CH501636A - Verfahren zur Herstellung von neuen N'-substituierten N-Arylsulfonylharnstoffen - Google Patents
Verfahren zur Herstellung von neuen N'-substituierten N-ArylsulfonylharnstoffenInfo
- Publication number
- CH501636A CH501636A CH1335766A CH1335766A CH501636A CH 501636 A CH501636 A CH 501636A CH 1335766 A CH1335766 A CH 1335766A CH 1335766 A CH1335766 A CH 1335766A CH 501636 A CH501636 A CH 501636A
- Authority
- CH
- Switzerland
- Prior art keywords
- tetrahydro
- group
- benzazepine
- hydrogen
- general formula
- Prior art date
Links
- 230000002218 hypoglycaemic effect Effects 0.000 title abstract description 3
- 235000013877 carbamide Nutrition 0.000 title abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 16
- MWVMYAWMFTVYED-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCCC2=CC=CC=C21 MWVMYAWMFTVYED-UHFFFAOYSA-N 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 150000007530 organic bases Chemical class 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 150000007529 inorganic bases Chemical class 0.000 claims description 7
- 230000009467 reduction Effects 0.000 claims description 6
- 238000006722 reduction reaction Methods 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 239000012948 isocyanate Substances 0.000 claims description 5
- 150000002513 isocyanates Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000006894 reductive elimination reaction Methods 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 150000001714 carbamic acid halides Chemical class 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 2
- 230000002829 reductive effect Effects 0.000 claims 1
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical compound O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 abstract description 2
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 238000002844 melting Methods 0.000 description 24
- 230000008018 melting Effects 0.000 description 24
- -1 methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentoxy, isopentoxy Chemical group 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- 239000004480 active ingredient Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
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- 229910021529 ammonia Inorganic materials 0.000 description 4
- FSZNYORWSWCYLN-UHFFFAOYSA-N n-(4-chlorophenyl)sulfonyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC(=O)N1CCC2=CC=CC=C2CC1 FSZNYORWSWCYLN-UHFFFAOYSA-N 0.000 description 4
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
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- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 244000215068 Acacia senegal Species 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- VQYLIIICFYEOEY-UHFFFAOYSA-N N-(4-aminophenyl)sulfonyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound NC1=CC=C(C=C1)S(=O)(=O)NC(=O)N1CCC2=C(CC1)C=CC=C2 VQYLIIICFYEOEY-UHFFFAOYSA-N 0.000 description 2
- FQLNOLGSLHCBKW-UHFFFAOYSA-N N-(4-fluorophenyl)sulfonyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound FC1=CC=C(C=C1)S(=O)(=O)NC(=O)N1CCC2=C(CC1)C=CC=C2 FQLNOLGSLHCBKW-UHFFFAOYSA-N 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
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- ZRERKMQKMINGSE-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-methylurea Chemical compound CNC(=O)NS(=O)(=O)C1=CC=CC=C1 ZRERKMQKMINGSE-UHFFFAOYSA-N 0.000 description 1
- ZGAIUFCXQBYBLT-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-nitrourea Chemical compound [N+](=O)([O-])NC(=O)NS(=O)(=O)C1=CC=CC=C1 ZGAIUFCXQBYBLT-UHFFFAOYSA-N 0.000 description 1
- 125000004716 2,2-dimethylpropylthio group Chemical group CC(CS*)(C)C 0.000 description 1
- WICMNXXWOAIBAV-UHFFFAOYSA-N 3-(4-ethoxyphenyl)sulfonyl-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C(C)OC1=CC=C(C=C1)S(=O)(=O)N1CCC2=C(CC1)C=CC=C2 WICMNXXWOAIBAV-UHFFFAOYSA-N 0.000 description 1
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- UBDDLABIBLKAHW-UHFFFAOYSA-N 3-(benzenesulfonyl)-1,1-diphenylurea Chemical compound C1(=CC=CC=C1)N(C(=O)NS(=O)(=O)C1=CC=CC=C1)C1=CC=CC=C1 UBDDLABIBLKAHW-UHFFFAOYSA-N 0.000 description 1
- JGHDVROWMPBQSR-UHFFFAOYSA-N 4-chloro-n-(oxomethylidene)benzenesulfonamide Chemical compound ClC1=CC=C(S(=O)(=O)N=C=O)C=C1 JGHDVROWMPBQSR-UHFFFAOYSA-N 0.000 description 1
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- VLJQDHDVZJXNQL-UHFFFAOYSA-N 4-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)N=C=O)C=C1 VLJQDHDVZJXNQL-UHFFFAOYSA-N 0.000 description 1
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- VJHMRYYWWDZAJI-UHFFFAOYSA-N N-(4-ethoxyphenyl)sulfonyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C(C)OC1=CC=C(C=C1)S(=O)(=O)NC(=O)N1CCC2=C(CC1)C=CC=C2 VJHMRYYWWDZAJI-UHFFFAOYSA-N 0.000 description 1
- YUKXDKDLTPHBIH-UHFFFAOYSA-N N-(4-methoxyphenyl)sulfonyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound COC1=CC=C(C=C1)S(=O)(=O)NC(=O)N1CCC2=C(CC1)C=CC=C2 YUKXDKDLTPHBIH-UHFFFAOYSA-N 0.000 description 1
- GYZSCRRRUYZAPO-UHFFFAOYSA-N N-(4-methylphenyl)sulfonyl-2-oxopiperidine-1-carboxamide Chemical compound C1(=CC=C(C=C1)S(=O)(=O)NC(=O)N1C(CCCC1)=O)C GYZSCRRRUYZAPO-UHFFFAOYSA-N 0.000 description 1
- VEBVDWFSTBELOW-UHFFFAOYSA-N N-(4-methylphenyl)sulfonyl-2-oxopyrrolidine-1-carboxamide Chemical compound C1(=CC=C(C=C1)S(=O)(=O)NC(=O)N1C(CCC1)=O)C VEBVDWFSTBELOW-UHFFFAOYSA-N 0.000 description 1
- DNSCADRMUDVKLX-UHFFFAOYSA-N N-(4-methylsulfanylphenyl)sulfonyl-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound CSC1=CC=C(C=C1)S(=O)(=O)NC(=O)N1CCC2=C(CC1)C=CC=C2 DNSCADRMUDVKLX-UHFFFAOYSA-N 0.000 description 1
- RHYBOIDYDHXTIP-UHFFFAOYSA-N N-(benzenesulfonyl)-1,2,4,5-tetrahydro-3-benzazepine-3-carboxamide Chemical compound C1(=CC=CC=C1)S(=O)(=O)NC(=O)N1CCC2=C(CC1)C=CC=C2 RHYBOIDYDHXTIP-UHFFFAOYSA-N 0.000 description 1
- YROBIWSICFFLLX-UHFFFAOYSA-N N-(benzenesulfonyl)-2-oxoazepane-1-carboxamide Chemical compound C1(=CC=CC=C1)S(=O)(=O)NC(=O)N1C(CCCCC1)=O YROBIWSICFFLLX-UHFFFAOYSA-N 0.000 description 1
- YJZUCKLMGVPUHK-UHFFFAOYSA-N N-(benzenesulfonyl)-2-oxopiperidine-1-carboxamide Chemical compound C1(=CC=CC=C1)S(=O)(=O)NC(=O)N1C(CCCC1)=O YJZUCKLMGVPUHK-UHFFFAOYSA-N 0.000 description 1
- RLYXEXJGNVILGY-UHFFFAOYSA-N N-(benzenesulfonyl)-2-oxopyrrolidine-1-carboxamide Chemical compound C1(=CC=CC=C1)S(=O)(=O)NC(=O)N1C(CCC1)=O RLYXEXJGNVILGY-UHFFFAOYSA-N 0.000 description 1
- KGINXYFISQQUQW-UHFFFAOYSA-N N-(benzenesulfonyl)carbamoyl chloride Chemical compound C1(=CC=CC=C1)S(=O)(=O)NC(=O)Cl KGINXYFISQQUQW-UHFFFAOYSA-N 0.000 description 1
- 150000001199 N-acyl amides Chemical class 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ZIHQUWYJSTVYAT-UHFFFAOYSA-N [NH-][N+]([O-])=O Chemical class [NH-][N+]([O-])=O ZIHQUWYJSTVYAT-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- DFWQXANLGSXMKF-UHFFFAOYSA-N ethyl n-(4-methylphenyl)sulfonylcarbamate Chemical compound CCOC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 DFWQXANLGSXMKF-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002641 lithium Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QHSZICITQBPJNK-UHFFFAOYSA-N methyl n-(benzenesulfonyl)carbamate Chemical compound COC(=O)NS(=O)(=O)C1=CC=CC=C1 QHSZICITQBPJNK-UHFFFAOYSA-N 0.000 description 1
- ITHCVNUFCWSLGQ-UHFFFAOYSA-N n-(benzenesulfonylcarbamoyl)benzamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(=O)NC(=O)C1=CC=CC=C1 ITHCVNUFCWSLGQ-UHFFFAOYSA-N 0.000 description 1
- NWIFRSJMWOEKNP-UHFFFAOYSA-N n-[(4-methylphenyl)sulfonylcarbamoyl]acetamide Chemical compound CC(=O)NC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 NWIFRSJMWOEKNP-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 150000003112 potassium compounds Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- WVAKABMNNSMCDK-UHFFFAOYSA-N sulfacarbamide Chemical compound NC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 WVAKABMNNSMCDK-UHFFFAOYSA-N 0.000 description 1
- 229950010053 sulfacarbamide Drugs 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1335766A CH501636A (de) | 1966-09-15 | 1966-09-15 | Verfahren zur Herstellung von neuen N'-substituierten N-Arylsulfonylharnstoffen |
| GB4187767A GB1139856A (en) | 1966-09-15 | 1967-09-14 | N'-substituted n-aryl sulphonyl ureas, their production and use |
| GR670137589A GR37589B (el) | 1966-09-15 | 1967-09-14 | Μεθοδος δια την παρασκευην ν-υποκατεστημενων ν-αρυλοσουλφονυλουριων. |
| DE19671695037 DE1695037A1 (de) | 1966-09-15 | 1967-09-14 | Verfahren zur Herstellung von neuen N'-subsituierten N-Aryl-sulfonylharnstoffen |
| BE703871D BE703871A (el) | 1966-09-15 | 1967-09-14 | |
| FR120993A FR1538845A (fr) | 1966-09-15 | 1967-09-14 | N-aryl-sulfonyl-urées et leur préparation |
| AT1086868A AT276428B (de) | 1966-09-15 | 1967-09-14 | Verfahren zur Herstellung von neuen N'-substituierten N-Arylsulfonylharnstoffen sowie ihren Salzen |
| ES345069A ES345069A1 (es) | 1966-09-15 | 1967-09-14 | Procedimiento para la preparacion de nuevas n - arilsulfo- nilureas n'-sustituidas. |
| SE1267767A SE329853B (el) | 1966-09-15 | 1967-09-14 | |
| NL6712587A NL6712587A (el) | 1966-09-15 | 1967-09-14 | |
| ES345070A ES345070A1 (es) | 1966-09-15 | 1967-09-14 | Procedimiento para la preparacion de nuevas n-arilsulfoni- lureas n'-sustituidas. |
| ES345068A ES345068A1 (es) | 1966-09-15 | 1967-09-14 | Procedimiento para la preparacion de nuevas n'- arilsulfo- nilureas n'-sustituidas. |
| AT1086968A AT276429B (de) | 1966-09-15 | 1967-09-14 | Verfahren zur Herstellung von neuen N'-substituierten N-Arylsulfonylharnstoffen sowie ihren Salzen |
| AT840667A AT275543B (de) | 1966-09-15 | 1967-09-14 | Verfahren zur Herstellung von neuen N'-substituierten N-Arylsulfonylharnstoffen sowie ihren Salzen |
| ES345071A ES345071A1 (es) | 1966-09-15 | 1967-09-14 | Procedimiento para la preparacion de nuevas n - arilsulfo- nilureas n'-sustituidas. |
| FR131837A FR7099M (el) | 1966-09-15 | 1967-12-12 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1335766A CH501636A (de) | 1966-09-15 | 1966-09-15 | Verfahren zur Herstellung von neuen N'-substituierten N-Arylsulfonylharnstoffen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH501636A true CH501636A (de) | 1971-01-15 |
Family
ID=4391718
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1335766A CH501636A (de) | 1966-09-15 | 1966-09-15 | Verfahren zur Herstellung von neuen N'-substituierten N-Arylsulfonylharnstoffen |
Country Status (10)
| Country | Link |
|---|---|
| AT (3) | AT276429B (el) |
| BE (1) | BE703871A (el) |
| CH (1) | CH501636A (el) |
| DE (1) | DE1695037A1 (el) |
| ES (4) | ES345069A1 (el) |
| FR (1) | FR7099M (el) |
| GB (1) | GB1139856A (el) |
| GR (1) | GR37589B (el) |
| NL (1) | NL6712587A (el) |
| SE (1) | SE329853B (el) |
-
1966
- 1966-09-15 CH CH1335766A patent/CH501636A/de not_active IP Right Cessation
-
1967
- 1967-09-14 AT AT1086968A patent/AT276429B/de active
- 1967-09-14 BE BE703871D patent/BE703871A/xx unknown
- 1967-09-14 DE DE19671695037 patent/DE1695037A1/de active Pending
- 1967-09-14 GB GB4187767A patent/GB1139856A/en not_active Expired
- 1967-09-14 AT AT840667A patent/AT275543B/de active
- 1967-09-14 NL NL6712587A patent/NL6712587A/xx unknown
- 1967-09-14 SE SE1267767A patent/SE329853B/xx unknown
- 1967-09-14 ES ES345069A patent/ES345069A1/es not_active Expired
- 1967-09-14 ES ES345071A patent/ES345071A1/es not_active Expired
- 1967-09-14 AT AT1086868A patent/AT276428B/de active
- 1967-09-14 ES ES345070A patent/ES345070A1/es not_active Expired
- 1967-09-14 GR GR670137589A patent/GR37589B/el unknown
- 1967-09-14 ES ES345068A patent/ES345068A1/es not_active Expired
- 1967-12-12 FR FR131837A patent/FR7099M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1695037A1 (de) | 1971-04-08 |
| GR37589B (el) | 1969-06-23 |
| SE329853B (el) | 1970-10-26 |
| AT275543B (de) | 1969-10-27 |
| ES345071A1 (es) | 1968-10-01 |
| ES345069A1 (es) | 1968-10-01 |
| AT276429B (de) | 1969-11-25 |
| BE703871A (el) | 1968-03-14 |
| AT276428B (de) | 1969-11-25 |
| FR7099M (el) | 1969-07-07 |
| ES345070A1 (es) | 1968-11-01 |
| ES345068A1 (es) | 1968-10-01 |
| NL6712587A (el) | 1968-03-18 |
| GB1139856A (en) | 1969-01-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |