Pyrano- and thiopyranoindole derivatives, compositions and methods of use

US4003913A · kind A · utility

Assignee

• Ayerst, McKenna & Harrison, Inc. · CA

Inventors

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

Key dates

• Filing date: Mar 5, 1975
• Grant date: Jan 18, 1977
• Expiry date: Mar 5, 1995

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D209/08
• 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]indole nucleus or having said radical attached to the 1 position of a pyrano[4,3-b]indole or thiopyrano[4,3-b]indole 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 pyrano[3,4-b]indole or thiopyrano[3,4-b]indole 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…