Pyrano- and thiopyranoindole derivatives

US4118394A · kind A · utility

Assignee

• Ayerst, McKenna & Harrison, Inc. · CA

Inventors

• Christopher A. Demerson · Plainsboro, US
• Leslie G. Humber · Dollard-Des-Ormeaux, CA
• Andre A. Asselin · Mahwah, US
• Ivo L. Jirkovsky · Montréal, CA
• Thomas A. Dobson · Dollard-Des-Ormeaux, CA

Key dates

• Filing date: Aug 8, 1977
• Grant date: Oct 3, 1978
• Expiry date: Aug 8, 1997

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D495/04
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Pyranoindole and thiopyranoindole derivatives characterized by having an amino(lower)alkyl radical attached to either or both the 1 and 9 position of a pyrano[3,4-b]indole or thiopyrano[3,4-b]indone nucleus are disclosed. The amino portion of the amino(lower)alkyl radical may be further substituted with one or two lower alkyl groups or incorporated into a heterocyclic amine radical. The derivatives having the amino(lower)alkyl radical only at position 1 are further substituted at position 1 and may be optionally substituted at positions 3, 4, 5, 6, 7, 8, and 9. The derivatives having the amino(lower)alkyl radical only at position 9 possess two substituents at position 1 and may be optionally substituted at position 3, 4, 5, 6, 7, and 8. The derivatives having an amino(lower)alkyl radical at both positions 1 and 9 are further substituted at position 1 and may be optionally substituted at positions 3, 4, 5, 6, 7 and 8. The pyrano- and thiopyranoindole derivatives of this invention are useful antidepressant and antiulcer agents. Methods for the preparation and use of these derivatives are also disclosed.