22-Thiavitamin D.sub.3 derivatives
First Claim
Patent Images
1. A compound of the general formula (I):
- ##STR21## wherein R1 represents a C1-10 alkyl group which may be substituted by one or more hydroxyl groups provided that the terminal carbon atom of R1 group is a primary carbon atom or a secondary carbon atom, or R1 is an unsubstituted alkyl group or an alkyl group substituted by 2 or more hydroxyl groups, R2 represents a hydrogen atom or a hydroxyl group, and R3 represents a hydrogen atom or a hydroxyl group.
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Abstract
Compounds of the general formula: ##STR1## wherein R1 represents a C1-10 alkyl group which may be substituted by one or more hydroxyl groups, R2 represents a hydrogen atom or a hydroxyl group, and R3 represents a hydrogen atom or a hydroxyl group; their intermediates; as well as synthesis processes of these compounds and intermediates are disclosed. The compounds of this invention, vitamin D derivatives substituted by sulfur atoms at the 22-position have a strong inhibitory effect against proliferation of keratinocytes.
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Citations
40 Claims
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1. A compound of the general formula (I):
- ##STR21## wherein R1 represents a C1-10 alkyl group which may be substituted by one or more hydroxyl groups provided that the terminal carbon atom of R1 group is a primary carbon atom or a secondary carbon atom, or R1 is an unsubstituted alkyl group or an alkyl group substituted by 2 or more hydroxyl groups, R2 represents a hydrogen atom or a hydroxyl group, and R3 represents a hydrogen atom or a hydroxyl group.
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10)
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11. A compound of the general formula (I):
- ##STR24## wherein R1 represents a C1-10 alkyl group which may be substituted by one or more hydroxyl groups, R2 represents a hydroxyl group, and R3 represents a hydrogen atom or a hydroxyl group.
- View Dependent Claims (12, 13, 14, 15, 16, 17, 18, 19, 20, 21)
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22. A compound of the formula (I):
- ##STR27## wherein R2 represents a hydrogen atom or a hydroxyl group, R3 represents a hydrogen atom or a hydroxyl group, and R1 is a straight chain C1-10 alkyl group which may be substituted by one or more hydroxyl groups, a branched chain C1-10 alkyl group which may be substituted by two or more hydroxyl groups, or a group of the formula (III);
##STR28## wherein R4 represents a hydroxyl group and R5 represents a hydrogen atom, m represents an integer of 1 through 4, and n represents an integer of 0 through 2.
- ##STR27## wherein R2 represents a hydrogen atom or a hydroxyl group, R3 represents a hydrogen atom or a hydroxyl group, and R1 is a straight chain C1-10 alkyl group which may be substituted by one or more hydroxyl groups, a branched chain C1-10 alkyl group which may be substituted by two or more hydroxyl groups, or a group of the formula (III);
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23. A compound of the formula (I):
- ##STR29## wherein R2 represents a hydrogen atom or a hydroxyl group, R3 represents a hydrogen atom or a hydroxyl group, and R1 is selected from the group consisting of 3-hydroxy-3-methylbutyl, 2-hydroxy-3-methylbutyl, 4-hydroxy-3-methylbutyl, 2,3-dihydroxy-3-methylbutyl, 2,4-dihydroxy-3-methylbutyl, 3,4-dihydroxy-3-methylbutyl, 3-hydroxy-3-ethylpentyl, 2-hydroxy-3-ethylpentyl, 4-hydroxy-3-ethylpentyl, 2,3-dihydroxy-3-ethylpentyl, 2,4-dihydroxy-3-ethylpentyl, 3,4-dihydroxy-3-ethylpentyl, 4-hydroxy-4-methylpentyl, 3-hydroxy-4-methylpentyl, 5-hydroxy-4-methylpentyl, 3,4-dihydroxy-4-methylpentyl, 3,5-dihydroxy-4-methylpentyl, 4,5-dihydroxy-4-methylpentyl, 3-hydroxy-3-(n-propyl)hexyl, 4-hydroxy-3-(n-propyl)hexyl, 2-hydroxy-3-(n-propyl)hexyl, 2,3-dihydroxy-3-(n-propyl)hexyl, 3,4-dihydroxy-3-(n-propyl)hexyl, 2,4-dihydroxy-3-(n-propyl)hexyl, 3-hydroxy-4-ethylhexyl, 4-hydroxy-4-ethylhexyl, 5-hydroxy-4-ethylhexyl, 3,4-dihydroxy-4-ethylhexyl, 3,5-dihydroxy-4-ethylhexyl, 4,5-dihydroxy-4-ethylhexyl, 4-hydroxy-5-methylhexyl, 5-hydroxy-5-methylhexyl, 6-hydroxy-5-methylhexyl, 4,5-dihydroxy-5-methylhexyl, 4,6-dihydroxy-5-methylhexyl, 5,6-dihydroxy-5-methylhexyl, 5-hydroxy-6-methylheptyl, 6-hydroxy-6-methylheptyl, 7-hydroxy-6-methylheptyl, 5,6-dihydroxy-6-methylheptyl, 5,7-dihydroxy-6-methylheptyl, 6,7-dihydroxy-6-methylheptyl, 4-hydroxy-5-ethylheptyl, 5-hydroxy-5-ethylheptyl, 6-hydroxy-5-ethylheptyl, 4,5-dihydroxy-5-ethylheptyl, 4,6-dihydroxy-5-ethylheptyl, 5,6-dihydroxy-5-ethylheptyl, 3-hydroxy-4-(n-propyl)heptyl, 4-hydroxy-4-(n-propyl)heptyl, 5-hydroxy-4-(n-propyl)heptyl, 3,4-dihydroxy-4-(n-propyl)heptyl, 3,5-dihydroxy-4-(n-propyl)heptyl and 4,5-dihydroxy-4-(n-propyl)heptyl groups, preferably 3-hydroxy-3-methylbutyl, 2,3-dihydroxy-3-methylbutyl, 3,4-dihydroxy-3-methylbutyl, 3-hydroxy-3-ethylpentyl, 2,3-dihydroxy-3-ethylpentyl, 3,4-dihydroxy-3-ethylpentyl, 4-hydroxy-4-methylpentyl, 3,4-dihydroxy-4-methylpentyl and 4,5-dihydroxy-4-methylpentyl.
- View Dependent Claims (24)
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25. A compound selected from the group consisting of 1α
- ,3β
-Dihydroxy-20(R)-(4-hydroxy-4-methylpentylthio)-9,10-secopregna-5,7,10(19)-triene;
1α
,3β
-Dihydroxy-20(R)-(3-ethyl-3-hydroxypentylthio)-9,10-secopregna-5,7,10(19)-triene; and
20(S)-(3-Ethyl-3-hydroxypentylthio)-1α
, 3β
,16α
-trihydroxy-9,10-secopregna-5,7,10(19)-triene.
- ,3β
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26. A compound of the general formula (VI):
- ##STR30## wherein R6 and R7, which may be the same or different, each represents a hydrogen atom or a protective group, and R8 represents a C1-10 alkyl group which may be substituted.
- View Dependent Claims (27, 28, 29, 30)
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31. A compound of the general formula (XI):
- ##STR33## wherein R15 and R16, which may be same or different, each represents a hydrogen atom or a protective group, and A1 represents --CHOH-- or --CO--.
- View Dependent Claims (32, 33)
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34. A compound of the general formula (XIII):
- ##STR35## wherein R19 and R20, which may be the same or different, each represents a hydrogen atom or a protective group, R21 represents a C1-10 alkyl group which may be substituted, and A3 represents --CHOH-- or --CO--.
- View Dependent Claims (35, 36, 37)
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38. A process for preparing a compound of the general formula (XVI):
- ##STR38## wherein R25 represents a C1-10 alkyl group which may be substituted by one or more hydroxyl groups, R26 and R27, which may be the same or different, each represents a hydrogen atom or a protective group, and R28 represents a hydrogen atom or a hydroxyl group, said process comprising the step of subjecting a compound of the general formula (XV);
##STR39## wherein R25, R26, R27 and R28 are as defined above, to a light irradiation reaction and a thermal isomerization reaction.
- ##STR38## wherein R25 represents a C1-10 alkyl group which may be substituted by one or more hydroxyl groups, R26 and R27, which may be the same or different, each represents a hydrogen atom or a protective group, and R28 represents a hydrogen atom or a hydroxyl group, said process comprising the step of subjecting a compound of the general formula (XV);
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39. A process for preparing a compound of the general formula (VI):
- ##STR40## wherein R6 and R7, which may be the same or different, each represents a hydrogen atom or a protective group, and R8 represents a C1-10 alkyl group which may be substituted, said process comprising the step of reacting a compound of the general formula (IV);
##STR41## wherein R6 and R7 are as defined above, with a compound of the general formula (V);
space="preserve" listing-type="equation">R.sub.8 --SH (V)wherein R8 is as defined above, under reducing conditions.
- ##STR40## wherein R6 and R7, which may be the same or different, each represents a hydrogen atom or a protective group, and R8 represents a C1-10 alkyl group which may be substituted, said process comprising the step of reacting a compound of the general formula (IV);
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40. A process for preparing a compound of the general formula (IX):
- ##STR42## wherein R9 and R10, which may be the same or different, each represents a hydrogen atom or a protective group, and R11 represents a C1-10 alkyl group which may be substituted, said process comprising the step of reacting a compound of the general formula (VII);
##STR43## wherein R9 and R10 are as defined above, with a compound of the general formula (VIII);
space="preserve" listing-type="equation">R.sub.11 --SH (VIII)wherein R11 is as defined above, under basic conditions.
- ##STR42## wherein R9 and R10, which may be the same or different, each represents a hydrogen atom or a protective group, and R11 represents a C1-10 alkyl group which may be substituted, said process comprising the step of reacting a compound of the general formula (VII);
Specification