US2015005488A1PendingUtilityA1
Process for the preparation of 17-(3-hydroxypropyl)-17-hydroxysteroids
Est. expiryJun 28, 2027(~0.9 yrs left)· nominal 20-yr term from priority
Y02P20/55C07J 53/008C07J 71/0005
44
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Claims
Abstract
The present invention relates to a process for the preparation of 17α-(3-hydroxypropyl)-17β-hydroxysteroids of the formula I starting from 17-ketosteroids of the formula III via the intermediates of the formula V wherein the radicals R 3 , R 5 , R 6 , R 7 , R 10 , R 13 , R 15 , R 16 , R 40 , R 41 and R 42 have the meaning indicated in the description.
Claims
exact text as granted — not AI-modified1 - 13 . (canceled)
14 . A process for preparing a compound of formula II
comprising oxidizing a compound of formula I
which compound of formula I has been synthesized by the complete catalytic hydrogenation of the alkyne function of a compound of formula V
and by removal of the benzylic protective group or groups,
wherein in the compounds of formulas I, II and V
R 3 is hydrogen or
R 30 , R 31 , R 32 are, independently of one another, hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy;
R 5 is hydrogen, or hydroxyl or together with R 6 can be a double bond;
R 6 is hydrogen, or together with R 5 or R 7 is a double bond; or together with R 7 is an α or β-CH 2 group;
R 7 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -thioacyl; or together with R 6 is a double bond or an α or β-CH 2 group;
R 10 is hydrogen, methyl or ethyl;
R 13 is methyl, or ethyl;
R 15 is hydrogen, or C 1 -C 4 -alkyl, or together with R 16 is a —CH 2 group or a double bond;
R 16 is hydrogen or together with R 15 is a —CH 2 group or a double bond, and
R 40 , R 41 , R 42 are, independently of one another, hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy.
15 . A process according to claim 14 , wherein a compound of formula I has been synthesized by the complete catalytic hydrogenation of the alkyne function of a compound of formula Va
wherein
R 3 is hydrogen or
R 30 , R 31 , R 32 are, independently of one another, hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; and
R 40 , R 41 , R 42 are, independently of one another, hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy;
and by removal of the benzylic protective group or groups.
16 . A process according to claim 14 , which is for the preparation of a compound of formula IIa
comprising oxidizing a compound of formula Ia
which compound of formula Ia has been synthesized by the complete catalytic hydrogenation of the alkyne function of a compound of formula Vb
and by removal of the benzylic protective group.
17 . A process according to claim 14 , wherein the compound of formula II is drospirenone.
18 . A process according to claim 15 , wherein the compound of formula II is drospirenone.
19 . A process in which a reaction of a compound of formula V
wherein
R 3 is hydrogen or
R 30 , R 31 , R 32 are, independently of one another, hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy;
R 5 is hydrogen, or hydroxyl or together with R 6 can be a double bond;
R 6 is hydrogen, or together with R 5 or R 7 is a double bond; or together with R 7 is an α or β-CH 2 group;
R 7 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -thioacyl; or together with R 6 is a double bond or an α or β-CH 2 group;
R 10 is hydrogen, methyl or ethyl;
R 13 is methyl, or ethyl;
R 15 is hydrogen, or C 1 -C 4 -alkyl, or together with R 16 is a —CH 2 group or a double bond;
R 16 is hydrogen or together with R 15 is a —CH 2 group or a double bond, and
R 40 , R 41 , R 42 are, independently of one another, hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy
leads to the preparation of a compound of formula II
wherein
R 6 is hydrogen, or together with R 7 is a double bond or an α or β-CH 2 group;
R 7 is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -thioacyl; or together with R 6 is a double bond or an α or β-CH 2 group;
R 10 is hydrogen, methyl or ethyl;
R 13 is methyl, or ethyl;
R 15 is hydrogen, or C 1 -C 4 -alkyl, or together with R 16 is a —CH 2 group or a double bond; and
R 16 is hydrogen or together with R 15 is a —CH 2 group or a double bond.
20 . A process according to claim 19 , wherein the compound of formula V is of formula Va
wherein
R 3 is hydrogen or
R 30 , R 31 , R 32 are, independently of one another, hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; and
R 40 , R 41 , R 42 are, independently of one another, hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy.
21 . A process according to claim 19 , wherein the compound of formula V is of formula Vb
22 . A process according to claim 19 , wherein the reaction of a compound of formula V leads to the preparation of drospirenone.
23 . A process according to claim 20 , wherein the reaction of a compound of formula Va leads to the preparation of drospirenone.
24 . A process according to claim 21 , wherein the reaction of a compound of formula Va leads to the preparation of drospirenone.
25 . A process for preparing a compound of formula II
comprising oxidizing a compound of formula I
which compound of formula I is provided from a process where it was synthesized by the complete catalytic hydrogenation of the alkyne function of a compound of formula V
and by removal of the benzylic protective group or groups,
wherein in the compounds of formulas I, II and V
R 3 is hydrogen or
R 30 , R 31 , R 32 are, independently of one another, hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy;
R 5 is hydrogen, or hydroxyl or together with R 6 can be a double bond;
R 6 is hydrogen, or together with R 5 or R 7 is a double bond; or together with R 7 is an α or β-CH 2 group;
R 7 is hydrogen, C 1 -C 4 -alkyl C 1 -C 4 -alkoxycarbonyl, C 1 -C 4 -thioacyl; or together with R 6 is a double bond or an α or β-CH 2 group;
R 10 is hydrogen, methyl or ethyl;
R 13 is methyl, or ethyl;
R 15 is hydrogen, or C 1 -C 4 -alkyl, or together with R 16 is a —CH 2 group or a double bond;
R 16 is hydrogen or together with R 15 is a —CH 2 group or a double bond, and
R 40 , R 41 , R 42 are, independently of one another, hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy.
26 . A process according to claim 25 , wherein a compound of formula I is provided from a process where it was synthesized by the complete catalytic hydrogenation of the alkyne function of a compound of formula Va
wherein
R 3 is hydrogen or
R 30 , R 31 , R 32 are, independently of one another, hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy; and
R 40 , R 41 , R 42 are, independently of one another, hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy;
and by removal of the benzylic protective group or groups.
27 . A process according to claim 25 , which is for the preparation of a compound of formula IIa
comprising oxidizing a compound of formula Ia
which compound of formula Ia is provided from a process where it was synthesized by the complete catalytic hydrogenation of the alkyne function of a compound of formula Vb
and by removal of the benzylic protective group.
28 . A process according to claim 25 , wherein the compound of formula II is drospirenone.
29 . A process according to claim 26 , wherein the compound of formula II is drospirenone.Join the waitlist — get patent alerts
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