74 results about "10-Deacetylbaccatin" patented technology

This invention relates to a process for preparation of taxanes comprisingsubjecting 7,10-diprotected intermediates 7-O-(2-haloacyl)baccatin III 6c or 7,10-O-di-(2-haloacyl)-10-deacetylbaccatin III 6b to a step of coupling with (4S,5R)-3-[(2-alkyl / aryl-2-trialkylsilyl)ethoxy-carbonyl]-4-aryl-2-substituted-1,3-oxazolidine-5-carboxylic acid 1 in the presence of a condensation agent, an activating agent and an aromatic hydrocarbon to obtain 7-O-[2-(haloacyl)]-13-[(4S,5R)-4-aryl-2-substituted-3(2-unsubstituted / substituted-2-trialkylsilyl)-ethoxycarbonyl-1,3-oxazolidinyl-5-carbonyl]baccatin III 7a or 7,10-di-O[2-(haloacyl)]-13-[(4S,5R)-4-aryl-2-substituted-3-(2-unsubstituted / substituted-2-trialkylsilyl)ethoxy-carbonyl-1,3-oxazolidinyl-5-carbonyl]-10-deacetylbaccatin III 7b;treating the coupled products 7-O-[2-(haloacyl)]-13-[(4S,5R)-4-aryl-2-substituted-3-(2-substituted-2-trialkylsilyl)ethoxy-carbonyl-1,3-oxazolidinyl-5-carbonyl]baccatin III 7a or 7,10-di-O-[2[(haloacyl)]-13-[(4S,5R)-4-aryl-2-substituted-3-(2-substituted-2-trialkylsilyl)ethoxycarbonyl-1,3-oxazolidinyl-5-carbonyl]-10-deacetylbaccatin III 7b with tetraalkylammonium halide in a haloalkane to obtain free amine of structure 8;treating free amine 8 with acid chloride or acid anhydride in the presence of a base in a heterogeneous phase to obtain the intermediates of structure 9;subjecting the intermediates of compound 9 to the deprotection of 2-haloacyl group under mild alkaline condition at −20 to +40° C. for 6–24 h in the presence of ammonia or aliphatic amines or aromatic amines or their combination to obtain paclitaxel or docetaxel.

A process is provided for the semi-synthesis of taxane intermediates useful in the preparation of paclitaxel and docetaxel, in particular, the semi-synthesis of 10-deacetylbaccatin III and baccatin III, and derivatives thereof, from a mixture of taxanes.

9-dihydro-13-acetylbaccatin III, one of the chemicals obtained from Taxus canadensis is used to produce, inter alia, 10-decetylbaccatin III, a useful intermediate for the preparation of paclitaxel and analogues thereof The 9-dihydro-13-acetylbaccatin III is converted into the 10-deacetylbaccatin III by a simple three step process involving (a) replacement of the C-7 hydroxyl group of tho 9-dihydro compound with a protecting group, (b) the oxidizing of the C-7 protected compound to produce a C-9 ketone, and (c) the deprotecting of the C-9 ketone to produce 10-deacetylbaccatin III.

The present invention relates to a process is provided for the conversion of 9-dihydro-13-acetylbaccatin to 10-deacetylbaccatin III. The process includes four specific interrelated steps. The first step involves protecting the 7-hydroxyl group of 9-dihydro-13-acetylbaccatin and converting that 7-hydroxyl-protected 9-dihydro-13-acetylbaccatin to 7, 13-diacetyl-9-dihydrobaccatin III. The second step involves reacting that 7, 13-diacetyl-9-dihydrobaccatin III with 4-methylmorpholine N-oxide in a suitable solvent and oxidizing that reaction product to yield 7, 13-diacetylbaccatin. The third step involves deacetylating that 7, 13-diacetyl-9-dihydrobaccatin III to yield 7-acetylbaccatin III. The fourth and final step involves converting that 7-acetylbaccatin III to 10-deacetylbaccatin III.

The invention discloses a method for improving yield of 10-deacetylbaccatin III produced by fungi. The method comprises the following steps: culturing in a culture medium to produce 10-deacetylbaccatin III, specifically, culturing at 25 DEG C for three days, then culturing at 10 DEG C for six hours, then culturing at 25 DEG C for 12 hours, and then culturing at 30 DEG C for six hours, and circulating like this at 12 variable temperatures. Therefore, the yield of 10-deacetylbaccatin III produced by fungi is stimulated by circulating excitation of high and low temperatures. Compared with the traditional culturing method, the method provided by the invention has the advantages that the yield of 10-deacetylbaccatin III is obviously improved, the operation is simple, the production cost is low, the purpose of improving the yield is achieved simply by changing the temperature, and the yield of 10-deacetylbaccatin III can be improved by 2.4 times.

A process is provided for the semi-synthesis and isolation of taxane intermediates useful in the preparation of paclitaxel and docetaxel, in particular, the semi-synthesis and isolation of 10-deacetylbaccatin III, and protected derivatives thereof, from a mixture of taxanes.

The invention relates to a method for using specific resin and silicon gel column chromatography purification via a negative pressure cavitation water extraction method to produce 10-deacetylbaccatin III and 7-xylose-10-deacetylpaclitaxel at high efficiency. The method comprises using taxus branch leaves as raw material, drying and breaking the raw material to process negative pressure cavitationwater extraction, filtering, using AB-8 resin to process dynamic absorption on filter liquor to concentrate 10-deacetylbaccatin III and 7-xylose-10-deacetylpaclitaxel and carrying out a further purification by middle pressure silicon gel column chromatography, to obtain the 10-deacetylbaccatin III of 60% purity or more and 7-xylose-10-deacetylpaclitaxel of 67% purity or more. The invention can use renewable taxus branch leaves to protect ecological resource and effectively extract effective component and biological semi synthesis precursor materials. The invention has simple operation, thus is suitable for industrial application and is important for industrial production.