Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Parecoxib derivative as well as preparation method and application thereof

A compound and solvate technology, applied in the field of pharmaceutical compounds, can solve problems such as precipitation, and achieve the effect of good patient compliance and operational safety

Active Publication Date: 2021-06-18
SUZHOU INTRAGRAND PHARMA CO LTD
View PDF6 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, in clinical practice, Parecoxib can only be administered through slow intramuscular injection, rapid intravenous injection or through existing intravenous access, and precipitation may occur when Parecoxib is mixed with other drugs in the solution, Parecoxib must not be mixed with other drugs during dissolution or injection
In addition, there are potential infections during the preparation and storage of parecoxib injection, and patients must be injected twice a day by hospital professionals

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
  • Parecoxib derivative as well as preparation method and application thereof
  • Parecoxib derivative as well as preparation method and application thereof
  • Parecoxib derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0096]

[0097] K 2 CO 3 (375 mg, 2.7mmol, 5.0eq), methyl chloroacetate (1.16g, 10.8mmol, 20eq), and stirred at room temperature for 18 hours. with H 2 The reaction mixture was diluted with O (20 mL), extracted with EtOAc (20 mL*2). The combined organic phases were washed with saturated brine (15 mL), washed with Na 2 SO 4 After drying, filter and concentrate in vacuo. The obtained crude product residue was purified by TLC (PE / EA=1.7:1) to obtain 50 mg of crude product, which was purified by prep-HPLC (0.1% HCOOH / H in ACN 2 O) Further purification gave white solid compound 1 (16.65 mg, yield 6%). LCMS: (M+H)+: 443.1

[0098] 1 H-NMR (400MHz, CDCl 3 )δ=8.00(m,2H),7.38(m,7H),5.91(s,2H),2.61(q,J=7.2Hz,2H),2.52(s,3H), 2.08(s,3H), 1.10(t,J=7.2Hz,3H).

Synthetic example 2

[0100]

[0101] K 2 CO 3 (746 mg, 5.41 mmol, 1.54 eq), chloromethyl isopropyl carbonate (4 mL), and stirred at room temperature for 18 hours. with H 2 The reaction mixture was diluted with O (30 mL), extracted with EtOAc (40 mL*3). The combined organic phases were washed with saturated brine (30mL*3), washed with Na 2 SO 4 It was dried, filtered, and concentrated to obtain a crude residue, which was purified by TLC (EtOAc:PE=1:2) to obtain white solid Example 2 (104.4 mg, yield 33.73%). LCMS: (M+H)+: 487.2

[0102] 1 H-NMR (400MHz, DMSO-d6) δ=8.01-7.94(m,2H),7.50-7.39(m,5H),7.35-7.30(m,2H),5.91(s,2H), 4.87-4.71( m,1H),2.65(dd,J=7.1Hz,2H),2.49(s,3H),1.23(d,J=6.2Hz,6H),0.92(t,J=7.2Hz,3H).

[0103] Synthetic Example 3.

[0104]

[0105] Add DIPEA (174 mg, 1.35mmol, 2.5eq), methyl chloromethyl carbonate (134.4mg, 1.08mmol , 2.0eq), the reaction was stirred at room temperature for 18 hours. Spin dry with H 2 The reaction mixture was diluted with O (3 mL), extracte...

Embodiment 1

[0113] Synthesize following compound 5-28 with reference to embodiment 1

[0114] List of specific examples

[0115]

[0116]

[0117]

[0118]

[0119] Also included within the scope of the present invention is a pharmaceutical combination comprising said active compound in admixture with one or more non-toxic pharmaceutically acceptable carriers and / or diluents and / or adjuvants (hereinafter collectively referred to as "carrier" materials) substances, which may also contain other pharmaceutically active ingredients as required. The active compound of the present invention can be administered orally or externally, preferably in the form of a drug combination suitable for the administration route and at an effective dose required for treatment.

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 relates to a parecoxib derivative as shown in a formula I, a racemate, a stereoisomer, a tautomer, an isotope label, a solvate, a polymorphic substance, ester or pharmaceutically acceptable salt thereof, a pharmaceutical composition containing the parecoxib derivative, a preparation method of the parecoxib derivative, and application of the parecoxib derivative to medicines and veterinary medicines. The structure of Formula I is as follows.

Description

[0001] This application claims the priority of the previous application submitted to the State Intellectual Property Office of China on November 24, 2020. The patent application number is 202011334249.8, and the title of the invention is "a parecoxib derivative and its preparation method and application". The entirety of this application is incorporated by reference into this application. technical field [0002] The invention belongs to the field of pharmaceutical compounds, and in particular relates to a parecoxib derivative, a preparation method thereof, and a medicine application. Background technique [0003] Safe and effective analgesics are still an unmet market need, especially for moderate to severe pain drugs, currently mainly opioids, narcotic analgesics and non-steroidal anti-inflammatory drugs (NSAIDs), but The adverse reactions of these different types of drugs limit their wide clinical application. And specific cyclooxygenase-2 (COX-2) inhibitors, such as Par...

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
Patent Type & Authority Applications(China)
IPC IPC(8): C07D261/08C07F9/653A61P29/00A61P1/02A61P19/02A61K31/42A61K31/675
CPCA61P1/02A61P19/02A61P29/00C07D261/08C07F9/653
Inventor 朱加望王泽根冯剑波姚瑶
Owner SUZHOU INTRAGRAND PHARMA CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com