NO311132B1 - Nye diosmetinforbindelser, fremgangsmåte ved deres fremstilling og farmasöytiske preparater inneholdende dem - Google Patents
Nye diosmetinforbindelser, fremgangsmåte ved deres fremstilling og farmasöytiske preparater inneholdende dem Download PDFInfo
- Publication number
- NO311132B1 NO311132B1 NO19954173A NO954173A NO311132B1 NO 311132 B1 NO311132 B1 NO 311132B1 NO 19954173 A NO19954173 A NO 19954173A NO 954173 A NO954173 A NO 954173A NO 311132 B1 NO311132 B1 NO 311132B1
- Authority
- NO
- Norway
- Prior art keywords
- hydroxy
- benzopyran
- formula
- compound
- methoxy
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 209
- 238000002360 preparation method Methods 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 10
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 18
- MBNGWHIJMBWFHU-UHFFFAOYSA-N diosmetin Chemical compound C1=C(O)C(OC)=CC=C1C1=CC(=O)C2=C(O)C=C(O)C=C2O1 MBNGWHIJMBWFHU-UHFFFAOYSA-N 0.000 claims abstract description 15
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 12
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims abstract description 8
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 26
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- 238000000692 Student's t-test Methods 0.000 description 1
- YDWKEUCCRAUKKM-AWEZNQCLSA-N [(2r)-2-hydroxy-3-[5-hydroxy-2-(3-hydroxy-4-methoxy-2-propylphenyl)-4-oxochromen-7-yl]oxypropyl] acetate Chemical compound CCCC1=C(O)C(OC)=CC=C1C1=CC(=O)C2=C(O)C=C(OC[C@@H](O)COC(C)=O)C=C2O1 YDWKEUCCRAUKKM-AWEZNQCLSA-N 0.000 description 1
- YDWKEUCCRAUKKM-CQSZACIVSA-N [(2s)-2-hydroxy-3-[5-hydroxy-2-(3-hydroxy-4-methoxy-2-propylphenyl)-4-oxochromen-7-yl]oxypropyl] acetate Chemical compound CCCC1=C(O)C(OC)=CC=C1C1=CC(=O)C2=C(O)C=C(OC[C@H](O)COC(C)=O)C=C2O1 YDWKEUCCRAUKKM-CQSZACIVSA-N 0.000 description 1
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- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- HDRXZJPWHTXQRI-BHDTVMLSSA-N diltiazem hydrochloride Chemical compound [Cl-].C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CC[NH+](C)C)C2=CC=CC=C2S1 HDRXZJPWHTXQRI-BHDTVMLSSA-N 0.000 description 1
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- 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
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- ABXSODXBCMKEND-UHFFFAOYSA-N methyl 3,4,5-triacetyloxy-6-[3-[7-[(2,2-dimethyl-1,3-dioxol-4-yl)methoxy]-5-methoxy-4-oxochromen-2-yl]-6-methoxy-2-propylphenoxy]oxane-2-carboxylate Chemical compound COC1=CC=C(C=2OC3=CC(OCC=4OC(C)(C)OC=4)=CC(OC)=C3C(=O)C=2)C(CCC)=C1OC1OC(C(=O)OC)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O ABXSODXBCMKEND-UHFFFAOYSA-N 0.000 description 1
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- 229960001412 pentobarbital Drugs 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
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- 229960003975 potassium Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- DITHIFQMPPCBCU-UHFFFAOYSA-N propa-1,2-diene Chemical compound [CH]=C=C DITHIFQMPPCBCU-UHFFFAOYSA-N 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 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
- 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
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Cardiology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9412783A FR2726273B1 (fr) | 1994-10-26 | 1994-10-26 | Nouveaux derives de la diosmetine, leur procede de preparation et les compositions pharmaceutiques les contenant |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO954173D0 NO954173D0 (no) | 1995-10-19 |
| NO954173L NO954173L (no) | 1996-04-29 |
| NO311132B1 true NO311132B1 (no) | 2001-10-15 |
Family
ID=9468215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19954173A NO311132B1 (no) | 1994-10-26 | 1995-10-19 | Nye diosmetinforbindelser, fremgangsmåte ved deres fremstilling og farmasöytiske preparater inneholdende dem |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5629339A (de) |
| EP (1) | EP0709383B1 (de) |
| JP (1) | JP3076231B2 (de) |
| CN (1) | CN1058494C (de) |
| AT (1) | ATE187720T1 (de) |
| AU (1) | AU693599B2 (de) |
| CA (1) | CA2161297C (de) |
| CY (1) | CY2173B1 (de) |
| DE (1) | DE69513935T2 (de) |
| DK (1) | DK0709383T3 (de) |
| ES (1) | ES2145234T3 (de) |
| FI (1) | FI118766B (de) |
| FR (1) | FR2726273B1 (de) |
| GR (1) | GR3032168T3 (de) |
| NO (1) | NO311132B1 (de) |
| NZ (1) | NZ280330A (de) |
| ZA (1) | ZA959076B (de) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2748025B1 (fr) * | 1996-04-25 | 1998-10-30 | Adir | Nouveaux acides et esters de la diosmetine, et les compositions pharmaceutiques les contenant |
| FR2778663B1 (fr) * | 1998-05-15 | 2001-05-18 | Coletica | Nouveaux esters de flavonoides,leur utilisation en cosmetique, dermopharmacie, en pharmacie et en agro-alimentaire |
| JP2001122791A (ja) * | 1999-10-20 | 2001-05-08 | Boehringer Ingelheim Internatl Gmbh | 下肢の慢性静脈不全の軽減および予防のための赤色ブドウ樹葉の水性抽出物よりなる食事補強剤 |
| EP1127572A3 (de) * | 2000-02-25 | 2003-05-02 | Basf Aktiengesellschaft | Verwendung von Flavonen zur Behandlung von Cyclooxygenase-2 ermittelten Krankheiten |
| US20040151794A1 (en) * | 2002-12-31 | 2004-08-05 | Boehringer Ingelheim International Gmbh | Method of improvement of blood circulation |
| US20040151769A1 (en) * | 2002-12-31 | 2004-08-05 | Boehringer Ingelheim International Gmbh | Film coated tablet containing an extract of red vine leaves |
| EP1550450A1 (de) * | 2003-12-29 | 2005-07-06 | Boehringer Ingelheim International GmbH | Behandlung von chronischer venöser Insuffizienz mit einem Extrakt aus Blättern von roten Weinreben und einem Blutumlauf verbesserndes Mittel |
| RU2367464C2 (ru) * | 2004-02-19 | 2009-09-20 | Берингер Ингельхайм Интернациональ Гмбх | Состав для лечения хронических венозных недостаточностей, содержащий водный экстракт листьев красного винограда и противовоспалительное средство |
| 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 |
| JP2019507796A (ja) * | 2016-03-11 | 2019-03-22 | エイチ リー モフィット キャンサー センター アンド リサーチ インスティテュート インコーポレイテッド | イカリイン及びイカリチン誘導体 |
| 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 (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB928150A (en) * | 1961-02-08 | 1963-06-06 | Upjohn Co | Topical pharmaceutical compositions comprising steroids and flavonoids |
| CH644374A5 (en) * | 1981-05-18 | 1984-07-31 | Espanola Prod Quimicos | Water-soluble hydroxyflavone ethers and medicaments containing them |
| 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 |
| FR2701261B1 (fr) * | 1993-02-05 | 1995-03-31 | Adir | Nouveaux composés glucuronides de la diosmétine, leur procédé de préparation et les compositions pharmaceutiques les renfermant. |
-
1994
- 1994-10-26 FR FR9412783A patent/FR2726273B1/fr not_active Expired - Fee Related
-
1995
- 1995-10-19 NO NO19954173A patent/NO311132B1/no not_active IP Right Cessation
- 1995-10-23 AU AU34404/95A patent/AU693599B2/en not_active Ceased
- 1995-10-24 CA CA002161297A patent/CA2161297C/fr not_active Expired - Fee Related
- 1995-10-24 JP JP07275292A patent/JP3076231B2/ja not_active Expired - Fee Related
- 1995-10-24 US US08/547,650 patent/US5629339A/en not_active Expired - Lifetime
- 1995-10-25 EP EP95402374A patent/EP0709383B1/de not_active Expired - Lifetime
- 1995-10-25 DK DK95402374T patent/DK0709383T3/da active
- 1995-10-25 AT AT95402374T patent/ATE187720T1/de active
- 1995-10-25 CN CN95117660A patent/CN1058494C/zh not_active Expired - Fee Related
- 1995-10-25 FI FI955085A patent/FI118766B/fi not_active IP Right Cessation
- 1995-10-25 NZ NZ280330A patent/NZ280330A/en not_active IP Right Cessation
- 1995-10-25 DE DE69513935T patent/DE69513935T2/de not_active Expired - Lifetime
- 1995-10-25 ES ES95402374T patent/ES2145234T3/es not_active Expired - Lifetime
- 1995-10-26 ZA ZA959076A patent/ZA959076B/xx unknown
-
1999
- 1999-12-17 GR GR990403253T patent/GR3032168T3/el unknown
-
2000
- 2000-05-30 CY CY0000020A patent/CY2173B1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0709383B1 (de) | 1999-12-15 |
| NO954173L (no) | 1996-04-29 |
| US5629339A (en) | 1997-05-13 |
| GR3032168T3 (en) | 2000-04-27 |
| CN1058494C (zh) | 2000-11-15 |
| FR2726273A1 (fr) | 1996-05-03 |
| FI955085A (fi) | 1996-04-27 |
| DE69513935D1 (de) | 2000-01-20 |
| NZ280330A (en) | 1996-12-20 |
| JPH08225563A (ja) | 1996-09-03 |
| ATE187720T1 (de) | 2000-01-15 |
| CA2161297C (fr) | 2001-10-09 |
| FR2726273B1 (fr) | 1996-12-06 |
| CN1129701A (zh) | 1996-08-28 |
| DK0709383T3 (da) | 2000-04-25 |
| ES2145234T3 (es) | 2000-07-01 |
| DE69513935T2 (de) | 2000-07-20 |
| FI118766B (fi) | 2008-03-14 |
| AU693599B2 (en) | 1998-07-02 |
| CY2173B1 (en) | 2002-08-23 |
| NO954173D0 (no) | 1995-10-19 |
| FI955085A0 (fi) | 1995-10-25 |
| ZA959076B (en) | 1996-05-22 |
| EP0709383A1 (de) | 1996-05-01 |
| JP3076231B2 (ja) | 2000-08-14 |
| CA2161297A1 (fr) | 1996-04-27 |
| AU3440495A (en) | 1996-05-09 |
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Legal Events
| Date | Code | Title | Description |
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| MM1K | Lapsed by not paying the annual fees |