AR049168A1 - BENZIMIDAZOL DERIVATIVES - Google Patents

BENZIMIDAZOL DERIVATIVES

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Publication number
AR049168A1
AR049168A1 ARP050101885A ARP050101885A AR049168A1 AR 049168 A1 AR049168 A1 AR 049168A1 AR P050101885 A ARP050101885 A AR P050101885A AR P050101885 A ARP050101885 A AR P050101885A AR 049168 A1 AR049168 A1 AR 049168A1
Authority
AR
Argentina
Prior art keywords
alkoxy
alkyl
hydroxy
hydrogen
amino
Prior art date
Application number
ARP050101885A
Other languages
Spanish (es)
Inventor
Peter Jan Zimmermann
Buhr Wilm Dr
Chiesa M Vittoria Dr
Andreas Palmer
Brehm Christof Dr
Simon Wolfgang-Alexander Dr
Postius Stefan Dr
Dr Kromer Wolfgang Prof
Original Assignee
Altana Pharma Ag
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 Altana Pharma Ag filed Critical Altana Pharma Ag
Publication of AR049168A1 publication Critical patent/AR049168A1/en

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    • 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
    • C07D235/08—Radicals containing only hydrogen and carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Reivindicacion 1: Un nuevo compuesto de 6-bencimidazol substituido, caracterizado por la formula (1), donde: R1 es hidrogeno, alquilo C1-4, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-4, alcoxi C1-4, alcoxi C1-4-alquilo C1-4, alcoxi C1-4- carbonilo, alquenilo C2-4, alquinilo C2-4, fluoro-alquilo C1-4, hidroxi-alquilo C1-4, mono- o di-alquil C1-4-amino o alquil C1-4-carboniloxi-alquilo C1-4; R2 es hidrogeno, alquilo C1-4, arilo, cicloalquilo C3-7, cicloalquil C3-7-alquilo C1-4, alcoxi C1-4-carbonilo, mono- o di-alquil C1-4-amino-alquil C1-4-carbonilo, hidroxi-alquilo C1-4, fluoro-alquilo C2-4, aril C1-4-alcoxi C1-4-alquilo C1-4, hidroxi o alcoxi C1-4; R3 es hidrogeno, halogeno, fluoro-alquilo C1-4, carboxilo, -CO-alcoxi C1-4, hidroxi-alquilo C1-4, alcoxi C1-4-alquilo C1-4, alcoxi C1-4-alcoxi C1-4-alquilo C1-4, fluoro-alcoxi C1-4-alquilo C1-4, ciano, el grupo -CO-NR31R32, el grupo SO2-NR31R32 o el grupo Het; donde R31 es hidrogeno, hidroxilo, alquilo C1-7, hidroxi-alquilo C1-4, alcoxi C1-4-alquilo C1-4 o cicloalquilo C3-7, amino; y R32 es hidrogeno, alquilo C1-7, hidroxi-alquilo C1-4 o alcoxi C1-4-alquilo C1-4; o donde R31 y R32 tomados conjuntamente, incluyendo el átomo de nitrogeno al cual están ligados, son un grupo pirrolidino, piperidino, piperazino, N-alquil C1-4-piperazino, morfolino, aziridino o acetidino; y Het es un residuo heterocíclico, sustituido por R33, R34 y R35, seleccionado del grupo formado por oxadiazol, dihidrooxazol, dihidroimidazol, oxazol, imidazol, isoxazol, dihidroisoxazol, pirazol y tetrazol; donde R33 es hidrogeno, alquilo C1-4, hidroxi-alquilo C1-4, alcoxi C1-4, alqueniloxi C2-4, alquil C1-4-carbonilo, carboxi, alcoxi C1-4-carbonilo, carboxi-alquilo C1-4, alcoxi C1-4- carbonil-alquilo C1-4, halogeno, hidroxi, arilo, aril-alquilo C1-4, aril-oxi, aril-alcoxi C1-4, trifluorometilo, nitro, amino, mono- o di-alquil C1-4-amino, alquil C1-4-carbonilamino, alcoxi C1-4-carbonilamino, alcoxi C1-4-alcoxi C1-4-carbonilamino o sulfonilo; R34 es hidrogeno, alquilo C1-4, alcoxi C1-4, alcoxi C1-4-carbonilo, halogeno, trifluorometilo o hidroxi; R35 es hidrogeno, alquilo C1-4, alcoxi C1-4, alcoxi C1-4-carbonilo, halogeno, trifluorometilo o hidroxi; X es O (oxígeno) o NH; y Y o tiene el significado -CH2-Ar; donde Ar es un residuo aromático mono- o bicíclico, sustituido por R4, R5, R6 y R7, que es seleccionado del grupo formado por fenilo, naftilo, pirrolilo, pirazolilo, imidazolilo, 1,2,3-triazolilo, indolilo, bencimidazolilo, furilo, benzofurilo, tienilo, benzotienilo, tiazolilo, isoxazolilo, piridinilo, pirimidinilo, quinolinilo o isoquinolinilo; o Y significado el grupo de formula (2), donde Z tiene el significado -CHR8- o -CHR8-CHR9- donde en Ar y/o en el grupo de formula (2); R4 es hidrogeno, alquilo C1-4, hidroxi-alquilo C1-4, alcoxi C1-4, alqueniloxi C2-4, alquil C1-4-carbonilo, carboxi, alcoxi C1-4-carbonilo, carboxi-alquilo C1-4, alcoxi C1-4-carbonil-alquilo C1-4, halogeno, hidroxi, arilo, aril-alquilo C1-4, aril-oxi, aril-alcoxi C1-4, trifluorometilo, fluoro-alcoxi C1-4, nitro, amino, mono- o di-alquil C1-4-amino, alquil C1-4-carbonilamino, alcoxi C1-4-carbonilamino, alcoxi C1-4-alcoxi C1-4-carbonilamino o sulfonilo; R5 es hidrogeno, alquilo C1-4, alcoxi C1-4, alcoxi C1-4-carbonilo, halogeno, trifluorometilo o hidroxi; R6 es hidrogeno, alquilo C1-4 o halogeno; y R7 es hidrogeno, alquilo C1-4 o halogeno; R8 es hidrogeno, alquilo C1-7, alquenilo C2-7, hidroxilo, alcoxi C1-4, alcoxi C1-4, oxo-substituido, cicloalcoxi C3-7, cicloalquil C3-7-alcoxi C1-4, hidroxi-alcoxi C1-4, alcoxi C1-4-alcoxi C1-4, alcoxi C1-4-alcoxi C1-4-alcoxi C1-4, cicloalcoxi C3-7-alcoxi C1-4, cicloalquil C3-7-alcoxi C1-4-alcoxi C1-4, alquil C1-4- carboniloxi, halo-alcoxi C1-4, amino, mono- o di-alquil C1-4-amino, alquil C1-4-carbonilamino, alcoxi C1-4-carbonilamino, mono- o di-alquil C1-4-amino-alquil C1-4-carboniloxi, alcoxi C1-4-alcoxi C1-4-carbonilamino o alcoxi C1-4-alquil C1-4- carboniloxi; R9 es hidrogeno, alquilo C1-7, alquenilo C2-7, hidroxilo, alcoxi C1-4, alcoxi C1-4 oxo-sustituido, cicloalcoxi C3-7, cicloalquil C3-7-alcoxi C1-4, hidroxi-alcoxi C1-4, alcoxi C1-4-alcoxi C1-4, alcoxi C1-4-alcoxi C1-4-alcoxi C1-4, cicloalcoxi C3-7-alcoxi C1-4, cicloalquil C3-7-alcoxi C1-4-alcoxi C1-4, alquil C1-4-carboniloxi, halo-alcoxi C1-4, amino, mono- o di-alquil C1-4-amino, alquil C1-4-carbonilamino, alcoxi C1-4-carbonilamino, mono- o di-alquil C1-4-amino-alquil C1-4- carboniloxi, alcoxi C1-4-alcoxi C1-4-carbonilamino o alcoxi C1-4-alquil C1-4-carboniloxi; y donde arilo es fenilo o fenilo sustituido por uno, dos o tres sustituyentes iguales o diferentes del grupo formado por alquilo C1-4, alcoxi C1-4, carboxi, alcoxi C1-4-carbonilo, halogeno, trifluorometilo, nitro, trifluorometoxi, hidroxi y ciano, y sus sales.Claim 1: A new substituted 6-benzimidazole compound, characterized by formula (1), wherein: R1 is hydrogen, C1-4 alkyl, C3-7 cycloalkyl, C3-7 cycloalkyl-C1-4 alkyl, C1-4 alkoxy , C1-4 alkoxy-C1-4 alkyl, C1-4 alkoxycarbonyl, C2-4 alkenyl, C2-4 alkynyl, C1-4 fluoro-alkyl, hydroxyC 1-4 alkyl, mono- or di-C1-alkyl 4-amino or C 1-4 alkylcarbonyloxyC 1-4 alkyl; R 2 is hydrogen, C 1-4 alkyl, aryl, C 3-7 cycloalkyl, C 3-7 cycloalkyl-C 1-4 alkyl, C 1-4 alkoxycarbonyl, mono- or di-C 1-4 alkyl-C 1-4 alkyl-alkyl carbonyl, hydroxy-C1-4 alkyl, fluoro-C2-4 alkyl, aryl C1-4-C1-4 alkoxy-C1-4 alkyl, hydroxy or C1-4 alkoxy; R3 is hydrogen, halogen, fluoro-C1-4 alkyl, carboxyl, -CO-C1-4 alkoxy, hydroxy-C1-4 alkyl, C1-4 alkoxy-C1-4 alkyl, C1-4 alkoxy-C1-4 alkoxy C1-4 alkyl, fluoro-C1-4 alkoxy-C1-4 alkyl, cyano, the -CO-NR31R32 group, the SO2-NR31R32 group or the Het group; where R31 is hydrogen, hydroxyl, C1-7 alkyl, hydroxy-C1-4 alkyl, C1-4 alkoxy-C1-4 alkyl or C3-7 cycloalkyl, amino; and R32 is hydrogen, C1-7 alkyl, hydroxy-C1-4 alkyl or C1-4 alkoxy-C1-4 alkyl; or where R31 and R32 taken together, including the nitrogen atom to which they are linked, are a pyrrolidino, piperidino, piperazino, N-C1-4-piperazino, morpholino, aziridino or acetidino group; and Het is a heterocyclic residue, substituted by R33, R34 and R35, selected from the group consisting of oxadiazole, dihydrooxazol, dihydroimidazole, oxazole, imidazole, isoxazole, dihydroisoxazole, pyrazole and tetrazole; where R33 is hydrogen, C1-4 alkyl, hydroxy C1-4 alkyl, C1-4 alkoxy, C2-4 alkenyloxy, C1-4 alkylcarbonyl, carboxy, C1-4 alkoxycarbonyl, carboxy C1-4 alkyl, C 1-4 alkoxycarbonylC 1-4 alkyl, halogen, hydroxy, aryl, arylC 1-4 alkyl, aryl-oxy, arylC 1-4 alkoxy, trifluoromethyl, nitro, amino, mono- or di-C 1- alkyl 4-amino, C 1-4 alkylcarbonylamino, C 1-4 alkoxycarbonylamino, C 1-4 alkoxy-C 1-4 alkoxycarbonylamino or sulfonyl; R34 is hydrogen, C1-4 alkyl, C1-4 alkoxy, C1-4 alkoxycarbonyl, halogen, trifluoromethyl or hydroxy; R35 is hydrogen, C1-4 alkyl, C1-4 alkoxy, C1-4 alkoxycarbonyl, halogen, trifluoromethyl or hydroxy; X is O (oxygen) or NH; and Y o has the meaning -CH2-Ar; where Ar is a mono- or bicyclic aromatic residue, substituted by R4, R5, R6 and R7, which is selected from the group consisting of phenyl, naphthyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, indolyl, benzimidazolyl, furyl, benzofuryl, thienyl, benzothienyl, thiazolyl, isoxazolyl, pyridinyl, pyrimidinyl, quinolinyl or isoquinolinyl; or Y meaning the group of formula (2), where Z has the meaning -CHR8- or -CHR8-CHR9- where in Ar and / or in the group of formula (2); R4 is hydrogen, C1-4 alkyl, hydroxy C1-4 alkyl, C1-4 alkoxy, C2-4 alkenyloxy, C1-4 alkylcarbonyl, carboxy, C1-4 alkoxycarbonyl, carboxy C1-4 alkyl, alkoxy C1-4-carbonyl-C1-4alkyl, halogen, hydroxy, aryl, aryl-C1-4alkyl, aryl-oxy, aryl-C1-4alkoxy, trifluoromethyl, C1-4 fluoroalkoxy, nitro, amino, mono- or di-C 1-4 alkyl-amino, C 1-4 alkylcarbonylamino, C 1-4 alkoxycarbonylamino, C 1-4 alkoxy-C 1-4 alkoxycarbonylamino or sulfonyl; R5 is hydrogen, C1-4 alkyl, C1-4 alkoxy, C1-4 alkoxycarbonyl, halogen, trifluoromethyl or hydroxy; R6 is hydrogen, C1-4 alkyl or halogen; and R7 is hydrogen, C1-4 alkyl or halogen; R8 is hydrogen, C1-7 alkyl, C2-7 alkenyl, hydroxyl, C1-4 alkoxy, C1-4 alkoxy, oxo-substituted, C3-7 cycloalkoxy, C3-7 cycloalkyl-C1-4 alkoxy, hydroxy-C1- alkoxy 4, C1-4 alkoxy-C1-4 alkoxy, C1-4 alkoxy-C1-4 alkoxy-C1-4 alkoxy, C3-7 cycloalkoxy C1-4 alkoxy, C3-7 alkoxy C1-4 alkoxy C1- alkoxy 4, C 1-4 alkylcarbonyloxy, haloC 1-4 alkoxy, amino, mono- or di-C 1-4 alkyl, C 1-4 alkylcarbonylamino, C 1-4 alkoxycarbonylamino, mono- or di-alkyl C1-4-amino-C1-4 alkylcarbonyloxy, C1-4 alkoxy-C1-4 alkoxycarbonylamino or C1-4 alkoxy-C1-4 alkylcarbonyloxy; R9 is hydrogen, C1-7 alkyl, C2-7 alkenyl, hydroxyl, C1-4 alkoxy, C1-4 oxo-substituted alkoxy, C3-7 cycloalkoxy, C3-7 cycloalkyl-C1-4 alkoxy, hydroxy-C1-4 alkoxy , C1-4 alkoxy-C1-4 alkoxy, C1-4 alkoxy-C1-4 alkoxy-C1-4 alkoxy, C3-7 cycloalkoxy C1-4 alkoxy, C3-7 alkoxy C1-4 alkoxy C1-4 alkoxy , C1-4 alkylcarbonyloxy, halo C1-4 alkoxy, amino, mono- or di-C1-4 alkyl, C1-4 alkylcarbonylamino, C1-4 alkoxycarbonylamino, mono- or di-C1 alkyl -4-amino-C 1-4 alkylcarbonyloxy, C 1-4 alkoxy-C 1-4 alkoxycarbonylamino or C 1-4 alkoxy-C 1-4 alkylcarbonyloxy; and where aryl is phenyl or phenyl substituted by one, two or three substituents the same or different from the group consisting of C1-4 alkyl, C1-4 alkoxy, carboxy, C1-4 alkoxycarbonyl, halogen, trifluoromethyl, nitro, trifluoromethoxy, hydroxy and cyano, and its salts.

ARP050101885A 2004-05-18 2005-05-10 BENZIMIDAZOL DERIVATIVES AR049168A1 (en)

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EP04102191 2004-05-18

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AR049168A1 true AR049168A1 (en) 2006-07-05

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Country Status (7)

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EP (1) EP1756067A1 (en)
JP (1) JP2007538047A (en)
AR (1) AR049168A1 (en)
AU (1) AU2005243434A1 (en)
CA (1) CA2566821A1 (en)
TW (1) TW200600502A (en)
WO (1) WO2005111000A1 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2619518A1 (en) * 2005-08-22 2007-03-01 Nycomed Gmbh Isotopically substituted benzimidazole derivatives
WO2007031860A1 (en) * 2005-09-15 2007-03-22 Pfizer Japan Inc. Indane substituted benzimidazoles and their use as acid pump inhibitors
WO2007072142A2 (en) * 2005-12-19 2007-06-28 Pfizer Japan Inc. Benzimidazole-5-carboxamide derivatives
KR101088247B1 (en) 2005-12-19 2011-11-30 라퀄리아 파마 인코포레이티드 Chromane substituted benzimidazoles and their use as acid pump inhibitors
KR20190057569A (en) * 2017-11-20 2019-05-29 제일약품주식회사 7-amino-1H-indole-5-carboxamide derivatives, and use thereof
WO2024087155A1 (en) * 2022-10-28 2024-05-02 深圳市华先医药科技有限公司 Method for synthesizing 4-hydroxy-n,n,2-trimethylbenzimidazole-6-carboxamide

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE8604566D0 (en) * 1986-10-27 1986-10-27 Haessle Ab NOVEL COMPUNDS
IL108520A (en) * 1993-02-15 1997-09-30 Byk Gulden Lomberg Chem Fab 2, 3, 8-TRISUBSTITUTED IMIDAZO £1, 2-a| PYRIDINE DERIVATIVES, PROCESSES FOR THE PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
WO1996004251A1 (en) * 1994-08-03 1996-02-15 Fujisawa Pharmaceutical Co., Ltd. Heterocyclic compound
SE9602286D0 (en) * 1996-06-10 1996-06-10 Astra Ab New compounds
AR043063A1 (en) * 2002-12-13 2005-07-13 Altana Pharma Ag 6-SUBSTITUTED BENCIMIDAZOLS AND THEIR USE AS INHIBITORS OF GASTRIC SECRETIONS

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JP2007538047A (en) 2007-12-27
TW200600502A (en) 2006-01-01
AU2005243434A1 (en) 2005-11-24
EP1756067A1 (en) 2007-02-28
CA2566821A1 (en) 2005-11-24
WO2005111000A1 (en) 2005-11-24

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