183133-97-3Relevant academic research and scientific papers
Taxol derivative cabazitaxel synthesis route using novel catalyst
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Paragraph 0017; 0019, (2020/09/24)
The invention belongs to the field of drug intermediate synthesis, and particularly relates to a paclitaxel derivative cabazitaxel synthetic route using a novel catalyst. The paclitaxel derivative cabazitaxel synthetic route comprises the following steps: adding Dimetoxy-10-DAB, (4S,5R)-2,2-dimethyl-4-phenyl-3-tert-butyloxycarbonyl-3,5-oxazacyclopentanecarboxylic acid, a solid catalyst Ti(SO4)O and a solvent toluene into a four-neck flask provided with a thermometer, a stirrer and a reflux condensing tube; heating to 60-80 DEG C, filtering, and carrying out reduced pressure distillation aftera TLC detection reaction is finished so as to obtain a faint yellow paste; and crystallizing petroleum ether and ethyl acetate so as to obtain white powder, namely a cabazacitaxel precursor. Accordingto the invention, a new solid superacid catalyst structure model is used in the method, and has potential high stability and reusability, so that the catalytic effect is guaranteed while the anaphylactic reaction caused by DCC is avoided, and it can also be guaranteed that DCC cannot be left in the product.
TAXANE COMPOUND, AND PREPARATION METHOD AND USE THEREOF
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, (2016/12/16)
Provided are taxanes compounds having the structure of formula I, preparation method thereof, and uses of compositions having the compound, pharmaceutical salts and solvates thereof as active ingredients in the preparation of oral antitumor drugs. In the formula, R1 is —COR6, —COOR6, and —CONR7aR7b; R2 is C1-C6 alkyl, C1-C6 alkenyl group, a substituted hydrocarbon group, a heterocyclic group, an aromatic group or a substituted aromatic group; R3 is —OR6, —OCOOR6, —OCOSR6, and —OCONR7aR7b; R4 is —OR6, —OCOOR6, —OCOSR6, —OCONR7aR7b, H, and OH; R6 is C1-C6 alkyl, C1-C6 alkenyl, C1-C6 alkynyl group, a substituted hydrocarbon group, an aromatic group or a heterocyclic group; and R7a and R7b are respectively hydrogen, a hydrocarbon group, a substituted hydrocarbon group or a heterocyclic group.
Taxanes Compounds, Preparation Method Therefor, and Uses Thereof
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, (2016/10/31)
The present invention provides taxanes compounds with a formula (I) or formula (II) structure, a method for preparing the compounds, as well as the use of the compositions containing the compounds, pharmaceutically acceptable salts and solvates thereof as active ingredients in manufacturing oral antitumor medicaments, In formula (I), R1 is —COR6, —COOR6 or —CONR7aR7b; R2 is a C1-C6 alkyl, a C1-C6 alkenyl, a substituted hydrocarbon group, a heterocyclic group, an aromatic group or a substituted aromatic group; R3 is —OR6, —OCOOR6, —OCOSR6 or —OCONR7aR7b; R4 is —OR6, —OCOOR6, —OCOSR6, —OCONR7aR7b or H; wherein, R6 is a C1-C6 alkyl, a C1-C6 alkenyl, a C1-C6 alkynyl, a substituted hydrocarbon group, an aromatic group or a heterocyclic group; R7a and R7b are respectively hydrogen, a hydrocarbon group, a substituted hydrocarbon group or a heterocyclic group. In formula (II), R1 is —COR6 or —COOR6; R2 is an aromatic group; R3 is —OR6; wherein, R6 is a C1-C6 alkyl, a C1-C6 alkenyl, a C1-C6 alkynyl, a substituted hydrocarbon group, an aromatic group or a heterocyclic group.
PROCESS FOR THE PREPARATION OF CABAZITAXEL AND ITS SOLVATES
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, (2015/06/25)
The present disclosure provides anisole and benzyl alcohol solvates of cabazitaxel and methods of their production. The solvates may be characterized by powder x-ray diffraction patterns. The present disclosure also provides methods for the synthesis of cabazitaxel.
NOVEL METHOD FOR PREPARING CABAZITAXEL FROM 10-DEACETYLBACCATIN III IN HIGH YIELD, AND NOVEL INTERMEDIATE THEREFOR
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, (2015/11/03)
The present invention relates to a novel method for preparing cabazitaxel from 10-deacetylbaccatin III, and a novel intermediate therefor, and more specifically, to: a method which allows cabazitaxel to be more easily prepared in a high yield and in a high purity within a short time compared with a conventional method by preparing cabazitaxel via a novel intermediate using 10-deacetylbaccatin III as a starting material, and thus is suitable for industrial mass production; and a novel intermediate therefor.
The synthesis of novel taxoids for oral administration
Jing, Yun-Rong,Zhou, Wei,Li, Wan-Liang,Zhao, Lin-Xiang,Wang, Yong-Feng
, p. 194 - 203 (2014/01/17)
A group of novel taxoids, with modifications at C-7, C-10, C-3′ and C-14 positions of paclitaxel, was synthesized in order to improve their biological profile by decreasing their affinity with P-glycoprotein (P-gp) and increasing cellular permeability. Most of the new taxoids demonstrated the similar potent cytotoxic activities in MCF-7 human tumor cell line as paclitaxel in vitro. In the permeability assay with monolayers of Caco-2 cells, most of the compounds demonstrated an increased trans-cellular transport in A-to-B direction in comparison with paclitaxel. Among them the compounds T-13, T-15 and T-26 showed the highest permeability, and with efflux ratios better than that of ortataxel. The interaction of the compounds T-13 and T-26 with P-gp was evaluated using Madin-Darby canine kidney (MDCK)-multidrug resistance-1(MDR1) and MDCK-wild-type (WT). The results indicated that T-13 and T-26 were poor substrates for P-gp and possessed inhibiting effects of P-gp mediated efflux. It was thus clear that simultaneous modifications at the C-7, C-10 and C-3′ positions of paclitaxel significantly impaired its interactions with P-gp and interfered with P-gp mediated efflux.
PROCESS FOR THE PREPARATION CABAZITAXEL
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, (2014/03/24)
The present invention discloses a process for the preparation of 4-acetoxy-2α-benzoyloxy-5β,20-epoxy-1-hydroxy-7β,10β-dimethoxy-9-oxotax-11-en-13α-yl(2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-3-phenyl-propionate Cabazitaxel (I).
PROCESS FOR MAKING AN INTERMEDIATE OF CABAZITAXEL
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, (2013/04/13)
A novel process of making 7,10-dialkyl-10-DAB of formula (I) which is useful as a key intermediate for the preparation of cabazitaxel, comprises selective elaboration of positions 7 and 10 of 10-deacetylbaccatin III.
PROCESSES FOR THE PREPARATION OF CABAZITAXEL INVOLVING C(7) -OH AND C(13) -OH SILYLATION OR JUST C(7) -OH SILYLATION
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, (2013/05/23)
Disclosed are processes towards Cabazitaxel (I) starting from 10-Deacetylbaccatin (III) that involve steps of either 7-OH monosilylation (passing through formula V) or 7,13-disilylation (passing through formulae XI, XII). Isopropanol Solvates of Cabazitaxel and processes to make this are also described.
PROCESS FOR CABAZITAXEL, AND INTERMEDIATES THEREOF
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, (2013/05/21)
The present invention relates to processes for making cabazitaxel, cabazitaxel analogues and intermediates thereof. The invention provides novel compounds useful in the synthesis of cabazitaxel.
