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US5494905A
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Vitamin D amide derivatives
Assignee: Research Institute for Medicine and Chemistry Inc
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Filing: 1992-11-06
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Granted: 1996-02-27
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Expires: 2012-11-06
Abstract
Abstract The invention pertains to vitamin D amide derivatives of formula (I). These novel 1α-hydroxy vitamin D derivatives and their 20-epi analogues comprise compounds of formula (I) and corresponding 5,6-trans isomers, where Y represents an alkylene or alkenylene group containing up to four carbon atoms; R 1 and R 2 independently represent a hydrogen atom or a lower alkyl or cycloalkyl group, or R 1 R 2 N-- represents a heterocyclic group; and R 3 and R 4 independently represent a hydrogen atom or an 0-protecting group. Active compounds, in which R 3 and R 4 are hydrogen atoms or metabolically labile 0-protecting groups exhibit potent cell modulating effect, but minimal effect on calcium metabolism.
Inventors
- 👤 Robert H. Hesse
- 👤 Gaddam S. Reddy
- 👤 Sundara K. S. Setty
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 20:02
CPC Classifications
C; C07; C07C; C07C401/00; A; A61; A61P; A61P19/00; A61P19/08; A61P19/10; A61P3/00; A61P3/02; A61P35/00; A61P37/00; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
85 words
Compounds of general formulae (I) and (II) ##STR6## wherein Y represents an alkylene or alkenylene group containing up to 4 carbon atoms; R 1 and R 2 , which may be the same or different, each represents a hydrogen atom or a lower alkyl or cycloalkyl group or together with the nitrogen atom to which they are attached form a piperidino group; and R 3 and R 4 , which may be the same or different, each represents a hydrogen atom or an O-protecting group.
Claim 2
Dependent Claim
85 words
Compounds of general formulae (I) and (II) ##STR6## wherein Y represents an alkylene or alkenylene group containing up to 4 carbon atoms; R 1 and R 2 , which may be the same or different, each represents a hydrogen atom or a lower alkyl or cycloalkyl group or together with the nitrogen atom to which they are attached form a piperidino group; and R 3 and R 4 , which may be the same or different, each represents a hydrogen atom or an O-protecting group.
Claim 3
Dependent Claim
48 words
Compounds as claimed in claim 1 wherein Y represents a group of formula --(R.sup.A).sub.m --(R.sup.B).sub.n -- wherein R A is --CH═CH--, R B is --CH 2 --, m is 0, 1 or 2 and n is 0 or an integer such that 2m+n =1, 2, 3 or 4.
Claim 4
Dependent Claim
14 words
Compounds as claimed in claim 1 wherein Y is a C 2-4 alkylene group.
Claim 5
Dependent Claim
20 words
Compounds as claimed in claim 1 wherein at least one of R 1 and R 2 is other than hydrogen.
Claim 6
Dependent Claim
31 words
Compounds as claimed in claim 1 wherein R 1 and R 2 are selected from hydrogen atoms, methyl and cyclopropyl groups, or R 1 R 2 N-- represents a piperidino group.
Claim 7
Dependent Claim
16 words
Compounds as claimed in claim 1 wherein R 3 and R 4 represent etherifying silyl groups.
Claim 8
Dependent Claim
24 words
Compounds as claimed in claim 1 wherein R 3 and R 4 are selected from hydrogen atoms and metabolically labile etherifying or esterifying groups.
Claim 9
Dependent Claim
16 words
The compounds: 1α,3β-dihydroxy-9,10-seco-25-azacholesta-5(Z),7,10(19)-trien-24-one; 1α,3β-dihydroxy-23,23-bishomo-24-aza-9,10-secosholesta-5(Z), 7,10(19)-trien-24-one; 1α,3β-dihydroxy-27-nor-9,10-secocholesta-5(Z), 7,10(19),22,24-pentaene-26-carboxylic acid, 26-dimethyl amide; N,N-pentamethylene-1α,3β-dihydroxy-9,10 -secocholanamide-5(Z), 7,10(19)-triene; N-cyclopropyl-1α,3β-dihydroxy-9,10 -secocholanamide-5(Z), 7,10(19)-triene;
Claim 10
Dependent Claim
16 words
The compounds: 1α,3β-dihydroxy-9,10-seco-25-azacholesta-5(Z),7,10(19)-trien-24-one; 1α,3β-dihydroxy-23,23-bishomo-24-aza-9,10-secosholesta-5(Z), 7,10(19)-trien-24-one; 1α,3β-dihydroxy-27-nor-9,10-secocholesta-5(Z), 7,10(19),22,24-pentaene-26-carboxylic acid, 26-dimethyl amide; N,N-pentamethylene-1α,3β-dihydroxy-9,10 -secocholanamide-5(Z), 7,10(19)-triene; N-cyclopropyl-1α,3β-dihydroxy-9,10 -secocholanamide-5(Z), 7,10(19)-triene;
Claim 11
Dependent Claim
12 words
α . 3β-dihydroxy-9,10 -secocholanamide-5(Z), 7,10(19)-triene; N,N-pentamethylene-1α,3β-dihydroxy-9,10 -seco-20 -epi-cholanamide-5(Z),7,10(19-triene; and corresponding 5(E)-isomers thereof.
Claim 12
Dependent Claim
12 words
α . 3β-dihydroxy-9,10 -secocholanamide-5(Z), 7,10(19)-triene; N,N-pentamethylene-1α,3β-dihydroxy-9,10 -seco-20 -epi-cholanamide-5(Z),7,10(19-triene; and corresponding 5(E)-isomers thereof.
Claim 13
Dependent Claim
22 words
Pharmaceutical compositions comprising a compound as claimed in claim 7 or in admixture with one or more physiologically acceptable carriers or excipients.
Claim 14
Dependent Claim
22 words
A pharmaceutical composition comprising a compound as claimed in claim 8 in admixture with one or more physiologically acceptable carriers or excipients.
References Cited (Backward Citations)
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