4-Amino-4-aryl-cyclohexanones

Claim 2

A compound of the formula: ##STR22## wherein X is oxo, aryl is ##STR23## wherein m is zero, one or two, and Y is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, alkoxy of 1 to 4 carbon atoms, inclusive, hydroxy, cycloalkyloxy of 3 to 6 carbon atoms, inclusive, alkylthio of 1 to 4 carbon atoms, inclusive, or ##STR24## where Y' is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, or alkoxy of 1 to 4 carbon atoms, inclusive; R 1 is hydrogen, or alkyl of 1 to 8 carbon atoms, inclusive, R 2 is hydrogen, alkyl of 1 to 8 carbon atoms, inclusive, --CH 2 --alkenyl wherein alkenyl is of 2 to 8 carbon atoms, inclusive, acetyl, cycloalkylalkyl wherein cycloalkyl is of 3 to 6 carbon atoms, inclusive, and alkyl is of 1 to 3 carbon atoms, inclusive, β-hydroxyethyl, cycloalkyl of 3 to 6 carbon atoms, inclusive, ##STR25## and R 3 is hydrogen, alkyl of 1 to 5 carbon atoms, inclusive, and the acid addition salts thereof.

Claim 3

A compound of claim 1 of the formula: ##STR26## wherein X is oxo, wherein Y is alkoxy of 1 to 4 carbon atoms, inclusive, hydroxy, cycloalkyloxy of 3 to 6 carbon atoms, inclusive, ##STR27## wherein Y' is alkyl of 1 to 4 carbon atoms, inclusive, or alkoxy of 1 to 4 carbon atoms, inclusive, and m=0, 1, or 2; R 1 is alkyl of 1 to 8 carbon atoms, inclusive, R 2 is alkyl of 1 to 8 carbon atoms, inclusive, acetyl, cycloalkylalkyl (cycloalkyl of 3 to 6 carbon atoms, inclusive, alkyl of 1 to 3 carbon atoms, inclusive), β-hydroxyethyl, or cycloalkyl of 3 to 6 carbon atoms, inclusive and R 3 is hydrogen, or alkyl of 1 to 5 carbon atoms, inclusive; and the acid addition salts thereof.

Claim 4

A compound of claim 1 of the formula: ##STR28## wherein X is oxo, wherein R 3 is hydrogen or alkyl of 1 to 5 carbon atoms, inclusive; Y is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, alkoxy of 1 to 4 carbon atoms, inclusive, hydroxy, or alkanoyloxy of 2 to 4 carbon atoms, inclusive; R 1 is hydrogen or alkyl of 1 to 8 carbon atoms, inclusive, R 2 is hydrogen, alkyl of 1 to 8 carbon atoms, inclusive,acetyl, cycloalkylalkyl (cycloalkyl of 3 to 6 carbon atoms, inclusive, and alkyl of 1 to 3 carbon atoms, inclusive), β-hydroxyethyl, cycloalkyl of 3 to 6 carbon atoms, inclusive, -CH 2 -alkenyl wherein alkenyl is of 2 to 8 carbon atoms, inclusive, ##STR29## wherein Y' is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, or alkoxy of 1 to 4 carbon atoms, inclusive, and m is 0, 1, or 2; and the acid addition salts thereof.

Claim 5

A compound according to claim 1 which is 4-(p-chlorophenyl)-4-dimethylaminocyclohexanone.

Claim 6

A compound according to claim 1 which is 4-(p-fluorophenyl)-4-dimethylaminocyclohexanone.

Claim 7

A compound according to claim 1 which is 4-(p-anisyl)-4-dimethylaminocyclohexanone free base.

Claim 8

A compound according to claim 1 which is 4-(o-chlorophenyl)-4-dimethylaminocyclohexanone.

Claim 9

A compound according to claim 1 which is 4-(m-anisyl)-4-dimethylaminocyclohexanone.

Claim 10

A compound according to claim 1 which is 4-dimethylamine-4-(p-tolyl)cyclohexanone.

Claim 11

A compound according to claim 1 which is 4-dimethylamine-4-phenylcyclohexanone.

Claim 12

A compound according to claim 1 which is 4-(p-bromophenyl)-4-dimethylaminocyclohexanone.

Claim 13

A compound according to claim 1 which is 4-(a-tolyl)-4-dimethylaminocyclohexanone free base.

Claim 14

A compound according to claim 1 which is 4-(a-hydroxyphenyl)-4-methyl-a-butylamino)cyclohexanone.

Claim 15

A compound according to claim 1 which is 4-(a-hydroxyphenyl)-4-dimethylaminocyclohexanone.

Claim 16

A compound according to claim 1 which is 4-(p-hydroxyphenyl)-4-(a-butylmethylamino)cyclohexanone.

Claim 17

A compound according to claim 1 which is 4-(p-chlorophenyl)-cis-2-methyl-4-dimethylaminocyclohexanone.

Claim 18

A compound according to claim 1 which is 4-(p-chlorophenyl)-trans-2-methyl-4-dimethylaminocyclohexanone.

Claim 19

An intermediate compound of the formula: ##STR30## wherein X is oxo aryl is ##STR31## wherein m is zero, one or two, and Y is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, alkoxy of 1 to 4 carbon atoms, inclusive, cycloalkyloxy of 3 to 6 carbon atoms, inclusive, alkylthio of 1 to 4 carbon atoms, inclusive, ##STR32## where Y' is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, or alkoxy of 1 to 4 carbon atoms, inclusive, or the acid addition salts thereof.

Claim 20

An intermediate compound of the formula: ##STR30## wherein X is oxo aryl is ##STR31## wherein m is zero, one or two, and Y is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, alkoxy of 1 to 4 carbon atoms, inclusive, cycloalkyloxy of 3 to 6 carbon atoms, inclusive, alkylthio of 1 to 4 carbon atoms, inclusive, ##STR32## where Y' is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, or alkoxy of 1 to 4 carbon atoms, inclusive, or the acid addition salts thereof.

Claim 21

An intermediate compound of the formula: ##STR33## wherein X is oxo, aryl is ##STR34## wherein m is zero, one or two, and Y is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, alkoxy of 1 to 4 carbon atoms, inclusive, cycloalkyloxy of 3 to 6 carbon atoms, inclusive, alkylthio of 1 to 4 carbon atoms, inclusive, ##STR35## wherein Y' is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, or alkoxy of 1 to 4 carbon atoms, inclusive, or the acid addition salts thereof.

Claim 22

An intermediate compound of the formula: ##STR33## wherein X is oxo, aryl is ##STR34## wherein m is zero, one or two, and Y is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, alkoxy of 1 to 4 carbon atoms, inclusive, cycloalkyloxy of 3 to 6 carbon atoms, inclusive, alkylthio of 1 to 4 carbon atoms, inclusive, ##STR35## wherein Y' is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, or alkoxy of 1 to 4 carbon atoms, inclusive, or the acid addition salts thereof.

Claim 23

An analgetic composition in unit dosage form comprising as an active ingredient an effective analgetic amount of a compound of the formula: ##STR36## wherein X is oxo, aryl is ##STR37## wherein m is zeor, one or two, and Y is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, alkoxy of 1 to 4 carbon atoms, inclusive, hydroxy, cycloalkyloxy of 3 to 6 carbon atoms, inclusive, alkylthio of 1 to 4 carbon atoms, inclusive, or ##STR38## where Y' is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, or alkoxy of 1 to 4 carbon atoms, inclusive; R 1 is hydrogen, or alkyl of 1 to 8 carbon atoms, inclusive, R 2 is hydrogen, alkyl of 1 to 8 carbon atoms, inclusive, -CH 2 -alkenyl wherein alkenyl is of 2 to 8 carbon atoms, inclusive, acetyl, cycloalkylalkyl wherein cycloalkyl of 3 to 6 carbon atoms, inclusive, and alkyl is of 1 to 3 carbon atoms, inclusive, β-hydroxyethyl, cycloalkyl of 3 to 6 carbon atoms, inclusive, ##STR39## and R 3 is hydrogen, alkyl of 1 to 5 carbon atoms, inclusive, and the acid addition salts thereof, in association with a pharmaceutical carrier.

Claim 24

An analgetic composition in unit dosage form comprising as an active ingredient an effective analgetic amount of a compound of the formula: ##STR36## wherein X is oxo, aryl is ##STR37## wherein m is zeor, one or two, and Y is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, alkoxy of 1 to 4 carbon atoms, inclusive, hydroxy, cycloalkyloxy of 3 to 6 carbon atoms, inclusive, alkylthio of 1 to 4 carbon atoms, inclusive, or ##STR38## where Y' is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, or alkoxy of 1 to 4 carbon atoms, inclusive; R 1 is hydrogen, or alkyl of 1 to 8 carbon atoms, inclusive, R 2 is hydrogen, alkyl of 1 to 8 carbon atoms, inclusive, -CH 2 -alkenyl wherein alkenyl is of 2 to 8 carbon atoms, inclusive, acetyl, cycloalkylalkyl wherein cycloalkyl of 3 to 6 carbon atoms, inclusive, and alkyl is of 1 to 3 carbon atoms, inclusive, β-hydroxyethyl, cycloalkyl of 3 to 6 carbon atoms, inclusive, ##STR39## and R 3 is hydrogen, alkyl of 1 to 5 carbon atoms, inclusive, and the acid addition salts thereof, in association with a pharmaceutical carrier.

Claim 25

A composition according to claim 20 wherein the active ingredient is a compound of the formula: ##STR40## wherein X is oxo wherein Y is alkoxy of 1 to 4 carbon atoms, inclusive, hydroxy, cycloalkyloxy of 3 to 6 carbon atoms, inclusive, ##STR41## wherein Y' is alkyl of 1 to 4 carbon atoms, inclusive, or alkoxy of 1 to 4 carbon atoms, inclusive, and m=0, 1, or 2; R 1 is alkyl of 1 to 8 carbon atoms, inclusive, R 2 is alkyl of 1 to 8 carbon atoms, inclusive, acetyl, cycloalkylalkyl (cycloalkyl of 3 to 6 carbon atoms, inclusive, alkyl of 1 to 3 carbon atoms, inclusive), β-hydroxyethyl, or cycloalkyl of 3 to 6 carbon atoms, inclusive, and R 3 is hydrogen, or alkyl of 1 to 5 carbon atoms, inclusive; and the acid addition salts thereof.

Claim 26

A composition according to claim 20 wherein the active ingredient is a compound of the formula: ##STR42## wherein X is oxo wherein R 3 is hydrogen or alkyl of 1 to 5 carbon atoms, inclusive; Y is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, alkoxy of 1 to 4 carbon atoms, inclusive, hydroxy, R 1 is hydrogen or alkyl of 1 to 8 carbon atoms, inclusive; R 2 is hydrogen, alkyl of 1 to 8 carbon atoms, inclusive, acetyl, cycloalkylalkyl (cycloalkyl of 3 to 6 carbon atoms, inclusive, and alkyl of 1 to 3 carbon atoms, inclusive), β-hydroxyethyl, cycloalkyl of 3 to 6 carbon atoms, inclusive, -CH 2 -alkenyl wherein alkenyl is of 2 to 8 carbon atoms, inclusive, ##STR43## wherein Y' is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, or alkoxy of 1 to 4 carbon atoms, inclusive, and m is 0, 1, or 2; and the acid addition salts thereof.

Claim 27

A composition according to claim 20 wherein the active ingredient is present in unit dosage form of from 0.5 mg. to 500 mg.

Claim 28

A composition according to claim 20 wherein the active ingretient is 4-(p-chlorophenyl)-4-dimethylaminocyclohexanone hydrochloride.

Claim 29

A composition according to claim 20 wherein the active ingredient is 4-(p-chlorophenyl)-4-dimethylaminocyclohexanone.

Claim 30

A composition according to claim 20 wherein the active ingredient is 4-(p-bromophenyl)-4-dimethylaminocyclohexanone.

Claim 31

A composition according to claim 20 wherein the active ingredient is 4-(p-bromophenyl)-4-dimethylaminocyclohexanone.

Claim 32

A process for inducing analgesia in humans and animals comprising the administration of an analgetic amount of a compound of the formula: ##STR44## wherein X is oxo aryl is ##STR45## wherein m is zero, one or two, and Y is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, alkoxy of 1 to 4 carbon atoms, inclusive, hydroxy, cycloalkyloxy of 3 to 6 carbon atoms, inclusive, alkylthio of 1 to 4 carbon atoms, inclusive, or ##STR46## where Y' is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, or alkoxy of 1 to 4 carbon atoms, inclusive; R 1 is hydrogen, or alkyl of 1 to 8 carbon atoms, inclusive, R 2 is hydrogen, alkyl of 1 to 8 carbon atoms, inclusive, -CH 2 -alkenyl wherein alkenyl is of 2 to 8 carbon atoms, inclusive, acetyl, cycloalkylalkyl wherein cycloalkyl is of 3 to 6 carbon atoms, inclusive, and alkyl is of 1 to 3 carbon atoms, inclusive, -hydroyethyl, cycloalkyl of 3 to 6 carbon atoms, inclusive ##STR47## and R 3 is hydrogen, alkyl of 1 to 5 carbon atoms, inclusive, and the acid addition salts thereof, to a human or animal subject.

Claim 33

A process for inducing analgesia in humans and animals comprising the administration of an analgetic amount of a compound of the formula: ##STR44## wherein X is oxo aryl is ##STR45## wherein m is zero, one or two, and Y is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, alkoxy of 1 to 4 carbon atoms, inclusive, hydroxy, cycloalkyloxy of 3 to 6 carbon atoms, inclusive, alkylthio of 1 to 4 carbon atoms, inclusive, or ##STR46## where Y' is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, or alkoxy of 1 to 4 carbon atoms, inclusive; R 1 is hydrogen, or alkyl of 1 to 8 carbon atoms, inclusive, R 2 is hydrogen, alkyl of 1 to 8 carbon atoms, inclusive, -CH 2 -alkenyl wherein alkenyl is of 2 to 8 carbon atoms, inclusive, acetyl, cycloalkylalkyl wherein cycloalkyl is of 3 to 6 carbon atoms, inclusive, and alkyl is of 1 to 3 carbon atoms, inclusive, -hydroyethyl, cycloalkyl of 3 to 6 carbon atoms, inclusive ##STR47## and R 3 is hydrogen, alkyl of 1 to 5 carbon atoms, inclusive, and the acid addition salts thereof, to a human or animal subject.

Claim 34

A process according to claim 28 wherein the compound administered is a compound of the formula: ##STR48## wherein X is oxo wherein Y is alkoxy of 1 to 4 carbon atoms, inclusive, hydroxy, cycloalkyloxy of 3 to 6 carbon atoms, inclusive, ##STR49## wherein Y' is alkyl of 1 to 4 carbon atoms, inclusive, or alkoxy of 1 to 4 carbon atoms, inclusive, and m=0, 1, or 2; R 1 is alkyl of 1 to 8 carbon atoms, inclusive, R 2 is alkyl of 1 to 8 carbon atoms, inclusive, acetyl, cycloalkylalkyl (cycloalkyl of 3 to 6 carbon atoms, inclusive, alkyl of 1 to 3 carbon atoms, inclusive), β-hydroxyethyl, or cycloalkyl of 3 to 6 carbon atoms, inclusive, and R 3 is hydrogen, or alkyl of 1 to 5 carbon atoms, inclusive, and the acid addition salts therof.

Claim 35

A process according to claim 28 wherein the compound administered is a compound of the formula: ##STR50## wherein X is oxo wherein R 3 is hydrogen or alkyl of 1 to 5 carbon atoms, inclusive; Y is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, alkoxy of 1 to 4 carbon atoms, inclusive, hydroxy; R 1 is hydrogen or alkyl of 1 to 8 carbon atoms, inclusive; R 2 is hydrogen, or alkyl of 1 to 8 carbon atoms, inclusive, acetyl, cycloalkylalkyl (cycloalkyl of 3 to 6 carbon atoms, inclusive, and alkyl of 1 to 3 carbon atoms, inclusive), β-hydroxyethyl, cycloalkyl of 3 to 6 carbon atoms, inclusive, -CH 2 -alkynyl wherein alkenyl is of 2 to 8 carbon atoms, inclusive, ##STR51## wherein Y' is halogen, CF 3 , alkyl of 1 to 4 carbon atoms, inclusive, or alkoxy of 1 to 4 carbon atoms, inclusive, and m is 0, 1, or 2; and the acid addition salts thereof.

Claim 36

A process to claim 28 wherein the amount of compound administered is from about 0.01 mg. to about 7 mg. per kilogram of human or animal weight.

Claim 37

A process according to claim 28 wherein the compound administered is 4-(p-chlorophenyl)-4-dimethylaminocyclehexanone hydrochloride.

Claim 38

A process according to claim 28 wherein the compound administered is 4-(p-chlorophenyl)-4-dimethylaminocyclohexanone.

Claim 39

A process according to claim 28 wherein the compound administered is 4-(p-bromophenyl)-4-dimothylaminocyclohexanone.

Claim 40

A process according to claim 28 wherein the compound administered is 4-(n-hydroxyphenyl)-4-dimethylaminocyclehexanone.