Title:
CONVENIENT SYNTHESIS OF S-FLUOROMETHYL 6ALPHA, 9ALPHA-DIFLUORO-11BETA-HYDROXY-16ALPHA- METHYL-17ALPHA-PROPIONYLOXY-3-OXOANDROSTA-1, 4-DIENE-17BETA-CARBOTHIOATE
Document Type and Number:
WIPO Patent Application WO2004001369
Kind Code:
A3
Abstract:
The present invention provides a convenient process for the preparation of S-fluoromethyl 6a, 9a-difluoro-11b-hydroxy-16a-methyl-17a-propionyloxy-3-oxoandrosta-1, 4-diene-17b-carbothioate, a compound of formula (1), comprising(a) treating 17b-[(N, N-dimethylcarbamoyl)thio]carbonyl-6a,9a-difluoro-11b-hydroxy-16a-methyl-17a-propionyloxy-3-oxoandrosta-1, 4-diene, a compound of formula (3) with alkali metal carbonate-alcohol system to obtain 6a, 9a-difluoro-11b-hydroxy-16a-methyl-17a-propionyloxy-3-oxoandrosta-1, 4-diene-17b-carbothioic acid, a compound of formula (4); (b) reacting the compound of formula (4) with bromofluoromethane to yield the compound of formula (1).The present invention also provides an improved process for preparation of compound of formula (1) comprising (a) reacting 6a, 9a-difluoro-11b-hydroxy-16a-methyl-3-oxo-17a-(propionyloxy) androsta-1, 4-dien-17b-carboxylic acid, a compound of formula (2), with N,N-dimethylthiocarbamoyl chloride in an inert aprotic solvent in the presence of an iodide catalyst and a base to give a compound of formula (3), (b) reacting the compound of formula (3) with a hydrosulfide reagent and bromofluromethane to obtain a compound of formula (1).
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Inventors:
JADAV KANAKSINH JESINGBHAI (IN)
KAMBHAMPATI SUDHAKAR (IN)
CHITTURI TRINADHA RAO (IN)
THENNATI RAJAMANNAR (IN)
KAMBHAMPATI SUDHAKAR (IN)
CHITTURI TRINADHA RAO (IN)
THENNATI RAJAMANNAR (IN)
Application Number:
PCT/IN2003/000219
Publication Date:
April 08, 2004
Filing Date:
June 16, 2003
Export Citation:
Assignee:
SUN PHARMACEUTICAL IND LTD (IN)
JADAV KANAKSINH JESINGBHAI (IN)
KAMBHAMPATI SUDHAKAR (IN)
CHITTURI TRINADHA RAO (IN)
THENNATI RAJAMANNAR (IN)
JADAV KANAKSINH JESINGBHAI (IN)
KAMBHAMPATI SUDHAKAR (IN)
CHITTURI TRINADHA RAO (IN)
THENNATI RAJAMANNAR (IN)
International Classes:
C07J3/00; C07J31/00; C07J41/00; (IPC1-7): C07J31/00; C07J75/00
Domestic Patent References:
| WO2001062722A2 | 2001-08-30 |
Foreign References:
| GB2088877A | 1982-06-16 |
Other References:
DATABASE CASREACT [online] XP002985181, accession no. STN-International, Kalsruhe (DE), CASREACT Database accession no. 129:276096
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