JPS62270559A - イサチン誘導体 - Google Patents
イサチン誘導体Info
- Publication number
- JPS62270559A JPS62270559A JP11328086A JP11328086A JPS62270559A JP S62270559 A JPS62270559 A JP S62270559A JP 11328086 A JP11328086 A JP 11328086A JP 11328086 A JP11328086 A JP 11328086A JP S62270559 A JPS62270559 A JP S62270559A
- Authority
- JP
- Japan
- Prior art keywords
- isatin
- formula
- value
- solvent
- elemental analysis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical class C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 title abstract description 45
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 23
- 239000002904 solvent Substances 0.000 abstract description 19
- 208000000718 duodenal ulcer Diseases 0.000 abstract description 15
- 208000007107 Stomach Ulcer Diseases 0.000 abstract description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 6
- 150000001412 amines Chemical class 0.000 abstract description 2
- 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 abstract 1
- 201000005917 gastric ulcer Diseases 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- 238000000921 elemental analysis Methods 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000012156 elution solvent Substances 0.000 description 13
- 238000001816 cooling Methods 0.000 description 12
- 239000003814 drug Substances 0.000 description 12
- 230000002496 gastric effect Effects 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 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 9
- 229940124597 therapeutic agent Drugs 0.000 description 9
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
- OWFDMTIOBATGBR-UHFFFAOYSA-N n-butyl-n-(2-chloroethyl)butan-1-amine;hydron;chloride Chemical compound Cl.CCCCN(CCCl)CCCC OWFDMTIOBATGBR-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 208000025865 Ulcer Diseases 0.000 description 7
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Substances CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 7
- 229940043279 diisopropylamine Drugs 0.000 description 7
- 238000003818 flash chromatography Methods 0.000 description 7
- -1 lithium aluminum hydride Chemical compound 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 238000010898 silica gel chromatography Methods 0.000 description 7
- 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
- 231100000397 ulcer Toxicity 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 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 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 208000008469 Peptic Ulcer Diseases 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- JECOSSASMXAXFV-UHFFFAOYSA-N chloroethane;hydrochloride Chemical compound Cl.CCCl JECOSSASMXAXFV-UHFFFAOYSA-N 0.000 description 4
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 4
- 229960001340 histamine Drugs 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 230000028327 secretion Effects 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- DMHGXMPXHPOXBF-UHFFFAOYSA-N 5-Methoxyisatin Chemical compound COC1=CC=C2NC(=O)C(=O)C2=C1 DMHGXMPXHPOXBF-UHFFFAOYSA-N 0.000 description 3
- 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 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 210000004211 gastric acid Anatomy 0.000 description 3
- 230000027119 gastric acid secretion Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 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
- MBVCESWADCIXJN-UHFFFAOYSA-N 5-Bromoisatin Chemical compound BrC1=CC=C2NC(=O)C(=O)C2=C1 MBVCESWADCIXJN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 2
- 241000700157 Rattus norvegicus Species 0.000 description 2
- 206010042220 Stress ulcer Diseases 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 229940069428 antacid Drugs 0.000 description 2
- 239000003159 antacid agent Substances 0.000 description 2
- 230000002467 anti-pepsin effect Effects 0.000 description 2
- 239000002249 anxiolytic agent Substances 0.000 description 2
- 230000000949 anxiolytic effect Effects 0.000 description 2
- 229940005530 anxiolytics Drugs 0.000 description 2
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 2
- 239000000812 cholinergic antagonist Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 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 2
- 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 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 229940044551 receptor antagonist Drugs 0.000 description 2
- 239000002464 receptor antagonist Substances 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 239000003204 tranquilizing agent Substances 0.000 description 2
- 230000002936 tranquilizing effect Effects 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
- 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 1
- 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 1
- MYAPUDLDPIKVNK-UHFFFAOYSA-N 1-[2-[di(propan-2-yl)amino]ethyl]-5-methoxyindole-2,3-dione Chemical compound COC1=CC=C2N(CCN(C(C)C)C(C)C)C(=O)C(=O)C2=C1 MYAPUDLDPIKVNK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- 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 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
- IDGDRZFXQRBZRR-UHFFFAOYSA-N 2-chloropropane;hydrochloride Chemical compound Cl.CC(C)Cl IDGDRZFXQRBZRR-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
- GKODDAXOSGGARJ-UHFFFAOYSA-N 5-Fluoroisatin Chemical compound FC1=CC=C2NC(=O)C(=O)C2=C1 GKODDAXOSGGARJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 201000004029 Immune dysregulation-polyendocrinopathy-enteropathy-X-linked syndrome Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- 108010079943 Pentagastrin Proteins 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
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 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
- 238000004364 calculation method Methods 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- RBNPZEHAODHBPZ-UHFFFAOYSA-M dihydroxyaluminium Chemical compound O.O.NCC(=O)O[Al] RBNPZEHAODHBPZ-UHFFFAOYSA-M 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 210000001156 gastric mucosa Anatomy 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
- 230000000147 hypnotic effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- OPNUBWBPOZDXDJ-UHFFFAOYSA-N n-(2-chloroethyl)-n-methylbutan-1-amine;hydrochloride Chemical compound Cl.CCCCN(C)CCCl OPNUBWBPOZDXDJ-UHFFFAOYSA-N 0.000 description 1
- UURRECHSOADBEG-UHFFFAOYSA-N n-butyl-n-(3-chloropropyl)butan-1-amine;hydrochloride Chemical compound Cl.CCCCN(CCCC)CCCCl UURRECHSOADBEG-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
- 229940094443 oxytocics prostaglandins Drugs 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
- 208000011906 peptic ulcer disease Diseases 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003349 semicarbazides Chemical class 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000017423 tissue regeneration Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Indole Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11328086A JPS62270559A (ja) | 1986-05-16 | 1986-05-16 | イサチン誘導体 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11328086A JPS62270559A (ja) | 1986-05-16 | 1986-05-16 | イサチン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62270559A true JPS62270559A (ja) | 1987-11-24 |
| JPH0533947B2 JPH0533947B2 (es) | 1993-05-20 |
Family
ID=14608176
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11328086A Granted JPS62270559A (ja) | 1986-05-16 | 1986-05-16 | イサチン誘導体 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62270559A (es) |
-
1986
- 1986-05-16 JP JP11328086A patent/JPS62270559A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0533947B2 (es) | 1993-05-20 |
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