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Preparation and application of amino substituted carboxylic acid compounds

A technology of compounds and carboxylic acids, which is applied in the field of two new types of amino-substituted carboxylic acid compounds and their preparation, can solve the problems of unsatisfactory effect of promoting drainage

Inactive Publication Date: 2014-04-30
FOURTH MILITARY MEDICAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The chelating agent combined with aminocarboxylic acid and phenolic hydroxyl overcomes some deficiencies of EDTA and DTPA, and enhances the chelating ability of the chelating agent. It has been observed in animal experiments that the excretion promoting effect of this type of chelating agent on most metals is enhanced, but the existing The effect of chelating agents on nuclides, especially uranium, is still not satisfactory

Method used

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  • Preparation and application of amino substituted carboxylic acid compounds
  • Preparation and application of amino substituted carboxylic acid compounds
  • Preparation and application of amino substituted carboxylic acid compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1 compound 2-carbonylmethylamino-2-2', 3'-dihydroxyphenylacetic acid (4, R in general formula (I) 1 = H, R 2 =H) Preparation

[0021] Add catechol (1, R 2 =H) 2.2g, 2-oxoacetic acid (2) 1.84g, 2-aminoacetic acid (3, R 1 =H) 1.65g and water 20mL, mix well, add 0.5mL acetic acid dropwise, heat to reflux for reaction (TLC detection end point), cool, filter with suction, wash with a small amount of ethanol, and dry to obtain 2.26g of white solid. Y=47%; mp: 220°C (decomposition); 1 H NMR (DMSO-d 6 , 400MHz): δ7.41 (d, J=8.2Hz, 1H), 6.80-7.21 (m, 2H), 3.23-3.11 (m, 3H) ppm; MS (m / z, ESI - ): 240[M-H] - ;IR (KBr): 3430, 3021, 2980, 1687, 1679, 1219cm -1 .

Embodiment 2

[0022] Example 2 Compound 2-N, N-dicarbonylmethylamino-2-2', 3'-dihydroxy-5'-methoxyphenylacetic acid (5, R in the general formula (I) 1 =CH 2 CO 2 H, R 2 =OCH 3 ) preparation

[0023] Add substituted catechol (1, R 2 =4-methoxy) 11.2g, 2-oxoacetic acid (2) 7.36g, iminodiacetic acid (3, R 1 =CH 2 CO 2 H) 10.64g and 80mL of water, mix well, add 0.5mL of acetic acid dropwise, heat to reflux for reaction (TLC detection end point), cool and suction filter to obtain 6.9g of white solid. Y=53%; mp: 250°C (decomposition); 1 H NMR (DMSO-d 6 , 400MHz): δ7.35-7.24 (m, 2H), 3.87 (s, 3H), 3.43 (s, 1H), 3.32-3.21 (m, 4H) ppm; MS (m / z, ESI - ): 328[M-H] - ;IR (KBr): 3430, 3052, 2992, 2635, 1695, 1637, 1210cm -1 .

Embodiment 3

[0024] Example 3 compound 2,2'-N,N-dicarbonylmethylamino-2',3'-dihydroxy 1',4'-phenyl diacetic acid (6, R in general formula (II) 1 =CH 2 CO 2 H, R 2 =H) Preparation

[0025] Add catechol (1, R 2 =H) 4.4g, 2-oxoacetic acid (2) 7.36g, iminodiacetic acid (3, R 1 =CH 2 CO 2 H) 10.64g and 70mL of water, after mixing evenly, add 0.5mL of acetic acid dropwise, heat to reflux for reaction (TLC detection end point), cool and filter with suction to obtain 6.8g of white solid. Y=70%; mp: 250°C (decomposition); 1 H NMR (DMSO-d 6 , 400MHz): δ7.42 (d, J=8.6Hz, 2H), 3.41 (s, 2H), 3.40-3.23 (m, 8H) ppm; MS (m / z, ESI - ): 487[M-H] - ;IR (KBr): 3435, 3052, 2987, 2685, 1701, 1629, 1265cm -1 .

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Abstract

The invention relates to two novel amino substituted carboxylic acid compounds and a preparation method thereof. The compounds can be used for the prevention and treatment of in-vivo metal poisoning and the preparation of metal decorporation medicaments and health products. The amino substituted carboxylic acid compounds combine the advantages of aminocarboxylic acid and phenolic hydroxyl; and the two novel chelators designed by effectively introducing carboxyl chelation groups onto the benzylic site of a benzene ring have fine metal poisoning prevention and treatment activity and metal decorporation activity. By adding the effective chelation groups on the benzylic site in the molecule chelation center, the nuclide ion bonding capability is enhanced, so that the compounds can be easily formed into stable complexes, thereby accelerating the in-vivo discharge and improving the decorporation effect and poisoning prevention and treatment effect of metal (especially uranium).

Description

Technical field [0001] The invention relates to two types of novel amino-substituted carboxylic acid compounds and a preparation method thereof, which can be used for the prevention and treatment of metal poisoning in the body and the preparation of metal excretion-promoting drugs and health care products. Background technique [0002] There are a variety of metal elements in nature, some elements such as iron, zinc, magnesium, calcium are necessary elements to maintain human health, but some metal elements such as lead, mercury, arsenic, especially actinide nuclides (uranium, thorium, etc.) Erosion of human health, and excessive essential elements will also affect human health. Due to the increasing application of radioactive elements, radionuclides caused by radioactive pollution enter the body and exist for a long time, which is also an important factor in carcinogenesis. The use of chelating agent drugs to accelerate the discharge of harmful metal elements in the body a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C227/14C07C229/36A61K31/198A61P39/04A23L1/29A23L33/00
Inventor 张邦乐何炜郭军周四元万宁李骅巨佳张芳芳
Owner FOURTH MILITARY MEDICAL UNIVERSITY
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