Androgen derivatives for use in the inhibition of sex steroid activity
AssigneeEndorecherche, Inc.
InventorsFernand Labrie, Yves Merand
Life of this patent
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Abstract
Methods for treating sex steroid-dependent diseases by inhibiting sex steroid activity include administration of novel compounds which include an androgenic nucleus substituted at a ring carbon with at least one substituent specified herein. Such compounds may function by inhibiting sex steroid synthesis (both estrogen and androgen synthesis) and/or by antagonistically blocking androgen receptors.
Claims18
A compound represented by the formula:
- wherein the dotted line represents an optional pi bond, and
- (i) R.sup.7.alpha. is (CH.sub.2).sub.y L--G wherein y is an integer from 4-20, L is selected from the group consisting of --CONR.sup.4 --, --CSNR.sup.4 --, --NR.sup.5 CS-- or --CH.sub.2 -- (R.sup.4 and R.sup.5 being H or methyl), and G is selected from the group consisting of lower alkyl, lower alkenyl and halo (C.sub.1 -C.sub.8) alkyl,
- R.sup.17.beta. is hydroxyl or alkanoyloxy, and
- R.sup.17.alpha. is hydrogen, (C.sub.1 -C.sub.8) alkyl, or R.sup.17.beta. and
- R.sup.17.alpha. together are represented by the formula ##STR19## (ii) R.sup.17.alpha. is --C.tbd.C--(CH.sub.2).sub.y --L--G, wherein y is an integer from 4-20, L is selected from the group consisting of --CONR.sup.4 --, --CSNR.sup.4 --, --NR.sup.5 CS-- or --CH.sub.2 -- (R.sup.4 and R.sup.5 being H or methyl), and G is selected from the group consisting lower alkyl, lower alkenyl and haloalkyl,
- R.sup.17.beta. is a hydroxyl group or an ester derivative thereof,
- R.sup.7.alpha. is hydrogen.
A compound represented by the formula:
- ##STR21## wherein the dotted lines represent optional carbon-carbon bonds;
- n is an integer from 1-14;
- R is selected from the group consisting of hydrogen, (C.sub.1 -C.sub.8) alkyl, (C.sub.1 -C.sub.20) alkanoyl, (C.sub.3 -C.sub.20) alkenoyl, (C.sub.3 -C.sub.20) alkynoyl, (C.sub.7 -C.sub.11) aryl and alkylsilyl;
- and
- X is selected from the group consisting of halogen, --CN, a 3-9 membered nitrogen hetero ring and N(R.sup.7).sub.2 (R.sup.7 being hydrogen or (C.sub.1 -C.sub.8) alkyl).
A compound selected from the group consisting of N-butyl, N-methyl- 11-(17'.beta.-hydroxy-4'-androsten-3'-on-7'.alpha.-yl) undecanamide, 17.beta.-hydroxy-17.alpha.-(12'-iodododecynyl)-4-androsten-3-one, and 17.beta.-hydroxy-17.alpha.-(5'-iodopentynyl)-4-androsten-3-one.
Dependencies are inferred from the claim text.