AR032175A1 - Proceso para la fabricacion de acidos n-aril-antranilicos y sus derivados - Google Patents

Proceso para la fabricacion de acidos n-aril-antranilicos y sus derivados

Info

Publication number
AR032175A1
AR032175A1 ARP010104047A ARP010104047A AR032175A1 AR 032175 A1 AR032175 A1 AR 032175A1 AR P010104047 A ARP010104047 A AR P010104047A AR P010104047 A ARP010104047 A AR P010104047A AR 032175 A1 AR032175 A1 AR 032175A1
Authority
AR
Argentina
Prior art keywords
group
aryl
alkyl
hydrogen
metal cation
Prior art date
Application number
ARP010104047A
Other languages
English (en)
Original Assignee
Warner Lambert Co
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 Warner Lambert Co filed Critical Warner Lambert Co
Publication of AR032175A1 publication Critical patent/AR032175A1/es

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/10—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
    • C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • 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
    • 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
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Indole Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

Se propone un proceso para la preparacion de ácidos N-aril-antranílicos, que son agentes farmacéuticos utiles, por ejemplo, como agentes antiinflamatorios. Dichos ácidos pueden servir como intermedios en la preparacion de amidas N-aril antranílicas, ácidos hidroxámicos N-aril-antranílicos y ésteres de ácidos hidroxámicos N-aril-antranílicos. Dichos compuestos inhiben ciertas enzimas quinasa de especificidad doble involucradas en enfermedades proliferativas tales como cáncer y restenosis. Un proceso para sintetizar un compuesto de formula (1), o una sal farmacéuticamente aceptable de él, en donde R1 es hidrogeno, alquilo, alcoxi, o arilo; R2, R3, R4, R5, R6, R7, R8, R9 y R10 se seleccionan cada uno independientemente de: hidrogeno, halo, alquilo, arilo, un grupo heterocíclico, haloalquilo, alcoxi, nitro, CN, -(=)m-(CH2) n-R11, en donde m, n, y R11 son lo definido abajo, o dos sustituyentes cualquiera de R2, R3, R4, R5, R6, R7, R8, R9 y R10 que están unidos a átomos de carbono de anillos contiguos, se pueden tomar junto con los átomos de carbono de los anillos contiguos, para formar un grupo arilo, heteroarilo, heterocíclico, o cicloalquilo de 4 a 7 átomos totales en el anillo, o R1 y R6 se pueden tomar junto con el átomo de nitrogeno, al cual está unido R1, el átomo de carbono al cual está unido R6 y el átomo de carbono contiguo a dicho átomo de carbono al cual está unido R6 para formar un anillo aromático o dihidroaromático de 5 o 6 miembros que tiene átomos de carbono en 1 o 2 átomos de nitrogeno; R11 es hidrogeno, hidroxi,, -CO2H, o N(R12)R13, R12 y R13 son cada uno independientemente hidrogeno, alquilo o R12 y R13 se toman junto con el átomo de nitrogeno al cual están unidos para formar un grupo heterocíclico de 3 a 10 miembros que tiene átomos de carbono y uno, dos o tres heteroátomos seleccionados de O, S, y NR14, en donde R14 es hidrogeno o alquilo; m es un numero entero de 0 a 1; n es un numero entero seleccionado de 0, 1, 2, 3, 4; y -Z es COOH, COOM, COOR15, -C(O)R15, -C(O)N(R16)R17, -C(O)N(R18)OR19, NO2, o CN, en donde M es un cation de metal del GrupoI metal o un hemication de metal del Grupo II, R15 es alquilo, alquenilo, arilo o un grupo heterocíclico, y R16, R17, R18 y R19 se seleccionan cada uno independientemente de hidrogeno, alquilo, alquenilo, fenilo, y bencilo, o R16 y R17 se toman junto con el átomo de nitrogeno al cual están unidos para formar un grupo heterocíclico de 3 a 10 miembros que tiene átomos de carbono y uno, dos o tres heteroátomos seleccionados de O, S, y NR14, en donde R14 es hidrogeno o alquilo; que comprende hacer reaccionar un compuesto de formula (2), en donde R1, R6, R7, R8, R9, y R10 son lo definido anteriormente, con un compuesto de la formula (3), en donde Z, R2, R3, R4 y R5 son lo definido anteriormente, y X es halo o O-LG, en donde LG es SO2R20 o P(=O) (OR20)2, donde R20 es alquilo o arilo, optativamente en un solvente, y en la presencia de 1 equivalente en moles a 10 equivalentes en moles de una base, en donde la base se selecciona de: un hidruro de cation de metal del Grupo I o un hidruro de cation de metal del Grupo II, que incluyen hidruro de litio, hidruro de sodio, hidruro de potasio, e hidruro de calcio, una dialquilamida de cation de metal del Grupo II, que incluyen diisopropilamida de litio, una amida de cation de metal del Grupo I o una amida de cation de metal del Grupo II, que incluyen amida de litio, amida de sodio, amida de potasio, y un alcoxido de cation de metal del Grupo I o un alcoxido de cation de metal del Grupo II, que incluyen etoxido de sodio, ter-butoxido de potasio, y etoxido de magnesio, durante un tiempo, y a una temperatura suficiente para dar un compuesto de la formula (1).
ARP010104047A 2000-08-25 2001-08-24 Proceso para la fabricacion de acidos n-aril-antranilicos y sus derivados AR032175A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US22820600P 2000-08-25 2000-08-25

Publications (1)

Publication Number Publication Date
AR032175A1 true AR032175A1 (es) 2003-10-29

Family

ID=22856235

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP010104047A AR032175A1 (es) 2000-08-25 2001-08-24 Proceso para la fabricacion de acidos n-aril-antranilicos y sus derivados

Country Status (31)

Country Link
EP (1) EP1313694A1 (es)
JP (1) JP2004507518A (es)
KR (1) KR20030059115A (es)
CN (1) CN1458921A (es)
AP (1) AP2001002249A0 (es)
AR (1) AR032175A1 (es)
AU (1) AU2001277044A1 (es)
BG (1) BG107635A (es)
BR (1) BR0113520A (es)
CA (1) CA2420003A1 (es)
CZ (1) CZ2003477A3 (es)
DO (1) DOP2001000238A (es)
EA (1) EA200300187A1 (es)
GT (1) GT200100174A (es)
HN (1) HN2001000216A (es)
HU (1) HUP0300828A2 (es)
IL (1) IL154507A0 (es)
IS (1) IS6724A (es)
MA (1) MA26949A1 (es)
MX (1) MXPA03001654A (es)
NO (1) NO20030844L (es)
PA (1) PA8526501A1 (es)
PE (1) PE20020393A1 (es)
PL (1) PL360699A1 (es)
SK (1) SK2072003A3 (es)
SV (1) SV2002000601A (es)
TN (1) TNSN01127A1 (es)
UY (1) UY26908A1 (es)
WO (1) WO2002018319A1 (es)
YU (1) YU14303A (es)
ZA (1) ZA200301182B (es)

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US7144907B2 (en) 2003-09-03 2006-12-05 Array Biopharma Inc. Heterocyclic inhibitors of MEK and methods of use thereof
KR101013932B1 (ko) 2003-10-21 2011-02-14 워너-램버트 캄파니 엘엘씨 Ｎ-[(ｒ)-2,3-디히드록시-프로폭시]-3,4-디플루오로-2-(2-플루오로-4-요오도페닐아미노)-벤자미드 다형체 형태
US7517994B2 (en) 2003-11-19 2009-04-14 Array Biopharma Inc. Heterocyclic inhibitors of MEK and methods of use thereof
SI1682138T1 (sl) 2003-11-19 2011-04-29 Array Biopharma Inc HETEROCIKLIÄŚNI INHIBITORJI MEK-a
US7732616B2 (en) 2003-11-19 2010-06-08 Array Biopharma Inc. Dihydropyridine and dihydropyridazine derivatives as inhibitors of MEK and methods of use thereof
NZ547327A (en) 2003-11-21 2009-08-28 Array Biopharma Inc AKT protein kinase inhibitors
UA89035C2 (ru) * 2003-12-03 2009-12-25 Лео Фарма А/С Эфиры гидроксамовых кислот и их фармацевтическое применение
TWI378090B (en) 2005-04-13 2012-12-01 Astex Therapeutics Ltd Pharmaceutical compounds
US8299076B2 (en) 2005-05-18 2012-10-30 Array Biopharma Inc. Crystalline forms of 2-(2-flouro-4-iodophenylamino)-N-(2-hydroxyethoxy)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxamide
US7754725B2 (en) 2006-03-01 2010-07-13 Astex Therapeutics Ltd. Dihydroxyphenyl isoindolymethanones
WO2008006032A1 (en) 2006-07-06 2008-01-10 Array Biopharma Inc. Cyclopenta [d] pyrimidines as akt protein kinase inhibitors
US8329701B2 (en) 2006-07-06 2012-12-11 Array Biopharma Inc. Dihydrofuro pyrimidines as AKT protein kinase inhibitors
US8063050B2 (en) 2006-07-06 2011-11-22 Array Biopharma Inc. Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors
ATE532789T1 (de) 2006-07-06 2011-11-15 Array Biopharma Inc Dihydrothienopyrimidine als akt-proteinkinase- inhibitoren
JP5518478B2 (ja) 2006-10-12 2014-06-11 アステックス、セラピューティックス、リミテッド 医薬化合物
WO2008044027A2 (en) 2006-10-12 2008-04-17 Astex Therapeutics Limited Pharmaceutical compounds having hsp90 inhibitory or modulating activity
JP5721949B2 (ja) 2006-10-12 2015-05-20 アステックス、セラピューティックス、リミテッドＡｓｔｅｘ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｌｉｍｉｔｅｄ 複合薬剤
WO2008044041A1 (en) 2006-10-12 2008-04-17 Astex Therapeutics Limited Pharmaceutical combinations
GB0620259D0 (en) 2006-10-12 2006-11-22 Astex Therapeutics Ltd Pharmaceutical compounds
EP2073807A1 (en) 2006-10-12 2009-07-01 Astex Therapeutics Limited Pharmaceutical combinations
EP2173723B3 (en) 2007-07-05 2014-11-19 Array Biopharma Inc. Pyrimidyl cyclopentanes as akt protein kinase inhibitors
US8846683B2 (en) 2007-07-05 2014-09-30 Array Biopharma, Inc. Pyrimidyl cyclopentanes as Akt protein kinase inhibitors
US9409886B2 (en) 2007-07-05 2016-08-09 Array Biopharma Inc. Pyrimidyl cyclopentanes as AKT protein kinase inhibitors
RU2486181C2 (ru) 2007-07-05 2013-06-27 Эррэй Биофарма Инк. Пиримидилциклопентаны как ингибиторы акт-протеинкиназ
ES2422733T3 (es) 2008-01-09 2013-09-13 Array Biopharma Inc Pirimidilciclopentanos hidroxilados como inhibidores de proteínas cinasas AKT
AU2009204019B2 (en) 2008-01-09 2014-02-20 Array Biopharma Inc. Hydroxylated pyrimidyl cyclopentane as AKT protein kinase inhibitor
GB0806527D0 (en) 2008-04-11 2008-05-14 Astex Therapeutics Ltd Pharmaceutical compounds
CN101985428B (zh) * 2009-07-29 2014-02-12 杭州民生药业有限公司 邻苯胺基苯甲酸衍生物或其药学上可接受的盐、其制备方法及其用途
JP2013519714A (ja) * 2010-02-19 2013-05-30 センター ナショナル デ ラ リシェルシェ サイエンティフィック 芳香族求核置換によって目的の化学化合物を調製するための方法
JP2013519715A (ja) * 2010-02-19 2013-05-30 センター ナショナル デ ラ リシェルシェ サイエンティフィック 少なくとも１つの電子求引性基を有する芳香族カルボン酸誘導体の芳香族求核置換による目的の化学化合物の調製方法
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JP6147246B2 (ja) 2011-04-01 2017-06-14 ジェネンテック， インコーポレイテッド Ａｋｔ及びｍｅｋ阻害剤化合物の組み合わせ、及び使用方法
BR112015008113B1 (pt) * 2012-10-12 2022-05-24 Exelixis, Inc. Novo processo para preparar compostos para uso no tratamento de câncer
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CA2348236A1 (en) * 1999-01-13 2000-07-20 Stephen Douglas Barrett 4-arylamino, 4-aryloxy, and 4-arylthio diarylamines and derivatives thereof as selective mek inhibitors
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Also Published As

Publication number Publication date
JP2004507518A (ja) 2004-03-11
SV2002000601A (es) 2002-04-03
WO2002018319A1 (en) 2002-03-07
IS6724A (is) 2003-02-20
NO20030844D0 (no) 2003-02-24
MXPA03001654A (es) 2004-09-10
AP2001002249A0 (en) 2001-09-30
YU14303A (sh) 2006-08-17
CN1458921A (zh) 2003-11-26
TNSN01127A1 (en) 2005-11-10
KR20030059115A (ko) 2003-07-07
HUP0300828A2 (hu) 2003-09-29
PE20020393A1 (es) 2002-05-09
DOP2001000238A (es) 2003-01-31
MA26949A1 (fr) 2004-12-20
SK2072003A3 (en) 2004-01-08
EP1313694A1 (en) 2003-05-28
AU2001277044A1 (en) 2002-03-13
PA8526501A1 (es) 2002-07-30
NO20030844L (no) 2003-02-25
UY26908A1 (es) 2001-11-30
BR0113520A (pt) 2003-06-24
BG107635A (bg) 2004-09-30
IL154507A0 (en) 2003-09-17
CA2420003A1 (en) 2002-03-07
GT200100174A (es) 2002-07-18
ZA200301182B (en) 2004-05-12
CZ2003477A3 (cs) 2003-10-15
EA200300187A1 (ru) 2003-08-28
PL360699A1 (en) 2004-09-20
HN2001000216A (es) 2002-05-22

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