NO862270L - Analogifremgangsmaate for fremstilling av terapeutisk aktive isatinforbindelser. - Google Patents
Analogifremgangsmaate for fremstilling av terapeutisk aktive isatinforbindelser.Info
- Publication number
- NO862270L NO862270L NO862270A NO862270A NO862270L NO 862270 L NO862270 L NO 862270L NO 862270 A NO862270 A NO 862270A NO 862270 A NO862270 A NO 862270A NO 862270 L NO862270 L NO 862270L
- Authority
- NO
- Norway
- Prior art keywords
- isatin
- diisopropylaminoethyl
- semicarbazone
- nmr
- vco
- Prior art date
Links
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical class C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 title claims description 45
- 238000000034 method Methods 0.000 title claims description 39
- 238000002360 preparation method Methods 0.000 title claims description 6
- 230000001225 therapeutic effect Effects 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- -1 amino compound Chemical class 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000003349 semicarbazides Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 84
- 239000000243 solution Substances 0.000 description 41
- 238000000921 elemental analysis Methods 0.000 description 35
- 239000000203 mixture Substances 0.000 description 35
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 239000000758 substrate Substances 0.000 description 31
- 235000019441 ethanol Nutrition 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- 239000002904 solvent Substances 0.000 description 18
- 239000000725 suspension Substances 0.000 description 17
- 239000002244 precipitate Substances 0.000 description 16
- 238000001953 recrystallisation Methods 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 15
- 208000025865 Ulcer Diseases 0.000 description 15
- 238000001816 cooling Methods 0.000 description 15
- 238000004458 analytical method Methods 0.000 description 14
- 238000001914 filtration Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- IOIOGEXCQPEOSV-UHFFFAOYSA-N 1-[2-[di(propan-2-yl)amino]ethyl]indole-2,3-dione Chemical compound C1=CC=C2N(CCN(C(C)C)C(C)C)C(=O)C(=O)C2=C1 IOIOGEXCQPEOSV-UHFFFAOYSA-N 0.000 description 11
- IUSXYVRFJVAVOB-UHFFFAOYSA-N n-(2-chloroethyl)-n-propan-2-ylpropan-2-amine;hydron;chloride Chemical compound Cl.CC(C)N(C(C)C)CCCl IUSXYVRFJVAVOB-UHFFFAOYSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000000767 anti-ulcer Effects 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- TVDWXWSYKVPNDU-XDJHFCHBSA-N [(e)-[1-[2-[di(propan-2-yl)amino]ethyl]-2-oxoindol-3-ylidene]amino]urea Chemical compound C1=CC=C2N(CCN(C(C)C)C(C)C)C(=O)\C(=N\NC(N)=O)C2=C1 TVDWXWSYKVPNDU-XDJHFCHBSA-N 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- ZSKBCYKDAAURSU-UHFFFAOYSA-N [(2-oxoindol-3-yl)amino]urea Chemical class C1=CC=CC2=NC(=O)C(NNC(=O)N)=C21 ZSKBCYKDAAURSU-UHFFFAOYSA-N 0.000 description 6
- NIAKTYVWEOJVEM-UHFFFAOYSA-N 1-[2-[di(propan-2-yl)amino]ethyl]-5-methylindole-2,3-dione Chemical compound CC1=CC=C2N(CCN(C(C)C)C(C)C)C(=O)C(=O)C2=C1 NIAKTYVWEOJVEM-UHFFFAOYSA-N 0.000 description 5
- SLEMRAMJSGBARH-UHFFFAOYSA-N [(2-oxoindol-3-yl)amino]thiourea Chemical class C1=CC=C2C(=NNC(=S)N)C(=O)NC2=C1 SLEMRAMJSGBARH-UHFFFAOYSA-N 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 238000011321 prophylaxis Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 231100000397 ulcer Toxicity 0.000 description 5
- CHLMVMWHBHBMPK-UHFFFAOYSA-N 5-bromo-1-[2-[di(propan-2-yl)amino]ethyl]indole-2,3-dione Chemical compound BrC1=CC=C2N(CCN(C(C)C)C(C)C)C(=O)C(=O)C2=C1 CHLMVMWHBHBMPK-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 230000027119 gastric acid secretion Effects 0.000 description 4
- 238000007654 immersion Methods 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- HLHNBMAQONZOIF-UHFFFAOYSA-N n-[1-[2-[di(propan-2-yl)amino]ethyl]-2,3-dioxoindol-5-yl]acetamide Chemical compound CC(=O)NC1=CC=C2N(CCN(C(C)C)C(C)C)C(=O)C(=O)C2=C1 HLHNBMAQONZOIF-UHFFFAOYSA-N 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- 239000001632 sodium acetate Substances 0.000 description 4
- 235000017281 sodium acetate Nutrition 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 210000002784 stomach Anatomy 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- LRTRJUOARYHNDB-UHFFFAOYSA-N (2-hydroxy-1H-indol-3-yl)iminourea Chemical compound C1=CC=C2C(=C1)C(=C(N2)O)N=NC(=O)N LRTRJUOARYHNDB-UHFFFAOYSA-N 0.000 description 3
- CKCTUTOUPKLMOE-UHFFFAOYSA-N 1-[1-[di(propan-2-yl)amino]propan-2-yl]indole-2,3-dione Chemical compound C1=CC=C2N(C(C)CN(C(C)C)C(C)C)C(=O)C(=O)C2=C1 CKCTUTOUPKLMOE-UHFFFAOYSA-N 0.000 description 3
- DOYHHIPXCTYCFL-UHFFFAOYSA-N 1-[2-(propan-2-ylamino)ethyl]indole-2,3-dione Chemical compound C1=CC=C2N(CCNC(C)C)C(=O)C(=O)C2=C1 DOYHHIPXCTYCFL-UHFFFAOYSA-N 0.000 description 3
- NPZDERHNKLUPKN-UHFFFAOYSA-N 1-[2-(tert-butylamino)ethyl]indole-2,3-dione Chemical compound C1=CC=C2N(CCNC(C)(C)C)C(=O)C(=O)C2=C1 NPZDERHNKLUPKN-UHFFFAOYSA-N 0.000 description 3
- UQSJPGRIFWUWJA-UHFFFAOYSA-N 1-[2-[benzyl(propan-2-yl)amino]ethyl]indole-2,3-dione Chemical compound O=C1C(=O)C2=CC=CC=C2N1CCN(C(C)C)CC1=CC=CC=C1 UQSJPGRIFWUWJA-UHFFFAOYSA-N 0.000 description 3
- NJWWRCCRZLWGTQ-UHFFFAOYSA-N 1-[2-[di(propan-2-yl)amino]ethyl]-5-fluoroindole-2,3-dione Chemical compound FC1=CC=C2N(CCN(C(C)C)C(C)C)C(=O)C(=O)C2=C1 NJWWRCCRZLWGTQ-UHFFFAOYSA-N 0.000 description 3
- PWHIJVXEWLSCHU-UHFFFAOYSA-N 1-[2-[di(propan-2-yl)amino]ethyl]-7-methylindole-2,3-dione Chemical compound C1=CC(C)=C2N(CCN(C(C)C)C(C)C)C(=O)C(=O)C2=C1 PWHIJVXEWLSCHU-UHFFFAOYSA-N 0.000 description 3
- OBRQJOPYHRMHAX-UHFFFAOYSA-N 1-[2-[di(propan-2-yl)amino]propyl]indole-2,3-dione Chemical compound C1=CC=C2N(CC(C)N(C(C)C)C(C)C)C(=O)C(=O)C2=C1 OBRQJOPYHRMHAX-UHFFFAOYSA-N 0.000 description 3
- UDVNIOJFSOLEIE-UHFFFAOYSA-N 1-[3-[di(propan-2-yl)amino]propyl]-5-methylindole-2,3-dione Chemical compound CC1=CC=C2N(CCCN(C(C)C)C(C)C)C(=O)C(=O)C2=C1 UDVNIOJFSOLEIE-UHFFFAOYSA-N 0.000 description 3
- QEGAVARNEWSVEJ-UHFFFAOYSA-N 1-[3-[di(propan-2-yl)amino]propyl]indole-2,3-dione Chemical compound C1=CC=C2N(CCCN(C(C)C)C(C)C)C(=O)C(=O)C2=C1 QEGAVARNEWSVEJ-UHFFFAOYSA-N 0.000 description 3
- CZEBIMVLTQEGMQ-UHFFFAOYSA-N 1-amino-3-benzylurea;hydrochloride Chemical compound Cl.NNC(=O)NCC1=CC=CC=C1 CZEBIMVLTQEGMQ-UHFFFAOYSA-N 0.000 description 3
- QETXPAUKWYVYCL-XTCLZLMSSA-N 1-benzyl-3-[(e)-[1-[2-[di(propan-2-yl)amino]ethyl]-2-oxoindol-3-ylidene]amino]urea Chemical compound C12=CC=CC=C2N(CCN(C(C)C)C(C)C)C(=O)\C1=N\NC(=O)NCC1=CC=CC=C1 QETXPAUKWYVYCL-XTCLZLMSSA-N 0.000 description 3
- AWLGINQJAVUHTR-UHFFFAOYSA-N 5-amino-1-[2-[di(propan-2-yl)amino]ethyl]indole-2,3-dione Chemical compound NC1=CC=C2N(CCN(C(C)C)C(C)C)C(=O)C(=O)C2=C1 AWLGINQJAVUHTR-UHFFFAOYSA-N 0.000 description 3
- RNFNKGPPFPRMFJ-UHFFFAOYSA-N 5-chloro-1-[2-[di(propan-2-yl)amino]ethyl]indole-2,3-dione Chemical compound ClC1=CC=C2N(CCN(C(C)C)C(C)C)C(=O)C(=O)C2=C1 RNFNKGPPFPRMFJ-UHFFFAOYSA-N 0.000 description 3
- VAJCSPZKMVQIAP-UHFFFAOYSA-N 5-methyl-1h-indole-2,3-dione Chemical compound CC1=CC=C2NC(=O)C(=O)C2=C1 VAJCSPZKMVQIAP-UHFFFAOYSA-N 0.000 description 3
- TWCMLOSSMDTNAR-UHFFFAOYSA-N 6-chloro-1-[2-[di(propan-2-yl)amino]ethyl]indole-2,3-dione Chemical compound C1=C(Cl)C=C2N(CCN(C(C)C)C(C)C)C(=O)C(=O)C2=C1 TWCMLOSSMDTNAR-UHFFFAOYSA-N 0.000 description 3
- AHQQISFKHQYNEL-UHFFFAOYSA-N 7-bromo-1-[2-[di(propan-2-yl)amino]ethyl]-5-methylindole-2,3-dione Chemical compound CC1=CC(Br)=C2N(CCN(C(C)C)C(C)C)C(=O)C(=O)C2=C1 AHQQISFKHQYNEL-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000004442 acylamino group Chemical group 0.000 description 3
- 230000000840 anti-viral effect Effects 0.000 description 3
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- AKAGAGZUNRXQDN-UHFFFAOYSA-N methyl 1-[2-[di(propan-2-yl)amino]ethyl]-2,3-dioxoindole-7-carboxylate Chemical compound COC(=O)C1=CC=CC2=C1N(CCN(C(C)C)C(C)C)C(=O)C2=O AKAGAGZUNRXQDN-UHFFFAOYSA-N 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- IVQKRNVROYLYQW-CAPFRKAQSA-N 1-[(e)-[1-[2-[di(propan-2-yl)amino]ethyl]-2-oxoindol-3-ylidene]amino]-3-methylurea Chemical compound C1=CC=C2C(=N/NC(=O)NC)\C(=O)N(CCN(C(C)C)C(C)C)C2=C1 IVQKRNVROYLYQW-CAPFRKAQSA-N 0.000 description 2
- IWMMBILXTRTTFE-UHFFFAOYSA-N 1-[2-[cyclohexyl(propan-2-yl)amino]ethyl]indole-2,3-dione Chemical compound O=C1C(=O)C2=CC=CC=C2N1CCN(C(C)C)C1CCCCC1 IWMMBILXTRTTFE-UHFFFAOYSA-N 0.000 description 2
- LHYKTQVFLKHQSR-UHFFFAOYSA-N 1-amino-3-methylurea Chemical compound CNC(=O)NN LHYKTQVFLKHQSR-UHFFFAOYSA-N 0.000 description 2
- VJQULJPYVAJZKN-UHFFFAOYSA-N 3-chloro-n,n-di(propan-2-yl)propan-1-amine;hydrochloride Chemical compound Cl.CC(C)N(C(C)C)CCCCl VJQULJPYVAJZKN-UHFFFAOYSA-N 0.000 description 2
- NPDJRIGMWAQKTQ-UHFFFAOYSA-N 7-bromo-5-methyl-1h-indole-2,3-dione Chemical compound BrC1=CC(C)=CC2=C1NC(=O)C2=O NPDJRIGMWAQKTQ-UHFFFAOYSA-N 0.000 description 2
- HTXOBILHAHJQHB-NJNXFGOHSA-N C12=CC=CC=C2N(CCN(C(C)C)C(C)C)C(=O)\C1=N\NC(=O)NC1CCCCC1 Chemical compound C12=CC=CC=C2N(CCN(C(C)C)C(C)C)C(=O)\C1=N\NC(=O)NC1CCCCC1 HTXOBILHAHJQHB-NJNXFGOHSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- OXPMMKBQCUQYIH-RELWKKBWSA-N [(e)-[1-[2-[cyclohexyl(propan-2-yl)amino]ethyl]-2-oxoindol-3-ylidene]amino]urea Chemical compound O=C1\C(=N\NC(N)=O)C2=CC=CC=C2N1CCN(C(C)C)C1CCCCC1 OXPMMKBQCUQYIH-RELWKKBWSA-N 0.000 description 2
- KCTDEHIFZWCLQZ-HMMYKYKNSA-N [(e)-[1-[2-[di(propan-2-yl)amino]ethyl]-5-fluoro-2-oxoindol-3-ylidene]amino]urea Chemical compound FC1=CC=C2N(CCN(C(C)C)C(C)C)C(=O)\C(=N\NC(N)=O)C2=C1 KCTDEHIFZWCLQZ-HMMYKYKNSA-N 0.000 description 2
- SJASSAIVEVVDRO-HMMYKYKNSA-N [(e)-[5-bromo-1-[2-[di(propan-2-yl)amino]ethyl]-2-oxoindol-3-ylidene]amino]urea Chemical compound BrC1=CC=C2N(CCN(C(C)C)C(C)C)C(=O)\C(=N\NC(N)=O)C2=C1 SJASSAIVEVVDRO-HMMYKYKNSA-N 0.000 description 2
- YSJVDJWYNDCBDR-HMMYKYKNSA-N [(e)-[5-chloro-1-[2-[di(propan-2-yl)amino]ethyl]-2-oxoindol-3-ylidene]amino]urea Chemical compound ClC1=CC=C2N(CCN(C(C)C)C(C)C)C(=O)\C(=N\NC(N)=O)C2=C1 YSJVDJWYNDCBDR-HMMYKYKNSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000000739 antihistaminic agent Substances 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000001120 cytoprotective effect Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 208000000718 duodenal ulcer Diseases 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 230000035876 healing Effects 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- YGWFBDFCQQEYTE-QNGOZBTKSA-N methyl (3z)-3-(carbamoylhydrazinylidene)-1-[2-[di(propan-2-yl)amino]ethyl]-2-oxoindole-7-carboxylate Chemical compound COC(=O)C1=CC=CC\2=C1N(CCN(C(C)C)C(C)C)C(=O)C/2=N\NC(N)=O YGWFBDFCQQEYTE-QNGOZBTKSA-N 0.000 description 2
- LYKHAUJOYOTMOW-UHFFFAOYSA-N n-(2-chloroethyl)-n-propan-2-ylcyclohexanamine;hydrochloride Chemical compound Cl.ClCCN(C(C)C)C1CCCCC1 LYKHAUJOYOTMOW-UHFFFAOYSA-N 0.000 description 2
- LGPKPGHKHGLXKI-UHFFFAOYSA-N n-benzyl-n-(2-chloroethyl)propan-2-amine Chemical compound ClCCN(C(C)C)CC1=CC=CC=C1 LGPKPGHKHGLXKI-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
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Classifications
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- 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
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- 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
- C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12491985 | 1985-06-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO862270D0 NO862270D0 (no) | 1986-06-06 |
| NO862270L true NO862270L (no) | 1986-12-09 |
Family
ID=14897377
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO862270A NO862270L (no) | 1985-06-08 | 1986-06-06 | Analogifremgangsmaate for fremstilling av terapeutisk aktive isatinforbindelser. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4780477A (ja) |
| EP (1) | EP0205299A3 (ja) |
| JP (1) | JPS6289661A (ja) |
| KR (1) | KR870000296A (ja) |
| AU (1) | AU584710B2 (ja) |
| DK (1) | DK268186A (ja) |
| ES (1) | ES8801205A1 (ja) |
| FI (1) | FI862400A (ja) |
| NO (1) | NO862270L (ja) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5198461A (en) * | 1989-12-11 | 1993-03-30 | Neurosearch A/S | Isatine derivatives, their preparation and use |
| US5164404A (en) * | 1991-03-15 | 1992-11-17 | Neurosearch A/S | Hydrazone derivatives and their use |
| ATE285769T1 (de) * | 1998-12-04 | 2005-01-15 | Neurosearch As | Verwendung von isatinderivaten als ionenkanalaktivierende mittel |
| KR100878859B1 (ko) * | 2007-11-27 | 2009-01-15 | 주식회사 아크로이엔지 | 세라믹제품 소성용 세라믹코팅 니켈 메쉬 받침대 및 그제조방법 |
| CN103554008B (zh) * | 2013-11-04 | 2016-05-04 | 天津科技大学 | 1,3-取代-5-乙酰氨基吲哚酮类化合物及其在抗肿瘤药物中的应用 |
| KR102161674B1 (ko) * | 2014-02-18 | 2020-10-05 | 주식회사 대웅제약 | 이사틴 유도체 및 이의 제조방법 |
| US11945809B2 (en) * | 2020-07-19 | 2024-04-02 | King Saud University | Isatin derivatives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE665245A (ja) * | 1964-06-11 | |||
| US3558646A (en) * | 1968-06-17 | 1971-01-26 | American Home Prod | 2-oxo-3-indolinylidene hydrazides of alkanoic acids |
| US3631063A (en) * | 1969-05-28 | 1971-12-28 | Upjohn Co | 1-aminoalkyl-2 2-disubstituted indolin-3-ones and a process for the production therefor |
| DE2931323A1 (de) * | 1979-08-02 | 1981-02-26 | Kali Chemie Pharma Gmbh | Neue n-aminoalkylindol-derivate und ihre salze |
-
1986
- 1986-05-29 US US06/868,146 patent/US4780477A/en not_active Expired - Fee Related
- 1986-06-03 EP EP86304195A patent/EP0205299A3/en not_active Withdrawn
- 1986-06-05 FI FI862400A patent/FI862400A/fi not_active Application Discontinuation
- 1986-06-05 JP JP61130949A patent/JPS6289661A/ja active Granted
- 1986-06-06 NO NO862270A patent/NO862270L/no unknown
- 1986-06-06 ES ES555835A patent/ES8801205A1/es not_active Expired
- 1986-06-06 AU AU58446/86A patent/AU584710B2/en not_active Ceased
- 1986-06-06 DK DK268186A patent/DK268186A/da not_active Application Discontinuation
- 1986-06-07 KR KR1019860004517A patent/KR870000296A/ko not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU584710B2 (en) | 1989-06-01 |
| DK268186A (da) | 1986-12-09 |
| ES555835A0 (es) | 1988-01-01 |
| US4780477A (en) | 1988-10-25 |
| EP0205299A3 (en) | 1988-01-20 |
| JPH0482146B2 (ja) | 1992-12-25 |
| JPS6289661A (ja) | 1987-04-24 |
| EP0205299A2 (en) | 1986-12-17 |
| FI862400A0 (fi) | 1986-06-05 |
| AU5844686A (en) | 1986-12-11 |
| KR870000296A (ko) | 1987-02-17 |
| ES8801205A1 (es) | 1988-01-01 |
| FI862400A (fi) | 1986-12-09 |
| NO862270D0 (no) | 1986-06-06 |
| DK268186D0 (da) | 1986-06-06 |
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