US4421752A
Expired / Lapsed
US
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Isoxazolyl indolamines as hypoglycemics
Assignee: Sandoz Inc
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Filing: 1982-03-19
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Granted: 1983-12-20
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Expires: 2002-03-19
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 and R3 each independently represent lower alkyl as defined above, or R2 and R3 together with N represent <IMAGE> wherein n is 1, 2 or 3, and R4 and R5 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 08:52
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
136 words
A pharmaceutical composition useful in treating diabetes as a hypoglycemic agent comprising a compound of the formula: ##STR10## or 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, R 2 and R 3 each independently represent lower alkyl having 1 to 4 carbon atoms, or R 2 and R 3 together with N represent ##STR12## wherein n is 1, 2 or 3, and R 4 and R 5 each independently represent hydrogen or lower alkyl having 1 to 4 carbon atoms, or a pharmaceutically acceptable acid addition salt thereof in association with a pharmaceutical carrier or diluent, said compound being present in an amount sufficient to provide a daily dose of 70 to 1000 milligrams of compound.
Claim 2
Dependent Claim
136 words
A pharmaceutical composition useful in treating diabetes as a hypoglycemic agent comprising a compound of the formula: ##STR10## or 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, R 2 and R 3 each independently represent lower alkyl having 1 to 4 carbon atoms, or R 2 and R 3 together with N represent ##STR12## wherein n is 1, 2 or 3, and R 4 and R 5 each independently represent hydrogen or lower alkyl having 1 to 4 carbon atoms, or a pharmaceutically acceptable acid addition salt thereof in association with a pharmaceutical carrier or diluent, said compound being present in an amount sufficient to provide a daily dose of 70 to 1000 milligrams of compound.
Claim 3
Dependent Claim
15 words
A pharmaceutical composition according to claim 1 comprising 17.5 to 1000 milligrams per unit dosage.
Claim 4
Dependent Claim
15 words
A pharmaceutical composition according to claim 1 comprising 17.5 to 500 milligrams per unit dosage.
Claim 5
Dependent Claim
21 words
A pharmaceutical composition according to claim 1 in which the compound is 3-dimethylamino-1-[2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indol-3-yl]-1-propanol or a pharmaceutically acceptable acid addition salt thereof.
Claim 6
Dependent Claim
21 words
A pharmaceutical composition according to claim 1 in which the compound is 3-dimethylamino-1-[2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indol-3-yl]-1-propanone or a pharmaceutically acceptable acid addition salt thereof.
Claim 7
Dependent Claim
135 words
A pharmaceutical composition useful in treating diabetes by inhibiting post-prandial hyperglycemia comprising a compound of the formula ##STR13## or the formula ##STR14## wherein R 1 represents hydrogen, fluoro, chloro, lower alkyl having 1 to 4 carbon atoms, or lower alkoxy having 1 to 4 carbon atoms, R 2 and R 3 each independently represent lower alkyl having 1 to 4 carbon atoms, or R 2 and R 3 together with N represent ##STR15## wherein n is 1, 2 or 3, and R 4 and R 5 each independently represent hydrogen or lower alkyl having 1 to 4 carbon atoms, or a pharmaceutically acceptable acid addition salt thereof in association with a pharmaceutical carrier or diluent, said compound being present in an amount sufficient to provide a daily dose of 25 to 1000 milligrams of compound.
Claim 8
Dependent Claim
135 words
A pharmaceutical composition useful in treating diabetes by inhibiting post-prandial hyperglycemia comprising a compound of the formula ##STR13## or the formula ##STR14## wherein R 1 represents hydrogen, fluoro, chloro, lower alkyl having 1 to 4 carbon atoms, or lower alkoxy having 1 to 4 carbon atoms, R 2 and R 3 each independently represent lower alkyl having 1 to 4 carbon atoms, or R 2 and R 3 together with N represent ##STR15## wherein n is 1, 2 or 3, and R 4 and R 5 each independently represent hydrogen or lower alkyl having 1 to 4 carbon atoms, or a pharmaceutically acceptable acid addition salt thereof in association with a pharmaceutical carrier or diluent, said compound being present in an amount sufficient to provide a daily dose of 25 to 1000 milligrams of compound.
Claim 9
Dependent Claim
17 words
A pharmaceutical composition according to claim 6 in units dosage form for administration 3 times a day.
Claim 10
Dependent Claim
21 words
A pharmaceutical composition according to claim 6 in which the compound is 3-dimethylamino-1-[2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indol-3-yl]-1-propanol or a pharmaceutically acceptable acid addition salt thereof.
Claim 11
Dependent Claim
21 words
A pharmaceutical composition according to claim 6 in which the compound is 3-dimethylamino-1-[2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indol-3-yl]-1-propanone or a pharmaceutically acceptable acid addition salt thereof.
Claim 12
Independent Claim
118 words
A method of treating diabetes in mammals which comprises administering to a mammal in need of such treatment an anti-diabetes effective amount of a compound of the formula ##STR16## or the formula ##STR17## wherein R 1 represents hydrogen, fluoro, chloro, lower alkyl having 1 to 4 carbon atoms, or lower alkoxy having 1 to 4 carbon atoms, R 2 and R 3 each independently represent lower alkyl having 1 to 4 carbon atoms, or R 2 and R 3 together with N represent ##STR18## wherein n is 1, 2 or 3, and R 4 and R 5 each independently represent hydrogen or lower alkyl having 1 to 4 carbon atoms, or a pharmaceutically acceptable acid addition salt thereof.
Claim 13
Independent Claim
118 words
A method of treating diabetes in mammals which comprises administering to a mammal in need of such treatment an anti-diabetes effective amount of a compound of the formula ##STR16## or the formula ##STR17## wherein R 1 represents hydrogen, fluoro, chloro, lower alkyl having 1 to 4 carbon atoms, or lower alkoxy having 1 to 4 carbon atoms, R 2 and R 3 each independently represent lower alkyl having 1 to 4 carbon atoms, or R 2 and R 3 together with N represent ##STR18## wherein n is 1, 2 or 3, and R 4 and R 5 each independently represent hydrogen or lower alkyl having 1 to 4 carbon atoms, or a pharmaceutically acceptable acid addition salt thereof.
Claim 14
Dependent Claim
22 words
A method according to claim 10 in which 70 to 1000 milligrams of the compound is administered daily as a hypoglycemic agent.
Claim 15
Dependent Claim
20 words
A method according to claim 11 in which 17.5 to 1000 milligrams of the compound is administered per unit dose.
Claim 16
Dependent Claim
20 words
A method according to claim 11 in which 17.5 to 500 milligrams of the compound is administered per unit dose.
Claim 17
Dependent Claim
20 words
A method according to claim 11 in which the compound is 3-dimethylamino-1-[2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indol-3-yl]-1-propanol or a pharmaceutically acceptable acid addition salt thereof.
Claim 18
Dependent Claim
20 words
A method according to claim 11 in which the compound is 3-dimethylamino-1-[2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indol-3-yl]-1-propanone or a pharmaceutically acceptable acid addition salt thereof.
Claim 19
Dependent Claim
22 words
A method according to claim 10 in which 25 to 1000 milligrams of the compound is administered daily to inhibit post-prandial hyperglycemia.
Claim 20
Dependent Claim
20 words
A method according to claim 16 in which the compound is administered in unit dosage form three times a day.
Claim 21
Dependent Claim
20 words
A method according to claim 16 in which the compound is 3-dimethylamino-1-[2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indol-3-yl]-1-propanol or a pharmaceutically acceptable acid addition salt thereof.
Claim 22
Dependent Claim
20 words
A method according to claim 16 in which the compound is 3-dimethylamino-1-[2-(3-ethyl-5-methyl-4-isoxazolyl)-1H-indol-3-yl]-1-propanone or a pharmaceutically acceptable acid addition salt thereof.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1986-12-19 | 1987-06-20 | 1987-12-20 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1990-12-19 | 1991-06-20 | 1991-12-20 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1994-12-19 | 1995-06-20 | 1995-12-20 | $7700.00 | Window Closed / Lapsed |