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Pyrazolopyrimidine compound and pharmaceutical composition thereof as well as pharmaceutical application of pyrazolopyrimidine compound

A technology for pyrazolopyrimidines and compounds, applied in the field of pyrazolopyrimidine compounds and their pharmaceutical compositions and their preparation, capable of solving problems such as inhibition

Active Publication Date: 2014-04-02
泸州天演生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Phosphorylation of threonine at position 69 of TRPC6 protein leads to inhibition of TRPC6 activity

Method used

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  • Pyrazolopyrimidine compound and pharmaceutical composition thereof as well as pharmaceutical application of pyrazolopyrimidine compound
  • Pyrazolopyrimidine compound and pharmaceutical composition thereof as well as pharmaceutical application of pyrazolopyrimidine compound
  • Pyrazolopyrimidine compound and pharmaceutical composition thereof as well as pharmaceutical application of pyrazolopyrimidine compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Compound M106, wherein R 1 is hydrogen, R 2 is 4-fluorophenyl, R 3 Yes where n=0, X is C, Y is N, R 6 is tert-butoxycarbonyl, R 4 The preparation process of the compound M106 that is a hydroxyl group is as follows:

[0049]

[0050] Step a: Synthesis of intermediate 1: Take 4.12g (32mmol) of the starting material 4-piperidinecarboxylic acid and add it to a 100mL round bottom flask, add water 32mL, K 2 CO 3 6.78g (64mmol), cool down to 0°C, take 6.98g (32mmol) of di-tert-butyl dicarbonate in anhydrous condition, dissolve it in freshly distilled THF 5mL, add dropwise to a 100mL round-bottomed flask, after the dropwise addition, raise to room temperature and stir for 4h . After the reaction was completed, the THF was removed by rotary evaporation, and the 2 Wash the aqueous phase with O (20mL×2), adjust the pH of the aqueous phase to 2 with 6M HCl, then extract with EA (30mL×3), combine the EA phases, and wash with anhydrous MgSO 4 Dried, filtered and spin-dri...

Embodiment 2

[0058] Compound M086, R 1 is hydrogen, R 2 is 4-fluorophenyl, R 3 Yes where n=0, X is H, Y is N, R 6 is benzyloxycarbonyl, R 4 The preparation process of the compound M086 that is a hydroxyl group is as follows:

[0059]

[0060] Step a: Synthesis of Intermediate 1: Take 6.46g (50mmol) of the starting material 4-piperidinecarboxylic acid and add it to a 100°C round bottom flask, add 4.4g (110mmol) of NaOH, add 25mL of water, cool down to 0°C, and add dropwise Benzyl chloroformate 9.38g (5.5mmol), after the dropwise addition was completed, it was raised to room temperature and stirred for 4h. After the reaction, use Et 2 Wash the reaction solution with O (20mL×2), adjust the pH of the aqueous phase to 2 with 6M HCl, then extract with EA (30mL×3), combine the EA phases, and wash with anhydrous MgSO 4 Dry, filter and spin-dry the obtained product Intermediate 1 as a white solid. Yield 94.9%.

[0061] Step b: Synthesis of Intermediate 2: Under anhydrous conditions, ta...

Embodiment 3

[0068] Compound M085, R 1 is hydrogen, R 2 is 4-fluorophenyl, R 3 Yes where n=0, X is H, Y is N, R 6 is ethoxycarbonyl, R 4 The preparation process of the compound M085 which is a hydroxyl group is as follows

[0069]

[0070] Step a: Synthesis of Intermediate 1: Take 5.16 g (40 mmol) of the starting material 4-piperidinecarboxylic acid and add it to a 100-degree round bottom flask, add Na 2 CO 3 Add 40mL of water to 5.04g (48mmol), dissolve 5.13g (48mmol) in 40mL of tetrahydrofuran, add dropwise to a round bottom flask, and stir at room temperature for 2h. At the end of the reaction, tetrahydrofuran was removed by rotary evaporation, 60 mL of water was added, the pH was adjusted to 2 with 2M HCl, and then extracted with EA (30 mL×3), the EA phases were combined and washed with anhydrous MgSO 4 Dry, filter and spin-dry the obtained product Intermediate 1 as a white solid. Yield 91.9%.

[0071] Step b: Synthesis of Intermediate 2: Under anhydrous conditions, take I...

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PUM

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Abstract

The invention provides a pyrazolopyrimidine compound shown as a structural formula (I), a pharmaceutical composition taking the pyrazolopyrimidine compound as an active component, a preparation method of the pyrazolopyrimidine compound and the pharmaceutical composition as well as an application of the pyrazolopyrimidine compound and the pharmaceutical composition in preparation of a TRPC6 (Transient Receptor Potential Channel 6) adjustor probe medicine and related medicines for preventing and treating glomerulopathy and myocardial hypertrophy. The pyrazolopyrimidine compound and derivatives provided by the invention can be used to prepare medical preparations in various forms which comprise oral liquids, injections, pulmonary inhalation preparations and transdermal preparations, specifically injections, oral liquids, troches, capsules, granules, aerosols, dry powder inhalation, patches and the like.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular, relates to a pyrazolopyrimidine compound and its pharmaceutical composition and their preparation method, as well as the preparation of TRPC6 modulator probe drug and the prevention and treatment of glomerular diseases and cardiac hypertrophy. applications in related medicines. Background technique [0002] The glomeruli are blood filters within the kidneys and play a very important role in regulating the composition of urine. The capillary wall of the glomerulus constitutes a highly selective filtration membrane. The filtration membrane has a three-layer structure. called the podocyte layer. The filter membrane has a high permeability to water and small molecules, which makes it easy to enter the urinary space, but it has a very high filtration function for plasma proteins such as albumin. [0003] Disruption of the glomerular filtration barrier leads to many kidney disea...

Claims

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Application Information

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IPC IPC(8): C07D487/04A61K31/519A61P13/12A61P9/00
CPCC07D487/04
Inventor 罗怀容洪学传朱曦朱进妹吴桂生邓子新朱颖旻陆云刚邓科瞿春容
Owner 泸州天演生物医药科技有限公司
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