ES2567133T3 - Proceso para preparar compuestos de benzoimidazol - Google Patents

Proceso para preparar compuestos de benzoimidazol Download PDF

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Publication number
ES2567133T3
ES2567133T3 ES06785244T ES06785244T ES2567133T3 ES 2567133 T3 ES2567133 T3 ES 2567133T3 ES 06785244 T ES06785244 T ES 06785244T ES 06785244 T ES06785244 T ES 06785244T ES 2567133 T3 ES2567133 T3 ES 2567133T3
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ES
Spain
Prior art keywords
formula
compound
hydrogen
preparing
alkyl
Prior art date
Legal status (The legal status 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 status listed.)
Active
Application number
ES06785244T
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English (en)
Inventor
John Demattei
Sagar Shakya
Anthony D. Piscopio
Bruno P. Hache
Matthew Evans
James Gair Ford
Simon Mark Pointon
Koen Peeters
Timothy John Lilley
John Leonard
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
AstraZeneca AB
Array Biopharma Inc
Original Assignee
AstraZeneca AB
Array Biopharma Inc
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, Array Biopharma Inc filed Critical AstraZeneca AB
Application granted granted Critical
Publication of ES2567133T3 publication Critical patent/ES2567133T3/es
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
    • C07D235/30—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • 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
    • C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
    • C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C205/58—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by halogen atoms
    • 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
    • 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
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C229/60—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in meta- or para- positions

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

Un proceso para preparar un compuesto de fórmula Ia-1**Fórmula** y sales y solvatos del mismo, en donde Z es -C(>=O)OR1; R1 es hidrógeno o alquilo C1-C10; R2 es hidrógeno; X1 y X2 son independientemente seleccionados de entre hidrógeno, F, Cl, Br e I; X5 es F, Cl, Br o I; y R10 es alquilo C1-C10; método que comprende: nitrar un compuesto que tiene la fórmula**Fórmula** en donde X3 y X4 son independientemente F, Cl, Br, I o un éster de sulfonato, para obtener un compuesto de fórmula II II**Fórmula** tratar dicho compuesto de fórmula II, opcionalmente a temperaturas y/o presión elevadas, con dos o más equivalentes de (i) un reactivo que contiene o genera amoníaco, o (ii) una amina primaria que no es una amina aromática, o (iii) un reactivo seleccionado de entre amoníaco protegido o equivalentes amídicos, agentes nucleófilos nitrogenados que tienen la fórmula MNR2R2a en donde M es un metal, y silil-amiduros metálicos, para obtener un compuesto de fórmula VI-11 en donde A es -NR2R2a,
ES06785244T 2005-06-23 2006-06-21 Proceso para preparar compuestos de benzoimidazol Active ES2567133T3 (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US69327005P 2005-06-23 2005-06-23
US693270P 2005-06-23
PCT/US2006/024084 WO2007002157A2 (en) 2005-06-23 2006-06-21 Process for preparing benzimidazole compounds

Publications (1)

Publication Number Publication Date
ES2567133T3 true ES2567133T3 (es) 2016-04-20

Family

ID=37595779

Family Applications (1)

Application Number Title Priority Date Filing Date
ES06785244T Active ES2567133T3 (es) 2005-06-23 2006-06-21 Proceso para preparar compuestos de benzoimidazol

Country Status (17)

Country Link
US (4) US8039637B2 (es)
EP (1) EP1904481B1 (es)
JP (1) JP5237798B2 (es)
KR (2) KR101351190B1 (es)
CN (1) CN101248060B (es)
AR (1) AR054623A1 (es)
AU (1) AU2006262259B2 (es)
BR (1) BRPI0611993B1 (es)
CA (1) CA2612419C (es)
ES (1) ES2567133T3 (es)
HK (1) HK1118809A1 (es)
IL (2) IL188273A (es)
MX (1) MX351820B (es)
MY (1) MY177122A (es)
SG (1) SG162815A1 (es)
TW (1) TWI391380B (es)
WO (1) WO2007002157A2 (es)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109456272A (zh) 2012-10-19 2019-03-12 阵列生物制药公司 Mek抑制剂的制备和包含mek抑制剂的制剂
RU2019110048A (ru) * 2016-10-06 2020-11-06 Ассиа Кемикал Индастрис Лтд. Твердые формы валбеназина

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2334973A1 (de) * 1973-07-10 1975-01-23 Boehringer Mannheim Gmbh Neue biphenyl-derivate
CZ284687B6 (cs) * 1986-04-30 1999-02-17 Dainippon Pharmaceutical Co., Ltd. Substituovaný benzamidový derivát, způsob jeho výroby a farmaceutický prostředek na jeho bázi
ES2150417T3 (es) 1990-11-06 2000-12-01 Yamanouchi Pharma Co Ltd Derivados de pirazina fusionados.
DE4115983A1 (de) * 1991-05-16 1992-11-19 Henkel Kgaa Haarfaerbemittel
JPH06332129A (ja) * 1993-03-25 1994-12-02 Konica Corp カラー画像の形成方法
AU688459B2 (en) 1994-04-08 1998-03-12 Shionogi & Co., Ltd. Oxopyridinylquinoxaline derivative
AU2351895A (en) 1994-04-28 1995-11-29 Yamanouchi Pharmaceutical Co., Ltd. N-(3-pyrrolidinyl)benzamide derivative
US5597823A (en) 1995-01-27 1997-01-28 Abbott Laboratories Tricyclic substituted hexahydrobenz [e]isoindole alpha-1 adrenergic antagonists
US6369235B1 (en) * 1997-02-25 2002-04-09 The United States Of America As Represented By The Department Of Health And Human Services Substituted benzimidazoles, and methods of use thereof, for the inhibition of HIV reverse transcription and for the treatment of HIV infection
US5817823A (en) * 1997-04-17 1998-10-06 Sepracor Inc. Method for synthesizing 2-substituted imidazoles
US6087368A (en) * 1998-06-08 2000-07-11 Bristol-Myers Squibb Company Quinazolinone inhibitors of cGMP phosphodiesterase
DE69926800T2 (de) 1999-01-13 2006-05-18 Warner-Lambert Company Llc Benzoheterozyklen und ihre verwendung als mek inhibitoren
KR20020015376A (ko) 1999-07-16 2002-02-27 로즈 암스트롱, 크리스틴 에이. 트러트웨인 Ｍｅｋ 억제제를 사용한 만성 통증의 치료 방법
TR200200205T2 (tr) 1999-07-16 2002-06-21 Warner-Lambert Company MEK inhibitörleri kullanılarak kronik ağrının tedavi edilmesi
US20030073832A1 (en) 2001-04-10 2003-04-17 Havez Sophie Elisabeth Novel aminophenyl ketone derivatives
DE60205100T2 (de) * 2001-04-12 2006-06-01 F. Hoffmann-La Roche Ag DIHYDRO-BENZO (b) (1,4) DIAZEPIN-2-ON-DERIVATE ALS MGLUR2 ANTAGONISTEN
DE60221866T2 (de) * 2001-10-19 2008-05-29 Ortho-Mcneil Pharmaceutical, Inc. 2-PHENYL BENZIMIDAZOLE UND IMIDAZO-i4,5ö-PYRIDINE ALS CDS1/CHK2-INHIBITOREN UND ADJUVANTIEN IN DER CHEMOTHERAPIE ODER STRAHLUNGSTHERAPIE ZUR BEHANDLUNG VON KREBS
PT3000810T (pt) * 2002-03-13 2017-10-25 Array Biopharma Inc Derivados de benzimidazole alquilado n3 como inibidores de mek
UA76837C2 (uk) 2002-03-13 2006-09-15 Еррей Байофарма Інк. N3 алкіловані похідні бензімідазолу як інгібітори мек
WO2004106348A1 (ja) * 2003-05-28 2004-12-09 Astellas Pharma Inc. アミノメチル置換フルオロチアゾロベンゾイミダゾール誘導体
ATE442847T1 (de) * 2003-07-24 2009-10-15 Warner Lambert Co Benzimidazol-derivate als mek-hemmer
JP4829506B2 (ja) 2004-02-17 2011-12-07 石原産業株式会社 チオアミド系化合物又はその塩、並びにそれらを含有するサイトカイン産生抑制剤
WO2005080352A2 (en) * 2004-02-19 2005-09-01 Rexahn Corporation Quinazoline derivatives and therapeutic use thereof

Also Published As

Publication number Publication date
WO2007002157A3 (en) 2007-11-01
JP5237798B2 (ja) 2013-07-17
IL223313A (en) 2015-07-30
KR20080028443A (ko) 2008-03-31
CN101248060B (zh) 2014-09-10
MY177122A (en) 2020-09-07
HK1118809A1 (zh) 2009-04-09
US20110319632A1 (en) 2011-12-29
SG162815A1 (en) 2010-07-29
US9024040B2 (en) 2015-05-05
EP1904481A4 (en) 2010-11-10
US20130245279A1 (en) 2013-09-19
BRPI0611993A2 (pt) 2010-10-13
IL223313A0 (en) 2013-02-03
MX351820B (es) 2017-10-30
AU2006262259A1 (en) 2007-01-04
US8039637B2 (en) 2011-10-18
KR20140000721A (ko) 2014-01-03
AR054623A1 (es) 2007-07-04
CA2612419C (en) 2017-06-13
TWI391380B (zh) 2013-04-01
US8383832B2 (en) 2013-02-26
IL188273A (en) 2015-03-31
WO2007002157A2 (en) 2007-01-04
IL188273A0 (en) 2008-04-13
EP1904481A2 (en) 2008-04-02
US20100145065A1 (en) 2010-06-10
EP1904481B1 (en) 2016-02-17
KR101351190B1 (ko) 2014-01-14
US8501956B2 (en) 2013-08-06
AU2006262259B2 (en) 2013-03-14
TW200738647A (en) 2007-10-16
CN101248060A (zh) 2008-08-20
US20110319631A1 (en) 2011-12-29
CA2612419A1 (en) 2007-01-04
BRPI0611993B1 (pt) 2023-11-28
JP2009501146A (ja) 2009-01-15

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