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Gamma-aminobutyric acid derivative and its preparing process

A technology of aminobutyric acid and derivatives, applied in the field of γ-aminobutyric acid derivatives, can solve problems such as increasing drug stability

Inactive Publication Date: 2008-09-10
BEIJING RUNDEKANG MEDICAL TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, it can avoid the lactamization impurities that are easily produced during the storage of existing γ-aminobutyric acid derivatives, and increase the stability of the drug

Method used

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  • Gamma-aminobutyric acid derivative and its preparing process
  • Gamma-aminobutyric acid derivative and its preparing process
  • Gamma-aminobutyric acid derivative and its preparing process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1 Compound I 1 preparation of

[0023] Add 8gNaOH and 150ml water into the reaction flask, stir to dissolve, cool in an ice bath, add 31.8g of pregabalin, and drop 52.4g of BOC anhydride-250ml dioxane solution and 8.8gNaOH-220ml aqueous solution at the same time after completely dissolving. The rate of addition is such that the pH of the reaction solution is controlled at about 9, and the addition is completed in about 1 hour. Then continue to react for 2h, rise to room temperature for 2h. Stop the reaction, extract excess BOC anhydride in the reaction solution with ether, extract 4 times, consume 250ml of ether each time, discard. Adjust the pH of the water phase to about 3 with 5% citric acid solution, extract 3 times with ethyl acetate, 600ml each time, combine the organic phases, wash 3 times with water, wash 3 times with saturated brine, and dry over anhydrous magnesium sulfate for more than 4 hours. After filtration and concentration, 44.5 g of BOC-preg...

Embodiment 2

[0026] Example 2 Compound I 2 preparation of

[0027] Referring to the method of Example 1, BOC-D-serine was replaced by BOC-L-serine to obtain compound I 2 . Elemental Analysis C 11 h 24 N 2 o 4 Cl 2 : Calculated (, %): C 41.38, H 7.52, N 8.78; Measured (, %): C 41.62, H 7.54, N 8.56. MS (ESI, m / e): 247.1 (M+1).

Embodiment 3

[0028] Example 3 Compound I 3 preparation of

[0029] Referring to the method of Example 1, BOC-L-threonine was replaced by BOC-L-serine to obtain compound I 3 . Elemental Analysis C 12 h 26 N 2 o 4 Cl 2 : Calculated value (, %): C 43.24, H 7.81, N 8.41; Measured value (, %): C 43.02, H 7.70, N 8.38. MS (ESI, m / e): 260.9 (M+1).

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PUM

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Abstract

The invention provides a gamma-amino butyric acid derivative shown in the formula(I), optical isomers or medicine salts of optical isomers accepted in the pharmacy and an application for preparing drugs for treating neuropathic pain and falling sickness, wherein R1 is H,R2 is CH2CH(CH3)2 or R1, R2 is cyclohexyl, and R is of alkyl with the number of carbon atoms of 1 to 6, substituted alkyl or cycloalkyl and hydroxy containing amino acid residue which includes serine residue and threonine residue and has the D, L or DL structure.

Description

technical field [0001] The present invention relates to gamma-aminobutyric acid derivatives, optical isomers or pharmaceutically acceptable salts thereof and their use in preparing medicines for neuropathic pain and epilepsy. Background technique [0002] Neuropathic pain refers to pain syndromes caused by primary lesions or dysfunctions of the central or peripheral nervous system. It can be caused by trauma or / and disease-induced damage to peripheral nerves, posterior roots of the spinal cord, spinal cord and some parts of the central nervous system above. According to the etiology, nature and degree of nerve injury, it is clinically divided into two categories: central nerve pain and peripheral nerve pain caused by peripheral nerve injury. Central nerve pain, referred to as central pain, is primary pain caused by damage or dysfunction of the pain conduction pathway of the central nervous system. It is commonly seen in spinal cord trauma or cerebrovascular diseases, multip...

Claims

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Application Information

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IPC IPC(8): C07C229/22A61K31/223A61P25/02A61P25/04A61P25/08
Inventor 姚勇敢
Owner BEIJING RUNDEKANG MEDICAL TECH CO LTD