SU525428A3 - Способ получени производных индолхинолинона или их -окисей, или их солей - Google Patents
Способ получени производных индолхинолинона или их -окисей, или их солейInfo
- Publication number
- SU525428A3 SU525428A3 SU1959333A SU1959333A SU525428A3 SU 525428 A3 SU525428 A3 SU 525428A3 SU 1959333 A SU1959333 A SU 1959333A SU 1959333 A SU1959333 A SU 1959333A SU 525428 A3 SU525428 A3 SU 525428A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- chloro
- indolo
- ethyl
- fluorophenyl
- square
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 9
- 150000003839 salts Chemical class 0.000 title description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 111
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 90
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 60
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 40
- -1 2-diethylaminoethyl Chemical group 0.000 description 37
- 239000000203 mixture Substances 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 238000010992 reflux Methods 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 20
- 239000000725 suspension Substances 0.000 description 14
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 13
- 239000012312 sodium hydride Substances 0.000 description 13
- 229910000104 sodium hydride Inorganic materials 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 239000012954 diazonium Substances 0.000 description 7
- 150000001989 diazonium salts Chemical class 0.000 description 7
- 239000000284 extract Substances 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 230000003993 interaction Effects 0.000 description 7
- 239000012299 nitrogen atmosphere Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 150000001204 N-oxides Chemical class 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 150000007942 carboxylates Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000001207 fluorophenyl group Chemical group 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 3
- VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001412 amines Chemical group 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 150000007857 hydrazones Chemical class 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- LWQDZLYINJRBFE-UHFFFAOYSA-N 3-(2-fluorophenyl)-5-methoxy-1h-indole-2-carboxylic acid Chemical compound C12=CC(OC)=CC=C2NC(C(O)=O)=C1C1=CC=CC=C1F LWQDZLYINJRBFE-UHFFFAOYSA-N 0.000 description 2
- CGWOEOXQHIMZEQ-UHFFFAOYSA-N 3-[1-[[4-(2-phenylquinolin-3-yl)phenyl]methyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound OC1=NC2=CC=CC=C2N1C(CC1)CCN1CC(C=C1)=CC=C1C1=CC2=CC=CC=C2N=C1C1=CC=CC=C1 CGWOEOXQHIMZEQ-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- LRQLLVZKTLUGND-UHFFFAOYSA-N 5-[2-(diethylamino)ethyl]-2-methyl-7h-indolo[2,3-c]quinolin-6-one Chemical compound C12=CC=CC=C2NC2=C1C1=CC(C)=CC=C1N(CCN(CC)CC)C2=O LRQLLVZKTLUGND-UHFFFAOYSA-N 0.000 description 2
- VPXJSTOFWHBSEJ-UHFFFAOYSA-N 5h-quinolin-6-one Chemical compound C1=CN=C2C=CC(=O)CC2=C1 VPXJSTOFWHBSEJ-UHFFFAOYSA-N 0.000 description 2
- VSXJRNVSOAFKJJ-UHFFFAOYSA-N 7-[2-(diethylamino)ethyl]-5-methylindolo[2,3-c]quinolin-6-one Chemical compound O=C1N(C)C2=CC=CC=C2C2=C1N(CCN(CC)CC)C1=CC=CC=C12 VSXJRNVSOAFKJJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- GKZCDKDXQHFKRV-UHFFFAOYSA-N ethyl 3-(2-fluorophenyl)-5-methoxy-1h-indole-2-carboxylate Chemical compound CCOC(=O)C=1NC2=CC=C(OC)C=C2C=1C1=CC=CC=C1F GKZCDKDXQHFKRV-UHFFFAOYSA-N 0.000 description 2
- BBERMKLZMWHBCY-UHFFFAOYSA-N ethyl 5-chloro-3-(2-fluorophenyl)-1h-indole-2-carboxylate Chemical compound CCOC(=O)C=1NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F BBERMKLZMWHBCY-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- HDQTVUYHPGMKBZ-UHFFFAOYSA-N 10-chloro-5-(2-hydroxyethyl)-7h-indolo[2,3-c]quinolin-6-one Chemical compound C12=CC(Cl)=CC=C2NC2=C1C1=CC=CC=C1N(CCO)C2=O HDQTVUYHPGMKBZ-UHFFFAOYSA-N 0.000 description 1
- MPCDCENMRZIMMZ-UHFFFAOYSA-N 2-(2-fluorophenyl)-5-nitro-1H-indole Chemical compound FC1=C(C=CC=C1)C=1NC2=CC=C(C=C2C1)[N+](=O)[O-] MPCDCENMRZIMMZ-UHFFFAOYSA-N 0.000 description 1
- ZUTPSWCCTNFCEG-UHFFFAOYSA-N 2-[5-chloro-3-(2-fluorophenyl)indol-1-yl]-N-methylethanamine Chemical compound ClC=1C=C2C(=CN(C2=CC=1)CCNC)C1=C(C=CC=C1)F ZUTPSWCCTNFCEG-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- MLGMEEZZYSKBHJ-UHFFFAOYSA-N 2-chloro-5-[2-(diethylamino)ethyl]-7h-indolo[2,3-c]quinolin-6-one Chemical compound C12=CC=CC=C2NC2=C1C1=CC(Cl)=CC=C1N(CCN(CC)CC)C2=O MLGMEEZZYSKBHJ-UHFFFAOYSA-N 0.000 description 1
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical compound OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 description 1
- 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 description 1
- IKCZUPRWPVLSLF-UHFFFAOYSA-N 2-methoxy-1h-indole Chemical compound C1=CC=C2NC(OC)=CC2=C1 IKCZUPRWPVLSLF-UHFFFAOYSA-N 0.000 description 1
- ZDEDYZBUKDYUGO-UHFFFAOYSA-N 3-(2-fluorophenyl)-5-nitro-1H-indole-2-carboxamide Chemical compound FC1=C(C=CC=C1)C1=C(NC2=CC=C(C=C12)[N+](=O)[O-])C(=O)N ZDEDYZBUKDYUGO-UHFFFAOYSA-N 0.000 description 1
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 1
- NZMLVFGJRKTQKT-UHFFFAOYSA-N 5-(2-aminoethyl)-10-chloro-7h-indolo[2,3-c]quinolin-6-one Chemical compound C12=CC(Cl)=CC=C2NC2=C1C1=CC=CC=C1N(CCN)C2=O NZMLVFGJRKTQKT-UHFFFAOYSA-N 0.000 description 1
- PWLKRHSDNXMRHB-UHFFFAOYSA-N 5-[2-(dimethylamino)ethyl]-10-ethyl-7h-indolo[2,3-c]quinolin-6-one Chemical compound C12=CC=CC=C2N(CCN(C)C)C(=O)C2=C1C1=CC(CC)=CC=C1N2 PWLKRHSDNXMRHB-UHFFFAOYSA-N 0.000 description 1
- QOHDTAKJYPQPHH-UHFFFAOYSA-N 5-[2-(dimethylamino)ethyl]-2-methyl-7h-indolo[2,3-c]quinolin-6-one Chemical compound C12=CC=CC=C2NC2=C1C1=CC(C)=CC=C1N(CCN(C)C)C2=O QOHDTAKJYPQPHH-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- ZSUGHPOZDXFEJZ-UHFFFAOYSA-N 5-chloro-3-(2-fluorophenyl)-1h-indole-2-carboxamide Chemical compound NC(=O)C=1NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F ZSUGHPOZDXFEJZ-UHFFFAOYSA-N 0.000 description 1
- GWQFYINGOBLJRX-UHFFFAOYSA-N 5-chloro-3-(2-fluorophenyl)-1h-indole-2-carboxylic acid Chemical compound OC(=O)C=1NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F GWQFYINGOBLJRX-UHFFFAOYSA-N 0.000 description 1
- FCEMGPZFLWVNLP-UHFFFAOYSA-N 5-chloro-3-(2-fluorophenyl)-n-(2-morpholin-4-ylethyl)-1h-indole-2-carboxamide Chemical compound FC1=CC=CC=C1C1=C(C(=O)NCCN2CCOCC2)NC2=CC=C(Cl)C=C12 FCEMGPZFLWVNLP-UHFFFAOYSA-N 0.000 description 1
- KKVRBSJVTBMGRP-UHFFFAOYSA-N 5-chloro-3-(2-fluorophenyl)-n-[2-(methylamino)ethyl]-1h-indole-2-carboxamide Chemical compound CNCCNC(=O)C=1NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F KKVRBSJVTBMGRP-UHFFFAOYSA-N 0.000 description 1
- HUKWSTMCAYSBRK-UHFFFAOYSA-N 7-[2-(dimethylamino)ethyl]-5h-indolo[2,3-c]quinolin-6-one Chemical compound O=C1NC2=CC=CC=C2C2=C1N(CCN(C)C)C1=CC=CC=C12 HUKWSTMCAYSBRK-UHFFFAOYSA-N 0.000 description 1
- 101100456282 Caenorhabditis elegans mcm-4 gene Proteins 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 150000000994 L-ascorbates Chemical class 0.000 description 1
- 241001139947 Mida Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- LHUZAYREVYDAGJ-UHFFFAOYSA-N dichloromethane;ethyl acetate;methanol Chemical compound OC.ClCCl.CCOC(C)=O LHUZAYREVYDAGJ-UHFFFAOYSA-N 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940031098 ethanolamine Drugs 0.000 description 1
- FYIXPASNYHVDHS-UHFFFAOYSA-N ethyl 2-[(2-fluorophenyl)methyl]-3-oxobutanoate Chemical compound CCOC(=O)C(C(C)=O)CC1=CC=CC=C1F FYIXPASNYHVDHS-UHFFFAOYSA-N 0.000 description 1
- WOWWDTFAOIFSCK-UHFFFAOYSA-N ethyl 3-(2-fluorophenyl)-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CC1=CC=CC=C1F WOWWDTFAOIFSCK-UHFFFAOYSA-N 0.000 description 1
- XJSARGBIJFYSEK-UHFFFAOYSA-N ethyl 5-chloro-3-(2-fluorophenyl)-1-methylindole-2-carboxylate Chemical compound C12=CC(Cl)=CC=C2N(C)C(C(=O)OCC)=C1C1=CC=CC=C1F XJSARGBIJFYSEK-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229950004696 flusalan Drugs 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- HJLHTTJLVALHOP-UHFFFAOYSA-N hexane;hydron;chloride Chemical compound Cl.CCCCCC HJLHTTJLVALHOP-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229940110676 inzo Drugs 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- RZEYXWBKDSNDCW-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-5-fluoro-3-(2-fluorophenyl)-1h-indole-2-carboxamide Chemical compound CN(C)CCNC(=O)C=1NC2=CC=C(F)C=C2C=1C1=CC=CC=C1F RZEYXWBKDSNDCW-UHFFFAOYSA-N 0.000 description 1
- MGNPLIACIXIYJE-UHFFFAOYSA-N n-fluoroaniline Chemical compound FNC1=CC=CC=C1 MGNPLIACIXIYJE-UHFFFAOYSA-N 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 229930185107 quinolinone Natural products 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29219372A | 1972-09-25 | 1972-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU525428A3 true SU525428A3 (ru) | 1976-08-15 |
Family
ID=23123617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1959333A SU525428A3 (ru) | 1972-09-25 | 1973-09-24 | Способ получени производных индолхинолинона или их -окисей, или их солей |
Country Status (17)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004108671A1 (en) * | 2003-06-06 | 2004-12-16 | Suven Life Sciences Limited | Substituted indoles with serotonin receptor affinity, process for their preparation and pharmaceutical compositions containing them |
| US20050089936A1 (en) * | 2003-10-23 | 2005-04-28 | Jianping Cai | Combinatorial library of 3-aryl-1H-indole-2-carboxylic acid amides |
| ITMI20040874A1 (it) * | 2004-04-30 | 2004-07-30 | Ist Naz Stud Cura Dei Tumori | Derivati indolici ed azaindolici con azione antitumorale |
| FR2887881B1 (fr) * | 2005-07-01 | 2009-10-09 | Pierre Fabre Medicament Sa | Inhibiteurs de proteines kinases |
| EP3243814B1 (en) | 2007-04-16 | 2018-10-17 | AbbVie Inc. | 7-substituted indole as mcl-1 inhibitors |
| CN114605407B (zh) * | 2022-03-14 | 2024-06-04 | 澳门科技大学 | 一种吲哚喹啉酮类化合物及其合成方法和应用 |
-
1973
- 1973-01-01 AR AR250218A patent/AR205437A1/es active
- 1973-08-20 ZA ZA735679A patent/ZA735679B/xx unknown
- 1973-08-30 CH CH1244073A patent/CH587274A5/xx not_active IP Right Cessation
- 1973-09-21 IE IE1693/73A patent/IE38331B1/xx unknown
- 1973-09-21 JP JP48106066A patent/JPS4969698A/ja active Pending
- 1973-09-21 IL IL43283A patent/IL43283A/en unknown
- 1973-09-24 LU LU68486A patent/LU68486A1/xx unknown
- 1973-09-24 BE BE135940A patent/BE805199A/xx unknown
- 1973-09-24 SU SU1959333A patent/SU525428A3/ru active
- 1973-09-24 DD DD173636A patent/DD109388A5/xx unknown
- 1973-09-24 GB GB4469173A patent/GB1400934A/en not_active Expired
- 1973-09-24 FR FR7334085A patent/FR2200004B1/fr not_active Expired
- 1973-09-24 AT AT818873A patent/AT340425B/de not_active IP Right Cessation
- 1973-09-25 NL NL7313186A patent/NL7313186A/xx not_active Application Discontinuation
- 1973-09-25 HU HUHO1616A patent/HU168788B/hu unknown
- 1973-09-25 DE DE19732348149 patent/DE2348149A1/de active Pending
-
1974
- 1974-09-24 ES ES419019A patent/ES419019A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ATA818873A (de) | 1977-04-15 |
| FR2200004A1 (enrdf_load_stackoverflow) | 1974-04-19 |
| DE2348149A1 (de) | 1974-04-04 |
| BE805199A (fr) | 1974-03-25 |
| FR2200004B1 (enrdf_load_stackoverflow) | 1976-07-02 |
| HU168788B (enrdf_load_stackoverflow) | 1976-07-28 |
| AR205437A1 (es) | 1976-05-07 |
| LU68486A1 (enrdf_load_stackoverflow) | 1975-06-16 |
| CH587274A5 (enrdf_load_stackoverflow) | 1977-04-29 |
| IE38331L (en) | 1974-03-25 |
| JPS4969698A (enrdf_load_stackoverflow) | 1974-07-05 |
| GB1400934A (en) | 1975-07-16 |
| AU6062073A (en) | 1975-03-27 |
| ES419019A1 (es) | 1976-06-16 |
| IE38331B1 (en) | 1978-02-15 |
| NL7313186A (enrdf_load_stackoverflow) | 1974-03-27 |
| DD109388A5 (enrdf_load_stackoverflow) | 1974-11-05 |
| ZA735679B (en) | 1974-07-31 |
| AT340425B (de) | 1977-12-12 |
| IL43283A (en) | 1976-12-31 |
| IL43283A0 (en) | 1975-08-31 |
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