# US 5,352,795 A · Alpha-heterocycle substituted tolunitriles

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- Number: US 5,352,795 A
- Document ID: US5352795A
- Status: Granted
- Kind: A
- Application number: 07/882,188
- Filed: 1992-05-11
- Granted: 1994-10-04
- Earliest claimed: 1986-03-07
- Assignees: Ciba-Geigy Corporation
- Inventors: Robert M. Bowman; Leslie J. Browne
- Web page: https://patentgrep.com/patent/US5352795A

## CPC

- C07D 231/12: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 213/57: Nitriles
- C07D 233/56: with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D 249/08: 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## 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.

## Claims

### Claim 1

A method for preparing 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 ting; R.sub.1 represents hydrogen; R.sub.2 represents 4-cyanophenyl; and W represents 1-(1,2,4)-triazolyl; which comprises condensing under basic conditions using an alkali metal aikoxide a compound of the formula XI ##STR17## wherein R, R.sub.o and W have meaning as defined above, with p-fluorobenzonitrile.

### Claim 2 (depends on 1)

A method according to claim 1 wherein the alkali metal alkoxide is potassium t-butoxide.

### Claim 3 (depends on 1)

A method according to claim 1 for preparing 4-[alpha-(4-cyanophenyl)-1-(1,2,4-triazolyl)-methyl]benzonitrile which comprises condensing 4-[1-(1,2,4)-triazolylmethyl]benzonitrile with 4-fluorobenzonitrile using potassium tert-butoxide in dimethylformamide.

### Claim 4 (depends on 1)

A process according to claim 1 for preparing 4-[alpha-(4-cyanophenyl)-1-(1,2,4-triazolyl)-methyl]benzonitrile.