TW448172B - Novel hydroxamic acid derivatives useful for the treatment of diseases related to connective tissue degradation - Google Patents
Novel hydroxamic acid derivatives useful for the treatment of diseases related to connective tissue degradation Download PDFInfo
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- TW448172B TW448172B TW086102076A TW86102076A TW448172B TW 448172 B TW448172 B TW 448172B TW 086102076 A TW086102076 A TW 086102076A TW 86102076 A TW86102076 A TW 86102076A TW 448172 B TW448172 B TW 448172B
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- TW
- Taiwan
- Prior art keywords
- oxy
- hydroxy
- methylpropyl
- ethyl
- phenylethyl
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- 201000010099 disease Diseases 0.000 title claims abstract description 19
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 19
- 210000002808 connective tissue Anatomy 0.000 title claims abstract description 13
- 239000002253 acid Substances 0.000 title abstract description 24
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 title abstract description 4
- 230000008354 tissue degradation Effects 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 217
- 239000011159 matrix material Substances 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 108060005980 Collagenase Proteins 0.000 claims abstract description 13
- 102000029816 Collagenase Human genes 0.000 claims abstract description 13
- 229960002424 collagenase Drugs 0.000 claims abstract description 13
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 8
- 206010027476 Metastases Diseases 0.000 claims abstract description 5
- 230000012010 growth Effects 0.000 claims abstract description 5
- 230000009545 invasion Effects 0.000 claims abstract description 5
- 230000009401 metastasis Effects 0.000 claims abstract description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 5
- 206010053555 Arthritis bacterial Diseases 0.000 claims abstract description 4
- 208000004575 Infectious Arthritis Diseases 0.000 claims abstract description 4
- 208000007565 gingivitis Diseases 0.000 claims abstract description 4
- 201000001223 septic arthritis Diseases 0.000 claims abstract description 4
- 208000025865 Ulcer Diseases 0.000 claims abstract 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 347
- -1 methylbutyl Chemical group 0.000 claims description 309
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 250
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 229
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 178
- 238000011049 filling Methods 0.000 claims description 125
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 105
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 104
- 230000002079 cooperative effect Effects 0.000 claims description 82
- 239000007787 solid Substances 0.000 claims description 77
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 71
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 31
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 24
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- 235000015170 shellfish Nutrition 0.000 claims description 21
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 20
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- 150000001412 amines Chemical class 0.000 claims description 19
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 18
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 13
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 13
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 12
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 11
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 11
- LXNHXLLTXMVWPM-UHFFFAOYSA-N pyridoxine Chemical compound CC1=NC=C(CO)C(CO)=C1O LXNHXLLTXMVWPM-UHFFFAOYSA-N 0.000 claims description 10
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 8
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 8
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 claims description 8
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- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims description 8
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 230000015556 catabolic process Effects 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000006731 degradation reaction Methods 0.000 claims description 6
- 230000008774 maternal effect Effects 0.000 claims description 6
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 5
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 235000008160 pyridoxine Nutrition 0.000 claims description 5
- 239000011677 pyridoxine Substances 0.000 claims description 5
- 229940011671 vitamin b6 Drugs 0.000 claims description 5
- FUZDFUUBQLKDPP-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanimidamide Chemical compound NC(=N)CN1CCCC1 FUZDFUUBQLKDPP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 4
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- 208000028169 periodontal disease Diseases 0.000 claims description 4
- TZFKKBRWQBLFRI-UHFFFAOYSA-N 2-pyrrolidin-3-ylethanimidamide Chemical compound NC(=N)CC1CCNC1 TZFKKBRWQBLFRI-UHFFFAOYSA-N 0.000 claims description 3
- WRXSZGQEKRITLR-UHFFFAOYSA-N C(C)(=N)N.N1CCCC1 Chemical compound C(C)(=N)N.N1CCCC1 WRXSZGQEKRITLR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
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- 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
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D231/08—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with oxygen or sulfur atoms directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
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- 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
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
-
- 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
- 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
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| US1309896P | 1996-03-08 | 1996-03-08 |
Publications (1)
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|---|---|
| TW448172B true TW448172B (en) | 2001-08-01 |
Family
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Family Applications (1)
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| TW086102076A TW448172B (en) | 1996-03-08 | 1997-02-21 | Novel hydroxamic acid derivatives useful for the treatment of diseases related to connective tissue degradation |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US5932579A (en) | 1996-06-18 | 1999-08-03 | Affymax Technologies N.V. | Collagenase-1 and stromelysin-1 inhibitors, pharmaceutical compositions comprising same and methods of their use |
| US5830869A (en) * | 1996-06-21 | 1998-11-03 | Mitchell; Mark Allen | Thiadiazole amide MMP inhibitors |
| EP0929519B1 (en) * | 1996-09-27 | 2005-02-23 | PHARMACIA & UPJOHN COMPANY | Beta-sulfonyl hydroxamic acids as matrix metalloproteinases inhibitors |
| GB9702088D0 (en) | 1997-01-31 | 1997-03-19 | Pharmacia & Upjohn Spa | Matrix metalloproteinase inhibitors |
| WO1998039326A1 (en) * | 1997-03-04 | 1998-09-11 | Monsanto Company | Aromatic sulfonyl alpha-hydroxy hydroxamic acid compounds |
| US6566373B2 (en) | 1997-05-06 | 2003-05-20 | Smithkline Beecham Corporation | Protease inhibitors |
| AR013079A1 (es) * | 1997-05-06 | 2000-12-13 | Smithkline Beecham Corp | Derivados sustituidos de tetrahidrofurano-3-onas, de tetrahidropirano-3- onas y tetrahidrotiofen-3-onas, un procedimiento para su preparacion unacomposicion farmaceutica de un medicamento util como inhibidores de proteasas e intermediarios |
| US5883131A (en) * | 1997-07-09 | 1999-03-16 | Pfizer Inc. | Cyclic sulfone derivatives |
| CA2298617A1 (en) | 1997-07-31 | 1999-02-11 | Yetunde Olabisi Taiwo | Acyclic metalloprotease inhibitors |
| DE19741235A1 (de) * | 1997-09-18 | 1999-03-25 | Hoechst Marion Roussel De Gmbh | Neue Imidazolidinderivate, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
| ZA988967B (en) * | 1997-10-03 | 2000-04-03 | Du Pont Pharm Co | Lactam metalloprotease inhibitors. |
| US6403632B1 (en) | 2000-03-01 | 2002-06-11 | Bristol Myers Squibb Pharma Co | Lactam metalloprotease inhibitors |
| EP1024134A4 (en) * | 1997-10-09 | 2003-05-14 | Ono Pharmaceutical Co | DERIVATIVES OF AMINOBUTANIC ACID |
| DK1004578T3 (da) * | 1998-11-05 | 2004-06-28 | Pfizer Prod Inc | 5-oxo-pyrrolidin-2-carboxylsyrehydroxamidderivater |
| GB9825988D0 (en) * | 1998-11-27 | 1999-01-20 | Pfizer Ltd | Indole derivatives |
| US20040122011A1 (en) * | 1998-12-23 | 2004-06-24 | Pharmacia Corporation | Method of using a COX-2 inhibitor and a TACE inhibitors as a combination therapy |
| RU2001126721A (ru) | 1999-03-03 | 2004-02-20 | Дзе Проктер Энд Гэмбл Компани (US) | Алкенил-и алкинилсодержащие ингибиторы металлопротезы |
| RU2001126719A (ru) | 1999-03-03 | 2004-02-20 | Дзе Проктер Энд Гэмбл Компани (US) | Дигетерозамещенные ингибиторы металлопротеазы |
| CA2361848A1 (en) * | 1999-04-02 | 2000-10-12 | Dupont Pharmaceuticals Company | Novel lactam inhibitors of matrix metalloproteinases, tnf-.alpha., and aggrecanase |
| US6797820B2 (en) | 1999-12-17 | 2004-09-28 | Vicuron Pharmaceuticals Inc. | Succinate compounds, compositions and methods of use and preparation |
| WO2002028829A2 (en) * | 2000-09-25 | 2002-04-11 | Questcor Pharmaceuticals, Inc. | Peptide deformylase inhibitors |
| CA2434205A1 (en) | 2001-01-11 | 2002-07-18 | Dupont Pharmaceuticals Company | 1,1-disubstituted cyclic inhibitors of matrix metalloprotease and tnf-.alpha. |
| US6642255B2 (en) | 2001-01-11 | 2003-11-04 | Bristol-Myers Squibb Pharma Company | 1,2,-Disubstituted cyclic inhibitors of matrix metalloproteases and TNF-alpha |
| EP1363623B1 (en) * | 2001-03-01 | 2005-11-16 | Smithkline Beecham Corporation | Peptide deformylase inhibitors |
| AR036053A1 (es) | 2001-06-15 | 2004-08-04 | Versicor Inc | Compuestos de n-formil-hidroxilamina, un proceso para su preparacion y composiciones farmaceuticas |
| EP1406893B1 (en) * | 2001-06-15 | 2007-04-18 | Vicuron Pharmaceuticals, Inc. | Pyrrolidine bicyclic compounds |
| PE20030701A1 (es) | 2001-12-20 | 2003-08-21 | Schering Corp | Compuestos para el tratamiento de trastornos inflamatorios |
| TWI294778B (en) * | 2002-03-13 | 2008-03-21 | Smithkline Beecham Corp | Peptide deformylase inhibitors |
| US7622117B2 (en) * | 2002-04-17 | 2009-11-24 | Dynamis Therapeutics, Inc. | 3-deoxyglucosone and skin |
| PL374117A1 (en) * | 2002-05-29 | 2005-10-03 | Merck & Co, Inc. | Compounds useful in the treatment of anthrax and inhibiting lethal factor |
| US20050176686A1 (en) * | 2002-07-23 | 2005-08-11 | 4Sc Ag | Novel compounds as histone deacetylase inhibitors |
| WO2004101523A1 (en) * | 2003-05-17 | 2004-11-25 | Korea Research Institute Of Bioscience And Biotechnology | Novel 2-oxo-heterocyclic compounds and the pharmaceutical compositions comprising the same |
| US7122560B2 (en) | 2003-06-18 | 2006-10-17 | Bristol-Myers Squibb Company | Lactam derivatives as inhibitors of matrix metalloproteinases and/or TNF-α converting enzyme |
| EP1663201A4 (en) * | 2003-07-15 | 2009-10-28 | Korea Res Inst Of Bioscience | USE OF NOVEL 2-OXO-HETEROCYCLIC COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME |
| RU2368390C2 (ru) * | 2003-07-23 | 2009-09-27 | Новартис Аг | Применение кальцитонина при остеоартрите |
| JP2007537256A (ja) * | 2004-05-11 | 2007-12-20 | メルク エンド カムパニー インコーポレーテッド | Ｎ−スルホン化アミノ酸誘導体調製のためのプロセス |
| US20100003276A1 (en) * | 2004-12-07 | 2010-01-07 | Hermes Jeffery D | Methods for treating anthrax and inhibiting lethal factor |
| DE102004060229A1 (de) * | 2004-12-15 | 2006-06-29 | Sanofi-Aventis Deutschland Gmbh | Neue zyklische Harnstoffe als Inhibitoren von Metallproteasen |
| US20080287516A1 (en) * | 2005-01-28 | 2008-11-20 | Irm Llc | Phenyl-Substituted Pyrrolidones |
| GB0811643D0 (en) | 2008-06-25 | 2008-07-30 | Cancer Rec Tech Ltd | New therapeutic agents |
| FR2947268B1 (fr) * | 2009-06-30 | 2011-08-26 | Galderma Res & Dev | Nouveaux composes benzene-sulfonamides, leur procede de synthese et leur utilisation en medecine ainsi qu'en cosmetique |
| WO2012031298A2 (en) | 2010-09-03 | 2012-03-08 | Duke University | Ethynylbenzene derivatives |
| US20140081017A1 (en) * | 2012-09-14 | 2014-03-20 | Methylgene Inc. | Histone Deacetylase Inhibitors for Enhancing Activity of Antifungal Agents |
| US9908851B2 (en) | 2013-08-16 | 2018-03-06 | Duke University | 2-piperidinyl substituted N,3-dihydroxybutanamides |
| EP3041354A4 (en) | 2013-08-16 | 2017-06-14 | Duke University | Substituted hydroxamic acid compounds |
| US10189786B2 (en) | 2013-08-16 | 2019-01-29 | Duke University | Antibacterial compounds |
| GB201517216D0 (en) | 2015-09-29 | 2015-11-11 | Cancer Res Technology Ltd And Astex Therapeutics Ltd | Pharmaceutical compounds |
| GB201517217D0 (en) | 2015-09-29 | 2015-11-11 | Astex Therapeutics Ltd And Cancer Res Technology Ltd | Pharmaceutical compounds |
| GB201704966D0 (en) | 2017-03-28 | 2017-05-10 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| GB201704965D0 (en) | 2017-03-28 | 2017-05-10 | Astex Therapeutics Ltd | Pharmaceutical compounds |
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| US1360583A (en) * | 1918-02-18 | 1920-11-30 | Great Lakes Dredge And Dock Co | Car-dumper |
| EP0042100A1 (de) * | 1980-06-13 | 1981-12-23 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Pyrazolopyridazin-Derivate, Zwischenprodukte und Verfahren zu deren Herstellung, sowie diese enthaltende Arzneimittel |
| DE3420193A1 (de) * | 1984-05-30 | 1985-12-05 | Boehringer Ingelheim KG, 6507 Ingelheim | Neue substituierte pyrrolidinone, verfahren zu ihrer herstellung und arzneimittel |
| EP0639982A1 (en) * | 1992-05-01 | 1995-03-01 | British Biotech Pharmaceuticals Limited | Use of mmp inhibitors |
| US5318964A (en) * | 1992-06-11 | 1994-06-07 | Hoffmann-La Roche Inc. | Hydroxamic derivatives and pharmaceutical compositions |
| ATE195117T1 (de) * | 1993-03-31 | 2000-08-15 | Searle & Co | 1-amdinophenyl-pyrrolidone/piperidinone als blutblättchen-aggregations inhibitoren |
| DE69415159T2 (de) * | 1993-08-02 | 1999-07-22 | Celltech Therapeutics Ltd., Slough, Berkshire | Succinamid-derivate, verfahren zu ihrer herstellung und ihre verwendung als gelatinase- und collagenase- inhibitoren |
| GB9320660D0 (en) * | 1993-10-07 | 1993-11-24 | British Bio Technology | Inhibition of cytokine production |
| US5403952A (en) * | 1993-10-08 | 1995-04-04 | Merck & Co., Inc. | Substituted cyclic derivatives as novel antidegenerative agents |
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- 1997-03-03 NZ NZ330922A patent/NZ330922A/xx unknown
- 1997-03-03 JP JP9531784A patent/JP2000506163A/ja not_active Withdrawn
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- 1997-03-03 ES ES97908674T patent/ES2191823T3/es not_active Expired - Lifetime
- 1997-03-03 CN CN97192171A patent/CN1210517A/zh active Pending
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1998
- 1998-09-07 NO NO19984112A patent/NO312956B1/no unknown
Also Published As
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| NO984112L (no) | 1998-11-06 |
| PE55698A1 (es) | 1998-09-16 |
| CN1210517A (zh) | 1999-03-10 |
| EP0898562B1 (en) | 2003-01-22 |
| ATE231490T1 (de) | 2003-02-15 |
| RU2168497C2 (ru) | 2001-06-10 |
| NO312956B1 (no) | 2002-07-22 |
| DE69718634D1 (de) | 2003-02-27 |
| NO984112D0 (no) | 1998-09-07 |
| AU2052597A (en) | 1997-09-22 |
| PL328693A1 (en) | 1999-02-15 |
| KR19990087597A (ko) | 1999-12-27 |
| WO1997032846A1 (en) | 1997-09-12 |
| US5712300A (en) | 1998-01-27 |
| ES2191823T3 (es) | 2003-09-16 |
| UA61906C2 (en) | 2003-12-15 |
| DK0898562T3 (da) | 2003-05-12 |
| PT898562E (pt) | 2003-06-30 |
| ZA971902B (en) | 1998-09-07 |
| JP2000506163A (ja) | 2000-05-23 |
| MY117762A (en) | 2004-08-30 |
| BR9707947A (pt) | 1999-07-27 |
| AU707180B2 (en) | 1999-07-01 |
| ID16144A (id) | 1997-09-04 |
| NZ330922A (en) | 2000-01-28 |
| DE69718634T2 (de) | 2003-10-30 |
| EP0898562A1 (en) | 1999-03-03 |
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