AU2004226853B2 - A process for the preparation of ferutinine from Ferula genus plants - Google Patents
A process for the preparation of ferutinine from Ferula genus plants Download PDFInfo
- Publication number
- AU2004226853B2 AU2004226853B2 AU2004226853A AU2004226853A AU2004226853B2 AU 2004226853 B2 AU2004226853 B2 AU 2004226853B2 AU 2004226853 A AU2004226853 A AU 2004226853A AU 2004226853 A AU2004226853 A AU 2004226853A AU 2004226853 B2 AU2004226853 B2 AU 2004226853B2
- Authority
- AU
- Australia
- Prior art keywords
- ferutinine
- ferula
- extracts
- process according
- jaeschkenadiol
- 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.)
- Ceased
Links
- CYSHNJQMYORNJI-YUVXSKOASA-N [(3r,3as,4s,8ar)-3-hydroxy-6,8a-dimethyl-3-propan-2-yl-1,2,3a,4,5,8-hexahydroazulen-4-yl] 4-hydroxybenzoate Chemical compound O([C@H]1CC(C)=CC[C@@]2(C)CC[C@@]([C@H]12)(O)C(C)C)C(=O)C1=CC=C(O)C=C1 CYSHNJQMYORNJI-YUVXSKOASA-N 0.000 title claims abstract description 39
- CYSHNJQMYORNJI-UHFFFAOYSA-N p-hydroxybenzoate of jaeschkeanadiol Natural products C12C(C(C)C)(O)CCC2(C)CC=C(C)CC1OC(=O)C1=CC=C(O)C=C1 CYSHNJQMYORNJI-UHFFFAOYSA-N 0.000 title claims abstract description 35
- 241000510609 Ferula Species 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims abstract description 16
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- HDPCDSVIGNIWKD-UHFFFAOYSA-N 4-(2,2-dimethylpropanoyloxy)benzoic acid Chemical compound CC(C)(C)C(=O)OC1=CC=C(C(O)=O)C=C1 HDPCDSVIGNIWKD-UHFFFAOYSA-N 0.000 claims description 7
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- 206010000496 acne Diseases 0.000 claims description 4
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- QYYMDNHUJFIDDQ-UHFFFAOYSA-N 5-chloro-2-methyl-1,2-thiazol-3-one;2-methyl-1,2-thiazol-3-one Chemical compound CN1SC=CC1=O.CN1SC(Cl)=CC1=O QYYMDNHUJFIDDQ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 2
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 2
- 239000002148 ERα-agonist Substances 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
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- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 2
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- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
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- A61K36/23—Apiaceae or Umbelliferae (Carrot family), e.g. dill, chervil, coriander or cumin
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
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- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
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- A—HUMAN NECESSITIES
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- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
- A61K8/9789—Magnoliopsida [dicotyledons]
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/08—Antiseborrheics
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P17/00—Drugs for dermatological disorders
- A61P17/16—Emollients or protectives, e.g. against radiation
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- A—HUMAN NECESSITIES
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- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/31—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/86—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
- C07C2602/30—Azulenes; Hydrogenated azulenes
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Botany (AREA)
- Microbiology (AREA)
- Mycology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Emergency Medicine (AREA)
- Toxicology (AREA)
- Alternative & Traditional Medicine (AREA)
- Medical Informatics (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT000661A ITMI20030661A1 (it) | 2003-04-04 | 2003-04-04 | Processo per la preparazione della ferutinina da piante del genere ferula |
| ITMI2003A000661 | 2003-04-04 | ||
| PCT/EP2004/003055 WO2004087179A1 (en) | 2003-04-04 | 2004-03-23 | A process for the preparation of ferutinine from ferula genus plants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2004226853A1 AU2004226853A1 (en) | 2004-10-14 |
| AU2004226853B2 true AU2004226853B2 (en) | 2009-06-04 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004226853A Ceased AU2004226853B2 (en) | 2003-04-04 | 2004-03-23 | A process for the preparation of ferutinine from Ferula genus plants |
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|---|---|
| US (4) | US7371886B2 (enExample) |
| EP (1) | EP1615651B1 (enExample) |
| JP (2) | JP4648305B2 (enExample) |
| KR (2) | KR101169893B1 (enExample) |
| CN (2) | CN101371818A (enExample) |
| AT (1) | ATE517631T1 (enExample) |
| AU (1) | AU2004226853B2 (enExample) |
| BR (1) | BRPI0409166B1 (enExample) |
| CA (2) | CA2521100C (enExample) |
| DK (1) | DK1615651T3 (enExample) |
| ES (1) | ES2367361T3 (enExample) |
| IL (1) | IL171230A (enExample) |
| IT (1) | ITMI20030661A1 (enExample) |
| NO (1) | NO333671B1 (enExample) |
| PL (1) | PL1615651T3 (enExample) |
| PT (1) | PT1615651E (enExample) |
| RU (2) | RU2342153C2 (enExample) |
| SI (1) | SI1615651T1 (enExample) |
| WO (1) | WO2004087179A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20032286A1 (it) * | 2003-11-24 | 2005-05-25 | Indena Spa | Composizioni per il trattamento di dermatiti atopiche di stati allergici cutanei e dell'acne |
| US8536584B2 (en) | 2007-11-14 | 2013-09-17 | Cree, Inc. | High voltage wire bond free LEDS |
| US20100260695A1 (en) * | 2009-04-09 | 2010-10-14 | Mary Kay Inc. | Combination of plant extracts to improve skin tone |
| CA2800383C (en) * | 2010-05-24 | 2019-06-25 | Indena S.P.A. | Tamarind seed polysaccharide for use in the treatment of inflammatory diseases |
| CA2834828A1 (en) | 2011-05-12 | 2012-11-15 | B.R.A.I.N. Biotechnology Research And Information Network Ag | Small molecule inhibitors of trpa1 |
| DE202015004868U1 (de) | 2014-07-11 | 2015-12-23 | Mary Kay Inc. | Topische Hautzusammensetzung und deren Verwendung |
| CN105820146A (zh) * | 2015-01-08 | 2016-08-03 | 辽宁医联新药研究所 | 一种阿魏内酯及其提取纯化的方法 |
| GB2570508A (en) * | 2018-01-30 | 2019-07-31 | Saeed Mohammad Sultan Alaryani Humaid | Preparation for treatment of wounds |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1604225A (en) * | 1978-05-15 | 1981-12-02 | Skourides A A | Extract of ambelferae for pharmacological use |
| CH672251A5 (enExample) * | 1987-05-29 | 1989-11-15 | Inst Khim Rastitelnykh Vesches |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2090198C1 (ru) * | 1991-03-12 | 1997-09-20 | Иван Иванович Уваров | Способ получения биологически активных веществ, обладающих противогрибковой активностью |
| DE4444238A1 (de) * | 1994-12-13 | 1996-06-20 | Beiersdorf Ag | Kosmetische oder dermatologische Wirkstoffkombinationen aus Zimtsäurederivaten und Flavonglycosiden |
| JP4244093B2 (ja) * | 2000-01-24 | 2009-03-25 | 三省製薬株式会社 | 美白化粧料 |
| CA2417552C (en) * | 2000-06-27 | 2014-05-13 | Qualilife Pharmaceuticals Inc. | Compositions and methods for treating females sexual response |
| US6623768B1 (en) * | 2002-04-16 | 2003-09-23 | Yousry M. A. Naguib | Pharmaceutically active composition extracted from Ferula hermonis and process of its extraction |
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2003
- 2003-04-04 IT IT000661A patent/ITMI20030661A1/it unknown
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2004
- 2004-03-23 KR KR1020117014703A patent/KR101169893B1/ko not_active Expired - Fee Related
- 2004-03-23 ES ES04722572T patent/ES2367361T3/es not_active Expired - Lifetime
- 2004-03-23 RU RU2005130639/15A patent/RU2342153C2/ru not_active IP Right Cessation
- 2004-03-23 AU AU2004226853A patent/AU2004226853B2/en not_active Ceased
- 2004-03-23 WO PCT/EP2004/003055 patent/WO2004087179A1/en not_active Ceased
- 2004-03-23 SI SI200431757T patent/SI1615651T1/sl unknown
- 2004-03-23 PL PL04722572T patent/PL1615651T3/pl unknown
- 2004-03-23 CN CNA2008101489166A patent/CN101371818A/zh active Pending
- 2004-03-23 CN CNB2004800091113A patent/CN100518732C/zh not_active Expired - Fee Related
- 2004-03-23 PT PT04722572T patent/PT1615651E/pt unknown
- 2004-03-23 CA CA2521100A patent/CA2521100C/en not_active Expired - Fee Related
- 2004-03-23 KR KR1020057018336A patent/KR101132526B1/ko not_active Expired - Fee Related
- 2004-03-23 DK DK04722572.7T patent/DK1615651T3/da active
- 2004-03-23 JP JP2006504815A patent/JP4648305B2/ja not_active Expired - Fee Related
- 2004-03-23 CA CA2766702A patent/CA2766702C/en not_active Expired - Fee Related
- 2004-03-23 EP EP04722572A patent/EP1615651B1/en not_active Expired - Lifetime
- 2004-03-23 US US10/551,772 patent/US7371886B2/en not_active Expired - Fee Related
- 2004-03-23 BR BRPI0409166-3A patent/BRPI0409166B1/pt not_active IP Right Cessation
- 2004-03-23 AT AT04722572T patent/ATE517631T1/de active
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2005
- 2005-10-02 IL IL171230A patent/IL171230A/en not_active IP Right Cessation
- 2005-10-03 NO NO20054545A patent/NO333671B1/no not_active IP Right Cessation
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2008
- 2008-03-31 US US12/058,776 patent/US20080248139A1/en not_active Abandoned
- 2008-06-03 RU RU2008122295/15A patent/RU2469733C2/ru not_active IP Right Cessation
-
2010
- 2010-05-06 JP JP2010106573A patent/JP5409505B2/ja not_active Expired - Fee Related
- 2010-06-16 US US12/816,671 patent/US8101215B2/en not_active Expired - Fee Related
-
2011
- 2011-12-13 US US13/324,339 patent/US8247005B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1604225A (en) * | 1978-05-15 | 1981-12-02 | Skourides A A | Extract of ambelferae for pharmacological use |
| CH672251A5 (enExample) * | 1987-05-29 | 1989-11-15 | Inst Khim Rastitelnykh Vesches |
Non-Patent Citations (3)
| Title |
|---|
| Journal of natural Products, vol 64, no 3, 2001, pages 399-400 * |
| Patents Abstracts of Japan,vol 2000, no 24, 2001 JP 2001206819 * |
| Phytochemistry, vol 58, no 5, 2001, pages 763-767 * |
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