# US 4,397,850 A · Isoxazolyl indolamines

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- Number: US 4,397,850 A
- Document ID: US4397850A
- Status: Granted
- Kind: A
- Application number: 06/309,255
- Filed: 1981-10-07
- Granted: 1983-08-09
- Earliest claimed: 1981-10-07
- Assignees: Sandoz Ltd.
- Inventors: Jeffrey Nadelson; Leonard J. Brand
- Web page: https://patentgrep.com/patent/US4397850A

## CPC

- C07D 413/04: directly linked by a ring-member-to-ring-member bond
- C07D 261/08: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

This disclosure describes compounds of the formula ##STR1## where R.sub.1 represents hydrogen, fluoro, chloro, lower alkyl having 1 to 4 carbon atoms or lower alkoxy having 1 to 4 carbon atoms, and R.sub.2 represents hydroxy, and R.sub.3 and R.sub.4 each independently represent lower alkyl as defined above, or R.sub.3 and R.sub.4 together with N represent ##STR2## wherein n is 1, 2, or 3, and R.sub.5 and R.sub.6 each independently represent hydrogen or lower alkyl as defined above, and R.sub.7 represents 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 postprandial hyperglycemia.

## Claims

### Claim 1

A compound of the formula ##STR12## wherein R.sub.1 represents hydrogen, fluoro, chloro, lower alkyl having 1 to 4 carbon atoms, or lower alkoxy having 1 to 4 carbon atoms, and
R.sub.2 represents hydroxy, and
R.sub.3 and R.sub.4 each independently represent lower alkyl having 1 to 4 carbon atoms, or
R.sub.3 and R.sub.4 together with N represent ##STR13## wherein n is 1, 2 or 3, and
R.sub.5 and R.sub.6 each independently represent hydrogen or lower alkyl having 1 to 4 carbon atoms, and
R.sub.7 represents lower alkyl having 1 to 4 carbon atoms
or a pharmaceutically acceptable acid addition salt thereof.

### Claim 2 (depends on 1)

A compound of the formula ##STR14## wherein R.sub.1, R.sub.3, R.sub.4, R.sub.5 and R.sub.7 are as defined in claim 1, or a pharmaceutically acceptable salt thereof.

### Claim 3 (depends on 1)

A compound of the formula ##STR15## where R.sub.2, R.sub.3, R.sub.4, R.sub.6 and R.sub.7 are as defined in claim 1, or a pharmaceutically acceptable salt thereof.

### Claim 4 (depends on 2)

The compound of claim 2 which is .alpha.-(dimethylaminomethyl)-2-(3-ethyl-5-methyl-4-isoxazolyl)-1-methyl-i ndole-3-methanol.

### Claim 5 (depends on 1)

A method for treating diabetes which comprises administering to an animal in need of said treatment a hypoglycemic effective amount of a compound of claim 1.

### Claim 6 (depends on 1)

A method of treating diabetes by inhibiting post-prandial hyperglycemia which comprises administering to an animal in need of said treatment an effective amount of a compound of claim 1.

### Claim 7 (depends on 1)

A pharmaceutical composition useful in treating diabetes comprising a hypoglycemic effective or post-prandial hyperglycemic inhibiting effective amount of a compound of claim 1 and a pharmaceutically acceptable diluent or carrier therefor.