NZ546435A - Imidazopyridine-derivatives as inducible NO-synthase inhibitors - Google Patents
Imidazopyridine-derivatives as inducible NO-synthase inhibitorsInfo
- Publication number
- NZ546435A NZ546435A NZ546435A NZ54643504A NZ546435A NZ 546435 A NZ546435 A NZ 546435A NZ 546435 A NZ546435 A NZ 546435A NZ 54643504 A NZ54643504 A NZ 54643504A NZ 546435 A NZ546435 A NZ 546435A
- Authority
- NZ
- New Zealand
- Prior art keywords
- alkyl
- phenyl
- ethyl
- pyridin
- alkoxy
- Prior art date
Links
- 102100029438 Nitric oxide synthase, inducible Human genes 0.000 title abstract description 31
- 101710089543 Nitric oxide synthase, inducible Proteins 0.000 title abstract description 30
- 239000003112 inhibitor Substances 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 159
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
- 238000011282 treatment Methods 0.000 claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 7
- 208000037976 chronic inflammation Diseases 0.000 claims abstract description 5
- 230000001154 acute effect Effects 0.000 claims abstract description 4
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims abstract description 4
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 4
- 210000000056 organ Anatomy 0.000 claims abstract description 4
- 230000002093 peripheral effect Effects 0.000 claims abstract description 3
- -1 1-4C-alkyl Chemical group 0.000 claims description 145
- 239000001257 hydrogen Substances 0.000 claims description 96
- 229910052739 hydrogen Inorganic materials 0.000 claims description 96
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 96
- 229910052736 halogen Inorganic materials 0.000 claims description 85
- 150000002367 halogens Chemical class 0.000 claims description 85
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 81
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 74
- 125000000229 (C1-C4)alkoxy group Chemical class 0.000 claims description 68
- 150000003839 salts Chemical class 0.000 claims description 59
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 43
- 150000001204 N-oxides Chemical class 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 36
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 125000004076 pyridyl group Chemical group 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 239000000460 chlorine Chemical group 0.000 claims description 21
- 229910052801 chlorine Inorganic materials 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 20
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 19
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 19
- 239000005977 Ethylene Substances 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 17
- 239000000470 constituent Substances 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 239000011737 fluorine Substances 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
- 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 9
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 8
- 229910052717 sulfur Chemical group 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 7
- 125000002393 azetidinyl group Chemical group 0.000 claims description 7
- 230000002401 inhibitory effect Effects 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 6
- 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Chemical group 0.000 claims description 6
- 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 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 6
- 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 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 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
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 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
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical group C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 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
- 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
- MCAXYBOJVGTFKA-UHFFFAOYSA-N 6-[2-fluoro-4-(4-methylpiperazin-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(C)CC2)F)=C1 MCAXYBOJVGTFKA-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
- 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
- GJCUZUJEQRQQON-UHFFFAOYSA-N n-cyclopropyl-4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]benzenesulfonamide Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)NC2CC2)=C1 GJCUZUJEQRQQON-UHFFFAOYSA-N 0.000 claims description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
- IWUWJMDAGHCEGR-UHFFFAOYSA-N 1-[4-[4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]phenyl]sulfonylpiperazin-1-yl]ethanone Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)N2CCN(CC2)C(C)=O)=C1 IWUWJMDAGHCEGR-UHFFFAOYSA-N 0.000 claims 1
- NCPQIHLSOULRHE-UHFFFAOYSA-N 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-[2-methyl-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)C)=C1 NCPQIHLSOULRHE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- JJYUUKAFDVDYFK-UHFFFAOYSA-N 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-[4-[4-(4-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(C)=CC=2)=C1 JJYUUKAFDVDYFK-UHFFFAOYSA-N 0.000 claims 1
- AHBJXZDULVLWFB-UHFFFAOYSA-N 4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]-n-methyl-n-(4-methylphenyl)benzenesulfonamide Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)N(C)C=2C=CC(C)=CC=2)=C1 AHBJXZDULVLWFB-UHFFFAOYSA-N 0.000 claims 1
- DHAVKGIGNSTUSO-UHFFFAOYSA-N 4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]-n-methyl-n-phenylbenzenesulfonamide Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)N(C)C=2C=CC=CC=2)=C1 DHAVKGIGNSTUSO-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- NABULSYQLYJQLW-UHFFFAOYSA-N 4-[4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-7-methyl-1h-imidazo[4,5-b]pyridin-6-yl]phenyl]sulfonylmorpholine Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C(C)=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)N2CCOCC2)=C1 NABULSYQLYJQLW-UHFFFAOYSA-N 0.000 claims 1
- LPIKXMRCNLQVRY-UHFFFAOYSA-N 4-[4-[4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]phenyl]sulfonylpiperazin-1-yl]benzonitrile 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#N)=C1 LPIKXMRCNLQVRY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- SHFWETIBRNSELW-UHFFFAOYSA-N 6-[3-chloro-4-(4-methylpiperazin-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=C(Cl)C(=CC=2)S(=O)(=O)N2CCN(C)CC2)=C1 SHFWETIBRNSELW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- MMPFTVHFXNBWIJ-UHFFFAOYSA-N 6-[4-[4-(2,4-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(C)=CC=2)C)=C1 MMPFTVHFXNBWIJ-UHFFFAOYSA-N 0.000 claims 1
- UBJXMIHDMMDBFI-UHFFFAOYSA-N 6-[4-[4-(2-methoxyethyl)piperazin-1-yl]sulfonylphenyl]-2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridine Chemical compound C1CN(CCOC)CCN1S(=O)(=O)C1=CC=C(C=2C=C3N=C(CCC=4N=CC=C(OC)C=4)NC3=NC=2)C=C1 UBJXMIHDMMDBFI-UHFFFAOYSA-N 0.000 claims 1
- GXHUCKDJEYQZMB-UHFFFAOYSA-N 6-[4-[4-(3,5-dichlorophenyl)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=C(Cl)C=C(Cl)C=2)=C1 GXHUCKDJEYQZMB-UHFFFAOYSA-N 0.000 claims 1
- KKWQQEJRJQKSCI-UHFFFAOYSA-N n,n-bis(2-methoxyethyl)-4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N(CCOC)CCOC)=CC=C1C1=CN=C(NC(CCC=2N=CC=C(OC)C=2)=N2)C2=C1 KKWQQEJRJQKSCI-UHFFFAOYSA-N 0.000 claims 1
- WMQRDRBTAVIEFL-UHFFFAOYSA-N n-(2-fluoro-4-methylphenyl)-4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]benzenesulfonamide Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C=CC(=CC=2)S(=O)(=O)NC=2C(=CC(C)=CC=2)F)=C1 WMQRDRBTAVIEFL-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 147
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 111
- 239000000203 mixture Substances 0.000 description 99
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 59
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 58
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 58
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 56
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 47
- 229940093499 ethyl acetate Drugs 0.000 description 37
- 235000019439 ethyl acetate Nutrition 0.000 description 37
- 239000007858 starting material Substances 0.000 description 35
- 239000000243 solution Substances 0.000 description 34
- 238000001819 mass spectrum Methods 0.000 description 33
- 239000012074 organic phase Substances 0.000 description 30
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Landscapes
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| EP03022046 | 2003-10-01 | ||
| PCT/EP2004/052377 WO2005030770A1 (en) | 2003-10-01 | 2004-09-30 | Imidazopyridine-derivatives as inducible no-synthase inhibitors |
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| MXPA06003351A (es) * | 2003-10-01 | 2006-06-08 | Altana Pharma Ag | Derivados de imidazopiridina como inhibidores de no-sintasa inducible. |
| EP1670798A1 (en) | 2003-10-01 | 2006-06-21 | Altana Pharma AG | Aminopyridine-derivatives as inductible no-synthase inhibitors |
| KR20060092221A (ko) | 2003-10-01 | 2006-08-22 | 알타나 파마 아게 | 유도성 ｎｏ-신타제 억제제로서의이미다조（4,5-ｂ）피리딘 유도체 |
| US7723523B2 (en) | 2004-05-28 | 2010-05-25 | 4Sc Ag | Tetrahydropyridothiophenes |
| CA2569623A1 (en) | 2004-06-11 | 2005-12-22 | Altana Pharma Ag | Novel compounds and use of tetrahydropyridothiophenes |
| AU2006212224A1 (en) | 2005-02-09 | 2006-08-17 | 4Sc Ag | Tetrahydropyridothiophenes for the treatment of proliferative diseases such as cancer |
| CA2596501A1 (en) | 2005-02-11 | 2006-08-17 | Altana Pharma Ag | Tetrahydropyridothiophenes as antripoliferative agents for the treatment of cancer |
| EP1893618A2 (en) | 2005-05-25 | 2008-03-05 | Nycomed GmbH | Tetrahydropyridothiophenes for use in the treatment of cancer |
| EP1896484A2 (en) | 2005-05-25 | 2008-03-12 | Nycomed GmbH | Tetrahydropyridothiophenes for use in the treatment of cancer |
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| EP1968962A2 (en) | 2005-12-14 | 2008-09-17 | Amgen Inc. | Diaza heterocyclic sulfonamide derivatives and their uses |
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| US4045564A (en) | 1974-02-18 | 1977-08-30 | Ab Hassle | Benzimidazole derivatives useful as gastric acid secretion inhibitors |
| SE418966B (sv) | 1974-02-18 | 1981-07-06 | Haessle Ab | Analogiforfarande for framstellning av foreningar med magsyrasekretionsinhiberande verkan |
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| ATE384722T1 (de) * | 2002-03-27 | 2008-02-15 | Nycomed Gmbh | Alkoxypyridinderivate |
| MXPA06003351A (es) * | 2003-10-01 | 2006-06-08 | Altana Pharma Ag | Derivados de imidazopiridina como inhibidores de no-sintasa inducible. |
| KR20060092220A (ko) * | 2003-10-01 | 2006-08-22 | 알타나 파마 아게 | 유도성 ｎｏ-신타아제 저해제로서의 이미다조피리딘 유도체 |
| KR20060092221A (ko) | 2003-10-01 | 2006-08-22 | 알타나 파마 아게 | 유도성 ｎｏ-신타제 억제제로서의이미다조（4,5-ｂ）피리딘 유도체 |
| BRPI0414873A (pt) | 2003-10-01 | 2006-12-12 | Altana Pharma Ag | derivados de imidazopiridina como inibidores de no-sintase induzìveis |
| EP1670798A1 (en) | 2003-10-01 | 2006-06-21 | Altana Pharma AG | Aminopyridine-derivatives as inductible no-synthase inhibitors |
-
2004
- 2004-09-30 MX MXPA06003351A patent/MXPA06003351A/es not_active Application Discontinuation
- 2004-09-30 AT AT04787262T patent/ATE399168T1/de not_active IP Right Cessation
- 2004-09-30 CN CNB2004800278331A patent/CN100422182C/zh not_active Expired - Fee Related
- 2004-09-30 EP EP04787262A patent/EP1670796B1/en not_active Expired - Lifetime
- 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 RS YUP-2006/0200A patent/RS20060200A/sr unknown
- 2004-09-30 EA EA200600607A patent/EA200600607A1/ru unknown
- 2004-09-30 BR BRPI0414933-5A patent/BRPI0414933A/pt not_active IP Right Cessation
- 2004-09-30 JP JP2006530263A patent/JP2007507466A/ja not_active Withdrawn
- 2004-09-30 KR KR1020067005902A patent/KR20060092297A/ko not_active Withdrawn
- 2004-09-30 NZ NZ546435A patent/NZ546435A/en unknown
- 2004-09-30 WO PCT/EP2004/052377 patent/WO2005030770A1/en not_active Ceased
- 2004-09-30 DE DE602004014628T patent/DE602004014628D1/de not_active Expired - Lifetime
- 2004-09-30 US US10/573,202 patent/US7279488B2/en not_active Expired - Fee Related
- 2004-09-30 ES ES04787262T patent/ES2308260T3/es 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 |
|---|---|
| EA200600607A1 (ru) | 2006-10-27 |
| CA2540243A1 (en) | 2005-04-07 |
| EP1670796B1 (en) | 2008-06-25 |
| NO20061317L (no) | 2006-03-23 |
| ATE399168T1 (de) | 2008-07-15 |
| EP1670796A1 (en) | 2006-06-21 |
| KR20060092297A (ko) | 2006-08-22 |
| US7709488B2 (en) | 2010-05-04 |
| US7279488B2 (en) | 2007-10-09 |
| ES2308260T3 (es) | 2008-12-01 |
| ZA200601553B (en) | 2007-04-25 |
| US20060293302A1 (en) | 2006-12-28 |
| IL173810A0 (en) | 2006-07-05 |
| CN1856495A (zh) | 2006-11-01 |
| CN100422182C (zh) | 2008-10-01 |
| HK1096549A1 (zh) | 2007-06-01 |
| DE602004014628D1 (de) | 2008-08-07 |
| WO2005030770A1 (en) | 2005-04-07 |
| AU2004276014A1 (en) | 2005-04-07 |
| BRPI0414933A (pt) | 2006-11-07 |
| RS20060200A (sr) | 2008-08-07 |
| MXPA06003351A (es) | 2006-06-08 |
| US20080021039A1 (en) | 2008-01-24 |
| US20100216790A1 (en) | 2010-08-26 |
| JP2007507466A (ja) | 2007-03-29 |
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Legal Events
| Date | Code | Title | Description |
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| PSEA | Patent sealed | ||
| RENW | Renewal (renewal fees accepted) |