TWI299732B - C10 ester substituted taxanes - Google Patents
C10 ester substituted taxanes Download PDFInfo
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- TWI299732B TWI299732B TW090102238A TW90102238A TWI299732B TW I299732 B TWI299732 B TW I299732B TW 090102238 A TW090102238 A TW 090102238A TW 90102238 A TW90102238 A TW 90102238A TW I299732 B TWI299732 B TW I299732B
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- tbuoco
- furyl
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- 229940123237 Taxane Drugs 0.000 title claims abstract description 9
- 125000004185 ester group Chemical group 0.000 title abstract 2
- 125000001424 substituent group Chemical group 0.000 claims abstract description 14
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 72
- -1 3 -pyranyl group Chemical group 0.000 claims description 45
- 239000008194 pharmaceutical composition Substances 0.000 claims description 42
- 229930192474 thiophene Natural products 0.000 claims description 35
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 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 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 150000002923 oximes Chemical group 0.000 claims description 3
- 125000001725 pyrenyl group Chemical group 0.000 claims description 3
- 101000919980 Homo sapiens Protoheme IX farnesyltransferase, mitochondrial Proteins 0.000 claims description 2
- 102100030729 Protoheme IX farnesyltransferase, mitochondrial Human genes 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 17
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 10
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 102100030878 Cytochrome c oxidase subunit 1 Human genes 0.000 claims 2
- 101000919849 Homo sapiens Cytochrome c oxidase subunit 1 Proteins 0.000 claims 2
- 101000605122 Homo sapiens Prostaglandin G/H synthase 1 Proteins 0.000 claims 2
- PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims 1
- 101100193633 Danio rerio rag2 gene Proteins 0.000 claims 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims 1
- 101100193635 Mus musculus Rag2 gene Proteins 0.000 claims 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
- 150000001345 alkine derivatives Chemical class 0.000 claims 1
- 230000000259 anti-tumor effect Effects 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 125000004050 enoyl group Chemical group 0.000 claims 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- GKROKAVBUIADBS-UHFFFAOYSA-N phenanthrene-2-carbaldehyde Chemical compound C1=CC=C2C3=CC=C(C=O)C=C3C=CC2=C1 GKROKAVBUIADBS-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 31
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 235000019439 ethyl acetate Nutrition 0.000 description 14
- 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 13
- 229930012538 Paclitaxel Natural products 0.000 description 12
- 229960001592 paclitaxel Drugs 0.000 description 12
- 125000000623 heterocyclic group Chemical group 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 150000003573 thiols Chemical class 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 230000002079 cooperative effect Effects 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- 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 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- 239000002246 antineoplastic agent Substances 0.000 description 5
- 125000004104 aryloxy group Chemical group 0.000 description 5
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- 125000004122 cyclic group Chemical group 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 206010036790 Productive cough Diseases 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 125000005133 alkynyloxy group Chemical group 0.000 description 4
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- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 3
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- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 description 3
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- 125000003545 alkoxy group Chemical group 0.000 description 3
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 3
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- 229960003668 docetaxel Drugs 0.000 description 3
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 3
- 125000006038 hexenyl group Chemical group 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical group CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Dispersion Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Mechanical Engineering (AREA)
- Engineering & Computer Science (AREA)
- Oncology (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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17978200P | 2000-02-02 | 2000-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI299732B true TWI299732B (en) | 2008-08-11 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW090102238A TWI299732B (en) | 2000-02-02 | 2001-03-27 | C10 ester substituted taxanes |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP1165553B1 (enExample) |
| JP (1) | JP2003522172A (enExample) |
| CN (1) | CN1380882A (enExample) |
| AT (1) | ATE432928T1 (enExample) |
| AU (1) | AU782150B2 (enExample) |
| BG (1) | BG64889B1 (enExample) |
| BR (1) | BR0104354A (enExample) |
| CA (1) | CA2368274C (enExample) |
| CZ (1) | CZ20013430A3 (enExample) |
| DE (1) | DE60138853D1 (enExample) |
| GE (1) | GEP20043323B (enExample) |
| HU (1) | HUP0600302A2 (enExample) |
| IL (1) | IL145638A (enExample) |
| MX (1) | MXPA01009905A (enExample) |
| NO (1) | NO327910B1 (enExample) |
| NZ (1) | NZ514382A (enExample) |
| PL (1) | PL202957B1 (enExample) |
| RO (1) | RO121270B1 (enExample) |
| RU (1) | RU2262506C2 (enExample) |
| SK (1) | SK13692001A3 (enExample) |
| TR (1) | TR200102858T1 (enExample) |
| TW (1) | TWI299732B (enExample) |
| UA (1) | UA75039C2 (enExample) |
| WO (1) | WO2001057032A1 (enExample) |
| ZA (1) | ZA200108055B (enExample) |
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 |
| SV2006002010A (es) | 2004-02-13 | 2006-08-23 | Univ Florida State Res Found | Taxanos sustituidos con esteres de ciclopentilo en c10 |
| WO2006088767A2 (en) * | 2005-02-14 | 2006-08-24 | Florida State University Research Foundation, Inc. | C10 cyclopropyl ester substituted taxane compositions |
| US8242166B2 (en) | 2008-03-31 | 2012-08-14 | Florida State University Research Foundation, Inc. | C(10) ethyl ester and C(10) cyclopropyl ester substituted taxanes |
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 |
| US5243045A (en) * | 1991-09-23 | 1993-09-07 | Florida State University | Certain alkoxy substituted taxanes and pharmaceutical compositions containing them |
| US5250683A (en) * | 1991-09-23 | 1993-10-05 | Florida State University | Certain 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 |
| CA2158863C (en) * | 1993-03-22 | 2006-12-19 | Robert A. Holton | Taxanes having a pyridyl substituted side-chain |
| EP0690711B1 (en) * | 1993-03-22 | 2000-08-16 | Florida State University | Taxanes having an amino substituted side-chain |
| PT1228759E (pt) * | 1993-03-22 | 2005-04-29 | Univ Florida State | Composicoes farmaceuticas contendo um taxano possuindo uma cadeia lateral substituida com furilo ou tienilo |
| 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 |
| WO1996013495A1 (en) * | 1994-10-28 | 1996-05-09 | The Research Foundation Of State University Of New York | Taxoid derivatives, their preparation and their use as antitumor agents |
| CA2255615C (en) * | 1996-05-22 | 2006-08-29 | Neuromedica, Inc. | Compositions comprising conjugates of cis-docosahexaenoic acid and docetaxel |
| US5795909A (en) * | 1996-05-22 | 1998-08-18 | Neuromedica, Inc. | DHA-pharmaceutical agent conjugates of taxanes |
| AU758418B2 (en) * | 1997-12-19 | 2003-03-20 | 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 RO ROA200101083A patent/RO121270B1/ro unknown
- 2001-02-02 CA CA002368274A patent/CA2368274C/en not_active Expired - Fee Related
- 2001-02-02 HU HU0600302A patent/HUP0600302A2/hu unknown
- 2001-02-02 CN CN01800568A patent/CN1380882A/zh active Pending
- 2001-02-02 SK SK1369-2001A patent/SK13692001A3/sk unknown
- 2001-02-02 IL IL145638A patent/IL145638A/en not_active IP Right Cessation
- 2001-02-02 PL PL351380A patent/PL202957B1/pl not_active IP Right Cessation
- 2001-02-02 JP JP2001557864A patent/JP2003522172A/ja active Pending
- 2001-02-02 GE GE4523A patent/GEP20043323B/en unknown
- 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 NZ NZ514382A patent/NZ514382A/en unknown
- 2001-02-02 UA UA2001106733A patent/UA75039C2/uk unknown
- 2001-02-02 AT AT01906971T patent/ATE432928T1/de not_active IP Right Cessation
- 2001-02-02 DE DE60138853T patent/DE60138853D1/de not_active Expired - Lifetime
- 2001-02-02 EP EP01906971A patent/EP1165553B1/en not_active Expired - Lifetime
- 2001-02-02 MX MXPA01009905A patent/MXPA01009905A/es active IP Right Grant
- 2001-02-02 RU RU2001129501/04A patent/RU2262506C2/ru active
- 2001-02-02 AU AU34809/01A patent/AU782150B2/en not_active Ceased
- 2001-02-02 BR BR0104354-4A patent/BR0104354A/pt not_active IP Right Cessation
- 2001-02-02 TR TR2001/02858T patent/TR200102858T1/xx unknown
- 2001-03-27 TW TW090102238A patent/TWI299732B/zh not_active IP Right Cessation
- 2001-10-01 NO NO20014754A patent/NO327910B1/no not_active IP Right Cessation
- 2001-10-01 ZA ZA200108055A patent/ZA200108055B/en unknown
- 2001-10-01 BG BG105965A patent/BG64889B1/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0600302A2 (en) | 2006-07-28 |
| TR200102858T1 (tr) | 2002-12-23 |
| RU2262506C2 (ru) | 2005-10-20 |
| PL351380A1 (en) | 2003-04-07 |
| ATE432928T1 (de) | 2009-06-15 |
| BG64889B1 (bg) | 2006-08-31 |
| IL145638A (en) | 2011-05-31 |
| IL145638A0 (en) | 2002-06-30 |
| GEP20043323B (en) | 2004-02-10 |
| AU3480901A (en) | 2001-08-14 |
| SK13692001A3 (sk) | 2002-07-02 |
| NZ514382A (en) | 2004-05-28 |
| JP2003522172A (ja) | 2003-07-22 |
| EP1165553B1 (en) | 2009-06-03 |
| RO121270B1 (ro) | 2007-02-28 |
| PL202957B1 (pl) | 2009-08-31 |
| CZ20013430A3 (cs) | 2002-04-17 |
| BR0104354A (pt) | 2002-01-02 |
| EP1165553A1 (en) | 2002-01-02 |
| NO20014754D0 (no) | 2001-10-01 |
| AU782150B2 (en) | 2005-07-07 |
| BG105965A (en) | 2002-07-31 |
| UA75039C2 (en) | 2006-03-15 |
| NO327910B1 (no) | 2009-10-19 |
| NO20014754L (no) | 2001-11-29 |
| CN1380882A (zh) | 2002-11-20 |
| ZA200108055B (en) | 2003-12-01 |
| CA2368274C (en) | 2009-10-13 |
| CA2368274A1 (en) | 2001-08-09 |
| MXPA01009905A (es) | 2003-08-20 |
| DE60138853D1 (de) | 2009-07-16 |
| WO2001057032A1 (en) | 2001-08-09 |
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