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N-substituted pyrrolidine derivates and uses thereof

A cyanopyrrolidine and oxo technology, applied in the field of N-substituted pyrrolidine derivatives, can solve the problems of low affinity and instability

Active Publication Date: 2009-04-01
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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  • N-substituted pyrrolidine derivates and uses thereof
  • N-substituted pyrrolidine derivates and uses thereof
  • N-substituted pyrrolidine derivates and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] (S)-1-(2-(2-(3-Phenyl-2-oxo-1-imidazolidinyl)ethylamino)acetyl)-2-cyanopyrrolidine oxalate, a compound of the invention 1.

[0067] A1,1-bis(2-hydroxyethyl)-3-phenylurea

[0068] 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).

[0069] B1-Bromoethyl-3-phenyl-2-imidazolidinone

[0070] 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 ph...

Embodiment 2

[0074] (S)-1-(2-(2-(3-(1,1-dimethylethyl)-2-oxo-1-imidazolidinyl)ethylamino)acetyl)-2-cyano Pyrrolidine oxalate, compound 2 of the present invention.

[0075] (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-NMR δ(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); m, 2H); 2.14-2.09 (m, 2H); 1.26 (s, 9H). ESI-MS: 322.

Embodiment 3

[0077] (S)-1-(2-(2-(3-(4-methoxyphenyl)-2-oxo-1-imidazolidinyl)ethylamino)acetyl)-2-cyanopyrrolidine Oxalate, Compound 3 of the present invention.

[0078] (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); MS: 372.

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Abstract

The invention relates to N-substituted pyrrolidine derivatives with the structure of formula (I), and active substances thereof which are taken as a DDP-IV depressor for treating and / or preventing diabetes and other diseases relevant to DPP-IV.

Description

technical field [0001] The invention relates to an N-substituted pyrrolidine derivative, which belongs to the field of medicine. Background technique [0002] 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 I diabetes (or insulin-dependent diabetes mellitus (IDDM)) produce little or no insulin at all; Insulin levels are often the same or even higher. In these patients, the main insulin-sensitive tissues, such as muscle, liver and adipose tissue, have developed resistance to the stimulation of insulin, and it is difficult for insulin to play its normal role in regulating blood sugar balance. [0003] At present, there are many methods and drugs for lowering blood sugar. Physical exercise and reduction of dietary calori...

Claims

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Application Information

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IPC IPC(8): C07D403/12A61K31/4178A61P3/10A61P29/00
Inventor 王学超王六堂张斌侯慧何兆权晏菊芳岑国栋张蔚瑜
Owner CHENGDU DIAO PHARMA GROUP
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