JPH0533947B2 - - Google Patents
Info
- Publication number
- JPH0533947B2 JPH0533947B2 JP61113280A JP11328086A JPH0533947B2 JP H0533947 B2 JPH0533947 B2 JP H0533947B2 JP 61113280 A JP61113280 A JP 61113280A JP 11328086 A JP11328086 A JP 11328086A JP H0533947 B2 JPH0533947 B2 JP H0533947B2
- Authority
- JP
- Japan
- Prior art keywords
- isatin
- nmr
- diisopropylaminoethyl
- elemental analysis
- cdcl
- 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.)
- Expired - Lifetime
Links
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical class C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- 150000001875 compounds Chemical class 0.000 description 42
- 238000000921 elemental analysis Methods 0.000 description 31
- 229910052739 hydrogen Inorganic materials 0.000 description 31
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- 238000002844 melting Methods 0.000 description 27
- 230000008018 melting Effects 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
- 239000002904 solvent Substances 0.000 description 18
- -1 2-(N-isopropylcyclohexylamino) Ethyl chloride hydrochloride N-isopropylcyclohexylamine Chemical compound 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 208000000718 duodenal ulcer Diseases 0.000 description 14
- 239000012156 elution solvent Substances 0.000 description 14
- 239000003814 drug Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 208000007107 Stomach Ulcer Diseases 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 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 12
- 238000003756 stirring Methods 0.000 description 12
- 230000002496 gastric effect Effects 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
- 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 229940124597 therapeutic agent Drugs 0.000 description 8
- 208000025865 Ulcer Diseases 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000003818 flash chromatography Methods 0.000 description 7
- 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 7
- 231100000397 ulcer Toxicity 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 208000008469 Peptic Ulcer Diseases 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000047 product Substances 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 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
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 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 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000767 anti-ulcer Effects 0.000 description 3
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
- 210000004211 gastric acid Anatomy 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 210000002784 stomach Anatomy 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 2
- 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 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
- 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
- GKODDAXOSGGARJ-UHFFFAOYSA-N 5-Fluoroisatin Chemical compound FC1=CC=C2NC(=O)C(=O)C2=C1 GKODDAXOSGGARJ-UHFFFAOYSA-N 0.000 description 2
- DMHGXMPXHPOXBF-UHFFFAOYSA-N 5-Methoxyisatin Chemical compound COC1=CC=C2NC(=O)C(=O)C2=C1 DMHGXMPXHPOXBF-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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 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
- 150000001412 amines Chemical class 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
- 230000037396 body weight Effects 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 239000000812 cholinergic antagonist Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000001079 digestive effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 230000027119 gastric acid secretion Effects 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 239000003485 histamine H2 receptor antagonist Substances 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 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
- 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
- 239000003208 petroleum Substances 0.000 description 2
- 235000009518 sodium iodide Nutrition 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
- SJALPCXFOSGNST-UHFFFAOYSA-N 1-(2-bromoethyl)indole-2,3-dione Chemical compound C1=CC=C2N(CCBr)C(=O)C(=O)C2=C1 SJALPCXFOSGNST-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
- 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 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
- 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 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
- 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
- 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 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
- DKAVQCARZCYRIS-UHFFFAOYSA-N 4-bromo-5-methyl-1h-indole-2,3-dione Chemical compound CC1=CC=C2NC(=O)C(=O)C2=C1Br DKAVQCARZCYRIS-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 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 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
- 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 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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241001235534 Graphis <ascomycete fungus> Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229940121948 Muscarinic receptor antagonist Drugs 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
- 230000003042 antagnostic effect Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 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
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000881 depressing 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
- 125000006202 diisopropylaminoethyl group Chemical group [H]C([H])([H])C([H])(N(C([H])([H])C([H])([H])*)C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 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
- 239000000706 filtrate Substances 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
- 125000004435 hydrogen atom Chemical group [H]* 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
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 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 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
- 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 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
- PDUSWJORWQPNRP-UHFFFAOYSA-N n-propan-2-ylacetamide Chemical compound CC(C)NC(C)=O PDUSWJORWQPNRP-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 208000011906 peptic ulcer disease Diseases 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000012545 processing Methods 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
- 238000011160 research Methods 0.000 description 1
- 150000003349 semicarbazides Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 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
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 JPS62270559A (ja) | 1987-11-24 |
| JPH0533947B2 true 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 |
|---|---|
| JPS62270559A (ja) | 1987-11-24 |
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