AR042877A1 - Sintesis de cloruro de 4-amino-2-butenoilo y su uso para la preparacion de 3-ciano quinolinas - Google Patents
Sintesis de cloruro de 4-amino-2-butenoilo y su uso para la preparacion de 3-ciano quinolinasInfo
- Publication number
- AR042877A1 AR042877A1 ARP040100092A ARP040100092A AR042877A1 AR 042877 A1 AR042877 A1 AR 042877A1 AR P040100092 A ARP040100092 A AR P040100092A AR P040100092 A ARP040100092 A AR P040100092A AR 042877 A1 AR042877 A1 AR 042877A1
- Authority
- AR
- Argentina
- Prior art keywords
- suspension
- compound
- formula
- alkenyl
- alkyl
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 title 1
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 239000000725 suspension Substances 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 abstract 4
- 125000003342 alkenyl group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 238000001816 cooling Methods 0.000 abstract 2
- 239000002244 precipitate Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- -1 -C6H5 Chemical class 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000012320 chlorinating reagent Substances 0.000 abstract 1
- 239000003086 colorant Substances 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 125000005309 thioalkoxy group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/30—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and unsaturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Quinoline Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
Reivindicación 1: Un compuesto de fórmula (1) en la cual S1 y S2 son cada uno independientemente H, cicloalquilo, cicloalquenilo, alquilo, alquenilo, alquinilo, aralquilo, arilo, o heteroarilo sustituido o no sustituido, o S1 y S2 conjuntamente con el N al cual están unidos, forman un heteroarilo que contiene N o un cicloheteroalquilo; o una sal de adición de ácido de dicho compuesto. Reivindicación 10: Un procedimiento para la preparación de un compuesto de fórmula (2) en la cual R1, R2, R3, R4 y R0 están independientemente seleccionados del grupo que consiste en -H, -CN, alquilo, alcoxi, vinilo, alquenilo, formilo, -CF3, -CCl3, haluro,-C6H5, amida, acilo, éster, amino, tioalcoxi, fosfino, y combinaciones de los mismos; o tomados conjuntamente, R1, y R2, R2 y R3, R3 y R4, o R4 y R0, junto con los átomos de C a los cuales están unidos forman un heteroarilo o cicloheteroalquilo opcionalmente sustituido; y S1 y S2 están independientemente seleccionados del grupo que consiste en H, alquilo, alquenilo, alquinilo, aralquilo, arilo sustituido o no sustituido, o S1 y S2 conjuntamente con el N al cual están unidos forman un heteroarilo que contiene N, que comprende: a) enfriar una suspensión de una sal de adición de ácido del compuesto de la fórmula (5), en la cual S1 y S2 son tal como se han definido anteriormente; b) agregar un agente clorante a la suspensión en la etapa (a); c) calentar y agitar la suspensión de la etapa (b) hasta que se consume completamente el agente colorante; d) enfriar la suspensión en la etapa (c); e) agregar una anilina de la fórmula (4) por goteo a la suspensión en la etapa (d) hasta que la concentración de la anilina es inferior a aproximadamente 5%; en la cual R1, R2, R3, R4 y R0 son tal como se han definido anteriormente; f) agregar una base acuosa a la suspensión en la etapa (e) para obtener un precipitado; y g) filtrar y lavar y secar el precipitado en la etapa (f) para proporcionar el compuesto de la fórmula (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44147003P | 2003-01-21 | 2003-01-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR042877A1 true AR042877A1 (es) | 2005-07-06 |
Family
ID=32825162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP040100092A AR042877A1 (es) | 2003-01-21 | 2004-01-14 | Sintesis de cloruro de 4-amino-2-butenoilo y su uso para la preparacion de 3-ciano quinolinas |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7126025B2 (es) |
| EP (1) | EP1585479A2 (es) |
| CN (1) | CN100537518C (es) |
| AR (1) | AR042877A1 (es) |
| AU (1) | AU2004207475A1 (es) |
| CA (1) | CA2514550A1 (es) |
| CL (2) | CL2004000016A1 (es) |
| CR (1) | CR7950A (es) |
| EC (1) | ECSP055974A (es) |
| MX (1) | MXPA05008876A (es) |
| NO (1) | NO20053890L (es) |
| RU (1) | RU2345984C2 (es) |
| SG (1) | SG166678A1 (es) |
| TW (1) | TW200418763A (es) |
| WO (1) | WO2004066919A2 (es) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA77200C2 (en) | 2001-08-07 | 2006-11-15 | Wyeth Corp | Antineoplastic combination of cci-779 and bkb-569 |
| CL2004000016A1 (es) | 2003-01-21 | 2005-04-15 | Wyeth Corp | Compuesto derivado de cloruro de 4-amino-2-butenoilo o una sal farmaceuticamente aceptable del mismo; procedimiento para preparar dicho compuesto, util como intermediario en la sintesis de compuestos inhibidores de proteina quinasa tirosina. |
| EP1694686A1 (en) | 2003-12-19 | 2006-08-30 | Takeda San Diego, Inc. | Kinase inhibitors |
| AU2005206541A1 (en) * | 2004-01-16 | 2005-08-04 | Wyeth | Quinoline intermediates of receptor tyrosine kinase inhibitors and the synthesis thereof |
| EP1778669A2 (en) | 2004-08-18 | 2007-05-02 | Takeda San Diego, Inc. | Kinase inhibitors |
| ATE479687T1 (de) | 2004-10-15 | 2010-09-15 | Takeda Pharmaceutical | Kinaseinhibitoren |
| DK1848414T3 (da) | 2005-02-03 | 2011-07-25 | Gen Hospital Corp | Fremgangsmåde til behandling af gefitinib-resistent cancer |
| KR20080016600A (ko) * | 2005-05-25 | 2008-02-21 | 와이어쓰 | 3-시아노-퀴놀린의 제조 방법 및 이에 의해 제조된 중간생성물 |
| CA2609186A1 (en) * | 2005-05-25 | 2006-11-30 | Wyeth | Methods of synthesizing substituted 3-cyanoquinolines and intermediates thereof |
| CA2608589A1 (en) * | 2005-05-25 | 2006-11-30 | Wyeth | Methods of synthesizing 6-alkylaminoquinoline derivatives |
| US8119655B2 (en) | 2005-10-07 | 2012-02-21 | Takeda Pharmaceutical Company Limited | Kinase inhibitors |
| AU2006311877A1 (en) | 2005-11-04 | 2007-05-18 | Wyeth Llc | Antineoplastic combinations with mTOR inhibitor, herceptin, and/orHKI-272 |
| CA2833852C (en) | 2005-11-11 | 2014-10-21 | Boehringer Ingelheim International Gmbh | Quinazoline derivatives for the treatment of cancer diseases |
| JP2010505962A (ja) | 2006-10-09 | 2010-02-25 | 武田薬品工業株式会社 | キナーゼ阻害剤 |
| US8022216B2 (en) | 2007-10-17 | 2011-09-20 | Wyeth Llc | Maleate salts of (E)-N-{4-[3-chloro-4-(2-pyridinylmethoxy)anilino]-3-cyano-7-ethoxy-6-quinolinyl}-4-(dimethylamino)-2-butenamide and crystalline forms thereof |
| SI2310011T1 (sl) | 2008-06-17 | 2013-10-30 | Wyeth Llc | Antineoplastične kombinacije, ki vsebujejo HKI-272 in vinorelbin |
| BRPI0916694B1 (pt) | 2008-08-04 | 2021-06-08 | Wyeth Llc | uso de neratinibe em combinação com capecitabina para tratar câncer de mama metastático de erbb-2 positivo, kit e produto compreendendo os mesmos |
| WO2010048477A2 (en) * | 2008-10-24 | 2010-04-29 | Wyeth Llc | Improved process for preparation of coupled products from 4-amino-3-cyanoquinolines using stabilized intermediates |
| CA2743728A1 (en) * | 2008-11-17 | 2010-05-20 | Novartis Ag | Enantioselective synthesis of .gamma.-amino-.alpha.,.beta.-unsaturated carboxylic acid derivatives |
| CA2755789C (en) | 2009-04-06 | 2016-01-19 | Wyeth Llc | Treatment regimen utilizing neratinib for breast cancer |
| WO2010131921A2 (ko) * | 2009-05-14 | 2010-11-18 | 코오롱생명과학 주식회사 | 알킬아민 유도체의 제조방법 |
| EP2451445B1 (en) | 2009-07-06 | 2019-04-03 | Boehringer Ingelheim International GmbH | Process for drying of bibw2992, of its salts and of solid pharmaceutical formulations comprising this active ingredient |
| CN107441058A (zh) | 2009-11-09 | 2017-12-08 | 惠氏有限责任公司 | 包衣药物球状体及消除或减少病症如呕吐和腹泻的用途 |
| CN102731395B (zh) * | 2011-04-15 | 2015-02-04 | 中国科学院上海药物研究所 | 抗肿瘤药物来那替尼的中间体及其制备与应用 |
| US9242965B2 (en) | 2013-12-31 | 2016-01-26 | Boehringer Ingelheim International Gmbh | Process for the manufacture of (E)-4-N,N-dialkylamino crotonic acid in HX salt form and use thereof for synthesis of EGFR tyrosine kinase inhibitors |
| CN104926669A (zh) * | 2014-03-18 | 2015-09-23 | 江苏豪森医药集团连云港宏创医药有限公司 | 反式-4-二甲基胺基巴豆酸盐酸盐的制备方法 |
| US9758471B2 (en) | 2014-06-02 | 2017-09-12 | Sun Pharmaceutical Industries Limited | Process for the preparation of 4-dimethylaminocrotonic acid |
| CN105439879B (zh) * | 2014-08-07 | 2018-08-10 | 天津法莫西医药科技有限公司 | 一种反式-4-二甲胺基巴豆酸盐酸盐的制备方法 |
| CN105669479B (zh) * | 2015-12-31 | 2018-04-13 | 重庆威鹏药业有限公司 | 一锅法制备高纯度反式‑4‑二甲基胺基巴豆酸盐酸盐的方法 |
| DK3447051T3 (da) * | 2016-04-28 | 2022-01-17 | Jiangsu Hengrui Medicine Co | Fremgangsmåde til fremstilling af tyrosinkinaseinhibitor og derivat deraf |
| AU2018351539A1 (en) | 2017-10-18 | 2020-05-28 | Jiangsu Hengrui Medicine Co., Ltd. | Preparation method for tyrosine kinase inhibitor and intermediate thereof |
| CN111217850B (zh) * | 2019-01-31 | 2023-05-26 | 微宏先进材料公司 | 硅基酯类化合物制备方法、硅基酯类化合物、包含其的电解液及二次电池 |
| CN112679473B (zh) * | 2019-10-18 | 2024-03-05 | 四川科伦药物研究院有限公司 | 来那替尼中间体晶体、制备方法及其用途 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4194050A (en) | 1976-04-30 | 1980-03-18 | Sumitomo Chemical Company, Limited | Process for producing an enamide |
| US4195021A (en) | 1977-10-26 | 1980-03-25 | Eli Lilly And Company | 1,3-Disubstituted 2-azetidinone antibitotics |
| US4193983A (en) | 1978-05-16 | 1980-03-18 | Syva Company | Labeled liposome particle compositions and immunoassays therewith |
| BE897134A (fr) | 1983-06-24 | 1983-12-27 | Solvay | Dienes polysubstitues |
| US4478959A (en) | 1983-09-29 | 1984-10-23 | Air Products And Chemicals, Inc. | Amino and amido divalent metal carboxylates useful as catalysts for polyurethane formulations |
| DE3347659A1 (de) | 1983-12-31 | 1985-07-11 | Bayer Ag, 5090 Leverkusen | Neue lackloesungen auf der basis von hydantoingruppen enthaltenden polymeren |
| US4664825A (en) | 1984-10-25 | 1987-05-12 | The Lubrizol Corporation | Sulfurized compositions and lubricants containing them |
| AU634871B2 (en) | 1990-03-20 | 1993-03-04 | Banyu Pharmaceutical Co., Ltd. | Substituted amine derivatives having anti-hyperlipemia activity |
| UA73073C2 (uk) | 1997-04-03 | 2005-06-15 | Уайт Холдінгз Корпорейшн | Заміщені 3-ціанохіноліни, спосіб їх одержання та фармацевтична композиція |
| US6002008A (en) | 1997-04-03 | 1999-12-14 | American Cyanamid Company | Substituted 3-cyano quinolines |
| UA77200C2 (en) * | 2001-08-07 | 2006-11-15 | Wyeth Corp | Antineoplastic combination of cci-779 and bkb-569 |
| CL2004000016A1 (es) | 2003-01-21 | 2005-04-15 | Wyeth Corp | Compuesto derivado de cloruro de 4-amino-2-butenoilo o una sal farmaceuticamente aceptable del mismo; procedimiento para preparar dicho compuesto, util como intermediario en la sintesis de compuestos inhibidores de proteina quinasa tirosina. |
-
2004
- 2004-01-05 CL CL200400016A patent/CL2004000016A1/es unknown
- 2004-01-12 TW TW093100676A patent/TW200418763A/zh unknown
- 2004-01-14 AR ARP040100092A patent/AR042877A1/es unknown
- 2004-01-15 US US10/758,187 patent/US7126025B2/en not_active Expired - Fee Related
- 2004-01-16 CN CNB2004800077239A patent/CN100537518C/zh not_active Expired - Fee Related
- 2004-01-16 MX MXPA05008876A patent/MXPA05008876A/es active IP Right Grant
- 2004-01-16 RU RU2005126418/04A patent/RU2345984C2/ru not_active IP Right Cessation
- 2004-01-16 CA CA002514550A patent/CA2514550A1/en not_active Abandoned
- 2004-01-16 SG SG200704889-5A patent/SG166678A1/en unknown
- 2004-01-16 WO PCT/US2004/001133 patent/WO2004066919A2/en not_active Ceased
- 2004-01-16 AU AU2004207475A patent/AU2004207475A1/en not_active Abandoned
- 2004-01-16 EP EP04702974A patent/EP1585479A2/en not_active Withdrawn
-
2005
- 2005-08-19 NO NO20053890A patent/NO20053890L/no not_active Application Discontinuation
- 2005-08-19 CR CR7950A patent/CR7950A/es not_active Application Discontinuation
- 2005-08-22 EC EC2005005974A patent/ECSP055974A/es unknown
-
2007
- 2007-05-07 CL CL2007001286A patent/CL2007001286A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CR7950A (es) | 2006-05-30 |
| CL2007001286A1 (es) | 2008-01-25 |
| CA2514550A1 (en) | 2004-08-12 |
| RU2345984C2 (ru) | 2009-02-10 |
| CN1761644A (zh) | 2006-04-19 |
| RU2005126418A (ru) | 2006-01-27 |
| EP1585479A2 (en) | 2005-10-19 |
| SG166678A1 (en) | 2010-12-29 |
| TW200418763A (en) | 2004-10-01 |
| CN100537518C (zh) | 2009-09-09 |
| NO20053890L (no) | 2005-10-20 |
| MXPA05008876A (es) | 2005-10-05 |
| US20040162442A1 (en) | 2004-08-19 |
| WO2004066919A3 (en) | 2005-01-27 |
| NO20053890D0 (no) | 2005-08-19 |
| ECSP055974A (es) | 2006-01-16 |
| WO2004066919A2 (en) | 2004-08-12 |
| US7126025B2 (en) | 2006-10-24 |
| AU2004207475A1 (en) | 2004-08-12 |
| CL2004000016A1 (es) | 2005-04-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |