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Pyrazole alcohol compound, pharmaceutical composition thereof and application thereof to drugs

A technology of compounds and solvates, applied in the field of medicinal chemistry, can solve the problems of application limitation, poor stability of drug metabolism, accumulation of poisoning, etc.

Active Publication Date: 2018-09-21
GUIZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Ligustrazine has poor fat solubility and low bioavailability, which leads to its fast metabolism, short half-life, and poor drug metabolism stability. In order to maintain an effective drug treatment concentration, it must be administered frequently clinically, which is easy to cause accumulation and poisoning, making its application restricted. certain limit
Edaravone is an antioxidant and free radical scavenger, which belongs to a small lipophilic molecule, which can form a high blood-brain barrier passage rate in the human body, and can prevent or treat neurons by protecting neurons in patients. The effect of treating cerebral apoplexy, but Edaravone has poor water solubility and is easy to oxidize in aqueous solution. In order to increase its water solubility and stability, it is often necessary to add alkaline substances and antioxidant substances in the preparation. The addition of these substances may give Patient causing unwanted side effects

Method used

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  • Pyrazole alcohol compound, pharmaceutical composition thereof and application thereof to drugs
  • Pyrazole alcohol compound, pharmaceutical composition thereof and application thereof to drugs
  • Pyrazole alcohol compound, pharmaceutical composition thereof and application thereof to drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0153] Example 1. 3-Methyl-1-(3,5,6-trimethylpyrazin-2-yl)-1H-pyrrol-5-ol (Compound 1): Yield 70.6%, oily liquid. 1 HNMR (500MHz, CDCl 3 )δ: 1 H NMR (400MHz, DMSO-d 6 ):δ:2.30(s,3H),2.51-2.54(m,9H),5.90(s,1H),12.2(s,1H,OH); HRMS(ESI) calculated value C 11 h 15 N 4 O[M+H] + :219.1246, measured value: 219.1247.

Embodiment 2

[0154] Example 2. 3-Ethyl-1-(3,5,6-trimethylpyrazin-2-yl)-1H-pyrrol-5-ol (compound 2): yield 65.6%, oily liquid. 1 HNMR (400MHz,d 6 -DMSO)δ: 1.14 (t, 3H, J=7.6Hz), 2.29 (s, 3H), 2.44-2.50 (m, 8H), 5.29 (s, 1H), 11.16 (s, 1H); HRMS (ESI ) Calculated value C 12 h 17 N 4 O[M+H] + :233.1402, measured value: 233.1396.

Embodiment 3

[0155] Example 3.3-tert-amyl-1-(3,5,6-trimethylpyrazin-2-yl)-1H-pyrrol-5-ol (compound 3): yield 49.8%, white solid, m.p.167 -168°C. 1 HNMR (400MHz,d 6 -DMSO) δ: 0.70(t, J=7.2Hz, 3H), 1.15(s, 6H), 1.49-1.54(m, 2H), 2.20(s, 3H), 2.44(s, 3H), 2.49(s ,3H),5.34(s,1H),11.07(s,1H); 13 CNMR (100MHz, d 6 -DMSO)δ: 9.1, 19.2, 20.8, 21.2, 27.1, 35.3, 35.5, 83.3, 142.7, 146.7, 148.4, 151.5, 153.5, 159.7; HRMS (ESI) calculated value C 15 h 23 N 4 o 2 [M+H] + : 275.1794, measured value 275.1789.

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Abstract

The invention discloses a 1-(3,5,6-trimethyl pyrazine-2-yl)-5-pyrazole alcohol compound, a tautomer thereof, a pharmaceutical composition thereof and application thereof to drugs. The 1-(3,5,6-trimethyl pyrazine-2-yl)-5-pyrazole alcohol compound has double effects of resisting platelet aggregation and protecting nerve cells, and comprises a compound as shown in the formula (I), a tautomer (Ia) thereof, or a stereoisomer, a geometrical isomer, a hydrate or a solvate thereof, or a pharmaceutically acceptable salt or prodrug as shown in the description. The 1-(3,5,6-trimethyl pyrazine-2-yl)-5-pyrazole alcohol compound and the pharmaceutical composition thereof provided by the invention can be used for preparing drugs for prevention and / or treatment and / or auxiliary treatment of cerebral apoplexy, cardiovascular and cerebrovascular diseases, senile dementia and complications thereof caused by thrombosis and excessive free radicals.

Description

field of invention [0001] The invention belongs to the technical field of medicinal chemistry, and specifically relates to 1-(3,5,6-trimethylpyrazin-2-yl)-5-pyrazolol compounds, tautomers thereof, and pharmaceutical compositions thereof and applications in medicine. Background of the invention [0002] Stroke is a refractory disease that seriously endangers the safety of human life and is characterized by high morbidity, disability and mortality. The survey results of the World Health Organization show that the incidence of stroke in China ranks first in the world, twice as high as that in the United States, and the incidence of cerebrovascular diseases in my country has increased significantly in recent years, with an annual growth rate of 9%. It is estimated that by 2030 In my country, 4 million people will die of stroke every year. Therefore, stroke has become an important disease affecting the health of Chinese people, and it is urgent to carry out the prevention and tr...

Claims

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Application Information

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IPC IPC(8): C07D403/04C07D401/14C07D405/14C07D409/14A61K31/497A61P9/00A61P25/00A61P7/02A61P9/10
CPCA61P7/02A61P9/00A61P9/10A61P25/00C07D401/14C07D403/04C07D405/14C07D409/14
Inventor 樊玲玲汤磊李毅李永刘健出良钊
Owner GUIZHOU MEDICAL UNIV
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