CA2558908C - Derives de 10-desacetylbaccatine iii et de 10-desacetyl-14.beta.-hydroxybaccatine iii et composes intermediaires pouvant servir a la synthese desdits derives - Google Patents

Derives de 10-desacetylbaccatine iii et de 10-desacetyl-14.beta.-hydroxybaccatine iii et composes intermediaires pouvant servir a la synthese desdits derives Download PDF

Info

Publication number: CA2558908C
Authority: CA; Canada
Prior art keywords: iii; deacetyl; preparation; hydroxybaccatine; compound
Prior art date: 1995-03-17
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

Application number

CA002558908A

Other languages

English (en)

Other versions

CA2558908A1 (fr

Inventor

Ezio Bombardelli

Paolo De Bellis

Bruno Gabetta

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Indena SpA

Original Assignee

Indena SpA

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.)

1995-03-17

Filing date

1996-03-04

Publication date

2009-12-22

1995-03-17 Priority claimed from IT95MI000533A external-priority patent/IT1275936B1/it

1996-03-04 Application filed by Indena SpA filed Critical Indena SpA

1996-09-26 Publication of CA2558908A1 publication Critical patent/CA2558908A1/fr

2009-12-22 Application granted granted Critical

2009-12-22 Publication of CA2558908C publication Critical patent/CA2558908C/fr

2016-03-04 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000000543 intermediate Substances 0.000 title claims abstract description 4
238000002360 preparation method Methods 0.000 title abstract description 13
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 title abstract description 8
YWLXLRUDGLRYDR-LUPIKGFISA-N 7-epi-10-deacetylbaccatin iii Chemical group 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-LUPIKGFISA-N 0.000 title description 3
125000000217 alkyl group Chemical group 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims 1
229940123237 Taxane Drugs 0.000 abstract description 10
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical group NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 7
230000003647 oxidation Effects 0.000 abstract description 6
238000007254 oxidation reaction Methods 0.000 abstract description 6
230000000259 anti-tumor effect Effects 0.000 abstract description 3
231100000433 cytotoxic Toxicity 0.000 abstract 1
230000001472 cytotoxic effect Effects 0.000 abstract 1
238000002347 injection Methods 0.000 abstract 1
239000007924 injection Substances 0.000 abstract 1
125000000468 ketone group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
150000001875 compounds Chemical class 0.000 description 26
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
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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
229930012538 Paclitaxel Natural products 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
229960001592 paclitaxel Drugs 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 5
238000000034 method Methods 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
-1 triethylsilyl Chemical group 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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 4
229940075614 colloidal silicon dioxide Drugs 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
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235000019359 magnesium stearate Nutrition 0.000 description 4
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QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
229920000168 Microcrystalline cellulose Polymers 0.000 description 3
206010028980 Neoplasm Diseases 0.000 description 3
229940125773 compound 10 Drugs 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
230000000694 effects Effects 0.000 description 3
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 3
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 3
229940016286 microcrystalline cellulose Drugs 0.000 description 3
235000019813 microcrystalline cellulose Nutrition 0.000 description 3
239000008108 microcrystalline cellulose Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000006884 silylation reaction Methods 0.000 description 3
DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical group 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 description 3
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
241000518994 Conta Species 0.000 description 2
229920002785 Croscarmellose sodium Polymers 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
229920000881 Modified starch Polymers 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000003158 alcohol group Chemical group 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000002775 capsule Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](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 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 description 2
235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 2
150000005676 cyclic carbonates Chemical group 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
239000012071 phase Substances 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
239000003826 tablet Substances 0.000 description 2
XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
HEVMDQBCAHEHDY-UHFFFAOYSA-N (Dimethoxymethyl)benzene Chemical compound COC(OC)C1=CC=CC=C1 HEVMDQBCAHEHDY-UHFFFAOYSA-N 0.000 description 1
KNWCDYSKJSREAQ-UHFFFAOYSA-N 1,3-oxazolidine-2-carboxylic acid Chemical class OC(=O)C1NCCO1 KNWCDYSKJSREAQ-UHFFFAOYSA-N 0.000 description 1
ADDGUHVEJPNWQZ-FIKJQGJASA-N 10-Deacetylcephalomannine Natural products O=C(O[C@@H]1C(C)=C2[C@@H](O)C(=O)[C@]3(C)[C@@H](O)C[C@@H]4[C@](OC(=O)C)([C@H]3[C@H](OC(=O)c3ccccc3)[C@@](O)(C2(C)C)C1)CO4)[C@H](O)[C@@H](NC(=O)/C(=C\C)/C)c1ccccc1 ADDGUHVEJPNWQZ-FIKJQGJASA-N 0.000 description 1
ADDGUHVEJPNWQZ-GJKIWTKTSA-N 10-deacetyltaxol b Chemical compound O([C@@H]1[C@]2(O)C[C@@H](C(=C([C@@H](O)C(=O)[C@]3(C)[C@@H](O)C[C@H]4OC[C@]4([C@H]31)OC(C)=O)C2(C)C)C)OC(=O)[C@H](O)[C@@H](NC(=O)C(/C)=C/C)C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 ADDGUHVEJPNWQZ-GJKIWTKTSA-N 0.000 description 1
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical class [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
229920002685 Polyoxyl 35CastorOil Polymers 0.000 description 1
241001116500 Taxus Species 0.000 description 1
241001330459 Taxus wallichiana var. wallichiana Species 0.000 description 1
JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229940009456 adriamycin Drugs 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000005103 alkyl silyl group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
230000003217 anti-cancerogenic effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
238000011717 athymic nude mouse Methods 0.000 description 1
230000003130 cardiopathic effect Effects 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000010949 copper Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
230000003013 cytotoxicity Effects 0.000 description 1
231100000135 cytotoxicity Toxicity 0.000 description 1
238000001212 derivatisation Methods 0.000 description 1
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
229930004069 diterpene Natural products 0.000 description 1
150000004141 diterpene derivatives Chemical class 0.000 description 1
125000000567 diterpene group Chemical group 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
239000007943 implant Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
QUANRIQJNFHVEU-UHFFFAOYSA-N oxirane;propane-1,2,3-triol Chemical compound C1CO1.OCC(O)CO QUANRIQJNFHVEU-UHFFFAOYSA-N 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
239000008389 polyethoxylated castor oil Substances 0.000 description 1
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
238000011160 research Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
239000005418 vegetable material Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

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Epoxy Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA002558908A 1995-03-17 1996-03-04 Derives de 10-desacetylbaccatine iii et de 10-desacetyl-14.beta.-hydroxybaccatine iii et composes intermediaires pouvant servir a la synthese desdits derives Expired - Lifetime CA2558908C (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
IT95MI000533A IT1275936B1 (it)	1995-03-17	1995-03-17	Derivati della 10-deacetilbaccatina iii e della 10-deacetil-14b- idrossibaccatina iii loro metodo di preparazione e formulazioni
ITMI95A000533		1995-03-17
CA002215682A CA2215682C (fr)	1995-03-17	1996-03-04	Derives de 10-deacetylbaccatine iii et de 10-deacetyl-14.beta.-hydroxybaccatine iii, leur procede de preparation et compositions pharmaceutiques les contenant

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002215682A Division CA2215682C (fr)	1995-03-17	1996-03-04	Derives de 10-deacetylbaccatine iii et de 10-deacetyl-14.beta.-hydroxybaccatine iii, leur procede de preparation et compositions pharmaceutiques les contenant

Publications (2)

Publication Number	Publication Date
CA2558908A1 CA2558908A1 (fr)	1996-09-26
CA2558908C true CA2558908C (fr)	2009-12-22

Family

ID=37441499

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002558908A Expired - Lifetime CA2558908C (fr)	1995-03-17	1996-03-04	Derives de 10-desacetylbaccatine iii et de 10-desacetyl-14.beta.-hydroxybaccatine iii et composes intermediaires pouvant servir a la synthese desdits derives

Country Status (1)

Country	Link
CA (1)	CA2558908C (fr)

1996
- 1996-03-04 CA CA002558908A patent/CA2558908C/fr not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CA2558908A1 (fr)	1996-09-26

Legal Events

Date	Code	Title	Description
2006-06-26	EEER	Examination request
2016-05-08	MKEX	Expiry	Effective date: 20160304

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JP2986550B2 (ja)	1999-12-06	抗腫瘍活性を有する半合成タキサン
JPH0641010A (ja)	1994-02-15	タキサン誘導体、その製造方法及びそれを含有する抗腫瘍剤
RU2233276C2 (ru)	2004-07-27	Способ получения таксанов и промежуточное соединение для их получения
AU759988B2 (en)	2003-05-01	Synthesis of paclitaxel baccatin III by protecting the 7-hydroxyl using a strong base and an electrophile
KR100399330B1 (ko)	2003-12-31	10-데아세틸-14베타-하이드록시바카틴iii유도체,그의제조방법및그를함유한제제
CA2558908C (fr)	2009-12-22	Derives de 10-desacetylbaccatine iii et de 10-desacetyl-14.beta.-hydroxybaccatine iii et composes intermediaires pouvant servir a la synthese desdits derives
WO2006102758A1 (fr)	2006-10-05	Preparation de taxanes a partir de la 9-dihydro-13-acetylbaccatine iii
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