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US4131744A
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4,5-Disubstituted-1-aminoalkyl cyclohexenes
Assignee: ER Squibb and Sons LLC
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Filing: 1977-04-25
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Granted: 1978-12-26
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Expires: 1997-04-25
Abstract
Abstract Compounds of the formula ##STR1## wherein R is hydrogen, ##STR2## R 1 and R 2 are independently selected from hydrogen, lower alkyl, and cycloalkyl or R 1 and R 2 taken together with the nitrogen atom to which they are attached form a ring of the formula ##STR3## N IS 0 OR AN INTEGER FROM 1 TO 3; M IS AN INTEGER FROM 1 TO 3; R 3 and R 4 are independently selected from hydrogen and lower alkyl; X is hydrogen, halogen, lower alkyl, lower alkoxy, or nitro; and their salts; are disclosed. These compounds possess useful antiinflammatory properties.
Inventors
- 👤 Joseph E. Sundeen
- 👤 Frederic P. Hauck
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 07:09
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/02; C07D295/027; C07D295/03; C07D295/04; C07D295/08; C07D295/096
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
82 words
A compound of the formula: ##STR92## including its stereoisomers wherein R is hydrogen ##STR93## R 1 and R 2 are independently selected from the group consisting of hydrogen, lower alkyl, and cycloalkyl of 3 to 7 carbons; R 3 and R 4 are independently selected from the group consisting of hydrogen and lower alkyl; n is 0 or an integer from 1 to 3; X is hydrogen, halogen, lower alkyl, lower alkoxy, or nitro; and a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
82 words
A compound of the formula: ##STR92## including its stereoisomers wherein R is hydrogen ##STR93## R 1 and R 2 are independently selected from the group consisting of hydrogen, lower alkyl, and cycloalkyl of 3 to 7 carbons; R 3 and R 4 are independently selected from the group consisting of hydrogen and lower alkyl; n is 0 or an integer from 1 to 3; X is hydrogen, halogen, lower alkyl, lower alkoxy, or nitro; and a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
48 words
The compound of claim 1 wherein R is hydrogen, ##STR94## R 1 and R 2 are independently selected from the group consisting of hydrogen, methyl, and ethyl; R 3 is hydrogen, methyl, or ethyl; R 4 is hydrogen; and X is hydrogen, Cl, Br, methyl, methoxy or nitro.
Claim 4
Dependent Claim
14 words
The compound of claim 2 wherein the --OR substituents are in the cis configuration.
Claim 5
Dependent Claim
37 words
The compound of claim 3 wherein R is hydrogen or ##STR95## R 1 and R 2 are independently selected from the group consisting of hydrogen and methyl; R 3 is hydrogen or methyl; and n is 1.
Claim 6
Dependent Claim
19 words
The compound of claim 4 wherein R, R 1 , R 2 , and R 3 are all hydrogen.
Claim 7
Dependent Claim
9 words
The compound of claim 5, dl-cis-4-(2-aminoethyl)-4-cyclohexene-1,2-diol, acetate salt (1:1).
Claim 8
Dependent Claim
19 words
The compound of claim 4 wherein R, R 1 and R 3 are hydrogen and R 2 is methyl.
Claim 9
Dependent Claim
9 words
The compound of claim 7, dl-cis-4-[2-(methylamino)-ethyl]-4-cyclohexene-1,2-diol, 4-methylbenzenesulfonate salt (1:1).
Claim 10
Dependent Claim
22 words
The compound of claim 4 wherein R and R 3 are both hydrogen and R 1 and R 2 are both methyl.
Claim 11
Dependent Claim
9 words
The compound of claim 9, dl-cis-4-[2-(dimethylamino)-ethyl]-4-cyclohexene-1,2-diol, 4-methylbenzenesulfonate salt (1:1).
Claim 12
Dependent Claim
20 words
The compound of claim 4 wherein R, R 1 and R 2 are all hydrogen and R 3 is methyl.
Claim 13
Dependent Claim
6 words
The compound of claim 11, dl-cis-4-(2-aminopropyl)-4-cyclohexene-1,2-diol.
Claim 14
Dependent Claim
22 words
The compound of claim 4 wherein R is ##STR96## R 1 and R 3 are both hydrogen; and R 2 is methyl.
Claim 15
Dependent Claim
11 words
The compound of claim 13, dl-cis-4-[2-(methylamino)-ethyl]-4-cyclohexene-1,2-diol, diacetate ester, hydrochloride salt (1:1).
Claim 16
Dependent Claim
22 words
The compound of claim 4 wherein R is ##STR97## R 1 and R 2 are both methyl; and R 3 is hydrogen.
Claim 17
Dependent Claim
11 words
The compound of claim 15, dl-cis-4-[2-(dimethylamino)-ethyl]-4-cyclohexene-1,2-diol, diacetate ester, oxalate salt (1:1).
Claim 18
Dependent Claim
14 words
The compound of claim 2 wherein the --OR substituents are in the trans configuration.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-12-25 | 1982-06-26 | 1982-12-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-12-25 | 1986-06-26 | 1986-12-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-12-25 | 1990-06-26 | 1990-12-26 | $7700.00 | Window Closed / Lapsed |