JPH0342270B2 - - Google Patents
Info
- Publication number
- JPH0342270B2 JPH0342270B2 JP5562885A JP5562885A JPH0342270B2 JP H0342270 B2 JPH0342270 B2 JP H0342270B2 JP 5562885 A JP5562885 A JP 5562885A JP 5562885 A JP5562885 A JP 5562885A JP H0342270 B2 JPH0342270 B2 JP H0342270B2
- Authority
- JP
- Japan
- Prior art keywords
- oxindole
- formula
- added
- chloro
- water
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- JNYLMODTPLSLIF-UHFFFAOYSA-N 6-(trifluoromethyl)pyridine-3-carboxylic acid Chemical group OC(=O)C1=CC=C(C(F)(F)F)N=C1 JNYLMODTPLSLIF-UHFFFAOYSA-N 0.000 claims 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
- 239000007787 solid Substances 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 31
- -1 2-ureidophenyl Chemical group 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 25
- 238000001914 filtration Methods 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- 238000000034 method Methods 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- 238000003756 stirring Methods 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 11
- 239000002002 slurry Substances 0.000 description 11
- 235000011054 acetic acid Nutrition 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- HSYFISNDMZKGRS-UHFFFAOYSA-N 4-chloro-1h-indole-2,3-dione Chemical compound ClC1=CC=CC2=C1C(=O)C(=O)N2 HSYFISNDMZKGRS-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 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 5
- 230000000202 analgesic effect Effects 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 5
- UYINJAQCJCYCGO-UHFFFAOYSA-N 2-oxo-3h-indole-1-carboxamide Chemical compound C1=CC=C2N(C(=O)N)C(=O)CC2=C1 UYINJAQCJCYCGO-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 4
- 229960002327 chloral hydrate Drugs 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QAHVHSLSRLSVGS-UHFFFAOYSA-N sulfamoyl chloride Chemical compound NS(Cl)(=O)=O QAHVHSLSRLSVGS-UHFFFAOYSA-N 0.000 description 4
- XNSPDJAXCBZCRV-UHFFFAOYSA-N 4-chloro-1,3-dihydroindol-2-one Chemical compound ClC1=CC=CC2=C1CC(=O)N2 XNSPDJAXCBZCRV-UHFFFAOYSA-N 0.000 description 3
- KWXPDYCLJCAFSN-UHFFFAOYSA-N 6-fluoro-5-methyl-1,3-dihydroindol-2-one Chemical compound C1=C(F)C(C)=CC2=C1NC(=O)C2 KWXPDYCLJCAFSN-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000003110 anti-inflammatory effect Effects 0.000 description 3
- 239000011260 aqueous acid Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- DOLQYFPDPKPQSS-UHFFFAOYSA-N 3,4-dimethylaniline Chemical compound CC1=CC=C(N)C=C1C DOLQYFPDPKPQSS-UHFFFAOYSA-N 0.000 description 2
- DCWSRBDYLSWXIS-UHFFFAOYSA-N 4,5-dimethyl-1,3-dihydroindol-2-one Chemical compound CC1=CC=C2NC(=O)CC2=C1C DCWSRBDYLSWXIS-UHFFFAOYSA-N 0.000 description 2
- UZQSNRWCIFIUSJ-UHFFFAOYSA-N 4,5-dimethyl-1h-indole-2,3-dione Chemical compound CC1=CC=C2NC(=O)C(=O)C2=C1C UZQSNRWCIFIUSJ-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- BXMRWUIRVNVUBM-UHFFFAOYSA-N 4-ethoxy-2-methyl-1-nitrobenzene Chemical compound CCOC1=CC=C([N+]([O-])=O)C(C)=C1 BXMRWUIRVNVUBM-UHFFFAOYSA-N 0.000 description 2
- SJIANDNABPJQQW-UHFFFAOYSA-N 5,6-dimethyl-1,3-dihydroindol-2-one Chemical compound C1=C(C)C(C)=CC2=C1NC(=O)C2 SJIANDNABPJQQW-UHFFFAOYSA-N 0.000 description 2
- DYYQFOLXWSGDTB-UHFFFAOYSA-N 5-butoxy-1,3-dihydroindol-2-one Chemical compound CCCCOC1=CC=C2NC(=O)CC2=C1 DYYQFOLXWSGDTB-UHFFFAOYSA-N 0.000 description 2
- WIEJKTTWCGNQHH-UHFFFAOYSA-N 5-butyl-1h-indole-2,3-dione Chemical compound CCCCC1=CC=C2NC(=O)C(=O)C2=C1 WIEJKTTWCGNQHH-UHFFFAOYSA-N 0.000 description 2
- UKNVMAPOVWLHAP-UHFFFAOYSA-N 5-cycloheptyl-1h-indole-2,3-dione Chemical compound C1=C2C(=O)C(=O)NC2=CC=C1C1CCCCCC1 UKNVMAPOVWLHAP-UHFFFAOYSA-N 0.000 description 2
- FYGKPUITCUFXLV-UHFFFAOYSA-N 5-cyclopropyl-1h-indole-2,3-dione Chemical compound C1=C2C(=O)C(=O)NC2=CC=C1C1CC1 FYGKPUITCUFXLV-UHFFFAOYSA-N 0.000 description 2
- DDIIYGHHUMKDGI-UHFFFAOYSA-N 5-fluoro-1,3-dihydroindol-2-one Chemical compound FC1=CC=C2NC(=O)CC2=C1 DDIIYGHHUMKDGI-UHFFFAOYSA-N 0.000 description 2
- FIWADZAJMKCAHJ-UHFFFAOYSA-N 5-fluoro-3-methyl-1,3-dihydroindole-2-thione Chemical compound C1=C(F)C=C2C(C)C(=S)NC2=C1 FIWADZAJMKCAHJ-UHFFFAOYSA-N 0.000 description 2
- JQCGHRDKVZPCRO-UHFFFAOYSA-N 5-nitro-1,3-dihydroindol-2-one Chemical compound [O-][N+](=O)C1=CC=C2NC(=O)CC2=C1 JQCGHRDKVZPCRO-UHFFFAOYSA-N 0.000 description 2
- CENVPIZOTHULGJ-UHFFFAOYSA-N 6-chloro-1,3-dihydroindol-2-one Chemical compound ClC1=CC=C2CC(=O)NC2=C1 CENVPIZOTHULGJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- MDIAKIHKBBNYHF-UHFFFAOYSA-N Ethyl 2-(methylthio)acetate Chemical compound CCOC(=O)CSC MDIAKIHKBBNYHF-UHFFFAOYSA-N 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000002260 anti-inflammatory agent Substances 0.000 description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- JNCFYJHIPGISLS-UHFFFAOYSA-N n-(2-oxo-3h-indole-1-carbonyl)sulfamoyl chloride Chemical class C1=CC=C2N(C(=O)NS(=O)(=O)Cl)C(=O)CC2=C1 JNCFYJHIPGISLS-UHFFFAOYSA-N 0.000 description 2
- 150000005623 oxindoles Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 2
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- NIXBYYISFAXGLX-UHFFFAOYSA-N 2,3,6,8-tetrahydro-[1,4]dioxino[2,3-f]indol-7-one Chemical class O1CCOC2=C1C=C1CC(=O)NC1=C2 NIXBYYISFAXGLX-UHFFFAOYSA-N 0.000 description 1
- VNMTZLQZNOJMHW-UHFFFAOYSA-N 2-(2-oxo-3h-indol-1-yl)acetamide Chemical class C1=CC=C2N(CC(=O)N)C(=O)CC2=C1 VNMTZLQZNOJMHW-UHFFFAOYSA-N 0.000 description 1
- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 1
- SGWARXIRNQTLND-UHFFFAOYSA-N 3-(2-phenoxyacetyl)-1,3-dihydroindol-2-one Chemical compound O=C1NC2=CC=CC=C2C1C(=O)COC1=CC=CC=C1 SGWARXIRNQTLND-UHFFFAOYSA-N 0.000 description 1
- XWLIAACTIOFOOA-UHFFFAOYSA-N 3-(2-thiophen-2-ylacetyl)-1,3-dihydroindol-2-one Chemical compound O=C1NC2=CC=CC=C2C1C(=O)CC1=CC=CS1 XWLIAACTIOFOOA-UHFFFAOYSA-N 0.000 description 1
- BZNRLFBUTXSYHJ-UHFFFAOYSA-N 3-(furan-3-carbonyl)-1,3-dihydroindol-2-one Chemical compound O=C1NC2=CC=CC=C2C1C(=O)C=1C=COC=1 BZNRLFBUTXSYHJ-UHFFFAOYSA-N 0.000 description 1
- JUPOEJXDARZUBY-UHFFFAOYSA-N 3-(thiophene-2-carbonyl)-1,3-dihydroindol-2-one Chemical compound O=C1NC2=CC=CC=C2C1C(=O)C1=CC=CS1 JUPOEJXDARZUBY-UHFFFAOYSA-N 0.000 description 1
- AROWMXMFGCAVGV-UHFFFAOYSA-N 3-acetyl-5-chloro-2-oxo-3h-indole-1-carboxamide Chemical compound C1=C(Cl)C=C2C(C(=O)C)C(=O)N(C(N)=O)C2=C1 AROWMXMFGCAVGV-UHFFFAOYSA-N 0.000 description 1
- PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
- KCHLDNLIJVSRPK-UHFFFAOYSA-N 3-methylsulfanylaniline Chemical compound CSC1=CC=CC(N)=C1 KCHLDNLIJVSRPK-UHFFFAOYSA-N 0.000 description 1
- OGIQUQKNJJTLSZ-UHFFFAOYSA-N 4-butylaniline Chemical compound CCCCC1=CC=C(N)C=C1 OGIQUQKNJJTLSZ-UHFFFAOYSA-N 0.000 description 1
- LPOAFPIPCHFMQF-UHFFFAOYSA-N 4-butylsulfanylaniline Chemical compound CCCCSC1=CC=C(N)C=C1 LPOAFPIPCHFMQF-UHFFFAOYSA-N 0.000 description 1
- LPBWEMHFJIWLDB-UHFFFAOYSA-N 4-cycloheptylaniline Chemical compound C1=CC(N)=CC=C1C1CCCCCC1 LPBWEMHFJIWLDB-UHFFFAOYSA-N 0.000 description 1
- UBXDNWVNEZBDBN-UHFFFAOYSA-N 4-cyclopropylaniline Chemical compound C1=CC(N)=CC=C1C1CC1 UBXDNWVNEZBDBN-UHFFFAOYSA-N 0.000 description 1
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 1
- RTZOGYCMIMOVHU-UHFFFAOYSA-N 4-methoxy-2-methyl-1-nitrobenzene Chemical compound COC1=CC=C([N+]([O-])=O)C(C)=C1 RTZOGYCMIMOVHU-UHFFFAOYSA-N 0.000 description 1
- PIIZYNQECPTVEO-UHFFFAOYSA-N 4-nitro-m-cresol Chemical compound CC1=CC(O)=CC=C1[N+]([O-])=O PIIZYNQECPTVEO-UHFFFAOYSA-N 0.000 description 1
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 1
- MSOLDJZABLHVER-UHFFFAOYSA-N 5,6-difluoro-1,3-dihydroindol-2-one Chemical compound C1=C(F)C(F)=CC2=C1NC(=O)C2 MSOLDJZABLHVER-UHFFFAOYSA-N 0.000 description 1
- FQIJOGDQWRLSQW-UHFFFAOYSA-N 5,6-difluoro-1h-indole-2,3-dione Chemical compound C1=C(F)C(F)=CC2=C1C(=O)C(=O)N2 FQIJOGDQWRLSQW-UHFFFAOYSA-N 0.000 description 1
- YUVNTBICDDRBFP-UHFFFAOYSA-N 5,6-dimethoxy-1,3-dihydroindol-2-one Chemical compound C1=C(OC)C(OC)=CC2=C1NC(=O)C2 YUVNTBICDDRBFP-UHFFFAOYSA-N 0.000 description 1
- BRWIXNVFRUVHEU-UHFFFAOYSA-N 5,6-dimethyl-1h-indole-2,3-dione Chemical compound C1=C(C)C(C)=CC2=C1C(=O)C(=O)N2 BRWIXNVFRUVHEU-UHFFFAOYSA-N 0.000 description 1
- RVFZMXCPHCAUQH-UHFFFAOYSA-N 5,7-dihydro-[1,3]dioxolo[4,5-f]indol-6-one Chemical compound C1=C2NC(=O)CC2=CC2=C1OCO2 RVFZMXCPHCAUQH-UHFFFAOYSA-N 0.000 description 1
- DJUVRTVJSHICLO-UHFFFAOYSA-N 5-(thiophene-2-carbonyl)-1,3-dihydroindol-2-one Chemical compound C=1C=C2NC(=O)CC2=CC=1C(=O)C1=CC=CS1 DJUVRTVJSHICLO-UHFFFAOYSA-N 0.000 description 1
- RANTVMNWZIWPNR-UHFFFAOYSA-N 5-(trifluoromethyl)-1,3-dihydroindol-2-one Chemical compound FC(F)(F)C1=CC=C2NC(=O)CC2=C1 RANTVMNWZIWPNR-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
- JIQWNLUFSNXDGO-UHFFFAOYSA-N 5-amino-2-oxo-3h-indole-1-carboxamide Chemical compound NC1=CC=C2N(C(=O)N)C(=O)CC2=C1 JIQWNLUFSNXDGO-UHFFFAOYSA-N 0.000 description 1
- DZNAJEDQDMDIEL-UHFFFAOYSA-N 5-benzoyl-1,3-dihydroindol-2-one Chemical compound C=1C=C2NC(=O)CC2=CC=1C(=O)C1=CC=CC=C1 DZNAJEDQDMDIEL-UHFFFAOYSA-N 0.000 description 1
- VIMNAEVMZXIKFL-UHFFFAOYSA-N 5-bromo-1,3-dihydroindol-2-one Chemical compound BrC1=CC=C2NC(=O)CC2=C1 VIMNAEVMZXIKFL-UHFFFAOYSA-N 0.000 description 1
- JSUXWKVCRKZYRP-UHFFFAOYSA-N 5-butyl-1,3-dihydroindol-2-one Chemical compound CCCCC1=CC=C2NC(=O)CC2=C1 JSUXWKVCRKZYRP-UHFFFAOYSA-N 0.000 description 1
- IGPDWKCUDHIIRL-UHFFFAOYSA-N 5-chloro-2-oxo-3-[oxo(thiophen-2-yl)methyl]-3H-indole-1-carboxamide Chemical compound C12=CC(Cl)=CC=C2N(C(=O)N)C(=O)C1C(=O)C1=CC=CS1 IGPDWKCUDHIIRL-UHFFFAOYSA-N 0.000 description 1
- OMWYWPNJQWIJRG-UHFFFAOYSA-N 5-chloro-3-(thiophene-2-carbonyl)-1,3-dihydroindol-2-one Chemical compound C12=CC(Cl)=CC=C2NC(=O)C1C(=O)C1=CC=CS1 OMWYWPNJQWIJRG-UHFFFAOYSA-N 0.000 description 1
- YZYLXNPSGVLBST-UHFFFAOYSA-N 5-cycloheptyl-1,3-dihydroindol-2-one Chemical compound C=1C=C2NC(=O)CC2=CC=1C1CCCCCC1 YZYLXNPSGVLBST-UHFFFAOYSA-N 0.000 description 1
- AJZMZMYIAKKFOG-UHFFFAOYSA-N 5-cyclopropyl-1,3-dihydroindol-2-one Chemical compound C=1C=C2NC(=O)CC2=CC=1C1CC1 AJZMZMYIAKKFOG-UHFFFAOYSA-N 0.000 description 1
- DYTNNGQPYKZMNF-UHFFFAOYSA-N 5-ethoxy-1,3-dihydroindol-2-one Chemical compound CCOC1=CC=C2NC(=O)CC2=C1 DYTNNGQPYKZMNF-UHFFFAOYSA-N 0.000 description 1
- DFGZEOUBIHLXFD-UHFFFAOYSA-N 5-methoxy-1,3-dihydroindol-2-one Chemical compound COC1=CC=C2NC(=O)CC2=C1 DFGZEOUBIHLXFD-UHFFFAOYSA-N 0.000 description 1
- HXQDSHSATAEREW-UHFFFAOYSA-N 5-methyl-1,3-dihydroindol-2-one Chemical compound CC1=CC=C2NC(=O)CC2=C1 HXQDSHSATAEREW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SYJHBRHSEPKLMR-UHFFFAOYSA-N 5-methyl-2-oxo-3h-indole-1-carboxamide Chemical compound CC1=CC=C2N(C(N)=O)C(=O)CC2=C1 SYJHBRHSEPKLMR-UHFFFAOYSA-N 0.000 description 1
- LZPKWQOLOCLSBO-UHFFFAOYSA-N 6-(trifluoromethyl)-1,3-dihydroindol-2-one Chemical compound FC(F)(F)C1=CC=C2CC(=O)NC2=C1 LZPKWQOLOCLSBO-UHFFFAOYSA-N 0.000 description 1
- PKQNTFAOZIVXCE-UHFFFAOYSA-N 6-fluoro-1,3-dihydroindol-2-one Chemical compound FC1=CC=C2CC(=O)NC2=C1 PKQNTFAOZIVXCE-UHFFFAOYSA-N 0.000 description 1
- OXOQGUGIJKUSRP-UHFFFAOYSA-N 6-methoxy-1,3-dihydroindol-2-one Chemical compound COC1=CC=C2CC(=O)NC2=C1 OXOQGUGIJKUSRP-UHFFFAOYSA-N 0.000 description 1
- FDUXWVHCBHIAEQ-UHFFFAOYSA-N 6-methyl-2-oxo-3h-indole-1-carbothioamide Chemical compound CC1=CC=C2CC(=O)N(C(N)=S)C2=C1 FDUXWVHCBHIAEQ-UHFFFAOYSA-N 0.000 description 1
- BRTXRFCARXOWJV-UHFFFAOYSA-N 6-phenyl-1,3-dihydroindol-2-one Chemical compound C1=C2NC(=O)CC2=CC=C1C1=CC=CC=C1 BRTXRFCARXOWJV-UHFFFAOYSA-N 0.000 description 1
- FPDLUAACCNVSQA-UHFFFAOYSA-N 7-chloro-1,3-dihydroindol-2-one Chemical compound ClC1=CC=CC2=C1NC(=O)C2 FPDLUAACCNVSQA-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 229960004424 carbon dioxide Drugs 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- IDKXMGZRWKCTGA-UHFFFAOYSA-N chloroimino(oxo)methane Chemical compound ClN=C=O IDKXMGZRWKCTGA-UHFFFAOYSA-N 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- YMAWHLWKSJTZPH-UHFFFAOYSA-N ethyl 2-oxo-6-phenyl-3h-indole-1-carboxylate Chemical compound C1=C2N(C(=O)OCC)C(=O)CC2=CC=C1C1=CC=CC=C1 YMAWHLWKSJTZPH-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 238000010667 large scale reaction Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N monofluoromethane Natural products FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- MDZULUPIIRBWJO-UHFFFAOYSA-N n-[5-chloro-2-oxo-3-(thiophene-2-carbonyl)-3h-indole-1-carbonyl]sulfamoyl chloride Chemical compound C12=CC(Cl)=CC=C2N(C(=O)NS(Cl)(=O)=O)C(=O)C1C(=O)C1=CC=CS1 MDZULUPIIRBWJO-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US59066784A | 1984-03-19 | 1984-03-19 | |
| US590667 | 1984-03-19 | ||
| US684889 | 1984-12-21 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2336861A Division JPH03178963A (ja) | 1984-03-19 | 1990-11-30 | ２―オキシインドール―１―カルボキサミド化合物の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60209565A JPS60209565A (ja) | 1985-10-22 |
| JPH0342270B2 true JPH0342270B2 (fi) | 1991-06-26 |
Family
ID=24363181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5562885A Granted JPS60209565A (ja) | 1984-03-19 | 1985-03-19 | Ｎ―クロロスルホニル―２―オキシインドール―１―カルボキサミド化合物 |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS60209565A (fi) |
| DD (1) | DD232265A5 (fi) |
| IN (1) | IN162626B (fi) |
| MW (1) | MW585A1 (fi) |
| SU (1) | SU1630611A3 (fi) |
| ZA (1) | ZA851994B (fi) |
| ZM (1) | ZM1085A1 (fi) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6570301B2 (ja) * | 2015-04-23 | 2019-09-04 | キヤノン株式会社 | ４−フルオロイサチン誘導体の製造方法 |
-
1985
- 1985-02-26 IN IN155/DEL/85A patent/IN162626B/en unknown
- 1985-03-18 SU SU853869756A patent/SU1630611A3/ru active
- 1985-03-18 MW MW585A patent/MW585A1/xx unknown
- 1985-03-18 ZA ZA851994A patent/ZA851994B/xx unknown
- 1985-03-18 DD DD85274213A patent/DD232265A5/de not_active IP Right Cessation
- 1985-03-19 JP JP5562885A patent/JPS60209565A/ja active Granted
- 1985-03-19 ZM ZM1085A patent/ZM1085A1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA851994B (en) | 1986-11-26 |
| DD232265A5 (de) | 1986-01-22 |
| MW585A1 (en) | 1986-04-09 |
| IN162626B (fi) | 1988-06-18 |
| ZM1085A1 (en) | 1985-09-20 |
| SU1630611A3 (ru) | 1991-02-23 |
| JPS60209565A (ja) | 1985-10-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |