AR100020A1 - Proceso para preparar (r)-5-bromo-4-(3-amino)piperidin-1-il)-3-(ciclopropancarboxamida)-1h-pirrolo[2,3-b]piridina - Google Patents
Proceso para preparar (r)-5-bromo-4-(3-amino)piperidin-1-il)-3-(ciclopropancarboxamida)-1h-pirrolo[2,3-b]piridinaInfo
- Publication number
- AR100020A1 AR100020A1 ARP140103155A ARP140103155A AR100020A1 AR 100020 A1 AR100020 A1 AR 100020A1 AR P140103155 A ARP140103155 A AR P140103155A AR P140103155 A ARP140103155 A AR P140103155A AR 100020 A1 AR100020 A1 AR 100020A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- amino
- piperidin
- bromo
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title 2
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 title 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- 125000006239 protecting group Chemical group 0.000 abstract 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 101000777293 Homo sapiens Serine/threonine-protein kinase Chk1 Proteins 0.000 abstract 1
- GVEBPZNSHYRHKS-UHFFFAOYSA-N N-pyrrolo[2,3-b]pyridin-1-ylcyclopropanecarboxamide Chemical compound C1(CC1)C(=O)NN1C=CC=2C1=NC=CC=2 GVEBPZNSHYRHKS-UHFFFAOYSA-N 0.000 abstract 1
- 102100031081 Serine/threonine-protein kinase Chk1 Human genes 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 abstract 1
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 125000006328 iso-butylcarbonyl group Chemical group [H]C([H])([H])C([H])(C(*)=O)C([H])([H])[H] 0.000 abstract 1
- -1 isopropylcarbonyl Chemical group 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229960002317 succinimide Drugs 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epidemiology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
La presente proporciona procesos para la preparación de aquellos útiles en la preparación de compuestos que se pueden usar como inhibidores de CHK1. Reivindicación 1: Un proceso para preparar (R)-5-bromo-4-(3-amino)piperidin-1-il)-3(ciclopropancarboxamido)-1H-pirrolo[2,3-b]piridina de fórmula (1) que comprende la etapa de hacer reaccionar un compuesto de fórmula (2) donde X es halógeno, con un compuesto de fórmula (3) donde R es un grupo protector amino, para proporcionar un compuesto de fórmula (4). Reivindicación 12: El proceso de cualquiera de las reivindicaciones 1 a 11, donde se comprende además la etapa de someter un compuesto de fórmula (4) donde R es un grupo protector amino, a una reducción de nitro para obtener un compuesto de fórmula (5). Reivindicación 18: El proceso de cualquiera de las reivindicaciones 12 a 17 que comprende además la etapa de hacer reaccionar un compuesto de fórmula (5) con un compuesto de fórmula (6) donde R¹ se selecciona del grupo que consiste en cloro, flúor, bromuro y OR², donde R² es seleccionado del grupo que consiste en ciclopropilcarbonilo, isobutilcarbonilo, isopropilcarbonilo, etilcarbonilo, metilcarbonilo, 2-piridilo, N-succinimida, para obtener un compuesto de fórmula (7). Reivindicación 19: El proceso de la reivindicación 18 que comprende además la etapa de eliminar el grupo protector R en el compuesto de fórmula (7) para obtener (R)-5-bromo-4-(3-(amino)piperidin-1il)-3-(ciclopropancarboxamido)-1H-pirrolo[2,3-b]piridina de fórmula (1).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361868933P | 2013-08-22 | 2013-08-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR100020A1 true AR100020A1 (es) | 2016-09-07 |
Family
ID=52484170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP140103155A AR100020A1 (es) | 2013-08-22 | 2014-08-22 | Proceso para preparar (r)-5-bromo-4-(3-amino)piperidin-1-il)-3-(ciclopropancarboxamida)-1h-pirrolo[2,3-b]piridina |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US10329288B2 (es) |
| EP (1) | EP3036227B1 (es) |
| JP (1) | JP6463758B2 (es) |
| KR (1) | KR102325163B1 (es) |
| CN (1) | CN105705499B (es) |
| AR (1) | AR100020A1 (es) |
| CA (1) | CA2921956C (es) |
| HK (1) | HK1222392A1 (es) |
| MX (1) | MX369174B (es) |
| RU (1) | RU2672725C2 (es) |
| WO (1) | WO2015027092A1 (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MA41599A (fr) * | 2015-02-26 | 2018-01-02 | Array Biopharma Inc | Formes cristallines d'un composé pyrrolopyridine |
| CN109796349A (zh) * | 2019-03-01 | 2019-05-24 | 西南石油大学 | 一种还原芳香硝基化合物制备芳胺类化合物的方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2154825T3 (es) * | 1995-05-19 | 2001-04-16 | Novartis Ag | Procedimiento para la hidrogenacion catalitica de nitro compuestos aromaticos. |
| YU83302A (sh) | 2000-06-26 | 2005-09-19 | Pfizer Products Inc. | Jedinjenja pirolo (2,3-d) pirimidina kao imunosupresivni agensi |
| WO2003028724A1 (en) * | 2001-10-04 | 2003-04-10 | Smithkline Beecham Corporation | Chk1 kinase inhibitors |
| GB0330043D0 (en) * | 2003-12-24 | 2004-01-28 | Pharmacia Italia Spa | Pyrrolo [2,3-b] pyridine derivatives active as kinase inhibitors process for their preparation and pharmaceutical compositions comprising them |
| SE0401001D0 (sv) * | 2004-03-31 | 2004-03-31 | Astrazeneca Ab | Chemical process |
| AR054416A1 (es) * | 2004-12-22 | 2007-06-27 | Incyte Corp | Pirrolo [2,3-b]piridin-4-il-aminas y pirrolo [2,3-b]pirimidin-4-il-aminas como inhibidores de las quinasas janus. composiciones farmaceuticas. |
| EP1851220A2 (en) * | 2005-02-23 | 2007-11-07 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazonaphthyridines |
| KR20080026654A (ko) * | 2005-07-14 | 2008-03-25 | 아스텔라스세이야쿠 가부시키가이샤 | 헤테로시클릭 야누스 키나제 3 억제제 |
| WO2009089352A1 (en) * | 2008-01-08 | 2009-07-16 | Array Biopharma Inc. | Pyrrolopyridines as kinase inhibitors |
| US8372842B2 (en) | 2008-01-09 | 2013-02-12 | Array Biopharma Inc. | Pyrazolopyridines as kinase inhibitors |
| CL2009001152A1 (es) * | 2008-05-13 | 2009-10-16 | Array Biopharma Inc | Compuestos derivados de n-(4-(cicloalquilo nitrogenado-1-il)-1h-pirrolo[2,3-b]piridin-3-il)amida, inhibidores de cinasa; proceso de preparacion; composicion farmaceutica; y su uso para el tratamiento de una enfermedad proliferativa. |
| BR112014003496B1 (pt) | 2011-08-18 | 2022-02-22 | Nippon Shinyaku Co., Ltd | Derivado heterocíclico, usos do mesmo e composição farmacêutica |
| GB201201566D0 (en) | 2012-01-30 | 2012-03-14 | Vernalis R&D Ltd | New chemical compounds |
-
2014
- 2014-08-21 CA CA2921956A patent/CA2921956C/en active Active
- 2014-08-21 CN CN201480054349.1A patent/CN105705499B/zh active Active
- 2014-08-21 RU RU2016110081A patent/RU2672725C2/ru active
- 2014-08-21 US US14/913,635 patent/US10329288B2/en active Active
- 2014-08-21 MX MX2016002198A patent/MX369174B/es active IP Right Grant
- 2014-08-21 KR KR1020167007101A patent/KR102325163B1/ko active IP Right Grant
- 2014-08-21 JP JP2016536458A patent/JP6463758B2/ja not_active Expired - Fee Related
- 2014-08-21 EP EP14838336.7A patent/EP3036227B1/en active Active
- 2014-08-21 WO PCT/US2014/052146 patent/WO2015027092A1/en active Application Filing
- 2014-08-22 AR ARP140103155A patent/AR100020A1/es unknown
-
2016
- 2016-09-06 HK HK16110566.5A patent/HK1222392A1/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN105705499B (zh) | 2018-10-12 |
| MX2016002198A (es) | 2016-09-08 |
| WO2015027092A1 (en) | 2015-02-26 |
| RU2672725C2 (ru) | 2018-11-19 |
| EP3036227B1 (en) | 2020-01-08 |
| RU2016110081A3 (es) | 2018-05-18 |
| US20160200723A1 (en) | 2016-07-14 |
| EP3036227A4 (en) | 2017-01-04 |
| MX369174B (es) | 2019-10-30 |
| CA2921956C (en) | 2021-10-19 |
| US10329288B2 (en) | 2019-06-25 |
| CA2921956A1 (en) | 2015-02-26 |
| KR102325163B1 (ko) | 2021-11-11 |
| HK1222392A1 (zh) | 2017-06-30 |
| CN105705499A (zh) | 2016-06-22 |
| KR20160043116A (ko) | 2016-04-20 |
| JP6463758B2 (ja) | 2019-02-06 |
| EP3036227A1 (en) | 2016-06-29 |
| JP2016528296A (ja) | 2016-09-15 |
| RU2016110081A (ru) | 2017-09-27 |
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