20(S)-25-hydroxy vitamin D compounds
First Claim
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1. A compound having the formula ##STR6## where the stereochemical center at carbon 20 in the side chain has the S configuration, R is hydrogen or a hydroxy-protecting group, and Z is selected from the group consisting of Y, --OY, CH2 OY, --C.tbd.CY and --CH═
- CHY, where the double bond may have the cis or trans stereochemical configuration, and where Y is a radical of the structure ##STR7## where m and n, independently, represent the integers from 0 to 5;
where R1 is selected from the group consisting of hydrogen, hydroxy, protected-hydroxy, fluoro, trifluoromethyl, and C1-5 alkyl, which may be straight-chain or branched and, optionally, bear a hydroxy or protected-hydroxy substituent;
where each of R2, R3 and R4, independently, is selected from the group consisting of hydrogen, fluoro, trifluoromethyl and C1-5 alkyl, which may be straight-chain or branched, and optionally bear a hydroxy or protected-hydroxy substituent;
where R1 and R2, taken together, represent an oxo group, or an alkylidene group, ═
CR2 R3, or the group --(CH2)p --, where p is an integer from 2 to 5;
where R3 and R4, taken together, represent an oxo group, or the group --(CH2)q --, where q is an integer from 2 to 5; and
where R5 represents hydrogen, hydroxy, protected-hydroxy, or C1-5 alkyl.
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Abstract
Vitamin D3 analogs in which the methyl group normally attached to the side chain at carbon 20 has been exchanged with the hydrogen atom to form the 20-epi configuration. The compounds are characterized by a marked intestinal calcium transport activity while exhibiting much higher activity than 1α,25-dihydroxyvitamin D3 in their ability to mobilize calcium from bone. Because of their preferential calemic activity, these compounds would be useful for the treatment of diseases such as hypoparathyroidism or where bone formation is desired, such as low bone turn over osteoporosis. This disclosure is also directed toward 20-epi-3,5-cyclovitamin D compounds useful as intermediates in a process for preparing 20-epi-vitamin D3 analogs.
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Citations
3 Claims
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1. A compound having the formula ##STR6## where the stereochemical center at carbon 20 in the side chain has the S configuration, R is hydrogen or a hydroxy-protecting group, and Z is selected from the group consisting of Y, --OY, CH2 OY, --C.tbd.CY and --CH═
- CHY, where the double bond may have the cis or trans stereochemical configuration, and where Y is a radical of the structure ##STR7## where m and n, independently, represent the integers from 0 to 5;
where R1 is selected from the group consisting of hydrogen, hydroxy, protected-hydroxy, fluoro, trifluoromethyl, and C1-5 alkyl, which may be straight-chain or branched and, optionally, bear a hydroxy or protected-hydroxy substituent;
where each of R2, R3 and R4, independently, is selected from the group consisting of hydrogen, fluoro, trifluoromethyl and C1-5 alkyl, which may be straight-chain or branched, and optionally bear a hydroxy or protected-hydroxy substituent;
where R1 and R2, taken together, represent an oxo group, or an alkylidene group, ═
CR2 R3, or the group --(CH2)p --, where p is an integer from 2 to 5;
where R3 and R4, taken together, represent an oxo group, or the group --(CH2)q --, where q is an integer from 2 to 5; and
where R5 represents hydrogen, hydroxy, protected-hydroxy, or C1-5 alkyl.
- CHY, where the double bond may have the cis or trans stereochemical configuration, and where Y is a radical of the structure ##STR7## where m and n, independently, represent the integers from 0 to 5;
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2. A compound having the formula ##STR8## where the stereochemical center at carbon 20 in the side chain has the S configuration, X4 and X5 which may be the same or different, is hydrogen, hydroxy, or oxygen, and Z is selected from the group consisting of Y, --OY, --CH2 OY, --C.tbd.CY and --CH═
- CHY, where the double bond may have the cis or trans stereochemical configuration, and where Y is selected from the group consisting of hydrogen, methyl, --CR5 O and a radical of the structure ##STR9## where m and n, independently, represent the integers from 0 to 5;
where R1 is selected from the group consisting of hydrogen, hydroxy, protected-hydroxy, fluoro, trifluoromethyl, and C1-5 alkyl, which may be straight chain or branched and, optionally, bear a hydroxy or protected-hydroxy substituent;
where each of R2, R3 and R4, independently, is selected from the group consisting of hydrogen, fluoro, trifluoromethyl and C1-5 alkyl, which may be straight-chain or branched, and optionally bear a hydroxy or protected-hydroxy substituent;
where R1 and R2, taken together, represent an oxo group, or an alkylidene group, ═
CR2 R3, or the group --(CH2)p --, where p is an integer from 2 to 5;
where R3 and R4, taken together, represent an oxo group, or the group --(CH2)q --, where q is an integer from 2 to 5; and
where R5 represents hydrogen, hydroxy, protected-hydroxy, or C1-5 alkyl.
- CHY, where the double bond may have the cis or trans stereochemical configuration, and where Y is selected from the group consisting of hydrogen, methyl, --CR5 O and a radical of the structure ##STR9## where m and n, independently, represent the integers from 0 to 5;
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3. (20S)-25-hydroxyvitamin D3.
Specification
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Current AssigneeWisconsin Alumni Research Foundation (University of Wisconsin System)
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Original AssigneeWisconsin Alumni Research Foundation (University of Wisconsin System)
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InventorsWicha, Jerzy, DeLuca, Hector F.
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Primary Examiner(s)Clardy, S. Mark
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Assistant Examiner(s)PRYOR, ALTON NATHANIEL
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Application NumberUS08/783,028Time in Patent Office679 DaysField of Search552/653US Class Current552/653CPC Class CodesA61K 31/593 9,10-Secocholestane derivat...
