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Amino propanediol derivatives, preparation method, drug compositions and uses thereof

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

Active Publication Date: 2015-08-19
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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  • Amino propanediol derivatives, preparation method, drug compositions and uses thereof
  • Amino propanediol derivatives, preparation method, drug compositions and uses thereof
  • Amino propanediol derivatives, preparation method, drug compositions and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0106] This experiment demonstrates the preparation of 2-amino-2-((4-((4-benzyloxyphenyl)thio)phenoxy)methylene)-1,3-propanediol hydrochloride

[0107]

[0108] (1-1) Preparation of 4-((4-benzyloxy)phenylthio)phenol

[0109]

[0110] Put 4,4-diphenylsulfide diphenol (10g, 45.8mmol, 1equiv) into a 250mL three-necked flask with a stirrer. The three-necked flask is equipped with a spherical condenser and a constant-pressure dropping funnel. Put 100mL N,N-dimethylformamide (DMF) into the reactor, stir until dissolved, put potassium hydroxide (2.827g, 50.4mmol, 1.1equiv), potassium iodide (380mg, 2.29mmol, 0.05equiv) into the reactor in turn, Stir for 5 minutes, add a DMF solution of benzyl bromide (6.0 mL benzyl bromide + 20 mL DMF) dropwise into the reactor, and the dropwise addition is completed in 4 hours, continue the reaction for 8 hours, and raise the temperature to 40°C for 4 hours. After the reaction was completed, the reaction liquid was poured into water, stirred ...

Embodiment 2

[0121] This experiment demonstrates that 2-amino-2-(4-(4-(4-((4-methyl)phenyl)phenylthio)phenoxymethylene))-1,3-propanediol hydrochloride preparation

[0122]

[0123] (2-1) Preparation of 4-((4-hydroxy)phenylthio)phenyltrifluoromethanesulfonate

[0124]

[0125]Put 4,4,-diphenyl sulfide diphenol (2.00g) and acetone (35mL) into a 100mL eggplant-shaped bottle in turn, cool to -15°C in an ice-salt bath, and add trifluoromethanesulfonic anhydride dropwise to the reaction solution The dichloromethane solution (1.6mL trifluoromethanesulfonic anhydride + 2mL dichloromethane), was added dropwise in 20 minutes, and reacted at room temperature for 3 hours. After the reaction, the reaction solution was poured into ice water, extracted with dichloromethane (20 mL×3), dried over anhydrous sodium sulfate, and the solvent was distilled off. Flash column chromatography gave 1.034 g off-white solid with a yield of 32.2%. 1 HNMR (400MHz, Acetone-d 6 )δ(ppm):8.890(s,1H),7.44(d,J=8.4,2...

Embodiment 3

[0136] This experiment demonstrates that 2-amino-2-(4-(4-((2-n-propyl)oxazol-4-yl)phenylthio)phenoxymethylene)-1,3-propanediol hydrochloride preparation of

[0137]

[0138] (3-1) 4-(Bromoacetyl) bromobenzene

[0139]

[0140] Bromobenzene (13.0mL, 0.127mmol, 1equiv), dichloromethane (200mL), and bromoacetyl bromide (11.0mL, 0.127mmol, 1equiv) were successively put into a 500mL three-necked flask, cooled to 0°C in an ice bath, and batch Aluminum trichloride powder (34.0 g, 0.254 mmol, 2 equiv) was added once, and the addition was completed in 1 hour, and the reaction was carried out at room temperature for 2 hours. After the reaction is complete, pour the reaction solution into 2N hydrochloric acid with ice cubes, stir at room temperature for 1 hour, separate the liquids, extract with dichloromethane (50mL×2), dry over anhydrous sodium sulfate, and distill off the dichloromethane to obtain 26.44g of yellow Solid, yield 74.9%. 1 H NMR (300MHz, CDCl 3 )δ (ppm): 7.86 (d...

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Abstract

The invention discloses a class of amino propanediol derivatives, a preparation method, drug compositions and uses thereof, and particularly relates to a class of new immunoloregulation agents represented by a general formula (I), a preparation method, drug compositions containing the immunoloregulation agents, and especially uses of the immunoloregulation agents as immunoloregulation drugs. The compound with characteristics of excellent treatment effect and low toxicity can be used in the fields of immunologic derangement and immunosuppression, and can further be used for treatment of hypoimmunity, organ transplant rejection and autoimmune diseases. The formula I is defined in the instruction.

Description

technical field [0001] The present invention relates to a new class of immunomodulators. The preparation method thereof, the pharmaceutical composition containing them, and the use thereof as a medicine, especially as an immunomodulatory medicine for preventing and treating diseases mediated by T lymphocytes belong to the technical field of medicine. 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 acting on different links of the immune response to play its regulatory role, so that the body's immune response is within the required range, so as to achieve the purpose of preve...

Claims

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Application Information

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IPC IPC(8): C07C323/20C07C319/20C07D263/32C07C217/34C07C213/02C07F9/09C07F9/653A61K31/145A61K31/421A61K31/138A61K31/661A61K31/675A61P37/02A61P37/04A61P37/06
Inventor 齐建国汪小涧金晶田育林周琬琪陈晓光尹大力
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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