FI112208B - Menetelmä lääkeaineina käyttökelpoisten taksaanijohdannaisten valmistamiseksi - Google Patents

Menetelmä lääkeaineina käyttökelpoisten taksaanijohdannaisten valmistamiseksi Download PDF

Info

Publication number: FI112208B
Authority: FI; Finland
Prior art keywords: compound; formula; preparation; group; hydrogen
Prior art date: 1992-03-06

Application number

FI930977A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI930977L (fi

FI930977A0 (fi

Inventor

Ezio Bombardelli

Bruno Gabetta

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.)

1992-03-06

Filing date

1993-03-04

Publication date

2003-11-14

1993-03-04 Application filed by Indena Spa filed Critical Indena Spa

1993-03-04 Publication of FI930977A0 publication Critical patent/FI930977A0/fi

1993-09-07 Publication of FI930977L publication Critical patent/FI930977L/fi

2003-11-14 Application granted granted Critical

2003-11-14 Publication of FI112208B publication Critical patent/FI112208B/fi

Links

238000002360 preparation method Methods 0.000 title claims abstract description 7
238000000034 method Methods 0.000 title claims description 9
230000008569 process Effects 0.000 title claims description 7
239000003814 drug Substances 0.000 title claims description 6
DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 title claims description 3
229940079593 drug Drugs 0.000 title description 3
241000196324 Embryophyta Species 0.000 claims abstract description 4
241001116500 Taxus Species 0.000 claims abstract description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
150000001875 compounds Chemical class 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
239000011541 reaction mixture Substances 0.000 claims description 6
LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
125000001589 carboacyl group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 3
229910052753 mercury Inorganic materials 0.000 claims description 3
238000010992 reflux Methods 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
230000001678 irradiating effect Effects 0.000 claims 1
150000002576 ketones Chemical class 0.000 claims 1
230000002634 anti-blastic effect Effects 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000002904 solvent Substances 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000003480 eluent Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
-1 aliphatic ketones Chemical class 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
229940125782 compound 2 Drugs 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
238000010898 silica gel chromatography Methods 0.000 description 4
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
229940125890 compound Ia Drugs 0.000 description 3
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
239000000284 extract Substances 0.000 description 3
238000000605 extraction Methods 0.000 description 3
229930014626 natural product Natural products 0.000 description 3
238000006349 photocyclization reaction Methods 0.000 description 3
239000000843 powder Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011877 solvent mixture Substances 0.000 description 3
WLWNRAWQDZRXMB-YLFCFFPRSA-N (2r,3r,4r,5s)-n,3,4,5-tetrahydroxy-1-(4-phenoxyphenyl)sulfonylpiperidine-2-carboxamide Chemical compound ONC(=O)[C@H]1[C@@H](O)[C@H](O)[C@@H](O)CN1S(=O)(=O)C(C=C1)=CC=C1OC1=CC=CC=C1 WLWNRAWQDZRXMB-YLFCFFPRSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
206010028980 Neoplasm Diseases 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
241001116498 Taxus baccata Species 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
230000000259 anti-tumor effect Effects 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
210000001638 cerebellum Anatomy 0.000 description 2
238000000262 chemical ionisation mass spectrometry Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000010828 elution Methods 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
238000002955 isolation Methods 0.000 description 2
238000006317 isomerization reaction Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
229930184616 taxin Natural products 0.000 description 2
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
229930190007 Baccatin Natural products 0.000 description 1
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241001279241 Laxus Species 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
229930012538 Paclitaxel Natural products 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
229940123237 Taxane Drugs 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000002927 anti-mitotic effect Effects 0.000 description 1
229940034982 antineoplastic agent Drugs 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000012790 confirmation Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000007913 intrathecal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
210000000265 leukocyte Anatomy 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229960001592 paclitaxel Drugs 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
230000029553 photosynthesis Effects 0.000 description 1
238000010672 photosynthesis Methods 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
239000010453 quartz Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](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)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000008791 toxic response Effects 0.000 description 1
230000009466 transformation Effects 0.000 description 1
230000007704 transition Effects 0.000 description 1
238000011282 treatment Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
- C07C69/618—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety having unsaturation outside the six-membered aromatic ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/76—Ring systems containing bridged rings containing three rings containing at least one ring with more than six ring members
- C07C2603/80—Ring systems containing bridged rings containing three rings containing at least one ring with more than six ring members containing eight-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/86—Ring systems containing bridged rings containing four rings

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Epoxy Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Steroid Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

FI930977A 1992-03-06 1993-03-04 Menetelmä lääkeaineina käyttökelpoisten taksaanijohdannaisten valmistamiseksi FI112208B (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ITMI920526A IT1254515B (it)	1992-03-06	1992-03-06	Tassani di interesse oncologico, loro metodo di preparazione ed uso
ITMI920526		1992-03-06

Publications (3)

Publication Number	Publication Date
FI930977A0 FI930977A0 (fi)	1993-03-04
FI930977L FI930977L (fi)	1993-09-07
FI112208B true FI112208B (fi)	2003-11-14

Family

ID=11362316

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI930977A FI112208B (fi)	1992-03-06	1993-03-04	Menetelmä lääkeaineina käyttökelpoisten taksaanijohdannaisten valmistamiseksi

Country Status (15)

Country	Link
US (1)	US5250722A (fr)
EP (1)	EP0559018B1 (fr)
JP (1)	JPH0641010A (fr)
KR (1)	KR100255524B1 (fr)
AT (1)	ATE137734T1 (fr)
CA (1)	CA2091002C (fr)
DE (2)	DE69302508T2 (fr)
DK (1)	DK0559018T3 (fr)
ES (1)	ES2049690T3 (fr)
FI (1)	FI112208B (fr)
GR (2)	GR930300141T1 (fr)
HK (1)	HK1007556A1 (fr)
IT (1)	IT1254515B (fr)
NO (1)	NO178965C (fr)
RU (2)	RU2112770C1 (fr)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5475120A (en) *	1990-11-02	1995-12-12	University Of Florida	Method for the isolation and purification of taxol and its natural analogues
JP2646942B2 (ja) *	1991-08-12	1997-08-27	松下電器産業株式会社	ガード体付電子部品の打抜装置および打抜方法
IT1261667B (it) *	1993-05-20	1996-05-29		Tassano ad attivita' antitumorale.
US5628978A (en) *	1994-12-23	1997-05-13	Intevep, S.A.	MTW zeolite for cracking feedstock into olefins and isoparaffins
US6177456B1 (en)	1995-10-02	2001-01-23	Xechem International, Inc.	Monohalocephalomannines having anticancer and antileukemic activity and method of preparation therefor
US5854278A (en) *	1995-12-13	1998-12-29	Xechem International, Inc.	Preparation of chlorinated paclitaxel analogues and use thereof as antitumor agents
US5840748A (en) *	1995-10-02	1998-11-24	Xechem International, Inc.	Dihalocephalomannine and methods of use therefor
US5654448A (en) *	1995-10-02	1997-08-05	Xechem International, Inc.	Isolation and purification of paclitaxel from organic matter containing paclitaxel, cephalomannine and other related taxanes
US5807888A (en) *	1995-12-13	1998-09-15	Xechem International, Inc.	Preparation of brominated paclitaxel analogues and their use as effective antitumor agents
US6576636B2 (en) *	1996-05-22	2003-06-10	Protarga, Inc.	Method of treating a liver disorder with fatty acid-antiviral agent conjugates
US5919815A (en) *	1996-05-22	1999-07-06	Neuromedica, Inc.	Taxane compounds and compositions
US5795909A (en) *	1996-05-22	1998-08-18	Neuromedica, Inc.	DHA-pharmaceutical agent conjugates of taxanes
JP4172726B2 (ja) *	1996-05-22	2008-10-29	ルイトポルド・ファーマシューティカルズ・インコーポレーテッド	シス―ドコサヘキサエン酸とドセタキセルとの共有複合体を含有する製剤
US7235583B1 (en)	1999-03-09	2007-06-26	Luitpold Pharmaceuticals, Inc.,	Fatty acid-anticancer conjugates and uses thereof
CA2385528C (fr)	1999-10-01	2013-12-10	Immunogen, Inc.	Compositions et methodes de traitement du cancer utilisant des immunoconjugues et des agents chimiotherapeutiques
US8552054B2 (en)	2001-03-23	2013-10-08	Luitpold Pharmaceuticals, Inc.	Fatty amine drug conjugates
JP4634694B2 (ja) *	2001-03-23	2011-02-16	ルイトポルド・ファーマシューティカルズ・インコーポレーテッド	脂肪アルコール薬物複合体
US7410980B2 (en) *	2001-11-29	2008-08-12	Daiichi Pharmaceutical Co., Ltd.	Crystals of taxane derivative and process for their production
US7201507B2 (en)	2003-12-25	2007-04-10	Ichikoh Industries, Ltd.	Projector type vehicle light
JP4405279B2 (ja)	2004-02-17	2010-01-27	市光工業株式会社	プロジェクタ型車両用灯具
JP4954983B2 (ja)	2005-05-18	2012-06-20	ファーマサイエンス・インコーポレイテッド	Ｂｉｒドメイン結合化合物
SG10201407457UA (en)	2006-05-16	2014-12-30	Pharmascience Inc	Iap bir domain binding compounds
MX340870B (es)	2010-02-12	2016-07-27	Pharmascience Inc	Compuestos de unión del dominio de repetición de inhibidores de proteínas de apoptosis de baculovirus.
CN105541631B (zh) *	2015-10-26	2017-09-05	云南西力生物技术股份有限公司	绣线菊阿替生素A(spiratisanin A)及其制备方法和在药物上的应用

Family Cites Families (3)

* 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
US5059699A (en) *	1990-08-28	1991-10-22	Virginia Tech Intellectual Properties, Inc.	Water soluble derivatives of taxol
US5380916A (en) *	1990-11-02	1995-01-10	University Of Florida	Method for the isolation and purification of taxane derivatives

1992
- 1992-03-06 IT ITMI920526A patent/IT1254515B/it active
- 1992-05-11 US US07/881,047 patent/US5250722A/en not_active Expired - Lifetime
1993
- 1993-02-19 ES ES93102632T patent/ES2049690T3/es not_active Expired - Lifetime
- 1993-02-19 EP EP93102632A patent/EP0559018B1/fr not_active Expired - Lifetime
- 1993-02-19 DE DE69302508T patent/DE69302508T2/de not_active Expired - Fee Related
- 1993-02-19 DE DE93102632T patent/DE559018T1/de active Pending
- 1993-02-19 DK DK93102632.2T patent/DK0559018T3/da active
- 1993-02-19 AT AT93102632T patent/ATE137734T1/de not_active IP Right Cessation
- 1993-03-03 NO NO930773A patent/NO178965C/no unknown
- 1993-03-04 RU RU93004649A patent/RU2112770C1/ru not_active IP Right Cessation
- 1993-03-04 JP JP5067348A patent/JPH0641010A/ja active Pending
- 1993-03-04 FI FI930977A patent/FI112208B/fi active
- 1993-03-04 RU RU93004623A patent/RU2119485C1/ru not_active IP Right Cessation
- 1993-03-04 KR KR1019930003212A patent/KR100255524B1/ko not_active Expired - Fee Related
- 1993-03-04 CA CA002091002A patent/CA2091002C/fr not_active Expired - Fee Related
1994
- 1994-02-28 GR GR930300141T patent/GR930300141T1/el unknown
1996
- 1996-05-09 GR GR960401123T patent/GR3019871T3/el unknown
1998
- 1998-06-25 HK HK98106815A patent/HK1007556A1/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPH0641010A (ja)	1994-02-15
ES2049690T1 (es)	1994-05-01
KR930019597A (ko)	1993-10-18
CA2091002C (fr)	2004-06-08
RU2112770C1 (ru)	1998-06-10
NO178965C (no)	1996-07-10
GR930300141T1 (en)	1994-02-28
DK0559018T3 (da)	1996-08-19
US5250722A (en)	1993-10-05
NO930773D0 (no)	1993-03-03
ITMI920526A1 (it)	1993-09-06
CA2091002A1 (fr)	1993-09-07
DE559018T1 (de)	1994-03-17
DE69302508T2 (de)	1996-09-12
GR3019871T3 (en)	1996-08-31
FI930977L (fi)	1993-09-07
RU2119485C1 (ru)	1998-09-27
ES2049690T3 (es)	1996-07-16
FI930977A0 (fi)	1993-03-04
DE69302508D1 (de)	1996-06-13
ATE137734T1 (de)	1996-05-15
IT1254515B (it)	1995-09-25
NO930773L (no)	1993-09-07
ITMI920526A0 (it)	1992-03-06
EP0559018A1 (fr)	1993-09-08
HK1007556A1 (en)	1999-04-16
EP0559018B1 (fr)	1996-05-08
KR100255524B1 (ko)	2000-05-01
NO178965B (no)	1996-04-01

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