RU2244717C2 - Оксазоло- и тиазоло-[4,5-с] -хинолин-4-амины, промежуточные соединения, фармацевтическая композиция на их основе и способ стимулирования цитокинетического биосинтеза - Google Patents

Info

Publication number

RU2244717C2

RU2244717C2 RU2001102777/04A RU2001102777A RU2244717C2 RU 2244717 C2 RU2244717 C2 RU 2244717C2 RU 2001102777/04 A RU2001102777/04 A RU 2001102777/04A RU 2001102777 A RU2001102777 A RU 2001102777A RU 2244717 C2 RU2244717 C2 RU 2244717C2

Authority

RU

Russia

Prior art keywords

quinolin

amine

quinoline

thiazolo

oxide

Prior art date

1998-07-28

Links

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• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 148
• 238000000034 method Methods 0.000 title claims abstract description 71
• 230000015572 biosynthetic process Effects 0.000 title claims abstract description 45
• 102000004127 Cytokines Human genes 0.000 title claims abstract description 24
• 108090000695 Cytokines Proteins 0.000 title claims abstract description 24
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 11
• 230000004936 stimulating effect Effects 0.000 title claims abstract description 8
• UQHKFADEQIVWID-UHFFFAOYSA-N cytokinin Natural products C1=NC=2C(NCC=C(CO)C)=NC=NC=2N1C1CC(O)C(CO)O1 UQHKFADEQIVWID-UHFFFAOYSA-N 0.000 title abstract description 3
• 239000004062 cytokinin Substances 0.000 title abstract description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
• 125000003118 aryl group Chemical group 0.000 claims abstract description 16
• 125000004434 sulfur atom Chemical group 0.000 claims abstract description 8
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 6
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
• 239000000203 mixture Substances 0.000 claims description 220
• FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 claims description 196
• 125000001424 substituent group Chemical group 0.000 claims description 53
• -1 2-phenyl-1-ethenyl Chemical group 0.000 claims description 52
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 32
• 229910052717 sulfur Inorganic materials 0.000 claims description 24
• 150000003839 salts Chemical class 0.000 claims description 20
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
• 239000011593 sulfur Substances 0.000 claims description 16
• 201000010099 disease Diseases 0.000 claims description 15
• 102000006992 Interferon-alpha Human genes 0.000 claims description 13
• 108010047761 Interferon-alpha Proteins 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
• 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 11
• 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims description 11
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 11
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 11
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
• 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims description 11
• VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 claims description 10
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 10
• KFAJXZVDBVRZRC-UHFFFAOYSA-N 1,5-naphthyridin-4-amine Chemical compound C1=CN=C2C(N)=CC=NC2=C1 KFAJXZVDBVRZRC-UHFFFAOYSA-N 0.000 claims description 8
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
• 230000002548 cytokinetic effect Effects 0.000 claims description 8
• 230000003612 virological effect Effects 0.000 claims description 8
• 206010028980 Neoplasm Diseases 0.000 claims description 7
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 125000005843 halogen group Chemical group 0.000 claims description 6
• 210000005260 human cell Anatomy 0.000 claims description 6
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
• CZHVSPXZCDPPAX-UHFFFAOYSA-N 2-butyl-7-methyl-[1,3]oxazolo[4,5-c]quinolin-4-amine Chemical compound C1=C(C)C=CC2=C(OC(CCCC)=N3)C3=C(N)N=C21 CZHVSPXZCDPPAX-UHFFFAOYSA-N 0.000 claims description 4
• UMMVLGBNCBOQTO-UHFFFAOYSA-N 7-fluoro-2-propyl-[1,3]oxazolo[4,5-c]quinolin-4-amine Chemical compound C1=C(F)C=CC2=C(OC(CCC)=N3)C3=C(N)N=C21 UMMVLGBNCBOQTO-UHFFFAOYSA-N 0.000 claims description 4
• FPUDMHYTEWTZKG-UHFFFAOYSA-N 7-methoxy-2-propyl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=C(OC)C=CC2=C(SC(CCC)=N3)C3=C(N)N=C21 FPUDMHYTEWTZKG-UHFFFAOYSA-N 0.000 claims description 4
• QMDADVZFXOAXPO-UHFFFAOYSA-N 7-methyl-2-propyl-[1,3]oxazolo[4,5-c]quinolin-4-amine Chemical compound C1=C(C)C=CC2=C(OC(CCC)=N3)C3=C(N)N=C21 QMDADVZFXOAXPO-UHFFFAOYSA-N 0.000 claims description 4
• KUVYHEWNVJZLEX-UHFFFAOYSA-N 8-methyl-2-propyl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=CC(C)=CC2=C(SC(CCC)=N3)C3=C(N)N=C21 KUVYHEWNVJZLEX-UHFFFAOYSA-N 0.000 claims description 4
• VNIYSXOHLPIAID-UHFFFAOYSA-N quinoline-4,8-diamine Chemical compound C1=CC=C2C(N)=CC=NC2=C1N VNIYSXOHLPIAID-UHFFFAOYSA-N 0.000 claims description 4
• DMQSUTMWSINPAJ-UHFFFAOYSA-N 2-ethyl-[1,3]oxazolo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(OC(CC)=N3)C3=C(N)N=C21 DMQSUTMWSINPAJ-UHFFFAOYSA-N 0.000 claims description 3
• DEUBWEBVMICKDO-UHFFFAOYSA-N 7-chloro-2-propyl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=C(Cl)C=CC2=C(SC(CCC)=N3)C3=C(N)N=C21 DEUBWEBVMICKDO-UHFFFAOYSA-N 0.000 claims description 3
• MKMMMNNPXSQTDW-UHFFFAOYSA-N 7-fluoro-2-propyl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=C(F)C=CC2=C(SC(CCC)=N3)C3=C(N)N=C21 MKMMMNNPXSQTDW-UHFFFAOYSA-N 0.000 claims description 3
• YLQAXUQWWPUTKB-UHFFFAOYSA-N 7-methyl-2-propyl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=C(C)C=CC2=C(SC(CCC)=N3)C3=C(N)N=C21 YLQAXUQWWPUTKB-UHFFFAOYSA-N 0.000 claims description 3
• OYCXOBUNIUHNOK-UHFFFAOYSA-N (4-amino-[1,3]thiazolo[4,5-c]quinolin-2-yl)methanol Chemical compound NC1=NC2=CC=CC=C2C2=C1N=C(CO)S2 OYCXOBUNIUHNOK-UHFFFAOYSA-N 0.000 claims description 2
• KTHVEAHLDBJOSB-UHFFFAOYSA-N 8-bromo-2-propyl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=CC(Br)=CC2=C(SC(CCC)=N3)C3=C(N)N=C21 KTHVEAHLDBJOSB-UHFFFAOYSA-N 0.000 claims description 2
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 150000003254 radicals Chemical class 0.000 claims description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
• 241000124008 Mammalia Species 0.000 claims 4
• 125000003277 amino group Chemical group 0.000 claims 2
• 150000001555 benzenes Chemical group 0.000 claims 2
• NFYMGJSUKCDVJR-UHFFFAOYSA-N 2-propyl-[1,3]thiazolo[4,5-c]quinolin-4-amine Chemical compound C1=CC=CC2=C(SC(CCC)=N3)C3=C(N)N=C21 NFYMGJSUKCDVJR-UHFFFAOYSA-N 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• 230000001737 promoting effect Effects 0.000 claims 1
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
• 239000000126 substance Substances 0.000 abstract description 22
• 230000004071 biological effect Effects 0.000 abstract description 10
• 125000000217 alkyl group Chemical group 0.000 abstract description 9
• 230000000694 effects Effects 0.000 abstract description 7
• 229910052760 oxygen Inorganic materials 0.000 abstract description 6
• 239000001301 oxygen Substances 0.000 abstract description 5
• 239000003814 drug Substances 0.000 abstract description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
• 125000002757 morpholinyl group Chemical group 0.000 abstract description 2
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 375
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 244
• 239000000243 solution Substances 0.000 description 187
• 229910052739 hydrogen Inorganic materials 0.000 description 161
• 229910052757 nitrogen Inorganic materials 0.000 description 160
• 229910052799 carbon Inorganic materials 0.000 description 148
• 239000007787 solid Substances 0.000 description 126
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 116
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 114
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 110
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 98
• 238000004458 analytical method Methods 0.000 description 93
• 239000000047 product Substances 0.000 description 93
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 87
• 238000002844 melting Methods 0.000 description 86
• 230000008018 melting Effects 0.000 description 86
• 239000011541 reaction mixture Substances 0.000 description 83
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 65
• 239000002244 precipitate Substances 0.000 description 63
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 58
• 238000006243 chemical reaction Methods 0.000 description 53
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 51
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 49
• 235000019341 magnesium sulphate Nutrition 0.000 description 49
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 48
• 239000000725 suspension Substances 0.000 description 48
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
• KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 40
• 239000000706 filtrate Substances 0.000 description 34
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 32
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 32
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 30
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
• GRNOZCCBOFGDCL-UHFFFAOYSA-N 2,2,2-trichloroacetyl isocyanate Chemical compound ClC(Cl)(Cl)C(=O)N=C=O GRNOZCCBOFGDCL-UHFFFAOYSA-N 0.000 description 27
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 24
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 24
• 235000017557 sodium bicarbonate Nutrition 0.000 description 24
• 150000001204 N-oxides Chemical class 0.000 description 23
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 22
• 239000003795 chemical substances by application Substances 0.000 description 22
• 238000001953 recrystallisation Methods 0.000 description 22
• 239000003480 eluent Substances 0.000 description 21
• 239000002904 solvent Substances 0.000 description 21
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
• 102000014150 Interferons Human genes 0.000 description 20
• 108010050904 Interferons Proteins 0.000 description 20
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
• 210000004027 cell Anatomy 0.000 description 20
• 239000013078 crystal Substances 0.000 description 19
• 239000012265 solid product Substances 0.000 description 19
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 18
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
• 239000003054 catalyst Substances 0.000 description 18
• 239000000284 extract Substances 0.000 description 18
• 239000012299 nitrogen atmosphere Substances 0.000 description 18
• 239000012044 organic layer Substances 0.000 description 18
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 17
• 239000000908 ammonium hydroxide Substances 0.000 description 17
• 229940079322 interferon Drugs 0.000 description 17
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 16
• 239000000843 powder Substances 0.000 description 16
• 239000000741 silica gel Substances 0.000 description 16
• 229910002027 silica gel Inorganic materials 0.000 description 16
• 238000010438 heat treatment Methods 0.000 description 15
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 14
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
• 238000003756 stirring Methods 0.000 description 14
• 238000012360 testing method Methods 0.000 description 14
• 238000004809 thin layer chromatography Methods 0.000 description 14
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
• 239000002253 acid Substances 0.000 description 13
• 239000003921 oil Substances 0.000 description 13
• 235000019198 oils Nutrition 0.000 description 13
• 238000003786 synthesis reaction Methods 0.000 description 13
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 150000001408 amides Chemical class 0.000 description 12
• 229910021529 ammonia Inorganic materials 0.000 description 12
• 239000012043 crude product Substances 0.000 description 12
• 239000012948 isocyanate Substances 0.000 description 12
• 239000012071 phase Substances 0.000 description 12
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 11
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 11
• 229910052698 phosphorus Inorganic materials 0.000 description 11
• 239000011574 phosphorus Substances 0.000 description 11
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 10
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 10
• 239000007864 aqueous solution Substances 0.000 description 10
• 239000012267 brine Substances 0.000 description 10
• 150000002513 isocyanates Chemical class 0.000 description 10
• 239000010410 layer Substances 0.000 description 10
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
• 239000001257 hydrogen Substances 0.000 description 9
• YJBLTYRYUXKJLE-UHFFFAOYSA-N 3-amino-1h-quinoline-4-thione Chemical compound C1=CC=C2C(=S)C(N)=CNC2=C1 YJBLTYRYUXKJLE-UHFFFAOYSA-N 0.000 description 8
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 8
• 241000700605 Viruses Species 0.000 description 8
• 239000012298 atmosphere Substances 0.000 description 8
• 238000009835 boiling Methods 0.000 description 8
• DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 8
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
• 229910052763 palladium Inorganic materials 0.000 description 8
• 238000002360 preparation method Methods 0.000 description 8
• 238000006722 reduction reaction Methods 0.000 description 8
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
• NIQNIQVCPKCNQS-UHFFFAOYSA-N 3-amino-1h-quinolin-4-one Chemical compound C1=CC=C2C(=O)C(N)=CNC2=C1 NIQNIQVCPKCNQS-UHFFFAOYSA-N 0.000 description 7
• 241001465754 Metazoa Species 0.000 description 7
• 238000007796 conventional method Methods 0.000 description 7
• 229910052740 iodine Inorganic materials 0.000 description 7
• 239000000463 material Substances 0.000 description 7
• 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 7
• 229910000029 sodium carbonate Inorganic materials 0.000 description 7
• UPQQXPKAYZYUKO-UHFFFAOYSA-N 2,2,2-trichloroacetamide Chemical compound OC(=N)C(Cl)(Cl)Cl UPQQXPKAYZYUKO-UHFFFAOYSA-N 0.000 description 6
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
• 239000001569 carbon dioxide Substances 0.000 description 6
• 229910002092 carbon dioxide Inorganic materials 0.000 description 6
• 238000004896 high resolution mass spectrometry Methods 0.000 description 6
• 230000028993 immune response Effects 0.000 description 6
• 230000003647 oxidation Effects 0.000 description 6
• 238000007254 oxidation reaction Methods 0.000 description 6
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
• 239000007858 starting material Substances 0.000 description 6
• MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical compound C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 5
• 238000002965 ELISA Methods 0.000 description 5
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
• 210000004369 blood Anatomy 0.000 description 5
• 239000008280 blood Substances 0.000 description 5
• 150000001805 chlorine compounds Chemical class 0.000 description 5
• 125000004122 cyclic group Chemical group 0.000 description 5
• 238000003818 flash chromatography Methods 0.000 description 5
• 125000001072 heteroaryl group Chemical group 0.000 description 5
• 125000000623 heterocyclic group Chemical group 0.000 description 5
• 239000007788 liquid Substances 0.000 description 5
• 229910017604 nitric acid Inorganic materials 0.000 description 5
• 239000002243 precursor Substances 0.000 description 5
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• GZNAASVAJNXPPW-UHFFFAOYSA-M tin(4+) chloride dihydrate Chemical compound O.O.[Cl-].[Sn+4] GZNAASVAJNXPPW-UHFFFAOYSA-M 0.000 description 1
• FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Substances O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 1
• LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
• 238000012546 transfer Methods 0.000 description 1
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
• 201000008827 tuberculosis Diseases 0.000 description 1
• 210000004881 tumor cell Anatomy 0.000 description 1
• 230000004614 tumor growth Effects 0.000 description 1
• 230000029663 wound healing Effects 0.000 description 1