Aminosalicylic acid derivative lysine complex salt, preparation method and application thereof

A technology of aminosalicylic acid and lysine, which is applied to the preparation of cyanide reaction, the preparation of organic compounds, chemical instruments and methods, etc., can solve the problems of poor solubility and achieve good water solubility

Inactive Publication Date: 2010-08-04
NANJING MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Derivatives of aminosalicylic acid with general structural formula 1 have definite PSD-95 / nNOS decoupling (Zhu Dongya et al., Chinese Patent Publication No. 101492384A), however, its solubility in water is not good

Method used

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  • Aminosalicylic acid derivative lysine complex salt, preparation method and application thereof
  • Aminosalicylic acid derivative lysine complex salt, preparation method and application thereof
  • Aminosalicylic acid derivative lysine complex salt, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Example 1 4-(5-fluoro-2-hydroxybenzylamino)-2-hydroxybenzoic acid lysine salt

[0016] Under room temperature and electromagnetic stirring, 1.46g (0.01mol) lysine 10mL was added dropwise to 2.77g (0.01mol) 4-(5-fluoro-2-hydroxybenzylamino)-2-hydroxybenzoic acid in 10mL ethanol solution The aqueous solution, then cooled to 5-15 ° C, reacted for 2-5 hours, and precipitated solid. Filter and dry in vacuo to obtain white crystals.

[0017] 1 H NMR (DMSO-d 6 )δ: 1.42(m, 2H); 1.56(m, 2H); 1.70(m, 2H); 2.77(t, J=7.5Hz, J=7.5Hz, 2H); 3.30(t, J=6Hz, J =6Hz, 1H); 4.21(s, 2H); 5.92-7.46(m, 6H); 9.60(s, 2H); 11.44(s, 1H);

Embodiment 2

[0018] Example 2 4-(5-bromo-2-hydroxybenzylamino)-2-hydroxybenzoic acid lysine salt

[0019] At room temperature and under electromagnetic stirring, add 1.46 g (0.01 mol) lysine 10 mL dropwise to 3.38 g (0.01 mol) of 4-(5-bromo-2-hydroxybenzylamino)-2-hydroxybenzoic acid in 10 mL of ethanol The aqueous solution, then cooled to 5-15 ° C, reacted for 2-5 hours, and precipitated solid. Filter and dry in vacuo to obtain white crystals.

[0020] 1 H NMR (DMSO-d 6 )δ: 1.42(m, 2H); 1.56(m, 2H); 1.70(m, 2H); 2.77(t, J=7.5Hz, J=7.5Hz, 2H); 3.30(t, J=6Hz, J =6Hz, 1H); 4.24(s, 2H); 6.72-7.78(m, 6H); 9.96(s, 2H); 11.44(s, 1H);

Embodiment 3

[0021] Example 3 4-(3,5-dichloro 2-hydroxybenzylamino) 2-hydroxybenzoic acid lysine salt (compound 1)

[0022] At room temperature and under electromagnetic stirring, 1.46 g (0.01 mol) of lysine was added dropwise to a solution of 3.28 g (0.01 mol) of 4-(3,5-dichloro-2-hydroxybenzylamino)-2-hydroxybenzoic acid in 10 mL of ethanol. Amino acid 10mL aqueous solution, then lower the temperature to 5-15°C, react for 2-5 hours, and a solid is precipitated. Filter and dry in vacuo to obtain white crystals.

[0023] 1 HNMR (DMSO-d 6 )δ: 1.42(m, 2H); 1.56(m, 2H); 1.70(m, 2H); 2.77(t, J=7.5Hz, J=7.5Hz, 2H); 3.30(t, J=6Hz, J =6Hz, 1H); 4.24(s, 2H); 5.74-7.39(m, 5H, ph); 8.41(s, 6H);

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Abstract

The invention relates to aminosalicylic acid derivative lysine complex salt, a preparation method and application thereof. The structure of the aminosalicylic acid derivative lysine complex salt conforms to the following general formula (I), R1 stands for -H, -Cl or -Br; R2 stands for -F, -Cl or -Br; one of R3 and R4 stands for COO-, and the other one stands for -OH or -OCOCH3. A target compound of the aminosalicylic acid derivative lysine complex salt has the pharmacological action of treating neuropathic pain.

Description

1. Technical field [0001] The invention belongs to the technical field of pharmacy, and in particular relates to a class of aminosalicylic acid derivative lysine double salt, a preparation method thereof and an application in preparation of medicines for treating neurogenic pain. 2. Background technology [0002] Compounds that specifically block the coupling of PSD-95 and nNOS have clear neuronal cell protection and analgesic effects (SK Florio, et al British Journal of Pharmacology, 158, 494-506; GWAG, Byonng-Joo, WO2007 / 119973A1 ; Zhu Dongya, etc., Chinese Patent Publication No. 101492384A). Therefore, the PSD-95 / nNOS uncoupler may become a new type of nerve cell protective agent, and it may also become a non-opioid central analgesic, which has a good research prospect. [0003] Derivatives of aminosalicylic acid with general structural formula 1 have definite PSD-95 / nNOS decoupling (Zhu Dongya et al., Chinese Patent Publication No. 101492384A), but their solubility in w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/64C07C227/18A61K31/606A61K31/616A61P25/04
Inventor 李飞朱东亚季兴罗春霞吴海银徐海兵
Owner NANJING MEDICAL UNIV
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