Eureka AIR delivers breakthrough ideas for toughest innovation challenges, trusted by R&D personnel around the world.

Method for preparing 3-amido quinine medically-acceptable salt

A technology for pharmaceutically acceptable salts of aminoquinine, which is applied to the preparation of pharmaceutically acceptable salts of 3-aminoquinine, the key intermediate field, can solve the problems of high cost and high equipment requirements, and achieve mild conditions, high reaction yield, Post-processing simple effects

Inactive Publication Date: 2008-04-16
SHANGHAI INST OF PHARMA IND CO LTD
View PDF0 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 1. The use of high-pressure hydrogenation kettles requires high equipment requirements;
[0007] 2. Use expensive Pearl’s catalyst

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
  • Method for preparing 3-amido quinine medically-acceptable salt
  • Method for preparing 3-amido quinine medically-acceptable salt

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Hydrogenate 5g (0.016mol) of (3S)-3-[(R)-1-phenyl]-ethylamine]-quinine dihydrochloride, 2.08g (0.033mol) of ammonium formate and 10% palladium on carbon Catalyst 0.25g, 200ml methanol was added and heated at 60°C for 3 hours, the catalyst was filtered off after cooling, the target product (S)-3-aminoquinine dihydrochloride 2.79g was collected after the solvent was recovered, the yield was 85%. 1 HNMR(DMSO-d 6 )δ: 1.75~1.94(m,3H,), 2.15~2.22(m,1H), 232(q,1H), 3.11~3.20(m,5H), 3.55~3.68(m,2H); ESI(m / z): 126[M-2HCl]; (C=1, H 2 O); mp>285°C.

Embodiment 2

[0031] Hydrogenate 5g (0.016mol) of (3R)-3-[(S)-1-phenyl]-ethylamine]-quinine dihydrochloride, 3.12g (0.05mol) of ammonium formate and 5% palladium on carbon The catalyst was 1.5g, 200ml of tetrahydrofuran was added, and the reaction was carried out at 30°C for 8 hours. After cooling, the catalyst was filtered off. After the solvent was recovered, 2.62g of the target product (R)-3-aminoquinine dihydrochloride was collected, with a yield of 80%. 1 HNMR(DMSO-d 6 )δ: 1.75~1.93(m,3H,), 2.14~2.20(m,1H), 2.31(q,1H), 3.10~3.24(m,5H), 3.55~3.68(m,2H); EI-MS (m / z): 126[M-2HCl]; (C=1, H 2 O); mp>285°C.

Embodiment 3

[0033] Add 5g (0.013mol) of (3S)-3-[(S)-1-phenyl]-ethylamine]-quinine dihydrobromide, 4.0g (0.063mol) of ammonium formate and 10% palladium on carbon Hydrogen catalyst 1g was added with 200m of toluene, heated to reflux at 90°C for 5 hours, the catalyst was filtered off after cooling, the target product (S)-3-aminoquinine dihydrobromide 3.04g was collected after the solvent was recovered, and the yield was 83%. 1 HNMR(DMSO-d 6 )δ: 1.75~1.94(m,3H,), 2.15~2.22(m,1H), 2.32(q,1H), 3.11~3.20(m,5H), 3.55~3.68(m,2H); ESI(m / z): 126[M-2HCl]; mp>285°C.

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 present invention discloses a preparation method, which pharmaceutically permits salt to be accepted by a intermediate of 3-amino-quinin, in which ammonium formate is used to supply hydrogen to make 3-[(1-phenyl)-ethylamine] quinine pharmaceutically feasible to accept salt, ammonium formate, and palladium hydrogenation catalyst to carry out hydrogenation-debenzyl reaction to produce the intended product. The method provided by the present invention uses cheap and easily accessible ammonium formate as the hydrogen provider to substitute for the hydrogen gas to supply the hydrogen, and the reactions can be performed in an ordinary container to avoid the application of high-pressure pot, therefore, the preparation method is easy and the scaled production is easily accomplishable.

Description

Technical field [0001] The present invention relates to the field of medicinal chemistry, in particular to a method for preparing 3-aminoquinine pharmaceutically acceptable salts, which are key intermediates of drugs such as palonosetron hydrochloride, a chemotherapy drug. Background technique [0002] Palonosetron hydrochloride is the third-generation setron antiemetic drug. 3 The receptor is highly selective antagonist, developed by Heisinn Healthcare SA of Switzerland, and listed in September 2003. [0003] Synthesis of 3-aminoquinine dihydrochloride, a key intermediate of Palonosetron hydrochloride and other drugs, literature Synthetic Communications, 1992, 22(13), 1895-1911 and Synthetic Communications, 1996, 26(10), 2009-2015 The reported method is mainly 3-[(1-phenyl)-ethylamine]quinine dihydrochloride through Pearl'S catalyst (Pd(OH) 2 / C) Preparation by catalytic hydrogenation debenzylation, the synthetic route is as follows: [0004] [0005] This method has the follo...

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): C07D453/02
Inventor 张福利胡猛谢美华
Owner SHANGHAI INST OF PHARMA IND CO LTD
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
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