DE2117429C3 - Verfahren zur Herstellung eines Injektions- bzw. Infusionspräparates mit einem Gehalt an einem Wirkstoffgemisch aus den Blättern von Ginkgo biloba - Google Patents
Verfahren zur Herstellung eines Injektions- bzw. Infusionspräparates mit einem Gehalt an einem Wirkstoffgemisch aus den Blättern von Ginkgo bilobaInfo
- Publication number
- DE2117429C3 DE2117429C3 DE2117429A DE2117429A DE2117429C3 DE 2117429 C3 DE2117429 C3 DE 2117429C3 DE 2117429 A DE2117429 A DE 2117429A DE 2117429 A DE2117429 A DE 2117429A DE 2117429 C3 DE2117429 C3 DE 2117429C3
- Authority
- DE
- Germany
- Prior art keywords
- methyl ethyl
- ethyl ketone
- alcohol
- phase
- separated
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
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- 239000000203 mixture Substances 0.000 title claims description 14
- 244000194101 Ginkgo biloba Species 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 13
- 238000002347 injection Methods 0.000 title claims description 11
- 239000007924 injection Substances 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 9
- 230000008569 process Effects 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 238000001802 infusion Methods 0.000 title claims description 3
- 239000013543 active substance Substances 0.000 title description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- 239000000243 solution Substances 0.000 claims description 32
- 239000012071 phase Substances 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 239000000284 extract Substances 0.000 claims description 25
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 14
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 14
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 14
- -1 methyl ethyl Chemical group 0.000 claims description 14
- 239000002244 precipitate Substances 0.000 claims description 11
- 239000004480 active ingredient Substances 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 7
- 239000012141 concentrate Substances 0.000 claims description 6
- 229910021514 lead(II) hydroxide Inorganic materials 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 5
- 239000008346 aqueous phase Substances 0.000 claims description 4
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 4
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- 239000006286 aqueous extract Substances 0.000 claims description 3
- 230000002227 vasoactive effect Effects 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
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- 238000001704 evaporation Methods 0.000 claims 1
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- 235000011201 Ginkgo Nutrition 0.000 description 11
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- 238000003756 stirring Methods 0.000 description 7
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- 229940075894 denatured ethanol Drugs 0.000 description 5
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- REFJWTPEDVJJIY-UHFFFAOYSA-N Quercetin Chemical compound C=1C(O)=CC(O)=C(C(C=2O)=O)C=1OC=2C1=CC=C(O)C(O)=C1 REFJWTPEDVJJIY-UHFFFAOYSA-N 0.000 description 4
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- 229910052757 nitrogen Inorganic materials 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 229930182448 Prodelphinidin Natural products 0.000 description 3
- 229920000124 Prodelphinidin Polymers 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 3
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- 230000004872 arterial blood pressure Effects 0.000 description 2
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 2
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- 230000004856 capillary permeability Effects 0.000 description 2
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- 229930003944 flavone Natural products 0.000 description 2
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- 235000017173 flavonoids Nutrition 0.000 description 2
- 229930182478 glucoside Natural products 0.000 description 2
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- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 description 2
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- XMOCLSLCDHWDHP-SWLSCSKDSA-N (+)-Epigallocatechin Natural products C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-SWLSCSKDSA-N 0.000 description 1
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- 101800004538 Bradykinin Proteins 0.000 description 1
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- OVSQVDMCBVZWGM-IDRAQACASA-N Hirsutrin Natural products O([C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1)C1=C(c2cc(O)c(O)cc2)Oc2c(c(O)cc(O)c2)C1=O OVSQVDMCBVZWGM-IDRAQACASA-N 0.000 description 1
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- 206010022562 Intermittent claudication Diseases 0.000 description 1
- 102100035792 Kininogen-1 Human genes 0.000 description 1
- XMOCLSLCDHWDHP-UHFFFAOYSA-N L-Epigallocatechin Natural products OC1CC2=C(O)C=C(O)C=C2OC1C1=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
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- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 description 1
- GMGLYSIINJPYLI-UHFFFAOYSA-N butan-2-one;propan-2-one Chemical compound CC(C)=O.CCC(C)=O GMGLYSIINJPYLI-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
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- XMOCLSLCDHWDHP-IUODEOHRSA-N epi-Gallocatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-IUODEOHRSA-N 0.000 description 1
- DZYNKLUGCOSVKS-UHFFFAOYSA-N epigallocatechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3cc(O)c(O)c(O)c3 DZYNKLUGCOSVKS-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 150000002212 flavone derivatives Chemical class 0.000 description 1
- 210000000232 gallbladder Anatomy 0.000 description 1
- 229930184727 ginkgolide Natural products 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
- 229960002456 hexobarbital Drugs 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
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- 229910052742 iron Inorganic materials 0.000 description 1
- OVSQVDMCBVZWGM-QCKGUQPXSA-N isoquercetin Natural products OC[C@@H]1O[C@@H](OC2=C(Oc3cc(O)cc(O)c3C2=O)c4ccc(O)c(O)c4)[C@H](O)[C@@H](O)[C@@H]1O OVSQVDMCBVZWGM-QCKGUQPXSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
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- OVSQVDMCBVZWGM-QSOFNFLRSA-N quercetin 3-O-beta-D-glucopyranoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(C=2C=C(O)C(O)=CC=2)OC2=CC(O)=CC(O)=C2C1=O OVSQVDMCBVZWGM-QSOFNFLRSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/16—Ginkgophyta, e.g. Ginkgoaceae (Ginkgo family)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Alternative & Traditional Medicine (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Medical Informatics (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Medicines Containing Plant Substances (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2117429A DE2117429C3 (de) | 1971-04-08 | 1971-04-08 | Verfahren zur Herstellung eines Injektions- bzw. Infusionspräparates mit einem Gehalt an einem Wirkstoffgemisch aus den Blättern von Ginkgo biloba |
| JP47035634A JPS4927323B1 (https=) | 1971-04-08 | 1972-04-07 | |
| BE781802A BE781802A (fr) | 1971-04-08 | 1972-04-07 | Procede pour extraire un medicament vasoactif a partir des feuille de ginkgo biloba ainsi que preparations pharmaceutiques |
| NLAANVRAGE7204696,A NL175383C (nl) | 1971-04-08 | 1972-04-07 | Werkwijze ter bereiding van een vaso-actief mengsel van werkzame stoffen uit de bladeren van ginkgo biloba en bereiding van geneeskundige preparaten daaruit. |
| LU65123D LU65123A1 (https=) | 1971-04-08 | 1972-04-07 | |
| FR7212288A FR2132761A1 (en) | 1971-04-08 | 1972-04-07 | Vasoactive substances produced by extracting from - ginkgo biloba leaves |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2117429A DE2117429C3 (de) | 1971-04-08 | 1971-04-08 | Verfahren zur Herstellung eines Injektions- bzw. Infusionspräparates mit einem Gehalt an einem Wirkstoffgemisch aus den Blättern von Ginkgo biloba |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2117429A1 DE2117429A1 (de) | 1972-10-12 |
| DE2117429B2 DE2117429B2 (de) | 1981-05-27 |
| DE2117429C3 true DE2117429C3 (de) | 1982-04-01 |
Family
ID=5804351
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2117429A Expired DE2117429C3 (de) | 1971-04-08 | 1971-04-08 | Verfahren zur Herstellung eines Injektions- bzw. Infusionspräparates mit einem Gehalt an einem Wirkstoffgemisch aus den Blättern von Ginkgo biloba |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS4927323B1 (https=) |
| BE (1) | BE781802A (https=) |
| DE (1) | DE2117429C3 (https=) |
| FR (1) | FR2132761A1 (https=) |
| LU (1) | LU65123A1 (https=) |
| NL (1) | NL175383C (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50144535U (https=) * | 1974-05-15 | 1975-11-28 | ||
| FR2518406A1 (fr) * | 1981-12-22 | 1983-06-24 | Prodipharm | Nouveau procede d'obtention de substances vaso-actives extraites de feuilles de ginkgo |
| GB8418424D0 (en) * | 1984-07-19 | 1984-08-22 | Scras | Inhibition of platelets aggregation |
| FR2627387B1 (fr) * | 1988-02-24 | 1992-06-05 | Fabre Sa Pierre | Procede d'obtention d'un extrait de feuilles de ginkgo biloba |
| FR2634380B1 (fr) | 1988-07-19 | 1990-10-12 | Beljanski Mirko | Regulateur biologique, actif dans diverses pathologies |
| JP2818220B2 (ja) * | 1988-11-04 | 1998-10-30 | フロイント産業株式会社 | 食品用の含水有機溶剤抽出物含有組成物および医薬用の含水有機溶剤抽出物含有組成物、並びにそれらの製造方法 |
| KR940002795B1 (ko) * | 1989-06-16 | 1994-04-02 | 주식회사 선경인더스트리 | 은행잎에서 징코라이드를 분리 및 정제하는 방법 |
| DE3940092A1 (de) * | 1989-12-04 | 1991-06-06 | Schwabe Willmar Gmbh & Co | Extrakt aus blaettern von ginkgo biloba, verfahren zu seiner herstellung und den extrakt enthaltende arzneimittel |
| DE3940094A1 (de) * | 1989-12-04 | 1991-06-06 | Montana Ltd | Wirkstoffkonzentrate und neue wirkstoff-kombinationen aus blaettern von ginkgo biloba, ein verfahren zu ihrer herstellung und die wirkstoff-konzentrate bzw. die wirkstoff-kombinationen enthaltenden arzneimittel |
| DE3940091A1 (de) * | 1989-12-04 | 1991-06-06 | Schwabe Willmar Gmbh & Co | Extrakt aus blaettern von ginkgo biloba, verfahren zu seiner herstellung und den extrakt enthaltende arzneimittel |
| US5158770A (en) * | 1989-12-29 | 1992-10-27 | Freund Industrial Co., Ltd. | Aqueous solution containing ginkgo leaf extract |
| DE4030758A1 (de) * | 1990-09-28 | 1992-04-02 | Schwabe Willmar Gmbh & Co | Extrakt aus blaettern von ginkgo biloba, insbesondere zur intravenoesen injektion oder infusion, verfahren zu seiner herstellung und den extrakt enthaltende ampullenpraeparate |
| ES2036951B1 (es) * | 1991-11-29 | 1994-01-16 | Euromed S A | Procedimiento de obtencion de un extracto esencialmente compuesto de ginkgoflavonoides a partir de las hojas de ginkgo biloba. |
| US6086883A (en) * | 1993-12-03 | 2000-07-11 | Montana Limited | Extract from the leaves of Ginkgo biloba |
| DE19829516B4 (de) † | 1998-07-02 | 2004-08-26 | Dr. Willmar Schwabe Gmbh & Co. Kg | Wasserlöslicher nativer Trockenextrakt aus Gingko biloba mit hohem Gehalt an Terpenoiden und Flavonglykosiden |
| DE10040610A1 (de) * | 2000-08-16 | 2002-03-07 | Schwabe Willmar Gmbh & Co | Flavonhaltige Pflanzenextraktlösungen mit verbesserter Lager- und Hitzestabilität |
| US6590109B2 (en) * | 2001-07-11 | 2003-07-08 | The Trustees Of Columbia University In The City Of New York | Method for isolating terpene trilactones (ginkgolides, bilobalide) from leaves and pharmaceutical powders of ginkgo biloba |
| WO2003082185A2 (en) | 2002-03-29 | 2003-10-09 | The Trustees Of Columbia University In The City Of New York | Analogs of terpene trilactones from ginkgo biloba and related compounds and uses thereof |
| US7429670B2 (en) | 2003-08-27 | 2008-09-30 | The Trustees Of Columbia University In The City Of New York | Synthesis of derivatives of ginkgolide C |
| WO2005046829A2 (en) | 2003-11-12 | 2005-05-26 | The Trustees Of Columbia University In The City Of New York | Separation of ginkgolides and bilobalide from g. biloba |
| CN1954826A (zh) | 2005-10-26 | 2007-05-02 | 上海生物芯片有限公司 | 银杏叶提取物在降低胆固醇方面的用途 |
| CN102659808B (zh) | 2012-04-23 | 2014-10-29 | 成都百裕科技制药有限公司 | 一种银杏内酯的提取分离方法 |
| DE102023131617A1 (de) | 2023-11-14 | 2025-05-15 | Dr. Willmar Schwabe Gmbh & Co. Kg | Verfahren zur Herstellung von Ginkgoextrakten mit hohem Gehalt an Proanthocyanidinen und Nahrungsergänzungsmittel und Arzneimittel enthaltend Ginkgoextrakte |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1418062A (fr) * | 1964-07-10 | 1965-11-19 | Organon Nv | Purification de préparation biologiquement actives de source animale |
| DE1767098C2 (de) * | 1968-03-29 | 1973-01-04 | Dr. Willmar Schwabe Gmbh, 7500 Karlsruhe-Durlach | Verfahren zur Gewinnung eines vasoaktiven Arzneimittels aus den Blättern von Ginkgo biloba |
-
1971
- 1971-04-08 DE DE2117429A patent/DE2117429C3/de not_active Expired
-
1972
- 1972-04-07 LU LU65123D patent/LU65123A1/xx unknown
- 1972-04-07 NL NLAANVRAGE7204696,A patent/NL175383C/xx not_active IP Right Cessation
- 1972-04-07 JP JP47035634A patent/JPS4927323B1/ja active Pending
- 1972-04-07 BE BE781802A patent/BE781802A/xx not_active IP Right Cessation
- 1972-04-07 FR FR7212288A patent/FR2132761A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2117429A1 (de) | 1972-10-12 |
| LU65123A1 (https=) | 1972-07-12 |
| DE2117429B2 (de) | 1981-05-27 |
| FR2132761B1 (https=) | 1975-10-10 |
| NL175383C (nl) | 1984-11-01 |
| NL7204696A (https=) | 1972-10-10 |
| FR2132761A1 (en) | 1972-11-24 |
| NL175383B (nl) | 1984-06-01 |
| JPS4927323B1 (https=) | 1974-07-17 |
| BE781802A (fr) | 1972-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: DR. WILLMAR SCHWABE GMBH & CO, 7500 KARLSRUHE, DE |