Title:
【発明の名称】カルシトリオールならびにその誘導体を製造するための原料化合物、これらの原料化合物の製造方法ならびにこの方法のための中間体
Document Type and Number:
Japanese Patent JP3037427
Kind Code:
B2
Abstract:
Starting compounds for preparing calcitriol (1$g(a), 25-dihydroxycholecalciferol) and its derivatives showing, as compared with calcitriol, some modifications, particularly in the C-17 lateral chain, a method for preparing these starting compounds and intermediate products for this method are described. The new compounds have the general formula (I), wherein R?1 stands for a hydrogen atom, an alkyl, silyl, acyl, aryl, alkoxycarbonyl or alkoxyalkyl group whose meaning is more closely defined in the description and either a) A stands for a methylene group and R the residue -(CH2?)n?-CH2?-CR?2R?3OH (n = 1, 2, 3, 4, 5, 6, 7), wherein R?2 and R?3 stand independently for a hydrogen atom, a C1-4? alkyl group or R?2 and R?3 stand for a cyclopropyl to cyclohexyl ring or b) A stands for a direct bond and R a carbaldehyde residue. The new compounds are prepared from the known compound (20S)-20-hydroxymethyl-1,1-4-pregnadien-3-one by isomerization to the 1,5-dien-3-one and then, in case a) conversion of the 20-hydroxymethyl group to a 20-sulfonyloxymethyl group, reduction of the 3-keto group to the hydroxy group, construction of the side chain, oxidation to the 7-keto compound, epoxidation in the 1,2 position, conversion of the 7-ketone to the corresponding tosylhydrazide and reduction of the 7-tosylhydrazide with lithium aluminium hydride. In case b), the 20-hydroxymethyl group is protected by a protective group which is readily split off, the 5,7-diene is prepared as in a), the protective group is split off and the 20-hydroxymethyl compound is oxidized to the corresponding aldehyde.
Inventors:
Schenecker, bruno
Dresser, peter
Adam, Gunter
Marquardt, Volker
Walter, Dirk
Fisher, Reinard
Richard
Dresser, peter
Adam, Gunter
Marquardt, Volker
Walter, Dirk
Fisher, Reinard
Richard
Application Number:
JP50485192A
Publication Date:
April 24, 2000
Filing Date:
February 19, 1992
Export Citation:
Assignee:
Jena Farm, Gezel Shaft, Mitt, Beschlenktel, Haftung
International Classes:
C07J9/00; C07J31/00; C07J41/00; C07J51/00; C07J71/00; C07J75/00; C07J3/00; (IPC1-7): C07J71/00; C07J3/00; C07J9/00; C07J31/00; C07J41/00; C07J75/00
Attorney, Agent or Firm:
Kazuo Sato (2 outside)