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Thienothiopyranopyrazole compounds and their medical applications

A compound, pyrazole technology, applied in the field of medicine, can solve problems such as adrenal cortex decline and dependence

Inactive Publication Date: 2017-04-26
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] For the treatment of inflammation, glucocorticoid anti-inflammatory drugs were widely used in the early days and achieved remarkable results, but long-term use of glucocorticoids will cause dependence and easily cause side effects such as adrenal cortical function decline

Method used

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  • Thienothiopyranopyrazole compounds and their medical applications
  • Thienothiopyranopyrazole compounds and their medical applications
  • Thienothiopyranopyrazole compounds and their medical applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0088] Example 1: 1-(7-bromo-1,4-dihydrothieno[3',2':5,6]thiapyrano[4,3-c]pyrazole-3-formyl)-4 Preparation of -(4-methylphenyl)piperazine (compound number 01)

[0089] Step A: Preparation of 5,6-dihydro-4H-thieno[2,3-b]thiopyran-4-one

[0090] Add 4.64g (0.04mol) of 2-mercaptothiophene into 80mL of tetrahydrofuran, add 11mL of triethylamine and 3.3mL of acrylic acid dropwise under stirring, and heat to reflux for 12h. After cooling slightly, tetrahydrofuran was distilled off. Add 40 mL of ethyl acetate and 20 mL of water, add 6 mol / L hydrochloric acid to adjust the pH to 2, and collect the organic layer. The aqueous phase was extracted with ethyl acetate, and the organic phases were combined and dried over anhydrous magnesium sulfate. Suction filtration and concentration gave a brown oil. Petroleum ether was recrystallized to obtain 6.02 g of white needle-like solid, yield 80.0%, m.p.: 43-45°C.

[0091] Add 3.76g (0.02mol) of 3-(thiophene-2-thio)propionic acid into 20mL o...

Embodiment 2

[0108] Example 2: 1-(7-bromo-1,4-dihydrothieno[3',2':5,6]thiapyrano[4,3-c]pyrazole-3-carbonyl)-4- Preparation of (diphenylmethyl)piperazine (compound number 02)

[0109] According to the method of Example 1, 1-(7-bromo-1,4-dihydrothieno[3',2':5,6]thiopyrano[4,3-c]pyrazole-3-carbonyl was obtained )-4-(diphenylmethyl)piperazine 0.77g, yield 35%. m.p.:175-176℃;IR(KBr,cm -1 ):3420,2921,2851,1607,1451,1384,1262,1154,1027,997,877,831,705; 1 H-NMR (600MHz, CDCl 3 ):δ2.44(4H,m),3.79(4H,m),4.16(2H,s),4.25(1H,s),7.19(2H,d,J=8.4Hz),7.28(4H,dd, J=7.2Hz, 8.4Hz), 7.41 (4H, d, J=7.2Hz); ESI-MS(m / z): 551.2[M+H] + .

Embodiment 3

[0110] Example 3: N,N-diethyl-7-bromo-1,4-dihydrothieno[3',2':5,6]thiapyrano[4,3-c]pyrazole-3- Preparation of amides (compound number 03)

[0111] According to the method of Example 1, N,N-diethyl-7-bromo-1,4-dihydrothieno[3',2':5,6]thiopyrano[4,3-c]pyridine was prepared Azole-3-amide (Compound No. 03) 0.75 g, yield 50%. m.p.:147-148℃;IR(KBr,cm -1 ):3212,2958,2917,2849,1735,1583,1535,1508,1485,1461,1375,1215,1159,967,849; 1 H-NMR (600MHz, CDCl 3 ):δ1.25(6H,m),3.54(4H,m),4.12(2H,s),7.72(1H,s); ESI-MS(m / z):372.0,374.0[M+H] + .

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Abstract

The invention belongs to the field of medical technologies, and relates to a thieno-thiopyrano pyrazole compound and pharmaceutical applications thereof. The thieno-thiopyrano pyrazole compound comprises derivatives of the thieno-thiopyrano pyrazole compound and pharmaceutical applicable salts. The thieno-thiopyrano pyrazole compound and salts added by pharmaceutically applicable acids of the compound can be combined with existing drugs or used alone as a lipoxygenase inhibitor, and used for treating related diseases such as chronic dull pains including inflammations, gout, headache, toothache, neuralgia and arthralgia which are relevant to an arachidonic acid metabolizing process.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to thienothiopyranopyrazole compounds and their application as lipoxygenase inhibitors, and a preparation method thereof. Background technique [0002] Inflammation is a basic pathological process caused by the body's tissue damage caused by various inflammatory stimuli, and it is also a defense mechanism of the body against infection. Inflammation is mainly manifested as redness, swelling, pain, etc. [0003] For the treatment of inflammation, glucocorticoid anti-inflammatory drugs were widely used in the early days and achieved remarkable results. However, long-term use of glucocorticoids will cause dependence and easily cause side effects such as adrenal cortex decline. Since the emergence of drugs such as Phenylbutazone, Indomethacin and Ibuprofen in the 1950s and 1960s, nonsteroidal anti-inflammatory drugs (NSAIDs) have attracted people's attention , and gradually become the fo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/14A61K31/496A61K31/4162A61K31/5377A61K31/454A61P29/00A61P25/04A61P19/06A61P19/02A61P1/02
CPCC07D495/14
Inventor 胡春王欣金辄刘晓平黄二芳孙蕊
Owner SHENYANG PHARMA UNIVERSITY