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Method for preparing N substituted pyrrolidine derivative through acylation of methyl sulfone chloride

A technology of substituents and general formula compounds, applied in organic chemistry and other fields, can solve problems such as low affinity and instability

Active Publication Date: 2014-03-26
CHENGDU DIAO PHARMA GROUP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the study of substrate analogs, it was found that the most effective inhibitors were aminoacylpyrrolidine boronic acids, but they were unstable and tended to cyclize, and some other more stable pyrrolidine and thiazolidine derivatives had a Low affinity, high doses required in clinical situations

Method used

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  • Method for preparing N substituted pyrrolidine derivative through acylation of methyl sulfone chloride
  • Method for preparing N substituted pyrrolidine derivative through acylation of methyl sulfone chloride
  • Method for preparing N substituted pyrrolidine derivative through acylation of methyl sulfone chloride

Examples

Experimental program
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Effect test

Embodiment 1

[0067] (S)-1-(2-(2-(3-Phenyl-2-oxo-1-imidazolidinyl)ethylamino)acetyl)-2-cyanopyrrolidine oxalate, a compound of the invention 1.

[0068] A 1,1-bis(2-hydroxyethyl)-3-phenylurea

[0069] Dissolve triphosgene (30g) in toluene, add aniline (18.5g) dropwise, and reflux for 5 hours after adding, and distill off excess phosgene under reduced pressure, then drop it into a dichloromethane solution of diethanolamine (24g) , stirred overnight, washed with saturated brine until clean, dried and concentrated to give 1,1-bis(2-hydroxyethyl)-3-phenylurea (36g).

[0070] B 1-Bromoethyl-3-phenyl-2-imidazolidinone

[0071] Dissolve 1,1-bis(2-hydroxyethyl)-3-phenylurea (36g) in dichloromethane, add phosphorus tribromide (40.6g) dropwise under ice cooling, and stir at room temperature for 5 Hour. The pH of the reaction solution was adjusted to about 10 with saturated sodium bicarbonate solution, and stirred at room temperature for 36 hours. The organic phase was separated, and the aqueous ...

Embodiment 2

[0075] (S)-1-(2-(2-(3-(1,1-dimethylethyl)-2-oxo-1-imidazolidinyl)ethylamino)acetyl)-2-cyano Pyrrolidine oxalate, compound 2 of the present invention.

[0076] (S)-1-(2-(2-(3-(1,1-dimethylethyl)-2-oxo-1-imidazolidinyl)ethylamino)acetyl)-2-cyano The preparation of pyrrolidine oxalate refers to Example 1, and is prepared by a conventional method. 1 H-NMRδ(DMSO-d 6 ):4.77(dd,1H,);4.09-4.03(m,2H);3.61-3.57(m,1H);3.46-3.40(m,5H);3.29-3.26(m,4H);2.28-2.24( m,2H);2.14-2.09(m,2H);1.26(s,9H).ESI-MS:322.

Embodiment 3

[0078] (S)-1-(2-(2-(3-(4-methoxyphenyl)-2-oxo-1-imidazolidinyl)ethylamino)acetyl)-2-cyanopyrrolidine Oxalate, Compound 3 of the present invention.

[0079] (S)-1-(2-(2-(3-(4-methoxyphenyl)-2-oxo-1-imidazolidinyl)ethylamino)acetyl)-2-cyanopyrrolidine The preparation of oxalate refers to Example 1 and is prepared by conventional methods. 1 H-NMR δ(DMSO-d 6):7.48(d,2H);6.92(d,2H);4.83(dd,1H);4.02-3.92(m,1H);3.77(t,2H);3.72(s,3H);3.61-3.58( m,1H);3.49-3.47(m,4H);3.46-3.42(m,1H);3.10(t,2H);2.18-2.16(m,2H);2.07-2.00(m,2H).ESI- MS:372.

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Abstract

The invention relates to an N-substituted pyrrolidine derivative with a structure shown in a formula (I) and a curative active substance of the N-substituted pyrrolidine derivative serving as a DPP-IV inhibitor for treating and / or preventing diabetes mellitus or other diseases relative to DPP-IV.

Description

[0001] This application is a divisional application of the Chinese invention patent application "N-substituted pyrrolidine derivatives and their uses" with the filing date of September 23, 2008 and the application number of CN 200810161373.1. technical field [0002] The invention relates to an N-substituted pyrrolidine derivative, which belongs to the field of medicine. Background technique [0003] Diabetes mellitus is a multifactorial disease process manifested by hyperglycemia, or elevated plasma glucose levels, in the fasted state or following the administration of glucose during an oral glucose tolerance test. There are two common forms of diabetes, type I and type II diabetes. Patients with type 1 diabetes (or insulin-dependent diabetes mellitus (IDDM)) produce little or no insulin at all; patients with type 2 diabetes (or non-insulin-dependent diabetes mellitus (NIDDM)) Insulin levels are often the same or even higher. In these patients, the main insulin-sensitive t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/12
Inventor 王学超王六堂张斌何兆权
Owner CHENGDU DIAO PHARMA GROUP
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