such as triethylamine, and pyridine, carbonic acid salt such as potassium carbonate, sodium carbonate, and potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide, and the like. Type of the solvent used for the reaction is not particularly limited so long as a solvent inert to the reduction reaction is chosen. Examples include a saturated hydrocarbon type solvent, a chlorinated hydrocarbon type solvent, an ether type solvent, an aromatic hydrocarbon type solvent, acetonitrile, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, and the like, and simple solvents and mixed solvents at an arbitrary ratio of these solvents are included. Examples of the saturated hydrocarbon type solvent include pentane, hexane, heptane, and cyclohexane, and examples of the chlorinated hydrocarbon type solvent include methylene chloride, chloroform, and 1,2-dichloroethane. Examples of the ether type solvent include tetrahydrofuran, diethyl ether, and 1,4-dioxane, and examples of the aromatic hydrocarbon type solvent include toluene, xylene, and the like. Preferred examples include methylene chloride, tetrahydrofuran, toluene, dimethylformamide, and the like. Further, it is also preferable to directly use a tertiary amine such as pyridine and triethylamine as the solvent, and pyridine is preferred for such a purpose. The base is preferably used in an amount of 0.8 mole or more, more preferably in an equimolar amount or more, based on the compound represented by the formula (7).
The compounds represented by the formula (7) can be obtained as commercial products, or can be synthesized according to known methods described in the literature (Toth, G. et al., Synth. Commun., Vol. 25, pp. 3067-3074, 1995; Uenishi, J. et al., J. Org. Chem.; Vol. 62, pp. 1692-1701, 1997 and the like). Alkali metal salts of the compounds represented by the formula (7) can be easily obtained by neutralizing a compound represented by the formula (7) with an equivalent amount of an alkali metal hydroxide compound such as lithium hydroxide, sodium hydroxide, and potassium hydroxide in an alcohol solvent such as methanol and ethanol, or water. Further, acid anhydrides or acid halides of the compounds of the formula (7) can also be easily synthesized by known methods described in publications (Jikken Kagaku Koza (Lecture of Experiment Chemistry), 4th-edition, Vol. 22, Chapter 1, Maruzen and the like).
The compounds represented by the formula (8) can be obtained as commercial products, or can be synthesized from a compound represented by the formula (5) according to known methods described in the literature (B. Sukanta et al., Syn. Lett., Vol. 11, pp. 1781-1783, 1999 and the like). Examples of the compounds represented by the formula (8) include the followings compounds.













The compounds represented by the formula (8) wherein B′ is a group represented by the formula B2′, and Y2 is CH can be synthesized by the method shown in the following scheme.




More specifically, a ketone represented by the formula (5B2-1) in the scheme is converted into an alcohol represented by the formula (8B2-1B) in the scheme by reduction with lithium aluminum hydride, and then the alcohol is reacted with phthalimide in the presence of tri-n-butylphosphine and 1,1′-azobis(N,N′-dimethylformamide) and thereby converted into a compound represented by the formula (8B2-1A) in the scheme. Finally, the resulting product can be deprotected with hydrazine to obtain a compound represented by the formula (8B2-1) in the scheme. The compounds represented by the formula (8B2-1) and (8B2-1A) in the scheme are novel substances, and are extremely useful compounds for carrying out the present invention. The reducing agent used for obtaining a compound represented by the formula (8B2-1B) in the scheme from a compound represented by the formula (5B2-1) in the scheme is not limited to lithium aluminum hydride, and various reducing agents can be used. Further, as the phosphine and azo regent used for obtaining a compound represented by the formula (8B2-1A) in the scheme from a compound represented by the formula (8B2-1B) in the scheme, those other than the substances mentioned in the scheme may be used, and instead of the phthalimide used in the scheme, other imides such as maleimide and succinimide may be used. Further, the deprotection agent used for obtaining a compound represented by the formula (8B2-1) in the scheme from a compound represented by the formula (8B2-1A) in the scheme is not limited to hydrazine, and various deprotection agents can be used. The compounds represented by the formulas (8B2-1B), (8B2-1A), and (8B2-1) in the scheme have asymmetric carbons indicated with *, and racemate of each can be separated by using a commercially available optically active column to obtain an optically active substance. Further, by performing the aforementioned asymmetric reduction reaction in the reaction for obtaining a compound represented by the formula (8B2-1B), an optically active substance can be obtained. Furthermore, the compounds represented by the formula (8B2-1) can also be obtained by carrying out fractionation recrystallization after formation of an addition salt with the aforementioned optically active acid.
Synthetic Method C
The compounds of the present invention represented by the formula (1) can also be produced by the following method, i.e., a method for synthesizing a compound represented by the formula (9):




wherein A′, B′, R1, n, and * have the same meanings as those defined above, then reducing the compound represented by the formula (9) to synthesize a compound represented by the formula (2), and further obtaining a compound represented by the formula (1) from the compound represented by the formula (2) according to the method described in Synthetic method A.

The method of reducing a compound represented by the formula (9) to obtain a compound of the formula (2) can be performed according to the method for obtaining a compound of the formula (2) from a compound of the formula (3) described in Synthetic method A.
The compounds represented by the formula (9) can be synthesized by reacting an amine represented by the formula (8):




with an aldehyde represented by the formula (10):





wherein A′ and n have the same meanings as those defined above.

The method for obtaining a compound of the formula (9) from a compound of the formula (8) and a compound of the formula (10) can be performed according to the method for obtaining a compound of the formula (3) from a compound of the formula (4) and a compound of the formula (5) described in Synthetic method A.
The compounds represented by the formula (10) can be obtained as commercial products, or can be synthesized according to known methods described in the literature (Roger et al., Bioorg. J. Med. Chem. Lett., Vol. 36, pp. 5461-5464, 1995; Williams J. M. et al., Tetrahedron Letters, Vol. 6, pp. 1691-1696, 1996). The compounds represented by the formula (10) can also be obtained by oxidizing a corresponding alcohol by the method described in publications (Jikken Kagaku Koza (Lecture of Experiment Chemistry), 4th-edition, Vol. 23, Maruzen). Carboxylic acids, esters, and alcohols corresponding to the compounds represented by the formula (10) can be obtained as commercial products, or can be easily synthesized by known methods.
Examples of the compounds represented by the formula (10) include the followings compounds.


































































































































The compounds of the formula (1) wherein the group represented by B is naphthalene group or a substituted naphthalene group also fall within the scope of the compounds of the present invention. As for the production of these compounds, they can be produced by according to Synthetic method A or Synthetic method B described above as the synthetic methods of the compounds represented by the formula (1). Namely, a compound represented by the formula (5) or (8) wherein the group represented by B′ is naphthalene group, or a substituted naphthalene group of which substituent may have a protective group may be used as a starting material.
The compounds represented by the formula (5) wherein the group represented by B′ is naphthalene group can be obtained as commercial products.
The compounds represented by the formula (5) wherein the group represented by B′ is a substituted naphthalene group of which substituent may have a protective group can be synthesized by acylating a commercially available substituted naphthalene using a Friedel-Craft reaction with a commercially available compound represented by R1COCl or (R1CO)2O in the presence of a Lewis acid such as aluminum chloride or titanium tetrachloride according to methods described in the literature (Brown et at., J. Org. Chem., Vol. 11, p. 163, 1946; Snatzke G. et al., Chem. Ber., Vol. 106, pp. 1341-1362, 1973 and the like). Further, they can also be synthesized according to another method described in the literature (Amin S. et at., J. Org. Chem., Vol. 46, pp. 2394-2398, 1981). The protective group in a substituent may be introduced at appropriate time before or after the acylation depending on the conditions.
The compounds represented by the formula (8) wherein the group represented by B′ is naphthalene group can be obtained as commercial products.
The compounds represented by the formula (8) wherein the group represented by B′ is a substituted naphthalene group of which substituent may have a protective group can be synthesized from a corresponding compound represented by the formula (5) according to methods described in the literature (B. Sukanta et at., Syn. Lett., Vol. 11, pp. 1781-1783, 1999; Roberts et al., J. Med. Chem., Vol. 15, pp. 1270-1273, 1972; Nagashima et at., Chem. Pharm. Bull., Vol. 15, pp. 251-257, 1984 and the like).
The compounds of the present invention obtained as described above as well as starting compounds and synthetic intermediates for said compounds can be isolated and purified by performing conventional operations such as extraction, distillation, and chromatography, as required. When a salt of a compound of the formula (1) is prepared, the compound of the formula (1) can be dissolved in an alcohol type solvent such as methanol and ethanol and converted into an acid addition salt by addition of an equivalent amount or an amount of several times of equivalents of an acid component. Examples of the acid component used include, for example, hydrochloric acid, hydrobromic acid, sulfuric acid, hydrogensulfate, dihydrogenphosphate, citric acid, maleic acid, tartaric acid, fumaric acid, gluconic acid, methanesulfonic acid, and the like, and it is preferable to use a physiologically acceptable mineral acid or organic acid.
The compounds of the present invention and physiologically acceptable salts thereof have no toxicity as demonstrated in the examples described later, and have a PTH depressing action, and therefore they are useful as active ingredients of medicaments. The PTH depressing agent of the present invention can be expected to exhibit a blood PTH concentration depressing action, or in addition, a PTH concentration depressing action in various organs and the like. The PTH depressing action of the compounds of the present invention or physiologically acceptable salts thereof can be evaluated by using the blood PTH concentration depressing action or the like observed, for example, when they are administered to laboratory animals such as rats, as a marker. Further, the PTH concentration depressing action can also be evaluated on the basis of the blood PTH concentration depressing action or bone metabolism improving action as a marker by using disease model animals such as rats with experimentally induced chronic renal failure.
The medicament of the present invention comprising a compound represented by the aforementioned formula (1) or a physiologically acceptable salt thereof as an active ingredient can depress PTH in vertebrates including human, preferably mammals, and is useful as a medicament for prophylactic and/or therapeutic treatment of, for example, hyperPTHemia. Furthermore, the medicament of the present invention is useful for prophylactic and/or therapeutic treatment of various bone diseases (e.g., osteoporosis and the like) associated with increase in blood PTH, or can depress blood PTH in patients of hypercalcemia to depress blood calcium concentration, and thereby prevent and/or cure hypercalcemia. Although the blood PTH concentration may not be so high as that in hyperPTHemia in these diseases, the medicament of the present invention can also be suitably used for these diseases.
The hyperPTHemia is defined as a disease exhibiting a high blood PTH concentration beyond the range of normal value. As for a human, a disease exhibiting a high blood PTH concentration beyond the range of normal value can be diagnosed by measuring the intact blood PTH concentration by applying an immunoradiometric assay (IRMA) method (Nihon Medi-Physics Co., Ltd, Allegro intact PTH kit) using a radiolabeled anti-human N-terminus (1-34) antibody and anti-human C-terminus (39-84) antibody, and comparing the measured value with the normal value of human measured by the same method (13 to 53 pg/ml) (Takuwa, A “V. Endocrinological Inspection, B. Thyroid and Parathyroid-Related Inspection, Parathyroid Hormone”, Nippon Rinsho (The Japanese Journal of Clinical Medicine), Vol. 53 (Special number), pp. 393-396, 1995). A normal value of the blood PTH concentration varies depending on a measurement system, an animal species and the like. Therefore, a normal value given by each of measurement systems, literature, or medical research facilities may be referred to.
Examples of the causative disease of hyperPTHemia include hyperparathyroidism and the like, and the hyperparathyroidism is basically classified into primary hyperparathyroidism and secondary hyperparathyroidism depending on critical pathological mechanism.
The primary hyperparathyroidism is a generic name of diseases in which abnormalities are observed in the PTH secretion regulation mechanism in the parathyroid, and PTH is secreted at an inappropriately high concentration compared with an extracellular calcium concentration. Specific examples thereof include parathyroid adenoma, parathyroid hyperplasia, parathyroid carcinoma, multiple endocrine neoplasia type 1, multiple endocrine neoplasia type 2A, familial isolated hyperparathyroidism (FIHP) hyperparathyroidism-lower jaw tumor syndrome (HPT-JT), familial hypocalciuric hypercalcaemia (FHH), and the like (Ohara, T., “4. Abnormality of Calcium Metabolism, (1) Primary Hyperparathyroidism”, Hormone to Rinsho (Clinical Endocrinology), 49, Suppl., pp. 74-76, 2001).
The secondary hyperparathyroidism is a generic term of diseases in which PTH secretion is promoted as a reaction to hypocalcemia, hyperphosphoremia, activated vitamin D resistance and the like induced by various causes other than those originated in the parathyroid. Specific examples thereof include hyperparathyroidism resulting from chronic renal failure, hyperparathyroidism resulting from osteomalacia (or rachitis), hyperparathyroidism resulting from renal tubule dysfunction, hyperparathyroidism resulting from malabsorption syndromes originating in stomach extraction, intestinal diseases, and the like, hyperparathyroidism resulting from vitamin D deficiency or vitamin D activation disorder, hyperparathyroidism resulting from osteoporosis, hyperparathyroidism resulting from pseudohypoparathyroidism, hyperparathyroidism resulting from pregnancy and breast-feeding, hyperparathyroidism resulting from Cushing syndrome, hyperparathyroidism resulting from hypercalcitonism, hyperparathyroidism resulting from administration of drug such as anticonvulsant, hyperparathyroidism resulting from shortage of calcium ingestion or excessive loss of calcium in urine, hyperparathyroidism resulting from excessive ingestion of phosphorus, and the like (Tabata, T. and Nishizawa, Y., “Secondary Hyperparathyroidism”, Igaku no Ayumi, Separate volume of October (Endocrinological and Metabolic Diseases), pp. 374-376, 1997; Tomita, A., “Secondary Hyperparathyroidism”, Saisin Naikagaku Taikei (Newest Internal Medicine Study System) 14, Endocrinological Diseases 3 (edited by Inoue, H. et al.), pp. 72-79, Nakayama Shoten, Tokyo, 1993; Nakanishi, S. and Fukagawa, M., “Pathological Mechanism of Renal Hyperparathyroidism”, CLINICAL CALCIUM, pp. 1625-1630, 2002).
Furthermore, hyperparathyroidism that originates in chronic renal failure is highly frequently complicated with various bone metabolic disorders. Such bone metabolic disorders generically called renal osteodystrophia (or renal osteopathy or dialysis osteopathy), and examples thereof include fibrous ostitis, osteomalacia (or rachitis), mixed ostitis, and the like (Tabata, T. and Nishizawa, Y., “Renal Osteodystrophia”, Newest Osteoporosis (edited by Orishige, H.), pp. 87-91, Life Science Publishing, Tokyo, 1999; Tsukamoto, Y., “Renal Osteodystrophia”, Hormone to Rinsho (Clinical Endocrinology), 49, Suppl., pp. 77-80, 2001). The fibrous ostitis is characterized by increase in intramedullary fibrous tissues, and osteomalacia (or rachitis) is characterized by excessive deposition of osteoid due to calcification disorder. Further, the mixed ostitis is characterized by intermingled pathological change of fibrous ostitis and osteomalacia in the same tissue. These fibrous ostitis, osteomalacia (or rachitis), and mixed ostitis are also included in the pathological conditions of hyperparathyroidism resulting from chronic renal failure, and they can be therapeutically or prophylactically treated by using the medicament of the present invention. Furthermore, chronic renal failure may be complicated with osteopenia or osteoporosis (osteoporosis is a generic term of systemic bone diseases characterized by decrease in bone mass, collapse of the microstructure of bone tissues, resulting increase in bone brittleness, bone fracture susceptibility, and the like), which is diagnosed by using the bone mineral amount as a marker (Taal et al. “Risk factors for reduced bone density in haemodialysis patients, “Nephrol. Dial. Transplant., 14. pp. 1922-1928, 1999). These conditions are also included in the pathological conditions of hyperparathyroidism, and can be therapeutically or prophylactically treated by using the medicament of the present invention.
Further, chronic renal failure may present various clinical symptoms besides the bone metabolic disorders. For example, influences on the cranial nerve system, cardiovascular system, skeletal muscles, hemopoietic and immune systems, endocrine and metabolic systems, and respiratory system are observed as peripheral influences, and systemic influences are also often observed. Specifically, for example, there are electroencephalographic dysrhythmia, behavior disorder, peripheral nerve disease and the like for the cranial nerve system, ventricular hypofunction, cardiac myopathy and the like for the cardiovascular system, hypodynamia, adynamic attack, tendon rupture and the like for skeletal muscles, anemia, leukocytic and lymphatic hypofunction and the like for the hemopoietic and immune systems, glucose tolerance abnormality, lipid metabolic disorders such as hyperlipidemia, hypogonadism and the like for the endocrine and metabolic system, diffusion disturbance, increased right ventricular pressure and the like for the respiratory system, ectopic calcification in arterial walls, eyes, visceral organs and circumferences of joints, itch, abnormal blood pressure and the like as systemic symptoms (Kurihara R., “Whether Optimum PTH Exists for Dialysis Patient?”, CLINICAL CALCIUM, 9, pp. 734-740, 1999; Tahara H. et al., “4. Pathological Conditions of Secondary Hyperparathyroidism, 1) Clinical Features”, Iyaku Journal, 37, pp. 148-152, 2001), and these conditions are also included in the pathological conditions of hyperparathyroidism, and can be therapeutically or prophylactically treated by using the medicament of the present invention.
Further, controlling progression of renal disorder on the basis of the effect of improving hyperPTHemia has been reported (Shigematsu et al. “Parathyroid removal prevents the progression of chronic renal failure induced by high protein diet”, Kidney Int., 44, pp. 173-181, 1993). The medicament of the present invention has an action of improving hyperPTHemia, and thus the medicament of the present invention is effective for pre-dialysis chronic renal failure (not yet in a stage of dialysis treatment) presenting hyperparathyroidism for improving renal disorder to prolong a period before dialysis theatment becomes necessary. Therefore, the use of the medicament of the present invention for the disease as a therapeutic or prophylactic agent is also included in the applications of the present invention.
Besides these diseases, any diseases exhibiting a high blood PTH concentration beyond a range of normal value are included in the category of hyperPTHemia, and can be therapeutically or prophylactically treated by using the medicament of the present invention.
The medicament of the present invention can be used for the prophylactic and/or therapeutic treatment of various bone diseases associated with relative increase in blood PTH, even if a blood PTH concentration before the administration of the medicament is within a range of normal value. Examples of such bone diseases include osteoporosis and the like, and examples of osteoporosis according to such classification include postmenopausal osteoporosis, senile osteoporosis, osteoporosis induced by a drug such as adrenal cortex hormone, and the like (Morii, H., “Definition and Concept of Osteoporosis”, Newest Osteoporosis (edited by Orishige H.), pp. 39-42, Life Science Publishing, Tokyo, 1999). It is pointed out that, in these types of osteoporosis, when a degree of bone mass reduction is higher or pathological condition is severer, a blood PTH concentration is relatively increased (most of the increase is observed within the range of the normal value), and as a result, bone resorption is being promoted to advance the bone mass reduction (Tomita, A. and Negoro, Y., “Biochemical Diagnosis Method of Osteoporosis”, Osteoporosis/Diagnosis and Treatment (edited by Fujita., T), pp. 285-293, Life Science Publishing, Tokyo, 1992). The medicament of the present invention achieves suppression of the increase of bone resorption by depressing PTH, and as a result, the medicament is useful for prophylactic and/or therapeutic treatment of osteoporosis.
Further, the medicament of the present invention exhibits an action of depressing the blood calcium concentration on the bases of the blood PTH concentration depressing action, and therefore the medicament can be used for prophylactic and/or therapeutic treatment of hypercalcemia and the like. Examples of hypercalcemia include hypercalcemia originating in a malignant tumor. Examples of hypercalcemia originating in a malignant tumor include humoral hypercalcemia of malignancy (HHM) in which bone resorption promotion factors, produced by tumor cells of epidermoid carcinoma, urologic cancer or the like, causes systemic bone resorption to induce hypercalcemia, and local osteolytic hypercalcemia (LOH) in which bone resorption promotion factor secreted from blood tumors such as multiple myeloma cause local osteolysis to induce hypercalcemia (Okano, K., “Concept and Pathology of Hypercalcemia”, Hormone to Rinsho (Clinical Endocrinology), 41, 1-6, 1993). Besides these diseases, any diseases for which prophylactic and/or therapeutic effect may be achieved by depressing the blood PTH concentration may be applicable by the medicament of the present invention.
The medicament of the present invention is preferably used for prophylactic and/or therapeutic treatment of hyperPTHemia, osteoporosis, and hypercalcemia, more preferably used for prophylactic and/or therapeutic treatment of hyperPTHemia, and still more preferably used for prophylactic and/or therapeutic treatment of hyperparathyroidism.
The medicament of the present invention can be prepared as a medicament comprising a compound represented by the formula (1) or a physiologically acceptable salt thereof as an active ingredient. For example, a compound or a salt thereof, which is administered as a prodrug and produces the compound represented by the formula (1) or a physiologically acceptable salt thereof after in vivo metabolism, also falls within the scope of the medicament of the present invention. A compound represented by the formula (1) or a physiologically acceptable salt thereof, per se, may be used as the medicament of the present invention. It is preferable to add one or more kinds of pharmaceutically acceptable carriers to the compound represented by the formula (1) or a physiologically acceptable salt thereof to prepare a pharmaceutical composition and administer the composition. Types of pharmacologically acceptable carriers are not particularly limited, and examples include, for example, excipients, binders such as carboxymethylcellulose, disintegrating agents, lubricants, additives, and the like. A hydrate or solvate of a compound represented by the formula (1) or a physiologically acceptable salt thereof may also be used as an active ingredient of the medicament of the present invention. When the medicament of the present invention is administered to a human, the medicament can be orally administered in a form of, for example, a tablet, a powder, a granule, a capsule, a sugar-coated pill, a solution, a syrup or the like, or the medicament can also be parenterally administered in a form of an injection, a drip infusion, a suppository, a transdermal preparation or the like.
An administration period of the medicament of the present invention is not particularly limited. In principle, the medicament is administered during a period where it is judged that clinical symptoms of a disease are expressed, and it is common to continue the administration for several weeks to one year. However, it is also possible to extend the administration period depending on pathological conditions, or continue the administration even after recovery of the clinical symptoms. The medicament may also be prophylactically administered by a decision of a medical doctor even if a clinical symptom is not expressed. A dose of the medicament of the present invention is not particularly limited. The medicament may generally be administered in an amount of 0.01 to 2000 mg per day as the active ingredient once or several times as divided portions. As for administration frequency, the medicament may be administered once a month to every day, and the medicament may preferably be administered once to three times per week or five times per week, or every day. The daily dose, administration period, and administration frequency may be suitably increased or decreased depending on various factors such as the age, weight, degree of physical healthiness of a patient, a type and severity of a disease to be treated.
For example, when hyperparathyroidism is prevented and/or treated with the medicament of the present invention, the medicament of the present invention can be used together with one or more kinds of medicaments selected from the group consisting of vitamin D agents including vitamin D derivatives and/or phosphorus depressing agents simultaneously or at different time. Further, the medicament of the present invention can also be prepared as a so-called combined medicament together with the medicament exemplified above and then administered. Examples of the vitamin D agents including vitamin D derivatives include, for example, calcitriol, alfacalcidol, farecalcitriol, paricalcitol, doxercalciferol, maxacalcitol, secalciferol, and the like, and examples of the phosphorus depressing agents include, for example, calcium carbonate, calcium lactate, calcium gluconate, calcium acetate, calcium chloride, calcium citrate, magnesium carbonate, calcium hydrogenphosphate, calcium L-aspartate, polynuclear ferric hydroxide, sevelamer hydrochloride, lanthanum carbonate, resin ion-exchange resins, colestimide, and the like. Further, agents having an inhibitory action on the phosphorus absorption mechanism from an alimentary canal such as niceritrol are also included in the phosphorus depressing agents. The vitamin D agents including vitamin D derivatives and/or phosphorus depressing agents, which are used together with the medicament of the present invention or used for preparing so-called combined drug to treat or prevent hyperparathyroidism, are not limited to these examples.
Further, when osteoporosis is prevented and/or treated with the medicament of the present invention, for example, the medicament of the present invention can be used together with one or more kinds of medicaments selected from the group consisting of bone activating agents, osteogenesis promoting agents, bone resorption suppressing agents, bone metabolism improving agents, sexual hormone preparations, and calcium preparations, simultaneously or at different time. Further, the medicament of the present invention can also be prepared as a so-called combined drug together with the medicament exemplified above and then administered. Examples of the bone activating agents include, for example, calcitriol, alfacalcidol, OCT, ED-71, and the like, examples of the osteogenesis promoting agents include, for example, menatetrenone, teriparatide, somatropin, insulin-like growth factor, EP4 agonist, EP2 agonist, growth hormone secretagogues, and the like, examples of the bone resorption suppressing agents include, for example, elcatonin, calcitonin salmon, etidronate, pamidronate, clodronate, alendronate, incadronate, risedronate, minodronate, ibandronate, cathepsin K inhibitors, osteoprotegerin, anti-RANKL antibodies, and the like, examples of the bone metabolism improving agents include, for example, fluoride, ipriflavone, and the like, examples of the sexual hormone preparations, include, for example, estriol, estradiol, conjugated estrogen, progesterone, medroxyprogesterone, testosterone, metyltestosterone, mestanolone, stanozolol, metenolone, nandrolone, selective estrogen receptor modulators (SERM: raloxifen, lasofoxifene, bazedoxifene, ospemifene, arzoxifene, CHF4227, PSK-3471, and the like), selective androgen receptor modulators (SARM), and the like, and examples of the calcium preparations include calcium carbonate, calcium lactate, calcium gluconate, calcium acetate, calcium chloride, calcium citrate, calcium hydrogenphosphate, calcium L-aspartate, and the like. The bone activating agents, osteogenesis promoting agents, bone resorption suppressing agents, bone metabolism improvement agents, sexual hormone preparations, and calcium preparations used together with the medicament of the present invention, or used for preparing the so-called combined drug together with the medicament of the present invention to treat or prevent osteoporosis are not limited to these examples.
Further, the medicament of the present invention can also be administered together with one or more kinds of medicaments suitably selected from prophylactic agents and curative agents for various abnormalities and diseases complicating with hyperPTHemia including hyperparathyroidism, osteoporosis, and hypercalcemia [e.g., antibacterial agents, antiviral agents, antifungal agents, antiparasitic (antihelminth, antiprotozoan) agents, vaccination agents, antiseptics, anticancer agents, immunosuppressive agents, adrenal-cortex steroids, nonsteroidal anti-inflammatory agents, antirheumatic agents, antarthritics, anti-inflammatory enzymes, antihistaminic agents, antiallergic agents, antidiabetic agents, female hormone preparations, male hormone preparations, other hormone preparations, thyroid disease curative agents, bone and calcium metabolic agents, vitamin preparations, fluid-therapy preparations (electrolyte fluid, dialysis and peritoneal dialysis solutions, and the like), blood preparations, hematopoietic agents, hypoleukocytemia curative agents, hemostatic agents, antithrombotic agents, antihyperlipidemic agents, cardiac stimulants (heart failure curative agents), antiarrhythmic agents, antianginal agents, vasodilators, antihypertensive agents, vasopressors, diuretic agents, bronchodilators, bronchial asthma curative agents, respiratory stimulants, antitussive agents, expectorants, stomachic digestants and gastrointestinal promotility agents, digestive ulcer curative agents (antacids, antispasmodic agents, antiulcer agents), intestinal disease curative agents, purgatives (cathartics), biliary disease curative agents, liver disease curative agents, pancreatic disease curative agents, hypnotic and sedative agents, analgetic and antipyretic agents and comprehensive cold remedies, antiepileptic agents, psychotropic agents (antipsychotics, antidepressants, antimanics, psychostimulants, antialcoholic agents, and the like), antianxiety agents (mild tranquilizers), cerebral circulation and metabolism improvers, autonomic agents, antiemetic agents and antidizziness agents, Parkinson's disease curative agents, muscle relaxants, local analgesics, general anesthetics, ophthalmologic agents (anticataract agents, and the like), otolaryngologic agents, dermatologic agents, agents for urinary and generative organs (calculus excretion promoting agents, and the like), antihemorrhoidal agents, agents for uterus, agents for dentistry and oral cavity, detoxification agents, anorectic agents, weight gaining agents, metabolic antagonists, carnitine deficiency improvers, phenylalaninemia curative agents, urea cycle abnormality curative agents, non-smoking auxiliary agents, patent ductus arteriosus curative agents, cardiac muscle protecting agents, anti-ALS agents, immune enhancement agents, Chinese medicines, contrast media, and the like]. Further, the medicament of the present invention can also be prepared as a so-called combined drug with one or more kinds of medicaments suitably selected from the medicaments exemplified above and then administered.
Examples of the antibacterial agents include, for example, penicillin agents such as ampicillin, cephem agents such as cefazolin and cephalexin, macrolide agents such as erythromycin, tetracycline agents such as minocycline, aminoglycoside agents such as gentamycin, quinolone agents such as ciprofloxacin, monobactam agents such as azthreonam, carbapenem agents such as meropenem, glycopeptide agents such as vancomycin, antituberculosis agents such as rifampicin, and ethambutol, and the like, examples of the antiviral agents include, for example, aciclovir, nevirapine, ritonavir, and the like, examples of the antifungal agents include, for example, amphotericin B, itraconazole, and the like, examples of the antiparasitic (antihelminth, antiprotozoan) agents include, for example, pyrantel pamoate, praziquantel, quinine, metronidazole, and the like, examples of the vaccination agents include, for example, adsorbed tetanus toxoid, influenza vaccine, and the like, examples of the anticancer agents include, for example, antimetabolites such as fluorouracil, anticancer antibiotics such as bleomycin and mitomycin-C, alkylating agents such as busulfan, alkaloids such as vincristine and paclitaxel, platinum preparations such as cisplatin, hormone therapy agents such as tamoxifen, immunostimulants such as interferon-α, interferon-β, interleukin-2, and OK-432, other substances such as octreotide, pentostatin, and the like, examples of the immunosuppressive agents include, for example, azathioprine, mizoribine, cyclosporin, cyclophosphamide, and the like, examples of the adrenal-cortex steroids include, for example, prednisolone, methylprednisolone, and the like, examples of the nonsteroidal antiinflammatory agents include, for example, salicylic acid agents such as sodium salicylate, fenam agents such as mefenamic acid, arylacetic acid agents such as indometacin, propionate agents such as ibuprofen, oxicam agents such as piroxicam, basic nonsteroidal agents such as tiaramide, cartilage protecting agents such as hyaluronate sodium, and the like,

    examples of the antirheumatic agents include, for example, auranofin, lobenzarit, methotrexate, and the like, examples of the antarthritics include, for example, colchicine, allopurinol, benzbromarone, and the like, examples of the antiinflammatory enzymes include, for example, bromelain, serrapeptase, lysozyme, and the like, examples of the antihistaminic agents include, for example, ethanolamine agents such as diphenhydramine, propylamine agents such as triprolidine, phenothiazine agents such as promethazine, piperazine agents such as and hydroxyzine, piperidine agents such as cyproheptadine, antirheumatic agents of the second or subsequent generation such as terfenadine, and loratadine, examples of the antiallergic agents include, for example, mediator release suppressing agents, such as tranilast, TXA2 inhibitors such as ozagrel, leucotriene inhibitors such as pranlukast, Th2 cytokine inhibitors such as suplatast, antihistaminic agents, and the like, examples of the antidiabetic agents include, for example, insulin preparations such as insulin, sulfonylurea agents such as tolbutamide, and glibenclamide, fast-acting insulin secretion promoting agents such as nateglinide, sulfonamide agents such as glybuzole, biguanide agents such as metformin, insulin resistance improving agents such as pioglitazone and rosiglitazone, α-glucosidase inhibitors such as voglibose, somatomedin C preparations such as mecasermin, GLP-1, DPP-IV inhibitors, and the like, examples of the female hormone preparations include, for example, estrogen agents such as estriol, estradiol, and conjugated estrogen, gestagen preparations such as progesterone, medroxyprogesterone, and norethisterone, as well as pregnanediol, matharmon-F, danazol, selective estrogen receptor modulators (SERM: raloxifen, lasofoxifene, bazedoxifene, ospemifene, arzoxifene, CHF4227, PSK-3471, and the like), and the like,
    examples of the male hormone preparations include, for example, male hormone preparations such as testosterone and metyltestosterone, protein assimilation steroids such as mestanolone, stanozolol, metenolone, and nandrolone, selective androgen receptor modulators (SARM), and the like, examples of other hormone preparations include, for example, hypothalamic hormones such as LH-RH, protirelin, somatorelin, and corticorelin, adenohypophysial hormones such as somatropin, gonadotrophic hormones such as ACTH (adrenocorticotropic hormone), HCG, and HMG, ovulation inducing agents such as cyclofenil, neurohypophyseal hormones such as oxytocin, vasopressin, and desmopressin, parotic gland hormones, ergot alkaloids such as glucagon, and terguride, anti-mammary gland tumor agents such as epitiostanol, adrenal cortex hormone synthesis inhibitors such as mitotane, somatostatin analogues such as octreotide, iodine preparations, and the like, examples of the thyroid disease curative agents include, for example, thyroid hormones such as levothyroxine, antithyroid agents such as propylthiouracil, and the like, examples of the bone and calcium metabolic agents include, for example, examples of the bone activating agents include, for example, calcitriol, alfacalcidol, OCT, ED-71, and the like, examples of the osteogenesis promoting agents include, for example, menatetrenone, teriparatide, somatropin, insulin-like growth factor, EP4 agonist, EP2 agonist, growth hormone secretagogues, and the like, examples of the bone resorption suppressing agents include, for example, elcatonin, calcitonin salmon, etidronate, pamidronate, clodronate, alendronate, incadronate, risedronate, minodronate, ibandronate, cathepsin K inhibitors, osteoprotegerin, anti-RANKL antibodies, and the like, examples of the bone metabolism improving agents include, for example, fluoride, ipriflavone, and the like, examples of the sexual hormone preparations include, for example, estriol, estradiol, conjugated estrogen, progesterone, medroxyprogesterone, testosterone, metyltestosterone, mestanolone, stanozolol, metenolone, nandrolone, selective estrogen receptor modulators (SERM: raloxifen, lasofoxifene, bazedoxifene, ospemifene, arzoxifene, CHF4227, PSK-3471, and the like), selective androgen receptor modulators (SARM), and the like,
    examples of the calcium preparations include, for example, calcium carbonate, calcium lactate, calcium gluconate, calcium acetate, calcium chloride, calcium citrate, calcium hydrogenphosphate, calcium L-aspartate, and the like, examples of the vitamin preparations include, for example, vitamin A and retinoids, vitamin B1 and vitamin B1 derivatives, vitamin B2, nicotinic acid, pantothenic acid, vitamin B6, vitamin B12, folic acid, mixed vitamin B, vitamin C, vitamin K, vitamin E, vitamin H, multiple vitamin agents, and the like, examples of the fluid therapy preparations include, for example, electrolyte fluids, potassium preparations, preparations for correction, carbohydrate fluids, comprehensive amino acid preparations, amino acid preparations for renal failure, amino acid preparations for hepatic failure, other amino acid preparations, fat emulsion preparations, basic solutions for high calorie fluid therapy, enteral hyperalimentation preparations, nutrient preparations of ingredients for hepatic insufficiency, plasma volume increasing agents, trace element preparations, dialysis and peritoneal dialysis solutions such as AK-solita-D, and kindaly AF-3, and the like, examples of the blood preparations include, for example, albumin preparations, globulin preparations, blood coagulation factor preparations, fibrinogen preparations, antilymphocyte globulin preparations, antithrombin III preparations, C1-inactivator preparations, haptoglobin preparations, arginine and vasopressin derivatives, and the like, examples of the hematopoietic agents include, for example, examples of the antianemic agents include, for example, iron agents such as sodium ferrous citrate, erythropoietin preparations such as epoetin alfa, G-CSF preparations such as filgrastim, M-CSF preparations such as mirimostim, immunoglobulin preparations, tubercle bacillus preparations, romurtide, imiglucerase, and the like, examples of the hypoleukocytemia curative agents include, for example, adenine, L-cystein, cepharanthin, glutathion, cytochrome C, and the like, examples of the hemostatic agents include, for example, adrenochromes such as carbazochrome, antiplasmin agents such as tranexamic acid, blood coagulation factor-like effect agents such as hemocoaglase, cellulose preparations, gelatin preparations, agents for esophageal varices sclerosing therapy such as poridocanol, and the like, examples of the antithrombotic agents include, for example, anticoagulants (heparin and heparinoids such as danaparoid, oral anticoagulants such as warfarin, antithrombin agents such as argatroban, FXa inhibitors, FVIIa inhibitors, thrombolytic agents (urokinase preparations, t-PA preparations, and the like), protease inhibitors such as nafamostat, and the like), antiplatelet agents (aspirin, ethyl icosapentate, beraprost, sarpogrelate, dilazep, dipyridamole, ticlopidine, cilostazol, P2Y12 inhibitors, and the like), dried and concentrated L active protein C, thrombomodulin preparations, and the like,
    examples of the antihyperlipidemic agents include, for example, fibrate agents such as clinofibrate, nicotinic acid agents such as niceritorol, HMG-CoA reductase inhibitors such as pravastatin, simvastatin, fluvastatin, cerivastatin, atorvastatin, and lovastatin, anion exchange resins such as cholestyramine, probucol, melinamide, pantethine, ethyl icosapentate, elastase, dextran sulfate sodium sulfur, polyenephosphatidylcholine, ezetimib, bile acid re-absorption inhibitors (IBAT inhibitors), ACAT inhibitors, MTP inhibitors, CETP inhibitors, LXR regulating agents, and the like, examples of the cardiac stimulants (heart failure curative agents) include, for example, examples of the cardiac stimulants include, for example, digitalis preparations such as digoxin, β-metildigoxin, and digitoxin, xanthine agents such as aminophylline, catecholamine agents such as docarpamine, PDEIII inhibitors such as amrinone, denopamine, ubidecarenone, vesnarinone, aminoethylsulfonic acid, pimobendan, carperitide, corforsin daropate, and the like, examples of the antiarrhythmic agents include, for example, class Ia agents such as procainamide and cibenzoline, class Ib agents such as lidocaine, aprindine, and mexiletine, class Ic agents such as flecainide, propafenone, and pilsicainide, class III agents such as nifekalant, and verapamil, β-blockers (class II agents), Ca antagonist (class IV agents), and the like, examples of the antianginal agents include, for example, nitric acid agents such as nitroglycerin and isosorbide dinitrate, β-blockers such as propranolol, Ca antagonists such as nifedipine, dipyridamole, etafenone, dilazep, trapidil, nicorandil, and the like, examples of the vasodilators include, for example, prostaglandin preparations such as limaprost alfadex, nicotinic acid agents such as tocopherol nicotinate, β-receptor stimulants such as isoxsuprine, β-receptor suppressants such as tolazoline, circulatory hormone preparations such as kallidinogenase, and the like,
    examples of the antihypertensive agents include, for example, Ca antagonists such as diltiazem, nicardipine, nisoldipine, barnidipine, nifedipine, aranidipine, cilnidipine, nitrendipine, nilvadipine, felodipine, benidipine, and amlodipine, β-blokers such as atenolol, alprenolol, bisoprolol, betaxolol, bevantolol, acebutolol, celiprolol, nipradilol, tilisolol, nadolol, indenolol, bunitrolol, penbutolol, bopindolol, propranolol, metoprolol, pindolol, carteolol, and timolol, diuretic agents such as furosemide, ACE inhibitors such as enalapril, lisinopril, captopril, alacepril, delapril, cilazapril, benazepril, imidapril, temocapril, quinapril, trandolapril, and perindopril, angiotensin II receptor antagonists such as losartan, candesartan, and valsartan, α-blockers such urapidil, terazosin, doxazosin, bunazosin, prazosin and phentolamine, α,β-blokers such as carvedilol, amosulalol, arotinolol, and labetalol, central sympathetic nerve suppressants such as methyldopa, clonidine, guanabenz, and guanfacine, peripheral sympathetic nerve blocking agents such as betanidine, autonomic nerve blocking agents such as trimetaphan, rauwolfia preparations such as reserpine, and rescinnamine, vasodilative antihypertensive agents such as hydralazine, todralazine, budralazine, and cadralazine, nitric acid agents such as nitroglycerin, circulatory system acting enzyme agents such as kallidinogenase, dihydroergotoxine, alprostadil alfadex, and the like,
    examples of the vasopressors include, for example, catecholamine agents such as norepinephrine, dopamine, and dobutamine, non-catecholamine agents such as metaraminol and amezinium metilsulfate, and the like, examples of the diuretic agents include, for example, thiazide diuretic agents such as hydrochlorothiazide, non-thiazide diuretic agents such as chlortalidone, loop diuretics such as furosemide, K sparing diuretic agents such as spironolactone, carbonic anhydrase inhibitors such as acetazolamide, and osmotic diuretic agents such as D-mannitol, examples of the bronchodilators include, for example, xanthine derivatives such as theophylline, β-stimulants such as epinephrine, ephedrine, dl-methylephedrine, isoprenaline, orciprenaline, clorprenaline, trimetoquinol, salbutamol, terbutaline, tulobuterol, procaterol, fenoterol, formoterol, and clenbuterol, parasympathetic blocking agents such as ipratropium, flutropium, and oxitropium, and the like, examples of the bronchial asthma curative agents include, for example, steroid agents for inhalation such as beclomethasone, and fluticasone, vaccine therapy agents, histamine-added human immunoglobulin, and the like, examples of the respiratory stimulants include, for example, central respiratory stimulants such as dimorpholamine, peripheral respiratory stimulants such as doxapram, xanthine derivatives such as theophylline, narcotic antagonists such as levallorphan, lung-surfactants, and the like, examples of the antitussive agents include, for example, centeral narcotic antitussive agents such as codein, dihydrocodeine, and oxymetebanol, central non-narcotic antitussive agents such as dextromethorphan, pentoxyverine, dimemorfan, cloperastine, benproperine, fominoben, and eprazinone, and the like,
    examples of the expectorants include, for example, respiratory tract mucus dissolving agents such as acetylcysteine, respiratory tract mucus healing agents such as bromhexine, respiratory tract lubricants such as ambroxol, surface active agents such as tyloxapol, salt expectorants, stimulant expectorants, herbal agent expectorants, and the like, examples of the stomachic digestants and gastrointestinal promotility agents include, for example, stomachic combination agents such as S-M, digestive enzyme agents such as diastase, and Takadiastase, parasympathomimetic agents such as carnitine and carpronium, serotonin agonists such as cisapride, and mosapride, antidopamine agents such as metoclopramide, domperidone, and itopride, opiate agonists such as trimebutine, and the like, examples of the digestive ulcer curative agents (antacids, antispasmodic agents, antiulcer agents) include, for example, antacids such as sodium hydrogencarbonate, dried aluminum hydroxide gel, and hydrotalcite, belladonna alkaloids such as atropine sulfate, cholinergic agents such as acetylcholine chloride, tertiary amine synthetic anticholinergic agents such as piperidolate, quarternary ammonium salt synthetic anticholinergic agents such as propantheline, methylbenactyzium, and methyloctatropine, selective antimuscarine agents such as tiquizium and pirenzepine, antigastrin agents such as secretin, proglumide, and urogastrone, histamine H2 receptor antagonists such as cimetidine, ranitidine, famotidine, roxatidine, nizatidine, and lafutidine, proton pump inhibitors such as omeprazole, lansoprazole, and rabeprazole, prostaglandin preparations such as ornoprostil, misoprostol, and enprostil, defensive factor enhancers such as methylmethionine sulfonium chloride, sucralfate, L-glutamine, sodium azulenesulfonate, gefarnate, aldioxa, aceglutamide aluminum, cetraxate, sofalcone, teprenone, sodium alginate, plaunotol, troxipide, benexate hydrochloride betadex, rebamipide, polaprezinc, irsogladine, ecabet, and egualen, antidopamine agents such as sulpiride, and clebopride, organ extracts such as Solcoseryl, combination agents such as aluminum hydroxide gel and magnesium hydroxide combination agents, and the like,
    examples of the intestinal disease curative agents include, for example, astringent agents such as albumin tannate, microbicides such as berberine, lactic acid bacterium preparations such as lactomin, lactose decomposition enzyme agents such as tilactase, adsorbents for alimentary canals such as natural aluminum silicate, antidiarrheal agents such as loperamide, alimentary canal gas elimination agents such as dimethicone, irritable colon syndrome curative agents such as mesalazine, betamethasone, mepenzolate, and polycarbophil calcium, and the like, examples of the purgatives (cathartics) include, for example, salt purgatives such as magnesium sulfate, bulk cathartics such as carmelose, infiltrative purgatives such as DSS, sugar purgatives such as lactulose, small intestine stimulating purgatives such as castor oil, large intestine stimulating purgatives such as senna, and rheum, glycerin, and the like, examples of the biliary disease curative agents include, for example, choleretics such as ursodeoxycholic acid, and chenodeoxycholic acid, cholekinetics such as papaverine, flopropione, hymecromone, and trepibutone, bile acid deposition agents such as colestyramine, and colestimide, and the like, examples of the liver disease curative agents include, for example, liver function improving agents such as glutathione, glucuronate, glycyrrhizin, tiopronin, and vitamin U, liver protein metabolism improving agents such as malotilate, hepatic insufficiency curative agents such as liver hydrolysates, liver extract preparations, sodium glutaminate, amino acid combination agents, lactulose, and lactitol hydrate, interferon-α, interferon-β, immunoglobulins, hepatitis vaccines, shosaikoto, and the like, examples of the pancreatic disease curative agents include, for example, protease inhibitors such as camostat, nafamostat, gabexate, and ulinastatin, pancreatitis curative agents such as citicolin, pancreatic exocrine stimulants such as fenipentol, and the like,
    examples of the hypnotic and sedative agents include, for example, barbituric acid agents such as barbital, amobarbital, and phenobarbital, non-barbituric acid agents such as triclofos and chloral hydrate, benzodiazepine agents such as triazolam, midazolam, lormetazepam, rilmazafone, estazolam, nimetazepam, flunitrazepam, haloxazolam, quazepam, brotizolam, nitrazepam, and flurazepam, cyclopyrrolone agents such as zopiclone, and zolpidem, belladonna alkaloids such as scopolamine, and the like, examples of the analgetic and antipyretic agents and comprehensive cold remedies include, for example, narcotic analgesics such as opium, morphine, pethidine, droperidol, and fentanyl citrate, non-narcotic analgesics such as pentazocine, tramadol, buprenorphine, eptazocine, and butorphanol, nonsteroidal antiinflammatory agents such as flurbiprofen, loxoprofen, indometacin, diclofenac, and sulindac, pyrazolone antipyretic analgesics such as sulpyrine, and migrenin, and combination agents containing these, non-pyrazolone antipyretic analgesics such as acetaminophen, phenacetin, and dimetotiazine, and cold remedies as combination agents containing these, xanthine preparations such as caffeine, ergotamine preparations such as dihydroergotamine, Ca antagonists such as lomerizine, triptane anti-migraine agents such as sumatriptan, and the like, examples of the antiepileptic agents include, for example, hydantoin agents such as phenyloin, barbituric acid agents such as primidone, acetyl ureas such as acetylpheneturide, benzisoxazole agents such as zonisamide, benzodiazepine agents such as clonazepam, diazepam, clobazam, and trimethadione, ethosuximide, carbamazepine, sultiame, sodium valproate, and the like,
    examples of the psychotropic agents (antipsychotics, antidepressants, psychostimulants, antialcoholic agents, and the like) include, for example, phenothiazine agents such as chlorpromazine, levomepromazine, fluphenazine, thioridazine, propericiazine, perphenazine, and prochlorperazine, butyrophenone agents such as haloperidol, bromperidol, pipamperone, spiperone, moperone, and timiperone, benzamide agents such as sultopride, nemonapride, sulpiride, and tiapride, serotonin and dopamine antagonists such as olanzapine, and risperidone, anti-schizophrenia agents such as pimozide, clocapramine, carpipramine, mosapramine, oxypertine, zotepine, and carbamazepin, tricyclic antidepressants such as imipramine, clomipramine, amitriptyline, lofepramine, amoxapine, dosuleptin, and nortriptyline, tetracyclic antidepressants such as maprotiline, and mianserin, selective serotonin reuptake inhibitors (SSRI) such as fluvoxamine, and paroxetine, serotonin and noradrenalin reuptake inhibitors (SNRI) such as milnacipran, antidepressants such as trazodone, psychostimulants such as methamphetamine, methylphenidate, and pemoline, and the like, examples of the antianxiety agents (mild tranquilizers) include, for example, benzodiazepine agents such as chlordiazepoxide, diazepam, cloxazolam, oxazolam, medazepam, bromazepam, lorazepam, prazepam, fludiazepam, clorazepate, mexazolam, alprazolam, flutazolam, flutoprazepam, ethyl loflazepate, clotiazepam, and etizolam, tandospirone, hydroxyzine, and the like, examples of the cerebral circulation and metabolism improvers include, for example, ifenprodil, vinpocetine, ibudilast, nicergoline, nilvadipine, amantadine, cytochrome C, ATP, meclofenoxate, citicolin, γ-aminobutyric acid, calcium hopantenate, dihydroergotoxine, fasudil, nizofenone, sodium ozagrel, donepezil, and the like,
    examples of the autonomic agents include, for example, choline analogue agents such as acetylcholine chloride, and bethanechol, anti-cholinesterase agents such as neostigmine, ambenonium, distigmine, pyridostigmine, and edrophonium, autonomic nerve regulating agents such as tofisopam and γ-oryzanol, β-blockers such as atenolol, alprenolol, bisoprolol, betaxolol, bevantolol, acebutolol, celiprolol, nipradilol, tilisolol, nadolol, indenolol, bunitrolol, penbutolol, bopindolol, propranolol, metoprolol, pindolol, carteolol, and timolol, α-blockers such as urapidil, terazosin, doxazosin, bunazosin, prazosin, and phentolamine, α,β-blockers such as carvedilol, amosulalol, arotinolol, and labetalol, β-stimulants such as epinephrine, ephedrine, dl-methylephedrine, isoprenaline, orciprenaline, clorprenaline, trimetoquinol, salbutamol, terbutaline, tulobuterol, procaterol, fenoterol, formoterol, and clenbuterol, parasympatholytic agents (anticholinergic agents) such as ipratropium, flutropium, and oxitropium, autonomic nerve blocking agents such as trimetaphan, and the like, examples of the antiemetic agents and antidizziness agents include, for example, phenothiazine agents such as perphenazine, and prochlorperazine, antihistaminic agents such as dimenhydrinate, and similar agents, 5-HT3 receptor antagonist type antiemetic agents such as granisetron, ondansetron, azasetron, ramosetron, and tropisetron, sympathetic nerve stimulants such as isoprenaline, antacidus neutralizers such as sodium hydrogencarbonate, antidizziness agents such as betahistine, and difenidol, cerebral circulation and metabolism improvers such as disodium adenosine triphosphate, phenothiazine agents such as prochlorperazine, benzodiazepine agents such as diazepam, gastroenteric promotility agents such as metoclopramide, domperidone, mosapride, cisapride, and trimebutine, gastric mucous membrane local analgesics such as oxethazaine, abirritants such as scopolamine, diphenhydramine, diprophylline, and the like,
    examples of the Parkinson's disease curative agents include, for example, L-DOPA containing preparations such as levodopa, dopamine release promoting agents such as amantadine, dopamine receptor agonists such as bromocriptine, pergolide, cabergoline, talipexole, and ropinirol, norepinephrine precursors such as droxidopa, monoamine oxidase (MAO) inhibitors such as selegiline, muscle relaxants such as tizanidine, dantrolene, and vecuronium, parasympatholytic agents such as profenamine, mazaticol, trihexyphenidyl, biperiden, piroheptine, and metixene, and the like, examples of the muscle relaxants include, for example, central muscle relaxants such as tolperisone, methocarbamol, pridinol, chlorphenesin, baclofen, and tizanidine, peripheral muscle relaxants such as suxamethonium, dantrolene, pancuronium, and vecuronium, and the like, examples of the local analgesics include, for example, procaine, ethyl aminobenzoate, cocaine, lidocaine, dibucaine, bupivacaine, and the like, examples of the general anesthetics include, for example, halogenated hydrocarbon preparations such as halothane, barbituric acid preparations such as thiamylal, thiopental, and pentobarbiturate, benzodiazepine preparations such as midazolam, halogenated ether preparations such as isoflurane, ketamine, droperidol, propofol, anesthetic ether, nitrous suboxide, and the like, examples of the ophthalmologic agents (anticataract agents, and the like) include, for example, miotic agents such as pilocarpine, mydriatic agents such as cyclopentolate, and epinephrine, anticataract agents such as pirenoxine, glutathione, tiopronin, and salivary gland hormone, cornea curative agents such as sodium chondroitinsulfate, vasoconstrictors such as naphazoline, tetrahydrozoline, and oxymetazoline, adrenal cortex hormones such as dexamethasone, and prednisolone, β-blockers such as timolol, befunolol, carteolol, betaxolol, nipradilol, and levobunolol, carbonate dehydratase inhibitors such as dorzolamide, antibiotic preparations such as sulfisoxazole, antiviral agents such as aciclovir, and idoxuridine, antiallergic agents such as sodium cromoglicate, amlexanox, ketotifen, tranilast, and levocabastine, prostaglandin preparations such as isopropyl unoprostoe, and latanoprost, antiinflammatory agents such as azulene, indometacin, and pranoprofen, cyanocobalamin, lysozyme chloride, and the like,
    examples of the otolaryngologic agents include, for example, vasoconstrictors such as naphazoline, tetrahydrozoline, oxymetazoline, and tramazoline, adrenal cortex hormones such as flunisolide, beclometasone, fluticasone, and dexamethasone, antibacterial agents such as cefinenoxime, antiallergic agents such as sodium cromoglicate, amlexanox, ketotifen, emedastine, epinastine, and suplatast, antihistaminic agents such as levocarbastine, anticholinergic agents such as flutropium, and ipratropium, respiratory tract mucus restoration agents such as carbocisteine, and the like, examples of the dermatologic agents include, for example, leukoderma curative agents such as methoxsalen, inflammatory anthema curative agents such as pregnanediol, keratosis curative agents such as etretinate, calcipotriol, urea, and tacalcitol, clavus curative agents such as salicyclic acid, psoriasis curative agents such as ciclosporin, depilation and leukoderma curative agents such as carpronium, Hansen's disease curative agents such as diaphenylsulfone, atopic dermatitis curative agents such as tacrolimus, antiallergic agents such as cromoglicate, tranilast, emedastine, epinastine, and suplatast, antipruritic agents such as crotamiton, and diphenhydramine, skin ulcer curative agents such as azulene, sulfadiazine, tretinoin tocoferil and bucladesine, and the like, examples of the agents for urinary and generative organs (calculus excretion promoting agents, and the like) include, for example, tertiary amine synthetic anticholinergic agents, quarternary ammonium salt synthetic anticholinergic agents, calculus excretion promoting agents such as flopropione, Quercus salicina extract, and α,β-pinene and d-camphene preparations, aciduria improving agents such as potassium citrate and sodium citrate preparations, thamuria curative agents such as flavoxate, oxybutynin, propiverine, clenbuterol, and mesna, urinary disturbance curative agents such as paraprost, neostigmine, oxendolone, prazosin, terazosin, urapidil, tamsulosin, and naftopidil, agents for generative organs (PDE-5 inhibitors and the like) such as sildenafil, and the like,
    examples of the antihemorrhoidal agents include, for example, tribenoside, Lithospermi radix extract, ethyl aminobenzoate and dibucaine hydrochloride preparations, and the like, examples of the agents for uterus include, for example, uterotonic agents such as ergometrine, dinoprost, dinoprostone, and gemeprost, uterine motility suppressing agents such as ritodrine, isoxsuprine, and piperidolate, hormone therapy agents such as danazol, buserelin, nafarelin, leuprorelin, goserelin, cetrorelix, teverelix, abarelix, and sodium prasterone sulfate, autonomic nerve controlling agents such as tofisopam, and the like, examples of the agents for dentistry and oral cavity include, for example, collutories such as azulene, and povidone-iodine, troches such as chlorhexidine, troches containing an antibiotic such as tetracycline, stomatitis curative agents such as azulene, triamcinolone, dexamethasone, and beclometasone, artificial saliva such as saliveht, and the like, examples of the detoxification agents include, for example, metal detoxification agents such as dimercaprol, anti-barbituric acid agents such as bemegride, narcotic antagonists such as naloxone, folic acid antagonists such as calcium folinate, iphosphamide-indeced bladder dyscrasia curative agents such as mesna, heparin antagonists such as protemin, antiallergic agents such as glycyrrhizin, antialcoholic agents such as cyanamide, and disulfiram, glutathione, ipecac, carbon (Kremezin), and the like, examples of the anorectic agents include, for example, mazindol, MCH antagonists, MC4 antagonists, and the like, examples of the weight gaining agents include, for example, somatropin and the like, examples of the metabolic antagonists include, for example, sodium chondroitinsulfate and the like, examples of the carnitine deficiency improving agents include, for example, levocarnitine and the like,
    examples of the phenylalaninemia curative agents include, for example, sapropterin, and the like, examples of the urea cycle abnormality curative agents include, for example, arginine hydrochloride, and the like, examples of the non-smoking auxiliary agents include, for example, nicotin, and the like, examples of the patent ductus arteriosus curative agents include, for example, indometacin, and the like, examples of the cardiac muscle protecting agents include, for example, miotecter, and the like, examples of the anti-ALS agents include, for example, riluzole, and the like, examples of the immune enhancement agents include, for example, interferon-β 1b, and the like, and examples of the Chinese drugs and contrast media include, for example, contrast media for urography such as iopamidol, iohexol, ioversol, iopromide, iomeprol, ioxilan, and ioxaglic acid, contrast media for retrograde urography such as amidotrizoic acid, and iothalamic acid, alimentary canal contrast media such as amidotrizoic acid, salivary gland contrast media such as amidotrizoic acid, contrast media for cisternography and myelography such as iotrolan, contrast media for spermatocystography such as iothalamic acid, contrast media for uterosalpingography such as iotrolan, contrast media for MRI such as gadodiamide hydrate, contrast media for echography such as galactose-palmitic acid, contrast media such as iodixanol, and the like (Jinzobyo Chiryoyaku Manual (Manual of Renal Disease Curative Agents), Ed. by Nihei H., Tokyo Igaku Sha, Tokyo, 2002; Konnichi no Tiryoyaku (Today's Curative Agents) 2001, Ed. by Mizushima H, Nankodo, Tokyo, 2001). However, examples of the prophylactic or therapeutic agents for the various abnormalities and diseases complicating with hyperPTHemia including hyperparathyroidism, osteoporosis, and hypercalcemia used in combination or prepared into a so-called combined drug with the medicament of the present invention are not limited to the aforementioned specific agents.


When a medicament used in combination or prepared into a so-called combined drug with the medicament of the present invention is selected, a type, dose, administration time and the like of the medicament may be appropriately selected and adjusted so that the interactions between the medicaments are minimized by referring to information of package inserts, product summaries, interview forms and the like of the medicaments. For example, it has been reported that the antihyperlipidemic drug, atorvastatin, is metabolized by the drug metabolism enzyme CYP3A4 in the liver after administration, and therefore if a medicament having a CYP3A4 enzyme inhibitory action (e.g., azole antifungal agents) is used in combination, blood level of atorvastatin rises, and risk of side effects such as rhabdomyolysis increases (Bernini et al., “Saftey of HMG-CoA reductase inhibitors: focus on atorvastatin”, Cardiovasc. Drugs Ther., 15, pp. 211-218, 2001). Further, it has been reported that the antidepressant, imipramine, is metabolized by the drug metabolism enzyme CYP2D6 in the liver after administration, and therefore, if a medicament having a CYP2D6 enzyme inhibitory action (e.g., paroxetine) is used in combination, blood level of the antidepressant rises, and undesirable excessive anticholinergic action is expressed (Albers et al., “Paroxetine shifts imipramine metabolism”, Psychiatry Res., 59, pp. 189-196, 1996). Therefore, for example, when the medicament of the present invention is administered to a patient of hyperPTHemia including hyperparathyroidism, osteoporosis, or hypercalcemia taking atorvastatin or imipramine, it is very desirable to choose a medicament having negligible CYP3A4 or CYP2D6 inhibitory action.
EXAMPLES
The present invention will be more specifically explained by referring to examples. However, the scope of the present invention is not limited by the following examples.
In the following examples, various analyses were performed as follows.
(1) Fast Atomic Bombardment Mass Spectrum (FAB-MS)
Spectra were measured by using a mass spectrometer Model JMS-AX500 or JMS-SX102 produced by JEOL Ltd. As the matrix, 3-nitrobenzyl alcohol was used.
(2) Liquid Chromatography-mass Spectrometry Spectrum (LC-MS)
As the mass spectrometer, Platform-LC type mass spectrometer produced by Micromass, England (electrospray ionization (ESI) method was used for ionization).
As the liquid chromatography apparatus, an apparatus produced by GILSON, France, was used. As the separation column, Mightysil RP-18 GP 50-4.6 produced by Kanto Kagaku, Japan (product number: 25468-96) was used. The elution conditions are mentioned below.

    Flow rate: 2 ml/minute
    Solvent:
    
        Solution A=water containing 0.1% (v/v) acetic acid
        Solution B=acetonitrile containing 0.1% (v/v) acetic acid
        Elution was performed with a linear gradient of 5 to 100% (v/v) of Solution B from 0 minute to 5 minutes.

(3) Proton Nuclear Magnetic Resonance (1H-NMR) Spectrum

    
    


Spectra were measured by using Gemini-300 nuclear magnetic resonance apparatus produced by Varian, U.S. As the internal standard, tetramethylsilane was used. Chemical shifts are indicated in terms of δ values (ppm). Splitting patterns are indicated with the following abbreviations: s: singlet, d: doublet, t: triplet, q: quadruplet, quintet: quintet, m: multiplet, dd: double doublet, dt: double triplet, and brs: broad singlet
(4) Thin Layer Chromatography (TLC)
A TLC plate produced by Merck, Germany (Silica Gel 60 F254, product number: 1,05715) was used. Compounds were detected by irradiating the TLC plate after deployment with an ultraviolet ray having a wavelength of 254 nm.
(5) Purification Chromatography
Silica gel column purification was performed by using Silica Gel 60 produced by Merck, Germany or a full automatic preparative chromatography apparatus Parallel Prep produced by YAMAZEN CORP. with a packed column for medium pressure preparation, Hi-Flash column (trade name), and objective substances were eluted with a mixed solvent (n-hexane/ethyl acetate, or chloroform/methanol).
For purification with a reverse phase column, a column produced by YMC, Japan (YMC CombiPrep ODS-A CCAAS05-0520WT) was used, and target substances were eluted with a water/acetonitrile (containing 0.1% (v/v) acetic acid) gradient.
Detailed elution conditions are mentioned below.

    Flow rate: 20 ml/minute
    Solvent:
    
        Solution A=water containing 0.1% (v/v) trifluoroacetic acid
        Solution B=acetonitrile containing 0.1% (v/v) trifluoroacetic acid
        Elution was performed with:
        5% of Solution B from 0 minute to 1 minute,
        linear gradient of 5 to 50% (v/v) of Solution B from 1 minute to 11 minutes
        linear gradient of 50 to 100% (v/v) of Solution B from 11 minutes to 16 minutes
    
    


Example 1
Synthesis of [1-(benzothiophen-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine hydrochloride
[3-(3-Trifluoromethylphenyl)propyl]amine (101.6 mg) synthesized according to a method described in the literature (Fujimura et al., Bioorg. Med. Chem., Vol. 5, pp. 1675-1684, 1997) and 3-acetylbenzothiophene (90 mg) were added to an argon substituted recovery flask, added with titanium tetraisopropoxide (190 μL), and stirred at room temperature for 17 minutes. The reaction mixture was added with dehyderated 2-propanol (0.5 mL), and stirred at room temperature for 14 hours and then at 100° C. for 6 hours. The reaction mixture was cooled to room temperature, added with sodium cyanoborohydride (34 mg) and dehydrated ethanol (0.75 mL), and stirred at room temperature for 38.5 hours. The reaction mixture was further added with sodium cyanoborohydride (35 mg), stirred at room temperature for 3 hours, then further added with sodium cyanoborohydride (100 mg), and stirred for 45 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified twice by silica gel column chromatography (chloroform:methanol=100:0→90:10) to obtain 156 mg of the title compound in the free form. This product was dissolved in chloroform, and added with a 0.1 N solution of hydrochloric acid in ethanol (4.8 mL), and the solvent was evaporated under reduced pressure to obtain 174 mg of the title compound.
1H-NMR (DMSO-d6); δ (ppm) 1.67 (3H, d, J=6.6), 1.96 (2H, m), 2.72 (2H, t, J=7.7), 2.70-2.84 (1H, m), 2.90-3.04 (1H, m), 4.92 (1H, m), 7.42-7.56 (6H, m), 8.02-8.12 (3H, m), 9.26 (1H, brs), 9.60 (1H, brs)
Reference Example
Synthesis of N-[1-(benzothiophen-3-yl)ethyl]-3-(2-furyl)propionamide
3-(2-Furyl)propionic acid (368 mg), 1-(benzothiophen-3-yl)ethylamine (443 mg), N-ethyl-N′-dimethylaminopropylcarbodiimide hydrochloride (575 mg), 1-hydroxybenzotriazole (405 mg), and triethylamine (304 mg) were added to dehydrated dimethylformamide (DMF, 15 mL), and stirred at room temperature for 12 hours. The reaction mixture was added with water, and extracted with ethyl acetate. The organic layer was dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain 628 mg of the title compound.
1H-NMR (CDCl3); δ (ppm) 1.67 (3H, d, J=6.6), 2.49 (2H, t, J=7.5), 3.00 (2H, t, J=7.5), 5.57 (1H, q, J=7.5), 5.62 (1H, brs), 5.98 (1H, d, J=0.9), 6.22 (1H, dd, J=1.20, 3.00), 7.23 (1H, d, 1.20), 7.35-7.39 (2H, m), 7.75-7.79 (1H, m), 7.80-7.88 (1H, m), 8.00 (1H, s)
Example 2
Synthesis of [1-(benzothiophen-3-yl)ethyl][3-(2-furyl)propyl]amine
The compound of Reference Example (600 mg) was dissolved in dehydrated THF, added with lithium aluminum hydride (379 mg), and refluxed under nitrogen atmosphere for 12 hours. The reaction mixture was cooled on ice, and carefully added with water with stirring. The solids were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to obtain 393 mg of the title compound.
1H-NMR (CDCl3); δ (ppm) 1.48 (3H, d, J=6.6), 1.85 (2H, quintet, J=7.2), 2.59-2.74 (4H, m), 4.24 (1H, q, J=6.6), 5.92 (1H, d, J=0.9), 6.25 (1H, dd, J=1.8, 2.7), 7.23-7.39 (4H, m), 7.84-7.91 (2H, m)
The compounds of Examples 3 to 8 were synthesized in the same manner as in Example 1, Reference Example, or Example 2.
Example 3
[1-(Benzothiophen-3-yl)ethyl][3-[5-(3-chlorophenyl)furan-2-yl]propyl]amine
1H-NMR (CDCl3); δ (ppm) 1.49 (3H, d, J=6.6), 1.89 (2H, m), 2.64-2.78 (4H, m), 4.26 (1H, q, J=6.6), 6.01 (1H, d, J=3.3), 6.51 (1H, d, J=3.3), 7.18-7.39 (5H, m), 7.60 (2H, d, J=8.4), 7.84-7.91 (2H, m)
Example 4
[1-(Benzothiophen-3-yl)ethyl][3-(3-furyl)propyl]amine
1H-NMR (CDCl3); δ (ppm) 1.49 (3H, d, J=6.6), 1.70-1.79 (2H, m), 2.36-2.52 (2H, m), 2.58-2.72 (2H, m), 4.23 (1H, q, J=6.6), 6.22 (1H, s), 7.14 (1H, s), 7.30-7.39 (4H, m), 7.84-7.90 (2H, m)
Example 5
[1-(Benzothiophen-3-yl)ethyl][3-(thiophen-3-yl)propyl]amine
1H-NMR (CDCl3); δ (ppm) 1.48 (3H, d, J=6.6), 1.77-1.87 (2H, m), 2.58-2.73 (4H, m), 4.23 (1H, q, J=6.6), 6.87-6.90 (2H, m), 7.20-7.22 (1H, m), 7.29 (1H, s), 7.31-7.40 (2H, m), 7.84-7.90 (2H, m)
Example 6
[1-(Azulen-1-yl)ethyl][3-(thiophen-3-yl)propyl]amine
1H-NMR (CDCl3); δ (ppm) 1.58 (3H, d, J=6.6), 1.75-1.88 (2H, m), 2.45-2.68 (5H, m), 4.57 (1H, q, J=6.6), 6.82-6.85 (2H, m), 7.09-7.19 (3H, m), 7.38 (1H, d, J=3.9), 7.57 (1H, t, J=9.9), 8.00 (1H, d, J=3.9), 8.29 (1H, d, J=9.9), 8.41 (1H, d, J=9.9)
Example 7
[1-(Azulen-1-yl)ethyl][3-(2-furyl)propyl]amine
1H-NMR (CDCl3); δ (ppm) 1.60 (3H, d, J=6.9), 1.82-1.88 (2H, m), 2.29 (1H, brs), 2.46-2.69 (4H, m), 4.59 (1H, q, J=6.9), 5.89-5.90 (1H, m), 6.20-6.22 (1H, m), 7.10-7.38 (3H, m), 7.37 (1H, d, J=3.9), 7.57 (1H, t, J=9.6), 8.01 (1H, d, J=3.9), 8.29 (1H, d, J=9.6), 8.42 (1H, d, J=9.6)
Example 8
[1-(Thieno[2,3-b]pyridin-3-yl)ethyl][3-(3-trifluoromethylphenyl)propyl]amine
1H-NMR (CDCl3); δ (ppm) 1.50 (3H, d, J=6.6), 1.80 (2H, quintet, J=7.2), 2.04 (1H, brs), 2.53-2.79 (4H, m), 4.20 (1H, q, J=6.6), 7.25-7.53 (6H, m), 8.23-8.27 (1H, m), 8.55-8.57 (1H, m)
The compounds mentioned in Tables 3, 4, 5, and 6 (Examples 9 to 71) were synthesized in the same manner as in Example 1, Reference Example, or Example 2. As a result of measurement of liquid chromatography mass spectrometry spectra (LC-MS) of the compounds mentioned in Tables 3, 4, 5, and 6, it was confirmed that the objective compounds were produced.







TABLE 3













 












Example
A
n
R1
Y1
R11





Example 9




3
CH3
S
5-CH3


 


Example 10




2
CH3
S
H


 


Example 11




3
CH3
S
H


 


Example 12




3
CH3
S
H


 


Example 13




3
CH3
S
H


 


Example 14




3
CH3
S
H


 


Example 15




3
CH3
S
H


 


Example 16




3
CH3
S
H


 


Example 17




3
CH3
S
H


 


Example 18




3
CH3
S
H


 


Example 19




3
CH3
S
H


 


Example 20




3
CH3
S
H


 


Example 21




2
CH3
S
H


 


Example 22




3
CH3
S
H


 


Example 23




2
CH3
S
H


 


Example 24




3
CH3
S
H


 


Example 25




3
CH3
S
H


 


Example 26




5
CH3
S
H


 


Example 27




3
CH3
S
5-Br


 


Example 28




3
CH3
S
5-NH2


 


Example 29




3
CH3
S
5-NHSO2CH3


 


Example 30




3
CH3
S
H


 


Example 31




3
CH3
S
H


 


Example 32




3
CH3
S
H


 


Example 33




3
CH3
S
5-OCH3


 


Example 34




3
CH3
S
5-OH


 


Example 35




3
CH3
S
5-CH2OH


 


Example 36




3
CH3
S
5-SCH3


 


Example 37




3
CH3
S
H


 


Example 38




3
CH3
S
H


 


Example 39




2
CH3
S
H


 


Example 40




3
CH3
S
H


 


Example 41




3
CH3
S
H


 


Example 42




3
CH3
S
H


 


Example 43




3
CH3
S
H


 


Example 44




3
CH3
S
H


 


Example 45




3
CH3
S
H


 


Example 46




3
CH3
S
H


 


Example 47




3
CH3
S
H


 


Example 48




3
CH3
S
H


 


Example 49




3
CH3
S
H


 


Example 50




3
CH3
S
H


 


Example 51




4
CH3
S
H


 


Example 52




3
CH3
S
H


 


Example 53




3
CH3
S
H


 


Example 54




3
CH3
S
H


 


Example 55




3
CH3
S
H


 


Example 56




3
CH3
S
H


 


Example 57




3
CH3
S
H
















TABLE 4













 












Example
A
n
R1
Y1
R12





Example 58




3
CH3
CH
H


 


Example 59




3
CH3
CH
6-iPr


 


Example 60




3
CH3
CH
H
















TABLE 5













 











Example
A
n
R1
B





Example 61




3
CH3






 


Example 62




3
CH3






 


Example 63




3
CH3






 


Example 64




3
CH3






 


Example 65




3
CH3




















TABLE 6













 









Example
A
n





Example 66




3


 


Example 67




3


 


Example 68




3


 


Example 69




3


 


Example 70




3


 


Example 71




3









Example 72
Synthesis of 1-(azulen-1-yl)ethylamine
A. Synthesis of 1-(azulen-1-yl)ethanol
1-(Azulen-1-yl)ethanone (13.0 g) prepared according to a method described in the literature (Mori et al., J. Heterocycl. Chem., Vol. 33, 1996, pp. 841-846) was dissolved in dehydrated THF (380 mL), and stirried with cooling on ice under nitrogen atmosphere. This reaction mixture was carefully added with lithium aluminum hydride (1.45 g, Wako Pure Chemical Industries), and stirried with cooling on ice for 1 hour. The reaction mixture was carefully added with 2 N aqueous sodium hydroxide with cooling on ice and stirring. The reaction mixture was added with anhydrous magnesium sulfate, and stirred, then the solid was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was used for the subsequent reaction as it was.
1H-NMR (CDCl3); δ (ppm) 1.74 (3H, d, J=6.6), 5.61 (1H, q, J=6.6), 7.17 (2H, q, J=9.3), 7.35 (1H, d, J=4.2), 7.99 (1H, d, J=4.2), 8.32 (1H, d, J=9.9), 8.54 (1H, d, J=9.9)
B. Synthesis of 2-[1-(azulen-1-yl)ethyl]-isoindole-1,3-dione
The crude 1-(azulen-1-yl)ethanol prepared in Example 72, Step A was dissolved in dehydrated THF (380 mL), and stirred with cooling on ice under nitrogen atmosphere. This reaction mixture was added with phthalimide (45.0 g, Kanto Kagaku), tri-n-butylphosphine (37.7 mL, Kanto Kagaku), and 1,1′-azobis(N,N′-dimethylformamide) (26.3 g, Midori Kagaku), and stirred at room temperature for 16 hours under nitrogen atmosphere. The solid was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was added with saturated aqueous sodium hydrogencarbonate, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=6:1), to obtain 16.8 g of the title compound.
1H-NMR (CDCl3); δ (ppm) 2.11 (3H, d, J=7.2), 6.30 (1H, q, J=7.2), 7.11-7.29 (2H, m), 7.39 (1H, d, J=4.2), 7.74-7.77 (2H, m), 7.83-7.86 (2H, m), 8.31 (1H, d, J=9.7), 8.39 (1H, d, J=4.2), 8.43 (1H, d, J=9.7)
C. Synthesis of 1-azulen-1-yl-ethylamine
2-[1-(Azulen-1-yl)ethyl]-isoindole-1,3-dione (16.8 g) prepared in Example 72, Step B was dissolved in ethanol (400 mL), added with hydrazine monohydrate (3.1 g, Wako Pure Chemical Industries), and stirred at 30° C. for 72 hours. The solid was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was added with saturated aqueous sodium hydrogencarbonate, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by NH silica gel chromatography (NH-DM1020, Fuji Silysia, hexane:ethyl acetate=3:1-1:1) to obtain 9.26 g of the title compound.
1H-NMR (CDCl3); δ (ppm) 1.60 (3H, d, J=6.6), 4.85 (1H, q, J=6.6), 7.12 (2H, q, J=9.3), 7.36 (1H, d, J=3.6), 7.56 (1H, t, J=9.9), 7.98 (1H, d, J=3.6), 8.29 (1H, d, J=9.6), 8.43 (1H, d, J=9.6)
HPLC


    Retention time: 8.82 minutes for S-isomer and 10.09 minutes for R-isomer
    Column: CHIRALCEL OJ (trade name of Daicel Chemical Industries, 4.6 mm ID×250 mm)
    Solvent: hexane/ethanol=50/50
    Flow rate: 0.5 ml/min
    Detection wavelength: 254 nm, 25° C.


Example 73
[1-(Azulen-1-yl)ethyl]-[3-(6-phenylpyridin-2-yl)propyl]amine hydrochloride
Dehydrated methylene chloride (2 mL) was added with 3-(6-phenylpyridin-2-yl)propane aldehyde (52.5 mg), [1-(azulen-1-yl)ethyl]amine (63.3 mg), and sodium triacetoxyborohydride (158.9 mg, Aldrich), and stirred at room temperature for 72 hours. The reaction mixture was added with 2 N sodium hydroxide, and extracted with chloroform. The organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (chloroform:methanol=15:1) to obtain 63.2 mg of the title compound in the free form. This compound was dissolved in chloroform, and added with 0.1 N solution of hydrochloric acid in methanol (1.7 mL), and the solvent was evaporated under reduced pressure to obtain 69.3 mg of the title compound.
1H-NMR (DMSO-d6); δ (ppm) 1.70 (3H, d, J=6.6), 2.03-2.56 (2H, m), 2.51-2.92 (4H, m), 4.53 (1H, brs), 5.15 (1H, s), 7.29-7.46 (2H, m), 7.47-7.48 (4H, m), 7.43-7.82 (4H, m), 8.30-8.34 (1H, m), 8.48 (1H, d, J=9.3), 8.75 (1H, d, J=9.9), 9.26 (1H, brs), 9.72 (1H, brs)
Example 74
Synthesis of [1-(azulen-1-yl)ethyl]-{3-[5-(4-trifluoromethoxyphenyl)furan-2-yl]propyl}amine hydrochloride
3-[5-(4-Trifluoromethoxyphenyl)furan-2-yl]propane aldehyde (44.3 mg), and [1-(azulen-1-yl)ethyl]amine (27.4 mg) were dissolved in dehydrated ethanol (1 mL), and this solution was added with titanium tetraisopropoxide (70.8 μL, Kanto Kagaku), and stirred at 40° C. for 2 hours. The reaction mixture was further added with sodium borohydride (10 mg, Wako Pure Chemical Industries), and stirred at room temperature for 1 hour. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=30:1-20:1) to obtain 43.2 mg of the title compound in the free form. This compound was dissolved in chloroform, and added with 0.1 N solution of hydrochloric acid in ethanol (980 μL), and the solvent was evaporated under reduced pressure to obtain 46.0 mg of the title compound.
1H-NMR (compound in the free form, CDCl3); δ (ppm) 2.06 (3H, d, J=6.9), 2.26-2.31 (2H, m), 2.56-2.76 (4H, m), 5.00 (1H, brs), 5.56 (1H, d, J=3.3), 6.31 (1H, d, J=3.3), 7.09 (2H, d, J=8.4), 7.21-7.27 (1H, m), 7.39-7.44 (4H, m), 7.64 (1H, t, J=9.9), 8.32 (2H, t, J=9.6), 8.49 (1H, d, J=3.9), 9.91 (1H, brs), 10.3 (1H, brs)
Example 75
Synthesis of [1-(azulen-1-yl)ethyl]-[3-(2-phenylthiazol-4-yl)propyl]amine hydrochloride
3-(2-Phenylthiazol-4-yl)propane aldehyde (60.9 mg), and [1-(azulen-1-yl)ethyl]amine (43.4 mg) were dissolved in dehydrated ethanol (3 mL), and stirred at room temperature for 2 hours under nitrogen atmosphere. The reaction mixture was cooled on ice, added with sodium borohydride (33.0 mg, Wako Pure Chemical Industries), and stirred at room temperature for 30 minutes. The reaction mixture was poured with saturated aqueous sodium hydrogencarbonate, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (chloroform:methanol=15:1) to obtain 82.5 mg of the title compound in the free form. This compound was dissolved in chloroform, and added with 0.1 N solution of hydrochloric acid in ethanol, and the solvent was evaporated under reduced pressure to obtain 90.5 mg of the title compounds.
1H-NMR (CDCl3); δ (ppm) 1.83 (3H, d, J=6.9), 2.26-2.36 (2H, m), 3.05-3.12 (3H, m), 3.19-3.28 (1H, m), 4.95 (1H, brs), 7.22 (1H, dt, J=4.5, 9.8), 7.27-7.32 (1H, m), 7.49-7.67 (7H, m), 7.86 (1H, t, J=8.1), 7.95 (2H, dd, J=1.5, 8.4), 8.14 (1H, d, J=4.2), 8.27 (1H, d, J=9.9), 8.31 (1H, d, J=9.3), 10.1 (1H, brs), 10.7 (1H, brs)
The compounds of Examples 76 to 785 shown in Tables 7 and 8 (in the table, example numbers are shown in the columns of “Exp-No”, reaction regents are shown in the columns of “regent”, and compounds of examples are shown in the columns of “ex-comp”) were obtained by using any of the various aldehydes (al-1) to (al-355) represented by the aforementioned formula (10) and any of the various amines (ami-1) to (ami-21) represented by the aforementioned formula (8) in the same manner as in Example 73 as shown in the following equation with carrying out deprotection, if deprotection was necessary. A in the formula represents any of (A-1) to (A-590) mentioned above, and B in the formula represents any of (B-1) to (B-21) mentioned above. Liquid chromatography mass spectrometry (LC-MS) spectra of the compounds mentioned in Tables 7 and 8 were measured to confirm that the objective compounds were produced.







TABLE 7













 










regent
ex-comp











exp-No
al
ami
A
B














76
al-1
ami-1
A-1
B-1


77
al-2
ami-1
A-2
B-1


78
al-3
ami-1
A-3
B-1


79
al-4
ami-1
A-4
B-1


80
al-5
ami-1
A-5
B-1


81
al-6
ami-1
A-6
B-1


82
al-7
ami-1
A-7
B-1


83
al-8
ami-1
A-8
B-1


84
al-9
ami-1
A-9
B-1


85
al-10
ami-1
A-10
B-1


86
al-11
ami-1
A-11
B-1


87
al-12
ami-1
A-12
B-1


88
al-13
ami-1
A-13
B-1


89
al-14
ami-1
A-14
B-1


90
al-15
ami-1
A-15
B-1


91
al-16
ami-1
A-16
B-1


92
al-17
ami-1
A-17
B-1


93
al-18
ami-1
A-18
B-1


94
al-19
ami-1
A-19
B-1


95
al-20
ami-1
A-20
B-1


96
al-21
ami-1
A-21
B-1


97
al-22
ami-1
A-22
B-1


98
al-23
ami-1
A-23
B-1


99
al-24
ami-1
A-24
B-1


100
al-25
ami-1
A-25
B-1


101
al-26
ami-1
A-26
B-1


102
al-27
ami-1
A-27
B-1


103
al-28
ami-1
A-28
B-1


104
al-29
ami-1
A-29
B-1


105
al-30
ami-1
A-30
B-1


106
al-31
ami-1
A-31
B-1


107
al-32
ami-1
A-32
B-1


108
al-33
ami-1
A-33
B-1


109
al-34
ami-1
A-34
B-1


110
al-35
ami-1
A-35
B-1


111
al-36
ami-1
A-36
B-1


112
al-37
ami-1
A-37
B-1


113
al-38
ami-1
A-38
B-1


114
al-39
ami-1
A-39
B-1


115
al-40
ami-1
A-40
B-1


116
al-41
ami-1
A-41
B-1


117
al-42
ami-1
A-42
B-1


118
al-43
ami-1
A-43
B-1


119
al-44
ami-1
A-44
B-1


120
al-45
ami-1
A-A5
B-1


121
al-46
ami-1
A-46
B-1


122
al-47
ami-1
A-47
B-1


123
al-48
ami-1
A-48
B-1


124
al-49
ami-1
A-49
B-1


125
al-50
ami-1
A-50
B-1


126
al-51
ami-1
A-51
B-1


127
al-52
ami-1
A-52
B-1


128
al-53
ami-1
A-53
B-1


129
al-54
ami-1
A-54
B-1


130
al-55
ami-1
A-55
B-1


131
al-56
ami-1
A-56
B-1


132
al-57
ami-1
A-57
B-1


133
al-58
ami-1
A-58
B-1


134
al-59
ami-1
A-59
B-1


135
al-60
ami-1
A-60
B-1


136
al-61
ami-1
A-61
B-1


137
al-62
ami-1
A-62
B-1


138
al-63
ami-1
A-63
B-1


139
al-64
ami-1
A-64
B-1


140
al-65
ami-1
A-65
B-1


141
al-66
ami-1
A-66
B-1


142
al-67
ami-1
A-67
B-1


143
al-68
ami-1
A-68
B-1


144
al-69
ami-1
A-69
B-1


145
al-70
ami-1
A-70
B-1


146
al-71
ami-1
A-71
B-1


147
al-72
ami-1
A-72
B-1


148
al-73
ami-1
A-73
B-1


149
al-74
ami-1
A-74
B-1


150
al-75
ami-1
A-75
B-1


151
al-76
ami-1
A-76
B-1


152
al-77
ami-1
A-77
B-1


153
al-78
ami-1
A-78
B-1


154
al-79
ami-1
A-79
B-1


155
al-80
ami-1
A-80
B-1


156
al-81
ami-1
A-81
B-1


157
al-82
ami-1
A-82
B-1


158
al-83
ami-1
A-83
B-1


159
al-84
ami-1
A-84
B-1


160
al-85
ami-1
A-85
B-1


161
al-86
ami-1
A-86
B-1


162
al-87
ami-1
A-87
B-1


163
al-88
ami-1
A-88
B-1


164
al-89
ami-1
A-89
B-1


165
al-90
ami-1
A-90
B-1


166
al-91
ami-1
A-91
B-1


167
al-92
ami-1
A-92
B-1


168
al-93
ami-1
A-93
B-1


169
al-94
ami-1
A-94
B-1


170
al-95
ami-1
A-95
B-1


171
al-96
ami-1
A-96
B-1


172
al-97
ami-1
A-97
B-1


173
al-98
ami-1
A-98
B-1


174
al-99
ami-1
A-99
B-1


175
al-100
ami-1
A-100
B-1


176
al-101
ami-1
A-101
B-1


177
al-102
ami-1
A-102
B-1


178
al-103
ami-1
A-103
B-1


179
al-104
ami-1
A-104
B-1


180
al-105
ami-1
A-105
B-1


181
al-106
ami-1
A-106
B-1


182
al-107
ami-1
A-107
B-1


183
al-108
ami-1
A-108
B-1


184
al-109
ami-1
A-109
B-1


185
al-110
ami-1
A-110
B-1


186
al-111
ami-1
A-111
B-1


187
al-112
ami-1
A-112
B-1


188
al-113
ami-1
A-113
B-1


189
al-114
ami-1
A-114
B-1


190
al-115
ami-1
A-115
B-1


191
al-116
ami-1
A-116
B-1


192
al-117
ami-1
A-117
B-1


193
al-118
ami-1
A-118
B-1


194
al-119
ami-1
A-119
B-1


195
al-120
ami-1
A-120
B-1


196
al-121
ami-1
A-121
B-1


197
al-122
ami-1
A-122
B-1


198
al-123
ami-1
A-123
B-1


199
al-124
ami-1
A-124
B-1


200
al-125
ami-1
A-125
B-1


201
al-126
ami-1
A-126
B-1


202
al-127
ami-1
A-127
B-1


203
al-128
ami-1
A-128
B-1


204
al-129
ami-1
A-129
B-1


205
al-130
ami-1
A-130
B-1


206
al-131
ami-1
A-131
B-1


207
al-132
ami-1
A-132
B-1


208
al-133
ami-1
A-133
B-1


209
al-134
ami-1
A-134
B-1


210
al-135
ami-1
A-135
B-1


211
al-136
ami-1
A-136
B-1


212
al-137
ami-1
A-137
B-1


213
al-138
ami-1
A-138
B-1


214
al-139
ami-1
A-139
B-1


215
al-140
ami-1
A-140
B-1


216
al-141
ami-1
A-141
B-1


217
al-142
ami-1
A-142
B-1


218
al-143
ami-1
A-143
B-1


219
al-144
ami-1
A-144
B-1


220
al-145
ami-1
A-145
B-1


221
al-146
ami-l
A-146
B-1


222
al-147
ami-1
A-147
B-1


223
al-148
ami-1
A-148
B-1


224
al-149
ami-1
A-149
B-1


225
al-150
ami-1
A-150
B-1


226
al-151
ami-1
A-151
B-1


227
al-152
ami-1
A-152
B-1


228
al-153
ami-1
A-153
B-1


229
al-154
ami-1
A-154
B-1


230
al-155
ami-1
A-155
B-1


231
al-156
ami-1
A-156
B-1


232
al-157
ami-1
A-157
B-1


233
al-158
ami-1
A-158
B-1


234
al-159
ami-1
A-159
B-1


235
al-160
ami-1
A-160
B-1


236
al-161
ami-1
A-161
B-1


237
al-162
ami-1
A-162
B-1


238
al-163
ami-1
A-163
B-1


239
al-164
ami-1
A-164
B-1


240
al-165
ami-1
A-165
B-1


241
al-166
ami-1
A-166
B-1


242
al-167
ami-1
A-167
B-1


243
al-168
ami-1
A-168
B-1


244
al-169
ami-1
A-169
B-1


245
al-170
ami-1
A-170
B-1


246
al-171
ami-1
A-171
B-1


247
al-172
ami-1
A-172
B-1


248
al-173
ami-1
A-173
B-1


249
al-174
ami-1
A-174
B-1


250
al-175
ami-1
A-175
B-1


251
al-176
ami-1
A-176
B-1


252
al-177
ami-1
A-177
B-1


253
al-178
ami-1
A-178
B-1


254
al-179
ami-1
A-179
B-1


255
al-180
ami-1
A-180
B-1


256
al-181
ami-1
A-181
B-1


257
al-182
ami-1
A-182
B-1


258
al-183
ami-1
A-183
B-1


259
al-184
ami-1
A-184
B-1


260
al-185
ami-1
A-185
B-1


261
al-186
ami-1
A-186
B-1


262
al-187
ami-1
A-187
B-1


263
al-188
ami-1
A-188
B-1


264
al-189
ami-1
A-189
B-1


265
al-190
ami-1
A-190
B-1


266
al-191
ami-1
A-191
B-1


267
al-192
ami-1
A-192
B-1


268
al-193
ami-1
A-193
B-1


269
al-194
ami-1
A-194
B-1


270
al-195
ami-1
A-195
B-1


271
al-196
ami-1
A-196
B-1


272
al-197
ami-1
A-197
B-1


273
al-198
ami-1
A-198
B-1


274
al-199
ami-1
A-199
B-1


275
al-200
ami-1
A-200
B-1


276
al-201
ami-1
A-201
B-1


277
al-202
ami-1
A-202
B-1


278
al-203
ami-1
A-203
B-1


279
al-204
ami-1
A-204
B-1


280
al-205
ami-1
A-205
B-1


281
al-206
ami-1
A-206
B-1


282
al-207
ami-1
A-207
B-1


283
al-208
ami-1
A-208
B-1


284
al-209
ami-1
A-209
B-1


285
al-210
ami-1
A-210
B-1


286
al-211
ami-1
A-211
B-1


287
al-212
ami-1
A-212
B-1


288
al-213
ami-1
A-213
B-1


289
al-214
ami-1
A-214
B-1


290
al-215
ami-1
A-215
B-1


291
al-216
ami-1
A-216
B-1


292
al-217
ami-1
A-217
B-1


293
al-218
ami-1
A-218
B-1


294
al-219
ami-1
A-219
B-1


295
al-220
ami-1
A-220
B-1


296
al-221
ami-1
A-221
B-1


297
al-222
ami-1
A-222
B-1


298
al-223
ami-1
A-223
B-1


299
al-224
ami-1
A-224
B-1


300
al-225
ami-1
A-225
B-1


301
al-226
ami-1
A-226
B-1


302
al-227
ami-1
A-227
B-1


303
al-228
ami-1
A-228
B-1


304
al-229
ami-1
A-229
B-1


305
al-230
ami-1
A-230
B-1


306
al-231
ami-1
A-231
B-1


307
al-232
ami-1
A-232
B-1


308
al-233
ami-1
A-233
B-1


309
al-234
ami-1
A-234
B-1


310
al-235
ami-1
A-235
B-1


311
al-236
ami-1
A-236
B-1


312
al-237
ami-1
A-237
B-1


313
al-238
ami-1
A-238
B-1


314
al-239
ami-1
A-239
B-1


315
al-240
ami-1
A-240
B-1


316
al-241
ami-1
A-241
B-1


317
al-242
ami-1
A-242
B-1


318
al-243
ami-1
A-243
B-1


319
al-244
ami-1
A-244
B-1


320
al-245
ami-1
A-245
B-1


321
al-246
ami-1
A-246
B-1


322
al-247
ami-1
A-247
B-1


323
al-248
ami-1
A-248
B-1


324
al-249
ami-1
A-249
B-1


325
al-250
ami-1
A-250
B-1


326
al-251
ami-1
A-251
B-1


327
al-252
ami-1
A-252
B-1


328
al-1
ami-5
A-1
B-5


329
al-2
ami-5
A-2
B-5


330
al-3
ami-5
A-3
B-5


331
al-4
ami-5
A-4
B-5


332
al-5
ami-5
A-5
B-5


333
al-6
ami-5
A-6
B-5


334
al-7
ami-5
A-7
B-5


335
al-8
ami-5
A-8
B-5


336
al-9
ami-5
A-9
B-5


337
al-10
ami-5
A-10
B-5


338
al-11
ami-5
A-11
B-5


339
al-12
ami-5
A-12
B-5


340
al-13
ami-5
A-13
B-5


341
al-14
ami-5
A-14
B-5


342
al-15
ami-5
A-15
B-5


343
al-16
ami-5
A-16
B-5


344
al-17
ami-5
A-17
B-5


345
al-18
ami-5
A-18
B-5


346
al-19
ami-5
A-19
B-5


347
al-20
ami-5
A-20
B-5


348
al-21
ami-5
A-21
B-5


349
al-22
ami-5
A-22
B-5


350
al-23
ami-5
A-23
B-5


351
al-24
ami-5
A-24
B-5


352
al-25
ami-5
A-25
B-5


353
al-26
ami-5
A-26
B-5


354
al-27
ami-5
A-27
B-5


355
al-28
ami-5
A-28
B-5


356
al-29
ami-5
A-29
B-5


357
al-30
ami-5
A-30
B-5


358
al-31
ami-5
A-31
B-5


359
al-32
ami-5
A-32
B-5


360
al-33
ami-5
A-33
B-5


361
al-34
ami-5
A-34
B-5


362
al-35
ami-5
A-35
B-5


363
al-36
ami-5
A-36
B-5


364
al-37
ami-5
A-37
B-5


365
al-38
ami-5
A-38
B-5


366
al-39
ami-5
A-39
B-5


367
al-40
ami-5
A-40
B-5


368
al-4i
ami-5
A-41
B-5


369
al-42
ami-5
A-42
B-5


370
al-43
ami-5
A-43
B-5


371
al-44
ami-5
A-44
B-5


372
al-45
ami-5
A-45
B-5


373
al-46
ami-5
A-46
B-5


374
al-47
ami-5
A-47
B-5


375
al-48
ami-5
A-48
B-5


376
al-49
ami-5
A-49
B-5


377
al-50
ami-5
A-50
B-5


378
al-51
ami-5
A-51
B-5


379
al-52
ami-5
A-52
B-5


380
al-53
ami-5
A-53
B-5


381
al-54
ami-5
A-54
B-5


382
al-55
ami-5
A-55
B-5


383
al-56
ami-5
A-56
B-5


384
al-57
ami-5
A-57
B-5


385
al-58
ami-5
A-58
B-5


386
al-59
ami-5
A-59
B-5


387
al-60
ami-5
A-60
B-5


388
al-61
ami-5
A-61
B-5


389
al-62
ami-5
A-62
B-5


390
al-63
ami-5
A-63
B-5


391
al-64
ami-5
A-64
B-5


392
al-65
ami-5
A-65
B-5


393
al-66
ami-5
A-66
B-5


394
al-67
ami-5
A-67
B-5


395
al-68
ami-5
A-68
B-5


396
al-69
ami-5
A-69
B-5


397
al-70
ami-5
A-70
B-5


398
al-71
ami-5
A-71
B-5


399
al-72
ami-5
A-72
B-5


400
al-73
ami-5
A-73
B-5


401
al-74
ami-5
A-74
B-5


402
al-75
ami-5
A-75
B-5


403
al-76
ami-5
A-76
B-5


404
al-77
ami-5
A-77
B-5


405
al-78
ami-5
A-78
B-5


406
al-79
ami-5
A-79
B-5


407
al-80
ami-5
A-80
B-5


408
al-81
ami-5
A-81
B-5


409
al-82
ami-5
A-82
B-5


410
al-83
ami-5
A-83
B-5


411
al-84
ami-5
A-84
B-5


412
al-85
ami-5
A-85
B-5


413
al-86
ami-5
A-86
B-5


414
al-87
ami-5
A-87
B-5


415
al-88
ami-5
A-88
B-5


416
al-89
ami-5
A-89
B-5


417
al-90
ami-5
A-90
B-5


418
al-91
ami-5
A-91
B-5


419
al-92
ami-5
A-92
B-5


420
al-93
ami-5
A-93
B-5


421
al-94
ami-5
A-94
B-5


422
al-95
ami-5
A-95
B-5


423
al-96
ami-5
A-96
B-5


424
al-97
ami-5
A-97
B-5


425
al-98
ami-5
A-98
B-5


426
al-99
ami-5
A-99
B-5


427
al-100
ami-5
A-100
B-5


428
al-101
ami-5
A-101
B-5


429
al-102
ami-5
A-102
B-5


430
al-103
ami-5
A-103
B-5


431
al-104
ami-5
A-104
B-5


432
al-105
ami-5
A-105
B-5


433
al-106
ami-5
A-106
B-5


434
al-107
ami-5
A-107
B-5


435
al-108
ami-5
A-108
B-5


436
al-109
ami-5
A-109
B-5


437
al-110
ami-5
A-110
B-5


438
al-111
ami-5
A-111
B-5


439
al-112
ami-5
A-112
B-5


440
al-113
ami-5
A-113
B-5


441
al-114
ami-5
A-114
B-5


442
al-115
ami-5
A-115
B-5


443
al-1h6
ami-5
A-116
B-5


444
al-117
ami-5
A-117
B-5


445
al-118
ami-5
A-118
B-5


446
al-119
ami-5
A-119
B-5


447
al-120
ami-5
A-120
B-5


448
al-121
ami-5
A-121
B-5


449
al-122
ami-5
A-122
B-5


450
al-123
ami-5
A-123
B-5


451
al-124
ami-5
A-124
B-5


452
al-125
ami-5
A-125
B-5


453
al-126
ami-5
A-126
B-5


454
al-127
ami-5
A-127
B-5


455
al-128
ami-5
A-128
B-5


456
al-129
ami-5
A-129
B-5


457
al-130
ami-5
A-130
B-5


458
al-131
ami-5
A-131
B-5


459
al-132
ami-5
A-132
B-5


460
al-133
ami-5
A-133
B-5


461
al-134
ami-5
A-134
B-5


462
al-135
ami-5
A-135
B-5


463
al-136
ami-5
A-136
B-5


464
al-137
ami-5
A-137
B-5


465
al-138
ami-5
A-138
B-5


466
al-139
ami-5
A-139
B-5


467
al-140
ami-5
A-140
B-5


468
al-141
ami-5
A-141
B-5


469
al-142
ami-5
A-142
B-5


470
al-143
ami-5
A-143
B-5


471
al-144
ami-5
A-144
B-5


472
al-145
ami-5
A-145
B-5


473
al-146
ami-5
A-146
B-5


474
al-147
ami-5
A-147
B-5


475
al-148
ami-5
A-148
B-5


476
al-149
ami-5
A-149
B-5


477
al-150
ami-5
A-150
B-5


478
al-151
ami-5
A-151
B-5


479
al-152
ami-5
A-152
B-5


480
al-153
ami-5
A-153
B-5


481
al-154
ami-5
A-154
B-5


482
al-155
ami-5
A-155
B-5


483
al-156
ami-5
A-156
B-5


484
al-157
ami-5
A-157
B-5


485
al-158
ami-5
A-158
B-5


486
al-159
ami-5
A-159
B-5


487
al-160
ami-5
A-160
B-5


488
al-161
ami-5
A-161
B-5


489
al-162
ami-5
A-162
B-5


490
al-163
ami-5
A-163
B-5


491
al-164
ami-5
A-164
B-5


492
al-165
ami-5
A-165
B-5


493
al-166
ami-5
A-166
B-5


494
al-167
ami-5
A-167
B-5


495
al-168
ami-5
A-168
B-5


496
al-169
ami-5
A-169
B-5


497
al-170
ami-5
A-170
B-5


498
al-171
ami-5
A-171
B-5


499
al-172
ami-5
A-172
B-5


500
al-173
ami-5
A-173
B-5


501
al-174
ami-5
A-174
B-5


502
al-175
ami-5
A-175
B-5


503
al-176
ami-5
A-176
B-5


504
al-177
ami-5
A-177
B-5


5O5
al-178
ami-5
A-178
B-5


506
al-179
ami-5
A-179
B-5


507
al-180
ami-5
A-180
B-5


508
al-181
ami-5
A-181
B-5


509
al-182
ami-5
A-182
B-5


510
al-183
ami-5
A-183
B-5


511
al-184
ami-5
A-184
B-5


512
al-185
ami-5
A-185
B-5


513
al-186
ami-5
A-186
B-5


514
al-187
ami-5
A-187
B-5


515
al-188
ami-5
A-188
B-5


516
al-189
ami-5
A-189
B-5


517
al-190
ami-5
A-190
B-5


518
al-19i
ami-5
A-191
B-5


519
al-192
ami-5
A-192
B-5


520
al-193
ami-5
A-193
B-5


521
al-194
ami-5
A-194
B-5


522
al-195
ami-5
A-195
B-5


523
al-196
ami-5
A-196
B-5


524
al-197
ami-5
A-197
B-5


525
al-198
ami-5
A-198
B-5


526
al-199
ami-5
A-199
B-5


527
al-200
ami-5
A-200
B-5


528
al-201
ami-5
A-201
B-5


529
al-202
ami-5
A-202
B-5


530
al-203
ami-5
A-203
B-5


531
al-204
ami-5
A-204
B-5


532
al-205
ami-5
A-205
B-5


533
al-206
ami-5
A-206
B-5


534
al-207
ami-5
A-207
B-5


535
al-208
ami-5
A-208
B-5


536
al-209
ami-5
A-209
B-5


537
al-210
ami-5
A-210
B-5


538
al-211
ami-5
A-211
B-5


539
al-212
ami-5
A-212
B-5


540
al-213
ami-5
A-213
B-5


541
al-214
ami-5
A-214
B-5


542
al-215
ami-5
A-215
B-5


543
al-216
ami-5
A-216
B-5


544
al-217
ami-5
A-217
B-5


545
al-218
ami-5
A-218
B-5


546
al-219
ami-5
A-219
B-5


547
al-220
ami-5
A-220
B-5


548
al-221
ami-5
A-221
B-5


549
al-222
ami-5
A-222
B-5


550
al-223
ami-5
A-223
B-5


551
al-224
ami-5
A-224
B-5


552
al-225
ami-5
A-225
B-5


553
al-226
ami-5
A-226
B-5


554
al-227
ami-5
A-227
B-5


555
al-228
ami-5
A-228
B-5


556
al-229
ami-5
A-229
B-5


557
al-230
ami-5
A-230
B-5


558
al-231
ami-5
A-231
B-5


559
al-232
ami-5
A-232
B-5


560
al-233
ami-5
A-233
B-5


561
al-234
ami-5
A-234
B-5


562
al-235
ami-5
A-235
B-5


563
al-236
ami-5
A-236
B-5


564
al-237
ami-5
A-237
B-5


565
al-238
ami-5
A-238
B-5


566
al-239
ami-5
A-239
B-5


567
al-240
ami-5
A-240
B-5


568
al-241
ami-5
A-241
B-5


569
al-242
ami-5
A-242
B-5


570
al-243
ami-5
A-243
B-5


571
al-244
ami-5
A-244
B-5


572
al-245
ami-5
A-245
B-5


573
al-246
ami-5
A-246
B-5


574
al-247
ami-5
A-247
B-5


575
al-248
ami-5
A-248
B-5


576
al-249
ami-5
A-249
B-5


577
al-250
ami-5
A-250
B-5


578
al-251
ami-5
A-251
B-5


579
al-252
ami-5
A-252
B-5



















TABLE 8









regent
ex-comp











exp-No
al
ami
A
B





580
al-253
ami-1
A-380
B-1


581
al-254
ami-1
A-381
B-1


582
al-255
ami-1
A-382
B-1


583
al-256
ami-1
A-383
B-1


584
al-257
ami-1
A-384
B-1


585
al-258
ami-1
A-385
B-1


586
al-259
ami-1
A-386
B-1


587
al-260
ami-1
A-387
B-1


588
al-261
ami-1
A-388
B-1


589
al-262
ami-1
A-389
B-1


590
al-263
ami-1
A-390
B-1


591
al-264
ami-1
A-391
B-1


592
al-265
ami-1
A-396
B-1


593
al-266
ami-1
A-397
B-1


594
al-267
ami-1
A-398
B-1


595
al-268
ami-1
A-399
B-1


596
al-269
ami-1
A-409
B-1


597
al-270
ami-1
A-410
B-1


598
al-271
ami-1
A-411
B-1


599
al-272
ami-1
A-412
B-1


600
al-273
ami-1
A-413
B-1


601
al-274
ami-1
A-414
B-1


602
al-275
ami-1
A-415
B-1


603
al-276
ami-1
A-416
B-1


604
al-277
ami-1
A-417
B-1


605
al-278
ami-1
A-418
B-1


606
al-279
ami-1
A-419
B-1


607
al-280
ami-1
A-420
B-1


608
al-281
ami-1
A-421
B-1


609
al-282
ami-1
A-422
B-1


610
al-283
ami-1
A-423
B-1


611
al-284
ami-1
A-424
B-1


612
al-285
ami-1
A-425
B-1


613
al-286
ami-1
A-426
B-1


614
al-287
ami-1
A-522
B-1


615
al-288
ami-1
A-523
B-1


616
al-289
ami-1
A-524
B-1


617
al-290
ami-1
A-525
B-1


618
al-291
ami-1
A-526
B-1


619
al-292
ami-1
A-527
B-1


620
al-293
ami-1
A-528
B-1


621
al-294
ami-1
A-529
B-1


622
al-295
ami-1
A-530
B-1


623
al-296
ami-1
A-531
B-1


624
al-297
ami-1
A-532
B-1


625
al-298
ami-1
A-533
B-1


626
al-299
ami-1
A-534
B-1


627
al-300
ami-1
A-535
B-1


628
al-301
ami-1
A-536
B-1


629
al-302
ami-1
A-537
B-1


630
al-303
ami-1
A-538
B-1


631
al-304
ami-1
A-539
B-1


632
al-305
ami-1
A-540
B-1


633
al-306
ami-1
A-541
B-1


634
al-307
ami-1
A-542
B-1


635
al-308
ami-1
A-543
B-1


636
al-309
ami-1
A-544
B-1


637
al-310
ami-1
A-545
B-1


638
al-311
ami-1
A-546
B-1


639
al-312
ami-1
A-547
B-1


640
al-313
ami-1
A-548
B-1


641
al-314
ami-1
A-549
B-1


642
al-315
ami-1
A-550
B-1


643
al-316
ami-1
A-551
B-1


644
al-317
ami-1
A-552
B-1


645
al-318
ami-1
A-553
B-1


646
al-319
ami-1
A-554
B-1


647
al-320
ami-1
A-555
B-1


648
al-321
ami-1
A-556
B-1


649
al-322
ami-1
A-557
B-1


650
al-323
ami-1
A-558
B-1


651
al-324
ami-1
A-559
B-1


652
al-325
ami-1
A-560
B-1


653
al-326
ami-1
A-561
B-1


654
al-327
ami-1
A-562
B-1


655
al-328
ami-1
A-563
B-1


656
al-329
ami-1
A-564
B-1


657
al-330
ami-1
A-565
B-1


658
al-331
ami-1
A-566
B-1


659
al-332
ami-1
A-567
B-1


660
al-333
ami-1
A-568
B-1


661
al-334
ami-1
A-569
B-1


662
al-335
ami-1
A-570
B-1


663
al-336
ami-1
A-571
B-1


664
al-337
ami-1
A-572
B-1


665
al-338
ami-1
A-573
B-1


666
al-339
ami-1
A-574
B-1


667
al-340
ami-1
A-575
B-1


668
al-341
ami-1
A-576
B-1


669
al-342
ami-1
A-577
B-1


670
al-343
ami-1
A-578
B-1


671
al-344
ami-1
A-579
B-1


672
al-345
ami-1
A-580
B-1


673
al-346
ami-1
A-581
B-1


674
al-347
ami-i
A-582
B-1


675
al-348
ami-1
A-583
B-1


676
al-349
ami-1
A-584
B-1


677
al-350
ami-1
A-585
B-1


678
al-351
ami-1
A-586
B-1


679
al-352
ami-1
A-587
B-1


680
al-353
ami-1
A-588
B-1


681
al-354
ami-1
A-589
B-1


682
al-355
ami-1
A-590
B-1


683
al-253
ami-5
A-380
B-5


684
al-254
ami-5
A-381
B-5


685
al-255
ami-5
A-382
B-5


686
al-256
ami-5
A-383
B-5


687
al-257
ami-5
A-384
B-5


688
al-258
ami-5
A-385
B-5


689
al-259
ami-5
A-386
B-5


690
al-260
ami-5
A-387
B-5


691
al-261
ami-5
A-388
B-5


692
al-262
ami-5
A-389
B-5


693
al-263
ami-5
A-390
B-5


694
al-264
ami-5
A-391
B-5


695
al-265
ami-5
A-396
B-5


696
al-266
ami-5
A-397
B-5


697
al-267
ami-5
A-398
B-5


698
al-268
ami-5
A-399
B-5


699
al-269
ami-5
A-409
B-5


700
al-270
ami-5
A-410
B-5


701
al-271
ami-5
A-411
B-5


702
al-272
ami-5
A-412
B-5


703
al-273
ami-5
A-413
B-5


704
al-274
ami-5
A-414
B-5


705
al-275
ami-5
A-415
B-5


706
al-276
ami-5
A-416
B-5


707
al-277
ami-5
A-417
B-5


708
al-278
ami-5
A-418
B-5


709
al-279
ami-5
A-419
B-5


710
al-280
ami-5
A-420
B-5


711
al-281
ami-5
A-421
B-5


712
al-282
ami-5
A-422
B-5


713
al-283
ami-5
A-423
B-5


714
al-284
ami-5
A-424
B-5


715
al-285
ami-5
A-425
B-5


716
al-286
ami-5
A-426
B-5


717
al-287
ami-5
A-522
B-5


718
al-288
ami-5
A-523
B-5


719
al-289
ami-5
A-524
B-5


720
al-290
ami-5
A-525
B-5


721
al-291
ami-5
A-526
B-5


722
al-292
ami-5
A-527
B-5


723
al-293
ami-5
A-528
B-5


724
al-294
ami-5
A-529
B-5


725
al-295
ami-5
A-530
B-5


726
al-296
ami-5
A-531
B-5


727
al-297
ami-5
A-532
B-5


728
al-298
ami-5
A-533
B-5


729
al-299
ami-5
A-534
B-5


730
al-300
ami-5
A-535
B-5


731
al-301
ami-5
A-536
B-5


732
al-302
ami-5
A-537
B-5


733
al-303
ami-5
A-538
B-5


734
al-304
ami-5
A-539
B-5


735
al-305
ami-5
A-540
B-5


736
al-306
ami-5
A-541
B-5


737
al-307
ami-5
A-542
B-5


738
al-308
ami-5
A-543
B-5


739
al-309
ami-5
A-544
B-5


740
al-310
ami-5
A-545
B-5


741
al-311
ami-5
A-546
B-5


742
al-312
ami-5
A-547
B-5


743
al-313
ami-5
A-548
B-5


744
al-314
ami-5
A-549
B-5


745
al-315
ami-5
A-550
B-5


746
al-316
ami-5
A-551
B-5


747
al-317
ami-5
A-552
B-5


748
al-318
ami-5
A-553
B-5


749
al-319
ami-5
A-554
B-5


750
al-320
ami-5
A-555
B-5


751
al-321
ami-5
A-556
B-5


752
al-322
ami-5
A-557
B-5


753
al-323
ami-5
A-558
B-5


754
al-324
ami-5
A-559
B-5


755
al-325
ami-5
A-560
B-5


756
al-326
ami-5
A-561
B-5


757
al-327
ami-5
A-562
B-5


758
al-328
ami-5
A-563
B-5


759
al-329
ami-5
A-564
B-5


760
al-330
ami-5
A-565
B-5


76i
al-331
ami-5
A-566
B-5


762
al-332
ami-5
A-567
B-5


763
al-333
ami-5
A-568
B-5


764
al-334
ami-5
A-569
B-5


765
al-335
ami-5
A-570
B-5


766
al-336
ami-5
A-571
B-5


767
al-337
ami-5
A-572
B-5


768
al-338
ami-5
A-573
B-5


769
al-339
ami-5
A-574
B-5


770
al-340
ami-5
A-575
B-5


77i
al-341
ami-5
A-576
B-5


772
al-342
ami-5
A-577
B-5


773
al-343
ami-5
A-578
B-5


774
al-344
ami-5
A-579
B-5


775
al-345
ami-5
A-580
B-5


776
al-346
ami-5
A-581
B-5


777
al-347
ami-5
A-582
B-5


778
al-348
ami-5
A-583
B-5


779
al-349
ami-5
A-584
B-5


780
al-350
ami-5
A-585
B-5


781
al-351
ami-5
A-586
B-5


782
al-352
ami-5
A-587
B-5


783
al-353
ami-5
A-588
B-5


784
al-354
ami-5
A-589
B-5


785
al-355
ami-5
A-590
B-5









Test Example 1
Blood PTH Concentration Depressing Action
Each of the compounds described in Examples 1 to 71 was dissolved in a suitable solvent (20 to 50% PEG400, 15% cyclodextrin, and the like), and intravenously administered to 8-week old SD rats (Charles River Japan, 250 to 300 g) at a dose of 1 mg/kg.
The rats were anesthetized with ether 20 minutes after the administration, and the whole blood was collected from the abdominal aortas into test tubes treated with heparin. Plasma was separated from the whole blood at 4° C. and 3000 rpm, and blood PTH concentration was measured by using Rat PTH IRMA Kit (Immutopics, 50-2000) to evaluate the blood PTH concentration depressing action.
All the compounds described in the example reduced the blood PTH concentration by 15 to 95% compared with the values observed before the administration. Further, no death was observed in the administration groups for any of the compounds, and thus it was demonstrated that the compounds of the present invention can be safely administered.
Test Example 2
Action on Blood PTH Concentration and Bone in HyperPTHemia Model (1)
Renal failure rats were prepared by referring to the literature (Jablonski G. et al., “Surgically induced uremia in rats 1: effect on bone strength and metabolism”, Biosci. Rep., 13, 275-287, 1993). Specifically, 2⁄3 each of left kidneys of 7-week old SD male rats (Charles River Japan, 230 to 255 g) was excised, and one week after, whole right kidneys were extracted to prepare 5/6-nephrectomized rats. Then, the rats were fed for 90 days, and used as renal failure rats.
Each of the compounds described in Examples 1 to 71 was dissolved in a suitable solvent (20 to 50% PEG400, 15% cyclodextrin, and the like), and orally adminstered every day to the rats at a dose of 50 mg/kg for 30 days. Twenty-four hours after the final administration, the animals were sacrificed by exsanguination, and non-decalcificated sections of left tibias were prepared. According to bone morphological measurement techniques, bone volume (BV/TV) and fibrosis tissue volume (Fb.V/TV) of the proximal epiphyses were measured to evaluate degree of onset of fibrous ostitis. Further, 1 hour after the final administration, blood was partially collected from the cervical veins, and the blood PTH concentration was measured by using Rat PTH IRMA Kit (Immutopics, 50-2000) to evaluate the blood PTH concentration depressing action.
The blood PTH concentrations observed in the pathological group (group administered with no compound) significantly increased (p<0.05) compared with the normal group (false operation group), and significant reduction (p<0.05) of bone volume and significant increase (p<0.01) of fibrosis tissue volume were observed in the pathological group.
Whilst, effects of depressing the blood PTH concentration by 20 to 95% was observed in the groups administered with the compounds of the examples as compared to the pathological group, and suppressing reduction of bone volume by 10 to 90% in the pathological group was also observed. Further, suppression of the increase in fibrosis tissue volume by 10 to 90% in the pathological group was typically demonstrated. No death was observed in the groups administered with the compounds.
Test Example 3
Action on Blood PTH Concentration and Bone in HyperPTHemia Model (2)
Renal failure rats were prepared by referring to the literature (Ishii H. et al., “Daily intermittent decreases in serum levels of parathyroid hormone have an anabolic-like action on the bones of uremic rats with low-turnover bone and osteomalacia”, Bone, 26, 175-182, 2000). Specifically, 5-week old SD male rats (Charles River Japan, 100 to 135 g) were intravenously administered with adriamycin (doxorubicin hydrochloride, Wako Pure Chemical Industries, 040-21521) at a dose of 3 mg/kg, and then, after 3 weeks, further administered with 2 mg/kg. After 14 weeks of the additional administration of adriamycin, each of the compounds described in Examples 1 to 71 dissolved in a suitable solvent (20 to 50% PEG400, 15% cyclodextrin, and the like) was orally administered every day to the rats at a dose of 50 mg/kg for 60 days.
Twenty-four hours after the final administration, the animals were sacrificed by exsanguination, and non-decalcificated sections of left tibias were prepared. According to bone morphological measurement techniques, bone volume (BV/TV) and osteoid volume (OV/TV) of the proximal metaphysis were measured to evaluate degree of onset of osteomalacia. Further, 1 hour after the final administration, blood was partially collected from the cervical veins, and the blood PTH concentration was measured by using Rat PTH IRMA Kit (Immutopics, 50-2000) to evaluate the blood PTH concentration depressing action.
The blood PTH concentrations observed in the pathological group (group administered with no compound) significantly increased (p<0.05) compared with the normal group (false operation group), and significant reduction (p<0.05) of bone volume and significant increase (p<0.01) of osteoid volume were observed in the pathological group.
Whilst, effects of depressing the blood PTH concentration by 20 to 95% in the groups administered with the compounds of the examples compared to the pathological group was observed, and suppressing reduction of bone volume by 10 to 90% in the pathological group was also observed. Further, suppression of the increase in osteoid volume by 10 to 90% in the pathological group were typically demonstrated. No death was observed in the groups administered with the compounds.
Test Example 4
Action on Blood PTH Concentration and Bone in HyperPTHemia Model (3)
Malabsorption rats were prepared by referring to the literature (Suzuki, H. “Experimental Analysis Concerning Osteopathia After Total Gastrectomy and Influence of Menopause”, Journal of Jikei University School of Medicine, 114, 77-87, 1999). Specifically, stomachs of 40-week old Wister male rats (Charles River Japan, 275 to 310 g) were totally extracted, and ends of esophagi and duodenums were anastomosed to prepare totally gastrectomized (malabsorption) rats. Eight weeks after the operation, each of the compounds described in Examples 1 to 71 dissolved in a suitable solvent (20 to 50% PEG400, 15% cyclodextrin, and the like) was orally administered every day to the rats at a dose of 50 mg/kg for 30 days. Twenty-four hours after the final administration, the animals were sacrificed by exsanguination, and non-decalcificated sections of left tibias were prepared. According to bone morphological measurement techniques, bone volume (BV/TV) and osteoid volume (OV/TV) of the proximal metaphysis were measured to evaluate degree of onset of osteomalacia. Further, 15 minutes, 30 minutes or 1 hour after the final administration, blood was partially collected from the cervical veins, and the blood PTH concentration was measured by using Rat PTH IRMA Kit (Immutopics, 50-2000) to evaluate the blood PTH concentration depressing action.
The blood PTH concentrations observed in the pathological group (group administered with no compound) significantly increased (p<0.05) compared with the normal group (false operation group), and significant reduction (p<0.05) of bone volume and significant increase (p<0.01) of osteoid volume were observed in the pathological group. Whilst, effects of depressing the blood PTH concentration by 20 to 95% was observed in the groups administered with the compounds of the examples compared to the pathological group. Suppressing reduction of bone volume by 10 to 90% in the pathological group was also observed. Further, suppression of the increase in osteoid volume by 10 to 90% in the pathological group were typically demonstrated. No death was observed in the groups administered with the compounds.
Test Example 5
Inhibitory Action Against Drug Metabolism Enzyme CYP3A4
Inhibitory action of the compounds of the present invention against the drug metabolism enzyme CYP3A4, which is considered to seriously affect drug interactions with a combination drug, was examined. A test compound was dissolved and diluted in a buffer (200 mM potassium phosphate, 1.3 mM NADP+, 3.3 mM magnesium chloride, 3.3 mM glucose-6-phosphate, 0.4 units/mL of glucose-6-phosphate dehydrogenase, 0.048 mg/mL of Control Microsome (produced by GENTEST, 242311), pH7.4), added with 5 nM CYP3A4 (produced by GENTEST, 242328) and 0.1 mM BFC ((7-benzyloxy-4-trifluoromethyl)coumarin) as a substrate, and incubated at 37° C. After 30 minutes, the reaction was terminated by addition of 0.1 M Tris containing 80% acetonitrile, and fluorescence was measured at Ex 409 nm/Em 530 nm. The enzyme inhibitory activity was represented in terms of IC50 value.
Typical IC50 values of the compounds described in the examples were found to be in a range of 100 nM to higher than 30 μM, and accordingly, it is concluded that a risk of occurrence of an interaction with the combination drug, which might result in side effects, is low.
Test Example 6
Inhibitory Action Against Drug Metabolism Enzyme CYP2D6
Inhibitory action of the compounds of the present invention against the drug metabolism enzyme CYP2D6, which is considered to seriously affect drug interactions with a combination drug, was examined. A test compound was dissolved and diluted in a buffer (100 mM potassium phosphate, 0.008 mM NADP+, 0.4 mM magnesium chloride, 0.4 mM glucose-6-phosphate, 0.4 units/mL of glucose-6-phosphate dehydrogenase, 0.048 mg/mL of Control Microsome (produced by GENTEST, 242311), pH7.4), added with 7.5 nM CYP2D6 (produced by GENTEST, 242217) and 0.0015 mM AMMC (3-[2-(N,N-diethyl-N-methylamino)ethyl]-7-methoxy-4-methylcoumarin) as a substrate, and incubated at 37° C. After 30 minutes, the reaction was terminated by addition of 0.1 M Tris containing 80% acetonitrile, and fluorescence was measured at Ex 390 nm/Em 460 nm. The enzyme inhibitory activity was represented in terms of IC50 value.
Typical IC50 values of the compounds described in the examples were found to be in a range of 100 nM to higher than 30 μM, and accordingly, it is concluded that a risk of occurrence of an interaction with the combination drug, which might result in side effects, is low.
Preparation Example
A preparation example will be specifically explained below. However, the scope of the present invention is not limited by the following example.
Preparation Example 1
Tablets
The compound of Example 1 in an amount of 2.5 g was mixed with 4.9 g of lactose, 2.1 g of cornstarch, and 0.4 g of hydroxypropylcellulose, granulated by using distilled water, and dried. Then, the granules were added with 0.1 g of magnesium stearate, and compressed by using a pressurization-type compressing machine to prepare tablets having a weight of 200 mg per tablet and a diameter of 8 mm.
INDUSTRIAL APPLICABILITY
The compounds of the present invention show potent PTH depressiong activity when they are administered to a human or animal in the free forms or salt forms thereof, and they are useful as an active ingredient of medicaments for prophylactic and/or therapeutic treatment of, for example, hyperPTHemia.

## Claims

1. A compound represented by the following formula (1) or a salt thereof:




wherein:
A represents a group selected from the group consisting of (1) a saturated heterocyclic group, (2) a 5-membered heteroaromatic group having two heteroatoms in the ring which may be substituted, (3) a group represented by the following formula A1, (4) a group represented by the following formula A2, and (5) a group represented by the following formula A3:





in which
R2, R3, and R4 may be the same or different, and independently represent a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group, a phenyl group, a substituted phenyl group, a benzyl group, a substituted benzyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, a nitro group, or N (R16) (R17), wherein R16 and R17 may be the same or different, and independently represent a hydrogen atom, an alkyl group, an acyl group, or SO2R18, wherein R18 represents a lower alkyl group, or R16 and R17 together form a 3- to 7-membered ring to represent a cyclic amine as N (R16) (R17);
R5, R6 and R7 may be the same or different, and independently represent a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group, a phenyl group, a substituted phenyl group, a benzyl group, a substituted benzyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, a nitro group, or N (R16) (R17), wherein R16 and R17 may be the same or different, and independently represent a hydrogen atom, an alkyl group, an acyl group, or SO2R18, wherein R18 represents a lower alkyl group, or R16 and R17 together form a 3- to 7-membered ring to represent a cyclic amine as N (R16) (R17);
R8, R9 and R10 independently represent a hydrogen atom, a hydroxyl group, a halogen atom, an alkyl group, a phenyl group, a substituted phenyl group, a benzyl group, a substituted benzyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, an alkoxyl group arbitrarily substituted with one or more halogen atoms, a nitro group, or N (R16) (R17), wherein R16 and R17 may be the same or different, and independently represent a hydrogen atom, an alkyl group, an acyl group, or SO2R18, wherein R18 represents a lower alkyl group, or R16 and R17 together form a 3- to 7-membered ring to represent a cyclic amine as N (R16) (R17), or R8 and R9 may together form a benzene ring to represent a bicyclic heteroaromatic group as the group represented by the formula A3;
X1 represents oxygen atom, sulfur atom, or N—R19 wherein R19 represents a hydrogen atom, an alkyl group, phenyl group, or a substituted phenyl group;
B is a group represented by the formula B2:




wherein R12 represents a hydrogen atom or an alkyl group, Y2 represents CH or a nitrogen atom;
R1 represents an alkyl group; and
n represents an integer of 2 to 6.

2. The compound or salt thereof according to claim 1, wherein A is a group represented by the formula A2.

3. The compound or salt thereof according to claim 2, wherein A is a group represented by the formula A2, wherein R6 and R7 are hydrogen atoms, and R5 is a phenyl group, a substituted phenyl group, a benzyl group, a substituted benzyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, or an alkoxyl group arbitrarily substituted with one or more halogen atoms, and
B is a group represented by the formula B2, wherein R12 is a hydrogen atom, and Y2 is CH.

4. The compound or salt thereof according to claim 3, wherein R5 is a substituted phenyl group, a monocyclic heteroaromatic group which may be substituted, or a bicyclic heteroaromatic group which may be substituted.

5. The compound or salt thereof according to claim 1, wherein A is a group represented by the formula A3.

6. The compound or salt thereof according to claim 5, wherein A is a group represented by the formula A3, wherein R8 and R10 are hydrogen atoms, and R9 is a phenyl group, a substituted phenyl group, a benzyl group, a substituted benzyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, or an alkoxyl group arbitrarily substituted with one or more halogen atoms, and
B is a group represented by the formula B2, wherein R12 is a hydrogen atom, and Y2 is CH.

7. The compound or salt thereof according to claim 6, wherein R9 is a substituted phenyl group, a monocyclic heteroaromatic group which may be substituted, or a bicyclic heteroaromatic group which may be substituted.

8. A compound represented by the following formula (1) or a salt thereof:




wherein:
A is a group represented by the following formula A4





in which
R23 is a phenyl group, a substituted phenyl group, a benzyl group, a substituted benzyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, or an alkoxyl group arbitrarily substituted with one or more halogen atoms;
X2 represents an oxygen atom, a sulfur atom, or N—R19, wherein R19 represents a hydrogen atom, an alkyl group, a phenyl group, or a substituted phenyl group, and
B is a group represented by the formula B2:





wherein R12 represents hydrogen atom or an alkyl group, Y2 represents CH or nitrogen atom,
R1 represents an alkyl group, and
n represents an integer of 2 to.

9. The compound or salt thereof according to claim 8, wherein A is a group represented by the formula A4, wherein R23 is a phenyl group, a substituted phenyl group, a benzyl group, a substituted benzyl group, a monocyclic heteroaromatic group which may be substituted, a bicyclic heteroaromatic group which may be substituted, an alkoxyl group, an alkyl group arbitrarily substituted with one or more halogen atoms, or an alkoxyl group arbitrarily substituted with one or more halogen atoms, and
B is a group represented by the formula B2, wherein R12 is a hydrogen atom, and Y2 is CH.

10. The compound or salt thereof according to claim 9, wherein R23 is a substituted phenyl group, a monocyclic heteroaromatic group which may be substituted, or a bicyclic heteroaromatic group which may be substituted.

11. The compound or salt thereof according to claim 1, wherein A is a group represented by the formula A2 or A3, or a 5-membered heteroaromatic group having two hetero atoms in the ring.

12. A medicament containing the compound according to claim 1 or a physiologically acceptable salt thereof as an active ingredient.

13. The medicament according to claim 12, which is used for therapeutic treatment of hyperparathormonemia.

14. The medicament according to claim 12, which is used for therapeutic treatment of hyperparathyroidism.

15. The medicament according to claim 12, which is used for therapeutic treatment of a bone disease associated with increase in blood parathyroid hormone level.

16. A method of treating condition selected from the group consisting of hyperparathormonemia, hyperparathyroidism, and bone disease associated with increase in blood parathyroid hormone level, said method comprising administering to a patient in need thereof a composition comprising an effective amount of the compound of claim 1.

17. A method of treating condition selected from the group consisting of hyperparathormonemia, hyperparathyroidism, and bone disease associated with increase in blood parathyroid hormone level, said method comprising administering to a patient in need thereof a composition comprising an effective amount of the compound of claim 2.

18. A method of treating condition selected from the group consisting of hyperparathormonemia, hyperparathyroidism, and bone disease associated with increase in blood parathyroid hormone level, said method comprising administering to a patient in need thereof a composition comprising an effective amount of the compound of claim 9.