High specific rotatory power levoleucovorin calcium and resolution method thereof

A technology of calcium leucovorin and calcium folinate, applied in organic chemistry and other fields, can solve problems such as unrepeatable results

Inactive Publication Date: 2003-03-12
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

D.B.Cosulich et al [D.B.Cosulich et al., J.Am.Chem.Soc., 74, 4215-16, 1952] reported as early as 1952 that there are two diastereomers of 6R and 6S in calcium folinate According to the difference in the solubility of the two in water, the 6S configuration of levofolinic acid calcium can be separated, but the results have not been replicated

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] 1. Mix 60g (6R, S)-calcium folinate with 540-690ml of distilled water, heat and dissolve, and add anhydrous CaCl with a molar mass 6.5 times that of calcium folinate 2 . The temperature was lowered to 30°C, and 25% ammonia water was added dropwise to adjust the pH value to 10. After the dropwise addition was completed, the temperature was slowly lowered to 18° C. and kept at a constant temperature for 18 hours. Filter the precipitate with 5% CaCl 2 The solution was washed with absolute ethanol and dried to obtain 25 g of light yellow solid. [α] D 20 =-12° (c=1, H 2 O, the concentration is based on anhydrous salt).

[0022] 2. In the first step, mix 60g of the split product with 540-690ml of distilled water and heat to about 60°C, adjust the pH value to about 5.5 with 20% HCl, and completely dissolve the solid, then adjust the pH value to 7.0- with 5% NaOH solution 7.5, add anhydrous CaCl with a molar mass 3.5 times that of calcium folinate 2 , After the dissolut...

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Abstract

The present invention relates to a calcium levofolite with high specific rotation and a process for obtaining said compound by resolution of the diastereisomerically mixed calcium folite. Its specific rotation is -17.7 deg. and its content of (6S)-calcium folite is greater than 99%.

Description

field of invention [0001] The invention relates to a high specific rotation calcium levofolinate and a method for separating the high specific rotation calcium levofolinate from diastereomeric mixed calcium folinate. technical background [0002] Calcium folinate {chemical name: N-[4-[(2-amino-5-formyl-1,4,5,6,7,8-hexahydro-4-oxo-6-pteridinyl) Methyl]amino]benzoyl-L-glutamic acid calcium salt pentahydrate} as an antidote and anti-anemia drug, its molecular structure is as follows: [0003] Since there are two chiral carbon atoms in the molecule, the configuration of the chiral carbon atom at the glutamic acid site is determined, and there are two configurations of R and S on the carbon atom at the 6th position, so calcium folinate It has been administered as a mixture of diastereomers. According to reports, the effects of the two isomers on enzymes in vivo are not the same, wherein the compound with the configuration of the carbon atom at the 6th position being the S con...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
Inventor 林国强孙江勤夏克敏许旭
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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