RU2370488C2 - Ингибиторы матриксных металлопротеиназ - Google Patents
Ингибиторы матриксных металлопротеиназ Download PDFInfo
- Publication number
- RU2370488C2 RU2370488C2 RU2006106850/04A RU2006106850A RU2370488C2 RU 2370488 C2 RU2370488 C2 RU 2370488C2 RU 2006106850/04 A RU2006106850/04 A RU 2006106850/04A RU 2006106850 A RU2006106850 A RU 2006106850A RU 2370488 C2 RU2370488 C2 RU 2370488C2
- Authority
- RU
- Russia
- Prior art keywords
- ethyl
- substituted
- formula
- dioxo
- alkyl
- Prior art date
Links
- 102000002274 Matrix Metalloproteinases Human genes 0.000 title claims abstract description 13
- 108010000684 Matrix Metalloproteinases Proteins 0.000 title claims abstract description 13
- 239000003112 inhibitor Substances 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 124
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 125000002619 bicyclic group Chemical group 0.000 claims abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- 238000000034 method Methods 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- 230000004968 inflammatory condition Effects 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- 208000023275 Autoimmune disease Diseases 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- FBIZVDRWRLXUPV-UHFFFAOYSA-N 2-[2-(1,3-dioxoisoindol-2-yl)ethyl]-3-hydroxy-5-(4-phenylphenyl)pentanoic acid Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC(C(O)=O)C(O)CCC(C=C1)=CC=C1C1=CC=CC=C1 FBIZVDRWRLXUPV-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- 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
- 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
- 108010076501 Matrix Metalloproteinase 12 Proteins 0.000 claims description 2
- HBKOYSSZMRCIIP-UHFFFAOYSA-N 2-[2-(1,3-dioxoisoindol-2-yl)ethyl]-3-hydroxy-5-[4-(4-methylsulfanylphenyl)phenyl]pentanoic acid Chemical compound C1=CC(SC)=CC=C1C(C=C1)=CC=C1CCC(O)C(C(O)=O)CCN1C(=O)C2=CC=CC=C2C1=O HBKOYSSZMRCIIP-UHFFFAOYSA-N 0.000 claims 1
- NPLXOLKSKYCTIJ-UHFFFAOYSA-N 2-[2-(1,3-dioxoisoindol-2-yl)ethyl]-3-hydroxy-5-[4-[4-(trifluoromethoxy)phenyl]phenyl]pentanoic acid Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC(C(O)=O)C(O)CCC(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1 NPLXOLKSKYCTIJ-UHFFFAOYSA-N 0.000 claims 1
- VNIQUALILQYNQH-UHFFFAOYSA-N 3-hydroxy-2-[2-(3-methyl-2,4-dioxopyrimidin-1-yl)ethyl]-5-(4-pyrimidin-5-ylphenyl)pentanoic acid Chemical compound O=C1N(C)C(=O)C=CN1CCC(C(O)=O)C(O)CCC1=CC=C(C=2C=NC=NC=2)C=C1 VNIQUALILQYNQH-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 102000011721 Matrix Metalloproteinase 12 Human genes 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- -1 OR16 Chemical group 0.000 abstract description 25
- 230000000694 effects Effects 0.000 abstract description 5
- 125000005843 halogen group Chemical group 0.000 abstract description 4
- 230000005764 inhibitory process Effects 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- 238000006243 chemical reaction Methods 0.000 description 32
- 239000000243 solution Substances 0.000 description 32
- 239000000203 mixture Substances 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 25
- 239000002904 solvent Substances 0.000 description 23
- 239000000543 intermediate Substances 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 239000012299 nitrogen atmosphere Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 229910052799 carbon Inorganic materials 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000007792 addition Methods 0.000 description 9
- 125000002877 alkyl aryl group Chemical group 0.000 description 9
- 239000003039 volatile agent Substances 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- 230000015572 biosynthetic process Effects 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 6
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- 125000001424 substituent group Chemical group 0.000 description 6
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- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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- 239000002585 base Substances 0.000 description 5
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
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- 238000007254 oxidation reaction Methods 0.000 description 5
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- TYHGKLBJBHACOI-UHFFFAOYSA-N (4-methoxyphenyl)methyl 2,2,2-trichloroethanimidate Chemical compound COC1=CC=C(COC(=N)C(Cl)(Cl)Cl)C=C1 TYHGKLBJBHACOI-UHFFFAOYSA-N 0.000 description 4
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
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- HZQLUIZFUXNFHK-UHFFFAOYSA-N 1-(bromomethyl)-4-phenylbenzene Chemical group C1=CC(CBr)=CC=C1C1=CC=CC=C1 HZQLUIZFUXNFHK-UHFFFAOYSA-N 0.000 description 2
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- JBKINHFZTVLNEM-UHFFFAOYSA-N 2-bromoethoxy-tert-butyl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCCBr JBKINHFZTVLNEM-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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Classifications
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- 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
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
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- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—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
- 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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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—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
- 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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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- 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
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- C07D—HETEROCYCLIC COMPOUNDS
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- 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)
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- Macromonomer-Based Addition Polymer (AREA)
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- 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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| GB0321538.1 | 2003-09-13 |
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| RU2008146479/04A Division RU2008146479A (ru) | 2003-09-13 | 2008-11-26 | Ингибиторы матриксных металлопротеиназ |
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|---|---|
| RU2006106850A RU2006106850A (ru) | 2007-10-20 |
| RU2370488C2 true RU2370488C2 (ru) | 2009-10-20 |
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| RU2008146479/04A RU2008146479A (ru) | 2003-09-13 | 2008-11-26 | Ингибиторы матриксных металлопротеиназ |
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| JP (3) | JP2007505081A (enExample) |
| KR (3) | KR20060120648A (enExample) |
| CN (1) | CN1849306B (enExample) |
| AT (2) | ATE502922T1 (enExample) |
| AU (1) | AU2004272280C1 (enExample) |
| BR (1) | BRPI0413791A (enExample) |
| CA (1) | CA2538315C (enExample) |
| CY (1) | CY1109400T1 (enExample) |
| 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) |
| SG (1) | SG145685A1 (enExample) |
| SI (1) | SI1663970T1 (enExample) |
| WO (1) | WO2005026120A1 (enExample) |
| ZA (1) | ZA200602070B (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| FR2949463B1 (fr) * | 2009-08-26 | 2011-09-16 | Commissariat Energie Atomique | Inhibiteurs de mmp |
| 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 |
|---|---|---|---|---|
| WO1997043238A1 (en) * | 1996-05-15 | 1997-11-20 | Bayer Corporation | Substituted oxobutyric acids as matrix metalloprotease inhibitors |
| RU2179553C2 (ru) * | 1996-04-19 | 2002-02-20 | Акцо Нобель Н.В. | Замещенные бензиламины и содержащая их фармацевтическая композиция для лечения депрессии |
| WO2002083642A1 (en) * | 2001-04-13 | 2002-10-24 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as anti-inflammatory agents |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4102024A1 (de) * | 1991-01-24 | 1992-07-30 | Thomae Gmbh Dr K | Biphenylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| AU2199195A (en) * | 1994-04-28 | 1995-11-29 | Uniroyal Chemical Company, Inc. | Fungicidal azole derivatives |
| CZ172498A3 (cs) * | 1995-12-06 | 1998-12-16 | Astra Pharmaceuticals Ltd. | Sloučenina |
| 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 |
| 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 |
| GB0312654D0 (en) * | 2003-06-03 | 2003-07-09 | Glaxo Group Ltd | Therapeutically useful compounds |
| 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 |
-
2003
- 2003-09-13 GB GBGB0321538.1A patent/GB0321538D0/en not_active Ceased
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- 2004-09-10 MX MXPA06002458A patent/MXPA06002458A/es active IP Right Grant
- 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
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- 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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- 2008-11-26 RU RU2008146479/04A patent/RU2008146479A/ru not_active Application Discontinuation
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- 2009-01-27 CY CY20091100090T patent/CY1109400T1/el unknown
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- 2009-09-01 US US12/551,892 patent/US8343986B2/en not_active Expired - Fee Related
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Patent Citations (3)
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| RU2179553C2 (ru) * | 1996-04-19 | 2002-02-20 | Акцо Нобель Н.В. | Замещенные бензиламины и содержащая их фармацевтическая композиция для лечения депрессии |
| WO1997043238A1 (en) * | 1996-05-15 | 1997-11-20 | Bayer Corporation | Substituted oxobutyric acids as matrix metalloprotease inhibitors |
| WO2002083642A1 (en) * | 2001-04-13 | 2002-10-24 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as anti-inflammatory agents |
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| MATCHUS MICHAEL et al. "Development of new Carboxylic Acid-Based MMP Inhybitors Derived from Functionalized Propargylglycines" J. of Medicinal Chemistry, 2001, v.41, p.1060-1071. * |
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