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WO2003033507A1 - Benzylmalonic acid derivatives and proteasome inhibitors contaiing the same - Google Patents

Benzylmalonic acid derivatives and proteasome inhibitors contaiing the same Download PDF

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Publication number
WO2003033507A1
WO2003033507A1 PCT/JP2002/010451 JP0210451W WO03033507A1 WO 2003033507 A1 WO2003033507 A1 WO 2003033507A1 JP 0210451 W JP0210451 W JP 0210451W WO 03033507 A1 WO03033507 A1 WO 03033507A1
Authority
WO
WIPO (PCT)
Prior art keywords
remedies
acid derivatives
alkyl
diseases
contaiing
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.)
Ceased
Application number
PCT/JP2002/010451
Other languages
French (fr)
Japanese (ja)
Inventor
Hiroaki Satoh
Yoji Tachibana
Koichi Nakamaru
Ryotaro Kojima
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.)
Kyorin Pharmaceutical Co Ltd
Nisshin Pharma Inc
Original Assignee
Kyorin Pharmaceutical Co Ltd
Nisshin Pharma 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 Kyorin Pharmaceutical Co Ltd, Nisshin Pharma Inc filed Critical Kyorin Pharmaceutical Co Ltd
Priority to JP2003536246A priority Critical patent/JPWO2003033507A1/en
Publication of WO2003033507A1 publication Critical patent/WO2003033507A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/025—Boronic and borinic acid compounds
    • 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
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Immunology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pulmonology (AREA)
  • Transplantation (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Novel benzylmalonic acid derivatives represented by the following general formula (I) which have a proteasome inhibitory effect: (I) wherein X represents N or CH; and R represents hydrogen, C1-6 alkyl, C3-7 cycloalkyl, phenyl-C1-6 alkyl or C3-6 cycloalkyl-C1-6 alkyl. These compounds, which selectively inhibit immunoproteasomes but scarcely inhibit constitutive proteasomes, are useful as immunosuppressants, anti-inflammatory agents, anti-allergic agents, remedies for autoimmune diseases, remedies for chronic inflammatory diseases such as inflammatory bowel diseases (ulcerative colitis, Crohn’s disease), anticancer agents and remedies for neurodegenerative diseases.
PCT/JP2002/010451 2001-10-12 2002-10-08 Benzylmalonic acid derivatives and proteasome inhibitors contaiing the same Ceased WO2003033507A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2003536246A JPWO2003033507A1 (en) 2001-10-12 2002-10-08 Benzylmalonic acid derivative and proteasome inhibitor containing the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2001-314732 2001-10-12
JP2001314732 2001-10-12

Publications (1)

Publication Number Publication Date
WO2003033507A1 true WO2003033507A1 (en) 2003-04-24

Family

ID=19132996

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2002/010451 Ceased WO2003033507A1 (en) 2001-10-12 2002-10-08 Benzylmalonic acid derivatives and proteasome inhibitors contaiing the same

Country Status (2)

Country Link
JP (1) JPWO2003033507A1 (en)
WO (1) WO2003033507A1 (en)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005021558A3 (en) * 2003-08-14 2005-05-12 Cephalon Inc Proteasome inhibitors and methods of using the same
EP2088205A1 (en) 2008-02-11 2009-08-12 Institut National De La Sante Et De La Recherche Medicale (Inserm) PSMB10: A diagnosis marker and therapeutic target of chronic rejection.
EP2377868A1 (en) 2004-03-30 2011-10-19 Millennium Pharmaceuticals, Inc. Synthesis of Bortezomib
US8283367B2 (en) 2005-02-11 2012-10-09 Cephalon, Inc. Proteasome inhibitors and methods of using the same
US8513218B2 (en) 2010-03-31 2013-08-20 Millennium Pharmaceuticals, Inc. Derivatives of 1-amino-2-cyclopropylethylboronic acid
US8530694B2 (en) 2007-08-06 2013-09-10 Millennium Pharmaceuticals, Inc. Proteasome inhibitors
US8541590B2 (en) 2009-12-22 2013-09-24 Cephalon, Inc. Proteasome inhibitors and processes for their preparation, purification and use
US8664200B2 (en) 2008-09-29 2014-03-04 Millennium Pharmaceuticals, Inc. Derivatives of 1-amino-2-cyclobutylethylboronic acid
US8859504B2 (en) 2008-06-17 2014-10-14 Millennium Pharmaceuticals, Inc. Boronate ester compounds and pharmaceutical compositions thereof
US9126997B1 (en) 2010-09-07 2015-09-08 Northwestern University Synergistic effect of glucocorticoid receptor agonists in combination with proteosome inhibitors for treating leukemia and myeloma
US11241448B2 (en) 2014-05-20 2022-02-08 Millennium Pharmaceuticals, Inc. Methods for cancer therapy
JP2025016652A (en) * 2020-02-18 2025-02-04 ミレニアム ファーマシューティカルズ， インコーポレイテッド Proteasome inhibitors

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996013266A1 (en) * 1994-10-28 1996-05-09 Proscript, Inc. Boronic ester and acid compounds, synthesis and uses
US5814622A (en) * 1996-02-27 1998-09-29 Adir Et Compagnie Compounds derived from boronic acid

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996013266A1 (en) * 1994-10-28 1996-05-09 Proscript, Inc. Boronic ester and acid compounds, synthesis and uses
US5814622A (en) * 1996-02-27 1998-09-29 Adir Et Compagnie Compounds derived from boronic acid

Cited By (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8546608B2 (en) 2003-08-14 2013-10-01 Cephalon, Inc. Proteasome inhibitors and methods of using the same
JP2007502304A (en) * 2003-08-14 2007-02-08 セファロン、インク． Proteasome inhibitors and methods of using them
EA010804B1 (en) * 2003-08-14 2008-12-30 Сефэлон, Инк. BORONIC ACID DERIVATIVES (OPTIONS), METHOD FOR THEIR PRODUCTION, INTERFRONTABLE APPLICATIONS, COMPOSITION FOR INHIBITING PROTEAS ACTIVITY, METHODS FOR INHIBITING PROTEASOM ACTIVITY, TRANSCRIPPRAPS ACTIVITY INACTIVATION, TRANSCRIPPRAPS ACTIVITY INACTIVATION, ACTIV INHIBITING, INTRIBRATION ACTIVITY, INHIBITION ACTIVITY
US7576206B2 (en) 2003-08-14 2009-08-18 Cephalon, Inc. Proteasome inhibitors and methods of using the same
US7915236B2 (en) 2003-08-14 2011-03-29 Cephalon, Inc. Proteasome inhibitors and methods of using the same
US8058262B2 (en) 2003-08-14 2011-11-15 Cephalon, Inc. Proteasome inhibitors and methods of using the same
JP4917431B2 (en) * 2003-08-14 2012-04-18 セファロン、インク． Proteasome inhibitors and methods of using them
US9233115B2 (en) 2003-08-14 2016-01-12 Millennium Pharmaceuticals Inc. Proteasome inhibitors and methods of using the same
WO2005021558A3 (en) * 2003-08-14 2005-05-12 Cephalon Inc Proteasome inhibitors and methods of using the same
CN107474062A (en) * 2004-03-30 2017-12-15 千禧药品公司 The synthesis of the ester and acid compound of boron
EP2377868A1 (en) 2004-03-30 2011-10-19 Millennium Pharmaceuticals, Inc. Synthesis of Bortezomib
US8283367B2 (en) 2005-02-11 2012-10-09 Cephalon, Inc. Proteasome inhibitors and methods of using the same
US8772536B2 (en) 2007-08-06 2014-07-08 Millennium Pharmaceuticals, Inc. Proteasome inhibitors
US8530694B2 (en) 2007-08-06 2013-09-10 Millennium Pharmaceuticals, Inc. Proteasome inhibitors
US8871745B2 (en) 2007-08-06 2014-10-28 Millennium Pharmaceuticals, Inc. Proteasome inhibitors
EP2088205A1 (en) 2008-02-11 2009-08-12 Institut National De La Sante Et De La Recherche Medicale (Inserm) PSMB10: A diagnosis marker and therapeutic target of chronic rejection.
US8859504B2 (en) 2008-06-17 2014-10-14 Millennium Pharmaceuticals, Inc. Boronate ester compounds and pharmaceutical compositions thereof
US11485746B2 (en) 2008-06-17 2022-11-01 Millennium Pharmaceuticals, Inc. Boronate ester compounds and pharmaceutical compositions thereof
US10604538B2 (en) 2008-06-17 2020-03-31 Millenium Pharmaceuticals, Inc. Boronate ester compounds and pharmaceutical compositions thereof
US10526351B2 (en) 2008-06-17 2020-01-07 Millennium Pharmaceuticals, Inc. Boronate ester compounds and pharmaceutical compositions thereof
US9175018B2 (en) 2008-06-17 2015-11-03 Millennium Pharmaceuticals, Inc. Boronate ester compounds and pharmaceutical compositions thereof
US9175017B2 (en) 2008-06-17 2015-11-03 Millennium Pharmaceuticals, Inc. Boronate ester compounds and pharmaceutical compositions thereof
US10035811B2 (en) 2008-09-29 2018-07-31 Millennium Pharmaceuticals, Inc. Derivatives of 1-amino-2-cyclobutylethylboronic acid
US9771381B2 (en) 2008-09-29 2017-09-26 Millennium Pharmaceuticals, Inc. Derivatives of 1-amino-2-cyclobutylethylboronic acid
US8664200B2 (en) 2008-09-29 2014-03-04 Millennium Pharmaceuticals, Inc. Derivatives of 1-amino-2-cyclobutylethylboronic acid
US8541590B2 (en) 2009-12-22 2013-09-24 Cephalon, Inc. Proteasome inhibitors and processes for their preparation, purification and use
US8513218B2 (en) 2010-03-31 2013-08-20 Millennium Pharmaceuticals, Inc. Derivatives of 1-amino-2-cyclopropylethylboronic acid
US9023832B2 (en) 2010-03-31 2015-05-05 Millennium Pharmaceuticals, Inc. Derivatives of 1-amino-2-cyclopropylethylboronic acid
US8703743B2 (en) 2010-03-31 2014-04-22 Millennium Pharmaceuticals, Inc. Derivatives of 1-amino-2-cyclopropylethylboronic acid
US9126997B1 (en) 2010-09-07 2015-09-08 Northwestern University Synergistic effect of glucocorticoid receptor agonists in combination with proteosome inhibitors for treating leukemia and myeloma
US11241448B2 (en) 2014-05-20 2022-02-08 Millennium Pharmaceuticals, Inc. Methods for cancer therapy
JP2025016652A (en) * 2020-02-18 2025-02-04 ミレニアム ファーマシューティカルズ， インコーポレイテッド Proteasome inhibitors

Also Published As

Publication number Publication date
JPWO2003033507A1 (en) 2005-02-03

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