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Phenylpropionic acid compound, preparation method therefor and medicinal use thereof

A compound, the technology of propionic acid, which is applied in the field of medicine and chemical industry, can solve the problems such as limited use

Active Publication Date: 2014-12-03
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, sphingosine 1-phosphate also has cardiovascular and bronchoconstrictive effects, which limit its usefulness as a therapeutic drug

Method used

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  • Phenylpropionic acid compound, preparation method therefor and medicinal use thereof
  • Phenylpropionic acid compound, preparation method therefor and medicinal use thereof
  • Phenylpropionic acid compound, preparation method therefor and medicinal use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0148] The preparation of embodiment 1:4-benzyloxybenzonitrile

[0149] According to the method of reaction scheme 1, the final product was obtained after infrared drying, and the yield was 98.4%.

[0150] 1 H-NMR (400MHz, DMSO-d6) δ (ppm): .7.78 (d, J=6.8, 2H), 7.31-7.48 (m, 5H), 7.19 (d, J=8.8, 2H), 5.21 (S , 2H), ESI-MS (M+H + ), 232.2.

Embodiment 2

[0151] Embodiment 2: the preparation of 4-benzyloxy thiobenzamide

[0152] According to the method of reaction scheme 1, the product was obtained after drying with a yield of 95.6%.

[0153] 1 H-NMR (400MHz, DMSO-d6) δ (ppm): 9.64, (s, 1H), 9.32, (s, 1H), 7.94 (d, J=8.8, 2H), 7.31—7.47 (brs, 5H) , 7.17 (d, J=9.2, 2H), 5.18 (S, 1H).

Embodiment 3

[0154] Embodiment 3: Preparation of 2-(4-benzyloxyphenyl)-4-thiazolic acid ethyl ester

[0155] According to the method in Reaction Scheme 1, the intermediate 2-(4-benzyloxyphenyl)-4-thiazole acid ethyl ester was obtained with a yield of 77.3%.

[0156] 1H-NMR (400MHz, DMSO-d6) δ (ppm): 8.50 (s, 1H), 7.93 (d, J = 8.8, 2H), 7.31—7.47 (brs, 5H), 7.17 (d, J = 8.8, 2H), 5.20 (S, 1H), 4.33 (q, J=6.8, 2H), 1.33 (t, J=7.2, 3H).

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Abstract

Disclosed is as represented by Formula I a compound or a pharmaceutically acceptable salt thereof. The compound or the pharmaceutically acceptable salt thereof of the present invention can be used as an immunosuppressant. By regulating the transport of leukocytes, and by regulating the cellular transport of lymphocytes, the lymphocytes are gathered in secondary lymphoid tissues, thus improving the integrity of blood vessels to allow for immunosuppression effect, anti-inflammatory activity, and hemostatic effect.

Description

technical field [0001] The invention belongs to the field of medicine and chemical industry, and relates to phenylpropionic acid compounds or pharmaceutically acceptable salts thereof, pharmaceutical compositions containing them, their preparation methods, and their medical applications. These compounds are SlP 1 / EDG1 receptor agonist, by regulating leukocyte transport, regulating lymphocyte cell transport, making lymphocytes gather in secondary lymphoid tissue, improving the integrity of blood vessels and exerting immunosuppressive effect, anti-inflammatory activity and hemostatic effect. Background technique [0002] Immunosuppressive and anti-inflammatory drugs have been shown to be useful in many autoimmune and chronic inflammatory diseases (including systemic lupus erythematosus, chronic rheumatoid arthritis, type 1 diabetes, inflammatory bowel disease, biliary cirrhosis, grapevine Meningitis, multiple sclerosis, and other diseases such as Crohn's disease, ulcerative ...

Claims

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Application Information

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IPC IPC(8): C07D277/56C07D277/42C07D277/30A61K31/426A61P37/02A61P37/06A61P29/00A61P9/10A61P31/04A61P31/12
CPCC07D277/56C07D277/30C07D277/42A61P9/10A61P29/00A61P31/04A61P31/12A61P37/02A61P37/06
Inventor 李松钟武林忠宝王晓奎刘洪英谢云德赵国明郑志兵肖军海李行舟
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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