US4670462A
Expired / Lapsed
US
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Substituted 1,3,4,9-tetrahydropyrano(3,4-B)indole-1-acetic acids
Assignee: Wyeth LLC
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Filing: 1986-03-11
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Granted: 1987-06-02
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Expires: 2006-03-11
Abstract
Abstract Indole derivatives characterized by having a 1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid nucleus bearing a substituent in position 1 and 4. The nucleus may be optionally substituted at positions 5, 6, 7 and 8. The derivatives are useful anti-inflammatory and analgesic agents and methods for their preparation and use are also disclosed.
Inventors
- 👤 Alan H. Katz
- 👤 Christopher A. Demerson
- 👤 Leslie G. Humber
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 14:16
CPC Classifications
C; C07; C07D; C07D491/00; C07D491/02; C07D491/04; C07D491/044; C07D491/052; A; A61; A61P; A61P25/00; A61P25/04; A61P29/00
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
64 words
The compounds having the structure ##STR8## wherein R 1 is lower alkyl containing 1 to 4 carbon atoms, R 2 and R 3 are hydrogen or R 2 and R 3 are joined together to give --CH═CH--CH═CH-- and form a benzene ring, R 4 and R 5 are hydrogen, alkyl containing 1 to 6 carbon atoms or halogen, and the pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
64 words
The compounds having the structure ##STR8## wherein R 1 is lower alkyl containing 1 to 4 carbon atoms, R 2 and R 3 are hydrogen or R 2 and R 3 are joined together to give --CH═CH--CH═CH-- and form a benzene ring, R 4 and R 5 are hydrogen, alkyl containing 1 to 6 carbon atoms or halogen, and the pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
58 words
The compounds according to claim 1 having the structure ##STR9## wherein R 2 and R 3 are hydrogen or R 2 and R 3 are joined together to give --CH═CH--CH═CH-- and form a benzene ring, R 4 and R 5 are hydrogen, lower alkyl containing 1 to 4 carbon atoms or halogen and the pharmaceutically acceptable salts thereof.
Claim 4
Dependent Claim
58 words
The compounds according to claim 2 having the structure ##STR10## wherein R 2 and R 3 are hydrogen or R 2 and R 3 are joined together to give --CH═CH--CH═CH-- and form a benzene ring, R 4 is hydrogen, or 5-, 6-, or 7-halogen, R 5 is hydrogen, methyl, ethyl or propyl and the pharmaceutically acceptable salts thereof.
Claim 5
Dependent Claim
15 words
A compound according to claim 3 designated 1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)-pyrano[3,4-b]indole-1-acetic acid and the pharmaceutically acceptable salts thereof.
Claim 6
Dependent Claim
17 words
The compound according to claim 4 designated 1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)-pyrano[3,4-b]indole-1-acetic acid (Isomer A) and the pharmaceutically acceptable salts thereof.
Claim 7
Dependent Claim
11 words
A compound according to claim 4 designated 1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)-pyrano[3,4-b]indole-1-acetic acid sodium salt.
Claim 8
Dependent Claim
13 words
The compound according to claim 5 designated 1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)-pyrano[3,4-b]indole-1-acetic acid sodium salt (Isomer A).
Claim 9
Dependent Claim
15 words
A compound according to claim 4 designated (+)-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)-pyrano[3,4-b]indole-1-acetic acid and the pharmaceutically acceptable salts thereof.
Claim 10
Dependent Claim
15 words
A compound according to claim 4 designated (-)-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)-pyrano[3,4-b]indole-1-acetic acid and the pharmaceutically acceptable salts thereof.
Claim 11
Dependent Claim
17 words
The compound according to claim 5 designated (+)-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)-pyrano[3,4-b]indole-1-acetic acid (Isomer A) and the pharmaceutically acceptable salts thereof.
Claim 12
Dependent Claim
17 words
The compound according to claim 5 designated (-)-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)-pyrano[3,4-b]indole-1-acetic acid (Isomer A) and the pharmaceutically acceptable salts thereof.
Claim 13
Dependent Claim
15 words
A compound according to claim 3 designated 7-chloro-1-ethyl-1,3,4,9-tetrahydro-8-methyl-4-(2-propenyl)-pyrano[3,4-b]indole-1-acetic acid and the pharmaceutically acceptable salts thereof.
Claim 14
Dependent Claim
15 words
A compound according to claim 3 designated 1-ethyl-7-fluoro-1,3,4,9-tetrahydro-8-methyl-4-(2-propenyl)-pyrano[3,4-b]indole-1-acetic acid and the pharmaceutically acceptable salts thereof.
Claim 15
Dependent Claim
15 words
A compound according to claim 3 designated 8-chloro-1-ethyl-1,3,4,9-tetrahydro-5-methyl-4-(phenylmethyl)-pyrano[3,4-b]indole-1-acetic acid and the pharmaceutically acceptable salts thereof.
Claim 16
Dependent Claim
15 words
A compound according to claim 3 designated 1,8-diethyl-1,3,4,9-tetrahydro-4-(2-propenyl)-pyrano[3,4-b]indole-1-acetic acid and the pharmaceutically acceptable salts thereof.
Claim 17
Dependent Claim
15 words
A compound according to claim 3 designated 1-ethyl-1,3,4,9-tetrahydro-8-methyl-4-(2-propenyl)-pyrano[3,4-b]indole-1-acetic acid and the pharmaceutically acceptable salts thereof.
Claim 18
Dependent Claim
15 words
A compound according to claim 3 designated 7-chloro-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)-pyrano[3,4,-b]indole-1-acetic acid and the pharmaceutically acceptable salts thereof.
Claim 19
Dependent Claim
15 words
A compound according to claim 3 designated 6-bromo-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)-pyrano[3,4,-b]indole-1-acetic acid and the pharmaceutically acceptable salts thereof.
Claim 20
Dependent Claim
15 words
A compound according to claim 3 designated 5-chloro-1-ethyl-1,3,4,9-tetrahydro-8-methyl-4-(phenylmethyl)-pyrano[3,4-b]indole-1-acetic acid and the pharmaceutically acceptable salts thereof.
Claim 21
Dependent Claim
15 words
A compound according to claim 3 designated 7,8-dichloro-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)-pyrano[3,4-b]indole-1-acetic acid and the pharmaceutically acceptable salts thereof.
Claim 22
Dependent Claim
15 words
A compound according to claim 3 designated 7-chloro-1-ethyl-1,3,4,9-tetrahydro-8-methyl-4-(phenylmethyl)-pyrano[3,4-b]indole-1-acetic acid and the pharmaceutically acceptable salts thereof.
Claim 23
Dependent Claim
15 words
A compound according to claim 3 designated 1-ethyl-1,3,4,9-tetrahydro-8-methyl-4-(phenylmethyl)-pyrano[3,4-b]indole-1-acetic acid and the pharmaceutically acceptable salts thereof.
Claim 24
Dependent Claim
15 words
A compound according to claim 3 designated 1-ethyl-1,3,4,9-tetrahydro-4-(2-propenyl)-8-propyl-pyrano[3,4-b]indole-1-acetic acid and the pharmaceutically acceptable salts thereof.
Claim 25
Dependent Claim
15 words
A compound according to claim 3 designated 1,8-diethyl-1,3,4,9-tetrahydro-4-(2-propenyl)-pyrano[3,4-b]indole-1-acetic acid and the pharmaceutically acceptable salts thereof.
Claim 26
Dependent Claim
40 words
A pharmaceutical composition for treating inflammatory conditions and for producing analgesia in a mammal comprising an effective amount of a compound of structure (I), or a pharmaceutically acceptable salt thereof, as defined in claim 1 and a pharmaceutically acceptable carrier.
Claim 27
Dependent Claim
44 words
A method for treating inflammatory conditions and for producing analgesia in a mammal which comprises the administration to said mammal of an effective amount of a compound selected from those of formula (I), or a pharmaceutically acceptable salt thereof, as claimed in claim 1.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-06-01 | 1990-12-01 | 1991-06-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-06-01 | 1994-12-01 | 1995-06-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-06-01 | 1998-12-01 | 1999-06-02 | $7700.00 | Window Closed / Lapsed |