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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000000069 prophylactic effect Effects 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- HZDNNJABYXNPPV-UHFFFAOYSA-N (2-chloro-2-oxoethyl) acetate Chemical compound CC(=O)OCC(Cl)=O HZDNNJABYXNPPV-UHFFFAOYSA-N 0.000 description 1
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- VRYALKFFQXWPIH-RANCGNPWSA-N (3r,4s,5r)-3,4,5,6-tetrahydroxy-2-tritiohexanal Chemical compound O=CC([3H])[C@@H](O)[C@H](O)[C@H](O)CO VRYALKFFQXWPIH-RANCGNPWSA-N 0.000 description 1
- MLLQNOZUDGFLEK-NJNXFGOHSA-N 1-[(e)-[1-[2-[di(propan-2-yl)amino]ethyl]-2-oxoindol-3-ylidene]amino]-3-phenylurea Chemical compound C12=CC=CC=C2N(CCN(C(C)C)C(C)C)C(=O)\C1=N\NC(=O)NC1=CC=CC=C1 MLLQNOZUDGFLEK-NJNXFGOHSA-N 0.000 description 1
- PDRUKQSCWCFVBX-HEHNFIMWSA-N 1-[(e)-[1-[2-[di(propan-2-yl)amino]ethyl]-5-methyl-2-oxoindol-3-ylidene]amino]-3-methylurea Chemical compound C1=C(C)C=C2C(=N/NC(=O)NC)\C(=O)N(CCN(C(C)C)C(C)C)C2=C1 PDRUKQSCWCFVBX-HEHNFIMWSA-N 0.000 description 1
- AZTSPXCTSCKUTH-GFMRDNFCSA-N 1-[(z)-[1-[2-[di(propan-2-yl)amino]ethyl]-2-oxoindol-3-ylidene]amino]-3-(3-methylbutyl)urea Chemical compound C1=CC=C2C(=N/NC(=O)NCCC(C)C)/C(=O)N(CCN(C(C)C)C(C)C)C2=C1 AZTSPXCTSCKUTH-GFMRDNFCSA-N 0.000 description 1
- VZVGVHNZWUQMRZ-UHFFFAOYSA-N 1-amino-3-cyclohexylurea Chemical compound NNC(=O)NC1CCCCC1 VZVGVHNZWUQMRZ-UHFFFAOYSA-N 0.000 description 1
- NGYQHDLOXMWUHZ-UHFFFAOYSA-N 1-amino-3-cyclohexylurea;hydrochloride Chemical compound Cl.NNC(=O)NC1CCCCC1 NGYQHDLOXMWUHZ-UHFFFAOYSA-N 0.000 description 1
- WFJFGMLKAISFOZ-UHFFFAOYSA-N 1-amino-3-iminourea Chemical compound NN=C(O)N=N WFJFGMLKAISFOZ-UHFFFAOYSA-N 0.000 description 1
- GDLGTQVLIXQMKO-SLEBQGDGSA-N 1-benzyl-3-[(e)-[1-[2-[di(propan-2-yl)amino]ethyl]-5-methyl-2-oxoindol-3-ylidene]amino]urea Chemical compound C12=CC(C)=CC=C2N(CCN(C(C)C)C(C)C)C(=O)\C1=N\NC(=O)NCC1=CC=CC=C1 GDLGTQVLIXQMKO-SLEBQGDGSA-N 0.000 description 1
- VDEMCLUFYJGNTM-UHFFFAOYSA-N 2-[cyclohexyl(propan-2-yl)amino]ethanol Chemical compound OCCN(C(C)C)C1CCCCC1 VDEMCLUFYJGNTM-UHFFFAOYSA-N 0.000 description 1
- PAAXJNZWJMMMNF-UHFFFAOYSA-N 2-chloro-n,n-di(propan-2-yl)propan-1-amine;hydrochloride Chemical compound Cl.CC(Cl)CN(C(C)C)C(C)C PAAXJNZWJMMMNF-UHFFFAOYSA-N 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- MBVCESWADCIXJN-UHFFFAOYSA-N 5-Bromoisatin Chemical compound BrC1=CC=C2NC(=O)C(=O)C2=C1 MBVCESWADCIXJN-UHFFFAOYSA-N 0.000 description 1
- XHDJYQWGFIBCEP-UHFFFAOYSA-N 5-Chloro-1H-indole-2,3-dione Chemical compound ClC1=CC=C2NC(=O)C(=O)C2=C1 XHDJYQWGFIBCEP-UHFFFAOYSA-N 0.000 description 1
- GKODDAXOSGGARJ-UHFFFAOYSA-N 5-Fluoroisatin Chemical compound FC1=CC=C2NC(=O)C(=O)C2=C1 GKODDAXOSGGARJ-UHFFFAOYSA-N 0.000 description 1
- RVXLBLSGEPQBIO-UHFFFAOYSA-N 6-chloro-1h-indole-2,3-dione Chemical compound ClC1=CC=C2C(=O)C(=O)NC2=C1 RVXLBLSGEPQBIO-UHFFFAOYSA-N 0.000 description 1
- UEHZKEABUOAZSH-UHFFFAOYSA-N 7-methyl-1h-indole-2,3-dione Chemical compound CC1=CC=CC2=C1NC(=O)C2=O UEHZKEABUOAZSH-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- AKPROAUJSUMBSC-YYADALCUSA-N C12=CC(Br)=CC=C2N(CCN(C(C)C)C(C)C)C(=O)\C1=N\NC(=O)NC1CCCCC1 Chemical compound C12=CC(Br)=CC=C2N(CCN(C(C)C)C(C)C)C(=O)\C1=N\NC(=O)NC1CCCCC1 AKPROAUJSUMBSC-YYADALCUSA-N 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 206010061164 Gastric mucosal lesion Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241001466453 Laminaria Species 0.000 description 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
- 108010079943 Pentagastrin Proteins 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 206010042220 Stress ulcer Diseases 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- LTUKQZJGYXOGDU-LDADJPATSA-N [(e)-[1-[2-(tert-butylamino)ethyl]-2-oxoindol-3-ylidene]amino]urea Chemical compound C1=CC=C2N(CCNC(C)(C)C)C(=O)\C(=N\NC(N)=O)C2=C1 LTUKQZJGYXOGDU-LDADJPATSA-N 0.000 description 1
- DLCRWXBHUGHQAY-QTCZRQAZSA-N [(e)-[1-[2-[di(propan-2-yl)amino]ethyl]-2-oxoindol-3-ylidene]amino]urea;hydrochloride Chemical compound Cl.C1=CC=C2N(CCN(C(C)C)C(C)C)C(=O)\C(=N\NC(N)=O)C2=C1 DLCRWXBHUGHQAY-QTCZRQAZSA-N 0.000 description 1
- AGZLBEOFTKUDME-CAPFRKAQSA-N [(e)-[1-[2-[di(propan-2-yl)amino]ethyl]-5-methyl-2-oxoindol-3-ylidene]amino]urea Chemical compound CC1=CC=C2N(CCN(C(C)C)C(C)C)C(=O)\C(=N\NC(N)=O)C2=C1 AGZLBEOFTKUDME-CAPFRKAQSA-N 0.000 description 1
- YPTVTINGHUWWFB-HMMYKYKNSA-N [(e)-[1-[2-[di(propan-2-yl)amino]ethyl]-7-methyl-2-oxoindol-3-ylidene]amino]urea Chemical compound C1=CC(C)=C2N(CCN(C(C)C)C(C)C)C(=O)\C(=N\NC(N)=O)C2=C1 YPTVTINGHUWWFB-HMMYKYKNSA-N 0.000 description 1
- LTKVNXHIXXUPCZ-CAPFRKAQSA-N [(e)-[1-[2-[di(propan-2-yl)amino]propyl]-2-oxoindol-3-ylidene]amino]urea Chemical compound C1=CC=C2N(CC(C)N(C(C)C)C(C)C)C(=O)\C(=N\NC(N)=O)C2=C1 LTKVNXHIXXUPCZ-CAPFRKAQSA-N 0.000 description 1
- QFXCKLCDAQOJJG-CAPFRKAQSA-N [(e)-[1-[3-[di(propan-2-yl)amino]propyl]-2-oxoindol-3-ylidene]amino]urea Chemical compound C1=CC=C2N(CCCN(C(C)C)C(C)C)C(=O)\C(=N\NC(N)=O)C2=C1 QFXCKLCDAQOJJG-CAPFRKAQSA-N 0.000 description 1
- NUSHQGQOCPMDLG-HEHNFIMWSA-N [(e)-[1-[3-[di(propan-2-yl)amino]propyl]-5-methyl-2-oxoindol-3-ylidene]amino]urea Chemical compound CC1=CC=C2N(CCCN(C(C)C)C(C)C)C(=O)\C(=N\NC(N)=O)C2=C1 NUSHQGQOCPMDLG-HEHNFIMWSA-N 0.000 description 1
- VUZYPEAZBWJORA-SFQUDFHCSA-N [(e)-[2-oxo-1-[2-(propan-2-ylamino)ethyl]indol-3-ylidene]amino]urea Chemical compound C1=CC=C2N(CCNC(C)C)C(=O)\C(=N\NC(N)=O)C2=C1 VUZYPEAZBWJORA-SFQUDFHCSA-N 0.000 description 1
- QUYARPNRTLDSRZ-HMMYKYKNSA-N [(e)-[5-amino-1-[2-[di(propan-2-yl)amino]ethyl]-2-oxoindol-3-ylidene]amino]urea Chemical compound NC1=CC=C2N(CCN(C(C)C)C(C)C)C(=O)\C(=N\NC(N)=O)C2=C1 QUYARPNRTLDSRZ-HMMYKYKNSA-N 0.000 description 1
- MDIUACLPNGVWML-HMMYKYKNSA-N [(e)-[6-chloro-1-[2-[di(propan-2-yl)amino]ethyl]-2-oxoindol-3-ylidene]amino]urea Chemical compound C1=C(Cl)C=C2N(CCN(C(C)C)C(C)C)C(=O)\C(=N\NC(N)=O)C2=C1 MDIUACLPNGVWML-HMMYKYKNSA-N 0.000 description 1
- WHCYLASKADCFJM-RCCKNPSSSA-N [(e)-[7-bromo-1-[2-[di(propan-2-yl)amino]ethyl]-5-methyl-2-oxoindol-3-ylidene]amino]urea Chemical compound CC1=CC(Br)=C2N(CCN(C(C)C)C(C)C)C(=O)\C(=N\NC(N)=O)C2=C1 WHCYLASKADCFJM-RCCKNPSSSA-N 0.000 description 1
- TVDWXWSYKVPNDU-CYVLTUHYSA-N [(z)-[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-CYVLTUHYSA-N 0.000 description 1
- ZCJZIESLHUNJKW-UHFFFAOYSA-N [2-[cyclohexyl(propan-2-yl)amino]-2-oxoethyl] acetate Chemical compound CC(=O)OCC(=O)N(C(C)C)C1CCCCC1 ZCJZIESLHUNJKW-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 230000009858 acid secretion Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 229940069428 antacid Drugs 0.000 description 1
- 239000003159 antacid agent Substances 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 229940006138 antiglaucoma drug and miotics prostaglandin analogues Drugs 0.000 description 1
- 239000003443 antiviral agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 1
- 229960004484 carbachol Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- MOCKWYUCPREFCZ-UHFFFAOYSA-N chondroitin sulfate E (GalNAc4,6diS-GlcA), precursor 5a Chemical compound NNC(=O)NC1=CC=CC=C1 MOCKWYUCPREFCZ-UHFFFAOYSA-N 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000002183 duodenal effect Effects 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GGQOPZKTDHXXON-UHFFFAOYSA-N hexane;methanol Chemical compound OC.CCCCCC GGQOPZKTDHXXON-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 229940102213 injectable suspension Drugs 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- LYBKPDDZTNUNNM-UHFFFAOYSA-N isopropylbenzylamine Chemical compound CC(C)NCC1=CC=CC=C1 LYBKPDDZTNUNNM-UHFFFAOYSA-N 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000004701 malic acid derivatives Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- BKMLLFWFPNUDNF-UHFFFAOYSA-N methyl 2,3-dioxo-1h-indole-7-carboxylate Chemical compound COC(=O)C1=CC=CC2=C1NC(=O)C2=O BKMLLFWFPNUDNF-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000037023 motor activity Effects 0.000 description 1
- 230000009854 mucosal lesion Effects 0.000 description 1
- LNVLCLWBIBORCX-UHFFFAOYSA-N n-(2,3-dioxo-1h-indol-5-yl)acetamide Chemical compound CC(=O)NC1=CC=C2NC(=O)C(=O)C2=C1 LNVLCLWBIBORCX-UHFFFAOYSA-N 0.000 description 1
- DBVADBHSJCWFKI-UHFFFAOYSA-N n-(2-chloroethyl)-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C(C)C)CCCl DBVADBHSJCWFKI-UHFFFAOYSA-N 0.000 description 1
- TXIKUOVQZLPBSA-OQKWZONESA-N n-[(3e)-3-(carbamoylhydrazinylidene)-1-[2-[di(propan-2-yl)amino]ethyl]-2-oxoindol-5-yl]acetamide Chemical compound CC(=O)NC1=CC=C2N(CCN(C(C)C)C(C)C)C(=O)\C(=N\NC(N)=O)C2=C1 TXIKUOVQZLPBSA-OQKWZONESA-N 0.000 description 1
- PMCFTLWMSKQBFS-UHFFFAOYSA-N n-benzyl-2-chloro-n-propan-2-ylacetamide Chemical compound ClCC(=O)N(C(C)C)CC1=CC=CC=C1 PMCFTLWMSKQBFS-UHFFFAOYSA-N 0.000 description 1
- UYYCVBASZNFFRX-UHFFFAOYSA-N n-propan-2-ylcyclohexanamine Chemical compound CC(C)NC1CCCCC1 UYYCVBASZNFFRX-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 1
- 229960000444 pentagastrin Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 230000004622 sleep time Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- MNQYNQBOVCBZIQ-JQOFMKNESA-A sucralfate Chemical compound O[Al](O)OS(=O)(=O)O[C@@H]1[C@@H](OS(=O)(=O)O[Al](O)O)[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](COS(=O)(=O)O[Al](O)O)O[C@H]1O[C@@]1(COS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)O1 MNQYNQBOVCBZIQ-JQOFMKNESA-A 0.000 description 1
- 229960004291 sucralfate Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (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 (fr) |
| EP (1) | EP0205299A3 (fr) |
| JP (1) | JPS6289661A (fr) |
| KR (1) | KR870000296A (fr) |
| AU (1) | AU584710B2 (fr) |
| DK (1) | DK268186A (fr) |
| ES (1) | ES8801205A1 (fr) |
| FI (1) | FI862400A (fr) |
| NO (1) | NO862270L (fr) |
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 |
| AU1648600A (en) * | 1998-12-04 | 2000-06-26 | Neurosearch A/S | Use of isatin derivatives as ion channel activating agents |
| 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 (fr) * | 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/fr not_active Withdrawn
- 1986-06-05 JP JP61130949A patent/JPS6289661A/ja active Granted
- 1986-06-05 FI FI862400A patent/FI862400A/fi not_active Application Discontinuation
- 1986-06-06 AU AU58446/86A patent/AU584710B2/en not_active Ceased
- 1986-06-06 NO NO862270A patent/NO862270L/no unknown
- 1986-06-06 DK DK268186A patent/DK268186A/da not_active Application Discontinuation
- 1986-06-06 ES ES555835A patent/ES8801205A1/es not_active Expired
- 1986-06-07 KR KR1019860004517A patent/KR870000296A/ko not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| KR870000296A (ko) | 1987-02-17 |
| DK268186D0 (da) | 1986-06-06 |
| FI862400A0 (fi) | 1986-06-05 |
| ES555835A0 (es) | 1988-01-01 |
| AU5844686A (en) | 1986-12-11 |
| FI862400A (fi) | 1986-12-09 |
| JPH0482146B2 (fr) | 1992-12-25 |
| DK268186A (da) | 1986-12-09 |
| US4780477A (en) | 1988-10-25 |
| JPS6289661A (ja) | 1987-04-24 |
| ES8801205A1 (es) | 1988-01-01 |
| NO862270D0 (no) | 1986-06-06 |
| EP0205299A2 (fr) | 1986-12-17 |
| EP0205299A3 (fr) | 1988-01-20 |
| AU584710B2 (en) | 1989-06-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4355040A (en) | Hypotensive imidazole-5-acetic acid derivatives | |
| US5571833A (en) | Tryptamine analogues, their synthesis and their use as 5-HT1 -like or 5-HT2 receptor agonists | |
| FI103409B (fi) | Menetelmä farmaseuttisesti käyttökelpoisten bentsimidatsolijohdannaist en valmistamiseksi | |
| EP0484573B1 (fr) | 4- et 6-Carbamates se rapportant à la physostigmine, procédé et intermédiaires pour leur préparation et leur utilisation comme médicaments | |
| US20060148805A1 (en) | Opthalmic compositions for treating ocular hypertension | |
| DD201782A5 (de) | Verfahren zur herstellung von octahydro-1-(omega-mercaptoalkanoyl)-1h-indol 2-carbonsaeure-verbindungen | |
| CZ404391A3 (en) | 3-imidazolylmethyl-1,2,3,9-tetrahydro-4h-carbazol-4-one derivatives, process of their preparation and pharmaceutical preparations containing thereof | |
| CZ301697B6 (cs) | Indolový derivát a jeho použití a farmaceutický prostredek s jeho obsahem | |
| WO1992006088A1 (fr) | Derives d'indole utilises utilises comme agents antiallergiques et anti-inflammatoires | |
| EP0389984B1 (fr) | Carbonates de l'éséroline, procédé pour leur préparation et leur utilisation comme médicaments | |
| DE68906200T2 (de) | Kondensierte pyrazol-3-oxo-propannitril-derivate und verfahren zu deren herstellung. | |
| US5330986A (en) | Indole-7-carboxamide derivatives | |
| NO862270L (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive isatinforbindelser. | |
| IE913175A1 (en) | Aryl-fused and hetaryl-fused-2, 4-diazepine and 2,¹4-diazocine antiarrhythmic agents | |
| JP3690831B2 (ja) | インドール含有スルホンアミド誘導体 | |
| US20040142850A1 (en) | Benzimidazolidinone derivatives | |
| NO912946L (no) | P-acylaminofenoksikarbamater og derivater. | |
| US7902249B2 (en) | Indole derivatives substituted with long-chain alcohols and medicaments containing them | |
| US4482714A (en) | Pyrazino[2',3'-3,4]pyrido[1,2-a]indole derivatives | |
| US5478839A (en) | Cyclohexane derivatives | |
| SE460419B (sv) | Substituerade 1-pyridyloxi-3-indolylalkylamino-2-propanoler, foerfarande foer framstaellning av dessa och en farmaceutisk komposition | |
| EP0145304B1 (fr) | Dérivés de la tétrahydro bêta-carboline et procédé pour leur préparation | |
| SK61597A3 (en) | 6-methoxy-1h-benzotriazole-5-carboxamide derivatives, process for producing the same, and medicinal composition containing the same | |
| JPH0482147B2 (fr) | ||
| EP0532754A1 (fr) | Derive de tetrahydroimidazopyridine ou son sel |