US5202448A
Expired / Lapsed
US
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Processes of converting taxanes into baccatin III
Assignee: Mayne Pharma USA Inc
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Filing: 1992-08-14
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Granted: 1993-04-13
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Expires: 2012-08-14
Abstract
Abstract The present invention relates to a process of converting partially purified taxane mixtures into Baccatin III. The process for the preparation of Baccatin III includes contacting a mixture containing at least one taxane compound having an ester linkage at the C-13 position with at least one borohydride reducing salt in a reaction solvent in the present of a Lewis acid.
Inventors
- 👤 David R. Carver
- 👤 Timothy R. Prout
- 👤 Hernita A. Ewald
- 👤 Donia L. Henderson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 13:28
CPC Classifications
C; C07; C07D; C07D305/00; C07D305/14
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
48 words
A process for the preparation of a compound of formula (I) ##STR3## comprising contacting a mixture containing at least one taxane compound having an ester linkage at the C-13 position with at least one borohydride reducing salt in a reaction solvent in the presence of a Lewis acid.
Claim 2
Dependent Claim
48 words
A process for the preparation of a compound of formula (I) ##STR3## comprising contacting a mixture containing at least one taxane compound having an ester linkage at the C-13 position with at least one borohydride reducing salt in a reaction solvent in the presence of a Lewis acid.
Claim 3
Dependent Claim
17 words
The process of claim 1 conducted at a range temperature of from room temperature to -30° C.
Claim 4
Dependent Claim
13 words
The process of claim 1 wherein the borohydride reducing salt is sodium borohydride.
Claim 5
Dependent Claim
13 words
The process of claim 1 wherein the borohydride reducing salt is tetrabutylammonium borohydride.
Claim 6
Dependent Claim
56 words
The process of claim 1 wherein the reaction solvent is selected from the group consisting of: CH 3 OCH 2 CH 2 OCH 2 , CH 3 OCH 2 CH 2 OCH 2 CH 2 OCH 3 , and CH 3 OCH 2 CH 2 OCH 2 CH 2 OCH 2 CH 2 OCH 3 .
Claim 7
Dependent Claim
11 words
The process of claim 1 wherein the reaction solvent is tetrahydrofuran.
Claim 8
Dependent Claim
11 words
The process of claim 1 wherein the reaction solvent is dichloromethane.
Claim 9
Dependent Claim
22 words
The process of claim 1 wherein the mixture contains at least 15%-50% taxanes which are taxol and the reaction solvent is tetrahydrofuran.
Claim 10
Dependent Claim
24 words
The process of claim wherein the mixture contains greater than 50% by weight of taxanes which are taxol and the reaction solvent is dichloromethane.
Claim 11
Dependent Claim
60 words
The process of claim 1 wherein the mixture contains less than 15% by weight of taxanes which are taxol and the reaction solvent is selected from the group consisting of CH 3 OCH 2 CH 2 OCH 3 , CH 3 O(CH 2 CH 2 O)CH 3 , and CH 3 O(CH 2 CH 2 O) 3 CH 3 .
Claim 12
Dependent Claim
13 words
The process of claim 1 wherein the Lewis acid is a metal halide.
Claim 13
Dependent Claim
12 words
The process of claim 11 wherein the metal halide is tin chloride.
Claim 14
Dependent Claim
12 words
The process of claim 11 wherein the metal halide is cobalt chloride.
Claim 15
Dependent Claim
39 words
A process for the preparation of a compound of formula (I) ##STR4## comprising contacting a mixture containing at least one taxane compound constituent having an ester linkage at the C-13 position with a borohydride reducing salt in aromatic hydrocarbons.
Claim 16
Dependent Claim
39 words
A process for the preparation of a compound of formula (I) ##STR4## comprising contacting a mixture containing at least one taxane compound constituent having an ester linkage at the C-13 position with a borohydride reducing salt in aromatic hydrocarbons.
Claim 17
Dependent Claim
12 words
The process according to claim 14 wherein said aromatic hydrocarbon is toluene
Claim 18
Dependent Claim
14 words
The process according to claim 14 wherein said borohydride reducing salt is tetrabutylammonium borohydride.
Claim 19
Dependent Claim
14 words
The process according to claim 14 is conducted at a temperature of 0° C.
Claim 20
Dependent Claim
70 words
A process for the preparation of a compound of formula (I) ##STR5## comprising contacting a mixture containing a taxane compound which is taxol and at least one other taxane compound having an ester linkage at the C-13 position that is not taxol with a borohydride reducing salt in a reaction solvent wherein the taxane compound which is taxol in the mixture is not converted to formula I as defined above.
Claim 21
Dependent Claim
70 words
A process for the preparation of a compound of formula (I) ##STR5## comprising contacting a mixture containing a taxane compound which is taxol and at least one other taxane compound having an ester linkage at the C-13 position that is not taxol with a borohydride reducing salt in a reaction solvent wherein the taxane compound which is taxol in the mixture is not converted to formula I as defined above.
Claim 22
Dependent Claim
13 words
The process according to claim 18 wherein the reducing salt is sodium borohydride.
Claim 23
Dependent Claim
12 words
The process according to claim 19 wherein the reaction solvent is ethanol.
Claim 24
Dependent Claim
13 words
The process according to claim 20 conducted at a temperature of -30° C.
References Cited (Backward Citations)
No citation records indexed.
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1996-04-12 | 1996-10-12 | 1997-04-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-04-12 | 2000-10-12 | 2001-04-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-04-12 | 2004-10-12 | 2005-04-13 | $7700.00 | Window Closed / Lapsed |