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Method for preparing ilomastat

A technology for ilomastat and intermediates, which is applied in the field of preparation of ilomastat, can solve the problems of cumbersome operation and dark product color, and achieve the effects of increasing solubility, high condensation efficiency, and not easy to deliquescence

Inactive Publication Date: 2010-02-24
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Abstract
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Problems solved by technology

Experiments have found that when trifluoroacetic acid is used to remove tert-butyl ester, it may be due to the indole group in the structure, resulting in a darker color of the product, and in the post-treatment process, it is necessary to repeatedly add solvents and distill to remove trifluoroacetic acid. Acetic acid, thereby obtaining solid intermediate, such operation is very loaded down with trivial details

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  • Method for preparing ilomastat
  • Method for preparing ilomastat
  • Method for preparing ilomastat

Examples

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Embodiment Construction

[0044] The present invention will be further illustrated by specific preparation examples below, however, it should be understood that these examples are only used for more detailed description and should not be construed as limiting the present invention in any form. In the description of the present invention, unless otherwise specified, the reagents, raw materials, intermediates, solvents, etc. used can be obtained from commercial sources or prepared by methods known to those skilled in the art.

[0045] 1, Preparation of L-Tryptophanamide (II)

[0046] Mix L-tryptophan methyl ester hydrochloride (144.74g, 0.57mol) with methylamine aqueous solution (25-30%) 430mL, stir at room temperature for 7 hours, use dichloromethane to carry out continuous extraction for 5 hours, separate , the obtained organic phase was dried with anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain a light yellow solid, which was washed with P 2 o 5 After dr...

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Abstract

The invention relates to a new method for preparing ilomastat, which comprises the following steps of: reacting a tryptophan methyl ester hydrochloride with a methylamine to prepare tryptophanyl methylamine; performing a condensation reaction between the tryptophanyl methylamine and a tert-butyl acetate succinate derivative to prepare a midbody of a formula (IV); removing the tert-butyl from the midbody of formula (IV) to form a midbody of a formula (V); and performing a condensation reaction between the midbody of formula (V) and a free hydroxylamine to form the ilomastat. The method of the invention is simple in the process and low in the cost.

Description

technical field [0001] The present invention relates to a new method for preparing ilomastat. Background technique [0002] Ilomastat (English name: Ilomastat, chemical name: N-[(2R)-2-(hydroxylaminecarbonylmethyl)-4-methylpentanylcarbonyl]-L-tryptophanamide), is a Broad-spectrum, potent matrix metalloproteinase inhibitor, which has a strong inhibitory effect on multiple members of the matrix metalloproteinase family. The chemical structural formula of ilomastat is as follows: [0003] [0004] In the 1990s, the American company Glycomed first developed it for the treatment of corneal ulcers. Clinical trials have shown that ilomastat has a good therapeutic effect on alkali-induced corneal damage. In recent years, it has been found that ilomastat has the effect of slowing down and improving facial wrinkles and preventing myopia. [0005] WO 9209563 discloses a method for preparing ilomastat as shown in the following scheme: [0006] [0007] The method disclosed in ...

Claims

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Application Information

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IPC IPC(8): C07D209/20
Inventor 刘克良韩寒梁远军许笑宇
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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