NO124695B - - Google Patents
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- Publication number
- NO124695B NO124695B NO16909467A NO16909467A NO124695B NO 124695 B NO124695 B NO 124695B NO 16909467 A NO16909467 A NO 16909467A NO 16909467 A NO16909467 A NO 16909467A NO 124695 B NO124695 B NO 124695B
- Authority
- NO
- Norway
- Prior art keywords
- parts
- oxindole
- nitro
- mixture
- melting point
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims description 34
- -1 alkenyl sulfonic acid Chemical compound 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 3
- 150000008053 sultones Chemical class 0.000 claims 3
- 239000003599 detergent Substances 0.000 claims 2
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 claims 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 238000006277 sulfonation reaction Methods 0.000 claims 1
- 239000004711 α-olefin Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 66
- 238000002844 melting Methods 0.000 description 30
- 230000008018 melting Effects 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 238000010992 reflux Methods 0.000 description 15
- 230000000844 anti-bacterial effect Effects 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- JPUYXUBUJJDJNL-UHFFFAOYSA-N 5-amino-1,3-dihydroindol-2-one Chemical compound NC1=CC=C2NC(=O)CC2=C1 JPUYXUBUJJDJNL-UHFFFAOYSA-N 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- BXWNKGSJHAJOGX-UHFFFAOYSA-N n-hexadecyl alcohol Natural products CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 8
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 7
- 239000007859 condensation product Substances 0.000 description 7
- 150000002475 indoles Chemical class 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000004359 castor oil Substances 0.000 description 6
- 235000019438 castor oil Nutrition 0.000 description 6
- 229940082500 cetostearyl alcohol Drugs 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000006185 dispersion Substances 0.000 description 6
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 229960000541 cetyl alcohol Drugs 0.000 description 5
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- LPYIXHHGKPBPCF-UHFFFAOYSA-N acetic acid;5-nitrofuran-2-carbaldehyde Chemical compound CC(O)=O.CC(O)=O.[O-][N+](=O)C1=CC=C(C=O)O1 LPYIXHHGKPBPCF-UHFFFAOYSA-N 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 4
- YPCRTQSPZPUZBW-UHFFFAOYSA-N n-(2-oxo-1,3-dihydroindol-5-yl)benzamide Chemical compound C=1C=C2NC(=O)CC2=CC=1NC(=O)C1=CC=CC=C1 YPCRTQSPZPUZBW-UHFFFAOYSA-N 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 230000002421 anti-septic effect Effects 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VTWWMSFVYMHCJI-UHFFFAOYSA-N n-(2-oxo-1,3-dihydroindol-4-yl)acetamide Chemical compound CC(=O)NC1=CC=CC2=C1CC(=O)N2 VTWWMSFVYMHCJI-UHFFFAOYSA-N 0.000 description 3
- HHYYCDSLDUDUBN-UHFFFAOYSA-N n-(2-oxo-1,3-dihydroindol-5-yl)propanamide Chemical compound CCC(=O)NC1=CC=C2NC(=O)CC2=C1 HHYYCDSLDUDUBN-UHFFFAOYSA-N 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 150000005623 oxindoles Chemical class 0.000 description 3
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IQXJCCZJOIKIAD-UHFFFAOYSA-N 1-(2-methoxyethoxy)hexadecane Chemical compound CCCCCCCCCCCCCCCCOCCOC IQXJCCZJOIKIAD-UHFFFAOYSA-N 0.000 description 2
- 229940093475 2-ethoxyethanol Drugs 0.000 description 2
- CBQDTCDOVVBGMN-UHFFFAOYSA-N 2-methyl-3-octylphenol Chemical compound CCCCCCCCC1=CC=CC(O)=C1C CBQDTCDOVVBGMN-UHFFFAOYSA-N 0.000 description 2
- GCBJSIMATFNFAB-UHFFFAOYSA-N 2-methyl-3-oxo-3-[(2-oxo-1,3-dihydroindol-5-yl)amino]propanoic acid Chemical compound C(=O)(O)C(C(=O)NC=1C=C2CC(NC2=CC1)=O)C GCBJSIMATFNFAB-UHFFFAOYSA-N 0.000 description 2
- ZNINKECAYRRRRK-UHFFFAOYSA-N 4-amino-1,3-dihydroindol-2-one Chemical compound NC1=CC=CC2=C1CC(=O)N2 ZNINKECAYRRRRK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000001856 Ethyl cellulose Substances 0.000 description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007765 cera alba Substances 0.000 description 2
- 229950009789 cetomacrogol 1000 Drugs 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 235000019325 ethyl cellulose Nutrition 0.000 description 2
- 229920001249 ethyl cellulose Polymers 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229940057838 polyethylene glycol 4000 Drugs 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- IFKPLJWIEQBPGG-QGZVFWFLSA-N (5s)-6-(dimethylamino)-5-methyl-4,4-diphenylhexan-3-one Chemical compound C=1C=CC=CC=1C([C@H](C)CN(C)C)(C(=O)CC)C1=CC=CC=C1 IFKPLJWIEQBPGG-QGZVFWFLSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-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
- ZGTUSQAQXWSMDW-UHFFFAOYSA-N 5-hydroxy-1,3-dihydroindol-2-one Chemical compound OC1=CC=C2NC(=O)CC2=C1 ZGTUSQAQXWSMDW-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
- 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 1
- OCOCBVKMMMIDLI-UHFFFAOYSA-N 6-amino-1,3-dihydroindol-2-one Chemical compound NC1=CC=C2CC(=O)NC2=C1 OCOCBVKMMMIDLI-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- MQHWFIOJQSCFNM-UHFFFAOYSA-L Magnesium salicylate Chemical compound [Mg+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O MQHWFIOJQSCFNM-UHFFFAOYSA-L 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 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
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012738 dissolution medium Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- GAPFXVWCGZCQPI-UHFFFAOYSA-N n-(2-oxo-1,3-dihydroindol-5-yl)acetamide Chemical compound CC(=O)NC1=CC=C2NC(=O)CC2=C1 GAPFXVWCGZCQPI-UHFFFAOYSA-N 0.000 description 1
- YLBYAZHPXJQIPP-UHFFFAOYSA-N n-(2-oxo-1,3-dihydroindol-6-yl)acetamide Chemical compound CC(=O)NC1=CC=C2CC(=O)NC2=C1 YLBYAZHPXJQIPP-UHFFFAOYSA-N 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/33—Amino carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
- C11D1/143—Sulfonic acid esters
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Detergent Compositions (AREA)
- Indole Compounds (AREA)
Description
Fremgangsmåte for fremstilling av nye antibakterielle indolderivater. Process for the production of new antibacterial indole derivatives.
Foreliggende oppfinnelse vedrører en The present invention relates to a
fremgangsmåte til fremstilling av nye method for the production of new
indolderivater og mer spesielt 3-(5-nitro-2-furfuryliden)oksindolderivater, som er i indole derivatives and more particularly 3-(5-nitro-2-furfurylidene)oxindole derivatives, which are in
besittelse av terapeutiske egenskaper. possession of therapeutic properties.
I henhold til oppfinnelsen fremstilles According to the invention is produced
nye indolderivater, som er forbindelser av new indole derivs., which are compounds of
formelen the formula
hvor R betyr hydrogen eller en acylgruppe, where R means hydrogen or an acyl group,
og hvor kjernen A eventuelt kan bære substituenter. and where the core A may optionally carry substituents.
Som skikkete substituenter i kjernen As suitable substituents in the core
A skal f. eks. nevnes halogen-, nitro-, acyl-amino-, alkyl-, hydroksy-, alkoksy- og karboksylsyreradikaler. A must e.g. halogen, nitro, acyl-amino, alkyl, hydroxy, alkoxy and carboxylic acid radicals are mentioned.
Som en særlig verdifull forbindelse skal As a particularly valuable connection should
nevnes 3-(5-nitro-2-furfuryliden)-oksindol. mention is made of 3-(5-nitro-2-furfurylidene)-oxindole.
I henhold til- oppfinnelsen fremstilles According to the invention is produced
de nye indolderivater ved at et oksindolderivat av formelen: the new indole derivatives in that an oxindole derivative of the formula:
bringes til å reagere med 5-nitro-2-fur-aldehyd eller med en forbindelse som er i stand til å virke som 5-nitro-2-furaldehyd. is reacted with 5-nitro-2-furaldehyde or with a compound capable of acting as 5-nitro-2-furaldehyde.
Som forbindelser som er i stand til å reagere som 5-nitro-2-furaldehyd skal f. eks. nevnes 5-nitro-2-furaldehyd-diacetat i nærvær av en vandig mineralsyre, som f. eks. vandig saltsyre. Reaksjonen kan hensiktsmessig utføres i et passende oppløs-ningsmiddel eller fortynningsmiddel, f. eks. eddiksyre, i vandig etanol eller i vannfri maursyre. Der kan også eventuelt være til stede en basisk katalysator, f. eks. natriumacetat. As compounds capable of reacting as 5-nitro-2-furaldehyde, e.g. mention is made of 5-nitro-2-furaldehyde diacetate in the presence of an aqueous mineral acid, such as aqueous hydrochloric acid. The reaction can conveniently be carried out in a suitable solvent or diluent, e.g. acetic acid, in aqueous ethanol or in anhydrous formic acid. A basic catalyst may also optionally be present, e.g. sodium acetate.
Som nevnt er de nye indolderivater i henhold til oppfinnelsen i besittelse av nyttige terapeutiske egenskaper. De er særlig nyttige som antibakterielle midler, særlig for antiseptiske øyemed. De er aktive mot et stort område av mikrobeorganismer innbefattet Gram-positive og Gram-nega-tive bakterier. As mentioned, the new indole derivatives according to the invention possess useful therapeutic properties. They are particularly useful as antibacterial agents, especially for antiseptic purposes. They are active against a large range of micro-organisms including Gram-positive and Gram-negative bacteria.
I henhold til et ytterligere trekk ved oppfinnelsen tilveiebringes nye antimi-krobepreparater, hvor den aktive bestanddel er i det minste ett av de nye indolderivater av den foran angitte formel. According to a further feature of the invention, new antimicrobial preparations are provided, where the active ingredient is at least one of the new indole derivatives of the above formula.
Som en særlig verdifull bestanddel skal f. eks. nevnes 3-(5-nitro-2-furfuryli-den)-oksindol. As a particularly valuable component, e.g. mention is made of 3-(5-nitro-2-furfurylidene)-oxindole.
De nevnte preparater kan foreligge i form av oppløsninger i polyetylenglykol, som eventuelt kan inneholde fuktnings-midler, f. eks. kondenseringsprodukter av alkylfenoler med etylenoksyd, f. eks. kon-denseringsproduktet av oktylkresol med 8 The preparations mentioned may be available in the form of solutions in polyethylene glycol, which may optionally contain wetting agents, e.g. condensation products of alkylphenols with ethylene oxide, e.g. the condensation product of octylcresol with 8
—10 molekylardeler etylenoksyd. Prepara-tene kan også foreligge i form av vandige —10 molecular parts of ethylene oxide. The preparations can also be available in aqueous form
dispersjoner, hvor et skikket dispergerings-middel eller overflateaktivt middel er polyoksyetylen-sorbitanmonooleat. Passende vandige dispers joner kan inneholde ikke-giftige bestanddeler som er blandbare med vann, f. eks. glyserin, fortykningsmidler eller gelatineringsmidler, f. eks. etylcellulose og kondenseringsprodukter av fettalkoholer og etylenoksyd ,f. eks. det voks-aktige, oljeaktige produkt som fåes fra kondenseringen av cetyl eller cetostearylalkohol og 20—24 molekylardeler etylenoksyd. De nevnte preparater kan også foreligge i form av oljeaktige oppløsninger, og et skikket oljeaktig oppløsningsmedium kan f. eks. være risinusolje. dispersions, where a suitable dispersant or surfactant is polyoxyethylene sorbitan monooleate. Suitable aqueous dispers ions may contain non-toxic ingredients which are miscible with water, e.g. glycerin, thickeners or gelatinizers, e.g. ethyl cellulose and condensation products of fatty alcohols and ethylene oxide, e.g. e.g. the waxy, oily product obtained from the condensation of cetyl or cetostearyl alcohol and 20-24 molecular parts of ethylene oxide. The aforementioned preparations can also be available in the form of oily solutions, and a suitable oily dissolution medium can e.g. be castor oil.
Antimikrobepreparatene kan også foreligge i form av kremer, salver og pastaer, og slike preparater kan inneholde hvilke som helst skikkete kjente ikke-giftige bestanddeler .Således kan et skikket salve-grunnlag bestå av en blanding av polyetylenglykol 400 og polyetylenglykol 4000 og en skikket pasta kan bestå av et for-tykningsmiddel, f. eks. sinkoksyd i blanding med et oljeaktig eller fettgrunnlag, f. eks. risinusolje og hvit bievoks, eventuelt i nærvær av en fettalkohol, f. eks. cetylalkohol eller cetostearylalkohol. Skikkete krem-grunnlag kan bestå av olje-i-vannemul-sjoner av den i teknikken kjente art, f. eks. risinusolje og fettalkoholer, f. eks. cetylalkohol og cetostearylalkohol dispergert i vann i nærvær av kondenseringsprodukter av fettalkoholer med etylenoksyd, f. eks. kondenseringsproduktet av cetyl eller cetostearylalkohol med 20—24 molekylardeler etylenoksyd. The antimicrobial preparations can also be in the form of creams, ointments and pastes, and such preparations can contain any suitable known non-toxic ingredients. Thus, a suitable ointment base can consist of a mixture of polyethylene glycol 400 and polyethylene glycol 4000, and a suitable paste can consist of a thickening agent, e.g. zinc oxide in mixture with an oily or fatty base, e.g. castor oil and white beeswax, possibly in the presence of a fatty alcohol, e.g. cetyl alcohol or cetostearyl alcohol. Suitable cream bases can consist of oil-in-water emulsions of the kind known in the art, e.g. castor oil and fatty alcohols, e.g. cetyl alcohol and cetostearyl alcohol dispersed in water in the presence of condensation products of fatty alcohols with ethylene oxide, e.g. the condensation product of cetyl or cetostearyl alcohol with 20-24 molecular parts of ethylene oxide.
Antimikrobepreparatene kan også foreligge i form av passende ikke-giftige forstøvningspulvere fremstilt på basis av inerte fortynningsmidler eller bæremidler, f. eks. talkum og/eller stivelse i nærvær av ytterligere bestanddeler, f. eks. sinkoksyd eller borsyre. The antimicrobial preparations may also be in the form of suitable non-toxic atomizing powders prepared on the basis of inert diluents or carriers, e.g. talc and/or starch in the presence of additional components, e.g. zinc oxide or boric acid.
De foran angitte preparater er i besittelse av antibakterielle egenskaper og de kan anvendes ved behandling av huden i slike tilfelle hvor der kreves et preparat som er i besittelse av antiseptiske egenskaper. The above mentioned preparations possess antibacterial properties and they can be used in the treatment of the skin in such cases where a preparation is required which possesses antiseptic properties.
Oppfinnelsen skal klargjøres ved hjelp av følgende eksempler, hvor deler er etter vekt: The invention shall be clarified by means of the following examples, where parts are by weight:
Ekesmpel 1: Example 1:
1,41 deler 5-nitro-2-furaldehyd, 1,33 deler oksindol og 8,5 deler eddiksyre opphetes sammen under tilbakeløp i 30 minutter. Blandingen kjøles og tilsettes til 100 1.41 parts of 5-nitro-2-furaldehyde, 1.33 parts of oxindole and 8.5 parts of acetic acid are heated together under reflux for 30 minutes. The mixture is cooled and added to 100
deler vann. Derpå filtreres, og der fåes 3-(5-nitro-2-furfuryliden)-oksindol, og der vaskes med vann. Det krystalliseres fra beta-etoksyetanol og har smeltepunktet 268° C under spaltning. shares water. It is then filtered, and 3-(5-nitro-2-furfurylidene)-oxindole is obtained, and washed with water. It crystallizes from beta-ethoxyethanol and has a melting point of 268° C during decomposition.
Eksempel 2: Example 2:
2,43 deler 5-nitro-2-furaldehyd-diace-tat, 1,33 deler oksindol og 1,06 deler 35 % vandig saltsyre opphetes sammen under tilbakeløp i vandig etanol i løpet av 1 time. Blandingen kjøles og filtreres, og der fåes 3-(5-nitro-2-furfuryliden)-oksindol, og der vaskes med vann. Det er identisk med forbindelsen som beskrevet i eksempel 1. 2.43 parts of 5-nitro-2-furaldehyde diacetate, 1.33 parts of oxindole and 1.06 parts of 35% aqueous hydrochloric acid are heated together under reflux in aqueous ethanol during 1 hour. The mixture is cooled and filtered, and 3-(5-nitro-2-furfurylidene)oxindole is obtained, and washed with water. It is identical to the compound described in Example 1.
Eksempel 3: Example 3:
En oppløsning av 0,37 deler natriumacetat i 5 deler eddiksyre tilsettes til en oppløsning av 1,33 deler 5-nitro-2-furalde-hyd og 2 deler 5-brom-oksindol (fremstillet i henhold til fremgangsmåten av Sumpter, Miller og Hendrick, Journal of the American Chemical Society, 1945, bind 67, side 1656) i 16 deler eddiksyre. Blandingen opphetes under tilbakeløp i løpet av 15 minutter, derpå kjøles og filtreres. Der fåes 5-brom-3-(5-nitro-2-furfuryliden)-oksindol, som når det krystalliseres fra (3-etoksyetanol, har smeltepunktet 305° C under spaltning. A solution of 0.37 parts of sodium acetate in 5 parts of acetic acid is added to a solution of 1.33 parts of 5-nitro-2-furaldehyde and 2 parts of 5-bromo-oxindole (prepared according to the method of Sumpter, Miller and Hendrick , Journal of the American Chemical Society, 1945, Volume 67, Page 1656) in 16 parts acetic acid. The mixture is heated under reflux for 15 minutes, then cooled and filtered. 5-bromo-3-(5-nitro-2-furfurylidene)-oxindole is obtained, which, when crystallized from (3-ethoxyethanol), has a melting point of 305° C during decomposition.
Eksempel 4: Example 4:
Fra 0,66 deler 5-nitro-2-furaldehyd, 0,8 deler 5-nitro-oksindol (fremstillet i henhold til fremgangsmåten av Sumpter, Miller og Magan, «Journal of the American Chemical Society», 1945, bind 67, side 499) og en oppløsning av 0,185 deler natriumacetat i 5 deler eddiksyre fåes der ved fremgangsmåten beskrevet i eksempel 3 5-nitro-3-(5-nitro-2-furfuryliden)-oksindol, som ikke smelter under 320° C. From 0.66 parts of 5-nitro-2-furaldehyde, 0.8 parts of 5-nitro-oxindole (prepared according to the method of Sumpter, Miller and Magan, "Journal of the American Chemical Society", 1945, vol. 67, p 499) and a solution of 0.185 parts sodium acetate in 5 parts acetic acid is obtained there by the method described in example 3 5-nitro-3-(5-nitro-2-furfurylidene)-oxindole, which does not melt below 320°C.
Eksempel 5: Example 5:
En oppløsning av 0,4 deler natriumacetat i 5 deler eddiksyre tilsettes til en oppløsning av 0,78 deler 5-nitro-2-furalde-hyd og 0,95 deler av 5-acetamido-oksindol (fremstillet ved acetylering av 5-amino-oksindol), i 7,5 deler eddiksyre. Blandingen opphetes ved 100° C i løpet av 3 timer, derpå kjøles og filtreres. Der fåes 5-acetamido-3-(5-nitro-2-furfury liden)-oksindol, som når det krystalliseres fra 50 % vandig eddiksyre har et smeltepunkt av 301° C under spaltning. A solution of 0.4 parts of sodium acetate in 5 parts of acetic acid is added to a solution of 0.78 parts of 5-nitro-2-furaldehyde and 0.95 parts of 5-acetamido-oxindole (produced by acetylation of 5-amino- oxindole), in 7.5 parts acetic acid. The mixture is heated at 100° C for 3 hours, then cooled and filtered. 5-acetamido-3-(5-nitro-2-furfury liden)-oxindole is obtained, which when crystallized from 50% aqueous acetic acid has a melting point of 301° C during decomposition.
Eksempel 6: Example 6:
En blanding av 2,3 deler 5-benzamido-oksindol, 1,3 deler 5-nitro-2-furaldehyd og 20 deler eddiksyre opphetes under tilbake-løp i løpet av 2 timer, og derpå kjøles og filtreres. Der fåes 5-benzamido-3-(5-nitro-2-furfuryliden)-oksindol, som når det krystalliseres fra dimetylformamid har smeltepunkt 274—276° C under spaltning. A mixture of 2.3 parts of 5-benzamido-oxindole, 1.3 parts of 5-nitro-2-furaldehyde and 20 parts of acetic acid is heated under reflux for 2 hours, then cooled and filtered. 5-benzamido-3-(5-nitro-2-furfurylidene)-oxindole is obtained, which when crystallized from dimethylformamide has a melting point of 274-276° C during decomposition.
5-benzamido-oksindolet som anvendtes som utgangsmateriale, kan fåes ved å ryste sammen 2,96 deler 5-amino-oksindol og 1,85 deler benzoylklorid med 20 deler 4 % vandig natriumhydroksyd. Blandingen filtreres, og det faste residuum vaskes med varmt vann, og der fåes på denne måte 5-benzamido-oksindol. The 5-benzamido-oxindole which was used as starting material can be obtained by shaking together 2.96 parts of 5-amino-oxindole and 1.85 parts of benzoyl chloride with 20 parts of 4% aqueous sodium hydroxide. The mixture is filtered, and the solid residue is washed with hot water, and 5-benzamido-oxindole is obtained in this way.
Eksempel 7: Fremgangsmåten som er beskrevet i eksempel 6, gjentaes, idet 2,3 deler av 5-benzamido-oksindol erstattes med en like stor mengde 5-p-klorbenzamido-oksindol. Der fåes på lignende måte 5-p-klorbenzamido-3- (5-nitro-2-f urf uryliden) -oksindol, smeltepunkt 318—319° C under rystning. Example 7: The procedure described in example 6 is repeated, replacing 2.3 parts of 5-benzamido-oxindole with an equal amount of 5-p-chlorobenzamido-oxindole. 5-p-chlorobenzamido-3-(5-nitro-2-fururylidene)-oxindole is obtained in a similar manner, melting point 318-319° C. with shaking.
5-p-klorbenzamido-oksindolet som anvendtes som utgangsmateriale, kan fåes ved å la 5-amino-oksindol og p-klorbenz-oylklorid reagere i nærvær av vandig natriumhydroksyd i henhold til fremgangsmåten som er beskrevet i slutten av eksempel 6. The 5-p-chlorobenzamido-oxindole used as starting material can be obtained by reacting 5-amino-oxindole and p-chlorobenzoyl chloride in the presence of aqueous sodium hydroxide according to the procedure described at the end of Example 6.
Eksempel 8: Example 8:
En blanding av 2,75 deler 5-propionamido-oksindol, 1,9 deler 5-nitro-2-furalde-hyd og 20 deler eddiksyre opphetes under tilbakeløp i løpet av 2 timer, og derpå kjø-les og filtreres. Det på denne måte erholdte faste residuum er 3-(5-nitro-2-fur-furyliden) -5-propionamido-oksindol, som krystallisert fra dimetylformamid har smeltepunkt 308—310° C under spaltning. A mixture of 2.75 parts of 5-propionamido-oxindole, 1.9 parts of 5-nitro-2-furaldehyde and 20 parts of acetic acid is heated under reflux for 2 hours, then cooled and filtered. The solid residue obtained in this way is 3-(5-nitro-2-fur-furylidene)-5-propionamido-oxindole, which crystallized from dimethylformamide has a melting point of 308-310° C during decomposition.
5-propionamido-oksindolet som anvendtes som utgangsmateriale, kan fåes ved tilsetning av 5,55 deler propionylklorid til en suspensjon av 5,92 deler 5-amino-oksindol i 100 deler dioksan og 8,6 deler, dietylanilin. Blandingen opphetes under tilbakeløp i løpet av 10 minutter og holdes over natten ved 18—23° C og filtreres. Der fåes 5-propionamidooksindol, som krystallisert fra vann har smeltepunkt 228—230° The 5-propionamido-oxindole, which was used as starting material, can be obtained by adding 5.55 parts of propionyl chloride to a suspension of 5.92 parts of 5-amino-oxindole in 100 parts of dioxane and 8.6 parts of diethylaniline. The mixture is heated under reflux for 10 minutes and kept overnight at 18-23° C and filtered. 5-propionamidooxindole is obtained, which crystallized from water has a melting point of 228-230°
C. C.
Eksempel 9: Example 9:
En blanding av 2,3 deler 5-n-valer amido-oksindol, 1,41 deler 5-nitro-2-fur-aldehyd og 20 deler eddiksyre opphetes under tilbakeløp i løpet av 3 timer, og derpå kjøles og filtreres. Det på denne måten erholdte faste residuum er 3-(5-nitro-2-fur-furyliden) -5-7i-valeramido-oksindol, som når det krystalliseres fra eddiksyre, har smeltepunktet 272—274° C under spaltning. 5-n-valeramido-oksindolet som anvendtes som utgangsmateriale, kan erhol-des ved å la en blanding av 5,7 deler 5-amino-oksindol, 6,8 deler n-valerylklorid og 50 deler pyridin stå over natten ved 18 —23° C, og derpå inndampes til tørrhet under redusert trykk. Residuet knuses med en liten mengde vann, og der blir tilbake 5-n-valeramido-oksindol, som krystallisert fra vann har smeltepunkt 226—228° C. A mixture of 2.3 parts 5-n valer amido-oxindole, 1.41 parts of 5-nitro-2-furaldehyde and 20 parts of acetic acid are heated under reflux for 3 hours, then cooled and filtered. The solid residue thus obtained is 3-(5-nitro-2-fur-furylidene)-5-7i-valeramido-oxindole, which, when crystallized from acetic acid, has a melting point of 272-274° C. during decomposition. The 5-n-valeramido-oxindole, which was used as starting material, can be obtained by allowing a mixture of 5.7 parts of 5-amino-oxindole, 6.8 parts of n-valeryl chloride and 50 parts of pyridine to stand overnight at 18-23 ° C, and then evaporated to dryness under reduced pressure. The residue is crushed with a small amount of water, and 5-n-valeramido-oxindole remains, which, crystallized from water, has a melting point of 226-228° C.
Eksempel 10: Fremgangsmåten som er beskrevet i eksempel 9, gjentas idet 5-n-valeramido-oksindolet erstattes med like stor mengde 5-7i-butyramido-oksindol. Der fåes på lignende måte 5-?z-butyramido-3-(5-nitro-2-furfuryliden) -oksindol, som krystallisert fra dimetylformamid har smeltepunktet 296—298° C under spaltning. Example 10: The procedure described in example 9 is repeated, replacing the 5-n-valeramido-oxindole with an equal amount of 5-7i-butyramido-oxindole. 5-?z-butyramido-3-(5-nitro-2-furfurylidene)-oxindole is obtained in a similar way, which, crystallized from dimethylformamide, has a melting point of 296-298° C. during decomposition.
5-n-butyramido-oksindolet som anvendtes som utgangsmateriale, kan fåes fra 5-amino-oksindol og n-butyryl-klorid. Det har smeltepunkt 236—238° C etter krystallisering fra vandig alkohol. The 5-n-butyramido-oxindole used as starting material can be obtained from 5-amino-oxindole and n-butyryl chloride. It has a melting point of 236-238° C after crystallization from aqueous alcohol.
Eksempel 11: Example 11:
En blanding av 0,8 deler 5-n-butyramido-oksindol i 10 deler vann og 0,5 deler 35 % vandig saltsyre og 0,95 deler 5-nitro-2-furaldehyd-diacetat i 10 deler etanol opphetes under tilbakeløp i løpet av 2 timer. Blandingen kjøles derpå og filtreres, og det faste residuum krystalliseres fra eddiksyre. Produktet som fåes på denne måte, er identisk med forbindelsen som er beskrevet i eksempel 10. A mixture of 0.8 parts of 5-n-butyramido-oxindole in 10 parts of water and 0.5 parts of 35% aqueous hydrochloric acid and 0.95 parts of 5-nitro-2-furaldehyde diacetate in 10 parts of ethanol is heated under reflux in the of 2 hours. The mixture is then cooled and filtered, and the solid residue is crystallized from acetic acid. The product obtained in this way is identical to the compound described in example 10.
Eksempel 12: Fremgangsmåten som er beskrevet i eksempel 9, gjentas idet man erstatter 5-n-valeramido-oksindolet med en ekvivalent mengde 5-zso-butyramido-oksindol. Der fåes på lignende måte 5-zso-butyramido-3-(5-nitro-2-f urf uryliden) -oksindol, som krystallisert fra dimetylformamid har smeltepunkt .314—316° C. Example 12: The procedure described in Example 9 is repeated, replacing the 5-n-valeramido-oxindole with an equivalent amount of 5-zso-butyramido-oxindole. 5-zso-butyramido-3-(5-nitro-2-fururylidene)-oxindole is obtained in a similar way, which crystallized from dimethylformamide has a melting point of .314—316° C.
5-iso-butyramido-oksindolet som anvendtes som utgangsmateriale, kan fåes The 5-iso-butyramido-oxindole used as starting material can be obtained
ved å la 5-amino-oksindol og iso-butyryl-klorid reagere i pyridin. Det har smeltepunkt 271—272° C etter krystallisering fra butanol. by reacting 5-amino-oxindole and iso-butyryl chloride in pyridine. It has a melting point of 271-272° C after crystallization from butanol.
Eksempel 13: Fremgangsmåten som er beskrevet i eksempel 9, gjentas idet man erstatter 5- n-valeramido-oksindolet med en ekvivalent mengde 5-kaproamido-oksindol. Der fåes på lignende måte 5-kaproamido-3-(5-nitro-2-furfuryliden)-oksindol, som når det krystalliseres fra butanol, har smeltepunkt 270° C. 5-kaproamido-oksindolet som anvendtes som utgangsmateriale kan fåes ved reaksjon av 5-amino-oksindol og kaproyl-klorid i pyridin. Det har smeltepunkt 224 —225° C etter krystallisering fra etanol. Example 13: The procedure described in example 9 is repeated, replacing the 5-n-valeramido-oxindole with an equivalent amount of 5-caproamido-oxindole. 5-caproamido-3-(5-nitro-2-furfurylidene)-oxindole is obtained in a similar way, which, when crystallized from butanol, has a melting point of 270° C. The 5-caproamido-oxindole that was used as starting material can be obtained by reaction of 5-amino-oxindole and caproyl chloride in pyridine. It has a melting point of 224 -225° C after crystallization from ethanol.
Eksempel 14: Fremgangsmåten som er beskrevet i eksempel 9, gjentas idet man erstatter 5- n-valeramido-oksindolet med en ekvivalent mengde 5-kaprylamido-oksindol. Der fåes på lignende måte 5-kaprylamido-3-(5-nitro-2-furfuryliden)-oksindol, som når det krystalliseres fra etanol, har smeltepunkt 222—223° C. Example 14: The procedure described in example 9 is repeated, replacing the 5-n-valeramido-oxindole with an equivalent amount of 5-caprylamido-oxindole. 5-caprylamido-3-(5-nitro-2-furfurylidene)-oxindole is obtained in a similar way, which, when crystallized from ethanol, has a melting point of 222-223°C.
5-kaprylamido-oksindolet som anvendtes som utgangsmateriale, kan fåes ved reaksjon av 5-amino-oksindol og kaprylylklo-rid i pyridin. Det har smeltepunkt 222— 223° C etter krystallisering fra etanol. The 5-caprylamido-oxindole, which was used as starting material, can be obtained by reaction of 5-amino-oxindole and caprylyl chloride in pyridine. It has a melting point of 222-223° C after crystallization from ethanol.
Eksempel 15: Fremgangsmåten som er beskrevet i eksempel 9, gjentas idet man erstatter 5-n-valeramido-oksindolet med en ekvivalent mengde 5-kapramido-oksindol. Der fåes på lignende måte, 5-kapramido-3-(5-nitro-2-f urf uryliden)-oksindol, som når det krystalliseres fra etanol, har smeltepunkt 225 —226° C. Example 15: The procedure described in example 9 is repeated, replacing the 5-n-valeramido-oxindole with an equivalent amount of 5-capramido-oxindole. There is obtained in a similar manner, 5-capramido-3-(5-nitro-2-fur urylidene)-oxindole, which, when crystallized from ethanol, has a melting point of 225 —226° C.
5-kapramido-oksindolet som anvendtes som utgangsmateriale, kan fåes ved reaksjon av 5-amino-oksindol og kaprylklorid i pyridin. Det har smeltepunkt 191—192° C etter krystallisering fra etanol. The 5-capramido-oxindole, which was used as starting material, can be obtained by reaction of 5-amino-oxindole and caprylic chloride in pyridine. It has a melting point of 191-192° C after crystallization from ethanol.
Eksempel 16: Example 16:
En blanding av 0,65 deler 5-(2-karbok-sypropionamido)-oksindol i 60 deler metanol, 0,37 deler 5-nitro-2-furaldehyd og 0,1 del natriumsuccinat opphetes under til-bakeløp i løpet av 16 timer. Blandingen kjøles derpå og filtreres, og det faste resi duum oppløses i vandig natriumkarbonat-oppløsning. Oppløsningen filtreres, og filtratet ansyres med vandig saltsyre. Derpå fåes 5-(2-karboksypropionamido)-3-(5-nitro-2-furfuryliden)-oksindol, smeltepunkt over 360° C. A mixture of 0.65 parts of 5-(2-carboxy-cypropionamido)-oxindole in 60 parts of methanol, 0.37 parts of 5-nitro-2-furaldehyde and 0.1 part of sodium succinate is heated under reflux for 16 hours . The mixture is then cooled and filtered, and the solid resi duum is dissolved in aqueous sodium carbonate solution. The solution is filtered, and the filtrate is acidified with aqueous hydrochloric acid. 5-(2-carboxypropionamido)-3-(5-nitro-2-furfurylidene)-oxindole is then obtained, melting point above 360° C.
5- (2-korboksypropionamido) -oksindolet som anvendtes som utgangsmateriale, kan fåes ved tilsetning av en oppløsning av 0,31 del ravsyreanhydrid i 30 deler benzen til en oppløsning av 0,45 del 5-amino-oksindol i 20 deler dioksan. Blandingen lar man henstå over natten ved 18—23° C, og det faste stoff oppsamles derpå og vaskes med petroleumeter (kokepunkt 60—80° C). Derpå fåes 5-(2-karboksypropionamido) - oksindol. The 5-(2-carboxypropionamido)-oxindole used as starting material can be obtained by adding a solution of 0.31 part of succinic anhydride in 30 parts of benzene to a solution of 0.45 part of 5-amino-oxindole in 20 parts of dioxane. The mixture is allowed to stand overnight at 18-23° C, and the solid is then collected and washed with petroleum ether (boiling point 60-80° C). 5-(2-carboxypropionamido)-oxindole is then obtained.
Eksempel 17: Example 17:
1,5 deler 6-amino-oksindol og 20 deler vannfri maursyre opphetes under tilbake-løp i løpet av 30 minutter. 1,5 deler 5-nitro-2-furaldehyd tilsettes derpå, og blandingen opphetes under tilbakeløp i løpet av ytterligere 30 minutter. Blandingen kjøles og filtreres, og det faste residuum som derpå fåes, er 6-formamido-3-(5-nitro-2-furfury-liden)-oksindol, smeltepunkt over 360° C. 1.5 parts of 6-amino-oxindole and 20 parts of anhydrous formic acid are heated under reflux for 30 minutes. 1.5 parts of 5-nitro-2-furaldehyde are then added, and the mixture is heated under reflux for a further 30 minutes. The mixture is cooled and filtered, and the solid residue that is then obtained is 6-formamido-3-(5-nitro-2-furfurylidene)oxindole, melting point above 360°C.
Eksempel 18: Example 18:
En blanding av 18 deler 6-acetamido-oksindol, 15 deler 5-nitro-2-furaldehyd og 100 deler eddiksyre opphetes under tilbake-løp i løpet av 2 timer. Derpå kjøles og filtreres, og det faste residuum vaskes med eddiksyre og metanol. Der fåes 6-acetamido-3-(5-nitro-2-furfuryliden)-oksindol, smeltepunkt over 330° C. A mixture of 18 parts of 6-acetamido-oxindole, 15 parts of 5-nitro-2-furaldehyde and 100 parts of acetic acid is heated under reflux for 2 hours. It is then cooled and filtered, and the solid residue is washed with acetic acid and methanol. This gives 6-acetamido-3-(5-nitro-2-furfurylidene)-oxindole, melting point above 330° C.
Eksempel 19: Example 19:
En blanding av 0,25 deler 4-acetamido-oksindol, 0,2 deler 5-nitro-2-furaldehyd og 3 deler eddiksyre opphetes under tilbakeløp i løpet av 30 minutter, og derpå kjøles og filtreres. Det på denne måte erholdte faste residuum er 4-acetamido-3-(5-nitro-2-fur-furyliden)-oksindol, som når det krystalliseres fra dimetylformamid har smeltepunkt over 360° C. A mixture of 0.25 parts of 4-acetamido-oxindole, 0.2 parts of 5-nitro-2-furaldehyde and 3 parts of acetic acid is heated under reflux for 30 minutes, then cooled and filtered. The solid residue obtained in this way is 4-acetamido-3-(5-nitro-2-fur-furylidene)-oxindole, which when crystallized from dimethylformamide has a melting point above 360°C.
4-acetamido-oksindolet som anvendtes som utgangsmateriale, kan fåes ved tilsetning av 24,2 deler 35 %'s vandig saltsyre i deler til en blanding av 4,2 deler 2 : 6-dinitrofenyleddiksyre, 10,22 deler tinn og 5 deler etanol. Etter at den kraftige reaksjon har avtatt, opphetes blandingen under til-bakeløp i løpet av 30 minutter. Derpå fil- The 4-acetamido-oxindole, which was used as starting material, can be obtained by adding 24.2 parts of 35% aqueous hydrochloric acid in parts to a mixture of 4.2 parts of 2:6-dinitrophenylacetic acid, 10.22 parts of tin and 5 parts of ethanol . After the vigorous reaction has subsided, the mixture is heated under reflux for 30 minutes. Then file-
treres, og filtratet kjøles og mettes med hydrogensulfid. Blandingen filtreres, og filtratet inndampes til tørrhet under redusert trykk. Residuet oppløses i vann, og der is filtered, and the filtrate is cooled and saturated with hydrogen sulphide. The mixture is filtered, and the filtrate is evaporated to dryness under reduced pressure. The residue dissolves in water, and there
tilsettes natriumbikarbonat. Der fåes 4-amino-oksindol, som etter krystallisering fra vann har smeltepunkt 180—182° C. 4-acetamido-oksindol fremstilles derpå fra sodium bicarbonate is added. 4-amino-oxindole is obtained, which after crystallization from water has a melting point of 180-182° C. 4-acetamido-oxindole is then prepared from
4- amino-oksindol ved reaksjon med acetyl-klorid i pyridin. Det har smeltepunkt 258— 260° C etter krystallisering fra etanol. 4-amino-oxindole by reaction with acetyl chloride in pyridine. It has a melting point of 258-260° C after crystallization from ethanol.
Eksempel 20: Example 20:
En blanding av 1 del 5-metyl-oksindol, 1 del 5-nitro-2-furaldehyd og 7 deler eddiksyre opphetes under tilbakeløp i løpet av 2 timer, og derpå kjøles og filtreres. Det faste residuum som derpå fåes, er 5-metyl-3-(5-nitro-2-furfuryliden) -oksindol, smeltepunkt 236° C under spaltning. A mixture of 1 part 5-methyl-oxindole, 1 part 5-nitro-2-furaldehyde and 7 parts acetic acid is heated under reflux for 2 hours, then cooled and filtered. The solid residue which is then obtained is 5-methyl-3-(5-nitro-2-furfurylidene)-oxindole, melting point 236° C during decomposition.
Eksempel 21: Example 21:
3 deler 5-hydroksy-oksindol, 5 deler 5-nitro-2-furaldehyd og 25 deler eddiksyre reageres ved fremgangsmåten som er beskrevet i eksempel 20. Der fåes på lignende måte 5-hydroksy-3-(5-nitro-2-furfuryli-den)-oksindol, smeltepunkt over 360° C. 3 parts of 5-hydroxy-oxindole, 5 parts of 5-nitro-2-furaldehyde and 25 parts of acetic acid are reacted by the method described in example 20. 5-hydroxy-3-(5-nitro-2-furfuryl) is obtained in a similar way -den)-oxindole, melting point above 360° C.
Eksempel. 22: Example. 22:
2 deler 5-metoksy-oksindol, 1,5 deler 5- nitro-2-furaldehyd og 20 deler eddiksyre reageres ved fremgangsmåten som er beskrevet i eksempel 20. Derpå fåes på lignende måte 5-metoksy-3-(5-nitro-2-fur-furyliden)-oksindol, som krystallisert fra 2-etoksyetanol har smeltepunkt 270° C under spaltning. 2 parts of 5-methoxy-oxindole, 1.5 parts of 5-nitro-2-furaldehyde and 20 parts of acetic acid are reacted by the method described in example 20. 5-methoxy-3-(5-nitro-2) is then obtained in a similar manner -fur-furylidene)-oxindole, which crystallized from 2-ethoxyethanol has a melting point of 270° C during decomposition.
Eksempel 23: Example 23:
1 del oksindol-6-karboksylsyre, 1 de: 5-nitro-2-furaldehyd og 20 deler eddiksyre bringes til reaksjon i henhold til fremgangsmåten beskrevet i eksempel 20. DerpÉ fåes på lignende måte 3-(5-nitro-2-fur-f uryliden) -oksindol-6-karboksylsyre son-etter krystallisering fra 2-etoksyetanol hai smeltepunkt over 360° C. 1 part oxindole-6-carboxylic acid, 1 de: 5-nitro-2-furaldehyde and 20 parts acetic acid are reacted according to the method described in example 20. DerpÉ is obtained in a similar way 3-(5-nitro-2-fur- (furylidene)-oxindole-6-carboxylic acid son-after crystallization from 2-ethoxyethanol has a melting point above 360° C.
Eksempel 24: Example 24:
1,3 deler 5 : 7-dibrom-oksindol, 0,63 de 1.3 parts 5 : 7-dibromo-oxindole, 0.63 de
5-nitro-2-furaldehyd og 20 deler eddiksyre bringes til reaksjon ved framgangsmåter som er beskrevet i eksempel 20. Derpå fåe: på lignende måte 5 : 7-dibrom-3-(5-nitro 2-furfuryliden)-oksindol, som etter kry 5-nitro-2-furaldehyde and 20 parts of acetic acid are brought into reaction by methods described in example 20. Then obtain: in a similar way 5 : 7-dibromo-3-(5-nitro 2-furfurylidene)-oxindole, as cry
stallisering fra dimetylformamid har smeltepunkt 308—310° C etter spaltning. Stallization from dimethylformamide has a melting point of 308-310° C after cleavage.
Eksempel. 25: Example. 25:
En oppløsning framstilles fra 1 del 3-(5-nitro-2-furfuryliden)-oksindol i 99 deler polyetylenglykol, og den på denne måte erholdte oppløsning er i besittelse av antibakterielle egenskaper. A solution is prepared from 1 part of 3-(5-nitro-2-furfurylidene)-oxindole in 99 parts of polyethylene glycol, and the solution obtained in this way possesses antibacterial properties.
Eksempel . 26: Example . 26:
En vandig dispersjon framstilles fra 0,5 del 3-(5-nitro-2-furfuryliden)-oksindol, 10 deler polyoksyetylen-sorbitanmonooleat og 89,5 deler vann, og den vandige dispersjon som fåes på denne måte, er i besittelse av antibakterielle egenskaper. An aqueous dispersion is prepared from 0.5 parts of 3-(5-nitro-2-furfurylidene)-oxindole, 10 parts of polyoxyethylene sorbitan monooleate and 89.5 parts of water, and the aqueous dispersion thus obtained possesses antibacterial properties.
Eksempel 27: Example 27:
En oppløsning framstilles fra 0,5 del 3-(5-nitro-2-furfuryliden)-oksindol og 99,9 deler risinusolje, og den på denne måte erholdte oljeaktige oppløsning er i besittelse av antibakterielle egenskaper. A solution is prepared from 0.5 part 3-(5-nitro-2-furfurylidene)-oxindole and 99.9 parts castor oil, and the oily solution obtained in this way possesses antibacterial properties.
Eksempel 28: Example 28:
En oppløsning fremstilles fra 0,5 del 3- (5-nitro-2-f urfuryliden) -oksindol, 24,5 deler av et kondenseringsprodukt erholdt fra oktylkresol og 8—10 molekylardeler • etylenoksyd og 75 deler polyetylenglycol 400. Den på denne måte erholdte oppløs-■ ning er i besittelse av antibakterielle egen-■ skaper, og den' kan fortynnes med vann så ■ at man får en vandig oppløsning, som er i i besittelse av antibakterielle rensende egen-■ skaper. A solution is prepared from 0.5 part of 3-(5-nitro-2-furfurylidene)-oxindole, 24.5 parts of a condensation product obtained from octylcresol and 8-10 molecular parts of • ethylene oxide and 75 parts of polyethylene glycol 400. It in this way the solution obtained has antibacterial properties, and it can be diluted with water so that an aqueous solution is obtained, which has antibacterial cleansing properties.
Eksempel . 29: Example . 29:
En vandig dispersjon fremstilles ved å 1 tilsette 5 deler 3-(5-nitro-2-f urfuryliden) - An aqueous dispersion is prepared by adding 5 parts of 3-(5-nitro-2-furfurylidene) -
; oksindol til en blanding av 0,05 del cetoma-- crogol 1000 B.P.C. (et kondenseringspro-i dukt av cetylalkohol og 20—24 molekylare deler av etylenoksyd), 2 deler etylcellulose, i 2 deler glycerol og 91 deler vann. Den på r denne måte erholdte vandige dispersjon er i besittelse av antibakterielle egenskaper. ; oxindole to a mixture of 0.05 part cetoma-- crogol 1000 B.P.C. (a condensation product of cetyl alcohol and 20-24 molecular parts of ethylene oxide), 2 parts ethyl cellulose, 2 parts glycerol and 91 parts water. The aqueous dispersion obtained in this way possesses antibacterial properties.
Eksempel 30: Example 30:
1 En salve dannes ved tilsetning av 1 del , 3-(5-nitro-2-furfuryliden)-oksindol til en i blanding av 60 deler polyetylenglykol 400 3 og 39 deler polyetylenglykol 4000. Der fåes - på denne måte en salve som er i besittelse 1 An ointment is formed by adding 1 part , 3-(5-nitro-2-furfurylidene)-oxindole to a mixture of 60 parts polyethylene glycol 400 3 and 39 parts polyethylene glycol 4000. In this way, an ointment is obtained which is in possession
- av antibakterielle egenskaper. - of antibacterial properties.
Eksempel 31: Example 31:
E pasta dannes på kjent måte ved inn-føring av 1 del 3-(5-nitro-2-f urfuryliden) - oksindol i en blanding av 78 deler risinusolje, 10 deler hvit bievoks og 3 deler cetostearylalkohol og derpå fortykkes produktet med 8 deler sinkoksyd. Der fåes på denne måte en pasta, som er i besittelse av antibakterielle egenskaper, og som kan anvendes for behandling av huden. E paste is formed in a known manner by introducing 1 part of 3-(5-nitro-2-furfurylidene)-oxindole in a mixture of 78 parts of castor oil, 10 parts of white beeswax and 3 parts of cetostearyl alcohol and then the product is thickened with 8 parts zinc oxide. In this way, a paste is obtained, which possesses antibacterial properties, and which can be used to treat the skin.
Eksempel 32: Example 32:
En krem framstilles på kjent måte ved innføring av 0,5 del 3-(5-nitro-2-furfuryli-den)-oksindol i en blanding av 20 deler risinusolje, 9 deler cetostearylalkohol, 2 deler cetomacrogol 1000 B.P.C. og 68,5 deler vann. Der fåes på denne måte en antisep-tisk krem som kan anvendes for behandling av huden. A cream is prepared in a known manner by introducing 0.5 part of 3-(5-nitro-2-furfurylidene)-oxindole into a mixture of 20 parts of castor oil, 9 parts of cetostearyl alcohol, 2 parts of cetomacrogol 1000 B.P.C. and 68.5 parts water. In this way, an antiseptic cream is obtained which can be used to treat the skin.
Eksempel 33: Example 33:
Et forstøvningspudder framstilles ved tilsetning av 0,05 del 3-(5-nitro-2-f urf ury-liden)-oksindol til en blanding av 10 deler stivelse, 10 deler borsyre og 80 deler talkum. Der fåes på denne måten et forstøv-ningspudder som er i besittelse av antibakterielle egenskaper, og som kan anvendes for behandling av huden. An atomizing powder is prepared by adding 0.05 part of 3-(5-nitro-2-fururylidene)-oxindole to a mixture of 10 parts of starch, 10 parts of boric acid and 80 parts of talc. In this way, an atomizing powder is obtained which possesses antibacterial properties and which can be used for treating the skin.
Eksempel 34: Example 34:
Et forstøvningspudder framstilles ved å tilsette 0,1 del 3-(5-nitro-2-furfuryli-den)-oksindol til en blanding av 74,9 deler stivelse og 25 deler sinkoksyd. Der fåes på denne måten et forstøvningspudder som er i besittelse av antibakterielle egenskaper, og som kan anvendes for behandling av huden. 1. Fremgangsmåte for framstilling av , nye antibakterielle indolderivater av formelen: hvor R betyr hydrogen elle ren acylgruppe og hvor kjernen A eventuelt kan bære substituenter, f. eks. halogen-, nitro-, acyla-mino-, alkyl-, hydroksy-, alkoksy- eller karboksylsyreradikaler, karakterisert ved at et oksindolderivat av formelen hvor A og R har den ovenfor angitte betyd-ning, bringes til å reagere med 5-nitro-2-furaldehyd eller men en forbindelse som er istand til å virke som 5-nitro-2-furaldehyd, som f. eks. 5-nitro-2-furaldehyd-diacetat, og i sist nevnte tilfelle i nærvær av vandig mineralsyre, f. eks. vandig saltsyre. 2. Fremgangsmåte som angitt i på-stand 1, karakterisert ved at der er tilstede et hensiktsmessig fortynningsmiddel eller oppløsningsmiddel, f. eks. eddiksyre, vandig etanol eller vannfri maursyre. 3. Fremgangsmåte som angitt i på-stand 1—2, karakterisert ved at der eventuelt er tilstede en basisk katalysator, f .eks. natriumacetat. 4. Anvendelse av indolderivater fram-stillet i henhold til påstandene 1—3 som aktiv bestanddel i antiseptiske midler. An atomizing powder is prepared by adding 0.1 part of 3-(5-nitro-2-furfurylidene)-oxindole to a mixture of 74.9 parts of starch and 25 parts of zinc oxide. In this way, an atomizing powder is obtained which possesses antibacterial properties, and which can be used for treating the skin. 1. Procedure for the production of , new antibacterial indole derivatives of the formula: where R means hydrogen or a pure acyl group and where the nucleus A may optionally carry substituents, e.g. halogen, nitro, acylamino, alkyl, hydroxy, alkoxy or carboxylic acid radicals, characterized in that an oxindole derivative of the formula where A and R have the meaning stated above, is made to react with 5-nitro-2-furaldehyde or a compound capable of acting as 5-nitro-2-furaldehyde, such as e.g. 5-nitro-2-furaldehyde diacetate, and in the last-mentioned case in the presence of aqueous mineral acid, e.g. aqueous hydrochloric acid. 2. Method as stated in claim 1, characterized in that an appropriate diluent or solvent is present, e.g. acetic acid, aqueous ethanol or anhydrous formic acid. 3. Method as stated in claims 1-2, characterized in that a basic catalyst is optionally present, e.g. sodium acetate. 4. Use of indole derivatives prepared according to claims 1-3 as active ingredient in antiseptics.
Claims (1)
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US56647366A | 1966-07-20 | 1966-07-20 |
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NO124695B true NO124695B (en) | 1972-05-23 |
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NO16909467A NO124695B (en) | 1966-07-20 | 1967-07-19 |
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AT (1) | AT279011B (en) |
BE (1) | BE700537A (en) |
CH (1) | CH493622A (en) |
DE (1) | DE1617066A1 (en) |
DK (1) | DK131732C (en) |
ES (1) | ES341533A1 (en) |
GB (1) | GB1195903A (en) |
NL (1) | NL6709856A (en) |
NO (1) | NO124695B (en) |
SE (2) | SE368224B (en) |
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JPS4839208B1 (en) * | 1968-11-18 | 1973-11-22 | ||
GB2146323B (en) * | 1983-09-09 | 1987-09-09 | Godrej Soaps Ltd | Production of sodium alpha olefin sulphonate and products containing it |
-
1967
- 1967-05-30 SE SE690770A patent/SE368224B/xx unknown
- 1967-05-30 SE SE753867A patent/SE345873B/xx unknown
- 1967-06-07 GB GB2622867A patent/GB1195903A/en not_active Expired
- 1967-06-08 DK DK302067A patent/DK131732C/en active
- 1967-06-08 ES ES341533A patent/ES341533A1/en not_active Expired
- 1967-06-26 BE BE700537D patent/BE700537A/xx unknown
- 1967-07-07 DE DE19671617066 patent/DE1617066A1/en active Pending
- 1967-07-10 AT AT641167A patent/AT279011B/en not_active IP Right Cessation
- 1967-07-11 CH CH982667A patent/CH493622A/en not_active IP Right Cessation
- 1967-07-14 NL NL6709856A patent/NL6709856A/xx unknown
- 1967-07-19 NO NO16909467A patent/NO124695B/no unknown
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DK131732B (en) | 1975-08-25 |
CH493622A (en) | 1970-07-15 |
AT279011B (en) | 1970-02-25 |
NL6709856A (en) | 1968-01-22 |
DK131732C (en) | 1976-01-26 |
GB1195903A (en) | 1970-06-24 |
ES341533A1 (en) | 1968-09-16 |
SE345873B (en) | 1972-06-12 |
SE368224B (en) | 1974-06-24 |
DE1617066A1 (en) | 1971-03-18 |
BE700537A (en) | 1967-12-01 |
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