SK3292002A3 - Benzopyran derivative - Google Patents

Benzopyran derivative Download PDF

Info

Publication number: SK3292002A3
Authority: SK; Slovakia
Prior art keywords: group; synthetic example; alkyl group; pharmaceutically acceptable; nmr
Prior art date: 1999-09-17

Application number

SK329-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Keizo Tanikawa

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.)

1999-09-17

Filing date

2000-09-14

Publication date

2003-04-01

2000-09-14 Application filed by Nissan Chemical Ind Ltd filed Critical Nissan Chemical Ind Ltd

2003-04-01 Publication of SK3292002A3 publication Critical patent/SK3292002A3/sk

Links

150000001562 benzopyrans Chemical class 0.000 title claims abstract description 20
-1 (substituted)phenyl group Chemical group 0.000 claims abstract description 254
150000003839 salts Chemical class 0.000 claims abstract description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
239000004480 active ingredient Substances 0.000 claims abstract description 9
125000003118 aryl group Chemical group 0.000 claims abstract description 6
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims abstract description 5
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 9
206010003119 arrhythmia Diseases 0.000 claims description 9
230000006793 arrhythmia Effects 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
150000002367 halogens Chemical group 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
238000011282 treatment Methods 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000003282 alkyl amino group Chemical group 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 65
230000000694 effects Effects 0.000 abstract description 20
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 6
239000003416 antiarrhythmic agent Substances 0.000 abstract description 6
230000036747 functional refractory period Effects 0.000 abstract 1
238000005160 1H NMR spectroscopy Methods 0.000 description 54
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 49
239000013078 crystal Substances 0.000 description 36
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 30
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 27
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 26
239000012071 phase Substances 0.000 description 26
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 23
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 23
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 22
239000000243 solution Substances 0.000 description 21
239000002904 solvent Substances 0.000 description 21
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 18
210000003205 muscle Anatomy 0.000 description 17
239000000203 mixture Substances 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000126 substance Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
230000001746 atrial effect Effects 0.000 description 10
238000000354 decomposition reaction Methods 0.000 description 10
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 10
230000002035 prolonged effect Effects 0.000 description 10
230000002861 ventricular Effects 0.000 description 10
150000003840 hydrochlorides Chemical class 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
238000000034 method Methods 0.000 description 7
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
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
230000036982 action potential Effects 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000002775 capsule Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000002674 ointment Substances 0.000 description 5
230000003389 potentiating effect Effects 0.000 description 5
ACUOAQKUXNEDQR-UHFFFAOYSA-N 2,2-dimethyl-7-nitrochromene Chemical compound [O-][N+](=O)C1=CC=C2C=CC(C)(C)OC2=C1 ACUOAQKUXNEDQR-UHFFFAOYSA-N 0.000 description 4
206010003130 Arrhythmia supraventricular Diseases 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
125000004744 butyloxycarbonyl group Chemical group 0.000 description 4
235000014113 dietary fatty acids Nutrition 0.000 description 4
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
239000000194 fatty acid Substances 0.000 description 4
229930195729 fatty acid Natural products 0.000 description 4
239000007924 injection Substances 0.000 description 4
238000002347 injection Methods 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
210000003540 papillary muscle Anatomy 0.000 description 4
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
230000000638 stimulation Effects 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
239000003826 tablet Substances 0.000 description 4
230000006794 tachycardia Effects 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
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 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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
239000000460 chlorine Substances 0.000 description 3
125000001309 chloro group Chemical group Cl* 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
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
239000008101 lactose Substances 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
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
238000010898 silica gel chromatography Methods 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000000829 suppository Substances 0.000 description 3
230000001225 therapeutic 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
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
241000416162 Astragalus gummifer Species 0.000 description 2
206010003658 Atrial Fibrillation Diseases 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 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
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
235000010643 Leucaena leucocephala Nutrition 0.000 description 2
240000007472 Leucaena leucocephala Species 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 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
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
206010044565 Tremor Diseases 0.000 description 2
206010047281 Ventricular arrhythmia Diseases 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
150000001412 amines Chemical class 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
229940126214 compound 3 Drugs 0.000 description 2
238000001816 cooling Methods 0.000 description 2
229950004210 cromakalim Drugs 0.000 description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
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 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
239000000839 emulsion Substances 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
229910052731 fluorine Inorganic materials 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
210000002837 heart atrium Anatomy 0.000 description 2
239000001863 hydroxypropyl cellulose Substances 0.000 description 2
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
230000001939 inductive effect Effects 0.000 description 2
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 2
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 2
210000005246 left atrium Anatomy 0.000 description 2
229940057995 liquid paraffin Drugs 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 description 2
125000004674 methylcarbonyl group Chemical group CC(=O)* 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
125000001624 naphthyl group Chemical group 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 2
235000019271 petrolatum Nutrition 0.000 description 2
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125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
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KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 1
125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- C07D311/68—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with nitrogen atoms directly attached in position 4
- 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

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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SK329-2002A 1999-09-17 2000-09-14 Benzopyran derivative SK3292002A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP26445599		1999-09-17
PCT/JP2000/006323 WO2001021610A1 (en)	1999-09-17	2000-09-14	Benzopyran derivative

Publications (1)

Publication Number	Publication Date
SK3292002A3 true SK3292002A3 (en)	2003-04-01

Family

ID=17403453

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK329-2002A SK3292002A3 (en)	1999-09-17	2000-09-14	Benzopyran derivative

Country Status (17)

Country	Link
US (1)	US6589983B1 (de)
EP (1)	EP1212314B1 (de)
KR (1)	KR100766676B1 (de)
CN (1)	CN1167697C (de)
AT (1)	ATE311378T1 (de)
AU (1)	AU766935B2 (de)
CA (1)	CA2383583C (de)
CZ (1)	CZ2002802A3 (de)
DE (1)	DE60024471T2 (de)
HK (1)	HK1047106B (de)
HU (1)	HUP0202690A3 (de)
IL (2)	IL147968A0 (de)
NO (1)	NO328013B1 (de)
NZ (1)	NZ517404A (de)
RU (1)	RU2234502C2 (de)
SK (1)	SK3292002A3 (de)
WO (1)	WO2001021610A1 (de)

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TW589305B (en) *	2001-02-14	2004-06-01	Nissan Chemical Ind Ltd	4-aminobenzopyran derivatives
FI20011507A0 (fi)	2001-07-10	2001-07-10	Orion Corp	Uusia yhdisteitä
JP2005505586A (ja) *	2001-10-04	2005-02-24	ワイス	５−ヒドロキシトリプタミン−６リガンドとしてのクロマン誘導体
KR101078357B1 (ko) *	2002-08-29	2011-10-31	닛산 가가쿠 고교 가부시키 가이샤	아미노벤조피란 화합물의 제조방법
FI20030030A0 (fi)	2003-01-09	2003-01-09	Orion Corp	Uusia yhdisteitä
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
ES2353021T3 (es)	2004-03-23	2011-02-24	Nissan Chemical Industries, Ltd.	Compuesto de benzopirano tricíclico como agentes anti-arrítmicos.
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
CA2591810A1 (en) *	2004-12-21	2006-06-29	F.Hoffmann-La Roche Ag	Chroman derivatives and uses thereof in the treatment of cns disorders
GB0525164D0 (en)	2005-12-09	2006-01-18	Xention Discovery Ltd	Compounds
RU2448112C2 (ru) *	2006-03-10	2012-04-20	Ниссан Кемикал Индастриз, Лтд.	Способ получения оптически активного соединения оксида хромена
GB0815784D0 (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
GB0815782D0 (en)	2008-08-29	2008-10-08	Xention Ltd	Novel potassium channel blockers
AU2011274369A1 (en) *	2010-07-02	2012-12-06	Ventana Medical Systems, Inc.	Hapten conjugates for target detection
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
HK1201455A1 (en)	2012-01-27	2015-09-04	Gilead Sciences Inc	Combination therapies using late sodium ion channel blockers and potassium ion channel blockers
US20220071951A1 (en)	2018-12-28	2022-03-10	Osaka University	Therapeutic agent for inherited bradyarrhythmia

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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
CZ24499A3 (cs) *	1996-07-26	1999-05-12	Nissan Chemical Industries, Ltd.	Derivát chromanu a farmaceutický prostředek, který ho obsahuje

2000
- 2000-09-14 CA CA002383583A patent/CA2383583C/en not_active Expired - Fee Related
- 2000-09-14 DE DE60024471T patent/DE60024471T2/de not_active Expired - Lifetime
- 2000-09-14 HK HK02108750.1A patent/HK1047106B/en not_active IP Right Cessation
- 2000-09-14 US US10/048,026 patent/US6589983B1/en not_active Expired - Fee Related
- 2000-09-14 AT AT00961032T patent/ATE311378T1/de not_active IP Right Cessation
- 2000-09-14 SK SK329-2002A patent/SK3292002A3/sk unknown
- 2000-09-14 IL IL14796800A patent/IL147968A0/xx active IP Right Grant
- 2000-09-14 RU RU2002110115/04A patent/RU2234502C2/ru not_active IP Right Cessation
- 2000-09-14 NZ NZ517404A patent/NZ517404A/xx unknown
- 2000-09-14 EP EP00961032A patent/EP1212314B1/de not_active Expired - Lifetime
- 2000-09-14 CN CNB008129509A patent/CN1167697C/zh not_active Expired - Fee Related
- 2000-09-14 CZ CZ2002802A patent/CZ2002802A3/cs unknown
- 2000-09-14 AU AU73143/00A patent/AU766935B2/en not_active Ceased
- 2000-09-14 KR KR1020027003510A patent/KR100766676B1/ko not_active Expired - Fee Related
- 2000-09-14 HU HU0202690A patent/HUP0202690A3/hu unknown
- 2000-09-14 WO PCT/JP2000/006323 patent/WO2001021610A1/en not_active Ceased
2002
- 2002-02-03 IL IL147968A patent/IL147968A/en not_active IP Right Cessation
- 2002-03-15 NO NO20021294A patent/NO328013B1/no not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU766935B2 (en)	2003-10-23
US6589983B1 (en)	2003-07-08
RU2234502C2 (ru)	2004-08-20
KR20020068505A (ko)	2002-08-27
CN1374957A (zh)	2002-10-16
CA2383583C (en)	2009-04-07
IL147968A (en)	2006-04-10
DE60024471D1 (de)	2006-01-05
NO20021294D0 (no)	2002-03-15
CA2383583A1 (en)	2001-03-29
HK1047106B (en)	2006-04-28
HUP0202690A3 (en)	2005-02-28
HUP0202690A2 (hu)	2002-12-28
DE60024471T2 (de)	2006-08-03
EP1212314B1 (de)	2005-11-30
AU7314300A (en)	2001-04-24
CZ2002802A3 (cs)	2003-02-12
CN1167697C (zh)	2004-09-22
EP1212314A1 (de)	2002-06-12
NO20021294L (no)	2002-03-15
ATE311378T1 (de)	2005-12-15
IL147968A0 (en)	2002-09-12
HK1047106A1 (en)	2003-02-07
NO328013B1 (no)	2009-11-09
KR100766676B1 (ko)	2007-10-15
NZ517404A (en)	2003-01-31
WO2001021610A1 (en)	2001-03-29

Legal Events

Date	Code	Title	Description
2011-03-04	FD9A	Suspended procedure due to non-payment of fee

Publication	Publication Date	Title
SK3292002A3 (en)	2003-04-01	Benzopyran derivative
RU2291867C2 (ru)	2007-01-20	Замещенные производные бензопирана против аритмии
US6555574B1 (en)	2003-04-29	4-oxybenzopyran derivative
US6677371B1 (en)	2004-01-13	4-oxybenzopyran derivative
RU2366658C2 (ru)	2009-09-10	Бензопирановое соединение
JP2001151767A (ja)	2001-06-05	ベンゾピラン誘導体
JP4386159B2 (ja)	2009-12-16	置換ベンゾピラン誘導体
JP2001172275A (ja)	2001-06-26	４−オキシベンゾピラン誘導体
JP2001158780A (ja)	2001-06-12	４−オキシベンゾピラン誘導体
AU2002309284A1 (en)	2003-01-08	Substituted benzopyran derivatives against arrhythmia
HK1063785B (en)	2006-04-07	Substituted benzopyran derivatives against arrhythmia