PATENT 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.

PATENT 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.  
                         
 
 wherein: 
        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=N, NH, O, NHR 8 , NR 8 , S, SO, SO 2 ;     n=an integer of from 0 to 2;     m=an integer of 1,2, or 3;     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;     Ar=phenyl, 
            substituted phenyl,     benzoheterocyclic ring,     substituted benzoheterocyclic ring,     heterocyclic ring, or     substituted heterocyclic ring, which have substitutions R 6  or R 7 ;    
            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;     R 6  and R 7  may also form a ring, optionally cycloalkyl or aryl or substituted aryl;     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  alloxy, 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 2-butylthio, l-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 14 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-benzimidazolyl, 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 0.0 1 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.  
         [heading-0066]     General Procedure 1 (for Singleton Synthesis):  
         [heading-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 sulfate 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. 
 
 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 (0.05mmol) 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 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 ) 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). 
 
 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). 
 
 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 (0.5 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).  
       General Procedure 5 for Multiple, Simultaneous Solution Phase Synthesis (Combinatorial Chemistry Synthesis):  
       [0075]    
       
                 
         
             
             
         
       
     
         [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 (˜25mg) 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 (S) 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).  
       General Procedure 6 for Multiple, Simultaneous Solution Phase Synthesis (Combinatorial Chemistry Synthesis):  
       [0077]    
       
                 
         
             
             
         
       
     
         [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).  
       General Procedure 7 for Multiple, Simultaneous Solution Phase Synthesis (Combinatorial Chemistry Synthesis):  
       [0079]    
       
                 
         
             
             
         
       
     
         [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-pyridinecarboixaldehyde       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)propionaldehyde       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:  
                                       1   (1-Cyclopropyl-ethyl)-(2-methoxy-dibenzofuran-3-           yl)-amine       2   Cyclopentyl-(9H-fluoren-2-yl)-amine       3   (1-Cyclopropyl-ethyl)-(9H-fluoren-2-yl)-amine       4   N 3 -Cyclopentyl-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine       5   Isopropyl-(2-methoxy-dibenzofuran-3-yl)-amine       6   (2-Methoxy-dibenzofuran-3-yl)-(tetrahydro-thiopyran-           4-yl)-amine       7   Cycloheptyl-(2-methoxy-dibenzofuran-3-yl)-amine       8   (1-Ethyl-propyl)-(2-methoxy-dibenzofuran-3-yl)-amine       9   sec-Butyl-(2-methoxy-dibenzofuran-3-yl)-amine       10   N 2 ,N 2 -Dimethyl-N 3 -piperidin-4-yl-9H-fluorene-2,3-           diamine       11   N 3 -(1-Benzyl-butyl)-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-           diamine       12   (9H-Fluoren-2-yl)-piperidin-4-yl-amine       13   (1-Benzyl-butyl)-(9H-fluoren-2-yl)-amine       14   sec-Butyl-(9H-fluoren-2-yl)-amine       15   (1,1-Dioxo-hexahydro-thiopyran-4-yl)-(2-methoxy-           dibenzofuran-3-yl)-amine       16   Dibenzofuran-2-yl-(3,3,5,5-tetramethyl-cyclohexyl)-           amine       17   (Decahydro-naphthalen-1-yl)-dibenzofuran-2-yl-amine       18   Adamantan-2-yl-dibenzofuran-2-yl-amine       19   Bicyclohexyl-4-yl-dibenzofuran-2-yl-amine       20   Bicyclo[2.2.1]hept-2-yl-dibenzofuran-2-yl-amine       21   (4-tert-Butyl-cyclohexyl)-dibenzofuran-2-yl-amine       22   Bicyclo[3.2.1]oct-2-yl-dibenzofuran-2-yl-amine       23   Cyclopentyl-dibenzofuran-2-yl-amine       24   Cyclohexyl-(2-methoxy-dibenzofuran-3-yl)-amine       25   Cyclohexyl-(9H-fluoren-2-yl)-amine       26   Dibenzofuran-2-yl-bis-(3-methylsulfanyl-propyl)-amine       27   Dibenzofuran-2-yl-bis-(3-methyl-butyl)-amine       28   Dibenzofuran-2-yl-dipropyl-amine       29   N 3 -(1,1-Dioxo-hexahydro-thiopyran-4-yl)-N 2 ,N 2 -dimethyl-           9H-fluorene-2,3-diamine       30   N 3 -Isopropyl-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine       31   N 2 ,N 2 -Dimethyl-N 3 -(tetrahydro-thiopyran-4-yl)-9H-           fluorene-2,3-diamine       32   N 3 -Cyclohexyl-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine       33   N 3 -Cycloheptyl-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine       34   N 3 -(1-Ethyl-propyl)-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-           diamine       35   N 3 -(1-Cyclopropyl-ethyl)-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-           diamine       36   N 3 -sec-Butyl-N 2 ,N 2 -dimethyl-9H-fluorene-2,3-diamine       37   (9H-Fluoren-2-yl)-isopropyl-amine       38   (9H-Fluoren-2-yl)-(tetrahydro-thiopyran-4-yl)-amine       39   Cycloheptyl-(9H-fluoren-2-yl)-amine       40   Dibenzofuran-2-yl-(1,1-dioxo-hexahydro-thiopyran-4-yl)-           amine       41   Dibenzofuran-2-yl-piperidin-4-yl-amine       42   Dibenzofuran-2-yl-isopropyl-amine       43   Cyclohexyl-dibenzofuran-2-yl-amine       44   (1-Cyclopropyl-ethyl)-dibenzofuran-2-yl-amine       45   Dibenzofuran-3-yl-(1,1-dioxo-hexahydro-thiopyran-4-yl)-           amine       46   Dibenzofuran-3-yl-piperidin-4-yl-amine       47   Dibenzoforan-3-yl-isopropyl-amine       48   Dibenzofuran-3-yl-(tetrahydro-thiopyran-4-yl)-amine       49   Cyclohexyl-dibenzofuran-3-yl-amine       50   Cycloheptyl-dibenzofuran-3-yl-amine       51   (4-Chloro-benzyl)-dibenzofuran-2-yl-amine       52   (4-Chloro-3-nitro-benzyl)-dibenzofuran-2-yl-amine       53   Dibenzofuran-2-yl-(3-trifluoromethoxy-benzyl)-amine       54   Benzo[l,3]dioxol-5-ylmethyl-dibenzofuran-2-yl-amine       55   Dibenzofuran-2-yl-(2,3-dihydro-benzo[1,4]dioxin-6-           ylmethyl)-amine       56   Dibenzofuran-2-yl-(3,5-dimethoxy-benzyl)-amine       57   Dibenzofuran-2-yl-(4-trifluoromethyl-benzyl)-amine       58   Dibenzoforan-2-yl-(2-methyl-benzyl)-amine       59   Dibenzofuran-2-yl-thiophen-3-ylmethyl-amine       60   Dibenzofuran-2-yl-(4-nitro-benzyl)-amine       61   Dibenzofuran-2-yl-(4-methylsulfanyl-benzyl)-amine       62   Dibenzofuran-2-yl-(4-methyl-benzyl)-amine       63   Benzyl-dibenzofuran-2-yl-amine       64   (3-Benzyloxy-benzyl)-dibenzofuran-2-yl-amine       65   (1-Benzyl-butyl)-dibenzofuran-2-yl-amine       66   Dibenzofuran-2-yl-[2-(2-methoxy-phenyl)-1-methyl-           ethyl]-amine       67   3-(Dibenzofuran-2-ylamino)-2-methyl-butan-1-ol       68   Dibenzofuran-2-yl-(1-ethyl-butyl)-amine       69   Dibenzofuran-2-yl-(1-ethyl-propyl)-amine       70   Dibenzofuran-2-yl-(1,3-dimethyl-butyl)-amine       71   (1-Cyclohexyl-ethyl)-dibenzofuran-2-yl-amine       72   Cyclooctyl-dibenzofuran-2-yl-amine       73   Cycloheptyl-dibenzofuran-2-yl-amine       74   Dibenzoforan-2-yl-(tetrahydro-thiopyran-4-yl)-amine       75   Dibenzofuran-2-yl-(tetrahydro-thiophen-3-yl)-amine       76   Dibenzofuran-2-yl-(1,2-dimethyl-propyl)-amine       77   Dibenzofuran-2-yl-(1-methyl-butyl)-amine       78   sec-Butyl-dibenzofuran-2-yl-amine       79   Benzofurp[3,2-b]pyridin-8-yl-(2-fluoro-benzyl)-amine       80   Benzofuro[3,3-b]pyridin-8-yl-pyridin-4-ylmethyl-amine       81   Benzofuro[3,2-b]pyridin-8-yl-(2-methyl-benzyl)-amine       82   N-(2-Fluoro-benzyl)-N′-methyl-dibenzoforan-2,8-diamine       83   N-Methyl-N′-quinolin-4-ylmethyl-dibenzofuran-2,8-           diamine       84   N-Methyl-N′-naphthanlen-1-ylmethyl-dibenzofuran-2,8-           diamine       85   N-(4-Methanesulfonyl-benzyl)-N′-methyl-diebnzofuran-           2,8-diamine       86   N-Methyl-N′-pyridin-4-ylmethyl-dibensofuran-2,8-diamine       87   N-Methyl-N′-(2-methyl-benzyl)-dibenzofuran-2,8-diamine       88   Naphthanlen-1-ylmethyl-(10H-phenothiazin-2-yl)-amine       89   (4-Methanesulfonyl-benzyl)-(10H-phenothiazin-2-yl)-amine       90   (3-Fluoro-2-methyl-benzyl)-(10-oxa-9-thia-1-aza-           anthracen-6-yl)-amine       91   (2-Fluoro-2-methyl-benzyl)-(10-oxa-9-thia-1-aza-           anthracen-6-yl)-amine       92   (10-Oxa-9-thia-1-aza-anthracen-6-yl)-qinolin-4-           ylmethyl-amine       93   Naphthalene-1-ylmethyl-(10-oxa-9-thia-1-aza-anthracen-           6-yl)-amine       94   (4-Methanesulfonyl-benzyl)-(10-oxa-9-thia-1-aza-           anthracen-6-yl)-amine       95   (10-Oxa-9-thia-1-aza-anthracen-6-yl)-pyridin-4-           ylmethyl-amine       96   (2-Methyl-benzyl)-(10-oxa-9-thia-1-aza-anthracen-           6-yl)-amine       97   Anthracen-2-yl-quinolin-4-ylmethyl-amine       98   Anthracen-2-yl-(4-methanesulfonyl-benzyl)-amine       99   Anthracen-2-yl-pyridin-4-ylmethyl-amine       100   Anthracen-2-yl-(2-methyl-benzyl)-amine       101   Dibenzo[b,e][1,4]-dioxin-2-yl-(2-fluoro-benzyl)-amine       102   Dibenzo[b,e][1,4]dioxin-2-yl-(2-fluoro-benzyl)-amine       103   Dibenzo[b,e][1,4]fioxin-2-yl-quinolin-4-ylmethyl-amine       104   Dibenzo[b,e][1,4]fioxin-2-yl-naphthalen-1-ylmethyl-amine       105   Dibenzo[b,e][1,4]fioxin-2-yl-(4-methanesulfonyl-benzyl)-           amine       106   Dibenzo[b,e][1,4]fioxin-2-yl-pyridin-4-ylmethyl-amine       107   8-(3-Fluoro-2-methyl-benzylamino)-dibenzofuran-2-ol       108   8-(2-Fluoro-benzylamino)-dibenzofuran2-ol       109   8-(4-Methanesulfonyl-benzylamino)-dibenzofuran-2-ol       110   8-[(Pyridin-4-ylmethyl)-amino]-dibenzofuran-2-ol       111   8-(2-Methyl-benzylamino)-dibenzofuran-2-ol       112   (8-Chloro-dibenzofuran-2-yl)-(2-fluoro-benzyl)-amine       113   8-Chloro-dibenzofuran-2-yl)-naphthalen-1-ylmethyl-amine       114   8-Chloro-dibenzofuran-2-yl)-(4-methanesulfonyl-benzyl)-           amine       115   (4-Methanesulfonyl-benzyl)-(6,7,8,9-tetrahydro-5H-           carbazol-3-yl)-amine       116   Pyridin-4-ylmethyl-(6,7,8,9-tetrahydro-5H-carbazol-3-yl)-           amine       117   Benzofuro[3,2-b]pyridin-8-yl-(3-fluoro-2-methyl-benzyl)-           amine       118   Dibenzofuran-2-yl-quinolin-4-ylmethyl-amine       119   Dibenzofuran-2-yl-quinolin-2-ylmethyl-amine       120   (4-Dimethylamino-benzyl)-(8-fluoro-dibenzofuran-2-yl)-           amine       121   Dibenzofuran-2-yl-(4-dimethylamino-benzyl)-amine       122   Diebnzofuran-2-yl-(5-nitro-thiophen-2-ylmethyl)-amine       123   Dibenzofuran-2-yl-thiazol-2-ylmethyl-amine       124   Benzyl-(8-fluoro-dibenzofuran-2-yl)-amine       125   N-(-3-Methoxybenzyl)-N′-methyl-dibenzofuran-2,8-diamine       126   N-(3,5-Dimethoxy-benzyl)-N′-methyl-dibenzofuran-2,8-           diamine       127   N-(4-tert-Butyl-benzyl)-N′-methyl-dibenzofuran-2,8-           diamine       128   N-Benzyl-N′-methyl-dibenzofaran-2,8-diamine       129   2-[(8-Methylamino-dibenzofuran-2-ylamino)-methyl]-           benzonitrile       130   (4-Methoxy-benzyl)-phenoxathiin-3-yl-amine       131   (8-Chloro-dibenzofuran-2-yl)-(3-methoxy-benzyl)-amine       132   (3-Methoxy-benzyl)-phenoxathiin-3-yl-amine       133   (3,5-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine       134   (3-Fluoro-4-methoxy-benzyl)-phenoxathiin-3-yl-amine       135   (4-tert-Butyl-benzyl)-phenoxathiin-3-yl-amine       136   Benzyl-phenoxathiin-3-yl-amine       137   (2-Ethoxy-benzyl)-phenoxathiin-3-yl-amine       138   (8-Chloro-dibenzofuran-2-yl)-(3,5-dimethoxy-benzyl)-           amine       139   (8-Chloro-dibenzofuran-2-yl)-(3-fluoro-4-methoxy-           benzyl)-amine       140   Benzyl-(8-chloro-dibenzofuran-2-yl)-amine       141   (9H-Fluoren-2-yl)-(4-methoxy-benzyl)-amine       142   (8-Chloro-dibenzofuran-2-yl)-thiazol-2-ylmethyl-amine       143   (9H-Fluoren-2-yl)-(3-methoxy-benzyl)-amine       144   (3,5-Dimethoxy-benzyl)-(9H-fluoren-2-yl)-amine       145   (9H-Fluoren-2-yl)-(3-fluoro-4-methoxy-benzyl)-amine       146   (4-tert-Butyl-benzyl)-(9H-fluoren-2-yl)-amine       147   Benzyl-(9H-fluoren-2-yl)-amine       148   (9H-Fluoren-2-yl)-thiazol-2-ylmethyl-amine       149   (2-Ethoxy-benzyl)-(9H-fluoren2-yl-amine       150   Dibenzofuran-4-yl-(4-methoxy-benzyl)-amine       151   2-[(8-Chloro-dibenzofuran-2-ylamino)-methyl]-benzonitrile       152   Dibenzofuran-4-yl-(3-methoxy-benzyl)-amine       153   Dibenzoforan-4-yl-(3,5-dimethoxy-benzyl)-amine       154   Dibenzofuran-4-yl-(3-fluoro-4-methoxy-benzyl)-amine       155   (4-tert-Butyl-benzyl)-dibenzofuran-4-yl-amine       156   Dibenzofuran-4-yl-(2-ethoxy-benzyl)-amine       157   N-(4-Methoxy-benzyl)-N′-methyl-dibenzofuran-2,8-diamine       158   (8-Chloro-dibenzofuran-2-yl)(4-methoxy-benzyl)-amine       159   (8-Chloro-dibenzofuran-2-yl)-(2-ethoxy-benzyl)-amine       160   Dibenzofuran-4-yl-(2,4-dimethyl-benzyl)-amine       161   N-Methyl-N′-thiophen-3-ylmethyl-dibenzofuran-2,8-diamine       162   N-Methyl-N′-pyridin-2-ylmethyl-dibenzofuran-2,8-diamine       163   (2-Bromo-benzyl)-phenoxathiin-3-yl-amine       164   Phenoxathiin-3-yl-quinolin-4-ylmethyl-amine       165   Phenoxathiin-3-yl-thiophen-3-ylmethyl-amine       166   (3-Methyl-pyridin-2-ylmethyl)-phenoxathiin-3-yl-amine       167   Phenoxathiin-3-yl-pyridin-3-ylmethyl-amine       168   Phenoxathiin-3-yl-pyridin-2-ylmethyl-amine       169   (8-Chloro-dibenzofuran-2-yl)-thiophen-3-ylmethyl-amine       170   (2-Bromo-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine       171   (8-Chloro-dibenzofuran-2-yl)-(3-methyl-pyridin-2-           ylmethyl)-amine       172   (9-Ethyl-9H-carbazol-3-yl)-thiophen-3-ylmethyl-amine       173   (5-Chloro-thiophen-2-ylmethyl)-(9-ethyl-9H-carbazol-3-           yl)-amine       174   (9-Ethyl-9H-carbazol-3-yl)-pyridin-3-ylmethyl-amine       175   (2-Bromo-benzyl)-(9H-fluoren-2-yl)-amine       176   (8-Chloro-dibenzofuran-2-yl)-pyridin-4-ylmethyl-amine       177   (9H-Fluoren-2-yl)-quinolin-2-ylmethyl-amine       178   (9H-Fluoren-2-yl)-thiophen-3-ylmethyl-amine       179   (9H-Fluoren-2-yl)-(3-methyl-pyridin-2-ylmethyl)-amine       180   (9H-Fluoren-2-yl)-pyridin-4-ylmethyl-amine       181   (9H-Fluoren-2-yl)-pyridin-3-ylmethyl-amine       182   (9H-Fluoren-2-yl)-pyridin-2-ylmethyl-amine       183   (8-Chloro-dibenzofuran-2-yl)-pyridin-3-ylmethyl-amine       184   Dibenzofuran-4-yl-quinolin-4-ylmethyl-amine       185   Dibenzofuran-4-yl-quinolin-2-ylmethyl-amine       186   Dibenzofuran-4-yl-thiophen-3-ylmethyl-amine       187   Dibenzofuran-4-yl-(3-methyl-pyridin-2-ylmethyl)-amine       188   Dibenzofuran-4-yl-pyridin-4-ylmethyl-amine       189   Dibenzofuran-4-yl-pyridin-3-ylmethyl-amine       190   Dibenzofuran-4-yl-pyridin-2-ylmethyl-amine       191   (2-Bromo-benzyl)-(8-chloro-dibenzofuran-2-yl)-amine       192   (8-Chloro-dibenzofuran-2-yl)-pyridin-2-ylmethyl-amine       193   N-Methyl-N′-(2,3,6-trifluoro-benzyl)-dibenzofuran-2,8-           diamine       194   N-Methyl-N′-(2,3,4-trifluoro-benzyl)-dibenzofuran-2,8-           diamine       195   N-(2,6-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-           diamine       196   N-(2,5-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-           diamine       197   N-(2,4-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-           diamine       198   N-(2,3-Difluoro-benzyl)-N′-methyl-dibenzofuran-2,8-           diamine       199   N-(2,5-Dimethyl-benzyl)-N′-methyl-dibenzofuran-2,8-           diamine       200   N-(2,4-Dimethyl-benzyl)-N′-methyl-dibenzofuran-2,8-           diamine       201   N-(2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-N′-methyl-           dibenzofuran-2,8-diamine       202   (3-Fluoro-2-methyl-benzyl)-phenoxathiin-3-yl-amine       203   (8-Chloro-dibenzofuran-2-yl)-(2,3,6-trifluoro-benzyl)-           amine       204   Phenoxathiin-3-yl-(2,3,6-trifluoro-benzyl)-amine       205   Phenoxathiin-3-yl-(2,3,4-trifluoro-benzyl)-amine       206   (2,6-Difluoro-benzyl)-phenoxathiin-3-yl-amine       207   (2,5-Difluoro-benzyl)-phenoxathiin-3-yl-amine       208   (2,4-Difluoro-benzyl)-phenoxathiin-3-yl-amine       209   (2,3-Difluoro-benzyl)-phenoxathiin-3-yl-amine       210   (2,4-Dimethyl-benzyl)-phenoxathiin-3-yl-amine       211   (2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-phenoxathiin-           3-yl-amine       212   Benzo[b]thiophen-5-yl-(3-fluoro-2-methyl-benzyl)-           amine       213   (8-Chloro-dibenzofuran-2-yl)-(2,3,4-trifluoro-benzyl)-           amine       214   (8-Chloro-dibenzofuran-2-yl)-(2,6-difluoro-benzyl)-           amine       215   (8-Chloro-dibenzofuran-2-yl)-(2,5-difluoro-benzyl)-           amine       216   (8-Chloro-dibenzofuran-2-yl)-(2,4-difluoro-benzyl)-           amine       217   (9-Ethyl-9H-carbazol-3-yl)-(3-fluoro-2-methyl-benzyl)-           amine       218   (8-Chloro-dibenzofuran-2-yl)-(2,3-difluoro-benzyl)-           amine       219   (9-Ethyl-9H-carbazol-3-yl)-(2,3,6-trifluoro-benzyl)-           amine       220   (9-Ethyl-9H-carbazol-3-yl)-(2,3,4-trifluoro-benzyl)-           amine       221   (2,6-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine       222   (2,5-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine       223   (2,4-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine       224   (2,3-Difluoro-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine       225   (2,5-Dimethyl-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine       226   (2,4-Dimethyl-benzyl)-(9-ethyl-9H-carbazol-3-yl)-amine       227   (2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-(9-ethyl-9H-           carbazol-3-yl)-amine       228   (9H-Fluoren-2-yl)-(3-fluoro-2-methyl-benzyl)-amine       229   (8-Chloro-dibenzofuran-2-yl)-(2,5-dimethyl-benzyl)-           amine       230   (9H-Fluoren-2-yl)-(2,3,6-trifluoro-benzyl)-amine       231   (9H-Fluoren-2-yl)-(2,3,4-trifluoro-benzyl)-amine       232   (2,5-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine       233   (2,4-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine       234   (2,3-Difluoro-benzyl)-(9H-fluoren-2-yl)-amine       235   (2,5-Dimethyl-benzyl)-(9H-fluoren-2-yl)-amine       236   (2,4-Dimethyl-benzyl)-(9H-fluoren-2-yl)-amine       237   (2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-(9H-fluoren-           2-yl)-amine       238   (8-Chloro-dibenzofuran-2-yl)-(2,4-dimethyl-benzyl)-           amine       239   Dibenzofuran-4-yl-(2,5-dimethyl-benzyl)-amine       240   Dibenzofuran-4-yl-(3-fluoro-2-methyl-benzyl)-amine       241   N-(3-Fluoro-2-methyl-benzyl)-N′-methyl-dibenzofuran-           2,8-diamine       242   (8-Chloro-dibenzofuran-2-yl)-(3-fluoro-2-methyl-benzyl)-           amine       243   (8-Chloro-dibenzofuran-2-yl)-(2,3-dihydro-           benzo[1,4]dioxin-6-ylmethyl)-amine       244   (2,5-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine       245   (2,3-Dimethoxy-benzyl)-phenoxathiin-3-yl-amine       246   (2-Chloro-benzyl)-phenoxathiin-3-yl-amine       247   (2-Methoxy-benzyl)-phenoxathiin-3-yl-amine       248   (2-Methyl-benzyl)-phenoxathiin-3-yl-amine       249   Anthracen-2-yl-(2-chloro-benzyl)-amine       250   Anthracen-2-yl-(2-fluoro-benzyl)-amine       251   Dibenzo[1,4]dioxin-2-yl-(2,3-dimethoxy-benzyl)-amine       252   (2-Chloro-benzyl)-dibenzo[1,4]dioxin-2-yl-amine       253   2-(Dibenzo[1,4]dioxin-2-ylaminomethyl)-phenol       254   Dibenzo[1,4]dioxin-2-yl-(2-methoxy-benzyl)-amine       255   2-[(9-Ethyl-9H-carbazol-3-ylamino)-methyl]-phenol       256   (9-Ethyl-9H-carbazol-3-yl)-(2-fluoro-benzyl)-amine       257   (9-Ethyl-9H-carbazol-3-yl)-(2-methyl-benzyl)-amine       258   (2-Chloro-benzyl)-(9H-fluoren-2-yl)-amine       259   2-[(9H-Fluoren-2-ylamino)-methyl]-phenol       260   (9H-Fluoren-2-yl)-(2-methoxy-benzyl)-amine       261   (9H-Fluoren-2-yl)-(2-trifluoromethyl-benzyl)-amine       262   (9H-Fluoren-2-yl)-(2-fluoro-benzyl)-amine       263   Dibenzofuran-4-yl-(2,5-dimethoxy-benzyl)-amine       264   Dibenzofuran-4-yl-(2,3-dimethoxy-benzyl)-amine       265   2-(Dibenzofuran-4-ylaminomethyl)-phenol       266   Dibenzoforan-4-yl-(2-methoxy-benzyl)-amine       267   (2,5-Dimethoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)-           amine       268   (2,3-Dimethoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)-           amine       269   (2-Methoxy-benzyl)-(3-methoxy-dibenzofuran-2-yl)-amine       270   Dibenzofuran-2-yl-(2,5-dimethoxy-benzyl)-amine       271   Dibenzofuran-2-yl-(4-methoxy-benzyl)-amine       272   (2-Bromo-benzyl)-dibenzofuran-2-yl-amine       273   (8-Fluoro-dibenzofuran-2-yl)-(3H-imidazol-4-ylmethyl)-           amine       274   2-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]-           benzonitrile       275   (2-Ethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine       276   (8-Fluoro-dibenzofuran-2-yl)-(4-methylsulfanyl-benzyl)-           amine       277   (2-Bromo-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine       278   (8-Fluoro-dibenzofuran-2-yl)-quinolin-4-ylmethyl-amine       279   (8-Fluoro-dibenzofuran-2-yl)-quinolin-2-ylmethyl-amine       280   Dibenzofuran-2-yl-naphthalen-1-ylmethyl-amine       281   (8-Fluoro-dibenzofuran-2-yl)-naphthalen-2-ylmethyl-           amine       282   (8-Fluoro-dibenzofuran-2-yl)-naphthalen-1-ylmethyl-           amine       283   Dibenzofuran-2-yl-(2-nitro-benzyl)-amine       284   Dibenzofuran-2-yl-(3H-imidazol-4-ylmethyl)-amine       285   2-(Dibenzofuran-2-ylaminomethyl)-benzonitrile       286   Dibenzofuran-2-yl-(2-ethoxy-benzyl)-amine       287   Dibenzofuran-2-yl-(3-trifluoromethyl-benzyl)-amine       288   (4-tert-Butyl-benzyl)-dibenzofuran-2-yl-amine       289   Dibenzofuran-2-yl-(3-fluoro-benzyl)-amine       290   (2,5-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-           amine       291   (2,3-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-           amine       292   (4-Benzyloxy-benzyl)-(8-fluoro-dibenzoforan-2-yl)-amine       293   (3-Benzyloxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine       294   (4-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine       295   (3-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine       296   (2-Chloro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine       297   4-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]-phenol       298   3-[(8-Fluoro-dibenzofuran-2-ylamino)-methyl]-phenol       299   Dibenzofuran-2-yl-(2-fluoro-benzyl)-amine       300   (8-Fluoro-dibenzofuran-2-yl)-(4-methoxy-benzyl)-amine       301   (8-Fluoro-dibenzofuran-2-yl)-(3-methoxy-benzyl)-amine       302   (8-Fluoro-dibenzofuran-2-yl)-(2-methoxy-benzyl)-amine       303   (8-Fluoro-dibenzofuran-2-yl)-(4-trifluoromethyl-benzyl)-           amine       304   (8-Fluoro-dibenzofuran-2-yl)-(3-trifluoromethyl-benzyl)-           amine       305   (4-tert-Butyl-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine       306   (4-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine       307   (3-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine       308   (2-Fluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine       309   (8-Fluoro-dibenzofuran-2-yl)-(4-methyl-benzyl)-amine       310   (8-Fluoro-dibenzofuran-2-yl)-(3-methyl-benzyl)-amine       311   Dibenzofuran-2-yl-(2,6-dimethoxy-benzyl)-amine       312   Dibenzofuran-2-yl-(2,4-dimethoxy-benzyl)-amine       313   Dibenzofuran-2-yl-(2,3-dimethoxy-benzyl)-amine       314   (4-Benzyloxy-benzyl)-dibenzofuran-2-yl-amine       315   Dibenzofuran-2-yl-(3-methyl-benzyl)-amine       316   (3-Chloro-benzyl)-dibenzofuran-2-yl-amine       317   3-(Dibenzoforan-2-ylaminomethyl)-phenol       318   (2-Chloro-benzyl)-dibenzofuran-2-yl-amine       319   Dibenzofuran-2-yl-(3-methoxy-benzyl)-amine       320   Dibenzofuran-2-yl-(2-methoxy-benzyl)-amine       321   (9H-Fluoren-2-yl)-(2-methyl-benzyl)-amine       322   Dibenzofuran-4-yl-(2-methyl-benzyl)-amine       323   (8-Chloro-dibenzofuran-2-yl)-(2-methyl-benzyl)-amine       324   (2-Methyl-benzyl)-(10H-phenothiazin-2-yl)-amine       325   Dibenzo[b,e][1,4]dioxin-2-yl-(2-methyl-benzyl)-amine       326   Dibenzofuran-2-yl-(2,6-difluoro-benzyl)-amine       327   Dibenzofuran-2-yl-(2,5-difluoro-benzyl)-amine       328   Dibenzofuran-2-yl-(2,4-difluoro-benzyl)-amine       329   Dibenzofuran-2-yl-(2,3-difluoro-benzyl)-amine       330   (8-Fluoro-dibenzofuran-2-yl)-thiophen-2-ylmethyl-amine       331   Dibenzofuran-2-yl-(2,5-dimethyl-benzyl)-amine       332   (8-Fluoro-dibenzofuran-2-yl)-thiophen-3-ylmethyl-amine       333   (8-Fluoro-dibenzofuran-2-yl)-furan-2-ylmethyl-amine       334   (8-Fluoro-dibenzofuran-2-yl)-furan-3-ylmethyl-amine       335   (8-Fluoro-dibenzofuran-2-yl)-(6-methyl-pyridin-2-           ylmethyl)-amine       336   (8-Fluoro-dibenzofuran-2-yl)-(4-methanesulfonyl-           benzyl)-amine       337   (8-Fluoro-dibenzofuran-2-yl)-pyridin-4-ylmethyl-amine       338   (8-Fluoro-dibenzofuran-2-yl)-pyridin-3-ylmethyl-amine       339   (8-Fluoro-dibenzofuran-2-yl)-pyridin-2-ylmethyl-amine       340   (8-Fluoro-dibenzofuran-2-yl)-(3-fluoro-4-methoxy-           benzyl)-amine       341   Dibenzofuran-2-yl-(2,4-dimethyl-benzyl)-amine       342   (8-Fluoro-dibenzofuran-2-yl)-(3-fluoro-2-methyl-           benzyl)-amine       343   (8-Fluoro-dibenzofuran-2-yl)-(2,3,6-trifluoro-benzyl)-           amine       344   (8-Fluoro-dibenzofuran-2-yl)-(2,3,4-trifluoro-benzyl)-           amine       345   (3,5-Difluoro-benzyl)-(8-fluoro-dibenzoforan-2-yl)-           amine       346   (3,4-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-           amine       347   (3,5-difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-           amine       348   (2,6-Difluoro-benzyl(2,5-Difluoro-benzyl)-(8-fluoro-           dibenzofuran-2-yl)-amine       349   (2,4-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine       350   (2,3-Difluoro-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine       351   (2,5-Dimethyl-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine       352   (2,4-Dimethyl-benzyl)-(8-fluoro-dibenzofuran-2-yl)-amine       353   (2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-(8-fluoro-           dibenzofuran-2-yl)-amine       354   (3,5-Dimethoxy-benzyl)-(8-fluoro-dibenzofuran-2-yl)-           amine       355   Dibenzofuran-2-yl-furan-2-ylmethyl-amine       356   Dibenzofuran-2-yl-furan-3-ylmethyl-amine       357   Dibenzofuran-2-yl-(6-methyl-pyridin-2-ylmethyl)-amine       358   Dibenzoforan-2-yl-(4-methanesulfonyl-benzyl)-amine       359   Dibenzofuran-2-yl-pyridin-4-ylmethyl-amine       360   Dibenzofuran-2-yl-pyridin-3-ylmethyl-amine       361   Dibenzofuran-2-yl-pyridin-2-ylmethyl-amine       362   Dibenzofuran-2-yl-(3-fluoro-4-methoxy-benzyl)-amine       363   Dibenzofuran-2-yl-(3-fluoro-2-methyl-benzyl)-amine       364   Dibenzofuran-2-yl-(2,3,6-trifluoro-benzyl)-amine       365   Dibenzofuran-2-yl-(2,3,4-trifluoro-benzyl)-amine       366   Dibenzofuran-2-yl-(3,5-difluoro-benzyl)-amine       367   Dibenzofuran-2-yl-(3,4-difluoro-benzyl)-amine       368   Dibenzofuran-2-yl-(3,4-dimethoxy-benzyl)-amine       369   Dibenzofuran-2-yl-methyl-(2-methyl-benzyl)-amine       370   Dibenzothiohen-2-yl-(2,4-dimethyl-benzyl)-amine       371   (4-tert-Butyl-benzyl)-dibenzothiohen-2-yl-amine       372   (2-Chloro-benzyl)-dibenzothiohen-2-yl-amine       373   Dibenzothiohen-2-yl-(2,6-difluoro-benzyl)-amine       374   Dibenzothiohen-2-yl-(2,3,6-trifluoro-benzyl)-amine       375   Dibenzothiohen-2-yl-(2-fluoro-benzyl)-amine       376   Benzyl-dibenzothiohen-2-yl-amine       377   Dibenzothiohen-2-yl-(4-methoxy-benzyl)-amine       378   Dibenzothiohen-2-yl-(2,3-dimethoxy-benzyl)-amine       379   Dibenzothiohen-2-yl-(2,5-difluoro-benzyl)-amine       380   Dibenzothiohen-2-yl-(3-methoxy-benzyl)-amine       381   Dibenzothiohen-2-yl-(2,3,4-trifluoro-benzyl)-amine       382   (-2-Bromo-benzyl)-dibenzothiohen-2-yl-amine       383   Dibenzothiohen-2-yl-(2,3-dihydro-1,4-benzodioxin-6-           ylmethyl)-amine       384   Dibenzothiohen-2-yl-(3-fluoro-4-methoxy-benzyl)-amine       385   Dibenzothiohen-2-yl-(2,5-dimethyl-benzyl)-amine       386   Dibenzothiohen-2-yl-thiophen-3-ylmethyl-amine       387   Dibenzothiohen-2-yl-naphthalene-1-ylmethyl-amine       388   Dibenzothiohen-2-yl-(2-trifluoromethyl-benzyl)-amine       389   Dibenzothiohen-2-yl-naphthalen-2-ylmethyl-amine       390   Dibenzothiohen-2-yl-(2-ethoxy-benzyl)-amine       391   (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3-fluoro-           2-methyl-benzyl)-amine       392   (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2-methyl-           benzyl)-amine       393   (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,4-           dimethyl-benzyl)-amine       394   (4-tert-Butyl-benzyl)-(10,11-dihydro-5H-           dibenz[b,f]azepin-2-yl)-amine       395   (2-Chloro-benzyl)-(10,11-dihydro-5H-           dibenz[b,f]azepin-2-yl)-amine       396   (2,6-Difluoro-benzyl)-(10,11-dihydro-5H-           dibenz[b,f]azepin-2-yl)-amine       397   (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-           (2,3,6-trifluoro-benzyl)-amine       398   (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2-           fluoro-benzyl)-amine       399   (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3,5-           dimethoxy-benzyl)-amine       400   Benzyl-(10,11-dihydro-5H-dibenz[b,f]azepin-2-yl)-amine       401   (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(4-           methoxy-benzyl)-amine       402   (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,3-           dimethoxy-benzyl)-amine       403   (2,5-difluoro-benzyl)-(10,11-dihydro-5H-           dibenz[b,f]azepin-2-yl)-amine       404   (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(3-           methoxy-benzyl)-amine       405   (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-(2,3,4-           trifluoro-benzyl)-amine       406   (2-Bromo-benzyl)-(10,11-dihydro-5H-           dibenz[b,f]azepin-2-yl)-amine       407   (2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-(10,11-           dihydro-5H-dibenz[b,f]azepin-2-yl)-amine       408   (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-           (3-fluoro-4-methoxy-benzyl)-amine       409   (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-           (2,5-dimethyl-benzyl)-amine       410   (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-           thiophen-3-ylmethyl-amine       411   (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-           naphthalen-1-ylmethyl-amine       412   (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-           (2-trifluoromethyl-benzyl)-amine       413   (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-           naphthalen-2-ylmethyl-amine       414   (10,11-Dihydro-5H-dibenz[b,f]azepin-2-yl)-           (2-ethoxy-benzyl)-amine       415   (3-Fluoro-2-methyl-benzyl)-(10H-phenothiazin-2-yl)-amine       416   (2,4-Dimethyl-benzyl)-(10H-phenothiazin-2-yl)-amine       417   (4-tert-Butyl-benzyl)-(10H-phenothiazin-2-yl)-amine       418   (2-Chloro-benzyl)-(10H-phenothiazin-2-yl)-amine       419   (2,6-Difluoro-benzyl)-(10H-phenothiazin-2-yl)-amine       420   (10H-Phenothiazin-2-yl)-(2,3,6-trifluorobenzyl)-amine       421   (2-Fluoro-benzyl)-(10H-phenothiazin-2-yl)-amine       422   (3,5-Dimethoxy-benzyl)-(10H-phenothiazin-2-yl)-amine       423   Benzyl-(10H-phenothiazin-2-yl)-amine       424   (4-Methoxy-benzyl)-(10H-phenothiazin-2-yl)-amine       425   (2,5-Difluoro-benzyl)-(10H-phenothiazin-2-yl)-amine       426   (10H-Phenothiazin-2-yl)-(2,3,4-trifluoro-benzyl)-amine       427   (2,3-Dihydro-1,4-benzodioxin-6-ylmethyl)-(10H-           phenothiazin-2-yl)-amine       428   (3-Fluoro-4-methoxy-benzyl)-(10H-phenothiazin-2-yl)-           amine       429   (2,5-Dimethyl-benzyl)-(10H-phenothiazin-2-yl)-amine       430   (10H-Phenothiazin-2-yl)-thiophen-3-ylmethyl-amine       431   (10H-Phenothiazin-2-yl)-(2-trifluoromethyl-benzyl)-           amine       432   (9H-Carbazol-3-yl)-(3-fluoro-2-methyl-benzyl)-amine       433   (9H-Carbazol-3-yl)-(2-methyl-benzyl)-amine       434   (9H-Carbazol-3-yl)-(2,4-dimethyl-benzyl)-amine       435   (4-tert-Butyl-benzyl)-(9H-carbazol-3-yl)-amine       436   (9H-Carbazol-3-yl)-(2-chloro-benzyl)-amine       437   (9H-Carbazol-3-yl)-(2,6-difluoro-benzyl)-amine       438   (9H-Carbazol-3-yl)-(2,3,6-trifluoro-benzyl)-amine       439   (9H-Carbazol-3-yl)-(3,5-dimethoxy-benzyl)-amine       440   (9H-Carbazol-3-yl)-(2,3-dimethoxy-benzyl)-amine       441   (9H-Carbazol-3-yl)-(2,5-difluoro-benzyl)-amine       442   (9H-Carbazol-3-yl)-(2,3,4-trifluoro-benzyl)-amine       443   (9H-Carbazol-3-yl)-(2,3-dihydro-1,4-benzodioxin-           6-ylmethyl)-amine       444   (9H-Carbazol-3-yl)-(2,5-dimethyl-benzyl)-amine       445   (9H-Carbazol-3-yl)-naphthalen-1-ylmethyl-amine       446   (9H-Carbazol-3-yl)-naphthalen-2-ylmethyl-amine       447   Dibenzofuran-2-yl-bis-(2,3-dihydro-benzo[1,4]dioxin-6-           ylmethyl)-amine       448   Dibenzofuran-2-yl-bis-thiophen-3-ylmethyl-amine       449   Dibenzofuran-2-yl-(4-phenoxy-benzyl)-amine       450   2-Dibenzofuran-2-yl-2,3-dihydro-1H-isoindole       451   2-Dibenzofuran-2-yl--1H-isoindole-1,3-dione       452   Dibenzofuran-2-yl-(4-trifluoromethoxy-benzyl)-amine       453   Dibenzofuran-2-yl-(2-methoxy-benzyl)-amine       454   Dibenzofuran-2-yl-(3-phenoxy-benzyl)-amine       455   Dibenzofuran-2-yl-methyl(2-methyl-benzyl)-amine       456   Dibenzofuran-2-yl-(1-phenyl-butyl)-amine       457   Dibenzofuran-2-yl-phenethyl-amine       458   Dibenzofuran-2-yl-(1-phenyl-ethyl)-amine                  
 
       EXAMPLES  
       [0088]    
       
         
               
               
               
               
               
             
               
               
               
               
               
             
           
               
                   
               
               
                   
               
               
                   
                   
                 General 
                   
                   
               
               
                   
                   
                 proce- 
                 M + H 
                 MOLECULAR 
               
               
                 Example 
                 MOL STRUCTURE 
                 dure 
                 (APCI) −   
                 FORMULA 
               
               
                   
               
             
             
               
                   
               
             
          
           
               
                   
                   
                   
                   
                   
               
               
                 1 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 7 
                 282 
                 C18H19NO2 
               
               
                   
               
               
                 2 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 7 
                 250 
                 C18H19N 
               
               
                   
               
               
                 3 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 7 
                 250 
                 C18H19N 
               
               
                   
               
               
                 4 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 7 
                 293 
                 C20H24N2 
               
               
                   
               
               
                 5 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 256 
                 C16H17NO2 
               
               
                   
               
               
                 6 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 314 
                 C18H19NO2S 
               
               
                   
               
               
                 7 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 310 
                 C20H23NO2 
               
               
                   
               
               
                 8 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 284 
                 C18H21NO2 
               
               
                   
               
               
                 9 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 270 
                 C17H19NO2 
               
               
                   
               
               
                 10 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 7, 5 
                 308 
                 C20H25N3 
               
               
                   
               
               
                 11 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 371 
                 C26H30N2 
               
               
                   
               
               
                 12 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 7 
                 265 
                 C18H20N2 
               
               
                   
               
               
                 13 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 328 
                 C24H25N 
               
               
                   
               
               
                 14 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 7 
                 238 
                 C17H19N 
               
               
                   
               
               
                 15 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 346 
                 C18H19NO4S 
               
               
                   
               
               
                 16 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 6 
                 322 
                 C22H27NO 
               
               
                   
               
               
                 17 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 6 
                 320 
                 C22H25NO 
               
               
                   
               
               
                 18 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 6 
                 318 
                 C22H23NO 
               
               
                   
               
               
                 19 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 6 
                 348 
                 C24H29NO 
               
               
                   
               
               
                 20 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 6 
                 278 
                 C19H19NO 
               
               
                   
               
               
                 21 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 6 
                 322 
                 C22H27NO 
               
               
                   
               
               
                 22 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 6 
                 292 
                 C20H21NO 
               
               
                   
               
               
                 23 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 6 
                 252 
                 C17H17NO 
               
               
                   
               
               
                 24 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 6, 5 
                 296 
                 C19H21NO2 
               
               
                   
               
               
                 25 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 6, 5 
                 264 
                 C19H21N 
               
               
                   
               
               
                 26 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 4 
                 3609 
                 C20H25NOS2 
               
               
                   
               
               
                 27 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 4 
                 324 
                 C22H29NO 
               
               
                   
               
               
                 28 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 4 
                 268 
                 C18H21NO 
               
               
                   
               
               
                 29 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 357 
                 C20H24N2O2S 
               
               
                   
               
               
                 30 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 7 
                 267 
                 C18H22N2 
               
               
                   
               
               
                 31 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 7 
                 325 
                 C20H24N2S 
               
               
                   
               
               
                 32 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 7 
                 307 
                 C21H26N2 
               
               
                   
               
               
                 33 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 7 
                 321 
                 C22H28N2 
               
               
                   
               
               
                 34 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 295 
                 C20H26N2 
               
               
                   
               
               
                 35 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 293 
                 C20H24N2 
               
               
                   
               
               
                 36 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 7 
                 281 
                 C19H24N2 
               
               
                   
               
               
                 37 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 7 
                 224 
                 C16H17N 
               
               
                   
               
               
                 38 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 282 
                 C18H19NS 
               
               
                   
               
               
                 39 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 7 
                 278 
                 C20H23N 
               
               
                   
               
               
                 40 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 316 
                 C17H17NO3S 
               
               
                   
               
               
                 41 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 6 
                 267 
                 C17H18N2O 
               
               
                   
               
               
                 42 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 6 
                 226 
                 C15H15NO 
               
               
                   
               
               
                 43 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 6 
                 266 
                 C18H19NO 
               
               
                   
               
               
                 44 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 252 
                 C17H17NO 
               
               
                   
               
               
                 45 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 316 
                 C17H17NO3S 
               
               
                   
               
               
                 46 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 267 
                 C17H18N2O 
               
               
                   
               
               
                 47 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 226 
                 C15H15NO 
               
               
                   
               
               
                 48 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 284 
                 C17H17NOS 
               
               
                   
               
               
                 49 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 266 
                 C18H19NO 
               
               
                   
               
               
                 50 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 280 
                 C19H21NO 
               
               
                   
               
               
                 51 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 308, 310 
                 C19H14ClNO 
               
               
                   
               
               
                 52 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 353, 355 
                 C19H13ClN2O3 
               
               
                   
               
               
                 53 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 358 
                 C20H14F3NO2 
               
               
                   
               
               
                 54 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 318 
                 C20H15NO3 
               
               
                   
               
               
                 55 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 332 
                 C21H17NO3 
               
               
                   
               
               
                 56 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C21H19NO3 
               
               
                   
               
               
                 57 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 342 
                 C20H14F3NO 
               
               
                   
               
               
                 58 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 1, 2, 3 
                 288 
                 C20H17NO 
               
               
                   
               
               
                 59 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 280 
                 C17H13NOS 
               
               
                   
               
               
                 60 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 319 
                 C19H14N2O3 
               
               
                   
               
               
                 61 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 320 
                 C20H17NOS 
               
               
                   
               
               
                 62 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 288 
                 C20H17NO 
               
               
                   
               
               
                 63 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 274 
                 C19H15NO 
               
               
                   
               
               
                 64 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 380 
                 C26H21NO2 
               
               
                   
               
               
                 65 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 330 
                 C23H23NO 
               
               
                   
               
               
                 66 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 332 
                 C22H21NO2 
               
               
                   
               
               
                 67 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 270 
                 C17H19NO2 
               
               
                   
               
               
                 68 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 268 
                 C18H21NO 
               
               
                   
               
               
                 69 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 254 
                 C17H19NO 
               
               
                   
               
               
                 70 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 268 
                 C18H21NO 
               
               
                   
               
               
                 71 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 294 
                 C20H23NO 
               
               
                   
               
               
                 72 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 294 
                 C20H23NO 
               
               
                   
               
               
                 73 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 6 
                 280 
                 C19H21NO 
               
               
                   
               
               
                 74 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 6 
                 284 
                 C17H17NOS 
               
               
                   
               
               
                 75 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 270 
                 C16H15NOS 
               
               
                   
               
               
                 76 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 254 
                 C17H19NO 
               
               
                   
               
               
                 77 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5 
                 254 
                 C17H19NO 
               
               
                   
               
               
                 78 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 5, 6 
                 240 
                 C16H17NO 
               
               
                   
               
               
                 79 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 293 
                 C18H13FN2O 
               
               
                   
               
               
                 80 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 276 
                 C17H13N2O 
               
               
                   
               
               
                 81 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 289 
                 C19H16N2O 
               
               
                   
               
               
                 82 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 321 
                 C20H17FN2O 
               
               
                   
               
               
                 83 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 354 
                 C23H19N3O 
               
               
                   
               
               
                 84 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 353 
                 C24H20N2O 
               
               
                   
               
               
                 85 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 381 
                 C21H20N2O3S 
               
               
                   
               
               
                 86 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 304 
                 C19H17N3O 
               
               
                   
               
               
                 87 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 317 
                 C21H20N2O 
               
               
                   
               
               
                 88 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3, 2 
                 355 
                 C23H18N2S 
               
               
                   
               
               
                 89 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 383 
                 C20H18N2O2S2 
               
               
                   
               
               
                 90 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 339 
                 C19H15FN2OS 
               
               
                   
               
               
                 91 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 325 
                 C18H13FN2OS 
               
               
                   
               
               
                 92 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 358 
                 C21H15N3OS 
               
               
                   
               
               
                 93 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 357 
                 C22H16N2OS 
               
               
                   
               
               
                 94 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 385 
                 C19H16N2O3S2 
               
               
                   
               
               
                 95 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 308 
                 C17H13N3OS 
               
               
                   
               
               
                 96 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 321 
                 C19H16N2OS 
               
               
                   
               
               
                 97 
                 p
                         
 
                 3 
                 335 
                 C24H18N2 
               
               
                   
               
               
                 98 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 362 
                 C22H19NO2S 
               
               
                   
               
               
                 99 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 285 
                 C20H16N2 
               
               
                   
               
               
                 100 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 298 
                 C22H19N 
               
               
                   
               
               
                 101 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 322 
                 C20H16FNO2 
               
               
                   
               
               
                 102 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 308 
                 C19H14FNO2 
               
               
                   
               
               
                 103 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 341 
                 C22H16N2O2 
               
               
                   
               
               
                 104 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 340 
                 C23H17NO2 
               
               
                   
               
               
                 105 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 368 
                 C20H17NO4S 
               
               
                   
               
               
                 106 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 291 
                 C18H14N2O2 
               
               
                   
               
               
                 107 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 322 
                 C20H16FNO2 
               
               
                   
               
               
                 108 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 308 
                 C19H14FNO2 
               
               
                   
               
               
                 109 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 368 
                 C20H17NO4S 
               
               
                   
               
               
                 110 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 291 
                 C18H14N2O2 
               
               
                   
               
               
                 111 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 304 
                 C20H17NO2 
               
               
                   
               
               
                 112 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 326, 328 
                 C19H13ClFNO 
               
               
                   
               
               
                 113 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 359 
                 C23H16ClNO 
               
               
                   
               
               
                 114 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 387 
                 C20H16ClNO3S 
               
               
                   
               
               
                 115 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 355 
                 C20H22N2O2S 
               
               
                   
               
               
                 124 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 292 
                 C19H14FNO 
               
               
                   
               
               
                 125 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 333 
                 C21H20N2O2 
               
               
                   
               
               
                 126 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 363 
                 C22H22N2O3 
               
               
                   
               
               
                 127 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 359 
                 C24H26N2O1 
               
               
                   
               
               
                 128 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 303 
                 C20H18N2O1 
               
               
                   
               
               
                 129 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 328 
                 C21H17N3O1 
               
               
                   
               
               
                 130 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 336 
                 C20H17N1O2S1 
               
               
                   
               
               
                 116 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 278 
                 C18H19N3 
               
               
                   
               
               
                 117 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 3 
                 307 
                 C19H15FN2O 
               
               
                   
               
               
                 118 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 325 
                 C22H16N2O 
               
               
                   
               
               
                 119 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 325 
                 C22H16N2O 
               
               
                   
               
               
                 120 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 335 
                 C21H19FN2O 
               
               
                   
               
               
                 121 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 317 
                 C21H20N2O 
               
               
                   
               
               
                 122 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 325 
                 C17H12N2O3S 
               
               
                   
               
               
                 123 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 281 
                 C16H12N2OS 
               
               
                   
               
               
                 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 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 22 
                 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 
                 C 16H14N2S 
               
               
                   
               
               
                 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 
                 C21H19NO 
               
               
                   
               
               
                 161 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 309 
                 C18H16N2OS 
               
               
                   
               
               
                 162 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 304 
                 C19H17N3O 
               
               
                   
               
               
                 163 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 383, 385 
                 C19H14BrNOS 
               
               
                   
               
               
                 164 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 357 
                 C22H16N2OS 
               
               
                   
               
               
                 165 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 312 
                 C17H13NOS2 
               
               
                   
               
               
                 166 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 321 
                 C19H16H2OS 
               
               
                   
               
               
                 167 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 307 
                 C18H14N2OS 
               
               
                   
               
               
                 168 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 307 
                 C18H14N2OS 
               
               
                   
               
               
                 169 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 314, 316 
                 C17H12ClNOS 
               
               
                   
               
               
                 170 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 379, 381 
                 C21H19BrN2 
               
               
                   
               
               
                 171 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 323, 325 
                 C19H15ClN2O 
               
               
                   
               
               
                 172 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 307 
                 C19H18N2S 
               
               
                   
               
               
                 173 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 341, 342 
                 C19H17ClN2S 
               
               
                   
               
               
                 174 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 302 
                 C20H19N3 
               
               
                   
               
               
                 175 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 350, 352 
                 C20H16BrN 
               
               
                   
               
               
                 176 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 309, 311 
                 C18H13ClN2O 
               
               
                   
               
               
                 177 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 323 
                 C23H18N2 
               
               
                   
               
               
                 178 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 278 
                 C18H15NS 
               
               
                   
               
               
                 179 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 287 
                 C20H18N2 
               
               
                   
               
               
                 180 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 273 
                 C19H16N2 
               
               
                   
               
               
                 181 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 273 
                 C19H16N2 
               
               
                   
               
               
                 182 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 273 
                 C19H16N2 
               
               
                   
               
               
                 183 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 309, 311 
                 C18H13ClN2O 
               
               
                   
               
               
                 184 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 325 
                 C22H16N2O 
               
               
                   
               
               
                 185 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 325 
                 C22H16N2O 
               
               
                   
               
               
                 186 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 280 
                 C17H13NOS 
               
               
                   
               
               
                 187 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 289 
                 C19H16N2O 
               
               
                   
               
               
                 188 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 275 
                 C18H14N2O 
               
               
                   
               
               
                 189 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 275 
                 C18H14N2O 
               
               
                   
               
               
                 190 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 275 
                 C18H14N2O 
               
               
                   
               
               
                 191 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 287, 289 
                 C19H13BrClNO 
               
               
                   
               
               
                 192 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 309, 311 
                 C18H13ClN2O 
               
               
                   
               
               
                 193 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 357 
                 C20H15F3N2O 
               
               
                   
               
               
                 194 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 357 
                 C20H15F3N2O 
               
               
                   
               
               
                 195 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 339 
                 C20H16F2N2O 
               
               
                   
               
               
                 196 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 339 
                 C20H16F2N2O 
               
               
                   
               
               
                 197 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 339 
                 C20H16F2N2O 
               
               
                   
               
               
                 198 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 339 
                 C20H16F2N2O 
               
               
                   
               
               
                 199 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 331 
                 C22H22N2O 
               
               
                   
               
               
                 200 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 331 
                 C22H22N2O 
               
               
                   
               
               
                 201 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 361 
                 C22H20N2O3 
               
               
                   
               
               
                 202 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 338 
                 C20H16FNOS 
               
               
                   
               
               
                 203 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 363 
                 C19H11ClF3NO 
               
               
                   
               
               
                 204 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 360 
                 C19H12F3NOS 
               
               
                   
               
               
                 205 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 360 
                 C19H12F3NOS 
               
               
                   
               
               
                 206 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 342 
                 C19H13F2NOS 
               
               
                   
               
               
                 207 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 342 
                 C19H13F2NOS 
               
               
                   
               
               
                 208 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 342 
                 C19H13F2NOS 
               
               
                   
               
               
                 209 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 342 
                 C19H13F2NOS 
               
               
                   
               
               
                 210 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C21H19NOS 
               
               
                   
               
               
                 211 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 364 
                 C21H17NO3S 
               
               
                   
               
               
                 212 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 272 
                 C16H14FNS 
               
               
                   
               
               
                 213 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 363 
                 C19H11ClF3NO 
               
               
                   
               
               
                 214 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 345 
                 C19H12ClF2NO 
               
               
                   
               
               
                 215 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 345 
                 C19H12ClF2NO 
               
               
                   
               
               
                 216 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 345 
                 C19H12ClF2NO 
               
               
                   
               
               
                 217 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 333 
                 C22H21FN2 
               
               
                   
               
               
                 218 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 345 
                 C19H12ClF2NO 
               
               
                   
               
               
                 219 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 355 
                 C21H17F3N2 
               
               
                   
               
               
                 220 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 355 
                 C21H17F3N2 
               
               
                   
               
               
                 221 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 337 
                 C21H18F2N2 
               
               
                   
               
               
                 222 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 337 
                 C21H18F2N2 
               
               
                   
               
               
                 223 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 337 
                 C21H18F2N2 
               
               
                   
               
               
                 224 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 337 
                 C21H18F2N2 
               
               
                   
               
               
                 225 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 329 
                 C23H24N2 
               
               
                   
               
               
                 226 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 329 
                 C23H24N2 
               
               
                   
               
               
                 227 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 359 
                 C23H22N2O2 
               
               
                   
               
               
                 228 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 304 
                 C21H18FN 
               
               
                   
               
               
                 229 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 337 
                 C21H18ClNO 
               
               
                   
               
               
                 230 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 326 
                 C20H14F3N 
               
               
                   
               
               
                 231 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 326 
                 C20H14F3N 
               
               
                   
               
               
                 232 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 308 
                 C20H15F2N 
               
               
                   
               
               
                 233 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 308 
                 C20H15F2N 
               
               
                   
               
               
                 234 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 308 
                 C20H15F2N 
               
               
                   
               
               
                 235 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 300 
                 C22H21N 
               
               
                   
               
               
                 236 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 300 
                 C22H21N 
               
               
                   
               
               
                 237 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 330 
                 C22H19NO2 
               
               
                   
               
               
                 238 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 336, 338 
                 C21H18ClNO 
               
               
                   
               
               
                 239 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 302 
                 C21H19NO 
               
               
                   
               
               
                 240 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 306 
                 C20H16FNO 
               
               
                   
               
               
                 241 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 335 
                 C21H19FN2O 
               
               
                   
               
               
                 242 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 341 
                 C20H15ClFNO 
               
               
                   
               
               
                 243 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 367 
                 C21H16ClNO3 
               
               
                   
               
               
                 244 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 366 
                 C21H19NO3S 
               
               
                   
               
               
                 245 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 366 
                 C21H19NO3S 
               
               
                   
               
               
                 246 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 340, 342 
                 C19H14ClNOS 
               
               
                   
               
               
                 247 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 336 
                 C20H17NO2S 
               
               
                   
               
               
                 248 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 320 
                 C20H17NOS 
               
               
                   
               
               
                 249 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 318, 320 
                 C21H16ClN 
               
               
                   
               
               
                 250 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 302 
                 C21H16FN 
               
               
                   
               
               
                 251 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 350 
                 C21H19NO4 
               
               
                   
               
               
                 252 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 324, 326 
                 C19H14ClNO2 
               
               
                   
               
               
                 253 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 306 
                 C19H15NO3 
               
               
                   
               
               
                 254 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 320 
                 C20H17NO3 
               
               
                   
               
               
                 255 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 317 
                 C21H20N2O 
               
               
                   
               
               
                 256 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 319 
                 C21H19FN2 
               
               
                   
               
               
                 257 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 315 
                 C22H22N2 
               
               
                   
               
               
                 258 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 306, 308 
                 C20H16ClN 
               
               
                   
               
               
                 259 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 288 
                 C20H17NO 
               
               
                   
               
               
                 260 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 302 
                 C21H19NO 
               
               
                   
               
               
                 261 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 340 
                 C21H16F3N 
               
               
                   
               
               
                 262 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 290 
                 C20H16FN 
               
               
                   
               
               
                 263 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C21H19NO3 
               
               
                   
               
               
                 264 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C21H19NO3 
               
               
                   
               
               
                 265 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 290 
                 C19H15NO2 
               
               
                   
               
               
                 266 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 304 
                 C20H17NO2 
               
               
                   
               
               
                 267 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 364 
                 C22H21NO4 
               
               
                   
               
               
                 268 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 364 
                 C22H21NO4 
               
               
                   
               
               
                 269 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C21H19NO3 
               
               
                   
               
               
                 270 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C21H19NO3 
               
               
                   
               
               
                 271 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 304 
                 C20H17NO2 
               
               
                   
               
               
                 272 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 351, 353 
                 C19H14BrNO 
               
               
                   
               
               
                 273 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 282 
                 C16H12FN3O 
               
               
                   
               
               
                 274 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 317 
                 C20H13FN2O 
               
               
                   
               
               
                 275 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 336 
                 C21H18FNO2 
               
               
                   
               
               
                 276 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 338 
                 C20H16FNOS 
               
               
                   
               
               
                 277 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 369, 371 
                 C19H13BrFNO 
               
               
                   
               
               
                 278 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 343 
                 C11H15FN2O 
               
               
                   
               
               
                 279 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 343 
                 C22H15FN2O 
               
               
                   
               
               
                 280 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 324 
                 C23H17NO 
               
               
                   
               
               
                 281 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 342 
                 C23H16FNO 
               
               
                   
               
               
                 282 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 342 
                 C23H16FNO 
               
               
                   
               
               
                 283 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 319 
                 C19H14N2O3 
               
               
                   
               
               
                 284 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 264 
                 C16H13N3O 
               
               
                   
               
               
                 285 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 299 
                 C20H14N2O 
               
               
                   
               
               
                 286 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 318 
                 C21H19NO2 
               
               
                   
               
               
                 287 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 342 
                 C20H14F3NO 
               
               
                   
               
               
                 288 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 330 
                 C23H23NO 
               
               
                   
               
               
                 289 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 292 
                 C19H14FNO 
               
               
                   
               
               
                 290 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 352 
                 C21H18FNO3 
               
               
                   
               
               
                 291 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 352 
                 C21H18FNO3 
               
               
                   
               
               
                 292 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 398 
                 C26H20FNO2 
               
               
                   
               
               
                 293 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 398 
                 C26H20FNO2 
               
               
                   
               
               
                 294 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 326, 328 
                 C19H13ClFNO 
               
               
                   
               
               
                 295 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 326, 328 
                 C19H13ClFNO 
               
               
                   
               
               
                 296 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 326, 328 
                 C19H13ClFNO 
               
               
                   
               
               
                 297 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 308 
                 C19H14FNO2 
               
               
                   
               
               
                 298 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 308 
                 C19H14FNO2 
               
               
                   
               
               
                 299 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 292 
                 C19H14FNO 
               
               
                   
               
               
                 300 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 322 
                 C20H16FNO2 
               
               
                   
               
               
                 301 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 322 
                 C20H16FNO2 
               
               
                   
               
               
                 302 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 322 
                 C20H16FNO2 
               
               
                   
               
               
                 303 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 360 
                 C20H13F4NO 
               
               
                   
               
               
                 304 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 360 
                 C20H13F4NO 
               
               
                   
               
               
                 305 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 348 
                 C23H22FNO 
               
               
                   
               
               
                 306 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 310 
                 C19H13F2NO 
               
               
                   
               
               
                 307 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 310 
                 C19H13F2NO 
               
               
                   
               
               
                 308 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 310 
                 C19H13F2NO 
               
               
                   
               
               
                 309 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 306 
                 C20H16FNO 
               
               
                   
               
               
                 310 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 306 
                 C20H16FNO 
               
               
                   
               
               
                 311 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C21H19NO3 
               
               
                   
               
               
                 312 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C21H19NO3 
               
               
                   
               
               
                 313 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C21H19NO3 
               
               
                   
               
               
                 314 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 380 
                 C26H21NO2 
               
               
                   
               
               
                 315 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 288 
                 C20H17NO 
               
               
                   
               
               
                 316 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 308, 310 
                 C19H14ClNO 
               
               
                   
               
               
                 317 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 290 
                 C19H15NO2 
               
               
                   
               
               
                 318 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 308, 310 
                 C19H14ClNO 
               
               
                   
               
               
                 319 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 304 
                 C20H17NO2 
               
               
                   
               
               
                 320 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 304 
                 C20H17NO2 
               
               
                   
               
               
                 321 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 286 
                 C21H19N 
               
               
                   
               
               
                 322 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 288 
                 C20H17NO 
               
               
                   
               
               
                 323 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 323 
                 C20H16ClNO 
               
               
                   
               
               
                 324 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 319 
                 C20H18N2S 
               
               
                   
               
               
                 325 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 304 
                 C20H17NO2 
               
               
                   
               
               
                 326 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 310 
                 C19H13F2NO 
               
               
                   
               
               
                 327 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 310 
                 CX19H13F2NO 
               
               
                   
               
               
                 328 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 310 
                 C19H13F2NO 
               
               
                   
               
               
                 329 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 310 
                 C19H13F2NO 
               
               
                   
               
               
                 330 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 298 
                 C17H12FNOS 
               
               
                   
               
               
                 331 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 302 
                 C21H19NO 
               
               
                   
               
               
                 332 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 298 
                 C17H12FNOS 
               
               
                   
               
               
                 333 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 282 
                 C17H12FNO2 
               
               
                   
               
               
                 334 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 282 
                 C17H12FNO2 
               
               
                   
               
               
                 335 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 307 
                 C19H15FN2O 
               
               
                   
               
               
                 336 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 370 
                 C20H16FNO3S 
               
               
                   
               
               
                 337 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 293 
                 C18H13FN2O 
               
               
                   
               
               
                 338 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 293 
                 C18H13FN2O 
               
               
                   
               
               
                 339 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 293 
                 C18H13FN2O 
               
               
                   
               
               
                 340 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 340 
                 C20H15F2NO2 
               
               
                   
               
               
                 341 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 302 
                 C21H19NO 
               
               
                   
               
               
                 342 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 324 
                 C20H15F2NO 
               
               
                   
               
               
                 343 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 346 
                 C19H11F4NO 
               
               
                   
               
               
                 344 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 346 
                 C19H11F4NO 
               
               
                   
               
               
                 345 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 328 
                 C19H12F3NO 
               
               
                   
               
               
                 346 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 328 
                 C19H12F3NO 
               
               
                   
               
               
                 347 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 328 
                 C129H12F3NO 
               
               
                   
               
               
                 348 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 328 
                 C19H12F3NO 
               
               
                   
               
               
                 349 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 328 
                 C19H12F3NO 
               
               
                   
               
               
                 350 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 328 
                 C19H12F3NO 
               
               
                   
               
               
                 351 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 320 
                 C21H19FNO 
               
               
                   
               
               
                 352 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 320 
                 C21H18FNO 
               
               
                   
               
               
                 353 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 350 
                 C21H16FNO3 
               
               
                   
               
               
                 354 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 352 
                 C21H18FNO3 
               
               
                   
               
               
                 355 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 264 
                 C17H13NO2 
               
               
                   
               
               
                 356 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 264 
                 C17H13NO2 
               
               
                   
               
               
                 357 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 289 
                 C19H16N2O 
               
               
                   
               
               
                 358 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 352 
                 C20H17NO3S 
               
               
                   
               
               
                 359 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 275 
                 C18H14N2O 
               
               
                   
               
               
                 360 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 275 
                 C18H14N2O 
               
               
                   
               
               
                 361 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 275 
                 C18H14N2O 
               
               
                   
               
               
                 362 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 322 
                 C20H16FNO2 
               
               
                   
               
               
                 363 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2, 3 
                 306 
                 C20H16FNO 
               
               
                   
               
               
                 364 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 328 
                 C19H12F3NO 
               
               
                   
               
               
                 365 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 328 
                 C19H12F3NO 
               
               
                   
               
               
                 366 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 310 
                 C19H13F2NO 
               
               
                   
               
               
                 367 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 310 
                 C19H13F2NO 
               
               
                   
               
               
                 368 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 334 
                 C21H19NO3 
               
               
                   
               
               
                 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 
                 C19H13F2N2S 
               
               
                   
               
               
                 427 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 363 
                 C21H18N2O2S 
               
               
                   
               
               
                 428 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 353 
                 C20H17FN2O2 
               
               
                   
               
               
                 429 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 333 
                 C21H20N2S 
               
               
                   
               
               
                 430 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 311 
                 C17H14N2S2 
               
               
                   
               
               
                 431 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 373 
                 C10H15F3N2S 
               
               
                   
               
               
                 432 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 305 
                 C20H17FN2 
               
               
                   
               
               
                 433 
                 
                   
                             
                     
                         
                         
                     
                   
                 
                 2 
                 287 
                 C20H18NM2 
               
               
                   
               
               
                 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 
               
               
                   
               
               
                   *Analysis was done by LCMS. Number shown is M + 1. In all cases mass shown agrees with the expected mass for the compound shown.    
               
             
          
         
       
     
         [0089]     The following compounds were prepared according 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).   —                  
 
 Antiviral Activity Assays: 
 
         [0091]     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.  
         [0092]     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.  
         [0093]     Secondary yield reduction assays: To determine the activity of compounds against HSV, Vero cells are plated in 6 well dishes at a density of 5×105 cells/well. Cells are infected at a multiplicity of infection of 0.01 with HSV (strain Syn17+). 30μL 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.  
         [0094]     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.  
         [0095]     Cellular toxicity assays: Cellular toxicity is measured in Ad 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.  
         [0096]     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.  
         [0097]     Table 3 contains the results of the antiviral efficacy (ISV: 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)                      
 
         [0098]     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)                      
 
         [0099]     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-μconcentrations.  
         [0100]     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.