Patent ID: RE39678

Claim:
A method of regulating meiosis comprising administering to a subject in need thereof an effective amount of the compound of formula Ic: wherein R 1 is hydrogen, halogen, methyl, hydroxyl or oxo; R 2 is selected from the group consisting of hydrogen, hydroxyl, C 1 -C 3 alkyl, vinyl, C 1 -C 3 alkoxy and halogen; R 3 is selected from the group consisting of hydrogen and optionally substituted alkoxy, acyloxy, sulphonyloxy, and phosphonyloxy; R′ 3 designates hydrogen or hydroxyl; R 4 and R′ 4 , which are different or identical with the proviso that they are not both hydroxyl, are selected from the group comprising hydrogen, halogen, hydroxyl and C 1 -C 6 alkyl which may be substituted by halogen, hydroxyl or cyano; R 5 is hydrogen, halogen, hydroxyl, lower alkyl, cyano, hydroxymethyl, a carbaldehyde, an oxime derived from a carbaldehyde, a carboxylic acid, a primary or secondary amine derived from a carboxylic acid or an ester with a C 1 -C 6 -alcohol group; R 6 is hydrogen, hydroxyl, halogen or oxo; R 7 is selected from the group consisting of hydrogen, hydroxyl, lower alkoxy, acyloxy, halogen and lower alkyl; R′ 7 is hydrogen, or, if R 7 is lower alkyl, R′ 7 is hydrogen or hydroxyl; R 8 designates together with R 9 an additional bond between the carbon atoms at which R 8 and R 9 are placed; R 11 is selected from the group consisting of hydrogen, hydroxyl, lower alkoxy, acyloxy, halogen and lower alkyl; R′ 11 is hydrogen or, if R 11 is lower alkyl, R′ 11 is hydrogen or hydroxyl; R 12 is selected from the group consisting of hydrogen, halogen, C 1 -C 4 alkyl, methylene, hydroxyl, lower alkoxy, acyloxy, oxo and a group of the general formula ═NOR 33 wherein R 33 is hydrogen or C 1 -C 3 alkyl; R 14 designates together with R 15 an additional bond between the carbon atoms at which R 14 and R 15 are placed; R 16 is selected from the group consisting of hydrogen, halogen, C 1 -C 3 alkyl, methylene, hydroxyl, lower alkoxy, oxo and a group of the general formula ═NOR 34 wherein R 34 is hydrogen or lower alkyl; R 17 is hydrogen or hydroxyl; R 20 is selected from the group consisting of hydrogen, lower alkyl and hydroxymethyl or R 20 and R′ 20 together designate methylene or oxo; R′ 20 is hydrogen, halogen, lower alkyl or hydroxyl; R′ 22 is hydrogen, hydroxyl or oxo; and R 22 is cyclohexyl or cyclohexylalkyl, each optionally substituted by one or more of the following groups which substituents may be different or identical: hydroxyl, lower alkoxy, halogen, amino, cyano, carboxy, a group of the general formula —COOR 39 , oxo, N-alkylamino or N,N-dialkylamino wherein the N-alkylamino or N,N-dialkylamino substituent optionally is substituted by carboxy, lower alkoxy or lower alkylthio; and wherein R 39 is lower alkyl or aralkyl.