ZA200607388B - Tricyclic benzopyran compound as anti-arrhythmic agents - Google Patents
Tricyclic benzopyran compound as anti-arrhythmic agents Download PDFInfo
- Publication number
- ZA200607388B ZA200607388B ZA200607388A ZA200607388A ZA200607388B ZA 200607388 B ZA200607388 B ZA 200607388B ZA 200607388 A ZA200607388 A ZA 200607388A ZA 200607388 A ZA200607388 A ZA 200607388A ZA 200607388 B ZA200607388 B ZA 200607388B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- halogen atom
- arbitrarily substituted
- amino
- alkoxy
- Prior art date
Links
- -1 benzopyran compound Chemical class 0.000 title claims description 17
- 239000003416 antiarrhythmic agent Substances 0.000 title abstract description 5
- 125000003277 amino group Chemical group 0.000 claims abstract description 109
- 150000001562 benzopyrans Chemical class 0.000 claims abstract description 93
- 150000003839 salts Chemical class 0.000 claims abstract description 91
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 64
- 150000001875 compounds Chemical class 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000004429 atom Chemical group 0.000 claims abstract description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 125000005843 halogen group Chemical group 0.000 claims description 247
- 125000003545 alkoxy group Chemical group 0.000 claims description 231
- 125000000217 alkyl group Chemical group 0.000 claims description 171
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 146
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 109
- 125000003118 aryl group Chemical group 0.000 claims description 77
- 125000001072 heteroaryl group Chemical group 0.000 claims description 66
- 125000003282 alkyl amino group Chemical group 0.000 claims description 46
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 37
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 28
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 25
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 22
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 18
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical group NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 16
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 16
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 15
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 14
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 12
- 125000001769 aryl amino group Chemical group 0.000 claims description 12
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 12
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 11
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 10
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 9
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 6
- 206010003119 arrhythmia Diseases 0.000 claims description 5
- 230000006793 arrhythmia Effects 0.000 claims description 5
- 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 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 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 34
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
- 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 2
- 239000004480 active ingredient Substances 0.000 claims 2
- IQQDNMHUOLMLNJ-UHFFFAOYSA-N quinolin-3-ol Chemical compound C1=CC=CC2=CC(O)=CN=C21 IQQDNMHUOLMLNJ-UHFFFAOYSA-N 0.000 claims 2
- WXXVQWSDMOAHHV-UHFFFAOYSA-N quinoline-7-carboxylic acid Chemical compound C1=CC=NC2=CC(C(=O)O)=CC=C21 WXXVQWSDMOAHHV-UHFFFAOYSA-N 0.000 claims 2
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 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 1
- CQICGZMHKYHZPH-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-n-(2-phenylbutyl)-3,4-dihydropyrano[2,3-g]quinolin-4-amine Chemical compound C1C(C)(C)OC2=CC3=C(C)C=C(Cl)N=C3C=C2C1NCC(CC)C1=CC=CC=C1 CQICGZMHKYHZPH-UHFFFAOYSA-N 0.000 claims 1
- GZXZYYGQCIHVPL-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-n-(2-phenylethyl)-3,4-dihydropyrano[2,3-g]quinolin-4-amine Chemical compound C1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCC1=CC=CC=C1 GZXZYYGQCIHVPL-UHFFFAOYSA-N 0.000 claims 1
- 102100023245 Asparagine-tRNA ligase, cytoplasmic Human genes 0.000 claims 1
- KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 claims 1
- 101000624939 Homo sapiens Asparagine-tRNA ligase, cytoplasmic Proteins 0.000 claims 1
- 241001553014 Myrsine salicina Species 0.000 claims 1
- 229920013632 Ryton Polymers 0.000 claims 1
- 239000004736 Ryton® Substances 0.000 claims 1
- 241000610375 Sparisoma viride Species 0.000 claims 1
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 2
- 239000000470 constituent Substances 0.000 abstract description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 2
- 125000004434 sulfur atom Chemical group 0.000 abstract description 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000005915 C6-C14 aryl group Chemical group 0.000 abstract 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 abstract 1
- 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 abstract 1
- 230000036279 refractory period Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 210000003205 muscle Anatomy 0.000 description 5
- 230000002861 ventricular Effects 0.000 description 3
- 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
- 230000036982 action potential Effects 0.000 description 2
- 229950004210 cromakalim Drugs 0.000 description 2
- 210000002837 heart atrium Anatomy 0.000 description 2
- VGCNVPXAIFXIDF-UHFFFAOYSA-N 2h-chromen-4-amine Chemical class C1=CC=C2C(N)=CCOC2=C1 VGCNVPXAIFXIDF-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241000269435 Rana <genus> Species 0.000 description 1
- 206010042434 Sudden death Diseases 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- IXTMWRCNAAVVAI-UHFFFAOYSA-N dofetilide Chemical compound C=1C=C(NS(C)(=O)=O)C=CC=1CCN(C)CCOC1=CC=C(NS(C)(=O)=O)C=C1 IXTMWRCNAAVVAI-UHFFFAOYSA-N 0.000 description 1
- 229960002994 dofetilide Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 229960002370 sotalol Drugs 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004084605 | 2004-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200607388B true ZA200607388B (en) | 2008-07-30 |
Family
ID=34962589
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200607388A ZA200607388B (en) | 2004-03-23 | 2005-03-23 | 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 |
Family Cites Families (22)
| 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 |
| JPH0699439B2 (ja) * | 1988-02-03 | 1994-12-07 | 日産化学工業株式会社 | ピラノベンゾオキサジアゾール誘導体 |
| JP2658198B2 (ja) * | 1988-06-23 | 1997-09-30 | 日産化学工業株式会社 | ピラノベンゾトリアゾール誘導体 |
| US5097037A (en) * | 1989-07-17 | 1992-03-17 | Nissan Chemical Industries, Ltd. | Process for the optical resolution of pyranobenzoxadiazole compounds |
| 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 |
| US5164509A (en) * | 1990-11-26 | 1992-11-17 | E. R. Squibb & Sons, Inc. | Benzodiazolo analogs |
| JPH07300414A (ja) * | 1993-04-02 | 1995-11-14 | Nissan Chem Ind Ltd | 心不全治療薬 |
| CZ254095A3 (en) * | 1993-04-02 | 1996-01-17 | Nissan Chemical Ind Ltd | Medicaments for heart insuffiency |
| 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
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