CA2521100C - 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 PDF

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Publication number
CA2521100C
CA2521100C CA2521100A CA2521100A CA2521100C CA 2521100 C CA2521100 C CA 2521100C CA 2521100 A CA2521100 A CA 2521100A CA 2521100 A CA2521100 A CA 2521100A CA 2521100 C CA2521100 C CA 2521100C
Authority
CA
Canada
Prior art keywords
ferutinine
ferula
jaeschkenadiol
process according
extracted
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 - Fee Related
Application number
CA2521100A
Other languages
English (en)
French (fr)
Other versions
CA2521100A1 (en
Inventor
Ezio Bombardelli
Gabriele Fontana
Aldo Cristoni
Enrico Mercalli
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Indena SpA
Original Assignee
Indena SpA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Indena SpA filed Critical Indena SpA
Priority to CA2766702A priority Critical patent/CA2766702C/en
Publication of CA2521100A1 publication Critical patent/CA2521100A1/en
Application granted granted Critical
Publication of CA2521100C publication Critical patent/CA2521100C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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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
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/23—Apiaceae or Umbelliferae (Carrot family), e.g. dill, chervil, coriander or cumin
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • 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]
    • 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
    • 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
    • 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
    • A61P17/10—Anti-acne agents
    • 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
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Botany (AREA)
  • Microbiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biotechnology (AREA)
  • Mycology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Emergency Medicine (AREA)
  • Gerontology & Geriatric Medicine (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Medical Informatics (AREA)
  • Toxicology (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA2521100A 2003-04-04 2004-03-23 A process for the preparation of ferutinine from ferula genus plants Expired - Fee Related CA2521100C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA2766702A CA2766702C (en) 2003-04-04 2004-03-23 A process for the preparation of ferutinine from ferula genus plants and uses therefor

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
ITMI2003A000661 2003-04-04
IT000661A ITMI20030661A1 (it) 2003-04-04 2003-04-04 Processo per la preparazione della ferutinina da piante del genere ferula
PCT/EP2004/003055 WO2004087179A1 (en) 2003-04-04 2004-03-23 A process for the preparation of ferutinine from ferula genus plants

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA2766702A Division CA2766702C (en) 2003-04-04 2004-03-23 A process for the preparation of ferutinine from ferula genus plants and uses therefor

Publications (2)

Publication Number Publication Date
CA2521100A1 CA2521100A1 (en) 2004-10-14
CA2521100C true CA2521100C (en) 2012-05-01

Family

ID=33105046

Family Applications (2)

Application Number Title Priority Date Filing Date
CA2521100A Expired - Fee Related CA2521100C (en) 2003-04-04 2004-03-23 A process for the preparation of ferutinine from ferula genus plants
CA2766702A Expired - Fee Related CA2766702C (en) 2003-04-04 2004-03-23 A process for the preparation of ferutinine from ferula genus plants and uses therefor

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA2766702A Expired - Fee Related CA2766702C (en) 2003-04-04 2004-03-23 A process for the preparation of ferutinine from ferula genus plants and uses therefor

Country Status (19)

Country Link
US (4) US7371886B2 (enExample)
EP (1) EP1615651B1 (enExample)
JP (2) JP4648305B2 (enExample)
KR (2) KR101132526B1 (enExample)
CN (2) CN100518732C (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)

* Cited by examiner, † Cited by third party
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
EP2575973B1 (en) * 2010-05-24 2017-06-28 Indena S.p.A. Tamarind seed polysaccharide and ferula hermonis extract for use in the treatment of inflammatory diseases
EP2706995B1 (en) * 2011-05-12 2016-11-30 B.R.A.I.N. Biotechnology Research and Information Network AG Small molecule inhibitors of trpa1
US9913799B2 (en) 2014-07-11 2018-03-13 Mary Kay Inc. Cosmetic compositions and methods of their use
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

Family Cites Families (7)

* Cited by examiner, † Cited by third party
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
WO1988009164A1 (fr) * 1987-05-29 1988-12-01 Institut Khimii Rastitelnykh Veschestv Akademii Na Preparation pharmaceutique a action oestrogenique
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
ATE369868T1 (de) * 2000-06-27 2007-09-15 Qualilife Pharmaceuticals Inc Zusammensetzungen und verfahren zur behandlung der weiblichen sexuellen reaktion
US6623768B1 (en) * 2002-04-16 2003-09-23 Yousry M. A. Naguib Pharmaceutically active composition extracted from Ferula hermonis and process of its extraction

Also Published As

Publication number Publication date
US8247005B2 (en) 2012-08-21
NO20054545D0 (no) 2005-10-03
CA2521100A1 (en) 2004-10-14
RU2342153C2 (ru) 2008-12-27
US7371886B2 (en) 2008-05-13
US8101215B2 (en) 2012-01-24
KR101169893B1 (ko) 2012-07-31
WO2004087179A1 (en) 2004-10-14
JP2010209099A (ja) 2010-09-24
RU2005130639A (ru) 2006-04-27
NO333671B1 (no) 2013-08-05
JP4648305B2 (ja) 2011-03-09
EP1615651B1 (en) 2011-07-27
EP1615651A1 (en) 2006-01-18
KR20110082091A (ko) 2011-07-15
SI1615651T1 (sl) 2011-11-30
HK1087618A1 (zh) 2006-10-20
JP5409505B2 (ja) 2014-02-05
ES2367361T3 (es) 2011-11-02
CA2766702A1 (en) 2004-10-14
US20120095094A1 (en) 2012-04-19
CN100518732C (zh) 2009-07-29
ATE517631T1 (de) 2011-08-15
RU2469733C2 (ru) 2012-12-20
JP2006522043A (ja) 2006-09-28
KR20060008307A (ko) 2006-01-26
CN101371818A (zh) 2009-02-25
CN1767841A (zh) 2006-05-03
BRPI0409166B1 (pt) 2015-09-01
PT1615651E (pt) 2011-09-02
RU2008122295A (ru) 2009-12-10
IL171230A (en) 2014-02-27
CA2766702C (en) 2015-09-29
US20100255125A1 (en) 2010-10-07
NO20054545L (no) 2005-10-06
US20080248139A1 (en) 2008-10-09
ITMI20030661A1 (it) 2004-10-05
PL1615651T3 (pl) 2011-12-30
AU2004226853B2 (en) 2009-06-04
BRPI0409166A (pt) 2006-04-11
AU2004226853A1 (en) 2004-10-14
US20060275246A1 (en) 2006-12-07
KR101132526B1 (ko) 2012-04-03
DK1615651T3 (da) 2011-10-24

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Effective date: 20190325