TWI402270B - 作為化學輻射敏感劑之喜樹鹼衍生物 - Google Patents

Info

Publication number

TWI402270B

TWI402270B TW095138924A TW95138924A TWI402270B TW I402270 B TWI402270 B TW I402270B TW 095138924 A TW095138924 A TW 095138924A TW 95138924 A TW95138924 A TW 95138924A TW I402270 B TWI402270 B TW I402270B

Authority

TW

Taiwan

Prior art keywords

group

cpt

alkyl

hydroxy

compound

Prior art date

2005-10-21

Links

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• Global Dossier
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• 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 description 374
• -1 9-fluorenyl Chemical group 0.000 claims description 344
• 125000000217 alkyl group Chemical group 0.000 claims description 270
• 125000003545 alkoxy group Chemical group 0.000 claims description 172
• 150000001875 compounds Chemical class 0.000 claims description 172
• 229910052739 hydrogen Inorganic materials 0.000 claims description 118
• 239000001257 hydrogen Substances 0.000 claims description 114
• 206010028980 Neoplasm Diseases 0.000 claims description 106
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 89
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 75
• 125000005843 halogen group Chemical group 0.000 claims description 72
• 230000005855 radiation Effects 0.000 claims description 68
• 150000002431 hydrogen Chemical class 0.000 claims description 65
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 64
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 60
• 239000000203 mixture Substances 0.000 claims description 58
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 56
• 235000000346 sugar Nutrition 0.000 claims description 56
• 150000001412 amines Chemical class 0.000 claims description 55
• 201000011510 cancer Diseases 0.000 claims description 51
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 49
• 125000001424 substituent group Chemical group 0.000 claims description 45
• 229910052799 carbon Inorganic materials 0.000 claims description 44
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 37
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
• 229920006395 saturated elastomer Polymers 0.000 claims description 37
• 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 36
• 125000000623 heterocyclic group Chemical group 0.000 claims description 35
• ZNPKAOCQMDJBIK-UHFFFAOYSA-N nitrocyanamide Chemical compound [O-][N+](=O)NC#N ZNPKAOCQMDJBIK-UHFFFAOYSA-N 0.000 claims description 32
• 229910052760 oxygen Inorganic materials 0.000 claims description 31
• 238000011282 treatment Methods 0.000 claims description 31
• 229910052717 sulfur Inorganic materials 0.000 claims description 29
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 26
• 239000000126 substance Substances 0.000 claims description 26
• 125000003277 amino group Chemical group 0.000 claims description 25
• 239000003814 drug Substances 0.000 claims description 25
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 24
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
• 125000004122 cyclic group Chemical group 0.000 claims description 22
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
• 125000005842 heteroatom Chemical group 0.000 claims description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims description 20
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 14
• RNIXSZHNJLUJGC-UHFFFAOYSA-N hydroxy(nitro)cyanamide Chemical compound N#CN(O)[N+]([O-])=O RNIXSZHNJLUJGC-UHFFFAOYSA-N 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 229920002554 vinyl polymer Polymers 0.000 claims description 14
• 125000003118 aryl group Chemical group 0.000 claims description 13
• 239000001301 oxygen Substances 0.000 claims description 13
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
• 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 12
• JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims description 10
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
• 239000011593 sulfur Substances 0.000 claims description 10
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 9
• 125000001360 methionine group Chemical group N[C@@H](CCSC)C(=O)* 0.000 claims description 9
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 9
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 8
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
• 125000004849 alkoxymethyl group Chemical group 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• MENHXVNCWVKFRA-UHFFFAOYSA-N 1,4-oxazin-2-one Chemical compound O=C1C=NC=CO1 MENHXVNCWVKFRA-UHFFFAOYSA-N 0.000 claims description 7
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 7
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 7
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 7
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
• 125000004429 atom Chemical group 0.000 claims description 6
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 6
• 150000003839 salts Chemical class 0.000 claims description 6
• 125000002947 alkylene group Chemical group 0.000 claims description 4
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• 125000006413 ring segment Chemical group 0.000 claims description 3
• RHUYHJGZWVXEHW-UHFFFAOYSA-N 1,1-Dimethyhydrazine Chemical compound CN(C)N RHUYHJGZWVXEHW-UHFFFAOYSA-N 0.000 claims description 2
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
• 150000002576 ketones Chemical class 0.000 claims description 2
• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 2
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 13
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 6
• 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 4
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 3
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
• PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims 1
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
• PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims 1
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
• 229910052698 phosphorus Inorganic materials 0.000 claims 1
• 239000011574 phosphorus Substances 0.000 claims 1
• 229940127093 camptothecin Drugs 0.000 description 526
• 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 description 513
• KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 description 511
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 73
• 210000004027 cell Anatomy 0.000 description 59
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 52
• 239000000243 solution Substances 0.000 description 48
• 238000000034 method Methods 0.000 description 45
• 238000005481 NMR spectroscopy Methods 0.000 description 33
• 239000002502 liposome Substances 0.000 description 33
• 238000006243 chemical reaction Methods 0.000 description 32
• 235000019439 ethyl acetate Nutrition 0.000 description 29
• 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 27
• 239000002904 solvent Substances 0.000 description 27
• 210000004881 tumor cell Anatomy 0.000 description 26
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 25
• 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 description 23
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
• 238000001959 radiotherapy Methods 0.000 description 21
• 239000011734 sodium Substances 0.000 description 21
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
• 125000004414 alkyl thio group Chemical group 0.000 description 20
• 229940079593 drug Drugs 0.000 description 20
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 19
• 150000002632 lipids Chemical class 0.000 description 18
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
• 230000005865 ionizing radiation Effects 0.000 description 17
• 239000012528 membrane Substances 0.000 description 17
• 241001465754 Metazoa Species 0.000 description 16
• 125000003282 alkyl amino group Chemical group 0.000 description 16
• 125000002837 carbocyclic group Chemical group 0.000 description 16
• 230000000694 effects Effects 0.000 description 16
• 238000003786 synthesis reaction Methods 0.000 description 15
• RRSNDVCODIMOFX-MPKOGUQCSA-N Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O Chemical compound Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O RRSNDVCODIMOFX-MPKOGUQCSA-N 0.000 description 14
• CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 14
• 150000002148 esters Chemical class 0.000 description 14
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
• 229960000583 acetic acid Drugs 0.000 description 13
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 13
• 238000002360 preparation method Methods 0.000 description 13
• 239000007787 solid Substances 0.000 description 13
• 231100000419 toxicity Toxicity 0.000 description 13
• 230000001988 toxicity Effects 0.000 description 13
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• 230000000259 anti-tumor effect Effects 0.000 description 12
• 239000002534 radiation-sensitizing agent Substances 0.000 description 12
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 11
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 11
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
• 238000000354 decomposition reaction Methods 0.000 description 11
• 230000002829 reductive effect Effects 0.000 description 11
• 239000012981 Hank's balanced salt solution Substances 0.000 description 10
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 10
• 239000002552 dosage form Substances 0.000 description 10
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• UIVFUQKYVFCEKJ-OPTOVBNMSA-N gimatecan Chemical compound C1=CC=C2C(\C=N\OC(C)(C)C)=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UIVFUQKYVFCEKJ-OPTOVBNMSA-N 0.000 description 8
• 231100000682 maximum tolerated dose Toxicity 0.000 description 8
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• 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 7
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• 125000004432 carbon atom Chemical group C* 0.000 description 6
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
• 230000000973 chemotherapeutic effect Effects 0.000 description 6
• 125000002704 decyl group Chemical group [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])* 0.000 description 6
• 239000012737 fresh medium Substances 0.000 description 6
• 229910052736 halogen Inorganic materials 0.000 description 6
• 150000002367 halogens Chemical class 0.000 description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
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• 235000019260 propionic acid Nutrition 0.000 description 6
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
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• QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 description 5
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• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 5
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• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 5
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• 206010006187 Breast cancer Diseases 0.000 description 4
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• 241000699666 Mus <mouse, genus> Species 0.000 description 4
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• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
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