Patent US4336379A successfully refreshed from Google Patents.
US4336379A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Isoxazolyl indolamines
Assignee: Sandoz Inc
•
Filing: 1981-03-18
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Granted: 1982-06-22
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Expires: 2001-03-18
Abstract
Abstract This disclosure describes compounds of the formula <IMAGE> where R1 represents hydrogen, fluoro, chloro, lower alkyl having 1 to 4 carbon atoms or lower alkoxy having 1 to 4 carbon atoms, and R2 represents hydroxy, and R3 and R4 each independently represent lower alkyl as defined above, or R3 and R4 together with N represent <IMAGE> wherein n is 1, 2 or 3, and R5 and R6 each independently represent hydrogen or lower alkyl as defined above, or a pharmaceutically acceptable acid addition salt thereof, which are useful as anti-diabetic agents, in particular as hypoglycemic agents and inhibiting or impeding post-prandial hyperglycemia.
Inventors
- 👤 Leonard J. Brand
- 👤 Jeffrey Nadelson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 09:14
CPC Classifications
C; C07; C07D; C07D413/00; C07D413/02; C07D413/04; C07D261/00; C07D261/02; C07D261/06; C07D261/08
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
97 words
A compound of the formula ##STR11## wherein R 1 represents hydrogen, fluoro, chloro, lower alkyl having 1 to 4 carbon atoms, or lower alkoxy having 1 to 4 carbon atoms, and R 2 represents hydroxy, and R 3 and R 4 each independently represent lower alkyl having 1 to 4 carbon atoms, or R 3 and R 4 together with N represent ##STR12## wherein n is 1, 2 or 3, and R 5 and R 6 each independently represent hydrogen or lower alkyl having 1 to 4 carbon atoms, or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
97 words
A compound of the formula ##STR11## wherein R 1 represents hydrogen, fluoro, chloro, lower alkyl having 1 to 4 carbon atoms, or lower alkoxy having 1 to 4 carbon atoms, and R 2 represents hydroxy, and R 3 and R 4 each independently represent lower alkyl having 1 to 4 carbon atoms, or R 3 and R 4 together with N represent ##STR12## wherein n is 1, 2 or 3, and R 5 and R 6 each independently represent hydrogen or lower alkyl having 1 to 4 carbon atoms, or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
30 words
A compound of the formula ##STR13## wherein R 1 , R 3 , R 4 & R 5 are as defined in claim 1, or a pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim
31 words
A compound of the formula ##STR14## where R 2 , R 3 , R 4 , and R 6 are as defined in claim 1, or a pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
8 words
The compound of claim 2 which is α-(dimethylaminomethyl)-2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indole-3-methanol.
Claim 6
Dependent Claim
8 words
The compound of claim 1 which is α-(dimethylaminomethyl)-2-(5-ethyl-3-methyl-4-isoxazolyl)-1H-indole-3-methanol.
Claim 7
Dependent Claim
8 words
The compound of claim 1 which is α-(dimethylaminomethyl)-2-(3-isopropyl-5-methyl-4-isoxazolyl)-1H-indole-3-methanol.
Claim 8
Dependent Claim
8 words
The compound of claim 1 which is α-(pyrrolidinomethyl)-5-fluoro-2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indole-3-methanol.
Claim 9
Dependent Claim
8 words
The compound of claim 1, which is α-(dimethylaminomethyl)-2-(3-ethyl-4-isoxazolyl)-1H-indole-3-methanol.
Claim 10
Dependent Claim
8 words
The compound of claim 1, which is α-(dimethylaminomethyl)-2-(3,5-dimethyl-4-isoxazolyl)-1H-indole-3-methanol.
Claim 11
Dependent Claim
8 words
The compound of claim 1, which is α-(dimethylaminomethyl)-2-(3,5-dimethyl-4-isoxazolyl)-1H-indole-3-methanol.
Claim 12
Dependent Claim
8 words
The compound of claim 1, which is α-(dimethylaminomethyl)-2-(5-methyl-3-propyl-4-isoxazolyl)-1H-indole-3-methanol.
Claim 13
Dependent Claim
8 words
The compound of claim 1, which is α-(dimethylaminomethyl)-2-(5-methyl-3-t-butyl-4-isoxazolyl)-1H-indole-3-methanol.
Claim 14
Dependent Claim
8 words
The compound of claim 1, which is α-(dimethylaminomethyl)-5-fluoro-2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indole-3-methanol.
Claim 15
Dependent Claim
8 words
The compound of claim 1, which is α-(diethylaminomethyl)-2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indole-3-methanol.
Claim 16
Dependent Claim
8 words
The compound of claim 1, which is α-(morpholinomethyl)-2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indole-3-methanol.
Claim 17
Dependent Claim
8 words
The compound of claim 1, which is α-(pyrrolidinomethyl)-2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indole-3-methanol.
Claim 18
Dependent Claim
8 words
The compound of claim 1, which is α-(piperidinomethyl)-2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indole-3-methanol.
Claim 19
Dependent Claim
8 words
The compound of claim 1, which is α-(dimethylaminomethyl)-5-fluoro-2-(3,5-dimethyl-4-isoxazolyl)-1H-indole-3-methanol.
Claim 20
Dependent Claim
8 words
The compound of claim 1, which is α-(dimethylaminomethyl)-5-fluoro-2-(3-methyl-5-ethyl-4-isoxazolyl)-1H-indole-3-methanol.
Claim 21
Dependent Claim
8 words
The compound of claim 1, which is α-(pyrrolidinomethyl)-5-fluoro-2-(5-ethyl-3-methyl-4-isoxazolyl)-1H-indole-3-methanol.
Claim 22
Dependent Claim
8 words
The compound of claim 1, which is α-(pyrrolidinomethyl)-5-fluoro-2-(3,5-dimethyl-4-isoxazolyl)-1H-indole-3-methanol.
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) | 1985-06-21 | 1985-12-21 | 1986-06-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-06-21 | 1989-12-21 | 1990-06-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-06-21 | 1993-12-21 | 1994-06-22 | $7700.00 | Window Closed / Lapsed |