PATENT DOCUMENT

Abstract:
The present invention provides a compound of the formula (I) and pharmaceutically acceptable salts having useful antiviral activity against viruses of the herpes family. In said formula, X=O, (CH 2 ) m , S, SO, SO 2 , NH, NR 8  or a chemical bond; Y=O, (CH 2 ) m , S, SO, SO 2 , NH, NR 8 ; Z=NH, O, NR 8 , S, SO, SO 2 . The remaining substituents are described in the specification.

Full Description:
FIELD OF THE INVENTION  
         [0001]    The present invention relates to compounds possessing antiviral activity against viruses of the herpes family, or a composition containing them. These compounds provide a method for treating herpes viral infections, including condition caused by herpes simplex I such as cold sores, herpes simplex II such as genital herpes, as well as shingles caused by herpes zoster and infections caused by cytomegalovirus, Epstein Barr Virus.  
         BACKGROUND OF THE INVENTION  
         [0002]    Various subfamilies of herpes viruses (Herpes viridae) exist: α-herpesvirinae, β-herpesvirinae, γ-herpesvirinae and cercopithecing Herpes virus I (B virus); some specific viruses are: Herpes simplex virus-1 (HSV-1), Herpes simplex virus-2 (HSV-2), Cytomegalovirus (CMV), Varicella Zoster virus (VZV), Epstein-Barr virus (EBV), human herpes virus-6 (HHV-6), human herpes virus-7 (HHV-7), human herpes virus-8 (HHV) as well as others which may not yet be defined.  
           [0003]    The incidence of infections by Herpes simplex virus is very high throughout the world. Serological studies showed that herpes viral infections affect a substantial percentage of the population. Reactivation of herpes virus infections may lead to recurrent infections. The risk of severe diseases increases with decreasing immunocompetence of the host. There is a pressing need for improved therapy for treating this disease. Currently, exclusive of vaccines, treatment involves primarily nucleoside drugs such as acyclovir, which target thymidine kinase and suffer from development of resistance.  
         SUMMARY OF THE INVENTION  
         [0004]    The present invention provides a compound of the formula and its pharmaceutically acceptable salts, or the compound and its pharmaceutical composition having useful antiviral activity against viruses of the herpes family.  
                         
 
           [0005]    wherein:  
           [0006]    X=O, (CH 2 ) m , S, SO, S 2 , NH, NR 8  or a chemical bond;  
           [0007]    Y=O, (CH 2 ) m , S, SO, S 2 , NH, NR 8 ;  
           [0008]    Z=N, NH, O, NHR 8 , NR 8 , S, SO, S 2 ;  
           [0009]    n=an integer of from 0 to 2;  
           [0010]    m=an integer of 1,2, or 3;  
           [0011]    R 1 , R 2 , R 3 , R 4 , R 5  independently are hydrogen, halogen, hydroxyl, amino, mono or dialkylamino, cyano, nitro, alkyl groups (1-6 carbon atoms), alkoxy groups (1-6 carbon atoms), CF 3 , OCF 3 , aminoalkyl (1-6 carbon atoms), aminoaryl, Oaryl, or a heterocyclic ring having 5-7 atoms with 1-4 hetero atoms of N, O or S;  
           [0012]    Ar=phenyl,  
           [0013]    substituted phenyl,  
           [0014]    benzoheterocyclic ring,  
           [0015]    substituted benzoheterocyclic ring,  
           [0016]    heterocyclic ring, or  
           [0017]    substituted heterocyclic ring, which have substitutions R 6  or R 7 ;  
           [0018]    R 6  and R 7  are independently hydrogen, alkyl group (1-6 carbon atoms), cycloalkyl (3-12 carbon atoms), halogen, alkoxy, CF 3 , aminoalkyl (1-6 carbon atoms), aminoaryl, or a heterocyclic ring of from 5-7 atoms with 1-4 heteroatoms of N, O or S;  
           [0019]    R 6  and R 7  may also form a ring, optionally cycloalkyl or aryl or substituted aryl;  
           [0020]    R 8  is hydrogen, alkyl (1-6 carbon atoms), cycloalkyl (3-12 carbon atoms), phenyl or substituted phenyl wherein the substituents are as defined above.  
           [0021]    The invention also provides for a pharmaceutical composition for the treatment of infection or disease caused by a virus, optionally a Herpes virus which comprises an amount of the compound of claim 1 sufficient to provide an antivirally effective dosage of the compound of Formula I and a pharmaceutically effective carrier.  
           [0022]    The invention also provides for a method of treatment of infection or disease caused by a virus, optionally a Herpes virus which comprises administering to a subject in need of such treatment an effective antivirally dosage of a composition of formula I.  
         DESCRIPTION OF PREFERRED EMBODIMENTS  
         [0023]    The present invention pertains to anti viral compounds. Preferred compounds are as follows:  
           [0024]    One preferred compound is:  
                         
 
           [0025]    Another preferred compound is:  
                         
 
           [0026]    Another preferred compound is:  
                         
 
           [0027]    Another preferred compound is:  
                         
 
           [0028]    Another preferred compound is:  
                         
 
           [0029]    Another preferred compound is:  
                         
 
           [0030]    Another preferred compound is:  
                         
 
           [0031]    The term “alkyl” means a straight or branched hydrocarbon radical having from 1 to 12 carbon atoms unless otherwise specified and includes, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, and dodecyl. The alkyl group may be unsubstituted or independently substituted by from 1 to 3 substituents selected from F, Cl, Br, I, OH, NH 2 , SH, CN, NO 2 , OCH 3 , OCH 2 CH 2 OH, NHCH 3 , or N(CH 3 ) 2 .  
           [0032]    The term “cycloalkyl” means a hydrocarbon ring, which contains from 3 to 12 carbon atoms unless otherwise specified, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl. Where possible, the cycloalkyl group may contain double bonds. The cycloalkyl ring may be unsubstituted or substituted by from 1 to 3 substituents selected from alkyl, cycloalkyl, alkoxy, thioalkoxy all as defined herein, hydroxy, thiol, nitro, halogen, amino, formyl, carboxyl, nitrile, —NH—CO—R, —CO—NHR—, —CO 2 R, —COR, aryl, or heteroaryl wherein alkyl (R), aryl, and heteroaryl are defined as herein.  
           [0033]    The term “alkoxy” having 1-6 carbon atoms means a C 1 -C 6  alkyl-O— group or radical wherein C 1 -C 6  alkyl has the meaning as defined above. Illustrative examples of a straight or branched alkoxy group or radical having from 1 to 6 carbon atoms, also known as a C 1 -C 6  alkoxy, include methoxy, ethoxy, 1-propoxy, 2-propoxy, 1-butoxy, 2-butoxy, 2-methyl-1-propoxy, and 1,1-dimethylethoxy, 1-pentoxy, 2-pentoxy, 3-pentoxy, 2,2-dimethylpropoxy, 1-hexoxy, 2-hexoxy, 3-hexoxy, and 4-methyl-1-pentoxy.  
           [0034]    The term “thioalkoxy” having 1-6 carbon atoms means a C 1 -C 6  alkyl-S— group or radical wherein C 1 -C 6  alkyl has the meaning as defined above. Illustrative examples of a straight or branched thioalkoxy group or radical having from 1 to 6 carbon atoms, also known as a C 1 -C 6  thioalkoxy, include methylthio, ethylthio, 1-propylthio, 2-propylthio, 1-butylthio and 1-pentylthio, 2-pentylthio, 3-pentylthio, 2,2-dimethylpropylthio, 1-hexylthio, 2-hexylthio, 3-hexylthio, and 4-methyl-1-pentylthio.  
           [0035]    The term “aryl” means an aromatic carbocyclic ring having from 6 to 10 carbon atoms. Illustrative examples of an aryl group or radical include phenyl, 1-naphthyl, and 2-napthyl. The aryl group may be unsubstituted or independently substituted by from 1 to 3 substituents selected, unless otherwise specified, from F, Cl, Br, I, OH, NH 2 , SH, CN, NO 2 , OCH 3 , OCH 2 CH 2 OH, NHCH 3 , or N(CH 3 ) 2 .  
           [0036]    The term “Oaryl” means an aryl-O— group or radical wherein aryl has the meaning as defined above. Illustrative examples of an Oaryl group or radical include phenoxy, 1-naphthyloxy, and 2-napthyloxy. Oaryl groups may be unsubstituted or independently substituted by from 1 to 3 substituents selected, unless otherwise specified, from F, Cl, Br, I, OH, NH 2 , SH, CN, NO 2 , OCH 3 , OCH 2 CH 2 OH, NHCH 3 , or N(CH 3 ) 2 .  
           [0037]    The term “halogen” means bromine, chlorine, fluorine or iodine.  
           [0038]    The term “monoalkylamino” means an NH-alkyl group or radical wherein alkyl has the meaning as defined above.  
           [0039]    The term “dialkylamino” means an N-(alkyl) 2  group or radical wherein alkyl has the meaning as defined above.  
           [0040]    The term “aminoalkyl” having 1-6 carbon atoms means an H 2 N-(C 1 -C 6  alkyl)-group or radical wherein C 1 -C 6  alkyl has the meaning as defined above. The aminoalkyl group is a substituted C 1 -C 6  alkyl group or radical containing at least one substituent which is NH 2 .  
           [0041]    The term “aminoaryl” means an H 2 N-aryl-group or radical wherein aryl has the meaning as defined above. The aminoaryl group is a substituted aryl group or radical containing at least one substituent which is NH 2 .  
           [0042]    The term “carbocycle” means cycloalkyl as defined above.  
           [0043]    The term “heteroatom” means a nitrogen, sulfur, or oxygen.  
           [0044]    The term “heterocycle” means a heterocyclic radical which are 5-7 atoms having 1-4 heteroatoms and are selected from: furan, pyrrole, thiophene, oxazole, isoxazole, thiazole, pyrazole, 1,2,3-triazole, 1,2,4-triazole, tetrazole, pyridine, pyridazine, pyrimidine, pyrazine, tetrahydrofuran, tetrahydrothiophene, pyrrolidine, piperazine, piperidine, morpholine, thiomorpholine, oxolane, dioxane, sulfolane, unsubstituted or substituted by 1 to 2 substituents selected from alkyl as defined above. For heterocycles containing sulfur, the oxidized sulfur heterocycles containing SO or SO 2  groups are also included.  
           [0045]    The term “benzoheterocyclic ring” (“fused heterocycle”) refers to a heterocycle that is adjoined at two consecutive positions with a phenyl ring or another heterocycle, such rings may include 2-, 3-, 4-, 5-, 6-, 7-, or 8-quinolinyl, 1-, 3-, 4-, 5-, 6-, 7-, or 8-isoquinolinyl, 2-, 3-, 4-, 5-, 6-, or 7-indolyl, 2-, 3-, 4-, 5-, 6-, or 7-benzo[b]thienyl, 2-, 4-, 5-, 6-, or 7-benzoxazolyl, 2-, 4-, 5-, 6-, or 7-benzimidazol, 2-, 4-, 5-, 6-, or 7-benzothiazolyl.  
           [0046]    Some of the compounds of Formula I are capable of further forming pharmaceutically acceptable acid-addition and/or base salts. All of these forms are within the scope of the present invention.  
           [0047]    Pharmaceutically acceptable acid addition salts of the compounds of Formula I include salts derived from nontoxic inorganic acids such as hydrochloric, nitric, phosphoric, sulfuric, hydrobromic, hydriodic, hydrofluoric, phosphorous, and the like, as well as the salts derived from nontoxic organic acids, such as aliphatic mono- and dicarboxylic acids, phenyl-substituted alkanoic acids, hydroxy alkanoic acids, alkanedioic acids, aromatic acids, aliphatic and aromatic sulfonic acids, etc. Such salts thus include sulfate, pyrosulfate, bisulfate, sulfite, bisulfite, nitrate, phosphate, monohydrogenphosphate, dihyrogenphosphate, metaphosphate, pyrophosphate, chloride, bromide, iodide, acetate, trifluoroacetate, propionate, caprylate, isobutyrate, oxalate, malonate, succinates suberate, sebacate, fumarate, maleate, mandelate, benzoate, chlorobenzoate, methylbenzoate, dinitrobenzoate, phthalate, benzenesulfonate, toluenesulfonate, phenylacetate, citrate, lactate, maleate, tartrate, methanesulfonate, and the like. Also contemplated are salts of amino acids such as arginate and the like and gluconate, galacturonate (see, for example, Berge S. M., et al., “Pharmaceutical Salts,”  Journal of Pharmaceutical Science,  1977;66:1-19.  
           [0048]    The acid addition salt of said basic compounds are prepared by contacting the free base form with a sufficient amount of the desired acid to produce the salt in the conventional manner.  
           [0049]    Pharmaceutically acceptable base addition salts are formed with metals or amines, such as alkali and alkaline earth metals or organic amines. Examples of metals used as cations are sodium, potassium, magnesium, calcium, and the like. Examples of suitable amines are N,N′-dibenzylethylenediamine, chloroprocaine, choline, diethanolamine, dicyclohexylamine, ethylenediamine, N-methylglucamine, and procaine (see, for example, Berge, supra., 1977).  
           [0050]    The base addition salts of said acidic compounds are prepared by contacting the free acid form with a sufficient amount of the desired base to produce the salt in the conventional manner.  
           [0051]    Certain of the compounds of the present invention can exist in unsolvated forms as well as solvated forms, including hydrated forms. In general, the solvated forms, including hydrated forms, are equivalent to unsolvated forms and are intended to be encompassed within the scope of the present invention.  
           [0052]    Certain of the compounds of the present invention possess one or more chiral centers and each center may exist in the R(D) or S(L) configuration. The present invention includes all enantiomeric and epimeric forms as well as the appropriate mixtures thereof. Configuration drawn is most preferred.  
           [0053]    The compounds of the present invention can be prepared and administered in a wide variety of oral and parenteral dosage forms. Thus, the compounds of the present invention can be administered by injection, that is, intravenously, intramuscularly, intracutaneously, subcutaneously, intraduodenally, or intraperitoneally. Also, the compounds of the present invention can be administered by inhalation, for example, intranasally. Additionally, the compounds of the present invention can be administered transdermally. It will be obvious to those skilled in the art that the following dosage forms may comprise as the active component, either a compound of Formula I or a corresponding pharmaceutically acceptable salt of a compound of Formula I.  
           [0054]    For preparing pharmaceutical compositions from the compounds of the present invention, pharmaceutically acceptable carriers can be either solid or liquid. Solid form preparations include powders, tablets, pills, capsules, cachets, suppositories, and dispersible granules. A solid carrier can be one or more substances, which may also act as diluents, flavoring agents, binders, preservatives, tablet disintegrating agents, or an encapsulating material.  
           [0055]    In powders, the carrier is a finely divided solid, which is in a mixture with the finely divided active component.  
           [0056]    In tablets, the active component is mixed with the carrier having the necessary binding properties in suitable proportions and compacted in the shape and size desired.  
           [0057]    The powders and tablets preferably contain from five or ten to about seventy percent of the active compound. Suitable carriers are magnesium carbonate, magnesium stearate, talc, sugar, lactose, pectin, dextrin, starch, gelatin, tragacanth, methylcellulose, sodium carboxymethylcellulose, a low melting wax, cocoa butter, and the like. The term “preparation” is intended to include the formulation of the active compound with encapsulating material as a carrier providing a capsule in which the active component with or without other carriers, is surrounded by a carrier, which is thus in association with it. Similarly, cachets and lozenges are included. Tablets, powders, capsules, pills, cachets, and lozenges can be used as solid dosage forms suitable for oral administration.  
           [0058]    For preparing suppositories, a low melting wax, such as a mixture of fatty acid glycerides or cocoa butter, is first melted, and the active component is dispersed homogeneously therein, as by stirring. The molten homogenous mixture is then poured into convenient sized molds, allowed to cool, and thereby to solidify.  
           [0059]    Liquid form preparations include solutions, suspensions, and emulsions, for example, water or water propylene glycol solutions. For parenteral injection, liquid preparations can be formulated in solution in aqueous polyethylene glycol solution.  
           [0060]    Aqueous solutions suitable for oral use can be prepared by dissolving the active component in water and adding suitable colorants, flavors, stabilizing and thickening agents as desired.  
           [0061]    Aqueous suspensions suitable for oral use can be made by dispersing the finely divided active component in water with viscous material, such as natural or, synthetic gums, resins, methylcellulose, sodium carboxymethylcellulose, and other well-known suspending agents.  
           [0062]    Also included are solid form preparations, which are intended to be converted, shortly before use, to liquid form preparations for oral administration. Such liquid forms include solutions, suspensions, and emulsions. These preparations may contain, in addition to the active component, colorants, flavors, stabilizers, buffers, artificial and natural sweeteners, dispersants, thickeners, solubilizing agents, and the like.  
           [0063]    The pharmaceutical preparation is preferably in unit dosage form. In such form the preparation is divided into unit doses containing appropriate quantities of the active component. The unit dosage form can be a packaged preparation, the package containing discrete quantities of preparation, such as packeted tablets, capsules, and powders in vials or ampoules. Also, the unit dosage form can be a capsule, tablet, cachet, or lozenge itself or it can be the appropriate number of any of these in packaged form.  
           [0064]    The quantity of active component in a unit dose preparation may be varied or adjusted from 0.1 mg to 100 mg preferably 0.5 mg to 100 mg according to the particular application and the potency of the active component. The composition can, if desired, also contain other compatible therapeutic agents.  
           [0065]    In therapeutic use as antagonists of a virus, as agents for the treatment of infections caused by a virus or as agents for the treatment of diseases due to a virus, the compounds utilized in the pharmaceutical method of this invention are administered at the initial dosage of about 0.01 mg to about 100 mg/kg daily. A daily dose range of about 0.01-mg to about 10 mg/kg is preferred. The dosages, however, may be varied depending upon the requirements of the patient, the severity of the condition being treated, the compound being employed. Determination of the proper dosage for a particular situation is within the skill of the art. Generally, treatment is initiated with smaller dosages, which are less than the optimum dose of the compound. Thereafter, the dosage is increased by small increments until the optimum effect under the circumstances is reached. For convenience, the total daily dosage may be divided and administered in portions during the day, if desired.  
           [0066]    General Procedure 1 (for Singleton Synthesis):  
           [0067]    Reductive Amination of Aryl Amines with Aldehydes or Ketones.  
           [0068]    Reagent 2 (1 eq.) was taken in a solvent (dichloromethane, 1,2-dichloroethane or tetrahydrofuran or diethyl ether) and to it reagent 1 (1 to 1.2 eq.) was added. To this solution cooled at 0° C. was added a reducing agent (sodium cyanoborohydride or sodium triacetoxyborohydride) (1 to 2 eq.). To it a drop of acetic acid was added and kept under stirring at room temperature for 6 to 24 hours. The excess hydride was quenched by adding methanol. The reaction mixture was diluted with ethyl acetate and washed with saturated ammonium chloride solution, aqueous sodium bisulfite and brine; dried over anhydrous magnesium sulfuate or sodium sulphate. Organic layer was concentrated and crude product was purified by flash silica gel chromatography to afford the final product. The products were characterized by spectral data. The compounds synthesized using this procedure are shown in Table 4.  
           [0069]    General Procedure 2 for Multiple, Simultaneous Solution Phase Synthesis (Combinatorial Chemistry Synthesis):  
                         
 
           [0070]    To a 2-dram glass vial were added, by Tecan liquid handling robot, a solution of reagent 2 (0.05 mmol) in trimethyl orthoformate (0.2 ml) followed by reagent 1 (0.05 mmol) in trimethyl orthoformate (0.2 ml). The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight), then concentrated to dryness. To each vial was added, by Tecan™ liquid handling robot, 1,2-dichloroethane (1 ml). Solid sodium triacetoxyborohydride (˜23 mg) was added manually to each vial. A a solution of acetic acid (0.05 mmol) in dichloroethane (0.05 ml) was added to each vial by Tecan™ liquid handling robot. The vial was again capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by Tecan liquid handling robot, methanol (1 ml). The reaction mixture was then transferred, by Tecan liquid handling robot, to be prewashed (That is washed with methanol (2 ml) and dichloroethane (1 ml)) BAKERBOND spe™ Aromatic Sulfonic Acid (SO 3 H) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2×1 ml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3×1 ml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromotography mass spec).  
           [0071]    General Procedure 3 for Multiple, Simultaneous Solution Phase Synthesis (Combinatorial Chemistry Synthesis):  
                         
 
           [0072]    To a 2-dram glass vial were added, by Tecan™ liquid handling robot, a solution of reagent 2 (0.05 mmol) in N,N-dimethylformamide (0.1 ml) followed by reagent 1 (0.05 mmol) in N,N-dimethylformamide (0.1 ml). Each vial was treated with trimethylorthoformate (0.2 ml) by Tecan™ liquid handling robot. The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight), then concentrated to dryness. To each vial was added, by Tecan™ liquid handling robot, 1,2-dichloroethane (1 ml). Solid sodium triacetoxyborohydride (˜23 mg) was added manually to each vial. A solution of acetic acid (0.05 mmol) in 1,2-dichloroethane (0.05 ml) was added to each vial by Tecan™ liquid handling robot. The vial was again capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by Tecan™ liquid handling robot, methanol (1 ml). The reaction mixture was then transferred, by Tecan™ liquid handling robot, to be prewashed (That is washed with methanol (2 ml) and 1,2-dichloroethane (1 ml)) BAKERBOND spe™ Aromatic Sulfonic Acid (SO 3 H) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2×1 ml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3×1 ml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromatography mass spec).  
           [0073]    General Procedure 4 for Multiple, Simultaneous Solution Phase Synthesis (Combinatorial Chemistry Synthesis):  
                         
 
           [0074]    To a 2-dram glass vial were added, by Tecan™ liquid handling robot, a solution of reagent 2 (0.05 mmol) in methanol (0.2 ml) followed by reagent 1 (0.2 mmol) in methanol (0.2 ml). To each vial was added, by Tecan™ liquid handling robot, a 1N solution of sodium cyanoborohydride in methanol (0.2 ml) and a 10% acetic acid in methanol (0.05 ml) solution. The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight), then concentrated to dryness. The vial was again capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by Tecan™ liquid handling robot, methanol (1 ml). The reaction mixture was then transferred, by Tecan™ liquid handling robot, to be prewashed (That is washed with methanol (2 ml) and 1,2-dichloroethane (1 ml)) BAKERBOND spe™ Aromatic Sulfonic Acid (SO 3 H) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2×1 ml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3×1 ml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromatography mass spec).  
           [0075]    General Procedure 5 for Multiple, Simultaneous Solution Phase Synthesis (Combinatorial Chemistry Synthesis):  
                         
 
           [0076]    To a 2-dram glass vial were added, by Tecan™ liquid handling robot, a solution of reagent 2 (0.05 mmol) in 1,2-dichloroethane (0.2 ml) followed by reagent 1 (0.15 mmol) in 1,2-dichloroethane (0.1 ml). To each vial solid sodium triacetoxyborohydride (˜25 mg) was added manually. A solution of acetic acid (0.05 mmol) in 1,2-dichloroethane (0.05 ml) was added to each vial by Tecan™ liquid handling robot. The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by Tecan™ liquid handling robot, methanol (1 ml). The reaction mixture was then transferred, by Tecan™ liquid handling robot, to be prewashed (washed with methanol (2 ml) and 1,2-dichloroethane (1 ml)) BAKERBOND spe™ Aromatic Sulfonic Acid (SO 3 H) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2×1 ml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3×1 ml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromatography mass spec).  
           [0077]    General Procedure 6 for Multiple, Simultaneous Solution Phase Synthesis (Combinatorial Chemistry Synthesis):  
                         
 
           [0078]    To a 2-dram glass vial were added, by Tecan™ liquid handling robot, a solution of reagent 2 (0.05 mmol) in methanol (0.2 ml) followed by reagent 1 (0.15 mmol) in methanol (0.1 ml). To each vial was added a 1N solution of sodium cyanoborohydride in methanol (0.1 ml) and a 10% acetic acid in methanol solution (0.05 ml). The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by Tecan™ liquid handling robot, methanol (1 ml). The reaction mixture was then transferred, by Tecan™ liquid handling robot, to be prewashed (washed with methanol (2 ml) and 1,2-dichloroethane (1 ml)) BAKERBOND spe™ Aromatic Sulfonic Acid (SO 3 H) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2×1 ml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3×1 ml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromatography mass spec).  
           [0079]    General Procedure 7 for Multiple, Simultaneous Solution Phase Synthesis (Combinatorial Chemistry Synthesis):  
                         
 
           [0080]    To a 2-dram glass vial were added, by Tecan™ liquid handling robot, a solution of reagent 2 (0.05 mmol) followed by reagent 1 in N,N-dimethylformamide (0.32 ml) or methanol (0.2 ml). The vials were then concentrated overnight to dryness. Each vial was treated by Tecan™ liquid handling robot with reagent 1 (0.15 mmol) in methanol (0.1 ml) and methanol (0.2 ml). To each vial was added a 1N solution of sodium cyanoborohydride in methanol (0.1 ml) and a 10% acetic acid in methanol solution (0.05 ml). The vial was capped and the reaction mixture was shaken at room temperature for 18 hours (overnight). To the reaction mixture was added, by Tecan™ liquid handling robot, methanol (1 ml). The reaction mixture was then transferred, by Tecan™ liquid handling robot, to be prewashed (washed with methanol (2 ml) and 1,2-dichloroethane (1 ml)) BAKERBOND spe™ Aromatic Sulfonic Acid (SO 3 H) disposable Extraction Columns. The columns were allowed to drain and then washed with methanol (2×1 ml) these solvents were discarded. The desired product was eluted from the column using a solution of 2M ammonia in methanol (3×1 ml) and concentrated to dryness in a tared 2-dram vial. The product was analyzed by LCMS (liquid chromatography mass spec).  
           [0081]    Synthesis of Compound 450: To dibenzofuran-2-yl-amine (0.91 g, 5 mmol) taken in dichloromethane (75 mL) was added α,α′-dibromo-ortho-xylene (1.85 g, 7 mmol) followed by triethylamine (3.03 g, 30 mmol). The reaction was stirred at room temperature for 24 hours. The solvents were evaporated and the residue was purified by flash silica gel chromatography to give the title compound (1.43 g).  
           [0082]    Synthesis of Compound 451: To dibenzofuran-2-yl-amine (0.91 g, 5 mmol) taken in dichloromethane (75 mL) was added phthaloyl dichloride (1.16 g, 6 mmol) followed by triethylamine (3.03 g, 30 mmol). The reaction was stirred at room temperature for 5 minutes. The reaction was quenched with sodium bicarbonate solution and the organic layer was separated. The crude product was purified by flash silica gel chromatography to give the title compound (0.51 g).  
           [0083]    Synthesis of Compound 463: To compound 58 (0.25 g, 0.87 mmol) taken in tetrahydrofuran (10 mL) was added sodium hydride (60% in mineral oil, 0.035 g, 0.87 mmol). To it methyl iodide (0.25 g, 1.74 mmol) was added. The reaction was stirred at room temperature for 24 hours. The solvents were evaporated and the residue was purified by flash silica gel chromatography to give the title compound (0.18 g).  
           [0084]    Deprotection of t-butyloxycarbonyl group: The general procedure for the removal of tert-butyoxycarbonyl (Boc) group is as follows: To the compound taken a flask was added hydrochloric acid in an appropriate solvent (dioxane, methanol, 1,2-dichloromethane and the reaction was kept under shaking for 5 to 18 hours. Removal of volatiles furnished the corresponding product.  
           [0085]    Reagents 1 are shown in Table 1.  
                                   TABLE 1                           Aldehydes/ketones (reagent 1)            No.   Reagent 1 (aldehydes/ketones)                    1   o-tolualdehyde       2   meta-tolualdehyde       3   para-tolualdehyde       4   2-fluorobenzaldehyde       5   3-fluorobenzaldehyde       6   4-fluorobenzaldehyde       7   4-tert-butylbenzaldehyde       8   α,α,α-Trilfluoro-o-tolualdehyde       9   α,α,α-Trilfluoro-m-tolualdehyde       10   α,α,α-Trilfluoro-p-tolualdehyde       11   o-anisaldehyde       12   m-anisaldehyde       13   p-anisaldehyde       14   Salicylaldehyde       15   3-hydroxybenzaldehyde       16   4-hydroxybenzaldehyde       17   2-chlorobenzaldehyde       18   3-chlorobenzaldehyde       19   4-chlorobenzaldehyde       20   3-benzyloxybenzaldehyde       21   4-benzyloxybenzaldehyde       22   2,3-dimethoxybenzaldehyde       23   2,4-dimethoxybenzaldehyde       24   2,5-dimethoxybenzaldehyde       25   2,6-dimethoxybenzaldehyde       26   3,4-dimethoxybenzaldehyde       27   3,5-dimethoxybenzaldehyde       28   1,4-Benzodioxan-6-carboxaldehyde       29   2,4-dimethylbenzaldehyde       30   2,5-dimethylbenzaldehyde       31   2,3-difluorobenzaldehyde       32   2,4-difluorobenzaldehyde       33   2,5-difluorobenzaldehyde       34   2,6-difluorobenzaldehyde       35   3,4-difluorobenzaldehyde       35   3,5-difluorobenzaldehyde       37   2,3,4-trifluorobenzaldehyde       38   2,3,6-trifluorobenzaldehyde       39   3-fluoro-2-methylbenzaldehyde       40   3-fluoro-p-anisaldehyde       41   2-pyridinecarboxaldehyde       42   3-pyridinecarboxaldehyde       43   4-pyridinecarboxaldehyde       44   4-pyridinecarboxaldehyde N-oxide       45   6-methyl-2-pyridinecarboxaldehyde       46   3-furaldehyde       47   2-furaldehyde       48   5-chloro-2-thiophenecarboxaldehyde       49   3-thiophenecarboxaldehyde       50   2-thiophenecarboxaldehyde       51   pyrrole-2-carboxaldehyde       52   1-methyl-2-pyrrolecarboxaldehyde       53   1-naphthaldehyde       54   2-naphthaldehyde       55   2-quinolinecarboxaldehyde       56   3-quinolinecarboxaldehyde       57   4-quinolinecarboxaldehyde       58   indole-3-carboxaldehyde       59   2-bromobenzaldehyde       60   2-chlorobenzaldehyde       61   2-ethoxybenzaldehyde       62   2-cyanobenzaldehyde       63   5-(2-chlorophenyl)furfural       64   5-(3-chlorophenyl)furfural       65   5-(4-chlorophenyl)furfural       66   2-thiazolecarboxaldehyde       67   2-imidazolecarboxaldehyde       68   4(5)-imidazolecaboxaldehyde       69   5-nitro-2-thiophenecarboxaldehyde       70   2-nitrobenzaldehyde       71   4-formyluracil       72   4-acetoxybenzaldehyde       73   4-(dimethylamino)benzaldehyde       74   1-acetyl-3-indolecarboxaldehyde       75   4-bromo-2-thiophenecarboxaldehyde       76   Piperonal       77   3-trifluoromethoxybenzaldehyde       78   4-chloro-3-nitro-benzaldehyde       79   Benzaldehyde       80   3-benzyloxybenzaldehyde       81   3-phenoxybenzaldehyde       82   2-butanone       83   2-Pentanone       84   3-Methyl-2-butanone       85   Tetrahydrothiophene-3-one       86   Tetrahydrothiopyran-4-one       87   Cycloheptanone       88   Cyclooctanone       89   Cyclohexylmethylketone       90   4-Methyl-2-pentanone       91   3-Pentanone       92   3-Hexanone       93   4-Hydroxy-3-methyl-2-butanon       94   2-Methoxyphenylacetone       95   4-nitrobenzaldehyde       96   4-(methylthio)benzaldehyde       97   Propionaldehyde       98   Isovaleraldehyde       99   3-(methylthio)propionaklehyde       100   1-phenyl-2-pentanone       101   Acetone       102   Cyclopropyl methyl ketone       103   Cyclohexanone       104   n-tert-butoxycarbonyl-4-piperidone       105   3,3,5,5-tetramethylcyclohexanone       106   1-decalone       107   4-cyclohexylcyclohexanone       108   2-norbornanone       109   4-tert-butylcyclohexanone       110   Cyclopentanone       111   2-adamantanone       112   Bicyclo[3,2,1]octan-2-one       113   1,1-dioxo-tetrahydro-thiopyran-4-one                  
 
           [0086]    Reagent 2 (amines) used in the above general procedures are shown in Table 2:  
                             TABLE 2                       No.   Reagent 2 (amines)                                1   Dibenzofuran-2-yl-methyl-amine       2   8-fluoro-dibenzofuran-2-yl-amine       3   8-chloro-dibenzofuran-2-yl-amine       4   8-amino-dibenzofuran-2-ol       5   3-methoxy-diebenzofuran-2-yl-amine       6   9H-Fluoren-3-yl-amine       7   9H-Fluorene-2-yl-amine       8   Dibenzofuran-4-yl-amine       9   Benzo[4,5]furo[2,3-H]pyridin-3-yl-amine       10   9-Ethyl-9H-carbazol-3-ylamine       11   3-Amino-carbazole-9-carboxylic acid tert-butyl ester       12   Dibenzofuran-2-yl-methyl-amine       13   Dibenzofuran-2-yl-dimethyl-amine       14   Dibenzothiophene-2-yl-amine       15   Dibenzothiophene-3-yl-amine       16   6-Amino-1,2,3,4-tetrahydro-carbazole-9-carboxylic acid           tert-butyl ester       17   Dibenzo[1,4]dioxin-2-yl-amine       18   Phenoxanthiin-3-yl-amine       19   10-Oxa-9-thia-1-aza-anthracen-3-yl-amine       20   10H-Benzo-b]pyrido[2,3-e][1,4]oxazin-3-ylamine acetic acid,           tert-butyl ester       21   Anthracen-2-yl-amine       22   10,111-Dihydro-5H-diebnzo[b,f]azepin-3-yl-amine       23   6,7,8,9-Tetrahydro-5H-carbazol-3-yl-amine       24   7-Amino-1-aza-phenoxathiin                  
 
           [0087]    The compounds of Formula I include:  
           [0088]    1 (1-Cyclopropyl-ethyl)-(2-methoxy-dibenzofuran-3-yl)-amine  
           [0089]    2 Cyclopentyl-(9H-fluoren-2-yl)-amine  
           [0090]    3 (1-Cyclopropyl-ethyl)-(9H-fluoren-2-yl)-amine  
           [0091]    4 N 3 -Cyclopentyl-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine  
           [0092]    5 Isopropyl-(2-methoxy-dibenzofuran-3-yl)-amine  
           [0093]    6 (2-Methoxy-dibenzofuran-3-yl)-(tetrahydro-thiopyran-4-yl)-amine  
           [0094]    7 Cycloheptyl-(2-methoxy-dibenzofuran-3-yl)-amine  
           [0095]    8 (1-Ethyl-propyl)-(2-methoxy-dibenzofuran-3-yl)-amine  
           [0096]    9 sec-Butyl-(2-methoxy-dibenzofuran-3-yl)-amine  
           [0097]    10 N 2 ,N 2 -Dimethyl-N 3 -piperidin-4-yl-9H-fluorene-2,3-diamine  
           [0098]    11 N 3 -(1-Benzyl-butyl)-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine  
           [0099]    12 (9H-Fluoren-2-yl)-piperidin-4-yl-amine  
           [0100]    13 (1-Benzyl-butyl)-(9H-fluoren-2-yl)-amine  
           [0101]    14 sec-Butyl-(9H-fluoren-2-yl)-amine  
           [0102]    15 (1,1-Dioxo-hexahydro-thiopyran-4-yl)-(2-methoxy-dibenzofuran-3-yl)-amine  
           [0103]    16 Dibenzofuran-2-yl-(3,3,5,5-tetramethyl-cyclohexyl)-amine  
           [0104]    17 (Decahydro-naphthalen-1-yl)-dibenzofuran-2-yl-amine  
           [0105]    18 Adamantan-2-yl-dibenzofuran-2-yl-amine  
           [0106]    19 Bicyclohexyl-4-yl-dibenzofuran-2-yl-amine  
           [0107]    20 Bicyclo[2.2.1]hept-2-yl-dibenzofuran-2-yl-amine  
           [0108]    21 (4-tert-Butyl-cyclohexyl)-dibenzofuran-2-yl-amine  
           [0109]    22 Bicyclo[3.2.1]oct-2-yl-dibenzofuran-2-yl-amine  
           [0110]    23 Cyclopentyl-dibenzofuran-2-yl-amine  
           [0111]    24 Cyclohexyl-(2-methoxy-dibenzofuran-3-yl)-amine  
           [0112]    25 Cyclohexyl-(9H-fluoren-2-yl)-amine  
           [0113]    26 Dibenzofuran-2-yl-bis-(3-methylsulfanyl-propyl)-amine  
           [0114]    27 Dibenzofuran-2-yl-bis-(3-methyl-butyl)-amine  
           [0115]    28 Dibenzofuran-2-yl-dipropyl-amine  
           [0116]    29 N 3 -(1,1-Dioxo-hexahydro-thiopyran-4-yl)-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine  
           [0117]    30 N 3 -Isopropyl-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine  
           [0118]    31 N 2 ,N 2 -Dimethyl-N 3 -(tetrahydro-thiopyran-4-yl)-9H-fluorene-2,3-diamine  
           [0119]    32 N 3 -Cyclohexyl-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine  
           [0120]    33 N 3 -Cycloheptyl-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine  
           [0121]    34 N 3 -(1-Ethyl-propyl)-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine  
           [0122]    35 N 3 -(1-Cyclopropyl-ethyl)-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine  
           [0123]    36 N 3 -sec-Butyl-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine  
           [0124]    37 (9H-Fluoren-2-yl)-isopropyl-amine  
           [0125]    38 (9H-Fluoren-2-yl)-(tetrahydro-thiopyran-4-yl)-amine  
           [0126]    39 Cycloheptyl-(9H-fluoren-2-yl)-amine  
           [0127]    40 Dibenzofuran-2-yl-(1,1-dioxo-hexahydro-thiopyran-4-yl)-amine  
           [0128]    41 Dibenzofuran-2-yl-piperidin-4-yl-amine  
           [0129]    42 Dibenzofuran-2-yl-isopropyl-amine  
           [0130]    43 Cyclohexyl-dibenzofuran-2-yl-amine  
           [0131]    44 (1-Cyclopropyl-ethyl)-dibenzofuran-2-yl-amine  
           [0132]    45 Dibenzofuran-3-yl-(1,1-dioxo-hexahydro-thiopyran-4-yl)-amine  
           [0133]    46 Dibenzofuran-3-yl-piperidin-4-yl-amine  
           [0134]    47 Dibenzofuran-3-yl-isopropyl-amine  
           [0135]    48 Dibenzofuran-3-yl-(tetrahydro-thiopyran-4-yl)-amine  
           [0136]    49 Cyclohexyl-dibenzofuran-3-yl-amine  
           [0137]    50 Cycloheptyl-dibenzofuran-3-yl-amine  
           [0138]    51 (4-Chloro-benzyl)-dibenzofuran-2-yl-amine  
           [0139]    52 (4-Chloro-3-nitro-benzyl)-dibenzofuran-2-yl-amine  
           [0140]    53 Dibenzofuran-2-yl-(3-trifluoromethoxy-benzyl)-amine  
           [0141]    54 Benzo[1,3]dioxol-5-ylmethyl-dibenzofuran-2-yl-amine  
           [0142]    55 Dibenzofuran-2-yl-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-amine  
           [0143]    56 Dibenzofuran-2-yl-(3,5-dimethoxy-benzyl)-amine  
           [0144]    57 Dibenzofuran-2-yl-(4-trifluoromethyl-benzyl)-amine  
           [0145]    58 Dibenzofuran-2-yl-(2-methyl-benzyl)-amine  
           [0146]    59 Dibenzofuran-2-yl-thiophen-3-ylmethyl-amine  
           [0147]    60 Dibenzofuran-2-yl-(4-nitro-benzyl)-amine  
           [0148]    61 Dibenzofuran-2-yl-(4-methylsulfanyl-benzyl)-amine  
           [0149]    62 Dibenzofuran-2-yl-(4-methyl-benzyl)-amine  
           [0150]    63 Benzyl-dibenzofuran-2-yl-amine  
           [0151]    64 (3-Benzyloxy-benzyl)-dibenzofuran-2-yl-amine  
           [0152]    65 (1-Benzyl-butyl)-dibenzofuran-2-yl-amine  
           [0153]    66 Dibenzofuran-2-yl-[2-(2-methoxy-phenyl)-1-methyl-ethyl]-amine  
           [0154]    67 3-(Dibenzofuran-2-ylamino)-2-methyl-butan-1-ol  
           [0155]    68 Dibenzofuran-2-yl-(1-ethyl-butyl)-amine  
           [0156]    69 Dibenzofuran-2-yl-(1-ethyl-propyl)-amine  
           [0157]    70 Dibenzofuran-2-yl-(1,3-dimethyl-butyl)-amine  
           [0158]    71 (1-Cyclohexyl-ethyl)-dibenzofuran-2-yl-amine  
           [0159]    72 Cyclooctyl-dibenzofuran-2-yl-amine  
           [0160]    73 Cycloheptyl-dibenzofuran-2-yl-amine  
           [0161]    74 Dibenzofuran-2-yl-(tetrahydro-thiopyran-4-yl)-amine  
           [0162]    75 Dibenzofuran-2-yl-(tetrahydro-thiophen-3-yl)-amine  
           [0163]    76 Dibenzofuran-2-yl-(1,2-dimethyl-propyl)-amine  
           [0164]    77 Dibenzofuran-2-yl-(1-methyl-butyl)-amine  
           [0165]    78 sec-Butyl-dibenzofuran-2-yl-amine  
           [0166]    79 Benzofurp[3,2-b]pyridin-8-yl-(2-fluoro-benzyl)-amine  
           [0167]    80 Benzofuro[3,3-b]pyridin-8-yl-pyridin4-ylmethyl-amine  
           [0168]    81 Benzofuro[3,2-b]pyridin-8-yl-(2-methyl-benzyl)-amine  
           [0169]    82 N-(2-Fluoro-benzyl)-N′-methyl-dibenzofuran-2,8-diamine  
           [0170]    83 N-Methyl-N′-quinolin-4-ylmethyl-dibenzofuran-2,8-diamine  
           [0171]    84 N-Methyl-N′-naphthanlen-1-ylmethyl-dibenzofuran-2,8-diamine  
           [0172]    85 N-(4-Methanesulfonyl-benzyl)-N′-methyl-dibezofuran-2,8-diamine  
           [0173]    86 N-Methyl-N′-pyridin-4-ylmethyl-dibenzofuran-2,8-diamine  
           [0174]    87 N-Methyl-N′-(2-methyl-benzyl)-dibenzofuran-2,8-diamine  
           [0175]    88 Naphthanlen-1-ylmethyl-(10H-phenothiazin-2-yl)-amine  
           [0176]    89 (4-Methanesulfonyl-benzyl)-(10H-phenothiazin-2-yl)-amine  
           [0177]    90 (3-Fluoro-2-methyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen-6-yl)-amine  
           [0178]    91 (2-Fluoro-2-methyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen-6-yl)-amine  
           [0179]    92 (10-Oxa-9-thia-1-aza-anthracen-6-yl)-qinolin-4-ylmethyl-amine  
           [0180]    93 Naphthalene-1-ylmethyl-(10-oxa-9-thia-1-aza-anthracen-6-yl)-amine  
           [0181]    94 (4-Methanesulfonyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen-6-yl)-amine  
           [0182]    95 (10-Oxa-9-thia-1-aza-anthracen-6-yl)-pyridin-4-ylmethyl-amine  
           [0183]    96 (2-Methyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen-6-yl)-amine  
           [0184]    97 Anthracen-2-yl-quinolin-4-ylmethyl-amine  
           [0185]    98 Anthracen-2-yl-(4-methanesulfonyl-benzyl)-amine  
           [0186]    99 Anthracen-2-yl-pyridin-4-ylmethyl-amine  
           [0187]    100 Anthracen-2-yl-(2-methyl-benzyl)-amine  
           [0188]    101 Dibenzo[b,e][1,4]-dioxin-2-yl-(2-fluoro-benzyl)-amine  
           [0189]    102 Dibenzo[b,e][1,4]dioxin-2-yl-(2-fluoro-benzyl)-amine  
           [0190]    103 Dibenzo[b,e][1,4]fioxin-2-yl-quinolin-4-ylmethyl-amine  
           [0191]    104 Dibenzo[b,e][1,4]fioxin-2-yl-naphthalen-1-ylmethyl-amine  
           [0192]    105 Dibenzo[b,e][1,4]fioxin-2-yl-(4-methanesulfonyl-benzyl)-amine  
           [0193]    106 Dibenzo[b,e][1,4]fioxin-2-yl-pyridin-4-ylmethyl-amine  
           [0194]    107 8-(3-Fluoro-2-methyl-benzylamino)-dibenzofuran-2-ol  
           [0195]    108 8-(2-Fluoro-benzylamino)-dibenzofuran2-ol  
           [0196]    109 8-(4-Methanesulfonyl-benzylamino)-dibenzofuran-2-ol  
           [0197]    110 8-[(Pyridin-4-ylmethyl)-amino]-dibenzofuran-2-ol  
           [0198]    111 8-(2-Methyl-benzylamino)-dibenzofuran-2-ol  
           [0199]    112 (8-Chloro-dibenzofuran-2-yl)-(2-fluoro-benzyl)-amine  
           [0200]    113 8-Chloro-dibenzofuran-2-yl)-naphthalen-1-ylmethyl-amine  
           [0201]    114 8-Chloro-dibenzofuran-2-yl)-(4-methanesulfonyl-benzyl)-amine  
           [0202]    115 (4-Methanesulfonyl-benzyl)-(6,7,8,9-tetrahydro-5H-carbazol-3-yl)-amine  
           [0203]    116 Pyridin-4-ylmethyl-(6,7,8,9-tetrahydro-5H-carbazol-3-yl)-amine  
           [0204]    117 Benzofuro[3,2-b]pyridin-8-yl-(3-fluoro-2-methyl-benzyl)-amine  
           [0205]    118 Dibenzofuran-2-yl-quinolin-4-ylmethyl-amine  
           [0206]    119 Dibenzofuran-2-yl-quinolin-2-ylmethyl-amine  
           [0207]    120 (4-Dimethylamino-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0208]    121 Dibenzofuran-2-yl-(4-dimethylamino-benzyl)-amine  
           [0209]    122 Dibnzofuran-2-yl-(5-nitro-thiophen-2-ylmethyl)-amine  
           [0210]    123 Dibenzofuran-2-yl-thiazol-2-ylmethyl-amine  
           [0211]    124 Benzyl-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0212]    125 N-(-3-Methoxybenzyl)-N′-methyl-dibenzofuran-2,8-diamine  
           [0213]    126 N-(3,5-Dimethoxy-benzyl)-N′-methyl-dibenzofuran-2,8-diamine  
           [0214]    127 N-(4-tert-Butyl-benzyl)-N′-methyl-dibenzofuran-2,8-diamine  
           [0215]    128 N-Benzyl-N′-methyl-dibenzofuran-2,8-diamine  
           [0216]    129 2-[(8-Methylamino-dibenzofuran-2-ylamino)-methyl]-benzonitrile  
           [0217]    130 (4-Methoxy-benzyl)-phenoxathiin-3-yl-amine  
           [0218]    131 (8-Chloro-dibenzofuran-2-yl)-(3-methoxy-benzyl)-amine  
           [0219]    132 (3-Methoxy-benzyl)-phenoxathiin-3-yl-amine  
           [0220]    133 (3,5-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine  
           [0221]    134 (3-Fluoro-4-methoxy-benzyl)-phenoxathiin-3-yl-amine  
           [0222]    135 (4-tert-Butyl-benzyl)-phenoxathiin-3-yl-amine  
           [0223]    136 Benzyl-phenoxathiin-3-yl-amine  
           [0224]    137 (2-Ethoxy-benzyl)-phenoxathiin-3-yl-amine  
           [0225]    138 (8-Chloro-dibenzofuran-2-yl)-(3,5-dimethoxy-benzyl)-amine  
           [0226]    139 (8-Chloro-dibenzofuran-2-yl)-(3-fluoro-4-methoxy-benzyl)-amine  
           [0227]    140 Benzyl-(8-chloro-dibenzofuran-2-yl)-amine  
           [0228]    141 (9H-Fluoren-2-yl)-(4-methoxy-benzyl)-amine  
           [0229]    142 (8-Chloro-dibenzofuran-2-yl)-thiazol-2-ylmethyl-amine  
           [0230]    143 (9H-Fluoren-2-yl)-(3-methoxy-benzyl)-amine  
           [0231]    144 (3,5-Dimethoxy-benzyl)-(9H-fluoren-2-yl)-amine  
           [0232]    145 (9H-Fluoren-2-yl)-(3-fluoro-4-methoxy-benzyl)-amine  
           [0233]    146 (4-tert-Butyl-benzyl)-(9H-fluoren-2-yl)-amine  
           [0234]    147 Benzyl-(9H-fluoren-2-yl)-amine  
           [0235]    148 (9H-Fluoren-2-yl)-thiazol-2-ylmethyl-amine  
           [0236]    149 (2-Ethoxy-benzyl)-(9H-fluoren2-yl-amine  
           [0237]    150 Dibenzofuran-4-yl-(4-methoxy-benzyl)-amine  
           [0238]    151 2-[(8-Chloro-dibenzofuran-2-ylamino)-methyl]-benzonitrile  
           [0239]    152 Dibenzofuran-4-yl-(3-methoxy-benzyl)-amine  
           [0240]    153 Dibenzofuran-4-yl-(3,5-dimethoxy-benzyl)-amine  
           [0241]    154 Dibenzofuran-4-yl-(3-fluoro-4-methoxy-benzyl)-amine  
           [0242]    155 (4-tert-Butyl-benzyl)-dibenzofuran-4-yl-amine  
           [0243]    156 Dibenzofuran-4-yl-(2-ethoxy-benzyl)-amine  
           [0244]    157 N-(4-Methoxy-benzyl)-N′-methyl-dibenzofuran-2,8-diamine  
           [0245]    158 (8-Chloro-dibenzofuran-2-yl)(4-methoxy-benzyl)-amine  
           [0246]    159 (8-Chloro-dibenzofuran-2-yl)-(2-ethoxy-benzyl)-amine  
           [0247]    160 Dibenzofuran-4yl-(2,4-dimethyl-benzyl)-amine  
           [0248]    161 N-Methyl-N′-thiophen-3-ylmethyl-dibenzofuran-2,8-diamine  
           [0249]    162 N-Methyl-N′-pyridin-2-ylmethyl-dibenzofuran-2,8-diamine  
           [0250]    163 (2-Bromo-benzyl)-phenoxathiin-3-yl-amine  
           [0251]    164 Phenoxathiin-3-yl-quinolin-4-ylmethyl-amine  
           [0252]    165 Phenoxathiin-3-yl-thiophen-3-ylmethyl-amine  
           [0253]    166 (3-Methyl-pyridin-2-ylmethyl)-phenoxathiin-3-yl-amine  
           [0254]    167 Phenoxathiin-3-yl-pyridin-3-ylmethyl-amine  
           [0255]    168 Phenoxathiin-3-yl-pyridin-2-ylmethyl-amine  
           [0256]    169 (8-Chloro-dibenzofuran-2-yl)-thiophen-3-ylmethyl-amine  
           [0257]    170 (2-Bromo-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine  
           [0258]    171 (8-Chloro-dibenzofuran-2-yl)-(3-methyl-pyridin-2-ylmethyl)-amine  
           [0259]    172 (9-Ethyl-9H-carbazol-3-yl)-thiophen-3-ylmethyl-amine  
           [0260]    173 (5-Chloro-thiophen-2-ylmethyl)-(9-ethyl-9H-carbazol-3-yl)-amine  
           [0261]    174 (9-Ethyl-9H-carbazol-3-yl)-pyridin-3-ylmethyl-amine  
           [0262]    175 (2-Bromo-benzyl)-(9H-fluoren-2-yl)-amine  
           [0263]    176 (8-Chloro-dibenzofuran-2-yl)-pyridin-4-ylmethyl-amine  
           [0264]    177 (9H-Fluoren-2-yl)-quinolin-2-ylmethyl-amine  
           [0265]    178 (9H-Fluoren-2-yl)-thiophen-3-ylmethyl-amine  
           [0266]    179 (9H-Fluoren-2-yl)-(3-methyl-pyridin-2-ylmethyl)-amine  
           [0267]    180 (9H-Fluoren-2-yl)-pyridin-4-ylmethyl-amine  
           [0268]    181 (9H-Fluoren-2-yl)-pyridin-3-ylmethyl-amine  
           [0269]    182 (9H-Fluoren-2-yl)-pyridin-2-ylmethyl-amine  
           [0270]    183 (8-Chloro-dibenzofuran-2-yl)-pyridin-3-ylmethyl-amine  
           [0271]    184 Dibenzofuran-4-yl-quinolin-4-ylmethyl-amine  
           [0272]    185 Dibenzofuran-4-yl-quinolin-2-ylmethyl-amine  
           [0273]    186 Dibenzofuran-4-yl-thiophen-3-ylmethyl-amine  
           [0274]    187 Dibenzofuran-4-yl-(3-methyl-pyridin-2-ylmethyl)-amine  
           [0275]    188 Dibenzofuran-4-yl-pyridin-4-ylmethyl-amine  
           [0276]    189 Dibenzofuran-4-yl-pyridin-3-ylmethyl-amine  
           [0277]    190 Dibenzofuran-4-yl-pyridin-2-ylmethyl-amine  
           [0278]    191 (2-Bromo-benzyl)-(8-chloro-dibenzofuran-2-yl)-amine  
           [0279]    192 (8-Chloro-dibenzofuran-2-yl)-pyridin-2-ylmethyl-amine  
           [0280]    193 N-Methyl-N′-(2,3,6-trifluoro-benzyl)-dibenzofuran-2,8-diamine  
           [0281]    194 N-Methyl-N′-(2,3,4-trifluoro-benzyl)-dibenzofuran-2,8-diamine  
           [0282]    195 N-(2,6-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-diamine  
           [0283]    196 N-(2,5-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-diamine  
           [0284]    197 N-(2,4-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-diamine  
           [0285]    198 N-(2,3-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-diamine  
           [0286]    199 N-(2,5-Dimethyl-benzyl)-N′-methyl-dibenzofuran-2,8-diamine  
           [0287]    200 N-(2,4-Dimethyl-benzyl)-N′-methyl-dibenzofuran-2,8-diamine  
           [0288]    201 N-(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-N′-methyl-dibenzofuran-2,8-diamine  
           [0289]    202 (3-Fluoro-2-methyl-benzyl)-phenoxathiin-3-yl-amine  
           [0290]    203 (8-Chloro-dibenzofuran-2-yl)-(2,3,6-trifluoro-benzyl)-amine  
           [0291]    204 Phenoxathiin-3-yl-(2,3,6-trifluoro-benzyl)-amine  
           [0292]    205 Phenoxathiin-3-yl-(2,3,4-trifluoro-benzyl)-amine  
           [0293]    206 (2,6-Difluoro-benzyl)-phenoxathiin-3-yl-amine  
           [0294]    207 (2,5-Difluoro-benzyl)-phenoxathiin-3-yl-amine  
           [0295]    208 (2,4-Difluoro-benzyl)-phenoxathiin-3-yl-amine  
           [0296]    209 (2,3-Difluoro-benzyl)-phenoxathiin-3-yl-amine  
           [0297]    210 (2,4-Dimethyl-benzyl)-phenoxathiin-3-yl-amine  
           [0298]    211 (2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-phenoxathiin-3-yl-amine  
           [0299]    212 Benzo[b]thiophen-5-yl-(3-fluoro-2-methyl-benzyl)-amine  
           [0300]    213 (8-Chloro-dibenzofuran-2-yl)-(2,3,4-trifluoro-benzyl)-amine  
           [0301]    214 (8-Chloro-dibenzofuran-2-yl)-(2,6-difluoro-benzyl)-amine  
           [0302]    215 (8-Chloro-dibenzofuran-2-yl)-(2,5-difluoro-benzyl)-amine  
           [0303]    216 (8-Chloro-dibenzofuran-2-yl)-(2,4-difluoro-benzyl)-amine  
           [0304]    217 (9-Ethyl-9H-carbazol-3-yl)-(3-fluoro-2-methyl-benzyl)-amine  
           [0305]    218 (8-Chloro-dibenzofuran-2-yl)-(2,3-difluoro-benzyl)-amine  
           [0306]    219 (9-Ethyl-9H-carbazol-3-yl)-(2,3,6-trifluoro-benzyl)-amine  
           [0307]    220 (9-Ethyl-9H-carbazol-3-yl)-(2,3,4-trifluoro-benzyl)-amine  
           [0308]    221 (2,6-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine  
           [0309]    222 (2,5-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine  
           [0310]    223 (2,4-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine  
           [0311]    224 (2,3-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine  
           [0312]    225 (2,5-Dimethyl-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine  
           [0313]    226 (2,4-Dimethyl-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine  
           [0314]    227 (2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-(9-ethyl-9H-carbazol-3-yl)-amine  
           [0315]    228 (9H-Fluoren-2-yl)-(3-fluoro-2-methyl-benzyl)-amine  
           [0316]    229 (8-Chloro-dibenzofuran-2-yl)-(2,5-dimethyl-benzyl)-amine  
           [0317]    230 (9H-Fluoren-2-yl)-(2,3,6-trifluoro-benzyl)-amine  
           [0318]    231 (9H-Fluoren-2-yl)-(2,3,4-trifluoro-benzyl)-amine  
           [0319]    232 (2,5-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine  
           [0320]    233 (2,4-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine  
           [0321]    234 (2,3-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine  
           [0322]    235 (2,5-Dimethyl-benzyl)-(9H-fluoren-2-yl)-amine  
           [0323]    236 (2,4-Dimethyl-benzyl)-(9H-fluoren-2-yl)-amine  
           [0324]    237 (2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-(9H-fluoren-2-yl)-amine  
           [0325]    238 (8-Chloro-dibenzofuran-2-yl)-(2,4-dimethyl-benzyl)-amine  
           [0326]    239 Dibenzofuran-4-yl-(2,5-dimethyl-benzyl)-amine  
           [0327]    240 Dibenzofuran-4-yl-(3-fluoro-2-methyl-benzyl)-amine  
           [0328]    241 N-(3-Fluoro-2-methyl-benzyl)-N′-methyl-dibenzofuran-2,8-diamine  
           [0329]    242 (8-Chloro-dibenzofuran-2-yl)-(3-fluoro-2-methyl-benzyl)-amine  
           [0330]    243 (8-Chloro-dibenzofuran-2-yl)-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-amine  
           [0331]    244 (2,5-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine  
           [0332]    245 (2,3-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine  
           [0333]    246 (2-Chloro-benzyl)-phenoxathiin-3-yl-amine  
           [0334]    247 (2-Methoxy-benzyl)-phenoxathiin-3-yl-amine  
           [0335]    248 (2-Methyl-benzyl)-phenoxathiin-3-yl-amine  
           [0336]    249 Anthracen-2-yl-(2-chloro-benzyl)-amine  
           [0337]    250 Anthracen-2-yl-(2-fluoro-benzyl)-amine  
           [0338]    251 Dibenzo[1,4]dioxin-2-yl-(2,3-dimethoxy-benzyl)-amine  
           [0339]    252 (2-Chloro-benzyl)-dibenzo[1,4]dioxin-2-yl-amine  
           [0340]    253 2-(Dibenzo[1,4]dioxin-2-ylaminomethyl)-phenol  
           [0341]    254 Dibenzo[1,4]dioxin-2-yl-(2-methoxy-benzyl)-amine  
           [0342]    255 2-[(9-Ethyl-9H-carbazol-3-ylamino)-methyl]-phenol  
           [0343]    256 (9-Ethyl-9H-carbazol-3-yl)-(2-fluoro-benzyl)-amine  
           [0344]    257 (9-Ethyl-9H-carbazol-3-yl)-(2-methyl-benzyl)-amine  
           [0345]    258 (2-Chloro-benzyl)-(9H-fluoren-2-yl)-amine  
           [0346]    259 2-[(9H-Fluoren-2-ylamino)-methyl]-phenol  
           [0347]    260 (9H-Fluoren-2-yl)-(2-methoxy-benzyl)-amine  
           [0348]    261 (9H-Fluoren-2-yl)-(2-trifluoromethyl-benzyl)-amine  
           [0349]    262 (9H-Fluoren-2-yl)-(2-fluoro-benzyl)-amine  
           [0350]    263 Dibenzofuran-4-yl-(2,5-dimethoxy-benzyl)-amine  
           [0351]    264 Dibenzofuran-4-yl-(2,3-dimethoxy-benzyl)-amine  
           [0352]    265 2-(Dibenzofuran4-ylaminomethyl)-phenol  
           [0353]    266 Dibenzofuran-4-yl-(2-methoxy-benzyl)-amine  
           [0354]    267 (2,5-Dimethoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)-amine  
           [0355]    268 (2,3-Dimethoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)-amine  
           [0356]    269 (2-Methoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)-amine  
           [0357]    270 Dibenzofuran-2-yl-(2,5-dimethoxy-benzyl)-amine  
           [0358]    271 Dibenzofuran-2-yl-(4-methoxy-benzyl)-amine  
           [0359]    272 (2-Bromo-benzyl)-dibenzofuran-2-yl-amine  
           [0360]    273 (8-Fluoro-dibenzofuran-2-yl)-(3H-imidazol-4-ylmethyl)-amine  
           [0361]    274 2-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]-benzonitrile  
           [0362]    275 (2-Ethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0363]    276 (8-Fluoro-dibenzofuran-2-yl)-(4-methylsulfanyl-benzyl)-amine  
           [0364]    277 (2-Bromo-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0365]    278 (8-Fluoro-dibenzofuran-2-yl)-quinolin-4-ylmethyl-amine  
           [0366]    279 (8-Fluoro-dibenzofuran-2-yl)-quinolin-2-ylmethyl-amine  
           [0367]    280 Dibenzofuran-2-yl-naphthalen-1-ylmethyl-amine  
           [0368]    281 (8-Fluoro-dibenzofuran-2-yl)-naphthalen-2-ylmethyl-amine  
           [0369]    282 (8-Fluoro-dibenzofuran-2-yl)-naphthalen-1-ylmethyl-amine  
           [0370]    283 Dibenzofuran-2-yl-(2-nitro-benzyl)-amine  
           [0371]    284 Dibenzofuran-2-yl-(3H-imidazol-4-ylmethyl)-amine  
           [0372]    285 2-(Dibenzofuran-2-ylaminomethyl)-benzonitrile  
           [0373]    286 Dibenzofuran-2-yl-(2-ethoxy-benzyl)-amine  
           [0374]    287 Dibenzofuran-2-yl-(3-trifluoromethyl-benzyl)-amine  
           [0375]    288 (4-tert-Butyl-benzyl)-dibenzofuran-2-yl-amine  
           [0376]    289 Dibenzofuran-2-yl-(3-fluoro-benzyl)-amine  
           [0377]    290 (2,5-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0378]    291 (2,3-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0379]    292 (4-Benzyloxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0380]    293 (3-Benzyloxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0381]    294 (4-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0382]    295 (3-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0383]    296 (2-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0384]    297 4-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]-phenol  
           [0385]    298 3-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]-phenol  
           [0386]    299 Dibenzofuran-2-yl-(2-fluoro-benzyl)-amine  
           [0387]    300 (8-Fluoro-dibenzofuran-2-yl)-(4-methoxy-benzyl)-amine  
           [0388]    301 (8-Fluoro-dibenzofuran-2-yl)-(3-methoxy-benzyl)-amine  
           [0389]    302 (8-Fluoro-dibenzofuran-2-yl)-(2-methoxy-benzyl)-amine  
           [0390]    303 (8-Fluoro-dibenzofuran-2-yl)-(4-trifluoromethyl-benzyl)-amine  
           [0391]    304 (8-Fluoro-dibenzofuran-2-yl)-(3-trifluoromethyl-benzyl)-amine  
           [0392]    305 (4-tert-Butyl-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0393]    306 (4-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0394]    307 (3-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0395]    308 (2-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0396]    309 (8-Fluoro-dibenzofuran-2-yl)-(4-methyl-benzyl)-amine  
           [0397]    310 (8-Fluoro-dibenzofuran-2-yl)-(3-methyl-benzyl)-amine  
           [0398]    311 Dibenzofuran-2-yl-(2,6-dimethoxy-benzyl)-amine  
           [0399]    312 Dibenzofuran-2-yl-(2,4-dimethoxy-benzyl)-amine  
           [0400]    313 Dibenzofuran-2-yl-(2,3-dimethoxy-benzyl)-amine  
           [0401]    314 (4Benzyloxy-benzyl)-dibenzofuran-2-yl-amine  
           [0402]    315 Dibenzofuran-2-yl-(3-methyl-benzyl)-amine  
           [0403]    316 (3-Chloro-benzyl)-dibenzofuran-2-yl-amine  
           [0404]    317 3-(Dibenzofuran-2-ylaminomethyl)-phenol  
           [0405]    318 (2-Chloro-benzyl)-dibenzofuran-2-yl-amine  
           [0406]    319 Dibenzofuran-2-yl-(3-methoxy-benzyl)-amine  
           [0407]    320 Dibenzofuran-2-yl-(2-methoxy-benzyl)-amine  
           [0408]    321 (9H-Fluoren-2-yl)-(2-methyl-benzyl)-amine  
           [0409]    322 Dibenzofuran-4-yl-(2-methyl-benzyl)-amine  
           [0410]    323 (8-Chloro-dibenzofuran-2-yl)-(2-methyl-benzyl)-amine  
           [0411]    324 (2-Methyl-benzyl)-(10H-phenothiazin-2-yl)-amine  
           [0412]    325 Dibenzo[b,e][1,4]dioxin-2-yl-(2-methyl-benzyl)-amine  
           [0413]    326 Dibenzofuran-2-yl-(2,6-difluoro-benzyl)-amine  
           [0414]    327 Dibenzofuran-2-yl-(2,5-difluoro-benzyl)-amine  
           [0415]    328 Dibenzofuran-2-yl-(2,4-difluoro-benzyl)-amine  
           [0416]    329 Dibenzofuran-2-yl-(2,3-difluoro-benzyl)-amine  
           [0417]    330 (8-Fluoro-dibenzofuran-2-yl)-thiophen-2-ylmethyl-amine  
           [0418]    331 Dibenzofuran-2-yl-(2,5-dimethyl-benzyl)-amine  
           [0419]    332 (8-Fluoro-dibenzofuran-2-yl)-thiophen-3-ylmethyl-amine  
           [0420]    333 (8-Fluoro-dibenzofuran-2-yl)-furan-2-ylmethyl-amine  
           [0421]    334 (8-Fluoro-dibenzofuran-2-yl)-furan-3-ylmethyl-amine  
           [0422]    335 (8-Fluoro-dibenzofuran-2-yl)-(6-methyl-pyridin-2-ylmethyl)-amine  
           [0423]    336 (8-Fluoro-dibenzofuran-2-yl)-(4-methanesulfonyl-benzyl)-amine  
           [0424]    337 (8-Fluoro-dibenzofuran-2-yl)-pyridin-4-ylmethyl-amine  
           [0425]    338 (8-Fluoro-dibenzofuran-2-yl)-pyridin-3-ylmethyl-amine  
           [0426]    339 (8-Fluoro-dibenzofuran-2-yl)-pyridin-2-ylmethyl-amine  
           [0427]    340 (8-Fluoro-dibenzofuran-2-yl)-(3-fluoro-4-methoxy-benzyl)-amine  
           [0428]    341 Dibenzofuran-2-yl-(2,4-dimethyl-benzyl)-amine  
           [0429]    342 (8-Fluoro-dibenzofuran-2-yl)-(3-fluoro-2-methyl-benzyl)-amine  
           [0430]    343 (8-Fluoro-dibenzofuran-2-yl)-(2,3,6-trifluoro-benzyl)-amine  
           [0431]    344 (8-Fluoro-dibenzofuran-2-yl)-(2,3,4-trifluoro-benzyl)-amine  
           [0432]    345 (3,5-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0433]    346 (3,4-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0434]    347 (3,5-difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0435]    348 (2,6-Difluoro-benzyl (2,5-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0436]    349 (2,4-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0437]    350 (2,3-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0438]    351 (2,5-Dimethyl-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0439]    352 (2,4-Dimethyl-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0440]    353 (2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0441]    354 (3,5-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine  
           [0442]    355 Dibenzofuran-2-yl-dibenzofuran-2-ylmethyl-amine  
           [0443]    356 Dibenzofuran-2-yl-dibenzofuran-3-ylmethyl-amine  
           [0444]    357 Dibenzofuran-2-yl-(6-methyl-pyridin-2-ylmethyl)-amine  
           [0445]    358 Dibenzofuran-2-yl-(4-methanesulfonyl-benzyl)-amine  
           [0446]    359 Dibenzofuran-2-yl-pyridin-4-ylmethyl-amine  
           [0447]    360 Dibenzofuran-2-yl-pyridin-3-ylmethyl-amine  
           [0448]    361 Dibenzofuran-2-yl-pyridin-2-ylmethyl-amine  
           [0449]    362 Dibenzofuran-2-yl-(3-fluoro-4-methoxy-benzyl)-amine  
           [0450]    363 Dibenzofuran-2-yl-(3-fluoro-2-methyl-benzyl)-amine  
           [0451]    364 Dibenzofuran-2-yl-(2,3,6-trifluoro-benzyl)-amine  
           [0452]    365 Dibenzofuran-2-yl-(2,3,4-trifluoro-benzyl)-amine  
           [0453]    366 Dibenzofuran-2-yl-(3,5-difluoro-benzyl)-amine  
           [0454]    367 Dibenzofuran-2-yl-(3,4-difluoro-benzyl)-amine  
           [0455]    368 Dibenzofuran-2-yl-(3,4-dimethoxy-benzyl)-amine  
           [0456]    369 Dibenzofuran-2-yl-methyl-(2-methyl-benzyl)-amine  
           [0457]    370 Dibenzothiohen-2-yl-(2,4-dimethyl-benzyl)-amine  
           [0458]    371 (4-tert-Butyl-benzyl)-dibenzothiohen-2-yl-amine  
           [0459]    372 (2-Chloro-benzyl)-dibenzothiohen-2-yl-amine  
           [0460]    373 Dibenzothiohen-2-yl-(2,6-difluoro-benzyl)-amine  
           [0461]    374 Dibenzothiohen-2-yl-(2,3,6-trifluoro-benzyl)-amine  
           [0462]    375 Dibenzothiohen-2-yl-(2-fluoro-benzyl)-amine  
           [0463]    376 Benzyl-dibenzothiohen-2-yl-amine  
           [0464]    377 Dibenzothiohen-2-yl-(4-methoxy-benzyl)-amine  
           [0465]    378 Dibenzothiohen-2-yl-(2,3-dimethoxy-benzyl)-amine  
           [0466]    379 Dibenzothiohen-2-yl-(2,5-difluoro-benzyl)-amine  
           [0467]    380 Dibenzothiohen-2-yl-(3-methoxy-benzyl)-amine  
           [0468]    381 Dibenzothiohen-2-yl-(2,3,4-trifuoro-benzyl)-amine  
           [0469]    382 (-2-Bromo-benzyl)-dibenzothiohen-2-yl-amine  
           [0470]    383 Dibenzothiohen-2-yl-(2,3-dihydro-1,4benzodioxin-6-ylmethyl)-amine  
           [0471]    384 Dibenzothiohen-2-yl-(3-fluoro-4-methoxy-benzyl)-amine  
           [0472]    385 Dibenzothiohen-2-yl-(2,5-dimethyl-benzyl)-amine  
           [0473]    386 Dibenzothiohen-2-yl-thiophen-3-ylmethyl-amine  
           [0474]    387 Dibenzothiohen-2-yl-naphthalene-1-ylmethyl-amine  
           [0475]    388 Dibenzothiohen-2-yl-(2-trifluoromethyl-benzyl)-amine  
           [0476]    389 Dibenzothiohen-2-yl-naphthalen-2-ylmethyl-amine  
           [0477]    390 Dibenzothiohen-2-yl-(2-ethoxy-benzyl)-amine  
           [0478]    391 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3-fluoro-2-methyl-benzyl)-amine  
           [0479]    392 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2-methyl-benzyl)-amine  
           [0480]    393 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,4-dimethyl-benzyl)-amine  
           [0481]    394 (4-tert-Butyl-benzyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine  
           [0482]    395 (2-Chloro-benzyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine  
           [0483]    396 (2,6-Difluoro-benzyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine  
           [0484]    397 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,3,6-trifluoro-benzyl)-amine  
           [0485]    398 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2-fluoro-benzyl)-amine  
           [0486]    399 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3,5-dimethoxy-benzyl)-amine  
           [0487]    400 Benzyl-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine  
           [0488]    401 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(4-methoxy-benzyl)-amine  
           [0489]    402 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,3-dimethoxy-benzyl)-amine  
           [0490]    403 (2,5-difluoro-benzyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine  
           [0491]    404 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3 -methoxy-benzyl)-amine  
           [0492]    405 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,3,-trifluoro-benzyl)-amine  
           [0493]    406 (2-Bromo-benzyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine  
           [0494]    407 (2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine  
           [0495]    408 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3-fluoro-4-methoxy-benzyl)-amine  
           [0496]    409 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,5-dimethyl-benzyl)-amine  
           [0497]    410 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-thiophen-3-ylmethyl-amine  
           [0498]    411 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-naphthalen-1-ylmethyl-amine  
           [0499]    412 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2-trifluoromethyl-benzyl)-amine  
           [0500]    413 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-naphthalen-2-ylmethyl-amine  
           [0501]    414 (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2-ethoxy-benzyl)-amine  
           [0502]    415 (3-Fluoro-2-methyl-benzyl)-(10H-phenothiazin-2-yl)-amine  
           [0503]    416 (2,4-Dimethyl-benzyl)-(10H-phenothiazin-2-yl)-amine  
           [0504]    417 (4-tert-Butyl-benzyl)-(10H-phenothiazin-2-yl)-amine  
           [0505]    418 (2-Chloro-benzyl)-(10H-phenothiazin-2-yl)-amine  
           [0506]    419 (2,6-Difluoro-benzyl)-(10H-phenothiazin-2-yl)-amine  
           [0507]    420 (10H-Phenothiazin-2-yl)-(2,3,6-trifluorobenzyl)-amine  
           [0508]    421 (2-Fluoro-benzyl)-(10H-phenothiazin-2-yl)-amine  
           [0509]    422 (3,5-Dimethoxy-benzyl)-(10H-phenothiazin-2-yl)-amine  
           [0510]    423 Benzyl-(10H-phenothiazin-2-yl)-amine  
           [0511]    424 (4-Methoxy-benzyl)-(10H-phenothiazin-2-yl)-amine  
           [0512]    425 (2,5-Difluoro-benzyl)-(10H-phenothiazin-2-yl)-amine  
           [0513]    426 (10H-Phenothiazin-2-yl)-(2,3,4-trifluoro-benzyl)-amine  
           [0514]    427 (2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-(10H-phenothiazin-2-yl)-amine  
           [0515]    428 (3-Fluoro-4-methoxy-benzyl)-(10H-phenothiazin-2-yl)-amine  
           [0516]    429 (2,5-Dimethyl-benzyl)-(10H-phenothiazin-2-yl)-amine  
           [0517]    430 (10H-Phenothiazin-2-yl)-thiophen-3-ylmethyl-amine  
           [0518]    431 (10H-Phenothiazin-2-yl)-(2-trifluoromethyl-benzyl)-amine  
           [0519]    432 (9H-Carbazol-3-yl)-(3-fluoro-2-methyl-benzyl)-amine  
           [0520]    433 (9H-Carbazol-3-yl)-(2-methyl-benzyl)-amine  
           [0521]    434 (9H-Carbazol-3-yl)-(2,4-dimethyl-benzyl)-amine  
           [0522]    435 (4-tert-Butyl-benzyl)-(9H-carbazol-3-yl)-amine  
           [0523]    436 (9H-Carbazol-3-yl)-(2-chloro-benzyl)-amine  
           [0524]    437 (9H-Carbazol-3-yl)-(2,6-difluoro-benzyl)-amine  
           [0525]    438 (9H-Carbazol-3-yl)-(2,3,6-trifluoro-benzyl)-amine  
           [0526]    439 (9H-Carbazol-3-yl)-(3,5-dimethoxy-benzyl)-amine  
           [0527]    440 (9H-Carbazol-3-yl)-(2,3-dimethoxy-benzyl)-amine  
           [0528]    441 (9H-Carbazol-3-yl)-(2,5-difluoro-benzyl)-amine  
           [0529]    442 (9H-Carbazol-3-yl)-(2,3,4-trifluoro-benzyl)-amine  
           [0530]    443 (9H-Carbazol-3-yl)-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-amine  
           [0531]    444 (9H-Carbazol-3-yl)-(2,5-dimethyl-benzyl)-amine  
           [0532]    445 (9H-Carbazol-3-yl)-naphthalen-1-ylmethyl-amine  
           [0533]    446 (9H-Carbazol-3-yl)-naphthalen-2-ylmethyl-amine  
           [0534]    447 Dibenzofuran-2-yl-bis-(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-amine  
           [0535]    448 Dibenzofuran-2-yl-bis-thiophen-3-ylmethyl-amine  
           [0536]    449 Dibenzofuran-2-yl-(4-phenoxy-benzyl)-amine  
           [0537]    450 2-Dibenzofuran-2-yl-2,3-dihydro-1H-isoindole  
           [0538]    451 2-Dibenzofuran-2-yl-1H-isoindole-1,3-dione  
           [0539]    452 Dibenzofuran-2-yl-(4-trifluoromethoxy-benzyl)-amine  
           [0540]    453 Dibenzofuran-2-yl-(2-methoxy-benzyl)-amine  
           [0541]    454 Dibenzofuran-2-yl-(3-phenoxy-benzyl)-amine  
           [0542]    455 Dibenzofuran-2-yl-methyl(2-methyl-benzyl)-amine  
           [0543]    456 Dibenzofuran-2-yl-(1-phenyl-butyl)-amine  
           [0544]    457 Dibenzofuran-2-yl-phenethyl-amine  
           [0545]    458 Dibenzofuran-2-yl-(1-phenyl-ethyl)-amine  
       
    
    
     EXAMPLES  
       [0546]    [0546]                                                                             General   M + H   MOLECULAR       Example   MOLSTRUCTURE   procedure   (APCl)*   FORMULA                                                        1                                 7   282   C18 H19 N O2               2                                 7   250   C18 H19 H               3                                 7   250   C18 H19 N               4                                 7   293   C20 H24 N2               5                                 5   256   C16 H17 N O2               6                                 5   314   C18 H19 N O2S               7                                 5   310   C20 H23 N O2               8                                 5   284   C18 H21 N O2               9                                 5   270   C17 H19 N O2               10                                 7, 5   308   C20 H25 N3               11                                 5   371   C26 H30 N2               12                                 5, 7   265   C18 H20 N2               13                                 5   328   C24 H25 N               14                                 5, 7   238   C17 H19 N               15                                 5   346   C18 H19 N O4S               16                                 6   322   C22 H27 N O               17                                 6   320   C22 H25 N O               18                                 6   318   C22 H23 N O               19                                 6   348   C24 H29 N O               20                                 6   278   C19 H19 N O               21                                 6   322   C22 H27 N O               22                                 6   292   C20 H21 N O               23                                 6   252   C17 H17 N O               24                                 6, 5   296   C19 H21 N O2               25                                 6, 5   264   C19 H21 N               26                                 4   360   C20 H25 N O S2               27                                 4   324   C22 H29 N O               28                                 4   268   C18 H21 N O               29                                 5   357   C20 H24 N2 O2 S               30                                 5, 7   267   C18 H22 N2               31                                 5, 7   325   C20 H24 N2 S               32                                 5, 7   307   C21 H26 N2               33                                 5, 7   321   C22 H28 N2               34                                 5   295   C20 H26 N2               35                                 5   293   C20 H24 N2               36                                 5, 7   281   C19 H24 N2               37                                 5, 7   224   C16 H17 N               38                                 5   282   C18 H19 N S               39                                 5, 7   278   C20 H23 N               40                                 5   316   C17 H17 N O3 S               41                                 5, 6   267   C17 H18 N2 O               42                                 5, 6   226   C15 H15 N O               43                                 5, 6   266   C18 H19 N O               44                                 5   252   C17 H17 N O               45                                 5   316   C17 H17 N O3 S               46                                 5   267   C17 H18 N2 O               47                                 5   226   C15 H15 N O               48                                 5   284   C17 H17 N O S               49                                 5   266   C18 H19 N O               50                                 5   280   C19 H21 N O               51                                 5   308, 310   C19 H14 Cl N O               52                                 2   353. 355   C19 H13 Cl N2 O3               53                                 2   358   C20 H14 F3 N O2               54                                 2   318   C20 H15 N O3               55                                 2   332   C21 H17 N O3               56                                 2   334   C21 H19 N O3               57                                 2   342   C20 H14 F3 N O               58                                 1, 2, 3   288   C20 H17 N O               59                                 2   280   C17 H13 N O S               60                                 2   319   C19 H14 N2 O3               61                                 2   320   C20 H17 N O S               62                                 2   288   C20 H17 N O               63                                 2   274   C19 H15 N O               64                                 2   380   C26 H21 N O2               65                                 5   330   C23 H23 N O               66                                 5   332   C22 H21 N O2               67                                 5   270   C17 H19 N O2               68                                 5   268   C18 H21 N O               69                                 5   254   C17 H19 N O               70                                 5   268   C18 H21 N O               71                                 5   294   C20 H23 N O               72                                 5   294   C20 H23 N O               73                                 5, 6   280   C19 H21 N O               74                                 5, 6   284   C17 H17 N O S               75                                 5   270   C16 H15 N O S               76                                 5   254   C17 H19 N O               77                                 5   254   C17 H19 N O               78                                 5, 6   240   C16 H17 N O               79                                 3   293   C18 H13 F N2 O               80                                 3   276   C17 H13 N3 O               81                                 3   289   C19 H16 N2 O               82                                 3   321   C20 H17 F N2 O               83                                 3   354   C23 H19 N3 O               85                                 3   381   C21 H20 N2 O3 S               86                                 3   304   C19 H17 N3 O               87                                 3   317   C21 H20 N2 O               88                                 3, 2   355   C23 H18 N2 S               89                                 3   383   C20 H18 N2 O2 S               90                                 3   339   C19 H15 F N2 O S               91                                 3   325   C18 H13 F N2 O S               92                                 3   358   C21 H15 N3 O S               93                                 3   357   C22 H16 N2 O S               94                                 3   385   C19 H16 N2 O3 S               95                                 3   308   C17 H13 N3 O S               96                                 3   321   C19 H16 N2 O S               97                                 3   335   C24 H18 N2               98                                 3   362   C22 H19 N O2 S               99                                 3   285   C20 H16 N2               100                                 3   298   C22 H19 N               101                                 3   322   C20 H16 F N O2               102                                 3   308   C19 H14 F N O2               103                                 3   341   C22 H16 N2 O2               104                                 3   340   C23 H17 N O2               105                                 3   368   C20 H17 N O4 S               106                                 3   291   C18 H14 N2 O2               107                                 3   322   C20 H16 F N O2               108                                 3   308   C19 H14 F N O2               109                                 3   368   C20 H17 N O4 S               110                                 3   291   C18 H14 N2 O2               111                                 3   304   C20 H17 N O2               112                                 3   326, 328   C19 H13 Cl F N O               113                                 3   359   C23 H16 Cl N O               114                                 3   387   C20 H16 Cl N O3 S               115                                 3   355   C20 H22 N2 O2 S               116                                 3   278   C18 H19 N3               117                                 3   307   C19 H15 F N2 O               118                                 2, 3   325   C22 H16 N2 O               119                                 2   325   C22 H16 N2 O               120                                 2   335   C21 H19 F N2 O               121                                 2   317   C21 H20 N2 O               122                                 2   325   C17 H12 N2 O3 S               123                                 2   281   C16 H12 N2 O S               124                                 2   292   C19 H14 F N O               125                                 2   333   C21 H20N2O2               126                                 2   363   C22H22N2O3               127                                 2   359   C24H26N2O1               128                                 2   303   C20H18N2O1               129                                 2   328   C21H17N3O1               130                                 2   336   C20H17N1O2S1               131                                 2   338, 340   C20H16N1O2Cl1               132                                 2   336   C20H17O2S1N1               133                                 2   366   C21H19O3N1S1               134                                 2   354   C20H16O2N1S1F1               135                                 2   362   C23H23O1N1S1               136                                 2   306   C19H15N1O1S1               137                                 2   350   C21H19N1O2S1               138                                 2   368, 370   C21H18N1O3Cl1               139                                 2   356, 358   C20H15N1O2Cl1F1               140                                 2   308, 310   C19H14NOCl               141                                 2   302   C21H19NO               142                                 2   315, 317   C15H11N2OClS               143                                 2   302   C21H19NO               144                                 2   332   C22H21NO2               145                                 2   320   C21H18NOF               146                                 2   328   C24H25N               147                                 2   272   C20H17N1               148                                 2   279   C16H14N2S               149                                 2   316   C22H21NO               150                                 2   304   C20H17NO2               151                                 2   334   C20H13N2Ocl               152                                 2   304   C20H17NO2               153                                 2   334   C21H19NO3               154                                 2   322   C20H16NFO2               155                                 2   330   C23H23NO               156                                 2   318   C21H19NO2               157                                 2   333   C21H20N2O2               158                                 2   338, 340   C20H16NO2Cl               159                                 2   352, 354   C21H18NO2Cl               160                                 2   302   C21 H19 N O               161                                 2   309   C18 H16 N2 O S               162                                 2   304   C19 H17 N3 O               163                                 2   383, 385   C19 H14 Br N O S               164                                 2   357   C22 H16 N2 O S               165                                 2   312   C17 H13 N O S2               166                                 2   321   C19 H16 N2 O S               167                                 2   307   C18 H14 N2 O S               168                                 2   307   C18 H14 N2 O S               169                                 2   314, 316   C17 H12 Cl N O S               170                                 2   379, 381   C21 H19 Br N2               171                                 2   323, 325   C19 H15 Cl N2 O               172                                 2   307   C19 H18 N2 S               173                                 2   341, 342   C19 H17 Cl N2 S               174                                 2   3O2   C20 H19 N3               175                                 2   350, 352   C20 H16 Br N               176                                 2, 3   309, 311   C18 H13 Cl N2 O               177                                 2   323   C23 H18 N2               178                                 2   278   C18 H15 N S               179                                 2   287   C20 H18 N2               180                                 2   273   C19 H16 N2               181                                 2   273   C19 H16 N2               182                                 2   273   C19 H16 N2               183                                 2   309, 311   C18 H13 Cl N2 O               184                                 2   325   C22 H16 N2 O               185                                 2   325   C22 H16 N2 O               186                                 2   280   C17 H13 N O S               187                                 2   289   C19 H16 N2 O               188                                 2   275   C18 H14 N2 O               189                                 2   275   C18 H14 N2 O               190                                 2   275   C18 H14 N2 O               191                                 2   387, 389   C19 H13 Br Cl N O               192                                 2   309, 311   C18 H13 Cl N2 O               193                                 2   357   C20 H15 F3 N2 O               194                                 2   357   C20 H15 F3 N2 O               195                                 2   339   C20 H16 F2 N2 O               196                                 2   339   C20 H16 F2 N2 O               197                                 2   339   C20 H16 F2 N2 O               198                                 2   339   C20 H16 F2 N2 O               199                                 2   331   C22 H22 N2 O               200                                 2   331   C22 H22 N2 O               201                                 2   361   C22 H20 N2 O3               202                                 2   338   C20 H16 F N O S               203                                 2   363   C19 H11 Cl F3 N O               204                                 2   360   C19 H12 F3 N O S               205                                 2   360   C19 H12 F3 N O S               206                                 2   342   C19 H13 F2 N O S               207                                 2   342   C19 H13 F2 N O S               208                                 2   342   C19 H13 F2 N O S               209                                 2   342   C19 H13 F2 N O S               210                                 2   334   C21 H19 N O S               211                                 2   364   C21 H17 N O3 S               212                                 2   272   C16 H14 F N S               213                                 2   363   C19 H11 Cl F3 N O               214                                 2   345   C19 H12 Cl F2 N O               215                                 2   345   C19 H12 Cl F2 N O               216                                 2   345   C19 H12 Cl F2 N O               217                                 2   333   C22 H21 F N2               218                                 2   345   C19 H12 Cl F2 N O               219                                 2   355   C21 H17 F3 N2               220                                 2   355   C21 H17 F3 N2               221                                 2   337   C21 H18 F2 N2               222                                 2   337   C21 H18 F2 N2               223                                 2   337   C21 H18 F2 N2               224                                 2   337   C21 H18 F2 N2               225                                 2   329   C23 H24 N2               226                                 2   329   C23 H24 N2               227                                 2   359   C23 H22 N2 O2               228                                 2   304   C21 H18 F N               229                                 2   337   C21 H18 Cl N O               230                                 2   326   C20 H14 F3 N               231                                 2   326   C20 H14 F3 N               232                                 2   308   C20 H15 F2 N               233                                 2   308   C20 H15 F2 N               234                                 2   308   C20 H15 F2 N               235                                 2   300   C22 H21 N               236                                 2   300   C22 H21 N               237                                 2   330   C22 H19 N O2               238                                 2   336, 338   C21 H18 Cl N O               239                                 2   302   C21 H19 N O               240                                 2   306   C20 H16 F N O               241                                 2, 3   335   C21 H19 F N2 O               242                                 2, 3   341   C20 H15 Cl F N O               243                                 2   367   C21 H16 Cl N O3               244                                 2   366   C21 H19 N O3 S               245                                 2   366   C21 H19 N O3 S               246                                 2   340, 342   C19 H14 Cl N O S               247                                 2   336   C20 H17 N O2 S               248                                 2   320   C20 H17 N O S               249                                 2   318, 320   C21 H16 Cl N               250                                 2   302   C21 H16 F N               251                                 2   350   C21 H19 N O4               252                                 2   324, 326   C19 H14 Cl N O2               253                                 2   306   C19 H15 N O3               254                                 2   320   C20 H17 N O3               255                                 2   317   C21 H20 N2 O               256                                 2   319   C21 H19 F N2               257                                 2   315   C22 H22 N2               258                                 2   306, 308   C20 H16 Cl N               259                                 2   288   C20 H17 N O               260                                 2   3O2   C21 H19 N O               261                                 2   340   C21 H16 F3 N               262                                 2   290   C20 H16 F N               263                                 2   334   C21 H19 N O3               264                                 2   334   C21 H19 N O3               265                                 2   290   C19 H15 N O2               266                                 2   304   C20 H17 N O2               267                                 2   364   C22 H21 N O4               268                                 2   364   C22 H21 N O4               269                                 2   334   C21 H19 N O3               270                                 2   334   C21 H19 N O3               271                                 2   304   C20 H17 N O2               272                                 2   351, 353   C19 H14 Br N O               273                                 2   282   C16 H12 F N3 O               274                                 2   317   C20 H13 F N2 O               275                                 2   336   C21 H18 F N O2               276                                 2   338   C20 H16 F N O S               277                                 2   369, 371   C19 H13 Br F N O               278                                 2   343   C22 H15 F N2 O               279                                 2   343   C22 H15 F N2 O               280                                 2, 3   324   C23 H17 N O               281                                 2   342   C23 H16 F N O               282                                 2   342   C23 H16 F N O               283                                 2   319   C19 H14 N2 O3               284                                 2   264   C16 H13 N3 O               285                                 2   299   C20 H14 N2 O               286                                 2   318   C21 H19 N O2               287                                 2   342   C20 H14 F3 N O               288                                 2   330   C23 H23 N O               289                                 2   292   C19 H14 F N O               290                                 2   352   C21 H18 F N O3               291                                 2   352   C21 H18 F N O3               292                                 2   398   C26 H20 F N O2               293                                 2   398   C26 H20 F N O2               294                                 2   326, 328   C19 H13 Cl F N O               295                                 2   326, 328   C19 H13 Cl F N O               296                                 2   326, 328   C19 H13 Cl F N O               297                                 2   308   C19 H14 F N O2               298                                 2, 3   308   C19 H14 F N O2               299                                 2   292   C19 H14 F N O               300                                 2   322   C20 H16 F N O2               301                                 2   322   C20 H16 F N O2               302                                 2   322   C20 H16 F N O2               303                                 2   360   C20 H13 F4 N O               304                                 2   360   C20 H13 F4 N O               305                                 2   348   C23 H22 F N O               306                                 2   310   C19 H13 F2 N O               307                                 2   310   C19 H13 F2 N O               308                                 2, 3   310   C19 H13 F2 N O               309                                 2   306   C20 H16 F N O               310                                 2   306   C20 H16 F N O               311                                 2   334   C21 H19 N O3               312                                 2   334   C21 H19 N O3               313                                 2   334   C21 H19 N O3               314                                 2   380   C26 H21 N O2               315                                 2   288   C20 H17 N O               316                                 2   308, 310   C19 H14 Cl N O               317                                 2   290   C19 H15 N O2               318                                 2   308, 310   C19 H14 Cl N O               319                                 2   304   C20 H17 N O2               320                                 2   304   C20 H17 N O2               321                                 2   286   C21 H19 N               322                                 2   288   C20 H17 N O               323                                 2, 3   323   C20 H16 Cl N O               324                                 2   319   C20 H18 N2 S               325                                 2, 3   304   C20 H17 N O2               326                                 2   310   C19 H13 F2 N O               327                                 2   310   C19 H13 F2 N O               328                                 2   310   C19 H13 F2 N O               329                                 2   310   C19 H13 F2 N O               330                                 2   298   C17 H12 F N O S               331                                 2   302   C21 H19 N O               332                                 2   298   C17 H12 F N O S               333                                 2   282   C17 H12 F N O2               334                                 2   282   C17 H12 F N O2               335                                 2   307   C19 H15 F N2 O               336                                 2   370   C20 H16 F N O3 S               337                                 2, 3   293   C18 H13 F N2 O               338                                 2   293   C18 H13 F N2 O               339                                 2   293   C18 H13 F N2 O               340                                 2   340   C20 H15 F2 N O2               341                                 2   302   C21 H19 N O               342                                 2, 3   324   C20 H15 F2 N O               343                                 2   346   C19 H11 F4 N O               344                                 2   346   C19 H11 F4 N O               345                                 2   328   C19 H12 F3 N O               346                                 2   328   C19 H12 F3 N O               347                                 2   328   C19 H12 F3 N O               348                                 2   328   C19 H12 F3 N O               349                                 2   328   C19 H12 F3 N O               350                                 2   328   C19 H12 F3 N O               351                                 2   320   C21 H18 F N O               352                                 2   320   C21 H18 F N O               353                                 2   350   C21 H16 F N O3               354                                 2   352   C21 H18 F N O3               355                                 2   264   C17 H13 N O2               356                                 2   264   C17 H13 N O2               357                                 2   289   C19 H16 N2 O               358                                 2, 3   352   C20 H17 N O3 S               359                                 2, 3   275   C18 H14 N2 O               360                                 2   275   C18 H14 N2 O               361                                 2   275   C18 H14 N2 O               362                                 2   322   C20 H16 F N O2               363                                 2, 3   306   C20 H16 F N O               364                                 2   328   C19 H12 F3 N O               365                                 2   328   C19 H12 F3 N O               366                                 2   310   C19 H13 F2 N O               367                                 2   310   C19 H13 F2 N O               368                                 2   334   C21 H19 N O3               369                                 2   304   C20H17NS               370                                 2   318   C21H19NS               371                                 2   346   C23H23NS               372                                 2   323, 325   C19H14ClNS               373                                 2   326   C19H13F2NS               374                                 2   344   C19H12F3NS               375                                 2   308   C19H14FNS               376                                 2   290   C19H15NS               377                                 2   320   C20H17NOS               378                                 2   350   C21H19NO2S               379                                 2   326   C19H13F2NS               380                                 2   320   C20H17NOS               381                                 2   344   C19H12F3NS               382                                 2   369   C19H14BrNS               383                                 2   348   C21H17NO2S               384                                 2   338   C20H16FNOS               385                                 2   318   C21H19NS               386                                 2   296   C17H13NS2               387                                 2   340   C23H17NS               388                                 2   358   C20H14F3NS               389                                 2   340   C23H17NS               390                                 2   334   C21H19NOS               391                                 2   333   C22H21FN2               392                                 2   315   C22H22N2               393                                 2   329   C23H24N2               394                                 2   357   C25H28N2               395                                 2   334, 336   C21H19ClN2               396                                 2   337   C21H18F2N2               397                                 2   355   C21H17F3N2               398                                 2   319   C21H19FN2               399                                 2   361   C23H24N2O2               400                                 2   301   C21H20N2               401                                 2   331   C22H22N2O               402                                 2   361   C23H24N2O2               403                                 2   337   C21H18F2N2               404                                 2   331   C22H22N2O               405                                 2   355   C21H17F3N2               406                                 2   380   C21H19BrN2               407                                 2   359   C23H22N2O2               408                                 2   349   C22H21FN2O               409                                 2   329   C23H24N2               410                                 2   307   C19H18N2S               411                                 2   351   C25H22N2               412                                 2   369   C22H19F3N2               413                                 2   351   C25H22N2               414                                 2   345   C23H24N2O               415                                 2   337   C20H17FN2S               416                                 2   333   C21H20N2S               417                                 2   361   C23H24N2S               418                                 2   338, 340   C19H15ClN2S               419                                 2   341   C19H14F2N2S               420                                 2   359   C19H13F3N2S               421                                 2   323   C19H15FN2S               422                                 2   365   C21H20N2O2S               423                                 2   305   C19H16N2S               424                                 2   335   C20H18N2OS               425                                 2   341   C19H14F2N2S               426                                 2   359   C19H13F3N2S               427                                 2   363   C21H18N2O2S               428                                 2   353   C20H17FN2OS               429                                 2   333   C21H2ON2S               430                                 2   311   C17H14N2S2               431                                 2   373   C20H15F3N2S               432                                 2   305   C20H17FN2               433                                 2   287   C20H18N2               434                                 2   301   C21H20N2               435                                 2   329   C23H24N2               436                                 2   306, 308   C19H15ClN2               437                                 2   309   C19H14F2N2               438                                 2   327   C19H13F3N2               439                                 2   333   C21H20N2O2               440                                 2   333   C21H20N2O2               441                                 2   309   C19H14F2N2               442                                 2   327   C19H13F3N2               443                                 2   331   C21H18N2O2               444                                 2   301   C21H20N2               445                                 2   323   C23H18N2               446                                 2   323   C23H18N2                            
         [0547]    The following compound were prepared to the general procedure 1:  
                                                       MS                       (M + H)     1 H-NMR in CDCl 3  unless   Mp       Example   Structure   APCI   otherwise noted (δ)   (° C.)                                            26                                 360   7.90(1H, d); 7.51(1H, d); 7.44-7.26(4H, m); 6.95(1H, d); 3.46(4H, t); 2.58(4H, t); 2.12(6H, s); 1.91(4H, quintet)   —                55                                 332   7.87(1H, d); 7.52(1H, d); 7.38-7.46(2H, quartet); 7.25-7.35(1H, t); 7.14(1H, s); 6.97-6.86(3H, m); 6.76-6.81(1H, d); 4.31 (2H, s) 4.25(4H, br s)   —               447                                 480   7.81(1H, d); 7.48(1H, d); 7.34-7.41(2H, m); 7.22-7.28(2H, t); 6.88-6.92(1H, d); 6.74-6.86(6H, m); 4.56(4H, br s); 4.23(8H, br s)   —               448                                 376   7.85(1H, d); 7.51(1H, d); 7.26-7.42(6H, m); 7.08(2H, br s); 6.99-7.06(3H, m); 4.60(4H, br s)   109-110                59                                 280   7.86(1H, d); 7.52(1H, d); 7.38-7.44(2H, m); 7.25-7.35(3H, m); 7.19(1H, s); 7.14(1H, s); 6.81(1H, s); 4.43(2H, s)   62-63                56                                 334   7.86(1H, d); 7.52(1H, d); 7.29-7.42(3H, m); 7.12(1H, s); 6.78(1H, d); 6.60(2H, s); 6.41(1H, t); 4.35(2H, s); 3.79(6H, s)   87-88                63                                 274   7.89(1H, d); 7.53(1H, d); 7.31-7.48(8H, m); 7.18(1H, s); 6.81(1H, d); 4.43(2H, s); 4.10(1H, br s)   81-82                61                                 320   IN DMSO 7.93(1H, d); 7.54(1H, d); 7.17-7.42(8H, m); 6.81(1H, d); 6.22(1H, t); 4.30(2H, d); 2.41(3H, s)   103-104                73                                 294   7.90(1H, d); 7.51(1H, d); 7.36-7.44(2H, quartet); 7.26-7.33(1H, t); 7.09(1H, s); 6.72(1H, d); 3.60(2H, br m); 1.95(2H, br m); 1.61 (12H, br m)   50-52                57                                 342   7.86(1H, d); 7.63(2H, d); 7.54(3H, t); 7.43(2H, quartet); 7.32(1H t); 7.11(1H, s); 6.77(1H, d); 4.46(2H, s) 4.15(1H, br s)   89-90               449                                 364   7.90(1H, d); 7.53(1H, d); 7.30-7.45(7H, m); 7.03-7.18(6H, m); 6.81(1H, d); 4.39(2H, s); 4.08(1H, br s)   91-93               450                                 286   7.96(1H, d); 7.31-7.55(8H, m); 7.15(1H, s); 6.83(1H, d); 4.73(4H, s)   193-195               451                                 314   IN DMSO 8.22(1H, s); 8.13(1H, d); 7.84-8.01(5H, m); 7.75(1H, d); 7.57(2H, m); 7.43(1H, t)   217-218                58                                 288   7.95(1H, d); 7.57(1H, d); 7.28-7.41(4H, m); 7.12-7.20(4H, m); 6.87(1H, d); 6.03(1H, t); 4.28(2H, d); 2.36(3H, s)   84-85               452                                 358   7.85(1H, d); 7.37-7.53(5H, m); 7.20-7.31(3H, m); 7.14(1H, s); 6.90(1H, d); 4.43(2H, s); 4.22(1H, br s)   75-77               453                                 290   7.86(1H, d); 7.55(1H, d); 7.41-7.47(3H, t); 7.18-7.34(4H, m); 6.89-7.02(3H, m); 4.52(2H, s)   145-147               454                                 366   7.85(1H, d); 7.51(1H, d); 7.26-7.44(6H, m); 7.17(1H, d); 7.06-7.13(3H, m); 6.99-7.02(2H, m); 6.95(1H, s); 6.77(1H, dd) 4.40(2H, s); 4.17(1H, s)   93-94                54                                 316   7.86(1H, d); 7.51(1H, d); 7.26-7.43(3H, m); 7.14(1H, s); 6.87-6.92(2H, m); 6.77-6.81(2H, m); 5.96(2H, s); 4.32(2H, s); 4.12(1H, br s)   85-86               455                                 302   7.99(1H, d); 7.52(1H, d); 7.44-7.39(2H, m); 7.32-7.15(6H, m); 6.89(1H, s); 4.52(2H, s); 3.09(3H, s); 2.37(3H, s)               456                                 316   7.77(1H, d); 7.48-7.21(9H, m); 7.00(1H, d); 6.70(1H, dd); 4.40(1H, t); 4.13(1H, br s) 1.88-1.78(2H, m); 1.51-1.38(2H, m); 0.97(3H, t)   —               457                                 392   7.87(1H, d); 7.53-7.26(9H, m); 7.16(1H, d); 6.77(1H, dd); 3.50(2H, t); 3.00(2H, t)   —               458                                 288   7.76(1H, d); 7.48-7.21(9H, m); 6.99(1H, d); 6.70(1H, dd); 4.57(1H, q); 4.07(1H, br s); 1.57(3H, d)   94-95               202                                 338   7.09(4H, m), 7.09(3H, m), 6.96(1H, d), 6.30(2H, m), 4.26(sH, s), 2.26(3H, s)   —               210                                 334   7.26(1H, s), 7.18(1H, d), 7.09(s, 1H), 7.07(1H, s), 7.02(1H, s), 6.95(1H, s), 6.97(2H, s), 6.96(1H, s), 6.87(1H, d), 6.36(1H, s), 6.34(1H, d), 4.2(2H, s), 2.31 (6H, s).   —               135                                 362   7.26(1H, s), 7.18(1H, d), 7.09(s, 1H), 7.07(1H, s), 7.02(1H, s), 6.95(1H, s), 6.97(2H, s), 6.96(1H, s), 6.87(1H, d), 6.36(1H, s), 6.34(1H, d), 4.2(2H, s), 1.3(9H, s).   —               146                                 328   7.61(d, 1H), 7.58(d, 1H), 7.45(d, 1H), 7.39(d, 1H), 7.37(s, 1H), 7.34(s, 1H), 7.32(s, 1H), 7.28(d, 1H), 7.16(t, 1H), 6.86(s, 1H), 6.68(dd, 1H), 4.35(s, 3H), 3.8(s, 2H), 1.31(s, 9H).   —                90                                 339   8.15(d, 1H), 7.22(s, 1H), 7.05(m, 3H), 6.98(m, 2H), 6.88(d, 1H), 6.32(d, 1H), 6.29(s, 1H), 4.3(s, 2H), 2.3(s, 3H).   —                  
 
         [0548]    Antiviral Activity Assays:  
         [0549]    Screening assays: Anti-herpes simplex virus-1 (HSV) activity is determined in a yield reduction assay utilizing a recombinant HSV (HSV US3: pgC-lacZ which expresses  E. coli  β-galactosidase (β-gal) under the control of an HSV late gene promoter (Fink, D. J.; Sternberg, L. R.; Weber, P. C.; Mata, M.; Goins, W. F.; Glorioso, J. C. Human Gene Therapy 3:11-19, 1992). Vero (African Green Monkey kidney) cells are infected at a multiplicity of infection of 0.01 with the virus, and serial dilutions of the compound in dimethyl sulfoxide (DMSO) are added. The final concentration of DMSO in all wells is 1%. DMSO is added to control wells. The infection is allowed to proceed for 2 days at which time the β-gal activity in cell lysates is measured. Activity in wells containing compound is compared to control wells and percent inhibition determined. The EC 50  is defined as the concentration of drug that produces a 50% reduction in β-gal production relative to control wells.  
         [0550]    Anti-human cytomegalovirus (HCMV) activity is determined in a yield reduction assay utilizing a recombinant HCMV (RC256) that produces β-gal (Spaete, R. R.; Mocarski, E. S. Proceedings of the National Academy of Sciences USA 84:7213-7217, 1987). Primary human diploid fibroblasts (HFF cells) are infected at an moi of 0.01 with RC256, and serial dilutions of the compound in DMSO are added. The final concentration of DMSO in all wells is 1%. The infection is allowed to proceed for 7 days at which time the β-gal activity in cell lysates is measured. Activity in wells containing compound is compared to control wells and percent inhibition determined. The EC 50  is defined as the concentration of compound that produces a 50% reduction in β-gal production relative to control wells. TC 50  is defined as concentration of compound that produces cytotoxicity in 50% of uninfected cells.  
         [0551]    Secondary yield reduction assays: To determine the activity of compounds against HSV, Vero cells are plated in 6 well dishes at a density of 5×10 5  cells/well. Cells are infected at a multiplicity of infection of 0.01 with HSV (strain Syn17+). 30 μL of one of six threefold serial dilutions of test compound in DMSO is added to each well at the time of infection. The plates are returned to a 37° C. incubator and the infection allowed to proceed for 2 days. Aliquots of the supernatant are harvested, and the virus titer determined. Vero cells in 24 well plates are infected with threefold serial dilutions of supernatant. The virus is allowed to adsorb to the monolayer for 1.5 hours, after which it is aspirated and replaced with growth medium containing 0.5% methylcellulose. Plaques are allowed to develop for 5 days, at which time the medium aspirated and the monolayer stained with crystal violet. The plaques are enumerated under low power magnification. Percent inhibition is determined by comparison with the titer from cells infected in the presence of DMSO alone.  
         [0552]    To determine the activity of compounds against CMV, HFF cells, plated in 24 well plates at 1×10 5  cells/well, are infected with CMV (strain AD169) at an moi of 0.01. 10 μL of one of six threefold dilutions of test compound in DMSO is added to each well at the time of infection. The plates are returned to a 37° C. incubator and the infection allowed to proceed for 7 days. Aliquots of the supernatant of infected cells are harvested and the virus titer determined. HFF cells in 24 well plates are infected with threefold serial dilutions of supernatant. The virus is allowed to adsorb to the cells for 2 hours, at which time the inoculum is aspirated and replaced with growth medium containing 0.5% methylcellulose. The plaques are allowed to develop for 7-10 days, at which time the medium is aspirated and the monolayer stained with crystal violet. The plaques are enumerated under low power magnification. Percent inhibition is determined by comparison with the titer from cells infected in the presence of DMSO alone.  
         [0553]    Cellular toxicity assays: Cellular toxicity is measured in HFF cells. Cells are plated in 96 well plates at 1×10 4  cells/well. Serial dilutions of compounds are added to the wells in DMSO, with the final concentration of DMSO in all wells at 1%, in a total volume of 200 μL. The plates are maintained in a 37° C. incubator for 7 days. 50 μL of a solution of XTT (sodium-3′[1-(phenyl-amino-carbonyl)-3,-tetrazolium]-bis(bis(4-methoxy-6-nitro)-benzene sulfonic acid hydrate) (3×10 −4  mg/ml) is added to each well, and the plates returned to the incubator for 4 hours, after which the A 450  (absorbance at wavelength of 450 nm) for each well is measured in a plate reader. (Roehm, N. W., et al J. Immunol. Meth. 142:257-265, 1991). Toxicity is determined by comparison of the OD (optical density) of a well containing compound to the OD of wells containing DMSO only.  
         [0554]    The effect of test compounds on cellular DNA synthesis is measured in a  14 C-thymidine incorporation assay, utilizing scintillation proximity assay technology. Cells are plated at 2×10 4  cells/well in Amersham Cytostar 96 well scintillating microplates. The following day, serial dilutions of test compounds in DMSO are added to the wells, along with 0.1 μCi/well of [methyl- 14 C]-thymidine (specific activity 50-62 mCi/mmol). The plates are counted immediately in a μBeta scintillation counter (Wallac), to determine background, then placed in a 37° C. incubator for 7 days. The plates are removed from the incubator at intervals and the thymidine incorporation into the cellular DNA determined by scintillation counting. Percent inhibition is determined by comparing  14 C incorporation in wells containing test compound to incorporation in wells containing DMSO only.  
         [0555]    Table 3 contains the results of the antiviral efficacy (HSV: EC 50 , TC 50  and TI) screening results, where TI is the therapeutic index (TC 50 /EC 50 ).  
                                                                     TABLE 3                           Antiviral Efficacy in a Yield Reduction Assay (HSV-1)                Antiviral Efficacy (Vero Cells)                Example   EC 50  (μM)   TC 50  (μM)   TI (EC 50 /TC 50 )                             60   0.5   &gt;100   &gt;200            57   0.81   &gt;100   &gt;124            56   0.7   &gt;100   &gt;143           208   0.26   &gt;100   &gt;385           217   0.32   &gt;100   &gt;313           139   0.4   &gt;100   &gt;250           150   0.85   &gt;100   &gt;118            93   1.3   &gt;100   &gt;77           Reference   0.2   &gt;100   &gt;500           Agent           (Acyclovir)                      
 
         [0556]    Table 4 contains the results of the antiviral efficacy (HSV: EC 50 , TC 50  and TI) screening results, where TI is the therapeutic index (TC 50 /EC 50 ).  
                                                                     TABLE 4                           Antiviral Efficacy in a Yield Reduction Assay (CMV)                Antiviral Efficacy (HFF Cells)                Example   EC 50  (μM)   TC 50  (μM)   TI (EC 50 /TC 50 )                            61   2.9   &gt;100   &gt;35           57   1.7   &gt;100   &gt;59           65   3.0   &gt;100   &gt;33           60   1.3   &gt;100   &gt;77           Reference   2.6   &gt;100   &gt;39           Agent           (Ganciclovir)                      
 
         [0557]    Tables 3 and 4 indicates that the compounds of the present invention have good to excellent activity in HSV infected cells from HSV pathogenecity at μM to sub-μM concentrations.  
         [0558]    While the forms of the invention herein disclosed constitute presently preferred embodiments, many others are possible. It is not intended herein to mention all of the possible equivalent forms or ramifications of the invention. It is understood that the terms used herein are merely descriptive, rather than limiting, and that various changes may be made without departing from the spirit or scope of the invention.