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

Processes for making ponatinib and intermediates thereof

a technology of ponatinib and synthesis method, applied in the field of ponatinib making process and its intermediates, can solve the problems of cumbersome ponatinib making method, inability to synthesize more than 20 steps, and few synthetic approaches, and achieve the effect of commercial economics

Inactive Publication Date: 2014-11-20
MYLAN PHARMA INC
View PDF0 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent text describes a new method for making the drug ponatinib, which is used to treat a type of cancer. The current methods are cumbersome and require many steps, so there is a need for a simpler and more scalable method. The new method involves a novel synthetic approach that allows for a simpler and easier scalable process. The technical effect of this new method is to provide a simpler and more scalable way to make ponatinib, which is a more commercially viable and easily scalable drug.

Problems solved by technology

There are few synthetic approaches available for the preparation of ponatinib.
This method of making ponatinib is cumbersome and involves a synthesis of more than 20 steps.

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
  • Processes for making ponatinib and intermediates thereof
  • Processes for making ponatinib and intermediates thereof
  • Processes for making ponatinib and intermediates thereof

Examples

Experimental program
Comparison scheme
Effect test

examples and experiments

[0074]The following are examples of process conditions and reagents that may be employed in connection with Schemes I-V.

Scheme-I

1-(bromomethyl)-4-nitro-2-(trifluoromethyl)benzene (Compound Ia)

[0075]A suspension of 2-methyl-5-nitrobenzotrifluoride (3.90 g, 19 mmol), N-bromosuccinimide (NBS, 3.56 g, 20 mmol) and 2,2′-azobis(2-methylpropionitrileXAIBN, 94 mg, 0.6 mmol) in CCl4 (40 mL) was refluxed under nitrogen for 16 h. HPLC indicated ca. 50% conversion. More NBS (10 mmol) and AIBN (0.6 mmol) was added, and the mixture was refluxed for another 14 h. HPLC indicated ca. 80% conversion. The reaction mixture was cooled down, and the solid was filtered off and washed with ethyl acetate. The combined filtrate was washed with aq. NaHCO3, dried over Na2SO4, filtered, concentrated on rotovap and further dried under vacuum to afford a solid (1-(bromomethyl)-4-nitro-2-(trifluoromethyl)benzene (Compound Ia)).

2-(4-nitro-2-(trifluoromethyl)benzyl)isoindoline-1,3-dione (Ib)

[0076]To a solution of 1-...

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

PropertyMeasurementUnit
temperatureaaaaaaaaaa
temperatureaaaaaaaaaa
hydrogen pressureaaaaaaaaaa
Login to View More

Abstract

Novel synthetic approaches to make 3-(imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyl-N-[4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide, intermediates and pharmaceutically acceptable salts thereof are provided.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS[0001]This application claims the benefit of U.S. Provisional Patent Application No. 61 / 824,070, filed May 16, 2013, the entirety of which is incorporated herein by reference.FIELD OF THE INVENTION[0002]The presently disclosed subject matter provides novel synthetic approaches to make 3-(imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyl-N-[4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide, intermediates and pharmaceutically acceptable salts thereof.BACKGROUND[0003]3-(imidazo[1,2-b]pyridazin-3-ylethynyl)-4-methyl-N-[4-[(4-methylpiperazin-1-yl)methyl]-3-(trifluoromethyl)phenyl]benzamide, also known as ponatinib, is a multi-targeted tyrosine-kinase inhibitor used in the treatment of chronic myeloid leukemia (CML) and Philadelphia chromosome positive (Ph+) acute lymphoblastic leukemia (ALL). Some forms of CML, those that have the T315I mutation, are resistant to current therapies such as imatinib. Ponatinib was designed to be effec...

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(United States)
IPC IPC(8): C07D487/04C07C233/76C07C233/75C07D209/48C07C233/80
CPCC07D487/04C07D209/48C07C233/76C07C233/75C07C233/80
Inventor KOVI, RAVISHANKERKANNAPAN, JAYARAMANTHAKOR, SANJAY F.PATEL, RAJESH A
Owner MYLAN PHARMA INC
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