Antigestagenically active steroids with a fluorinated 17-alpha-alkyl chain
AssigneeSchering Corporation
InventorsWolfgang Schwede, Arwed Cleve, Ulrich Klar, Gunter Neef, Kristof Chwalisz, Martin Schneider, Ulrike Fuhrmann, Holger Heb-Stumpp
Life of this patent
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Abstract
17α-fluoroalkyl steroids of formula I as well as their physiologically compatible salts with acids and for —CO2R9 radicals with R9 meaning hydrogen, as well their physiologically compatible salts with bases, have an extraordinarily strong antigestagenic action and are suitable for the production of pharmaceutical preparations.
Claims25
A method for treating breast cancer or post-coital birth control comprising administering to a human in need thereof an effective amount of a 17α-Fluoroalkyl steroid of general formula I
- in which
- R1 stands for a methyl or ethyl group,
- R2 stands for a radical of formula CnFmHo, whereby n is 2, 3, 4, 5 or 6, m>1 and m+o=2n+1,
- R3 stands for a free etherified or esterified hydroxy group,
- R4 and R5 each stand for a hydrogen atom, together for an additional bond or a methylene group,
- St stands for a steroidal ABC-ring system of partial formula A, B or C
- in which
- R6 means a hydrogen atom, a straight-chain C1-C4 alkyl group or branched C3-C4 alkyl group or a halogen atom,
- R7 means a hydrogen atom, a straight-chain C1-C4 alkyl group or a branched C3-C4 alkyl group, or
- if St stands for a steroidal ABC-ring system A or B, in addition
- R6 and R7 together mean an additional bond,
- X means an oxygen atom, a hydroxyimino grouping=N—OH or two hydrogen atoms,
- R8 means a radical Y or an aryl radical that is optionally substituted in several places with a group Y, whereby Y is a hydrogen atom, a halogen atom, an —OH, —NO2, —N3, —CN, —NR9aR9b, —NHSO2R9, —CO2R9, C1-C10 alkyl, C1-C10 alkoxy, C1-C10 alkanoyloxy, benzoyloxy, C1-C10 alkanoyl, C1-C10 hydroxyalkyl or benzoyl group, and R9a and R9b are the same or different and represent a hydrogen atom or a C1-C10 alkyl group,
- or for a —NR9aR9b radical, also a physiologically compatible salt thereof with an acid, or for a —CO2R9 radical in which R9 is hydrogen, also a physiologically compatible salt thereof with a base.
Dependencies are inferred from the claim text.