Vitamin D amide derivatives
AssigneeResearch Institute for Medicine and Chemistry Inc.
InventorsRobert H. Hesse, Gaddam S. Reddy, Sundara K. S. Setty
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Abstract
The invention pertains to vitamin D amide derivatives of formula (I). These novel 1.alpha.-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.sup.1 and R.sup.2 independently represent a hydrogen atom or a lower alkyl or cycloalkyl group, or R.sup.1 R.sup.2 N-- represents a heterocyclic group; and R.sup.3 and R.sup.4 independently represent a hydrogen atom or an 0-protecting group. Active compounds, in which R.sup.3 and R.sup.4 are hydrogen atoms or metabolically labile 0-protecting groups exhibit potent cell modulating effect, but minimal effect on calcium metabolism.
Claims10
Compounds of general formulae (I) and (II) ##STR6## wherein Y represents an alkylene or alkenylene group containing up to 4 carbon atoms;
- R.sup.1 and R.sup.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.sup.3 and R.sup.4, which may be the same or different, each represents a hydrogen atom or an O-protecting group.
The compounds:
- 1.alpha.,3.beta.-dihydroxy-9,10-seco-25-azacholesta-5(Z),7,10(19)-trien-24- one;
- 1.alpha.,3.beta.-dihydroxy-23,23-bishomo-24-aza-9,10-secosholesta-5(Z), 7,10(19)-trien-24-one;
- 1.alpha.,3.beta.-dihydroxy-27-nor-9,10-secocholesta-5(Z), 7,10(19),22,24-pentaene-26-carboxylic acid, 26-dimethyl amide;
- N,N-pentamethylene-1.alpha.,3.beta.-dihydroxy-9,10 -secocholanamide-5(Z), 7,10(19)-triene;
- N-cyclopropyl-1.alpha.,3.beta.-dihydroxy-9,10 -secocholanamide-5(Z), 7,10(19)-triene;
- .alpha. . 3.beta.-dihydroxy-9,10 -secocholanamide-5(Z), 7,10(19)-triene;
- N,N-pentamethylene-1.alpha.,3.beta.-dihydroxy-9,10 -seco-20 -epi-cholanamide-5(Z),7,10(19-triene;
- and corresponding 5(E)-isomers thereof.
Dependencies are inferred from the claim text.