KR20020000159A - 항종양제로서의 ｃ10 카르바모일옥시 치환된 탁산 - Google Patents
항종양제로서의 ｃ10 카르바모일옥시 치환된 탁산 Download PDFInfo
- Publication number
- KR20020000159A KR20020000159A KR1020017012573A KR20017012573A KR20020000159A KR 20020000159 A KR20020000159 A KR 20020000159A KR 1020017012573 A KR1020017012573 A KR 1020017012573A KR 20017012573 A KR20017012573 A KR 20017012573A KR 20020000159 A KR20020000159 A KR 20020000159A
- Authority
- KR
- South Korea
- Prior art keywords
- pyridyl
- thienyl
- furyl
- alkyl
- substituted
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 229940123237 Taxane Drugs 0.000 title claims abstract description 162
- -1 Carbamoyloxy Chemical group 0.000 title claims abstract description 110
- 239000002246 antineoplastic agent Substances 0.000 title description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 161
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 159
- 150000001875 compounds Chemical class 0.000 claims description 145
- 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 86
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 68
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 61
- 125000002541 furyl group Chemical group 0.000 claims description 53
- 125000001544 thienyl group Chemical group 0.000 claims description 52
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 48
- 125000003342 alkenyl group Chemical group 0.000 claims description 46
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 46
- 125000004076 pyridyl group Chemical group 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 36
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 34
- 229930194542 Keto Natural products 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 125000000468 ketone group Chemical group 0.000 claims description 25
- 125000001145 hydrido group Chemical group *[H] 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 239000008194 pharmaceutical composition Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 18
- 125000004423 acyloxy group Chemical group 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 14
- 239000003937 drug carrier Substances 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 100
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 76
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 68
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 68
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 65
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 65
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 65
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 65
- 241000125205 Anethum Species 0.000 claims 35
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 30
- 230000004614 tumor growth Effects 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 abstract description 29
- 239000000243 solution Substances 0.000 description 49
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 125000004122 cyclic group Chemical group 0.000 description 18
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- 229960003668 docetaxel Drugs 0.000 description 14
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 13
- 125000003118 aryl group Chemical group 0.000 description 12
- 239000000839 emulsion Substances 0.000 description 12
- 125000006239 protecting group Chemical group 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- 150000003952 β-lactams Chemical class 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 10
- 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 10
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 9
- 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 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 229930012538 Paclitaxel Natural products 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 8
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 8
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 8
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 125000006038 hexenyl group Chemical group 0.000 description 8
- 125000005980 hexynyl group Chemical group 0.000 description 8
- 229960001592 paclitaxel Drugs 0.000 description 8
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 8
- 229920002472 Starch Polymers 0.000 description 7
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
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- 125000005981 pentynyl group Chemical group 0.000 description 7
- 239000008389 polyethoxylated castor oil Substances 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- 150000001241 acetals Chemical class 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 125000003368 amide group Chemical group 0.000 description 6
- 125000004104 aryloxy group Chemical group 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 6
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- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 6
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- 235000000346 sugar Nutrition 0.000 description 6
- 150000003573 thiols Chemical class 0.000 description 6
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- 150000002367 halogens Chemical group 0.000 description 5
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- 239000000843 powder Substances 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 4
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- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
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- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 4
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
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Classifications
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- 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
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- 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
- A61K9/08—Solutions
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17979300P | 2000-02-02 | 2000-02-02 | |
| US60/179,793 | 2000-02-02 | ||
| PCT/US2001/003633 WO2001057033A1 (en) | 2000-02-02 | 2001-02-02 | C10 carbamoyloxy substituted taxanes as antitumor agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20020000159A true KR20020000159A (ko) | 2002-01-04 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020017012573A Abandoned KR20020000159A (ko) | 2000-02-02 | 2001-02-02 | 항종양제로서의 ｃ10 카르바모일옥시 치환된 탁산 |
Country Status (20)
| Country | Link |
|---|---|
| US (3) | US6596737B2 (https=) |
| EP (1) | EP1165551B1 (https=) |
| JP (1) | JP2003522173A (https=) |
| KR (1) | KR20020000159A (https=) |
| CN (1) | CN1362959A (https=) |
| AT (1) | ATE401325T1 (https=) |
| AU (1) | AU783422B2 (https=) |
| BR (1) | BR0104352A (https=) |
| CA (1) | CA2368541A1 (https=) |
| CZ (1) | CZ20013520A3 (https=) |
| DE (1) | DE60134814D1 (https=) |
| HK (1) | HK1047936A1 (https=) |
| HU (1) | HUP0200721A3 (https=) |
| IL (1) | IL145640A (https=) |
| MX (1) | MXPA01009921A (https=) |
| NO (1) | NO20014760L (https=) |
| NZ (1) | NZ514407A (https=) |
| PL (1) | PL350331A1 (https=) |
| WO (1) | WO2001057033A1 (https=) |
| ZA (1) | ZA200108053B (https=) |
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| EP1165551B1 (en) * | 2000-02-02 | 2008-07-16 | Florida State University Research Foundation, Inc. | C10 carbamoyloxy substituted taxanes as antitumor agents |
| MXPA01009900A (es) * | 2000-02-02 | 2003-08-20 | Univ Florida State Res Found | Formulaciones de taxano que tienen solubilidad mejorada. |
| CN1712399B (zh) * | 2004-06-24 | 2010-08-11 | 中国医学科学院药物研究所 | 紫杉醇和免疫增强剂胞壁酰二肽共轭物的制备及用途 |
| WO2007112570A1 (en) * | 2006-04-03 | 2007-10-11 | Pharmatherm Chemicals Inc. | Thermal extraction method and product |
| CN103183724B (zh) | 2010-05-27 | 2015-01-14 | 深圳信立泰药业股份有限公司 | 多西紫杉醇共缀物的制备方法 |
| JP6959096B2 (ja) * | 2017-10-13 | 2021-11-02 | エイブリック株式会社 | 充放電制御回路及びこれを備えたバッテリ装置 |
Family Cites Families (34)
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| US5175315A (en) | 1989-05-31 | 1992-12-29 | Florida State University | Method for preparation of taxol using β-lactam |
| FR2679230B1 (fr) * | 1991-07-16 | 1993-11-19 | Rhone Poulenc Rorer Sa | Nouveaux derives d'analogues du taxol, leur preparation et les compositions qui les contiennent. |
| US5243045A (en) | 1991-09-23 | 1993-09-07 | Florida State University | Certain alkoxy substituted taxanes and pharmaceutical compositions containing them |
| US5283253A (en) | 1991-09-23 | 1994-02-01 | Florida State University | Furyl or thienyl carbonyl substituted taxanes 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 |
| SG46582A1 (en) | 1991-09-23 | 1998-02-20 | Univ Florida State | 10-Desacetoxytaxol derivatives |
| US5721268A (en) | 1991-09-23 | 1998-02-24 | Florida State University | C7 taxane derivatives and pharmaceutical compositions containing them |
| US5714513A (en) | 1991-09-23 | 1998-02-03 | Florida State University | C10 taxane derivatives and pharmaceutical compositions |
| US5430160A (en) | 1991-09-23 | 1995-07-04 | Florida State University | Preparation of substituted isoserine esters using β-lactams and metal or ammonium alkoxides |
| PT552041E (pt) | 1992-01-15 | 2000-12-29 | Squibb & Sons Inc | Processo enzimaticos para a resolucao de misturas enantiomericas de compostos uteis como intermediarios para a preparacao de taxanos |
| US5272171A (en) | 1992-02-13 | 1993-12-21 | Bristol-Myers Squibb Company | Phosphonooxy and carbonate derivatives of taxol |
| FR2691460B1 (fr) | 1992-05-21 | 1994-07-22 | Rhone Poulenc Rorer Sa | Nouveaux derives du taxane, leur preparation et les compositions qui les contiennent. |
| CA2109861C (en) | 1992-12-04 | 1999-03-16 | Shu-Hui Chen | 6,7-modified paclitaxels |
| ES2145829T3 (es) | 1993-06-11 | 2000-07-16 | Upjohn Co | Uso antineoplasico de delta 6,7-taxoles y composiciones farmaceuticas que los contienen. |
| IL109926A (en) | 1993-06-15 | 2000-02-29 | Bristol Myers Squibb Co | Methods for the preparation of taxanes and microorganisms and enzymes utilized therein |
| TW397866B (en) | 1993-07-14 | 2000-07-11 | Bristol Myers Squibb Co | Enzymatic processes for the resolution of enantiomeric mixtures of compounds useful as intermediates in the preparation of taxanes |
| 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 |
| FR2732342B1 (fr) * | 1995-04-03 | 1997-04-30 | Rhone Poulenc Rorer Sa | Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent |
| FR2732968B1 (fr) | 1995-04-14 | 1997-05-16 | Rhone Poulenc Rorer Sa | Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent |
| US5780653A (en) | 1995-06-07 | 1998-07-14 | Vivorx Pharmaceuticals, Inc. | Nitrophenyl, 10-deacetylated substituted taxol derivatives as dual functional cytotoxic/radiosensitizers |
| CA2231837A1 (en) | 1995-09-13 | 1997-03-20 | Florida State University | Radiosensitizing taxanes and their pharmaceutical preparations |
| WO1997042181A1 (en) | 1996-05-06 | 1997-11-13 | Florida State University | 1-deoxy baccatin iii, 1-deoxy taxol and 1-deoxy taxol analogs and method for the preparation thereof |
| CA2259977C (en) * | 1996-07-15 | 2005-06-28 | Kabushiki Kaisha Yakult Honsha | Taxane derivatives and drugs containing the same |
| US5811452A (en) | 1997-01-08 | 1998-09-22 | The Research Foundation Of State University Of New York | Taxoid reversal agents for drug-resistance in cancer chemotherapy and pharmaceutical compositions thereof |
| US5912264A (en) | 1997-03-03 | 1999-06-15 | Bristol-Myers Squibb Company | 6-halo-or nitrate-substituted paclitaxels |
| US7288665B1 (en) | 1997-08-18 | 2007-10-30 | Florida State University | Process for selective derivatization of taxanes |
| JPH1192468A (ja) * | 1997-09-17 | 1999-04-06 | Yakult Honsha Co Ltd | 新規なタキサン誘導体 |
| 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 |
| EP1165551B1 (en) * | 2000-02-02 | 2008-07-16 | Florida State University Research Foundation, Inc. | C10 carbamoyloxy substituted taxanes as antitumor agents |
| KR20010111580A (ko) | 2000-02-02 | 2001-12-19 | 플로리다 스테이트 유니버시티 리서치 파운데이션, 인크 | 개선된 용해도를 갖는 탁산 제형물 |
| MXPA01009900A (es) * | 2000-02-02 | 2003-08-20 | Univ Florida State Res Found | Formulaciones de taxano que tienen solubilidad mejorada. |
| GB2370649B (en) * | 2000-11-09 | 2003-06-25 | Toppan Printing Co Ltd | Measurement of rate of transmission of a vapour through a sample |
-
2001
- 2001-02-02 EP EP01905434A patent/EP1165551B1/en not_active Expired - Lifetime
- 2001-02-02 BR BR0104352-8A patent/BR0104352A/pt not_active IP Right Cessation
- 2001-02-02 NZ NZ51440701A patent/NZ514407A/xx unknown
- 2001-02-02 AT AT01905434T patent/ATE401325T1/de not_active IP Right Cessation
- 2001-02-02 US US09/775,852 patent/US6596737B2/en not_active Expired - Fee Related
- 2001-02-02 AU AU33313/01A patent/AU783422B2/en not_active Ceased
- 2001-02-02 HK HK03100170.9A patent/HK1047936A1/zh unknown
- 2001-02-02 KR KR1020017012573A patent/KR20020000159A/ko not_active Abandoned
- 2001-02-02 DE DE60134814T patent/DE60134814D1/de not_active Expired - Fee Related
- 2001-02-02 CN CN01800317A patent/CN1362959A/zh active Pending
- 2001-02-02 IL IL145640A patent/IL145640A/en not_active IP Right Cessation
- 2001-02-02 CA CA002368541A patent/CA2368541A1/en not_active Withdrawn
- 2001-02-02 CZ CZ20013520A patent/CZ20013520A3/cs unknown
- 2001-02-02 JP JP2001557865A patent/JP2003522173A/ja not_active Withdrawn
- 2001-02-02 MX MXPA01009921A patent/MXPA01009921A/es active IP Right Grant
- 2001-02-02 WO PCT/US2001/003633 patent/WO2001057033A1/en not_active Ceased
- 2001-02-02 PL PL01350331A patent/PL350331A1/xx not_active Application Discontinuation
- 2001-02-02 HU HU0200721A patent/HUP0200721A3/hu unknown
- 2001-10-01 NO NO20014760A patent/NO20014760L/no not_active Application Discontinuation
- 2001-10-01 ZA ZA200108053A patent/ZA200108053B/en unknown
-
2003
- 2003-07-11 US US10/618,063 patent/US6906088B2/en not_active Expired - Fee Related
-
2005
- 2005-02-28 US US11/067,882 patent/US7230013B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BR0104352A (pt) | 2002-01-02 |
| US20050182098A1 (en) | 2005-08-18 |
| MXPA01009921A (es) | 2003-08-01 |
| ZA200108053B (en) | 2003-12-01 |
| JP2003522173A (ja) | 2003-07-22 |
| HUP0200721A3 (en) | 2005-02-28 |
| PL350331A1 (en) | 2002-12-02 |
| EP1165551B1 (en) | 2008-07-16 |
| HUP0200721A2 (hu) | 2002-07-29 |
| US6596737B2 (en) | 2003-07-22 |
| US20020077341A1 (en) | 2002-06-20 |
| EP1165551A1 (en) | 2002-01-02 |
| NO20014760L (no) | 2001-11-30 |
| ATE401325T1 (de) | 2008-08-15 |
| IL145640A (en) | 2007-02-11 |
| CN1362959A (zh) | 2002-08-07 |
| CA2368541A1 (en) | 2001-08-09 |
| IL145640A0 (en) | 2002-06-30 |
| AU783422B2 (en) | 2005-10-27 |
| US6906088B2 (en) | 2005-06-14 |
| DE60134814D1 (de) | 2008-08-28 |
| CZ20013520A3 (cs) | 2002-03-13 |
| WO2001057033A1 (en) | 2001-08-09 |
| NO20014760D0 (no) | 2001-10-01 |
| HK1047936A1 (zh) | 2003-03-14 |
| US7230013B2 (en) | 2007-06-12 |
| NZ514407A (en) | 2004-12-24 |
| US20040034230A1 (en) | 2004-02-19 |
| AU3331301A (en) | 2001-08-14 |
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