NO328708B1 - 4-Aminobenzopyranderivater - Google Patents

4-Aminobenzopyranderivater Download PDF

Info

Publication number: NO328708B1
Authority: NO; Norway
Prior art keywords: group; hydrogen atom; pharmaceutically acceptable; acceptable salt; compound
Prior art date: 2001-02-14

Application number

NO20033561A

Other languages

English (en)

Norwegian (no)

Other versions

NO20033561D0 (no

NO20033561L (no

Inventor

Yoshio Ohara

Kazuhiko Ohrai

Kazufumi Yanagihara

Yukihiro Shigeta

Toru Tsukagoshi

Toru Yamashita

Original Assignee

Nissan Chemical Ind Ltd

Priority date (The priority date 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 date listed.)

2001-02-14

Filing date

2003-08-12

Publication date

2010-05-03

2003-08-12 Application filed by Nissan Chemical Ind Ltd filed Critical Nissan Chemical Ind Ltd

2003-08-12 Publication of NO20033561D0 publication Critical patent/NO20033561D0/no

2003-10-14 Publication of NO20033561L publication Critical patent/NO20033561L/no

2010-05-03 Publication of NO328708B1 publication Critical patent/NO328708B1/no

Links

125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
150000003839 salts Chemical class 0.000 claims abstract description 18
150000001562 benzopyrans Chemical class 0.000 claims abstract description 16
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 5
125000002947 alkylene group Chemical group 0.000 claims abstract description 4
125000003277 amino group Chemical group 0.000 claims abstract description 3
206010003119 arrhythmia Diseases 0.000 claims description 11
230000006793 arrhythmia Effects 0.000 claims description 11
239000004480 active ingredient Substances 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
238000011282 treatment Methods 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 5
229940079593 drug Drugs 0.000 claims description 4
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 2
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
150000001875 compounds Chemical class 0.000 abstract description 52
239000003416 antiarrhythmic agent Substances 0.000 abstract description 4
125000003545 alkoxy group Chemical group 0.000 abstract description 2
125000004466 alkoxycarbonylamino group Chemical group 0.000 abstract description 2
125000000217 alkyl group Chemical group 0.000 abstract description 2
125000004414 alkyl thio group Chemical group 0.000 abstract description 2
125000003282 alkyl amino group Chemical group 0.000 abstract 1
-1 2-pentyl Chemical group 0.000 description 35
230000000694 effects Effects 0.000 description 23
230000036279 refractory period Effects 0.000 description 16
238000003786 synthesis reaction Methods 0.000 description 15
210000003205 muscle Anatomy 0.000 description 14
230000015572 biosynthetic process Effects 0.000 description 13
239000002904 solvent Substances 0.000 description 13
230000002861 ventricular Effects 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
230000001746 atrial effect Effects 0.000 description 11
239000000243 solution Substances 0.000 description 11
230000037024 effective refractory period Effects 0.000 description 10
238000005160 1H NMR spectroscopy Methods 0.000 description 9
239000000126 substance Substances 0.000 description 9
238000004519 manufacturing process Methods 0.000 description 8
238000000034 method Methods 0.000 description 8
230000000638 stimulation Effects 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
239000002775 capsule Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
239000000829 suppository Substances 0.000 description 6
206010003658 Atrial Fibrillation Diseases 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
230000036982 action potential Effects 0.000 description 5
238000007796 conventional method Methods 0.000 description 5
239000004615 ingredient Substances 0.000 description 5
239000002674 ointment Substances 0.000 description 5
206010003130 Arrhythmia supraventricular Diseases 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
210000002837 heart atrium Anatomy 0.000 description 4
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
230000006794 tachycardia Effects 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000002202 Polyethylene glycol Substances 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
206010003668 atrial tachycardia Diseases 0.000 description 3
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 3
229910001486 lithium perchlorate Inorganic materials 0.000 description 3
239000000203 mixture Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
210000005036 nerve Anatomy 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
230000002265 prevention Effects 0.000 description 3
230000002035 prolonged effect Effects 0.000 description 3
239000003826 tablet Substances 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
230000001515 vagal effect Effects 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
241000416162 Astragalus gummifer Species 0.000 description 2
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
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
206010042434 Sudden death Diseases 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
208000018452 Torsade de pointes Diseases 0.000 description 2
208000002363 Torsades de Pointes Diseases 0.000 description 2
229920001615 Tragacanth Polymers 0.000 description 2
206010047281 Ventricular arrhythmia Diseases 0.000 description 2
KYOIPUDHYRWSFO-UHFFFAOYSA-N [Br].[Li] Chemical compound [Br].[Li] KYOIPUDHYRWSFO-UHFFFAOYSA-N 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
230000002763 arrhythmic effect Effects 0.000 description 2
239000002585 base Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
229950004210 cromakalim Drugs 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
150000003840 hydrochlorides Chemical class 0.000 description 2
230000001939 inductive effect Effects 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
150000002688 maleic acid derivatives Chemical class 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
235000010981 methylcellulose Nutrition 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
150000002825 nitriles Chemical class 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
239000008177 pharmaceutical agent Substances 0.000 description 2
239000006187 pill Substances 0.000 description 2
230000003449 preventive effect Effects 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
239000007901 soft capsule Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
229960002370 sotalol Drugs 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
239000000196 tragacanth Substances 0.000 description 2
235000010487 tragacanth Nutrition 0.000 description 2
229940116362 tragacanth Drugs 0.000 description 2
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
208000003663 ventricular fibrillation Diseases 0.000 description 2
206010047302 ventricular tachycardia Diseases 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
229940058015 1,3-butylene glycol Drugs 0.000 description 1
WORJRXHJTUTINR-UHFFFAOYSA-N 1,4-dioxane;hydron;chloride Chemical compound Cl.C1COCCO1 WORJRXHJTUTINR-UHFFFAOYSA-N 0.000 description 1
KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
MFJCPDOGFAYSTF-UHFFFAOYSA-N 1H-isochromene Chemical class C1=CC=C2COC=CC2=C1 MFJCPDOGFAYSTF-UHFFFAOYSA-N 0.000 description 1
150000005168 4-hydroxybenzoic acids Chemical class 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical class [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
208000005189 Embolism Diseases 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
239000004166 Lanolin Substances 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
AQLLBJAXUCIJSR-UHFFFAOYSA-N OC(=O)C[Na] Chemical class OC(=O)C[Na] AQLLBJAXUCIJSR-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
229920001214 Polysorbate 60 Polymers 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
208000003734 Supraventricular Tachycardia Diseases 0.000 description 1
206010042600 Supraventricular arrhythmias Diseases 0.000 description 1
244000299461 Theobroma cacao Species 0.000 description 1
235000009470 Theobroma cacao Nutrition 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000005196 alkyl carbonyloxy group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000003288 anthiarrhythmic effect Effects 0.000 description 1
238000013459 approach Methods 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000003126 arrythmogenic effect Effects 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
238000011914 asymmetric synthesis Methods 0.000 description 1
229960000686 benzalkonium chloride Drugs 0.000 description 1
TXVHTIQJNYSSKO-UHFFFAOYSA-N benzo[e]pyrene Chemical class C1=CC=C2C3=CC=CC=C3C3=CC=CC4=CC=C1C2=C34 TXVHTIQJNYSSKO-UHFFFAOYSA-N 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000002146 bilateral effect Effects 0.000 description 1
235000019437 butane-1,3-diol Nutrition 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
TXKMVPPZCYKFAC-UHFFFAOYSA-N disulfur monoxide Inorganic materials O=S=S TXKMVPPZCYKFAC-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
230000000857 drug effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000001727 glucose Nutrition 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 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
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000008311 hydrophilic ointment Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229940039717 lanolin Drugs 0.000 description 1
235000019388 lanolin Nutrition 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
229960003511 macrogol Drugs 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
150000004701 malic acid derivatives Chemical class 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
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 1
229920001206 natural gum Polymers 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000001314 paroxysmal effect Effects 0.000 description 1
125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 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
229960002275 pentobarbital sodium Drugs 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
210000003516 pericardium Anatomy 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229940051841 polyoxyethylene ether Drugs 0.000 description 1
229920000056 polyoxyethylene ether Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229950008882 polysorbate Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
230000002980 postoperative effect Effects 0.000 description 1
230000002028 premature Effects 0.000 description 1
238000004393 prognosis Methods 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
229940082004 sodium laurate Drugs 0.000 description 1
WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical class C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012360 testing method Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6
- C07D311/72—3,4-Dihydro derivatives having in position 2 at least one methyl radical and in position 6 one oxygen atom, e.g. tocopherols
- 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
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/70—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with two hydrocarbon radicals attached in position 2 and elements other than carbon and hydrogen in position 6

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrane Compounds (AREA)
Saccharide Compounds (AREA)
Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Organic Insulating Materials (AREA)
External Artificial Organs (AREA)
Non-Adjustable Resistors (AREA)
Discharging, Photosensitive Material Shape In Electrophotography (AREA)

NO20033561A 2001-02-14 2003-08-12 4-Aminobenzopyranderivater NO328708B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP2001036293		2001-02-14
PCT/JP2002/001236 WO2002064581A1 (en)	2001-02-14	2002-02-14	4-aminobenzopyran derivatives

Publications (3)

Publication Number	Publication Date
NO20033561D0 NO20033561D0 (no)	2003-08-12
NO20033561L NO20033561L (no)	2003-10-14
NO328708B1 true NO328708B1 (no)	2010-05-03

Family

ID=18899587

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20033561A NO328708B1 (no)	2001-02-14	2003-08-12	4-Aminobenzopyranderivater

Country Status (19)

Country	Link
US (1)	US6809114B2 (de)
EP (1)	EP1360182B1 (de)
JP (1)	JP2002316981A (de)
KR (1)	KR100849351B1 (de)
CN (1)	CN1250536C (de)
AT (1)	ATE273294T1 (de)
AU (1)	AU2002232182B2 (de)
CA (1)	CA2436438C (de)
CZ (1)	CZ20032145A3 (de)
DE (1)	DE60200937T2 (de)
HU (1)	HUP0303186A3 (de)
IL (2)	IL156943A0 (de)
NO (1)	NO328708B1 (de)
NZ (1)	NZ527040A (de)
RU (1)	RU2288226C2 (de)
SK (1)	SK287023B6 (de)
TW (1)	TW589305B (de)
UA (1)	UA74052C2 (de)
WO (1)	WO2002064581A1 (de)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB0315950D0 (en)	2003-06-11	2003-08-13	Xention Discovery Ltd	Compounds
TWI346112B (en)	2004-02-25	2011-08-01	Nissan Chemical Ind Ltd	Benzopyran compound
JP4840594B2 (ja)	2004-03-23	2011-12-21	日産化学工業株式会社	抗不整脈薬としての３環性ベンゾピラン化合物
GB0412986D0 (en)	2004-06-10	2004-07-14	Xention Discovery Ltd	Compounds
US7576212B2 (en)	2004-12-09	2009-08-18	Xention Limited	Thieno[2,3-B] pyridines as potassium channel inhibitors
GB0525164D0 (en)	2005-12-09	2006-01-18	Xention Discovery Ltd	Compounds
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
GB0815784D0 (en)	2008-08-29	2008-10-08	Xention Ltd	Novel potassium channel blockers
GB0815782D0 (en)	2008-08-29	2008-10-08	Xention Ltd	Novel potassium channel blockers
GB0815781D0 (en)	2008-08-29	2008-10-08	Xention Ltd	Novel potassium channel blockers
GB201105659D0 (en)	2011-04-01	2011-05-18	Xention Ltd	Compounds
NO3175985T3 (de)	2011-07-01	2018-04-28
AR090037A1 (es)	2011-11-15	2014-10-15	Xention Ltd	Derivados de tieno y/o furo-pirimidinas y piridinas inhibidores de los canales de potasio
JP2014533258A (ja)	2011-11-15	2014-12-11	ゼンション・リミテッドＸｅｎｔｉｏｎＬｉｍｉｔｅｄ	カリウムチャネル阻害剤としてのチエノ［２，３−ｃ］ピラゾールの使用
JP2015504923A (ja)	2012-01-27	2015-02-16	ギリアードサイエンシーズ，インコーポレイテッド	後期ナトリウムイオンチャネル遮断剤およびカリウムイオンチャネル遮断剤を使用する併用療法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9005318D0 (en) *	1990-03-09	1990-05-02	Isis Innovation	Antiarrhythmic agents
AU651105B2 (en) *	1990-06-18	1994-07-14	E.R. Squibb & Sons, Inc.	Benzopyran derivatives and heterocyclic analogs thereof as antiischemic agents
GB9301611D0 (en) *	1993-08-04	1993-08-04	Parisella Gerald	Dexterity game
DE19742508A1 (de) *	1997-09-26	1999-04-01	Hoechst Marion Roussel De Gmbh	Sulfonamid-substituierte Chromane, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltende pharmazeutische Zubereitungen
WO2001021610A1 (en) *	1999-09-17	2001-03-29	Nissan Chemical Industries, Ltd.	Benzopyran derivative
US6555574B1 (en) *	1999-09-24	2003-04-29	Nissan Chemical Industries, Ltd.	4-oxybenzopyran derivative
US6677371B1 (en) *	1999-10-05	2004-01-13	Nissan Chemical Industries, Ltd.	4-oxybenzopyran derivative

2001
- 2001-12-27 TW TW090132570A patent/TW589305B/zh not_active IP Right Cessation
2002
- 2002-02-13 JP JP2002034753A patent/JP2002316981A/ja active Pending
- 2002-02-14 CZ CZ20032145A patent/CZ20032145A3/cs unknown
- 2002-02-14 IL IL15694302A patent/IL156943A0/xx active IP Right Grant
- 2002-02-14 CA CA002436438A patent/CA2436438C/en not_active Expired - Fee Related
- 2002-02-14 KR KR1020037010673A patent/KR100849351B1/ko not_active Expired - Fee Related
- 2002-02-14 NZ NZ527040A patent/NZ527040A/en unknown
- 2002-02-14 HU HU0303186A patent/HUP0303186A3/hu unknown
- 2002-02-14 EP EP02712344A patent/EP1360182B1/de not_active Expired - Lifetime
- 2002-02-14 RU RU2003127748/04A patent/RU2288226C2/ru not_active IP Right Cessation
- 2002-02-14 CN CNB02804746XA patent/CN1250536C/zh not_active Expired - Fee Related
- 2002-02-14 UA UA2003098375A patent/UA74052C2/uk unknown
- 2002-02-14 AT AT02712344T patent/ATE273294T1/de not_active IP Right Cessation
- 2002-02-14 AU AU2002232182A patent/AU2002232182B2/en not_active Ceased
- 2002-02-14 US US10/466,175 patent/US6809114B2/en not_active Expired - Fee Related
- 2002-02-14 SK SK1000-2003A patent/SK287023B6/sk not_active IP Right Cessation
- 2002-02-14 DE DE60200937T patent/DE60200937T2/de not_active Expired - Lifetime
- 2002-02-14 WO PCT/JP2002/001236 patent/WO2002064581A1/en not_active Ceased
2003
- 2003-07-15 IL IL156943A patent/IL156943A/en not_active IP Right Cessation
- 2003-08-12 NO NO20033561A patent/NO328708B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
CN1250536C (zh)	2006-04-12
ATE273294T1 (de)	2004-08-15
CA2436438A1 (en)	2002-08-22
SK10002003A3 (sk)	2004-04-06
KR100849351B1 (ko)	2008-07-29
US20040068002A1 (en)	2004-04-08
EP1360182A1 (de)	2003-11-12
IL156943A0 (en)	2004-02-08
NO20033561D0 (no)	2003-08-12
WO2002064581A1 (en)	2002-08-22
NZ527040A (en)	2004-04-30
UA74052C2 (en)	2005-10-17
DE60200937T2 (de)	2005-07-28
HUP0303186A2 (hu)	2003-12-29
JP2002316981A (ja)	2002-10-31
RU2288226C2 (ru)	2006-11-27
RU2003127748A (ru)	2005-03-20
US6809114B2 (en)	2004-10-26
CZ20032145A3 (cs)	2003-12-17
DE60200937D1 (de)	2004-09-16
EP1360182B1 (de)	2004-08-11
CA2436438C (en)	2009-04-07
KR20040018334A (ko)	2004-03-03
HUP0303186A3 (en)	2007-06-28
AU2002232182B2 (en)	2006-09-21
CN1529702A (zh)	2004-09-15
SK287023B6 (sk)	2009-09-07
TW589305B (en)	2004-06-01
IL156943A (en)	2007-05-15
NO20033561L (no)	2003-10-14

Legal Events

Date	Code	Title	Description
2011-09-26	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
US6262068B1 (en)	2001-07-17	Lactam derivatives as antiarrhythmic agents
HUP0202690A2 (hu)	2002-12-28	Antiaritmiás hatású benzopiránszármazékok
US6809114B2 (en)	2004-10-26	4-aminobenzopyran derivatives
US7041700B2 (en)	2006-05-09	Substituted benzopyran derivatives against arrhythmia
EP1214307B1 (de)	2004-04-07	4-oxybenzopyran derivate
US20030114438A1 (en)	2003-06-19	Lactam derivatives as antiarrhythmic agents
AU2002232182A1 (en)	2003-02-20	4-aminobenzopyran derivatives
CA2028668A1 (en)	1991-05-01	Compounds
US4999371A (en)	1991-03-12	Substituted 3,4-dihydro-2H-benzopyrans, processes for their preparation, their use and pharmaceutical products based on these compounds
JPH0717966A (ja)	1995-01-20	４−置換ベンゾピランおよび関連化合物
NO339495B1 (no)	2016-12-19	Trisyklisk benzopyranforbindelse
US6514990B2 (en)	2003-02-04	Pharmaceutically active compounds and methods of use
WO2000012492A1 (en)	2000-03-09	Benzoxazine derivatives
US5097037A (en)	1992-03-17	Process for the optical resolution of pyranobenzoxadiazole compounds
EP0411912A2 (de)	1991-02-06	Cumarinderivate, ihre Herstellung und ihre Verwendung zur Behandlung von zerebrovaskulären Störungen
ES2401587T3 (es)	2013-04-22	Compuesto de benzopirano
US20030069274A1 (en)	2003-04-10	Pharmaceutically active compounds and methods of use
KR100254106B1 (ko)	2000-05-01	4-퀴놀리논 유도체 또는 그의 염
HK1097831B (en)	2013-06-14	Benzopyran compounds useful for the treatment of arrhytmia
EP0033613A1 (de)	1981-08-12	Chromanolderivate, Verfahren zu ihrer Herstellung und diese enthaltende Präparate
HK1063785B (en)	2006-04-07	Substituted benzopyran derivatives against arrhythmia