CZ20013520A3 - C10 - Karbamoyloxy substituované taxany jako protinádorová činidla - Google Patents
C10 - Karbamoyloxy substituované taxany jako protinádorová činidla Download PDFInfo
- Publication number
- CZ20013520A3 CZ20013520A3 CZ20013520A CZ20013520A CZ20013520A3 CZ 20013520 A3 CZ20013520 A3 CZ 20013520A3 CZ 20013520 A CZ20013520 A CZ 20013520A CZ 20013520 A CZ20013520 A CZ 20013520A CZ 20013520 A3 CZ20013520 A3 CZ 20013520A3
- Authority
- CZ
- Czechia
- Prior art keywords
- pyridyl
- thienyl
- furyl
- taxane
- alkyl
- Prior art date
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- 229940123237 Taxane Drugs 0.000 title claims abstract description 154
- 239000002246 antineoplastic agent Substances 0.000 title description 6
- -1 carbamoyloxy substituent Chemical group 0.000 claims abstract description 124
- 125000000217 alkyl group Chemical group 0.000 claims description 188
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 160
- 125000003342 alkenyl group Chemical group 0.000 claims description 148
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 claims description 139
- 125000000304 alkynyl group Chemical group 0.000 claims description 135
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 81
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 72
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 70
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 70
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 69
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 69
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 69
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 65
- 125000002541 furyl group Chemical group 0.000 claims description 54
- 125000001544 thienyl group Chemical group 0.000 claims description 54
- 125000000623 heterocyclic group Chemical group 0.000 claims description 50
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 49
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 47
- 125000004076 pyridyl group Chemical group 0.000 claims description 47
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 36
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 34
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 33
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 125000000468 ketone group Chemical group 0.000 claims description 25
- 229930194542 Keto Natural products 0.000 claims description 24
- 125000001145 hydrido group Chemical group *[H] 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 20
- 125000004423 acyloxy group Chemical group 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 239000003937 drug carrier Substances 0.000 claims description 13
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 230000004614 tumor growth Effects 0.000 claims description 4
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 13
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 3
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract description 24
- 150000001875 compounds Chemical class 0.000 description 59
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- 239000000243 solution Substances 0.000 description 51
- 230000000259 anti-tumor effect Effects 0.000 description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
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- 235000019441 ethanol Nutrition 0.000 description 20
- 125000004122 cyclic group Chemical group 0.000 description 18
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- 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 14
- 229960003668 docetaxel Drugs 0.000 description 14
- 239000000839 emulsion Substances 0.000 description 13
- 125000001072 heteroaryl group Chemical group 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 125000003118 aryl group Chemical group 0.000 description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- 239000008389 polyethoxylated castor oil Substances 0.000 description 11
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
- 238000007911 parenteral administration Methods 0.000 description 9
- 125000006239 protecting group Chemical group 0.000 description 9
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 229930012538 Paclitaxel Natural products 0.000 description 8
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 8
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 8
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 8
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 8
- 125000006038 hexenyl group Chemical group 0.000 description 8
- 125000005980 hexynyl group Chemical group 0.000 description 8
- 229960001592 paclitaxel Drugs 0.000 description 8
- 229920001223 polyethylene glycol Polymers 0.000 description 8
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
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- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 7
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 7
- 125000005981 pentynyl group Chemical group 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- 125000004104 aryloxy group Chemical group 0.000 description 6
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- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
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- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010483 polyoxyethylene sorbitan monopalmitate Nutrition 0.000 description 1
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- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
- 229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-M ricinoleate Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O WBHHMMIMDMUBKC-QJWNTBNXSA-M 0.000 description 1
- 229940066675 ricinoleate Drugs 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 239000010686 shark liver oil Substances 0.000 description 1
- 229940069764 shark liver oil Drugs 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229940082004 sodium laurate Drugs 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
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- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229940032094 squalane Drugs 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940114926 stearate Drugs 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 150000003538 tetroses Chemical class 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
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- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
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- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003641 trioses Chemical class 0.000 description 1
- SCEZSEOTDXHAOD-UHFFFAOYSA-N tris(2,3-dihydroxypropyl) 2-hydroxypropane-1,2,3-tricarboxylate Chemical class OCC(O)COC(=O)CC(O)(C(=O)OCC(O)CO)CC(=O)OCC(O)CO SCEZSEOTDXHAOD-UHFFFAOYSA-N 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
- 235000001892 vitamin D2 Nutrition 0.000 description 1
- 239000011653 vitamin D2 Substances 0.000 description 1
- 235000019386 wax ester Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003953 γ-lactams Chemical class 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
-
- 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
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/08—Solutions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17979300P | 2000-02-02 | 2000-02-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CZ20013520A3 true CZ20013520A3 (cs) | 2002-03-13 |
Family
ID=22658023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ20013520A CZ20013520A3 (cs) | 2000-02-02 | 2001-02-02 | C10 - Karbamoyloxy substituované taxany jako protinádorová činidla |
Country Status (20)
| Country | Link |
|---|---|
| US (3) | US6596737B2 (enExample) |
| EP (1) | EP1165551B1 (enExample) |
| JP (1) | JP2003522173A (enExample) |
| KR (1) | KR20020000159A (enExample) |
| CN (1) | CN1362959A (enExample) |
| AT (1) | ATE401325T1 (enExample) |
| AU (1) | AU783422B2 (enExample) |
| BR (1) | BR0104352A (enExample) |
| CA (1) | CA2368541A1 (enExample) |
| CZ (1) | CZ20013520A3 (enExample) |
| DE (1) | DE60134814D1 (enExample) |
| HK (1) | HK1047936A1 (enExample) |
| HU (1) | HUP0200721A3 (enExample) |
| IL (1) | IL145640A (enExample) |
| MX (1) | MXPA01009921A (enExample) |
| NO (1) | NO20014760L (enExample) |
| NZ (1) | NZ514407A (enExample) |
| PL (1) | PL350331A1 (enExample) |
| WO (1) | WO2001057033A1 (enExample) |
| ZA (1) | ZA200108053B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL350075A1 (en) * | 2000-02-02 | 2002-11-04 | Univ Florida State Res Found | Taxane formulations having improved solubility |
| MXPA01009921A (es) * | 2000-02-02 | 2003-08-01 | Univ Florida State Res Found | Taxanos sustituidos como carbamoiloxilo en c10 como agentes antitumorales. |
| CN1712399B (zh) * | 2004-06-24 | 2010-08-11 | 中国医学科学院药物研究所 | 紫杉醇和免疫增强剂胞壁酰二肽共轭物的制备及用途 |
| EP3252128B1 (en) * | 2006-04-03 | 2019-01-02 | Pharmatherm Chemicals Inc. | Thermal extraction method for producing a taxane extract |
| WO2011147330A1 (zh) | 2010-05-27 | 2011-12-01 | 中国医学科学院药物研究所 | 双功能共缀物的化学合成及抗肿瘤与抗肿瘤转移作用 |
| JP6959096B2 (ja) * | 2017-10-13 | 2021-11-02 | エイブリック株式会社 | 充放電制御回路及びこれを備えたバッテリ装置 |
Family Cites Families (34)
| 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 |
| FR2679230B1 (fr) | 1991-07-16 | 1993-11-19 | Rhone Poulenc Rorer Sa | Nouveaux derives d'analogues du taxol, leur preparation et les compositions qui les contiennent. |
| US5243045A (en) | 1991-09-23 | 1993-09-07 | Florida State University | Certain alkoxy substituted taxanes and pharmaceutical compositions containing them |
| US5721268A (en) | 1991-09-23 | 1998-02-24 | Florida State University | C7 taxane derivatives and pharmaceutical compositions containing them |
| US5350866A (en) | 1991-09-23 | 1994-09-27 | Bristol-Myers Squibb Company | 10-desacetoxytaxol derivatives |
| US5714513A (en) | 1991-09-23 | 1998-02-03 | Florida State University | C10 taxane derivatives and pharmaceutical compositions |
| US5227400A (en) | 1991-09-23 | 1993-07-13 | Florida State University | Furyl and thienyl substituted taxanes and pharmaceutical compositions containing them |
| US5283253A (en) | 1991-09-23 | 1994-02-01 | Florida State University | Furyl or thienyl carbonyl substituted taxanes and pharmaceutical compositions containing them |
| US5430160A (en) | 1991-09-23 | 1995-07-04 | Florida State University | Preparation of substituted isoserine esters using β-lactams and metal or ammonium alkoxides |
| ES2230790T3 (es) | 1992-01-15 | 2005-05-01 | E.R. SQUIBB & SONS, INC. | Procedimientos enzimaticos para la resolucion de mezclas enantiomericas de compuestos utiles como intermedios en la preparacion de taxanos. |
| US5272171A (en) | 1992-02-13 | 1993-12-21 | Bristol-Myers Squibb Company | Phosphonooxy and carbonate derivatives of taxol |
| FR2691460B1 (fr) | 1992-05-21 | 1994-07-22 | Rhone Poulenc Rorer Sa | Nouveaux derives du taxane, leur preparation et les compositions qui les contiennent. |
| CA2109861C (en) | 1992-12-04 | 1999-03-16 | Shu-Hui Chen | 6,7-modified paclitaxels |
| DE69424166T2 (de) | 1993-06-11 | 2000-10-05 | Pharmacia & Upjohn Co., Kalamazoo | Delta 6, 7-taxolen, antineoplastische verwendung und diese enthaltende pharmazeutische zusammenstellungen |
| IL109926A (en) | 1993-06-15 | 2000-02-29 | Bristol Myers Squibb Co | Methods for the preparation of taxanes and microorganisms and enzymes utilized therein |
| TW397866B (en) | 1993-07-14 | 2000-07-11 | Bristol Myers Squibb Co | Enzymatic processes for the resolution of enantiomeric mixtures of compounds useful as intermediates in the preparation of taxanes |
| US6100411A (en) * | 1994-10-28 | 2000-08-08 | The Research Foundation Of State University Of New York | Taxoid anti-tumor agents and pharmaceutical compositions thereof |
| WO1996013495A1 (en) * | 1994-10-28 | 1996-05-09 | The Research Foundation Of State University Of New York | Taxoid derivatives, their preparation and their use as antitumor agents |
| FR2732342B1 (fr) | 1995-04-03 | 1997-04-30 | Rhone Poulenc Rorer Sa | Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent |
| FR2732968B1 (fr) | 1995-04-14 | 1997-05-16 | Rhone Poulenc Rorer Sa | Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent |
| US5780653A (en) | 1995-06-07 | 1998-07-14 | Vivorx Pharmaceuticals, Inc. | Nitrophenyl, 10-deacetylated substituted taxol derivatives as dual functional cytotoxic/radiosensitizers |
| CA2231837A1 (en) | 1995-09-13 | 1997-03-20 | Florida State University | Radiosensitizing taxanes and their pharmaceutical preparations |
| IL126856A0 (en) | 1996-05-06 | 1999-09-22 | Univ Florida State | 1-Deoxy baccatin iii 1-deoxy taxol and 1-deoxy taxol analogs and method for the preparation thereof |
| BR9710366A (pt) | 1996-07-15 | 1999-08-17 | Yakult Honsha Kk | Derivados de taxane e drogas que os contêm |
| US5811452A (en) | 1997-01-08 | 1998-09-22 | The Research Foundation Of State University Of New York | Taxoid reversal agents for drug-resistance in cancer chemotherapy and pharmaceutical compositions thereof |
| US5912264A (en) | 1997-03-03 | 1999-06-15 | Bristol-Myers Squibb Company | 6-halo-or nitrate-substituted paclitaxels |
| US7288665B1 (en) | 1997-08-18 | 2007-10-30 | Florida State University | Process for selective derivatization of taxanes |
| JPH1192468A (ja) | 1997-09-17 | 1999-04-06 | Yakult Honsha Co Ltd | 新規なタキサン誘導体 |
| EP1044971A4 (en) * | 1997-12-19 | 2001-11-07 | Yakult Honsha Kk | TAXAN DERIVATIVES |
| JP2003026673A (ja) * | 1999-03-05 | 2003-01-29 | Asahi Kasei Corp | 骨形成促進剤 |
| PL350075A1 (en) * | 2000-02-02 | 2002-11-04 | Univ Florida State Res Found | Taxane formulations having improved solubility |
| MXPA01009921A (es) * | 2000-02-02 | 2003-08-01 | Univ Florida State Res Found | Taxanos sustituidos como carbamoiloxilo en c10 como agentes antitumorales. |
| EP1175414A1 (en) | 2000-02-02 | 2002-01-30 | Florida State University Research Foundation, Inc. | Taxane formulations having improved solubility |
| GB2370649B (en) * | 2000-11-09 | 2003-06-25 | Toppan Printing Co Ltd | Measurement of rate of transmission of a vapour through a sample |
-
2001
- 2001-02-02 MX MXPA01009921A patent/MXPA01009921A/es active IP Right Grant
- 2001-02-02 AT AT01905434T patent/ATE401325T1/de not_active IP Right Cessation
- 2001-02-02 NZ NZ51440701A patent/NZ514407A/xx unknown
- 2001-02-02 JP JP2001557865A patent/JP2003522173A/ja not_active Withdrawn
- 2001-02-02 KR KR1020017012573A patent/KR20020000159A/ko not_active Abandoned
- 2001-02-02 BR BR0104352-8A patent/BR0104352A/pt not_active IP Right Cessation
- 2001-02-02 AU AU33313/01A patent/AU783422B2/en not_active Ceased
- 2001-02-02 CZ CZ20013520A patent/CZ20013520A3/cs unknown
- 2001-02-02 CN CN01800317A patent/CN1362959A/zh active Pending
- 2001-02-02 PL PL01350331A patent/PL350331A1/xx not_active Application Discontinuation
- 2001-02-02 US US09/775,852 patent/US6596737B2/en not_active Expired - Fee Related
- 2001-02-02 CA CA002368541A patent/CA2368541A1/en not_active Withdrawn
- 2001-02-02 DE DE60134814T patent/DE60134814D1/de not_active Expired - Fee Related
- 2001-02-02 WO PCT/US2001/003633 patent/WO2001057033A1/en not_active Ceased
- 2001-02-02 HK HK03100170.9A patent/HK1047936A1/zh unknown
- 2001-02-02 HU HU0200721A patent/HUP0200721A3/hu unknown
- 2001-02-02 EP EP01905434A patent/EP1165551B1/en not_active Expired - Lifetime
- 2001-02-02 IL IL145640A patent/IL145640A/en not_active IP Right Cessation
- 2001-10-01 ZA ZA200108053A patent/ZA200108053B/en unknown
- 2001-10-01 NO NO20014760A patent/NO20014760L/no not_active Application Discontinuation
-
2003
- 2003-07-11 US US10/618,063 patent/US6906088B2/en not_active Expired - Fee Related
-
2005
- 2005-02-28 US US11/067,882 patent/US7230013B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| IL145640A0 (en) | 2002-06-30 |
| ZA200108053B (en) | 2003-12-01 |
| IL145640A (en) | 2007-02-11 |
| WO2001057033A1 (en) | 2001-08-09 |
| US6596737B2 (en) | 2003-07-22 |
| US7230013B2 (en) | 2007-06-12 |
| BR0104352A (pt) | 2002-01-02 |
| NZ514407A (en) | 2004-12-24 |
| HUP0200721A2 (hu) | 2002-07-29 |
| EP1165551A1 (en) | 2002-01-02 |
| US6906088B2 (en) | 2005-06-14 |
| DE60134814D1 (de) | 2008-08-28 |
| NO20014760D0 (no) | 2001-10-01 |
| NO20014760L (no) | 2001-11-30 |
| HK1047936A1 (zh) | 2003-03-14 |
| PL350331A1 (en) | 2002-12-02 |
| KR20020000159A (ko) | 2002-01-04 |
| EP1165551B1 (en) | 2008-07-16 |
| US20050182098A1 (en) | 2005-08-18 |
| US20040034230A1 (en) | 2004-02-19 |
| US20020077341A1 (en) | 2002-06-20 |
| AU3331301A (en) | 2001-08-14 |
| CN1362959A (zh) | 2002-08-07 |
| CA2368541A1 (en) | 2001-08-09 |
| AU783422B2 (en) | 2005-10-27 |
| HUP0200721A3 (en) | 2005-02-28 |
| JP2003522173A (ja) | 2003-07-22 |
| MXPA01009921A (es) | 2003-08-01 |
| ATE401325T1 (de) | 2008-08-15 |
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