LT4944B - C-21 modifikuoti epotilonai - Google Patents

Info

Publication number

LT4944B

LT4944B LT2001086A LT2001086A LT4944B LT 4944 B LT4944 B LT 4944B LT 2001086 A LT2001086 A LT 2001086A LT 2001086 A LT2001086 A LT 2001086A LT 4944 B LT4944 B LT 4944B

Authority

LT

Lithuania

Prior art keywords

group

methyl

dione

dihydroxy

thiazolyl

Prior art date

1999-02-22

Links

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• Global Dossier
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• -1 C-21 modified epothilones Chemical class 0.000 title claims description 72
• 238000000034 method Methods 0.000 claims abstract description 13
• 239000003814 drug Substances 0.000 claims abstract description 12
• 238000002360 preparation method Methods 0.000 claims abstract description 8
• 229940124597 therapeutic agent Drugs 0.000 claims abstract description 7
• 125000000217 alkyl group Chemical group 0.000 claims description 146
• 150000001875 compounds Chemical class 0.000 claims description 120
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 93
• 125000002252 acyl group Chemical group 0.000 claims description 70
• 125000003118 aryl group Chemical group 0.000 claims description 56
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 48
• LZWPOLSJFGLQCE-UHFFFAOYSA-N heptadecane-5,9-dione Chemical compound CCCCCCCCC(=O)CCCC(=O)CCCC LZWPOLSJFGLQCE-UHFFFAOYSA-N 0.000 claims description 41
• 125000003107 substituted aryl group Chemical group 0.000 claims description 37
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
• 125000000623 heterocyclic group Chemical group 0.000 claims description 24
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 150000002367 halogens Chemical class 0.000 claims description 21
• 239000004593 Epoxy Substances 0.000 claims description 20
• 206010028980 Neoplasm Diseases 0.000 claims description 19
• 229910052739 hydrogen Inorganic materials 0.000 claims description 16
• 125000005843 halogen group Chemical group 0.000 claims description 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
• 150000003839 salts Chemical class 0.000 claims description 14
• 238000011282 treatment Methods 0.000 claims description 14
• 201000010099 disease Diseases 0.000 claims description 12
• JCBJVAJGLKENNC-UHFFFAOYSA-N potassium;ethoxymethanedithioic acid Chemical group [K+].CCOC(S)=S JCBJVAJGLKENNC-UHFFFAOYSA-N 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 10
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
• OADTZFQWKOAHJF-UHFFFAOYSA-N C=1/C(CCCC(CCCCCCCCCC1)=O)=O Chemical compound C=1/C(CCCC(CCCCCCCCCC1)=O)=O OADTZFQWKOAHJF-UHFFFAOYSA-N 0.000 claims description 9
• 201000011510 cancer Diseases 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 8
• 230000001093 anti-cancer Effects 0.000 claims description 8
• 125000003147 glycosyl group Chemical group 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 230000002062 proliferating effect Effects 0.000 claims description 8
• 229940127089 cytotoxic agent Drugs 0.000 claims description 7
• 239000002254 cytotoxic agent Substances 0.000 claims description 7
• 231100000599 cytotoxic agent Toxicity 0.000 claims description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
• 239000002246 antineoplastic agent Substances 0.000 claims description 5
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
• 230000009467 reduction Effects 0.000 claims description 5
• 239000012453 solvate Substances 0.000 claims description 5
• 125000004434 sulfur atom Chemical group 0.000 claims description 5
• WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 claims description 4
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
• 239000004480 active ingredient Substances 0.000 claims description 4
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
• 238000010534 nucleophilic substitution reaction Methods 0.000 claims description 4
• 230000004913 activation Effects 0.000 claims description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 229910052794 bromium Inorganic materials 0.000 claims description 3
• 125000001072 heteroaryl group Chemical group 0.000 claims description 3
• 150000004677 hydrates Chemical class 0.000 claims description 3
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
• 230000008569 process Effects 0.000 claims description 3
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 2
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
• 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 2
• 229910052740 iodine Inorganic materials 0.000 claims description 2
• HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 2
• 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
• DBYQXFVQRDJZLC-UHFFFAOYSA-N 13,17-dioxabicyclo[14.1.0]heptadecane-8,12-dione Chemical compound C1COC(=O)CCCC(=O)CCCCCCC2OC21 DBYQXFVQRDJZLC-UHFFFAOYSA-N 0.000 claims 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
• AGPIEXYQSXIXAQ-UHFFFAOYSA-N 1-hydroxy-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione Chemical compound CC1CCCC2(C)OC2(O)CCOC(=O)CCC(C)(C)C(=O)C(C)C1 AGPIEXYQSXIXAQ-UHFFFAOYSA-N 0.000 claims 1
• FMGNVEVLMGMCNQ-UHFFFAOYSA-N 15-oxabicyclo[14.1.0]heptadecane-8,12-dione Chemical compound O1CCC(=O)CCCC(=O)CCCCCCC2CC21 FMGNVEVLMGMCNQ-UHFFFAOYSA-N 0.000 claims 1
• 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
• NYTZJURBIUIUQY-UHFFFAOYSA-N 4-ethenyl-2-[(4-methylpiperazin-1-yl)methyl]-1,3-thiazole Chemical group C1CN(C)CCN1CC1=NC(C=C)=CS1 NYTZJURBIUIUQY-UHFFFAOYSA-N 0.000 claims 1
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
• 239000005977 Ethylene Substances 0.000 claims 1
• 239000003054 catalyst Substances 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• 238000005984 hydrogenation reaction Methods 0.000 claims 1
• 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
• 230000006882 induction of apoptosis Effects 0.000 claims 1
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims 1
• 230000014399 negative regulation of angiogenesis Effects 0.000 claims 1
• 239000008024 pharmaceutical diluent Substances 0.000 claims 1
• 229930013356 epothilone Natural products 0.000 abstract description 24
• HESCAJZNRMSMJG-KKQRBIROSA-N epothilone A Chemical class C/C([C@@H]1C[C@@H]2O[C@@H]2CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(C)=N1 HESCAJZNRMSMJG-KKQRBIROSA-N 0.000 abstract description 16
• 229940121375 antifungal agent Drugs 0.000 abstract description 3
• 230000000843 anti-fungal effect Effects 0.000 abstract description 2
• 239000003429 antifungal agent Substances 0.000 abstract description 2
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 114
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
• 239000000203 mixture Substances 0.000 description 58
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
• 239000000243 solution Substances 0.000 description 44
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 34
• 239000011541 reaction mixture Substances 0.000 description 32
• 239000002904 solvent Substances 0.000 description 32
• 239000000460 chlorine Substances 0.000 description 30
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
• 238000005160 1H NMR spectroscopy Methods 0.000 description 28
• 150000003883 epothilone derivatives Chemical class 0.000 description 26
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
• 238000006243 chemical reaction Methods 0.000 description 23
• 239000000741 silica gel Substances 0.000 description 20
• 229910002027 silica gel Inorganic materials 0.000 description 20
• 229910052786 argon Inorganic materials 0.000 description 17
• 238000003756 stirring Methods 0.000 description 17
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
• OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 15
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
• 239000011734 sodium Substances 0.000 description 13
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
• 210000004027 cell Anatomy 0.000 description 12
• 239000012044 organic layer Substances 0.000 description 12
• 230000015572 biosynthetic process Effects 0.000 description 11
• 125000001424 substituent group Chemical group 0.000 description 11
• 238000003786 synthesis reaction Methods 0.000 description 11
• 239000013058 crude material Substances 0.000 description 10
• 239000012043 crude product Substances 0.000 description 10
• 239000003921 oil Substances 0.000 description 10
• UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 9
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 9
• 238000002953 preparative HPLC Methods 0.000 description 9
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
• 150000001204 N-oxides Chemical class 0.000 description 8
• 239000002585 base Substances 0.000 description 8
• 239000003085 diluting agent Substances 0.000 description 8
• HESCAJZNRMSMJG-HGYUPSKWSA-N epothilone A Natural products O=C1[C@H](C)[C@H](O)[C@H](C)CCC[C@H]2O[C@H]2C[C@@H](/C(=C\c2nc(C)sc2)/C)OC(=O)C[C@H](O)C1(C)C HESCAJZNRMSMJG-HGYUPSKWSA-N 0.000 description 8
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 8
• 239000012074 organic phase Substances 0.000 description 8
• 229920006395 saturated elastomer Polymers 0.000 description 8
• 239000007787 solid Substances 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• UKIMCRYGLFQEOE-RLHMMOOASA-N (-)-Epothilone F Natural products O=C1[C@H](C)[C@H](O)[C@@H](C)CCC[C@@]2(C)O[C@H]2C[C@@H](/C(=C\c2nc(CO)sc2)/C)OC(=O)C[C@H](O)C1(C)C UKIMCRYGLFQEOE-RLHMMOOASA-N 0.000 description 7
• UKIMCRYGLFQEOE-UHFFFAOYSA-N Epothilone F Natural products O1C(=O)CC(O)C(C)(C)C(=O)C(C)C(O)C(C)CCCC2(C)OC2CC1C(C)=CC1=CSC(CO)=N1 UKIMCRYGLFQEOE-UHFFFAOYSA-N 0.000 description 7
• 239000003795 chemical substances by application Substances 0.000 description 7
• UKIMCRYGLFQEOE-RGJAOAFDSA-N epothilone f Chemical compound C/C([C@@H]1C[C@@H]2O[C@]2(C)CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(CO)=N1 UKIMCRYGLFQEOE-RGJAOAFDSA-N 0.000 description 7
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
• XTEOJPUYZWEXFI-UHFFFAOYSA-N butyl n-[3-[4-(imidazol-1-ylmethyl)phenyl]-5-(2-methylpropyl)thiophen-2-yl]sulfonylcarbamate Chemical compound S1C(CC(C)C)=CC(C=2C=CC(CN3C=NC=C3)=CC=2)=C1S(=O)(=O)NC(=O)OCCCC XTEOJPUYZWEXFI-UHFFFAOYSA-N 0.000 description 6
• 229940125782 compound 2 Drugs 0.000 description 6
• 229940125810 compound 20 Drugs 0.000 description 6
• 125000004122 cyclic group Chemical group 0.000 description 6
• JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 6
• 239000001257 hydrogen Substances 0.000 description 6
• 229910052757 nitrogen Inorganic materials 0.000 description 6
• 229940002612 prodrug Drugs 0.000 description 6
• 239000000651 prodrug Substances 0.000 description 6
• 239000003381 stabilizer Substances 0.000 description 6
• XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 5
• WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 5
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
• NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 5
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
• 125000003710 aryl alkyl group Chemical group 0.000 description 5
• 125000004432 carbon atom Chemical group C* 0.000 description 5
• 229940125773 compound 10 Drugs 0.000 description 5
• 238000010586 diagram Methods 0.000 description 5
• 125000005842 heteroatom Chemical group 0.000 description 5
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
• ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 5
• 239000007858 starting material Substances 0.000 description 5
• FCCNKYGSMOSYPV-DEDISHTHSA-N (-)-Epothilone E Natural products O=C1[C@H](C)[C@H](O)[C@@H](C)CCC[C@H]2O[C@H]2C[C@@H](/C(=C\c2nc(CO)sc2)/C)OC(=O)C[C@H](O)C1(C)C FCCNKYGSMOSYPV-DEDISHTHSA-N 0.000 description 4
• PFJFPBDHCFMQPN-RGJAOAFDSA-N (1s,3s,7s,10r,11s,12s,16r)-3-[(e)-1-[2-(aminomethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl]-7,11-dihydroxy-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione Chemical compound C/C([C@@H]1C[C@@H]2O[C@]2(C)CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(CN)=N1 PFJFPBDHCFMQPN-RGJAOAFDSA-N 0.000 description 4
• IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 4
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
• 239000002253 acid Substances 0.000 description 4
• RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 4
• 125000003545 alkoxy group Chemical group 0.000 description 4
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 4
• 239000011230 binding agent Substances 0.000 description 4
• 125000001589 carboacyl group Chemical group 0.000 description 4
• 150000001732 carboxylic acid derivatives Chemical group 0.000 description 4
• 238000002285 desorption chemical ionisation mass spectrometry Methods 0.000 description 4
• 229940079593 drug Drugs 0.000 description 4
• FCCNKYGSMOSYPV-UHFFFAOYSA-N epothilone E Natural products O1C(=O)CC(O)C(C)(C)C(=O)C(C)C(O)C(C)CCCC2OC2CC1C(C)=CC1=CSC(CO)=N1 FCCNKYGSMOSYPV-UHFFFAOYSA-N 0.000 description 4
• FCCNKYGSMOSYPV-OKOHHBBGSA-N epothilone e Chemical compound C/C([C@@H]1C[C@@H]2O[C@@H]2CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(CO)=N1 FCCNKYGSMOSYPV-OKOHHBBGSA-N 0.000 description 4
• 125000003700 epoxy group Chemical group 0.000 description 4
• 238000001704 evaporation Methods 0.000 description 4
• 230000008020 evaporation Effects 0.000 description 4
• 238000004128 high performance liquid chromatography Methods 0.000 description 4
• 230000003647 oxidation Effects 0.000 description 4
• 238000007254 oxidation reaction Methods 0.000 description 4
• 239000003755 preservative agent Substances 0.000 description 4
• 238000006722 reduction reaction Methods 0.000 description 4
• 239000003826 tablet Substances 0.000 description 4
• 125000000335 thiazolyl group Chemical group 0.000 description 4
• 238000004809 thin layer chromatography Methods 0.000 description 4
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
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