US3939178A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Certain pyrano [3,4-b]indoles and thiopyrano[3,4-b]indoles
Assignee: Wyeth LLC
•
Filing: 1972-09-15
•
Granted: 1976-02-17
•
Expires: 1992-09-15
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
2026-10-27 06:16
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: 58
Claim 1
Independent Claim
181 words
A compound of the formula Ia ##SPC7## 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, hydroxy, lower alkoxy, benzyloxy, lower alkanoyloxy, 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, ##EQU8## 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, or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
181 words
A compound of the formula Ia ##SPC7## 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, hydroxy, lower alkoxy, benzyloxy, lower alkanoyloxy, 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, ##EQU8## 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, or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
7 words
1-Ethyl-5,8-dimethoxy-1,3,4,9-tetrahydropyrano[3,4-b]indole1-acetic acid, as claimed in claim 1.
Claim 4
Dependent Claim
9 words
1-Methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid ethyl ester, as claimed in claim 1.
Claim 5
Dependent Claim
7 words
1,9-Dimethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 6
Dependent Claim
7 words
1-Methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 7
Dependent Claim
9 words
1-Methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid methyl ester, as claimed in claim 1.
Claim 8
Dependent Claim
7 words
1-Methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-propionic acid, as claimed in claim 1.
Claim 9
Dependent Claim
9 words
1-Methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-propionic acid ethyl ester, as claimed in claim 1.
Claim 10
Dependent Claim
9 words
1-Methyl-1,3,4,9-tetrahydrothiopyrano[3,4-b]indole-1-acetic acid methyl ester, as claimed in claim 1.
Claim 11
Dependent Claim
7 words
1-Methyl-1,3,4,9-tetrahydrothiopyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 12
Dependent Claim
7 words
1-Ethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 13
Dependent Claim
7 words
1-Propyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 14
Dependent Claim
7 words
1-Isopropyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 15
Dependent Claim
7 words
3-Methyl-1-propyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 16
Dependent Claim
7 words
4-Ethyl-1-ethynyl-3-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 17
Dependent Claim
8 words
α, 1-Dimethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 18
Dependent Claim
7 words
1-Phenyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 19
Dependent Claim
7 words
1-t-Butyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 20
Dependent Claim
7 words
1-Butyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 21
Dependent Claim
7 words
8-Methyl-1-propyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 22
Dependent Claim
7 words
1-(2-Thienyl)-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 23
Dependent Claim
7 words
6-Bromo-1-ethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 24
Dependent Claim
7 words
6-Methoxy-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 25
Dependent Claim
7 words
6-Acetoxy-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 26
Dependent Claim
7 words
6-Benzyloxy-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 27
Dependent Claim
7 words
5-Methyl-1-propyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 28
Dependent Claim
7 words
7-Methyl-1-propyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 29
Dependent Claim
7 words
6-Nitro-1-propyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 30
Dependent Claim
7 words
4,4-Dimethyl-1-propyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 31
Dependent Claim
7 words
1-Methyl-1,3,4,9-tetrahydropyrano[3,4-b]-indole-1-acetic acid, as claimed in claim 1.
Claim 32
Dependent Claim
7 words
1-Ethyl-1,3,4,9-tetrahydrothiopyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 33
Dependent Claim
7 words
1-Propyl-1,3,4,9-tetrahydrothiopyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 34
Dependent Claim
7 words
1-Methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-carboxylic acid, as claimed in claim 1.
Claim 35
Dependent Claim
7 words
1,9-Dimethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 36
Dependent Claim
7 words
9-Allyl-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 37
Dependent Claim
7 words
6-Hydroxy-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 38
Dependent Claim
9 words
6-Hydroxy-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid benzylamine salt, as claimed in claim 1.
Claim 39
Dependent Claim
7 words
1,9-Dimethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-propionic acid, as claimed in claim 1.
Claim 40
Dependent Claim
7 words
1,4,-Dimethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 41
Dependent Claim
7 words
9-Ethyl-1-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1acetic acid, as claimed in claim 1.
Claim 42
Dependent Claim
7 words
1-Methyl-9-propyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 43
Dependent Claim
7 words
1-Methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-butyric acid, as claimed in claim 1.
Claim 44
Dependent Claim
7 words
5-Chloro-1-ethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 45
Dependent Claim
7 words
1-t-Butyl-4-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 46
Dependent Claim
7 words
5-Methoxy-1-propyl-1,3,4,9-tetrahydropyrano[3,4b]indole-1-acetic acid, as claimed in claim 1.
Claim 47
Dependent Claim
7 words
1-Ethyl-8-methyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 48
Dependent Claim
7 words
4,8-Dimethyl-1-ethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 49
Dependent Claim
7 words
1,4,8-Trimethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 50
Dependent Claim
7 words
8-Chloro-1-ethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 51
Dependent Claim
7 words
7-Chloro-1-ethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 52
Dependent Claim
7 words
7-Chloro-1-propyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 53
Dependent Claim
7 words
1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 54
Dependent Claim
7 words
1-Ethyl-8-methoxy-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 55
Dependent Claim
7 words
5,8-Dimethyl-1-ethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 56
Dependent Claim
7 words
5,8-Dichloro-1-ethyl-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 57
Dependent Claim
7 words
1-Ethyl-5,8-dimethoxy-1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acid, as claimed in claim 1.
Claim 58
Dependent Claim
7 words
1-Ethyl-7-trifluoromethyl-1,3,4,9-tetrahydropyrano[3,4-b]-indole-1-acetic acid, as claimed in claim 1.
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) | 1979-02-16 | 1979-08-18 | 1980-02-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-02-16 | 1983-08-18 | 1984-02-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-02-16 | 1987-08-18 | 1988-02-17 | $7700.00 | Window Closed / Lapsed |