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US4065573A
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4-Amino-4-phenylcyclohexanone ketal compositions and process of use
Assignee: Pharmacia and Upjohn Co
•
Filing: 1976-06-03
•
Granted: 1977-12-27
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Expires: 1996-06-03
Abstract
Abstract A class of new 4-amino-4-arylcyclohexanones, their ketals, and acid addition salts have been synthesized and found to be useful for relieving pain in animals. Their analgesic activity appears to be of high order, and in addition some exhibit narcotic antagonist activity that is useful in modifying the cardiovascular, respiratory, and behavioral depression caused by other analgesics. Several show mixed analgesic and narcotic antagonist activity. Preferred compounds of the class are 4-(m-hydroxyphenyl)-4-dimethylaminocyclohexanone ethylene ketal, and 4-(m-hydroxyphenyl)-4-(n-butylmethylamino)cyclohexanone ethylene ketal as free bases and as their hydrochloride salts. Processes for synthesis and intermediates are described. Unit dosage forms and therapeutic treatments are disclosed.
Inventors
- 👤 Daniel Lednicer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 22:11
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/04; C07D295/10; C07D295/112; C07D295/116; A; A61; A61P; A61P25/00; A61P25/04; C07C; C07C255/00; C07D317/00; C07D317/08; C07D317/72; C07D319/00; C07D319/04; C07D319/08; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/14; C07D333/16; C07D333/24; C07C2601/00; C07C2601/12; C07C2601/14
Claims Analysis
Total Claims: 77
Claim 1
Independent Claim
217 words
A compound of the formula: ##STR23## wherein X is ##STR24## wherein n is zero or one and R 4 is hydrogen or methyl; R 5 is hydrogen, phenyl, --CH 2 -alkenyl wherein alkenyl is of 2 to 4 carbon atoms, inclusive, or methyl; aryl is ##STR25## 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, alkanoyloxy of 2 to 4 carbon atoms, inclusive, alkylthio of 1 to 4 carbon atoms, inclusive, or ##STR26## 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, carbethoxymethyl, cycloalkyl of 3 to 6 carbon atoms, inclusive, ##STR27## and R 3 is hydrogen, alkyl of 1 to 5 carbon atoms, inclusive, and the acid addition salts thereof.
Claim 2
Dependent Claim
217 words
A compound of the formula: ##STR23## wherein X is ##STR24## wherein n is zero or one and R 4 is hydrogen or methyl; R 5 is hydrogen, phenyl, --CH 2 -alkenyl wherein alkenyl is of 2 to 4 carbon atoms, inclusive, or methyl; aryl is ##STR25## 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, alkanoyloxy of 2 to 4 carbon atoms, inclusive, alkylthio of 1 to 4 carbon atoms, inclusive, or ##STR26## 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, carbethoxymethyl, cycloalkyl of 3 to 6 carbon atoms, inclusive, ##STR27## and R 3 is hydrogen, alkyl of 1 to 5 carbon atoms, inclusive, and the acid addition salts thereof.
Claim 3
Dependent Claim
140 words
A compound of claim 1 of the formula: ##STR28## wherein X is ##STR29## wherein Y is alkoxy of 1 to 4 carbon atoms, inclusive, hydroxy, cycloalkyloxy of 3 to 6 carbon atoms, inclusive, alkanoyloxy of 2 to 4 carbon atoms, inclusive, ##STR30## 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 (cycloalklyl of 3 to 6 carbon atoms, inclusive, alkyl of 1 to 3 carbon atoms, inclusive), β-hydroxyethyl, carbethoxymethyl, 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
Dependent Claim
166 words
A compound of claim 1 of the formula: ##STR31## wherein X is ##STR32## 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, carbethoxymethyl, cycloalkyl of 3 to 6 carbon atoms, inclusive, -CH 2 -alkenyl wherein alkenyl is of 2 to 8 carbon atoms, inclusive, ##STR33## and ##STR34## 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
Dependent Claim
13 words
A compound according to claim 1 which is 4-(p-chlorophenyl)-4-dimethylaminocyclohexanone, ethylene ketal free base.
Claim 6
Dependent Claim
12 words
A compound according to claim 1 which is 4-(p-chlorophenyl)-4-dimethylaminocyclohexanone, ethylene ketal hydrochloride.
Claim 7
Dependent Claim
13 words
A compound according to claim 1 which is 4-(p-fluorophenyl)-4-dimethylaminocyclohexanone, ethylene ketal free base.
Claim 8
Dependent Claim
12 words
A compound according to claim 1 which is 4-(p-fluorophenyl)-4-dimethylaminocyclohexanone, ethylene ketal hydrochloride.
Claim 9
Dependent Claim
13 words
A compound according to claim 1 which is 4-(p-anisyl)-4-dimethylaminocyclohexanone, ethylene ketal free base.
Claim 10
Dependent Claim
12 words
A compound according to claim 1 which is 4-(p-anisyl)-4-dimethylaminocyclohexanone, ethylene ketal hydrochloride.
Claim 11
Dependent Claim
13 words
A compound according to claim 1 which is 4-(o-chlorophenyl)-4-dimethylaminocyclohexanone, ethylene ketal free base.
Claim 12
Dependent Claim
12 words
A compound according to claim 1 which is 4-(o-chlorophenyl)-4-dimethylaminocyclohexanone, ethylene ketal hydroiodide.
Claim 13
Dependent Claim
13 words
A compound according to claim 1 which is 4-(m-anisyl)-4-dimethylaminocyclohexanone, ethylene ketal free base.
Claim 14
Dependent Claim
12 words
A compound according to claim 1 which is 4-(m-anisyl)-4-dimethylaminocyclohexanone, ethylene ketal hydrochloride.
Claim 15
Dependent Claim
13 words
A compound according to claim 1 which is 4-dimethylamino-4-(p-tolyl)cyclohexanone, ethylene ketal free base.
Claim 16
Dependent Claim
12 words
A compound according to claim 1 which is 4-dimethylamino-4-(p-tolyl)cyclohexanone, ethylene ketal hydrochloride.
Claim 17
Dependent Claim
13 words
A compound according to claim 1 which is 4-(p-bromophenyl)-4-dimethylaminocyclohexanone, ethylene ketal free base.
Claim 18
Dependent Claim
12 words
A compound according to claim 1 which is 4-(p-bromophenyl)-4-dimethylaminocyclohexanone, ethylene ketal hydrochloride.
Claim 19
Dependent Claim
13 words
A compound according to claim 1 which is 4-(2,4-dichlorophenyl)-4-dimethylaminocyclohexanone, ethylene ketal free base.
Claim 20
Dependent Claim
12 words
A compound according to claim 1 which is 4-(2,4-dichlorophenyl)-4-dimethylaminocyclohexanone, ethylene ketal hydrochloride.
Claim 21
Dependent Claim
13 words
A compound according to claim 1 which is 4-(methyl-n-butylamino)-4-(m-hydroxyphenyl)cyclohexan-1-one, ethylene ketal free base.
Claim 22
Dependent Claim
12 words
A compound according to claim 1 which is 4-(methyl-n-butylamino)-4-(m-hydroxyphenyl)cyclohexan-1-one, ethylene ketal hydrochloride.
Claim 23
Dependent Claim
11 words
A compound according to claim 1 which is 4-(m-hydroxyphenyl)-4-dimethylaminocyclohexanone, ethylene ketal.
Claim 24
Dependent Claim
13 words
A compound according to claim 1 which is 4-(p-hydroxyphenyl)-4-(n-butylmethylamino)cyclohexanone ethylene ketal free base.
Claim 25
Dependent Claim
12 words
A compound according to claim 1 which is 4-(p-hydroxyphenyl)-4-(n-butylmethylamino)cyclohexanone ethylene ketal hydrochloride.
Claim 26
Dependent Claim
13 words
A compound according to claim 1 which is 4-(p-trifluoromethylphenyl)-4-dimethylaminocyclohexanone, ethylene ketal free base.
Claim 27
Dependent Claim
11 words
A compound to claim 1 which is 4-(p-trifluoromethylphenyl)-4-dimethylaminocyclohexanone, ethylene ketal hydrochloride.
Claim 28
Dependent Claim
13 words
A compound according to claim 1 which is 4-(m-hydroxyphenyl)-4-(n-propylmethylamino)cyclohexanone ethylene ketal free base.
Claim 29
Dependent Claim
12 words
A compound according to claim 1 which is 4-(m-hydroxyphenyl)-4-(n-propylmethylamino)cyclohexanone ethylene ketal hydrochloride.
Claim 30
Dependent Claim
13 words
A compound according to claim 1 which is 4-(m-hydroxyphenyl)-4-(methyl-n-pentylamino)cyclohexanone ethylene ketal free base.
Claim 31
Dependent Claim
12 words
A compound according to claim 1 which is 4-(m-hydroxyphenyl)-4-(methyl-n-pentylamino)cyclohexanone ethylene ketal hydrochloride.
Claim 32
Dependent Claim
13 words
A compound according to claim 1 which is 4-(m-hydroxyphenyl)-4-(i-butylmethylamino)cyclohexanone ethylene ketal free base.
Claim 33
Dependent Claim
12 words
A compound according to claim 1 which is 4-(m-hydroxyphenyl)-4-(i-butylmethylamino)cyclohexanone ethylene ketal hydrochloride.
Claim 34
Dependent Claim
11 words
A compound according to claim 1 which is 4-(m-hydroxyphenyl)-4-dimethylaminocyclohexanone trimethylene ketal.
Claim 35
Dependent Claim
11 words
A compound according to claim 1 which is 4-(m-benzyloxyphenyl)-4-(methyl-n-butylamino)cyclohexanone, ethylene ketal.
Claim 36
Dependent Claim
124 words
An intermediate compound of the formula: ##STR35## wherein X is ##STR36## wherein n is zero or one and R 4 is hydrogen or methyl; R 5 is hydrogen, methyl, phenyl, or --CH 2 -alkenyl wherein alkenyl is of 2 to 4 carbon atoms, inclusive; aryl is ##STR37## 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, ##STR38## 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 37
Dependent Claim
124 words
An intermediate compound of the formula: ##STR35## wherein X is ##STR36## wherein n is zero or one and R 4 is hydrogen or methyl; R 5 is hydrogen, methyl, phenyl, or --CH 2 -alkenyl wherein alkenyl is of 2 to 4 carbon atoms, inclusive; aryl is ##STR37## 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, ##STR38## 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 38
Dependent Claim
11 words
A compound according to claim 35 which is 4-(p-chlorophenyl)-4-methylaminocyclohexanone, ethylene ketal.
Claim 39
Dependent Claim
11 words
A compound according to claim 35 which is 4-(p-fluorophenyl)-4-methylaminocyclohexanone, ethylene ketal.
Claim 40
Dependent Claim
12 words
A compound according to claim 35 which is 4-(p-fluorophenyl)-4-methylaminocyclohexanone, ethylene ketal hydrochloride.
Claim 41
Dependent Claim
13 words
A compound according to claim 35 which is 4-(p-anisyl)-4-methylaminocyclohexanone, ethylene ketal free base.
Claim 42
Dependent Claim
12 words
A compound according to claim 35 which is 4-(p-anisyl)-4-methylaminocyclohexanone, ethylene ketal p-toluenesulfonate.
Claim 43
Dependent Claim
13 words
A compound according to claim 35 which is 4-(m-anisyl)-4-methylaminocyclohexanone, ethylene ketal free base.
Claim 44
Dependent Claim
12 words
A compound according to claim 35 which is 4-(m-anisyl)-4-methylaminocyclohexanone, ethylene ketal hydrochloride.
Claim 45
Dependent Claim
11 words
A compound according to claim 35 which is 4-methylamino-4-(p-tolyl)cyclohexanone, ethylene ketal.
Claim 46
Dependent Claim
13 words
A compound according to claim 35 which is 4-(p-bromophenyl)-4-methylaminocyclohexanone, ethylene ketal free base.
Claim 47
Dependent Claim
12 words
A compound according to claim 35 which is 4-(p-bromophenyl)-4-methylaminocyclohexanone, ethylene ketal hydrochloride.
Claim 48
Dependent Claim
11 words
A compound according to claim 35 which is 4-(m-benzyloxyphenyl)-4-(methylamino)cyclohexan-1-one, ethylene ketal.
Claim 49
Dependent Claim
11 words
A compound according to claim 35 which is 4-methylamino-4-(p-benzyloxyphenyl)cyclohexanone ethylene ketal.
Claim 50
Dependent Claim
123 words
An intermediate compound of the formula: ##STR39## wherein X is ##STR40## wherein n is zero or one and R 4 is hydrogen or methyl; R 5 is hydrogen, methyl, phenyl, --CH 2 -alkenyl wherein alkenyl is of 2 to 4 carbon atoms, inclusive; aryl is ##STR41## 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, ##STR42## 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 51
Dependent Claim
123 words
An intermediate compound of the formula: ##STR39## wherein X is ##STR40## wherein n is zero or one and R 4 is hydrogen or methyl; R 5 is hydrogen, methyl, phenyl, --CH 2 -alkenyl wherein alkenyl is of 2 to 4 carbon atoms, inclusive; aryl is ##STR41## 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, ##STR42## 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 52
Dependent Claim
13 words
A compound according to claim 48 which is 4-amino-4-phenylcyclohexanone, ethylene ketal free base.
Claim 53
Dependent Claim
12 words
A compound according to claim 48 which is 4-amino-4-phenylcyclohexanone, ethylene ketal hydrochloride.
Claim 54
Dependent Claim
247 words
A pharmaceutical composition in unit dosage form for relieving pain in animals comprising as an active ingredient an analgetic effective amount of a compound of the formula: ##STR43## wherein X is ##STR44## wherein n is zero or one and R 4 is hydrogen or methyl; R 5 is hydrogen, phenyl, --CH 2 -alkenyl wherein alkenyl is of 2 to 4 carbon atoms, inclusive, or methyl; 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, alkanoyloxy of 2 to 4 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, or 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, carbethoxymethyl, cycloalkyl of 3 to 6 carbon atoms, inclusive, ##STR47## or ##STR48## 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 55
Dependent Claim
247 words
A pharmaceutical composition in unit dosage form for relieving pain in animals comprising as an active ingredient an analgetic effective amount of a compound of the formula: ##STR43## wherein X is ##STR44## wherein n is zero or one and R 4 is hydrogen or methyl; R 5 is hydrogen, phenyl, --CH 2 -alkenyl wherein alkenyl is of 2 to 4 carbon atoms, inclusive, or methyl; 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, alkanoyloxy of 2 to 4 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, or 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, carbethoxymethyl, cycloalkyl of 3 to 6 carbon atoms, inclusive, ##STR47## or ##STR48## 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 56
Dependent Claim
148 words
A composition according to claim 51 wherein the active ingredient is a compound of the formula: ##STR49## wherein X is ##STR50## wherein Y is alkoxy of 1 to 4 carbon atoms, inclusive, hydroxy, cycloalkyloxy of 3 to 6 carbon atoms, inclusive, alkanoyloxy of 2 to 4 carbon atoms, inclusive, ##STR51## 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, carbethoxymethyl, 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 57
Dependent Claim
174 words
A composition according to claim 51 wherein the active ingredient is a compound of the formula: ##STR52## wherein X is ##STR53## 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, carbethoxymethyl, cycloalkyl of 3 to 6 carbon atoms, inclusive, --CH 2 -alkenyl wherein alkenyl is of 2 to 8 carbon atoms, inclusive, ##STR54## and ##STR55## 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 58
Dependent Claim
23 words
A composition according to claim 51 wherein the active ingredient is present in unit dosage form of from 0.5 mg. to 500 mg.
Claim 59
Dependent Claim
16 words
A composition according to claim 51 wherein the active ingredient is 4-(p-chlorophenyl)-4-dimethylaminocyclohexanone, ethylene ketal free base.
Claim 60
Dependent Claim
15 words
A composition according to claim 51 wherein the active ingredient is 4-(p-chlorophenyl)-4-dimethylaminocyclohexanone ethylene ketal hydrochloride.
Claim 61
Dependent Claim
15 words
A composition according to claim 51 wherein the active ingredient is 4-(m-anisyl)-4-dimethylaminocyclohexanone, ethylene ketal hydrochloride.
Claim 62
Dependent Claim
15 words
A composition according to claim 51 wherein the active ingredient is 4-(p-bromophenyl)-4-dimethylaminocyclohexanone, ethylene ketal hydrochloride.
Claim 63
Dependent Claim
15 words
A composition according to claim 51 wherein the active ingredient is 4-(2,4-dichlorophenyl)-4-dimethylaminocyclohexanone, ethylene ketal hydrochloride.
Claim 64
Dependent Claim
14 words
A composition according to claim 51 wherein the active ingredient is 4-(methyl-n-butylamino)-4-(m-hydroxyphenyl)cyclohexan-1-one, ethylene ketal.
Claim 65
Dependent Claim
15 words
A composition according to claim 51 wherein the active ingredient is 4-(methyl-n-butylamino)-4-(m-hydroxyphenyl)cyclohexan-1-one ethylene ketal hydrochloride.
Claim 66
Dependent Claim
242 words
A process for inducing analgesia in humans and animals comprising the administration of an analgetic amount of a compound of the formula: ##STR56## wherein X is ##STR57## wherein n is zero or one and R 4 is hydrogen or methyl; R 5 is hydrogen, phenyl, --CH 2 -alkenyl wherein alkenyl is of 2 to 4 carbon atoms, inclusive, or methyl; aryl is ##STR58## 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, alkanoyloxy of 2 to 4 carbon atoms, inclusive, alkylthio of 1 to 4 carbon atoms, inclusive, or ##STR59## 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-hyhydroyethyl, carbethoxymethyl, cycloalkyl of 3 to 6 carbon atoms, inclusive, ##STR60## or ##STR61## 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 67
Dependent Claim
242 words
A process for inducing analgesia in humans and animals comprising the administration of an analgetic amount of a compound of the formula: ##STR56## wherein X is ##STR57## wherein n is zero or one and R 4 is hydrogen or methyl; R 5 is hydrogen, phenyl, --CH 2 -alkenyl wherein alkenyl is of 2 to 4 carbon atoms, inclusive, or methyl; aryl is ##STR58## 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, alkanoyloxy of 2 to 4 carbon atoms, inclusive, alkylthio of 1 to 4 carbon atoms, inclusive, or ##STR59## 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-hyhydroyethyl, carbethoxymethyl, cycloalkyl of 3 to 6 carbon atoms, inclusive, ##STR60## or ##STR61## 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 68
Dependent Claim
148 words
A process according to claim 62 wherein the compound administered is a compound of the formula: ##STR62## wherein X is ##STR63## wherein Y is alkoxy of 1 to 4 carbon atoms, inclusive, hydroxy, cycloalkyloxy of 3 to 6 carbon atoms, inclusive, alkanoyloxy of 2 to 4 carbon atoms, inclusive, ##STR64## 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, carbethoxymethyl, 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 69
Dependent Claim
174 words
A process according to claim 62 wherein the compound administered is a compound of the formula: ##STR65## wherein X is ##STR66## 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, carbethoxymethyl, cycloalkyl of 3 to 6 carbon atoms, inclusive, --CH 2 -alkenyl wherein alkenyl is of 2 to 8 carbon atoms, inclusive, ##STR67## and ##STR68## 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 70
Dependent Claim
28 words
A process according to claim 62 wherein the amount of compound administered is from about 0.01 mg. to about 7 mg. per kilogram of human or animal weight.
Claim 71
Dependent Claim
16 words
A process according to claim 62 wherein the compound administered is 4-(p-chlorophenyl)-4-dimethylaminocyclohexanone, ethylene ketal free base.
Claim 72
Dependent Claim
15 words
A process according to claim 62 wherein the compound administered is 4-(p-chlorophenyl)-4-dimethylaminocyclohexanone ethylene ketal hydrochloride.
Claim 73
Dependent Claim
15 words
A process according to claim 62 wherein the compound administered is 4-(m-anisyl)-4-dimethylaminocyclohexanone, ethylene ketal hydrochloride.
Claim 74
Dependent Claim
15 words
A process according to claim 62 wherein the compound administered is 4-(p-bromophenyl)-4-dimethylaminocyclohexanone, ethylene ketal hydrochloride.
Claim 75
Dependent Claim
15 words
A process according to claim 62 wherein the compound administered is 4-(2,4-dichlorophenyl)-4-dimethylaminocyclohexanone, ethylene ketal hydrochloride.
Claim 76
Dependent Claim
14 words
A process according to claim 62 wherein the compound administered is 4-(methyl-n-butylamino)-4-(m-hydroxyphenyl)-cyclohexan-1-one, ethylene ketal.
Claim 77
Dependent Claim
15 words
A process according to claim 62 wherein the compound administered is 4-(methyl-n-butylamino)-4-(m-hydroxyphenyl)-cyclohexan-1-one ethylene ketal hydrochloride.
References Cited (Backward Citations)
US3901920A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-12-26 | 1981-06-27 | 1981-12-27 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-12-26 | 1985-06-27 | 1985-12-27 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-12-26 | 1989-06-27 | 1989-12-27 | $7700.00 | Window Closed / Lapsed |