16-ene-vitamin D derivatives
AssigneeChugai Seiyaku Kabushiki Kaisha
InventorAkira Kawase
Life of this patent
Estimating the term…
Abstract
A vitamin D derivative of general formula (1): wherein X represents an oxygen or sulfur atom, R11 represents a saturated or unsaturated aliphatic hydrocarbon group which may be substituted by a hydroxyl group or a protected hydroxyl group, or a —COR12 group where R12 represents an alkyl, aryl or alkoxy group, R2 represents —OR9 or a hydrogen atom, and R9 and R10 each represent a hydrogen atom or a hydroxyl group.
Claims21
A vitamin D derivative of general formula (1):
- wherein
- X represents an oxygen or sulfur atom,
- R11 represents a saturated or unsaturated aliphatic hydrocarbon group which may be substituted by a hydroxyl group or a protected hydroxyl group, a —COR12 group where R12 represents an alkyl, aryl or alkoxy group, or
- wherein R5 and R6 each represent a hydrogen atom or a hydroxyl group, m represents an integer of 1 to 4, and n represents an integer of 0 to 2,
- R2 represents —OR9 or a hydrogen atom, and
- R9 and R10 may by the same or different and each represents a hydrogen atom or a protecting group.
1,3-Dihydroxy-20-(3-hydroxy-3-methylbutylthio)-9,10-secopregna-5,7,10(19),16-tetraene.
1α,3β-Dihydroxy-20(S)-(3-hydroxy-3-methylbutylthio)-9,10-secopregna-5,7,10(19),16-tetraene.
1α,3β-Dihydroxy-20(R)-(3-hydroxy-3-methylbutylthio)-9,10-secopregna-5,7,10(19),16-tetraene.
1α,3β-Dihydroxy-20(R)-((E)-4-hydroxy-4-methyl-2-pentenylthio)-9,10-secopregna-5,7,10(19),16-tetraene.
1α,3β-Dihydroxy-20(R)-((E)-4-ethyl-4-hydroxy-2-hexenylthio)-9,10-secopregna-5,7,10(19),16-tetraene.
1α,3β-Dihydroxy-20(S)-(2-hydroxy-2-methylpropylthio)-9,10-secopregna-5,7,10(19),16-tetraene.
1α,3β-Dihydroxy-20(R)-(2-hydroxy-2-methylpropylthio)-9,10-secopregna-5,7,10(19),16-tetraene.
1α,3β-Dihydroxy-20(S)-{2(S)-hydroxy-3-methylbutyloxy}-9,10-secopregna-5,7,10(19),16-tetraene.
1α,3β-Dihydroxy-20(S)-{2(R)-hydroxy-3-methylbutyloxy}-9,10-secopregna-5,7,10 ,(19),16-tetraene.
1α,3β-dihydroxy-20(S)-(2-ethyl-2-hydroxybutylthio)-9,10-secopregna-5,7,10(19),16-tetraene.
1α,3β-Dihydroxy-20(R)-(2-ethyl-2-hydroxybutylthio)-9,10-secopregna-5,7,10(19),16-tetraene.
A pharmaceutical composition comprising a carrier and a vitamin D derivative of general formula (1):
- wherein
- X represents an oxygen or sulfur atom,
- R11 represents a saturated or unsaturated aliphatic hydrocarbon group which may be substituted by a hydroxyl group or a protected hydroxyl group, a —COR12 group where R12 represents an alkyl, aryl or alkoxy group, or
- wherein R5 and R6 each represent a hydrogen atom or a hydroxyl group, m represents an integer of 1 to 4, and n represents an integer of 0 to 2,
- R2 represents —OR9 or a hydrogen atom, and
- R9 and R10 may be the same or different and each represent a hydrogen atom or a hydroxyl group.
A process for preparing a vitamin D derivative of general formula (1):
- wherein X represents an oxygen or sulfur atom, R11 represents a saturated or unsaturated aliphatic hydrocarbon group which may be substituted by a hydroxyl group or a protected hydroxyl group, a —COR12 group where R12 represents an alkyl, aryl or alkoxy group, or
- wherein R5 and R6 each represent a hydrogen atom or a hydroxyl group, m represents an integer of 1 to 4, and n represents an integer of 0 to 2, R2 represents —OR9, or a hydrogen atom, and R9 and R10 may be the same or different and each represents a hydrogen atom or a protecting group, which process comprises subjecting a compound of general formula (4a):
- wherein X represents an oxygen or sulfur atom, R1 represents a saturated or unsaturated aliphatic hydrocarbon group which may be substituted by an optionally protected hydroxyl group, or a —COR12 group where R12 represents an alkyl, aryl or alkoxy group, and R9 and R10 may be the same or different and each represent a hydrogen atom or a protecting group, to photoreaction, thermal isomerization and deprotection.
Dependencies are inferred from the claim text.