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WO2000049007A8 - Acetamido acetonitrile derivatives as inhibitors of cathepsin l and/or cathepsin s - Google Patents

Acetamido acetonitrile derivatives as inhibitors of cathepsin l and/or cathepsin s

Info

Publication number
WO2000049007A8
WO2000049007A8 PCT/GB2000/000532 GB0000532W WO0049007A8 WO 2000049007 A8 WO2000049007 A8 WO 2000049007A8 GB 0000532 W GB0000532 W GB 0000532W WO 0049007 A8 WO0049007 A8 WO 0049007A8
Authority
WO
WIPO (PCT)
Prior art keywords
cathepsin
compound
formula
medicament
acetamido
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/GB2000/000532
Other languages
French (fr)
Other versions
WO2000049007A1 (en
Inventor
Howard Tucker
Michael Stewart Large
John Oldfield
Craig Johnstone
Philip Neil Edwards
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.)
AstraZeneca AB
Original Assignee
AstraZeneca AB
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 claimed from GBGB9903857.2A external-priority patent/GB9903857D0/en
Priority claimed from GBGB9916098.8A external-priority patent/GB9916098D0/en
Application filed by AstraZeneca AB filed Critical AstraZeneca AB
Priority to JP2000599747A priority Critical patent/JP2002537293A/en
Priority to EP00903848A priority patent/EP1155010A1/en
Priority to AU25603/00A priority patent/AU2560300A/en
Publication of WO2000049007A1 publication Critical patent/WO2000049007A1/en
Publication of WO2000049007A8 publication Critical patent/WO2000049007A8/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
    • A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
    • C07C255/29—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton containing cyano groups and acylated amino groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/57—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/84—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (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)
  • Engineering & Computer Science (AREA)
  • Rheumatology (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Pulmonology (AREA)
  • Endocrinology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Furan Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Pyrrole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)

Abstract

A compound of formula (I) wherein Ar, R?1, R2, R3, R4 and R5¿ are defined; a composition comprising a compound of formula (I) and a carrier or diluent; a compound of formula (I) for use as a medicament, the use of a compound of formula (I) in the manufacture of a medicament for use in the inhibition of a cysteine protease in a warn blooded animal; the use of a compound of formula (I) in the manufacture of a medicament for use in the treatment of chronic obstructive pulmonary disease in a warm blooded animal; and a method of treating a Cathepsin L or Cathepsin S mediated disease state in mammals which comprises administering to a mammal in need of such treatment an effective amount of a compound of formula (I).
PCT/GB2000/000532 1999-02-20 2000-02-16 Acetamido acetonitrile derivatives as inhibitors of cathepsin l and/or cathepsin s Ceased WO2000049007A1 (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2000599747A JP2002537293A (en) 1999-02-20 2000-02-16 Acetamide acetonitrile derivatives as inhibitors of cathepsin L and / or cathepsin S
EP00903848A EP1155010A1 (en) 1999-02-20 2000-02-16 Acetamido acetonitrile derivatives as inhibitors of cathepsin l and/or cathepsin s
AU25603/00A AU2560300A (en) 1999-02-20 2000-02-16 Acetamido acetonitrile derivatives as inhibitors of cathepsin l and/or cathepsins

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GBGB9903857.2A GB9903857D0 (en) 1999-02-20 1999-02-20 Chemical compounds
GB9903857.2 1999-07-10
GBGB9916098.8A GB9916098D0 (en) 1999-07-10 1999-07-10 Chemical compounds
GB9916098.8 1999-07-10

Publications (2)

Publication Number Publication Date
WO2000049007A1 WO2000049007A1 (en) 2000-08-24
WO2000049007A8 true WO2000049007A8 (en) 2001-03-15

Family

ID=26315158

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2000/000532 Ceased WO2000049007A1 (en) 1999-02-20 2000-02-16 Acetamido acetonitrile derivatives as inhibitors of cathepsin l and/or cathepsin s

Country Status (4)

Country Link
EP (1) EP1155010A1 (en)
JP (1) JP2002537293A (en)
AU (1) AU2560300A (en)
WO (1) WO2000049007A1 (en)

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JP2002538151A (en) * 1999-03-02 2002-11-12 ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド Compounds useful as reversible inhibitors of cathepsin
EP1452522A3 (en) * 1999-03-15 2005-02-09 Axys Pharmaceuticals, Inc. Novel compounds and compositions as protease inhibitors
UA76088C2 (en) 1999-03-15 2006-07-17 Axys Pharm Inc N-cyanomethyl amides as cysteine protease inhibitors
ATE387199T1 (en) * 2000-01-06 2008-03-15 Merck Frosst Canada Ltd NEW SUBSTANCES AND COMPOUNDS AS PROTEASE INHIBITORS
GB0003111D0 (en) 2000-02-10 2000-03-29 Novartis Ag Organic compounds
US6812237B2 (en) 2000-05-15 2004-11-02 Novartis Ag N-substituted peptidyl nitriles as cysteine cathepsin inhibitors
DE60113406T2 (en) * 2000-05-15 2006-06-29 Novartis Ag N-SUBSTITUTED PEPTIDYL NITRILES AS CYSTEIN CATHEPSIN INHIBITORS
AU2002224942A1 (en) * 2000-12-20 2002-07-01 Syngenta Participations Ag N-acyl aminoacetonitriles having pesticidal properties
US7030116B2 (en) 2000-12-22 2006-04-18 Aventis Pharmaceuticals Inc. Compounds and compositions as cathepsin inhibitors
IL156577A0 (en) 2000-12-22 2004-01-04 Axys Pharm Inc Selective cathepsin s inhibitors and pharmaceutical compositions containing the same
DE60229114D1 (en) 2001-03-02 2008-11-13 Axys Pharm Inc Cathepsincystein-proteasehemmer
US6982263B2 (en) * 2001-06-08 2006-01-03 Boehringer Ingelheim Pharmaceuticals, Inc. Nitriles useful as reversible inhibitors of cysteine proteases
BR0212535A (en) 2001-09-14 2004-10-19 Aventis Pharma Inc Compounds and compositions as cathepsin inhibitors
US6977256B2 (en) 2001-11-14 2005-12-20 Aventis Pharmaceuticals Inc. Compounds and compositions as cathepsin S inhibitors
US20030232863A1 (en) * 2002-03-05 2003-12-18 Bayly Christopher I. Cathepsin cysteine protease inhibitors
AU2003230772A1 (en) * 2002-04-05 2003-10-27 Boehringer Ingelheim Pharmaceuticals, Inc. Cyanamides useful as reversible inhibitors of cysteine proteases
US6878706B1 (en) 2002-04-05 2005-04-12 Boehringer Ingelheim Pharmaceuticals Inc. Cyanamides useful as reversible inhibitors of cysteine proteases
KR100962972B1 (en) 2002-07-26 2010-06-09 주식회사유한양행 1-phenylpiperidin-3-one derivatives and preparation method thereof
EP1537074B1 (en) * 2002-09-04 2019-02-27 Merck Canada Inc. Cathepsin cysteine protease inhibitors
CN102526079B (en) 2002-09-24 2014-06-18 诺华股份有限公司 Sphingosine-1-phosphate receptor agonists in the treatment of demyelinating disorders
US7465745B2 (en) 2003-03-13 2008-12-16 Boehringer Ingelheim Pharmaceuticals, Inc. Cathepsin S inhibitors
US7326719B2 (en) 2003-03-13 2008-02-05 Boehringer Ingelheim Pharmaceuticals, Inc. Cathepsin S inhibitors
WO2004089395A2 (en) * 2003-04-01 2004-10-21 Aventis Pharmaceuticals Inc. Use of an inhibitor of cathepsin-s or -b to treat or prevent chronic obstructive pulmonary disease
US7297714B2 (en) * 2003-10-21 2007-11-20 Irm Llc Inhibitors of cathepsin S
US7423176B2 (en) * 2004-04-13 2008-09-09 Cephalon, Inc. Bicyclic aromatic sulfinyl derivatives
KR20070061877A (en) * 2004-09-17 2007-06-14 바이엘 쉐링 파마 악티엔게젤샤프트 Methods and Intermediates for the Preparation of Cysteine Protease Inhibitors
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EP1910278A1 (en) * 2005-07-25 2008-04-16 Novartis AG Amidonitrile compounds
EP2719700A1 (en) 2008-01-09 2014-04-16 Amura Therapeutics Limited Tetrahydrofuro(3,2-b)pyrrol-3-one derivatives as inhibitors of cysteine proteinases
EP3545953A1 (en) 2008-06-20 2019-10-02 Novartis AG Paediatric compositions for treating1 multiple sclerosis
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EP2920158A1 (en) * 2012-11-14 2015-09-23 F. Hoffmann-La Roche AG Novel acetamide derivatives as trp channel antagonists
PL3043791T3 (en) * 2013-09-13 2019-08-30 Pitney Pharmaceuticals Pty Limited Anticancer agent comprising aminoacetonitrile compound as active ingredient
CN115466225B (en) * 2022-08-16 2025-03-07 中国科学院上海药物研究所 An amide compound and its preparation method, pharmaceutical composition and use
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Also Published As

Publication number Publication date
EP1155010A1 (en) 2001-11-21
WO2000049007A1 (en) 2000-08-24
JP2002537293A (en) 2002-11-05
AU2560300A (en) 2000-09-04

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