IN2014DN05281A - - Google Patents

Info

Publication number
IN2014DN05281A
IN2014DN05281A IN5281DEN2014A IN2014DN05281A IN 2014DN05281 A IN2014DN05281 A IN 2014DN05281A IN 5281DEN2014 A IN5281DEN2014 A IN 5281DEN2014A IN 2014DN05281 A IN2014DN05281 A IN 2014DN05281A
Authority
IN
India
Prior art keywords
compound
reacted
pyrazolo
fluorobenzyl
pyridin
Prior art date
Application number
Inventor
Jin Li
Xiaoyu Yang
Jingwei Zhu
Minmin Yang
Xihan Wu
Original Assignee
Pharmablock Nanjing R & D Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Pharmablock Nanjing R & D Co Ltd filed Critical Pharmablock Nanjing R & D Co Ltd
Publication of IN2014DN05281A publication Critical patent/IN2014DN05281A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The present invention relates to the field of chemical synthesis, and in particular t o a method for synthesizing l-(2- fluorobenzyl)-lH-pyrazolo[3,4-b]pyridin-3-formamidine hydrochloride, which i s an important intermediate of Riociguat that i s an anti-thromboembolic-disease medicine. The method i s characterized in that: -iodo- 1H-pyrazolo [ ,4-b]pyridine i s used as a raw m a terial; the raw material i s reacted with fluorobenzyl bromide t o form a compound (10); the compound (10) i s reacted with zinc cyan - ide t o form a compound (6); the compound (6) i s reacted with sodium methoxide, ammonium chloride, acetic acid and methanol to form a compound (8); and the compound (8) i s reacted with chlorine hydride gas t o form l-(2-fluorobenzyl)-lH-pyrazolo[3,4- b]pyridin-3-formamidine hydrochloride. The method has the characteristics of cheap and readily available raw materials, high yield, mild reaction conditions and the like, and i s a synthesis method having a large-scale preparation value.
IN5281DEN2014 2011-12-12 2012-11-28 IN2014DN05281A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201110414004.0A CN102491974B (en) 2011-12-12 2011-12-12 Method for synthesizing 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-formamidine hydrochloride
PCT/CN2012/085451 WO2013086935A1 (en) 2011-12-12 2012-11-28 Method for synthesizing 1-(2-fluorobenzyl)-1h-pyrazolo[3,4-b]pyridin-3-formamidine hydrochloride

Publications (1)

Publication Number Publication Date
IN2014DN05281A true IN2014DN05281A (en) 2015-04-03

Family

ID=46183843

Family Applications (1)

Application Number Title Priority Date Filing Date
IN5281DEN2014 IN2014DN05281A (en) 2011-12-12 2012-11-28

Country Status (7)

Country Link
US (1) US8957210B2 (en)
JP (1) JP5791825B2 (en)
CN (1) CN102491974B (en)
DE (1) DE112012005176B4 (en)
IL (1) IL233066B (en)
IN (1) IN2014DN05281A (en)
WO (1) WO2013086935A1 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102491974B (en) 2011-12-12 2013-08-07 南京药石药物研发有限公司 Method for synthesizing 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-formamidine hydrochloride
CN104086545A (en) * 2014-07-29 2014-10-08 安徽联创药物化学有限公司 Synthesis method of 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridyl-3-formamidine hydrochloride
CN105237531A (en) * 2015-10-15 2016-01-13 湖南华腾制药有限公司 Method for preparing riociguat intermediate and intermediate compound
AU2016371762A1 (en) 2015-12-14 2018-06-21 Cyclerion Therapeutics, Inc. Use of sGC stimulators for the treatment of gastrointestinal sphincter dysfunction
US20190381039A1 (en) 2016-12-13 2019-12-19 Cyclerion Therapeutics, Inc. USE OF sGC STIMULATORS FOR THE TREATMENT OF ESOPHAGEAL MOTILITY DISORDERS
BR112021000358A2 (en) 2018-07-11 2021-04-06 Cyclerion Therapeutics, Inc. USE OF SGC STIMULATORS TO TREAT MITOCONDDRIAL DISORDERS

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR031176A1 (en) * 2000-11-22 2003-09-10 Bayer Ag NEW DERIVATIVES OF PIRAZOLPIRIDINA SUBSTITUTED WITH PIRIDINE
DE10220570A1 (en) 2002-05-08 2003-11-20 Bayer Ag Carbamate-substituted pyrazolopyridines
AU2009222144A1 (en) 2008-02-29 2009-09-11 Array Biopharma Inc. Pyrazole [3, 4-b] pyridine Raf inhibitors
EP2352501B1 (en) 2008-11-03 2014-01-01 ChemoCentryx, Inc. Compounds for use in the treatment of osteoporosis
CN101648909B (en) * 2009-09-14 2011-10-05 南京第一农药集团有限公司 Method for preparing cyanopyridine by using chloropyridine under the catalysis of ligand-free palladium
US20110225969A1 (en) 2010-03-19 2011-09-22 Gm Global Technology Operations, Inc. Compressor bypass to exhaust for particulate trap regeneration
ES2549979T3 (en) * 2010-05-26 2015-11-03 Adverio Pharma Gmbh The use of sGC stimulators, sGC activators, alone and in combinations with PDE5 inhibitors for the treatment of systemic sclerosis (EcS)
DE102010021637A1 (en) 2010-05-26 2011-12-01 Bayer Schering Pharma Aktiengesellschaft Substituted 5-fluoro-1H-pyrazolopyridines and their use
MA34330B1 (en) * 2010-05-27 2013-06-01 Merck Sharp & Dohme SOLUBLE GUANYLATE CYCLASE ACTIVATORS
DK2699576T3 (en) 2011-04-22 2016-02-15 Pfizer Pyrazolospiroketon derivatives for use as acetyl-CoA carboxylase inhibitors
BR112014005110A2 (en) * 2011-09-02 2017-04-18 Bayer Ip Gmbh substituted ring pyrimidines and their use
CN102491974B (en) 2011-12-12 2013-08-07 南京药石药物研发有限公司 Method for synthesizing 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-formamidine hydrochloride

Also Published As

Publication number Publication date
US20140309425A1 (en) 2014-10-16
CN102491974A (en) 2012-06-13
IL233066A0 (en) 2014-07-31
IL233066B (en) 2019-01-31
DE112012005176T5 (en) 2014-08-28
WO2013086935A1 (en) 2013-06-20
CN102491974B (en) 2013-08-07
DE112012005176B4 (en) 2018-10-11
JP5791825B2 (en) 2015-10-07
JP2015500248A (en) 2015-01-05
US8957210B2 (en) 2015-02-17

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