FI109792B - Menetelmä bakkatiini-III- ja 10-desasetyylibakkatiini-III-johdannaisten valmistamiseksi - Google Patents

Menetelmä bakkatiini-III- ja 10-desasetyylibakkatiini-III-johdannaisten valmistamiseksi Download PDF

Info

Publication number: FI109792B
Authority: FI; Finland
Prior art keywords: general formula; radical; acetyl; protecting group; iii
Prior art date: 1991-07-10

Application number

FI940075A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI940075L (fi

FI940075A0 (fi

Inventor

Augustin Hittinger

Original Assignee

Aventis Pharma 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.)

1991-07-10

Filing date

1994-01-07

Publication date

2002-10-15

1994-01-07 Application filed by Aventis Pharma Sa filed Critical Aventis Pharma Sa

1994-01-07 Publication of FI940075L publication Critical patent/FI940075L/fi

1994-01-07 Publication of FI940075A0 publication Critical patent/FI940075A0/fi

2002-10-15 Application granted granted Critical

2002-10-15 Publication of FI109792B publication Critical patent/FI109792B/fi

Links

238000000034 method Methods 0.000 title claims abstract description 10
238000002360 preparation method Methods 0.000 title claims abstract description 9
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 title claims description 8
229930014667 baccatin III Natural products 0.000 title claims description 4
YWLXLRUDGLRYDR-SKXCCXORSA-N 10-dab iii Chemical class O([C@H]1C2[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-SKXCCXORSA-N 0.000 title 1
125000006239 protecting group Chemical group 0.000 claims abstract description 15
-1 t-butoxy Chemical group 0.000 claims abstract description 15
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 7
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims abstract description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
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 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
150000002148 esters Chemical class 0.000 claims description 6
YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical class 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 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical class [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
150000002170 ethers Chemical class 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
125000004356 hydroxy functional group Chemical group O* 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
239000011701 zinc Substances 0.000 description 4
229910052725 zinc Inorganic materials 0.000 description 4
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
125000004797 2,2,2-trichloroethoxy group Chemical group ClC(CO*)(Cl)Cl 0.000 description 3
ZLRFPQPVXRIBCQ-UHFFFAOYSA-N 2-$l^{1}-oxidanyl-2-methylpropane Chemical group CC(C)(C)[O] ZLRFPQPVXRIBCQ-UHFFFAOYSA-N 0.000 description 3
NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
TYLVGQKNNUHXIP-MHHARFCSSA-N 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)C=4C=CC=CC=4)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 TYLVGQKNNUHXIP-MHHARFCSSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
229930190007 Baccatin Natural products 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
125000004665 trialkylsilyl group Chemical group 0.000 description 2
238000005406 washing Methods 0.000 description 2
RZARFIRJROUVLM-GVHYBUMESA-N (3r)-3-amino-2-hydroxy-3-phenylpropanoic acid Chemical class OC(=O)C(O)[C@H](N)C1=CC=CC=C1 RZARFIRJROUVLM-GVHYBUMESA-N 0.000 description 1
229930182986 10-Deacetyltaxol Natural products 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
229930012538 Paclitaxel Natural products 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
ZCHPKWUIAASXPV-UHFFFAOYSA-N acetic acid;methanol Chemical compound OC.CC(O)=O ZCHPKWUIAASXPV-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000000719 anti-leukaemic effect Effects 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000005587 carbonate group Chemical group 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
230000001472 cytotoxic effect Effects 0.000 description 1
230000003013 cytotoxicity Effects 0.000 description 1
231100000135 cytotoxicity Toxicity 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
229960001592 paclitaxel Drugs 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
208000019745 retinal vasculopathy with cerebral leukodystrophy Diseases 0.000 description 1
208000029941 retinal vasculopathy with cerebral leukoencephalopathy and systemic manifestations Diseases 0.000 description 1
238000000926 separation method Methods 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

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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Epoxy Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Peptides Or Proteins (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Cephalosporin Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Steroid Compounds (AREA)
Saccharide Compounds (AREA)

FI940075A 1991-07-10 1994-01-07 Menetelmä bakkatiini-III- ja 10-desasetyylibakkatiini-III-johdannaisten valmistamiseksi FI109792B (fi)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
FR9108673		1991-07-10
FR9108673A FR2678930B1 (fr)	1991-07-10	1991-07-10	Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii.
PCT/FR1992/000649 WO1993001179A1 (fr)	1991-07-10	1992-07-08	Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii
FR9200649		1992-07-08

Publications (3)

Publication Number	Publication Date
FI940075L FI940075L (fi)	1994-01-07
FI940075A0 FI940075A0 (fi)	1994-01-07
FI109792B true FI109792B (fi)	2002-10-15

Family

ID=9414931

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI940075A FI109792B (fi)	1991-07-10	1994-01-07	Menetelmä bakkatiini-III- ja 10-desasetyylibakkatiini-III-johdannaisten valmistamiseksi

Country Status (25)

Country	Link
US (1)	US5578739A (de)
EP (2)	EP0593641B1 (de)
JP (1)	JP3085710B2 (de)
KR (1)	KR100206458B1 (de)
AT (1)	ATE132145T1 (de)
AU (1)	AU662346B2 (de)
CA (1)	CA2111319C (de)
CZ (1)	CZ281288B6 (de)
DE (1)	DE69207194T2 (de)
DK (1)	DK0593641T3 (de)
ES (1)	ES2081120T3 (de)
FI (1)	FI109792B (de)
FR (1)	FR2678930B1 (de)
GR (1)	GR3018543T3 (de)
HU (1)	HU217115B (de)
IE (1)	IE73637B1 (de)
MX (1)	MX9204029A (de)
NO (2)	NO302521B1 (de)
NZ (1)	NZ243491A (de)
PL (1)	PL169780B1 (de)
RU (1)	RU2088578C1 (de)
SK (1)	SK281560B6 (de)
WO (1)	WO1993001179A1 (de)
YU (1)	YU49175B (de)
ZA (1)	ZA925098B (de)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6794523B2 (en)	1991-09-23	2004-09-21	Florida State University	Taxanes having t-butoxycarbonyl substituted side-chains and pharmaceutical compositions containing them
US5272171A (en) *	1992-02-13	1993-12-21	Bristol-Myers Squibb Company	Phosphonooxy and carbonate derivatives of taxol
US5294637A (en) *	1992-07-01	1994-03-15	Bristol-Myers Squibb Company	Fluoro taxols
US5380751A (en) *	1992-12-04	1995-01-10	Bristol-Myers Squibb Company	6,7-modified paclitaxels
CA2111527C (en) *	1992-12-24	2000-07-18	Jerzy Golik	Phosphonooxymethyl ethers of taxane derivatives
US5646176A (en) *	1992-12-24	1997-07-08	Bristol-Myers Squibb Company	Phosphonooxymethyl ethers of taxane derivatives
FR2703049B1 (fr) *	1993-03-22	1995-04-21	Rhone Poulenc Rorer Sa	Procédé de purification des taxoïdes.
CA2129288C (en) *	1993-08-17	2000-05-16	Jerzy Golik	Phosphonooxymethyl esters of taxane derivatives
FR2718135B1 (fr) *	1994-04-05	1996-04-26	Rhone Poulenc Rorer Sa	Procédé de préparation d'hydroxy-7 taxanes.
US5580899A (en) *	1995-01-09	1996-12-03	The Liposome Company, Inc.	Hydrophobic taxane derivatives
US6051600A (en) *	1995-09-12	2000-04-18	Mayhew; Eric	Liposomal hydrolysis-promoting hydrophobic taxane derivatives
US6107332A (en)	1995-09-12	2000-08-22	The Liposome Company, Inc.	Hydrolysis-promoting hydrophobic taxane derivatives
FR2740451B1 (fr) *	1995-10-27	1998-01-16	Seripharm	Nouveaux intermediaires pour l'hemisynthese de taxanes, leurs procedes de preparation et leur utilisation dans la synthese generale des taxanes
FR2742751B1 (fr) *	1995-12-22	1998-01-30	Rhone Poulenc Rorer Sa	Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent
US7288665B1 (en) *	1997-08-18	2007-10-30	Florida State University	Process for selective derivatization of taxanes
US6111144A (en)	1997-08-21	2000-08-29	Florida State University	Method for the synthesis of a taxane intermediate
US5917062A (en) *	1997-11-21	1999-06-29	Indena S.P.A	Intermediates and methods useful in the semisynthesis of paclitaxel and analogs
EP1068192B1 (de) *	1998-01-14	2002-06-12	Bristol-Myers Squibb Company	Neue kristallkomplexe von baccatin iii mit imidazol, 2-methylimidazol or isopropanol
ATE269854T1 (de)	1998-05-01	2004-07-15	Napro Biotherapeutics Inc	Verfahren und verwendbare zwischenprodukte für paclitaxel synthese von c-7,c-10 di-cbz baccatin iii
CA2385528C (en)	1999-10-01	2013-12-10	Immunogen, Inc.	Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents
IT1319168B1 (it) *	2000-03-17	2003-09-26	Indena Spa	Derivati di condensazione ad attivita' antitumorale, loro metodo dipreparazione e formulazioni che li contengono.
CN101437536A (zh)	2006-03-23	2009-05-20	诺华有限公司	抗肿瘤细胞抗原抗体治疗
DE102008013929B3 (de) *	2008-03-12	2009-04-09	Wieland-Werke Ag	Verdampferrohr mit optimierten Hinterschneidungen am Nutengrund
CN101531645B (zh) *	2009-04-29	2012-08-22	深圳万乐药业有限公司	一种多西他赛的合成方法
WO2013188763A1 (en)	2012-06-15	2013-12-19	The Brigham And Women's Hospital, Inc.	Compositions for treating cancer and methods for making the same
RU2016140160A (ru)	2014-04-03	2018-05-07	Инвиктус Онколоджи Пвт. Лтд.	Супрамолекулярные комбинаторные лекарственные средства

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
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

1991
- 1991-07-10 FR FR9108673A patent/FR2678930B1/fr not_active Expired - Fee Related
1992
- 1992-07-08 DE DE69207194T patent/DE69207194T2/de not_active Expired - Lifetime
- 1992-07-08 DK DK92915477.1T patent/DK0593641T3/da active
- 1992-07-08 AT AT92915477T patent/ATE132145T1/de active
- 1992-07-08 HU HU9400062A patent/HU217115B/hu unknown
- 1992-07-08 SK SK17-94A patent/SK281560B6/sk not_active IP Right Cessation
- 1992-07-08 WO PCT/FR1992/000649 patent/WO1993001179A1/fr not_active Ceased
- 1992-07-08 EP EP92915477A patent/EP0593641B1/de not_active Expired - Lifetime
- 1992-07-08 CA CA002111319A patent/CA2111319C/fr not_active Expired - Lifetime
- 1992-07-08 ES ES92915477T patent/ES2081120T3/es not_active Expired - Lifetime
- 1992-07-08 PL PL92302030A patent/PL169780B1/pl unknown
- 1992-07-08 KR KR1019940700046A patent/KR100206458B1/ko not_active Expired - Lifetime
- 1992-07-08 EP EP92401958A patent/EP0522958A1/de active Pending
- 1992-07-08 ZA ZA925098A patent/ZA925098B/xx unknown
- 1992-07-08 AU AU23280/92A patent/AU662346B2/en not_active Expired
- 1992-07-08 RU RU9294016161A patent/RU2088578C1/ru active
- 1992-07-08 JP JP05502037A patent/JP3085710B2/ja not_active Expired - Lifetime
- 1992-07-08 CZ CZ9431A patent/CZ281288B6/cs not_active IP Right Cessation
- 1992-07-09 IE IE922234A patent/IE73637B1/en not_active IP Right Cessation
- 1992-07-09 NZ NZ243491A patent/NZ243491A/en not_active IP Right Cessation
- 1992-07-09 MX MX9204029A patent/MX9204029A/es unknown
- 1992-07-10 YU YU68792A patent/YU49175B/sh unknown
1993
- 1993-12-08 NO NO934485A patent/NO302521B1/no not_active IP Right Cessation
- 1993-12-08 NO NO934485D patent/NO934485D0/no unknown
1994
- 1994-01-07 FI FI940075A patent/FI109792B/fi not_active IP Right Cessation
1995
- 1995-07-06 US US08/498,613 patent/US5578739A/en not_active Expired - Lifetime
- 1995-12-28 GR GR950402328T patent/GR3018543T3/el unknown

Also Published As

Publication number	Publication date
FR2678930A1 (fr)	1993-01-15
CA2111319A1 (fr)	1993-01-21
MX9204029A (es)	1993-01-01
CZ281288B6 (cs)	1996-08-14
IE922234A1 (en)	1993-01-13
HU217115B (hu)	1999-11-29
DE69207194T2 (de)	1996-09-05
HUT66018A (en)	1994-08-29
CZ3194A3 (en)	1994-04-13
ZA925098B (en)	1993-04-28
EP0522958A1 (de)	1993-01-13
EP0593641A1 (de)	1994-04-27
ES2081120T3 (es)	1996-02-16
FI940075L (fi)	1994-01-07
DE69207194D1 (de)	1996-02-08
SK281560B6 (sk)	2001-05-10
GR3018543T3 (en)	1996-03-31
YU68792A (sh)	1995-10-03
CA2111319C (fr)	2003-04-08
SK1794A3 (en)	1994-11-09
AU662346B2 (en)	1995-08-31
FI940075A0 (fi)	1994-01-07
NO934485L (no)	1993-12-08
US5578739A (en)	1996-11-26
IE73637B1 (en)	1997-06-18
RU2088578C1 (ru)	1997-08-27
YU49175B (sh)	2004-07-15
AU2328092A (en)	1993-02-11
KR100206458B1 (ko)	1999-07-01
NO302521B1 (no)	1998-03-16
NZ243491A (en)	1995-05-26
ATE132145T1 (de)	1996-01-15
FR2678930B1 (fr)	1995-01-13
NO934485D0 (no)	1993-12-08
JP3085710B2 (ja)	2000-09-11
EP0593641B1 (de)	1995-12-27
DK0593641T3 (da)	1996-01-29
HU9400062D0 (en)	1994-05-30
PL169780B1 (pl)	1996-08-30
JPH06509082A (ja)	1994-10-13
WO1993001179A1 (fr)	1993-01-21

Legal Events

Date	Code	Title	Description
2012-08-10	MA	Patent expired

Publication	Publication Date	Title
IE922234A1 (en)	1993-01-13	Process for the preparation of derivatives of baccatin III and of 10-deacetylbaccatin III
CA2077598C (en)	1997-11-25	Alkoxy substituted taxanes and pharmaceutical compositions containing them
FI113267B (fi)	2004-03-31	Menetelmä terapeuttisesti käyttökelpoisten taksaanijohdannaisten valmistamiseksi
CA1308417C (fr)	1992-10-06	Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii
PL175539B1 (pl)	1999-01-29	Nowe taksoidy
FR2601676A1 (fr)	1988-01-22	Procede de preparation du taxol et du desacetyl-10 taxol
SI9520078A (en)	1997-06-30	Semi-synthetic taxanes with anti-tumoural activity
US5907042A (en)	1999-05-25	Intermediates and methods useful in the semisynthesis of paclitaxel and analogs
RU2168513C2 (ru)	2001-06-10	Производные таксана, способ их получения и фармацевтическая композиция
JP4068663B2 (ja)	2008-03-26	バッカチン誘導体の選択的保護のための方法及びタキサン合成へのその適用
AU2003219094B2 (en)	2008-06-26	A semi-synthetic process for the preparation of N debenzoylpaclitaxel
Díaz et al.	1996	Enantioselective synthesis of novel homochiral α-substituted (S)-isoserine derivatives. Incorporation of this amino acid in a highly conformationally constrained dipeptide surrogate
WO2002012216A1 (en)	2002-02-14	An improved process for the preparation of docetaxel
US5648505A (en)	1997-07-15	Method for the preparation of a novel C-ring precursor for taxoids and novel intermediates
CN101128448A (zh)	2008-02-20	制备紫杉醇的方法
WO2007051306A1 (en)	2007-05-10	New methods for the preparation of taxanes using chiral auxiliaries
FR2661410A1 (fr)	1991-10-31	Nouveaux derives heterocycliques: 2-styryl 4h-1-benzopyrane-4-ones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
HK1005242A1 (en)	1998-12-31	10-deacetylbaccatine iii and 10-deacetyl 14 beta-hydroxybaccatine iii derivatives, a process for the preparation thereof and pharmaceutical compositions containing them
CA2479828A1 (en)	1999-06-03	Intermediates and methods useful in the semisynthesis of paclitaxel and analogs
FR2742754A1 (fr)	1997-06-27	Procede de preparation de taxoides
JPH08295682A (ja)	1996-11-12	バッカチン誘導体及びその製法
HK1028046B (en)	2006-02-24	Intermediates and methods useful in the semisynthesis of paclitaxel and analogs