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Maleic acid salt of(2s)-N-{5-[amino(imino)methyl]-2-thienyl}methyl-1-{(2R)-2-[(carboxymethyl)amino]-3,3-diphenylpropanoyl}-2-pyrrolidine carboxamide and a process for preparing same

A maleate and thienyl technology, applied to (2S)-N-{5-[amino(imino)methyl]-2-thienyl}methyl-1-{(2R)-2- [(carboxymethyl)amino]3, which can solve the problems of difficult absorption and low dissolution of compounds

Inactive Publication Date: 2005-07-20
LG LIFE SCI LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] Some compounds may be poorly absorbed due to low dissolution rates

Method used

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  • Maleic acid salt of(2s)-N-{5-[amino(imino)methyl]-2-thienyl}methyl-1-{(2R)-2-[(carboxymethyl)amino]-3,3-diphenylpropanoyl}-2-pyrrolidine carboxamide and a process for preparing same
  • Maleic acid salt of(2s)-N-{5-[amino(imino)methyl]-2-thienyl}methyl-1-{(2R)-2-[(carboxymethyl)amino]-3,3-diphenylpropanoyl}-2-pyrrolidine carboxamide and a process for preparing same
  • Maleic acid salt of(2s)-N-{5-[amino(imino)methyl]-2-thienyl}methyl-1-{(2R)-2-[(carboxymethyl)amino]-3,3-diphenylpropanoyl}-2-pyrrolidine carboxamide and a process for preparing same

Examples

Experimental program
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Effect test

Embodiment 1

[0024] Amorphous (2S)-N-{5-[amino(imino)methyl]-2-thienyl}methyl-1-{(2R)-2-[(carboxymethyl)amino]-3, Preparation of 3-diphenylpropionyl}-2-pyrrolidinecarboxamide maleate

[0025] The free compound of Formula 1 (1 g) was dissolved in methanol (30 ml), and water (30 ml) was added thereto. One equivalent of maleic acid was added dropwise thereto, and the mixture was stirred for one hour. The solvent was removed under reduced pressure using a still to obtain the title amorphous maleate salt (1.1 g, yield 95%).

Embodiment 2

[0027] Crystalline (2S)-N-{5-[amino(imino)methyl]-2-thienyl}methyl-1-{(2R)-2-[(carboxymethyl)amino]-3,3 Preparation of -diphenylpropionyl}-2-pyrrolidinecarboxamide maleate (1)

[0028] The free compound of Formula 1 (3 g) was dispersed in methanol (50 ml), to which was added 1M maleic acid in methanol (30 ml), and the mixture was stirred for 0.5 hr. Subsequently, acetonitrile (300 ml) was added thereto. The mixture was stirred for 1 hour and then stood to obtain white crystals. The crystals were filtered, washed with acetonitrile, and dried in vacuo (2.25 g, 61.7% yield).

Embodiment 3

[0030] Crystalline (2S)-N-{5-[amino(imino)methyl]-2-thienyl}methyl-1-{(2R)-2-[(carboxymethyl)amino]-3,3 Preparation of -diphenylpropionyl}-2-pyrrolidinecarboxamide maleate (2)

[0031] The free compound of Formula 1 (2.3 g) was dispersed in ethanol (100 ml), to which was added 1M maleic acid in methanol (4.3 ml), and the mixture was stirred for 0.5 hr. Subsequently, acetonitrile (500 ml) was added thereto. The mixture was stirred for 1 hour and then stood to obtain white crystals. The crystals were filtered, washed with acetonitrile, and dried in vacuo (1.04 g, 38.3% yield).

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Abstract

The present invention relates to a maleic acid salt of (2S)-N-{5-[amino(imino)methyl]-2-thienyl}methyl-1-{(2R)-2-[(carboxymethyl)amino]-3,3-diphenylpropanoyl}-2-pyrrolidinecarboxamide.

Description

technical field [0001] The present invention relates to (2S)-N-{5-[amino(imino)methyl]-2-thienyl}methyl-1-{(2R)-2-[(carboxymethyl) represented by the following formula (1) Base) amino]-3,3-diphenylpropionyl}-2-pyrrolidinecarboxamide maleate, and a method for preparing the salt: [0002] [Formula 1] [0003] Background of the invention [0004] The free compound of formula (1), that is, the compound to which no acid is added, and pharmaceutically acceptable salts, hydrates, solvates and isomers thereof are Korean Patent Publication No. 2000-047461 and WO 0039124, and can be effectively used as a new thrombin inhibitor. [0005] If a drug does not have the right physical properties for its development, several methods can be used to improve them. Specifically, if a certain drug has low solubility, the preparation of a salt of the drug is used as a general method for improving solubility. Methods for preparing its salts are generally well known (...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61P7/02C07C51/41C07D409/12C07K1/30C07K5/065A61K38/00
CPCC07K2299/00C07K5/06078A61P7/02C07D409/12
Inventor 金爱梨朴宰玄尹奭均朴哲院赵官衡
Owner LG LIFE SCI LTD
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