ES2308260T3 - Derivados de imidazopiridinas como inhibidores de no-sintasa inducible. - Google Patents
Derivados de imidazopiridinas como inhibidores de no-sintasa inducible. Download PDFInfo
- Publication number
- ES2308260T3 ES2308260T3 ES04787262T ES04787262T ES2308260T3 ES 2308260 T3 ES2308260 T3 ES 2308260T3 ES 04787262 T ES04787262 T ES 04787262T ES 04787262 T ES04787262 T ES 04787262T ES 2308260 T3 ES2308260 T3 ES 2308260T3
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- Spain
- Prior art keywords
- quad
- alkyl
- phenyl
- ethyl
- pyridin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000003112 inhibitor Substances 0.000 title abstract description 10
- 230000001939 inductive effect Effects 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 161
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 169
- -1 ethylenedioxy group Chemical group 0.000 claims description 157
- 239000001257 hydrogen Substances 0.000 claims description 96
- 229910052739 hydrogen Inorganic materials 0.000 claims description 96
- 125000003545 alkoxy group Chemical group 0.000 claims description 86
- 229910052736 halogen Inorganic materials 0.000 claims description 85
- 150000002367 halogens Chemical group 0.000 claims description 85
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 76
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 75
- 150000003839 salts Chemical class 0.000 claims description 60
- 239000011737 fluorine Substances 0.000 claims description 51
- 229910052731 fluorine Inorganic materials 0.000 claims description 51
- 239000000460 chlorine Chemical group 0.000 claims description 50
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 49
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 49
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 45
- 125000001153 fluoro group Chemical group F* 0.000 claims description 42
- 150000001204 N-oxides Chemical class 0.000 claims description 41
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- 125000000623 heterocyclic group Chemical group 0.000 claims description 35
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 33
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 125000004076 pyridyl group Chemical group 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 125000006272 (C3-C7) cycloalkyl group Chemical group 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 18
- 150000001721 carbon Chemical group 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- 229920006395 saturated elastomer Polymers 0.000 claims description 16
- 239000000470 constituent Substances 0.000 claims description 15
- 229910052717 sulfur Chemical group 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 11
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 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
- 238000011282 treatment Methods 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 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
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 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 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 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
- 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
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 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
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 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 compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 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
- 230000001154 acute effect Effects 0.000 claims description 3
- 230000001684 chronic effect Effects 0.000 claims description 3
- 230000002757 inflammatory effect Effects 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 210000000056 organ Anatomy 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 compound 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
- 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 description 2
- FWRGKKMQLQXOLD-UHFFFAOYSA-N 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-(4-piperidin-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)N2CCCCC2)=C1 FWRGKKMQLQXOLD-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
- 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 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
- VGENBLARBITTCS-UHFFFAOYSA-N 2-[2-(4-methoxypyridin-2-yl)ethyl]-6-[4-(4-methylpiperidin-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)N2CCC(C)CC2)=C1 VGENBLARBITTCS-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
- 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 description 2
- BNZLGOCEWCGPJV-UHFFFAOYSA-N 2-[2-(4-methoxypyridin-2-yl)ethyl]-7-methyl-6-(4-piperidin-1-ylsulfonylphenyl)-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)N2CCCCC2)=C1 BNZLGOCEWCGPJV-UHFFFAOYSA-N 0.000 claims description 2
- AAKZNRPYQMZCHN-UHFFFAOYSA-N 2-[2-(4-methoxypyridin-2-yl)ethyl]-7-methyl-6-(4-pyrrolidin-1-ylsulfonylphenyl)-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)N2CCCC2)=C1 AAKZNRPYQMZCHN-UHFFFAOYSA-N 0.000 claims description 2
- DEODHXJCWPSXSZ-UHFFFAOYSA-N 4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]-n,n,3-trimethylbenzenesulfonamide Chemical compound COC1=CC=NC(CCC=2NC3=NC=C(C=C3N=2)C=2C(=CC(=CC=2)S(=O)(=O)N(C)C)C)=C1 DEODHXJCWPSXSZ-UHFFFAOYSA-N 0.000 claims description 2
- GLJSKFVMAXSSSM-UHFFFAOYSA-N 4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]-n,n-dimethyl-2-(trifluoromethoxy)benzenesulfonamide 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)N(C)C)=C1 GLJSKFVMAXSSSM-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
- XHWUMEKWSNEQQH-UHFFFAOYSA-N 4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]-n-(4-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(C)=CC=2)=C1 XHWUMEKWSNEQQH-UHFFFAOYSA-N 0.000 claims description 2
- ODVLESNQCLONMS-UHFFFAOYSA-N 4-[2-[2-(4-methoxypyridin-2-yl)ethyl]-1h-imidazo[4,5-b]pyridin-6-yl]-n-methyl-n-(2-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=CC=2)C)=C1 ODVLESNQCLONMS-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- 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 description 2
- 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 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
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Rheumatology (AREA)
- Transplantation (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Oncology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Communicable Diseases (AREA)
- Ophthalmology & Optometry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03022046 | 2003-10-01 | ||
| EP03022046 | 2003-10-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2308260T3 true ES2308260T3 (es) | 2008-12-01 |
Family
ID=34384570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES04787262T Expired - Lifetime ES2308260T3 (es) | 2003-10-01 | 2004-09-30 | Derivados de imidazopiridinas como inhibidores de no-sintasa inducible. |
Country Status (19)
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20060092220A (ko) | 2003-10-01 | 2006-08-22 | 알타나 파마 아게 | 유도성 ｎｏ-신타아제 저해제로서의 이미다조피리딘 유도체 |
| 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 |
| AR057525A1 (es) * | 2005-10-03 | 2007-12-05 | Astrazeneca Ab | Compuestos inhibidores selectivos de gsk3 y un proceso para su preparacion |
| AR055669A1 (es) * | 2005-10-03 | 2007-08-29 | Astrazeneca Ab | Derivados de 3h - imidazo[4, 5 -b]piridina como inhibidores selectivos de gsk3, metodos e internediarios para su preparacion, composiciones farmaceuticas que los contienen y su uso para la elaboracion de un medicamento para el tratamiento de enfermedades neurodegenerativas y mentales. |
| WO2007045622A1 (en) * | 2005-10-18 | 2007-04-26 | Nycomed Gmbh | Oxazolo [4 , 5-b] pyridine compounds as nitric oxide synthase inhibitors |
| EP1968962A2 (en) | 2005-12-14 | 2008-09-17 | Amgen Inc. | Diaza heterocyclic sulfonamide derivatives and their uses |
| KR20220020412A (ko) | 2015-03-16 | 2022-02-18 | 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 |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
| NZ546435A (en) | 2009-08-28 |
| 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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