US4447454A
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Analgetic compounds, compositions and process of treatment
Assignee: Pharmacia and Upjohn Co
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Filing: 1981-05-15
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Granted: 1984-05-08
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Expires: 2001-05-15
Abstract
Abstract Novel compounds of the formula: ##STR1## wherein R 1 is a variable consisting of hydrogen, alkyl of from 1 to 8 carbon atoms, CH 2 -alkenyl wherein alkenyl is from 2 to 4 carbon atoms, inclusive, cycloalkyl of from 3 to 6 carbon atoms, inclusive, cycloalkylmethyl of from 3 to 6 carbon atoms, inclusive; R 2 is a variable consisting of hydrogen, alkyl of from 1 to 8 carbon atoms, inclusive, with the proviso that R 1 and R 2 cannot both be hydrogen at the same time; Y is a variable consisting of alkyl of from 1 to 4 carbon atoms, inclusive, halogen, trifluoromethyl, hydroxy, alkanoyloxy from 2 to 5 carbon atoms, inclusive, alkoxy of from 1 to 4 carbon atoms, inclusive, cycloalkyloxy of from 3 to 6 carbon atoms, inclusive, benzyloxy; m is an integer 0, 1, 2; R 5 is a variable consisting of hydrogen and alkyl of from 1 to 4 carbon atoms, inclusive; R 3 is a variable consisting of alkyl of from 1 to 4 carbon atoms, inclusive; R 4 is a variable consisting of alkyl of from 1 to 4 carbon atoms, inclusive, CH 2 -alkenyl wherein alkenyl is of from 2 to 4 carbon atoms, inclusive, and arylalkyl wherein alkyl is from 1 to 4 carbon atoms, inclusive, and aryl is ##STR2## wherein Y' is CF 3 , halogen, alkyl of 1 to 4 carbon atoms, inclusive, and alkoxy of from 1 to 4 carbon atoms, inclusive; and R 3 and R 4 when taken together with the nitrogen atom to which they are attached can form saturated heterocycles of from 5 to 7 ring members, a second hetero atom of said ring can be oxygen or nitrogen, e.g., morpholine, piperazine, and said heterocycles can be monosubstituted having a total of up to 9 carbon atoms, with the proviso that when ##STR3## is pyrrolidinyl, then m=1, 2, having analgetic activity in humans and animals are prepared in unit dosage forms. The compositions are useful in relieving pain by administering orally, parenterally, and rectally to humans and animals.
Inventors
- 👤 Daniel Lednicer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 06:28
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/04; C07D295/12; C07D295/135; C07C; C07C255/00; C07D317/00; C07D317/08; C07D317/72
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
208 words
A compound of the formula: ##STR9## wherein R 1 is hydrogen, alkyl of from 1 to 8 carbon atoms, CH 2 -alkenyl wherein alkenyl is from 2 to 4 carbon atoms, inclusive, cycloalkyl of from 3 to 6 carbon atoms, inclusive, or cycloalkylmethyl of from 3 to 6 carbon atoms, inclusive: R 2 is hydrogen, or alkyl of from 1 to 8 carbon atoms, inclusive, with the proviso that R 1 and R 2 cannot both be hydrogen at the same time; Y is alkyl of from 1 to 4 carbon atoms, inclusive, halogen, trifluoromethyl, hydroxy, alkoxy of from 1 to 4 carbon atoms, inclusive, cycloalkyloxy of from 3 to 6 carbon atoms, inclusive, or benzyloxy; m is an integer 0, 1, or 2; R 3 is alkyl of from 1 to 4 carbon atoms, inclusive; R 4 is alkyl of from 1 to 4 carbon atoms, inclusive, CH 2 -alkenyl wherein alkenyl is of from 2 to 4 carbon atoms, inclusive, and arylalkyl wherein alkyl is from 1 to 4 carbon atoms, inclusive, and aryl is ##STR10## wherein Y' is CF 3 , halogen, alkyl of 1 to 4 carbon atoms, inclusive, and alkoxy of from 1 to 4 carbon atoms, inclusive; and its acid addition salts.
Claim 2
Dependent Claim
208 words
A compound of the formula: ##STR9## wherein R 1 is hydrogen, alkyl of from 1 to 8 carbon atoms, CH 2 -alkenyl wherein alkenyl is from 2 to 4 carbon atoms, inclusive, cycloalkyl of from 3 to 6 carbon atoms, inclusive, or cycloalkylmethyl of from 3 to 6 carbon atoms, inclusive: R 2 is hydrogen, or alkyl of from 1 to 8 carbon atoms, inclusive, with the proviso that R 1 and R 2 cannot both be hydrogen at the same time; Y is alkyl of from 1 to 4 carbon atoms, inclusive, halogen, trifluoromethyl, hydroxy, alkoxy of from 1 to 4 carbon atoms, inclusive, cycloalkyloxy of from 3 to 6 carbon atoms, inclusive, or benzyloxy; m is an integer 0, 1, or 2; R 3 is alkyl of from 1 to 4 carbon atoms, inclusive; R 4 is alkyl of from 1 to 4 carbon atoms, inclusive, CH 2 -alkenyl wherein alkenyl is of from 2 to 4 carbon atoms, inclusive, and arylalkyl wherein alkyl is from 1 to 4 carbon atoms, inclusive, and aryl is ##STR10## wherein Y' is CF 3 , halogen, alkyl of 1 to 4 carbon atoms, inclusive, and alkoxy of from 1 to 4 carbon atoms, inclusive; and its acid addition salts.
Claim 3
Dependent Claim
11 words
A compound according to claim 1 in its less polar form.
Claim 4
Dependent Claim
10 words
A compound according to claim 1 which is 1-p-chlorophenyl-1-dimethylamino 4-(N-allyl-N-methylamino)cyclohexane.
Claim 5
Dependent Claim
225 words
A composition for relief of pain comprising an analgetic amount of a compound of the formula: ##STR11## wherein R 1 is hydrogen, alkyl of from 1 to 8 carbon atoms, CH 2 -alkenyl wherein alkenyl is from 2 to 4 carbon atoms, inclusive, cycloalkyl of from 3 to 6 carbon atoms, inclusive, or cycloalkylmethyl of from 3 to 6 carbon atoms, inclusive; R 2 is hydrogen, or alkyl of from 1 to 8 carbon atoms, inclusive, with the proviso that R 1 and R 2 cannot both be hydrogen at the same time; Y is alkyl of from 1 to 4 carbon atoms, inclusive, halogen, trifluoromethyl, hydroxy, alkoxy of from 1 to 4 carbon atoms, inclusive, cycloalkyloxy of from 3 to 6 carbon atoms, inclusive, or benzyloxy; m is an integer 0, 1, or 2; R 3 is alkyl of from 1 to 4 carbon atoms, inclusive; R 4 is alkyl of from 1 to 4 carbon atoms, inclusive, CH 2 -alkenyl wherein alkenyl is of from 2 to 4 carbon atoms, inclusive, and arylalkyl wherein alkyl is from 1 to 4 carbon atoms, inclusive, and aryl is ##STR12## wherein Y' is CF 3 , halogen, alkyl of 1 to 4 carbon atoms, inclusive, and alkoxy of from 1 to 4 carbon atoms, inclusive; or its pharmacologically acceptable salts, in association with a pharmaceutical carrier.
Claim 6
Dependent Claim
225 words
A composition for relief of pain comprising an analgetic amount of a compound of the formula: ##STR11## wherein R 1 is hydrogen, alkyl of from 1 to 8 carbon atoms, CH 2 -alkenyl wherein alkenyl is from 2 to 4 carbon atoms, inclusive, cycloalkyl of from 3 to 6 carbon atoms, inclusive, or cycloalkylmethyl of from 3 to 6 carbon atoms, inclusive; R 2 is hydrogen, or alkyl of from 1 to 8 carbon atoms, inclusive, with the proviso that R 1 and R 2 cannot both be hydrogen at the same time; Y is alkyl of from 1 to 4 carbon atoms, inclusive, halogen, trifluoromethyl, hydroxy, alkoxy of from 1 to 4 carbon atoms, inclusive, cycloalkyloxy of from 3 to 6 carbon atoms, inclusive, or benzyloxy; m is an integer 0, 1, or 2; R 3 is alkyl of from 1 to 4 carbon atoms, inclusive; R 4 is alkyl of from 1 to 4 carbon atoms, inclusive, CH 2 -alkenyl wherein alkenyl is of from 2 to 4 carbon atoms, inclusive, and arylalkyl wherein alkyl is from 1 to 4 carbon atoms, inclusive, and aryl is ##STR12## wherein Y' is CF 3 , halogen, alkyl of 1 to 4 carbon atoms, inclusive, and alkoxy of from 1 to 4 carbon atoms, inclusive; or its pharmacologically acceptable salts, in association with a pharmaceutical carrier.
Claim 7
Dependent Claim
18 words
A composition according to claim 4 wherein the compound of the Formula is in its less polar form.
Claim 8
Dependent Claim
25 words
A composition according to claim 4, in unit dosage form where the concentration of the compound is from 5 to 500 mg. per dosage unit.
Claim 9
Dependent Claim
11 words
A composition according to claim 4 wherein the compound is 1-p-chlorophenyl-1-dimethylamino-4-(N-allyl-N-methylamino)cyclohexane.
Claim 10
Independent Claim
231 words
A method for the relief of pain comprising the systemic administration to a human or animal of an analgetic amount of a compound of the formula: ##STR13## wherein R 1 is hydrogen, alkyl of from 1 to 8 carbon atoms, CH 2 -alkenyl wherein alkenyl is from 2 to 4 carbon atoms, inclusive, cycloalkyl of from 3 to 6 carbon atoms, inclusive, or cycloalkylmethyl of from 3 to 6 carbon atoms, inclusive; R 2 is hydrogen, or alkyl of from 1 to 8 carbon atoms, inclusive, with the proviso that R 1 and R 2 cannot both be hydrogen at the same time; Y is alkyl of from 1 to 4 carbon atoms, inclusive, halogen, trifluoromethyl, hydroxy, alkoxy of from 1 to 4 carbon atoms, inclusive, cycloalkyloxy of from 3 to 6 carbon atoms, inclusive, or benzyloxy; m is an integer 0, 1, or 2; R 3 is alkyl of from 1 to 4 carbon atoms, inclusive; R 4 is alkyl of from 1 to 4 carbon atoms, inclusive, CH 2 -alkenyl wherein alkenyl is of from 2 to 4 carbon atoms, inclusive, and arylalkyl wherein alkyl is from 1 to 4 carbon atoms, inclusive, and aryl is ##STR14## wherein Y' is CF 3 , halogen, alkyl of 1 to 4 carbon atoms, inclusive, and alkoxy of from 1 to 4 carbon atoms, inclusive; or its pharmacologically acceptable acid addition salts.
Claim 11
Independent Claim
231 words
A method for the relief of pain comprising the systemic administration to a human or animal of an analgetic amount of a compound of the formula: ##STR13## wherein R 1 is hydrogen, alkyl of from 1 to 8 carbon atoms, CH 2 -alkenyl wherein alkenyl is from 2 to 4 carbon atoms, inclusive, cycloalkyl of from 3 to 6 carbon atoms, inclusive, or cycloalkylmethyl of from 3 to 6 carbon atoms, inclusive; R 2 is hydrogen, or alkyl of from 1 to 8 carbon atoms, inclusive, with the proviso that R 1 and R 2 cannot both be hydrogen at the same time; Y is alkyl of from 1 to 4 carbon atoms, inclusive, halogen, trifluoromethyl, hydroxy, alkoxy of from 1 to 4 carbon atoms, inclusive, cycloalkyloxy of from 3 to 6 carbon atoms, inclusive, or benzyloxy; m is an integer 0, 1, or 2; R 3 is alkyl of from 1 to 4 carbon atoms, inclusive; R 4 is alkyl of from 1 to 4 carbon atoms, inclusive, CH 2 -alkenyl wherein alkenyl is of from 2 to 4 carbon atoms, inclusive, and arylalkyl wherein alkyl is from 1 to 4 carbon atoms, inclusive, and aryl is ##STR14## wherein Y' is CF 3 , halogen, alkyl of 1 to 4 carbon atoms, inclusive, and alkoxy of from 1 to 4 carbon atoms, inclusive; or its pharmacologically acceptable acid addition salts.
Claim 12
Dependent Claim
17 words
The method of claim 8 wherein the compound of the Formula is in its less polar form.
Claim 13
Dependent Claim
30 words
The method of claim 8 wherein the compound is administered in an amount of from 0.1 mg. to 7 mg. per kg. body weight of the said human or animal.
Claim 14
Dependent Claim
12 words
The method of claim 8 wherein the compound administered is 1-p-chlorophenyl-1-dimethylamino-4-(N-allyl-N-methylamino cyclohexane.
References Cited (Backward Citations)
US4113866A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-05-08 | 1987-11-07 | 1988-05-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-05-08 | 1991-11-07 | 1992-05-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-05-08 | 1995-11-07 | 1996-05-08 | $7700.00 | Window Closed / Lapsed |