CA2558139C - Tricyclic benzopyran compound as anti-arrhythmic agents - Google Patents
Tricyclic benzopyran compound as anti-arrhythmic agents Download PDFInfo
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- CA2558139C CA2558139C CA2558139A CA2558139A CA2558139C CA 2558139 C CA2558139 C CA 2558139C CA 2558139 A CA2558139 A CA 2558139A CA 2558139 A CA2558139 A CA 2558139A CA 2558139 C CA2558139 C CA 2558139C
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- amino
- halogen atom
- arbitrarily substituted
- npr
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- -1 benzopyran compound Chemical class 0.000 title claims description 850
- 239000003416 antiarrhythmic agent Substances 0.000 title abstract description 5
- 125000003277 amino group Chemical group 0.000 claims abstract description 142
- 150000001562 benzopyrans Chemical class 0.000 claims abstract description 130
- 150000003839 salts Chemical class 0.000 claims abstract description 128
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 92
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 83
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims abstract description 31
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
- 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 claims abstract description 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 500
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 414
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 406
- 125000005843 halogen group Chemical group 0.000 claims description 296
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 195
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 175
- 125000003545 alkoxy group Chemical group 0.000 claims description 157
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 157
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 136
- 125000000217 alkyl group Chemical group 0.000 claims description 129
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 108
- 125000000286 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 107
- 125000001072 heteroaryl group Chemical group 0.000 claims description 69
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 53
- 125000003118 aryl group Chemical group 0.000 claims description 53
- 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 49
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 49
- 125000000623 heterocyclic group Chemical group 0.000 claims description 38
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 25
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 22
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 claims description 18
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 18
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 16
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical group NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 15
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 14
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000001769 aryl amino group Chemical group 0.000 claims description 13
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 13
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 13
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 12
- 125000006636 (C3-C8) cycloalkylcarbonyl group Chemical group 0.000 claims description 9
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
- IQQDNMHUOLMLNJ-UHFFFAOYSA-N quinolin-3-ol Chemical compound C1=CC=CC2=CC(O)=CN=C21 IQQDNMHUOLMLNJ-UHFFFAOYSA-N 0.000 claims description 9
- 206010003119 arrhythmia Diseases 0.000 claims description 7
- 230000006793 arrhythmia Effects 0.000 claims description 7
- 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 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 5
- CHIOVPNYOWEUJW-UHFFFAOYSA-N 2,2,7-trimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound C12=CC3=NC(C)=CC=C3C=C2OC(C)(C)C(O)C1NCCC1=CC=CC=C1 CHIOVPNYOWEUJW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- IJBQSFCBZCLRHT-UHFFFAOYSA-N 4-[2-(4-aminophenyl)ethylamino]-7-chloro-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCC1=CC=C(N)C=C1 IJBQSFCBZCLRHT-UHFFFAOYSA-N 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- ZZUSANGEAUESFL-UHFFFAOYSA-N 7-(hydroxymethyl)-2,2,9-trimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(CO)=NC3=CC=2C1NCCC1=CC=CC=C1 ZZUSANGEAUESFL-UHFFFAOYSA-N 0.000 claims description 4
- KMKAFGPNRRAYKI-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-(2-piperidin-1-ylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCN1CCCCC1 KMKAFGPNRRAYKI-UHFFFAOYSA-N 0.000 claims description 4
- ACZVHCBJCSMHIL-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-(pentylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound C1=C(Cl)N=C2C=C3C(NCCCCC)C(O)C(C)(C)OC3=CC2=C1C ACZVHCBJCSMHIL-UHFFFAOYSA-N 0.000 claims description 4
- SJROYWSEXZWKAM-UHFFFAOYSA-N 7-chloro-4-[2-(4-fluorophenyl)ethylamino]-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCC1=CC=C(F)C=C1 SJROYWSEXZWKAM-UHFFFAOYSA-N 0.000 claims description 4
- NFWWZVHIWDPWEY-UHFFFAOYSA-N 7-chloro-4-[2-(cyclopenten-1-yl)ethylamino]-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCC1=CCCC1 NFWWZVHIWDPWEY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- IDLTUNKJYAGSFN-UHFFFAOYSA-N 2,2-dimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC2=CC3=CC=CN=C3C=C2C1NCCC1=CC=CC=C1 IDLTUNKJYAGSFN-UHFFFAOYSA-N 0.000 claims description 3
- NGWVFMQMEXBFMD-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCC1=CC=CC=C1 NGWVFMQMEXBFMD-UHFFFAOYSA-N 0.000 claims description 3
- HZIDZZCZABOJDG-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-(3-methylbutylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound C1=C(Cl)N=C2C=C3C(NCCC(C)C)C(O)C(C)(C)OC3=CC2=C1C HZIDZZCZABOJDG-UHFFFAOYSA-N 0.000 claims description 3
- KTZDNDVKDFBDHQ-UHFFFAOYSA-N 7-chloro-4-[2-(2-fluorophenyl)ethylamino]-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCC1=CC=CC=C1F KTZDNDVKDFBDHQ-UHFFFAOYSA-N 0.000 claims description 3
- ODTMNOQRTBPFTK-UHFFFAOYSA-N 7-chloro-4-[2-(4-chlorophenyl)ethylamino]-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCC1=CC=C(Cl)C=C1 ODTMNOQRTBPFTK-UHFFFAOYSA-N 0.000 claims description 3
- FQNGONYRIBIZMD-UHFFFAOYSA-N 7-chloro-4-[2-(4-chloropyrazol-1-yl)ethylamino]-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCN1C=C(Cl)C=N1 FQNGONYRIBIZMD-UHFFFAOYSA-N 0.000 claims description 3
- WXXVQWSDMOAHHV-UHFFFAOYSA-N quinoline-7-carboxylic acid Chemical compound C1=CC=NC2=CC(C(=O)O)=CC=C21 WXXVQWSDMOAHHV-UHFFFAOYSA-N 0.000 claims description 3
- XEQQREZFQJPKEY-UHFFFAOYSA-N 3,3-dimethyl-1-(2-phenylethylamino)-1,2-dihydropyrano[3,2-f]quinolin-2-ol Chemical compound OC1C(C)(C)OC2=CC=C3N=CC=CC3=C2C1NCCC1=CC=CC=C1 XEQQREZFQJPKEY-UHFFFAOYSA-N 0.000 claims description 2
- YHKRTDZFVQAXNA-UHFFFAOYSA-N 4-(2-anilinoethylamino)-7-chloro-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCNC1=CC=CC=C1 YHKRTDZFVQAXNA-UHFFFAOYSA-N 0.000 claims description 2
- LCMZFFXCFJBKEW-UHFFFAOYSA-N 7-chloro-4-(ethylamino)-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound C1=C(Cl)N=C2C=C3C(NCC)C(O)C(C)(C)OC3=CC2=C1C LCMZFFXCFJBKEW-UHFFFAOYSA-N 0.000 claims description 2
- AHJQDTJTOLKGCR-UHFFFAOYSA-N 7-chloro-4-[2-(n-ethyl-3-methylanilino)ethylamino]-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC2=CC3=C(C)C=C(Cl)N=C3C=C2C1NCCN(CC)C1=CC=CC(C)=C1 AHJQDTJTOLKGCR-UHFFFAOYSA-N 0.000 claims description 2
- WPHXOSQLRPKBQC-UHFFFAOYSA-N 7-chloro-4-[[6-(4-chlorophenyl)pyridin-3-yl]methylamino]-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCC(C=N1)=CC=C1C1=CC=C(Cl)C=C1 WPHXOSQLRPKBQC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- ZELBDNYRCFQHLE-UHFFFAOYSA-N 7,7-dimethyl-9-(2-phenylethylamino)-8,9-dihydropyrano[2,3-g]quinoxalin-8-ol Chemical compound OC1C(C)(C)OC2=CC3=NC=CN=C3C=C2C1NCCC1=CC=CC=C1 ZELBDNYRCFQHLE-UHFFFAOYSA-N 0.000 claims 3
- JSXRAXHZNAUXQG-UHFFFAOYSA-N 7,7-dimethyl-9-(pentylamino)-8,9-dihydropyrano[2,3-g]quinoxalin-8-ol Chemical compound C1=CN=C2C=C3C(NCCCCC)C(O)C(C)(C)OC3=CC2=N1 JSXRAXHZNAUXQG-UHFFFAOYSA-N 0.000 claims 2
- KBOCOAKGVSVDNO-UHFFFAOYSA-N 7-chloro-4-[(2-hydroxy-2-phenylethyl)amino]-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCC(O)C1=CC=CC=C1 KBOCOAKGVSVDNO-UHFFFAOYSA-N 0.000 claims 2
- NJRSHQBOZFCMIQ-UHFFFAOYSA-N 9-(2-cyclohexylethylamino)-7,7-dimethyl-8,9-dihydropyrano[2,3-g]quinoxalin-8-ol Chemical compound OC1C(C)(C)OC2=CC3=NC=CN=C3C=C2C1NCCC1CCCCC1 NJRSHQBOZFCMIQ-UHFFFAOYSA-N 0.000 claims 2
- CYRVNMMXCDNQLC-UHFFFAOYSA-N 9-(hydroxymethyl)-2,2-dimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC2=CC3=C(CO)C=CN=C3C=C2C1NCCC1=CC=CC=C1 CYRVNMMXCDNQLC-UHFFFAOYSA-N 0.000 claims 2
- BKBDBYALOHIIGP-UHFFFAOYSA-N 9-[2-(2-fluorophenyl)ethylamino]-7,7-dimethyl-8,9-dihydropyrano[2,3-g]quinoxalin-8-ol Chemical compound OC1C(C)(C)OC2=CC3=NC=CN=C3C=C2C1NCCC1=CC=CC=C1F BKBDBYALOHIIGP-UHFFFAOYSA-N 0.000 claims 2
- XNKQFMWBOGFGTO-UHFFFAOYSA-N 9-[2-(4-fluorophenyl)ethylamino]-7,7-dimethyl-8,9-dihydropyrano[2,3-g]quinoxalin-8-ol Chemical compound OC1C(C)(C)OC2=CC3=NC=CN=C3C=C2C1NCCC1=CC=C(F)C=C1 XNKQFMWBOGFGTO-UHFFFAOYSA-N 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- GTUXVIDPBHVDBF-UHFFFAOYSA-N 2,3,7,7-tetramethyl-9-(2-phenylethylamino)-8,9-dihydropyrano[2,3-g]quinoxalin-8-ol Chemical compound C1=2C=C3N=C(C)C(C)=NC3=CC=2OC(C)(C)C(O)C1NCCC1=CC=CC=C1 GTUXVIDPBHVDBF-UHFFFAOYSA-N 0.000 claims 1
- OKNVFTMHUWDCQC-UHFFFAOYSA-N 3,7,7-trimethyl-9-(2-phenylethylamino)-8,9-dihydropyrano[3,2-g]quinoxalin-8-ol Chemical compound OC1C(C)(C)OC2=CC3=NC(C)=CN=C3C=C2C1NCCC1=CC=CC=C1 OKNVFTMHUWDCQC-UHFFFAOYSA-N 0.000 claims 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- LGIXAJJEPAQTJA-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-ylmethylamino)-7-chloro-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound C1=C2OCOC2=CC(CNC2C=3C=C4N=C(Cl)C=C(C4=CC=3OC(C)(C)C2O)C)=C1 LGIXAJJEPAQTJA-UHFFFAOYSA-N 0.000 claims 1
- VNWFRXCRHVNMIC-UHFFFAOYSA-N 4-(1-benzofuran-2-ylmethylamino)-7-chloro-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound C1=CC=C2OC(CNC3C=4C=C5N=C(Cl)C=C(C5=CC=4OC(C)(C)C3O)C)=CC2=C1 VNWFRXCRHVNMIC-UHFFFAOYSA-N 0.000 claims 1
- ZVQPSPFZVMLTID-UHFFFAOYSA-N 4-(benzylamino)-7-chloro-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCC1=CC=CC=C1 ZVQPSPFZVMLTID-UHFFFAOYSA-N 0.000 claims 1
- ILAFKBRUZSFDLN-UHFFFAOYSA-N 4-[2-(1,3-benzodioxol-5-yl)ethylamino]-7-chloro-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound C1=C2OCOC2=CC(CCNC2C=3C=C4N=C(Cl)C=C(C4=CC=3OC(C)(C)C2O)C)=C1 ILAFKBRUZSFDLN-UHFFFAOYSA-N 0.000 claims 1
- AOKCDZVLSLZJQS-UHFFFAOYSA-N 7-(aminomethyl)-2,2,9-trimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(CN)=NC3=CC=2C1NCCC1=CC=CC=C1 AOKCDZVLSLZJQS-UHFFFAOYSA-N 0.000 claims 1
- XPLJCDNSBAXQRO-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-(2-methylpropylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound C1=C(Cl)N=C2C=C3C(NCC(C)C)C(O)C(C)(C)OC3=CC2=C1C XPLJCDNSBAXQRO-UHFFFAOYSA-N 0.000 claims 1
- WQZQDRKMVROFHJ-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-(2-phenylbutylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC2=CC3=C(C)C=C(Cl)N=C3C=C2C1NCC(CC)C1=CC=CC=C1 WQZQDRKMVROFHJ-UHFFFAOYSA-N 0.000 claims 1
- BRRSSWQQYAKFDT-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-(2-pyrazol-1-ylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCN1C=CC=N1 BRRSSWQQYAKFDT-UHFFFAOYSA-N 0.000 claims 1
- HZUJFGLZSGYMQT-UHFFFAOYSA-N 8-hydroxy-7,7-dimethyl-9-(2-phenylethylamino)-8,9-dihydro-1h-pyrano[3,2-g][1,4]benzoxazin-2-one Chemical compound OC1C(C)(C)OC2=CC=3OCC(=O)NC=3C=C2C1NCCC1=CC=CC=C1 HZUJFGLZSGYMQT-UHFFFAOYSA-N 0.000 claims 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 14
- 125000004429 atom Chemical group 0.000 abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 7
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 7
- 125000004434 sulfur atom Chemical group 0.000 abstract description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 3
- 239000000470 constituent Substances 0.000 abstract description 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 abstract description 2
- 239000000460 chlorine Substances 0.000 description 832
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 description 589
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 360
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 346
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 311
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 290
- 229910006069 SO3H Inorganic materials 0.000 description 247
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 184
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 170
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 description 59
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 46
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 32
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 13
- 125000003282 alkyl amino group Chemical group 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 9
- 230000036279 refractory period Effects 0.000 description 9
- 229910007219 SnPr Inorganic materials 0.000 description 8
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 210000003205 muscle Anatomy 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
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- 125000005842 heteroatom Chemical group 0.000 description 4
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- 230000002861 ventricular Effects 0.000 description 3
- KEOCMVKQQCQIJF-UHFFFAOYSA-N 8-hydroxy-4,7,7-trimethyl-9-(2-phenylethylamino)-8,9-dihydropyrano[2,3-g][1,4]benzoxazin-3-one Chemical compound OC1C(C)(C)OC=2C=C3N(C)C(=O)COC3=CC=2C1NCCC1=CC=CC=C1 KEOCMVKQQCQIJF-UHFFFAOYSA-N 0.000 description 2
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- TVZCRIROJQEVOT-CABCVRRESA-N Cromakalim Chemical compound N1([C@@H]2C3=CC(=CC=C3OC([C@H]2O)(C)C)C#N)CCCC1=O TVZCRIROJQEVOT-CABCVRRESA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229950004210 cromakalim Drugs 0.000 description 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004672 ethylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C(*)=O 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 210000002837 heart atrium Anatomy 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000006252 n-propylcarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- RGVPOXRFEPSFGH-UHFFFAOYSA-N 1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol Chemical compound COC1=C(OC)C(OC)=CC(CC2C3=CC(O)=C(O)C=C3CCN2)=C1 RGVPOXRFEPSFGH-UHFFFAOYSA-N 0.000 description 1
- MNCMBBIFTVWHIP-UHFFFAOYSA-N 1-anthracen-9-yl-2,2,2-trifluoroethanone Chemical group C1=CC=C2C(C(=O)C(F)(F)F)=C(C=CC=C3)C3=CC2=C1 MNCMBBIFTVWHIP-UHFFFAOYSA-N 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- LMVGPQNBHMECBB-UHFFFAOYSA-N 2,2,7,9-tetramethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound C12=CC3=NC(C)=CC(C)=C3C=C2OC(C)(C)C(O)C1NCCC1=CC=CC=C1 LMVGPQNBHMECBB-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003890 2-phenylbutyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- VGCNVPXAIFXIDF-UHFFFAOYSA-N 2h-chromen-4-amine Chemical class C1=CC=C2C(N)=CCOC2=C1 VGCNVPXAIFXIDF-UHFFFAOYSA-N 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- HVQPLDFHLAONCL-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-(3-phenylpropylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCCC1=CC=CC=C1 HVQPLDFHLAONCL-UHFFFAOYSA-N 0.000 description 1
- FPRQSHYHIOERJP-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-[2-(4-methylpyrazol-1-yl)ethylamino]-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound C1=C(C)C=NN1CCNC1C2=CC3=NC(Cl)=CC(C)=C3C=C2OC(C)(C)C1O FPRQSHYHIOERJP-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 101001081172 Homo sapiens Humanin-like 11 Proteins 0.000 description 1
- 102100027736 Humanin-like 11 Human genes 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 206010042434 Sudden death Diseases 0.000 description 1
- 208000018452 Torsade de pointes Diseases 0.000 description 1
- 208000002363 Torsades de Pointes Diseases 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- IXTMWRCNAAVVAI-UHFFFAOYSA-N dofetilide Chemical compound C=1C=C(NS(C)(=O)=O)C=CC=1CCN(C)CCOC1=CC=C(NS(C)(=O)=O)C=C1 IXTMWRCNAAVVAI-UHFFFAOYSA-N 0.000 description 1
- 229960002994 dofetilide Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000005933 neopentyloxycarbonyl group Chemical group 0.000 description 1
- 231100001143 noxa Toxicity 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 229960002370 sotalol Drugs 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
-
- 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
-
- 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
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D515/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D515/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D515/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Dental Preparations (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004-084605 | 2004-03-23 | ||
| JP2004084605 | 2004-03-23 | ||
| PCT/JP2005/006004 WO2005090357A1 (en) | 2004-03-23 | 2005-03-23 | Tricyclic benzopyran compound as anti-arrhythmic agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2558139A1 CA2558139A1 (en) | 2005-09-29 |
| CA2558139C true CA2558139C (en) | 2012-01-17 |
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| Application Number | Title | Priority Date | Filing Date |
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| CA2558139A Expired - Fee Related CA2558139C (en) | 2004-03-23 | 2005-03-23 | Tricyclic benzopyran compound as anti-arrhythmic agents |
Country Status (30)
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| US (2) | US7652008B2 (https=) |
| EP (1) | EP1732929B1 (https=) |
| JP (1) | JP4840594B2 (https=) |
| KR (2) | KR101085979B1 (https=) |
| CN (3) | CN102190661B (https=) |
| AT (1) | ATE485299T1 (https=) |
| AU (2) | AU2005223612B2 (https=) |
| BR (1) | BRPI0508768A (https=) |
| CA (1) | CA2558139C (https=) |
| CY (1) | CY1111250T1 (https=) |
| CZ (1) | CZ2006598A3 (https=) |
| DE (1) | DE602005024245D1 (https=) |
| DK (1) | DK1732929T3 (https=) |
| EG (1) | EG27163A (https=) |
| ES (1) | ES2353021T3 (https=) |
| HR (1) | HRP20110005T1 (https=) |
| IL (1) | IL177950A (https=) |
| MX (1) | MXPA06010880A (https=) |
| NO (1) | NO339495B1 (https=) |
| NZ (2) | NZ549570A (https=) |
| PL (1) | PL1732929T3 (https=) |
| PT (1) | PT1732929E (https=) |
| RS (1) | RS51742B (https=) |
| RU (1) | RU2380370C2 (https=) |
| SI (1) | SI1732929T1 (https=) |
| SK (1) | SK287994B6 (https=) |
| TW (1) | TWI352704B (https=) |
| UA (1) | UA91189C2 (https=) |
| WO (1) | WO2005090357A1 (https=) |
| ZA (1) | ZA200607388B (https=) |
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| ES2353021T3 (es) * | 2004-03-23 | 2011-02-24 | Nissan Chemical Industries, Ltd. | Compuesto de benzopirano tricíclico como agentes anti-arrítmicos. |
| RU2448112C2 (ru) | 2006-03-10 | 2012-04-20 | Ниссан Кемикал Индастриз, Лтд. | Способ получения оптически активного соединения оксида хромена |
| TW201022223A (en) * | 2008-08-14 | 2010-06-16 | Nissan Chemical Ind Ltd | Di-substituted benzopyrane compound |
| KR101703202B1 (ko) * | 2009-04-30 | 2017-02-06 | 닛산 가가쿠 고교 가부시키 가이샤 | 3환성 벤조피란 화합물의 신규한 결정형태 및 그 제조방법 |
| US8431576B2 (en) | 2009-06-25 | 2013-04-30 | Alkermes Pharma Ireland Limited | Heterocyclic compounds for the treatment of neurological and psychological disorders |
| JPWO2014051077A1 (ja) * | 2012-09-27 | 2016-08-25 | 日産化学工業株式会社 | 高純度の含窒素複素環化合物の製造方法 |
| JP6202280B2 (ja) * | 2012-09-27 | 2017-09-27 | 日産化学工業株式会社 | 含窒素複素環ｎ−オキシド化合物の製造方法 |
| JPWO2015012271A1 (ja) * | 2013-07-25 | 2017-03-02 | 日産化学工業株式会社 | 複素環化合物の製造方法 |
| US11168094B2 (en) | 2017-01-06 | 2021-11-09 | Azcuris Co., Ltd. | Quinolinone derivative and pharmaceutical composition for preventing or treating allergic diseases such as asthma or atopic dermatitis including the quinolinone derivative as active ingredient |
| EP3761983A1 (en) | 2018-03-05 | 2021-01-13 | Alkermes Pharma Ireland Limited | Aripiprazole dosing strategy |
| CN108727261B (zh) * | 2018-06-21 | 2021-09-24 | 济南大学 | 一种硝基取代喹那啶的制备方法 |
| US20220071951A1 (en) * | 2018-12-28 | 2022-03-10 | Osaka University | Therapeutic agent for inherited bradyarrhythmia |
| RU2754610C1 (ru) * | 2020-04-14 | 2021-09-03 | Георгий Викторович ТЕЦ | Препарат для лечения заболеваний, вызванных бактериями |
| CN115916201B (zh) * | 2020-06-26 | 2024-09-17 | 国立大学法人大阪大学 | 药剂诱发性心动过缓及心动过缓性心律失常治疗药 |
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| ZM7682A1 (en) | 1981-09-25 | 1983-05-23 | Beecham Group Plc | Active compounds |
| JPS5867683U (ja) | 1981-10-28 | 1983-05-09 | 株式会社ナムコ | 歩行ロボツト |
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| US5097037A (en) * | 1989-07-17 | 1992-03-17 | Nissan Chemical Industries, Ltd. | Process for the optical resolution of pyranobenzoxadiazole compounds |
| US5164509A (en) * | 1990-11-26 | 1992-11-17 | E. R. Squibb & Sons, Inc. | Benzodiazolo analogs |
| JPH07300414A (ja) * | 1993-04-02 | 1995-11-14 | Nissan Chem Ind Ltd | 心不全治療薬 |
| UA27973C2 (uk) * | 1993-04-02 | 2000-10-16 | Ніссан Кемікал Індастріз Лтд | Лікарський засіб для лікування серцевої недостатності |
| JP2734457B2 (ja) | 1994-02-23 | 1998-03-30 | 日産化学工業株式会社 | 不斉エポキシ化反応 |
| WO1995034547A1 (en) * | 1994-06-10 | 1995-12-21 | Smithkline Beecham Plc | C-4 amide substituted compounds and their use as therapeutic agents |
| HRP970255B1 (en) * | 1996-05-15 | 2003-10-31 | Hoechst Ag | Sulfonamido substituted chromane derivatives, method for their preparation, their use as medicaments or diagnostic agents as well as medicaments containing them |
| US6486178B1 (en) | 1998-06-03 | 2002-11-26 | Nissan Chemical Industries, Ltd. | Indane derivatives |
| AU5444499A (en) | 1998-09-01 | 2000-03-21 | Nissan Chemical Industries Ltd. | Benzoxazine derivatives |
| AU2830800A (en) | 1999-03-25 | 2000-10-16 | Nissan Chemical Industries Ltd. | Chroman derivatives |
| CA2383583C (en) * | 1999-09-17 | 2009-04-07 | Nissan Chemical Industries, Ltd. | Benzopyran derivative |
| EP1214307B1 (en) | 1999-09-24 | 2004-04-07 | Nissan Chemical Industries, Ltd. | 4-oxybenzopyran derivative |
| US6677371B1 (en) | 1999-10-05 | 2004-01-13 | Nissan Chemical Industries, Ltd. | 4-oxybenzopyran derivative |
| TW589305B (en) | 2001-02-14 | 2004-06-01 | Nissan Chemical Ind Ltd | 4-aminobenzopyran derivatives |
| EP1401823B1 (en) | 2001-06-25 | 2005-10-05 | Nissan Chemical Industries, Ltd. | Substituted benzopyran derivatives against arrhythmia |
| WO2003014113A1 (en) | 2001-08-06 | 2003-02-20 | Glenmark Pharmaceuticals Limited | Novel benzopyran compounds and process for their preparation and use |
| ES2353021T3 (es) * | 2004-03-23 | 2011-02-24 | Nissan Chemical Industries, Ltd. | Compuesto de benzopirano tricíclico como agentes anti-arrítmicos. |
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2005
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