JP2007507466A - 誘導性ｎｏシンターゼ阻害剤としてのイミダゾピリジン誘導体 - Google Patents
誘導性ｎｏシンターゼ阻害剤としてのイミダゾピリジン誘導体 Download PDFInfo
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- JP2007507466A JP2007507466A JP2006530263A JP2006530263A JP2007507466A JP 2007507466 A JP2007507466 A JP 2007507466A JP 2006530263 A JP2006530263 A JP 2006530263A JP 2006530263 A JP2006530263 A JP 2006530263A JP 2007507466 A JP2007507466 A JP 2007507466A
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- Prior art keywords
- alkyl
- phenyl
- ethyl
- pyridin
- imidazo
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- 102100029438 Nitric oxide synthase, inducible Human genes 0.000 title abstract description 30
- 101710089543 Nitric oxide synthase, inducible Proteins 0.000 title abstract description 30
- 239000003112 inhibitor Substances 0.000 title abstract description 7
- 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 title description 4
- -1 ethylenedioxy group Chemical group 0.000 claims description 199
- 150000001875 compounds Chemical class 0.000 claims description 163
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 100
- 239000001257 hydrogen Substances 0.000 claims description 97
- 229910052739 hydrogen Inorganic materials 0.000 claims description 97
- 229910052736 halogen Inorganic materials 0.000 claims description 85
- 150000002367 halogens Chemical class 0.000 claims description 85
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 78
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 74
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 70
- 239000000460 chlorine Chemical group 0.000 claims description 49
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 48
- 239000011737 fluorine Substances 0.000 claims description 48
- 229910052731 fluorine Inorganic materials 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 47
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 44
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 44
- 125000001153 fluoro group Chemical group F* 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 39
- 150000001204 N-oxides Chemical class 0.000 claims description 35
- 125000000623 heterocyclic group Chemical group 0.000 claims description 31
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
- 125000004076 pyridyl group Chemical group 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 19
- 239000005977 Ethylene Substances 0.000 claims description 19
- 150000001721 carbon Chemical group 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- 229920006395 saturated elastomer Polymers 0.000 claims description 13
- 229910052717 sulfur Chemical group 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 11
- 125000003386 piperidinyl group Chemical group 0.000 claims description 11
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 7
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
- 125000002393 azetidinyl group Chemical group 0.000 claims description 7
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 239000001301 oxygen Chemical group 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 5
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 208000037976 chronic inflammation Diseases 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 210000000056 organ Anatomy 0.000 claims description 5
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- CHVLLOYBRQEGEM-UHFFFAOYSA-N 4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]-n-phenylbenzenesulfonamide Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)NC=2C=CC=CC=2)=C1 CHVLLOYBRQEGEM-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 230000001154 acute effect Effects 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 230000002093 peripheral effect Effects 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims description 3
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical group C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 2
- LLVLJQGDQPJQDW-UHFFFAOYSA-N 1-[4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]phenyl]sulfonyl-1,4-diazepan-5-one Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)N2CCC(=O)NCC2)=C1 LLVLJQGDQPJQDW-UHFFFAOYSA-N 0.000 claims description 2
- CJZSLOGARPSYAU-UHFFFAOYSA-N 1-[4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]phenyl]sulfonyl-4-methyl-1,4-diazepan-5-one Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)N2CCC(=O)N(C)CC2)=C1 CJZSLOGARPSYAU-UHFFFAOYSA-N 0.000 claims description 2
- MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 claims description 2
- UQCGBFFEFMDNQP-UHFFFAOYSA-N 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-(4-pyrrolidin-1-ylsulfonylphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)N2CCCC2)=C1 UQCGBFFEFMDNQP-UHFFFAOYSA-N 0.000 claims description 2
- AYYFUKWCLZOHPE-UHFFFAOYSA-N 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-[3-(4-methylpiperazin-1-yl)sulfonylphenyl]-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=C(C=CC=2)S(=O)(=O)N2CCN(C)CC2)=C1 AYYFUKWCLZOHPE-UHFFFAOYSA-N 0.000 claims description 2
- UIXHHDQYIINPBD-UHFFFAOYSA-N 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-[4-(4-methylpiperazin-1-yl)sulfonyl-3-(trifluoromethoxy)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=C(OC(F)(F)F)C(=CC=2)S(=O)(=O)N2CCN(C)CC2)=C1 UIXHHDQYIINPBD-UHFFFAOYSA-N 0.000 claims description 2
- IIWHSJWNULMGNK-UHFFFAOYSA-N 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-[4-(4-methylpiperazin-1-yl)sulfonyl-3-(trifluoromethyl)phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=C(C(=CC=2)S(=O)(=O)N2CCN(C)CC2)C(F)(F)F)=C1 IIWHSJWNULMGNK-UHFFFAOYSA-N 0.000 claims description 2
- UQRYDMSZRQQKGV-UHFFFAOYSA-N 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-[4-(4-methylpiperazin-1-yl)sulfonylphenyl]-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)N2CCN(C)CC2)=C1 UQRYDMSZRQQKGV-UHFFFAOYSA-N 0.000 claims description 2
- KCVMUQHTORHZGX-UHFFFAOYSA-N 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-[4-(4-phenylpiperazin-1-yl)sulfonylphenyl]-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)N2CCN(CC2)C=2C=CC=CC=2)=C1 KCVMUQHTORHZGX-UHFFFAOYSA-N 0.000 claims description 2
- UEMAFCQRUKCPOR-UHFFFAOYSA-N 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-[4-[(4-methyl-1,4-diazepan-1-yl)sulfonyl]phenyl]-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)N2CCN(C)CCC2)=C1 UEMAFCQRUKCPOR-UHFFFAOYSA-N 0.000 claims description 2
- BJIDRNQMIWZUMQ-UHFFFAOYSA-N 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-[4-[4-(2-methylphenyl)piperazin-1-yl]sulfonylphenyl]-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)N2CCN(CC2)C=2C(=CC=CC=2)C)=C1 BJIDRNQMIWZUMQ-UHFFFAOYSA-N 0.000 claims description 2
- UXQFUHBKCGXENA-UHFFFAOYSA-N 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-[4-[4-(2-phenylethyl)piperazin-1-yl]sulfonylphenyl]-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)N2CCN(CCC=3C=CC=CC=3)CC2)=C1 UXQFUHBKCGXENA-UHFFFAOYSA-N 0.000 claims description 2
- ZTVZRODAAUIGDP-UHFFFAOYSA-N 4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]-n-(2-methylphenyl)benzenesulfonamide Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)NC=2C(=CC=CC=2)C)=C1 ZTVZRODAAUIGDP-UHFFFAOYSA-N 0.000 claims description 2
- NTJDZDSQJQMQCO-UHFFFAOYSA-N 4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]-n-methyl-n-pyridin-4-ylbenzenesulfonamide Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)N(C)C=2C=CN=CC=2)=C1 NTJDZDSQJQMQCO-UHFFFAOYSA-N 0.000 claims description 2
- RLALJVXOXTVMIQ-UHFFFAOYSA-N 4-[4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]phenyl]sulfonylmorpholine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)N2CCOCC2)=C1 RLALJVXOXTVMIQ-UHFFFAOYSA-N 0.000 claims description 2
- JUOMGMHCJKNQIL-UHFFFAOYSA-N 4-[4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]phenyl]sulfonylthiomorpholine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)N2CCSCC2)=C1 JUOMGMHCJKNQIL-UHFFFAOYSA-N 0.000 claims description 2
- QIVNJPUJPXAISM-UHFFFAOYSA-N 4-benzyl-1-[4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]phenyl]sulfonyl-1,4-diazepan-5-one Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)N2CCC(=O)N(CC=3C=CC=CC=3)CC2)=C1 QIVNJPUJPXAISM-UHFFFAOYSA-N 0.000 claims description 2
- XKNQXNRMXIDQMT-UHFFFAOYSA-N 4-ethyl-1-[4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]phenyl]sulfonyl-1,4-diazepan-5-one Chemical compound C1CC(=O)N(CC)CCN1S(=O)(=O)C1=CC=C(C=2C=C3N=C(CCC=4N=CC=C(OC)C=4)NC3=NC=2)C=C1 XKNQXNRMXIDQMT-UHFFFAOYSA-N 0.000 claims description 2
- RKDSRDVECWGUQK-UHFFFAOYSA-N 6,7-diethoxy-2-[4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]phenyl]sulfonyl-3,4-dihydro-1h-isoquinoline Chemical compound C1C=2C=C(OCC)C(OCC)=CC=2CCN1S(=O)(=O)C(C=C1)=CC=C1C(C=C1N=2)=CN=C1NC=2CCC1=CC(OC)=CC=N1 RKDSRDVECWGUQK-UHFFFAOYSA-N 0.000 claims description 2
- MKDKTQNUBJGNJL-UHFFFAOYSA-N 6,7-dimethoxy-2-[4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]phenyl]sulfonyl-3,4-dihydro-1h-isoquinoline Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)N2CC3=CC(OC)=C(OC)C=C3CC2)=C1 MKDKTQNUBJGNJL-UHFFFAOYSA-N 0.000 claims description 2
- JZRXSLZWWJFFGE-UHFFFAOYSA-N 6-[4-(4-benzylpiperazin-1-yl)sulfonylphenyl]-2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)N2CCN(CC=3C=CC=CC=3)CC2)=C1 JZRXSLZWWJFFGE-UHFFFAOYSA-N 0.000 claims description 2
- DCLHVGYQJVQKPE-UHFFFAOYSA-N 6-[4-(4-ethylpiperazin-1-yl)sulfonylphenyl]-2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridine Chemical compound C1CN(CC)CCN1S(=O)(=O)C1=CC=C(C=2C=C3N=C(CCC=4N=CC=C(OC)C=4)NC3=NC=2)C=C1 DCLHVGYQJVQKPE-UHFFFAOYSA-N 0.000 claims description 2
- IMPGAKUCBTZIBR-UHFFFAOYSA-N 6-[4-(azetidin-1-ylsulfonyl)phenyl]-2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)N2CCC2)=C1 IMPGAKUCBTZIBR-UHFFFAOYSA-N 0.000 claims description 2
- NFQMBGJBDOOKAE-UHFFFAOYSA-N 6-[4-(azetidin-1-ylsulfonyl)phenyl]-2-[2-(4-methoxypyridin-2-yl)ethyl]-7-methyl-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C(C)=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)N2CCC2)=C1 NFQMBGJBDOOKAE-UHFFFAOYSA-N 0.000 claims description 2
- GCVOIDGBTSJEFB-UHFFFAOYSA-N 6-[4-[4-(2,6-dimethylphenyl)piperazin-1-yl]sulfonylphenyl]-2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)N2CCN(CC2)C=2C(=CC=CC=2C)C)=C1 GCVOIDGBTSJEFB-UHFFFAOYSA-N 0.000 claims description 2
- KZYRAAIBSKICOP-UHFFFAOYSA-N 8-[4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]phenyl]sulfonyl-1,4-dioxa-8-azaspiro[4.5]decane Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)N2CCC3(CC2)OCCO3)=C1 KZYRAAIBSKICOP-UHFFFAOYSA-N 0.000 claims description 2
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical group C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 2
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Psychology (AREA)
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- Communicable Diseases (AREA)
- Endocrinology (AREA)
- Ophthalmology & Optometry (AREA)
- Transplantation (AREA)
- Oncology (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Psychiatry (AREA)
- Hematology (AREA)
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- Vascular Medicine (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03022046 | 2003-10-01 | ||
| PCT/EP2004/052377 WO2005030770A1 (en) | 2003-10-01 | 2004-09-30 | Imidazopyridine-derivatives as inducible no-synthase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007507466A true JP2007507466A (ja) | 2007-03-29 |
| JP2007507466A5 JP2007507466A5 (enExample) | 2007-11-15 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006530263A Withdrawn JP2007507466A (ja) | 2003-10-01 | 2004-09-30 | 誘導性ｎｏシンターゼ阻害剤としてのイミダゾピリジン誘導体 |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US7279488B2 (enExample) |
| EP (1) | EP1670796B1 (enExample) |
| JP (1) | JP2007507466A (enExample) |
| KR (1) | KR20060092297A (enExample) |
| CN (1) | CN100422182C (enExample) |
| AT (1) | ATE399168T1 (enExample) |
| AU (1) | AU2004276014A1 (enExample) |
| BR (1) | BRPI0414933A (enExample) |
| CA (1) | CA2540243A1 (enExample) |
| DE (1) | DE602004014628D1 (enExample) |
| EA (1) | EA200600607A1 (enExample) |
| ES (1) | ES2308260T3 (enExample) |
| IL (1) | IL173810A0 (enExample) |
| MX (1) | MXPA06003351A (enExample) |
| NO (1) | NO20061317L (enExample) |
| NZ (1) | NZ546435A (enExample) |
| RS (1) | RS20060200A (enExample) |
| WO (1) | WO2005030770A1 (enExample) |
| ZA (1) | ZA200601553B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE602004014523D1 (de) | 2003-10-01 | 2008-07-31 | Nycomed Gmbh | Imidazoä4,5-büpyridinderivate als inhibitoren der induzierbaren no-synthase |
| JP2007507464A (ja) | 2003-10-01 | 2007-03-29 | アルタナ ファルマ アクチエンゲゼルシャフト | 新規のアミノピリジン誘導体 |
| EA010261B1 (ru) | 2003-10-01 | 2008-06-30 | Алтана Фарма Аг | Производные имидазопиридина как ингибиторы индуцируемой no - синтазы |
| NZ546435A (en) * | 2003-10-01 | 2009-08-28 | Altana Pharma Ag | Imidazopyridine-derivatives as inducible NO-synthase inhibitors |
| EA012280B1 (ru) | 2004-05-28 | 2009-08-28 | 4Сц Аг | Новые производные тетрагидропиридотиофена |
| WO2005120642A2 (en) | 2004-06-11 | 2005-12-22 | Altana Pharma Ag | Tetrahydropyridothiophenes for treating hyperproliferative disorders |
| CA2596202A1 (en) | 2005-02-09 | 2006-08-17 | Altana Pharma Ag | Tetrahydropyridothiophenes for the treatment of proliferative diseases such as cancer |
| WO2006084904A1 (en) | 2005-02-11 | 2006-08-17 | Nycomed Gmbh | Tetrahydropyridothiophenes as antripoliferative agents for the treatment of cancer |
| JP2008542243A (ja) | 2005-05-25 | 2008-11-27 | ニコメッド ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規のテトラヒドロピリドチオフェン |
| US7714136B2 (en) | 2005-05-25 | 2010-05-11 | 4Sc Ag | Tetrahydropyridothiophenes |
| AR057525A1 (es) * | 2005-10-03 | 2007-12-05 | Astrazeneca Ab | Compuestos inhibidores selectivos de gsk3 y un proceso para su preparacion |
| UY29825A1 (es) * | 2005-10-03 | 2007-05-31 | Astrazeneca Ab | Derivados sustituidos de 3h-imidazol-(4,5 b (beta))piridina-2-il benzoatos y benzamidas, composiciones farmacéuticas que los contienen y aplicaciones |
| WO2007045622A1 (en) * | 2005-10-18 | 2007-04-26 | Nycomed Gmbh | Oxazolo [4 , 5-b] pyridine compounds as nitric oxide synthase inhibitors |
| CA2632027A1 (en) | 2005-12-14 | 2007-06-21 | Amgen Inc. | Diaza heterocyclic sulfonamide derivatives and their uses |
| KR102359212B1 (ko) | 2015-03-16 | 2022-02-08 | 에프. 호프만-라 로슈 아게 | Tlr7 작용제 및 hbv 캡시드 조립 억제제를 사용하는 병용 치료 |
| GB201512635D0 (en) | 2015-07-17 | 2015-08-26 | Ucl Business Plc | Uses of therapeutic compounds |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE418966B (sv) | 1974-02-18 | 1981-07-06 | Haessle Ab | Analogiforfarande for framstellning av foreningar med magsyrasekretionsinhiberande verkan |
| US4045564A (en) * | 1974-02-18 | 1977-08-30 | Ab Hassle | Benzimidazole derivatives useful as gastric acid secretion inhibitors |
| GB8307865D0 (en) * | 1983-03-22 | 1983-04-27 | Fujisawa Pharmaceutical Co | Benzimidazole derivatives |
| AU650953B2 (en) * | 1991-03-21 | 1994-07-07 | Novartis Ag | Inhaler |
| SE512835C2 (sv) | 1996-01-08 | 2000-05-22 | Astrazeneca Ab | Doseringsform innehållande en mångfald enheter alla inneslutande syralabil H+K+ATPas-hämmare |
| AUPP873799A0 (en) * | 1999-02-17 | 1999-03-11 | Fujisawa Pharmaceutical Co., Ltd. | Pyridine compounds |
| CN1307176C (zh) | 2002-03-27 | 2007-03-28 | 奥坦纳医药公司 | 新的烷氧基吡啶衍生物 |
| DE602004014523D1 (de) | 2003-10-01 | 2008-07-31 | Nycomed Gmbh | Imidazoä4,5-büpyridinderivate als inhibitoren der induzierbaren no-synthase |
| NZ546435A (en) * | 2003-10-01 | 2009-08-28 | Altana Pharma Ag | Imidazopyridine-derivatives as inducible NO-synthase inhibitors |
| EA010261B1 (ru) * | 2003-10-01 | 2008-06-30 | Алтана Фарма Аг | Производные имидазопиридина как ингибиторы индуцируемой no - синтазы |
| EA200600609A1 (ru) | 2003-10-01 | 2006-10-27 | Алтана Фарма Аг | Производные имидазопиридина в качестве ингибиторов индуцируемой no-синтазы |
| JP2007507464A (ja) | 2003-10-01 | 2007-03-29 | アルタナ ファルマ アクチエンゲゼルシャフト | 新規のアミノピリジン誘導体 |
-
2004
- 2004-09-30 NZ NZ546435A patent/NZ546435A/en unknown
- 2004-09-30 US US10/573,202 patent/US7279488B2/en not_active Expired - Fee Related
- 2004-09-30 JP JP2006530263A patent/JP2007507466A/ja not_active Withdrawn
- 2004-09-30 RS YUP-2006/0200A patent/RS20060200A/sr unknown
- 2004-09-30 EA EA200600607A patent/EA200600607A1/ru unknown
- 2004-09-30 WO PCT/EP2004/052377 patent/WO2005030770A1/en not_active Ceased
- 2004-09-30 CA CA002540243A patent/CA2540243A1/en not_active Abandoned
- 2004-09-30 AU AU2004276014A patent/AU2004276014A1/en not_active Abandoned
- 2004-09-30 BR BRPI0414933-5A patent/BRPI0414933A/pt not_active IP Right Cessation
- 2004-09-30 AT AT04787262T patent/ATE399168T1/de not_active IP Right Cessation
- 2004-09-30 MX MXPA06003351A patent/MXPA06003351A/es not_active Application Discontinuation
- 2004-09-30 KR KR1020067005902A patent/KR20060092297A/ko not_active Withdrawn
- 2004-09-30 CN CNB2004800278331A patent/CN100422182C/zh not_active Expired - Fee Related
- 2004-09-30 ES ES04787262T patent/ES2308260T3/es not_active Expired - Lifetime
- 2004-09-30 DE DE602004014628T patent/DE602004014628D1/de not_active Expired - Lifetime
- 2004-09-30 EP EP04787262A patent/EP1670796B1/en not_active Expired - Lifetime
-
2006
- 2006-02-19 IL IL173810A patent/IL173810A0/en unknown
- 2006-02-22 ZA ZA200601553A patent/ZA200601553B/en unknown
- 2006-03-23 NO NO20061317A patent/NO20061317L/no not_active Application Discontinuation
-
2007
- 2007-09-27 US US11/905,033 patent/US7709488B2/en not_active Expired - Fee Related
-
2010
- 2010-05-03 US US12/772,455 patent/US20100216790A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| DE602004014628D1 (de) | 2008-08-07 |
| MXPA06003351A (es) | 2006-06-08 |
| US7709488B2 (en) | 2010-05-04 |
| CN1856495A (zh) | 2006-11-01 |
| US20080021039A1 (en) | 2008-01-24 |
| CN100422182C (zh) | 2008-10-01 |
| NZ546435A (en) | 2009-08-28 |
| KR20060092297A (ko) | 2006-08-22 |
| WO2005030770A1 (en) | 2005-04-07 |
| US20100216790A1 (en) | 2010-08-26 |
| IL173810A0 (en) | 2006-07-05 |
| ATE399168T1 (de) | 2008-07-15 |
| EA200600607A1 (ru) | 2006-10-27 |
| US7279488B2 (en) | 2007-10-09 |
| BRPI0414933A (pt) | 2006-11-07 |
| NO20061317L (no) | 2006-03-23 |
| US20060293302A1 (en) | 2006-12-28 |
| ZA200601553B (en) | 2007-04-25 |
| EP1670796B1 (en) | 2008-06-25 |
| AU2004276014A1 (en) | 2005-04-07 |
| CA2540243A1 (en) | 2005-04-07 |
| RS20060200A (sr) | 2008-08-07 |
| ES2308260T3 (es) | 2008-12-01 |
| HK1096549A1 (zh) | 2007-06-01 |
| EP1670796A1 (en) | 2006-06-21 |
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