WO1996030395A3 - Cysteine protease inhibitor - Google Patents

Cysteine protease inhibitor Download PDF

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Publication number
WO1996030395A3
WO1996030395A3 PCT/JP1996/000840 JP9600840W WO9630395A3 WO 1996030395 A3 WO1996030395 A3 WO 1996030395A3 JP 9600840 W JP9600840 W JP 9600840W WO 9630395 A3 WO9630395 A3 WO 9630395A3
Authority
WO
WIPO (PCT)
Prior art keywords
group
formula
hydrogen atom
amino acid
cysteine protease
Prior art date
Application number
PCT/JP1996/000840
Other languages
French (fr)
Other versions
WO1996030395A2 (en
Inventor
Tsunehiko Fukuda
Yukio Fujisawa
Hiroyuki Watanabe
Original Assignee
Takeda Chemical Industries Ltd
Tsunehiko Fukuda
Yukio Fujisawa
Hiroyuki Watanabe
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 Takeda Chemical Industries Ltd, Tsunehiko Fukuda, Yukio Fujisawa, Hiroyuki Watanabe filed Critical Takeda Chemical Industries Ltd
Priority to US08/648,145 priority Critical patent/US6162828A/en
Priority to AU51221/96A priority patent/AU5122196A/en
Priority to EP96907705A priority patent/EP0820464A2/en
Publication of WO1996030395A2 publication Critical patent/WO1996030395A2/en
Publication of WO1996030395A3 publication Critical patent/WO1996030395A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/20—Esters of monothiocarboxylic acids
    • C07C327/32—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid, pantothenic acid
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid, pantothenic acid
    • A61K31/198—Alpha-aminoacids, e.g. alanine, edetic acids [EDTA]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0202—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/0205—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)3-C(=0)-, e.g. statine or derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Epidemiology (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Genetics & Genomics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

A pharmaceutical composition for inhibiting cysteine protease which comprises a compound of formula (I), wherein R1 is a hydrogen atom or an acyl group; R?2, R3 and R4¿, same or different, are a bond, an amino acid residue or a group of the formula -Y-R5-, in which R5 is a group resulting from imino group removal from an amino acid residue; Y is -O-, -S- or -NR6-, in which R6 is a hydrogen atom or a lower alkyl group; A is (a) or (b); Z is a hydrogen atom, an acyl group or an optionally substituted hydrocarbon group; n is 1 or 2; provided that when n is 1, then A is (a) and Y is -S- or -NR6-, and, at least one of R?2, R3 and R4¿ is the formula -Y-R5-, provided that when further all Y are -NR6-, at least one of the amino acid residues is not bound to an hydrogen atom at the α-carbon thereof but substituted via carbon; provided that when n is 2 and Z is an aldehyde group, then R1 is an acyl group having 6 or more carbon atoms; provided that when n is 2 and A is (a), then at least one of R?2, R3 and R4¿ is the formula -Y-R5-; or an ester or a salt thereof, and a pharmaceutically acceptable carrier.
PCT/JP1996/000840 1995-03-31 1996-03-29 Cysteine protease inhibitor WO1996030395A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US08/648,145 US6162828A (en) 1995-03-31 1996-03-29 Cysteine protease inhibitor
AU51221/96A AU5122196A (en) 1995-03-31 1996-03-29 Cysteine protease inhibitor
EP96907705A EP0820464A2 (en) 1995-03-31 1996-03-29 Cysteine protease inhibitor

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP7/75594 1995-03-31
JP7/75593 1995-03-31
JP7559395 1995-03-31
JP7559495 1995-03-31
JP7/265723 1995-10-13
JP26572395 1995-10-13

Publications (2)

Publication Number Publication Date
WO1996030395A2 WO1996030395A2 (en) 1996-10-03
WO1996030395A3 true WO1996030395A3 (en) 1996-12-27

Family

ID=27301885

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1996/000840 WO1996030395A2 (en) 1995-03-31 1996-03-29 Cysteine protease inhibitor

Country Status (5)

Country Link
US (1) US6162828A (en)
EP (1) EP0820464A2 (en)
AU (1) AU5122196A (en)
CA (1) CA2215211A1 (en)
WO (1) WO1996030395A2 (en)

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US5744451A (en) * 1995-09-12 1998-04-28 Warner-Lambert Company N-substituted glutamic acid derivatives with interleukin-1 β converting enzyme inhibitory activity
HUP9700816A3 (en) * 1997-04-28 1999-06-28 Gyogyszerkutato Intezet 3(r)-3-amino-4-carboxy-butiraldehyde derivatives inhibiting release of interleukin-1-beta
EP1062210B1 (en) 1998-03-09 2005-06-01 Vertex Pharmaceuticals Incorporated 1,2-diazepane derivatives as interleukin-1beta converting enzyme inhibitors
PT1064298E (en) 1998-03-19 2009-01-02 Vertex Pharma Inhibitors of caspases
US6242422B1 (en) * 1998-10-22 2001-06-05 Idun Pharmacueticals, Inc. (Substituted)Acyl dipeptidyl inhibitors of the ice/ced-3 family of cysteine proteases
US7157430B2 (en) 1998-10-22 2007-01-02 Idun Pharmaceuticals, Inc. (Substituted)acyl dipeptidyl inhibitors of the ICE/CED-3 family of cysteine proteases
JP4273662B2 (en) * 1999-04-26 2009-06-03 味の素株式会社 Melanocyte stimulating hormone inhibitor
PA8507801A1 (en) 1999-12-03 2002-08-26 Agouron Pharma ANTIPICORNAVIRAL COMPOUNDS AND COMPOSITIONS, THEIR PHARMACEUTICAL USES AND THE MATERIALS FOR SYNTHESIS
SK13922002A3 (en) 2000-03-29 2003-09-11 Vertex Pharmaceuticals Incorporated Carbamate caspase inhibitors and uses thereof
PA8515201A1 (en) * 2000-04-14 2002-10-24 Agouron Pharma ANTIPICORNAVIRAL COMPOUNDS AND COMPOSITIONS; YOUR PHARMACEUTICAL USES AND MATERIALS FOR SYNTHESIS
US6525024B1 (en) 2000-04-17 2003-02-25 Idun Pharmaceuticals, Inc. Inhibitors of the ICE/ced-3 family of cysteine proteases
PE20011350A1 (en) 2000-05-19 2002-01-15 Vertex Pharma PROPHARMAC OF AN INHIBITOR OF INTERLEUKIN-1ß CONVERTER ENZYME (ICE)
CA2412618A1 (en) 2000-06-14 2001-12-20 Agouron Pharmaceuticals, Inc. Antipicornaviral compounds and compositions, their pharmaceutical uses, and materials for their synthesis
EP1315971A2 (en) * 2000-07-31 2003-06-04 The Regents of The University of California Model for alzheimer's disease and other neurodegenerative diseases
US20020052323A1 (en) * 2000-08-30 2002-05-02 Jinhai Wang Quinoline-(C=O)-(multiple amino acids)-leaving group compounds for pharmaceutical compositions and reagents
US6777443B2 (en) * 2001-05-15 2004-08-17 Novartis Ag Dipeptide derivatives
US7153822B2 (en) * 2002-01-29 2006-12-26 Wyeth Compositions and methods for modulating connexin hemichannels
US20040052928A1 (en) * 2002-09-06 2004-03-18 Ehud Gazit Peptides and methods using same for diagnosing and treating amyloid-associated diseases
US7781396B2 (en) * 2002-01-31 2010-08-24 Tel Aviv University Future Technology Development L.P. Peptides directed for diagnosis and treatment of amyloid-associated disease
US7491699B2 (en) * 2002-12-09 2009-02-17 Ramot At Tel Aviv University Ltd. Peptide nanostructures and methods of generating and using the same
WO2004060791A1 (en) 2003-01-07 2004-07-22 Ramot At Tel Aviv University Ltd. Peptide nanostructures encapsulating a foreign material and method of manufacturing same
US7176208B2 (en) 2003-04-18 2007-02-13 Enanta Pharmaceuticals, Inc. Quinoxalinyl macrocyclic hepatitis C serine protease inhibitors
JP5137400B2 (en) 2003-06-30 2013-02-06 テル アヴィヴ ユニヴァーシティ フューチャー テクノロジー ディヴェロップメント エル．ピー． Peptides for diagnosing and treating amyloid-related diseases, antibodies thereto, and methods of use thereof
CA2540407A1 (en) * 2003-09-25 2005-03-31 Tel Aviv University Future Technology Development L.P. Compositions and methods using same for treating amyloid-associated diseases
AU2004275821A1 (en) * 2003-09-25 2005-04-07 Dmi Biosciences Inc. Methods and products which utilize N-acyl-L-aspartic acid
US7625707B2 (en) * 2003-10-02 2009-12-01 Ramot At Tel Aviv University Ltd. Antibacterial agents and methods of identifying and utilizing same
AU2005249503B2 (en) 2003-11-10 2011-08-25 Vertex Pharmaceuticals Incorporated ICE inhibitors for the treatment of autoinflammatory diseases
WO2006013552A2 (en) 2004-08-02 2006-02-09 Ramot At Tel Aviv University Ltd. Articles of peptide nanostructures and method of forming the same
US7732479B2 (en) * 2004-08-19 2010-06-08 Tel Aviv University Future Technology Development L.P. Compositions for treating amyloid associated diseases
US7786086B2 (en) 2004-09-08 2010-08-31 Ramot At Tel-Aviv University Ltd. Peptide nanostructures containing end-capping modified peptides and methods of generating and using the same
US10004828B2 (en) 2005-10-11 2018-06-26 Romat at Tel-Aviv University Ltd. Self-assembled Fmoc-ff hydrogels
US7879212B2 (en) * 2005-11-03 2011-02-01 Ramot At Tel-Aviv University Ltd. Peptide nanostructure-coated electrodes
JP3975226B2 (en) * 2006-01-11 2007-09-12 生化学工業株式会社 Cycloalkylcarbonylamino acid derivative and process for producing the same
JP4047365B2 (en) * 2006-01-11 2008-02-13 生化学工業株式会社 Cycloalkanecarboxamide derivative and method for producing the same
CA2636765C (en) * 2006-01-11 2014-03-18 Seikagaku Corporation Cycloalkylcarbonylamino acid ester derivative and process for producing the same
US20080227688A1 (en) * 2007-03-13 2008-09-18 Johnston Randal N Inhibition of viral replication
US8791235B2 (en) * 2008-05-21 2014-07-29 Novagenesis Foundation Selective caspase inhibitors and uses thereof
WO2010133000A1 (en) 2009-05-21 2010-11-25 New World Laboratories Inc. Selective caspase inhibitors and uses thereof
GB201001070D0 (en) 2010-01-22 2010-03-10 St George's Hospital Medical School Theraputic compounds and their use
GB201011411D0 (en) 2010-07-06 2010-08-18 St Georges Hosp Medical School Therapeutic compounds and their use
WO2012061785A2 (en) 2010-11-05 2012-05-10 Brandeis University Ice inhibiting compounds and uses thereof
US9944674B2 (en) 2011-04-15 2018-04-17 Genesis Technologies Limited Selective cysteine protease inhibitors and uses thereof
US9956260B1 (en) 2011-07-22 2018-05-01 The J. David Gladstone Institutes Treatment of HIV-1 infection and AIDS
JP2022538360A (en) * 2019-07-01 2022-09-01 ビーエーエスエフ ソシエタス・ヨーロピア Peptide acetals to stabilize enzymes

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Also Published As

Publication number Publication date
US6162828A (en) 2000-12-19
AU5122196A (en) 1996-10-16
WO1996030395A2 (en) 1996-10-03
CA2215211A1 (en) 1996-10-03
EP0820464A2 (en) 1998-01-28

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