Patent ID: 6645953
Filing Date: 2003-11-11
Classification: C07J,Y10S

Abstract:
A method of regulating meiosis in a mammalian germ cell comprising administering to a germ cell in need of such regulation, an effective amount of a compound of formula (I) wherein R1 and R2, independently, are selected from the group consisting of hydrogen and branched or unbranched C1-C6 alkyl which may be substituted by halogen, hydroxy or cyano, or wherein R1 and R2 together designate methylene or, together with the carbon atom to which they are bound, form a cyclopropane ring, a cyclopentane ring, or a cyclohexane ring; R3 is selected from the group consisting of hydrogen, methylene, hydroxy, methoxy, acetoxy, oxo, &boxH;NOR26 wherein R26 is hydrogen or C1-C3 alkyl, halogen, and C1-C4 alkyl; R4 is selected from the group consisting of hydrogen, methylene, hydroxy, methoxy, acetoxy, oxo, &boxH;NOR27 wherein R27 is hydrogen or C1-C3 alkyl, halogen, and C1-C4 alkyl; R5 designates, together with R6, an additional bond between the carbon atoms to which R5 and R6 are bound; R9 is hydrogen; R10 is hydrogen; R11 is selected from the group consisting of hydroxy, alkoxy, substituted alkoxy, alkanoyloxyalkyl, acyloxy, sulphonyloxy, phosphonyloxy, oxo, &boxH;NOR28 wherein R28 is hydrogen or C1-C3 alkyl, halogen and C1-C4 alkyl; R12 is selected from the group consisting of hydrogen, C1-C3 alkyl, vinyl, C1-C3 alkoxy and halogen; R13 designates, together with R14, an additional bond between the carbon atoms to which R13 and R14 are bound; R15 is selected from the group consisting of hydrogen, C1-C4 alkyl, methylene, hydroxy, methoxy, acetoxy, oxo, and &boxH;NOR23 wherein R23 is hydrogen or C1-C3 alkyl; R16 is selected from the group consisting of hydrogen, C1-C3 alkyl, methylene, hydroxy, methoxy, oxo and &boxH;NOR24 wherein R24 is hydrogen or C1-C3 alkyl; R17 is hydrogen or hydroxy; R18 and R19 are, independently, hydrogen or fluoro; R25 is selected from the group consisting of hydrogen, C1-4 alkyl, methylene, hydroxy and oxo; A is a carbon atom; R7 is selected from the group consisting of hydrogen, hydroxy and fluoro, and R8 is selected from the group consisting of hydrogen, C1-C4 alkyl, methylene and halogen; R20 is selected from the group consisting of C1-C4 alkyl, trifluoromethyl and C3-C6 cycloalkyl and R21 is selected from the group consisitning of C1-C4 alkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkyl containing up to three halogen atoms, methoxymethyl, acetoxymethyl, and C3-C6 cycloalkyl; provided that the compound of formula (I) does not have any cumulated double bonds and further provided that the compound is not one of the following compounds:Cholesta-8,14-diene-3&bgr;-ol; 4-Methylcholesta-8,14-diene-3&bgr;-ol; 4-Ethylcholesta-8,14-diene-3&bgr;-ol; 4,4-Dimethylcholesta-8,14-diene-3&bgr;-ol; 4&agr;-Methyl-4&bgr;-ethylcholesta-8,14-diene-3&bgr;-ol; 4&agr;-Ethyl-4&bgr;-methylcholesta-8,14-diene-3&bgr;-ol; 4,4-Diethylcholesta-8,14-diene-3&bgr;-ol; 4-Propylcholesta-8,14-diene-3&bgr;-ol; 4-Butylcholesta-8,14-diene-3&bgr;-ol; 4-Isobutylcholesta-8,14-diene-3&bgr;-ol; 4,4-Tetramethylenecholesta-8,14-diene-3&bgr;-ol; and 4,4-Pentamethylenecholesta-8,14-diene-3&bgr;-ol; or esters or ethers thereof.