LV11031B - Method for purifying taxoids - Google Patents

Method for purifying taxoids Download PDF

Info

Publication number: LV11031B
Authority: LV; Latvia
Prior art keywords: water; mixture; est; heptane; taxotere
Prior art date: 1993-03-22

Application number

LVP-95-292A

Other languages

English (en)

Latvian (lv)

Other versions

LV11031A (lv

Inventor

Andre Durand

Alain Gerbaud

Rodolphe Margraff

Original Assignee

Rhone Poulenc Rorer Sa

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.)

1993-03-22

Filing date

1995-09-22

Publication date

1996-06-20

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=9445195&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=LV11031(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1995-09-22 Application filed by Rhone Poulenc Rorer Sa filed Critical Rhone Poulenc Rorer Sa

1996-02-20 Publication of LV11031A publication Critical patent/LV11031A/xx

1996-06-20 Publication of LV11031B publication Critical patent/LV11031B/lv

Links

238000000034 method Methods 0.000 title claims abstract description 13
YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 claims abstract 8
239000000203 mixture Substances 0.000 claims description 23
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 18
229940063683 taxotere Drugs 0.000 claims description 17
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 16
ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 15
238000000746 purification Methods 0.000 claims description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 6
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 5
-1 aliphatic ketones Chemical class 0.000 claims description 5
150000004684 trihydrates Chemical class 0.000 claims description 3
238000004587 chromatography analysis Methods 0.000 claims description 2
150000002170 ethers Chemical class 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 10
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 3
239000004615 ingredient Substances 0.000 claims 3
238000005192 partition Methods 0.000 claims 3
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 2
150000001298 alcohols Chemical class 0.000 claims 2
229940043265 methyl isobutyl ketone Drugs 0.000 claims 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
150000002576 ketones Chemical class 0.000 claims 1
231100000252 nontoxic Toxicity 0.000 claims 1
230000003000 nontoxic effect Effects 0.000 claims 1
OESAARIFYLCHNG-UHFFFAOYSA-N propanoic acid trihydrate Chemical compound O.O.O.CCC(O)=O OESAARIFYLCHNG-UHFFFAOYSA-N 0.000 claims 1
238000004810 partition chromatography Methods 0.000 abstract 1
OVMSOCFBDVBLFW-VHLOTGQHSA-N 5beta,20-epoxy-1,7beta,13alpha-trihydroxy-9-oxotax-11-ene-2alpha,4alpha,10beta-triyl 4,10-diacetate 2-benzoate Chemical compound O([C@@H]1[C@@]2(C[C@H](O)C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)O)C(=O)C1=CC=CC=C1 OVMSOCFBDVBLFW-VHLOTGQHSA-N 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
MVFGXYPEQHIKIX-UHFFFAOYSA-N acetic acid;heptane Chemical compound CC(O)=O.CCCCCCC MVFGXYPEQHIKIX-UHFFFAOYSA-N 0.000 description 4
230000014759 maintenance of location Effects 0.000 description 4
239000011701 zinc Substances 0.000 description 4
229910052725 zinc Inorganic materials 0.000 description 4
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
239000007924 injection Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
230000006378 damage Effects 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
238000010606 normalization Methods 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
206010011878 Deafness Diseases 0.000 description 1
201000004624 Dermatitis Diseases 0.000 description 1
241001644893 Entandrophragma utile Species 0.000 description 1
241000233866 Fungi Species 0.000 description 1
NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
101100406879 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) par-2 gene Proteins 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
241001080024 Telles Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
MOQOOKGPCBQMCY-UHFFFAOYSA-N acetic acid;hexane Chemical compound CC(O)=O.CCCCCC MOQOOKGPCBQMCY-UHFFFAOYSA-N 0.000 description 1
238000013019 agitation Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000001715 carotid artery Anatomy 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000013461 design Methods 0.000 description 1
JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
238000010828 elution Methods 0.000 description 1
229940082150 encore Drugs 0.000 description 1
239000000686 essence Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000013213 extrapolation Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000000004 hemodynamic effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
235000021116 parmesan Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229930189271 taxine Natural products 0.000 description 1
QDLAHUFDHRJWOE-UHFFFAOYSA-N tert-butyl 3-nitropyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC([N+]([O-])=O)C1 QDLAHUFDHRJWOE-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Epidemiology (AREA)
Epoxy Compounds (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)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Compounds Of Unknown Constitution (AREA)
Auxiliary Devices For Music (AREA)
Investigating Or Analysing Biological Materials (AREA)
Extraction Or Liquid Replacement (AREA)

LVP-95-292A 1993-03-22 1995-09-22 Method for purifying taxoids LV11031B (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9303251A FR2703049B1 (fr)	1993-03-22	1993-03-22	Procédé de purification des taxoïdes.
PCT/FR1994/000300 WO1994021622A1 (fr)	1993-03-22	1994-03-18	Procede de purification des taxoides

Publications (2)

Publication Number	Publication Date
LV11031A LV11031A (lv)	1996-02-20
LV11031B true LV11031B (en)	1996-06-20

Family

ID=9445195

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LVP-95-292A LV11031B (en)	1993-03-22	1995-09-22	Method for purifying taxoids

Country Status (28)

Country	Link
US (3)	US5723635A (2)
EP (1)	EP0690852B1 (2)
JP (3)	JP3470721B2 (2)
KR (1)	KR100320802B1 (2)
CN (2)	CN1119860A (2)
AT (1)	ATE149160T1 (2)
AU (1)	AU687039B2 (2)
CA (1)	CA2157905C (2)
CZ (2)	CZ283363B6 (2)
DE (1)	DE69401810T2 (2)
DK (1)	DK0690852T3 (2)
EE (1)	EE03100B1 (2)
ES (1)	ES2098127T3 (2)
FI (1)	FI119023B (2)
FR (1)	FR2703049B1 (2)
GE (1)	GEP20012581B (2)
GR (1)	GR3022681T3 (2)
HU (1)	HU221303B1 (2)
LT (1)	LT3238B (2)
LV (1)	LV11031B (2)
NO (1)	NO312403B1 (2)
NZ (1)	NZ262917A (2)
PL (1)	PL178496B1 (2)
RU (1)	RU2125563C1 (2)
SK (2)	SK282842B6 (2)
UA (1)	UA43333C2 (2)
WO (1)	WO1994021622A1 (2)
ZA (1)	ZA941968B (2)

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2696462B1 (fr) *	1992-10-05	1994-11-25	Rhone Poulenc Rorer Sa	Procédé d'obtention de la désacétyl-10 baccatine III.
FR2698871B1 (fr)	1992-12-09	1995-02-24	Rhone Poulenc Rorer Sa	Nouveau taxoïdes, leur préparation et les compositions pharmaceutiques qui les contiennent.
FR2729666A1 (fr) *	1995-01-25	1996-07-26	Rhone Poulenc Rorer Sa	Procede de preparation du trihydrate du (2r, 3s)- benzoylamino-2-hydroxy-3-phenylpropionate de 4,10-diacetoxy- 2alpha-benzoyloxy-5beta,20-epoxy-1,7beta-dihydroxy-9-oxo- tax-11-en-13alpha-yle
US6150541A (en) *	1995-12-14	2000-11-21	Aventis Pharma S.A.	4,10-β-diacetoxy-2α-benzoyloxy-5β,20-epoxy-1-hydroxy-9-oxo-19-norcyclopropa[g]t ax-11-en-13α-yl (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionate dihydrate and its process of preparation
FR2750133B1 (fr) *	1996-06-21	1998-08-28	Ifremer	Procede de purification de phospholipides par chromatographie de partage centrifuge
US6174974B1 (en)	1996-07-05	2001-01-16	Bayer Aktiengesellschaft	Method for producing thermoplastic elastomers
US6066748A (en) *	1997-12-17	2000-05-23	Han; Man Woo	Process of extracting TAXOL® from taxus cuspidata
FR2774094B1 (fr) *	1998-01-26	2001-04-13	Ifremer	Procede de purification de sulfoquinovosyldiacylglycerol par chromatographie de partage centrifuge
US6136989A (en) *	1998-12-30	2000-10-24	Phytogen Life Sciences, Incorporated	Method for high yield and large scale extraction of paclitaxel from paclitaxel-containing material
US6333419B1 (en) *	2000-11-28	2001-12-25	Indena Spa	Chromatographic separation method of paclitaxel and cephalomannin
US6891050B2 (en) *	2001-08-10	2005-05-10	Dabur India Limited	Process for the preparation of taxanes such as paclitaxel, docetaxel and structurally similar analogs
US6881852B2 (en) *	2002-02-05	2005-04-19	Dabur India Limited	Process of purification of paclitaxel and docetaxel
US7247738B2 (en) *	2002-05-07	2007-07-24	Dabur India Limited	Method of preparation of anticancer taxanes using 3-[(substituted-2-trialkylsilyl) ethoxycarbonyl]-5-oxazolidine carboxylic acids
US6900342B2 (en) *	2002-05-10	2005-05-31	Dabur India Limited	Anticancer taxanes such as paclitaxel, docetaxel and their structural analogs, and a method for the preparation thereof
US6838569B2 (en) *	2002-12-16	2005-01-04	Dabur India Limited	Process for preparation of paclitaxel trihydrate and docetaxel trihydrate
US8703982B2 (en)	2003-03-17	2014-04-22	Phyton Holdings Llc	Purification of taxanes
US7169307B2 (en)	2004-09-02	2007-01-30	Jian Liu	Process for the extraction of paclitaxel and 9-dihydro-13-acetylbaccatin III from Taxus
CN101094850A (zh) *	2005-01-03	2007-12-26	特瓦制药工业有限公司	具有较低水平杂质的奥美沙坦酯
DK1869065T3 (da) *	2005-03-11	2020-06-08	Wyeth Llc	Fremgangsmåde til kromatografi med svag opdeling
CN1300131C (zh) *	2005-04-27	2007-02-14	浙江钱江生物化学股份有限公司	赤霉素ga3纯化分离方法
TW200730518A (en) *	2005-10-12	2007-08-16	Sicor Inc	Crystalline forms of docetaxel and processes for their preparation
AU2007226937A1 (en) *	2006-03-21	2007-09-27	Dr. Reddy's Laboratories Ltd.	Docetaxel polymorphs and processes
FR2903104B1 (fr) *	2006-07-03	2008-09-26	Pierre Fabre Medicament Sa	Purification de la 10-dab iii par chromatographie de partage centrifuge
JP2010506932A (ja) *	2006-10-20	2010-03-04	シノファームシンガポールピーティーイー，リミテッド	結晶性の無水ドセタキセルの製造方法
WO2009006590A2 (en) *	2007-07-04	2009-01-08	Dr. Reddy's Laboratories Ltd.	Docetaxel process and polymorphs
DE102008031208B4 (de) *	2008-07-03	2010-03-25	Technische Universität Dortmund	Prozess zur großtechnischen Produktion von Taxanen
PL388144A1 (pl)	2009-05-29	2010-12-06	Przedsiębiorstwo Produkcyjno-Wdrożeniowe Ifotam Spółka Z Ograniczoną Odpowiedzialnością	Solwaty (2R,3S)-3-tert-butoksykarbonylamino-2-hydroksy-3-fenylopropionianu 4-acetoksy-2α-benzoiloksy -5β,20-epoksy-1,7β,10β-trihydroksy-9-okso-taks-11-en-13α-ylu, sposób ich otrzymywania i zastosowanie
US8686165B2 (en) *	2009-11-04	2014-04-01	Emcure Pharmaceuticals Limited	Process for preparation of taxane derivatives
JP5824511B2 (ja)	2010-05-03	2015-11-25	テイコクファーマユーエスエーインコーポレーテッド	非水タキサンプロエマルジョン配合物ならびにそれを調製および使用する方法
US8842114B1 (en)	2011-04-29	2014-09-23	Nvidia Corporation	System, method, and computer program product for adjusting a depth of displayed objects within a region of a display
JO3685B1 (ar)	2012-10-01	2020-08-27	Teikoku Pharma Usa Inc	صيغ التشتيت الجسيمي للتاكسين غير المائي وطرق استخدامها
HUP1500603A2 (en)	2015-12-11	2017-06-28	Rotachrom Tech Kft	Process for the separation of 10-deacetyl baccatin iii

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2601675B1 (fr) *	1986-07-17	1988-09-23	Rhone Poulenc Sante	Derives du taxol, leur preparation et les compositions pharmaceutiques qui les contiennent
FR2629819B1 (fr) *	1988-04-06	1990-11-16	Rhone Poulenc Sante	Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii
FR2629818B1 (fr) *	1988-04-06	1990-11-16	Centre Nat Rech Scient	Procede de preparation du taxol
US5175315A (en) *	1989-05-31	1992-12-29	Florida State University	Method for preparation of taxol using β-lactam
MX9102128A (es) *	1990-11-23	1992-07-08	Rhone Poulenc Rorer Sa	Derivados de taxano,procedimiento para su preparacion y composicion farmaceutica que los contiene
JPH04367829A (ja) *	1991-06-17	1992-12-21	Toppan Printing Co Ltd	焼結体バリスタ素子の製造方法
FR2678930B1 (fr) *	1991-07-10	1995-01-13	Rhone Poulenc Rorer Sa	Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii.
US5229526A (en) *	1991-09-23	1993-07-20	Florida State University	Metal alkoxides

1993
- 1993-03-22 FR FR9303251A patent/FR2703049B1/fr not_active Expired - Fee Related
1994
- 1994-03-04 LT LTIP1891A patent/LT3238B/lt not_active IP Right Cessation
- 1994-03-18 KR KR1019950704029A patent/KR100320802B1/ko not_active Expired - Lifetime
- 1994-03-18 DE DE69401810T patent/DE69401810T2/de not_active Expired - Lifetime
- 1994-03-18 CN CN94191548A patent/CN1119860A/zh active Pending
- 1994-03-18 CZ CZ972085A patent/CZ283363B6/cs not_active IP Right Cessation
- 1994-03-18 ES ES94910438T patent/ES2098127T3/es not_active Expired - Lifetime
- 1994-03-18 CZ CZ952442A patent/CZ283334B6/cs not_active IP Right Cessation
- 1994-03-18 NZ NZ262917A patent/NZ262917A/en not_active IP Right Cessation
- 1994-03-18 HU HU9502758A patent/HU221303B1/hu unknown
- 1994-03-18 SK SK1414-2000A patent/SK282842B6/sk not_active IP Right Cessation
- 1994-03-18 DK DK94910438.4T patent/DK0690852T3/da active
- 1994-03-18 AT AT94910438T patent/ATE149160T1/de active
- 1994-03-18 EP EP94910438A patent/EP0690852B1/fr not_active Expired - Lifetime
- 1994-03-18 AU AU62853/94A patent/AU687039B2/en not_active Expired
- 1994-03-18 JP JP52072194A patent/JP3470721B2/ja not_active Expired - Lifetime
- 1994-03-18 SK SK1163-95A patent/SK281542B6/sk not_active IP Right Cessation
- 1994-03-18 RU RU95122764A patent/RU2125563C1/ru active
- 1994-03-18 PL PL94310697A patent/PL178496B1/pl unknown
- 1994-03-18 GE GEAP19942884A patent/GEP20012581B/en unknown
- 1994-03-18 CA CA002157905A patent/CA2157905C/fr not_active Expired - Lifetime
- 1994-03-18 US US08/522,418 patent/US5723635A/en not_active Expired - Lifetime
- 1994-03-18 UA UA95094232A patent/UA43333C2/uk unknown
- 1994-03-18 WO PCT/FR1994/000300 patent/WO1994021622A1/fr not_active Ceased
- 1994-03-18 CN CNA031206395A patent/CN1504465A/zh active Pending
- 1994-03-21 ZA ZA941968A patent/ZA941968B/xx unknown
- 1994-11-02 EE EE9400110A patent/EE03100B1/xx unknown
1995
- 1995-09-13 NO NO19953617A patent/NO312403B1/no not_active IP Right Cessation
- 1995-09-19 FI FI954423A patent/FI119023B/fi not_active IP Right Cessation
- 1995-09-22 LV LVP-95-292A patent/LV11031B/lv unknown
1997
- 1997-02-27 GR GR960402769T patent/GR3022681T3/el unknown
- 1997-08-20 US US08/915,146 patent/US6008385A/en not_active Expired - Lifetime
1999
- 1999-08-20 US US09/377,488 patent/US6197980B1/en not_active Expired - Lifetime
2003
- 2003-02-06 JP JP2003029438A patent/JP4367829B2/ja not_active Expired - Lifetime
- 2003-02-06 JP JP2003029432A patent/JP3953428B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
FR2703049B1 (fr)	1995-04-21
LV11031A (lv)	1996-02-20
FI954423A0 (fi)	1995-09-19
HU9502758D0 (en)	1995-11-28
CA2157905C (fr)	2006-10-10
JP2003201287A (ja)	2003-07-18
FR2703049A1 (fr)	1994-09-30
EP0690852A1 (fr)	1996-01-10
DE69401810D1 (de)	1997-04-03
EE03100B1 (et)	1998-06-15
UA43333C2 (uk)	2001-12-17
LTIP1891A (en)	1994-10-25
US6197980B1 (en)	2001-03-06
KR960701036A (ko)	1996-02-24
JP3953428B2 (ja)	2007-08-08
HUT73139A (en)	1996-06-28
US6008385A (en)	1999-12-28
JPH08508026A (ja)	1996-08-27
RU2125563C1 (ru)	1999-01-27
SK281542B6 (sk)	2001-04-09
CZ208597A3 (en)	1997-12-17
DE69401810T2 (de)	1997-07-31
PL310697A1 (en)	1995-12-27
JP2003238549A (ja)	2003-08-27
CN1119860A (zh)	1996-04-03
AU687039B2 (en)	1998-02-19
NZ262917A (en)	1997-01-29
PL178496B1 (pl)	2000-05-31
HU221303B1 (en)	2002-09-28
ES2098127T3 (es)	1997-04-16
JP4367829B2 (ja)	2009-11-18
CN1504465A (zh)	2004-06-16
AU6285394A (en)	1994-10-11
JP3470721B2 (ja)	2003-11-25
GEP20012581B (en)	2001-11-26
FI119023B (fi)	2008-06-30
LT3238B (en)	1995-04-25
US5723635A (en)	1998-03-03
CZ244295A3 (en)	1996-01-17
ATE149160T1 (de)	1997-03-15
WO1994021622A1 (fr)	1994-09-29
KR100320802B1 (ko)	2002-07-27
DK0690852T3 (2)	1997-03-17
GR3022681T3 (en)	1997-05-31
EP0690852B1 (fr)	1997-02-26
SK116395A3 (en)	1996-01-10
NO953617L (no)	1995-09-13
FI954423L (fi)	1995-09-19
ZA941968B (en)	1994-10-19
SK282842B6 (sk)	2002-12-03
CZ283363B6 (cs)	1998-03-18
CZ283334B6 (cs)	1998-02-18
NO953617D0 (no)	1995-09-13
NO312403B1 (no)	2002-05-06
CA2157905A1 (fr)	1994-09-29

Publication	Publication Date	Title
CA2157905C (fr)	2006-10-10	Procede de purification des taxoides
EP0663909B1 (fr)	1997-01-08	Procede d'obtention de la desacetyl-10 baccatine iii
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CA2299149C (fr)	2010-09-21	Procede d'isolation et de purification du paclitaxel a partir de sources naturelles
JP6087147B2 (ja)	2017-03-01	プロスタグランジンの精製方法
JPH11500753A (ja)	1999-01-19	パクリタキセルおよびセファロマンニンの分離および精製
EP2613792B1 (fr)	2016-09-21	Procédé de préparation d'un extrait raffiné de centella asiatica
US11667619B2 (en)	2023-06-06	Synthesis and purification of cannabinol from cannabidiol
ES2424636T3 (es)	2013-10-07	Proceso para la preparación del ajoeno
EP0698595B1 (fr)	1998-06-24	Procédé d'estérification d'un extrait oligomère polyphénolique d'origine végétale, composition ainsi obtenue et son utilisation
WO2003046014A1 (fr)	2003-06-05	Procede de sulfonation de composes comprenant des groupements hydroxyles (oh) libres ou des amines primaires ou secondaires
EP0738284A1 (fr)	1996-10-23	Derives polysaccharidiques et leur emploi pour la preparation de phases stationnaires chirales utiles pour la separation d'isomeres
WO2012156917A2 (fr)	2012-11-22	Procede d'obtention d'epsilon-viniferine et/ou de resveratrol et produits correspondants
WO2004091603A1 (fr)	2004-10-28	Utilisation d’un ester de dha pour le traitement des malades cardiovasculaires
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CA2460783A1 (fr)	2003-03-27	Bioprecurseurs destines a une application percutanee
CA1181415A (fr)	1985-01-22	Esters terbutyliques derives de l'acide 2,2-dimethyl cyclopropane 1,3-dicarboxylique, et leur preparation
CH626359A5 (en)	1981-11-13	Process for extracting flavanol oligomers
EP0262010A1 (fr)	1988-03-30	Procédé d'estérification stéréospécifique d'un mélange d'acides aminés par réaction dudit mélange en solution dans l'alcool d'estérification en présence de papaine
MC1849A1 (fr)	1988-09-30	Procede pour la fabrication d'esters du 1-methyl-10 methoxylumilysergol
WO2018091479A1 (fr)	2018-05-24	Procédé de purification d'iridals
FR2911872A1 (fr)	2008-08-01	Procede d'enrichissement d'un extrait contenant de l'oleocanthal.
CA2275980A1 (fr)	2000-12-22	Procede de recuperation de pacitaxeline a partir de sources naturelles
BE476705A (2)
BE885558A (fr)	1981-04-07	Procede pour l'extraction de silymarine a partir des plantes silymarine ainsi obtenue et son utilisation en therapeutique