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Propylene glycol derivatives, preparation method thereof, pharmaceutical composition and use thereof

A compound and pharmaceutical technology, applied in the field of medicine, can solve problems such as adverse reactions

Inactive Publication Date: 2011-11-30
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, currently clinically used immunosuppressants also have many adverse reactions

Method used

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  • Propylene glycol derivatives, preparation method thereof, pharmaceutical composition and use thereof
  • Propylene glycol derivatives, preparation method thereof, pharmaceutical composition and use thereof
  • Propylene glycol derivatives, preparation method thereof, pharmaceutical composition and use thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0249] This example demonstrates Preparation of 2-acetamido-2-[2-(4-(7-oxazole-10-phenyl)phenyl)-2-oxo-ethyl]-1,3-malonic acid diethyl ester

[0250] (9-1) Preparation of phenacyl n-phenylbutyrate

[0251]

[0252] Dissolve 4-phenylbutyric acid (12.2g, 74mmol) in 40mL of acetonitrile, add chloroacetylbenzene (5g, 32.5mmol) and triethylamine (6.9g, 68.2mmol), heat to reflux for 4h, evaporate the solvent under reduced pressure , the residue with CH 2 Cl 2 Extracted, washed with water to neutral, anhydrous NaSO 4 After drying, filtering and concentrating, 9 g of yellow oil was obtained, and the product was directly sent to the next step without separation and purification.

[0253] (9-2) Preparation of 2-n-phenylpropyl-4-phenyloxazole

[0254]

[0255] The raw material phenacyl n-phenylbutyrate (9.2 g, 33 mmol) was dissolved in 90 mL of xylene, acetamide (9.7 g, 165 mmol) and 47% of BF 3 Diethyl ether solution 3.2mL, heated to reflux for 40h, evaporated the solvent u...

preparation example 2

[0269] This example demonstrates

[0270] Preparation of 2-amino-2-[2-(4-(6-oxazole-9-phenyl)phenyl)-2-oxo-ethyl]-1,3-propanediol hydrochloride.

[0271] (10-1) Preparation of phenacyl n-phenylpropionate

[0272]

[0273] Dissolve 3-phenylpropionic acid (11.1g, 74mmol) in 40mL of acetonitrile, add chloroacetylbenzene (5g, 32.5mmol) and triethylamine (6.9g, 68.2mmol), heat to reflux for 4h, evaporate the solvent under reduced pressure , the residue with CH 2 Cl 2 Extracted, washed with water to neutral, anhydrous NaSO 4 Dry, filter, and concentrate to obtain 8.5 g of a yellow oil, which is directly sent to the next step without separation and purification.

[0274] 1 HNMR (MERCURY300MHz, CDCl 3 ) δ7.91 (dd, J=8.7Hz, 1.5Hz, 2H, 2ArH) 7.61 (t, J=7.2Hz, 1H, ArH) 7.48 (t, J=7.5Hz, 2H, 2ArH) 7.33-7.18 (m , 5H, 5ArH) 5.34 (s, 2H, CH 2 )3.04(t, J=7.5Hz, 2H, CH 2 ) 2.82 (t, J = 7.5Hz, 2H, CH 2 )

[0275] ESI (m / z) 291 (M+Na + )

[0276] (10-2) Preparation of 2-pheneth...

preparation example 3

[0292] This example demonstrates

[0293] Preparation of 2-amino-2-[2-(4-(4-(4-n-butanol acetate)phenethyl)phenyl)-2-oxo-ethyl]-1,3-propanediol hydrochloride .

[0294] (11-1) Preparation of 4-bibenzyl-4-oxo-butyric acid

[0295]

[0296] Under ice-bath cooling (0 °C), the starting material diphenylethane (19.7 g, 108.8 mmol) was dissolved in 500 mL of dry CH 2 Cl 2 , added ground succinic anhydride (10.8 g, 108.8 mmol), and then slowly added AlCl in portions 3 (31.9g, 240.5mmol), when AlCl 3 After adding all the mixture, continue to stir for 1 hour, point the board to find that the raw material point disappears, add 16mL of concentrated hydrochloric acid and 50mL of water to decompose, evaporate the solvent to dryness, a white solid precipitates, filter with suction, wash the filter cake with 32mL (1:3) diluted hydrochloric acid, Then wash with 4 mL of water. Add the filter cake to the eggplant-shaped bottle, add 13gNa 2 CO 3 Boil with 81mL water for 30min, cool,...

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Abstract

The invention discloses a new class of propylene glycol derivatives represented by the general formula (I), a preparation method thereof, a pharmaceutical composition containing them, and their use as medicines, especially immunomodulatory medicines. This kind of compound with excellent curative effect and low toxicity can be used for immune disorder and immunosuppression; and can be used for treatment and / or low immunity, rejection after organ transplantation and autoimmune disease. General formula (I)

Description

technical field [0001] The present invention relates to a new class of immunomodulators, their preparation method, pharmaceutical composition containing them, and their use as drugs, especially as immunomodulatory drugs for the prevention and treatment of diseases mediated by T lymphocytes, which belong to medical technology field. Background technique [0002] The body's immune response is an important defense mechanism for antibodies to eliminate foreign substances such as bacteria, viruses, and grafts, and is also an important self-stabilizing mechanism for preventing self-cell mutations and causing diseases. The means of preventing and treating diseases by affecting the immune function of the body is called immunotherapy or immunotherapy. [0003] Immunomodulation refers to the mutual restriction regulatory network formed by the stimulation and inhibition between various immune cells and their subgroups, between cells and various cytokines, or between positive and negat...

Claims

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Application Information

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IPC IPC(8): C07C215/28C07C271/16C07C219/22C07C309/66C07D263/32C07D311/58A61K31/137A61K31/27A61K31/222A61K31/255A61K31/421A61K31/353A61P37/02A61P37/06
Inventor 韩伟娟周婉琪李志永张翼陈晓光尹大力
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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