Dopaminergic stimulating and antianoxic 4-substituted 2H-indole-2-ones

• US 4,435,408 A
• Filed: 07/15/1982
• Issued: 03/06/1984
• Est. Priority Date: 07/24/1981
• Status: Expired due to Fees

• Current Assignee: Roussel Uclaf
• Original Assignee: Roussel Uclaf
• Inventors: Nedelec, Lucien, Guillaume, Jacques, Dumont, Claude
• Primary Examiner(s): Schwartz, Richard A.
• Application Number:
  US06/398,576
• Time in Patent Office: 600 Days
• Field of Search: 546/201, 546/273, 424/263, 424/267
• US Class Current: 514/323
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond

Abstract

Novel 2H-indole-2-ones of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms and aralkyl of 7 to 12 carbon atoms, a and b are both hydrogen or together form a carbon-carbon bond, Z is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, hydroxyalkyl of 2 to 8 carbon atoms, aryloxyalkyl of 7 to 12 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms, alkenyl and alkynyl of 3 to 8 carbon atoms and aralkyl of 7 to 12 carbon atoms optionally substituted with at least one member of the group consisting of halogen, alkoxy of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms, --OH, --CF₃, --OCF₃, --NO₂ and --NH₂ and their nontoxic, pharmaceutically acceptable acid addition salts having remarkable dopaminergic stimulating and antianoxic properties and their preparation.

Claims

1. A compound selected from the group consisting of 2H-indole-2-ones of the formula ##STR8## wherein R is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms and aralkyl of 7 to 12 carbon atoms, a and b are both hydrogen or together form a carbon-carbon bond, Z is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, hydroxyalkyl of 2 to 8 carbon atoms, aryloxyalkyl of 7 to 12 carbon atoms, cycloalkylalkyl of 4 to 12 carbon atoms, alkenyl and alkynyl of 3 to 8 carbon atoms and aralkyl of 7 to 12 carbon atoms optionally substituted with at least one member of the group consisting of halogen, alkoxy of 1 to 4 carbon atoms, alkyl of 1 to 4 carbon atoms, --OH, --CF₃, --OCF₃, --NO₂ and --NH₂ and their non-toxic, pharmaceutically acceptable acid addition salts.

2. A compound of claim 1 wherein R is selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms.

3. A compound of claim 1 or 2 wherein Z is selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms.

4. A compound of claim 1 selected from the group consisting of 1,3-dihydro-4-(1-propyl-1,2,5,6-tetrahydropyridin-3-yl)-2H-indole-2-one and its non-toxic, pharmaceutically acceptable acid addition salts.

5. A compound of claim 1 selected from the group consisting of 1,3-dihydro-4-(piperidin-3-yl)-2H-indole-2-one and its non-toxic, pharmaceutically acceptable acid addition salts.

6. A dopaminergic stimulating and antianoxic composition comprising a dopaminergic stimulating and antianoxically effective amount of at least one compound of claim 1 and a pharmaceutical carrier.

7. A composition of claim 6 wherein in the compound R is selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms.

8. A composition of claim 6 or 7 wherein in the compound Z is selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms.

9. A composition of claim 6 wherein the active compound is selected from the group consisting of 1,3-dihydro-4-(1-propyl-1,2,5,6-tetrahydropyridin-3-yl)-2H-indole-2-one and its non-toxic, pharmaceutically acceptable acid addition salts.

10. A composition of claim 6 wherein the active compound is selected from the group consisting of 1,3-dihydro-4-(piperidin-3-yl)-2H-indole-2-one and its non-toxic, pharmaceutically acceptable acid addition salts.

11. A method of inducing dopaminergic stimulating and antianoxic activity in warm-blooded animals comprising administering to warm-blooded animals a dopaminergic stimulating and antianoxically effective amount of at least one compound of claim 1.

12. A method of claim 11 wherein in the compound R is selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms.

13. A method of claim 11 wherein in the compound Z is selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms.

14. A method of claim 11 wherein the active compound is selected from the group consisting of 1,3-dihydro-4-(1-propyl-1,2,5,6-tetrahydropyridin-3-yl)-2H-indole-2-one and its non-toxic, pharmaceutically acceptable acid addition salts.

15. A method of claim 11 wherein the active compound is selected from the group consisting of 1,3-dihydro-4-(piperidin-3-yl)-2H-indole-2-one and its non-toxic, pharmaceutically acceptable acid addition salts.