scispace - formally typeset
Search or ask a question
Patent

Intermediates for the hemisynthesis of taxanes and preparation processes therefor

TL;DR: In this paper, the present invention generally relates to at least one precursor compound and derivatives thereof, a process for preparing a taxane, and a baccatin derivative, and is related to the present paper.
Abstract: The present invention generally relates to at least one precursor compound and derivatives thereof, a process for preparing a taxane, and a baccatin derivative.
Citations
More filters
Patent
06 Jul 2012
TL;DR: In this article, a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product from a feed mixture which is a fish oil or which is derived from fish oil is presented.
Abstract: The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product from a feed mixture which is a fish oil or which is derived from fish oil, which process comprises the steps of: (i) purifying the feed mixture in a chromatographic separation step, to obtain a first intermediate product; and (ii) purifying the first intermediate product obtained in (i) in a simulated or actual moving bed chromatographic separation step, to obtain a second intermediate product; and (iii) purifying the second intermediate product obtained in (ii) in a simulated or actual moving bed chromatographic separation step, to obtain the PUFA product; wherein an aqueous organic solvent is used as eluent in each separation step; saturated and/or monounsaturated fatty acids present in the feed mixture are removed in the first separation step; the PUFA product is separated from different components of the feed mixture in steps (ii) and (iii); and the PUFA product obtained in the third separation step contains EPA or an EPA derivative in an amount greater than 90 wt%.

14 citations

Patent
24 Dec 2010
TL;DR: In this paper, a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product from a feed mixture, which process comprises introducing the feed mixture to a simulated or actual moving bed chromatography apparatus having a plurality of linked chromatography columns containing, as eluent, an aqueous alcohol, was presented.
Abstract: The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product, from a feed mixture, which process comprises introducing the feed mixture to a simulated or actual moving bed chromatography apparatus having a plurality of linked chromatography columns containing, as eluent, an aqueous alcohol, wherein the apparatus has a plurality of zones comprising at least a first zone and second zone, each zone having an extract stream and a raffinate stream from which liquid can be collected from said plurality of linked chromatography columns, and wherein (a) a raffinate stream containing the PUFA product together with more polar components is collected from a column in the first zone and introduced to a nonadjacent column in the second zone, and/or (b) an extract stream containing the PUFA product together with less polar components is collected from a column in the second zone and introduced to a nonadjacent column in the first zone, said PUFA product being separated from different components of the feed mixture in each zone.

11 citations

Patent
09 Jan 2014
TL;DR: In this paper, a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product from a feed mixture is presented, where the PUFA product is other than alpha-linolenic acid.
Abstract: The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product from a feed mixture, which comprises: (a) purifying the feed mixture in a first chromatographic separation step using an eluent a mixture of water and a first organic solvent, to obtain an intermediate product; and (b) purifying the intermediate product in a second chromatographic separation step using as eluent a mixture of water and a second organic solvent, to obtain the PUFA product, wherein the second organic solvent is different from the first organic solvent and has a polarity index which differs from the polarity index of the first organic solvent by between 0.1 and 2.0, wherein the PUFA product is other than alpha-linolenic acid (ALA), gamma-linolenic acid (GLA), linoleic acid, an ALA mono- di- or triglyceride, a GLA mono- di- or triglyceride, a linoleic acid mono- di- or triglyceride, an ALA C1-C4 alkyl ester, a GLA C1-C4 alkyl ester or a linoleic acid C1-C4 alkyl ester or a mixture thereof.

10 citations

Patent
07 Jan 2014
TL;DR: In this paper, a process for recovering a first polyunsaturated fatty acid from a feed mixture, wherein the feed mixture comprises at least a second fatty acid in addition to the first PUFA, was proposed.
Abstract: The invention relates to a process for recovering a first polyunsaturated fatty acid from a feed mixture, wherein the feed mixture comprises at least a second fatty acid in addition to the first polyunsaturated fatty acid, the process comprising: - performing a main step of chromatographic separation using an aqueous organic eluent and thereby collecting a first stream of eluent enriched in the first polyunsaturated fatty acid and a second stream of eluent enriched in the second fatty acid; - subjecting the second stream of eluent to a concentration step so as to obtain a stream of concentrated fatty acids on the one hand and a depleted second stream of eluent on the other hand, wherein the water-to-organic ratio of the depleted second stream of eluent is lower than the water-to-organic ratio of the second stream of eluent; recycling at least part of the depleted second stream of eluent to use it in the main step of chromatographic separation.

9 citations

Patent
06 Jul 2012
TL;DR: In this paper, a chromatographic separation process for recovering polyunsaturated fatty acid (PUFA) product from a feed mixture is presented, which process comprises passing the feed mixture through one or more columns containing, as eluent, an aqueous organic solvent, wherein the temperature of at least one of the chromatogram columns through which the feed is passed is greater than room temperature.
Abstract: The present invention provides a chromatographic separation process for recovering a polyunsaturated fatty acid (PUFA) product from a feed mixture, which process comprises passing the feed mixture through one or more chromatographic columns containing, as eluent, an aqueous organic solvent, wherein the temperature of at least one of the chromatographic columns through which the feed mixture is passed is greater than room temperature.

7 citations

References
More filters
Patent
02 Nov 1987
TL;DR: In this paper, the authors present an approach for the extraction of taxols useful as chemotherapeutic agents, and the present invention is directed to the process of preparing taxols and various intermediates in said process.
Abstract: The present invention is directed to novel taxols useful as a chemotherapeutic agent. Moreover, the present invention is directed to the process of preparing taxols and various intermediates in said process. A key intermediate is this process is 2,5-dihydroxy-2-patchoulenes. Therefore the present invention is also related to said intermediate and the process for its preparation.

104 citations

Journal ArticleDOI
TL;DR: In this paper, the half-lives of O and N substituted 2.2′ and 7-polyethylene glycol esters of taxol were measured under neutral, acidic and physiological (basic) conditions.

92 citations

Patent
19 Nov 1992
TL;DR: In this paper, a method for the production of a substantially optically pure taxane side chain comprising the steps of synthesizing a racemic mixture of enantiomers of the side chain that is capable of exhibiting conglomerate behavior was proposed.
Abstract: This invention relates to a method for the production of a substantially optically pure taxane side chain comprising the steps of synthesizing a racemic mixture of enantiomers of the taxane side chain that is capable of exhibiting conglomerate behavior and resolving the substantially optically pure enantiomers by direct crystallization methods. This invention also relates to the semisynthesis of taxanes such as taxol through coupling the substantially optically pure taxane side chain to a taxane ring nucleus.

58 citations

Patent
20 Feb 1991
TL;DR: In this paper, a method for the preparation of β-phenylglycidic-(2R, 3R) acid optionally in the form of salt or ester was proposed.
Abstract: Method for the preparation of β-phenylglycidic-(2R,3R) acid optionally in the form of salt or ester by precipitation of the salt of the β-phenylglycidic-(2R,3R) acid with (+)-α-methylbenzylamine-(R) in a solution of a mixture of salts of cis and trans β-phenylglycidic acids with (+)-α-methylbenzylamine-(R). Utilisation of the resulting product for implementing the method for the preparation of taxol and its analogues.

19 citations

Patent
13 Sep 1990
TL;DR: In this paper, a process for preparing optically active 3-phenylglycidic acid ester compound is described, which comprises permitting a culture broth, cells or treated cells of a microorganism having the ability of stereoselectively hydrolyzing a (2R, 3S)-3-PNE compound to act on a racemic 3-PNEster compound which may also have a substituent on the phenyl group.
Abstract: There is disclosed a process for preparing optically active 3-phenylglycidic acid ester compound, which comprises permitting a culture broth, cells or treated cells of a microorganism having an ability of stereoselectively hydrolyzing a (2R, 3S)-3-phenylglycidic acid ester compound to act on a racemic 3-phenylglycidic acid ester compound which may also have a substituent on the phenyl group, thereby hydrolyzing the (2R, 3S) optically active isomer and separating and collecting the (2S, 3R) antipode from the reaction mixture.

13 citations