SK283199B6 - Taxánové deriváty, prostriedok s ich obsahom a ich použitie - Google Patents

Taxánové deriváty, prostriedok s ich obsahom a ich použitie Download PDF

Info

Publication number: SK283199B6
Authority: SK; Slovakia
Prior art keywords: chx; taxane; hydrogen; paclitaxel; group
Prior art date: 1995-09-12

Application number

SK334-98A

Other languages

English (en)

Slovak (sk)

Other versions

SK33498A3 (en

Inventor

Eric Mayhew

Shaukat Ali

Andrew S. Janoff

Original Assignee

The Liposome Company, Inc.

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.)

1995-09-12

Filing date

1996-09-12

Publication date

2003-03-04

1996-09-12 Application filed by The Liposome Company, Inc. filed Critical The Liposome Company, Inc.

1998-08-05 Publication of SK33498A3 publication Critical patent/SK33498A3/sk

2003-03-04 Publication of SK283199B6 publication Critical patent/SK283199B6/sk

Links

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 abstract description 85
238000002360 preparation method Methods 0.000 title claims description 5
239000000203 mixture Substances 0.000 claims abstract description 33
241001465754 Metazoa Species 0.000 claims abstract description 25
206010028980 Neoplasm Diseases 0.000 claims abstract description 20
230000007062 hydrolysis Effects 0.000 claims abstract description 12
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 12
150000002632 lipids Chemical class 0.000 claims description 49
239000002502 liposome Substances 0.000 claims description 47
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 22
201000011510 cancer Diseases 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
239000012867 bioactive agent Substances 0.000 claims description 12
229910052794 bromium Inorganic materials 0.000 claims description 12
230000001737 promoting effect Effects 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 8
238000011282 treatment Methods 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 7
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230000037396 body weight Effects 0.000 claims description 4
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125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
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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 52
125000002252 acyl group Chemical group 0.000 description 41
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VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
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125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
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AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 7
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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 description 2
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YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
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HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
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POULHZVOKOAJMA-UHFFFAOYSA-N methyl undecanoic acid Natural products CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
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KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
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125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
230000017095 negative regulation of cell growth Effects 0.000 description 1
230000017066 negative regulation of growth Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
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229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229950004354 phosphorylcholine Drugs 0.000 description 1
PYJNAPOPMIJKJZ-UHFFFAOYSA-N phosphorylcholine chloride Chemical group [Cl-].C[N+](C)(C)CCOP(O)(O)=O PYJNAPOPMIJKJZ-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000008389 polyethoxylated castor oil Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000009101 premedication Methods 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
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239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
238000000527 sonication Methods 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
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235000003702 sterols Nutrition 0.000 description 1
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239000001384 succinic acid Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
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125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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239000011701 zinc Substances 0.000 description 1
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DTOSIQBPPRVQHS-UHFFFAOYSA-N α-Linolenic acid Chemical compound CCC=CCC=CCC=CCCCCCCCC(O)=O DTOSIQBPPRVQHS-UHFFFAOYSA-N 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/127—Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Epidemiology (AREA)
Dispersion Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Epoxy Compounds (AREA)
Medicinal Preparation (AREA)

SK334-98A 1995-09-12 1996-09-12 Taxánové deriváty, prostriedok s ich obsahom a ich použitie SK283199B6 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US357595P	1995-09-12	1995-09-12
PCT/US1996/014631 WO1997010234A1 (en)	1995-09-12	1996-09-12	Hydrolysis-promoting taxane hydrophobic derivatives

Publications (2)

Publication Number	Publication Date
SK33498A3 SK33498A3 (en)	1998-08-05
SK283199B6 true SK283199B6 (sk)	2003-03-04

Family

ID=21706522

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK334-98A SK283199B6 (sk)	1995-09-12	1996-09-12	Taxánové deriváty, prostriedok s ich obsahom a ich použitie

Country Status (21)

Country	Link
US (1)	US5703117A (cs)
EP (1)	EP0902783B1 (cs)
JP (1)	JP4192208B2 (cs)
KR (1)	KR100401220B1 (cs)
CN (1)	CN1100770C (cs)
AT (2)	ATE309235T1 (cs)
CA (1)	CA2231750C (cs)
CZ (1)	CZ288562B6 (cs)
DE (2)	DE69635428T2 (cs)
DK (2)	DK0902783T3 (cs)
ES (2)	ES2252347T3 (cs)
HU (1)	HU226325B1 (cs)
IL (1)	IL123595A (cs)
MX (1)	MX9801871A (cs)
NO (1)	NO319521B1 (cs)
NZ (1)	NZ318300A (cs)
PL (1)	PL187738B1 (cs)
PT (1)	PT902783E (cs)
SK (1)	SK283199B6 (cs)
TR (1)	TR199800443T1 (cs)
WO (1)	WO1997010234A1 (cs)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6107332A (en) *	1995-09-12	2000-08-22	The Liposome Company, Inc.	Hydrolysis-promoting hydrophobic taxane derivatives
US6667053B1 (en) *	1996-02-16	2003-12-23	Elan Pharmaceuticals, Inc.	D and L etherlipid stereoisomers and liposomes
US5912264A (en) *	1997-03-03	1999-06-15	Bristol-Myers Squibb Company	6-halo-or nitrate-substituted paclitaxels
US8853260B2 (en)	1997-06-27	2014-10-07	Abraxis Bioscience, Llc	Formulations of pharmacological agents, methods for the preparation thereof and methods for the use thereof
TR200002243T2 (tr) *	1997-11-10	2000-12-21	Memorial Sloan-Kettering Cancer Center	Arsenik trioksitin hazırlanması için işlem ve bunların kanser tedavisi için kullanımı.
SK17422000A3 (sk) *	1998-05-20	2001-09-11	The Liposome Company, Inc.	Kompozöcie ¬astöc
US6146659A (en) *	1998-07-01	2000-11-14	Neopharm, Inc.	Method of administering liposomal encapsulated taxane
US7314637B1 (en)	1999-06-29	2008-01-01	Neopharm, Inc.	Method of administering liposomal encapsulated taxane
JP2002534461A (ja) *	1999-01-12	2002-10-15	クアナムメディカルコーポレイション	水不溶性のパクリタキセル誘導体の投与のための組成物および方法
AU775373B2 (en)	1999-10-01	2004-07-29	Immunogen, Inc.	Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents
CA2410632A1 (en)	2000-06-22	2001-12-27	David S. Garvey	Nitrosated and nitrosylated taxanes, compositions and methods of use
US6607689B1 (en) *	2000-08-29	2003-08-19	Micron Technology, Inc.	Layer thickness control for stereolithography utilizing variable liquid elevation and laser focal length
EP1304103B1 (en) *	2001-10-22	2008-12-31	Viroblock SA	New non-phospholipid lipid vesicles (npLV) and their use in cosmetic, therapeutic and prophylactic applications
US6710195B2 (en) *	2001-11-26	2004-03-23	Supergen, Inc.	Method for preparing and using polyoxyethylated castor oil in pharmaceutical compositions
EP1553924B1 (en) *	2002-06-26	2010-12-08	MediGene AG	Novel method of stabilizing diagnostic and therapeutic compounds in a cationic carrier system
BRPI0407096A (pt)	2003-02-03	2006-01-24	Neopharm Inc	Taxano encapsulado em lipossomo estável, estéril e filtrável e outros fármacos antineoplásicos
US20090130163A1 (en) *	2005-02-18	2009-05-21	Abraxis Bio Scoence, Inc.	Drugs With Improved Hydrophobicity For Incorporation in Medical Devices
AU2006235538A1 (en) *	2005-04-12	2006-10-19	Wisconsin Alumni Research Foundation	Micelle composition of polymer and passenger drug
TW200942233A (en) *	2008-04-10	2009-10-16	Abraxis Bioscience Llc	Compositions of hydrophobic taxane derivatives and uses thereof
MX2010011165A (es) *	2008-04-10	2011-02-22	Abraxis Bioscience Llc	Composiciones de derivados de taxano hidrofobos y sus usos.
EP2480207B1 (en)	2009-09-25	2016-11-09	Wisconsin Alumni Research Foundation	Micelle encapsulation of therapeutic agents
CN105503844A (zh) *	2015-12-11	2016-04-20	上海大学	C-13和c-7位结构改造的紫杉醇类化合物及其制备方法
CN111004195B (zh) *	2019-12-03	2022-01-28	沈阳药科大学	卡巴他赛弱碱性衍生物及其制剂

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5059699A (en) *	1990-08-28	1991-10-22	Virginia Tech Intellectual Properties, Inc.	Water soluble derivatives of taxol
US5278324A (en) *	1990-08-28	1994-01-11	Virginia Tech Intellectual Properties, Inc.	Water soluble derivatives of taxol
CZ292993B6 (cs) *	1992-12-23	2004-01-14	Bristol-Myers Squibb Company	Způsob přípravy taxanu nesoucího oxazolinový postranní řetězec a taxan tímto způsobem připravený
IL108316A (en) *	1993-01-15	2006-10-31	Univ Florida State	C10 taxane derivatives and pharmaceutical compositions containing them
US5580899A (en) *	1995-01-09	1996-12-03	The Liposome Company, Inc.	Hydrophobic taxane derivatives

1996
- 1996-09-12 AT AT02008590T patent/ATE309235T1/de not_active IP Right Cessation
- 1996-09-12 US US08/712,684 patent/US5703117A/en not_active Expired - Fee Related
- 1996-09-12 AT AT96930847T patent/ATE216377T1/de not_active IP Right Cessation
- 1996-09-12 CZ CZ1998711A patent/CZ288562B6/cs not_active IP Right Cessation
- 1996-09-12 TR TR1998/00443T patent/TR199800443T1/xx unknown
- 1996-09-12 SK SK334-98A patent/SK283199B6/sk unknown
- 1996-09-12 DE DE69635428T patent/DE69635428T2/de not_active Expired - Fee Related
- 1996-09-12 DK DK96930847T patent/DK0902783T3/da active
- 1996-09-12 EP EP96930847A patent/EP0902783B1/en not_active Expired - Lifetime
- 1996-09-12 ES ES02008590T patent/ES2252347T3/es not_active Expired - Lifetime
- 1996-09-12 HU HU9901433A patent/HU226325B1/hu unknown
- 1996-09-12 PL PL96325477A patent/PL187738B1/pl not_active IP Right Cessation
- 1996-09-12 WO PCT/US1996/014631 patent/WO1997010234A1/en not_active Ceased
- 1996-09-12 DK DK02008590T patent/DK1229030T3/da active
- 1996-09-12 MX MX9801871A patent/MX9801871A/es not_active IP Right Cessation
- 1996-09-12 JP JP51210297A patent/JP4192208B2/ja not_active Expired - Fee Related
- 1996-09-12 CA CA002231750A patent/CA2231750C/en not_active Expired - Fee Related
- 1996-09-12 IL IL12359596A patent/IL123595A/xx not_active IP Right Cessation
- 1996-09-12 KR KR10-1998-0701653A patent/KR100401220B1/ko not_active Expired - Fee Related
- 1996-09-12 DE DE69620802T patent/DE69620802T2/de not_active Expired - Fee Related
- 1996-09-12 ES ES96930847T patent/ES2179208T3/es not_active Expired - Lifetime
- 1996-09-12 PT PT96930847T patent/PT902783E/pt unknown
- 1996-09-12 CN CN96198237A patent/CN1100770C/zh not_active Expired - Fee Related
- 1996-09-12 NZ NZ318300A patent/NZ318300A/xx unknown
1998
- 1998-03-11 NO NO19981071A patent/NO319521B1/no unknown

Also Published As

Publication number	Publication date
KR100401220B1 (ko)	2004-03-20
ES2179208T3 (es)	2003-01-16
DE69620802T2 (de)	2002-10-10
SK33498A3 (en)	1998-08-05
US5703117A (en)	1997-12-30
KR19990044409A (ko)	1999-06-25
JP2001519755A (ja)	2001-10-23
PL187738B1 (pl)	2004-09-30
HK1016169A1 (en)	1999-10-29
JP4192208B2 (ja)	2008-12-10
MX9801871A (es)	1998-05-31
AU6975696A (en)	1997-04-01
HUP9901433A3 (en)	2001-05-28
IL123595A0 (en)	1998-10-30
HU226325B1 (en)	2008-08-28
NO319521B1 (no)	2005-08-22
NO981071D0 (no)	1998-03-11
CA2231750C (en)	2006-07-11
HUP9901433A2 (hu)	2001-04-28
ATE216377T1 (de)	2002-05-15
EP0902783B1 (en)	2002-04-17
EP0902783A4 (cs)	1999-03-24
IL123595A (en)	2000-10-31
DK0902783T3 (da)	2002-07-22
CZ71198A3 (cs)	1998-07-15
DE69635428T2 (de)	2006-06-14
DE69620802D1 (de)	2002-05-23
CZ288562B6 (cs)	2001-07-11
CN1202166A (zh)	1998-12-16
ATE309235T1 (de)	2005-11-15
ES2252347T3 (es)	2006-05-16
CA2231750A1 (en)	1997-03-20
AU706290B2 (en)	1999-06-10
WO1997010234A1 (en)	1997-03-20
EP0902783A1 (en)	1999-03-24
CN1100770C (zh)	2003-02-05
DK1229030T3 (da)	2006-02-13
NO981071L (no)	1998-05-12
PL325477A1 (en)	1998-07-20
NZ318300A (en)	1999-08-30
TR199800443T1 (xx)	1998-06-22
DE69635428D1 (de)	2005-12-15
PT902783E (pt)	2002-09-30

Publication	Publication Date	Title
SK283199B6 (sk)	2003-03-04	Taxánové deriváty, prostriedok s ich obsahom a ich použitie
US5939567A (en)	1999-08-17	Synthesis of hydrophobic taxane derivatives
US5614549A (en)	1997-03-25	High molecular weight polymer-based prodrugs
US5880131A (en)	1999-03-09	High molecular weight polymer-based prodrugs
US6482850B2 (en)	2002-11-19	Hydrolysis-promoting hydrophobic taxane derivatives
US6051600A (en)	2000-04-18	Liposomal hydrolysis-promoting hydrophobic taxane derivatives
AU706290C (en)	2001-02-22	Hydrolysis-promoting taxane hydrophobic derivatives
EP1229030B1 (en)	2005-11-09	Hydrolysis-promoting taxane hydrophobic derivates
HK1016169B (en)	2003-10-17	Hydrolysis-promoting taxane hydrophobic derivatives