CO5670368A2 - Procedimiento para la sisntesis de 6-amino-4-[(3-cloro-4-fluorofenil)amino]-7-etoxiquinolin-3-carbonitrilo - Google Patents

Procedimiento para la sisntesis de 6-amino-4-[(3-cloro-4-fluorofenil)amino]-7-etoxiquinolin-3-carbonitrilo

Info

Publication number
CO5670368A2
CO5670368A2 CO06023402A CO06023402A CO5670368A2 CO 5670368 A2 CO5670368 A2 CO 5670368A2 CO 06023402 A CO06023402 A CO 06023402A CO 06023402 A CO06023402 A CO 06023402A CO 5670368 A2 CO5670368 A2 CO 5670368A2
Authority
CO
Colombia
Prior art keywords
acetamido
chloro
cyano
amino
compound
Prior art date
Application number
CO06023402A
Other languages
English (en)
Inventor
Sylvain Daigneault
Ronald Stanley Michalak
Michel Bernatchez
Original Assignee
Wyeth Corp
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 Wyeth Corp filed Critical Wyeth Corp
Publication of CO5670368A2 publication Critical patent/CO5670368A2/es

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/43—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/30—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same unsaturated acyclic carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1.- Un compuesto, caracterizado porque consiste del éster etílico del ácido 3-(4-acetamido-3-etoxianilina)-2-cianopropenoico.2.- Un compuesto, caracterizado porque consiste de3-ciano-7-etoxi-4-hidroxi-6-N-acetilquinolina.3.- Un compuesto, caracterizado porque consiste de4-cloro-3-ciano-7-etoxi-6-N-acetilquinolina.4.- Un compuesto, caracterizado porque consiste deN-[4-(3-cloro-4-fluorofenilamino)-3-ciano-7-etoxiquinolin-6-il]acetamida.5.- Un compuesto, caracterizado porque consiste de 6-amino-4-(3-cloro-4-fluorofenilamino)-7-etoxiquinolin-3-carbonitrilo.6.- Un compuesto, caracterizado porque consiste de 4-acetamido-3-etoxianilina.7.- Un compuesto, caracterizado porque consiste de2-acetamido-5-nitrofenol.8.- Un compuesto, caracterizado porque consiste de2-acetamido-3-etoxinitrobenceno.9.- Un procedimiento para producir 6-amino-4-(3-cloro-4-fluorofenilamino)-7-etoxiquinolin-3-carbonitrilo caracterizado porque comprende: (a) acilar 2-amino-5-nitrofenol con un agente acilante para obtener 2-acetamido-5-nitrofenol; (b) alquilar 2-acetamido-5-nitrofenol en la etapa (a) con un haluro alquilante en presencia de una base para obtener 4-acetamido-3-etoxinitrobenceno; (c) reducir la 4-acetamida-3-etoxinitrobenceno de la etapa (b) para obtener 4-acetamido-3-etoxianilina; (d) condensar la 4-acetamido-3-etoxianilina de la etapa (c) con (etoximetilen)cianoacetato de etilo para proporcionar el éster etílico del ácido 3-(4-acetamido-3-etoxianilina)-2-ciano-propenoico; (e) ciclizar el éster etílico del ácido 3-(4-acetamido-3-etoxianilina)-2-ciano-propenoico de la etapa (d) para proporcionar 3-ciano-7 -etoxi-4-hidroxi-6-N-acetilquinolina; (f) reducir la 3-ciano-7-etoxi-4-hidroxi-6-N-acetilquinolina de la etapa (e) con un reactivo que sustituye cloro para obtener el 4-cloro-3-ciano-7 -etoxi-3-quinolincarbonitrilo; y (g) hidrolizar el 4-cloro-3-ciano-7-etoxi-3-quinolincarbonitrilo de la etapa (f) con ácido para proporcionar 6-amino-4-(3-cloro-4-fluorofenilamino)-7 -etoxiquinolin-3-carbonitrilo o la sal del mismo.
CO06023402A 2003-09-15 2006-03-08 Procedimiento para la sisntesis de 6-amino-4-[(3-cloro-4-fluorofenil)amino]-7-etoxiquinolin-3-carbonitrilo CO5670368A2 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US50310603P 2003-09-15 2003-09-15

Publications (1)

Publication Number Publication Date
CO5670368A2 true CO5670368A2 (es) 2006-08-31

Family

ID=34375310

Family Applications (1)

Application Number Title Priority Date Filing Date
CO06023402A CO5670368A2 (es) 2003-09-15 2006-03-08 Procedimiento para la sisntesis de 6-amino-4-[(3-cloro-4-fluorofenil)amino]-7-etoxiquinolin-3-carbonitrilo

Country Status (19)

Country Link
US (2) US7365203B2 (es)
EP (1) EP1663951A2 (es)
JP (1) JP2007505910A (es)
KR (1) KR20060079217A (es)
CN (2) CN100395231C (es)
AU (1) AU2004274450A1 (es)
BR (1) BRPI0414377A (es)
CA (1) CA2536439A1 (es)
CO (1) CO5670368A2 (es)
CR (1) CR8277A (es)
EC (1) ECSP066423A (es)
IL (1) IL173750A0 (es)
MX (1) MXPA06002796A (es)
NO (1) NO20060767L (es)
RU (1) RU2006105263A (es)
SG (1) SG146645A1 (es)
UA (1) UA87474C2 (es)
WO (1) WO2005028421A2 (es)
ZA (1) ZA200602149B (es)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW200526219A (en) * 2004-01-16 2005-08-16 Wyeth Corp Quinoline intermediates of receptor tyrosine kinase inhibitors and the synthesis thereof
CA2609186A1 (en) * 2005-05-25 2006-11-30 Wyeth Methods of synthesizing substituted 3-cyanoquinolines and intermediates thereof
EP1984325A4 (en) * 2006-02-03 2011-08-10 Univ Ohio State Res Found SULFONANILID ANALOGUE AS SELECTIVE AROMATASE MODULATORS
JP2008102489A (ja) * 2006-09-19 2008-05-01 Ricoh Co Ltd 現像剤搬送装置、現像装置、プロセスユニット及び画像形成装置
CN102070524A (zh) * 2011-01-12 2011-05-25 无锡好芳德药业有限公司 一种3-氰基-4-卤代喹啉衍生物的制备方法
CN103275002A (zh) * 2013-06-14 2013-09-04 苏州明锐医药科技有限公司 培利替尼的制备方法
CN108675958A (zh) * 2018-03-23 2018-10-19 孙金霞 一种抗肿瘤药物培利替尼中间体的清洁生产方法
CN111848581B (zh) * 2020-08-19 2021-08-10 昆明学院 3-氰基-4-苯胺基-6-氨基喹啉衍生物的制备方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6002008A (en) * 1997-04-03 1999-12-14 American Cyanamid Company Substituted 3-cyano quinolines
US6384051B1 (en) * 2000-03-13 2002-05-07 American Cyanamid Company Method of treating or inhibiting colonic polyps
AR035851A1 (es) * 2000-03-28 2004-07-21 Wyeth Corp 3-cianoquinolinas, 3-ciano-1,6-naftiridinas y 3-ciano-1,7-naftiridinas como inhibidoras de proteina quinasas
ATE370123T1 (de) * 2001-11-27 2007-09-15 Wyeth Corp 3-cyanochinoline als inhibitoren von egf-r- und her2-kinasen

Also Published As

Publication number Publication date
MXPA06002796A (es) 2006-06-14
US20080161575A1 (en) 2008-07-03
NO20060767L (no) 2006-06-07
SG146645A1 (en) 2008-10-30
CA2536439A1 (en) 2005-03-31
RU2006105263A (ru) 2007-11-10
IL173750A0 (en) 2006-07-05
KR20060079217A (ko) 2006-07-05
JP2007505910A (ja) 2007-03-15
CN101318908A (zh) 2008-12-10
WO2005028421A8 (en) 2005-06-16
WO2005028421A3 (en) 2005-05-19
ECSP066423A (es) 2006-09-18
US20050065181A1 (en) 2005-03-24
CN1849299A (zh) 2006-10-18
CN100395231C (zh) 2008-06-18
BRPI0414377A (pt) 2007-04-10
ZA200602149B (en) 2009-09-30
US7365203B2 (en) 2008-04-29
CR8277A (es) 2006-07-14
EP1663951A2 (en) 2006-06-07
UA87474C2 (ru) 2009-07-27
WO2005028421A2 (en) 2005-03-31
AU2004274450A1 (en) 2005-03-31

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