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PE71599A1 - PROTEASE INHIBITORS - Google Patents

PROTEASE INHIBITORS

Info

Publication number
PE71599A1
PE71599A1 PE1998000336A PE00033698A PE71599A1 PE 71599 A1 PE71599 A1 PE 71599A1 PE 1998000336 A PE1998000336 A PE 1998000336A PE 00033698 A PE00033698 A PE 00033698A PE 71599 A1 PE71599 A1 PE 71599A1
Authority
PE
Peru
Prior art keywords
alkyl
alkyll
ccero
alkylll
amino
Prior art date
Application number
PE1998000336A
Other languages
Spanish (es)
Inventor
Robert W Marquis
Daniel F Veber
Andrew D Gribble
Jason Witherington
Ashley Edward Fenwick
Original Assignee
Smithkline Beecham Plc
Smithkline Beecham Corp
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 Smithkline Beecham Plc, Smithkline Beecham Corp filed Critical Smithkline Beecham Plc
Publication of PE71599A1 publication Critical patent/PE71599A1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/99—Enzyme inactivation by chemical treatment
    • 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
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D307/32—Oxygen atoms
    • 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
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/06—Anabolic agents
    • 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
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/18—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no 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
    • C07D307/22—Nitrogen atoms not forming part of a nitro radical
    • 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
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
    • C07D307/83—Oxygen 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
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D309/30—Oxygen atoms, e.g. delta-lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Rheumatology (AREA)
  • Genetics & Genomics (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Endocrinology (AREA)
  • Immunology (AREA)
  • Microbiology (AREA)
  • Molecular Biology (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • General Engineering & Computer Science (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Peptides Or Proteins (AREA)

Abstract

SE REFIERE A UN COMPUESTO DE FORMULA (I) O SU SAL, DONDE: R1 ES R", R"C(O), R"R`NC(O), ENTRE OTROS; R2 Y R4 SON H, ALQUILO C1-C6, ALQUENILO C2-C6, Ar-ALQUILO Ccero-C6, Het-ALQUILO Ccero-C6; R3 ES H, ALQUILO C1-C6, ALQUENILO C2-C6, ALQUINILO C2-C6, ENTRE OTROS; R5 ES H, ALQUILO C1-C6, ALQUENILO C2-C6, ENTRE OTROS; R6 ES H, ALQUILO C1-C6, ALQUENILO C2-C6, ENTRE OTROS; R' ES H, ALQUILO C1-C6, ALQUENILO C2-C6, ENTRE OTROS; R" ES ALQUILO C1-C6, Ar-ALQUILO C CERO-C6, ENTRE OTROS; X ES O o S; n ES 1-3. SON COMPUESTOS PREFERIDOS 4-(R,S)-AMINO-N-[(3,4-METILENDIOXIBENZOIL)-S-LEUCINA]-TETRAHIDROFURAN-3-ONA, TRANS-4-(R,S)-AMINO-N-[BENCILOXICARBONIL)-S-LEUCINA]-3-HIDROXITETRAHIDROFURANO, ENTRE OTROS. TAMBIEN SE REFIERE A UN PROCEDIMIENTO PARA LA PREPARACION. EL COMPUESTO (I) INHIBE LA ENZIMA CISTEINA PROTEASA EN PARTICULAR LA CATEPSINA K, POR LO QUE PUEDE SER UTIL PARA INHIBIR PERDIDA OSEA, OSTEOPOROSIS, ENFERMEDAD GINGIVAL O PERIODONTAL; TRATAR UNA ENFERMEDAD CARACTERIZADA POR UNA DEGRADACION EXCESIVA DE CARTILAGO O MATRIZ COMO LA OSTEOARTRITIS O ARTRITIS REUMATOIDEREFERS TO A COMPOUND OF FORMULA (I) OR ITS SALT, WHERE: R1 IS R ", R" C (O), R "R`NC (O), AMONG OTHERS; R2 AND R4 ARE H, RENT C1-C6 , C2-C6 ALKYYL, Ar-Ccero-C6 ALKYL, Het-Ccero-C6 ALKYL; R3 ES H, C1-C6 ALKYL, C2-C6 ALKYLL, AMONG OTHERS; R5 IS H, C1-C6 ALKYL , C2-C6 ALKYLLL, AMONG OTHERS; R6 IS H, C1-C6 ALKYLL, C2-C6 ALKYLL, AMONG OTHERS; R 'ES H, C1-C6 ALKYLL, C2-C6 ALKYLLL, R1 IS C1- C6, Ar-ALKYL C ZERO-C6, AMONG OTHERS; X IS O or S; n IS 1-3. THEY ARE PREFERRED COMPOUNDS 4- (R, S) -AMINO-N - [(3,4-METHYLENDIOXIBENZOIL) -S-LEUCINE] -TETRAHYDROFURAN-3-ONA, TRANS-4- (R, S) -AMINO-N- [ BENCILOXICARBONIL) -S-LEUCINA] -3-HIDROXITETRAHIDROFURANO, AMONG OTHERS. IT ALSO REFERS TO A PROCEDURE FOR PREPARATION. COMPOUND (I) INHIBITS THE CYSTEINE ENZYME PROTEASE IN PARTICULAR CATEPSIN K, SO IT MAY BE USEFUL TO INHIBIT LOSS OF OSEA, OSTEOPOROSIS, GINGIVAL OR PERIODONTAL DISEASE; TREAT A DISEASE CHARACTERIZED BY EXCESSIVE DEGRADATION OF CARTILAGO OR MATRIX LIKE OSTEOARTHRITIS OR RHEUMATOID ARTHRITIS

PE1998000336A 1997-05-06 1998-05-05 PROTEASE INHIBITORS PE71599A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US4575897P 1997-05-06 1997-05-06

Publications (1)

Publication Number Publication Date
PE71599A1 true PE71599A1 (en) 1999-09-15

Family

ID=21939723

Family Applications (1)

Application Number Title Priority Date Filing Date
PE1998000336A PE71599A1 (en) 1997-05-06 1998-05-05 PROTEASE INHIBITORS

Country Status (19)

Country Link
EP (1) EP1003846A4 (en)
JP (1) JP2001525804A (en)
KR (1) KR20010012256A (en)
CN (1) CN1255161A (en)
AR (1) AR013079A1 (en)
AU (1) AU7562598A (en)
BR (1) BR9809306A (en)
CA (1) CA2288868A1 (en)
CO (1) CO4950618A1 (en)
HU (1) HUP0002247A3 (en)
IL (1) IL132088A0 (en)
NO (1) NO995434D0 (en)
NZ (1) NZ337889A (en)
PE (1) PE71599A1 (en)
PL (1) PL336856A1 (en)
TR (1) TR199902766T2 (en)
UY (1) UY25143A1 (en)
WO (1) WO1998050533A1 (en)
ZA (1) ZA983762B (en)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CO5150165A1 (en) * 1998-11-13 2002-04-29 Smithkline Beecham Plc PROTEASE INHIBITORS: KATEPSIN K TYPE
DZ3083A1 (en) * 1999-02-19 2004-06-02 Smithkline Beecham Corp New protease inhibitor compounds, process for their preparation and pharmaceutical compositions containing them
GB9911417D0 (en) * 1999-05-18 1999-07-14 Peptide Therapeutics Ltd Furanone derivatives as inhibitors of cathepsin s
EP1232155A4 (en) * 1999-11-10 2002-11-20 Smithkline Beecham Corp Protease inhibitors
US20040024000A1 (en) * 2000-10-19 2004-02-05 Rajeshwar Singh Dihydropyrimidine derivatives as cysteine protease inhibitors
IL155961A0 (en) * 2000-11-17 2003-12-23 Medivir Uk Ltd Cysteine protease inhibitors
DE60118793T2 (en) * 2000-11-17 2007-04-26 Medivir Ab CYSTEIN PROTEASE INHIBITORS
US7132449B2 (en) 2001-01-17 2006-11-07 Amura Therapeutics Limited Inhibitors of cruzipain and other cysteine proteases
CN1269822C (en) * 2001-01-17 2006-08-16 阿姆拉医疗有限公司 Inhibitors of cruzipain and other cysteine proteases
NZ526912A (en) * 2001-01-17 2005-02-25 Amura Therapeutics Ltd Inhibitors of cruzipain and other cysteine proteases
IL156775A0 (en) * 2001-01-17 2004-02-08 Amura Therapeutics Ltd Cyclic 2-carbonylaminoketones as inhibitors of cruzipain and other cysteine proteases
JP2005508979A (en) * 2001-10-29 2005-04-07 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 cysteine proteases
DE60326473D1 (en) * 2002-07-16 2009-04-16 Amura Therapeutics Ltd Pyrrolderivate als hemmstoffe von cystein proteasen
KR100962972B1 (en) 2002-07-26 2010-06-09 주식회사유한양행 1-phenylpiperidin-3-one derivatives and processes for the preparation thereof
AU2016206281B2 (en) * 2003-08-06 2017-11-30 Senomyx, Inc. Novel flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof
CL2004002015A1 (en) 2003-08-06 2005-05-13 Senomyx Inc AMIDA DERIVATIVES, PRODUCTS THAT CONTAIN THEM, USEFUL TO MODIFY THE FLAVOR OF FOODS AND MEDICINES.
CA2552739A1 (en) * 2004-01-08 2005-07-21 Medivir Ab Cysteine protease inhibitors
MX2008002363A (en) * 2005-08-17 2008-03-18 Schering Corp Novel high affinity quinoline-based kinase ligands.
GB0614042D0 (en) 2006-07-14 2006-08-23 Amura Therapeutics Ltd Compounds
CN101784516B (en) * 2007-06-13 2014-07-02 百时美施贵宝公司 Dipeptide analogs as coagulation factor inhibitors
US7893067B2 (en) 2007-06-27 2011-02-22 Medivir Ab Cysteine protease inhibitors
JP5587790B2 (en) 2008-01-09 2014-09-10 アミュラ セラピューティクス リミティド Compound
GB0817424D0 (en) 2008-09-24 2008-10-29 Medivir Ab Protease inhibitors

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3190431B2 (en) * 1991-07-01 2001-07-23 三菱化学株式会社 Ketone derivatives
JPH05140063A (en) * 1991-11-19 1993-06-08 Suntory Ltd Dipeptide derivative and medicine for preventing and improving osteopathy, containing the same compound as active component
CA2111930A1 (en) * 1992-12-25 1994-06-26 Ryoichi Ando Aminoketone derivatives
JP2848232B2 (en) * 1993-02-19 1999-01-20 武田薬品工業株式会社 Aldehyde derivatives
JP3599287B2 (en) * 1993-04-28 2004-12-08 三菱化学株式会社 Sulfonamide derivative
US5403952A (en) * 1993-10-08 1995-04-04 Merck & Co., Inc. Substituted cyclic derivatives as novel antidegenerative agents
WO1997016177A1 (en) * 1995-10-30 1997-05-09 Smithkline Beecham Corporation Method of inhibiting cathepsin k
TW448172B (en) * 1996-03-08 2001-08-01 Pharmacia & Upjohn Co Llc Novel hydroxamic acid derivatives useful for the treatment of diseases related to connective tissue degradation
WO1998004539A1 (en) * 1996-07-29 1998-02-05 Mitsubishi Chemical Corporation Oxygenic heterocyclic derivatives

Also Published As

Publication number Publication date
TR199902766T2 (en) 2000-02-21
EP1003846A4 (en) 2002-11-13
IL132088A0 (en) 2001-03-19
PL336856A1 (en) 2000-07-17
KR20010012256A (en) 2001-02-15
NZ337889A (en) 2001-09-28
AR013079A1 (en) 2000-12-13
CN1255161A (en) 2000-05-31
JP2001525804A (en) 2001-12-11
NO995434L (en) 1999-11-05
CO4950618A1 (en) 2000-09-01
EP1003846A1 (en) 2000-05-31
NO995434D0 (en) 1999-11-05
BR9809306A (en) 2000-07-04
UY25143A1 (en) 1998-11-27
WO1998050533A1 (en) 1998-11-12
AU7562598A (en) 1998-11-27
ZA983762B (en) 1998-11-06
HUP0002247A3 (en) 2003-01-28
HUP0002247A2 (en) 2001-05-28
CA2288868A1 (en) 1998-11-12

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