Process for the glycosidation of colchicine and thiocolchicine

一种化合物、甲硫基的技术，应用在制备秋水仙碱和硫秋水仙碱糖苷及其衍生物领域，能够解决冗长时间、产率低、不令人满意等问题

Inactive Publication Date: 2011-05-04
INDENA SPA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method is unsatisfactory due to the low yield and the time required for the lengthy and sectioned method

Method used

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  • Process for the glycosidation of colchicine and thiocolchicine
  • Process for the glycosidation of colchicine and thiocolchicine
  • Process for the glycosidation of colchicine and thiocolchicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0027] The following examples illustrate the invention in more detail.

[0028] 1) Synthesis of thiocolchicoside (3-O-β-D-glucopyranosyl-3-O-demethylthiocolchicine)

[0029] Suspend 3-O-demethylthiocolchicine (2.0 g) in acetonitrile (20 ml) at room temperature under a nitrogen atmosphere, and then add 1,1,3,3-tetramethylguanidine (1.8 ml) in sequence A solution of 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose (5.60 g) in acetonitrile (10 ml) and finally boron trifluoride (7.2 ml).

[0030] The reaction mixture was stirred at room temperature for 2 hours, then cooled to 5°C and quenched by adding 2M KOH to pH ≈ 6 (approximately 20 ml). The aqueous layer was separated and extracted with acetonitrile (10ml). The combined organic layers were sequentially washed with NaHSO 4 0.5M (20ml), NaHCO 3 6% (20ml) and brine (20ml) washes.

[0031] The solvent was removed under vacuum and replaced with 95% ethanol (30ml). 2M NaOH (40ml) was added and the solution was stirred until compl...

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Abstract

A process for the preparation of compounds having formula (I) is disclosed, wherein: - R1 is a methoxy or methylthio group; - R2 is a O-glycosyloxy residue. Compounds having formula (I) are prepared by reacting the corresponding precursor having R2 = OH and the suitably protected 1-acetyl-glycose.

Description

technical field [0001] The invention discloses a method for preparing colchicine and thiocolchicine (thiocolchicine) glycosides and derivatives thereof. Background of the invention [0002] Colchicine (I, R 1 = R 2 =OMe) is an alkaloid that has long been widely used in the treatment of gout. In addition, colchicine is also a very potent bacteriostatic agent, which acts by blocking the formation of the mitotic spindle in cell division; this property has been well studied for any antitumor activity, and large quantities have been prepared for this purpose. Colchicine derivatives. colchicine and thiocolchicine (I, R 1 =SMe,R 2 =OMe) is a raw material that can be used in the preparation of a range of active pharmaceuticals. [0003] 3-O-demethyl-thiocolchicine glucoside or thiocolchicine (I R 1 =SMe,R 2 =β-D-O-glucosyl) is an active ingredient that has a very important use in the field of pharmacy, mainly in the treatment of diseases of the musculoskeletal system. 3-O-D...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/248C07C49/755
CPCC07H1/00C07H15/248C07C231/12C07C319/20Y02P20/55C07C2603/34A61P19/00A61P21/00C07C323/41C07C233/25
Inventor S·拜斯赞特B·加贝塔
Owner INDENA SPA
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