SK13692001A3 - Taxány substituované v polohe C10 esterovou skupinou - Google Patents

Taxány substituované v polohe C10 esterovou skupinou Download PDF

Info

Publication number: SK13692001A3
Authority: SK; Slovakia
Prior art keywords: pyridyl; thienyl; taxane; alkyl; furyl
Prior art date: 2000-02-02

Application number

SK1369-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Robert A. Holton

Original Assignee

Florida State University Research Foundation, Inc.

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.)

2000-02-02

Filing date

2001-02-02

Publication date

2002-07-02

2001-02-02 Application filed by Florida State University Research Foundation, Inc. filed Critical Florida State University Research Foundation, Inc.

2002-07-02 Publication of SK13692001A3 publication Critical patent/SK13692001A3/sk

Links

229940123237 Taxane Drugs 0.000 title claims abstract description 158
125000004185 ester group Chemical group 0.000 title abstract 2
239000002246 antineoplastic agent Substances 0.000 title description 5
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 145
125000000217 alkyl group Chemical group 0.000 claims description 143
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 124
-1 C 1 -C 6 alkyl Chemical group 0.000 claims description 117
125000003342 alkenyl group Chemical group 0.000 claims description 115
125000000304 alkynyl group Chemical group 0.000 claims description 105
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 75
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 71
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 61
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 60
125000002541 furyl group Chemical group 0.000 claims description 57
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 54
125000001544 thienyl group Chemical group 0.000 claims description 53
239000000203 mixture Substances 0.000 claims description 47
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 46
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 41
125000001183 hydrocarbyl group Chemical group 0.000 claims description 41
239000001257 hydrogen Substances 0.000 claims description 27
229910052739 hydrogen Inorganic materials 0.000 claims description 27
239000008194 pharmaceutical composition Substances 0.000 claims description 27
125000000468 ketone group Chemical group 0.000 claims description 25
229930194542 Keto Natural products 0.000 claims description 24
125000004423 acyloxy group Chemical group 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 20
238000000034 method Methods 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
229910052799 carbon Inorganic materials 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
239000003937 drug carrier Substances 0.000 claims description 9
150000001721 carbon Chemical group 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 8
125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 5
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
241000124008 Mammalia Species 0.000 claims description 3
230000002401 inhibitory effect Effects 0.000 claims description 3
230000004614 tumor growth Effects 0.000 claims description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 59
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 58
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 35
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 23
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 21
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims 12
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 4
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 2
125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims 1
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
125000001424 substituent group Chemical group 0.000 abstract description 18
239000000243 solution Substances 0.000 description 76
150000001875 compounds Chemical class 0.000 description 68
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 47
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
125000004076 pyridyl group Chemical group 0.000 description 42
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 37
230000000259 anti-tumor effect Effects 0.000 description 36
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
125000004122 cyclic group Chemical group 0.000 description 25
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
150000002148 esters Chemical group 0.000 description 18
235000019441 ethanol Nutrition 0.000 description 18
125000004453 alkoxycarbonyl group Chemical group 0.000 description 16
239000000839 emulsion Substances 0.000 description 14
125000003118 aryl group Chemical group 0.000 description 13
PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
125000001072 heteroaryl group Chemical group 0.000 description 12
125000005842 heteroatom Chemical group 0.000 description 12
239000002904 solvent Substances 0.000 description 12
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
239000003921 oil Substances 0.000 description 11
235000019198 oils Nutrition 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
235000019439 ethyl acetate Nutrition 0.000 description 10
235000002639 sodium chloride Nutrition 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
125000003545 alkoxy group Chemical group 0.000 description 9
125000003368 amide group Chemical group 0.000 description 9
125000004104 aryloxy group Chemical group 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
235000014113 dietary fatty acids Nutrition 0.000 description 9
239000000194 fatty acid Substances 0.000 description 9
229930195729 fatty acid Natural products 0.000 description 9
238000007911 parenteral administration Methods 0.000 description 9
239000008389 polyethoxylated castor oil Substances 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
150000003573 thiols Chemical class 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
150000002367 halogens Chemical group 0.000 description 8
239000011780 sodium chloride Substances 0.000 description 8
229930012538 Paclitaxel Natural products 0.000 description 7
150000001241 acetals Chemical class 0.000 description 7
239000002552 dosage form Substances 0.000 description 7
229910052736 halogen Inorganic materials 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
229960001592 paclitaxel Drugs 0.000 description 7
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 7
239000007787 solid Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)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 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
229920002472 Starch Polymers 0.000 description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
125000002252 acyl group Chemical group 0.000 description 6
125000004429 atom Chemical group 0.000 description 6
230000000694 effects Effects 0.000 description 6
125000001033 ether group Chemical group 0.000 description 6
150000002430 hydrocarbons Chemical class 0.000 description 6
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
229920001223 polyethylene glycol Polymers 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 5
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 5
239000003814 drug Substances 0.000 description 5
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 5
235000011187 glycerol Nutrition 0.000 description 5
125000000623 heterocyclic group Chemical group 0.000 description 5
125000006038 hexenyl group Chemical group 0.000 description 5
125000005980 hexynyl group Chemical group 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
229910052698 phosphorus Inorganic materials 0.000 description 5
239000011574 phosphorus Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
239000003826 tablet Substances 0.000 description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
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 4
206010028980 Neoplasm Diseases 0.000 description 4
239000002202 Polyethylene glycol Substances 0.000 description 4
235000021355 Stearic acid Nutrition 0.000 description 4
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
229930006000 Sucrose Natural products 0.000 description 4
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
239000002585 base Substances 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
239000012267 brine Substances 0.000 description 4
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 4
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
229960003668 docetaxel Drugs 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000003480 eluent Substances 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
239000000284 extract Substances 0.000 description 4
150000004665 fatty acids Chemical class 0.000 description 4
238000009472 formulation Methods 0.000 description 4
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
238000007913 intrathecal administration Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
210000004185 liver Anatomy 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000002609 medium Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 4
125000005981 pentynyl group Chemical group 0.000 description 4
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
239000003549 soybean oil Substances 0.000 description 4
235000012424 soybean oil Nutrition 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
239000008117 stearic acid Substances 0.000 description 4
229960004274 stearic acid Drugs 0.000 description 4
239000005720 sucrose Substances 0.000 description 4
235000000346 sugar Nutrition 0.000 description 4
239000000725 suspension Substances 0.000 description 4
150000003626 triacylglycerols Chemical class 0.000 description 4
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 3
ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
241000283690 Bos taurus Species 0.000 description 3
229920002261 Corn starch Polymers 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
229920002690 Polyoxyl 40 HydrogenatedCastorOil Polymers 0.000 description 3
235000019485 Safflower oil Nutrition 0.000 description 3
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000004703 alkoxides Chemical class 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
229910052796 boron Inorganic materials 0.000 description 3
125000004744 butyloxycarbonyl group Chemical group 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000004359 castor oil Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
239000008120 corn starch Substances 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
229940127089 cytotoxic agent Drugs 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 3
239000000945 filler Substances 0.000 description 3
238000003818 flash chromatography Methods 0.000 description 3
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
239000008101 lactose Substances 0.000 description 3
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
239000001267 polyvinylpyrrolidone Substances 0.000 description 3
229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
229920001592 potato starch Polymers 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000003813 safflower oil Substances 0.000 description 3
235000005713 safflower oil Nutrition 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
229910052710 silicon Inorganic materials 0.000 description 3
239000010703 silicon Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
150000008163 sugars Chemical class 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
230000001988 toxicity Effects 0.000 description 3
231100000419 toxicity Toxicity 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
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230000000144 pharmacologic effect Effects 0.000 description 1
239000008196 pharmacological composition Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920001522 polyglycol ester Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010483 polyoxyethylene sorbitan monopalmitate Nutrition 0.000 description 1
239000000249 polyoxyethylene sorbitan monopalmitate Substances 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229950008882 polysorbate Drugs 0.000 description 1
229940068968 polysorbate 80 Drugs 0.000 description 1
235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
229920000523 polyvinylpolypyrrolidone Polymers 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
230000002633 protecting effect Effects 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
239000012744 reinforcing agent Substances 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
125000006413 ring segment Chemical group 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
150000004671 saturated fatty acids Chemical class 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000010686 shark liver oil Substances 0.000 description 1
229940069764 shark liver oil Drugs 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
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
BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
229940082004 sodium laurate Drugs 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000011343 solid material 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
229940035044 sorbitan monolaurate Drugs 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
239000012177 spermaceti Substances 0.000 description 1
229940084106 spermaceti Drugs 0.000 description 1
229940032094 squalane Drugs 0.000 description 1
229940038774 squalene oil Drugs 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229940012831 stearyl alcohol Drugs 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
150000003505 terpenes Chemical class 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
150000003538 tetroses Chemical class 0.000 description 1
238000011287 therapeutic dose Methods 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
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 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
230000000699 topical effect Effects 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
125000004665 trialkylsilyl group Chemical group 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
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
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000001993 wax Substances 0.000 description 1
235000019386 wax ester Nutrition 0.000 description 1
239000000080 wetting agent Substances 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)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Dispersion Chemistry (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Oncology (AREA)
Engineering & Computer Science (AREA)
Mechanical Engineering (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)

SK1369-2001A 2000-02-02 2001-02-02 Taxány substituované v polohe C10 esterovou skupinou SK13692001A3 (sk)

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
SK13692001A3 true SK13692001A3 (sk)	2002-07-02

Family

ID=22657972

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1369-2001A SK13692001A3 (sk)	2000-02-02	2001-02-02	Taxány substituované v polohe C10 esterovou skupinou

Country Status (25)

Country	Link
EP (1)	EP1165553B1 (he)
JP (1)	JP2003522172A (he)
CN (1)	CN1380882A (he)
AT (1)	ATE432928T1 (he)
AU (1)	AU782150B2 (he)
BG (1)	BG64889B1 (he)
BR (1)	BR0104354A (he)
CA (1)	CA2368274C (he)
CZ (1)	CZ20013430A3 (he)
DE (1)	DE60138853D1 (he)
GE (1)	GEP20043323B (he)
HU (1)	HUP0600302A2 (he)
IL (1)	IL145638A (he)
MX (1)	MXPA01009905A (he)
NO (1)	NO327910B1 (he)
NZ (1)	NZ514382A (he)
PL (1)	PL202957B1 (he)
RO (1)	RO121270B1 (he)
RU (1)	RU2262506C2 (he)
SK (1)	SK13692001A3 (he)
TR (1)	TR200102858T1 (he)
TW (1)	TWI299732B (he)
UA (1)	UA75039C2 (he)
WO (1)	WO2001057032A1 (he)
ZA (1)	ZA200108055B (he)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
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
EP2276755A4 (en) *	2008-03-31	2011-05-04	Univ Florida State Res Found	C (10) -ETHYESTER- AND C (10) -CYCLOPROPYLESTER-SUBSTITUTED TAXANES

Family Cites Families (13)

* Cited by examiner, † Cited by third party
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
JPH08508469A (ja) *	1993-03-22	1996-09-10	フロリダ・ステート・ユニバーシティー	アルコキシ、アルケンオキシまたはアリールオキシ置換側鎖を有するタキサンおよびそれを含有する薬剤組成物
ATE209489T1 (de) *	1993-03-22	2001-12-15	Univ Florida State	Taxane mit pyridyl-substituierter seitenkette
AU686148B2 (en) *	1993-03-22	1998-02-05	Florida State University	Taxanes having an amino substituted side-chain
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
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
US5795909A (en) *	1996-05-22	1998-08-18	Neuromedica, Inc.	DHA-pharmaceutical agent conjugates of taxanes
ATE196844T1 (de) *	1996-05-22	2000-10-15	Protarga Inc	Zusammensetzungen die konjugate von cis- docosahexaenoic-säure und taxotere enthalten
US6268381B1 (en) *	1997-12-19	2001-07-31	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 AU AU34809/01A patent/AU782150B2/en not_active Ceased
- 2001-02-02 HU HU0600302A patent/HUP0600302A2/hu unknown
- 2001-02-02 RU RU2001129501/04A patent/RU2262506C2/ru active
- 2001-02-02 WO PCT/US2001/003623 patent/WO2001057032A1/en active Application Filing
- 2001-02-02 UA UA2001106733A patent/UA75039C2/uk unknown
- 2001-02-02 PL PL351380A patent/PL202957B1/pl not_active IP Right Cessation
- 2001-02-02 IL IL145638A patent/IL145638A/he not_active IP Right Cessation
- 2001-02-02 JP JP2001557864A patent/JP2003522172A/ja active Pending
- 2001-02-02 NZ NZ514382A patent/NZ514382A/en unknown
- 2001-02-02 CA CA002368274A patent/CA2368274C/en not_active Expired - Fee Related
- 2001-02-02 GE GE4523A patent/GEP20043323B/en unknown
- 2001-02-02 EP EP01906971A patent/EP1165553B1/en not_active Expired - Lifetime
- 2001-02-02 TR TR2001/02858T patent/TR200102858T1/xx unknown
- 2001-02-02 MX MXPA01009905A patent/MXPA01009905A/es active IP Right Grant
- 2001-02-02 RO ROA200101083A patent/RO121270B1/ro unknown
- 2001-02-02 DE DE60138853T patent/DE60138853D1/de not_active Expired - Lifetime
- 2001-02-02 CN CN01800568A patent/CN1380882A/zh active Pending
- 2001-02-02 AT AT01906971T patent/ATE432928T1/de not_active IP Right Cessation
- 2001-02-02 BR BR0104354-4A patent/BR0104354A/pt not_active IP Right Cessation
- 2001-02-02 SK SK1369-2001A patent/SK13692001A3/sk unknown
- 2001-02-02 CZ CZ20013430A patent/CZ20013430A3/cs 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 BG BG105965A patent/BG64889B1/bg unknown
- 2001-10-01 ZA ZA200108055A patent/ZA200108055B/en unknown

Also Published As

Publication number	Publication date
AU782150B2 (en)	2005-07-07
DE60138853D1 (de)	2009-07-16
PL202957B1 (pl)	2009-08-31
BG105965A (en)	2002-07-31
AU3480901A (en)	2001-08-14
PL351380A1 (en)	2003-04-07
CN1380882A (zh)	2002-11-20
GEP20043323B (en)	2004-02-10
MXPA01009905A (es)	2003-08-20
NZ514382A (en)	2004-05-28
BG64889B1 (bg)	2006-08-31
CA2368274A1 (en)	2001-08-09
TWI299732B (en)	2008-08-11
CZ20013430A3 (cs)	2002-04-17
NO20014754L (no)	2001-11-29
NO327910B1 (no)	2009-10-19
EP1165553A1 (en)	2002-01-02
CA2368274C (en)	2009-10-13
IL145638A0 (en)	2002-06-30
RU2262506C2 (ru)	2005-10-20
WO2001057032A1 (en)	2001-08-09
NO20014754D0 (no)	2001-10-01
JP2003522172A (ja)	2003-07-22
BR0104354A (pt)	2002-01-02
RO121270B1 (ro)	2007-02-28
UA75039C2 (en)	2006-03-15
ATE432928T1 (de)	2009-06-15
ZA200108055B (en)	2003-12-01
TR200102858T1 (tr)	2002-12-23
EP1165553B1 (en)	2009-06-03
IL145638A (he)	2011-05-31
HUP0600302A2 (en)	2006-07-28

Publication	Publication Date	Title
RU2265017C2 (ru)	2005-11-27	С7 сложноэфирзамещенные таксаны в качестве противоопухолевых средств
US20070249707A1 (en)	2007-10-25	Taxanes having c7 hydroxy and c10 heterosubstituted acetate substituents
US7256213B2 (en)	2007-08-14	Taxanes having a C10 carbonate substituent
US6673833B2 (en)	2004-01-06	C7 heterosubstituted acetate taxanes
US7226944B2 (en)	2007-06-05	Taxanes having a C7 carbonate substituent
US6649632B2 (en)	2003-11-18	C10 ester substituted taxanes
SK13692001A3 (sk)	2002-07-02	Taxány substituované v polohe C10 esterovou skupinou
US6750245B2 (en)	2004-06-15	C7 carbamate substituted taxanes

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Date	Code	Title	Description
2010-02-08	FB9A	Suspension of patent application procedure