KR20060120648A - 기질 금속단백분해효소 억제제 - Google Patents
기질 금속단백분해효소 억제제 Download PDFInfo
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- KR20060120648A KR20060120648A KR1020067005114A KR20067005114A KR20060120648A KR 20060120648 A KR20060120648 A KR 20060120648A KR 1020067005114 A KR1020067005114 A KR 1020067005114A KR 20067005114 A KR20067005114 A KR 20067005114A KR 20060120648 A KR20060120648 A KR 20060120648A
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- 239000003771 matrix metalloproteinase inhibitor Substances 0.000 title 1
- 229940121386 matrix metalloproteinase inhibitor Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 140
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 77
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 25
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 10
- 125000000524 functional group Chemical group 0.000 claims abstract description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims abstract description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 6
- 125000006168 tricyclic group Chemical group 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 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
- 208000027866 inflammatory disease Diseases 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- 208000023275 Autoimmune disease Diseases 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 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 3
- 230000001363 autoimmune Effects 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
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- 229940124597 therapeutic agent Drugs 0.000 claims description 3
- 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
- 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 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
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 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
- 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 1
- 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 1
- 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 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 108010000684 Matrix Metalloproteinases Proteins 0.000 abstract description 10
- 102000002274 Matrix Metalloproteinases Human genes 0.000 abstract description 10
- 238000002360 preparation method Methods 0.000 abstract description 9
- 239000003112 inhibitor Substances 0.000 abstract description 7
- 125000001475 halogen functional group Chemical group 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
- 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
- 238000006243 chemical reaction Methods 0.000 description 40
- 239000000243 solution Substances 0.000 description 40
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- -1 Cyano, hydroxy, nitro, amino Chemical group 0.000 description 16
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 15
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 239000000725 suspension Substances 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 239000003039 volatile agent Substances 0.000 description 9
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000002366 halogen compounds Chemical class 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
- 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
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 6
- 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
- 229940088598 enzyme Drugs 0.000 description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000000010 aprotic solvent Substances 0.000 description 5
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- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 230000003647 oxidation Effects 0.000 description 5
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- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 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
- 206010061218 Inflammation Diseases 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
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- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 4
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- 125000006239 protecting group Chemical group 0.000 description 4
- 239000012453 solvate Substances 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- 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 3
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
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- 239000005557 antagonist Substances 0.000 description 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 3
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
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- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 3
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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
- ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 2
- JBKINHFZTVLNEM-UHFFFAOYSA-N 2-bromoethoxy-tert-butyl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCCBr JBKINHFZTVLNEM-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 2
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- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
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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
- 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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- A61K31/40—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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- A61K31/395—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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- 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
-
- 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
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Transplantation (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Soft Magnetic Materials (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Lubricants (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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0321538.1A GB0321538D0 (en) | 2003-09-13 | 2003-09-13 | Therapeutically useful compounds |
| GB0321538.1 | 2003-09-13 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020127000264A Division KR20120007566A (ko) | 2003-09-13 | 2004-09-10 | 기질 금속단백분해효소 억제제 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20060120648A true KR20060120648A (ko) | 2006-11-27 |
Family
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Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020067005114A Ceased KR20060120648A (ko) | 2003-09-13 | 2004-09-10 | 기질 금속단백분해효소 억제제 |
| KR1020127000264A Ceased KR20120007566A (ko) | 2003-09-13 | 2004-09-10 | 기질 금속단백분해효소 억제제 |
| KR1020137014317A Ceased KR20130079628A (ko) | 2003-09-13 | 2004-09-10 | 기질 금속단백분해효소 억제제 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020127000264A Ceased KR20120007566A (ko) | 2003-09-13 | 2004-09-10 | 기질 금속단백분해효소 억제제 |
| KR1020137014317A Ceased KR20130079628A (ko) | 2003-09-13 | 2004-09-10 | 기질 금속단백분해효소 억제제 |
Country Status (28)
| Country | Link |
|---|---|
| US (3) | US7601729B2 (https=) |
| EP (3) | EP1663970B1 (https=) |
| JP (3) | JP2007505081A (https=) |
| KR (3) | KR20060120648A (https=) |
| CN (1) | CN1849306B (https=) |
| AT (2) | ATE413384T1 (https=) |
| AU (1) | AU2004272280C1 (https=) |
| BR (1) | BRPI0413791A (https=) |
| CA (1) | CA2538315C (https=) |
| CY (1) | CY1109400T1 (https=) |
| DE (2) | DE602004031991D1 (https=) |
| DK (1) | DK1663970T3 (https=) |
| ES (2) | ES2362954T3 (https=) |
| GB (1) | GB0321538D0 (https=) |
| HR (1) | HRP20080668T3 (https=) |
| IL (1) | IL173305A (https=) |
| IS (2) | IS2622B (https=) |
| MA (1) | MA28039A1 (https=) |
| MX (1) | MXPA06002458A (https=) |
| NO (1) | NO20060540L (https=) |
| NZ (2) | NZ545211A (https=) |
| PL (1) | PL1663970T3 (https=) |
| PT (1) | PT1663970E (https=) |
| RU (2) | RU2370488C2 (https=) |
| SG (1) | SG145685A1 (https=) |
| SI (1) | SI1663970T1 (https=) |
| WO (1) | WO2005026120A1 (https=) |
| ZA (1) | ZA200602070B (https=) |
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 |
| AP2413A (en) * | 2005-02-22 | 2012-06-01 | Ranbaxy Lab Ltd | 5-phenyl-pentanoic acid derivatives as matrix metalloproteinase inhibitors for the treatment of asthma and other disease. |
| AU2013200728B2 (en) * | 2006-08-22 | 2014-12-18 | Sun Pharmaceutical Industries Limited | Matrix metalloproteinase inhibitors |
| PL2074093T3 (pl) * | 2006-08-22 | 2013-03-29 | Sun Pharmaceutical Ind Ltd | Sposób przygotowywania inhibitorów metaloproteinazy macierzy i chiralnego środka wspomagającego |
| MX2009013332A (es) | 2007-06-08 | 2010-01-25 | Mannkind Corp | Inhibidores de ire-1 alfa. |
| FR2949463B1 (fr) * | 2009-08-26 | 2011-09-16 | Commissariat Energie Atomique | Inhibiteurs de mmp |
| MX2013001240A (es) | 2010-07-30 | 2013-08-27 | Ranbaxy Lab Ltd | Inhibidores de metaloproteinas de matriz. |
| WO2012038942A1 (en) | 2010-09-24 | 2012-03-29 | Ranbaxy Laboratories Limited | Matrix metalloproteinase inhibitors |
| WO2014083229A1 (es) | 2012-11-28 | 2014-06-05 | Administración General De La Comunidad Autónoma De Euskadi | Uso de inhibidores de metaloproteasas en el tratamiento de enfermedades hepáticas poliquísticas |
| SG11201806416XA (en) | 2016-02-12 | 2018-08-30 | Astellas Pharma Inc | Tetrahydroisoquinoline derivatives |
| JP7143334B2 (ja) * | 2017-06-13 | 2022-09-28 | エシコン エルエルシー | 治癒を制御させる手術用ステープラ |
Family Cites Families (21)
| 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 |
| WO1995029901A1 (en) * | 1994-04-28 | 1995-11-09 | Uniroyal Chemical Company, Inc. | Fungicidal azole derivatives |
| TR199801000T2 (xx) * | 1995-12-06 | 1998-08-21 | Astra Pharmaceuticals Ltd. | Bile�ikler |
| WO1997040027A1 (en) | 1996-04-19 | 1997-10-30 | Akzo Nobel N.V. | Substituted benzylamines and their use for the treatment of depression |
| CO4990925A1 (es) * | 1996-05-15 | 2000-12-26 | Bayer Corp | Acidos oxibutiricos sustituidos como inhibidores de la metaloproteasa de matriz |
| 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 |
| US6242616B1 (en) * | 1996-12-03 | 2001-06-05 | The Trustees Of The University Of Pennsylvania | Synthetic techniques and intermediates for polyhydroxy, dienyl lactone derivatives |
| 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 |
| WO2002083642A1 (en) | 2001-04-13 | 2002-10-24 | 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 |
| AU2003290120A1 (en) * | 2002-11-19 | 2004-06-15 | Galderma Research & Development, S.N.C. | Biaromatic compounds which activate PPAR-Gama type receptors, and use thereof in cosmetic or pharmaceutical compositions |
| 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 |
| AP2413A (en) * | 2005-02-22 | 2012-06-01 | Ranbaxy Lab Ltd | 5-phenyl-pentanoic acid derivatives as matrix metalloproteinase inhibitors for the treatment of asthma and other disease. |
| PL2074093T3 (pl) * | 2006-08-22 | 2013-03-29 | Sun Pharmaceutical Ind Ltd | Sposób przygotowywania inhibitorów metaloproteinazy macierzy i chiralnego środka wspomagającego |
-
2003
- 2003-09-13 GB GBGB0321538.1A patent/GB0321538D0/en not_active Ceased
-
2004
- 2004-09-10 KR KR1020067005114A patent/KR20060120648A/ko not_active Ceased
- 2004-09-10 EP EP04765231A patent/EP1663970B1/en not_active Expired - Lifetime
- 2004-09-10 ES ES08163972T patent/ES2362954T3/es not_active Expired - Lifetime
- 2004-09-10 WO PCT/EP2004/010319 patent/WO2005026120A1/en not_active Ceased
- 2004-09-10 DE DE602004031991T patent/DE602004031991D1/de not_active Expired - Lifetime
- 2004-09-10 KR KR1020127000264A patent/KR20120007566A/ko not_active Ceased
- 2004-09-10 NZ NZ545211A patent/NZ545211A/en not_active IP Right Cessation
- 2004-09-10 EP EP08163972A patent/EP2042488B1/en not_active Expired - Lifetime
- 2004-09-10 JP JP2006525794A patent/JP2007505081A/ja active Pending
- 2004-09-10 KR KR1020137014317A patent/KR20130079628A/ko not_active Ceased
- 2004-09-10 RU RU2006106850/04A patent/RU2370488C2/ru not_active IP Right Cessation
- 2004-09-10 SG SG200805432-2A patent/SG145685A1/en unknown
- 2004-09-10 ES ES04765231T patent/ES2314436T3/es not_active Expired - Lifetime
- 2004-09-10 CN CN200480026229.7A patent/CN1849306B/zh not_active Expired - Fee Related
- 2004-09-10 MX MXPA06002458A patent/MXPA06002458A/es active IP Right Grant
- 2004-09-10 BR BRPI0413791-4A patent/BRPI0413791A/pt not_active IP Right Cessation
- 2004-09-10 EP EP10176905A patent/EP2295408A1/en not_active Withdrawn
- 2004-09-10 AT AT04765231T patent/ATE413384T1/de active
- 2004-09-10 AU AU2004272280A patent/AU2004272280C1/en not_active Ceased
- 2004-09-10 HR HR20080668T patent/HRP20080668T3/xx unknown
- 2004-09-10 PL PL04765231T patent/PL1663970T3/pl unknown
- 2004-09-10 DE DE602004017622T patent/DE602004017622D1/de not_active Expired - Lifetime
- 2004-09-10 SI SI200431008T patent/SI1663970T1/sl unknown
- 2004-09-10 AT AT08163972T patent/ATE502922T1/de not_active IP Right Cessation
- 2004-09-10 NZ NZ573479A patent/NZ573479A/en not_active IP Right Cessation
- 2004-09-10 PT PT04765231T patent/PT1663970E/pt unknown
- 2004-09-10 DK DK04765231T patent/DK1663970T3/da active
- 2004-09-10 US US10/571,443 patent/US7601729B2/en not_active Expired - Fee Related
- 2004-09-10 CA CA2538315A patent/CA2538315C/en not_active Expired - Fee Related
-
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
-
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
-
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
-
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
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