PE20011003A1 - METALOPROTEASE INHIBITORS - Google Patents

METALOPROTEASE INHIBITORS

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Publication number
PE20011003A1
PE20011003A1 PE2000001097A PE0010972000A PE20011003A1 PE 20011003 A1 PE20011003 A1 PE 20011003A1 PE 2000001097 A PE2000001097 A PE 2000001097A PE 0010972000 A PE0010972000 A PE 0010972000A PE 20011003 A1 PE20011003 A1 PE 20011003A1
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PE
Peru
Prior art keywords
alkyl
alkenyl
alkinyl
sulfonylamino
biphenyl
Prior art date
Application number
PE2000001097A
Other languages
Spanish (es)
Inventor
Neil Gregory Almstead
Biswanath De
Kelly Michelle Solinsky
Norman Eugene Ohler
Stanislaw Pikul
Michael George Natchus
Original Assignee
Procter & Gamble
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Filing date
Publication date
Application filed by Procter & Gamble filed Critical Procter & Gamble
Publication of PE20011003A1 publication Critical patent/PE20011003A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon 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
    • 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
    • A61P17/00—Drugs for dermatological 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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • C07C323/59—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton with acylated amino groups bound to the carbon skeleton
    • 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
    • C07D233/72—Two oxygen atoms, e.g. hydantoin
    • C07D233/80—Two oxygen atoms, e.g. hydantoin with hetero atoms or acyl radicals directly attached to ring nitrogen atoms
    • 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
    • C07D233/86—Oxygen and sulfur atoms, e.g. thiohydantoin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D405/06—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 carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Cardiology (AREA)
  • Rheumatology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Immunology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pain & Pain Management (AREA)
  • Urology & Nephrology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Dermatology (AREA)
  • Pulmonology (AREA)
  • Vascular Medicine (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

SE REFIERE A BIFENIL-4-SULFONILAMINO DE FORMULA I, R1 ES OH, NHOH; R2 ES H, OH, ALCOXI, ALQUILO, ENTRE OTROS; R3 ES H, ALQUILO, ALQUENILO, ALQUINILO, ENTRE OTROS; R4 ES (CR7R7`)k-X-(CR8R8')l-E-A; k Y l SON 0-4; R7, R7', R8, R8' SON H, ALQUILO, ENTRE OTROS; X ES O, S, SO, SO2, NR9, ENTRE OTROS; R9 Y R9' H, ALQUILO, ALQUENILO, ENTRE OTROS; E ES UN ENLACE, O, S, SO, SO2, NR10; R10 Y R10' SON H, ALQUILO, ALQUENILO, ALQUINILO, ENTRE OTROS; A ES H, ALQUILO, ALQUENILO, ALQUINILO, ENTRE OTROS; A JUNTO CON R7, R7', R8, R8', R9, R9', R10, R10' FORMAN UN HETEROCICLO; R5 ES H, ALQUILO, ALQUENILO, ALQUINILO, HETEROALQUILO, ENTRE OTROS; R6 ES ALQUILO, ALQUENILO, ENTRE OTROS; G ES S, O, NR11, R11C=CR11', ENTRE OTROS; R11 Y R11' SON H, ALQUILO, ALQUENILO, ENTRE OTROS; Z ES CICLOALQUILO, HETEROCICLOALQUILO; L-(CR12R12')aR13, ENTRE OTROS; a ES 0-4; L ES C­C, HC=CH, N=N, O, S, SO2; R12 Y R12' SON H, ALQUILO, ALQUENILO, ENTRE OTROS; R13 ES H, ARILO, HETEROARILO, ENTRE OTROS. SON COMPUESTOS PREFERIDOS ACIDO (2R,3S)-2-(4'-METOXI-BIFENIL-4-SULFONILAMINO-3-(4-METIL-BENCILOXI)-3-TIAZOL-2-IL-PROPIONICO, ACIDO (2R,3S)-2-(4'-METILSULFANIL-BIFENIL-4-SULFONILAMINO)-3-(4-METIL-BENCILOXI)-3-TIAZOL-2-IL-PROPIONICO, ENTRE OTROS. EL COMPUESTO I ES INHIBIDOR DE METALOPROTEASAS Y PUEDE SER UTIL PARA TRATAR ARTRITIS, CANCER, TRASTORNOS CARDIOVASCULARESREFERS TO BIPHENYL-4-SULFONYLAMINO OF FORMULA I, R1 IS OH, NHOH; R2 IS H, OH, ALCOXY, ALKYL, AMONG OTHERS; R3 IS H, ALKYL, ALKENYL, ALKINYL, AMONG OTHERS; R4 IS (CR7R7 ') k-X- (CR8R8') l-E-A; k AND l ARE 0-4; R7, R7 ', R8, R8' ARE H, ALKYL, AMONG OTHERS; X IS O, S, SO, SO2, NR9, AMONG OTHERS; R9 AND R9 'H, ALKYL, ALKENYL, AMONG OTHERS; E IS A LINK, O, S, SO, SO2, NR10; R10 AND R10 'ARE H, ALKYL, ALKENYL, ALKINYL, AMONG OTHERS; A IS H, ALKYL, ALKENYL, ALKINYL, AMONG OTHERS; TOGETHER WITH R7, R7 ', R8, R8', R9, R9 ', R10, R10' FORM A HETEROCYCLE; R5 IS H, ALKYL, ALKENYL, ALKINYL, HETEROALKYL, AMONG OTHERS; R6 IS RENT, ALKENYL, AMONG OTHERS; G IS S, O, NR11, R11C = CR11 ', AMONG OTHERS; R11 AND R11 'ARE H, ALKYL, ALKENYL, AMONG OTHERS; Z IS CYCLOALKYL, HETEROCYCLOALKYL; L- (CR12R12 ') aR13, AMONG OTHERS; a ES 0-4; L IS CC, HC = CH, N = N, O, S, SO2; R12 AND R12 'ARE H, ALKYL, ALKENYL, AMONG OTHERS; R13 IS H, ARYL, HETEROARYL, AMONG OTHERS. THE PREFERRED COMPOUNDS ARE ACID (2R, 3S) -2- (4'-METHOXY-BIPHENYL-4-SULFONYLAMINO-3- (4-METHYL-BENZYLOXY) -3-THIAZOL-2-IL-PROPIONICO, ACIDO (2R, 3S) -2- (4'-METHYLSULFANIL-BIPHENYL-4-SULFONYLAMINO) -3- (4-METHYL-BENZYLLOXY) -3-THIAZOL-2-IL-PROPIONICO, AMONG OTHERS. COMPOUND I IS INHIBITOR OF METALOPROTEASES AND MAY BE USEFUL TO TREAT ARTHRITIS, CANCER, CARDIOVASCULAR DISORDERS

PE2000001097A 1999-10-14 2000-10-13 METALOPROTEASE INHIBITORS PE20011003A1 (en)

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EP (1) EP1224171A1 (en)
JP (1) JP2003519100A (en)
KR (1) KR20020038951A (en)
CN (1) CN1379762A (en)
AU (1) AU8014500A (en)
BR (1) BR0014759A (en)
CA (1) CA2386485A1 (en)
CO (1) CO5271694A1 (en)
CZ (1) CZ20021161A3 (en)
HU (1) HUP0203118A3 (en)
IL (1) IL148893A0 (en)
MA (1) MA25561A1 (en)
MX (1) MXPA02003811A (en)
NO (1) NO20021748L (en)
NZ (1) NZ517983A (en)
PE (1) PE20011003A1 (en)
PL (1) PL355764A1 (en)
SK (1) SK5082002A3 (en)
TR (1) TR200200977T2 (en)
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US20050227994A1 (en) * 2002-03-27 2005-10-13 Shionogi & Co., Ltd. Decomposition inhibitor for extracellular matrix of cartilage
AU2003304456A1 (en) 2002-12-23 2005-03-16 Wyeth Holdings Corporation Acetylenic aryl sulfonate hydroxamic acid tace and matrix metalloproteinase inhibitors
WO2005061477A1 (en) 2003-12-04 2005-07-07 Wyeth Biaryl sulfonamides as mmp inhibitors
AU2003304638A1 (en) 2003-12-04 2005-07-14 Wyeth Biaryl sulfonamides and methods for using same
US7576222B2 (en) 2004-12-28 2009-08-18 Wyeth Alkynyl-containing tryptophan derivative inhibitors of TACE/matrix metalloproteinase
EP1904465B1 (en) * 2005-06-29 2010-03-31 Janssen Pharmaceutica N.V. Method of synthesis of imidazole-amino acid derivatives and related compounds
CN107224675B (en) * 2016-03-25 2023-06-02 南京中硼联康医疗科技有限公司 Boron neutron capture therapy system
EP3946301A4 (en) * 2019-04-02 2023-08-09 The University of Chicago Remodilins for airway remodeling and organ fibrosis

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DE69827940T2 (en) * 1997-03-04 2005-06-09 Pharmacia Corp.(N.D.Ges.D.Staates Delaware) THIARYLSULFONAMID-hydroxamic acid
WO1999006340A2 (en) * 1997-07-31 1999-02-11 The Procter & Gamble Company Sulfonylamino substituted hydroxamic acid derivatives as metalloprotease inhibitors
US6455522B1 (en) * 1998-02-11 2002-09-24 Bristol-Myers Squibb Pharma Company Cyclic sulfonamide derivatives as metalloproteinase inhibitors
AU6542298A (en) * 1998-03-04 1998-09-22 Monsanto Company Thioaryl sulfonamide hydroxamic acid compounds
EP0967201A1 (en) * 1998-05-20 1999-12-29 Roche Diagnostics GmbH Pharmaceutical agents containing sulfonamids as matrix metalloproteinase inhibitors
SK12462001A3 (en) * 1999-03-03 2002-04-04 The Procter & Gamble Company Dihetero-substituted metalloprotease inhibitors
BR0008716A (en) * 1999-03-03 2002-09-24 Procter & Gamble Metalloprotease inhibitors containing alkenyl or alkynyl

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HUP0203118A2 (en) 2003-01-28
MA25561A1 (en) 2002-10-01
HUP0203118A3 (en) 2003-05-28
KR20020038951A (en) 2002-05-24
BR0014759A (en) 2002-07-02
EP1224171A1 (en) 2002-07-24
NO20021748L (en) 2002-06-14
IL148893A0 (en) 2002-09-12
CZ20021161A3 (en) 2002-08-14
WO2001027084A1 (en) 2001-04-19
CA2386485A1 (en) 2001-04-19
ZA200202207B (en) 2002-12-24
JP2003519100A (en) 2003-06-17
PL355764A1 (en) 2004-05-17
CO5271694A1 (en) 2003-04-30
SK5082002A3 (en) 2002-10-08
TR200200977T2 (en) 2002-08-21
AU8014500A (en) 2001-04-23
MXPA02003811A (en) 2002-09-30
NO20021748D0 (en) 2002-04-12
NZ517983A (en) 2004-01-30
CN1379762A (en) 2002-11-13

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