2-(Phenylmethylene)cycloalkylamines and -azetidines
AssigneeThe Upjohn Company
InventorJacob Szmuszkovicz
Life of this patent
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Abstract
2-(Phenylmethylene)cycloalkylamines and -azetidines of the formula ##STR1## and acid addition salts thereof, e.g., 1-[2-(phenylmethylene)cyclohexyl]azetidine, and related compounds, which have analgesic, antidepressant and mixed analgesic/antidepressant central nervous system (CNS) activities, and which are useful in treating pain and/or depression in mammals including humans. The invention provides processes for preparing the compounds as well as compositions containing the compounds and methods for using the compounds as analgesic and/or antidepressant drugs for humans and valuable mammalian animals.
Claims51
A compound of the formula
- wherein
- n is 1, 2, 3 or 4 so that the resulting cycloalkyl ring is cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl;
- R is hydrogen, C.sub.1 to C.sub.3 -alkyl;
- R.sub.1 represents hydrogen or from one to two substituents on the phenyl ring selected from the group consisting of a halogen having an atomic number of from 9 to 35;
- C.sub.1 to C.sub.4 -alkyl,
- trifluoromethyl,
- hydroxy, carboxyl, and sodium and potassium salts thereof,
- C.sub.1 to C.sub.2 -alkyloxy,
- (C.sub.1 to C.sub.2 -alkyloxy)carbonyl (--C(O)O--C.sub.1 to C.sub.2 -alkyl),
- C.sub.2 to C.sub.5 -alkanoyloxy (--OC(O)--C.sub.1 to C.sub.4 -alkyl), hydroxymethyl,
- (C.sub.1 to C.sub.2 -alkanoyl)oxymethyl (C.sub.1 to C.sub.2 -alkanoyl-OCH.sub.2),
- --O--(CH).sub.2).sub.r --O-- bonded to the 3- and 4-ring carbons, where r is 1 or 2,
- (C.sub.1 to C.sub.3 -alkyl)oxymethyl (C.sub.1 to C.sub.3 -alkyl-OCH.sub.2),
- (C.sub.1 to C.sub.2 -alkyl)oxycarbonylmethyl, (C.sub.1 to C.sub.2 -alkyl--O--C(O)--CH.sub.2 --),
- --CH((R.sub.10)--C(O)--OR.sub.11 wherein R.sub.10 is hydrogen or C.sub.1 to C.sub.3 -alkyl and R.sub.11
- is hydrogen or C.sub.1 to C.sub.3 -alkyl,
- phenyl,
- phenoxy,
- benzyloxy,
- benzoyloxy,
- phenyl-C.sub.1 to C.sub.3 -alkyl,
- phenylethenyl,
- phenoxymethyl,
- and such phenyl, phenoxy, benzyloxy, benzoyloxy, phenyl-(C.sub.1 to C.sub.3 -alkyl), phenylethenyl, and phenoxymethyl groups substituted on the phenyl ring carbon atoms thereof with one or two substituents selected from the group consisting of halogen as defined above, trifluoromethyl, C.sub.1 to C.sub.2 -alkyl, C.sub.1 to C.sub.2 -alkyl, C.sub.1 to C.sub.2 -alkyloxy, and hydroxy;
- R.sub.2 and R.sub.3 are taken together with the nitrogen to which they are bonded to complete an azetidine ring of the formula ##STR12## wherein R.sub.4 denotes hydrogen, C.sub.1 to C.sub.2 -alkyl, 3-hydroxy, 3-(C.sub.1 to C.sub.2 -alkyloxy)- or 3-(C.sub.1 to C.sub.2 -alkanoyloxy);
- and the acid addition salts of such compounds.
Dependencies are inferred from the claim text.