CZ292443B6 - Benzofuransulfonamid, farmaceutický prostředek jej obsahující a jeho použití - Google Patents
Benzofuransulfonamid, farmaceutický prostředek jej obsahující a jeho použití Download PDFInfo
- Publication number
- CZ292443B6 CZ292443B6 CZ19981714A CZ171498A CZ292443B6 CZ 292443 B6 CZ292443 B6 CZ 292443B6 CZ 19981714 A CZ19981714 A CZ 19981714A CZ 171498 A CZ171498 A CZ 171498A CZ 292443 B6 CZ292443 B6 CZ 292443B6
- Authority
- CZ
- Czechia
- Prior art keywords
- alkyl
- group
- heteroaryl
- defined above
- methoxy
- Prior art date
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- PBECZJTWMSIKFE-UHFFFAOYSA-N 1-benzofuran-2-sulfonamide Chemical compound C1=CC=C2OC(S(=O)(=O)N)=CC2=C1 PBECZJTWMSIKFE-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims abstract description 22
- 238000011282 treatment Methods 0.000 claims abstract description 18
- 208000006673 asthma Diseases 0.000 claims abstract description 7
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- 230000004054 inflammatory process Effects 0.000 claims abstract description 3
- 102000003390 tumor necrosis factor Human genes 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 102
- 239000000203 mixture Substances 0.000 claims description 51
- -1 -OH Chemical group 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 201000010099 disease Diseases 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 230000005764 inhibitory process Effects 0.000 claims description 9
- 239000003981 vehicle Substances 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 5
- 208000010496 Heart Arrest Diseases 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
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- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 5
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- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000002950 monocyclic group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
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- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
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- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 4
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- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 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 3
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- 125000001769 aryl amino group Chemical group 0.000 claims description 3
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
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- ZAVUXVWEXGZBFP-UHFFFAOYSA-N 2-acetyl-n-(furan-2-ylmethyl)-7-methoxy-1-benzofuran-4-sulfonamide Chemical compound C1=2C=C(C(C)=O)OC=2C(OC)=CC=C1S(=O)(=O)NCC1=CC=CO1 ZAVUXVWEXGZBFP-UHFFFAOYSA-N 0.000 claims description 2
- YYYNQDSQFHHLDF-UHFFFAOYSA-N 2-ethyl-7-methoxy-n-methylsulfonyl-n-(pyridin-3-ylmethyl)-1-benzofuran-4-sulfonamide Chemical compound C1=CC(OC)=C2OC(CC)=CC2=C1S(=O)(=O)N(S(C)(=O)=O)CC1=CC=CN=C1 YYYNQDSQFHHLDF-UHFFFAOYSA-N 0.000 claims description 2
- UBSVHVBMOJSDOV-UHFFFAOYSA-N 2-ethyl-7-methoxy-n-methylsulfonyl-n-(pyridin-3-ylmethyl)-1-benzofuran-4-sulfonamide;hydrochloride Chemical compound Cl.C1=CC(OC)=C2OC(CC)=CC2=C1S(=O)(=O)N(S(C)(=O)=O)CC1=CC=CN=C1 UBSVHVBMOJSDOV-UHFFFAOYSA-N 0.000 claims description 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
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- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
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- 206010027175 memory impairment Diseases 0.000 claims description 2
- AHGCKRVJQYBCRZ-UHFFFAOYSA-N n-benzyl-2-ethyl-7-methoxy-1-benzofuran-4-sulfonamide Chemical compound C1=CC(OC)=C2OC(CC)=CC2=C1S(=O)(=O)NCC1=CC=CC=C1 AHGCKRVJQYBCRZ-UHFFFAOYSA-N 0.000 claims description 2
- RTMNIUUBYBNFHX-UHFFFAOYSA-N n-benzyl-2-ethyl-7-methoxy-n-(pyridin-2-ylmethyl)-1-benzofuran-4-sulfonamide Chemical compound C1=CC(OC)=C2OC(CC)=CC2=C1S(=O)(=O)N(CC=1N=CC=CC=1)CC1=CC=CC=C1 RTMNIUUBYBNFHX-UHFFFAOYSA-N 0.000 claims description 2
- SCACIMJYGFQKOY-UHFFFAOYSA-N n-benzyl-2-ethyl-7-methoxy-n-methylsulfonyl-1-benzofuran-4-sulfonamide Chemical compound C1=CC(OC)=C2OC(CC)=CC2=C1S(=O)(=O)N(S(C)(=O)=O)CC1=CC=CC=C1 SCACIMJYGFQKOY-UHFFFAOYSA-N 0.000 claims description 2
- 201000008383 nephritis Diseases 0.000 claims description 2
- 201000008482 osteoarthritis Diseases 0.000 claims description 2
- 230000036303 septic shock Effects 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 3
- 206010017533 Fungal infection Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- HPGNBYRSHKEFTM-UHFFFAOYSA-N 2-acetyl-n-(furan-2-ylmethyl)-7-methoxy-n-propyl-1-benzofuran-4-sulfonamide Chemical compound C=1C=C(OC)C=2OC(C(C)=O)=CC=2C=1S(=O)(=O)N(CCC)CC1=CC=CO1 HPGNBYRSHKEFTM-UHFFFAOYSA-N 0.000 claims 1
- 208000030507 AIDS Diseases 0.000 claims 1
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- 208000006386 Bone Resorption Diseases 0.000 claims 1
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- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract description 4
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 207
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 120
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 111
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 60
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 40
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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 22
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Classifications
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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
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
-
- 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
- C07D405/02—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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9524832.4A GB9524832D0 (en) | 1995-12-05 | 1995-12-05 | Novel compounds |
| GBGB9610515.0A GB9610515D0 (en) | 1996-05-20 | 1996-05-20 | Novel compounds |
| GBGB9610712.3A GB9610712D0 (en) | 1995-12-05 | 1996-05-22 | Novel compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ171498A3 CZ171498A3 (cs) | 1998-10-14 |
| CZ292443B6 true CZ292443B6 (cs) | 2003-09-17 |
Family
ID=27268015
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ19981714A CZ292443B6 (cs) | 1995-12-05 | 1996-12-05 | Benzofuransulfonamid, farmaceutický prostředek jej obsahující a jeho použití |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US5773467A (enExample) |
| EP (1) | EP0873331B1 (enExample) |
| JP (1) | JP2000501411A (enExample) |
| KR (1) | KR19990071894A (enExample) |
| CN (1) | CN1100773C (enExample) |
| AT (1) | ATE215540T1 (enExample) |
| AU (1) | AU697976B2 (enExample) |
| BR (1) | BR9611897A (enExample) |
| CA (1) | CA2238376C (enExample) |
| CZ (1) | CZ292443B6 (enExample) |
| DE (1) | DE69620458T2 (enExample) |
| ES (1) | ES2172695T3 (enExample) |
| HU (1) | HUP9903797A3 (enExample) |
| NO (1) | NO982570L (enExample) |
| PL (1) | PL327181A1 (enExample) |
| WO (1) | WO1997020833A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5972936A (en) * | 1996-05-20 | 1999-10-26 | Darwin Discover Limited | Benzofuran carboxamides and their therapeutic use |
| ES2188983T4 (es) * | 1996-08-19 | 2004-06-01 | Altana Pharma Ag | Nuevas benzofuran-4-carboxamidas. |
| JP3268236B2 (ja) | 1997-07-22 | 2002-03-25 | シャープ株式会社 | 電子写真感光体、及びビスヒドラゾン化合物およびその中間体、ならびにそれら化合物の製造方法 |
| EP1029860B1 (en) | 1997-10-01 | 2003-04-16 | Kyowa Hakko Kogyo Co., Ltd. | Benzofuran derivatives |
| AU1983599A (en) * | 1998-01-26 | 1999-08-09 | Kyowa Hakko Kogyo Co. Ltd. | Oxygenic heterocyclic compounds |
| AU2529799A (en) * | 1998-02-09 | 1999-08-23 | Darwin Discovery Limited | Benzofuran-4-carboxamides and their therapeutic use |
| FR2778662B1 (fr) * | 1998-05-12 | 2000-06-16 | Adir | Nouveaux composes cycliques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| TW555759B (en) * | 1998-06-08 | 2003-10-01 | Darwin Discovery Ltd | Heterocyclic compounds and their therapeutic use |
| WO1999064414A1 (de) * | 1998-06-10 | 1999-12-16 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Benzamide mit tetrahydrofuranyloxy-substituenten als inhibitoren der phosphodiesterase 4 |
| EP1671651B1 (en) | 1999-08-21 | 2009-11-11 | Nycomed GmbH | Synergistic combination of pumafentrine and salmeterol |
| US7217722B2 (en) | 2000-02-01 | 2007-05-15 | Kirin Beer Kabushiki Kaisha | Nitrogen-containing compounds having kinase inhibitory activity and drugs containing the same |
| GB0011802D0 (en) * | 2000-05-16 | 2000-07-05 | Smithkline Beecham | Method for enhancing cognitive function |
| JP2006522151A (ja) | 2003-04-01 | 2006-09-28 | アプライド リサーチ システムズ エーアールエス ホールディング ナームロゼ フェンノートシャップ | 不妊症におけるホスホジエステラーゼ阻害剤 |
| FR2903106B1 (fr) * | 2006-07-03 | 2010-07-30 | Sanofi Aventis | Utilisations de 2-benzoyl-imidazopyridines en therapeutique |
| EP2196465A1 (en) | 2008-12-15 | 2010-06-16 | Almirall, S.A. | (3-oxo)pyridazin-4-ylurea derivatives as PDE4 inhibitors |
| AR074760A1 (es) * | 2008-12-18 | 2011-02-09 | Metabolex Inc | Agonistas del receptor gpr120 y usos de los mismos en medicamentos para el tratamiento de diabetes y el sindrome metabolico. |
| EP2226323A1 (en) | 2009-02-27 | 2010-09-08 | Almirall, S.A. | New tetrahydropyrazolo[3,4-c]isoquinolin-5-amine derivatives |
| EP2380890A1 (en) | 2010-04-23 | 2011-10-26 | Almirall, S.A. | New 7,8-dihydro-1,6-naphthyridin-5(6h)-one-derivatives as PDE4 inhibitors |
| EP2394998A1 (en) | 2010-05-31 | 2011-12-14 | Almirall, S.A. | 3-(5-Amino-6-oxo-1,6-dihydropyridazin-3-yl)-biphenyl derivatives as PDE4 inhibitors |
| EP2597093B1 (en) | 2010-07-22 | 2014-11-05 | Fuso Pharmaceutical Industries, Ltd. | Benzofuranone compound and pharmaceutical composition containing same |
| US10196372B2 (en) | 2015-01-05 | 2019-02-05 | 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 |
| CN114149457B (zh) * | 2021-11-03 | 2024-04-12 | 湖北民族大学 | 一种苯并[c][1,2]氧杂硼戊环-1(3H)-醇类合物及其用途 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES8705871A1 (es) * | 1984-12-29 | 1987-05-16 | Kaken Pharma Co Ltd | Un procedimiento para preparar un derivado de benzofurano |
| ES2127966T3 (es) * | 1994-05-31 | 1999-05-01 | Bayer Ag | Derivados de amino-benzofurilo y -benzotienilo. |
| ES2152414T3 (es) * | 1994-07-22 | 2001-02-01 | Byk Gulden Lomberg Chem Fab | Dihidrobenzofuranos. |
| WO1996036624A1 (en) * | 1995-05-19 | 1996-11-21 | Kyowa Hakko Kogyo Co., Ltd. | Oxygen-containing heterocyclic compounds |
| US5972936A (en) * | 1996-05-20 | 1999-10-26 | Darwin Discover Limited | Benzofuran carboxamides and their therapeutic use |
-
1996
- 1996-12-05 JP JP9521090A patent/JP2000501411A/ja not_active Ceased
- 1996-12-05 BR BR9611897-0A patent/BR9611897A/pt active Search and Examination
- 1996-12-05 EP EP96941138A patent/EP0873331B1/en not_active Expired - Lifetime
- 1996-12-05 CA CA002238376A patent/CA2238376C/en not_active Expired - Fee Related
- 1996-12-05 WO PCT/GB1996/003012 patent/WO1997020833A1/en not_active Ceased
- 1996-12-05 AT AT96941138T patent/ATE215540T1/de not_active IP Right Cessation
- 1996-12-05 HU HU9903797A patent/HUP9903797A3/hu unknown
- 1996-12-05 PL PL96327181A patent/PL327181A1/xx unknown
- 1996-12-05 CN CN96198844A patent/CN1100773C/zh not_active Expired - Fee Related
- 1996-12-05 KR KR1019980704179A patent/KR19990071894A/ko not_active Ceased
- 1996-12-05 AU AU10386/97A patent/AU697976B2/en not_active Ceased
- 1996-12-05 US US08/761,102 patent/US5773467A/en not_active Expired - Fee Related
- 1996-12-05 ES ES96941138T patent/ES2172695T3/es not_active Expired - Lifetime
- 1996-12-05 CZ CZ19981714A patent/CZ292443B6/cs not_active IP Right Cessation
- 1996-12-05 DE DE69620458T patent/DE69620458T2/de not_active Expired - Fee Related
-
1998
- 1998-06-04 NO NO982570A patent/NO982570L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| MX9804466A (es) | 1998-12-31 |
| CN1208411A (zh) | 1999-02-17 |
| NO982570L (no) | 1998-08-04 |
| EP0873331A1 (en) | 1998-10-28 |
| KR19990071894A (ko) | 1999-09-27 |
| PL327181A1 (en) | 1998-11-23 |
| AU697976B2 (en) | 1998-10-22 |
| AU1038697A (en) | 1997-06-27 |
| CA2238376C (en) | 2006-08-15 |
| NO982570D0 (no) | 1998-06-04 |
| CZ171498A3 (cs) | 1998-10-14 |
| CN1100773C (zh) | 2003-02-05 |
| JP2000501411A (ja) | 2000-02-08 |
| DE69620458D1 (de) | 2002-05-08 |
| WO1997020833A1 (en) | 1997-06-12 |
| ES2172695T3 (es) | 2002-10-01 |
| US5773467A (en) | 1998-06-30 |
| HUP9903797A2 (hu) | 2001-04-28 |
| HUP9903797A3 (en) | 2001-08-28 |
| CA2238376A1 (en) | 1997-06-12 |
| ATE215540T1 (de) | 2002-04-15 |
| BR9611897A (pt) | 1999-12-28 |
| DE69620458T2 (de) | 2002-10-02 |
| EP0873331B1 (en) | 2002-04-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PD00 | Pending as of 2000-06-30 in czech republic | ||
| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20041205 |