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US4076831A
Expired / Lapsed
US
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Pyrano[3,4-b]-indole derivatives, pharmaceutical compositions and methods of use
Assignee: Wyeth LLC
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Filing: 1976-12-13
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Granted: 1978-02-28
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Expires: 1996-12-13
Abstract
Abstract Indole derivatives characterized by having a 1,3,4,9-tetrahydropyrano[3,4-b]indole or 1,3,4,9-tetrahydrothiopyrano[3,4-b]indole nucleus bearing a substituent in position 1, said substituent incorporating an acid, ester or amide function therein, are disclosed. The nucleus is further substituted at position 1 and may be optionally substituted at positions 3, 4, 5, 6, 7, 8, and 9. The derivatives are useful antiinflammatory, analgesic, antibacterial and antifungal agents and methods for their preparation and use are also disclosed.
Inventors
- 👤 Christopher A. Demerson
- 👤 Leslie G. Humber
- 👤 Thomas A. Dobson
- 👤 Ivo L. Jirkovsky
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 16:57
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/04; C07D311/00; C07D311/02; C07D311/76; C07D409/00; C07D409/02; C07D409/04; C07D491/00; C07D491/02; C07D491/04; C07D491/044; C07D491/052; C07D495/00; C07D495/02; C07D495/04; H; H10; H10D; H10D10/00
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
161 words
A compound of the formula Ia ##STR129## in which R 1 is selected from the group consisting of lower alkyl, lower alkenyl, lower alkynyl, lower cycloalkyl, phenyl, benzyl and 2-thienyl, R 2 , R 3 , R 4 and R 5 are the same or different and are each selected from the group consisting of hydrogen and lower alkyl, R 6a , R 6b , R 6c , and R 6d are the same or different and selected from the group consisting of lower cycloalkyl and phenyl R 7 is selected from the group consisting of hydrogen, lower alkyl and lower alkenyl, X is selected from the group consisting of oxy and thio, Y is selected from the group consisting of carbonyl, ##STR130## which each of R 8 , R 9 , R 10 , R 11 , R 12 and R 13 is hydrogen or lower alkyl, and Z is selected from the group consisting of hydroxy and lower alkoxy.
Claim 2
Dependent Claim
161 words
A compound of the formula Ia ##STR129## in which R 1 is selected from the group consisting of lower alkyl, lower alkenyl, lower alkynyl, lower cycloalkyl, phenyl, benzyl and 2-thienyl, R 2 , R 3 , R 4 and R 5 are the same or different and are each selected from the group consisting of hydrogen and lower alkyl, R 6a , R 6b , R 6c , and R 6d are the same or different and selected from the group consisting of lower cycloalkyl and phenyl R 7 is selected from the group consisting of hydrogen, lower alkyl and lower alkenyl, X is selected from the group consisting of oxy and thio, Y is selected from the group consisting of carbonyl, ##STR130## which each of R 8 , R 9 , R 10 , R 11 , R 12 and R 13 is hydrogen or lower alkyl, and Z is selected from the group consisting of hydroxy and lower alkoxy.
Claim 3
Dependent Claim
7 words
8-Cyclopropyl-1-ethyl-1,3,4,9-tetrahydropyrano[3,4-b]-indole-1-acetic acid, as claimed in claim 1.
Claim 4
Dependent Claim
7 words
8-Cyclopentyl-1-ethyl-1,3,4,9-tetrahydropyrano[3,4-b]-indole-1-acetic acid, as claimed in claim 1.
Claim 5
Dependent Claim
7 words
8-Cyclohexyl-1-ethyl-1,3,4,9-tetrahydropyrano[3,4-b]-indole-1-acetic acid, as claimed in claim 1.
Claim 6
Dependent Claim
7 words
1-Ethyl-8-phenyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 7
Independent Claim
199 words
A method of treating inflammation in a warm-blooded animal, comprising: administering perorally to said animal an antiinflammatorily effective amount of the compound of the following formula Ib ##STR131## in which R 1 is selected from the group consisting of lower alkyl, lower alkenyl, lower alkynyl, lower cycloalkyl, phenyl, benzyl and 2-thienyl, R 2 , R 3 , R 4 and R 5 are the same or different and are each selected from the group consisting of hydrogen and lower alkyl, R 6a , R 6b , R 6c , and R 6d are the same or different and selected from the group consisting of hydrogen, lower alkyl, lower cycloalkyl, hydroxy, lower alkoxy, benzyloxy, lower alkanoyloxy, phenyl, nitro, halo, mercapto, lower alkylthio, trifluoromethyl, amino and sulfamoyl, R 7 is selected from the group consisting of hydrogen, lower alkyl and lower alkenyl, X is selected from the group consisting of oxy and thio, Y is selected from the group consisting of carbonyl, ##STR132## which each of R 8 , R 9 , R 10 , R 11 , R 12 and R 13 is hydrogen or lower alkyl, and Z is selected from the group consisting of hydroxy and lower alkoxy.
Claim 8
Independent Claim
199 words
A method of treating inflammation in a warm-blooded animal, comprising: administering perorally to said animal an antiinflammatorily effective amount of the compound of the following formula Ib ##STR131## in which R 1 is selected from the group consisting of lower alkyl, lower alkenyl, lower alkynyl, lower cycloalkyl, phenyl, benzyl and 2-thienyl, R 2 , R 3 , R 4 and R 5 are the same or different and are each selected from the group consisting of hydrogen and lower alkyl, R 6a , R 6b , R 6c , and R 6d are the same or different and selected from the group consisting of hydrogen, lower alkyl, lower cycloalkyl, hydroxy, lower alkoxy, benzyloxy, lower alkanoyloxy, phenyl, nitro, halo, mercapto, lower alkylthio, trifluoromethyl, amino and sulfamoyl, R 7 is selected from the group consisting of hydrogen, lower alkyl and lower alkenyl, X is selected from the group consisting of oxy and thio, Y is selected from the group consisting of carbonyl, ##STR132## which each of R 8 , R 9 , R 10 , R 11 , R 12 and R 13 is hydrogen or lower alkyl, and Z is selected from the group consisting of hydroxy and lower alkoxy.
Claim 9
Dependent Claim
28 words
A method of producing analgesia in a warm-blooded animal, comprising: administering perorally to said animal an analgesically effective amount of the compound of formula 1b of claim 6.
Claim 10
Dependent Claim
22 words
A pharmaceutical composition comprising: an anti-inflammatory effective amount of the compound of formula 1b of claim 6 and a pharmaceutically acceptable carrier.
Claim 11
Dependent Claim
22 words
A pharmaceutical composition, comprising: an analgesically effective amount of the compound of Formula 1b of claim 6 and a pharmaceutically acceptable carrier.
Claim 12
Dependent Claim
13 words
A method according to claim 6 wherein 1-propyl-1,3,4,9,tetrahydropyrano[3,4-b]indole-1-acetic acid is the compound administered.
Claim 13
Dependent Claim
13 words
A method according to claim 6 wherein 1,8-diethyl-1,3,4,9-tetrahydropyrano-[3,4-b]indole-1-acetic acid is the compound administered.
Claim 14
Dependent Claim
13 words
A method according to claim 7 wherein 1-propyl-1,3,4,9,tetrahydropyrano[3,4-b]indole-1-acetic acid is the compound administered.
Claim 15
Dependent Claim
13 words
A method according to claim 7 wherein 1,8-diethyl-1,3,4,9-tetrahydropyrano-[3,4-b]indole-1-acetic acid is the compound administered.
Claim 16
Dependent Claim
16 words
A pharmaceutical composition according to claim 8 wherein the compound of Formula 1b is 1-propyl-1,3,4,9,-tetrahydropyrano[3,4-b]indole-1-acetic acid.
Claim 17
Dependent Claim
16 words
A pharmaceutical composition according to claim 8 wherein the compound of Formula 1b is 1,8-diethyl-1,3,4,9-tetrahydropyrano-[3,4-b]indole-1-acetic acid.
Claim 18
Dependent Claim
16 words
A pharmaceutical composition according to claim 9 wherein the compound of Formula 1b is 1-propyl-1,3,4,9,tetrahydropyrano[3,4-b]indole-1-acetic acid.
Claim 19
Dependent Claim
16 words
A pharmaceutical composition according to claim 9 wherein the compound of Formula 1b is 1,8-diethyl-1,3,4,9-tetrahydropyrano-[3,4-b]indole-1-acetic acid.
References Cited (Backward Citations)
US3939178A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-02-27 | 1981-08-29 | 1982-02-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-02-27 | 1985-08-29 | 1986-02-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-02-27 | 1989-08-29 | 1990-02-28 | $7700.00 | Window Closed / Lapsed |