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
Links
- 150000001875 compounds Chemical class 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 abstract 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 239000002994 raw material Substances 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- 208000001435 Thromboembolism Diseases 0.000 abstract 1
- AVPMRIWGOGRNBF-UHFFFAOYSA-N [bromo(fluoro)methyl]benzene Chemical compound FC(Br)C1=CC=CC=C1 AVPMRIWGOGRNBF-UHFFFAOYSA-N 0.000 abstract 1
- 235000019270 ammonium chloride Nutrition 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- WXXSNCNJFUAIDG-UHFFFAOYSA-N riociguat Chemical compound N1=C(N)C(N(C)C(=O)OC)=C(N)N=C1C(C1=CC=CN=C11)=NN1CC1=CC=CC=C1F WXXSNCNJFUAIDG-UHFFFAOYSA-N 0.000 abstract 1
- 229960000529 riociguat Drugs 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 abstract 1
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.
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 (8)
| 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 |
| CN108463224A (en) | 2015-12-14 | 2018-08-28 | 铁木医药有限公司 | Application of sGC stimulators in the treatment of gastrointestinal dysfunction |
| EP3554488A2 (en) | 2016-12-13 | 2019-10-23 | Cyclerion Therapeutics, Inc. | Use of sgc stimulators for the treatment of esophageal motility disorders |
| US12220414B2 (en) | 2018-07-11 | 2025-02-11 | Tisento Therapeutics Inc. | Use of sGC stimulators for the treatment of mitochondrial disorders |
| CN115947689B (en) * | 2022-09-23 | 2025-08-29 | 湖南华腾制药有限公司 | A method for synthesizing riociguat intermediates using a continuous flow microreactor |
| CN117024334A (en) * | 2023-07-20 | 2023-11-10 | 重庆医药高等专科学校 | A kind of synthesis method of 2-fluoro-3-hydroxypyridine |
Family Cites Families (12)
| 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 |
| KR20100117686A (en) * | 2008-02-29 | 2010-11-03 | 어레이 바이오파마 인크. | Pyrazole [3,4-b] pyridine raf inhibitors |
| AU2009308687A1 (en) | 2008-11-03 | 2010-05-06 | Chemocentryx, Inc. | Compounds for the treatment of osteoporosis and cancers |
| 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 |
| WO2011147810A1 (en) | 2010-05-26 | 2011-12-01 | Bayer Pharma Aktiengesellschaft | THE USE OF sGC STIMULATORS, sGC ACTIVATORS, ALONE AND COMBINATIONS WITH PDE5 INHIBITORS FOR THE TREATMENT OF SYSTEMIC SCLEROSIS (SSc). |
| DE102010021637A1 (en) | 2010-05-26 | 2011-12-01 | Bayer Schering Pharma Aktiengesellschaft | Substituted 5-fluoro-1H-pyrazolopyridines and their use |
| EP2575473B1 (en) * | 2010-05-27 | 2016-01-20 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| GEP20166474B (en) | 2011-04-22 | 2016-05-10 | Pfizer | Pyrazolospiroketone derivatives for use as acetyl-coa carboxylase inhibitors |
| JP6054967B2 (en) * | 2011-09-02 | 2016-12-27 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | Substituted annelated pyrimidines and uses thereof |
| 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 |
-
2011
- 2011-12-12 CN CN201110414004.0A patent/CN102491974B/en active Active
-
2012
- 2012-11-28 JP JP2014545075A patent/JP5791825B2/en active Active
- 2012-11-28 WO PCT/CN2012/085451 patent/WO2013086935A1/en not_active Ceased
- 2012-11-28 US US14/364,040 patent/US8957210B2/en active Active
- 2012-11-28 IN IN5281DEN2014 patent/IN2014DN05281A/en unknown
- 2012-11-28 DE DE112012005176.9T patent/DE112012005176B4/en active Active
-
2014
- 2014-06-10 IL IL233066A patent/IL233066B/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| DE112012005176T5 (en) | 2014-08-28 |
| IL233066A0 (en) | 2014-07-31 |
| IL233066B (en) | 2019-01-31 |
| US8957210B2 (en) | 2015-02-17 |
| DE112012005176B4 (en) | 2018-10-11 |
| JP2015500248A (en) | 2015-01-05 |
| WO2013086935A1 (en) | 2013-06-20 |
| US20140309425A1 (en) | 2014-10-16 |
| CN102491974A (en) | 2012-06-13 |
| JP5791825B2 (en) | 2015-10-07 |
| CN102491974B (en) | 2013-08-07 |
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