NO320727B1 - Benzofuran- eller benzopyranderivater med fundusavslappende egenskaper, deres fremstilling og farmasoytiske sammensetninger inneholdende denne - Google Patents
Benzofuran- eller benzopyranderivater med fundusavslappende egenskaper, deres fremstilling og farmasoytiske sammensetninger inneholdende denne Download PDFInfo
- Publication number
- NO320727B1 NO320727B1 NO20002074A NO20002074A NO320727B1 NO 320727 B1 NO320727 B1 NO 320727B1 NO 20002074 A NO20002074 A NO 20002074A NO 20002074 A NO20002074 A NO 20002074A NO 320727 B1 NO320727 B1 NO 320727B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- alkyl
- hydrogen
- compound
- radical
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 230000002040 relaxant effect Effects 0.000 title description 5
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 title 2
- 150000001562 benzopyrans Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 98
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- -1 cyano, nitro, amino Chemical group 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000000815 N-oxide group Chemical group 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 150000001721 carbon Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000013067 intermediate product Substances 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- HTHYHKLEFHPLHL-UHFFFAOYSA-N 1-[3-(3,4-dihydro-2h-chromen-2-ylmethylamino)propyl]-1,3-diazinan-2-one Chemical compound O=C1NCCCN1CCCNCC1OC2=CC=CC=C2CC1 HTHYHKLEFHPLHL-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 230000009466 transformation Effects 0.000 claims description 2
- 125000004951 trihalomethoxy group Chemical group 0.000 claims description 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims 1
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- 239000000203 mixture Substances 0.000 description 63
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- 239000000543 intermediate Substances 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
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- 238000010992 reflux Methods 0.000 description 7
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- WFKLUNLIZMWKNF-UHFFFAOYSA-N tert-butyl n-(1-benzylpiperidin-4-yl)carbamate Chemical compound C1CC(NC(=O)OC(C)(C)C)CCN1CC1=CC=CC=C1 WFKLUNLIZMWKNF-UHFFFAOYSA-N 0.000 description 1
- 230000036977 tonic contraction Effects 0.000 description 1
- 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
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- 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
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97203808 | 1997-12-05 | ||
| PCT/EP1998/007771 WO1999029687A1 (en) | 1997-12-05 | 1998-11-27 | (benzodioxan, benzofuran or benzopyran) derivatives having fundic relaxation properties |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20002074D0 NO20002074D0 (no) | 2000-04-19 |
| NO20002074L NO20002074L (no) | 2000-06-02 |
| NO320727B1 true NO320727B1 (no) | 2006-01-23 |
Family
ID=8229014
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20002074A NO320727B1 (no) | 1997-12-05 | 2000-04-19 | Benzofuran- eller benzopyranderivater med fundusavslappende egenskaper, deres fremstilling og farmasoytiske sammensetninger inneholdende denne |
Country Status (32)
| Country | Link |
|---|---|
| US (4) | US6133277A (cs) |
| EP (1) | EP1036073B8 (cs) |
| JP (1) | JP2001525407A (cs) |
| KR (1) | KR100591605B1 (cs) |
| CN (1) | CN1155597C (cs) |
| AR (1) | AR017195A1 (cs) |
| AT (1) | ATE334125T1 (cs) |
| AU (1) | AU748669B2 (cs) |
| BG (1) | BG64624B1 (cs) |
| BR (1) | BR9814256A (cs) |
| CA (1) | CA2311669C (cs) |
| CO (1) | CO5011114A1 (cs) |
| CZ (1) | CZ297895B6 (cs) |
| DE (1) | DE69835372T2 (cs) |
| EA (1) | EA003365B1 (cs) |
| EE (1) | EE04438B1 (cs) |
| ES (1) | ES2270541T3 (cs) |
| HK (1) | HK1028400A1 (cs) |
| HR (1) | HRP20000340B1 (cs) |
| HU (1) | HU224813B1 (cs) |
| ID (1) | ID24616A (cs) |
| IL (1) | IL136529A (cs) |
| MY (1) | MY124586A (cs) |
| NO (1) | NO320727B1 (cs) |
| NZ (1) | NZ503603A (cs) |
| PL (1) | PL191144B1 (cs) |
| SK (1) | SK286268B6 (cs) |
| TR (1) | TR200001542T2 (cs) |
| TW (1) | TW577886B (cs) |
| UA (1) | UA70308C2 (cs) |
| WO (1) | WO1999029687A1 (cs) |
| ZA (1) | ZA9811081B (cs) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6133277A (en) | 1997-12-05 | 2000-10-17 | Janssen Pharmaceutica N.V. | (Benzodioxan, benzofuran or benzopyran) derivatives having fundic relaxation properties |
| PL198532B1 (pl) * | 1999-06-02 | 2008-06-30 | Janssen Pharmaceutica Nv | Pochodna benzopiranu podstawiona pirolidynylem, piperydynylem lub homopiperydynylem i sposób jej otrzymywania oraz kompozycja farmaceutyczna i sposób jej otrzymywania |
| DK1187829T3 (da) * | 1999-06-02 | 2004-04-13 | Janssen Pharmaceutica Nv | Aminoalkylsubstituerede (benzodioxan, benzofuran eller benzopyran) derivater |
| JO2352B1 (en) * | 2000-06-22 | 2006-12-12 | جانسين فارماسيوتيكا ان. في | Compounds for the treatment of non-adaptation of the bottom of the uterus |
| JO2654B1 (en) | 2000-09-04 | 2012-06-17 | شركة جانسين فارماسوتيكا ان. في | Multiple aryl caroxa amides are useful as lipid - lowering agents |
| JO2409B1 (en) * | 2000-11-21 | 2007-06-17 | شركة جانسين فارماسوتيكا ان. في | Second-phenyl carboxy amides are useful as lipid-lowering agents |
| US6688079B2 (en) | 2001-04-18 | 2004-02-10 | Kraft Foods Holdings, Inc. | Method for manufacturing flexible packages having slide closures |
| US20050014818A1 (en) * | 2001-11-09 | 2005-01-20 | Masaru Mitsuda | Process for producing optically active chroman derivative and intermediate |
| ES2199086B1 (es) | 2002-07-31 | 2005-06-01 | Cepa Schwarz Pharma Sl | Nuevos derivados de cicloalcanodionas, procedimiento para su preparacion y sus aplicaciones farmacologicas. |
| US7071821B2 (en) * | 2003-05-14 | 2006-07-04 | Bellsouth Intellectual Property Corporation | Method and system for alerting a person to a situation |
| ITTO20030140U1 (it) * | 2003-09-16 | 2005-03-17 | Interfila Srl | Matita cosmetica |
| WO2005032544A1 (en) | 2003-09-19 | 2005-04-14 | Galileo Pharmaceuticals, Inc. | Treatment of mitochondrial diseases |
| EP1687277B1 (en) | 2003-11-20 | 2018-04-04 | Janssen Pharmaceutica NV | 6-alkenyl and 6-phenylalkyl substituted 2-quinolinones and 2-quinoxalinones as poly(adp-ribose) polymerase inhibitors |
| CN1882549B (zh) | 2003-11-20 | 2011-02-23 | 詹森药业有限公司 | 用作聚(adp-核糖)聚合酶抑制剂的7-苯基烷基取代的2-喹啉酮和2-喹喔啉酮 |
| ES2238015B1 (es) * | 2004-01-30 | 2006-11-01 | Cepa Schwarz Pharma, S.L. | Derivados de cicloalcanodionas con actividad neuroprotectora. |
| EP1771175B1 (en) | 2004-06-30 | 2015-12-23 | Janssen Pharmaceutica NV | Phthalazine derivatives as parp inhibitors |
| NZ551801A (en) * | 2004-06-30 | 2009-11-27 | Janssen Pharmaceutica Nv | Quinazolinedione derivatives as PARP inhibitors |
| AU2005259188B2 (en) | 2004-06-30 | 2011-03-31 | Janssen Pharmaceutica N.V. | Quinazolinone derivatives as PARP inhibitors |
| DE102004032277A1 (de) * | 2004-07-02 | 2006-01-19 | Basell Polyolefine Gmbh | Verfahren zur racemoselektiven Synthese von ansa-Metallocenen |
| JP2008530229A (ja) | 2005-02-17 | 2008-08-07 | ワイス | シクロアルキル縮合インドール、ベンゾチオフェン、ベンゾフランおよびインデン誘導体 |
| RU2007139541A (ru) * | 2005-04-22 | 2009-05-27 | Вайет (Us) | Производные хромана и хромена и их применение |
| WO2008015538A2 (en) * | 2006-07-31 | 2008-02-07 | Schwarz Pharma S.L. | Use of diaza- and thiaza-cycloalkanediones for preventing and/or treating pain and /or migraine |
| US20080033050A1 (en) | 2006-08-04 | 2008-02-07 | Richards Patricia Allison Tewe | Method of treating thermoregulatory disfunction with paroxetine |
| US8503431B2 (en) * | 2006-08-25 | 2013-08-06 | Wireless Wonders Ltd. | Mobile phone related indirect communication system and method |
| DK2134691T3 (da) | 2007-03-08 | 2012-05-07 | Janssen Pharmaceutica Nv | Quinolinonderivativer som parp- og tank-inhibitorer |
| JP5017703B2 (ja) * | 2007-05-16 | 2012-09-05 | 住友ゴム工業株式会社 | ビードエイペックスおよびタイヤ |
| ES2448870T3 (es) | 2007-10-26 | 2014-03-17 | Janssen Pharmaceutica, N.V. | Derivados de quinolina como inhibidores de PARP |
| ATE513818T1 (de) | 2008-03-27 | 2011-07-15 | Janssen Pharmaceutica Nv | Chinazolinonderivate als tubulinpolymerisationshemmer |
| EP2271626B1 (en) | 2008-03-27 | 2014-11-26 | Janssen Pharmaceutica, N.V. | Tetrahydrophenanthridinones and tetrahydrocyclopentaquinolinones as parp and tubulin polymerization inhibitors |
| RS59172B1 (sr) | 2012-02-24 | 2019-10-31 | Lupin Ltd | Supstituisana jedinjenja hromana kao modulatori receptora osetljivog na kalcijum |
| US9040533B2 (en) | 2012-12-27 | 2015-05-26 | Purdue Pharma L.P. | Oxime-substituted-quinoxaline-type piperidine compounds as ORL-1 modulators |
| DE102013207163B4 (de) | 2013-04-19 | 2022-09-22 | Adidas Ag | Schuhoberteil |
| DE102014220087B4 (de) | 2014-10-02 | 2016-05-12 | Adidas Ag | Flachgestricktes Schuhoberteil für Sportschuhe |
| WO2017115372A1 (en) | 2015-12-30 | 2017-07-06 | Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd | Pt(IV) PRODRUGS |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3910930A (en) * | 1973-01-04 | 1975-10-07 | Janssen Pharmaceutica Nv | 1-{55 1-{8 2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl{9 -4-piperidyl{56 -2-benzimidazolinones |
| US3929801A (en) * | 1973-11-20 | 1975-12-30 | Janssen Pharmaceutica Nv | 2-Benzimidazolinones |
| GB1599296A (en) * | 1977-07-06 | 1981-09-30 | Brewster D L | Ice making machine |
| GR71865B (cs) * | 1978-03-20 | 1983-07-07 | Ciba Geigy | |
| DE2852945A1 (de) * | 1978-12-07 | 1980-06-26 | Boehringer Sohn Ingelheim | Benzodioxanyl-hydroxyaethylpiperidyl- imidazolidinone, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| US4329348A (en) * | 1979-02-26 | 1982-05-11 | Ciba-Geigy Corporation | N-Oxacyclic-alkylpiperidines as psychostimulants |
| US4239348A (en) * | 1979-11-30 | 1980-12-16 | Hughes Aircraft Company | High resolution AC silicon MOS light-valve substrate |
| DE3901814A1 (de) * | 1988-07-28 | 1990-02-01 | Bayer Ag | Substituierte aminomethylzetraline sowie ihre heterocyclischen analoga |
| DE4140540A1 (de) * | 1991-12-09 | 1993-06-17 | Bayer Ag | Neue azaheterocyclylmethyl-chromane |
| SI9300097B (en) * | 1992-02-27 | 2001-12-31 | Janssen Pharmaceutica Nv | (benzodioxan, benzofuran or benzopyran) alkylamino) alkyl substituted guanidines |
| DE4319038A1 (de) * | 1993-06-08 | 1994-12-15 | Bayer Ag | Verwendung von teilweise bekannten substituierten Chromanen als Arzneimittel, neue Wirkstoffe und Verfahren zu ihrer Herstellung |
| CN1052006C (zh) * | 1993-08-19 | 2000-05-03 | 詹森药业有限公司 | 血管收缩剂二氢苯并吡喃衍生物,制备方法和用途 |
| US5541199A (en) * | 1995-06-02 | 1996-07-30 | American Home Products Corporation | Chroman-2-ylmethylamino derivatives |
| FR2744451B1 (fr) * | 1996-02-01 | 1998-04-24 | Pf Medicament | Nouvelles imidazolidinones, pyrimidinones, et 1,3-diazepin-2 -ones, leur preparation et leurs applications en therapeutique |
| US5696653A (en) * | 1996-12-13 | 1997-12-09 | Phase Metrics | Tooling for holding a head gimbal assembly |
| US6133277A (en) * | 1997-12-05 | 2000-10-17 | Janssen Pharmaceutica N.V. | (Benzodioxan, benzofuran or benzopyran) derivatives having fundic relaxation properties |
-
1998
- 1998-11-16 US US09/192,686 patent/US6133277A/en not_active Expired - Lifetime
- 1998-11-25 TW TW087119526A patent/TW577886B/zh not_active IP Right Cessation
- 1998-11-27 SK SK803-2000A patent/SK286268B6/sk not_active IP Right Cessation
- 1998-11-27 TR TR2000/01542T patent/TR200001542T2/xx unknown
- 1998-11-27 PL PL341007A patent/PL191144B1/pl not_active IP Right Cessation
- 1998-11-27 ID IDW20001041D patent/ID24616A/id unknown
- 1998-11-27 CZ CZ20002018A patent/CZ297895B6/cs not_active IP Right Cessation
- 1998-11-27 IL IL13652998A patent/IL136529A/xx not_active IP Right Cessation
- 1998-11-27 UA UA2000053031A patent/UA70308C2/uk unknown
- 1998-11-27 ES ES98966603T patent/ES2270541T3/es not_active Expired - Lifetime
- 1998-11-27 AU AU24127/99A patent/AU748669B2/en not_active Ceased
- 1998-11-27 AT AT98966603T patent/ATE334125T1/de not_active IP Right Cessation
- 1998-11-27 EP EP98966603A patent/EP1036073B8/en not_active Expired - Lifetime
- 1998-11-27 JP JP2000524281A patent/JP2001525407A/ja active Pending
- 1998-11-27 BR BR9814256-9A patent/BR9814256A/pt not_active Application Discontinuation
- 1998-11-27 HU HU0004492A patent/HU224813B1/hu not_active IP Right Cessation
- 1998-11-27 EA EA200000616A patent/EA003365B1/ru not_active IP Right Cessation
- 1998-11-27 WO PCT/EP1998/007771 patent/WO1999029687A1/en active IP Right Grant
- 1998-11-27 CA CA2311669A patent/CA2311669C/en not_active Expired - Lifetime
- 1998-11-27 NZ NZ503603A patent/NZ503603A/en unknown
- 1998-11-27 DE DE69835372T patent/DE69835372T2/de not_active Expired - Lifetime
- 1998-11-27 EE EEP200000328A patent/EE04438B1/xx not_active IP Right Cessation
- 1998-11-27 KR KR1020007003796A patent/KR100591605B1/ko not_active IP Right Cessation
- 1998-11-27 CN CNB988118319A patent/CN1155597C/zh not_active Expired - Fee Related
- 1998-12-01 CO CO98071204A patent/CO5011114A1/es unknown
- 1998-12-01 MY MYPI98005442A patent/MY124586A/en unknown
- 1998-12-03 ZA ZA9811081A patent/ZA9811081B/xx unknown
- 1998-12-04 AR ARP980106182A patent/AR017195A1/es active IP Right Grant
-
2000
- 2000-04-19 NO NO20002074A patent/NO320727B1/no not_active IP Right Cessation
- 2000-04-24 BG BG104372A patent/BG64624B1/bg unknown
- 2000-05-25 HR HR20000340A patent/HRP20000340B1/xx not_active IP Right Cessation
- 2000-08-18 US US09/641,485 patent/US6495547B1/en not_active Expired - Lifetime
- 2000-12-07 HK HK00107845A patent/HK1028400A1/xx not_active IP Right Cessation
-
2002
- 2002-04-03 US US10/116,590 patent/US6747045B2/en not_active Expired - Lifetime
- 2002-09-05 US US10/235,623 patent/US6852714B2/en not_active Expired - Lifetime
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO320727B1 (no) | Benzofuran- eller benzopyranderivater med fundusavslappende egenskaper, deres fremstilling og farmasoytiske sammensetninger inneholdende denne | |
| US7358239B2 (en) | Pyrrolidinyl, piperidinyl or homopiperidinyl substituted (benzodioxan, benzofuran or benzopyran) derivatives | |
| KR100699512B1 (ko) | 아미노알킬 치환된 (벤조디옥산, 벤조푸란 또는 벤조피란)유도체 | |
| MXPA00005524A (en) | (benzodioxan, benzofuran or benzopyran) derivatives having fundic relaxation properties |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |