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Pyrrolopyrimidines and preparation method and application thereof

A compound and medicinal salt technology, applied in the field of autoimmune disease drugs, pyrrolopyrimidine compounds and their preparation, can solve the problems of low selectivity and large side effects

Inactive Publication Date: 2018-11-13
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Existing JAK inhibitors have some problems such as low selectivity and large side effects, so it is necessary to study new specific JAK kinase inhibitors to improve the status quo

Method used

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  • Pyrrolopyrimidines and preparation method and application thereof
  • Pyrrolopyrimidines and preparation method and application thereof
  • Pyrrolopyrimidines and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: Add 4-(4-nitrophenyl)piperazine (20.7g, 0.1mol), 4-chloro-pyrrolo[2,3-d]pyrimidine into a reaction flask equipped with a thermometer and a stirring device (15.3g, 0.1mmol), K 2 CO 3 (32g) and DMF (300mL), reacted at 70°C for 6h, TLC showed that the reaction was complete, the reaction solution was poured into 500mL cold water, extracted with ethyl acetate, the extract was dried with anhydrous magnesium sulfate, filtered, and the organic solvent was evaporated under reduced pressure , and separated by column chromatography to obtain compound Ⅰ-1. The yield is 66.5%.

[0036] 1 H NMR (400MHz, DMSO-d 6 )δ: 3.70(t, J=5.2Hz, 4H), 4.07(d, J=5.2Hz, 4H), 6.63(t, J=1.6Hz, 1H), 7.00(d, J=9.2Hz, 2H) ,7.20(t,J=2.8Hz,1H),8.09(d,J=9.2Hz,2H),8.17(s,1H),11.71(s,1H).HRMS m / z,[M+H] + 325.1410.

Embodiment 2

[0037] Embodiment 2: with reference to the method of embodiment 1, take 4-(2-cyanophenyl) piperazine as raw material synthesis I-2, yield 59.1%,

[0038] 1H NMR (400MHz, DMSO-d 6 )δ: 3.30(t, J=4.8Hz, 5H), 4.06(t, J=4.8Hz, 4H), 6.67(q, J=1.6Hz, 1H), 7.12(t, J=7.2Hz, 1H) ,7.19-7.21(m,2H),7.59-7.63(m,1H),7.73(dd,J1=1.2Hz,J2=7.6Hz,1H),8.18(s,1H),11.72(s,1H). HRMS m / z, [M+H] + 305.1512.

Embodiment 3— Embodiment 6

[0039] Example 3-Example 6: With reference to the method of Example 1, the corresponding substituted piperazines are used as raw materials to synthesize I-3-I-6.

[0040] Table 1 Structure and characterization data of Ⅰ-3-Ⅰ-6 series compounds

[0041]

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PUM

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Abstract

The invention relates to pyrrolopyrimidines and a preparation method and application thereof, in particular to pyrrolopyrimidines having formula I structure, their pharmaceutically acceptable salts, their preparation method, a pharmaceutical composition using the pyrrolopyrimidines of formula I structure and their pharmaceutically acceptable salts as active effective ingredients, and pharmaceutical application of the pharmaceutical composition in the treatment of diseases due to JAK kinase-mediated signaling pathway functional disorders, and autoimmune diseases such as rheumatoid arthritis, psoriasis and organ rejection.

Description

technical field [0001] The present invention belongs to the technical field of medicine, and more specifically, relates to a class of pyrrolopyrimidine compounds and a preparation method thereof, a pharmaceutical composition containing the compound as an active ingredient and its use in medicines for treating autoimmune diseases. Background technique [0002] Janus kinase is a cytoplasmic non-transmembrane non-receptor tyrosine kinase, which contains 4 subtypes: JAK1, JAK2, JAK3, and TYK2, of which JAK3 is only expressed in bone marrow and lymphoid tissues, and the other three are widely present. in the whole body tissue. The JAK / STAT signal transduction pathway is widely involved in cell proliferation, differentiation, apoptosis and immune regulation, and is closely related to various systemic diseases [Aringer M, et al, (1999), Life Science, 64(24):2173- 2186], such as rheumatoid arthritis, psoriasis, chronic colitis, organ transplant rejection and other immune diseases, ...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61K31/519A61P19/02A61P29/00A61P17/06A61P37/02
CPCC07D487/04
Inventor 刘登科刘冰妮支爽刘颖张士俊
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH