WO2004009583A3 - Benzimidazole derivatives and their use as prodrugs of proton pump inhibitor - Google Patents

Benzimidazole derivatives and their use as prodrugs of proton pump inhibitor Download PDF

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Publication number
WO2004009583A3
WO2004009583A3 PCT/US2003/022419 US0322419W WO2004009583A3 WO 2004009583 A3 WO2004009583 A3 WO 2004009583A3 US 0322419 W US0322419 W US 0322419W WO 2004009583 A3 WO2004009583 A3 WO 2004009583A3
Authority
WO
WIPO (PCT)
Prior art keywords
prodrugs
proton pump
pump inhibitor
benzimidazole derivatives
bioavailability
Prior art date
Application number
PCT/US2003/022419
Other languages
French (fr)
Other versions
WO2004009583A2 (en
Inventor
Michael E Garst
George Sachs
Jai Moo Shin
Original Assignee
Michael E Garst
George Sachs
Jai Moo Shin
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
Priority to NZ538221A priority Critical patent/NZ538221A/en
Application filed by Michael E Garst, George Sachs, Jai Moo Shin filed Critical Michael E Garst
Priority to CA2492718A priority patent/CA2492718C/en
Priority to MXPA05000657A priority patent/MXPA05000657A/en
Priority to DE60304726T priority patent/DE60304726T2/en
Priority to EP03765694A priority patent/EP1556371B1/en
Priority to AU2003259154A priority patent/AU2003259154B2/en
Priority to JP2004523537A priority patent/JP4463103B2/en
Priority to BR0312802-4A priority patent/BR0312802A/en
Publication of WO2004009583A2 publication Critical patent/WO2004009583A2/en
Publication of WO2004009583A3 publication Critical patent/WO2004009583A3/en
Priority to IL16637105A priority patent/IL166371A0/en
Priority to NO20050801A priority patent/NO20050801L/en
Priority to HK06100445A priority patent/HK1079207A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/04—Drugs for disorders of the respiratory system for throat disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • 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
    • A61P31/04—Antibacterial agents
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

Abstract

Prodrugs of proton pump inhibitors of Formulas 1 through 4, (I-IV), where the symbols are as defined in the specification, and the R group includes at least one acidic group or its pharmaceutically acceptable salt, have improved aqueous solubility and bioavailability.
PCT/US2003/022419 2002-07-19 2003-07-15 Benzimidazole derivatives and their use as prodrugs of proton pump inhibitor WO2004009583A2 (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
AU2003259154A AU2003259154B2 (en) 2002-07-19 2003-07-15 Benzimidazole derivatives and their use as prodrugs of proton pump inhibitor
CA2492718A CA2492718C (en) 2002-07-19 2003-07-15 Prodrugs of proton pump inhibitors
MXPA05000657A MXPA05000657A (en) 2002-07-19 2003-07-15 Benzimidazole derivatives and their use as prodrugs of proton pump inhibitor.
DE60304726T DE60304726T2 (en) 2002-07-19 2003-07-15 BENZIMIDAZOLE DERIVATIVES AND THEIR USE AS PRODRUGS FOR PROTONAL PUMP INHIBITORS
EP03765694A EP1556371B1 (en) 2002-07-19 2003-07-15 Benzimidazole derivatives and their use as prodrugs of proton pump inhibitor
NZ538221A NZ538221A (en) 2002-07-19 2003-07-15 Benzimidazole derivatives and their use as prodrugs of proton pump inhibitor for treating gastrointestinal inflammatory diseases
JP2004523537A JP4463103B2 (en) 2002-07-19 2003-07-15 Benzimidazole derivatives and their use as prodrugs of proton pump inhibitors
BR0312802-4A BR0312802A (en) 2002-07-19 2003-07-15 Proton pump inhibitor prodrugs
IL16637105A IL166371A0 (en) 2002-07-19 2005-01-18 Benzimidazole derivatives and their use as prodrugs of proton pump inhibitor
NO20050801A NO20050801L (en) 2002-07-19 2005-02-15 Prodrug of proton pump inhibitors
HK06100445A HK1079207A1 (en) 2002-07-19 2006-01-11 Benzimidazole derivatives and their use as prodrugs of proton pump inhibitor

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US39745902P 2002-07-19 2002-07-19
US60/397,459 2002-07-19

Publications (2)

Publication Number Publication Date
WO2004009583A2 WO2004009583A2 (en) 2004-01-29
WO2004009583A3 true WO2004009583A3 (en) 2004-03-18

Family

ID=30771064

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2003/022419 WO2004009583A2 (en) 2002-07-19 2003-07-15 Benzimidazole derivatives and their use as prodrugs of proton pump inhibitor

Country Status (23)

Country Link
US (3) US6897227B2 (en)
EP (1) EP1556371B1 (en)
JP (1) JP4463103B2 (en)
KR (2) KR100788778B1 (en)
AT (1) ATE323695T1 (en)
AU (1) AU2003259154B2 (en)
BR (1) BR0312802A (en)
CA (1) CA2492718C (en)
CO (1) CO5690576A2 (en)
DE (1) DE60304726T2 (en)
DK (1) DK1556371T3 (en)
ES (1) ES2263028T3 (en)
HK (1) HK1079207A1 (en)
IL (1) IL166371A0 (en)
MX (1) MXPA05000657A (en)
NO (1) NO20050801L (en)
NZ (1) NZ538221A (en)
PL (1) PL375255A1 (en)
PT (1) PT1556371E (en)
RU (1) RU2292342C2 (en)
TW (1) TW200502231A (en)
WO (1) WO2004009583A2 (en)
ZA (1) ZA200501116B (en)

Families Citing this family (23)

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Publication number Priority date Publication date Assignee Title
US6852739B1 (en) * 1999-02-26 2005-02-08 Nitromed Inc. Methods using proton pump inhibitors and nitric oxide donors
EP1534278A4 (en) * 2002-08-01 2006-09-06 Nitromed Inc Nitrosated proton pump inhibitors, compositions and methods of use
EP1644352A1 (en) * 2003-07-15 2006-04-12 Allergan, Inc. Process for preparing isomerically pure prodrugs of proton pump inhibitors
WO2005039640A1 (en) * 2003-10-03 2005-05-06 Allergan Inc. Compositions comprising trefoil factor family peptides and/or mucoadhesives and proton pump inhibitor prodrugs
US20050075371A1 (en) * 2003-10-03 2005-04-07 Allergan, Inc. Methods and compositions for the oral administration of prodrugs of proton pump inhibitors
AU2005216862A1 (en) * 2004-02-18 2005-09-09 Allergan, Inc. Compositions comprising prodrugs of proton pump inhibitors
EP1715854A2 (en) * 2004-02-18 2006-11-02 Allergan, Inc. Prodrugs for the intravenous administration of proton pump inhibitors
BRPI0507796A (en) * 2004-03-11 2007-07-17 Allergan Inc methods and compositions for treating conditions related to gastric acid secretion
US7176319B2 (en) 2004-04-28 2007-02-13 Hetero Drugs Limited Process for substituted sulfoxides
WO2007073301A1 (en) * 2005-12-23 2007-06-28 Astrazeneca Ab Benzoimidazole derivatives as prodrugs of proton pump inhibitors
WO2007081871A1 (en) * 2006-01-10 2007-07-19 Allergan, Inc. Therapeutic salt compositions of sulfonyl ester prodrugs of proton pump inhibitors and methods for their preparation
JP2009536195A (en) * 2006-05-09 2009-10-08 アストラゼネカ・アクチエボラーグ Parenteral formulations containing proton pump inhibitors sterilized by ionizing radiation in the final container
US20070293543A1 (en) * 2006-06-19 2007-12-20 Edward Lee THRESHOLD BLOOD OMEPRAZOLE CONCENTRATION IS 50 NG/ML FOR THE MAINTENANCE OF INTRAGASTRIC pH OF AT LEAST 4.0 AFTER ORAL DOSING WITH CMA-OMEPRAZOLE, AGN 201904-Z
WO2008036211A1 (en) * 2006-09-19 2008-03-27 Alevium Pharmaceuticals, Inc. Prodrugs of proton pump inhibitors including the (1h-pyrrol-1-yl)-1h-benzimidazole moiety
WO2008036201A1 (en) * 2006-09-19 2008-03-27 Alevium Pharmaceuticals, Inc. Prodrugs of proton pump inhibitors including the 1h-imidazo[4,5-b] pyridine moiety
KR20090035195A (en) * 2007-10-05 2009-04-09 엘지전자 주식회사 Plasma display apparatus
US20100265240A1 (en) * 2007-10-05 2010-10-21 Lg Electronics Inc. Plasma display device
KR100895333B1 (en) * 2007-11-01 2009-05-07 엘지전자 주식회사 Method for driving plasma display panel and plasma display device thereof
WO2012051036A1 (en) 2010-10-11 2012-04-19 Merck Sharp & Dohme Corp. Quinazolinone-type compounds as crth2 antagonists
EP2661265B1 (en) 2010-12-23 2017-03-08 Merck Sharp & Dohme Corp. Quinolines and aza-quinolines as crth2 receptor modulators
RU2589709C2 (en) 2010-12-23 2016-07-10 Мерк Шарп Энд Домэ Корп. Quinoxalines and azaquinoxalines as crth2 receptor modulators
CA2973370A1 (en) * 2015-01-09 2016-07-14 The Regents Of The University Of California Compositions and methods for treating gastrointestinal infections
CN108997177A (en) * 2018-09-04 2018-12-14 邵阳学院 A kind of method of microwave assisted N- benzenesulfonyl nitrobenzene amine compound synthesis

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5859030A (en) * 1994-06-10 1999-01-12 Byk Gulden Lomberg Chemische Fabrik Gmbh Substituted arylalkylthioalkylthiopyridines for use in the control of helicobacter bacteria
WO2000009498A1 (en) * 1998-08-10 2000-02-24 Partnership Of Michael E. Garst, George Sachs And Jai Moo Shin Prodrugs of proton pump inhibitors
WO2002030920A1 (en) * 2000-10-12 2002-04-18 Takeda Chemical Industries, Ltd. Benzimidazole compounds, process for producing the same and use thereof

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SE416649B (en) 1974-05-16 1981-01-26 Haessle Ab PROCEDURE FOR THE PREPARATION OF SUBSTANCES WHICH PREVENT Gastric acid secretion
SE7804231L (en) 1978-04-14 1979-10-15 Haessle Ab Gastric acid secretion
JPS6150978A (en) 1984-08-16 1986-03-13 Takeda Chem Ind Ltd Pyridine derivative and preparation thereof
IL76839A (en) 1984-10-31 1988-08-31 Byk Gulden Lomberg Chem Fab Picoline derivatives,processes for the preparation thereof and pharmaceutical compositions containing the same
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Patent Citations (5)

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Publication number Priority date Publication date Assignee Title
US5859030A (en) * 1994-06-10 1999-01-12 Byk Gulden Lomberg Chemische Fabrik Gmbh Substituted arylalkylthioalkylthiopyridines for use in the control of helicobacter bacteria
WO2000009498A1 (en) * 1998-08-10 2000-02-24 Partnership Of Michael E. Garst, George Sachs And Jai Moo Shin Prodrugs of proton pump inhibitors
US6559167B1 (en) * 1998-08-10 2003-05-06 Regents Of The University Of California Prodrugs of proton pump inhibitors
WO2002030920A1 (en) * 2000-10-12 2002-04-18 Takeda Chemical Industries, Ltd. Benzimidazole compounds, process for producing the same and use thereof
EP1334971A1 (en) * 2000-10-12 2003-08-13 Takeda Chemical Industries, Ltd. Benzimidazole compounds, process for producing the same and use thereof

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KAMINSKI J J ET AL: "ANTIULCER AGENTS. 5. INHIBITION OF GASTRIC H+/K+-ATPASE BY SUBSITUTED IMIDAZOL1,2-A PYRIDINES AND RELATED ANALOGUES AND ITS IMPLICATION IN MODELING THE HIGH AFFINITY POTASSIUM ION BINDING SITE OF THE GASTRIC PROTON PUMP ENZYME", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY. WASHINGTON, US, vol. 34, 1991, pages 533 - 541, XP000919185, ISSN: 0022-2623 *

Also Published As

Publication number Publication date
US6897227B2 (en) 2005-05-24
PL375255A1 (en) 2005-11-28
KR100822981B1 (en) 2008-04-16
ATE323695T1 (en) 2006-05-15
PT1556371E (en) 2006-09-29
DK1556371T3 (en) 2006-08-21
ES2263028T3 (en) 2006-12-01
BR0312802A (en) 2005-04-19
CA2492718A1 (en) 2004-01-29
TW200502231A (en) 2005-01-16
US20040102484A1 (en) 2004-05-27
NZ538221A (en) 2006-11-30
ZA200501116B (en) 2006-11-29
AU2003259154B2 (en) 2006-12-07
EP1556371B1 (en) 2006-04-19
MXPA05000657A (en) 2005-08-19
CA2492718C (en) 2010-12-21
WO2004009583A2 (en) 2004-01-29
RU2292342C2 (en) 2007-01-27
CO5690576A2 (en) 2006-10-31
JP4463103B2 (en) 2010-05-12
JP2005536519A (en) 2005-12-02
AU2003259154A1 (en) 2004-02-09
EP1556371A2 (en) 2005-07-27
DE60304726T2 (en) 2007-08-09
US20050143423A1 (en) 2005-06-30
HK1079207A1 (en) 2006-03-31
IL166371A0 (en) 2006-01-16
KR100788778B1 (en) 2007-12-27
US20050182101A1 (en) 2005-08-18
DE60304726D1 (en) 2006-05-24
AU2003259154C1 (en) 2004-02-09
KR20070005029A (en) 2007-01-09
KR20050047078A (en) 2005-05-19
RU2005105564A (en) 2005-10-10
NO20050801L (en) 2005-02-15

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