IL138590A

IL138590A - Antitumor factors

Antitumor factors

Info

Publication number: IL138590A
Authority: IL; Israel
Prior art keywords: alkyl; alkoxy; methyl; hydrogen; amino
Prior art date: 1998-03-20

Application number

IL13859099A

Other languages

English (en)

Hebrew (he)

Other versions

IL138590A0 (en

Original Assignee

Astrazeneca Ab

Priority date

1998-03-20

Filing date

1999-03-16

Publication date

2004-08-31

1999-03-16 Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab

2001-10-31 Publication of IL138590A0 publication Critical patent/IL138590A0/xx

2004-08-31 Publication of IL138590A publication Critical patent/IL138590A/en

Links

230000000259 anti-tumor effect Effects 0.000 title claims abstract description 49
125000000217 alkyl group Chemical group 0.000 claims abstract description 183
-1 benzensulphonyloxy Chemical group 0.000 claims abstract description 154
125000003545 alkoxy group Chemical group 0.000 claims abstract description 104
239000001257 hydrogen Substances 0.000 claims abstract description 73
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 73
239000003795 chemical substances by application Substances 0.000 claims abstract description 42
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 41
150000002431 hydrogen Chemical group 0.000 claims abstract description 36
150000003839 salts Chemical class 0.000 claims abstract description 34
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
125000005843 halogen group Chemical group 0.000 claims abstract description 15
125000003342 alkenyl group Chemical group 0.000 claims abstract description 13
125000000304 alkynyl group Chemical group 0.000 claims abstract description 12
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 11
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 11
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
125000005277 alkyl imino group Chemical group 0.000 claims abstract description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 5
125000001424 substituent group Chemical group 0.000 claims abstract description 5
125000005115 alkyl carbamoyl group Chemical group 0.000 claims abstract description 4
125000005133 alkynyloxy group Chemical group 0.000 claims abstract description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
125000005236 alkanoylamino group Chemical group 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 75
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 46
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 38
238000000034 method Methods 0.000 claims description 27
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 23
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 20
230000009467 reduction Effects 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 18
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
239000007858 starting material Substances 0.000 claims description 18
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 14
241001465754 Metazoa Species 0.000 claims description 13
125000001153 fluoro group Chemical group F* 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
230000008569 process Effects 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 6
125000004154 1,4-benzoquinonyl group Chemical group C1(C(=CC(C=C1)=O)*)=O 0.000 claims description 5
230000001028 anti-proliverative effect Effects 0.000 claims description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 4
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 3
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
125000002346 iodo group Chemical group I* 0.000 claims description 3
GFWZPTGIVKRQNM-UHFFFAOYSA-N n,3-dimethylbutanamide Chemical compound CNC(=O)CC(C)C GFWZPTGIVKRQNM-UHFFFAOYSA-N 0.000 claims description 3
DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
OLLZXQIFCRIRMH-UHFFFAOYSA-N n-methylbutanamide Chemical compound CCCC(=O)NC OLLZXQIFCRIRMH-UHFFFAOYSA-N 0.000 claims 1
125000003302 alkenyloxy group Chemical group 0.000 abstract description 3
125000004414 alkyl thio group Chemical group 0.000 abstract description 2
229910052757 nitrogen Inorganic materials 0.000 abstract description 2
239000000203 mixture Substances 0.000 description 88
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 81
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 65
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 41
239000000243 solution Substances 0.000 description 39
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 35
101150041968 CDC13 gene Proteins 0.000 description 32
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 32
238000012360 testing method Methods 0.000 description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
206010028980 Neoplasm Diseases 0.000 description 25
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
210000004027 cell Anatomy 0.000 description 22
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 21
238000004440 column chromatography Methods 0.000 description 20
239000003480 eluent Substances 0.000 description 20
239000000377 silicon dioxide Substances 0.000 description 20
238000011282 treatment Methods 0.000 description 20
239000012074 organic phase Substances 0.000 description 18
239000000463 material Substances 0.000 description 16
229940127089 cytotoxic agent Drugs 0.000 description 15
239000002254 cytotoxic agent Substances 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
206010021143 Hypoxia Diseases 0.000 description 14
229910052943 magnesium sulfate Inorganic materials 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
230000000694 effects Effects 0.000 description 12
230000001146 hypoxic effect Effects 0.000 description 12
229940002612 prodrug Drugs 0.000 description 12
239000000651 prodrug Substances 0.000 description 12
239000011780 sodium chloride Substances 0.000 description 12
239000001963 growth medium Substances 0.000 description 11
239000011369 resultant mixture Substances 0.000 description 11
229920006395 saturated elastomer Polymers 0.000 description 11
239000003208 petroleum Substances 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
231100000599 cytotoxic agent Toxicity 0.000 description 9
125000006239 protecting group Chemical group 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
241001529936 Murinae Species 0.000 description 7
230000001472 cytotoxic effect Effects 0.000 description 7
125000004356 hydroxy functional group Chemical group O* 0.000 description 7
238000001819 mass spectrum Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
108020004414 DNA Proteins 0.000 description 6
102000053602 DNA Human genes 0.000 description 6
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 6
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
125000002252 acyl group Chemical group 0.000 description 6
238000013459 approach Methods 0.000 description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
210000000481 breast Anatomy 0.000 description 6
231100000433 cytotoxic Toxicity 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
239000001301 oxygen Substances 0.000 description 6
229910052760 oxygen Inorganic materials 0.000 description 6
239000003826 tablet Substances 0.000 description 6
BVYCLBMEDGNBRV-UHFFFAOYSA-N 4-n,4-n-bis(2-chloroethyl)-1-n-methylbenzene-1,4-diamine;dihydrochloride Chemical compound Cl.Cl.CNC1=CC=C(N(CCCl)CCCl)C=C1 BVYCLBMEDGNBRV-UHFFFAOYSA-N 0.000 description 5
239000000443 aerosol Substances 0.000 description 5
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 5
239000000499 gel Substances 0.000 description 5
239000003112 inhibitor Substances 0.000 description 5
239000003921 oil Substances 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
239000000047 product Substances 0.000 description 5
239000012258 stirred mixture Substances 0.000 description 5
210000001519 tissue Anatomy 0.000 description 5
239000004338 Dichlorodifluoromethane Substances 0.000 description 4
241000282414 Homo sapiens Species 0.000 description 4
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
239000004147 Sorbitan trioleate Substances 0.000 description 4
PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000000872 buffer Substances 0.000 description 4
201000011510 cancer Diseases 0.000 description 4
239000002775 capsule Substances 0.000 description 4
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 4
235000019404 dichlorodifluoromethane Nutrition 0.000 description 4
239000007924 injection Substances 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000008101 lactose Substances 0.000 description 4
239000013612 plasmid Substances 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
235000019337 sorbitan trioleate Nutrition 0.000 description 4
229960000391 sorbitan trioleate Drugs 0.000 description 4
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 4
239000012085 test solution Substances 0.000 description 4
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 4
229940029284 trichlorofluoromethane Drugs 0.000 description 4
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 3
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
VMUXSMXIQBNMGZ-UHFFFAOYSA-N 3,4-dihydrocoumarin Chemical compound C1=CC=C2OC(=O)CCC2=C1 VMUXSMXIQBNMGZ-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
241000219198 Brassica Species 0.000 description 3
235000003351 Brassica cretica Nutrition 0.000 description 3
235000003343 Brassica rupestris Nutrition 0.000 description 3
206010006187 Breast cancer Diseases 0.000 description 3
208000026310 Breast neoplasm Diseases 0.000 description 3
229920002261 Corn starch Polymers 0.000 description 3
229920002785 Croscarmellose sodium Polymers 0.000 description 3
208000012766 Growth delay Diseases 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
235000019759 Maize starch Nutrition 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
239000004037 angiogenesis inhibitor Substances 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
125000003435 aroyl group Chemical group 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
125000001589 carboacyl group Chemical group 0.000 description 3
230000032823 cell division Effects 0.000 description 3
238000002512 chemotherapy Methods 0.000 description 3
229960001681 croscarmellose sodium Drugs 0.000 description 3
235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 3
229940087091 dichlorotetrafluoroethane Drugs 0.000 description 3
DMSHWWDRAYHEBS-UHFFFAOYSA-N dihydrocoumarin Natural products C1CC(=O)OC2=C1C=C(OC)C(OC)=C2 DMSHWWDRAYHEBS-UHFFFAOYSA-N 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
125000001841 imino group Chemical group [H]N=* 0.000 description 3
238000000099 in vitro assay Methods 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
235000010460 mustard Nutrition 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
238000001959 radiotherapy Methods 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 3
239000006228 supernatant Substances 0.000 description 3
238000010998 test method Methods 0.000 description 3
239000008215 water for injection Substances 0.000 description 3
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
XGFABYCTEQAZOP-UHFFFAOYSA-N 2,3-dimethoxybenzene-1,4-diol Chemical compound COC1=C(O)C=CC(O)=C1OC XGFABYCTEQAZOP-UHFFFAOYSA-N 0.000 description 2
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 2
125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 2
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
AZKSAVLVSZKNRD-UHFFFAOYSA-M 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide Chemical compound [Br-].S1C(C)=C(C)N=C1[N+]1=NC(C=2C=CC=CC=2)=NN1C1=CC=CC=C1 AZKSAVLVSZKNRD-UHFFFAOYSA-M 0.000 description 2
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
XDPDIBVNRXJOLJ-UHFFFAOYSA-N 6-hydroxy-4,4,5,8-tetramethyl-3h-chromen-2-one Chemical compound O1C(=O)CC(C)(C)C2=C1C(C)=CC(O)=C2C XDPDIBVNRXJOLJ-UHFFFAOYSA-N 0.000 description 2
HEQKLQIMTAKRHU-UHFFFAOYSA-N 6-hydroxy-4,4,7-trimethyl-3h-chromen-2-one Chemical compound O1C(=O)CC(C)(C)C2=C1C=C(C)C(O)=C2 HEQKLQIMTAKRHU-UHFFFAOYSA-N 0.000 description 2
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 2
102000018233 Fibroblast Growth Factor Human genes 0.000 description 2
108050007372 Fibroblast Growth Factor Proteins 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
238000003820 Medium-pressure liquid chromatography Methods 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
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