US2012010231A1PendingUtilityA1
Dihydroetorphines and Their Preparation
Est. expiryDec 8, 2028(~2.4 yrs left)· nominal 20-yr term from priority
A61P 25/04A61P 29/00C07D 489/02C07D 489/12A61K 31/485C07D 489/10A61K 9/7023
61
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Claims
Abstract
The present invention provides a process for the preparation of a compound of formula (VI), or a salt or derivative thereof, wherein R 1 and R 2 are independently C 1-8 alkyl and * represents a stereocentre.
Claims
exact text as granted — not AI-modified1 . A process for the preparation of a compound of formula (VI), or a salt or derivative thereof
(wherein R 1 and R 2 are independently C 1-8 alkyl and * represents a stereocentre) comprising hydrolysing a compound of formula (V)
wherein R 1 , R 2 and * are as hereinbefore defined.
2 . A process as claimed in claim 1 , wherein said compound of formula (V) is prepared by reacting a compound of formula (IV)
(wherein R 1 is as hereinbefore defined);
with a compound of formula R 2 M(X) p , wherein R 2 is C 1-8 alkyl, M is metal, X is halide and p is 1 or O.
3 . A process as claimed in claim 2 , wherein said compound of formula (IV) is prepared by reducing a compound of formula (III)
(wherein R 1 is as hereinbefore defined);
4 . A process as claimed in claim 3 , wherein said compound of formula (III) is prepared by reacting a compound of formula (I)
with a compound of formula (II)
(wherein R 1 is C 1-8 alkyl).
5 . A process for the preparation of a compound of formula (VI), or a salt or derivative thereof,
(wherein R 1 and R 2 are independently C 1-8 alkyl and * represents a stereocentre) comprising:
reacting a compound of formula (I)
with a compound of formula (II)
(wherein R 1 is C 1-8 alkyl) to give a compound of formula (III)
(wherein R 1 is as hereinbefore defined);
reducing said compound of formula (III) to produce a compound of formula (IV)
(wherein R 1 is as hereinbefore defined);
reacting said compound of formula (IV) with a compound of formula R 2 M(X) p , wherein R 2 is C 1-8 alkyl, M is metal, X is halide and p is 1 or 0, to give a compound of formula (V)
wherein R 1 , R 2 and * are as hereinbefore defined;
(iv) hydrolysing said compound of formula (V) to give a compound of formula (VI).
6 . A process as claimed any one of claims 1 to 5 , further comprising the step of crystallising said compound of formula (VI).
7 . A process as claimed in any one of claims 1 to 6 , wherein R 1 is propyl.
8 . A process as claimed in any one of claims 1 to 7 , wherein R 2 is methyl.
9 . A process as claimed in any one of claims 1 to 8 , wherein the stereocentre (*) in formulae (V) and (VI) is (S).
10 . A process as claimed in any one of claims 1 to 9 , wherein the compound of formula (V) is:
11 . A process as claimed in any one of claims 1 to 10 , wherein the compound of formula (VI) is:
12 . A process as claimed in any one of claims 1 to 8 , wherein the stereocentre (*) in formulae (V) and (VI) is (R).
13 . A compound of formula (VI), or a salt or derivative thereof,
wherein R 1 and R 2 are independently C 1-8 alkyl and the * represents a (S) stereocentre.
14 . A compound as claimed in claim 13 of formula (VI)
15 . A compound of formula (V), or a salt or derivative thereof,
wherein R 1 and R 2 are independently C 1-8 alkyl and the (*) represents a (S) or (R) stereocentre, preferably a (S) stereocentre.
16 . A compound as claimed in claim 15 of formula (Va)
17 . A compound of formula (IV)
(wherein R 1 is C 1-8 alkyl).
18 . A compound of formula (III)
(wherein R 1 is C 1-8 alkyl).
19 . A compound as claimed in claim 17 or claim 18 , wherein R 1 is propyl.
20 . A process for making a compound of formula (III) comprising reacting a compound of formula (I)
with a compound of formula (II)
(wherein R 1 is C 1-8 alkyl)
21 . A pharmaceutical composition comprising a compound as claimed in any one of claims 13 to 19 .
22 . A compound as claimed in any one of claims 13 to 19 for use in medicine.
23 . A compound as claimed in any one of claims 13 to 19 for use as an analgesic.
24 . Use of a compound as claimed in any one of claims 13 to 19 in the manufacture of a medicament for the treatment of pain.
25 . A method of treating a subject in need of pain relief comprising administering to said subject a therapeutically effective amount of a compound as claimed in any one of claims 13 to 19 .Join the waitlist — get patent alerts
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