UA75039C2 - Taxanes having an ester substituent at c10, pharmaceutical composition based thereon and a method for inhibiting tumors growth - Google Patents
Taxanes having an ester substituent at c10, pharmaceutical composition based thereon and a method for inhibiting tumors growth Download PDFInfo
- Publication number
- UA75039C2 UA75039C2 UA2001106733A UA2001106733A UA75039C2 UA 75039 C2 UA75039 C2 UA 75039C2 UA 2001106733 A UA2001106733 A UA 2001106733A UA 2001106733 A UA2001106733 A UA 2001106733A UA 75039 C2 UA75039 C2 UA 75039C2
- Authority
- UA
- Ukraine
- Prior art keywords
- pyridyl
- furyl
- thienyl
- substituted
- taxane
- Prior art date
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- 229940123237 Taxane Drugs 0.000 title claims abstract description 146
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 27
- 238000000034 method Methods 0.000 title claims description 19
- 230000002401 inhibitory effect Effects 0.000 title claims description 4
- 125000004185 ester group Chemical group 0.000 title abstract description 3
- 206010028980 Neoplasm Diseases 0.000 title 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 description 131
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 112
- 125000000217 alkyl group Chemical group 0.000 claims description 106
- 125000003342 alkenyl group Chemical group 0.000 claims description 82
- 125000000304 alkynyl group Chemical group 0.000 claims description 77
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 65
- 125000002541 furyl group Chemical group 0.000 claims description 58
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 57
- 125000001544 thienyl group Chemical group 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 52
- 125000004076 pyridyl group Chemical group 0.000 claims description 48
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 45
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 44
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 40
- 229930194542 Keto Natural products 0.000 claims description 24
- 125000000468 ketone group Chemical group 0.000 claims description 24
- 125000001145 hydrido group Chemical group *[H] 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 125000004423 acyloxy group Chemical group 0.000 claims description 18
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 3
- 230000004614 tumor growth Effects 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 61
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 61
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 56
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 56
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 56
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 50
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 2
- 241000689227 Cora <basidiomycete fungus> Species 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract description 20
- -1 nitro, amino Chemical group 0.000 description 78
- 239000000243 solution Substances 0.000 description 74
- 150000001875 compounds Chemical class 0.000 description 67
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 49
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- 230000000259 anti-tumor effect Effects 0.000 description 36
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
- 125000004122 cyclic group Chemical group 0.000 description 20
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 16
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 125000003368 amide group Chemical group 0.000 description 9
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- 125000004429 atom Chemical group 0.000 description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
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- 150000002367 halogens Chemical group 0.000 description 7
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
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- 238000007911 parenteral administration Methods 0.000 description 7
- 229910052698 phosphorus Inorganic materials 0.000 description 7
- 239000011574 phosphorus Substances 0.000 description 7
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- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 239000003002 pH adjusting agent Substances 0.000 description 1
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- 229920001515 polyalkylene glycol Polymers 0.000 description 1
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- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
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- 235000010483 polyoxyethylene sorbitan monopalmitate Nutrition 0.000 description 1
- 239000000249 polyoxyethylene sorbitan monopalmitate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
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- 239000003755 preservative agent Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
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- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
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- 229940005550 sodium alginate Drugs 0.000 description 1
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- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
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- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229940082004 sodium laurate Drugs 0.000 description 1
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- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 229940100515 sorbitan Drugs 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
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- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
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- 229960004274 stearic acid Drugs 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
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- 150000003892 tartrate salts Chemical class 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
- 150000003538 tetroses Chemical class 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003641 trioses Chemical class 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- CKLHRQNQYIJFFX-UHFFFAOYSA-K ytterbium(III) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Yb+3] CKLHRQNQYIJFFX-UHFFFAOYSA-K 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms 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
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- B65D83/00—Containers or packages with special means for dispensing contents
- B65D83/14—Containers for dispensing liquid or semi-liquid contents by internal gaseous pressure, i.e. aerosol containers comprising propellant
- B65D83/75—Aerosol containers not provided for in groups B65D83/16 - B65D83/74
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Mechanical Engineering (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Epoxy Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17978200P | 2000-02-02 | 2000-02-02 | |
| PCT/US2001/003623 WO2001057032A1 (en) | 2000-02-02 | 2001-02-02 | C10 ester substituted taxanes as antitumor agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA75039C2 true UA75039C2 (en) | 2006-03-15 |
Family
ID=22657972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2001106733A UA75039C2 (en) | 2000-02-02 | 2001-02-02 | Taxanes having an ester substituent at c10, pharmaceutical composition based thereon and a method for inhibiting tumors growth |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP1165553B1 (https=) |
| JP (1) | JP2003522172A (https=) |
| CN (1) | CN1380882A (https=) |
| AT (1) | ATE432928T1 (https=) |
| AU (1) | AU782150B2 (https=) |
| BG (1) | BG64889B1 (https=) |
| BR (1) | BR0104354A (https=) |
| CA (1) | CA2368274C (https=) |
| CZ (1) | CZ20013430A3 (https=) |
| DE (1) | DE60138853D1 (https=) |
| GE (1) | GEP20043323B (https=) |
| HU (1) | HUP0600302A2 (https=) |
| IL (1) | IL145638A (https=) |
| MX (1) | MXPA01009905A (https=) |
| NO (1) | NO327910B1 (https=) |
| NZ (1) | NZ514382A (https=) |
| PL (1) | PL202957B1 (https=) |
| RO (1) | RO121270B1 (https=) |
| RU (1) | RU2262506C2 (https=) |
| SK (1) | SK13692001A3 (https=) |
| TR (1) | TR200102858T1 (https=) |
| TW (1) | TWI299732B (https=) |
| UA (1) | UA75039C2 (https=) |
| WO (1) | WO2001057032A1 (https=) |
| ZA (1) | ZA200108055B (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6649632B2 (en) | 2000-02-02 | 2003-11-18 | Fsu Research Foundation, Inc. | C10 ester substituted taxanes |
| CA2354471A1 (en) * | 2001-07-31 | 2003-01-31 | Florida State University Research Foundation, Inc. | C10 ester substituted taxanes |
| SG129990A1 (en) * | 2001-08-01 | 2007-03-20 | Univ Florida State Res Found | C10 ester substituted taxanes |
| HN2005000054A (es) | 2004-02-13 | 2009-02-18 | Florida State University Foundation Inc | Taxanos sustituidos con esteres de ciclopentilo en c10 |
| US20060189679A1 (en) * | 2005-02-14 | 2006-08-24 | Florida State University Research Foundation, Inc. | C10 cyclopropyl ester substituted taxane compositions |
| JP2011517455A (ja) * | 2008-03-31 | 2011-06-09 | フロリダ・ステイト・ユニバーシティ・リサーチ・ファウンデイション・インコーポレイテッド | Ｃ（１０）エチルエステルおよびｃ（１０）シクロプロピルエステル置換タキサン |
Family Cites Families (14)
| 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 |
| US5250683A (en) * | 1991-09-23 | 1993-10-05 | Florida State University | Certain substituted taxanes and pharmaceutical compositions containing them |
| US5243045A (en) * | 1991-09-23 | 1993-09-07 | Florida State University | Certain alkoxy substituted taxanes and pharmaceutical compositions containing them |
| IL108443A0 (en) * | 1993-01-29 | 1994-04-12 | Univ Florida State | C7 taxane derivatives and pharmaceutical compositions containing them |
| IL109051A0 (en) * | 1993-03-22 | 1994-06-24 | Univ Florida State | Taxanes having an amino substituted side-chain and pharmaceutical compositions containing them |
| ATE284689T1 (de) * | 1993-03-22 | 2005-01-15 | Univ Florida State | Pharmazeutische zusammenstellungen enthaltende eine furyl oder thienyl substituierte seitenkette |
| ATE209489T1 (de) * | 1993-03-22 | 2001-12-15 | Univ Florida State | Taxane mit pyridyl-substituierter seitenkette |
| US5475011A (en) * | 1993-03-26 | 1995-12-12 | The Research Foundation Of State University Of New York | Anti-tumor compounds, pharmaceutical compositions, methods for preparation thereof and for treatment |
| US6100411A (en) * | 1994-10-28 | 2000-08-08 | The Research Foundation Of State University Of New York | Taxoid anti-tumor agents and pharmaceutical compositions thereof |
| EP0788493A1 (en) * | 1994-10-28 | 1997-08-13 | The Research Foundation Of State University Of New York | Taxoid derivatives, their preparation and their use as antitumor agents |
| WO1997044026A1 (en) * | 1996-05-22 | 1997-11-27 | Neuromedica, Inc. | Compositions comprising conjugates of cis-docosahexaenoic acid and taxotere |
| US5795909A (en) * | 1996-05-22 | 1998-08-18 | Neuromedica, Inc. | DHA-pharmaceutical agent conjugates of taxanes |
| CA2314071A1 (en) * | 1997-12-19 | 1999-07-01 | Kabushiki Kaisha Yakult Honsha | Taxane derivatives |
| JP2003026673A (ja) * | 1999-03-05 | 2003-01-29 | Asahi Kasei Corp | 骨形成促進剤 |
-
2001
- 2001-02-02 PL PL351380A patent/PL202957B1/pl not_active IP Right Cessation
- 2001-02-02 EP EP01906971A patent/EP1165553B1/en not_active Expired - Lifetime
- 2001-02-02 RO ROA200101083A patent/RO121270B1/ro unknown
- 2001-02-02 AT AT01906971T patent/ATE432928T1/de not_active IP Right Cessation
- 2001-02-02 WO PCT/US2001/003623 patent/WO2001057032A1/en not_active Ceased
- 2001-02-02 CZ CZ20013430A patent/CZ20013430A3/cs unknown
- 2001-02-02 JP JP2001557864A patent/JP2003522172A/ja active Pending
- 2001-02-02 IL IL145638A patent/IL145638A/en not_active IP Right Cessation
- 2001-02-02 MX MXPA01009905A patent/MXPA01009905A/es active IP Right Grant
- 2001-02-02 GE GE4523A patent/GEP20043323B/en unknown
- 2001-02-02 HU HU0600302A patent/HUP0600302A2/hu unknown
- 2001-02-02 NZ NZ514382A patent/NZ514382A/en unknown
- 2001-02-02 SK SK1369-2001A patent/SK13692001A3/sk unknown
- 2001-02-02 CN CN01800568A patent/CN1380882A/zh active Pending
- 2001-02-02 AU AU34809/01A patent/AU782150B2/en not_active Ceased
- 2001-02-02 CA CA002368274A patent/CA2368274C/en not_active Expired - Fee Related
- 2001-02-02 UA UA2001106733A patent/UA75039C2/uk unknown
- 2001-02-02 RU RU2001129501/04A patent/RU2262506C2/ru active
- 2001-02-02 DE DE60138853T patent/DE60138853D1/de not_active Expired - Lifetime
- 2001-02-02 TR TR2001/02858T patent/TR200102858T1/xx unknown
- 2001-02-02 BR BR0104354-4A patent/BR0104354A/pt not_active IP Right Cessation
- 2001-03-27 TW TW090102238A patent/TWI299732B/zh not_active IP Right Cessation
- 2001-10-01 BG BG105965A patent/BG64889B1/bg unknown
- 2001-10-01 ZA ZA200108055A patent/ZA200108055B/en unknown
- 2001-10-01 NO NO20014754A patent/NO327910B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL145638A (en) | 2011-05-31 |
| PL351380A1 (en) | 2003-04-07 |
| NZ514382A (en) | 2004-05-28 |
| SK13692001A3 (sk) | 2002-07-02 |
| PL202957B1 (pl) | 2009-08-31 |
| NO20014754L (no) | 2001-11-29 |
| NO327910B1 (no) | 2009-10-19 |
| EP1165553B1 (en) | 2009-06-03 |
| BG64889B1 (bg) | 2006-08-31 |
| TWI299732B (en) | 2008-08-11 |
| BR0104354A (pt) | 2002-01-02 |
| CZ20013430A3 (cs) | 2002-04-17 |
| CN1380882A (zh) | 2002-11-20 |
| TR200102858T1 (tr) | 2002-12-23 |
| CA2368274A1 (en) | 2001-08-09 |
| WO2001057032A1 (en) | 2001-08-09 |
| AU3480901A (en) | 2001-08-14 |
| CA2368274C (en) | 2009-10-13 |
| GEP20043323B (en) | 2004-02-10 |
| IL145638A0 (en) | 2002-06-30 |
| NO20014754D0 (no) | 2001-10-01 |
| JP2003522172A (ja) | 2003-07-22 |
| EP1165553A1 (en) | 2002-01-02 |
| BG105965A (en) | 2002-07-31 |
| MXPA01009905A (es) | 2003-08-20 |
| AU782150B2 (en) | 2005-07-07 |
| HUP0600302A2 (en) | 2006-07-28 |
| DE60138853D1 (de) | 2009-07-16 |
| ZA200108055B (en) | 2003-12-01 |
| ATE432928T1 (de) | 2009-06-15 |
| RO121270B1 (ro) | 2007-02-28 |
| RU2262506C2 (ru) | 2005-10-20 |
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