NO315468B1 - Nye syrer og estere av diosmetin og farmasöytiske sammensetninger inneholdende dem, samt deres anvendelse - Google Patents
Nye syrer og estere av diosmetin og farmasöytiske sammensetninger inneholdende dem, samt deres anvendelse Download PDFInfo
- Publication number
- NO315468B1 NO315468B1 NO19971861A NO971861A NO315468B1 NO 315468 B1 NO315468 B1 NO 315468B1 NO 19971861 A NO19971861 A NO 19971861A NO 971861 A NO971861 A NO 971861A NO 315468 B1 NO315468 B1 NO 315468B1
- Authority
- NO
- Norway
- Prior art keywords
- hydroxy
- benzopyran
- methoxy
- methoxyphenyl
- carboxymethoxy
- Prior art date
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- MYPLZOPBQZGJQO-UHFFFAOYSA-N ethyl 2-[5-hydroxy-2-(4-methoxy-3-propoxyphenyl)-4-oxochromen-7-yl]oxyacetate Chemical compound C1=C(OC)C(OCCC)=CC(C=2OC3=CC(OCC(=O)OCC)=CC(O)=C3C(=O)C=2)=C1 MYPLZOPBQZGJQO-UHFFFAOYSA-N 0.000 description 1
- CUGAZQSLALFJAH-UHFFFAOYSA-N ethyl 2-[5-hydroxy-2-[4-methoxy-3-(3-methylbut-2-enoxy)phenyl]-4-oxochromen-7-yl]oxyacetate Chemical compound C=1C(OCC(=O)OCC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OCC=C(C)C)=C1 CUGAZQSLALFJAH-UHFFFAOYSA-N 0.000 description 1
- YDSQRJPSDYCORN-UHFFFAOYSA-N ethyl 2-[5-hydroxy-2-[5-hydroxy-4-methoxy-2-(3-methylbutyl)phenyl]-4-oxochromen-7-yl]oxyacetate Chemical compound C=1C(OCC(=O)OCC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC(O)=C(OC)C=C1CCC(C)C YDSQRJPSDYCORN-UHFFFAOYSA-N 0.000 description 1
- OADUUHKWNGFZSI-UHFFFAOYSA-N ethyl 2-[7-[(2,2-dimethyl-1,3-dioxol-4-yl)methoxy]-2-[3-(2-ethoxy-2-oxoethoxy)-4-methoxy-2-propylphenyl]-4-oxochromen-5-yl]oxyacetate Chemical compound CCCC1=C(OCC(=O)OCC)C(OC)=CC=C1C(OC1=C2)=CC(=O)C1=C(OCC(=O)OCC)C=C2OCC1=COC(C)(C)O1 OADUUHKWNGFZSI-UHFFFAOYSA-N 0.000 description 1
- IAMGWHLMQJQUSY-UHFFFAOYSA-N ethyl 2-[7-[(2,2-dimethyl-1,3-dioxol-4-yl)methoxy]-2-[3-(2-ethoxy-2-oxoethoxy)-4-methoxyphenyl]-4-oxochromen-5-yl]oxyacetate Chemical compound C1=C(OC)C(OCC(=O)OCC)=CC(C=2OC3=CC(OCC=4OC(C)(C)OC=4)=CC(OCC(=O)OCC)=C3C(=O)C=2)=C1 IAMGWHLMQJQUSY-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000012771 intravital microscopy Methods 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000006462 rearrangement reaction Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- IKGXIBQEEMLURG-NVPNHPEKSA-N rutin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-NVPNHPEKSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 229960003232 troxerutin Drugs 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- 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]
-
- 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
-
- 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
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9605247A FR2748025B1 (fr) | 1996-04-25 | 1996-04-25 | Nouveaux acides et esters de la diosmetine, et les compositions pharmaceutiques les contenant |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO971861D0 NO971861D0 (no) | 1997-04-23 |
| NO971861L NO971861L (no) | 1997-10-27 |
| NO315468B1 true NO315468B1 (no) | 2003-09-08 |
Family
ID=9491593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19971861A NO315468B1 (no) | 1996-04-25 | 1997-04-23 | Nye syrer og estere av diosmetin og farmasöytiske sammensetninger inneholdende dem, samt deres anvendelse |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5792789A (es) |
| EP (1) | EP0803503B1 (es) |
| JP (1) | JP4144917B2 (es) |
| CN (1) | CN1098848C (es) |
| AT (1) | ATE186299T1 (es) |
| AU (1) | AU707156B2 (es) |
| CA (1) | CA2203463C (es) |
| DE (1) | DE69700719T2 (es) |
| DK (1) | DK0803503T3 (es) |
| ES (1) | ES2143833T3 (es) |
| FR (1) | FR2748025B1 (es) |
| GR (1) | GR3031752T3 (es) |
| HU (1) | HU223349B1 (es) |
| NO (1) | NO315468B1 (es) |
| NZ (1) | NZ314678A (es) |
| PL (1) | PL187257B1 (es) |
| ZA (1) | ZA973646B (es) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5821361A (en) | 1996-06-11 | 1998-10-13 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
| FR2753969B1 (fr) * | 1996-09-27 | 1998-10-30 | Adir | Nouveaux derives de flavones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US6083553A (en) * | 1998-06-05 | 2000-07-04 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
| US20030229136A1 (en) * | 2002-04-18 | 2003-12-11 | Nurulain Zaveri | Novel flavanoids as chemotherapeutic, chemopreventive, and antiangiogenic agents |
| US7638554B2 (en) * | 2002-04-18 | 2009-12-29 | Sri International | Flavanoids as chemotherapeutic, chemopreventive, and antiangiogenic agents |
| FR2882654B1 (fr) * | 2005-03-01 | 2007-04-27 | Servier Lab | Utilisation de derives de la diosmetine pour le traitement et la prevention des pathologies thrombotiques |
| FR2929276B1 (fr) * | 2008-04-01 | 2010-04-23 | Servier Lab | Nouveaux derives de diosmetine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US9209585B2 (en) * | 2010-02-18 | 2015-12-08 | Tyco Electronics Corporation | Crimping tool head |
| CZ304045B6 (cs) | 2012-04-10 | 2013-09-04 | Univerzita Palackého | Pouzití komplexu medi obsahujících 2-fenyl-3-hydroxychinolin-4(1H)-on a deriváty 1,10-fenanthrolinu pro prípravu léciv pro lécbu nádorových onemocnení |
| FR2999934B1 (fr) * | 2012-12-21 | 2015-02-20 | Servier Lab | Composition pharmaceutique sous la forme d'une suspension orale comprenant une fraction flavonoique et de la gomme xanthane |
| CN106031723A (zh) * | 2015-09-29 | 2016-10-19 | 西南大学 | 香叶木素的抗炎活性及其制剂应用 |
| CN109280067B (zh) * | 2017-07-21 | 2022-07-05 | 南京正大天晴制药有限公司 | 香叶木苷衍生物、其制备方法以及医药用途 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2350804A (en) * | 1939-07-22 | 1944-06-06 | Ohta Masaki | Derivatives of hesperidin and process for preparing the same |
| US2897211A (en) * | 1955-11-02 | 1959-07-28 | Recordati Lab Farmacologico S | Hydroxychromone derivatives and method of preparing the same |
| FR1273871A (fr) * | 1958-05-05 | 1961-10-20 | Recordati Lab Farmacologico S | Procédé pour la préparation du flavone-7-oxyacétate d'éthyle |
| BE606547A (fr) * | 1960-08-04 | 1961-11-16 | Ind Chimique Sa | Nouveaux dérivés flavoniques et leur procédé de préparation |
| CH477435A (fr) * | 1960-08-04 | 1969-08-31 | Blaise Rolland | Procédé de préparation de nouveaux dérivés flavoniques |
| FR2081569A1 (en) * | 1970-03-10 | 1971-12-10 | Savel Jean | Diethyl flavone-5,7-dioxyacetate vitamin p - combines coronary, vaso-dilator, lipid - and urea-metabolic activities |
| FR2088127B1 (es) * | 1970-05-21 | 1973-04-06 | Biosedra Lab | |
| FR2281112A1 (fr) * | 1974-08-05 | 1976-03-05 | Lipha | Nouveau medicament choleretique et anti-inflammatoire |
| FR2623808B1 (fr) * | 1987-12-01 | 1990-03-09 | Adir | Nouveaux derives flavonoides (benzyl-4 piperazinyl-1)-2 oxo-2 ethylene substitues, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent |
| FR2726273B1 (fr) * | 1994-10-26 | 1996-12-06 | Adir | Nouveaux derives de la diosmetine, leur procede de preparation et les compositions pharmaceutiques les contenant |
-
1996
- 1996-04-25 FR FR9605247A patent/FR2748025B1/fr not_active Expired - Fee Related
-
1997
- 1997-04-23 AT AT97400912T patent/ATE186299T1/de active
- 1997-04-23 DK DK97400912T patent/DK0803503T3/da active
- 1997-04-23 NO NO19971861A patent/NO315468B1/no not_active IP Right Cessation
- 1997-04-23 CA CA002203463A patent/CA2203463C/fr not_active Expired - Fee Related
- 1997-04-23 JP JP10599297A patent/JP4144917B2/ja not_active Expired - Fee Related
- 1997-04-23 EP EP97400912A patent/EP0803503B1/fr not_active Expired - Lifetime
- 1997-04-23 DE DE69700719T patent/DE69700719T2/de not_active Expired - Lifetime
- 1997-04-23 AU AU19027/97A patent/AU707156B2/en not_active Ceased
- 1997-04-23 ES ES97400912T patent/ES2143833T3/es not_active Expired - Lifetime
- 1997-04-24 PL PL97319652A patent/PL187257B1/pl not_active IP Right Cessation
- 1997-04-24 NZ NZ314678A patent/NZ314678A/xx not_active IP Right Cessation
- 1997-04-24 CN CN97110377A patent/CN1098848C/zh not_active Expired - Fee Related
- 1997-04-25 HU HU9700810A patent/HU223349B1/hu not_active IP Right Cessation
- 1997-04-25 US US08/842,988 patent/US5792789A/en not_active Expired - Lifetime
- 1997-04-25 ZA ZA9703646A patent/ZA973646B/xx unknown
-
1999
- 1999-11-04 GR GR990402721T patent/GR3031752T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE69700719T2 (de) | 2000-06-08 |
| PL319652A1 (en) | 1997-10-27 |
| CA2203463C (fr) | 2002-08-20 |
| HUP9700810A2 (hu) | 1999-09-28 |
| DE69700719D1 (de) | 1999-12-09 |
| HU9700810D0 (en) | 1997-06-30 |
| CA2203463A1 (fr) | 1997-10-25 |
| NO971861D0 (no) | 1997-04-23 |
| DK0803503T3 (da) | 2000-04-10 |
| FR2748025B1 (fr) | 1998-10-30 |
| NZ314678A (en) | 1998-12-23 |
| PL187257B1 (pl) | 2004-06-30 |
| ES2143833T3 (es) | 2000-05-16 |
| AU1902797A (en) | 1997-10-30 |
| CN1167763A (zh) | 1997-12-17 |
| CN1098848C (zh) | 2003-01-15 |
| ZA973646B (en) | 1997-11-19 |
| EP0803503B1 (fr) | 1999-11-03 |
| JP4144917B2 (ja) | 2008-09-03 |
| GR3031752T3 (en) | 2000-02-29 |
| US5792789A (en) | 1998-08-11 |
| FR2748025A1 (fr) | 1997-10-31 |
| HU223349B1 (hu) | 2004-06-28 |
| HUP9700810A3 (en) | 2000-06-28 |
| NO971861L (no) | 1997-10-27 |
| EP0803503A1 (fr) | 1997-10-29 |
| JPH1036365A (ja) | 1998-02-10 |
| ATE186299T1 (de) | 1999-11-15 |
| AU707156B2 (en) | 1999-07-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |