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
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 |
|---|---|---|---|---|
| EP1194418A1 (de) * | 1999-06-21 | 2002-04-10 | Boehringer Ingelheim Pharma KG | Bicyclische heterocyclen, diese verbindungen enthaltende arzneimittel, deren verwendung und verfahren zu ihrer herstellung |
| US7019012B2 (en) * | 2000-12-20 | 2006-03-28 | Boehringer Ingelheim International Pharma Gmbh & Co. Kg | Quinazoline derivatives and pharmaceutical compositions containing them |
| CN103664802B (zh) * | 2003-08-14 | 2015-08-05 | 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 |
| DK1746999T3 (da) * | 2004-05-06 | 2012-01-23 | Warner Lambert Co | 4-phenylamino-quinazolin-6-yl-amider |
| KR100735639B1 (ko) * | 2004-12-29 | 2007-07-04 | 한미약품 주식회사 | 암세포 성장 억제 효과를 갖는 퀴나졸린 유도체 및 이의제조방법 |
| KR100832593B1 (ko) * | 2005-11-08 | 2008-05-27 | 한미약품 주식회사 | 신호전달 저해제로서의 퀴나졸린 유도체 및 이의 제조방법 |
| EP1948179A1 (en) | 2005-11-11 | 2008-07-30 | Boehringer Ingelheim International GmbH | Quinazoline derivatives for the treatment of cancer diseases |
| ES2335535T3 (es) | 2005-11-15 | 2010-03-29 | Array Biopharma Inc. | Derivados de n4-fenil-quinazolin-4-amina ycompuestos afines como inhibidores de la tirosina quinasa receptora erbb tipo i para el tratamiento de enfermedades hiperproliferativas. |
| BRPI0717586A2 (pt) * | 2006-09-18 | 2013-10-29 | Boehringer Ingelheim Int | Método para tratar câncer apresentando mutações do egfr |
| JP5474792B2 (ja) * | 2007-09-10 | 2014-04-16 | キュリス，インコーポレイテッド | 亜鉛結合部分を含むキナゾリンベースｅｇｆｒインヒビターの酒石酸塩またはその複合体 |
| US7855204B2 (en) * | 2008-01-22 | 2010-12-21 | Concert Pharmaceuticals Inc. | Derivatives of gefitinib |
| US8609673B2 (en) * | 2008-01-22 | 2013-12-17 | Concert Pharmaceuticals, Inc. | Vandetanib derivatives |
| WO2010028236A1 (en) * | 2008-09-05 | 2010-03-11 | Avila Therapeutics, Inc. | Algorithm for designing irreversible inhibitors |
| DK2451445T3 (da) | 2009-07-06 | 2019-06-24 | Boehringer Ingelheim Int | Fremgangsmåde til at tørre bibw2992, dets salte og faste farmaceutiske formuleringer omfattende denne aktive ingrediens |
| RU2012114902A (ru) | 2009-09-16 | 2013-10-27 | Авила Терапьютикс, Инк. | Конъюгаты и ингибиторы протеинкиназы |
| JP2013516422A (ja) | 2009-12-30 | 2013-05-13 | アビラ セラピューティクス， インコーポレイテッド | タンパク質のリガンド−指向性共有的修飾 |
| CN102382106A (zh) | 2010-08-30 | 2012-03-21 | 黄振华 | 苯胺取代的喹唑啉衍生物 |
| CN102898386B (zh) * | 2011-07-27 | 2015-07-29 | 上海医药集团股份有限公司 | 喹唑啉衍生物、其制备方法、中间体、组合物及其应用 |
| WO2013053206A1 (en) | 2011-10-12 | 2013-04-18 | Teligene Ltd | Quinazoline derivatives as kinases inhibitors and methods of use thereof |
| US9388170B2 (en) | 2012-05-07 | 2016-07-12 | Teligene Ltd. | Substituted aminoquinazolines useful as kinases inhibitors |
| 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 |
| MX2020009228A (es) | 2018-03-08 | 2021-01-08 | Incyte Corp | Compuestos diolicos de aminopirazina como inhibidores de fosfoinositida 3-cinasas-gamma. |
| WO2020010003A1 (en) | 2018-07-02 | 2020-01-09 | Incyte Corporation | AMINOPYRAZINE DERIVATIVES AS PI3K-γ INHIBITORS |
| CA3113241A1 (en) | 2018-09-25 | 2020-04-02 | Black Diamond Therapeutics, Inc. | Quinazoline derivatives as tyrosine kinase inhibitor, compositions, methods of making them and their use |
| 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 |
| KR20220147021A (ko) * | 2021-04-22 | 2022-11-02 | 보로노이 주식회사 | 헤테로아릴 유도체 화합물 및 이의 용도 |
| 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 |
|---|---|---|---|---|
| NZ332119A (en) * | 1996-04-12 | 2001-08-31 | Warner Lambert Co | Quinazoline compounds which are irreversible inhibitors of tyrosine kinases |
| 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 |
| 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 |
| 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 MX MXPA05007831A patent/MXPA05007831A/es unknown
- 2004-02-03 CN CNA2004800032079A patent/CN1745073A/zh active Pending
- 2004-02-03 AU AU2004209452A patent/AU2004209452A1/en not_active Abandoned
- 2004-02-03 BR BR0407249-9A patent/BRPI0407249A/pt not_active IP Right Cessation
- 2004-02-03 RU RU2005122322/04A patent/RU2005122322A/ru not_active Application Discontinuation
- 2004-02-03 KR KR1020057014036A patent/KR20050095916A/ko not_active Application Discontinuation
- 2004-02-03 JP JP2006502417A patent/JP2006517959A/ja not_active Abandoned
- 2004-02-03 CA CA002514933A patent/CA2514933A1/en not_active Abandoned
- 2004-02-03 EP EP04707601A patent/EP1618095A2/en not_active Withdrawn
- 2004-02-03 PL PL378576A patent/PL378576A1/pl 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
- 2004-02-04 US US10/771,774 patent/US20040158065A1/en not_active Abandoned
- 2004-02-04 AR ARP040100350A patent/AR043027A1/es unknown
- 2004-02-04 UY UY28177A patent/UY28177A1/es not_active Application Discontinuation
- 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 |
|---|---|
| UY28177A1 (es) | 2004-09-30 |
| NL1029762A1 (nl) | 2005-10-13 |
| NL1025414A1 (nl) | 2004-08-06 |
| EP1618095A2 (en) | 2006-01-25 |
| US20040158065A1 (en) | 2004-08-12 |
| TW200420544A (en) | 2004-10-16 |
| NL1029763C2 (nl) | 2006-03-06 |
| BRPI0407249A (pt) | 2006-01-31 |
| CN1745073A (zh) | 2006-03-08 |
| NL1025414C2 (nl) | 2005-11-01 |
| KR20050095916A (ko) | 2005-10-04 |
| PE20040945A1 (es) | 2004-12-14 |
| JP2006517959A (ja) | 2006-08-03 |
| WO2004069791A2 (en) | 2004-08-19 |
| AU2004209452A1 (en) | 2004-08-19 |
| PL378576A1 (pl) | 2006-05-02 |
| NL1029763A1 (nl) | 2005-10-13 |
| CA2514933A1 (en) | 2004-08-19 |
| RU2005122322A (ru) | 2006-03-10 |
| WO2004069791A3 (en) | 2004-12-16 |
| NL1029762C2 (nl) | 2006-03-06 |
| MXPA05007831A (es) | 2005-10-18 |
| PA8595201A1 (es) | 2004-09-16 |
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