# US 4,395,414 A · Substituted quinolinone-alkanecarboxylic acids and medicaments containing them, having a hyperglycaemic action

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- Number: US 4,395,414 A
- Document ID: US4395414A
- Status: Granted
- Kind: A
- Application number: 06/256,247
- Filed: 1981-04-21
- Granted: 1983-07-26
- Earliest claimed: 1980-08-14
- Assignees: Byk Gulden Lomberg Chemische Fabrik GmbH
- Inventors: Klaus Eistetter; Erich Rapp; Horst Wolf
- Web page: https://patentgrep.com/patent/US4395414A

## CPC

- C07D 215/227: only one oxygen atom which is attached in position 2
- C07D 215/38: Nitrogen atoms (nitro radicals C07D215/18)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Quinolinone-alkanecarboxylic acids of the formula I ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 are identical or different and denote hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group with 1 to 4 carbon atoms, an amino group, a dialkylamino group, the alkyl radicals having 1 to 4 carbon atoms, or a nitro group, R.sup.4 and R.sup.5 are identical or different and denote a hydrogen atom, a halogen atom, an alkoxy group with 1 to 4 carbon atoms, a hydroxyl group, an amino group or a dialkylamino group, the alkyl radicals having 1 to 4 carbon atoms, or R.sup.4 and R.sup.5 together denote a methylenedioxy group bonded to two adjacent ring carbon atoms, and A denotes an alkylene group with 1 to 5 carbon atoms, and esters thereof with alkanols with 1 to 5 carbon atoms, and salts thereof with inorganic and organic bases are new compounds. They display a hyperglycaemic action in warm-blooded animals. Processes for the preparation of the new compounds are given.

## Claims

### Claim 1

A substituted quinolinone of the general formula I ##STR13## wherein R.sup.1, R.sup.2 and R.sup.3 are identical or different and each denotes a hydrogen atom, a halogen atom, a hydroxyl group, an alkoxy group with 1 to 4 carbon atoms, an amino group, a dialkylamino group, each alkyl radical having 1 to 4 carbon atoms, or a nitro group,
R.sup.4 and R.sup.5 are identical or different and each denotes a hydrogen atom, a halogen atom, an alkoxy group with 1 to 4 carbon atoms, a hydroxyl group, an amino group or a dialkylamino group, each alkyl radical having 1 to 4 carbon atoms, or
R.sup.4 and R.sup.5 together denote a methylenedioxy group bonded to two adjacent ring carbon atoms, and A denotes an alkylene group with 1 to 5 carbon atoms,
an ester thereof with an alkanol with 1 to 5 carbon atoms, or a salt thereof with an inorganic and organic base.

### Claim 2

A substituted quinolinone of the general formula I* ##STR14## wherein R.sup.1*, R.sup.2* and R.sup.3* are identical or different and each denotes a hydrogen atom, a halogen atom, an alkoxy group with 1 to 4 carbon atoms or a hydroxyl group,
R.sup.4* and R.sup.5* are identical or different and each denotes a hydrogen atom, a halogen atom, an alkoxy group with 1 to 4 carbon atoms or a hydroxyl group, or
R.sup.4* and R.sup.5* together denote a methylenedioxy group, and
A* denotes an alkylene group with 1 to 5 carbon atoms,
an ester thereof with an alkanol with 1 to 5 carbon atoms, or a salt thereof with an organic or organic base.

### Claim 3

A substituted quinolinone of the general formula I** ##STR15## wherein R.sup.1*** and R.sup.2** denote a hydrogen atom,
R.sup.3** denotes a hydrogen atom or a chlorine atom,
R.sup.4** and R.sup.5** are identical or different and each denotes a hydrogen atom, a chlorine atom or a methoxy group and
A** denotes a methylene, ethylene, n-propylene or n-butylene group,
a methyl or ethyl ester thereof and or a salt thereof with an inorganic or organic base.

### Claim 4

7-Chloro-1,2-dihydro-2-oxo-3-phenyl-quinol-1-yl-acetic acid or a salt thereof with inorganic and organic base.

### Claim 5 (depends on 1, 2, 3, 4)

A pharmaceutical composition containing from 1% to 95% by weight of the total mixture of at least one compound according to claim 1, 2, 3 or 4 in admixture with one or more solid or liquid pharmaceutically acceptable inert carriers.

### Claim 6 (depends on 1, 2, 3, 4)

A feed additive containing from 0.1% to 50% by weight of the total mixture of at least one compound according to claim 1, 2, 3 or 4 in admixture with one or more solid or liquid nutritionally acceptable inert carriers.

### Claim 7 (depends on 1, 2, 3, 4)

A hyperglycaemic pharmaceutical composition having pharmaceutically-acceptable inert carrier in admixture with an effective amount of a pharmaceutically-acceptable compound according to claim 1, 2, 3 or 4.

### Claim 8 (depends on 1, 2, 3, 4)

A compound according to claim 1, 2, 3 or 4 which is an acid, an ester or a pharmacologically-acceptable salt.