JP2009512714A5 - - Google Patents
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- Publication number
- JP2009512714A5 JP2009512714A5 JP2008536850A JP2008536850A JP2009512714A5 JP 2009512714 A5 JP2009512714 A5 JP 2009512714A5 JP 2008536850 A JP2008536850 A JP 2008536850A JP 2008536850 A JP2008536850 A JP 2008536850A JP 2009512714 A5 JP2009512714 A5 JP 2009512714A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- lower alkyl
- hydrogen
- amino
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 114
- -1 camptothecin scaffold compound Chemical class 0.000 claims description 105
- 125000003545 alkoxy group Chemical group 0.000 claims description 81
- 150000001875 compounds Chemical class 0.000 claims description 76
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- 239000001257 hydrogen Substances 0.000 claims description 52
- 235000000346 sugar Nutrition 0.000 claims description 44
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 36
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 36
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 34
- 150000002431 hydrogen Chemical class 0.000 claims description 33
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 30
- 125000000623 heterocyclic group Chemical class 0.000 claims description 24
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 22
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 21
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000002837 carbocyclic group Chemical class 0.000 claims description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- 230000005855 radiation Effects 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 229940127093 camptothecin Drugs 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 210000004881 tumor cell Anatomy 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical group C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 4
- 230000000118 anti-neoplastic effect Effects 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- MQTMHRXULFJFOC-UHFFFAOYSA-N 2-[(2,4,5,7-tetranitrofluoren-9-ylidene)amino]oxypropanoic acid Chemical group C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1C(=NOC(C)C(O)=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C12 MQTMHRXULFJFOC-UHFFFAOYSA-N 0.000 claims description 3
- SNLFYGIUTYKKOE-UHFFFAOYSA-N 4-n,4-n-bis(4-aminophenyl)benzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1N(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 SNLFYGIUTYKKOE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims description 3
- 208000035269 cancer or benign tumor Diseases 0.000 claims description 3
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 230000001235 sensitizing effect Effects 0.000 claims description 3
- 230000002195 synergetic effect Effects 0.000 claims description 3
- MSBZUOIIUNSSRF-UHFFFAOYSA-N 1-oxido-1,2,3-benzotriazin-1-ium Chemical compound C1=CC=C2[N+]([O-])=NN=CC2=C1 MSBZUOIIUNSSRF-UHFFFAOYSA-N 0.000 claims description 2
- UJKDDHMBQYSTLZ-UHFFFAOYSA-N 2-[(2,4,5,7-tetranitrofluoren-9-ylidene)amino]oxyacetic acid Chemical group C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1C(=NOCC(=O)O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C12 UJKDDHMBQYSTLZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 35
- 125000001475 halogen functional group Chemical group 0.000 claims 23
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 8
- 125000004414 alkyl thio group Chemical group 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 125000002947 alkylene group Chemical group 0.000 claims 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims 5
- MENHXVNCWVKFRA-UHFFFAOYSA-N 1,4-oxazin-2-one Chemical compound O=C1C=NC=CO1 MENHXVNCWVKFRA-UHFFFAOYSA-N 0.000 claims 4
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 4
- 125000004665 trialkylsilyl group Chemical group 0.000 claims 4
- 150000001720 carbohydrates Chemical class 0.000 claims 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 3
- 125000005277 alkyl imino group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 241000790917 Dioxys <bee> Species 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 150000001717 carbocyclic compounds Chemical class 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims 1
- 210000004027 cell Anatomy 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 125000005843 halogen group Chemical group 0.000 description 9
- 239000002502 liposome Substances 0.000 description 8
- 239000012528 membrane Substances 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 5
- 239000002609 medium Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 230000000637 radiosensitizating effect Effects 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 150000002466 imines Chemical class 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 150000008163 sugars Chemical group 0.000 description 3
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000012981 Hank's balanced salt solution Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 230000005757 colony formation Effects 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000005865 ionizing radiation Effects 0.000 description 2
- 230000003211 malignant effect Effects 0.000 description 2
- 239000000693 micelle Substances 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- JOERSAVCLPYNIZ-UHFFFAOYSA-N 2,4,5,7-tetranitrofluoren-9-one Chemical compound O=C1C2=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C2C2=C1C=C([N+](=O)[O-])C=C2[N+]([O-])=O JOERSAVCLPYNIZ-UHFFFAOYSA-N 0.000 description 1
- 125000001698 2H-pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001826 4H-pyranyl group Chemical group O1C(=CCC=C1)* 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 0 CC[C@](C(C=C1N2Cc3c(*)c(c(*)c(*)c(*)c4*)c4nc13)=C(CO1)C2=O)(C1=O)OC(***)=O Chemical compound CC[C@](C(C=C1N2Cc3c(*)c(c(*)c(*)c(*)c4*)c4nc13)=C(CO1)C2=O)(C1=O)OC(***)=O 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 108700041567 MDR Genes Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229930012538 Paclitaxel Natural products 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 229940034982 antineoplastic agent Drugs 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical class 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003012 bilayer membrane Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
- 230000003833 cell viability Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 238000010293 colony formation assay Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- QDYBCIWLGJMJGO-UHFFFAOYSA-N dinitromethanone Chemical class [O-][N+](=O)C(=O)[N+]([O-])=O QDYBCIWLGJMJGO-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 239000012737 fresh medium Substances 0.000 description 1
- 150000003949 imides Chemical group 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical group 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 230000009826 neoplastic cell growth Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960001592 paclitaxel Drugs 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 239000002534 radiation-sensitizing agent Substances 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 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 1
- 230000004614 tumor growth Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72892405P | 2005-10-21 | 2005-10-21 | |
| US60/728,924 | 2005-10-21 | ||
| US11/444,150 | 2006-05-30 | ||
| US11/444,150 US7875602B2 (en) | 2005-10-21 | 2006-05-30 | Camptothecin derivatives as chemoradiosensitizing agents |
| PCT/US2006/041175 WO2007048002A2 (en) | 2005-10-21 | 2006-10-19 | Camptothecin derivatives as chemoradiosensitizing agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009512714A JP2009512714A (ja) | 2009-03-26 |
| JP2009512714A5 true JP2009512714A5 (enExample) | 2009-12-03 |
| JP5328357B2 JP5328357B2 (ja) | 2013-10-30 |
Family
ID=37963356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008536850A Expired - Fee Related JP5328357B2 (ja) | 2005-10-21 | 2006-10-19 | 化学放射線増感剤としてのカンプトテシン誘導体 |
Country Status (11)
| Country | Link |
|---|---|
| US (3) | US7875602B2 (enExample) |
| EP (1) | EP1951231B1 (enExample) |
| JP (1) | JP5328357B2 (enExample) |
| KR (1) | KR101320160B1 (enExample) |
| CN (1) | CN101300009B (enExample) |
| AU (1) | AU2006304811C1 (enExample) |
| CA (1) | CA2626032C (enExample) |
| ES (1) | ES2428088T3 (enExample) |
| NZ (2) | NZ593706A (enExample) |
| TW (1) | TWI402270B (enExample) |
| WO (1) | WO2007048002A2 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101402640B (zh) * | 2008-09-02 | 2011-06-15 | 暨南大学 | 双酯化喜树碱衍生物及其制备方法和应用 |
| DE102009004204A1 (de) * | 2009-01-09 | 2010-07-15 | Christian-Albrechts-Universität Zu Kiel | Verfahren zur verbesserten Bioaktivierung von Arzneistoffen |
| US8168648B2 (en) * | 2009-03-06 | 2012-05-01 | Taiwan Liposome Co., Ltd. | Camptothecin derivatives and uses thereof |
| US8575188B2 (en) | 2009-06-17 | 2013-11-05 | Threshold Pharmaceuticals, Inc. | Camptothecin derivatives |
| US10391056B2 (en) | 2011-11-03 | 2019-08-27 | Taiwan Lipsome Company, LTD. | Pharmaceutical compositions of hydrophobic camptothecin derivatives |
| US10980798B2 (en) | 2011-11-03 | 2021-04-20 | Taiwan Liposome Company, Ltd. | Pharmaceutical compositions of hydrophobic camptothecin derivatives |
| US20140135357A1 (en) * | 2012-11-12 | 2014-05-15 | Taiwan Liposome Company, Ltd. | Dose regime for camptothecin derivatives |
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- 2006-10-19 CN CN2006800390612A patent/CN101300009B/zh not_active Expired - Fee Related
- 2006-10-19 ES ES06836448T patent/ES2428088T3/es active Active
- 2006-10-19 KR KR1020087012095A patent/KR101320160B1/ko not_active Expired - Fee Related
- 2006-10-19 AU AU2006304811A patent/AU2006304811C1/en not_active Ceased
- 2006-10-19 NZ NZ593706A patent/NZ593706A/xx not_active IP Right Cessation
- 2006-10-19 JP JP2008536850A patent/JP5328357B2/ja not_active Expired - Fee Related
- 2006-10-19 CA CA2626032A patent/CA2626032C/en active Active
- 2006-10-19 NZ NZ567454A patent/NZ567454A/en not_active IP Right Cessation
- 2006-10-19 EP EP06836448.8A patent/EP1951231B1/en active Active
- 2006-10-20 TW TW095138924A patent/TWI402270B/zh not_active IP Right Cessation
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2008
- 2008-07-29 US US12/124,712 patent/US8563537B2/en not_active Expired - Fee Related
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- 2011-01-24 US US13/012,772 patent/US8779138B2/en active Active
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