FI69064C - Foerfarande foer framstaellning av farmakologiskt vaerdefulla karbostyril- och oxindolderivat - Google Patents

Info

Publication number

FI69064C

FI69064C FI790507A FI790507A FI69064C FI 69064 C FI69064 C FI 69064C FI 790507 A FI790507 A FI 790507A FI 790507 A FI790507 A FI 790507A FI 69064 C FI69064 C FI 69064C

Authority

FI

Finland

Prior art keywords

dihydrocarbostyril

butoxy

melting point

theory

yield

Prior art date

1978-02-17

Links

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• Global Dossier
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• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title claims description 44
• 238000000034 method Methods 0.000 title claims description 14
• 230000000144 pharmacologic effect Effects 0.000 title description 4
• -1 hydroxy, methoxy, amino, acetylamino Chemical group 0.000 claims description 129
• 150000001875 compounds Chemical class 0.000 claims description 45
• 125000004432 carbon atom Chemical group C* 0.000 claims description 21
• 238000002360 preparation method Methods 0.000 claims description 15
• 239000002904 solvent Substances 0.000 claims description 14
• 125000005843 halogen group Chemical group 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 238000006243 chemical reaction Methods 0.000 claims description 11
• 125000000217 alkyl group Chemical group 0.000 claims description 10
• 230000003647 oxidation Effects 0.000 claims description 10
• 238000007254 oxidation reaction Methods 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• 230000008569 process Effects 0.000 claims description 9
• 239000001257 hydrogen Substances 0.000 claims description 8
• 229910052739 hydrogen Inorganic materials 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
• 239000007800 oxidant agent Substances 0.000 claims description 6
• 239000008096 xylene Chemical group 0.000 claims description 6
• 150000001721 carbon Chemical group 0.000 claims description 5
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
• 125000002130 sulfonic acid ester group Chemical group 0.000 claims description 5
• TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 claims description 4
• 125000003118 aryl group Chemical group 0.000 claims description 4
• 238000009835 boiling Methods 0.000 claims description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
• 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 3
• 125000002947 alkylene group Chemical group 0.000 claims description 3
• 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• 229910052757 nitrogen Inorganic materials 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 239000001301 oxygen Substances 0.000 claims description 3
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
• 125000006839 xylylene group Chemical group 0.000 claims description 3
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
• 125000001072 heteroaryl group Chemical group 0.000 claims description 2
• 150000002440 hydroxy compounds Chemical class 0.000 claims description 2
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
• 150000007530 organic bases Chemical group 0.000 claims description 2
• 150000003839 salts Chemical class 0.000 claims description 2
• 229910052717 sulfur Inorganic materials 0.000 claims description 2
• 125000004434 sulfur atom Chemical group 0.000 claims description 2
• 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 239000003513 alkali Substances 0.000 claims 1
• 239000000427 antigen Substances 0.000 claims 1
• 102000036639 antigens Human genes 0.000 claims 1
• 108091007433 antigens Proteins 0.000 claims 1
• 239000002585 base Substances 0.000 claims 1
• 125000005606 carbostyryl group Chemical group 0.000 claims 1
• 125000003700 epoxy group Chemical group 0.000 claims 1
• 159000000011 group IA salts Chemical class 0.000 claims 1
• 239000012038 nucleophile Substances 0.000 claims 1
• 230000000269 nucleophilic effect Effects 0.000 claims 1
• 125000004095 oxindolyl group Chemical class N1(C(CC2=CC=CC=C12)=O)* 0.000 claims 1
• 238000002844 melting Methods 0.000 description 296
• 230000008018 melting Effects 0.000 description 296
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 248
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 41
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 36
• WMNKNHUCSKDKMK-UHFFFAOYSA-N 6-(4-bromobutoxy)-3,4-dihydro-1h-quinolin-2-one Chemical compound N1C(=O)CCC2=CC(OCCCCBr)=CC=C21 WMNKNHUCSKDKMK-UHFFFAOYSA-N 0.000 description 30
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 25
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
• 239000000243 solution Substances 0.000 description 23
• 241001465754 Metazoa Species 0.000 description 22
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 22
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
• 229960000583 acetic acid Drugs 0.000 description 20
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
• 239000012362 glacial acetic acid Substances 0.000 description 19
• 239000000741 silica gel Substances 0.000 description 19
• 229910002027 silica gel Inorganic materials 0.000 description 19
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
• 239000013078 crystal Substances 0.000 description 16
• 239000003480 eluent Substances 0.000 description 16
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
• VENNVOFVJKOLBZ-UHFFFAOYSA-N 6-(4-bromobutoxy)-1h-quinolin-2-one Chemical compound N1C(=O)C=CC2=CC(OCCCCBr)=CC=C21 VENNVOFVJKOLBZ-UHFFFAOYSA-N 0.000 description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• 238000003756 stirring Methods 0.000 description 14
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 13
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 11
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 11
• LNSCJIIRQOWTJJ-UHFFFAOYSA-N 6-(4-chlorobutoxy)-3,4-dihydro-1h-quinolin-2-one Chemical compound N1C(=O)CCC2=CC(OCCCCCl)=CC=C21 LNSCJIIRQOWTJJ-UHFFFAOYSA-N 0.000 description 11
• 235000019253 formic acid Nutrition 0.000 description 11
• 230000000740 bleeding effect Effects 0.000 description 10
• UBTYAHFMUFSMLS-UHFFFAOYSA-N 4-bromobutylsulfanylbenzene Chemical compound BrCCCCSC1=CC=CC=C1 UBTYAHFMUFSMLS-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 229960001760 dimethyl sulfoxide Drugs 0.000 description 9
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
• 239000000460 chlorine Substances 0.000 description 8
• HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 7
• VNKUIWUYOIQBMP-UHFFFAOYSA-N 6-(4-phenylsulfanylbutoxy)-3,4-dihydro-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCSC1=CC=CC=C1 VNKUIWUYOIQBMP-UHFFFAOYSA-N 0.000 description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
• 229910052801 chlorine Inorganic materials 0.000 description 7
• 239000000203 mixture Substances 0.000 description 7
• 229910000027 potassium carbonate Inorganic materials 0.000 description 7
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
• BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 6
• YVXQAFVXOFICMM-UHFFFAOYSA-N 4-bromobutylsulfinylbenzene Chemical compound BrCCCCS(=O)C1=CC=CC=C1 YVXQAFVXOFICMM-UHFFFAOYSA-N 0.000 description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
• 229910021529 ammonia Inorganic materials 0.000 description 6
• 125000004076 pyridyl group Chemical group 0.000 description 6
• 238000010992 reflux Methods 0.000 description 6
• HNJZDPKMMZXSKT-UHFFFAOYSA-N 3,4-dichlorobenzenethiol Chemical compound SC1=CC=C(Cl)C(Cl)=C1 HNJZDPKMMZXSKT-UHFFFAOYSA-N 0.000 description 5
• XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 5
• KKJNBSJAFMXOMS-UHFFFAOYSA-N 6-(4-phenylsulfanylbutoxy)-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)C=CC2=CC=1OCCCCSC1=CC=CC=C1 KKJNBSJAFMXOMS-UHFFFAOYSA-N 0.000 description 5
• DVHFRAJZCBPZIP-UHFFFAOYSA-N 6-[4-(benzenesulfinyl)butoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCS(=O)C1=CC=CC=C1 DVHFRAJZCBPZIP-UHFFFAOYSA-N 0.000 description 5
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
• XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 5
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
• 229910052794 bromium Inorganic materials 0.000 description 5
• 238000011282 treatment Methods 0.000 description 5
• JXPXIYVBJNQZFQ-UHFFFAOYSA-N 4-bromobutylsulfonylbenzene Chemical compound BrCCCCS(=O)(=O)C1=CC=CC=C1 JXPXIYVBJNQZFQ-UHFFFAOYSA-N 0.000 description 4
• FUGQUCMNPGLMPE-UHFFFAOYSA-N 5-[4-(benzenesulfonyl)butoxy]-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)C=CC2=C1OCCCCS(=O)(=O)C1=CC=CC=C1 FUGQUCMNPGLMPE-UHFFFAOYSA-N 0.000 description 4
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• KGRQYHTYSZXZPI-UHFFFAOYSA-N 6-(4-pyridin-2-ylsulfanylbutoxy)-3,4-dihydro-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCSC1=CC=CC=N1 KGRQYHTYSZXZPI-UHFFFAOYSA-N 0.000 description 4
• YMKRFROZWPCYSD-UHFFFAOYSA-N 6-[4-(4-bromo-3-methylphenyl)sulfanylbutoxy]-1h-quinolin-2-one Chemical compound C1=C(Br)C(C)=CC(SCCCCOC=2C=C3C=CC(=O)NC3=CC=2)=C1 YMKRFROZWPCYSD-UHFFFAOYSA-N 0.000 description 4
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• LKLSFDWYIBUGNT-UHFFFAOYSA-N 7-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical compound C1CC(=O)NC2=CC(O)=CC=C21 LKLSFDWYIBUGNT-UHFFFAOYSA-N 0.000 description 4
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 4
• 102000008186 Collagen Human genes 0.000 description 4
• 108010035532 Collagen Proteins 0.000 description 4
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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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• 239000008280 blood Substances 0.000 description 4
• 125000004799 bromophenyl group Chemical group 0.000 description 4
• 244000309464 bull Species 0.000 description 4
• 239000003054 catalyst Substances 0.000 description 4
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• 238000005345 coagulation Methods 0.000 description 4
• 229920001436 collagen Polymers 0.000 description 4
• 229910052740 iodine Inorganic materials 0.000 description 4
• 125000001624 naphthyl group Chemical group 0.000 description 4
• AQLYZDRHNHZHIS-UHFFFAOYSA-N quinoline-2,6-diol Chemical compound N1C(=O)C=CC2=CC(O)=CC=C21 AQLYZDRHNHZHIS-UHFFFAOYSA-N 0.000 description 4
• 239000011541 reaction mixture Substances 0.000 description 4
• JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
• 208000010110 spontaneous platelet aggregation Diseases 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 3
• KXZSVYHFYHTNBI-UHFFFAOYSA-N 1h-quinoline-2-thione Chemical compound C1=CC=CC2=NC(S)=CC=C21 KXZSVYHFYHTNBI-UHFFFAOYSA-N 0.000 description 3
• ZFIYVFOYYNSXCZ-UHFFFAOYSA-N 4-methyl-6-(4-pyridin-2-ylsulfanylbutoxy)-1h-quinolin-2-one Chemical compound C1=C2C(C)=CC(=O)NC2=CC=C1OCCCCSC1=CC=CC=N1 ZFIYVFOYYNSXCZ-UHFFFAOYSA-N 0.000 description 3
• PVPDNEDYZLHIOF-UHFFFAOYSA-N 4-methyl-6-(4-quinolin-2-ylsulfanylbutoxy)-1h-quinolin-2-one Chemical compound C1=CC=CC2=NC(SCCCCOC3=CC=C4NC(=O)C=C(C4=C3)C)=CC=C21 PVPDNEDYZLHIOF-UHFFFAOYSA-N 0.000 description 3
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• JUWWIEBUASTETF-UHFFFAOYSA-N 5-[4-(benzenesulfonyl)butoxy]-3,4-dihydro-1h-quinolin-2-one Chemical compound N1C(=O)CCC2=C1C=CC=C2OCCCCS(=O)(=O)C1=CC=CC=C1 JUWWIEBUASTETF-UHFFFAOYSA-N 0.000 description 3
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• XDHDJRGEIFPHNL-UHFFFAOYSA-N 6-(4-naphthalen-2-ylsulfanylbutoxy)-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=CC2=CC(SCCCCOC=3C=C4CCC(NC4=CC=3)=O)=CC=C21 XDHDJRGEIFPHNL-UHFFFAOYSA-N 0.000 description 3
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• KTKAABDWIKFSFR-UHFFFAOYSA-N 6-(4-quinolin-2-ylsulfanylbutoxy)-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=CC2=NC(SCCCCOC=3C=C4CCC(NC4=CC=3)=O)=CC=C21 KTKAABDWIKFSFR-UHFFFAOYSA-N 0.000 description 3
• IECJJZMTGNTYEO-UHFFFAOYSA-N 6-(5-phenylsulfanylpentoxy)-3,4-dihydro-1h-quinolin-2-one Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCCSC1=CC=CC=C1 IECJJZMTGNTYEO-UHFFFAOYSA-N 0.000 description 3
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