AR063449A1 - Proceso quimico para derivados de quinazolina, intermediarios - Google Patents

Proceso quimico para derivados de quinazolina, intermediarios

Info

Publication number
AR063449A1
AR063449A1 ARP070104874A ARP070104874A AR063449A1 AR 063449 A1 AR063449 A1 AR 063449A1 AR P070104874 A ARP070104874 A AR P070104874A AR P070104874 A ARP070104874 A AR P070104874A AR 063449 A1 AR063449 A1 AR 063449A1
Authority
AR
Argentina
Prior art keywords
compound
formula
manufacture
reacting
salt
Prior art date
Application number
ARP070104874A
Other languages
English (en)
Inventor
Ian M Mcfarlane
Original Assignee
Astrazeneca Ab
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab
Publication of AR063449A1 publication Critical patent/AR063449A1/es

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • 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
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • 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
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
    • C07C201/06—Preparation of nitro compounds
    • C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/06—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • 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
    • C07D239/88—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/10—Spiro-condensed systems
    • 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

Abstract

Procesos químicos para la fabricacion de determinados derivados de quinazolina, o sales de éstos aceptables para el uso farmacéutico. Procesos para la fabricacion de determinados intermediarios utiles en la fabricacion de los derivados de quinazolina y procesos para la fabricacion de los derivados de quinazolina donde se utilizan dichos intermediarios. En particular, la presente se relaciona con procesos químicos e intermediarios utiles en la fabricacion del compuesto 4-(4-fluoro-2- metilindol-5-iloxi)-6-metoxi-7-(3-pirrolidin-1-ilpropoxi) quinazolina. Reivindicacion 1: Un proceso para la fabricacion de un compuesto de formula (1) a partir de un compuesto de formula (2) donde R1 y R2 se seleccionan independientemente entre cloro, bromo, fluor, iodo y alquilsulfoniloxilo opcionalmente sustituido; caracterizado porque comprende los pasos de: (a) hacer reaccionar un compuesto de formula (2) con un éster de formula (3) donde R3 es un grupo esterificante apropiado; para formar un compuesto de formula (4); (b) hacer reaccionar un compuesto de formula (4) con un ion hidroxido en presencia de una sal de aril-alquil amonio o una sal de tetra-alquil amonio, para formar un compuesto de formula (5); (c) hacer reaccionar un compuesto de formula (5) para formar un compuesto de formula (6); (d) reducir el compuesto de formula (6) para formar un compuesto de formula (1). Reivindicacion 7: Un proceso para la fabricacion de un compuesto de formula (7), donde R4 es un grupo protector a partir de un compuesto de formula (8) caracterizado porque comprende los pasos de: (f) hacer reaccionar un compuesto de formula (8) con un agente derivatizante para formar un compuesto de formula (9), donde L1 es un grupo saliente; y (g) hacer reaccionar el compuesto de formula (9) con un compuesto de formula (1) (2-metil-4-fluoro-5-hidroxi-indol) para formar el compuesto de formula (7). Reivindicacion 12: Un proceso para la fabricacion de un compuesto de formula (10) a partir de un compuesto de formula (8) donde R4 es un grupo protector, caracterizado porque comprende los pasos de: (f) hacer reaccionar un compuesto de formula (8) con un agente derivatizante para formar un compuesto de formula (9) donde L1 es un grupo saliente; (g) hacer reaccionar el compuesto de formula (9) con un compuesto de formula (1) (2-metil-4-fluoro-5-hidroxi-indol) para formar un compuesto de formula (7); e (i) eliminar R4 del compuesto de formula (7) in situ, en presencia del solvente usado en los pasos (f) y (g), para formar el compuesto de formula (10), o una sal de éste; después de lo cual es posible convertir el compuesto de formula (10) obtenido en forma de base libre en una forma de sal, y convertir el compuesto de formula (10) obtenido en forma de sal en una forma de base libre o en forma de una sal alternativa, segun sea necesario.
ARP070104874A 2006-11-02 2007-11-01 Proceso quimico para derivados de quinazolina, intermediarios AR063449A1 (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US86403606P 2006-11-02 2006-11-02
US95740107P 2007-08-22 2007-08-22

Publications (1)

Publication Number Publication Date
AR063449A1 true AR063449A1 (es) 2009-01-28

Family

ID=39284186

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP070104874A AR063449A1 (es) 2006-11-02 2007-11-01 Proceso quimico para derivados de quinazolina, intermediarios

Country Status (18)

Country Link
US (2) US7851623B2 (es)
EP (3) EP2540706A3 (es)
JP (1) JP2010508340A (es)
KR (1) KR20090079247A (es)
CN (3) CN102584798A (es)
AR (1) AR063449A1 (es)
AU (1) AU2007315982B2 (es)
BR (1) BRPI0717751A2 (es)
CA (1) CA2667920A1 (es)
CL (1) CL2007003158A1 (es)
IL (1) IL198117A0 (es)
MX (1) MX2009004708A (es)
MY (2) MY150219A (es)
NO (1) NO20091588L (es)
RU (2) RU2012139318A (es)
SG (2) SG176447A1 (es)
TW (1) TW200833667A (es)
WO (1) WO2008053221A2 (es)

Families Citing this family (15)

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KR20080015482A (ko) 1999-02-10 2008-02-19 아스트라제네카 아베 혈관형성 억제제로서의 퀴나졸린 유도체
CA2473572C (en) * 2002-02-01 2011-05-10 Astrazeneca Ab Quinazoline compounds
WO2010071885A1 (en) 2008-12-19 2010-06-24 Cephalon, Inc. Pyrrolotriazines as alk and jak2 inhibitors
CN102603718B (zh) * 2012-02-08 2014-01-29 武汉凯斯瑞科技有限公司 西地尼布的合成方法
WO2014127214A1 (en) 2013-02-15 2014-08-21 Kala Pharmaceuticals, Inc. Therapeutic compounds and uses thereof
AU2014219024B2 (en) 2013-02-20 2018-04-05 KALA BIO, Inc. Therapeutic compounds and uses thereof
US9688688B2 (en) 2013-02-20 2017-06-27 Kala Pharmaceuticals, Inc. Crystalline forms of 4-((4-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazolin-7-yl)oxy)-1-(2-oxa-7-azaspiro[3.5]nonan-7-yl)butan-1-one and uses thereof
CN103275069B (zh) * 2013-05-22 2015-03-11 苏州明锐医药科技有限公司 西地尼布的制备方法
AU2014342042B2 (en) 2013-11-01 2017-08-17 KALA BIO, Inc. Crystalline forms of therapeutic compounds and uses thereof
US9890173B2 (en) 2013-11-01 2018-02-13 Kala Pharmaceuticals, Inc. Crystalline forms of therapeutic compounds and uses thereof
US10392399B2 (en) 2016-09-08 2019-08-27 Kala Pharmaceuticals, Inc. Crystalline forms of therapeutic compounds and uses thereof
CA3036336A1 (en) 2016-09-08 2018-03-15 Kala Pharmaceuticals, Inc. Crystalline forms of therapeutic compounds and uses thereof
BR112019004463A2 (pt) 2016-09-08 2019-05-28 Kala Pharmaceuticals Inc formas cristalinas de compostos terapêuticos, seus processos de obtenção e seus métodos de uso
CN107840843A (zh) * 2017-10-17 2018-03-27 浙江工业大学义乌科学技术研究院有限公司 一种西地尼布中间体的合成方法
WO2023080193A1 (ja) * 2021-11-04 2023-05-11 日産化学株式会社 インドール化合物の製造方法

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US5710158A (en) 1991-05-10 1998-01-20 Rhone-Poulenc Rorer Pharmaceuticals Inc. Aryl and heteroaryl quinazoline compounds which inhibit EGF and/or PDGF receptor tyrosine kinase
GB9508538D0 (en) * 1995-04-27 1995-06-14 Zeneca Ltd Quinazoline derivatives
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US7645878B2 (en) 2002-03-22 2010-01-12 Bayer Healthcare Llc Process for preparing quinazoline Rho-kinase inhibitors and intermediates thereof
TWI272271B (en) * 2002-07-19 2007-02-01 Bristol Myers Squibb Co Process for preparing certain pyrrolotriazine compounds
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JP4255057B2 (ja) 2003-03-12 2009-04-15 日本カーリット株式会社 導電性付与剤及び導電性材料
GB0318422D0 (en) * 2003-08-06 2003-09-10 Astrazeneca Ab Chemical compounds
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WO2005097137A2 (en) * 2004-03-31 2005-10-20 The Scripps Research Institute Advanced quinazoline based protein kinase inhibitors
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Also Published As

Publication number Publication date
MX2009004708A (es) 2009-05-15
RU2012139318A (ru) 2014-03-20
US8754240B2 (en) 2014-06-17
CN101528688A (zh) 2009-09-09
CN101528688B (zh) 2012-09-05
SG176447A1 (en) 2011-12-29
MY179610A (en) 2020-11-11
KR20090079247A (ko) 2009-07-21
US20080221322A1 (en) 2008-09-11
US20110257395A1 (en) 2011-10-20
WO2008053221A2 (en) 2008-05-08
MY150219A (en) 2013-12-31
NO20091588L (no) 2009-05-28
IL198117A0 (en) 2009-12-24
WO2008053221A3 (en) 2008-12-31
AU2007315982B2 (en) 2012-07-12
CN102532108A (zh) 2012-07-04
RU2012139319A (ru) 2014-03-20
RU2009120567A (ru) 2010-12-10
CN102584798A (zh) 2012-07-18
JP2010508340A (ja) 2010-03-18
US7851623B2 (en) 2010-12-14
SG176446A1 (en) 2011-12-29
EP2540705A2 (en) 2013-01-02
EP2540706A2 (en) 2013-01-02
BRPI0717751A2 (pt) 2013-10-22
EP2540706A3 (en) 2013-11-06
CA2667920A1 (en) 2008-05-08
AU2007315982A1 (en) 2008-05-08
CL2007003158A1 (es) 2008-05-16
EP2540705A3 (en) 2013-10-30
EP2129657A2 (en) 2009-12-09
TW200833667A (en) 2008-08-16

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