ZA200202696B - Pentacyclic taxane compounds. - Google Patents
Pentacyclic taxane compounds. Download PDFInfo
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- ZA200202696B ZA200202696B ZA200202696A ZA200202696A ZA200202696B ZA 200202696 B ZA200202696 B ZA 200202696B ZA 200202696 A ZA200202696 A ZA 200202696A ZA 200202696 A ZA200202696 A ZA 200202696A ZA 200202696 B ZA200202696 B ZA 200202696B
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- South Africa
- Prior art keywords
- group
- compound
- salt
- following formula
- compound represented
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- 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 title 1
- 150000001875 compounds Chemical class 0.000 claims description 152
- 238000000034 method Methods 0.000 claims description 33
- -1 butyldimethylsilyl group Chemical group 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 30
- 239000003814 drug Substances 0.000 claims description 17
- 206010028980 Neoplasm Diseases 0.000 claims description 13
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 239000002246 antineoplastic agent Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 230000036961 partial effect Effects 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 339
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
- 239000000243 solution Substances 0.000 description 44
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 238000005160 1H NMR spectroscopy Methods 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 239000010410 layer Substances 0.000 description 20
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 14
- 230000000259 anti-tumor effect Effects 0.000 description 14
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- 238000012360 testing method Methods 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 230000002829 reductive effect Effects 0.000 description 12
- 238000000926 separation method Methods 0.000 description 12
- 229940079593 drug Drugs 0.000 description 11
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
- 241000282693 Cercopithecidae Species 0.000 description 10
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 210000004185 liver Anatomy 0.000 description 9
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 8
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- 238000002360 preparation method Methods 0.000 description 8
- 238000010189 synthetic method Methods 0.000 description 8
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- 210000004369 blood Anatomy 0.000 description 7
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 229930012538 Paclitaxel Natural products 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 229960001592 paclitaxel Drugs 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 6
- 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 6
- 150000004579 taxol derivatives Chemical class 0.000 description 6
- WCMBUDUPBVQEDN-VHSXEESVSA-N (2r,3s)-3-(3-fluoropyridin-2-yl)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H]([C@@H](O)C(O)=O)C1=NC=CC=C1F WCMBUDUPBVQEDN-VHSXEESVSA-N 0.000 description 5
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- 108090000623 proteins and genes Proteins 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 239000002207 metabolite Substances 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 description 4
- LJMYTCUKRWYGMQ-VQTJNVASSA-N tert-butyl (2s,3r)-2-(5-methoxypyridin-2-yl)-4-oxo-3-tri(propan-2-yl)silyloxyazetidine-1-carboxylate Chemical compound N1=CC(OC)=CC=C1[C@@H]1N(C(=O)OC(C)(C)C)C(=O)[C@@H]1O[Si](C(C)C)(C(C)C)C(C)C LJMYTCUKRWYGMQ-VQTJNVASSA-N 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- HLGFPNSOTOYHLN-RBUKOAKNSA-N (2R,3S)-3-(3-fluoropyridin-2-yl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-tri(propan-2-yl)silyloxypropanoic acid Chemical compound CC(C)[Si](C(C)C)(C(C)C)O[C@@H](C(O)=O)[C@@H](NC(=O)OC(C)(C)C)C1=NC=CC=C1F HLGFPNSOTOYHLN-RBUKOAKNSA-N 0.000 description 3
- DRPHKDAYDWBZPT-VQTJNVASSA-N (2R,3S)-3-(5-methoxypyridin-2-yl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-tri(propan-2-yl)silyloxypropanoic acid Chemical compound COC1=CC=C([C@H](NC(=O)OC(C)(C)C)[C@@H](O[Si](C(C)C)(C(C)C)C(C)C)C(O)=O)N=C1 DRPHKDAYDWBZPT-VQTJNVASSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 3
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- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
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- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 210000003484 anatomy Anatomy 0.000 description 1
- 230000000702 anti-platelet effect Effects 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 125000006630 butoxycarbonylamino group Chemical group 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229920003123 carboxymethyl cellulose sodium Polymers 0.000 description 1
- 229940063834 carboxymethylcellulose sodium Drugs 0.000 description 1
- 230000032823 cell division Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 210000000805 cytoplasm Anatomy 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009510 drug design Methods 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 230000036267 drug metabolism Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 201000010536 head and neck cancer Diseases 0.000 description 1
- 208000014829 head and neck neoplasm Diseases 0.000 description 1
- 201000005787 hematologic cancer Diseases 0.000 description 1
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 210000004276 hyalin Anatomy 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 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
- 238000007689 inspection Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 201000010982 kidney cancer Diseases 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 201000005202 lung cancer Diseases 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 231100000682 maximum tolerated dose Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000006241 metabolic reaction Methods 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 210000004688 microtubule Anatomy 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 208000025189 neoplasm of testis Diseases 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 1
- 239000012285 osmium tetroxide Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- XCLDDMCNFANFBG-DLBZAZTESA-N tert-butyl (2s,3r)-2-(3-fluoropyridin-2-yl)-4-oxo-3-phenylmethoxyazetidine-1-carboxylate Chemical compound O([C@@H]1[C@@H](N(C1=O)C(=O)OC(C)(C)C)C=1C(=CC=CN=1)F)CC1=CC=CC=C1 XCLDDMCNFANFBG-DLBZAZTESA-N 0.000 description 1
- GZSZOHPUGGDAGX-RBUKOAKNSA-N tert-butyl (2s,3r)-2-(5-chloropyridin-2-yl)-4-oxo-3-tri(propan-2-yl)silyloxyazetidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1C(=O)[C@H](O[Si](C(C)C)(C(C)C)C(C)C)[C@@H]1C1=CC=C(Cl)C=N1 GZSZOHPUGGDAGX-RBUKOAKNSA-N 0.000 description 1
- 201000003120 testicular cancer Diseases 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 206010046766 uterine cancer Diseases 0.000 description 1
Classifications
-
- 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
- C07D493/04—Ortho-condensed systems
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4355—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having oxygen as a ring hetero atom
-
- 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)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29335699 | 1999-10-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200202696B true ZA200202696B (en) | 2003-09-23 |
Family
ID=17793741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200202696A ZA200202696B (en) | 1999-10-15 | 2002-04-05 | Pentacyclic taxane compounds. |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP1221445B1 (ko) |
| JP (1) | JP3776799B2 (ko) |
| KR (1) | KR100706566B1 (ko) |
| CN (1) | CN1203074C (ko) |
| AR (1) | AR026026A1 (ko) |
| AT (1) | ATE405569T1 (ko) |
| AU (1) | AU774787B2 (ko) |
| BR (1) | BR0014687A (ko) |
| CA (1) | CA2386772C (ko) |
| DE (1) | DE60039998D1 (ko) |
| DK (1) | DK1221445T3 (ko) |
| ES (1) | ES2311473T3 (ko) |
| HK (1) | HK1044000B (ko) |
| IL (2) | IL149007A0 (ko) |
| MX (1) | MXPA02003797A (ko) |
| MY (1) | MY125378A (ko) |
| NO (1) | NO328418B1 (ko) |
| PT (1) | PT1221445E (ko) |
| RU (1) | RU2257387C2 (ko) |
| TW (1) | TWI225062B (ko) |
| WO (1) | WO2001027115A1 (ko) |
| ZA (1) | ZA200202696B (ko) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003045953A1 (fr) * | 2001-11-29 | 2003-06-05 | Daiichi Pharmaceutical Co., Ltd. | Cristaux de derive de taxane et procede de production associe |
| TW200533339A (en) | 2004-03-16 | 2005-10-16 | Bristol Myers Squibb Co | Therapeutic synergy of anti-cancer compounds |
| ATE526332T1 (de) * | 2004-04-30 | 2011-10-15 | Daiichi Seiyaku Co | Verfahren zur herstellung von pentacyclischem taxan |
| US20090186868A1 (en) * | 2005-10-25 | 2009-07-23 | Daiichi Sankyo Company Limited | Taxane Compound Having Azetidine Ring Structure |
| CN100516067C (zh) * | 2006-01-10 | 2009-07-22 | 上海恒瑞医药有限公司 | 具有抗肿瘤活性的紫杉酚衍生物 |
| US8785669B2 (en) | 2010-06-30 | 2014-07-22 | Gfv, Llc | Taxane compounds, compositions and methods |
| AU2012290979A1 (en) | 2011-08-02 | 2014-02-13 | Astellas Pharma Inc. | Method for treating cancer by combined use of medicinal agents |
| FR2986526A1 (fr) | 2012-02-03 | 2013-08-09 | Sanofi Sa | Procede de preparation de derives du taxol et certains composes intermediaires |
| CN104650109B (zh) * | 2013-11-22 | 2019-01-01 | 江苏天士力帝益药业有限公司 | 紫杉烷类化合物 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2712289B1 (fr) * | 1993-11-08 | 1996-01-05 | Rhone Poulenc Rorer Sa | Nouveaux dérivés de taxicine, leur préparation et les compositions pharmaceutiques qui les contiennent. |
| DK0826688T3 (da) * | 1995-04-28 | 2001-10-22 | Daiichi Seiyaku Co | Pentacykliske forbindelser |
| TW527183B (en) * | 1996-06-06 | 2003-04-11 | Daiichi Seiyaku Co | Drug complex |
-
2000
- 2000-10-12 ES ES00966445T patent/ES2311473T3/es not_active Expired - Lifetime
- 2000-10-12 AT AT00966445T patent/ATE405569T1/de active
- 2000-10-12 EP EP00966445A patent/EP1221445B1/en not_active Expired - Lifetime
- 2000-10-12 DE DE60039998T patent/DE60039998D1/de not_active Expired - Lifetime
- 2000-10-12 BR BR0014687-0A patent/BR0014687A/pt not_active IP Right Cessation
- 2000-10-12 CA CA002386772A patent/CA2386772C/en not_active Expired - Fee Related
- 2000-10-12 KR KR1020027004826A patent/KR100706566B1/ko not_active IP Right Cessation
- 2000-10-12 CN CNB008169780A patent/CN1203074C/zh not_active Expired - Fee Related
- 2000-10-12 MX MXPA02003797A patent/MXPA02003797A/es active IP Right Grant
- 2000-10-12 WO PCT/JP2000/007087 patent/WO2001027115A1/ja active IP Right Grant
- 2000-10-12 RU RU2002109593/04A patent/RU2257387C2/ru active IP Right Revival
- 2000-10-12 JP JP2001530333A patent/JP3776799B2/ja not_active Expired - Lifetime
- 2000-10-12 IL IL14900700A patent/IL149007A0/xx active IP Right Grant
- 2000-10-12 MY MYPI20004781A patent/MY125378A/en unknown
- 2000-10-12 PT PT00966445T patent/PT1221445E/pt unknown
- 2000-10-12 AU AU76851/00A patent/AU774787B2/en not_active Ceased
- 2000-10-12 DK DK00966445T patent/DK1221445T3/da active
- 2000-10-13 TW TW089121432A patent/TWI225062B/zh not_active IP Right Cessation
- 2000-10-13 AR ARP000105381A patent/AR026026A1/es active IP Right Grant
-
2002
- 2002-04-04 IL IL149007A patent/IL149007A/en unknown
- 2002-04-05 ZA ZA200202696A patent/ZA200202696B/en unknown
- 2002-04-12 NO NO20021753A patent/NO328418B1/no not_active IP Right Cessation
- 2002-08-01 HK HK02105667.9A patent/HK1044000B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| MY125378A (en) | 2006-07-31 |
| DE60039998D1 (de) | 2008-10-02 |
| KR20020035901A (ko) | 2002-05-15 |
| NO20021753L (no) | 2002-06-12 |
| HK1044000A1 (en) | 2002-10-04 |
| IL149007A (en) | 2006-12-10 |
| EP1221445A4 (en) | 2003-05-28 |
| BR0014687A (pt) | 2002-11-19 |
| AU774787B2 (en) | 2004-07-08 |
| CN1409714A (zh) | 2003-04-09 |
| ES2311473T3 (es) | 2009-02-16 |
| WO2001027115A1 (fr) | 2001-04-19 |
| MXPA02003797A (es) | 2002-12-13 |
| HK1044000B (zh) | 2008-11-21 |
| ATE405569T1 (de) | 2008-09-15 |
| CA2386772C (en) | 2009-01-13 |
| TWI225062B (en) | 2004-12-11 |
| KR100706566B1 (ko) | 2007-04-13 |
| DK1221445T3 (da) | 2008-11-24 |
| EP1221445A1 (en) | 2002-07-10 |
| IL149007A0 (en) | 2002-11-10 |
| NO20021753D0 (no) | 2002-04-12 |
| AU7685100A (en) | 2001-04-23 |
| EP1221445B1 (en) | 2008-08-20 |
| PT1221445E (pt) | 2008-10-08 |
| JP3776799B2 (ja) | 2006-05-17 |
| CN1203074C (zh) | 2005-05-25 |
| AR026026A1 (es) | 2002-12-26 |
| CA2386772A1 (en) | 2001-04-19 |
| NO328418B1 (no) | 2010-02-15 |
| RU2257387C2 (ru) | 2005-07-27 |
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