SK101198A3 - Taxane derivatives having a pyridil substituted c13 side chain, their preparation and their use as anti-tumor agents - Google Patents

Taxane derivatives having a pyridil substituted c13 side chain, their preparation and their use as anti-tumor agents Download PDF

Info

Publication number: SK101198A3
Authority: SK; Slovakia
Prior art keywords: compounds; formula; group; pyridyl; desphenyl
Prior art date: 1996-01-31

Application number

SK1011-98A

Other languages

English (en)

Slovak (sk)

Inventor

Ulrich Klar

Gunter Neef

Hermann Graf

Original Assignee

Schering Ag

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.)

1996-01-31

Filing date

1997-01-31

Publication date

1998-12-02

1997-01-31 Application filed by Schering Ag filed Critical Schering Ag

1998-12-02 Publication of SK101198A3 publication Critical patent/SK101198A3/sk

Links

238000002360 preparation method Methods 0.000 title claims description 19
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 4
239000002246 antineoplastic agent Substances 0.000 title description 3
PIINXYKJQGMIOZ-UHFFFAOYSA-N 1,2-dipyridin-2-ylethane-1,2-dione Chemical group C=1C=CC=NC=1C(=O)C(=O)C1=CC=CC=N1 PIINXYKJQGMIOZ-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 78
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 13
230000032050 esterification Effects 0.000 claims abstract description 10
238000005886 esterification reaction Methods 0.000 claims abstract description 10
238000006266 etherification reaction Methods 0.000 claims abstract description 8
229920000858 Cyclodextrin Polymers 0.000 claims abstract description 6
229940123237 Taxane Drugs 0.000 claims abstract description 4
125000002252 acyl group Chemical group 0.000 claims abstract description 4
229920001450 Alpha-Cyclodextrin Polymers 0.000 claims abstract description 3
HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims abstract description 3
229940043377 alpha-cyclodextrin Drugs 0.000 claims abstract description 3
WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims abstract description 3
229960004853 betadex Drugs 0.000 claims abstract description 3
GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims abstract description 3
229940080345 gamma-cyclodextrin Drugs 0.000 claims abstract description 3
239000002502 liposome Substances 0.000 claims abstract description 3
125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 34
238000000034 method Methods 0.000 claims description 25
230000008569 process Effects 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000003545 alkoxy group Chemical class 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
239000000654 additive Substances 0.000 claims description 2
239000012876 carrier material Substances 0.000 claims 1
229960001592 paclitaxel Drugs 0.000 abstract description 24
229930012538 Paclitaxel Natural products 0.000 abstract description 15
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 abstract description 15
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230000000694 effects Effects 0.000 abstract description 5
230000006641 stabilisation Effects 0.000 abstract description 2
229910052739 hydrogen Inorganic materials 0.000 abstract 2
239000001257 hydrogen Substances 0.000 abstract 2
125000000027 (C1-C10) alkoxy group Chemical class 0.000 abstract 1
125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
229910052736 halogen Inorganic materials 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
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239000000203 mixture Substances 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
-1 methoxy, ethoxy, propoxy, isopropoxy Chemical group 0.000 description 14
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
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XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 6
230000004071 biological effect Effects 0.000 description 6
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FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
MQLACMBJVPINKE-UHFFFAOYSA-N 10-[(3-hydroxy-4-methoxyphenyl)methylidene]anthracen-9-one Chemical compound C1=C(O)C(OC)=CC=C1C=C1C2=CC=CC=C2C(=O)C2=CC=CC=C21 MQLACMBJVPINKE-UHFFFAOYSA-N 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
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IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 4
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 4
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 4
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GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 3
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CGPUWJWCVCFERF-UHFFFAOYSA-N staurosporine Natural products C12=C3N4C5=CC=CC=C5C3=C3CNC(=O)C3=C2C2=CC=CC=C2N1C1CC(NC)C(OC)C4(OC)O1 CGPUWJWCVCFERF-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229960001603 tamoxifen Drugs 0.000 description 1
229940063683 taxotere Drugs 0.000 description 1
NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 1
229960001278 teniposide Drugs 0.000 description 1
238000012360 testing method Methods 0.000 description 1
229960002784 thioridazine Drugs 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 1
229960000303 topotecan Drugs 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000009529 traumatic brain injury Effects 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
229960002324 trifluoperazine Drugs 0.000 description 1
ZEWQUBUPAILYHI-UHFFFAOYSA-N trifluoperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 ZEWQUBUPAILYHI-UHFFFAOYSA-N 0.000 description 1
210000005239 tubule Anatomy 0.000 description 1
239000005483 tyrosine kinase inhibitor Substances 0.000 description 1
229960001722 verapamil Drugs 0.000 description 1
229960003048 vinblastine Drugs 0.000 description 1
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
229960004528 vincristine Drugs 0.000 description 1
OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
239000000341 volatile oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Epoxy Compounds (AREA)
Medicinal Preparation (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)

SK1011-98A 1996-01-31 1997-01-31 Taxane derivatives having a pyridil substituted c13 side chain, their preparation and their use as anti-tumor agents SK101198A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19605024A DE19605024A1 (de)	1996-01-31	1996-01-31	Neue selektive Taxane, Verfahren zu ihrer Herstellung und ihre pharmazeutische Verwendung
PCT/EP1997/000440 WO1997028156A1 (en)	1996-01-31	1997-01-31	Taxane derivatives having a pyridyl substituted c13 side chain, their preparation and their use as anti-tumor agents

Publications (1)

Publication Number	Publication Date
SK101198A3 true SK101198A3 (en)	1998-12-02

Family

ID=7785142

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1011-98A SK101198A3 (en)	1996-01-31	1997-01-31	Taxane derivatives having a pyridil substituted c13 side chain, their preparation and their use as anti-tumor agents

Country Status (25)

Country	Link
US (1)	US6162920A (de)
EP (1)	EP0896577B1 (de)
JP (1)	JP2001505527A (de)
KR (1)	KR19990082151A (de)
CN (1)	CN1073108C (de)
AT (1)	ATE233757T1 (de)
AU (1)	AU714313B2 (de)
BR (1)	BR9708295A (de)
CA (1)	CA2244746A1 (de)
CZ (1)	CZ292504B6 (de)
DE (2)	DE19605024A1 (de)
DK (1)	DK0896577T3 (de)
ES (1)	ES2192261T3 (de)
HU (1)	HUP9901027A3 (de)
IL (1)	IL124951A (de)
NO (1)	NO983509D0 (de)
PL (1)	PL186796B1 (de)
PT (1)	PT896577E (de)
RU (1)	RU2163599C2 (de)
SK (1)	SK101198A3 (de)
TR (1)	TR199801415T2 (de)
TW (1)	TW444015B (de)
UA (1)	UA49007C2 (de)
WO (1)	WO1997028156A1 (de)
ZA (1)	ZA97847B (de)

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KR100851515B1 (ko)	2001-03-07	2008-08-11	다이이찌 세이야꾸 가부시기가이샤	2-아제티디논 유도체의 제조방법
DE60328486D1 (de) *	2002-05-24	2009-09-03	Angiotech Int Ag	Zusammensetzungen und verfahren zur beschichtung medizinischer implantate
CN1678310A (zh) *	2002-08-24	2005-10-05	赞塔里斯有限公司	用于治疗良性和恶性肿瘤疾病的含有disorazole及其衍生物的药物
US20040220655A1 (en)	2003-03-03	2004-11-04	Sinus Rhythm Technologies, Inc.	Electrical conduction block implant device
CN1296391C (zh) *	2004-03-04	2007-01-24	中国人民解放军第二军医大学	氟代羧烷基环糊精醚类化合物及其制备方法和应用
KR101223366B1 (ko)	2004-05-03	2013-01-16	헤르메스 바이오사이언스, 인코포레이티드	약물 전달에 유용한 리포좀
US8658203B2 (en)	2004-05-03	2014-02-25	Merrimack Pharmaceuticals, Inc.	Liposomes useful for drug delivery to the brain
AU2013202947B2 (en)	2012-06-13	2016-06-02	Ipsen Biopharm Ltd.	Methods for treating pancreatic cancer using combination therapies comprising liposomal irinotecan
US9717724B2 (en)	2012-06-13	2017-08-01	Ipsen Biopharm Ltd.	Methods for treating pancreatic cancer using combination therapies
US11318131B2 (en)	2015-05-18	2022-05-03	Ipsen Biopharm Ltd.	Nanoliposomal irinotecan for use in treating small cell lung cancer
KR20180037210A (ko)	2015-08-20	2018-04-11	입센 바이오팜 리미티드	암 치료를 위한 리포좀 이리노테칸 및 parp 저해제를 이용하는 조합요법
KR102714060B1 (ko)	2015-08-21	2024-10-08	입센 바이오팜 리미티드	리포솜 이리노테칸 및 옥살리플라틴을 포함하는 병용 치료를 이용하여 전이성 췌장암을 치료하는 방법
NZ741291A (en)	2015-10-16	2022-10-28	Ipsen Biopharm Ltd	Stabilizing camptothecin pharmaceutical compositions
WO2018083470A1 (en)	2016-11-02	2018-05-11	Ipsen Biopharm Ltd.	Treating gastric cancer using combination therapies comprising liposomal irinotecan, oxaliplatin, 5-fluoruracil (and leucovorin)

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2017744C1 (ru) *	1987-09-21	1994-08-15	Фудзисава Фармасьютикал Ко., Лтд.	Способ получения соединений цефема или их кислотно-аддитивных солей
US5489601A (en) *	1991-09-23	1996-02-06	Florida State University	Taxanes having a pyridyl substituted side-chain and pharmaceutical compositions containing them
US5227400A (en) *	1991-09-23	1993-07-13	Florida State University	Furyl and thienyl substituted taxanes and pharmaceutical compositions containing them
WO1994021252A1 (en) *	1993-03-22	1994-09-29	Florida State University	Taxanes having a pyridyl substituted side-chain
US5415869A (en) *	1993-11-12	1995-05-16	The Research Foundation Of State University Of New York	Taxol formulation
FR2715307B1 (fr) *	1994-01-25	1996-04-05	Commissariat Energie Atomique	Procédé de solubilisation dans un milieu aqueux d'agents antitumoraux de la famille du taxol, et cyclodextrines ramifiées utilisables pour cette solubilisation.
DE69504843T2 (de) *	1994-06-28	1999-02-11	Pharmacia & Upjohn Co., Kalamazoo, Mich.	7-äther-taxol ähnliche verbindungen antineoplastische verwendung und diese enthaltende pharmazeutische zusammenstellungen

1996
- 1996-01-31 DE DE19605024A patent/DE19605024A1/de not_active Withdrawn
1997
- 1997-01-31 DE DE69719502T patent/DE69719502T2/de not_active Expired - Lifetime
- 1997-01-31 BR BR9708295A patent/BR9708295A/pt not_active Application Discontinuation
- 1997-01-31 EP EP97902286A patent/EP0896577B1/de not_active Expired - Lifetime
- 1997-01-31 SK SK1011-98A patent/SK101198A3/sk unknown
- 1997-01-31 CZ CZ19982426A patent/CZ292504B6/cs not_active IP Right Cessation
- 1997-01-31 IL IL12495197A patent/IL124951A/xx not_active IP Right Cessation
- 1997-01-31 DK DK97902286T patent/DK0896577T3/da active
- 1997-01-31 PL PL97328055A patent/PL186796B1/pl not_active IP Right Cessation
- 1997-01-31 UA UA98084638A patent/UA49007C2/uk unknown
- 1997-01-31 JP JP52730897A patent/JP2001505527A/ja active Pending
- 1997-01-31 CN CN97192006A patent/CN1073108C/zh not_active Expired - Fee Related
- 1997-01-31 KR KR1019980705874A patent/KR19990082151A/ko not_active Ceased
- 1997-01-31 ES ES97902286T patent/ES2192261T3/es not_active Expired - Lifetime
- 1997-01-31 AT AT97902286T patent/ATE233757T1/de not_active IP Right Cessation
- 1997-01-31 HU HU9901027A patent/HUP9901027A3/hu unknown
- 1997-01-31 WO PCT/EP1997/000440 patent/WO1997028156A1/en not_active Ceased
- 1997-01-31 RU RU98116122/04A patent/RU2163599C2/ru not_active IP Right Cessation
- 1997-01-31 ZA ZA9700847A patent/ZA97847B/xx unknown
- 1997-01-31 PT PT97902286T patent/PT896577E/pt unknown
- 1997-01-31 TR TR1998/01415T patent/TR199801415T2/xx unknown
- 1997-01-31 AU AU15984/97A patent/AU714313B2/en not_active Ceased
- 1997-01-31 CA CA002244746A patent/CA2244746A1/en not_active Abandoned
- 1997-01-31 TW TW086101169A patent/TW444015B/zh active
- 1997-01-31 US US09/117,506 patent/US6162920A/en not_active Expired - Fee Related
1998
- 1998-07-30 NO NO983509A patent/NO983509D0/no unknown

Also Published As

Publication number	Publication date
JP2001505527A (ja)	2001-04-24
UA49007C2 (uk)	2002-09-16
EP0896577A1 (de)	1999-02-17
CN1210535A (zh)	1999-03-10
BR9708295A (pt)	1999-08-03
RU2163599C2 (ru)	2001-02-27
DE69719502D1 (de)	2003-04-10
IL124951A0 (en)	1999-01-26
ATE233757T1 (de)	2003-03-15
HUP9901027A3 (en)	2001-08-28
CZ292504B6 (cs)	2003-10-15
ZA97847B (en)	1997-08-04
DE69719502T2 (de)	2004-02-19
AU1598497A (en)	1997-08-22
CN1073108C (zh)	2001-10-17
PT896577E (pt)	2003-06-30
WO1997028156A1 (en)	1997-08-07
PL186796B1 (pl)	2004-02-27
TR199801415T2 (xx)	1998-10-21
EP0896577B1 (de)	2003-03-05
DK0896577T3 (da)	2003-05-19
AU714313B2 (en)	1999-12-23
US6162920A (en)	2000-12-19
NO983509L (no)	1998-07-30
CA2244746A1 (en)	1997-08-07
ES2192261T3 (es)	2003-10-01
CZ242698A3 (cs)	1999-07-14
HK1018778A1 (en)	2000-01-07
PL328055A1 (en)	1999-01-04
DE19605024A1 (de)	1997-08-07
IL124951A (en)	2003-12-10
NO983509D0 (no)	1998-07-30
KR19990082151A (ko)	1999-11-15
TW444015B (en)	2001-07-01
HUP9901027A2 (hu)	2001-05-28

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KR100297196B1 (ko)	2001-11-22	신규택소이드,이의제조법및이를함유한약학조성물
SK101198A3 (en)	1998-12-02	Taxane derivatives having a pyridil substituted c13 side chain, their preparation and their use as anti-tumor agents
BG63204B1 (bg)	2001-06-29	Нови таксоиди, получаването им и фармацевтични състави, които ги съдържат
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EP1669358A1 (de)	2006-06-14	Cytotoxische Wirkstoffen auf Basis von neuen Taxanen
HUT74069A (en)	1996-10-28	Novel method for preparing taxane derivatives, novel derivatives thus obtained and compositions containing them
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HK1018778B (en)	2002-03-22	Taxane derivatives having a pyridyl substituted c13 side chain, their preparation and their use as anti-tumor agents
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