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Pyrazol alcohol-pyridazinone coupling compound and pharmaceutical composition thereof and application of pyrazol pyridazinone-pyridazinone coupling compound in medicine

A technology of pyridazinone and pyrazolol, which is applied in the field of medicinal chemistry, can solve the problems of increased drug burden for patients, and achieve the effects of reduced drug burden, excellent neuroprotective effect, and low drug resistance

Pending Publication Date: 2022-01-28
GUIZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Combined medication will lead to an increase in the burden of medication for patients. In addition, the interaction between drugs is also a problem that cannot be ignored

Method used

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  • Pyrazol alcohol-pyridazinone coupling compound and pharmaceutical composition thereof and application of pyrazol pyridazinone-pyridazinone coupling compound in medicine
  • Pyrazol alcohol-pyridazinone coupling compound and pharmaceutical composition thereof and application of pyrazol pyridazinone-pyridazinone coupling compound in medicine
  • Pyrazol alcohol-pyridazinone coupling compound and pharmaceutical composition thereof and application of pyrazol pyridazinone-pyridazinone coupling compound in medicine

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] This embodiment provides a compound of formula 1- particular compound of Formula 7 and Table 1:

[0033] Table 1

[0034]

[0035] The compound 6- (4- (5-hydroxy-1-phenyl--1H- pyrazol-3-yl) phenyl) -4,5-dihydro-pyridazin -3 (2H) - one; Mp257- 261 ℃. 1 H NMR (400MHz, DMSO-D 6 ) Δ11.88 (s, 1H), 10.95 (s, 1H), 7.88 (d, J = 8.5Hz, 2H), 7.81 (dd, J = 10.4,8.4Hz, 4H), 7.49 (dd, J = 10.8 , 5.1Hz, 2H), 7.30 (t, J = 7.4Hz, 1H), 6.08 (s, 1H), 2.98 (t, J = 8.2Hz, 2H), 2.47 (t, J = 8.2Hz, 2H). 13 C NMR (100MHz, DMSO-D 6 ) Δ167.49,154.33,149.56,149.39,139.26,135.65,134.58,129.40,126.34,126.28,125.52,121.68,85.77,26.47,22.26.HRMS (ESI) calcd for C 19 Hide 17 N 4 O 2 [M + h] + : 333.1352, found 333.1341.

[0036] Compound 2 6- (4- (5-hydroxy-1- (pyridin-2-yl) lH-pyrazol-3-yl) phenyl) -4,5-dihydro-pyridazin -3 (2H) - ketones; Mp253-256 ℃. 1 H NMR (600MHz, DMSO-D 6 ) Δ12.60 (s, 1H), 10.99 (s, 1H), 8.49 (dd, J = 4.9,0.9Hz, 1H), 8.10 (t, J = 7.4Hz, 1H), 7.93 (t, J = 8.6 hz, 3H), 7.83 (d, J ...

Embodiment 2

[0062] This embodiment provides a compound 8-16, which is as follows:

[0063]

[0064] The specific chemical structural formula of Compound 8-16 is shown in Table 3:

[0065] table 3

[0066]

[0067]

[0068] Compound 8 is 6- (4- (5-hydroxy-3-methyl-1H-pyrazole-1-yl) phenyl) -4,5-dihydroxazine-3 (2H)-ketone; MP258- 261 ° C. 1 H NMR (600MHz, DMSO-D 6 Δ11.69 (S, 1H), 10.94 (S, 1H), 7.81 (S, 4H), 5.41 (S, 1H), 2.96 (T, J = 8.2 Hz, 2H), 2.46 (T, J = 8.2 Hz, 2H), 2.12 (D, J = 5.7 Hz, 3H). 13 C NMR (150MHz, DMSO-D 6 Δ167.46, 153.92, 149.31, 140.13, 132.63, 126.74, 12.20, 117.79, 88.35, 24.45, 22.21, 14.78.HRMS (ESI) Calcd for C 14 Hide 15 N 4 O 2 [M + h] + : 271.1195, Found271.1200.

[0069] Compound 9 is 6- (4- (5-hydroxy-3-phenyl-1H-pyrazole-1-yl) phenyl) -4,5-dihydroxazine-3 (2H)-ketone; MP254- 257 ° C. 1 H NMR (600MHz, DMSO-D 6 δ12.06 (S, 1H), 10.98 (S, 1H), 7.93 (D, J = 8.7 Hz, 2H), 7.86 (DD, J = 11.6, 8.5 Hz, 4H), 7.43 (T, J = 7.5 Hz, 2H), 7.34 (T, J = 7.2 Hz, 1H), 6.05 (S...

Embodiment 3

[0096] The present embodiments provide compounds 17-19, having the general formula:

[0097]

[0098] Specific compounds of formula 17-19 as shown in Table 5:

[0099] table 5

[0100]

[0101] Compound 17 3- (4- (6-methoxy-pyridazin-3-yl) phenyl) -1-phenyl -1H- pyrazole -5 (4H) - one; M.p.198-201 ℃. 1 H NMR (600MHz, DMSO-D 6 ) Δ11.92 (s, 1H), 8.22 (d, J = 9.3Hz, 1H), 8.14 (d, J = 8.3Hz, 2H), 7.99 (d, J = 8.4Hz, 2H), 7.85 (d, J = 8.0Hz, 2H), 7.50 (t, J = 7.9Hz, 2H), 7.32 (dd, J = 17.3,8.3Hz, 2H), 6.13 (s, 1H), 4.09 (s, 3H). 13 C NMR (150MHz, DMSO-D 6 ) Δ164.58,154.87,154.35,149.40,139.29,135.59,134.83,129.41,128.15,126.97,126.29,125.98,121.70,118.06,85.83,54.97.HRMS (ESI) calcd for C 20 Hide 17 N 4 O 2 [M + h] + : 345.1352, found345.1351.

[0102] Compound 18 3- (4- (6-bromo-pyridazin-3-yl) phenyl) -1-phenyl -1H- pyrazole -5 (4H) - one; M.p.243-246 ℃. 1 H NMR (400MHz, DMSO-D 6 ) Δ11.91 (s, 1H), 8.27 (d, J = 9.1Hz, 1H), 8.21 (d, J = 8.3Hz, 2H), 8.12 (d, J = 9.0Hz, 1H), 8.03 (d,...

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Abstract

The invention belongs to the technical field of pharmaceutical chemistry, and particularly relates to a pyrazole alcohol-pyridazinone coupling compound and a pharmaceutical composition thereof and application of the pyrazole alcohol-pyridazinone coupling compound in medicine. The pyrazole alcohol-pyridazinone coupled compound has dual action mechanisms of resisting platelet aggregation and protecting nerve cells, and is applied to preparation of medicines for preventing or treating cerebral apoplexy, cardiovascular and cerebrovascular diseases, senile dementia and complications thereof caused by thrombus and excessive free radicals.

Description

Technical field [0001] The present invention belongs to the technical field of pharmaceutical chemistry, specifically relates to a pyrazole alcohol - coupling pyridazinone compounds, pharmaceutical compositions and their use in medicine. Background technique [0002] Stroke, also known as cerebral infarction, mainly due to thromboembolism leading to brain tissue and blood supply disorders occur, then along with hypoxic-ischemic brain cell death. With a high incidence, high morbidity, high mortality, etc., to become one of refractory disease hazard to human health. With the rapid aging of society and increasing the pace of life, the incidence of stroke is increasing and tend to be younger, presumably by 2030 the incidence of cerebrovascular disease than in 2010, an increase of about 50%. 2016 Global Burden of Disease (GBD) data show that stroke is caused by the loss of life in our country's first cause, the annual cost for treatment of stroke up to 20 billion, to stroke patients a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/10A61K31/501A61P25/28A61P9/00A61P9/10A61P7/02A61P25/00
CPCC07D403/10A61P25/28A61P9/00A61P9/10A61P7/02A61P25/00
Inventor 李毅汤磊樊玲玲李永张毅罗碧兰
Owner GUIZHOU MEDICAL UNIV
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