RU2162467C2 - Карбоксамиды бензофурана и их фармацевтическая композиция - Google Patents
Карбоксамиды бензофурана и их фармацевтическая композиция Download PDFInfo
- Publication number
- RU2162467C2 RU2162467C2 RU98123097/04A RU98123097A RU2162467C2 RU 2162467 C2 RU2162467 C2 RU 2162467C2 RU 98123097/04 A RU98123097/04 A RU 98123097/04A RU 98123097 A RU98123097 A RU 98123097A RU 2162467 C2 RU2162467 C2 RU 2162467C2
- Authority
- RU
- Russia
- Prior art keywords
- methoxy
- benzofurancarboxamide
- acetyl
- alkyl
- compound according
- Prior art date
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- QHKJIJXBJCOABP-UHFFFAOYSA-N 1-benzofuran-2-carboxamide Chemical class C1=CC=C2OC(C(=O)N)=CC2=C1 QHKJIJXBJCOABP-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 118
- -1 heterocyclic radical Chemical class 0.000 claims abstract description 56
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 34
- 125000003118 aryl group Chemical group 0.000 claims abstract description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 27
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 14
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 12
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 58
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 22
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 14
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
- 230000002401 inhibitory effect Effects 0.000 claims description 7
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims description 5
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims description 5
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 102000003390 tumor necrosis factor Human genes 0.000 claims 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
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- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 238000011282 treatment Methods 0.000 abstract description 14
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- 239000002571 phosphodiesterase inhibitor Substances 0.000 abstract description 2
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- 239000001257 hydrogen Substances 0.000 abstract 8
- 150000002431 hydrogen Chemical class 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 320
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 186
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 174
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 135
- 235000019439 ethyl acetate Nutrition 0.000 description 108
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- 239000007787 solid Substances 0.000 description 79
- 239000000243 solution Substances 0.000 description 60
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 50
- 238000000746 purification Methods 0.000 description 47
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 23
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- LSMORADTGBFWAQ-UHFFFAOYSA-N 2-acetyl-7-methoxy-1-benzofuran-4-carbonyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C2=C1OC(C(C)=O)=C2 LSMORADTGBFWAQ-UHFFFAOYSA-N 0.000 description 20
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
- 235000019341 magnesium sulphate Nutrition 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
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- 239000000284 extract Substances 0.000 description 11
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000012267 brine Substances 0.000 description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 9
- 239000012043 crude product Substances 0.000 description 9
- 239000012312 sodium hydride Substances 0.000 description 9
- 229910000104 sodium hydride Inorganic materials 0.000 description 9
- 239000012265 solid product Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 239000002585 base Substances 0.000 description 8
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- 239000002244 precipitate Substances 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 241000700605 Viruses Species 0.000 description 7
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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Images
Classifications
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- 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
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
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- A—HUMAN NECESSITIES
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
-
- 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
- C07D405/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Medicinal Chemistry (AREA)
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- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Biomedical Technology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Neurosurgery (AREA)
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- Immunology (AREA)
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- Communicable Diseases (AREA)
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- Hospice & Palliative Care (AREA)
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- Vascular Medicine (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9610515.0 | 1996-05-20 | ||
| GBGB9610515.0A GB9610515D0 (en) | 1996-05-20 | 1996-05-20 | Novel compounds |
| WO???/GB96/03012 | 1996-12-05 | ||
| WOPCT/GB96/03012 | 1996-12-05 | ||
| PCT/GB1996/003012 WO1997020833A1 (en) | 1995-12-05 | 1996-12-05 | Benzofuran carboxamides and sulphonamides |
| GBGB9708070.9A GB9708070D0 (en) | 1997-04-22 | 1997-04-22 | Compounds |
| GB9708070.9 | 1997-04-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU98123097A RU98123097A (ru) | 2000-11-20 |
| RU2162467C2 true RU2162467C2 (ru) | 2001-01-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU98123097/04A RU2162467C2 (ru) | 1996-05-20 | 1997-05-20 | Карбоксамиды бензофурана и их фармацевтическая композиция |
Country Status (19)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2286344C2 (ru) * | 2002-03-28 | 2006-10-27 | Танабе Сейяку Ко.,Лтд | Производные бензофурана |
| RU2319700C1 (ru) * | 2003-09-26 | 2008-03-20 | Танабе Сейяку Ко., Лтд. | Производные бензофурана, содержащие группу карбамоильного типа |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69620458T2 (de) * | 1995-12-05 | 2002-10-02 | Darwin Discovery Ltd., Cambridge | Benzofuran-carboxamide und -sulfonamide |
| ATE229516T1 (de) * | 1996-08-19 | 2002-12-15 | Altana Pharma Ag | Benzofuran-4-carboxamide |
| US6395738B1 (en) | 1997-10-01 | 2002-05-28 | Kyowa Hakko Kogyo Co., Ltd. | Benzofuran derivatives |
| CN1290266A (zh) * | 1998-02-09 | 2001-04-04 | 达尔文发现有限公司 | 苯并呋喃－4－甲酰胺和其治疗用途 |
| ES2196806T3 (es) * | 1998-05-08 | 2003-12-16 | Smithkline Beecham Plc | Derivados de fenilurea y de feniltiourea. |
| TW555759B (en) * | 1998-06-08 | 2003-10-01 | Darwin Discovery Ltd | Heterocyclic compounds and their therapeutic use |
| US7217722B2 (en) | 2000-02-01 | 2007-05-15 | Kirin Beer Kabushiki Kaisha | Nitrogen-containing compounds having kinase inhibitory activity and drugs containing the same |
| GB0003257D0 (en) * | 2000-02-11 | 2000-04-05 | Darwin Discovery Ltd | Heterocyclic compounds and their therapeutic use |
| WO2002012189A1 (en) * | 2000-08-09 | 2002-02-14 | Mitsubishi Pharma Corporation | Fused bicyclic amide compounds and medicinal use thereof |
| US6953774B2 (en) | 2000-08-11 | 2005-10-11 | Applied Research Systems Ars Holding N.V. | Methods of inducing ovulation |
| DK1463493T3 (da) | 2001-12-14 | 2008-02-04 | Serono Lab | Fremgangsmåder til at inducere æglösning ved anvendelse af en ikke polypeptid-cAMP-niveaumodulator |
| AU2003225048A1 (en) * | 2002-04-19 | 2003-11-03 | Integrated Magnetoelectronics Corporation | Interfaces between semiconductor circuitry and transpinnor-based circuitry |
| ES2195785B1 (es) * | 2002-05-16 | 2005-03-16 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| DE10238257B4 (de) * | 2002-08-21 | 2007-04-19 | Johannes-Gutenberg-Universität Mainz | Sorbicillacton A und Sorbicillacton-A-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
| US20050215626A1 (en) * | 2003-09-25 | 2005-09-29 | Wyeth | Substituted benzofuran oximes |
| ES2251866B1 (es) * | 2004-06-18 | 2007-06-16 | Laboratorios Almirall S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| ES2251867B1 (es) * | 2004-06-21 | 2007-06-16 | Laboratorios Almirall S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| JPWO2006088246A1 (ja) * | 2005-02-18 | 2008-07-10 | 武田薬品工業株式会社 | Ｇｐｒ３４受容体機能調節剤 |
| EP2258359A3 (en) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation with sabcomelin |
| CA2620333A1 (en) | 2005-08-26 | 2007-03-01 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| AU2006304787A1 (en) | 2005-10-21 | 2007-04-26 | Braincells, Inc. | Modulation of neurogenesis by PDE inhibition |
| EP2314289A1 (en) | 2005-10-31 | 2011-04-27 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| US7842713B2 (en) * | 2006-04-20 | 2010-11-30 | Pfizer Inc | Fused phenyl amido heterocyclic compounds |
| EP2021000A2 (en) | 2006-05-09 | 2009-02-11 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| EP2865381A1 (en) | 2006-05-18 | 2015-04-29 | Pharmacyclics, Inc. | ITK inhibitors for treating blood cell malignancies |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| CN100434426C (zh) * | 2006-10-10 | 2008-11-19 | 中国科学院昆明植物研究所 | 盐肤木内酯a,其制备方法和其在制药中的应用 |
| CN101631792B (zh) * | 2007-02-28 | 2013-05-01 | 利奥制药有限公司 | 新的磷酸二酯酶抑制剂 |
| SI2114951T1 (sl) * | 2007-02-28 | 2014-08-29 | Leo Pharma A/S | Novi zaviralci fosfodiesteraze |
| ES2320954B1 (es) * | 2007-03-02 | 2010-03-16 | Laboratorio Almirall S.A. | Nuevo procedimiento de preparacion de 3-metil-4-fenilisoxazolo (3,4-d)iridazin-7(6h)-ona. |
| KR100752613B1 (ko) * | 2007-05-02 | 2007-08-29 | 우석대학교 산학협력단 | 신규 벤조푸란 유도체를 포함하는 부정맥 예방용 식품 |
| AR067354A1 (es) | 2007-06-29 | 2009-10-07 | Sunesis Pharmaceuticals Inc | Compuestos utiles como inhibidores de la raf quinasa |
| CA2735184C (en) | 2008-09-11 | 2013-05-28 | Pfizer Inc. | Heteroaryls amide derivatives and their use as glucokinase activators |
| US20100216805A1 (en) | 2009-02-25 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| PL2406253T3 (pl) * | 2009-03-11 | 2013-10-31 | Pfizer | Pochodne benzofuranylu jako inhibitory glukokinazy |
| SI2585469T1 (sl) * | 2010-06-24 | 2016-11-30 | Leo Pharma A/S | Heterociklične spojine benzodioksola ali benzodioksepina kot zaviralci fostodiesteraze |
| CN102010405B (zh) * | 2010-11-08 | 2012-07-25 | 湖南大学 | 4-(苯并呋喃-5-基)-2-苄亚氨基噻唑及其作为抗肿瘤药物的应用 |
| WO2013106547A1 (en) | 2012-01-10 | 2013-07-18 | President And Fellows Of Harvard College | Beta-cell replication promoting compounds and methods of their use |
| WO2016112036A1 (en) | 2015-01-05 | 2016-07-14 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Myc g-quadruplex stabilizing small molecules and their use |
| AR119059A1 (es) * | 2019-06-04 | 2021-11-17 | Nippon Soda Co | Compuesto de benzamida y herbicida |
| GB202306662D0 (en) | 2023-05-05 | 2023-06-21 | Union Therapeutics As | Dosage regimen |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62155269A (ja) * | 1984-12-29 | 1987-07-10 | Kaken Pharmaceut Co Ltd | ベンゾフラン誘導体 |
| WO1992003427A1 (fr) * | 1990-08-17 | 1992-03-05 | Yoshitomi Pharmaceutical Industries, Ltd. | Compose de cetone et remede pour l'osteoporose |
| AU675680B2 (en) * | 1992-10-14 | 1997-02-13 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| GB9309324D0 (en) * | 1993-05-06 | 1993-06-16 | Bayer Ag | Venzofuranyl-and-thiophenyl-alkanecarboxyclic acids derivatives |
| DE69418789T2 (de) * | 1993-08-05 | 1999-12-02 | Hoechst Marion Roussel, Inc. | 2-(Piperidin-4-yl, Pyridin-4-yl und Tetrahydropyridin-4-yl)-benzofuran-7-carbamat Derivate, ihre Herstellung und Verwendung als Acetylcholinesterase Inhibitoren |
| DE69507197T2 (de) * | 1994-05-31 | 1999-05-27 | Bayer Ag, 51373 Leverkusen | Aminobenzofuryl- und -thienylderivate |
| RU2138498C1 (ru) * | 1994-07-22 | 1999-09-27 | Бык Гульден Ломберг Хемише Фабрик Гмбх | Дигидробензофураны, способ их получения и фармацевтическая композиция на их основе |
| AU5772296A (en) * | 1995-05-19 | 1996-11-29 | Chiroscience Limited | 3,4-disubstituted-phenylsulphonamides and their therapeutic use |
| EP0771794B1 (en) * | 1995-05-19 | 2006-05-03 | Kyowa Hakko Kogyo Co., Ltd. | Oxygen-containing heterocyclic compounds |
| JPH10147585A (ja) * | 1996-11-19 | 1998-06-02 | Kyowa Hakko Kogyo Co Ltd | 含酸素複素環化合物 |
| US5728712A (en) * | 1995-05-19 | 1998-03-17 | Chiroscience Limited | 3,4-disubstituted-phenylsulphonamides and their therapeutic use |
| WO1996036596A1 (en) * | 1995-05-19 | 1996-11-21 | Chiroscience Limited | 3,4-disubstituted-phenylsulphonamides and their therapeutic use |
| DE69620458T2 (de) * | 1995-12-05 | 2002-10-02 | Darwin Discovery Ltd., Cambridge | Benzofuran-carboxamide und -sulfonamide |
| ATE229516T1 (de) * | 1996-08-19 | 2002-12-15 | Altana Pharma Ag | Benzofuran-4-carboxamide |
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1997
- 1997-05-20 CA CA002252537A patent/CA2252537A1/en not_active Abandoned
- 1997-05-20 BR BR9709113A patent/BR9709113A/pt active Search and Examination
- 1997-05-20 PL PL97329912A patent/PL329912A1/xx unknown
- 1997-05-20 AT AT97923193T patent/ATE239004T1/de not_active IP Right Cessation
- 1997-05-20 WO PCT/GB1997/001361 patent/WO1997044337A1/en not_active Ceased
- 1997-05-20 HU HU0100042A patent/HUP0100042A3/hu unknown
- 1997-05-20 TR TR1998/02386T patent/TR199802386T2/xx unknown
- 1997-05-20 EP EP97923193A patent/EP0901482B1/en not_active Expired - Lifetime
- 1997-05-20 CN CN97194736A patent/CN1219171A/zh active Pending
- 1997-05-20 IL IL12655897A patent/IL126558A/en not_active IP Right Cessation
- 1997-05-20 NZ NZ332340A patent/NZ332340A/xx unknown
- 1997-05-20 US US08/859,509 patent/US5925636A/en not_active Expired - Fee Related
- 1997-05-20 RU RU98123097/04A patent/RU2162467C2/ru not_active IP Right Cessation
- 1997-05-20 US US08/859,510 patent/US5972936A/en not_active Expired - Fee Related
- 1997-05-20 JP JP09541240A patent/JP2000510848A/ja not_active Ceased
- 1997-05-20 CZ CZ983719A patent/CZ371998A3/cs unknown
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1998
- 1998-11-19 NO NO985375A patent/NO985375D0/no not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2286344C2 (ru) * | 2002-03-28 | 2006-10-27 | Танабе Сейяку Ко.,Лтд | Производные бензофурана |
| RU2319700C1 (ru) * | 2003-09-26 | 2008-03-20 | Танабе Сейяку Ко., Лтд. | Производные бензофурана, содержащие группу карбамоильного типа |
Also Published As
| Publication number | Publication date |
|---|---|
| BR9709113A (pt) | 1999-08-03 |
| EP0901482A1 (en) | 1999-03-17 |
| SK160498A3 (en) | 1999-06-11 |
| IL126558A0 (en) | 1999-08-17 |
| HUP0100042A3 (en) | 2003-01-28 |
| EP0901482B1 (en) | 2003-05-02 |
| PL329912A1 (en) | 1999-04-26 |
| TR199802386T2 (xx) | 1999-02-22 |
| WO1997044337A1 (en) | 1997-11-27 |
| DE69721526D1 (de) | 2003-06-05 |
| CN1219171A (zh) | 1999-06-09 |
| SK282676B6 (sk) | 2002-11-06 |
| ES2193376T3 (es) | 2003-11-01 |
| NO985375L (no) | 1998-11-19 |
| NO985375D0 (no) | 1998-11-19 |
| NZ332340A (en) | 2000-04-28 |
| CZ371998A3 (cs) | 1999-03-17 |
| DE69721526T2 (de) | 2004-04-08 |
| JP2000510848A (ja) | 2000-08-22 |
| ATE239004T1 (de) | 2003-05-15 |
| US5925636A (en) | 1999-07-20 |
| HUP0100042A2 (hu) | 2002-01-28 |
| US5972936A (en) | 1999-10-26 |
| IL126558A (en) | 2002-07-25 |
| CA2252537A1 (en) | 1997-11-27 |
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