AU2005223612B2 - Tricyclic benzopyran compound as anti-arrhythmic agents - Google Patents
Tricyclic benzopyran compound as anti-arrhythmic agents Download PDFInfo
- Publication number
- AU2005223612B2 AU2005223612B2 AU2005223612A AU2005223612A AU2005223612B2 AU 2005223612 B2 AU2005223612 B2 AU 2005223612B2 AU 2005223612 A AU2005223612 A AU 2005223612A AU 2005223612 A AU2005223612 A AU 2005223612A AU 2005223612 B2 AU2005223612 B2 AU 2005223612B2
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- AU
- Australia
- Prior art keywords
- group
- halogen atom
- arbitrarily substituted
- npr
- amino
- 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.)
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- -1 benzopyran compound Chemical class 0.000 title claims description 851
- 239000003416 antiarrhythmic agent Substances 0.000 title abstract description 5
- 125000003277 amino group Chemical group 0.000 claims abstract description 154
- 150000001562 benzopyrans Chemical class 0.000 claims abstract description 139
- 150000003839 salts Chemical class 0.000 claims abstract description 139
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 98
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- 125000004429 atom Chemical group 0.000 claims abstract description 12
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims abstract description 8
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 claims abstract description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 12
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 919
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 492
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 465
- 125000005843 halogen group Chemical group 0.000 claims description 328
- 125000003545 alkoxy group Chemical group 0.000 claims description 262
- 125000000217 alkyl group Chemical group 0.000 claims description 207
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 195
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 181
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 113
- 125000003118 aryl group Chemical group 0.000 claims description 107
- 125000001072 heteroaryl group Chemical group 0.000 claims description 96
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 76
- 125000003282 alkyl amino group Chemical group 0.000 claims description 63
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 63
- 125000000623 heterocyclic group Chemical group 0.000 claims description 52
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 50
- 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
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 46
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 41
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 40
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 39
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 38
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 37
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 34
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 26
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 25
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical group NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 24
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 24
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 19
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 18
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 18
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 17
- 125000001769 aryl amino group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 17
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 16
- 206010003119 arrhythmia Diseases 0.000 claims description 12
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 11
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 9
- 230000006793 arrhythmia Effects 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- IQQDNMHUOLMLNJ-UHFFFAOYSA-N quinolin-3-ol Chemical compound C1=CC=CC2=CC(O)=CN=C21 IQQDNMHUOLMLNJ-UHFFFAOYSA-N 0.000 claims description 7
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 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
- 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 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 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
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 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 4
- 239000003814 drug Substances 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
- KCHOBYCFOXAKNM-UHFFFAOYSA-N 7-chloro-4-(2-cyclohexylethylamino)-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=2C1NCCC1CCCCC1 KCHOBYCFOXAKNM-UHFFFAOYSA-N 0.000 claims description 3
- 125000005974 C6-C14 arylcarbonyl group Chemical group 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 150000003857 carboxamides Chemical class 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- PUSKHXMZPOMNTQ-UHFFFAOYSA-N ethyl 2,1,3-benzoselenadiazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=[Se]=NC2=C1 PUSKHXMZPOMNTQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 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 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims 1
- YFUJXCXOIXYJBA-UHFFFAOYSA-N 3-hydroxy-2,2,9-trimethyl-4-(2-phenylethylamino)-4,6-dihydro-3h-pyrano[2,3-g]quinolin-7-one Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(O)=NC3=CC=2C1NCCC1=CC=CC=C1 YFUJXCXOIXYJBA-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 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
- 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
- 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 1
- 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 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims 1
- 125000006038 hexenyl group Chemical group 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 231100001143 noxa Toxicity 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 9
- 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 5
- 239000000470 constituent Substances 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 abstract description 2
- 239000000460 chlorine Substances 0.000 description 505
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 425
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 345
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 264
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 249
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 241
- 239000002904 solvent Substances 0.000 description 80
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 54
- 229920000728 polyester Polymers 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 235000019441 ethanol Nutrition 0.000 description 15
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 11
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 10
- 150000002825 nitriles Chemical class 0.000 description 10
- 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 229910007219 SnPr Inorganic materials 0.000 description 8
- 239000003377 acid catalyst Substances 0.000 description 8
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 8
- 230000036279 refractory period Effects 0.000 description 8
- 102100024007 Neurofilament heavy polypeptide Human genes 0.000 description 7
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 229960004132 diethyl ether Drugs 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 6
- 150000003462 sulfoxides Chemical class 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000006636 (C3-C8) cycloalkylcarbonyl group Chemical group 0.000 description 5
- 238000001321 HNCO Methods 0.000 description 5
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
- 210000003205 muscle Anatomy 0.000 description 5
- 108010091047 neurofilament protein H Proteins 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
- 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 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 4
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 229910052707 ruthenium Inorganic materials 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229910052703 rhodium Inorganic materials 0.000 description 3
- 239000010948 rhodium Substances 0.000 description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- 230000002861 ventricular Effects 0.000 description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 2
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- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [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 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
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 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
- MMCIXNVRVDTQSG-UHFFFAOYSA-N quinoline-7-carboxamide Chemical compound C1=CC=NC2=CC(C(=O)N)=CC=C21 MMCIXNVRVDTQSG-UHFFFAOYSA-N 0.000 description 1
- 229930185107 quinolinone Natural products 0.000 description 1
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical compound C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 150000003303 ruthenium Chemical class 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229960002370 sotalol Drugs 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000010189 synthetic method Methods 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
- 150000003892 tartrate salts Chemical class 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
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 description 1
- BKHZQJRTFNFCTG-UHFFFAOYSA-N tris(2-methylphenyl) phosphite Chemical compound CC1=CC=CC=C1OP(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C BKHZQJRTFNFCTG-UHFFFAOYSA-N 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Classifications
-
- 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
- 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
-
- 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)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2010202900A AU2010202900B2 (en) | 2004-03-23 | 2010-07-08 | Tricyclic benzopyran compound as anti-arrhythmic agents |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004084605 | 2004-03-23 | ||
| JP2004-084605 | 2004-03-23 | ||
| PCT/JP2005/006004 WO2005090357A1 (en) | 2004-03-23 | 2005-03-23 | Tricyclic benzopyran compound as anti-arrhythmic agents |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2010202900A Division AU2010202900B2 (en) | 2004-03-23 | 2010-07-08 | Tricyclic benzopyran compound as anti-arrhythmic agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2005223612A1 AU2005223612A1 (en) | 2005-09-29 |
| AU2005223612B2 true AU2005223612B2 (en) | 2010-06-24 |
Family
ID=34962589
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005223612A Ceased AU2005223612B2 (en) | 2004-03-23 | 2005-03-23 | Tricyclic benzopyran compound as anti-arrhythmic agents |
| AU2010202900A Ceased AU2010202900B2 (en) | 2004-03-23 | 2010-07-08 | Tricyclic benzopyran compound as anti-arrhythmic agents |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2010202900A Ceased AU2010202900B2 (en) | 2004-03-23 | 2010-07-08 | Tricyclic benzopyran compound as anti-arrhythmic agents |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US7652008B2 (https=) |
| EP (1) | EP1732929B1 (https=) |
| JP (1) | JP4840594B2 (https=) |
| KR (2) | KR101085979B1 (https=) |
| CN (3) | CN101429200B (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) | NZ585606A (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=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101085979B1 (ko) * | 2004-03-23 | 2011-11-22 | 닛산 가가쿠 고교 가부시키 가이샤 | 항부정맥제로 사용되는 삼환계 벤조피란 화합물 |
| AU2007225765B2 (en) | 2006-03-10 | 2012-05-24 | Nissan Chemical Industries, Ltd. | Process for producing optically active chromene oxide compound |
| WO2010018867A1 (ja) * | 2008-08-14 | 2010-02-18 | 日産化学工業株式会社 | ジ置換ベンゾピラン化合物 |
| RU2523279C2 (ru) * | 2009-04-30 | 2014-07-20 | Ниссан Кемикал Индастриз, Лтд. | Новая кристаллическая форма соединения трициклического бензопирана и способ его производства |
| LT2445502T (lt) | 2009-06-25 | 2017-09-25 | Alkermes Pharma Ireland Limited | Heterocikliniai junginiai, skirti neurologinių ir fiziologinių susirgimų gydymui |
| WO2014050613A1 (ja) * | 2012-09-27 | 2014-04-03 | 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 |
| CN104507949B (zh) * | 2012-09-27 | 2017-07-28 | 日产化学工业株式会社 | 高纯度的含氮杂环化合物的制造方法 |
| EP3026047A4 (en) * | 2013-07-25 | 2017-05-17 | Nissan Chemical Industries, Ltd. | Method for producing heterocyclic compound |
| EP3567044A4 (en) * | 2017-01-06 | 2020-06-10 | Korea University Research and Business Foundation, Sejong Campus | INNOVATIVE CHINOLINONE DERIVATIVE AND PHARMACEUTICAL COMPOSITION FOR THE PREVENTION OR TREATMENT OF ALLERGIC DISEASES LIKE ASTHMA OR ATOPIA THEREFORE AS AN ACTIVE SUBSTANCE |
| 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 |
| EP3903882B1 (en) * | 2018-12-28 | 2025-05-21 | 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 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0327127A1 (en) * | 1988-02-03 | 1989-08-09 | Nissan Chemical Industries Ltd. | Pyranobenzoxadiazole derivatives, preparation, use and compositions comprising them |
| JPH024791A (ja) * | 1988-06-23 | 1990-01-09 | Nissan Chem Ind Ltd | ピラノベンゾトリアゾール誘導体 |
| EP0409165A2 (en) * | 1989-07-17 | 1991-01-23 | Nissan Chemical Industries Ltd. | Process for the optical resolution of pyranobenzoxadiazole compounds |
| EP0488107A2 (en) * | 1990-11-26 | 1992-06-03 | E.R. SQUIBB & SONS, INC. | Tricyclic benzodiazole analogs and their use in the treatment of cardiovascular disorders |
| EP0693283A1 (en) * | 1993-04-02 | 1996-01-24 | Nissan Chemical Industries, Limited | Heart failure remedy |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP2876712B2 (ja) * | 1989-07-17 | 1999-03-31 | 日産化学工業株式会社 | 光学活性ピラノベンゾオキサジアゾール誘導体 |
| JPH07300414A (ja) * | 1993-04-02 | 1995-11-14 | Nissan Chem Ind Ltd | 心不全治療薬 |
| 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 |
| AR007115A1 (es) * | 1996-05-15 | 1999-10-13 | Hoechst Ag | Cromanos sustituidos con sulfonamida, procedimiento para su preparacion, su empleo para la preparacion de medicamento o agente de diagnostico, asi como medicamento que los contiene |
| 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 |
| WO2000058300A1 (en) | 1999-03-25 | 2000-10-05 | Nissan Chemical Industries, Ltd. | Chroman derivatives |
| HUP0202690A3 (en) * | 1999-09-17 | 2005-02-28 | Nissan Chemical Ind Ltd | Benzopyran derivative having antiarrhytmic activity |
| US6555574B1 (en) | 1999-09-24 | 2003-04-29 | Nissan Chemical Industries, Ltd. | 4-oxybenzopyran derivative |
| WO2001025224A1 (en) | 1999-10-05 | 2001-04-12 | Nissan Chemical Industries, Ltd. | 4-oxybenzopyran derivative |
| TW589305B (en) | 2001-02-14 | 2004-06-01 | Nissan Chemical Ind Ltd | 4-aminobenzopyran derivatives |
| HUP0400362A3 (en) | 2001-06-25 | 2007-05-29 | Nissan Chemical Ind Ltd | Substituted benzopyran derivetives against arrhythmia |
| WO2003014113A1 (en) | 2001-08-06 | 2003-02-20 | Glenmark Pharmaceuticals Limited | Novel benzopyran compounds and process for their preparation and use |
| KR101085979B1 (ko) * | 2004-03-23 | 2011-11-22 | 닛산 가가쿠 고교 가부시키 가이샤 | 항부정맥제로 사용되는 삼환계 벤조피란 화합물 |
-
2005
- 2005-03-23 KR KR1020107027058A patent/KR101085979B1/ko not_active Expired - Fee Related
- 2005-03-23 CA CA2558139A patent/CA2558139C/en not_active Expired - Fee Related
- 2005-03-23 US US10/590,975 patent/US7652008B2/en active Active
- 2005-03-23 SI SI200531171T patent/SI1732929T1/sl unknown
- 2005-03-23 KR KR1020067021988A patent/KR101019402B1/ko not_active Expired - Lifetime
- 2005-03-23 WO PCT/JP2005/006004 patent/WO2005090357A1/en not_active Ceased
- 2005-03-23 PT PT05727581T patent/PT1732929E/pt unknown
- 2005-03-23 NZ NZ585606A patent/NZ585606A/en not_active IP Right Cessation
- 2005-03-23 PL PL05727581T patent/PL1732929T3/pl unknown
- 2005-03-23 UA UAA200611101A patent/UA91189C2/ru unknown
- 2005-03-23 ZA ZA200607388A patent/ZA200607388B/en unknown
- 2005-03-23 CN CN2008101707921A patent/CN101429200B/zh not_active Expired - Fee Related
- 2005-03-23 SK SK5079-2006A patent/SK287994B6/sk not_active IP Right Cessation
- 2005-03-23 CN CN2005800090295A patent/CN1934116B/zh not_active Expired - Lifetime
- 2005-03-23 CZ CZ20060598A patent/CZ2006598A3/cs unknown
- 2005-03-23 AT AT05727581T patent/ATE485299T1/de active
- 2005-03-23 HR HR20110005T patent/HRP20110005T1/hr unknown
- 2005-03-23 AU AU2005223612A patent/AU2005223612B2/en not_active Ceased
- 2005-03-23 JP JP2006530022A patent/JP4840594B2/ja not_active Expired - Lifetime
- 2005-03-23 TW TW094108962A patent/TWI352704B/zh not_active IP Right Cessation
- 2005-03-23 CN CN2011100751168A patent/CN102190661B/zh not_active Expired - Fee Related
- 2005-03-23 RU RU2006137284/04A patent/RU2380370C2/ru not_active IP Right Cessation
- 2005-03-23 DE DE602005024245T patent/DE602005024245D1/de not_active Expired - Lifetime
- 2005-03-23 RS RS20110028A patent/RS51742B/sr unknown
- 2005-03-23 ES ES05727581T patent/ES2353021T3/es not_active Expired - Lifetime
- 2005-03-23 DK DK05727581.0T patent/DK1732929T3/da active
- 2005-03-23 EP EP05727581A patent/EP1732929B1/en not_active Expired - Lifetime
- 2005-03-23 BR BRPI0508768-6A patent/BRPI0508768A/pt not_active Application Discontinuation
- 2005-03-23 MX MXPA06010880A patent/MXPA06010880A/es active IP Right Grant
- 2005-03-23 NZ NZ549570A patent/NZ549570A/en not_active IP Right Cessation
-
2006
- 2006-09-02 EG EGNA2006000900 patent/EG27163A/xx active
- 2006-09-07 IL IL177950A patent/IL177950A/en not_active IP Right Cessation
- 2006-10-23 NO NO20064819A patent/NO339495B1/no not_active IP Right Cessation
-
2009
- 2009-11-17 US US12/591,353 patent/US7964623B2/en not_active Expired - Fee Related
-
2010
- 2010-07-08 AU AU2010202900A patent/AU2010202900B2/en not_active Ceased
-
2011
- 2011-01-19 CY CY20111100060T patent/CY1111250T1/el unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0327127A1 (en) * | 1988-02-03 | 1989-08-09 | Nissan Chemical Industries Ltd. | Pyranobenzoxadiazole derivatives, preparation, use and compositions comprising them |
| JPH024791A (ja) * | 1988-06-23 | 1990-01-09 | Nissan Chem Ind Ltd | ピラノベンゾトリアゾール誘導体 |
| EP0409165A2 (en) * | 1989-07-17 | 1991-01-23 | Nissan Chemical Industries Ltd. | Process for the optical resolution of pyranobenzoxadiazole compounds |
| EP0488107A2 (en) * | 1990-11-26 | 1992-06-03 | E.R. SQUIBB & SONS, INC. | Tricyclic benzodiazole analogs and their use in the treatment of cardiovascular disorders |
| EP0693283A1 (en) * | 1993-04-02 | 1996-01-24 | Nissan Chemical Industries, Limited | Heart failure remedy |
Also Published As
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