NO329403B1 - Semisyntetiske taksaner med antitumor, antiangiogenetiske og anti-artrose aktiviteter, farmasoytiske sammensetninger inneholdende dem og anvendelse av forbindelsene - Google Patents

Semisyntetiske taksaner med antitumor, antiangiogenetiske og anti-artrose aktiviteter, farmasoytiske sammensetninger inneholdende dem og anvendelse av forbindelsene Download PDF

Info

Publication number: NO329403B1
Authority: NO; Norway
Prior art keywords: hydrogen; seco; acetyl; tert; baccatin iii
Prior art date: 2000-01-18

Application number

NO20023428A

Other languages

English (en)

Norwegian (no)

Other versions

NO20023428D0 (no

NO20023428L (no

Inventor

Ezio Bombardelli

Alessandro Pontiroli

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.)

2000-01-18

Filing date

2002-07-17

Publication date

2010-10-11

2002-07-17 Application filed by Indena Spa filed Critical Indena Spa

2002-07-17 Publication of NO20023428D0 publication Critical patent/NO20023428D0/no

2002-09-16 Publication of NO20023428L publication Critical patent/NO20023428L/no

2010-10-11 Publication of NO329403B1 publication Critical patent/NO329403B1/no

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 4
150000001875 compounds Chemical class 0.000 title claims description 29
230000000259 anti-tumor effect Effects 0.000 title claims description 4
230000000694 effects Effects 0.000 title description 4
229940123237 Taxane Drugs 0.000 title description 2
230000002926 anti-osteoarthritic effect Effects 0.000 title 1
239000001257 hydrogen Substances 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 24
-1 n-propanoyl Chemical group 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 5
230000001772 anti-angiogenic effect Effects 0.000 claims description 5
239000000203 mixture Substances 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 4
150000002431 hydrogen Chemical group 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
229940079593 drug Drugs 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 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 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
201000008482 osteoarthritis Diseases 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims 1
238000000034 method Methods 0.000 abstract description 4
206010028980 Neoplasm Diseases 0.000 abstract description 3
230000033115 angiogenesis Effects 0.000 abstract description 2
201000011510 cancer Diseases 0.000 abstract description 2
206010003246 arthritis Diseases 0.000 abstract 1
230000002401 inhibitory effect Effects 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000002904 solvent Substances 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
238000002360 preparation method Methods 0.000 description 8
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
OVMSOCFBDVBLFW-VHLOTGQHSA-N (-)-Baccatin III Natural products 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 3
229930012538 Paclitaxel Natural products 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
229930014667 baccatin III Natural products 0.000 description 3
239000004202 carbamide Substances 0.000 description 3
229960001592 paclitaxel Drugs 0.000 description 3
239000008188 pellet Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
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 3
KULPPBMTPPOXOY-CTDRKSARSA-N (4s,5r)-2-(2,4-dimethoxyphenyl)-3-[(2-methylpropan-2-yl)oxycarbonyl]-4-(2-methylpropyl)-1,3-oxazolidine-5-carboxylic acid Chemical compound COC1=CC(OC)=CC=C1C1N(C(=O)OC(C)(C)C)[C@@H](CC(C)C)[C@H](C(O)=O)O1 KULPPBMTPPOXOY-CTDRKSARSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical group NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
108010082117 matrigel Proteins 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
230000004580 weight loss Effects 0.000 description 2
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 1
GAZNVVBKELWTBC-UHFFFAOYSA-N 2,3,4-trimethoxybenzoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C(OC)=C1OC GAZNVVBKELWTBC-UHFFFAOYSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
102000003974 Fibroblast growth factor 2 Human genes 0.000 description 1
108090000379 Fibroblast growth factor 2 Proteins 0.000 description 1
102000001554 Hemoglobins Human genes 0.000 description 1
108010054147 Hemoglobins Proteins 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
206010029350 Neurotoxicity Diseases 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
206010044221 Toxic encephalopathy Diseases 0.000 description 1
206010044565 Tremor Diseases 0.000 description 1
102000004243 Tubulin Human genes 0.000 description 1
108090000704 Tubulin Proteins 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000006427 angiogenic response Effects 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 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
150000005690 diesters Chemical class 0.000 description 1
229930004069 diterpene Natural products 0.000 description 1
125000000567 diterpene group Chemical group 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
230000007135 neurotoxicity Effects 0.000 description 1
231100000228 neurotoxicity Toxicity 0.000 description 1
238000011580 nude mouse model Methods 0.000 description 1
150000002917 oxazolidines Chemical class 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000003756 stirring Methods 0.000 description 1
231100000057 systemic toxicity Toxicity 0.000 description 1
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 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
230000004614 tumor growth Effects 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
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Physical Education & Sports Medicine (AREA)
Immunology (AREA)
Vascular Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
Rheumatology (AREA)
Oncology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Epoxy Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

NO20023428A 2000-01-18 2002-07-17 Semisyntetiske taksaner med antitumor, antiangiogenetiske og anti-artrose aktiviteter, farmasoytiske sammensetninger inneholdende dem og anvendelse av forbindelsene NO329403B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT2000MI000056A IT1317731B1 (it)	2000-01-18	2000-01-18	Tassani semisintetici con attivita' antitumorale ed antiangiogenetica.
PCT/EP2001/000386 WO2001053282A1 (en)	2000-01-18	2001-01-15	Semi-synthetic taxanes with antitumor and antiangiogenetic activities

Publications (3)

Publication Number	Publication Date
NO20023428D0 NO20023428D0 (no)	2002-07-17
NO20023428L NO20023428L (no)	2002-09-16
NO329403B1 true NO329403B1 (no)	2010-10-11

Family

ID=11443708

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20023428A NO329403B1 (no)	2000-01-18	2002-07-17	Semisyntetiske taksaner med antitumor, antiangiogenetiske og anti-artrose aktiviteter, farmasoytiske sammensetninger inneholdende dem og anvendelse av forbindelsene

Country Status (24)

Country	Link
US (2)	US6589979B2 (cs)
EP (1)	EP1248776B1 (cs)
JP (1)	JP4986354B2 (cs)
KR (1)	KR100813704B1 (cs)
CN (1)	CN1176916C (cs)
AT (1)	ATE271044T1 (cs)
AU (1)	AU781650B2 (cs)
CA (1)	CA2397591C (cs)
CZ (1)	CZ301251B6 (cs)
DE (1)	DE60104281T2 (cs)
DK (1)	DK1248776T3 (cs)
ES (1)	ES2223778T3 (cs)
HK (1)	HK1049998B (cs)
HU (1)	HU229347B1 (cs)
IL (1)	IL150787A0 (cs)
IT (1)	IT1317731B1 (cs)
NO (1)	NO329403B1 (cs)
PL (1)	PL202591B1 (cs)
PT (1)	PT1248776E (cs)
RU (1)	RU2259363C2 (cs)
SI (1)	SI1248776T1 (cs)
SK (1)	SK285683B6 (cs)
TR (1)	TR200401811T4 (cs)
WO (1)	WO2001053282A1 (cs)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1688415A1 (en) *	2004-12-07	2006-08-09	Aventis Pharma S.A.	Cytotoxic agents comprising new C-2 modified taxanes
ITMI20050415A1 (it) *	2005-03-15	2006-09-16	Indena Spa	Derivati tassanici semi-sintetici ad attivita' antitumorale
AU2012395148B2 (en)	2012-11-24	2016-10-27	Hangzhou Dac Biotech Co., Ltd.	Hydrophilic linkers and their uses for conjugation of drugs to cell binding molecules
FI3122757T3 (fi)	2014-02-28	2023-10-10	Hangzhou Dac Biotech Co Ltd	Varautuneita linkkereitä ja niiden konjugointikäyttötapoja
EP3319936B1 (en)	2015-07-12	2025-12-17	Hangzhou Dac Biotech Co., Ltd.	Bridge linkers for conjugation of cell-binding molecules
US9839687B2 (en)	2015-07-15	2017-12-12	Suzhou M-Conj Biotech Co., Ltd.	Acetylenedicarboxyl linkers and their uses in specific conjugation of a cell-binding molecule
AU2016429272A1 (en)	2016-11-14	2019-05-02	Hangzhou Dac Biotech Co., Ltd.	Conjugation linkers, cell binding molecule-drug conjugates containing the likers, methods of making and uses such conjugates with the linkers
CN117980327A (zh)	2021-11-03	2024-05-03	杭州多禧生物科技有限公司	抗体的特异性偶联

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
RU2059631C1 (ru) *	1991-11-29	1996-05-10	Дзе Юниверсити оф Канзас	Производные таксола и фармацевтическая композиция, обладающая противоопухолевой активностью
CA2109861C (en) *	1992-12-04	1999-03-16	Shu-Hui Chen	6,7-modified paclitaxels
HU222496B1 (hu) *	1994-07-26	2003-07-28	Indena S.P.A.	Félszintetikus taxánszármazékok, eljárás ezek előállítására, valamint ezeket tartalmazó gyógyászati készítmények

2000
- 2000-01-18 IT IT2000MI000056A patent/IT1317731B1/it active
2001
- 2001-01-15 RU RU2002119060/04A patent/RU2259363C2/ru not_active IP Right Cessation
- 2001-01-15 HU HU0204344A patent/HU229347B1/hu not_active IP Right Cessation
- 2001-01-15 DE DE60104281T patent/DE60104281T2/de not_active Expired - Lifetime
- 2001-01-15 CZ CZ20022478A patent/CZ301251B6/cs not_active IP Right Cessation
- 2001-01-15 PL PL356272A patent/PL202591B1/pl unknown
- 2001-01-15 AU AU33694/01A patent/AU781650B2/en not_active Ceased
- 2001-01-15 TR TR2004/01811T patent/TR200401811T4/xx unknown
- 2001-01-15 SI SI200130147T patent/SI1248776T1/xx unknown
- 2001-01-15 IL IL15078701A patent/IL150787A0/xx active IP Right Grant
- 2001-01-15 SK SK1056-2002A patent/SK285683B6/sk not_active IP Right Cessation
- 2001-01-15 KR KR1020027009182A patent/KR100813704B1/ko not_active Expired - Fee Related
- 2001-01-15 AT AT01905668T patent/ATE271044T1/de active
- 2001-01-15 CA CA002397591A patent/CA2397591C/en not_active Expired - Lifetime
- 2001-01-15 JP JP2001553757A patent/JP4986354B2/ja not_active Expired - Fee Related
- 2001-01-15 DK DK01905668T patent/DK1248776T3/da active
- 2001-01-15 CN CNB018038344A patent/CN1176916C/zh not_active Expired - Fee Related
- 2001-01-15 EP EP01905668A patent/EP1248776B1/en not_active Expired - Lifetime
- 2001-01-15 ES ES01905668T patent/ES2223778T3/es not_active Expired - Lifetime
- 2001-01-15 PT PT01905668T patent/PT1248776E/pt unknown
- 2001-01-15 WO PCT/EP2001/000386 patent/WO2001053282A1/en not_active Ceased
- 2001-01-15 HK HK03102021.6A patent/HK1049998B/zh not_active IP Right Cessation
2002
- 2002-07-03 US US10/187,995 patent/US6589979B2/en not_active Ceased
- 2002-07-17 NO NO20023428A patent/NO329403B1/no not_active IP Right Cessation
2005
- 2005-06-20 US US11/158,323 patent/USRE39723E1/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
ITMI20000056A0 (it)	2000-01-18
CA2397591A1 (en)	2001-07-26
ES2223778T3 (es)	2005-03-01
CZ301251B6 (cs)	2009-12-23
HUP0204344A3 (en)	2004-01-28
DE60104281D1 (de)	2004-08-19
NO20023428D0 (no)	2002-07-17
DK1248776T3 (da)	2004-11-22
CZ20022478A3 (cs)	2002-10-16
SK285683B6 (sk)	2007-06-07
US20030028038A1 (en)	2003-02-06
PL356272A1 (en)	2004-06-28
JP2003520792A (ja)	2003-07-08
WO2001053282A1 (en)	2001-07-26
TR200401811T4 (tr)	2004-09-21
HK1049998A1 (en)	2003-06-06
RU2259363C2 (ru)	2005-08-27
AU781650B2 (en)	2005-06-02
USRE39723E1 (en)	2007-07-10
AU3369401A (en)	2001-07-31
SI1248776T1 (en)	2004-10-31
US6589979B2 (en)	2003-07-08
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IT1317731B1 (it)	2003-07-15
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EP1248776B1 (en)	2004-07-14
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Publication	Publication Date	Title
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RU2419622C2 (ru)	2011-05-27	Производные таксола с противоопухолевой активностью