1,3-dihydroxy-20,20-dialkyl-vitamin D3 analogs
OwnerPercy Sarwood Manchand, Milan Radoje Uskokovicinventors
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Abstract
This invention relates to 1,3-dihydroxy-20,20-dialkyl-vitamin D3 analogs of Formula (I): 1 compositions comprising the analogs, methods of preparing the analogs and methods of treatment of osteoporosis, secondary hyperparathyroidism, cancer and autoimmune diseases using such analogs.
Claims30
A compound selected from the group of compounds represented by Formula (I)
- 17
- wherein:
- X is hydrogen or ═CH2;
- R1 and R2 are, independently of each other, a (C1-C4)alkyl or (C1-C4)fluoroalkyl, or R1 and R2 together with C20 form a (C3-C6)cycloalkyl or (C3-C6)cyclofluoroalkyl, or R1 and R2 together form ═CH2;
- R3 and R4 are, independently of each other, a (C1-C4)alkyl or (C1-C4)fluoroalkyl, or R3 and R4 together with C25 form a (C3-C9)cycloalkyl or (C3-C9)cyclofluoroalkyl;
- A is a single or a double bond;
- and
- B is a single, double or triple bond;
- and prodrugs thereof, provided that:
- (i) when R1 and R2 are (C1-C4)alkyl or R1 and R2 together with C20 form a cyclopropyl group or ═CH2, R3 and R4 are (C1-C4)alkyl, trifluoromethyl or R3 and R4 together with C25 form (C3-C6)cycloalkyl and A is a single bond, then B is not a trans double bond;
- (ii) when B is a single bond, then R1 and R2 together with C20 form a (C3-C6)-cycloalkyl or (C3-C6)cyclofluoroalkyl group;
- and
- (iii) when R1 and R2 are (C1-C4)alkyl, R3 and R4 are (C1-C4)alkyl, X═CH2 and A is a single bond, then B is not a double bond.
A method of treating osteoporosis via administration of a therapeutically effective amount of a compound of Formula (I)
- 18
- wherein:
- X is hydrogen or ═CH2;
- R1 and R2 are, independently of each other, a (C1-C4)alkyl or (C1-C4)fluoroalkyl, or R1 and R2 together with C20 form a (C3-C6)cycloalkyl or (C3-C6)cyclofluoroalkyl, or R1 and R2 together form ═CH2;
- R3 and R4 are, independently of each other, a (C1-C4)alkyl or (C1-C4)fluoroalkyl, or R3 and R4 together with C25 form a (C3-C9)cycloalkyl or (C3-C9)cyclofluoroalkyl;
- A is a single or a double bond;
- and
- B is a single, double or triple bond;
- and prodrugs thereof.
A method of treating cancer via administration of a therapeutically effective amount of a compound of Formula (I)
- 19
- wherein:
- X is hydrogen or ═CH2;
- R1 and R2 are, independently of each other, a (C1-C4)alkyl or (C1-C4)fluoroalkyl, or R1 and R2 together with C20 form a (C3-C6)cycloalkyl or (C3-C6)cyclofluoroalkyl, or R1 and R2 together form ═CH2;
- R3 and R4 are, independently of each other, a (C1-C4)alkyl or (C1-C4)fluoroalkyl, or R3 and R4 together with C25 form a (C3-C9)cycloalkyl or (C3-C9)cyclofluoroalkyl;
- A is a single or a double bond;
- and
- B is a single, double or triple bond;
- and prodrugs thereof, provided that:
- (i) when R1 and R2 are (C1-C4)alkyl or R1 and R2 together with C20 form a cyclopropyl group or ═CH2, R3 and R4 are (C1-C4)alkyl, trifluoromethyl or R3 and R4 together with C25 form (C3-C6)cycloalkyl and A is a single bond, then B is not a trans double bond;
- (ii) when B is a single bond, then R1 and R2 together with C20 form a (C3-C6)cycloalkyl or (C3-C6)cyclofluoroalkyl group;
- and
- (iii) when R1 and R2 are (C1-C4)alkyl, R3 and R4 are (C1-C4)alkyl, X═CH2 and A is a single bond, then B is not a double bond.
A method of treating secondary hyperparathyroidism via administration of a therapeutically effective amount of a compound of Formula (I)
- 20
- wherein:
- X is hydrogen or ═CH2;
- R1 and R2 are, independently of each other, a (C1-C4)alkyl or (C1-C4)fluoroalkyl, or R1 and R2 together with C20 form a (C3-C6)cycloalkyl or (C3-C6)cyclofluoroalkyl, or R1 and R2 together form ═CH2;
- R3 and R4 are, independently of each other, a (C1-C4)alkyl or (C1-C4)fluoroalkyl, or R3 and R4 together with C25 form a (C3-C9)cycloalkyl or (C3-C9)cyclofluoroalkyl;
- A is a single or a double bond;
- and
- B is a single, double or triple bond;
- and prodrugs thereof.
Dependencies are inferred from the claim text.