Vitamin D analogues having a halogen-or azido- substituted side chain

US5612325A · kind A · utility

Assignee

• Leo Pharmaceutical Products Ltd.A/S/ (L.o slashed.vens kemiske Fabrik Produktionsaktieselskab) · DK

Inventors

• Kai Hansen · Avenue Madeleine, DK
• Henrik Pedersen · Hjørring, DK

Key dates

• Filing date: Jan 3, 1995
• Grant date: Mar 18, 1997
• Expiry date: Jan 3, 2015

Classification

• Technology area (CPC A): Human Necessities
• CPC primary: A61P43/00
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

A compound of formula I ##STR1## wherein R stands for a straight or branched, saturated or unsaturated alkyl group containing from 4 to 12 carbon atoms optionally substituted with a hydroxy group, and possibly containing a ring structure, and in which at least one of the carbon atoms not bearing hydroxyl group is substituted with one or more halogen atoms or an azido group; and prodrugs of I in which one or more of the hydroxy groups are masked as groups which can be reconverted to hydroxy groups in vivo, in pure form or in mixtures. The compounds show antiinflammatory and immunomodulating effects as well as strong activity in inducing differentiation and inhibiting undesirable proliferation of certain cells. The compounds are prepared by oxidizing 1(S),3(R)-bis-(tert-butyldimethylsilyloxy)-20(S)formyl-9,10-seco-pregna-5( E),7(E),10(19)-triene, reducing the resulting product; alkylating the reduction product and then subjecting the alkylated product to triplet-sensitized photoisomerization.