ZA200202207B - Beta disubstituted metalloprotease inhibitors. - Google Patents
Beta disubstituted metalloprotease inhibitors. Download PDFInfo
- Publication number
- ZA200202207B ZA200202207B ZA200202207A ZA200202207A ZA200202207B ZA 200202207 B ZA200202207 B ZA 200202207B ZA 200202207 A ZA200202207 A ZA 200202207A ZA 200202207 A ZA200202207 A ZA 200202207A ZA 200202207 B ZA200202207 B ZA 200202207B
- Authority
- ZA
- South Africa
- Prior art keywords
- biphenyl
- sulfonylamino
- methoxy
- phenyl
- propionic acid
- Prior art date
Links
- 239000003475 metalloproteinase inhibitor Substances 0.000 title description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 102
- 125000003118 aryl group Chemical group 0.000 claims description 95
- 150000001875 compounds Chemical class 0.000 claims description 84
- 239000001257 hydrogen Substances 0.000 claims description 83
- 229910052739 hydrogen Inorganic materials 0.000 claims description 83
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 82
- 125000001072 heteroaryl group Chemical group 0.000 claims description 80
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 79
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 73
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 69
- 125000001188 haloalkyl group Chemical group 0.000 claims description 64
- 125000003342 alkenyl group Chemical group 0.000 claims description 61
- 125000000304 alkynyl group Chemical group 0.000 claims description 60
- 150000002431 hydrogen Chemical class 0.000 claims description 58
- -1 4'-Methoxy-biphenyl-4-sulfonyl Chemical group 0.000 claims description 41
- 125000005842 heteroatom Chemical group 0.000 claims description 37
- 125000004429 atom Chemical group 0.000 claims description 29
- 125000000623 heterocyclic group Chemical group 0.000 claims description 26
- 208000035475 disorder Diseases 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 23
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000006413 ring segment Chemical group 0.000 claims description 21
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 150000002148 esters Chemical class 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 239000003937 drug carrier Substances 0.000 claims description 11
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- 150000001408 amides Chemical class 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 6
- 206010003246 arthritis Diseases 0.000 claims description 5
- 150000003949 imides Chemical class 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 4
- 238000002399 angioplasty Methods 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 3
- 206010019280 Heart failures Diseases 0.000 claims description 3
- 208000022873 Ocular disease Diseases 0.000 claims description 3
- 208000024693 gingival disease Diseases 0.000 claims description 3
- 208000017520 skin disease Diseases 0.000 claims description 3
- 230000004614 tumor growth Effects 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- 206010056370 Congestive cardiomyopathy Diseases 0.000 claims description 2
- 201000010046 Dilated cardiomyopathy Diseases 0.000 claims description 2
- 206010063837 Reperfusion injury Diseases 0.000 claims description 2
- 208000007474 aortic aneurysm Diseases 0.000 claims description 2
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- 208000037803 restenosis Diseases 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 10
- 235000019260 propionic acid Nutrition 0.000 claims 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
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- CRMUWSRQOOCXDT-LEWJYISDSA-N (2r,3r)-3-hydroxy-2-[[4-(4-methoxyphenyl)phenyl]sulfonylamino]-4-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethoxy]butanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(S(=O)(=O)N[C@H]([C@@H](O)COCCNC(=O)OC(C)(C)C)C(O)=O)C=C1 CRMUWSRQOOCXDT-LEWJYISDSA-N 0.000 claims 1
- VPEVWKZCYZRMKW-RTBURBONSA-N (2r,3r)-3-hydroxy-2-[[4-(4-methoxyphenyl)phenyl]sulfonylamino]-5-[(1-methyl-1,2,4-triazol-3-yl)sulfanyl]pentanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(S(=O)(=O)N[C@H]([C@H](O)CCSC2=NN(C)C=N2)C(O)=O)C=C1 VPEVWKZCYZRMKW-RTBURBONSA-N 0.000 claims 1
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- OMIANILESCGFKJ-NHCUHLMSSA-N (2r,3r)-3-hydroxy-2-[[4-(4-methoxyphenyl)phenyl]sulfonylamino]-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(S(=O)(=O)N[C@H]([C@H](O)CCCNC(=O)OC(C)(C)C)C(O)=O)C=C1 OMIANILESCGFKJ-NHCUHLMSSA-N 0.000 claims 1
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- KPEVWUYOJHMHOL-RTBURBONSA-N (2r,3s)-3-hydroxy-2-[[4-(4-methoxyphenyl)phenyl]sulfonylamino]-4-(1-methylimidazol-2-yl)oxybutanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(S(=O)(=O)N[C@H]([C@H](O)COC=2N(C=CN=2)C)C(O)=O)C=C1 KPEVWUYOJHMHOL-RTBURBONSA-N 0.000 claims 1
- LQXICCARCFRCSE-RTBURBONSA-N (2r,3s)-3-hydroxy-2-[[4-(4-methoxyphenyl)phenyl]sulfonylamino]-4-(1-methylimidazol-2-yl)sulfanylbutanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(S(=O)(=O)N[C@H]([C@H](O)CSC=2N(C=CN=2)C)C(O)=O)C=C1 LQXICCARCFRCSE-RTBURBONSA-N 0.000 claims 1
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- OBWYXROJNYVDHH-VSGBNLITSA-N (2s,3r)-2-[[4-(4-bromophenyl)phenyl]sulfonylamino]-3-[2-[methylsulfonyl(pyridin-3-yl)amino]ethylsulfanyl]-3-phenylpropanoic acid Chemical compound N([C@H]([C@H](SCCN(S(=O)(=O)C)C=1C=NC=CC=1)C=1C=CC=CC=1)C(O)=O)S(=O)(=O)C(C=C1)=CC=C1C1=CC=C(Br)C=C1 OBWYXROJNYVDHH-VSGBNLITSA-N 0.000 claims 1
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Classifications
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- 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
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Ophthalmology & Optometry (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Pulmonology (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)
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US15932099P | 1999-10-14 | 1999-10-14 |
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JP (1) | JP2003519100A (de) |
KR (1) | KR20020038951A (de) |
CN (1) | CN1379762A (de) |
AU (1) | AU8014500A (de) |
BR (1) | BR0014759A (de) |
CA (1) | CA2386485A1 (de) |
CO (1) | CO5271694A1 (de) |
CZ (1) | CZ20021161A3 (de) |
HU (1) | HUP0203118A3 (de) |
IL (1) | IL148893A0 (de) |
MA (1) | MA25561A1 (de) |
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PE (1) | PE20011003A1 (de) |
PL (1) | PL355764A1 (de) |
SK (1) | SK5082002A3 (de) |
TR (1) | TR200200977T2 (de) |
WO (1) | WO2001027084A1 (de) |
ZA (1) | ZA200202207B (de) |
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WO2003080042A1 (fr) * | 2002-03-27 | 2003-10-02 | Shionogi & Co., Ltd. | Inhibiteur de decomposition pour matrice extracellulaire de cartilage |
US7199155B2 (en) | 2002-12-23 | 2007-04-03 | Wyeth Holdings Corporation | Acetylenic aryl sulfonate hydroxamic acid TACE and matrix metalloproteinase inhibitors |
JP2007525406A (ja) | 2003-12-04 | 2007-09-06 | ワイス | ビアリールスルホンアミドおよびその使用方法 |
CA2548518A1 (en) | 2003-12-04 | 2005-07-07 | Wyeth | Biaryl sulfonamides as mmp inhibitors |
US7576222B2 (en) | 2004-12-28 | 2009-08-18 | Wyeth | Alkynyl-containing tryptophan derivative inhibitors of TACE/matrix metalloproteinase |
CA2613047C (en) * | 2005-06-29 | 2013-10-22 | Janssen Pharmaceutica N.V. | Method of synthesis of azole-containing amino acids |
CN107224675B (zh) * | 2016-03-25 | 2023-06-02 | 南京中硼联康医疗科技有限公司 | 硼中子捕获治疗系统 |
WO2020206109A1 (en) * | 2019-04-02 | 2020-10-08 | The University Of Chicago | Remodilins for airway remodeling and organ fibrosis |
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US6451791B1 (en) * | 1997-03-04 | 2002-09-17 | Monsanto Company | Amidoaromatic ring sulfonamide hydroxamic acid compounds |
IL134273A0 (en) * | 1997-07-31 | 2001-04-30 | Procter & Gamble | Acyclic metalloprotease inhibitors |
AU2594799A (en) * | 1998-02-11 | 1999-08-30 | Du Pont Pharmaceuticals Company | Novel cyclic sulfonamide derivatives as metalloproteinase inhibitors |
AU6542298A (en) * | 1998-03-04 | 1998-09-22 | Monsanto Company | Thioaryl sulfonamide hydroxamic acid compounds |
EP0967201A1 (de) * | 1998-05-20 | 1999-12-29 | Roche Diagnostics GmbH | Sulphonamide enthaltende Arzneimittel als Matrix Metalloproteinase Inhibitoren |
US6566381B1 (en) * | 1999-03-03 | 2003-05-20 | The Procter & Gamble Company | Hetero-substituted metalloprotease inhibitors |
WO2000051975A1 (en) * | 1999-03-03 | 2000-09-08 | The Procter & Gamble Company | Alkenyl- and alkynyl-containing metalloprotease inhibitors |
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MXPA02003811A (es) | 2002-09-30 |
IL148893A0 (en) | 2002-09-12 |
KR20020038951A (ko) | 2002-05-24 |
EP1224171A1 (de) | 2002-07-24 |
CO5271694A1 (es) | 2003-04-30 |
CA2386485A1 (en) | 2001-04-19 |
BR0014759A (pt) | 2002-07-02 |
TR200200977T2 (tr) | 2002-08-21 |
CN1379762A (zh) | 2002-11-13 |
MA25561A1 (fr) | 2002-10-01 |
JP2003519100A (ja) | 2003-06-17 |
NO20021748D0 (no) | 2002-04-12 |
SK5082002A3 (en) | 2002-10-08 |
HUP0203118A2 (hu) | 2003-01-28 |
PL355764A1 (en) | 2004-05-17 |
AU8014500A (en) | 2001-04-23 |
NO20021748L (no) | 2002-06-14 |
NZ517983A (en) | 2004-01-30 |
CZ20021161A3 (cs) | 2002-08-14 |
PE20011003A1 (es) | 2001-09-26 |
HUP0203118A3 (en) | 2003-05-28 |
WO2001027084A1 (en) | 2001-04-19 |
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