Thieno-thiopyrano pyrazole compound and pharmaceutical applications thereof

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

Inactive Publication Date: 2014-08-13
SHENYANG PHARMA UNIVERSITY
View PDF3 Cites 6 Cited by
  • 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

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Thieno-thiopyrano pyrazole compound and pharmaceutical applications thereof
  • Thieno-thiopyrano pyrazole compound and pharmaceutical applications thereof
  • Thieno-thiopyrano pyrazole compound and pharmaceutical applications thereof

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 of...

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] + .

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

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 cortical function 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 be...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap