2,9-Dioxa tricyclo [4,3,1,0.sup.3,7 ] decane compounds and process of making same

US4391819A · kind A · utility

Assignee

• Kali-Chemie Pharma GmbH · DE

Inventors

• Peter W. Thies · Hannover, DE
• Samuel David · Dorval, CA

Key dates

• Filing date: Jul 13, 1981
• Grant date: Jul 5, 1983
• Expiry date: Jul 13, 2001

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D311/94
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Novel and highly effective sleep inducing 3.beta.-hydroxy methyl-4.alpha.-hydroxy-8.beta.-alkoxy-2,9-dioxa tricyclo [4,3,1,0.sup.3,7 ] decane compounds of the following Formula: ##STR1## in which R.sub.1 indicates an alkoxy group and preferably a lower alkoxy group, such as the methoxy group, the ethoxy group, or the n-butoxy group, while PA1 R.sub.2 indicates the 10-methylene group or the 10.beta.-methyl group, are produced from didrovaltratum, i.e., 1-isovaleroxy-4-isovaleroxy methyl-7-acetoxy-spiro-oxirano-1,9-dihydrocyclopenta(c)pyrane or from extracts of plants of the genus Valerianaceae which contain about 70% of didrovaltratum. The novel compounds have a surprisingly low toxicity.