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Claims for Patent: 4,978,672

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Claims for Patent: 4,978,672

Title: Alpha-heterocyclc substituted tolunitriles
Abstract:The invention is concerned with aromatase inhibiting compounds of formula I ##STR1## wherein R and Ro represent hydrogen or lower alkyl; or R and Ro located on adjacent carbon atoms and together when combined with the benzene ring to which they are attached form a naphthalene or tetrahydronaphthalene ring; R.sub.1 and R.sub.2 independently represent hydrogen, lower alkyl, (lower alkyl, aryl or aryl-lower alkyl)-thio, lower alkenyl, aryl, aryl-lower alkyl, C.sub.3 -C.sub.6 -cycloalkyl, or C.sub.3 -C.sub.6 -cycloalkyl-lower alkyl; or R.sub.1 and R.sub.2 combined represent lower alkylidene, mono- or di-aryl-lower alkylidene; R.sub.1 and R.sub.2 combined also represent C.sub.4 -C.sub.6 -straight chain alkylene, lower alkyl-substituted straight chain alkylene or ortho-phenylene bridged-C.sub.2 -C.sub.4 -straight chain alkylene, each forming with the carbon atom attached thereto a corresponding optionally substituted or benzo-fused 5, 6 or 7-membered ring; W represents 1-imidazolyl, 1-(1,2,4- or 1,3,4)-triazolyl or 3-pyridyl; or W represents 1-imidazolyl, 1-(1,2,4 or 1,3,4)-triazolyl or 3-pyridyl substituted by lower alkyl; and pharmaceutically acceptable salts thereof.
Inventor(s): Bowman; Robert M. (Summit, NJ), Steele; Ronald E. (Long Valley, NJ), Browne; Leslie (Aesch, CH)
Assignee: Ciba-Geigy Corporation (Ardsley, NY)
Application Number:07/240,862
Patent Claims: 1. A compound of the formula ##STR16## wherein R and R.sub.o represent hydrogen or lower alkyl; or R and R.sub.o located on adjacent carbon atoms and together when combined with the benzene ring to which they are attached form a naphthalene or tetrahydronaphthalene ring; R.sub.1 represents hydrogen; R.sub.2 represents hydrogen, lower alkyl, (lower alkyl, aryl or aryl-lower alkyl)-thio, lower alkenyl, aryl, aryl-lower alkyl, C.sub.3 -C.sub.6 -cycloalkyl, or C.sub.3 -C.sub.6 -cycloalkyl-lower alkyl; or R.sub.1 and R.sub.2 combined represent lower alkylidene, mono- or di-aryl-lower alkylidene; R.sub.1 and R.sub.2 combined also represent C.sub.4 -C.sub.6 -straight chain alkylene, lower alkyl-substituted straight chain alkylene or CH.sub.2 -ortho-phenylene-CH.sub.2 ; W represents 1-(1,2,4- or 1,3,4))-triazolyl or 1-(1,2,4 or 1,3,4-triazolyl substituted by lower alkyl; aryl within the above definitions represents phenyl or phenyl substituted by one or two substituents selected from lower alkyl, lower alkoxy, hydroxy, lower alkanoyloxy, aroyloxy, nitro, amino, halogen, trifluoromethyl, cyano, carboxy, carboxy funtionalized in form of a pharmaceutically acceptable ester or amide, lower alkanoyl, aroyl, lower alkylsulfonyl, sulfamoyl, N-lower alkylsulfamoyl or N,N-di-lower alkylsulfamoyl; and aryl within the above definitions also represents 2-, 3-, or 4-pyridyl or a said heterocyclic radical monosubstituted by lower alkyl, lower alkoxy, cyano or halogen; and aroyl within the above definitions represents benzoyl or benzoyl substituted by lower alkyl, lower alkoxy, halogen or trifluoromethyl; or a pharmaceutically acceptable salt thereof.

2. A compound according to claim 1 of the formula ##STR17## wherein R.sub.1 ' represents hydrogen; R.sub.2 ' represents hydrogen, lower alkyl, phenyl, pyridyl or benzyl; or R.sub.2 ' represents phenyl or benzyl, each monosubstituted on the phenyl ring by cyano, lower alkyl, lower alkoxy, hydroxy, lower alkanoyloxy, aroyloxy, nitro, halogen, trifluoromethyl, lower alkanoyl, aroyl, lower alkylsulfonyl carbamoyl, N-mono- or N,N-di-lower alkylcarbamoyl, sulfamoyl, N-mono- or N,N-di-lower alkylsulfamoyl; or R.sub.1 ' and R.sub.2 ' combined represent together lower alkylidene, benzylidene or diphenylmethylidene; or R.sub.1 ' and R.sub.2 'combined represent together C.sub.4 -C.sub.6 straight chain alkylene R.sub.3 ' represents hydrogen or lower alkyl; aroyl within the above definitions has meaning as defined in said claim; or a pharmaceutically acceptable salt thereof.

3. A compound according to claim 1 wherein R.sub.1 ' represents hydrogen; R.sub.2 ' represents hydrogen, lower alkyl or pyridyl; or R.sub.2 ' represents benzyl or phenyl, each unsubstituted or monosubstituted on phenyl by cyano, lower alkyl, lower alkoxy, hydroxy, lower alkanoyloxy, halogen, nitro, trifluoromethyl, lower alkanoyl, aroyl, lower alkylsulfonyl, carbamoyl, N-mono- or N,N-di-lower alkylcarbamoyl,sulfamoyl, N-mono-or N,N-di-lower alkylsulfamoyl; R.sub.3 ' represents hydrogen or lower alkyl; aroyl within the above definitions has meaning as defined in said claim; or a pharmaceutically acceptable salt thereof.

4. A compound according to claim 2 wherein R.sub.1 ' and R.sub.3 ' represent hydrogen; R.sub.2 ' represents 3-pyridyl, p-cyanobenzyl or p-cyanophenyl; or a pharmaceutically acceptable salt thereof.

5. A compound according to claim 2 wherein R.sub.1 ' represents hydrogen; R.sub.2 ' represents hydrogen, lower alkyl, benzyl, phenyl, or 3- or 4-pyridyl; or R.sub.2 ' represents phenyl or benzyl, each monosubstituted on phenyl by cyano, halogen, lower alkoxy, lower alkyl or trifluoromethyl; R.sub.3 represents hydrogen or lower alkyl; or a pharmaceutically acceptable salt thereof.

6. A compound according to claim 2 being 4-[alpha-(4-cyanophenyl)-1-(1,2,4-triazolyl)-methyl]-benzonitrile or a pharmaceutically acceptable salt thereof.

7. An aromatase inhibiting pharmaceutical composition comprising an effective aromatase inhibiting amount of a compound of claim 1 in combination with one or more pharmaceutically acceptable carriers.

8. An aromatase inhibiting pharmaceutical composition comprising an effective aromatase inhibiting amount of a compound of claim 6 in combination with one or more pharmaceutically acceptable carriers.

9. A method of inhibiting aromatase activity and suppressing estrogen synthesis in mammals which comprises administering to a mammal in need thereof an effective amount of a compound of claim 2 or a pharmaceutical composition comprising a said compound in combination with one or more pharmaceutically acceptable carriers.

10. A method of treating or suppressing estrogen dependent diseases in mammals which comprises administering to a mammal in need thereof an effective aromatase inhibiting amount of a compound of claim 2 or of a pharmaceutical composition comprising a said compound in combination with one or more pharmaceutically acceptable carriers.

11. A method of treating or suppressing estrogen dependent tumors in mammals which comprises administering to a mammal in need thereof an effective amount of a compound of claim 2 or of a pharmaceutical composition comprising a said compound in combination with one or more pharmaceutically acceptable carriers.

12. A method of inhibiting aromatase activity and suppressing estrogen synthesis in mammals which comprises administering to a mammal in need thereof an effective amount of a compound of claim 1 or of a said compound in combination with one or more pharmaceutically acceptable carriers.

13. A method of inhibiting aromatase activity and suppressing estrogen synthesis in mammals which comprises administering to a mammal in need thereof an effective amount of a compound of claim 6 or of a said compound in combination with one or more pharmaceutically acceptable carriers.

14. A method of treating or suppressing estrogen dependent tumors in mammals which comprises administering to a mammal in need thereof an effective amount of a compound of claim 6 or of a said compound in combination with on one or more pharmaceutically acceptable carriers.

15. A method according to claim 14 of treating mammary tumors in mammals

16. A method of inhibiting fertility in female mammals which comprises administering to a mammal in need thereof an effective amount of a compound claim 1.

17. A method according to claim 16 wherein implantation is inhibited.

18. A method according to claim 16 wherein fetal resorption is induced.
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