WO1996016079A3 - Alpha-ketoamide derivatives as cathepsin l inhibitor - Google Patents

Alpha-ketoamide derivatives as cathepsin l inhibitor Download PDF

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Publication number
WO1996016079A3
WO1996016079A3 PCT/JP1995/002389 JP9502389W WO9616079A3 WO 1996016079 A3 WO1996016079 A3 WO 1996016079A3 JP 9502389 W JP9502389 W JP 9502389W WO 9616079 A3 WO9616079 A3 WO 9616079A3
Authority
WO
WIPO (PCT)
Prior art keywords
substituted
cathepsin
inhibitor
group
alpha
Prior art date
Application number
PCT/JP1995/002389
Other languages
French (fr)
Other versions
WO1996016079A2 (en
Inventor
Takashi Sohda
Yukio Fujisawa
Tsuneo Yasuma
Junji Mizoguchi
Original Assignee
Takeda Chemical Industries Ltd
Takashi Sohda
Yukio Fujisawa
Tsuneo Yasuma
Junji Mizoguchi
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, Takashi Sohda, Yukio Fujisawa, Tsuneo Yasuma, Junji Mizoguchi filed Critical Takeda Chemical Industries Ltd
Priority to CA002200964A priority Critical patent/CA2200964A1/en
Priority to AU39358/95A priority patent/AU3935895A/en
Priority to EP95937173A priority patent/EP0793673A1/en
Publication of WO1996016079A2 publication Critical patent/WO1996016079A2/en
Publication of WO1996016079A3 publication Critical patent/WO1996016079A3/en

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Classifications

    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms 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
    • A61K38/00—Medicinal preparations containing peptides

Landscapes

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

Abstract

The present invention relates to a cathepsin L inhibitor comprising a compound of general formula (Ia), wherein Q represents a direct bond or 1 or 2 amino acid residues that may be substituted; R1 represents a hydrogen atom or a hydrocarbon group or heterocyclic group that may be substituted; R4 represents an acyl group or a carboxyl group that may be esterified and R?5 and R6¿ independently represent a hydrogen atom or a hydrocarbon group or heterocyclic group that may be substituted or R?5 and R6¿ may bind together to form a ring; or a salt thereof, which has strong bone resorption-suppressing action and is useful for preventing or treating osteoporosis.
PCT/JP1995/002389 1994-11-24 1995-11-24 Alpha-ketoamide derivatives as cathepsin l inhibitor WO1996016079A2 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
CA002200964A CA2200964A1 (en) 1994-11-24 1995-11-24 Alpha-ketoamide derivatives as cathepsin l inhibitor
AU39358/95A AU3935895A (en) 1994-11-24 1995-11-24 Alpha-ketoamide derivatives as cathepsin l inhibitor
EP95937173A EP0793673A1 (en) 1994-11-24 1995-11-24 Alpha-ketoamide derivatives as cathepsin l inhibitor

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP29013294 1994-11-24
JP6/290132 1994-11-24

Publications (2)

Publication Number Publication Date
WO1996016079A2 WO1996016079A2 (en) 1996-05-30
WO1996016079A3 true WO1996016079A3 (en) 1996-09-12

Family

ID=17752214

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1995/002389 WO1996016079A2 (en) 1994-11-24 1995-11-24 Alpha-ketoamide derivatives as cathepsin l inhibitor

Country Status (4)

Country Link
EP (1) EP0793673A1 (en)
AU (1) AU3935895A (en)
CA (1) CA2200964A1 (en)
WO (1) WO1996016079A2 (en)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2959397A (en) * 1996-05-31 1998-01-05 Novartis Ag Process for the preparation of hydrazine derivatives useful as intermediates for the preparation of peptide analogues
US6150378A (en) * 1997-10-07 2000-11-21 Cephalon, Inc. Peptidyl-containing α-ketoamide cysteine and serine protease inhibitors
JP2003526634A (en) * 1999-12-03 2003-09-09 ブリストル−マイヤーズ スクイブ ファーマ カンパニー Α-Ketoamide inhibitors of hepatitis C virus NS3 protease
US6703513B1 (en) 2000-06-02 2004-03-09 K-Quay Enterprises Llc Production and use of derivatized homoserine lactones
EP2289888A3 (en) * 2000-06-30 2011-07-13 Seikagaku Corporation Epoxycarboxylic acid amides, azides and amino alcohols and processes for preparation of alpha-keto amides by using them
US20050107616A1 (en) * 2001-08-03 2005-05-19 David Gene Barrett Alpha-ketoamide derivatives as cathepsin k inhibitors
JP2005515254A (en) * 2002-01-17 2005-05-26 スミスクライン ビーチャム コーポレーション Cycloalkylketoamide derivatives useful as cathepsin K inhibitors
WO2003086385A1 (en) * 2002-04-10 2003-10-23 Smithkline Beecham Corporation Derivatives of 1-(oxoaminoacetyl) pentylcarbamate as cathepsin k inhibitors for the treatment of bone loss
JP4549851B2 (en) 2002-07-22 2010-09-22 千寿製薬株式会社 Novel α-ketoamide derivatives and uses thereof
WO2010070615A1 (en) * 2008-12-19 2010-06-24 Medivir Uk Ltd Cysteine protease inhibitors
GB201001070D0 (en) 2010-01-22 2010-03-10 St George's Hospital Medical School Theraputic compounds and their use
EP2633855A1 (en) 2012-03-01 2013-09-04 Veterinärmedizinische Universität Wien Protease inhibitors for treating Trichomonas gallinae infections
US9809571B2 (en) 2013-01-07 2017-11-07 University Of Southern California Deoxyuridine triphosphatase inhibitors
WO2014182928A2 (en) 2013-05-08 2014-11-13 Board Of Regents, The University Of Texas System Stat6 inhibitors
WO2017006283A1 (en) 2015-07-08 2017-01-12 Cv6 Therapeutics (Ni) Limited Deoxyuridine triphosphatase inhibitors containing cyclopropano linkage
EA037990B1 (en) 2015-07-08 2021-06-21 Св6 Терапьютикс (Най) Лимитед Hydantoin containing deoxyuridine triphosphatase inhibitors
US10570100B2 (en) 2015-07-08 2020-02-25 University Of Southern California Deoxyuridine triphosphatase inhibitors containing amino sulfonyl linkage
WO2017006270A1 (en) 2015-07-08 2017-01-12 University Of Southern California Deoxyuridine triphosphatase inhibitors
PL3464336T3 (en) 2016-06-01 2022-05-16 Athira Pharma, Inc. Compounds
US10526315B2 (en) 2016-06-21 2020-01-07 Orion Ophthalmology LLC Carbocyclic prolinamide derivatives
EA201990069A1 (en) 2016-06-21 2019-06-28 ОРИОН ОФТАЛМОЛОДЖИ ЭлЭлСи DERIVATIVES OF HETEROCYCLIC PROLINAMIDE
WO2018098209A1 (en) 2016-11-23 2018-05-31 Cv6 Therapeutics (Ni) Limited Amino sulfonyl compounds
WO2018098206A1 (en) 2016-11-23 2018-05-31 Cv6 Therapeutics (Ni) Limited Hydantoin containing deoxyuridine triphosphatase inhibitors
WO2018098204A1 (en) 2016-11-23 2018-05-31 Cv6 Therapeutics (Ni) Limited 6-membered uracil isosteres
WO2018098208A1 (en) * 2016-11-23 2018-05-31 Cv6 Therapeutics (Ni) Limited Nitrogen ring linked deoxyuridine triphosphatase inhibitors
US11014924B2 (en) 2016-11-23 2021-05-25 Cv6 Therapeutics (Ni) Limited Hydantoin containing deoxyuridine triphosphatase inhibitors
US11247984B2 (en) 2017-01-05 2022-02-15 Cv6 Therapeutics (Ni) Limited Uracil containing compounds

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0468339A2 (en) * 1990-07-27 1992-01-29 Nippon Kayaku Kabushiki Kaisha Alpha-keto-amide derivatives having protease inhibiting activity
WO1992012140A1 (en) * 1990-12-28 1992-07-23 Georgia Tech Research Corporation Peptides ketoamides, ketoacids, and ketoesters
WO1992011850A2 (en) * 1990-12-28 1992-07-23 Cortex Pharmaceuticals, Inc. Use of calpain inhibitors in the inhibition and treatment of neurodegeneration
WO1994000095A2 (en) * 1992-06-24 1994-01-06 Cortex Pharmaceuticals, Inc. Use of calpain inhibitors in the inhibition and treatment of medical conditions associated with increased calpain activity
WO1994008941A1 (en) * 1992-10-16 1994-04-28 Corvas International, Inc. Arginine keto-amide enzyme inhibitors
EP0603769A1 (en) * 1992-12-25 1994-06-29 Mitsubishi Chemical Corporation Alpha-Aminoketone derivatives

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0468339A2 (en) * 1990-07-27 1992-01-29 Nippon Kayaku Kabushiki Kaisha Alpha-keto-amide derivatives having protease inhibiting activity
WO1992012140A1 (en) * 1990-12-28 1992-07-23 Georgia Tech Research Corporation Peptides ketoamides, ketoacids, and ketoesters
WO1992011850A2 (en) * 1990-12-28 1992-07-23 Cortex Pharmaceuticals, Inc. Use of calpain inhibitors in the inhibition and treatment of neurodegeneration
WO1994000095A2 (en) * 1992-06-24 1994-01-06 Cortex Pharmaceuticals, Inc. Use of calpain inhibitors in the inhibition and treatment of medical conditions associated with increased calpain activity
WO1994008941A1 (en) * 1992-10-16 1994-04-28 Corvas International, Inc. Arginine keto-amide enzyme inhibitors
EP0603769A1 (en) * 1992-12-25 1994-06-29 Mitsubishi Chemical Corporation Alpha-Aminoketone derivatives

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ESSER, R.E. ET AL.: "Cysteine proteinase inhibitors decrease articular cartilage and bone destruction in chronic inflammatory arthritis", ARTHRITIS & RHEUMATISM, vol. 37, no. 2, 1 February 1994 (1994-02-01), pages 236 - 247, XP000566128 *
LI, Z. ET AL.: "Peptide alpha-keto ester, alpha-keto amide, and alpha-keto acid inhibitors of calpains and other csyteine proteases", J. MED. CHEM., vol. 36, 1993, pages 3472 - 3480, XP000565670 *

Also Published As

Publication number Publication date
CA2200964A1 (en) 1996-05-30
EP0793673A1 (en) 1997-09-10
WO1996016079A2 (en) 1996-05-30
AU3935895A (en) 1996-06-17

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