AR043027A1 - Preparacion de quinazolinas substituidas - Google Patents
Preparacion de quinazolinas substituidasInfo
- Publication number
- AR043027A1 AR043027A1 ARP040100350A ARP040100350A AR043027A1 AR 043027 A1 AR043027 A1 AR 043027A1 AR P040100350 A ARP040100350 A AR P040100350A AR P040100350 A ARP040100350 A AR P040100350A AR 043027 A1 AR043027 A1 AR 043027A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- independently
- cycloalkyl
- formula
- halogen
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dermatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Se describen métodos y materiales para la preparación de inhibidores irreversibles de tirosina quinasas de fórmula general (1) e intermediarios. Dichos inhibidores, que incluyen N-[4-(3-cloro-4-fluoro-fenilamino)-7-(3-morfolin-4-il-propoxi)-quinazolin-6-il]-acrilamida, son útiles para el tratamiento del cáncer, restenosis, ateroesclerosis, endometriosis y psoriasis. Los métodos descritos emplean estrategias protectoras para minimizar productos laterales diacriloilamino-quinasolina indeseables. Reivindicación 1: Un método para la elaboración de un compuesto de fórmula (1), o su sal, éster, amida o profármaco farmacéuticamente aceptables, en la que R1, R2 y R3 son independientemente H, halógeno, NO2, CN, CF3, alquilo C1-6, haloalquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-8, heterociclilo C3-8, carboxi, alcoxicarbonilo C1-6, alquilcarbamoilo C1-6, (CH2)m-arilo, (CH2)m-heteroarilo, (CH2)m-heterociclilo, (CH2)mCO2R8, (CH2)mS(O)nR8, (CH2)mSO2NR8R9, OR8, SR8, (CH2)mNR8R9, (CH2)mN(O)R8R9, (CH2)mP(O)(OR8)(OR9), (CH2)mCOR8, (CH2)mCO2R8, (CH2)mC(O)NR8R9, (CH2)mC(O)NR8SO2R8, (CH2)mNR8SO2R9, (CH2)mC(O)NR8OR9, (CH2)mS(O)nR8, o (CH2)mSO2NR8R9, en la que (CH2)m-arilo incluye fenilalquilo o fenilalquilo sustituido que tiene de uno a tres sustituyentes que son independientemente NO2, CN, CF3, NH(alquilo C1-6), N(alquilo C1-6)2, o heteroarilo monocíclico y cada alquilo C1-6 está opcionalmente sustituido con OH, NH2 o -N(A)B; R4 y R6 son independientemente H, hidroxi, halógeno, alquilo C1-4, alcoxi C1-4, alquilamino C1-4, alquildiamino C1-4, alquiltio C1-4, alquilsulfinilo C1-4, alquilsulfonilo C1-4,alquilcarbonilo C1-4, alquilcarbamoilo C1-4, dicarbamoilo, carbamilo, alcoxicarbonilo C1-4,ciano, nitro, o trifluorometilo; R5 es fenilo, piridilo, furilo, tiazolilo, imidazolilo o tienilo, teniendo cada uno de ellos opcionalmente uno o dos sustituyentes que son independientemente halógeno, alquilo C1-6, alcoxi C1-6, hidroxi, amino, ciano, NH(alquilo C1-6) o N(alquilo C1-6)2; W es SR7, OR7 o NHR7; y Z es H, halógeno, alquilo C1-6, cicloalquilo C3-8, alcoxi C1-6, cicloalcoxi C3-8,nitro, haloalquilo C1-6, hidroxi, aciloxi C1-6, NH2, NH(alquilo C1-6), N(alquilo C1-6)2, NH(cicloalquilo C3-8), N(cicloalquilo C3-8)2, hidroximetilo, alquilcarbonilo C1-6, ciano, azido, tioalquilo C1-6, sulfinilalquilo C1-6, sulfonilalquilo C1-6, tiocicloalquilo C3-8, sulfinilcicloalquilo C3-8, sulfonilcicloalquilo C3-8, mercapto, alcoxicarbonilo C1-6, cicloalcoxicarbonilo C3-8, alquenilo C2-4, cicloalquenilo C4-8, o alquinilo C2-4, siempre que Z es monovalente, R5 está ausente, en la que , R7 es H, alquilo C1-6, piperidín-1-il-(CH2)m, 4-alquilo C1-6-piperazin-1-il-(CH2)m, pirrolidin-1-il-(CH2)m, piridinil-(CH2)m, imidazolil-(CH2)m, imidazol-1-il-(CH2)m, morfolin-4-il-(CH2)m, tiomorfolin-4-il-(CH2)m, o hexahidroazepin-1-il-(CH2)m, en la que cada alquilo C1-6 incluye opcionalmente uno o más sustituyentes que son OH, NH2 o -N(A)B; R8 y R9 son independientemente H, alquilo C1-6, haloalquilo C1-6,alquenilo C2-6, alquinilo C2-6, arilalquilo, cicloalquilo, heterociclilo, arilo, heteroarilo, o heteroarilalquilo; A y B son independientemente H, alquilo C1-6, (CH2)mOH, piperidin-1-il-(CH2)m, piperazin-1-il-(CH2)m, 4-alquilo C1-6-piperazin-1-il-(CH2)m, pirrolidin-1-il-(CH2)m, piridinil-(CH2)m, imidazolil-(CH2)m, o imidazol-1-il-(CH2)m; y n y m son, respectivamente, números enteros entre 0 y 2, inclusive y entre 0 y 4 inclusive; caracterizado porque el método comprende: la eliminación de un grupo protector, G, de un compuesto de fórmula (10), para dar el compuesto de fórmula (1); y convertir opcionalmente el compuesto de fórmula (1) en su sal, éster, amida o profármaco farmacéuticamente aceptables.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44509503P | 2003-02-05 | 2003-02-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR043027A1 true AR043027A1 (es) | 2005-07-13 |
Family
ID=32850969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP040100350A AR043027A1 (es) | 2003-02-05 | 2004-02-04 | Preparacion de quinazolinas substituidas |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US20040158065A1 (es) |
| EP (1) | EP1618095A2 (es) |
| JP (1) | JP2006517959A (es) |
| KR (1) | KR20050095916A (es) |
| CN (1) | CN1745073A (es) |
| AR (1) | AR043027A1 (es) |
| AU (1) | AU2004209452A1 (es) |
| BR (1) | BRPI0407249A (es) |
| CA (1) | CA2514933A1 (es) |
| MX (1) | MXPA05007831A (es) |
| NL (3) | NL1025414C2 (es) |
| PA (1) | PA8595201A1 (es) |
| PE (1) | PE20040945A1 (es) |
| PL (1) | PL378576A1 (es) |
| RU (1) | RU2005122322A (es) |
| TW (1) | TW200420544A (es) |
| UY (1) | UY28177A1 (es) |
| WO (1) | WO2004069791A2 (es) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT1731511E (pt) * | 1999-06-21 | 2015-11-13 | Boehringer Ingelheim Pharma | Heterociclos bicíclicos, medicamentos contendo estes compostos, a sua utilização e processos para a sua preparação |
| US7019012B2 (en) * | 2000-12-20 | 2006-03-28 | Boehringer Ingelheim International Pharma Gmbh & Co. Kg | Quinazoline derivatives and pharmaceutical compositions containing them |
| CN102432552B (zh) * | 2003-08-14 | 2016-01-20 | 阿雷生物药品公司 | 作为受体酪氨酸激酶抑制剂的喹唑啉类似物 |
| US7501427B2 (en) | 2003-08-14 | 2009-03-10 | Array Biopharma, Inc. | Quinazoline analogs as receptor tyrosine kinase inhibitors |
| DE10349113A1 (de) * | 2003-10-17 | 2005-05-12 | Boehringer Ingelheim Pharma | Verfahren zur Herstellung von Aminocrotonylverbindungen |
| ME01267B (me) * | 2004-05-06 | 2013-06-20 | Warner Lambert Co | 4-fenilaminokinazolin-6-ilamidi |
| KR100735639B1 (ko) * | 2004-12-29 | 2007-07-04 | 한미약품 주식회사 | 암세포 성장 억제 효과를 갖는 퀴나졸린 유도체 및 이의제조방법 |
| KR100832594B1 (ko) * | 2005-11-08 | 2008-05-27 | 한미약품 주식회사 | 다중저해제로서의 퀴나졸린 유도체 및 이의 제조방법 |
| CA2629244C (en) | 2005-11-11 | 2014-08-05 | Boehringer Ingelheim International Gmbh | Quinazoline derivatives for the treatment of cancer diseases |
| ES2364901T3 (es) * | 2005-11-15 | 2011-09-16 | Array Biopharma, Inc. | Procesos e intermedios para la preparación de derivados de n4-fenil-quinazolin-4-amina. |
| WO2008034776A1 (en) * | 2006-09-18 | 2008-03-27 | Boehringer Ingelheim International Gmbh | Method for treating cancer harboring egfr mutations |
| AU2008299896B2 (en) | 2007-09-10 | 2012-02-02 | Curis, Inc. | Tartrate salts or complexes of quinazoline based EGFR inhibitors containing a zinc binding moiety |
| EP2242493B1 (en) * | 2008-01-22 | 2013-06-05 | Concert Pharmaceuticals Inc. | Derivatives of gefitinib |
| WO2009094210A1 (en) * | 2008-01-22 | 2009-07-30 | Concert Pharmaceuticals Inc. | Vandetanib derivatives |
| WO2010028236A1 (en) * | 2008-09-05 | 2010-03-11 | Avila Therapeutics, Inc. | Algorithm for designing irreversible inhibitors |
| ES2731901T3 (es) | 2009-07-06 | 2019-11-19 | Boehringer Ingelheim Int | Proceso para el secado de BIBW2992, de sus sales y de formulaciones farmacéuticas sólidas que comprenden este ingrediente activo |
| KR20120093220A (ko) | 2009-09-16 | 2012-08-22 | 아빌라 테라퓨틱스, 인크. | 단백질 키나아제 컨쥬게이트 및 인히비터 |
| CN102812167A (zh) | 2009-12-30 | 2012-12-05 | 阿维拉制药公司 | 蛋白的配体-介导的共价修饰 |
| CN102382106A (zh) | 2010-08-30 | 2012-03-21 | 黄振华 | 苯胺取代的喹唑啉衍生物 |
| US9371292B2 (en) | 2011-07-27 | 2016-06-21 | Shanghai Pharmaceuticals Holdings Co., Ltd. | Quinazoline derivative, preparation method therefor, intermediate, composition and application thereof |
| WO2013053206A1 (en) | 2011-10-12 | 2013-04-18 | Teligene Ltd | Quinazoline derivatives as kinases inhibitors and methods of use thereof |
| CN104350049B (zh) | 2012-05-07 | 2016-07-13 | 苏州韬略生物科技有限公司 | 作为激酶抑制剂的取代氨基喹唑啉 |
| CN103965120B (zh) * | 2013-01-25 | 2016-08-17 | 上海医药集团股份有限公司 | 喹啉及喹唑啉衍生物、制备方法、中间体、组合物及应用 |
| CN103242244B (zh) * | 2013-05-16 | 2015-03-25 | 苏州明锐医药科技有限公司 | 一种卡奈替尼的制备方法 |
| CN105408334B (zh) | 2013-05-21 | 2017-10-10 | 江苏迈度药物研发有限公司 | 作为激酶抑制剂的取代的吡唑并嘧啶类化合物 |
| 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 |
| JP7068280B2 (ja) * | 2016-09-23 | 2022-05-16 | シャンハイ ファーマシューティカルズ ホールディング カンパニー，リミティド | キナゾリン誘導体の塩、その製造方法および使用 |
| HUE057970T2 (hu) | 2018-03-08 | 2022-06-28 | Incyte Corp | Aminopirazindiol-vegyületek mint PI3K-Y inhibitorok |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
| BR112021005513A2 (pt) | 2018-09-25 | 2021-06-22 | Black Diamond Therapeutics, Inc. | derivados de quinazolina como inibidor de tirosina quinase, composições, métodos de fabricação e uso dos mesmos |
| CN113518775A (zh) * | 2019-03-07 | 2021-10-19 | 生物技术公司 | 用于制备经取代的咪唑并喹啉的方法 |
| EP4328222A1 (en) * | 2021-04-22 | 2024-02-28 | Voronoi Inc. | Heteroaryl derivative compound and use thereof |
| WO2023044364A1 (en) | 2021-09-15 | 2023-03-23 | Enko Chem, Inc. | Protoporphyrinogen oxidase inhibitors |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RO121900B1 (ro) * | 1996-04-12 | 2008-07-30 | Warner-Lambert Company | Compuşi inhibitori, ireversibili, ai tirozin kinazelor, compoziţie farmaceutică care îi conţine şi utilizarea acestora |
| DE10009267A1 (de) * | 2000-02-26 | 2001-08-30 | Goedecke Ag | Verfahren zur einfachen Herstellung von (3-Chlor-4-fluor-phenyl)-[7-(3-morpholin-4-yl-propoxy)-6-nitro-quinazolin-4-yl]-amin bzw. (3-Chlor-4-fluor-phenyl)-[7-(3-morpholin-4-yl-propoxy)-6-amino-quinazolin-4-yl]-amin |
| US6664390B2 (en) * | 2000-02-02 | 2003-12-16 | Warner-Lambert Company Llc | Method for the simplified production of (3-chloro-4-fluorophenyl)-[7-(3-morpholin-4-yl-propoxy)-6-nitro-quinazoline-4-yl]-amine or (3-chloro-4-fluorophenyl)-[7-(3-morpholin-4-yl-propoxy)-6-amino-quinazoline-4-yl]-amine |
| US6627634B2 (en) * | 2000-04-08 | 2003-09-30 | Boehringer Ingelheim Pharma Kg | Bicyclic heterocycles, pharmaceutical compositions containing them, their use, and processes for preparing them |
| DE10063435A1 (de) * | 2000-12-20 | 2002-07-04 | Boehringer Ingelheim Pharma | Chinazolinderviate,diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
-
2004
- 2004-02-02 PE PE2004000120A patent/PE20040945A1/es not_active Application Discontinuation
- 2004-02-03 AU AU2004209452A patent/AU2004209452A1/en not_active Abandoned
- 2004-02-03 RU RU2005122322/04A patent/RU2005122322A/ru not_active Application Discontinuation
- 2004-02-03 TW TW093102396A patent/TW200420544A/zh unknown
- 2004-02-03 WO PCT/IB2004/000321 patent/WO2004069791A2/en active Application Filing
- 2004-02-03 KR KR1020057014036A patent/KR20050095916A/ko not_active Application Discontinuation
- 2004-02-03 CN CNA2004800032079A patent/CN1745073A/zh active Pending
- 2004-02-03 MX MXPA05007831A patent/MXPA05007831A/es unknown
- 2004-02-03 EP EP04707601A patent/EP1618095A2/en not_active Withdrawn
- 2004-02-03 JP JP2006502417A patent/JP2006517959A/ja not_active Abandoned
- 2004-02-03 PL PL378576A patent/PL378576A1/pl not_active Application Discontinuation
- 2004-02-03 CA CA002514933A patent/CA2514933A1/en not_active Abandoned
- 2004-02-03 BR BR0407249-9A patent/BRPI0407249A/pt not_active IP Right Cessation
- 2004-02-04 UY UY28177A patent/UY28177A1/es not_active Application Discontinuation
- 2004-02-04 US US10/771,774 patent/US20040158065A1/en not_active Abandoned
- 2004-02-04 AR ARP040100350A patent/AR043027A1/es unknown
- 2004-02-05 PA PA20048595201A patent/PA8595201A1/es unknown
- 2004-02-05 NL NL1025414A patent/NL1025414C2/nl not_active IP Right Cessation
-
2005
- 2005-08-18 NL NL1029763A patent/NL1029763C2/nl not_active IP Right Cessation
- 2005-08-18 NL NL1029762A patent/NL1029762C2/nl not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PA8595201A1 (es) | 2004-09-16 |
| MXPA05007831A (es) | 2005-10-18 |
| UY28177A1 (es) | 2004-09-30 |
| US20040158065A1 (en) | 2004-08-12 |
| KR20050095916A (ko) | 2005-10-04 |
| NL1029762A1 (nl) | 2005-10-13 |
| AU2004209452A1 (en) | 2004-08-19 |
| EP1618095A2 (en) | 2006-01-25 |
| CN1745073A (zh) | 2006-03-08 |
| CA2514933A1 (en) | 2004-08-19 |
| PE20040945A1 (es) | 2004-12-14 |
| PL378576A1 (pl) | 2006-05-02 |
| NL1029763A1 (nl) | 2005-10-13 |
| BRPI0407249A (pt) | 2006-01-31 |
| JP2006517959A (ja) | 2006-08-03 |
| WO2004069791A2 (en) | 2004-08-19 |
| NL1029763C2 (nl) | 2006-03-06 |
| NL1025414C2 (nl) | 2005-11-01 |
| NL1029762C2 (nl) | 2006-03-06 |
| NL1025414A1 (nl) | 2004-08-06 |
| RU2005122322A (ru) | 2006-03-10 |
| TW200420544A (en) | 2004-10-16 |
| WO2004069791A3 (en) | 2004-12-16 |
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