CH415593A - Verfahren zur Herstellung von neuen Benzolsulfonylalkoxyharnstoffen - Google Patents

Verfahren zur Herstellung von neuen Benzolsulfonylalkoxyharnstoffen

Info

Publication number: CH415593A
Authority: CH; Switzerland
Prior art keywords: benzenesulfonyl; carbon atoms; urea; formula; methyl
Prior art date: 1960-04-29

Application number

CH492561A

Other languages

German (de)

English (en)

Inventor

Aumueller Walter

Korger Gerhard

Weyer Rudi

Weber Helmut

Baender Alfred

Original Assignee

Hoechst Ag

Priority date (The priority date 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 date listed.)

1960-04-29

Filing date

1961-04-26

Publication date

1966-06-30

1961-04-26 Application filed by Hoechst Ag filed Critical Hoechst Ag

1966-06-30 Publication of CH415593A publication Critical patent/CH415593A/de

Links

238000000034 method Methods 0.000 title claims description 15
238000002360 preparation method Methods 0.000 title claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 12
150000001875 compounds Chemical class 0.000 claims description 11
239000004202 carbamide Substances 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
239000000460 chlorine Chemical group 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000003884 phenylalkyl group Chemical group 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
229910021529 ammonia Inorganic materials 0.000 description 10
-1 benzenesulfonyl alkoxy ureas Chemical class 0.000 description 10
239000008280 blood Substances 0.000 description 9
210000004369 blood Anatomy 0.000 description 9
UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
235000013877 carbamide Nutrition 0.000 description 7
XYOMSHZQCMRGNN-UHFFFAOYSA-N CCCCONC(NS(C1=CC=C(C)C=C1)(=O)=O)=O Chemical compound CCCCONC(NS(C1=CC=C(C)C=C1)(=O)=O)=O XYOMSHZQCMRGNN-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
230000000694 effects Effects 0.000 description 5
WCVVIGQKJZLJDB-UHFFFAOYSA-N o-butylhydroxylamine Chemical compound CCCCON WCVVIGQKJZLJDB-UHFFFAOYSA-N 0.000 description 5
238000001816 cooling Methods 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000000155 melt Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
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 3
241000282472 Canis lupus familiaris Species 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
241000283973 Oryctolagus cuniculus Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
206010012601 diabetes mellitus Diseases 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
HWLKXAHZLJBRNM-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(=O)NC(=O)NOC1CCCCC1)C Chemical compound C1(=CC=C(C=C1)S(=O)(=O)NC(=O)NOC1CCCCC1)C HWLKXAHZLJBRNM-UHFFFAOYSA-N 0.000 description 2
PBSCOZAFBYEBAK-UHFFFAOYSA-N CCCONC(NS(C1=CC=C(C)C=C1)(=O)=O)=O Chemical compound CCCONC(NS(C1=CC=C(C)C=C1)(=O)=O)=O PBSCOZAFBYEBAK-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
KYKNGOPXRHUCHC-UHFFFAOYSA-N o-cyclohexylhydroxylamine Chemical compound NOC1CCCCC1 KYKNGOPXRHUCHC-UHFFFAOYSA-N 0.000 description 2
PRAARDGLAWZXML-UHFFFAOYSA-N o-propylhydroxylamine Chemical compound CCCON PRAARDGLAWZXML-UHFFFAOYSA-N 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000001226 reprecipitation Methods 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
210000004291 uterus Anatomy 0.000 description 2
KLHUBDSZIPFYGP-UHFFFAOYSA-N (4-chlorophenyl)sulfonyl-methylcarbamic acid Chemical compound CN(C(O)=O)S(=O)(=O)C1=CC=C(C=C1)Cl KLHUBDSZIPFYGP-UHFFFAOYSA-N 0.000 description 1
PHPKGFJFAMVVTI-UHFFFAOYSA-N (4-methoxyphenyl)sulfonylcarbamic acid Chemical compound COC1=CC=C(S(=O)(=O)NC(O)=O)C=C1 PHPKGFJFAMVVTI-UHFFFAOYSA-N 0.000 description 1
OXIHBMGOHJFHII-UHFFFAOYSA-N (4-methoxyphenyl)sulfonylurea Chemical compound COC1=CC=C(S(=O)(=O)NC(N)=O)C=C1 OXIHBMGOHJFHII-UHFFFAOYSA-N 0.000 description 1
VATAIZDYZPAXOX-UHFFFAOYSA-N (4-methylphenyl)sulfonylcarbamic acid Chemical compound CC1=CC=C(S(=O)(=O)NC(O)=O)C=C1 VATAIZDYZPAXOX-UHFFFAOYSA-N 0.000 description 1
RUTYWCZSEBLPAK-UHFFFAOYSA-N (4-methylphenyl)sulfonylurea Chemical compound CC1=CC=C(S(=O)(=O)NC(N)=O)C=C1 RUTYWCZSEBLPAK-UHFFFAOYSA-N 0.000 description 1
NDMSWZCITKBOIH-UHFFFAOYSA-N (4-propoxyphenyl)sulfonylcarbamic acid Chemical compound CCCOC1=CC=C(S(=O)(=O)NC(O)=O)C=C1 NDMSWZCITKBOIH-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
HEBTZZBBPUFAFE-UHFFFAOYSA-N 2-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=CC=C1S(=O)(=O)N=C=O HEBTZZBBPUFAFE-UHFFFAOYSA-N 0.000 description 1
PQWRIGCASGGXIN-UHFFFAOYSA-N 3-(4-methylphenyl)sulfonyl-1,1-diphenylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)N(C=1C=CC=CC=1)C1=CC=CC=C1 PQWRIGCASGGXIN-UHFFFAOYSA-N 0.000 description 1
NRPHEJYDQNWSJF-UHFFFAOYSA-N 3-methyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CC1=CC=CC(S(=O)(=O)N=C=O)=C1 NRPHEJYDQNWSJF-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
ZPBSZCDTNNYFHY-UHFFFAOYSA-N 4-ethyl-n-(oxomethylidene)benzenesulfonamide Chemical compound CCC1=CC=C(S(=O)(=O)N=C=O)C=C1 ZPBSZCDTNNYFHY-UHFFFAOYSA-N 0.000 description 1
RGVBEISMHCYSNF-UHFFFAOYSA-N 4-methoxy-n-(oxomethylidene)benzenesulfonamide Chemical compound COC1=CC=C(S(=O)(=O)N=C=O)C=C1 RGVBEISMHCYSNF-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
ILUXYYLNJNAMFH-UHFFFAOYSA-N CCCCONC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 Chemical compound CCCCONC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 ILUXYYLNJNAMFH-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
238000005773 Enders reaction Methods 0.000 description 1
206010018473 Glycosuria Diseases 0.000 description 1
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 1
KGINXYFISQQUQW-UHFFFAOYSA-N N-(benzenesulfonyl)carbamoyl chloride Chemical class C1(=CC=CC=C1)S(=O)(=O)NC(=O)Cl KGINXYFISQQUQW-UHFFFAOYSA-N 0.000 description 1
CWUGNINSJRGCOH-UHFFFAOYSA-N N-[(4-chlorophenyl)sulfonylcarbamoyl]acetamide Chemical compound ClC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC(C)=O CWUGNINSJRGCOH-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
XNOPRXBHLZRZKH-UHFFFAOYSA-N Oxytocin Natural products N1C(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CC(C)C)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C(C(C)CC)NC(=O)C1CC1=CC=C(O)C=C1 XNOPRXBHLZRZKH-UHFFFAOYSA-N 0.000 description 1
101800000989 Oxytocin Proteins 0.000 description 1
102100031951 Oxytocin-neurophysin 1 Human genes 0.000 description 1
229940100389 Sulfonylurea Drugs 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
150000008331 benzenesulfonamides Chemical class 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000035606 childbirth Effects 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000035780 glucosuria Effects 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
KNVDHKOSDVFZTO-UHFFFAOYSA-N methyl n-(4-methylphenyl)sulfonylcarbamate Chemical compound COC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 KNVDHKOSDVFZTO-UHFFFAOYSA-N 0.000 description 1
GPUWWYFDBGWKFK-UHFFFAOYSA-N n-(4-chlorophenyl)sulfonylcarbamoyl chloride Chemical compound ClC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 GPUWWYFDBGWKFK-UHFFFAOYSA-N 0.000 description 1
SBFRBCWEYRIGAS-UHFFFAOYSA-N n-(4-methylphenyl)sulfonylcarbamoyl chloride Chemical compound CC1=CC=C(S(=O)(=O)NC(Cl)=O)C=C1 SBFRBCWEYRIGAS-UHFFFAOYSA-N 0.000 description 1
BGUPWXNCOACHRQ-UHFFFAOYSA-N n-propoxyaniline Chemical compound CCCONC1=CC=CC=C1 BGUPWXNCOACHRQ-UHFFFAOYSA-N 0.000 description 1
RUMFZCKCISCDMG-UHFFFAOYSA-N o-(2-methylpropyl)hydroxylamine Chemical compound CC(C)CON RUMFZCKCISCDMG-UHFFFAOYSA-N 0.000 description 1
BZCDKOOXCPRISF-UHFFFAOYSA-N o-(2-phenylethyl)hydroxylamine Chemical compound NOCCC1=CC=CC=C1 BZCDKOOXCPRISF-UHFFFAOYSA-N 0.000 description 1
PXWPXXJVCQOIPH-UHFFFAOYSA-N o-(3-methylbutyl)hydroxylamine Chemical compound CC(C)CCON PXWPXXJVCQOIPH-UHFFFAOYSA-N 0.000 description 1
XYEOALKITRFCJJ-UHFFFAOYSA-N o-benzylhydroxylamine Chemical compound NOCC1=CC=CC=C1 XYEOALKITRFCJJ-UHFFFAOYSA-N 0.000 description 1
HWWCBAWGNJYHPP-UHFFFAOYSA-N o-cyclopentylhydroxylamine Chemical compound NOC1CCCC1 HWWCBAWGNJYHPP-UHFFFAOYSA-N 0.000 description 1
AQTGLKJBMFAKJH-UHFFFAOYSA-N o-heptylhydroxylamine Chemical compound CCCCCCCON AQTGLKJBMFAKJH-UHFFFAOYSA-N 0.000 description 1
AIPBDRLFQKUETL-UHFFFAOYSA-N o-hexylhydroxylamine Chemical compound CCCCCCON AIPBDRLFQKUETL-UHFFFAOYSA-N 0.000 description 1
VBPVZDFRUFVPDV-UHFFFAOYSA-N o-pentylhydroxylamine Chemical compound CCCCCON VBPVZDFRUFVPDV-UHFFFAOYSA-N 0.000 description 1
HLYVNXRHROOICH-UHFFFAOYSA-N o-propan-2-ylhydroxylamine Chemical compound CC(C)ON HLYVNXRHROOICH-UHFFFAOYSA-N 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 description 1
229960001723 oxytocin Drugs 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
230000035935 pregnancy Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
210000001625 seminal vesicle Anatomy 0.000 description 1
210000000813 small intestine Anatomy 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
229910052717 sulfur Chemical group 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
201000010653 vesiculitis Diseases 0.000 description 1
229940100445 wheat starch Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
- C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
- C07C311/61—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups further bound to another hetero atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH492561A 1960-04-29 1961-04-26 Verfahren zur Herstellung von neuen Benzolsulfonylalkoxyharnstoffen CH415593A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF31115A DE1139830B (de)	1960-04-29	1960-04-29	Verfahren zur Herstellung von Benzolsulfonyl-alkoxyharnstoffen

Publications (1)

Publication Number	Publication Date
CH415593A true CH415593A (de)	1966-06-30

Family

ID=7094056

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH492561A CH415593A (de)	1960-04-29	1961-04-26	Verfahren zur Herstellung von neuen Benzolsulfonylalkoxyharnstoffen

Country Status (4)

Country	Link
BE (1)	BE603268A (fr)
CH (1)	CH415593A (fr)
DE (1)	DE1139830B (fr)
GB (1)	GB976533A (fr)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1106310B (de)	1959-04-23	1961-05-10	Bayer Ag	Verfahren zur Herstellung von Harnstoffderivaten

1960
- 1960-04-29 DE DEF31115A patent/DE1139830B/de active Pending
1961
- 1961-04-26 GB GB1516861A patent/GB976533A/en not_active Expired
- 1961-04-26 CH CH492561A patent/CH415593A/de unknown
- 1961-05-02 BE BE603268A patent/BE603268A/fr unknown

Also Published As

Publication number	Publication date
DE1139830B (de)	1962-11-22
BE603268A (fr)	1961-11-03
GB976533A (en)	1964-11-25

Publication	Publication Date	Title
DE1185180B (de)	1965-01-14	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
DE2759241C3 (de)	1981-05-21	N-(4-(2-(pyrazol-1-carbonamido)-athyl)-benzolsulfonyl) carbonide, verfahren zu ihrer herstellung und arzneimittel
DE1493672B2 (de)	1973-09-27	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
DE2419198C3 (de)	1980-12-11	Benzolsulfonylharnstoffe und ihre Verwendung zur Bekämpfung von Diabetes
CH415593A (de)	1966-06-30	Verfahren zur Herstellung von neuen Benzolsulfonylalkoxyharnstoffen
DE1201337B (de)	1965-09-23	Verfahren zur Herstellung von Benzol-sulfonylharnstoffen
DE2238870B2 (de)	1978-02-16	Benzolsulfonylharnstoffe
AT227715B (de)	1963-06-10	Verfahren zur Herstellung von neuen Benzolsulfonyl-alkoxy-harnstoffen
DE1181208B (de)	1964-11-12	Verfahren zur Herstellung von N-Benzolsulfonyl-N'-cyclohexyl-harnstoffen
CH370766A (de)	1963-07-31	Verfahren zur Herstellung von oral wirksamen Antidiabetika
DE2230543A1 (de)	1974-01-17	Benzolsulfonylharnstoffe und verfahren zu ihrer herstellung
DE1518895C3 (de)	1978-12-07	Benzolsulfonylharnstoffe, Verfahren zu ihrer Herstellung und deren Verwendung
AT226725B (de)	1963-04-10	Verfahren zur Herstellung von neuen Sulfonylharnstoffen
DE2000339C3 (de)	1979-04-19	Isochinolinderivate
DE1933388C (de)	1972-07-13	l-(2-Acyl- 1,2,3,4-tetrahydroisochinolin-7sulfonyl)-harnstoffe
AT216521B (de)	1961-08-10	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
AT212312B (de)	1960-12-12	Verfahren zur Herstellung von neuen 2-Sulfonamidothiadiazol-Derivaten
CH441274A (de)	1967-08-15	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
CH427794A (de)	1967-01-15	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden
CH438263A (de)	1967-06-30	Verfahren zur Herstellung von Hydroxybenzolsulfonylharnstoffen
AT236402B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonyl-semicarbaziden
CH363652A (de)	1962-08-15	Verfahren zur Herstellung von Sulfonylharnstoffen
DE1668168C3 (de)	1973-09-27	N1 substituierte N Arylsulfonyl harnstoffe, deren pharmakologisch ver fragliche Salze, Verfahren zu deren Her Stellung und diese enthaltende pharma zeutische Präparate
DE1199765B (de)	1965-09-02	Verfahren zur Herstellung von Benzolsulfonyl-harnstoffderivaten
DE1076664B (de)	1960-03-03	Verfahren zur Herstellung von neuen N-Benzolsulfonyl-N'-benzyl-harnstoffen