US4924012A
Expired / Lapsed
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Process for preparing derivatives of baccatine III and of 10-deacetyl baccatine III
Assignee: Aventis Pharma SA
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Filing: 1989-04-03
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Granted: 1990-05-08
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Expires: 2009-04-03
Abstract
Abstract Process for preparing derivatives of baccatine III and of 10-deacetylbaccatine III, of general formula (I), in which R is hydrogen or acetyl, by condensation of an acid of general formula (II) with a derivative of baccatine III or of 10-deacetylbaccatine III of general formula (III), R 1 , R 2 and R 3 denoting hydroxy-protecting groups, followed by the replacement of the protecting groups by hydrogen. ##STR1##
Inventors
- 👤 Michel Colin
- 👤 Daniel Guenard
- 👤 Francoise Gueritte-Voegelein
- 👤 Pierre Potier
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 08:58
CPC Classifications
C; C07; C07D; C07D305/00; C07D305/14; A; A61; A61P; A61P35/00; A61P35/02; Y; Y02; Y02P; Y02P20/00; Y02P20/50; Y02P20/55
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
87 words
A process for preparing a derivative of baccatine III or of 10-deacetylbaccatine III, of general formula: ##STR13## in which R denotes hydrogen or acetyl, wherein an acid of general formula: ##STR14## in which R 1 is a hydroxy-protecting group, is condensed with a taxan derivative of general formula ##STR15## in which R 2 is an acetyl group or a hydroxy-protecting group and R 3 is a hydroxy-protecting group, and the protecting groups R 1 , R 3 and, where appropriate, R 2 are then replaced by hydrogen.
Claim 2
Dependent Claim
87 words
A process for preparing a derivative of baccatine III or of 10-deacetylbaccatine III, of general formula: ##STR13## in which R denotes hydrogen or acetyl, wherein an acid of general formula: ##STR14## in which R 1 is a hydroxy-protecting group, is condensed with a taxan derivative of general formula ##STR15## in which R 2 is an acetyl group or a hydroxy-protecting group and R 3 is a hydroxy-protecting group, and the protecting groups R 1 , R 3 and, where appropriate, R 2 are then replaced by hydrogen.
Claim 3
Dependent Claim
22 words
A process according to claim 1, wherein R 1 is chosen from the group comprising methoxymethyl, 1-ethoxyethyl, benzyloxymethyl, (β-trimethylsilylethoxy)methyl, tetrahydropyranyl and 2,2,2-trichloroethoxycarbonyl.
Claim 4
Dependent Claim
11 words
A process according to claim 2, wherein R 1 is 1-ethoxyethyl.
Claim 5
Dependent Claim
41 words
A process according to claim 1, wherein the hydroxy-protecting groups R 2 and R 3 which may be the same or different are each chosen from 2,2,2-trichloroethoxycarbonyl or trialkylsilyl groups in which each alkyl portion contains 1 to 3 carbon atoms.
Claim 6
Dependent Claim
12 words
A process according to claim 4, wherein the hydroxy-protecting group is 2,2,2-trichloroethoxyoarbonyl.
Claim 7
Dependent Claim
22 words
A process according to claim 1, wherein the condensation is performed in the presence of a condensing agent and an activating agent.
Claim 8
Dependent Claim
25 words
A process according to claim 6, wherein the condensing agent is chosen from carbodiimides and reactive carbonates and the activating agent is chosen from dialkylaminopyridines.
Claim 9
Dependent Claim
23 words
A process according to claim 7, wherein the condensing agent is chosen from dicyclohexylcarbodiimide and di-2-pyridyl carbonate, and the activating agent is 4-dimethylaminopyridine.
Claim 10
Dependent Claim
24 words
A process according to claim 1, wherein the condensation is preformed in an aromatic solvent chosen from benzene, toluene, xylenes, ethylbenzene, isopropylbenzene and chlorobenzene.
Claim 11
Dependent Claim
20 words
A process according to claim 1, wherein the condensation is performed at a temperature of between 60° and 90° C.
Claim 12
Dependent Claim
62 words
A process according to claim 1, for replacing by hydrogen of the protecting groups R 1 , R 3 and, where appropriate, R 2 on the intermediate product of general formula: ##STR16## comprising treating said intermediate with zinc in the presence of acetic acid or with an inorganic or organic acid dissolved in an aliphatic alcohol containing 1 to 3 carbon atoms.
References Cited (Backward Citations)
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| 3.5 Years (Year 4) | 1993-05-07 | 1993-11-06 | 1994-05-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-05-07 | 1997-11-06 | 1998-05-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-05-07 | 2001-11-06 | 2002-05-08 | $7700.00 | Window Closed / Lapsed |