HRP20030752A2 - Pyridazinone aldose reductase inhibitors - Google Patents

Info

Publication number

HRP20030752A2

HRP20030752A2 HR20030752A HRP20030752A HRP20030752A2 HR P20030752 A2 HRP20030752 A2 HR P20030752A2 HR 20030752 A HR20030752 A HR 20030752A HR P20030752 A HRP20030752 A HR P20030752A HR P20030752 A2 HRP20030752 A2 HR P20030752A2

Authority

HR

Croatia

Prior art keywords

sulfonyl

pyridazin

alkyl

chloro

methylbenzofuran

Prior art date

2001-03-30

Links

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• 239000003288 aldose reductase inhibitor Substances 0.000 title description 13
• 229940090865 aldose reductase inhibitors used in diabetes Drugs 0.000 title description 8
• AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title description 4
• 150000001875 compounds Chemical class 0.000 claims description 343
• -1 cinolinyl Chemical group 0.000 claims description 252
• 229940002612 prodrug Drugs 0.000 claims description 102
• 239000000651 prodrug Substances 0.000 claims description 102
• 150000003839 salts Chemical class 0.000 claims description 86
• 238000000034 method Methods 0.000 claims description 83
• 125000001424 substituent group Chemical group 0.000 claims description 60
• 235000019000 fluorine Nutrition 0.000 claims description 59
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 55
• 125000001153 fluoro group Chemical group F* 0.000 claims description 41
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 40
• 239000000460 chlorine Substances 0.000 claims description 32
• 229910052801 chlorine Inorganic materials 0.000 claims description 32
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 32
• 241000124008 Mammalia Species 0.000 claims description 30
• 229910052736 halogen Inorganic materials 0.000 claims description 29
• 150000002367 halogens Chemical class 0.000 claims description 29
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 28
• 229910052794 bromium Inorganic materials 0.000 claims description 25
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 24
• 229910052739 hydrogen Inorganic materials 0.000 claims description 24
• 239000001257 hydrogen Substances 0.000 claims description 24
• 125000002883 imidazolyl group Chemical group 0.000 claims description 24
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 23
• 125000002971 oxazolyl group Chemical group 0.000 claims description 23
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 23
• 125000000335 thiazolyl group Chemical group 0.000 claims description 23
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
• 125000004647 alkyl sulfenyl group Chemical group 0.000 claims description 21
• 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 21
• 208000028867 ischemia Diseases 0.000 claims description 21
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 20
• 229910052731 fluorine Inorganic materials 0.000 claims description 20
• 239000011737 fluorine Substances 0.000 claims description 20
• 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 20
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 19
• 208000002249 Diabetes Complications Diseases 0.000 claims description 18
• 206010012655 Diabetic complications Diseases 0.000 claims description 18
• 125000004076 pyridyl group Chemical group 0.000 claims description 18
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 18
• 125000001544 thienyl group Chemical group 0.000 claims description 18
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 17
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 17
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 17
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
• 125000002541 furyl group Chemical group 0.000 claims description 17
• 125000005956 isoquinolyl group Chemical group 0.000 claims description 17
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 17
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 17
• 125000005493 quinolyl group Chemical group 0.000 claims description 17
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 17
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 17
• 125000001425 triazolyl group Chemical group 0.000 claims description 17
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 16
• 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 15
• 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 15
• 125000004534 benzothien-2-yl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 15
• FXFPQPNUMWQRAO-UHFFFAOYSA-N 6-[(5-chloro-3-methyl-1-benzofuran-2-yl)sulfonyl]pyridazin-3(2h)-one Chemical compound O1C2=CC=C(Cl)C=C2C(C)=C1S(=O)(=O)C=1C=CC(=O)NN=1 FXFPQPNUMWQRAO-UHFFFAOYSA-N 0.000 claims description 14
• 125000005554 pyridyloxy group Chemical group 0.000 claims description 14
• 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 13
• 125000001624 naphthyl group Chemical group 0.000 claims description 13
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 13
• 239000003085 diluting agent Substances 0.000 claims description 12
• HXNAGYMCTAINEA-UHFFFAOYSA-N 3-(1h-indol-2-ylsulfonyl)-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)C=2NC3=CC=CC=C3C=2)=N1 HXNAGYMCTAINEA-UHFFFAOYSA-N 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 9
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 9
• HTJQFBOZQJFYDR-UHFFFAOYSA-N 3-[(3-methyl-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound O1C2=CC=CC=C2C(C)=C1S(=O)(=O)C=1C=CC(=O)NN=1 HTJQFBOZQJFYDR-UHFFFAOYSA-N 0.000 claims description 9
• DXMRTFOZJATGPZ-UHFFFAOYSA-N 3-[[3-methyl-5-(trifluoromethyl)-1-benzofuran-2-yl]sulfonyl]-1h-pyridazin-6-one Chemical compound O1C2=CC=C(C(F)(F)F)C=C2C(C)=C1S(=O)(=O)C=1C=CC(=O)NN=1 DXMRTFOZJATGPZ-UHFFFAOYSA-N 0.000 claims description 9
• 210000005003 heart tissue Anatomy 0.000 claims description 9
• PESVWIXUZNFVOB-UHFFFAOYSA-N 3-[(5-chloro-3-methyl-1-benzofuran-2-yl)sulfonyl]-6-methoxypyridazine Chemical compound N1=NC(OC)=CC=C1S(=O)(=O)C1=C(C)C2=CC(Cl)=CC=C2O1 PESVWIXUZNFVOB-UHFFFAOYSA-N 0.000 claims description 8
• BVGVSUYAYNIIGE-UHFFFAOYSA-N 3-[(5-fluoro-3-methyl-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound O1C2=CC=C(F)C=C2C(C)=C1S(=O)(=O)C=1C=CC(=O)NN=1 BVGVSUYAYNIIGE-UHFFFAOYSA-N 0.000 claims description 8
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 8
• 125000000217 alkyl group Chemical group 0.000 claims description 8
• JOGGJDKLNQCAQJ-UHFFFAOYSA-N 3-[(5-chloro-3-methyl-1-benzothiophen-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound S1C2=CC=C(Cl)C=C2C(C)=C1S(=O)(=O)C=1C=CC(=O)NN=1 JOGGJDKLNQCAQJ-UHFFFAOYSA-N 0.000 claims description 7
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 7
• 125000004536 indazol-1-yl group Chemical group N1(N=CC2=CC=CC=C12)* 0.000 claims description 7
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 6
• ZCHJRGKQXZDDOT-UHFFFAOYSA-N 3-(1h-indol-3-ylsulfonyl)-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)C=2C3=CC=CC=C3NC=2)=N1 ZCHJRGKQXZDDOT-UHFFFAOYSA-N 0.000 claims description 6
• CABVMWOKBSURKS-UHFFFAOYSA-N 3-[(3-hydroxy-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound O1C2=CC=CC=C2C(O)=C1S(=O)(=O)C=1C=CC(=O)NN=1 CABVMWOKBSURKS-UHFFFAOYSA-N 0.000 claims description 6
• CJENBJORWKGVTB-UHFFFAOYSA-N 3-thieno[2,3-b]pyridin-2-ylsulfonyl-1H-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)C=2SC3=NC=CC=C3C=2)=N1 CJENBJORWKGVTB-UHFFFAOYSA-N 0.000 claims description 6
• RBZSSTPBYFHRSR-UHFFFAOYSA-N 3-(1-benzofuran-2-ylsulfonyl)-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)C=2OC3=CC=CC=C3C=2)=N1 RBZSSTPBYFHRSR-UHFFFAOYSA-N 0.000 claims description 5
• WFJJYKJYGCGPFS-UHFFFAOYSA-N 3-(1-benzylindol-5-yl)sulfonyl-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)C=2C=C3C=CN(CC=4C=CC=CC=4)C3=CC=2)=N1 WFJJYKJYGCGPFS-UHFFFAOYSA-N 0.000 claims description 5
• YVEUDWZQMUISKP-UHFFFAOYSA-N 3-(1-methylindol-2-yl)sulfonyl-1h-pyridazin-6-one Chemical compound C=1C2=CC=CC=C2N(C)C=1S(=O)(=O)C=1C=CC(=O)NN=1 YVEUDWZQMUISKP-UHFFFAOYSA-N 0.000 claims description 5
• NQJFBHVHPOEWLC-UHFFFAOYSA-N 3-(3,4,4a,5-tetrahydro-2h-quinolin-1-ylsulfonyl)-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)N2C3=CC=CCC3CCC2)=N1 NQJFBHVHPOEWLC-UHFFFAOYSA-N 0.000 claims description 5
• SOVXTIRUOWJZSS-UHFFFAOYSA-N 3-[(3-chloro-1h-indol-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound N1C2=CC=CC=C2C(Cl)=C1S(=O)(=O)C=1C=CC(=O)NN=1 SOVXTIRUOWJZSS-UHFFFAOYSA-N 0.000 claims description 5
• OLKIXQGJDUXXTC-UHFFFAOYSA-N 3-[(5,7-dichloro-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound C=1C2=CC(Cl)=CC(Cl)=C2OC=1S(=O)(=O)C=1C=CC(=O)NN=1 OLKIXQGJDUXXTC-UHFFFAOYSA-N 0.000 claims description 5
• ZDIDXSOYTUCPQE-UHFFFAOYSA-N 3-[(5-chloro-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound C=1C2=CC(Cl)=CC=C2OC=1S(=O)(=O)C=1C=CC(=O)NN=1 ZDIDXSOYTUCPQE-UHFFFAOYSA-N 0.000 claims description 5
• WGSUFIBFKNDTGJ-UHFFFAOYSA-N 3-[(5-chloro-1h-indol-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound C=1C2=CC(Cl)=CC=C2NC=1S(=O)(=O)C=1C=CC(=O)NN=1 WGSUFIBFKNDTGJ-UHFFFAOYSA-N 0.000 claims description 5
• DDADXEQGUNIKPT-UHFFFAOYSA-N 3-[(5-chloro-3-ethyl-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound O1C2=CC=C(Cl)C=C2C(CC)=C1S(=O)(=O)C=1C=CC(=O)NN=1 DDADXEQGUNIKPT-UHFFFAOYSA-N 0.000 claims description 5
• MVDAJCXOQBRPQC-UHFFFAOYSA-N 3-[(5-chloro-3-propan-2-yl-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound O1C2=CC=C(Cl)C=C2C(C(C)C)=C1S(=O)(=O)C=1C=CC(=O)NN=1 MVDAJCXOQBRPQC-UHFFFAOYSA-N 0.000 claims description 5
• PJMQRZZJOSLFBJ-UHFFFAOYSA-N 3-imidazo[1,2-a]pyridin-3-ylsulfonyl-1H-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)C=2N3C=CC=CC3=NC=2)=N1 PJMQRZZJOSLFBJ-UHFFFAOYSA-N 0.000 claims description 5
• TWBJWMKHMNWGNT-UHFFFAOYSA-N 3-pyrrol-1-ylsulfonyl-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)N2C=CC=C2)=N1 TWBJWMKHMNWGNT-UHFFFAOYSA-N 0.000 claims description 5
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• UIJXWCKFKVXTRU-UHFFFAOYSA-N 2-[(6-oxo-1h-pyridazin-3-yl)sulfonyl]-5h-furo[3,2-c]pyridin-4-one Chemical compound N1C(=O)C=CC(S(=O)(=O)C=2OC3=C(C(NC=C3)=O)C=2)=N1 UIJXWCKFKVXTRU-UHFFFAOYSA-N 0.000 claims description 4
• GJSIXQDXGNTUSN-UHFFFAOYSA-N 3-[[3-(4-fluorophenyl)-1-benzofuran-2-yl]sulfonyl]-1h-pyridazin-6-one Chemical compound C1=CC(F)=CC=C1C1=C(S(=O)(=O)C2=NNC(=O)C=C2)OC2=CC=CC=C12 GJSIXQDXGNTUSN-UHFFFAOYSA-N 0.000 claims description 4
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
• 125000003118 aryl group Chemical group 0.000 claims description 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
• ULUKHVCKTFCDRT-UHFFFAOYSA-N 3-(3-chloroindazol-1-yl)sulfonyl-1h-pyridazin-6-one Chemical compound C12=CC=CC=C2C(Cl)=NN1S(=O)(=O)C=1C=CC(=O)NN=1 ULUKHVCKTFCDRT-UHFFFAOYSA-N 0.000 claims description 3
• MUEYUVJYJZJUIE-UHFFFAOYSA-N 3-(3-chloroindol-1-yl)sulfonyl-1h-pyridazin-6-one Chemical compound C12=CC=CC=C2C(Cl)=CN1S(=O)(=O)C=1C=CC(=O)NN=1 MUEYUVJYJZJUIE-UHFFFAOYSA-N 0.000 claims description 3
• FFQYWMOJPDVLPU-UHFFFAOYSA-N 3-(3-methylindol-1-yl)sulfonyl-1h-pyridazin-6-one Chemical compound C12=CC=CC=C2C(C)=CN1S(=O)(=O)C=1C=CC(=O)NN=1 FFQYWMOJPDVLPU-UHFFFAOYSA-N 0.000 claims description 3
• LCVXWZKNHISEPA-UHFFFAOYSA-N 3-(5h-[1,3]dioxolo[4,5-f]indol-6-ylsulfonyl)-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)C=2NC3=CC=4OCOC=4C=C3C=2)=N1 LCVXWZKNHISEPA-UHFFFAOYSA-N 0.000 claims description 3
• NTJWJLZMOKBOFA-UHFFFAOYSA-N 3-[(3,5-dimethyl-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound O1C2=CC=C(C)C=C2C(C)=C1S(=O)(=O)C=1C=CC(=O)NN=1 NTJWJLZMOKBOFA-UHFFFAOYSA-N 0.000 claims description 3
• YWFVMRGAGDNRMA-UHFFFAOYSA-N 3-[(3-phenyl-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)C2=C(C3=CC=CC=C3O2)C=2C=CC=CC=2)=N1 YWFVMRGAGDNRMA-UHFFFAOYSA-N 0.000 claims description 3
• MDZSNXLRKIMZRY-UHFFFAOYSA-N 3-[(5-chloro-3-hydroxy-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound O1C2=CC=C(Cl)C=C2C(O)=C1S(=O)(=O)C=1C=CC(=O)NN=1 MDZSNXLRKIMZRY-UHFFFAOYSA-N 0.000 claims description 3
• BRGJYGOQKYCMGP-UHFFFAOYSA-N 3-[(5-methoxy-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound C=1C2=CC(OC)=CC=C2OC=1S(=O)(=O)C=1C=CC(=O)NN=1 BRGJYGOQKYCMGP-UHFFFAOYSA-N 0.000 claims description 3
• IIWJPLYZNNZNGB-UHFFFAOYSA-N 3-[(5-methoxy-1h-indol-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound C=1C2=CC(OC)=CC=C2NC=1S(=O)(=O)C=1C=CC(=O)NN=1 IIWJPLYZNNZNGB-UHFFFAOYSA-N 0.000 claims description 3
• QSROOXVEHSOUBU-UHFFFAOYSA-N 3-[(5-methyl-1-benzothiophen-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound C=1C2=CC(C)=CC=C2SC=1S(=O)(=O)C=1C=CC(=O)NN=1 QSROOXVEHSOUBU-UHFFFAOYSA-N 0.000 claims description 3
• YCAYZFGZUUVLMY-UHFFFAOYSA-N 3-[(6-chloro-1h-indol-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound N1C2=CC(Cl)=CC=C2C=C1S(=O)(=O)C=1C=CC(=O)NN=1 YCAYZFGZUUVLMY-UHFFFAOYSA-N 0.000 claims description 3
• VTAPFQFGVVPFNM-UHFFFAOYSA-N 3-[(6-chloro-3-methyl-1-benzofuran-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound O1C2=CC(Cl)=CC=C2C(C)=C1S(=O)(=O)C=1C=CC(=O)NN=1 VTAPFQFGVVPFNM-UHFFFAOYSA-N 0.000 claims description 3
• PGWALDLWZWXTRU-UHFFFAOYSA-N 3-[(6-fluoro-1h-indol-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound N1C2=CC(F)=CC=C2C=C1S(=O)(=O)C=1C=CC(=O)NN=1 PGWALDLWZWXTRU-UHFFFAOYSA-N 0.000 claims description 3
• VOZMFKBTMUXWCT-UHFFFAOYSA-N 3-[(7-chloro-1h-indol-2-yl)sulfonyl]-1h-pyridazin-6-one Chemical compound N1C=2C(Cl)=CC=CC=2C=C1S(=O)(=O)C=1C=CC(=O)NN=1 VOZMFKBTMUXWCT-UHFFFAOYSA-N 0.000 claims description 3
• UGTGRHZJGQIRBG-UHFFFAOYSA-N 3-imidazol-1-ylsulfonyl-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)N2C=NC=C2)=N1 UGTGRHZJGQIRBG-UHFFFAOYSA-N 0.000 claims description 3
• BCXKKVQJDYCMAD-UHFFFAOYSA-N 3-indol-1-ylsulfonyl-1h-pyridazin-6-one Chemical compound N1C(=O)C=CC(S(=O)(=O)N2C3=CC=CC=C3C=C2)=N1 BCXKKVQJDYCMAD-UHFFFAOYSA-N 0.000 claims description 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000001041 indolyl group Chemical group 0.000 claims description 3
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 3
• UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 3
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 3
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 125000006085 pyrrolopyridyl group Chemical group 0.000 claims description 3
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
• 159000000000 sodium salts Chemical class 0.000 claims description 3
• 125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 claims description 3
• CYXNLUKXQVTYHT-UHFFFAOYSA-N 3-[(5-chloro-3-methyl-1-benzofuran-2-yl)sulfanyl]-6-methoxypyridazine Chemical group N1=NC(OC)=CC=C1SC1=C(C)C2=CC(Cl)=CC=C2O1 CYXNLUKXQVTYHT-UHFFFAOYSA-N 0.000 claims description 2
• GTSQOJISPPCBEE-UHFFFAOYSA-N 3-[(5-chloro-3-methyl-1-benzofuran-2-yl)sulfinyl]-6-methoxypyridazine Chemical compound N1=NC(OC)=CC=C1S(=O)C1=C(C)C2=CC(Cl)=CC=C2O1 GTSQOJISPPCBEE-UHFFFAOYSA-N 0.000 claims description 2
• CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 2
• 125000001246 bromo group Chemical group Br* 0.000 claims description 2
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
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