ES2295937T3 - Analogos de 9,10-alfa,alfa-oh-taxano y procedimientos para su produccion. - Google Patents
Analogos de 9,10-alfa,alfa-oh-taxano y procedimientos para su produccion. Download PDFInfo
- Publication number
- ES2295937T3 ES2295937T3 ES04789167T ES04789167T ES2295937T3 ES 2295937 T3 ES2295937 T3 ES 2295937T3 ES 04789167 T ES04789167 T ES 04789167T ES 04789167 T ES04789167 T ES 04789167T ES 2295937 T3 ES2295937 T3 ES 2295937T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- reaction
- baselineskip
- mmol
- group
- 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.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title abstract description 41
- 238000004519 manufacturing process Methods 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 93
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 21
- 201000011510 cancer Diseases 0.000 claims abstract description 19
- 238000011282 treatment Methods 0.000 claims abstract description 12
- 239000003814 drug Substances 0.000 claims description 9
- 229940079593 drug Drugs 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 4
- 208000016691 refractory malignant neoplasm Diseases 0.000 claims 1
- 229940123237 Taxane Drugs 0.000 abstract description 58
- 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 abstract description 55
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 20
- 125000000217 alkyl group Chemical group 0.000 abstract description 17
- 125000003118 aryl group Chemical group 0.000 abstract description 15
- 239000007858 starting material Substances 0.000 abstract description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 4
- 230000008569 process Effects 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 140
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 93
- 239000000243 solution Substances 0.000 description 92
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 44
- 239000007787 solid Substances 0.000 description 40
- 239000000047 product Substances 0.000 description 37
- 238000010586 diagram Methods 0.000 description 36
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 34
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 32
- 229930012538 Paclitaxel Natural products 0.000 description 29
- 229960001592 paclitaxel Drugs 0.000 description 29
- 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 29
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 238000004128 high performance liquid chromatography Methods 0.000 description 23
- 239000012267 brine Substances 0.000 description 22
- 235000019439 ethyl acetate Nutrition 0.000 description 22
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 22
- 229940011051 isopropyl acetate Drugs 0.000 description 22
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 22
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 22
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 16
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 16
- 238000005406 washing Methods 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
- 229910052938 sodium sulfate Inorganic materials 0.000 description 15
- 235000011152 sodium sulphate Nutrition 0.000 description 15
- -1 COOH carboxylic acid Chemical class 0.000 description 14
- 239000005457 ice water Substances 0.000 description 14
- 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 13
- 239000002253 acid Substances 0.000 description 13
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 11
- 238000005917 acylation reaction Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 10
- 150000001241 acetals Chemical class 0.000 description 10
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
- 230000010933 acylation Effects 0.000 description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
- 238000010511 deprotection reaction Methods 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- TYLVGQKNNUHXIP-MHHARFCSSA-N 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)C=4C=CC=CC=4)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 TYLVGQKNNUHXIP-MHHARFCSSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 238000007792 addition Methods 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 230000001012 protector Effects 0.000 description 6
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 101100189356 Mus musculus Papolb gene Proteins 0.000 description 5
- 239000007832 Na2SO4 Substances 0.000 description 5
- 235000019270 ammonium chloride Nutrition 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 238000007865 diluting Methods 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 5
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- 230000002441 reversible effect Effects 0.000 description 4
- FDTAUJJRHBRHIJ-FDJAAIFISA-N tpi-287 Chemical compound O([C@@H]1[C@]2(O)C[C@@H](C(=C([C@H](OC(C)=O)[C@@H]3OC(O[C@H]4C[C@H]5OC[C@]5([C@@H]1[C@]34C)OC(C)=O)C=C)C2(C)C)C)OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)CC(C)C)C(=O)C1=CC=CC=C1 FDTAUJJRHBRHIJ-FDJAAIFISA-N 0.000 description 4
- NNHYAHOTXLASEA-UHFFFAOYSA-N 1-(dimethoxymethyl)-4-methoxybenzene Chemical compound COC(OC)C1=CC=C(OC)C=C1 NNHYAHOTXLASEA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006359 acetalization reaction Methods 0.000 description 3
- 239000002246 antineoplastic agent Substances 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 230000008034 disappearance Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- 230000017095 negative regulation of cell growth Effects 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000009834 vaporization Methods 0.000 description 3
- 230000008016 vaporization Effects 0.000 description 3
- KIELDCCFMKNOOM-AWZPIEEASA-N 2'-o-(tert-butyldimethylsilyl)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(C21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 KIELDCCFMKNOOM-AWZPIEEASA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- OBWGMYALGNDUNM-UHFFFAOYSA-N 3,3-dimethoxyprop-1-ene Chemical compound COC(OC)C=C OBWGMYALGNDUNM-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 239000012223 aqueous fraction Substances 0.000 description 2
- 238000010936 aqueous wash Methods 0.000 description 2
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 229960003668 docetaxel Drugs 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000006698 hydrazinolysis reaction Methods 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- CPZBTYRIGVOOMI-UHFFFAOYSA-N methylsulfanyl(methylsulfanylmethoxy)methane Chemical compound CSCOCSC CPZBTYRIGVOOMI-UHFFFAOYSA-N 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical group CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 description 1
- FNQOMITVJQBKPZ-UHFFFAOYSA-N CC[S](F)(F)(F)CC Chemical compound CC[S](F)(F)(F)CC FNQOMITVJQBKPZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000012448 Lithium borohydride Substances 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000719 anti-leukaemic effect Effects 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- JWMLCCRPDOIBAV-UHFFFAOYSA-N chloro(methylsulfanyl)methane Chemical compound CSCCl JWMLCCRPDOIBAV-UHFFFAOYSA-N 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000011549 crystallization solution Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 230000003013 cytotoxicity Effects 0.000 description 1
- 231100000135 cytotoxicity Toxicity 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 1
- CETVQRFGPOGIQJ-UHFFFAOYSA-N lithium;hexane Chemical compound [Li+].CCCCC[CH2-] CETVQRFGPOGIQJ-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002633 protecting effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000011894 semi-preparative HPLC Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000008259 solid foam Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
- 125000005607 tigloyl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
Classifications
-
- 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
- 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
- A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
-
- 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
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50668003P | 2003-09-25 | 2003-09-25 | |
| US506680P | 2003-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2295937T3 true ES2295937T3 (es) | 2008-04-16 |
Family
ID=34393186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES04789167T Expired - Lifetime ES2295937T3 (es) | 2003-09-25 | 2004-09-27 | Analogos de 9,10-alfa,alfa-oh-taxano y procedimientos para su produccion. |
Country Status (14)
| Country | Link |
|---|---|
| US (8) | US7745650B2 (enExample) |
| EP (2) | EP1785416A3 (enExample) |
| JP (5) | JP4874102B2 (enExample) |
| CN (1) | CN1886400A (enExample) |
| AT (1) | ATE377593T1 (enExample) |
| AU (1) | AU2004275881A1 (enExample) |
| CA (1) | CA2539975C (enExample) |
| DE (1) | DE602004009943T2 (enExample) |
| DK (1) | DK1664033T3 (enExample) |
| ES (1) | ES2295937T3 (enExample) |
| HR (1) | HRP20080057T3 (enExample) |
| PL (1) | PL1664033T3 (enExample) |
| PT (1) | PT1664033E (enExample) |
| WO (1) | WO2005030150A2 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1785416A3 (en) | 2003-09-25 | 2007-05-30 | Tapestry Pharmaceuticals, Inc. | 9, 10-alpha, alpha-OH-Taxane Analogs and methods for production thereof |
| JP2008536479A (ja) | 2005-02-11 | 2008-09-11 | ユニバーシティ オブ サザン カリフォルニア | ジスルフィド架橋を有するタンパク質の発現法 |
| CA2634453A1 (en) * | 2005-12-21 | 2007-06-28 | Tapestry Pharmaceuticals, Inc. | Novel compounds and methods for forming taxanes and using the same |
| MX2008008119A (es) * | 2005-12-21 | 2008-09-24 | Tapestry Pharmaceuticals Inc | Procesos para derivados de taxano y compuestos intermedios utiles en los mismos. |
| WO2007126893A2 (en) * | 2006-03-27 | 2007-11-08 | Tapestry Pharmaceuticals, Inc. | A convergent process for the synthesis of taxane derivatives |
| US8008256B2 (en) * | 2006-05-01 | 2011-08-30 | University Of Southern California | Combination therapy for treatment of cancer |
| US7847111B2 (en) | 2006-06-19 | 2010-12-07 | Canada Inc. | Semi-synthetic route for the preparation of paclitaxel, docetaxel, and 10-deacetylbaccatin III from 9-dihydro-13-acetylbaccatin III |
| WO2007143839A1 (en) * | 2006-06-12 | 2007-12-21 | 6570763 Canada Inc. | Semi-synthetic route for the preparation of paclitaxel, docetaxel and 10-deacetylbaccatin iii from 9-dihydro-13-acetylbaccatin iii |
| US11786504B2 (en) | 2006-09-28 | 2023-10-17 | Tapestry Pharmaceuticals, Inc. | Taxane analogs for the treatment of brain cancer |
| US11873308B2 (en) | 2006-11-06 | 2024-01-16 | Tapestry Pharmaceuticals, Inc. | Biologically active taxane analogs and methods of treatment by oral administration |
| WO2008121476A1 (en) | 2007-03-28 | 2008-10-09 | Tapestry Pharmaceuticals, Inc. | Biologically active taxane analogs and methods of treatment by oral administration |
| US20080207743A1 (en) * | 2007-02-28 | 2008-08-28 | Rodger Lamb | Biologically Active Taxane Analogs and Methods of Treatment |
| WO2008109360A1 (en) * | 2007-02-28 | 2008-09-12 | Tapestry Pharmaceuticals, Inc | Taxane analogs for the treatment of brain cancer |
| US8802394B2 (en) | 2008-11-13 | 2014-08-12 | Radu O. Minea | Method of expressing proteins with disulfide bridges with enhanced yields and activity |
| EP2694055A4 (en) * | 2011-04-07 | 2014-09-10 | Arbor Therapeutics Llc | ANALOGUES OF TAXANE AND ABÉO-TAXANE |
| US9227983B2 (en) | 2011-04-07 | 2016-01-05 | Arbor Therapeutics, LLC | Taxane and abeo-taxane analogs |
| MX337464B (es) * | 2011-06-06 | 2016-03-07 | Arbor Therapeutics Llc | Profarmacos lipofilicos labiles al acido de los agentes quimioterapeuticos contra el cancer. |
| AU2021231831A1 (en) | 2020-03-04 | 2022-09-08 | Aquedeon Medical, Inc. | Vascular and aortic grafts with telescoping sheath and deployment methods thereof |
| US12622797B2 (en) | 2021-03-04 | 2026-05-12 | Aquedeon Medical, Inc. | Vascular and aortic connectors with robotic delivery and deployment methods thereof |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX9102128A (es) * | 1990-11-23 | 1992-07-08 | Rhone Poulenc Rorer Sa | Derivados de taxano,procedimiento para su preparacion y composicion farmaceutica que los contiene |
| US6794523B2 (en) * | 1991-09-23 | 2004-09-21 | Florida State University | Taxanes having t-butoxycarbonyl substituted side-chains and pharmaceutical compositions containing them |
| DE69325454T2 (de) * | 1992-04-17 | 2000-01-20 | Abbott Laboratories, Abbott Park | Taxol-derivate |
| FR2697019B1 (fr) * | 1992-10-15 | 1994-11-25 | Rhone Poulenc Rorer Sa | Nouveaux dérivés du taxane, leur préparation et les compositions pharmaceutiques qui les contiennent. |
| EP0668762B1 (en) * | 1992-11-13 | 2003-09-17 | Florida State University | Isobutenyl-substituted taxanes and their pharmaceutical compositions |
| US6710191B2 (en) * | 1993-03-05 | 2004-03-23 | Florida State University | 9β-hydroxytetracyclic taxanes |
| EP0687260B1 (en) * | 1993-03-05 | 2003-02-19 | Florida State University | Process for the preparation of 9-desoxotaxanes |
| EP1148055A1 (en) * | 1993-03-05 | 2001-10-24 | Florida State University | C9 taxane derivatives and pharmaceutical compositions containing them |
| DK0690867T3 (da) | 1993-03-22 | 2003-06-10 | Univ Florida State | Taxaner med furyl- eller thienylsubstitueret sidekæde |
| FR2707293A1 (fr) * | 1993-07-08 | 1995-01-13 | Rhone Poulenc Rorer Sa | Nouveaux taxoides, leur préparation et les compositions pharmaceutiques qui les contiennent. |
| FR2715846A1 (fr) * | 1994-02-07 | 1995-08-11 | Rhone Poulenc Rorer Sa | Nouvelle composition pharmceutique à base de taxoïdes. |
| IT1275936B1 (it) | 1995-03-17 | 1997-10-24 | Indena Spa | Derivati della 10-deacetilbaccatina iii e della 10-deacetil-14b- idrossibaccatina iii loro metodo di preparazione e formulazioni |
| US5635531A (en) * | 1996-07-08 | 1997-06-03 | Bristol-Myers Squibb Company | 3'-aminocarbonyloxy paclitaxels |
| US5739359A (en) * | 1997-01-24 | 1998-04-14 | Virginia Tech Intellectual Properties, Inc. | Methods for preparing 1-deoxy paclitaxels |
| US6048990A (en) * | 1998-05-01 | 2000-04-11 | Napro Biotherapeutics, Inc. | Method for selective acylation of C-2'-O-protected-10-hydroxy-taxol at the C-10 position |
| CO5280224A1 (es) | 2000-02-02 | 2003-05-30 | Univ Florida State Res Found | Taxanos sustituidos con ester en c7, utiles como agentes antitumorales y composiciones farmaceuticas que los contienen |
| HUP0200750A3 (en) * | 2000-02-02 | 2005-02-28 | Univ Florida State Res Found | C10 heterosubstituted acetate taxanes as antitumor agents and pharmaceutical compositions containing them and their use |
| EP1383492A4 (en) | 2001-03-23 | 2008-12-24 | Napro Biotherapeutics Inc | MOLECULAR CONJUGATES FOR USE IN CANCER THERAPY |
| CA2354471A1 (en) | 2001-07-31 | 2003-01-31 | Florida State University Research Foundation, Inc. | C10 ester substituted taxanes |
| EP1465618A2 (en) | 2001-12-20 | 2004-10-13 | Bristol-Myers Squibb Company | Pharmaceutical compositions of orally active taxane derivatives having enhanced bioavailability |
| US6898834B1 (en) * | 2003-03-03 | 2005-05-31 | Westbridge Pty Ltd | Barrel stave reclaim |
| EP1894921A3 (en) | 2003-09-25 | 2008-03-12 | Tapestry Pharmaceuticals, Inc. | 9, 10-Alpha, Alpha-Oh-Taxane analogs and methods for production thereof |
| EP1785416A3 (en) * | 2003-09-25 | 2007-05-30 | Tapestry Pharmaceuticals, Inc. | 9, 10-alpha, alpha-OH-Taxane Analogs and methods for production thereof |
| AU2006247471A1 (en) | 2005-05-12 | 2006-11-23 | Tapestry Pharmaceuticals, Inc. | Molecular constructs suitable for targeted conjugates |
| MX2008008119A (es) | 2005-12-21 | 2008-09-24 | Tapestry Pharmaceuticals Inc | Procesos para derivados de taxano y compuestos intermedios utiles en los mismos. |
| CA2634453A1 (en) | 2005-12-21 | 2007-06-28 | Tapestry Pharmaceuticals, Inc. | Novel compounds and methods for forming taxanes and using the same |
| WO2007126893A2 (en) | 2006-03-27 | 2007-11-08 | Tapestry Pharmaceuticals, Inc. | A convergent process for the synthesis of taxane derivatives |
| WO2008121476A1 (en) | 2007-03-28 | 2008-10-09 | Tapestry Pharmaceuticals, Inc. | Biologically active taxane analogs and methods of treatment by oral administration |
| WO2008109360A1 (en) | 2007-02-28 | 2008-09-12 | Tapestry Pharmaceuticals, Inc | Taxane analogs for the treatment of brain cancer |
| US20080207743A1 (en) | 2007-02-28 | 2008-08-28 | Rodger Lamb | Biologically Active Taxane Analogs and Methods of Treatment |
-
2004
- 2004-09-27 EP EP06026009A patent/EP1785416A3/en not_active Withdrawn
- 2004-09-27 CA CA2539975A patent/CA2539975C/en not_active Expired - Lifetime
- 2004-09-27 PL PL04789167T patent/PL1664033T3/pl unknown
- 2004-09-27 ES ES04789167T patent/ES2295937T3/es not_active Expired - Lifetime
- 2004-09-27 EP EP04789167A patent/EP1664033B1/en not_active Expired - Lifetime
- 2004-09-27 HR HR20080057T patent/HRP20080057T3/xx unknown
- 2004-09-27 AT AT04789167T patent/ATE377593T1/de not_active IP Right Cessation
- 2004-09-27 WO PCT/US2004/031816 patent/WO2005030150A2/en not_active Ceased
- 2004-09-27 PT PT04789167T patent/PT1664033E/pt unknown
- 2004-09-27 JP JP2006528316A patent/JP4874102B2/ja not_active Expired - Lifetime
- 2004-09-27 AU AU2004275881A patent/AU2004275881A1/en not_active Abandoned
- 2004-09-27 CN CNA2004800346381A patent/CN1886400A/zh active Pending
- 2004-09-27 DE DE602004009943T patent/DE602004009943T2/de not_active Expired - Fee Related
- 2004-09-27 US US10/951,555 patent/US7745650B2/en not_active Expired - Lifetime
- 2004-09-27 DK DK04789167T patent/DK1664033T3/da active
-
2010
- 2010-06-02 US US12/792,427 patent/US7879904B2/en not_active Expired - Lifetime
- 2010-09-07 JP JP2010200399A patent/JP5525394B2/ja not_active Expired - Lifetime
- 2010-11-24 US US12/954,253 patent/US8962870B2/en active Active
-
2011
- 2011-04-08 JP JP2011086840A patent/JP5629632B2/ja not_active Expired - Lifetime
-
2014
- 2014-07-10 JP JP2014141964A patent/JP6106634B2/ja not_active Expired - Lifetime
-
2015
- 2015-01-23 US US14/604,147 patent/US9402824B2/en not_active Expired - Lifetime
-
2016
- 2016-07-12 JP JP2016137271A patent/JP6216417B2/ja not_active Expired - Lifetime
- 2016-07-27 US US15/220,975 patent/US9820962B2/en not_active Expired - Fee Related
-
2017
- 2017-10-09 US US15/728,049 patent/US10238621B2/en not_active Expired - Lifetime
-
2019
- 2019-01-14 US US16/247,425 patent/US10639293B2/en not_active Expired - Lifetime
-
2020
- 2020-04-15 US US16/849,879 patent/US20200237708A1/en not_active Abandoned
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP6216417B2 (ja) | ９，１０−α，α−ＯＨ−タキサンアナログおよびその生成のための方法 | |
| FI115056B (fi) | Uusia välituotteena käytettäviä oksatsoliinisivuketjullisia taksaaneja ja menetelmä niiden valmistamiseksi | |
| CA2179176A1 (en) | .delta.12,13-iso-taxol analogs, antineoplastic use and pharmaceutical compositions containing them | |
| SK13712001A3 (sk) | C7 esterom substituované taxány ako protinádorové látky | |
| JPH08225558A (ja) | パクリタクセルのアミノ酸誘導体 | |
| JP2026510566A (ja) | カンプトテシン誘導体及びその複合体、並びにその調製方法および医療用途 | |
| US20250340532A1 (en) | Heterocyclic compound ccr4 inhibitor and user thereof | |
| AU758418B2 (en) | Taxane derivatives | |
| JP4823456B2 (ja) | タクサン誘導体及びその製造方法 | |
| KR19980702749A (ko) | 10-데아세틸-14베타-하이드록시바카틴iii 유도체, 그의 제조방법 및 그를 함유한 제제. | |
| EP2233467B1 (en) | Alpha-amino-n-substituted amides, pharmaceutical composition containing them and uses thereof | |
| ES2223778T3 (es) | Taxanos semisinteticos con actividad antitumoral y antiangiogenica. | |
| EP1894921A2 (en) | 9, 10-Alpha, Alpha-Oh-Taxane analogs and methods for production thereof | |
| ES2287310T3 (es) | Derivados de c-2' metilados de paclitaxel para usar como agentes antitumorales. |