FI120398B - Puolisynteettiset taksaanit, joilla on kasvaimia torjuvaa vaikutusta, sekä niiden valmistusmenetelmät, välituotteet ja farmaseuttiset koostumukset - Google Patents
Puolisynteettiset taksaanit, joilla on kasvaimia torjuvaa vaikutusta, sekä niiden valmistusmenetelmät, välituotteet ja farmaseuttiset koostumukset Download PDFInfo
- Publication number
- FI120398B FI120398B FI970271A FI970271A FI120398B FI 120398 B FI120398 B FI 120398B FI 970271 A FI970271 A FI 970271A FI 970271 A FI970271 A FI 970271A FI 120398 B FI120398 B FI 120398B
- Authority
- FI
- Finland
- Prior art keywords
- formula
- hydroxy
- tert
- phenyl
- compound
- Prior art date
Links
- 230000000259 anti-tumor effect Effects 0.000 title claims abstract description 8
- 229940123237 Taxane Drugs 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 239000000543 intermediate Substances 0.000 title description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical group NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 29
- 238000002360 preparation method Methods 0.000 claims description 16
- -1 2,2,2-trichloroethoxycarbonyloxy Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000004423 acyloxy group Chemical group 0.000 claims description 10
- 238000003786 synthesis reaction Methods 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 238000007796 conventional method Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 208000019622 heart disease Diseases 0.000 claims 1
- 125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 claims 1
- 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 abstract description 11
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical class 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 abstract description 11
- 230000001472 cytotoxic effect Effects 0.000 abstract description 3
- 230000032050 esterification Effects 0.000 abstract description 3
- 238000005886 esterification reaction Methods 0.000 abstract description 3
- 230000003647 oxidation Effects 0.000 abstract description 2
- 238000007254 oxidation reaction Methods 0.000 abstract description 2
- 231100000433 cytotoxic Toxicity 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- 230000000707 stereoselective effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000000203 mixture Substances 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 229930012538 Paclitaxel Natural products 0.000 description 11
- 229960001592 paclitaxel Drugs 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 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 9
- DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 3
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000005828 desilylation reaction Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation 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
- 239000012071 phase Substances 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 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
- 239000010949 copper Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VAHXMEZCPGHDBJ-QWHCGFSZSA-N (4s,5r)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-4-phenyl-1,3-oxazolidine-5-carboxylic acid Chemical compound OC(=O)[C@@H]1OC(C)(C)N(C(=O)OC(C)(C)C)[C@H]1C1=CC=CC=C1 VAHXMEZCPGHDBJ-QWHCGFSZSA-N 0.000 description 1
- QDQPKMKYUPYWLM-ABZYKWASSA-N (4s,5r)-2-(2,4-dimethoxyphenyl)-3-[(2-methylpropan-2-yl)oxycarbonyl]-4-phenyl-1,3-oxazolidine-5-carboxylic acid Chemical compound COC1=CC(OC)=CC=C1C1N(C(=O)OC(C)(C)C)[C@@H](C=2C=CC=CC=2)[C@H](C(O)=O)O1 QDQPKMKYUPYWLM-ABZYKWASSA-N 0.000 description 1
- AQOXAQNPPJHPAD-JKSUJKDBSA-N (4s,5r)-3-benzoyl-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid Chemical compound N1([C@H]([C@@H](OC1(C)C)C(O)=O)C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 AQOXAQNPPJHPAD-JKSUJKDBSA-N 0.000 description 1
- 241000208140 Acer Species 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 206010048610 Cardiotoxicity Diseases 0.000 description 1
- 240000003550 Eusideroxylon zwageri Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 241001116500 Taxus Species 0.000 description 1
- 241001116498 Taxus baccata Species 0.000 description 1
- 235000009065 Taxus cuspidata Nutrition 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 229940009456 adriamycin Drugs 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 231100000259 cardiotoxicity Toxicity 0.000 description 1
- 230000007681 cardiovascular toxicity Effects 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 229930004069 diterpene Natural products 0.000 description 1
- 125000000567 diterpene group Chemical group 0.000 description 1
- ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- 229940042880 natural phospholipid Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 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
- 239000002244 precipitate Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000002992 thymic effect Effects 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000002100 tumorsuppressive effect Effects 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI941592 | 1994-07-26 | ||
| ITMI941592A IT1274356B (it) | 1994-07-26 | 1994-07-26 | Tassani semisintetici odtati di attivita' antitumorale |
| IT95RM000413A IT1278108B1 (it) | 1995-06-19 | 1995-06-19 | Secotassani dotati di attivita' antitumorale. |
| ITRM950413 | 1995-06-19 | ||
| PCT/EP1995/002896 WO1996003394A1 (en) | 1994-07-26 | 1995-07-21 | Semi-synthetic taxanes with anti-tumoural activity |
| EP9502896 | 1995-07-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI970271A0 FI970271A0 (fi) | 1997-01-23 |
| FI970271A FI970271A (fi) | 1997-03-19 |
| FI120398B true FI120398B (fi) | 2009-10-15 |
Family
ID=26331178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI970271A FI120398B (fi) | 1994-07-26 | 1997-01-23 | Puolisynteettiset taksaanit, joilla on kasvaimia torjuvaa vaikutusta, sekä niiden valmistusmenetelmät, välituotteet ja farmaseuttiset koostumukset |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US5756776A (zh) |
| EP (1) | EP0773938B1 (zh) |
| JP (1) | JP2986550B2 (zh) |
| KR (1) | KR100220490B1 (zh) |
| CN (4) | CN1073105C (zh) |
| AT (1) | ATE176464T1 (zh) |
| AU (1) | AU684218B2 (zh) |
| BG (1) | BG62851B1 (zh) |
| CA (1) | CA2195844C (zh) |
| CZ (1) | CZ293076B6 (zh) |
| DE (1) | DE69507702T2 (zh) |
| DK (1) | DK0773938T3 (zh) |
| ES (1) | ES2126919T3 (zh) |
| FI (1) | FI120398B (zh) |
| GR (1) | GR3029309T3 (zh) |
| HK (1) | HK1011687A1 (zh) |
| HU (1) | HU222496B1 (zh) |
| NO (1) | NO315116B1 (zh) |
| PL (1) | PL187579B1 (zh) |
| RO (2) | RO116549B1 (zh) |
| RU (1) | RU2134688C1 (zh) |
| SI (1) | SI9520078B (zh) |
| SK (1) | SK281526B6 (zh) |
| WO (1) | WO1996003394A1 (zh) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6107332A (en) | 1995-09-12 | 2000-08-22 | The Liposome Company, Inc. | Hydrolysis-promoting hydrophobic taxane derivatives |
| US6395770B1 (en) * | 1995-10-26 | 2002-05-28 | Baker Norton Pharmaceuticals, Inc. | Method and compositions for administering taxanes orally to human patients |
| FR2745814B1 (fr) * | 1996-03-06 | 1998-04-03 | Rhone Poulenc Rorer Sa | Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent |
| EP0868422A1 (de) * | 1996-09-24 | 1998-10-07 | Marigen S.A. | Ultramikroemulsionen aus spontan dispergierbaren konzentraten mit antitumoral und antiviral wirksamen estern von baccatin-iii-verbindungen |
| US5773464A (en) * | 1996-09-30 | 1998-06-30 | Bristol-Myers Squibb Company | C-10 epoxy taxanes |
| US5977386A (en) * | 1996-12-24 | 1999-11-02 | Bristol-Myers Squibb Company | 6-thio-substituted paclitaxels |
| US5902822A (en) * | 1997-02-28 | 1999-05-11 | Bristol-Myers Squibb Company | 7-methylthiooxomethyl and 7-methylthiodioxomethyl paclitaxels |
| US5912264A (en) * | 1997-03-03 | 1999-06-15 | Bristol-Myers Squibb Company | 6-halo-or nitrate-substituted paclitaxels |
| US6017935A (en) * | 1997-04-24 | 2000-01-25 | Bristol-Myers Squibb Company | 7-sulfur substituted paclitaxels |
| IL132992A0 (en) * | 1997-05-27 | 2001-03-19 | Baker Norton Pharma | Method and compositions for administering taxanes orally to human patients |
| IT1308636B1 (it) * | 1999-03-02 | 2002-01-09 | Indena Spa | Procedimento per la preparazione di tassani da 10-desacetilbaccatinaiii. |
| AU775373B2 (en) | 1999-10-01 | 2004-07-29 | Immunogen, Inc. | Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents |
| IT1317731B1 (it) * | 2000-01-18 | 2003-07-15 | Indena Spa | Tassani semisintetici con attivita' antitumorale ed antiangiogenetica. |
| US6649632B2 (en) | 2000-02-02 | 2003-11-18 | Fsu Research Foundation, Inc. | C10 ester substituted taxanes |
| EP1129991A1 (de) * | 2000-03-02 | 2001-09-05 | Degussa AG | Verfahren zur Herstellung eines titanhaltigen Zeolithen |
| US7064980B2 (en) * | 2003-09-17 | 2006-06-20 | Sandisk Corporation | Non-volatile memory and method with bit line coupled compensation |
| PE20050693A1 (es) * | 2004-02-13 | 2005-09-27 | Univ Florida State Res Found | Taxanos sustituidos con esteres de ciclopentilo en c10 |
| AU2006214498A1 (en) * | 2005-02-14 | 2006-08-24 | Florida State University Research Foundation, Inc. | C10 cyclopropyl ester substituted taxane compositions |
| ITMI20050415A1 (it) * | 2005-03-15 | 2006-09-16 | Indena Spa | Derivati tassanici semi-sintetici ad attivita' antitumorale |
| ITMI20062479A1 (it) * | 2006-12-21 | 2008-06-22 | Indena Spa | Processo per la preparazione di secotassani |
| CA2696856A1 (en) * | 2007-08-22 | 2009-02-26 | 6570763 Canada Inc. | Process for converting 9-dihydro-13-acetylbaccatin iii into docetaxel or paclitaxel |
| CA2718567A1 (en) * | 2008-03-31 | 2009-12-03 | Florida State University Research Foundation, Inc. | C(10) ethyl ester and c(10) cyclopropyl ester substituted taxanes |
| AU2009282413B2 (en) | 2008-08-11 | 2014-07-17 | Nektar Therapeutics | Multi-arm polymeric alkanoate conjugates |
| WO2012088422A1 (en) | 2010-12-22 | 2012-06-28 | Nektar Therapeutics | Multi-arm polymeric prodrug conjugates of taxane-based compounds |
| US20130338216A1 (en) * | 2010-12-22 | 2013-12-19 | Nektar Therapeutics | Deuterated and/or fluorinated taxane derivatives |
| WO2012088391A1 (en) * | 2010-12-22 | 2012-06-28 | Nektar Therapeutics | Non-ring hydroxy substituted taxanes and methods for synthesizing the same |
| WO2012088445A1 (en) | 2010-12-22 | 2012-06-28 | Nektar Therapeutics | Multi-arm polymeric prodrug conjugates of cabazitaxel-based compounds |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5175315A (en) * | 1989-05-31 | 1992-12-29 | Florida State University | Method for preparation of taxol using β-lactam |
| KR930702323A (ko) * | 1991-07-17 | 1993-09-08 | 하지메 나까가와 | 항종양 활성을 가진 화합물(nsc-lsc1) 및 그의 제조방법 |
| US5399726A (en) * | 1993-01-29 | 1995-03-21 | Florida State University | Process for the preparation of baccatin III analogs bearing new C2 and C4 functional groups |
| FR2688499B1 (fr) * | 1992-03-10 | 1994-05-06 | Rhone Poulenc Rorer Sa | Procede de preparation de la beta-phenylisoserine et de ses analogues. |
| US5200534A (en) * | 1992-03-13 | 1993-04-06 | University Of Florida | Process for the preparation of taxol and 10-deacetyltaxol |
-
1995
- 1995-07-21 PL PL95318289A patent/PL187579B1/pl not_active IP Right Cessation
- 1995-07-21 DK DK95927699T patent/DK0773938T3/da active
- 1995-07-21 WO PCT/EP1995/002896 patent/WO1996003394A1/en active IP Right Grant
- 1995-07-21 SK SK100-97A patent/SK281526B6/sk not_active IP Right Cessation
- 1995-07-21 DE DE69507702T patent/DE69507702T2/de not_active Expired - Lifetime
- 1995-07-21 EP EP95927699A patent/EP0773938B1/en not_active Expired - Lifetime
- 1995-07-21 HU HU9700206A patent/HU222496B1/hu not_active IP Right Cessation
- 1995-07-21 RU RU97102722A patent/RU2134688C1/ru not_active IP Right Cessation
- 1995-07-21 RO ROA200000502A patent/RO116549B1/ro unknown
- 1995-07-21 ES ES95927699T patent/ES2126919T3/es not_active Expired - Lifetime
- 1995-07-21 CN CN95194333A patent/CN1073105C/zh not_active Expired - Fee Related
- 1995-07-21 SI SI9520078A patent/SI9520078B/sl not_active IP Right Cessation
- 1995-07-21 AT AT95927699T patent/ATE176464T1/de active
- 1995-07-21 CZ CZ1997199A patent/CZ293076B6/cs not_active IP Right Cessation
- 1995-07-21 JP JP8505456A patent/JP2986550B2/ja not_active Ceased
- 1995-07-21 AU AU31641/95A patent/AU684218B2/en not_active Ceased
- 1995-07-21 KR KR1019970700442A patent/KR100220490B1/ko not_active IP Right Cessation
- 1995-07-21 CA CA002195844A patent/CA2195844C/en not_active Expired - Fee Related
- 1995-07-21 RO RO97-00125A patent/RO115875B1/ro unknown
- 1995-07-24 US US08/505,924 patent/US5756776A/en not_active Expired - Lifetime
-
1997
- 1997-01-23 BG BG101165A patent/BG62851B1/bg unknown
- 1997-01-23 NO NO19970296A patent/NO315116B1/no not_active IP Right Cessation
- 1997-01-23 FI FI970271A patent/FI120398B/fi not_active IP Right Cessation
-
1998
- 1998-12-07 HK HK98112903A patent/HK1011687A1/xx not_active IP Right Cessation
-
1999
- 1999-02-09 GR GR990400393T patent/GR3029309T3/el unknown
-
2000
- 2000-09-29 CN CN00129055A patent/CN1130356C/zh not_active Expired - Fee Related
- 2000-09-29 CN CN00129056A patent/CN1128795C/zh not_active Expired - Fee Related
- 2000-09-29 CN CN00129054A patent/CN1120161C/zh not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI120398B (fi) | Puolisynteettiset taksaanit, joilla on kasvaimia torjuvaa vaikutusta, sekä niiden valmistusmenetelmät, välituotteet ja farmaseuttiset koostumukset | |
| FI109904B (fi) | Menetelmä lääkeaineina käyttökelpoisten 14-b-hydroksi-10-asetyylibakkatiini-III:n ja sen johdannaisten valmistamiseksi | |
| RU2119485C1 (ru) | Производные таксана ш, способы их получения и фармацевтическая композиция | |
| JP2011046744A (ja) | １０−デアセチルバッカチンＩＩＩおよび１０−デアセチル１４β−ヒドロキシバッカチンＩＩＩ誘導体類、それらの調製方法およびそれらを含む医薬製剤 | |
| Zhou et al. | Antitumor agents. 144. New. gamma.-lactone ring-modified arylamino etoposide analogs as inhibitors of human DNA topoisomerase II | |
| RU2168513C2 (ru) | Производные таксана, способ их получения и фармацевтическая композиция | |
| WO1999033462A9 (en) | 2-aroyl-4-acyl paclitaxel (taxol) analogs | |
| US20020045771A1 (en) | Family of canadensol taxanes, the semi-synthetic preparation and therapeutic use thereof | |
| GB2289277A (en) | Taxane derivatives | |
| AU2007204520A1 (en) | Taxol derivatives with antitumor activity |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Patent granted |
Ref document number: 120398 Country of ref document: FI |
|
| MM | Patent lapsed |