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Paclitaxel derivatives, preparation method and medicinal composition and usage thereof

The technology of paclitaxel analogs and compounds is applied in the field of preparation of drugs for the treatment of cancer, which can solve the problems that have not been developed into clinical drugs, and achieve the effect of simple preparation method and high yield

Inactive Publication Date: 2007-10-31
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Patent WO9638138 (Protaxel, Noveltaxoids, Biophysica Foundation), WO98 / 58927 (Buck Norton Pharmaceutical Co., Ltd.), CN00115426.5 (polyhydroxy water-soluble derivatives of paclitaxel and preparation method thereof, Fudan University) disclose several novel soluble Paclitaxel derivatives, used to treat tumors or other paclitaxel-sensitive diseases, but have not yet been developed into clinical therapeutic drugs

Method used

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  • Paclitaxel derivatives, preparation method and medicinal composition and usage thereof
  • Paclitaxel derivatives, preparation method and medicinal composition and usage thereof
  • Paclitaxel derivatives, preparation method and medicinal composition and usage thereof

Examples

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preparation example 1

[0041] Preparation Example 1 Preparation of 10-deacetyl-7,10-TROC-baccatin III (II 1 , R 1 =R 4 =TROC).

[0042] Add 500 mg (0.92 mmol) of 10-deacetylbaccatin III to the dry reaction flask, dissolve it in 10 ml of anhydrous pyridine, and place it in ice-salt water to cool. 0.43ml (32mmol) of 2,2,2-trichloroethoxycarbonyl chloride was added dropwise to the reaction liquid, after the dropwise addition was completed, the reaction was continued for 3 hours, and water was added to terminate the reaction. The reaction solution was extracted three times with 50 ml of ethyl acetate, the combined organic solution was washed with 1N hydrochloric acid and saturated sodium chloride, and dried over anhydrous sodium sulfate. After filtration and concentration, 1.14 g of a yellow oil was obtained, which was separated through a silica gel column and recrystallized from methanol to obtain 715 mg of a white solid. Yield 87%, melting point: 233-235°C.

preparation example 2

[0043] Preparation Example 2 Preparation of 7-TROC-Baccatin III (II 2 , R 1 =OAc,R 4 =TROC).

[0044] 7.38g (12.6mmol) of baccatin III, 3.4ml (25.2mmol) of 2,2,2-trichloroethoxycarbonyl chloride, and the other conditions were the same as in Preparation Example 1 to obtain 6g of white solid. Yield: 63%, melting point: 232-235°C.

preparation example 3

[0045] Preparation Example 3 Preparation of 13-[(2′R,3′S)-3′-phenyl-2′-hydroxyl-3′-amino-propionyl]-10-deacetyl-7,10-TROC-bar Cardin III (III 1 , R 1 =R 4 =TROC,R 3 =Ph).

[0046] Add 600 mg (0.673 mmol) of 10-deacetyl-7,10-TROC-baccatin III (II 1 , R 1 =R 4 =TROC), dissolved in 30ml of anhydrous toluene, then added 345mg (1.08mmol) (4S, 5R)-N-tert-butoxycarbonyl-2,2-dimethyl-phenyl-5-oxazolidinecarboxylic acid, 173mg (0.84mmol) of dicyclohexylcarbodiimide and 41mg (0.34mmol) of N,N-dimethylaminopyridine were reacted at 80°C for 4 hours, the reaction solution was washed with water, and the organic layer was concentrated to dryness. Add 7ml of formic acid to the residue, stir at room temperature until the solid dissolves, and continue to react at room temperature for 5 hours. Then, the reaction liquid was added into ice water containing 18 g of sodium bicarbonate, extracted three times with 60 ml of dichloromethane, the organic layers were combined, washed with saturate...

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Abstract

The invention discloses a new Paclitaxel derivant with second class amido group in lateral chain and good water-solubility as general formula (I), preparing method, medicinal compound with this chemical compound and application to prepare the cancer treatment medicine.

Description

technical field [0001] The present invention relates to a new class of paclitaxel derivatives, a preparation method thereof, a pharmaceutical composition containing the compound, and an application of the compound in preparing medicines for treating cancer. Background technique [0002] Paclitaxel was isolated from Taxus brevifolia by Wani et al. in 1971 (Wani MC, Taylor HL, Wall ME. The isolation and structure of taxol, a novel antileukemic and antitumor agent from taus brevifolia.J.Am.Chem .Soc.1971, 93, 2325), its structure is complex, but its anti-cancer mechanism is unique, it can promote microtubule polymerization and inhibit microtubule depolymerization (Horwitz SB, Fant J, Schiff PB.Promoton of microtubule assembly in vitro by taxol . Nature, 1979, 277, 665). After in-depth research, it has been found that it has broad-spectrum anti-cancer activity, and has been approved for marketing in many countries around the world. It is clinically used to treat ovarian cancer,...

Claims

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Application Information

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IPC IPC(8): C07D305/14C07D417/12A61K31/337A61P35/00
CPCY02P20/55
Inventor 吴克美叶仙蓉籍秀娟张福荣王凤
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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