JP2007505081A - 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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- JP2007505081A JP2007505081A JP2006525794A JP2006525794A JP2007505081A JP 2007505081 A JP2007505081 A JP 2007505081A JP 2006525794 A JP2006525794 A JP 2006525794A JP 2006525794 A JP2006525794 A JP 2006525794A JP 2007505081 A JP2007505081 A JP 2007505081A
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- 102000002274 Matrix Metalloproteinases Human genes 0.000 title abstract description 11
- 108010000684 Matrix Metalloproteinases Proteins 0.000 title abstract description 11
- 239000003112 inhibitor Substances 0.000 title abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 77
- 238000000034 method Methods 0.000 claims abstract description 27
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 26
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 23
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 23
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 10
- 125000000524 functional group Chemical group 0.000 claims abstract description 8
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims abstract description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 125000006168 tricyclic group Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 116
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 239000003153 chemical reaction reagent Substances 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 11
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- 239000003814 drug Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 208000023275 Autoimmune disease Diseases 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- DRNXZLHDIMEWHO-UHFFFAOYSA-N 2-[2-(1,3-dioxoisoindol-2-yl)ethyl]-3-hydroxy-5-(4-pyrimidin-5-ylphenyl)pentanoic acid Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC(C(O)=O)C(O)CCC(C=C1)=CC=C1C1=CN=CN=C1 DRNXZLHDIMEWHO-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 150000003457 sulfones Chemical class 0.000 claims description 3
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- 229940124597 therapeutic agent Drugs 0.000 claims description 3
- TYNXKLBAMDKDHF-UHFFFAOYSA-N 3-hydroxy-2-[2-(3-methyl-2,4-dioxopyrimidin-1-yl)ethyl]-5-(4-phenylphenyl)pentanoic acid Chemical compound O=C1N(C)C(=O)C=CN1CCC(C(O)=O)C(O)CCC1=CC=C(C=2C=CC=CC=2)C=C1 TYNXKLBAMDKDHF-UHFFFAOYSA-N 0.000 claims description 2
- WRTBLWFQLQBUBR-UHFFFAOYSA-N 3-hydroxy-2-[2-(3-methyl-2,4-dioxopyrimidin-1-yl)ethyl]-5-[4-[4-(trifluoromethoxy)phenyl]phenyl]pentanoic acid Chemical compound O=C1N(C)C(=O)C=CN1CCC(C(O)=O)C(O)CCC1=CC=C(C=2C=CC(OC(F)(F)F)=CC=2)C=C1 WRTBLWFQLQBUBR-UHFFFAOYSA-N 0.000 claims description 2
- BHLJQPGIHDTZBX-UHFFFAOYSA-N 3-hydroxy-2-[2-(3-methyl-2,6-dioxopyrimidin-1-yl)ethyl]-5-(4-phenylphenyl)pentanoic acid Chemical compound O=C1N(C)C=CC(=O)N1CCC(C(O)=O)C(O)CCC1=CC=C(C=2C=CC=CC=2)C=C1 BHLJQPGIHDTZBX-UHFFFAOYSA-N 0.000 claims description 2
- NAAQNJLBTAIZDO-UHFFFAOYSA-N 5-[4-(1-benzofuran-2-yl)phenyl]-2-[2-(1,3-dioxoisoindol-2-yl)ethyl]-3-hydroxypentanoic acid Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC(C(O)=O)C(O)CCC1=CC=C(C=2OC3=CC=CC=C3C=2)C=C1 NAAQNJLBTAIZDO-UHFFFAOYSA-N 0.000 claims description 2
- KXJLRFIYARWGFH-UHFFFAOYSA-N 5-[4-(4-acetylphenyl)phenyl]-2-[2-(1,3-dioxoisoindol-2-yl)ethyl]-3-hydroxypentanoic acid Chemical compound C1=CC(C(=O)C)=CC=C1C(C=C1)=CC=C1CCC(O)C(C(O)=O)CCN1C(=O)C2=CC=CC=C2C1=O KXJLRFIYARWGFH-UHFFFAOYSA-N 0.000 claims description 2
- MSYHSDYSURKJEX-UHFFFAOYSA-N 5-[4-(4-acetylphenyl)phenyl]-3-hydroxy-2-[2-(3-methyl-2,4-dioxopyrimidin-1-yl)ethyl]pentanoic acid Chemical compound C1=CC(C(=O)C)=CC=C1C(C=C1)=CC=C1CCC(O)C(C(O)=O)CCN1C(=O)N(C)C(=O)C=C1 MSYHSDYSURKJEX-UHFFFAOYSA-N 0.000 claims description 2
- UIZCUKPUFVLHGU-UHFFFAOYSA-N 5-[4-(4-cyanophenyl)phenyl]-2-[2-(1,3-dioxoisoindol-2-yl)ethyl]-3-hydroxypentanoic acid Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC(C(O)=O)C(O)CCC(C=C1)=CC=C1C1=CC=C(C#N)C=C1 UIZCUKPUFVLHGU-UHFFFAOYSA-N 0.000 claims description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- 208000037979 autoimmune inflammatory disease Diseases 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- KDSNLLCOUMXHFV-UHFFFAOYSA-N CC(CCN1C(=O)C2=CC=CC=C2C1=O)C(CCC3=CC=C(C=C3)C4=CC=C(C=C4)SC)O Chemical compound CC(CCN1C(=O)C2=CC=CC=C2C1=O)C(CCC3=CC=C(C=C3)C4=CC=C(C=C4)SC)O KDSNLLCOUMXHFV-UHFFFAOYSA-N 0.000 claims 1
- OVHDDQBXGFOIAB-UHFFFAOYSA-N CC(CCN1C=CC(=O)N(C1=O)C)C(CCC2=CC=C(C=C2)C3=CN=CN=C3)O Chemical compound CC(CCN1C=CC(=O)N(C1=O)C)C(CCC2=CC=C(C=C2)C3=CN=CN=C3)O OVHDDQBXGFOIAB-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 3
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 39
- 239000000243 solution Substances 0.000 description 29
- 239000000203 mixture Substances 0.000 description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000000543 intermediate Substances 0.000 description 21
- 238000003756 stirring Methods 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000012299 nitrogen atmosphere Substances 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- -1 cyano, hydroxy, nitro, amino Chemical group 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 9
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 8
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- 238000004440 column chromatography Methods 0.000 description 7
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
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- 125000001424 substituent group Chemical group 0.000 description 6
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 description 5
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- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 4
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- 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
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- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
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- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
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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
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- 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
- C07D403/10—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 aromatic rings
-
- 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
- C07D405/10—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 aromatic rings
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Soft Magnetic Materials (AREA)
- Indole Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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| GBGB0321538.1A GB0321538D0 (en) | 2003-09-13 | 2003-09-13 | Therapeutically useful compounds |
| PCT/EP2004/010319 WO2005026120A1 (en) | 2003-09-13 | 2004-09-10 | Matrix metalloproteinase inhibitors |
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| JP2012012663A Division JP2012107031A (ja) | 2003-09-13 | 2012-01-25 | マトリックスメタロプロテイナーゼの阻害剤 |
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| JP2011132261A Withdrawn JP2011231118A (ja) | 2003-09-13 | 2011-06-14 | マトリックスメタロプロテイナーゼの阻害剤 |
| JP2012012663A Pending JP2012107031A (ja) | 2003-09-13 | 2012-01-25 | マトリックスメタロプロテイナーゼの阻害剤 |
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| DE (2) | DE602004031991D1 (enExample) |
| DK (1) | DK1663970T3 (enExample) |
| ES (2) | ES2314436T3 (enExample) |
| GB (1) | GB0321538D0 (enExample) |
| HR (1) | HRP20080668T3 (enExample) |
| IL (1) | IL173305A (enExample) |
| IS (2) | IS2622B (enExample) |
| MA (1) | MA28039A1 (enExample) |
| MX (1) | MXPA06002458A (enExample) |
| NO (1) | NO20060540L (enExample) |
| NZ (2) | NZ545211A (enExample) |
| PL (1) | PL1663970T3 (enExample) |
| PT (1) | PT1663970E (enExample) |
| RU (2) | RU2370488C2 (enExample) |
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| SI (1) | SI1663970T1 (enExample) |
| WO (1) | WO2005026120A1 (enExample) |
| ZA (1) | ZA200602070B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011231118A (ja) * | 2003-09-13 | 2011-11-17 | Glaxo Group Ltd | マトリックスメタロプロテイナーゼの阻害剤 |
| JP2013503142A (ja) * | 2009-08-26 | 2013-01-31 | コミッサリア ア レネルジ アトミック エ オー エネルジ アルターネイティブス | Ｍｍｐインヒビターとしてのシュードジペプチド |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA013539B1 (ru) * | 2005-02-22 | 2010-06-30 | Рэнбакси Лабораториз Лимитед | Производные 5-фенилпентановой кислоты в качестве ингибиторов матричной металлопротеиназы для лечения астмы и других заболеваний |
| AU2013200728B2 (en) * | 2006-08-22 | 2014-12-18 | Sun Pharmaceutical Industries Limited | Matrix metalloproteinase inhibitors |
| JO2868B1 (en) * | 2006-08-22 | 2015-03-15 | رانبكسي لابوراتوريز ليمتد | Inhibitors of metabolic protein protein enzyme |
| ES2569660T3 (es) | 2007-06-08 | 2016-05-12 | Mannkind Corporation | Inhibidores de la IRE-1alfa |
| CN103119030A (zh) | 2010-07-30 | 2013-05-22 | 兰贝克赛实验室有限公司 | 基质金属蛋白酶抑制剂 |
| US20140148459A1 (en) | 2010-09-24 | 2014-05-29 | Ranbaxy Laboratories Limited | Matrix metalloproteinase inhibitors |
| EP2926808A1 (en) | 2012-11-28 | 2015-10-07 | Administración General De La Communidad Autónoma De Euskadi | Use of metalloprotease inhibitors for the treatment of polycystic liver diseases |
| SG11201806416XA (en) | 2016-02-12 | 2018-08-30 | Astellas Pharma Inc | Tetrahydroisoquinoline derivatives |
| CN110769866B (zh) * | 2017-06-13 | 2022-07-29 | 爱惜康有限责任公司 | 具有可控愈合的外科缝合器 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995029901A1 (en) * | 1994-04-28 | 1995-11-09 | Uniroyal Chemical Company, Inc. | Fungicidal azole derivatives |
| JP2000501700A (ja) * | 1995-12-06 | 2000-02-15 | アストラ・フアーマシユウテイカルズ・リミテツド | 化合物 |
| JP2006526590A (ja) * | 2003-06-03 | 2006-11-24 | グラクソ グループ リミテッド | マトリックスメタロプロテイナーゼ阻害剤 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE4102024A1 (de) * | 1991-01-24 | 1992-07-30 | Thomae Gmbh Dr K | Biphenylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| DK0898566T3 (da) | 1996-04-19 | 2003-03-03 | Akzo Nobel Nv | Substituerede benzylaminer og anvendelse deraf til behandling af depression |
| MY132470A (en) * | 1996-05-15 | 2007-10-31 | Bayer Corp | Substituted oxobutyric acids as matrix metalloprotease inhibitors |
| US6242616B1 (en) * | 1996-12-03 | 2001-06-05 | The Trustees Of The University Of Pennsylvania | Synthetic techniques and intermediates for polyhydroxy, dienyl lactone derivatives |
| US6870058B2 (en) * | 1996-12-03 | 2005-03-22 | The Trustees Of The University Of Pennsylvania | Compounds which mimic the chemical and biological properties of discodermolide |
| US20050065353A1 (en) * | 1996-12-03 | 2005-03-24 | Smith Amos B. | Synthetic techniques and intermediates for polyhydroxy dienyl lactones and mimics thereof |
| US5789605A (en) * | 1996-12-03 | 1998-08-04 | Trustees Of The University Of Pennsylvania | Synthetic techniques and intermediates for polyhydroxy, dienyl lactones and mimics thereof |
| US6096904A (en) | 1996-12-03 | 2000-08-01 | The Trustees Of The University Of Pennsylvania | Synthetic techniques and intermediates for polyhydroxy, dienyl lactone derivatives |
| US5804581A (en) * | 1997-05-15 | 1998-09-08 | Bayer Corporation | Inhibition of matrix metalloproteases by substituted phenalkyl compounds |
| US6608052B2 (en) * | 2000-02-16 | 2003-08-19 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as anti-inflammatory agents |
| JP2005504727A (ja) * | 2001-04-13 | 2005-02-17 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | 抗炎症薬として有用なウレア化合物 |
| US7102008B2 (en) | 2002-08-01 | 2006-09-05 | Bristol-Myers Squibb Company | Hydantoin derivatives as inhibitors of matrix metalloproteinases and/or TNF-α converting enzyme |
| BR0314898A (pt) * | 2002-11-19 | 2005-08-02 | Galderma Res & Dev | Compostos, composição cosmética, uso cosmético de uma composição, uso de um composto e composição farmacêutica |
| GB0314488D0 (en) * | 2003-06-20 | 2003-07-23 | Glaxo Group Ltd | Therapeutically useful compounds |
| GB0319069D0 (en) * | 2003-08-14 | 2003-09-17 | Glaxo Group Ltd | Therapeutically useful compounds |
| GB0321538D0 (en) | 2003-09-13 | 2003-10-15 | Glaxo Group Ltd | Therapeutically useful compounds |
| EA013539B1 (ru) * | 2005-02-22 | 2010-06-30 | Рэнбакси Лабораториз Лимитед | Производные 5-фенилпентановой кислоты в качестве ингибиторов матричной металлопротеиназы для лечения астмы и других заболеваний |
| JO2868B1 (en) * | 2006-08-22 | 2015-03-15 | رانبكسي لابوراتوريز ليمتد | Inhibitors of metabolic protein protein enzyme |
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2003
- 2003-09-13 GB GBGB0321538.1A patent/GB0321538D0/en not_active Ceased
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2004
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- 2004-09-10 DK DK04765231T patent/DK1663970T3/da active
- 2004-09-10 AU AU2004272280A patent/AU2004272280C1/en not_active Ceased
- 2004-09-10 NZ NZ545211A patent/NZ545211A/en not_active IP Right Cessation
- 2004-09-10 KR KR1020067005114A patent/KR20060120648A/ko not_active Ceased
- 2004-09-10 PT PT04765231T patent/PT1663970E/pt unknown
- 2004-09-10 HR HR20080668T patent/HRP20080668T3/xx unknown
- 2004-09-10 KR KR1020127000264A patent/KR20120007566A/ko not_active Ceased
- 2004-09-10 RU RU2006106850/04A patent/RU2370488C2/ru not_active IP Right Cessation
- 2004-09-10 EP EP10176905A patent/EP2295408A1/en not_active Withdrawn
- 2004-09-10 BR BRPI0413791-4A patent/BRPI0413791A/pt not_active IP Right Cessation
- 2004-09-10 ES ES04765231T patent/ES2314436T3/es not_active Expired - Lifetime
- 2004-09-10 AT AT04765231T patent/ATE413384T1/de active
- 2004-09-10 SG SG200805432-2A patent/SG145685A1/en unknown
- 2004-09-10 US US10/571,443 patent/US7601729B2/en not_active Expired - Fee Related
- 2004-09-10 EP EP08163972A patent/EP2042488B1/en not_active Expired - Lifetime
- 2004-09-10 EP EP04765231A patent/EP1663970B1/en not_active Expired - Lifetime
- 2004-09-10 SI SI200431008T patent/SI1663970T1/sl unknown
- 2004-09-10 PL PL04765231T patent/PL1663970T3/pl unknown
- 2004-09-10 WO PCT/EP2004/010319 patent/WO2005026120A1/en not_active Ceased
- 2004-09-10 CN CN200480026229.7A patent/CN1849306B/zh not_active Expired - Fee Related
- 2004-09-10 CA CA2538315A patent/CA2538315C/en not_active Expired - Fee Related
- 2004-09-10 DE DE602004031991T patent/DE602004031991D1/de not_active Expired - Lifetime
- 2004-09-10 KR KR1020137014317A patent/KR20130079628A/ko not_active Ceased
- 2004-09-10 ES ES08163972T patent/ES2362954T3/es not_active Expired - Lifetime
- 2004-09-10 DE DE602004017622T patent/DE602004017622D1/de not_active Expired - Lifetime
- 2004-09-10 JP JP2006525794A patent/JP2007505081A/ja active Pending
- 2004-09-10 NZ NZ573479A patent/NZ573479A/en not_active IP Right Cessation
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2006
- 2006-01-23 IL IL173305A patent/IL173305A/en not_active IP Right Cessation
- 2006-01-26 IS IS8268A patent/IS2622B/is unknown
- 2006-02-02 NO NO20060540A patent/NO20060540L/no not_active Application Discontinuation
- 2006-03-10 ZA ZA200602070A patent/ZA200602070B/en unknown
- 2006-03-14 MA MA28873A patent/MA28039A1/fr unknown
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2008
- 2008-11-07 US US12/266,767 patent/US8263602B2/en not_active Expired - Fee Related
- 2008-11-26 RU RU2008146479/04A patent/RU2008146479A/ru not_active Application Discontinuation
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2009
- 2009-01-27 CY CY20091100090T patent/CY1109400T1/el unknown
- 2009-08-19 IS IS8843A patent/IS8843A/is unknown
- 2009-09-01 US US12/551,892 patent/US8343986B2/en not_active Expired - Fee Related
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2011
- 2011-06-14 JP JP2011132261A patent/JP2011231118A/ja not_active Withdrawn
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2012
- 2012-01-25 JP JP2012012663A patent/JP2012107031A/ja active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995029901A1 (en) * | 1994-04-28 | 1995-11-09 | Uniroyal Chemical Company, Inc. | Fungicidal azole derivatives |
| JP2000501700A (ja) * | 1995-12-06 | 2000-02-15 | アストラ・フアーマシユウテイカルズ・リミテツド | 化合物 |
| JP2006526590A (ja) * | 2003-06-03 | 2006-11-24 | グラクソ グループ リミテッド | マトリックスメタロプロテイナーゼ阻害剤 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011231118A (ja) * | 2003-09-13 | 2011-11-17 | Glaxo Group Ltd | マトリックスメタロプロテイナーゼの阻害剤 |
| JP2013503142A (ja) * | 2009-08-26 | 2013-01-31 | コミッサリア ア レネルジ アトミック エ オー エネルジ アルターネイティブス | Ｍｍｐインヒビターとしてのシュードジペプチド |
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