Fluorinated vitamin d3 analogs

Details Fluorinated vitamin d3 analogs Fluorinated vitamin d3 analogs

C - Chemistry, Metallurgy

07

C

C07C 401/00 (2006.01) A61K 31/59 (2006.01) C07C 49/743 (2006.01) C07F 7/18 (2006.01)

Patent

CA 2205315

The novel fluorinated Vitamin D3 analogs of formula (see formula I) wherein: X is (H, H) or =CH2; R1 and R2 are, independently of each other, hydrogen, (C1-C4) alkyl or fluoroalkyl, or R1 and R2 together with C-20 form a (C3-C6) cycloalkyl or cyclofluoroalkyl, or R1 and R2 together form =CH2; R3 and R4 are, independently of each other, a (C1-C4) alkyl or fluoroalkyl, or R3 and R4 together with C-25 form a (C3-C9) cycloalkyl or cyclofluoroalkyl; A is a single bond or a double bond; and B is a double bond or a triple bond; except that: (i) when X is =CH2, R3 and R4 are each CF3, A is a double bond and one of R1 or R2 is hydrogen, then the other of R1 or R2 cannot be CH3; (ii) when X is =CH2, R3 and R4 are each a (C1-C2) alkyl, A is a double bond and R2 is hydrogen, then R1 cannot be CH3; (iii) when X is =CH2, R3 and R4 are each a (C1-C4) alkyl, A is a double bond and R1 is hydrogen, then R2 cannot be CH3; (iv) when X is =CH2, one of R3 or R4 is a CF3, A is a double bond, R1 is CH3 and R2 is hydrogen, then the other of R3 or R4 cannot be CH3; and (v) when X is (H,H), R3 and R4 are each CF3, A is a double bond, B is a triple bond and R2 is hydrogen, then R1 cannot be CH3, and the compounds of the above formula I wherein: X i s ( H , H ) or =CH2 ; R1 and R2 are, independently of each other, hydrogen, (C1-C4) alkyl or fluoroalkyl, or R1 and R2 together with C-20 form a (C3-C6) cycloalkyl or cyclofluoroalkyl, or R1 and R2 together form =CH2; R3 and R4 are, independently of each other, a (C1-C4) alkyl or fluoroalkyl, or R3 and R4 together with C-25 form a (C3-C9) cycloalkyl or cyclofluoroalkyl; A is a single bond or a double bond; and B is a double bond or a triple bond; except that where R3 and R4 are each CF3 and A is a double bond and B is a triple bond and R2 is hydrogen, then R1 cannot be CH3, are useful in the treatment of osteoporosis.

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