Meiosis regulating compounds
AssigneeNovo Nordisk A/S
InventorsChristian Grondahl, Frederik Christian Gronvald, Peter Faarup, Anthony Murray, Jan Lund Ottesen
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Abstract
Certain compounds, structurally related to natural compounds which can be extracted i.a. from bull testes and from human follicular fluid, can be used for regulating the meiosis in oocytes and in male germ cells. Some of these compounds are useful in the treatment of infertility, whereas other compounds are useful as contraceptives. These compounds have the structural formula wherein the substituents are as defined in the specification.
Claims6
A method of regulating meiosis in a mammalian germ cell comprising administering to a germ cell in need thereof an effective amount of a compound of formula Ic:
- wherein R1 and R2, which are different or identical provided that they are not both hydroxy, are hydrogen, halogen, hydroxy or branched or unbranched C1-C6 alkyl which may be substituted by halogen, hydroxy or cyano, or wherein R1 and R2 together designate methylene or oxo;
- R3 is hydrogen, methylene, hydroxy, methoxy, acetoxy, oxo, halogen, C1-C4 αalkandiyl (bound to the same carbon atom of the sterol skeleton) or ═NOR26 wherein R26 is hydrogen or C1-C3 alkyl, or R3 designates, together with R9, an additional bond between the carbon atoms at which R3 and R9 are placed;
- R4 is hydrogen, methylene, hydroxy, methoxy, acetoxy, oxo, halogen, C1-C4 alkandiyl (bound to the same carbon atom of the sterol skeleton) or ═NOR27 wherein R27 is hydrogen or C1-C3 alkyl,;
- R5 is hydrogen, halogen, C1-C4 alkyl, methylene, hydroxy, methoxy, oxo or ═NOR22 wherein R22 is hydrogen or C1-C3 alkyl;
- R6 is hydrogen or hydroxy;
- R9 is hydrogen, hydroxy, halogen or oxo or R9 designates, together with R3, an additional bond between the carbon atoms at which R9 and R3 are placed;
- R10 is hydrogen, halogen or hydroxy;
- R11 is hydroxy, optionally substituted alkoxy, acyloxy, sulphonyloxy, phosphonyloxy, oxo, halogen, C1-C4 alkandiyl (bound to the same carbon atom of the sterol skeleton) or ═NOR28 wherein R28 is hydrogen or C1-C3 alkyl;
- R12 is hydrogen, hydroxy, C1-C3 alkyl, vinyl, C1-C3 alkoxy or halogen;
- R13 is hydrogen, hydroxy or halogen;
- R14 is hydrogen, hydroxy or halogen;
- R15 is hydrogen, halogen, C1-C4 alkyl, methylene, hydroxy, methoxy, acetoxy, oxo or ═NOR23 wherein R23 is hydrogen or C1-C3 alkyl;
- R16 is hydrogen, halogen, C1-C3 alkyl, methylene, hydroxy, methoxy, oxo or ═NOR24 wherein R24 is hydrogen or C1-C3 alkyl;
- R17 is hydrogen or hydroxy;
- R18 and R19 are both hydrogen, or one of R18 and R19 is hydrogen while the other is halogen, hydroxy or methoxy, or R18 and R19 together designate oxo;
- R25 is C1-C4 alkyl or hydroxymethyl, or R25 and R31 together designate methylene or oxo;
- R29 is hydrogen, halogen, methyl, hydroxy or oxo;
- R30 is hydrogen, halogen, methyl or hydroxy;
- R31 is hydrogen, halogen, methyl or hydroxy, or R31, together with R25, designates methylene or oxo;
- and A is a carbon atom;
- and when A is a carbon atom, R7 is hydrogen, hydroxy or halogen;
- and R8 is hydrogen, halogen, hydroxy, C1-C4 alkyl, methylene or oxo;
- R20 is C1-C4 alkyl, trifluoromethyl or C3-C6 cycloalkyl;
- provided that at least one of R1, R2, R6, R8, R9, R10, R12, R13, R14, R18, R19, R29, R30 and R31 is hydroxy or R25 is hydroxymethyl and further provided that R9, R10 and R11 are not all hydroxy;
- wherein the compound is useful for regulating meiosis in a mammalian germ cell.
Dependencies are inferred from the claim text.