JP2007502259A - マトリックスメタロプロテイナーゼの阻害剤 - Google Patents
マトリックスメタロプロテイナーゼの阻害剤 Download PDFInfo
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- JP2007502259A JP2007502259A JP2006522996A JP2006522996A JP2007502259A JP 2007502259 A JP2007502259 A JP 2007502259A JP 2006522996 A JP2006522996 A JP 2006522996A JP 2006522996 A JP2006522996 A JP 2006522996A JP 2007502259 A JP2007502259 A JP 2007502259A
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- formula
- compound
- alkyl
- optionally substituted
- heteroaryl
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- 102000002274 Matrix Metalloproteinases Human genes 0.000 title abstract description 14
- 108010000684 Matrix Metalloproteinases Proteins 0.000 title abstract description 14
- 239000003112 inhibitor Substances 0.000 title abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 46
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 42
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- -1 phenylmethoxy Chemical group 0.000 claims abstract description 19
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 15
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 13
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 229960005137 succinic acid Drugs 0.000 claims abstract description 7
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- IKVMMPXMDYEXIX-UHFFFAOYSA-N 2-(3-acetamido-4-cyclohexylphenyl)butanedioic acid Chemical compound CC(=O)NC1=CC(C(CC(O)=O)C(O)=O)=CC=C1C1CCCCC1 IKVMMPXMDYEXIX-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims abstract description 3
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims abstract description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 125000006168 tricyclic group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 126
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- 241001465754 Metazoa Species 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229940124597 therapeutic agent Drugs 0.000 claims description 3
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- 125000005843 halogen group Chemical group 0.000 claims description 2
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- 125000001424 substituent group Chemical group 0.000 claims description 2
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- 238000002360 preparation method Methods 0.000 abstract description 8
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- 238000006243 chemical reaction Methods 0.000 description 29
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000001246 bromo group Chemical group Br* 0.000 description 5
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- 230000004054 inflammatory process Effects 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 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 description 4
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
- 102100027998 Macrophage metalloelastase Human genes 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
- C07C235/76—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C235/78—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
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- 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]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/51—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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- Chemical & Material Sciences (AREA)
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- General Health & Medical Sciences (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0319069.1A GB0319069D0 (en) | 2003-08-14 | 2003-08-14 | Therapeutically useful compounds |
| PCT/EP2004/009087 WO2005016868A2 (en) | 2003-08-14 | 2004-08-12 | Matrix metalloproteinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007502259A true JP2007502259A (ja) | 2007-02-08 |
| JP2007502259A5 JP2007502259A5 (enExample) | 2007-08-30 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006522996A Pending JP2007502259A (ja) | 2003-08-14 | 2004-08-12 | マトリックスメタロプロテイナーゼの阻害剤 |
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| Country | Link |
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| US (1) | US7476759B2 (enExample) |
| EP (1) | EP1654218A2 (enExample) |
| JP (1) | JP2007502259A (enExample) |
| GB (1) | GB0319069D0 (enExample) |
| WO (1) | WO2005016868A2 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0321538D0 (en) * | 2003-09-13 | 2003-10-15 | Glaxo Group Ltd | Therapeutically useful compounds |
| US20140316336A1 (en) * | 2011-01-11 | 2014-10-23 | Abu Dhabi National Industrial Projects Co. | Auto-disable safety syringe |
| CN107793415A (zh) * | 2016-12-01 | 2018-03-13 | 湖南省食品药品检验研究院 | 酒石酸唑吡坦杂质的合成方法 |
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| JPS58180473A (ja) * | 1982-04-16 | 1983-10-21 | Shikoku Chem Corp | イミダゾリル琥珀酸化合物および該化合物を用いるエポキシ樹脂硬化方法 |
| JPS60105645A (ja) * | 1983-11-12 | 1985-06-11 | Yasumitsu Tamura | アリ−ルコハク酸エステルの製造法 |
| JPS6456763A (en) * | 1987-07-01 | 1989-03-03 | Ciba Geigy Ag | Photosensitive epoxy resin and its use |
| DD271903A1 (de) * | 1988-05-17 | 1989-09-20 | Univ Halle Wittenberg | Verfahren zur herstellung stabiler, 2-unsubstituierter imidazol-3-oxide |
| WO1998031697A1 (en) * | 1997-01-15 | 1998-07-23 | Sankyo Company, Limited | Aryl c-glycoside compounds and sulfated esters thereof |
| JP2000271485A (ja) * | 1999-03-24 | 2000-10-03 | Kazuhiko Saigo | オレフィン類のビスアルコキシカルボニル化触媒、及びコハク酸エステル誘導体の製造法 |
| JP2002508345A (ja) * | 1997-12-17 | 2002-03-19 | カイロテック・テクノロジー・リミテッド | 不斉水素化 |
| JP2002541138A (ja) * | 1999-04-02 | 2002-12-03 | デュポン ファーマシューティカルズ カンパニー | マトリックスメタロプロテアーゼ、TNF−α、およびアグレカナーゼの阻害剤としての新規アミド誘導体 |
| WO2003006670A2 (en) * | 2001-07-09 | 2003-01-23 | Axys Pharmaceuticals, Inc. | 2-[5-(5-carbamimidoyl-1h-heteroaryl)-6-hydroxybiphenyl-3-yl]-succinic acid derivatives as factor viia inhibitors |
| JP2003523931A (ja) * | 1998-12-04 | 2003-08-12 | スミスクライン・ビーチャム・コーポレイション | ビトロネクチンレセプター拮抗物質 |
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| SE367181B (enExample) | 1969-05-14 | 1974-05-20 | Takeda Chemical Industries Ltd | |
| US3644479A (en) * | 1970-02-09 | 1972-02-22 | Bristol Myers Co | 1-indancarboxylic acids and derivatives |
| US3663627A (en) * | 1970-06-01 | 1972-05-16 | Bristol Myers Co | 1-indanmethanols |
| CH585687A5 (enExample) * | 1972-08-24 | 1977-03-15 | Ciba Geigy Ag | |
| ZA98376B (en) * | 1997-01-23 | 1998-07-23 | Hoffmann La Roche | Sulfamide-metalloprotease inhibitors |
| US5804581A (en) * | 1997-05-15 | 1998-09-08 | Bayer Corporation | Inhibition of matrix metalloproteases by substituted phenalkyl compounds |
| US6130220A (en) * | 1997-10-16 | 2000-10-10 | Syntex (Usa) Inc. | Sulfamide-metalloprotease inhibitors |
| US20010039287A1 (en) * | 1997-11-14 | 2001-11-08 | Thomas E Barta | Aromatic sulfone hydroxamic acid metalloprotease inhibitor |
| US20010014688A1 (en) * | 1997-11-14 | 2001-08-16 | Thomas E. Barta | Aromatic sulfone hydroxamic acid metalloprotease inhibitor |
| PA8469501A1 (es) * | 1998-04-10 | 2000-09-29 | Pfizer Prod Inc | Hidroxamidas del acido (4-arilsulfonilamino)-tetrahidropiran-4-carboxilico |
| ES2220004T3 (es) * | 1998-04-10 | 2004-12-01 | Pfizer Products Inc. | Derivados del acido ciclobutil-ariloxiarilsulfonilaminohidroxamico. |
| AU775701B2 (en) * | 1999-02-08 | 2004-08-12 | G.D. Searle & Co. | Sulfamato hydroxamic acid metalloprotease inhibitor |
| CZ20013338A3 (cs) * | 1999-03-18 | 2002-03-13 | Celgene Corporation | Substituované 1-oxo-a l,3-dioxoisoindoliny a jejich pouľití ve farmaceutických prostředcích pro sníľení koncentrací zánětlivých cytokinů |
| EP1181286B1 (en) * | 1999-05-28 | 2003-11-12 | Pfizer Products Inc. | 3-(arylsulfonylamino)-tetrahydropyran-3-carboxylic acid hydroxamides |
| HN2000000052A (es) * | 1999-05-28 | 2001-02-02 | Pfizer Prod Inc | Hidroxiamidas de acidos 3- (arilsulfonilamino)- tetrahidrofuran-3-carboxilicos. |
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| US20010049449A1 (en) * | 1999-12-23 | 2001-12-06 | Becker Daniel P. | Aromatic sulfonyl alpha-cycloamino hydroxamates and their use as MMP inhibitors |
| US6458822B2 (en) * | 2000-03-13 | 2002-10-01 | Pfizer Inc. | 2-oxo-imidazolidine-4-carboxylic acid hydroxamide compounds that inhibit matrix metalloproteinases |
| JP2006506446A (ja) * | 2002-11-19 | 2006-02-23 | ガルデルマ・リサーチ・アンド・デヴェロップメント・エス・エヌ・セ | PPAR−γ型レセプターを活性化する新規二芳香族化合物、および化粧品組成物または薬剤組成物におけるその使用 |
-
2003
- 2003-08-14 GB GBGB0319069.1A patent/GB0319069D0/en not_active Ceased
-
2004
- 2004-08-12 US US10/569,812 patent/US7476759B2/en not_active Expired - Fee Related
- 2004-08-12 EP EP04764084A patent/EP1654218A2/en not_active Withdrawn
- 2004-08-12 JP JP2006522996A patent/JP2007502259A/ja active Pending
- 2004-08-12 WO PCT/EP2004/009087 patent/WO2005016868A2/en not_active Ceased
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5053364A (enExample) * | 1973-09-11 | 1975-05-12 | ||
| JPS5312851A (en) * | 1976-07-22 | 1978-02-04 | Hexachimie | Novel phenoxyhydroxypropylamine* its preparation and its application for medical treatment |
| JPS58180473A (ja) * | 1982-04-16 | 1983-10-21 | Shikoku Chem Corp | イミダゾリル琥珀酸化合物および該化合物を用いるエポキシ樹脂硬化方法 |
| JPS60105645A (ja) * | 1983-11-12 | 1985-06-11 | Yasumitsu Tamura | アリ−ルコハク酸エステルの製造法 |
| JPS6456763A (en) * | 1987-07-01 | 1989-03-03 | Ciba Geigy Ag | Photosensitive epoxy resin and its use |
| DD271903A1 (de) * | 1988-05-17 | 1989-09-20 | Univ Halle Wittenberg | Verfahren zur herstellung stabiler, 2-unsubstituierter imidazol-3-oxide |
| WO1998031697A1 (en) * | 1997-01-15 | 1998-07-23 | Sankyo Company, Limited | Aryl c-glycoside compounds and sulfated esters thereof |
| JP2002508345A (ja) * | 1997-12-17 | 2002-03-19 | カイロテック・テクノロジー・リミテッド | 不斉水素化 |
| JP2003523931A (ja) * | 1998-12-04 | 2003-08-12 | スミスクライン・ビーチャム・コーポレイション | ビトロネクチンレセプター拮抗物質 |
| JP2000271485A (ja) * | 1999-03-24 | 2000-10-03 | Kazuhiko Saigo | オレフィン類のビスアルコキシカルボニル化触媒、及びコハク酸エステル誘導体の製造法 |
| JP2002541138A (ja) * | 1999-04-02 | 2002-12-03 | デュポン ファーマシューティカルズ カンパニー | マトリックスメタロプロテアーゼ、TNF−α、およびアグレカナーゼの阻害剤としての新規アミド誘導体 |
| WO2003006670A2 (en) * | 2001-07-09 | 2003-01-23 | Axys Pharmaceuticals, Inc. | 2-[5-(5-carbamimidoyl-1h-heteroaryl)-6-hydroxybiphenyl-3-yl]-succinic acid derivatives as factor viia inhibitors |
| JP2007525516A (ja) * | 2004-02-27 | 2007-09-06 | アムジエン・インコーポレーテツド | 代謝疾患の治療に使用するための、化合物、薬学的組成物及び方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1654218A2 (en) | 2006-05-10 |
| US20060235074A1 (en) | 2006-10-19 |
| WO2005016868A2 (en) | 2005-02-24 |
| GB0319069D0 (en) | 2003-09-17 |
| WO2005016868A3 (en) | 2005-05-19 |
| US7476759B2 (en) | 2009-01-13 |
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