US4598087A
Expired / Lapsed
US
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Substituted trans-1,2-diaminocyclohexyl amide compounds
Assignee: Warner Lambert Co LLC
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Filing: 1984-11-13
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Granted: 1986-07-01
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Expires: 2004-11-13
Abstract
Abstract Substituted trans-1,2-diaminocyclohexyl amide compounds demonstrating selective opioid receptor binding possess utility as analgesic, diuretic, and psychotherapeutic agents. A method of preparing the compounds, pharmaceutical compositions employing the compounds, and a method of alleviating pain employing the compounds are also disclosed.
Inventors
- 👤 David C. Horwell
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 21:20
CPC Classifications
A; A61; A61K; A61K31/00; A61K31/16; A61K31/165; C; C07; C07C; C07C233/00
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
55 words
A compound having the structural formula ##STR11## where n is one or two; X is --O--, --S--, or --NH--; and R 6 and R 7 are independently hydrogen, fluorine, chlorine, nitro, alkyl of from one to six carbon atoms, phenyl, or alkoxy of from one to six carbon atoms; and the pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
55 words
A compound having the structural formula ##STR11## where n is one or two; X is --O--, --S--, or --NH--; and R 6 and R 7 are independently hydrogen, fluorine, chlorine, nitro, alkyl of from one to six carbon atoms, phenyl, or alkoxy of from one to six carbon atoms; and the pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
26 words
A compound selected from the group consisting of trans-2-(2,3-dichlorophenoxy)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-2-(3,4-dichlorophenoxy)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-2-(2,4-dichlorophenoxy)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-2-(2,6-dichlorophenoxy)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-2-(3-chlorophenoxy)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-2-(2-chlorophenoxy)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-2-(4-fluorophenoxy)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-2-[(4-chlorophenyl)thio]-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-3-(4-chlorophenoxy)-N-methyl-N-[2-(1-pyrrolidinyl)-cyclohexyl]propanamide; trans-N-methyl-2-(2-nitrophenoxy)-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide. and the pharmaceutically acceptable acid addition salts thereof.
Claim 4
Dependent Claim
26 words
A compound selected from the group consisting of trans-2-(2,3-dichlorophenoxy)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-2-(3,4-dichlorophenoxy)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-2-(2,4-dichlorophenoxy)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-2-(2,6-dichlorophenoxy)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-2-(3-chlorophenoxy)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-2-(2-chlorophenoxy)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-2-(4-fluorophenoxy)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-2-[(4-chlorophenyl)thio]-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-3-(4-chlorophenoxy)-N-methyl-N-[2-(1-pyrrolidinyl)-cyclohexyl]propanamide; trans-N-methyl-2-(2-nitrophenoxy)-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide. and the pharmaceutically acceptable acid addition salts thereof.
Claim 5
Dependent Claim
23 words
A compound selected from the group consisting of: trans-N-methyl-2-(phenylthio)-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-N-methyl-2-phenoxy-N-[2-(1-pyrrolidinyl)cyclohexyl]-acetamide; trans-N-methyl-2-(3-methylphenoxy)-N-[2-(1-pyrrolidinyl)-cyclohexyl]acetamide; trans-N-methyl-2-(4-methylphenoxy)-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-2-[4-(1,1-dimethylethyl)phenoxy]-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-methyl-2-(phenylamino)-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-2-([1,1-biphenyl]-4-yloxy)-N-methyl-N-[2-(1-pyrrolinyl)cyclohexyl]acetamide; and the pharmaceutically acceptable acid addition salts thereof.
Claim 6
Dependent Claim
23 words
A compound selected from the group consisting of: trans-N-methyl-2-(phenylthio)-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-N-methyl-2-phenoxy-N-[2-(1-pyrrolidinyl)cyclohexyl]-acetamide; trans-N-methyl-2-(3-methylphenoxy)-N-[2-(1-pyrrolidinyl)-cyclohexyl]acetamide; trans-N-methyl-2-(4-methylphenoxy)-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-2-[4-(1,1-dimethylethyl)phenoxy]-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-methyl-2-(phenylamino)-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; trans-2-([1,1-biphenyl]-4-yloxy)-N-methyl-N-[2-(1-pyrrolinyl)cyclohexyl]acetamide; and the pharmaceutically acceptable acid addition salts thereof.
Claim 7
Dependent Claim
15 words
A compound selected from the group consisting of: trans-2-(2-methoxyphenoxy)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; and the pharmaceutically acceptable salts thereof.
Claim 8
Dependent Claim
15 words
A compound selected from the group consisting of: trans-2-(2-methoxyphenoxy)-N-methyl-N-[2-(1-pyrrolidinyl)cyclohexyl]acetamide; and the pharmaceutically acceptable salts thereof.
Claim 9
Dependent Claim
32 words
A pharmaceutical composition useful for alleviating pain in a mammal, said composition comprising an analgesically effective amount of a compound in accordance with claim 1 in combination with a pharmaceutically acceptable carrier.
Claim 10
Dependent Claim
37 words
A method of alleviating pain in a mammal in need of such treatment, said method comprising administering to said mammal an analgesically effective amount of a pharmaceutical composition in accordance with claim 5 in unit dosage form.
References Cited (Backward Citations)
US4098904A
Cited
US4359476A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-06-30 | 1989-12-30 | 1990-07-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-06-30 | 1993-12-30 | 1994-07-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-06-30 | 1997-12-30 | 1998-07-01 | $7700.00 | Window Closed / Lapsed |