MXPA03006405A - Derivados de camptotecina. - Google Patents
Derivados de camptotecina.Info
- Publication number
- MXPA03006405A MXPA03006405A MXPA03006405A MXPA03006405A MXPA03006405A MX PA03006405 A MXPA03006405 A MX PA03006405A MX PA03006405 A MXPA03006405 A MX PA03006405A MX PA03006405 A MXPA03006405 A MX PA03006405A MX PA03006405 A MXPA03006405 A MX PA03006405A
- Authority
- MX
- Mexico
- Prior art keywords
- cpt
- hydroxy
- further characterized
- compound according
- amino
- Prior art date
Links
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical class C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 title abstract description 623
- 150000001875 compounds Chemical class 0.000 claims abstract description 205
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 54
- 201000011510 cancer Diseases 0.000 claims abstract description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 228
- -1 cyano, nitro, amino Chemical group 0.000 claims description 203
- 125000000217 alkyl group Chemical group 0.000 claims description 141
- 125000003545 alkoxy group Chemical group 0.000 claims description 110
- 239000000203 mixture Substances 0.000 claims description 85
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 60
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 55
- 229910052736 halogen Inorganic materials 0.000 claims description 51
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 44
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 44
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 41
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 41
- 125000001424 substituent group Chemical group 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 150000002367 halogens Chemical group 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 24
- 150000002431 hydrogen Chemical group 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 241001465754 Metazoa Species 0.000 claims description 11
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 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 claims description 7
- 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 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 238000001990 intravenous administration Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 238000007918 intramuscular administration Methods 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 claims 1
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000007822 coupling agent Substances 0.000 claims 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical group ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
- 229940127093 camptothecin Drugs 0.000 abstract description 830
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 abstract description 764
- 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 abstract description 764
- 239000002253 acid Substances 0.000 abstract description 36
- 150000002148 esters Chemical class 0.000 abstract description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 168
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 60
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 44
- 239000002904 solvent Substances 0.000 description 44
- 229920006395 saturated elastomer Polymers 0.000 description 42
- 239000000243 solution Substances 0.000 description 40
- 239000000126 substance Substances 0.000 description 40
- 239000002502 liposome Substances 0.000 description 39
- 230000002829 reductive effect Effects 0.000 description 37
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 238000004458 analytical method Methods 0.000 description 36
- 239000012267 brine Substances 0.000 description 35
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 35
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 30
- 235000019341 magnesium sulphate Nutrition 0.000 description 30
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 30
- 239000007787 solid Substances 0.000 description 30
- FBDOJYYTMIHHDH-OZBJMMHXSA-N (19S)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-2,4,6,8,10,14,20-heptaen-18-one Chemical compound CC[C@@]1(O)C(=O)OCC2=CN3Cc4cc5ccccc5nc4C3C=C12 FBDOJYYTMIHHDH-OZBJMMHXSA-N 0.000 description 29
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 29
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 29
- UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 description 29
- 229960000303 topotecan Drugs 0.000 description 29
- FUXVKZWTXQUGMW-FQEVSTJZSA-N 9-Aminocamptothecin Chemical compound C1=CC(N)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 FUXVKZWTXQUGMW-FQEVSTJZSA-N 0.000 description 28
- 239000007864 aqueous solution Substances 0.000 description 28
- 210000004027 cell Anatomy 0.000 description 28
- 238000004440 column chromatography Methods 0.000 description 28
- 239000003480 eluent Substances 0.000 description 28
- 239000012044 organic layer Substances 0.000 description 28
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 27
- 229960004768 irinotecan Drugs 0.000 description 26
- GURKHSYORGJETM-WAQYZQTGSA-N irinotecan hydrochloride (anhydrous) Chemical compound Cl.C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 GURKHSYORGJETM-WAQYZQTGSA-N 0.000 description 26
- 150000003254 radicals Chemical class 0.000 description 26
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 23
- 239000012528 membrane Substances 0.000 description 23
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 23
- 241000699670 Mus sp. Species 0.000 description 22
- 235000017557 sodium bicarbonate Nutrition 0.000 description 22
- 230000015572 biosynthetic process Effects 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 239000003814 drug Substances 0.000 description 16
- 150000002632 lipids Chemical class 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 229940079593 drug Drugs 0.000 description 15
- 229910000027 potassium carbonate Inorganic materials 0.000 description 15
- 239000000693 micelle Substances 0.000 description 14
- 231100000419 toxicity Toxicity 0.000 description 14
- 230000001988 toxicity Effects 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- OHPMDIAHFMBXQX-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yloxy)acetic acid Chemical compound OC(=O)COC1=CC=C2OCOC2=C1 OHPMDIAHFMBXQX-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 230000004083 survival effect Effects 0.000 description 8
- GSSWQWTVYDDKER-UHFFFAOYSA-N 2-quinolin-4-yloxyacetic acid Chemical compound C1=CC=C2C(OCC(=O)O)=CC=NC2=C1 GSSWQWTVYDDKER-UHFFFAOYSA-N 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 230000002427 irreversible effect Effects 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- OPQIOIYLAKHILI-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yloxy)acetic acid Chemical compound C1=CC=C2SC(OCC(=O)O)=NC2=C1 OPQIOIYLAKHILI-UHFFFAOYSA-N 0.000 description 6
- VRJLOBMJAAAJSB-UHFFFAOYSA-N 2-(4-cyano-3-fluorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(C#N)C(F)=C1 VRJLOBMJAAAJSB-UHFFFAOYSA-N 0.000 description 6
- FMMDNTXLWDHKSS-UHFFFAOYSA-N 2-[4-nitro-3-(trifluoromethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 FMMDNTXLWDHKSS-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- HLXKPIIPUSQUSR-UHFFFAOYSA-N 2-(2,6-dichloro-4-fluorophenoxy)acetic acid Chemical compound OC(=O)COC1=C(Cl)C=C(F)C=C1Cl HLXKPIIPUSQUSR-UHFFFAOYSA-N 0.000 description 5
- KMLUCDZQWFPSAT-UHFFFAOYSA-N 2-(2-iodo-6-methylpyridin-3-yl)oxyacetic acid Chemical compound CC1=CC=C(OCC(O)=O)C(I)=N1 KMLUCDZQWFPSAT-UHFFFAOYSA-N 0.000 description 5
- BHFSBJHPPFJCOS-UHFFFAOYSA-N 2-(4-methoxyphenoxy)acetic acid Chemical compound COC1=CC=C(OCC(O)=O)C=C1 BHFSBJHPPFJCOS-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000012010 growth Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 238000001727 in vivo Methods 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 238000007912 intraperitoneal administration Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- WGUJIFSGTIEUPS-UHFFFAOYSA-N 1-methyl-5-propan-2-ylpyrazole-3-carboxylic acid Chemical compound CC(C)C1=CC(C(O)=O)=NN1C WGUJIFSGTIEUPS-UHFFFAOYSA-N 0.000 description 4
- SMXPFEBIAASLOR-UHFFFAOYSA-N 2-(2,3,4,5,6-pentafluorophenoxy)acetic acid Chemical compound OC(=O)COC1=C(F)C(F)=C(F)C(F)=C1F SMXPFEBIAASLOR-UHFFFAOYSA-N 0.000 description 4
- RBJIGQRZLITQJG-UHFFFAOYSA-N 2-(2,3-dichlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=CC(Cl)=C1Cl RBJIGQRZLITQJG-UHFFFAOYSA-N 0.000 description 4
- MXLOCRJKRZBQBM-UHFFFAOYSA-N 2-(3-chloro-4-methyl-2-oxochromen-7-yl)oxyacetic acid Chemical compound C1=C(OCC(O)=O)C=CC2=C1OC(=O)C(Cl)=C2C MXLOCRJKRZBQBM-UHFFFAOYSA-N 0.000 description 4
- SZEBGAQWWSUOHT-UHFFFAOYSA-N 2-(4-bromophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(Br)C=C1 SZEBGAQWWSUOHT-UHFFFAOYSA-N 0.000 description 4
- ZBIULCVFFJJYTN-UHFFFAOYSA-N 2-(4-fluorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(F)C=C1 ZBIULCVFFJJYTN-UHFFFAOYSA-N 0.000 description 4
- OYNIIKHNXNPSAG-UHFFFAOYSA-N 2-(4-formylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(C=O)C=C1 OYNIIKHNXNPSAG-UHFFFAOYSA-N 0.000 description 4
- RKORKXFKXYYHAQ-UHFFFAOYSA-N 2-(4-iodophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(I)C=C1 RKORKXFKXYYHAQ-UHFFFAOYSA-N 0.000 description 4
- SFTDDFBJWUWKMN-UHFFFAOYSA-N 2-(4-methylphenoxy)acetic acid Chemical compound CC1=CC=C(OCC(O)=O)C=C1 SFTDDFBJWUWKMN-UHFFFAOYSA-N 0.000 description 4
- MSTODKGDFXWAIO-UHFFFAOYSA-N 2-[3-(bromomethyl)phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=CC(CBr)=C1 MSTODKGDFXWAIO-UHFFFAOYSA-N 0.000 description 4
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 4
- RZCJYMOBWVJQGV-UHFFFAOYSA-N 2-naphthyloxyacetic acid Chemical compound C1=CC=CC2=CC(OCC(=O)O)=CC=C21 RZCJYMOBWVJQGV-UHFFFAOYSA-N 0.000 description 4
- LABJFIBQJFPXHZ-UHFFFAOYSA-N 4-(carboxymethoxy)benzoic acid Chemical compound OC(=O)COC1=CC=C(C(O)=O)C=C1 LABJFIBQJFPXHZ-UHFFFAOYSA-N 0.000 description 4
- GKBDXTNCBPZMFX-UHFFFAOYSA-N 4-(trifluoromethyl)benzohydrazide Chemical compound NNC(=O)C1=CC=C(C(F)(F)F)C=C1 GKBDXTNCBPZMFX-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000002246 antineoplastic agent Substances 0.000 description 4
- 229940041181 antineoplastic drug Drugs 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- BPHQZTVXXXJVHI-UHFFFAOYSA-N dimyristoyl phosphatidylglycerol Chemical compound CCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCCCCCCCC BPHQZTVXXXJVHI-UHFFFAOYSA-N 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 150000002596 lactones Chemical class 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 239000011593 sulfur Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- FPVCSFOUVDLTDG-UHFFFAOYSA-N 2-(4-propan-2-ylphenoxy)acetic acid Chemical compound CC(C)C1=CC=C(OCC(O)=O)C=C1 FPVCSFOUVDLTDG-UHFFFAOYSA-N 0.000 description 3
- CILPHQCEVYJUDN-VWYCJHECSA-N 2-[(1s,2s,5r)-5-methyl-2-propan-2-ylcyclohexyl]oxyacetic acid Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1OCC(O)=O CILPHQCEVYJUDN-VWYCJHECSA-N 0.000 description 3
- REIVHYDACHXPNH-UHFFFAOYSA-N 2-fluoro-4-hydroxybenzonitrile Chemical compound OC1=CC=C(C#N)C(F)=C1 REIVHYDACHXPNH-UHFFFAOYSA-N 0.000 description 3
- AJQOASGWDCBKCJ-UHFFFAOYSA-N Butoxyacetic acid Chemical compound CCCCOCC(O)=O AJQOASGWDCBKCJ-UHFFFAOYSA-N 0.000 description 3
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
-
- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4738—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4745—Quinolines; Isoquinolines ortho- or peri-condensed with heterocyclic ring systems condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines
-
- 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)
- 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26304001P | 2001-01-18 | 2001-01-18 | |
| US09/797,769 US6350756B1 (en) | 2001-01-18 | 2001-03-01 | Camptothecin derivatives |
| PCT/US2001/050288 WO2002056885A1 (en) | 2001-01-18 | 2001-12-20 | Camptothecin derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA03006405A true MXPA03006405A (es) | 2004-12-02 |
Family
ID=26949624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA03006405A MXPA03006405A (es) | 2001-01-18 | 2001-12-20 | Derivados de camptotecina. |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US6350756B1 (https=) |
| EP (1) | EP1353673B1 (https=) |
| JP (1) | JP4243484B2 (https=) |
| KR (1) | KR100879489B1 (https=) |
| CN (1) | CN100406013C (https=) |
| AT (1) | ATE359786T1 (https=) |
| AU (1) | AU2002243367B2 (https=) |
| CA (1) | CA2434747C (https=) |
| DE (1) | DE60128003T2 (https=) |
| ES (1) | ES2284716T3 (https=) |
| IL (2) | IL156967A0 (https=) |
| MX (1) | MXPA03006405A (https=) |
| NZ (1) | NZ527078A (https=) |
| WO (1) | WO2002056885A1 (https=) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6350756B1 (en) | 2001-01-18 | 2002-02-26 | California Pacific Medical Center | Camptothecin derivatives |
| US6855720B2 (en) * | 2001-03-01 | 2005-02-15 | California Pacific Medical Center | Nitrogen-based camptothecin derivatives |
| US6403604B1 (en) * | 2001-03-01 | 2002-06-11 | California Pacific Medical Center | Nitrogen-based camptothecin derivatives |
| US6699875B2 (en) * | 2002-05-06 | 2004-03-02 | The Stehlin Foundation For Cancer Research | Cascade esters of camptothecins and methods of treating cancer using these compounds |
| US6703399B2 (en) | 2002-05-06 | 2004-03-09 | The Stehlin Foundation For Cancer Research | Halo-alkyl esters of camptothecins and methods of treating cancer using these compounds |
| US6933302B2 (en) * | 2002-06-03 | 2005-08-23 | California Pacific Medical Center | Nitrogen-based homo-camptothecin derivatives |
| AU2003243397A1 (en) * | 2002-06-03 | 2003-12-19 | California Pacific Medical Center | Homo-camptothecin derivatives |
| US20050129719A1 (en) * | 2003-12-15 | 2005-06-16 | Yu-Fang Hu | Concentrated emulsion formulation for silatecan |
| RU2413731C2 (ru) * | 2004-04-09 | 2011-03-10 | Чугаи Сейяку Кабусики Кайся | Новые растворимые в воде пролекарства |
| US20060003976A1 (en) * | 2004-06-04 | 2006-01-05 | Yuehua Zhang | Cholesterol/bile acid/bile acid derivative-modified therapeutic drug compounds |
| TW200744603A (en) | 2005-08-22 | 2007-12-16 | Chugai Pharmaceutical Co Ltd | Novel anticancer concomitant drug |
| US20090105202A1 (en) * | 2005-10-20 | 2009-04-23 | California Pacific Medical Center | Androsterone Derivatives and Method of Use thereof |
| US7875602B2 (en) * | 2005-10-21 | 2011-01-25 | Sutter West Bay Hospitals | Camptothecin derivatives as chemoradiosensitizing agents |
| WO2012134446A1 (en) * | 2011-03-29 | 2012-10-04 | SUTTER WEST BAY HOSPITALS doing business as CALIFORNIA PACIFIC MEDICAL CENTER | Epiandrosterone and/or androsterone derivatives and method of use thereof |
| TWI549679B (zh) | 2011-11-03 | 2016-09-21 | 台灣微脂體股份有限公司 | 疏水性喜樹鹼衍生物之醫藥組合物 |
| US10980798B2 (en) | 2011-11-03 | 2021-04-20 | Taiwan Liposome Company, Ltd. | Pharmaceutical compositions of hydrophobic camptothecin derivatives |
| CN102516258B (zh) * | 2011-11-11 | 2014-06-25 | 正大天晴药业集团股份有限公司 | 水溶性维生素e衍生物修饰的脂溶性抗癌药物化合物和制剂、该化合物的制备方法及应用 |
| CN104163823B (zh) * | 2014-04-30 | 2016-03-09 | 浙江工业大学 | 一种喜树碱与青蒿琥酯偶联物及其制备方法与应用 |
| CN110590796B (zh) * | 2018-06-12 | 2022-07-15 | 青岛海洋生物医药研究院股份有限公司 | 喜树碱衍生物及其制备方法和应用 |
| MX2022000474A (es) | 2019-07-11 | 2022-03-11 | Sun Pharma Advanced Res Co Ltd | Derivados de camptotecina con un resto disulfuro y un resto piperazina. |
| TW202547842A (zh) | 2021-04-29 | 2025-12-16 | 愛爾蘭商艾伯維製造管理無限公司 | 抗c-Met抗體藥物結合物 |
| WO2023150899A1 (en) * | 2022-02-08 | 2023-08-17 | Canwell Biotech Limited | Conjugates of chemotherapy agents and tissue-binding small molecules, compositions and methods thereof |
| PE20252282A1 (es) | 2022-10-09 | 2025-09-18 | Lanova Medicines Ltd | Compuestos, composiciones y metodos |
| CN117285540B (zh) * | 2023-09-27 | 2025-07-11 | 中国海洋大学 | 12-位取代的喜树碱衍生物及其用途 |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4399282A (en) * | 1979-07-10 | 1983-08-16 | Kabushiki Kaisha Yakult Honsha | Camptothecin derivatives |
| US4943579A (en) | 1987-10-06 | 1990-07-24 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Water soluble prodrugs of camptothecin |
| JP2524803B2 (ja) * | 1988-03-29 | 1996-08-14 | 株式会社ヤクルト本社 | 新規なカンプトテシン誘導体およびその製造法 |
| JP2524804B2 (ja) * | 1988-03-29 | 1996-08-14 | 株式会社ヤクルト本社 | 新規なカンプトテシン誘導体及びその製造法 |
| GB9320781D0 (en) | 1993-10-08 | 1993-12-01 | Erba Carlo Spa | Polymer-bound camptothecin derivatives |
| US5965566A (en) | 1993-10-20 | 1999-10-12 | Enzon, Inc. | High molecular weight polymer-based prodrugs |
| US5919455A (en) | 1993-10-27 | 1999-07-06 | Enzon, Inc. | Non-antigenic branched polymer conjugates |
| US5646159A (en) | 1994-07-20 | 1997-07-08 | Research Triangle Institute | Water-soluble esters of camptothecin compounds |
| GB9504065D0 (en) | 1995-03-01 | 1995-04-19 | Pharmacia Spa | Poly-pyrrolecarboxamidonaphthalenic acid derivatives |
| JPH08333370A (ja) | 1995-06-08 | 1996-12-17 | Kyorin Pharmaceut Co Ltd | 水に可溶な新規フルオロエチルカンプトテシン誘導体、及びその製造方法 |
| US6339091B1 (en) | 1995-06-21 | 2002-01-15 | Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R.A.S.) | Comptothecin analogues, preparation methods therefor, use thereof as drugs, and pharmaceutical compositions containing said analogues |
| AU7732996A (en) | 1995-11-22 | 1997-06-11 | Research Triangle Institute | Camptothecin compounds with combined topoisomerase i inhibition and dna alkylation properties |
| US6096336A (en) | 1996-01-30 | 2000-08-01 | The Stehlin Foundation For Cancer Research | Liposomal prodrugs comprising derivatives of camptothecin and methods of treating cancer using these prodrugs |
| US5731316A (en) | 1996-01-30 | 1998-03-24 | The Stehlin Foundation For Cancer Research | Derivatives of camptothecin and methods of treating cancer using these derivatives |
| IL127800A (en) | 1996-08-19 | 2005-11-20 | Bionumerik Pharmaceuticals Inc | Highly lipophilic 7-substituted camptothecin derivatives and pharmaceutical compositions containing them |
| EP0961619A4 (en) | 1996-09-27 | 2001-09-26 | Bristol Myers Squibb Co | HYDROLYSABLE DRUGS FOR THE RELEASE OF ANTI-CANCER DRUGS IN METASTATIC CELLS |
| ATE210673T1 (de) | 1996-09-30 | 2001-12-15 | Bayer Ag | Glycokonjugate von modifizierten camptothecin- derivaten (20-o-verknüpfung) |
| TW464652B (en) | 1996-10-30 | 2001-11-21 | Tanabe Seiyaku Co | S type 2-substituted hydroxy-2-indolidinylbutyric ester compounds and process for preparation thereof |
| UA57757C2 (uk) | 1996-12-20 | 2003-07-15 | Сос'Єте Де Консей Де Решерш Е Даплікасьон С'Єнтіфік (С.К.Р.А.С.) | Аналоги камптотецину, спосіб їх отримання (варіанти) і фармацевтична композиція |
| US6169080B1 (en) * | 1997-02-13 | 2001-01-02 | Bionumerik Pharmaceuticals, Inc. | Highly lipophilic camptothecin derivatives |
| ATE329903T1 (de) * | 1997-02-14 | 2006-07-15 | Bionumerik Pharmaceuticals Inc | Hochgradig lipophile camptothecin-derivate |
| ID23424A (id) | 1997-05-14 | 2000-04-20 | Bayer Ag | Glikokonjugat dari 20(s)-kamptotesin |
| GB9721070D0 (en) | 1997-10-03 | 1997-12-03 | Pharmacia & Upjohn Spa | Bioactive derivatives of camptothecin |
| US6153655A (en) | 1998-04-17 | 2000-11-28 | Enzon, Inc. | Terminally-branched polymeric linkers and polymeric conjugates containing the same |
| US6057303A (en) | 1998-10-20 | 2000-05-02 | Bionumerik Pharmaceuticals, Inc. | Highly lipophilic Camptothecin derivatives |
| US6207832B1 (en) | 1999-04-09 | 2001-03-27 | University Of Pittsburgh | Camptothecin analogs and methods of preparation thereof |
| WO2000066127A1 (en) | 1999-05-04 | 2000-11-09 | Bionumerik Pharmaceuticals, Inc. | Novel highly lipophilic camptothecin analogs |
| US6765019B1 (en) | 1999-05-06 | 2004-07-20 | University Of Kentucky Research Foundation | Permeable, water soluble, non-irritating prodrugs of chemotherapeutic agents with oxaalkanoic acids |
| US6350756B1 (en) | 2001-01-18 | 2002-02-26 | California Pacific Medical Center | Camptothecin derivatives |
| US6403604B1 (en) | 2001-03-01 | 2002-06-11 | California Pacific Medical Center | Nitrogen-based camptothecin derivatives |
| GB0119578D0 (en) | 2001-08-10 | 2001-10-03 | Pharmacia & Upjohn Spa | Fluoro linkers |
-
2001
- 2001-03-01 US US09/797,769 patent/US6350756B1/en not_active Ceased
- 2001-12-20 NZ NZ527078A patent/NZ527078A/en not_active IP Right Cessation
- 2001-12-20 EP EP01989260A patent/EP1353673B1/en not_active Expired - Lifetime
- 2001-12-20 ES ES01989260T patent/ES2284716T3/es not_active Expired - Lifetime
- 2001-12-20 AT AT01989260T patent/ATE359786T1/de not_active IP Right Cessation
- 2001-12-20 AU AU2002243367A patent/AU2002243367B2/en not_active Ceased
- 2001-12-20 MX MXPA03006405A patent/MXPA03006405A/es active IP Right Grant
- 2001-12-20 JP JP2002557393A patent/JP4243484B2/ja not_active Expired - Fee Related
- 2001-12-20 KR KR1020037009586A patent/KR100879489B1/ko not_active Expired - Fee Related
- 2001-12-20 DE DE60128003T patent/DE60128003T2/de not_active Expired - Lifetime
- 2001-12-20 CN CNB018227384A patent/CN100406013C/zh not_active Expired - Fee Related
- 2001-12-20 CA CA2434747A patent/CA2434747C/en not_active Expired - Fee Related
- 2001-12-20 WO PCT/US2001/050288 patent/WO2002056885A1/en not_active Ceased
- 2001-12-20 IL IL15696701A patent/IL156967A0/xx unknown
-
2003
- 2003-01-16 US US10/346,835 patent/USRE39707E1/en not_active Expired - Lifetime
- 2003-07-16 IL IL156967A patent/IL156967A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2434747C (en) | 2012-02-07 |
| JP4243484B2 (ja) | 2009-03-25 |
| ES2284716T3 (es) | 2007-11-16 |
| IL156967A (en) | 2009-08-03 |
| CN100406013C (zh) | 2008-07-30 |
| CA2434747A1 (en) | 2002-07-25 |
| JP2004521105A (ja) | 2004-07-15 |
| ATE359786T1 (de) | 2007-05-15 |
| WO2002056885A1 (en) | 2002-07-25 |
| KR100879489B1 (ko) | 2009-01-20 |
| IL156967A0 (en) | 2004-02-08 |
| AU2002243367B2 (en) | 2006-10-05 |
| DE60128003T2 (de) | 2007-12-27 |
| DE60128003D1 (en) | 2007-05-31 |
| EP1353673B1 (en) | 2007-04-18 |
| CN1553802A (zh) | 2004-12-08 |
| US6350756B1 (en) | 2002-02-26 |
| NZ527078A (en) | 2005-12-23 |
| EP1353673A1 (en) | 2003-10-22 |
| USRE39707E1 (en) | 2007-06-26 |
| KR20040035588A (ko) | 2004-04-29 |
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| Date | Code | Title | Description |
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| FG | Grant or registration |