NO162864B - PROCEDURE FOR HYDROGENERATION OF COAL, LONG OIL, BITUMEN AND LIKE. - Google Patents
PROCEDURE FOR HYDROGENERATION OF COAL, LONG OIL, BITUMEN AND LIKE. Download PDFInfo
- Publication number
- NO162864B NO162864B NO821844A NO821844A NO162864B NO 162864 B NO162864 B NO 162864B NO 821844 A NO821844 A NO 821844A NO 821844 A NO821844 A NO 821844A NO 162864 B NO162864 B NO 162864B
- Authority
- NO
- Norway
- Prior art keywords
- benzenesulfonyl
- ethyl
- substituted
- semicarbazide
- residue
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 239000010426 asphalt Substances 0.000 title 1
- 239000003245 coal Substances 0.000 title 1
- -1 alkenoxy Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 239000008280 blood Substances 0.000 claims description 12
- 210000004369 blood Anatomy 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- LSNDGFYQJRXEAR-UHFFFAOYSA-N benzenesulfonamidourea Chemical class NC(=O)NNS(=O)(=O)C1=CC=CC=C1 LSNDGFYQJRXEAR-UHFFFAOYSA-N 0.000 claims description 10
- 150000001555 benzenes Chemical class 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 235000013877 carbamide Nutrition 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 150000003672 ureas Chemical class 0.000 claims description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000002429 hydrazines Chemical class 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- JWPWVPPTDSULMI-UHFFFAOYSA-N benzenesulfonamidothiourea Chemical class NC(=S)NNS(=O)(=O)C1=CC=CC=C1 JWPWVPPTDSULMI-UHFFFAOYSA-N 0.000 claims description 3
- FCXSGAKSWAEXPU-UHFFFAOYSA-N iminocarbamic acid Chemical class OC(=O)N=N FCXSGAKSWAEXPU-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 150000008331 benzenesulfonamides Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
- MBTLHVYOEGCXPI-UHFFFAOYSA-N iminocarbamothioic s-acid Chemical class OC(=S)N=N MBTLHVYOEGCXPI-UHFFFAOYSA-N 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 2
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 2
- IYMAUEAFOBSGCY-UHFFFAOYSA-N benzene;sulfurochloridic acid Chemical class OS(Cl)(=O)=O.C1=CC=CC=C1 IYMAUEAFOBSGCY-UHFFFAOYSA-N 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 213
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 78
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
- 238000000354 decomposition reaction Methods 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000155 melt Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000004202 carbamide Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- WWECJGLXBSQKRF-UHFFFAOYSA-N n,n-dimethylformamide;methanol Chemical compound OC.CN(C)C=O WWECJGLXBSQKRF-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 3
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical group CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 3
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ASRMWYDEZPXXBA-UHFFFAOYSA-N (sulfonylamino)urea Chemical class NC(=O)NN=S(=O)=O ASRMWYDEZPXXBA-UHFFFAOYSA-N 0.000 description 2
- RZNHSEZOLFEFGB-UHFFFAOYSA-N 2-methoxybenzoyl chloride Chemical compound COC1=CC=CC=C1C(Cl)=O RZNHSEZOLFEFGB-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical compound OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- FDPGUECLKNPLOB-UHFFFAOYSA-N (n-phenylanilino)urea Chemical class C=1C=CC=CC=1N(NC(=O)N)C1=CC=CC=C1 FDPGUECLKNPLOB-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004945 acylaminoalkyl group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 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
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 239000003538 oral antidiabetic agent Substances 0.000 description 1
- ZFLIKDUSUDBGCD-UHFFFAOYSA-N parabanic acid Chemical class O=C1NC(=O)C(=O)N1 ZFLIKDUSUDBGCD-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000002071 phenylalkoxy group Chemical group 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 150000003349 semicarbazides Chemical class 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000007970 thio esters Chemical class 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
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
- C10G1/002—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal in combination with oil conversion- or refining processes
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
- C10G1/06—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal by destructive hydrogenation
- C10G1/065—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal by destructive hydrogenation in the presence of a solvent
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Working-Up Tar And Pitch (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
Fremgangsmåte til fremstilling av benzolsulfonylsemikarbazider med blodsukkersenkende virkning. Process for the production of benzenesulfonyl semicarbazides with a blood sugar-lowering effect.
Oppfinnelsen vedrører en fremgangsmåte til fremstilling av benzolsulfonylsemikarbazider med blodsukkersenkende virkning og med formel The invention relates to a method for the production of benzenesulfonyl semicarbazides with a blood sugar-lowering effect and with a formula
hvori R betyr en fenylrest som eventuelt er substituert 1 eller 3 ganger med lavmolekylært alkyl, alkenyl, alkoksy, alkenoksy, alkoksyalkoksy, halogen, eller med en metylendioksygruppe eller en trifluormetylgruppe, in which R means a phenyl radical which is optionally substituted 1 or 3 times with low molecular weight alkyl, alkenyl, alkoxy, alkenoxy, alkyloxy, halogen, or with a methylenedioxy group or a trifluoromethyl group,
eller or
en tiofenrest som eventuelt er substituert 1-2 ganger med halogen, lavmolekylært alkyl, alkoksy, alkenyloksy, alkoksyalkoksy, fenylalkoksy eller aryl eller substituert med en ved begge ender med tiofenresten sammenknyttet polymetylenkjede med 3-4 C-atomer, eller a thiophene residue which is optionally substituted 1-2 times with halogen, low molecular weight alkyl, alkoxy, alkenyloxy, alkyloxy, phenylalkoxy or aryl or substituted with a polymethylene chain with 3-4 C atoms linked at both ends to the thiophene residue, or
en furylrest som eventuelt er substituert med en metylgruppe eller et halogenatom eller a furyl residue which is optionally substituted with a methyl group or a halogen atom or
en fenylrest som er bundet gjennom en mettet, umettet eller eventuelt forgrenet hydrokarbonkjede med 1-4 C-atomer, hvori den ene -CH2-gruppe kan være erstattet med oksygen, og fenylresten eventuelt kan være substituert med en lavmolekylær alkyl- eller alkoksyrest eller halogen, a phenyl residue which is bound through a saturated, unsaturated or optionally branched hydrocarbon chain with 1-4 C atoms, in which one -CH2 group may be replaced by oxygen, and the phenyl residue may optionally be substituted with a low molecular weight alkyl or alkoxy acid residue or halogen ,
eller or
en cykloheksyl- eller cykloheksenylrest, a cyclohexyl or cyclohexenyl residue,
eller or
en eventuelt umettet alkylrest med 1-11 C-atomer, an optionally unsaturated alkyl residue with 1-11 C atoms,
R"*- betyr en alkyleniminorest med 3-7 C-atomer, idet alkylenkjeden eventuelt kan være substituert med 2-4 metylgrupper eller med en alkyl- eller alkoksyrest med inntil 3 C-atomer, eller hvis den inneholder 5 C-atomer som eventuelt kan være substituert med lavmolekylært alkyl- eller alkoksy, ;eller ;resten ;;hvori R^ og R2 betyr lavmolekylært alkyl, R2 også ;benzyl, ;samt deres syreaddisjonssalter, eller salter med en base, ;idet fremgangsmåten er karakterisert ved at mari enten ;a) omsetter med gruppen R-CO-NH-CH2-CH2-substituerte benzolsulfon-amider, hensiktsmessig i form av deres salter, med iminokarbaminsyreestere, imino-tiokarbaminsyreestere eller iminourinstoffer, som som iminorest inneholder grupperingen R A eller b) omsetter hydraziner med formel R-^-NHg eller deres salter med substituerte benzolsulfonylisocyanater-, -karbaminsyreestere, ;-tiokarbaminsyreestere, -karbaminsyrehalogenider eller urinstoffer som er substituert med gruppen R-CO-NH-CH2-CH2- i benzolkjernen, eller ;c) omsetter benzolsulfoklorider som er substituert med gruppen R-CO-NH-CH2-CH"2- med urinstoffer som er substituert med gruppen ;R<1>, eller ;d) hydrolyserer benzolsulfonylisosemikarbazidetere, ;-isotiosemikarbazidetere eller benzolsulfonyl-iminoparabansyrer som i benzolkjernen er substituert med gruppen R-CO-NH-CH2-CH2- eller ;e) i benzolsulfonyltiosemikarbazider med formel ;utveksler svovelatomet med et oksygenatom, eller f) i benzolsulfonylsemikarbazider med formel ;eventuelt trinnvis innfører resten R-CO- og hvis ønsket, behandler ;de dannede benzolsulfonylsemikarbazider med fysiologisk tålbare uorganiske eller organiske syrer, eller med en base for saltdannelse. ;Som semikarbazider, resp. iminourinurinstoffer for den under a) nevnte syntese egner seg slike med formel R^-NH-CO-NHp eller acylerte forbindelser med formel R -NH-CO-NH-acyl, hvori acyl betyr en fortrinnsvis lavmolekylær alifatisk eller aromatisk syrerest, eller difenylsemikarbazider med formel R<1->NH-CO-N (CgH^)2, idet fenylrestene kan være substituert såvel som også forbundet med hverandre direkte eller over en bro, eller N,N'-disubstituerte karbohydrazider med formel R-^NH-CO-NH-R<1>. ;Som benzolsulfonyl-karbaminsyrehalogenider egner seg i første rekke kloridene. Videre lar også tilsvarende, ved den til sul-fonylgruppen bortvendte side av urinstoffmolekylet usubstituerte eller ved andre alkylrester eller arylrester en eller to ganger substituerte benzolsulfonylurinstoffer seg overføre ved omsetning med hydraziner av formel R^-NHg, eventuelt i form av deres salter, i de ønskede forbindelser. I stedet for på slik måte substituerte benzolsulfonylurin-stof f er kan det også anvendes tilsvarende N-benzolsulfonyl-N'-acyl-urinstoffer eller bis-(benzolsulfonyl)-urinstoffer. Man kan eksempelvis behandle slike bis-(benzolsulfonyl)-urinstoffer eller N-benzolsulf onyl-N' -acyl-urinstof f er med hydraziner av formel R^-NHg og opp-varme de dannede salter til høyere temperaturer, hensiktsmessig slike på minst 80°C. De nevnte iminokarbaminsyreestere eller benzolsulfonyl-karbaminsyreestere såvel som de tilsvarende tioestere inneholder hensiktsmessig i esterkomponenten en lavmolekylær alkylrest eller en fenylrest. ;De likeledes som utgangsstoffer aktuelle med gruppen R-CO-NH-Y substituerte benzolsulfonyl-isosemikarbazidetere, -isotiosemikarbazidetere eller -parabansyrer lar seg fremstille ved omsetningen av tilsvarende isosemikarbazidetere, isotiosemikarbazidetere eller parabansyrer med R-CO-NH-Y substituerte benzolsulfoklorider. Likeledes fører avsvovlingen av R-CO-NH-Y substituerte benzolsulfonyltiosemikarbazider i metanol i første rekke til R-CO-NH-Y substituerte benzolsulfonylisosemikarbazidetere som deretter ved hydrolyse overføres i benzolsulfonylsemikarbazider. ;Alt etter naturen av leddet R-CO- vil i enkelte tilfelle den ene eller den andre av de nevnte fremgangsmåter for fremstilling av de individuelle forbindelser som faller inn under den generelle formel være uegnet eller i det minste nødvendiggjøre forholdsregler til beskyttelse av aktive grupper. Slike forholdsvis sjeldent opptredende tilfelle kan lett erkjennes av fagfolk, og det byr ikke på noen vanskeligheter i slike tilfelle med resultat å anvende en annen av de omtalte syntesemåter. ;Utførelsen av fremgangsmåten ifølge oppfinnelsen kan variere sterkt generelt med hensyn til reaksjonsbetingelsene og tilpasses de foreliggende forhold. Eksempelvis kan omsetningene gjennomføres under anvendelse av oppløsningsmidler, ved værelsetemperatur eller forhøyet temperatur. ;Som utgangsstoffer anvender man på den ene side slike forbindelser som inneholder en med gruppen R-CO-NH-Y substituert benzolrest. ;De ved fremgangsmåten ifølge oppfinnelsen oppnåelige sulfonylsemikarbazid-derivater er verdifulle legemidler som utmerker seg ved en sterk og langvarig blodsukkersenkende virkning. Dette gjelder spesielt for slike forbindelser hvori R betyr en fenylrest som i 2-stilling har en alkoksygruppe. Fremgangsmåteproduktenes blodsukkersenkende virkning kan f.eks. fastslås på kaniner ved at man fdrer fremgangsmåteproduktene i doser på 10 mg/kg og bestemmer blodsukkerverdien etter den kjente metode av Hagédorn-Jensen over en lengere tid. I følgende tabell er det sammenstillet den blodsukkersenkende virkning av noen ifølge oppfinnelsen fremstilte forbindelser: ;I forhold til dette viser ved sammenligningsforsøk det som oralt antidiabetikum kjente og som legemiddel anvendte N-(4-metylbenzolsulfonyl)-N'-n-butyl-urinstoff ved en dosering på ;25 mg/kg ingen senkning av blodsukkerspeilet mer. ;I fra belgisk patent nr. 654.561 er det kjent benzolsulf onylurinstoffer, hvis terskelverdi ligger i samme størrelses-orden som for forbindelsene fremstilt ifølge oppfinnelsen. I motset-ning til dette vedrører foreliggende oppfinnelse fremstilling av benzolsulfonylsemikarbazider. Med forbindelsene fra det belgiske patent oppnås ved en dosering på 400 mg/kg resp. 50 mg/kg en virknings-varighet og virkningsstyrke som oppnås med forbindelsene fremstilt ifølge oppfinnelsen med en dosering på bare 10 mg/kg. ;Fra norsk patent nr. 105.565 er det kjent benzolsulf onylsemikarbazider som ved benzolkjernen i p-stilling til sulfonylsemikarbazidgruppen mangler den for forbindelsene fremstilt ifølge oppfinnelsen karakteristiske acylaminoalkylgruppe. ;Den blodsukkersenkende virkning av benzolsulfonyl-aemikarbazidene ifølge norsk patent nr. IO5.565 utgjør ved en dosering på 400 mg/kg resp. 100 mg/kg etter 6 timer 36 resp. 30$. ;En sammenlignbar virkningsstyrke oppnås med forbindelsene fremstilt ifølge oppfinnelsen ved en dosering på 10 mg/kg, dosen er altså ;40 resp. 10 ganger mindre. ;Dessuten er forbindelsene fremstilt ifølge oppfinnelsen vesentlig lenger virksomme ved betraktelig mindre doseringer. ;Følgende tabell viser virkningsvarigheten av noen forbindelser ;ifølge norsk patent nr. IO5.565 ved en dosering på 400 resp. 100 mg/kg. Ved en dosering på bare 10 mg/kg viser disse forbindelser ingen blodsukkersenkende virkning. Grensedosen for forbindelsene ifølge det norske patent på 1,25 - 2,5 mg/kg har bare gyldighet når forbindelsene appliseres intravenøst, ved oral applikasjon utgjør grensedosen 5 mg/kg. ;Virkningsvarigheten av noen forbindelser ifølge norsk patent nr. 105.565. ;K 400 resp. K 100 betyr blodsukkersenkende virkning på kaniner i ;% etter oral applikasjon av 400 resp. 100 mg stoff pr. kg forsøksdyr. ;;Fremgangsmåteproduktene skal fortrinnsvis anvendes til fremstilling av oralt administrerbare preparater med blodsukkersenkende virkning for behandling av diabetes mellitus og kan appliseres som sådanne eller i form av deres salter, resp. i nærvær av stoffer som fører til en saltdannelse. Til saltdannelse kan eksempelvis anvendes: alkaliske midler som alkali- eller jordalkalihydroksyder, -karbonater eller -bikarbonater eller fysiologisk tålbare syrer. Som medisinske preparater kommer det fortrinnsvis i betraktning tabletter som ved siden av fremgangsmåteproduktene inneholder de vanlige hjelpe- og bærestoffer som talkum, stivelse, melkesukker, tragant, magnesium-stearat osv. ;Eksempel 1. ;a) 6-<3-klor-benzamido>-etyl)-benzolsulfonyl7-l,l-pentametylen-semikarbazid. 10 g N-/—4-($-<3-klorbenzamido>-etyl)-benzolsulfonyl7-metyluretan (smp. 173-175°C) suspenderes i 100 ml dioksan og blandes under omrøring med 2,8 g 1,1-pentametylenhydrazin. Man oppvarmer blandingen i 1 time ved 120-130°C, idet den ved omsetningen dannede metanol avdestillerer sammen med noe dioksan. Ved avkjøling faller det ut det dannede B-<3-klor-benzamido>-etyl)-benzolsulfonyl7-1,1-pentametylen-semikarbazid i krystallinsk form og renses ved opp-løsning i fortynnet ammoniakk med etterfølgende utfelling med fortynnet eddiksyre. Etter omkrystallisering fra metanol/dimetylformamid smelter semikarbazidet ved 229_231°C under spaltning. ;På analog måte får man ;b) 4-/?-(g-<3-klor-benzamido>-etyl)-benzolsulfonyl7-l,1-heksametylensemikarbazid med smp. 207-209°C (spaltning) av metanoldimetylformamid ;og ;c ) 4-/4~- (3-<3-klor-benzamido>-etyl) -benzolsulf onyl7-l-metyl-l-benzyl-semikarbazid med smp. 112-111I0C (ved spaltning) (av metanol/vann), ;av ;N-/TT-(B-<4-klor-benzamido>-etyl)-benzolsulfonyl7-metyluretan (smp. 213-215°C) får man d) '4-/?-(3-<4-klor-benzamido>-etyl)-benzolsulfonyl7-l,1-pentametylen-semikarbazid med smp. 220-223°C (under spaltning) (av dimetylformamid/vann) og e) 4-/4~- (g-<4-klor-benzamido>-etyl)-benzolsulfonyl7-l, 1-heksametylensemikarbazid med smp. 195-198°C (under spaltning) (av dimetylformamid /metanol ), ;av ;N-/4~-($-<4-fluor-benzamido>-etyl)-benzolsulfonyl7-metyluretan (smp. 194-196°C) får man f) 4-/4~-($-<4-fluor-benzamido>-etyl)-benzolsulfonyl7-l,1-pentametylen-semikarbazid med smp. 238-240°C (under spaltning) (av metanol-dimetylf ormamid ) og g) 4-/4"-(3-<<>4-fluor-benzamido<>->etyl)-benzolsulfonyl7-l,l-heksa-metylen-semikarbazid med smp. 208-210°C (under spaltning) (av ;metanol/dimetylformamid), ;av ;N-/4~- (g-<4-metyl-benzamido>-etyl)-benzolsulfonyl7-metyluretan (smp. 200-202°C) får man ;h) 4-/4~- ($-<3-metyl-benzamido>-etyl)-benzolsulfonyl7-l, 1-pentametylen-semikarbazid med smp. 24l-243°C (under spaltning) (av ;metanol-dimetylformamid) og ;i) 4-(g-<3-metyl-benzamido>-etyl)-benzolsulfonyl7-l,1-heksametylensemikarbazid med smp. 209-211°C (av metanol/dimetylformamid), ;av ;N-/4~- (g-< 2-metoksy-benzamido>-etyl) -benzolsulf onyl7-metyluretan ;(smp. 174-176°C) får man ;k) 4-/IT-(3-<2-metoksy-benzamido>-etyl)-benzolsulfonyl7-l ,1-pentametylen-semikarbazid med smp. 157_159°C (av metanol), ;1) 4-/¥-($-<2-metoksy-benzamido>-etyl)-benzolsulfonyl7-l,1-heksa-metylen-semikarbazid med smp. 155-157°C (av metanol), og m) 4-/^-(3-<2-metoksy-benzajnido>-etyl)-benzolsulfonyl7-l,l-tetramety-len-semikarbazid med smp. 172-174°C (av metanol/dimetylformamid), ;av N-/4~-(3-<3-metoksy-benzamido>-etyl)-benzolsulfonyl7-metyluretan (smp. 173-175°C) får man ;n) 4-/4"-(3-<<>3_metoksy-benzamido<>->etyl)-benzolsulfonyl7-l,l-penta--metylen-semikarbazid med smp. 230-232°C (under spaltning) av metanol-dimetylformamid og ;o) 4-/4~- (0-<3-metoksy-benzamido>-etyl)-benzolsulfonyl7-l, 1-heksa-metylen-semikarbazid med smp. 207-209°C (under spaltning) (av metanol/ dimetylformamid), ;av ;N-/4~- (3-<2-allyloksy-benzamido>-etyl)-benzolsulfonyl7-metyluretan (smp. 145-148°C) får man ;p) 4-/T-(8-<2-allyloksy-benzamido>-etyl)-benzolsulfonyl7-l,1-pentametylen-semikarbazid med smp. 157_159°C (av metanol), ;av ;N-/4-(B-<2-metoksy-5-metyl-benzamido>-etyI)-benzolsulfonyl7-metyluretan (smp. 175-177°C) får man ;q) 4-/¥-(B-<2-metoksy-5-metyl-benzamido>-etyl)-benzolsulfonyl7-l,l-pentametylen-semikarbazid med smp. 176-178°C (under spaltning) ;(av metanol), ;av ;N-/¥-(B-<<>0-fenyl-propionamido<>->etyl)-benzolsulfonyl.7-metyluretan ;(smp. 137-139°C) får man ;r) 4-/4~-(B-<<>3-fenyl-propionamido<>->etyl)-benzolsulfonyl7-l,1-pentametylen-semikarbazid med smp. 173~175°C (under spaltning)(av metanol), av ;N-/¥-(3-<3-trifluormetyl-benzamido>-etyl)-benzolsulfonyl7-metyluretan (smp. 178-180°C) får man ;s) 4-/4~-($-<3-trifluormetyl-benzamido>-etyl)-benzolsulfonyl7-l,l-pentametylen-semikarbazid med smp. 209-211°C (under spaltning) (av metanol-dimetylformamid) og ;t) 4-/¥-(3-<3-trifluormetyl-benzamido>-etyl)-benzolsulfonyl7-l,l-heksametylen-semikarbazid med smp. 201-202°C (av metahol-dimetylformamid), ;av ;N-/4~-( 8-<3-metoksy-tiof en-2-karbonamido>-etyl) -benzolsulf onyl7-metyluretan (smp. 226-228°C) (under spaltning) får man u) 4-_/ 4-( 0-<3-metoksy-tiofen-2-karbonamidé>-etyl)-benzolsulfonyl7-1,1-<p>entametylen-semikarbazid med smp. 202-204°C (av metanol/ dimetylformamid) og ;v) 4-_/ 4-( g-<3-metoksy-tiofen-2-karbonamido>-etyl)-benzolsulfonyl7-1,1-heksametylen-semikarbazid med smp. l8l-l82°C (av metanol/ dimetylformamid), ;av ;N-_/ 4-( g-<f enoksyacetamido>-etyl)-benzolsulfonyl7-metyluretan ;(smp. 136-138°C) får man ;w) 4-/_ 4- ( g-<fenoksyacetamido>-etyl)-benzolsulfonylj-l,1-pentametylen-semikarbazid med smp. 150-151°C (av metanol), ;x) 4-_/ 4-( g-<fenoksyacetamido>-etyl)-benzolsulfonyl/-l,1-heksa-metylen-semikarbazid med smp. 111-113°C (av metanol) og y) 4-/ 4-(g-<fenoksyacetamido>-etyl)-benzolsulfonyl/-l,l-(3-metyl-pentametylen)-semikarbazid med smp. 153-155°C (av metanol), ;av ;N-/_ 4-(g-<g-fen<y>l<p>ro<p>ionamido>-et<y>l)-benzolsulfon<y>l/-metyluretan ;(smp. 142-144°C) får man ;z) 4-/~4-(g-< g-fenylpropionamido>-etyl)-benzolsulfonyl7-l,1-heksametylensemikarbazid med smp. l48-150°C (av.metanol), ;aa) 4-/~4-(g-<g-fenylpropionamido>-etyl)-benzolsulfonyl7-l,1-tetrametylensemikarbazid med smp. l67-l68°C (av metanol), ;ab) 4- £~ 4-(g-< g-fenylpropionamido>-etyl)-benzolsulfonyl7-l-metyl-1-benzyl-semikarbazid med smp. 158-l60°C (av metanol) og ac) 4- £" k-(g-<g-fenylpropionamido>-etyl)-benzolsulfony17-1,l-(3-metylpentametylen)-semikarbazid med smp. l80-l82°C (av metanol), ;av ;N-_/ 4-( g-<cinnamoylamido>-etyl)-benzolsulf onyl7-metyluretan (smp. 198-200°C) får man ;ad) 4-/~~4-( g-<cinnamoylamido>etyl)-benzolsulf ony 1/-1 ,l-( 3-metyl-pentametylen)-semikarbazid med smp. 198-200°C (av metanol/dimetylformamid), ;av ;N-/_ 4-(g-<A^-tetrahydrobenzamido>-etyl)-benzolsulfonyl/metyluretan ;(smp. 151-153°C) får man ae) 4-_/ 4-(g-<A^-tetrahydrobenzamido>-etyl)-benzolsulfonyl/-l ,1-heksametylensemikarbazid med smp. 170-171°C (spaltning) (av metanol) ;og ;af) 4-/~~4-( 3-<A^-tetrahydrobenzamido>-etyl)-benzolsulfonyl7-l,l-(3-metylpentametylen)-semikarbazid med smp. l84-l86°C (spaltning) ;(av metanol), ;av ;N-/<->4-(3-<3-trifluormetylbenzamido>-etyl)-benzolsulfonyl7-metyluretan (smp. 178-180°C) får nan ;ag) 4-/~4-( 3-<3_trif luormetylbenzamido>-etyl)-benzolsulf ony 1/-1,1-(3-metylpentametylen)-semikarbazid med smp. 222-224°C (av metanol/ dimetylformamid), ;av ;N-_/— 4-(3_<3-fluorbenzamido>-etyl)-benzolsulfonyl7-metyluretan ;(smp. l84-l86°C) får man ;ah) 4-/~4-(3-<3-fluorbenzamido>-etyl)-benzolsulfony17-1,1-pentametylen-semikarbazid med smp. 210-212°C (spaltning) (av metanol/ dimetylformamid), ;ai) 4-/~4-(3~<3-f luorbenzamido>-etyl) -benzolsulf onyl7-l 51-heksa-metylen-semikarbazid med smp. 198-200°C (av metanol) og ak) 4-/~4-( 3~<3-f luorbenzamido>-etyl)-benzolsulf onyl7-l,l-tetra-metylen-semikarbazid med smp. 200-202°C (av metanol/dimetylformamid), av ;N-/~4-(3-<3-klorbenzamido>-etyl)-benzolsulfonyl/-metyluretan (smp. 173-175°C) får man ;al) 4-_/—4-(3-<3-klorbenzamido>-etyl)-benzolsulf onyl7-l,l-( 1-metyl-pentametylen)-semikarbazid med smp. 210-211°C (av metanol/dimetylformamid) og ;am) 4-J/—4-( 3-<3_klorbenzamido>-etyl)-benzolsulf onyl/-l-metyl-l-isopropyl-semikarbazid med smp. 176-177°C (av metanol/dimetylformamid ), ;av ;N-/~4-(3-<4-fluorbenzamido>-etyl)-benzolsulfonyl7-metyluretan (smp. 194-196°C) får man ;an) 4-/—4-(3-<4-fluorbenzamido-etyl)-benzolsulfonyl/-l,l-(3-metylpentametylen)-semikarbazid med smp. 215-217°C (spaltning) (av metanol/dimetylformamid), ;av ;N-/~4-(3-kapronamido-etyl)-benzolsulfonyl/-metyluretan (smp. 113-115°C) får man ;ao) 4- /"4- (3 -kapronamido-etyl) -benzolsulf ony 3.7-1,1- (3-metyl-pentametylen)-semikarbazid med smp. l63_l65°C (av metanol), ;av ;N-/-4-(g-<3-etoksytiofen-2-karbonamido>-etyl)-benzolsulfonyl7-metyluretan (smp. l63_l65°C) får man ;ap) 4-/~"4-(g-< 3-etoksytiofen-2-karbonamido>-etyl)-benzolsulfonyl7-1,1-pentametylen-semikarbazid med smp. 159-l6l°C (av metanol) og aq) 4-_/ 4-(g-<3-etoksytiofen-2-karbonamido>-etyl)-benzolsulfonyl7-1,1-heksametylen-semikarbazid med smp. 152-l63°C (av metanol), ;av ;N-/_ 4-(3-<3-metoksybenzamido>-etyl)-benzolsulfonyl7-metyluretan (smp. 173-175°C) får man ;ar) 4-_/ 4-( g-<3-metoksybenzamido>-etyl)-benzolsulfonyl7-l ,l-(3-metylpentametylen)-semikarbazid med smp. 237-239°C (spaltning) (av metanol/dimetylformamid), ;av ;N-_/ 4-( g-<2-etoksybenzamido>-etyl)-benzolsulf onyl/-metyluretan (smp. 172-174°C) får man ;as) 4-( g-<2-etoksybenzamido>-etyl)-benzolsulfonyl/-l,l-pentametylen-semikarbazid med smp. 153-154°C (av metanol), ;at) 4-/_ 4-(g-<2-etoksybenzamido>-etyl)-benzolsulfonyl/-l,1-heksametylen-semikarbazid med smp. 135-137°C (av metanol) og au) 4-/ 4-(g-<2-etoksybenzamido>-etyl)-benzolsulfonyl/-l,l-(l-metylpentametylen)-semikarbazid med smp. 137-139°C (av metanol), av ;N-_/ 4-( g-<2-propoksybenzamido>-etyl)-benzolsulf ony l/-mety luret an (smp. 159-161°C) får man ;av) k-/_ 4-( g-<2-propotsybenzamido>-etyl)benzolsulfonyl/-l ,l-(3-metylpentametylen)-semikarbazid med smp. 171-173°C (av metanol/ dimetylformamid), ;av ;N-/<->4-(g-<2-metoksy-5-klorbenzamido>-etyl)-benzolsulfonyl7-metyluretan (smp. l89-192°C) får man ;aw) 4-/^—4- ( g-<2-metoksy-5-klorbenzamido>-etyl)-benzolsulf onyl/- 1,1-pentametylen-semikarbazid med smp. l64-l66°C (av metanol) og ax) 4-_/ 4-( g-<2-metoksy-5-klorbenzamido>-etyl)-benzolsulfonyl7-1,1-heksametylen-semikarbazid med smp. l6l-l63°C (av metanol), ;av ;Nt A~4-(g-<2-metoksy-4-klorbenzamido >-etyl)-benzdlsulfonyl7-metyluretan (smp. 178-l80°C) får man ay) 4-/~4-( g-<2-metoksy-4-klorbenzamido>-etyl) -benzolsulf ony l7-l,l-(3-metylpentametylen)-semikarbazid med smp. 177-179°G (av metanol), ;av ;N-/~4-(g-< 2-metoksy-3_klorbenzamido>-etyl)-benzolsulfonyl/-metyluretan (smp. 151-153°C) får man ;az) 4-_/—4-(g-<2-met oksy-3_klorbHnzamido>-etyl)-benzolsulf ony l7-1,1-pentametylen-semikarbazid med smp. 173_175°C (av metanol), ;av ;N-/~4-( g-< 3-et oksybenzamido-etyl)-benzolsulf ony l/-mety lur et an ;(smp. 165-167°C) får man ;ba) 4-/~4-(g-<3-etoksybenzamido>-etyl)-benzolsulfonyl7-l,l-pentametylen-semikarbazid med smp. 207-20$°C (spaltning) (av metanol/ dimetylformamid), ;bb) 4-/—4-(g-<3-etoksybenzamido>-etyl)-benzolsulfonyl7-l,1-heksa-metylen-semikarbazid med smp. 177-179°C (av metanol/dimetylformamid) og ;bc) 4-/~4-(g-<3-etoksybenzamido>-etyl)-benzolsulfonyl7-l,l-(3-metylpentametylen)-semikarbazid med smp. 224-226°C (spaltning) ;(av metanol/dimetylformamid), ;av ;N-_/~4-( g-<2-metoksy-5-metylbenzamido>-et yl)-benzolsulf ony l7-metyluretan (smp. 175-177°C) får man ;bd) 4-/~4-(g-< 2-metoksy-5_metylbenzamido>-etyl)-benzolsulfonyl/- 1,1-heksametylensemikarbazid med smp. 155-157°C (av metanol) og be) 4-/.—4- (g-<2-metoksy-5-metylbenzamido>-etyl) -benzolsulf onyl /l,l-(3-metylpentametylen)-semikarbazid med smp. 176-178°C (av metanol), av ;N-/<->4-(g<-><2-g<->metoksyetoksy-benzamido<>->etyl)-benzolsulfonyl7-metyluretan (smp. 123-125°C) får man ;bf) 4-/~" 4-(g-<2-g-metoksyetoksybenzamido>-etyl)-benzolsulfonyl7-1,1-pentametylen-semikarbazid (av smp. l43-l45°C) (av metanol) og bg) 4-/ 4-(g-<2-g-metoksyetoksybenzamido>-etyl)-benzolsulfonyl7-l,l-(3_metylpentametylen)-semikarbazid med smp. 157-159°C (av metanol), av ;N-_/ 4-( g-<2-etoksy-5_klorbenzamid6>-etyl)-benzolsulf onyl/-met y lur et an (smp. 203-205°C) får man ;bh) 4-/~ 4-(g-<2-etoksy-5-klorbenzamido>-etyl)-benzolsulfonyl7-l,l-pentametylen-semikarbazid med smp. l63-l65°C.(av metanol) og ;bi) 4-/—4-(g-<2-etoksy-5_klorbenzamido>-etyl)-benzolsulfonyl7-1,1-heksametylen-semikarbazid med smp. 164-166°C (av metanol), ;av ;N-/<->4-(g-<2-metoksy-3-metylbenzamido>-etyl)-benzolsulfonyl7-metyluretan (smp. 153-155°C) får en ;bk) 4-/—4-(g-<2-metoksy-3-metylbenzamido>-etyl)-benzolsulfonyl7-l,l-(3-metylpentametylen)-semikarbazid med smp. 170-172°C (av metanol), av ;N-_/ 4-( 0-<2-g-metoksyetoksy-5-metylbenzamido>-etyl)-benzolsulfonyl7-metyluretan (smp. 160-162°C) får man ;bl) 4-_/ 4-( g-<2-0-metoksyetoksy-5_metylbenzamido>-etyl)-benzolsulfonyl/-l,l-(3-metylpentametylen)-semikarbazid med .smp. 151-153°C ;(av metanol), ;av ;N-/ 4-(g-<3~klorfenoksyacetamido>-etyl)-benzolsulfonyl/-metyluretan ;(smp. 121-123°C) får man bm) 4-/ 4-(g-<3-klorfenoksyacetamido>-etyl)-benzolsulfonyl7-l,l-(3-metylpentametylen)-semikarbazid med smp. 106-108°C (spaltning) ;(av metanol), ;av ;N-_/ 4-( g-<g-4-klorfenylpropionamido>-etyl)-benzolsulfonyl7-metyl- ;uretan (smp. 165-167°C) får man ;bn) 4-/~4-(g-<g-4-klorfenylpropionamido-etyl)-benzolsulfonyl7-1,1-pentametylen-semikarbazid med smp. 179-l8l°C (spaltning) (av metanol) og ;bo) 4-_/ 4-(g-<g-4-klorfenylpropionamido>-etyl)-benzolsulfonyl/- l,l-(3_metylpentametylen)-semikarbazid med smp. l63-l65°C (av metanol), av ;N-/_ 4-(g-<g-3~klorfenylpropionamido>-ety1)-benzolsulfonyl7-metyl- ;uretan (smp. 128-130°C) får man ;bp) -4-_/ 4-(g-<g-3-klorfenylpropionamido>-etyl)-benzolsulfonyl/- 1,1-heksametylen-semikarbazid med smp. l6l-l63°C (av metanol) og bq) 4-_/—4-(g-< g-3-klorfenylpropionamido>-etyl)-benzolsulfonyl7-1,I-(3-metylpentametylen)-semikarbazid med smp. 137-139°C (av metanol), av ;N-_/ 4-(g-<3,4-tetrametylentiofen-2-karbonamido>-etyl)-benzolsulfonyl/- metyluretan (smp. 194-196°C) får man ;br) 4-/—4-(g-< 3,4-tetrametylentiofen-2-karbonamido>-etyl)-benzolsulf onyl/-l,l-pentametylen-semikarbazid med smp. 149-151°C (av ;metanol/dimetylformamid) og ;bs) 4-/ 4-(g-<3,4-tetrametylentiofen-2-karbonamido>-etyl)-benzolsulfonyl7-l,l-(3-metylpentametylen)-semikarbazid med smp. 168-169°C ;(av metanol), ;av ;N-/<->4-(g-<2-metoksy-3,5-diklorbenzamido>-etyl)-benzolsulfonyl/~uret<y>l-metan (smp. l87-l88°C) får man ;bt) 4-/~4-(g-<2-metoksy-3,5-diklorbenzamido>-etyl)-benzolsulfonyl7-l,l-(3-metylpentametylen)-semikarbazid med smp. l6l-l63°C (av metanol/ dimetylformamid), ;av ;N-_/ 4-( g-<2-metoksy-benzamido>-etyl)-benzolsulf onyl7-ety luret an ;(smp. 168°C) får man bu) 4-/~4-(g-<2-metoksybenzamido>-etyl)-benzolsulfonyl7-(y-dimetyl-pentametylen)-semikarbazid, smp. 155-157°C, ;bv) 4-_/—4-( 0-<2-metoksybenzamido>-etyl)-benzolsulfonyl7-(1-isonor-ganatanyl)-nrinstoff, smp. 170-171°C, ;bw) 4-_/ 4- (g-<2-metoksybenzamido>-etyl)-benzolsulfonyl7-l,1-(2,6-dimetylpentametylen)-semikarbazid, smp. 203-204°C, ;bx) 4-/—4-(g-<2-metoksybenzamido>-etyl)-benzolsulfony17-1,l-(g-pentametylen)-semikarbazidj smp. 175"176°C, ;by) N1~4-_/ 4-( g-<2-metoksybenzamido>-etyl)-benzolsulfonyl7-N2-_/_norgranatyl-(9_).7-urinstoff, smp. 190-191°C, ;bz) N1~4-_/ 4-( g-<2-metoksybenzamido>-etyl)-benzolsulfonyl7-N2~ /<->nortropanyl-(827-urinstoff, smp. 213-2l4°C, ;ca) N1-4-/~4-(g-<2-metoksybenzamido>-etyl)-benzolsulfonyl7-N2~;(lj2,5,6-tetrahydropyridyl-l)-urinstoff, smp. 156-157°C ;Eksempel 2. ;4- /~ 4-( g- benzamido- etyl)- benzolsulfony j. 7- 1, 1- pentametylen- semikarbazid. a) 14,7 g 4,4-difenyl-l,1-pentametylen-semikarbazid suspenderes med 16,3 g av natriumsaltet av 4-(g-benzamido-etyl)-benzolsulfonamid i 100 ml dimetylformamid og oppvarmes i tre timer ved 100°C. Man fortynner etter avkjøling med vann, gjør reaksjons-blandingen alkalisk med ammoniakk og fjerner det dannede difenylamin ved tre gangers utrystning med eter. Den vandige fase filtreres og surgjøres ved iseddik. Det i krystallinsk form dannede 4-/~4-(g-benzamido-etyl)-benzolsulfony17-1,l-pentametylen-semikarbazid smelter etter omkrystallisering fra dimetylformamid/vann ved 217-218°C. ;På analog måte får man: b) 4-/"4-( Ø-benzamido-etyl)-benzolsulfonyl7-l,l-heksametylensemikarbazid med smp. 233-236°C (av dimetylformamid/vann). ;Eksempel 3. ;4-/~ 4-( g- benzamido- etyl)- benzolsulfonyl7- l, 1- pentametylen- semikarbazid. ;a) 5)9 g 1-pentametylenimino-parabansyre suspenderes i 240 ml benzol. Etter tilsetning av 3 g trimetylamin går blandingen ;i oppløsning og blandes under omrøring med 9>7 g 4-(g-benzamido-etyl) -benzolsulf oklorid. Man lar det etter 3 timers koking under tilbakeløp avkjøle og dekantere fra seigt residuum. Dette digereres for å fjerne dannet trietylamin-hydroklorid med vann og bringes ved utrivning med alkohol/vann til krystallisering. Det således dannede 4-/—4-(g<->benzamido-etyl)-benzolsulfonyl7-3_pentametylen-iminoparaban-syre renses ved utkoking med metanol og smelter ved 228°C under spaltning. ;b) 0,5 g av det ovenfor dannede parabansyrederivat opp- ;varmes med 5 ml l-n natronlut i 10 min. på dampbad. Etter kort tid ;krystalliserer saltet av 4-/~4-(g-benzamido-etyl)-benzolsulfonyl/- 1,1-pentametylen-semikarbazid ut. -Ved surgjøring med fortynnet eddiksyre fåes herav den fri forbindelse med smp. 2l8°C. ;Eksempel 4. ;4-/_ 4-(g-4-klor-benzamido-etyl)-benzolsulfonyl7-l,1-pentametylen-semikarbazid . ;9») g N-_/7T-( g-4-klor-benzamido-etyl)-benzolsulf onyl7-urinstoff (smp. 194-196°C) oppvarmes i 100 ml dioksan med 5 g N-aminopiperidin under tilbakeløp til koking. Etter dannelsen av en klar oppløsning avdamper man oppløsningsmidler under nedsatt trykk, behandler residuet med ca. 1%- ig ammoniakk, filtrerer og surgjør filtratet med fortynnet eddiksyre. Det utfelte 4-/~4-(g-4-klor-benzamido-etyl)-benzolsulfonyl/-1,1-pentametylen-semikarbazid omkrystalliseres fra vann-dimetylformamid og smelter ved 220-223°C ;under spaltning. ;Eksempel 5- ;4-/ 4-(g-$3-metyl-4-klor-benzamido>- etyl)-benzolsulfonyl7-l,1-pentametylen- semikarbazid.. a) 16,8 g 4-(g-<3-metyl-4-klor-benzamido>-etyl)-benzol-sulfonamid-natrium oppvarmes med 11,1 g 1,1,5,5-bis-pentametylen-kårbohydrazid (smp. 178°C) i et foroppvarmet oljebad i 10-15 min. ;ved 180 C. Blandingen blir grøtaktig og stivner deretter igjenT;Man behandler etter avkjøling med vann, filtrerer, surgjør filtratet med eddiksyre og omkrystalliserer reaksjonsproduktet av metanol. 4-/~4-(3-<3-metyl-4-klor-benzamido>-etyl)-benzolsulf onyl<7>-l ,1-pentametylen-semikarbazid smelter ved 204-206°C. ;På analog måte får man ;b) 4-/~4-(3-< 3-metyl-4-klor-benzamido>-etyl) -benzolsulf ony l7-1jl-tetrametylen-semikarbazid med smp. 174-176°C (av metanol/vann) ;og av 4-(3-<a-metoksy-fenylacetamido>-etyl)-benzolsulfonamid (smp. 167-169°C) og 1,1,5,5-bis-pentametylen-karbohydrazid får man c) 4-/~4-( 3-<ot-metoksy-f eny lacetamido>-etyl) -benzolsulf onyl7-l,1-pentametylen-semikarbazid med smp. 146-148°C. ;Eksempel 6. ;a) - 4-/—4-(3-benzamidoetyl)-benzolsulfonyl7-l,l-(Y-mety1-pentametylen)- semikarbazid. ;0,01 mol N-_/ 4-(3-benzamidoetyl)-benzolsulfonyl7-metyluretan oppvarmes i 135 ml toluol med 0,01 mol 1,1-y-metyl-pentametylen-hydrazin under omrøring ved 110-120°C. Den dannede metylalkohol avdestilleres. Etter 2-3 timers oppvarming lar man det avkjøle og suger fra. Residuet gjenutfelles fra Na^O^/HCl. Det dannede k-/_ 4-(3-benzamidoetyl)-benzolsulfonyl/-1 ,l-(y-metylpenta-metylen)-semikarbazid smelter ved 212°C. ;På analog måte får man: ;b) 4-/~p-(3-benzamidoetyl)-benzolsulfonyl7-l-metyl-l-isopropyl-semikarbazid, smp. 204°C, c) 4-/~ p-(3-benzamidoetyl)-benzolsulfonyl7-l,l-(y-metoksy-pentametylen)-semikarbazid, smp. 212°C, d) 4-/~p-(3-benzamidoetyl)-benzolsulfonyl7-l,1-(Y-isopropoksy-pentametylen)-semikarbazid, smp. 210°C, e) N-L-/-p-( 3-benzamidoetyl)-benzolsulf onyl7-N2-/._norgranatanyl-( 9^7-urinstoff, smp. 229-230°C, f) 4-/~4-(3-acetamidoetyl)-benzolsulfonyl7-l,1-pentametylen-semikarbazid, smp. 203°C, g) 4-/—4-( 3-ac etamidoetyl) -benzolsulf ony 1^7-1 ,l-( y-met yl-pent amety len) - semikarbazid, smp. l87-l89°C. ;Eksempel 7• ;4-/~ 4-( 3- benzamidoetyl)- benzolsulfonyl7- l, 1- pentametylen- semikarbazid. ;0,013 mol 4-/~4-(3-aminoetyl)-benzolsulfonyl7-l,l-pentametylen-semikarbazid (fremstilt ved forsåpning av 4-/~"4-(3-acetyl-aminoetyl)-benzolsulfonyl7-l,1-pentametylen-semikarbazid, ;smp. 198-199°C, oppvarmes i 15 ml kloroform med 0,024 ml pyridin og 0,013 mi benzoylklorid i 6 timer ved 35°C. Residuet suges fra og ;gjenutfelles fra Na^O^/HCl. Forbindelsen smelter ved 2l6-2l8°C. Eksempel 8. a) 4-/_ 4-(3-2-metoksybenzamidoetyl)-benzolsulfonyl7-l,1-pentametylen-semikarbazid. ;0,01 mol 4-/~4-(3-aminoetyl)-benzolsulfonyl7-1,1-pentametylen-semikarbazid oppløses i 0,01 mol 2-n NaOH og blandes dråpevis under omrøring med 0,01 mol 2-metoksybenzoylklorid. For fullstendig omsetning oppvarmer man. i to timer ved 40°C . Det utfelte stoff suges fra og residuet gjenutfelles fra Na2C0^/HCl. Stoffet smelter ved 156°C. ;På tilsvarende måte får man ;b) 4-/—4-(3-trimetylacetamidoetyl)-benzolsulfonyl7-pentametylen-semikarbazid, smp. l87-l89°C, c) 4-/ 4-(3-3'-toluylamidoetyl)-benzolsulfonyl7-l,l-(Y-metylpenta-metylen)-semikarbazid, smp. 234-1235°C, d) 4-/~4-(3-3'-klorbenzamidoetyl)-benzolsulfonyl7-l,l-(Y-metyl-pentametylen)-semikarbazid, smp. 223-224°C, Eksempel" 9• a) 4-/~4-(3-2-metoksybenzamidoetyl)-benzolsulfonyl7-l,l-(Y-metyl-pentametylen)- semikarbazid. ;0,01 mol 4-_/-4-( 3-aminoetyl)-benzolsulfonyi7-1,1-(y-metyl-pentametylen)-semikarbazid, smp. l87-l89°C (fremstilt ved forsåpning av 4-_/ 4-( 3-acetylaminoetyl)-benzolsulf onyl7-l,l-(Y_metyl-pentametylen)-semikarbazid) has i 10 ml pyridin og 0,01 mol 2-metoksybenzoylklorid tilsettes dråpevis. Under oppvarming inntrer reaksjon. Man lar det stå i 12 timer og oppvarmer deretter i 30 min. på dampbad. Etter avkjøling helles det på is og utfellingen suges fra og gjen-utf elles fra Na2C03/HCl. Det rene stoff smelter ved 164°C. ;På analog måte får man: ;b) 4-/_ 4-(3-5'-klor-2'-metoksybenzamidoetyl)-benzolsulfonyl7-l,1-(Y-metylpentametylen)-semikarbazid, smp. 165-168°C, c ) 4-_/—4-( 3-3 ' -metoksytiof en-2-karbamidoetyl)-benzolsulf onyl7-l ,1-(Y-metylpentametylen)-semikarbazid, smp. 174-177°C, d) 4-_/ 4-( 3-21-etoksybenzamidoetyl)-benzolsulf onyl7-l,l-( Y-metyl-pentametylen)-semikarbazid, smp. l69-171°C, e) 4-/ 4-(3-2'-metoksybenzamidoetyl)-benzolsulfonyl7-l,l-YY~etyl-pentametylen)-semikarbazid, smp. 160°C, sintring 166°C. ;Eksempel 10. ;*~ L 4-( 3-<2-metoksy-benzamido>-etyl)-benzolsulf onyl7-l, 1-penta-metylensemikarbazid. a) Hj7 g N-/~4-(3-<2-metoksy-benzamido>-etyl)-benzolsulf onyl7-N' -fenyl-tiourinstoff, R"*- means an alkylene imino residue with 3-7 C atoms, as the alkylene chain can optionally be substituted with 2-4 methyl groups or with an alkyl or alkoxy acid residue with up to 3 C atoms, or if it contains 5 C atoms which optionally may be substituted with low molecular weight alkyl or alkoxy, ;or ;the remainder ;;in which R^ and R 2 mean low molecular weight alkyl, R 2 also ;benzyl, ;as well as their acid addition salts, or salts with a base, ;wherein the method is characterized by mari either ;a) reacts with the group R-CO-NH-CH2-CH2-substituted benzenesulfonamides, suitably in the form of their salts, with iminocarbamic acid esters, imino-thiocarbamic acid esters or iminoureas, which as an imino residue contain the grouping R A or b) reacts hydrazines of formula R-^-NHg or their salts with substituted benzenesulfonyl isocyanates-, -carbamic acid esters, ;-thiocarbamic acid esters, -carbamic acid halides or ureas which are substituted with the group R-CO-NH-CH2-CH2- in the benzene nucleus, or ;c) reacts benzenesulfochlorides that are substituted with the group R-CO-NH-CH2-CH"2- with ureas that are substituted with the group ;R<1>, or ;d) hydrolyzes benzenesulfonyl isosemicarbazide ethers, ;-isothiosemicarbazide ethers or benzenesulfonyl-iminoparabanic acids which in the benzene nucleus are substituted with the group R-CO-NH-CH2-CH2- or ;e) in benzenesulfonylthiosemicarbazides of formula ;exchanges the sulfur atom with an oxygen atom, or f) in benzenesulfonylsemicarbazides of formula ;optionally stepwise introducing the residue R-CO- and, if desired, treating ; they formed benzenesulfonyl semicarbazides with physiologically tolerable inorganic or organic acids, or with a base for salt formation. ;As semicarbazides, resp. iminoureas for the synthesis mentioned under a) are suitable those with the formula R^-NH-CO-NHp or acylated compounds with the formula R-NH-CO-NH-acyl, in which acyl means a preferably low molecular weight aliphatic or aromatic acid residue, or diphenylsemicarbazides with formula R<1->NH-CO-N (CgH^)2, wherein the phenyl residues can be substituted as well as connected to each other directly or via a bridge, or N,N'-disubstituted carbohydrazides with formula R-^NH-CO -NH-R<1>. As benzolsulfonyl-carbamic acid halides, the chlorides are primarily suitable. Furthermore, correspondingly, on the side of the urea molecule facing away from the sulfonyl group, unsubstituted or by other alkyl residues or aryl residues once or twice substituted benzenesulfonylureas can also be transferred by reaction with hydrazines of the formula R^-NHg, possibly in the form of their salts, in the desired connections. Instead of benzenesulfonylureas substituted in this way, corresponding N-benzenesulfonyl-N'-acyl ureas or bis-(benzenesulfonyl)ureas can also be used. One can, for example, treat such bis-(benzenesulfonyl)-ureas or N-benzenesulfonyl-N'-acyl-ureas with hydrazines of the formula R^-NHg and heat the formed salts to higher temperatures, suitably those of at least 80 °C. The aforementioned iminocarbamic acid esters or benzenesulfonyl-carbamic acid esters as well as the corresponding thioesters appropriately contain in the ester component a low molecular weight alkyl residue or a phenyl residue. ;The same as starting materials relevant with the group R-CO-NH-Y substituted benzenesulfonyl isosemicarbazide ethers, -isothiosemicarbazide ethers or -parabanic acids can be prepared by the reaction of corresponding isosemicarbazide ethers, isothiosemicarbazide ethers or parabanic acids with R-CO-NH-Y substituted benzenesulfochlorides. Likewise, the desulphurisation of R-CO-NH-Y substituted benzenesulfonyl thiosemicarbazides in methanol primarily leads to R-CO-NH-Y substituted benzenesulfonyl isosemicarbazides which are then transferred by hydrolysis into benzenesulfonyl semicarbazides. Depending on the nature of the link R-CO-, in some cases one or the other of the aforementioned methods for preparing the individual compounds that fall under the general formula will be unsuitable or at least require precautions to protect active groups. Such relatively rarely occurring cases can be easily recognized by experts, and it does not present any difficulties in such cases with results to use another of the described synthesis methods. The implementation of the method according to the invention can vary greatly in general with regard to the reaction conditions and can be adapted to the present conditions. For example, the reactions can be carried out using solvents, at room temperature or elevated temperature. As starting materials, on the one hand, such compounds are used which contain a benzene residue substituted with the group R-CO-NH-Y. The sulphonyl semicarbazide derivatives obtainable by the method according to the invention are valuable drugs which are distinguished by a strong and long-lasting blood sugar-lowering effect. This applies in particular to such compounds in which R means a phenyl radical which has an alkoxy group in the 2-position. The blood sugar-lowering effect of the method products can e.g. is determined on rabbits by feeding the process products in doses of 10 mg/kg and determining the blood sugar value according to the known method of Hagédorn-Jensen over a longer period of time. In the following table, the blood sugar-lowering effect of some compounds produced according to the invention is compiled: In relation to this, comparative tests show that N-(4-methylbenzenesulfonyl)-N'-n-butyl urea, known as an oral antidiabetic agent and used as a medicine, at a dosage of ;25 mg/kg no further lowering of the blood sugar level. From Belgian patent no. 654,561, benzolsulphonylureas are known, the threshold value of which is in the same order of magnitude as for the compounds produced according to the invention. In contrast to this, the present invention relates to the production of benzenesulfonyl semicarbazides. With the compounds from the Belgian patent, a dosage of 400 mg/kg resp. 50 mg/kg a duration of action and strength of action which is achieved with the compounds produced according to the invention with a dosage of only 10 mg/kg. From Norwegian patent no. 105,565, benzenesulfonylsemicarbazides are known which, at the benzene nucleus in the p-position to the sulfonylsemicarbazide group, lack the acylaminoalkyl group characteristic of the compounds produced according to the invention. ;The blood sugar-lowering effect of the benzolsulfonyl-aemicarbazides according to Norwegian patent no. 105,565 amounts to a dosage of 400 mg/kg resp. 100 mg/kg after 6 hours 36 resp. 30$. A comparable potency is achieved with the compounds produced according to the invention at a dosage of 10 mg/kg, the dose is thus ;40 resp. 10 times less. ;Furthermore, the compounds produced according to the invention are significantly longer effective at considerably smaller dosages. The following table shows the duration of action of some compounds according to Norwegian patent no. 105,565 at a dosage of 400 resp. 100 mg/kg. At a dosage of only 10 mg/kg, these compounds show no blood sugar-lowering effect. The limit dose for the compounds according to the Norwegian patent of 1.25 - 2.5 mg/kg is only valid when the compounds are applied intravenously, with oral application the limit dose is 5 mg/kg. ;The duration of action of some compounds according to Norwegian patent no. 105,565. K 400 or K 100 means blood sugar-lowering effect on rabbits in ;% after oral application of 400 resp. 100 mg substance per kg experimental animals. ;;The process products should preferably be used for the production of orally administrable preparations with a blood sugar-lowering effect for the treatment of diabetes mellitus and can be applied as such or in the form of their salts, resp. in the presence of substances that lead to salt formation. For salt formation, for example, alkaline agents such as alkali or alkaline earth hydroxides, carbonates or bicarbonates or physiologically tolerable acids can be used. As medicinal preparations, tablets are preferably taken into consideration which, in addition to the process products, contain the usual auxiliary and carrier substances such as talc, starch, milk sugar, tragacanth, magnesium stearate, etc. ;Example 1. ;a) 6-<3-chloro-benzamido >-ethyl)-benzenesulfonyl 7-1,1-pentamethylene-semicarbazide. 10 g of N-/-4-($-<3-chlorobenzamido>-ethyl)-benzenesulfonyl-7-methylurethane (m.p. 173-175°C) are suspended in 100 ml of dioxane and mixed with stirring with 2.8 g of 1,1- pentamethylenehydrazine. The mixture is heated for 1 hour at 120-130°C, the methanol formed during the reaction distilling off together with some dioxane. On cooling, the formed B-(3-chloro-benzamido>-ethyl)-benzenesulfonyl7-1,1-pentamethylene-semicarbazide precipitates out in crystalline form and is purified by dissolving in dilute ammonia with subsequent precipitation with dilute acetic acid. After recrystallization from methanol/dimethylformamide, the semicarbazide melts at 229-231°C with decomposition. ;B) 4-/?-(g-<3-chloro-benzamido>-ethyl)-benzenesulfonyl7-1,1-hexamethylenesemicarbazide with m.p. 207-209°C (decomposition) of methanol dimethylformamide ; and ; c ) 4-(4~-(3-<3-chloro-benzamido>-ethyl)-benzenesulfonyl 7-1-methyl-1-benzyl-semicarbazide with m.p. 112-11110C (by decomposition) (of methanol/water), ;of ;N-/TT-(B-<4-chloro-benzamido>-ethyl)-benzenesulfonyl7-methylurethane (m.p. 213-215°C) is obtained d) '4-/?-(3-<4-chloro-benzamido>-ethyl)-benzenesulfonyl 7-1,1-pentamethylene-semicarbazide with m.p. 220-223°C (under decomposition) (of dimethylformamide/water) and e) 4-/4~-(g-<4-chloro-benzamido>-ethyl)-benzenesulfonyl7-1,1-hexamethylenesemicarbazide with m.p. 195-198°C (under decomposition) (of dimethylformamide / methanol ), ;of ;N-/4~-($-<4-fluoro-benzamido>-ethyl)-benzenesulfonyl7-methylurethane (m.p. 194-196°C ) one obtains f) 4-[4--($-<4-fluoro-benzamido>-ethyl)-benzenesulfonyl 7-1,1-pentamethylene-semicarbazide with m.p. 238-240°C (under decomposition) (of methanol-dimethylformamide) and g) 4-[4"-(3-<<>4-fluoro-benzamido<>->ethyl)-benzenesulfonyl 7-1,1-hexa -methylene-semicarbazide with m.p. 208-210°C (under decomposition) (from ;methanol/dimethylformamide), ;from ;N-/4~-(g-<4-methyl-benzamido>-ethyl)-benzenesulfonyl7-methylurethane (m.p. 200-202°C) one obtains ;h) 4-/4~- ($-<3-methyl-benzamido>-ethyl)-benzenesulfonyl7-1,1-pentamethylene-semicarbazide with m.p. 24l-243° C (under cleavage) (from ;methanol-dimethylformamide) and ;i) 4-(g-<3-methyl-benzamido>-ethyl)-benzenesulfonyl7-1,1-hexamethylenesemicarbazide with m.p. 209-211°C (from methanol /dimethylformamide), ;from ;N-/4~- (g-< 2-methoxy-benzamido>-ethyl)-benzenesulfonyl7-methylurethane ;(m.p. 174-176°C) one obtains ;k) 4-/IT -(3-<2-methoxy-benzamido>-ethyl)-benzenesulfonyl7-1,1-pentamethylene-semicarbazide with m.p. 157-159°C (from methanol), ;1) 4-/¥-($-<2-methoxy -benzamido>-ethyl)-benzenesulfonyl 7-1,1-hexa-methylene-semicarbazide with m.p. 155-157°C (from methanol), and m) 4-[^-(3-<2-methoxy-benzajnido>- ethyl)-benzenesulfonyl7-l ,1-tetramethylene-semicarbazide with m.p. 172-174°C (from methanol/dimethylformamide), ;from N-/4~-(3-<3-methoxy-benzamido>-ethyl)-benzenesulfonyl7-methylurethane (m.p. 173-175°C) you get ;n ) 4-/4"-(3-<<>3_methoxy-benzamido<>->ethyl)-benzenesulfonyl7-1,1-penta--methylene-semicarbazide with m.p. 230-232°C (under decomposition) of methanol- dimethylformamide and ;o) 4-/4~-(O-<3-methoxy-benzamido>-ethyl)-benzenesulfonyl7-1, 1-hexa-methylene-semicarbazide with mp 207-209°C (under decomposition) (of methanol/dimethylformamide), ;from ;N-/4~- (3-<2-allyloxy-benzamido>-ethyl)-benzenesulfonyl7-methylurethane (m.p. 145-148°C) one obtains ;p) 4-/T- (8-<2-allyloxy-benzamido>-ethyl)-benzenesulfonyl7-1,1-pentamethylene-semicarbazide with m.p. 157-159°C (from methanol), ;of ;N-/4-(B-<2-methoxy- 5-methyl-benzamido>-ethyl)-benzenesulfonyl-7-methylurethane (m.p. 175-177°C) gives ;q) 4-[¥-(B-<2-methoxy-5-methyl-benzamido>-ethyl)- benzenesulfonyl7-l,l-pentamethylene-semicarbazide with m.p. 176-178°C (under decomposition) ;(of methanol), ;of ;N-/¥-(B-<<>0-phenyl-propionamido<>-> ethyl)-benzenesulfonyl.7-methylurethane; (m.p. 137-139°C) one obtains ;r) 4-(B-<<>3-phenyl-propionamido<>->ethyl)-benzenesulfonyl 7-1,1-pentamethylene-semicarbazide with m.p. 173~175°C (under decomposition) (of methanol), from ;N-/¥-(3-<3-trifluoromethyl-benzamido>-ethyl)-benzenesulfonyl7-methylurethane (m.p. 178-180°C) one obtains ; s) 4-[4~-($-<3-trifluoromethyl-benzamido>-ethyl)-benzenesulfonyl 7-1,1-pentamethylene-semicarbazide with m.p. 209-211°C (under decomposition) (of methanol-dimethylformamide) and ;t) 4-[¥-(3-<3-trifluoromethyl-benzamido>-ethyl)-benzenesulfonyl 7-1,1-hexamethylene-semicarbazide with m.p. 201-202°C (from methanol-dimethylformamide), ;from ;N-/4~-(8-<3-methoxythiophene-2-carbonamido>-ethyl)-benzenesulfonyl7-methylurethane (m.p. 226-228 °C) (during cleavage) u) 4-_/ 4-(0-<3-methoxythiophene-2-carbonamide>-ethyl)-benzenesulfonyl7-1,1-<p>entamethylene-semicarbazide is obtained with m.p. 202-204°C (from methanol/dimethylformamide) and ;v) 4-_/ 4-(g-<3-methoxy-thiophene-2-carbonamido>-ethyl)-benzenesulfonyl7-1,1-hexamethylene-semicarbazide with m.p. . l8l-l82°C (from methanol/dimethylformamide), ;from ;N-_/ 4-( g-<f enoxyacetamido>-ethyl)-benzenesulfonyl7-methylurethane ; (m.p. 136-138°C) one obtains ;w) 4-/_ 4-( g -<phenoxyacetamido>-ethyl)-benzenesulfonyl l-1,1-pentamethylene-semicarbazide with m.p. 150-151°C (from methanol), ;x) 4-_/ 4-(g-<phenoxyacetamido>-ethyl)-benzenesulfonyl/-1,1-hexa-methylene-semicarbazide with m.p. 111-113°C (from methanol) and y) 4-/ 4-(g-<phenoxyacetamido>-ethyl)-benzenesulfonyl/-1,1-(3-methyl-pentamethylene)-semicarbazide with m.p. 153-155°C (of methanol), ;of ;N-/_ 4-(g-<g-phen<y>l<p>ro<p>ionamido>-et<y>l)-benzenesulfon<y >l/-methylurethane; (m.p. 142-144°C) one obtains;z) 4-/~4-(g-<g-phenylpropionamido>-ethyl)-benzenesulfonyl7-1,1-hexamethylenesemicarbazide with m.p. l48-150°C (from methanol), ;aa) 4-/~4-(g-<g-phenylpropionamido>-ethyl)-benzenesulfonyl7-1,1-tetramethylenesemicarbazide with m.p. 167-168°C (from methanol), ;ab) 4-£~ 4-(g-<g-phenylpropionamido>-ethyl)-benzenesulfonyl 7-1-methyl-1-benzyl-semicarbazide with m.p. 158-160°C (from methanol) and ac) 4-£" k-(g-<g-phenylpropionamido>-ethyl)-benzenesulfony17-1,1-(3-methylpentamethylene)-semicarbazide with m.p. 180-182° C (from methanol), ;from ;N-_/ 4-(g-<cinnamoylamido>-ethyl)-benzenesulfonyl7-methylurethane (m.p. 198-200°C) you get ;ad) 4-/~~4- (g-<cinnamoylamido>ethyl)-benzenesulfony 1/-1 ,1-(3-methyl-pentamethylene)-semicarbazide with m.p. 198-200°C (from methanol/dimethylformamide), ;of ;N-/_ 4 -(g-<A^-tetrahydrobenzamido>-ethyl)-benzenesulfonyl/methylurethane; (m.p. 151-153°C) one obtains ae) 4-_/ 4-(g-<A^-tetrahydrobenzamido>-ethyl)- benzenesulfonyl/-1,1-hexamethylenesemicarbazide with m.p. 170-171°C (decomposition) (of methanol) ;and ;af) 4-/~~4-( 3-<A^-tetrahydrobenzamido>-ethyl)-benzenesulfonyl7- 1,1-(3-methylpentamethylene)-semicarbazide with m.p. 184-186°C (decomposition) ;(of methanol), ;of ;N-/<->4-(3-<3-trifluoromethylbenzamido>-ethyl) -benzenesulfonyl7-methylurethane (m.p. 178-180°C) gives nan;ag) 4-/~4-( 3-<3_trifluoromethylbenzamido>-ethyl)-benzenesulfony 1/-1,1-(3-methylpentamethylene)- semicarbazide with m.p. 222-224°C (from methanol/dimethylformamide), ;of ;N-_/— 4-(3_<3-fluorobenzamido>-ethyl)-benzenesulfonyl7-methylurethane ;(m.p. l84-l86°C) one obtains ;ah) 4-[4-(3-<3-fluorobenzamido>-ethyl)-benzenesulfonyl-17-1,1-pentamethylene-semicarbazide with m.p. 210-212°C (decomposition) (of methanol/dimethylformamide), ;ai) 4-/~4-(3~<3-fluorobenzamido>-ethyl)-benzenesulfonyl7-151-hexa-methylene-semicarbazide with m.p. . 198-200°C (from methanol) and ak) 4-/~4-( 3~<3-fluorobenzamido>-ethyl)-benzenesulfonyl7-1,1-tetra-methylene-semicarbazide with m.p. 200-202°C (from methanol/dimethylformamide), from ;N-/~4-(3-<3-chlorobenzamido>-ethyl)-benzenesulfonyl/-methylurethane (m.p. 173-175°C) you get ;al) 4-_/—4-(3-<3-chlorobenzamido>-ethyl)-benzenesulfonyl7-1,1-(1-methyl-pentamethylene)-semicarbazide with m.p. 210-211°C (from methanol/dimethylformamide) and ;am) 4-J/-4-(3-<3_chlorobenzamido>-ethyl)-benzenesulfonyl/-1-methyl-1-isopropyl-semicarbazide with m.p. 176-177°C (from methanol/dimethylformamide), ;from ;N-/~4-(3-<4-fluorobenzamido>-ethyl)-benzenesulfonyl7-methylurethane (m.p. 194-196°C) you get ;an) 4-[4-(3-<4-Fluorobenzamido-ethyl)-benzenesulfonyl]-1,1-(3-methylpentamethylene)-semicarbazide with m.p. 215-217°C (decomposition) (of methanol/dimethylformamide), ;of ;N-/~4-(3-capronamido-ethyl)-benzenesulfonyl/-methylurethane (m.p. . methanol), ;from ;N-/-4-(g-<3-ethoxythiophene-2-carbonamido>-ethyl)-benzenesulfonyl-7-methylurethane (m.p. l63-165°C) one obtains ;ap) 4-/~"4- (g-<3-ethoxythiophene-2-carbonamido>-ethyl)-benzenesulfonyl 7-1,1-pentamethylene-semicarbazide with m.p. 159-161°C (from methanol) and aq) 4-_/ 4-(g-<3-ethoxythiophene-2-carbonamido>-ethyl)-benzenesulfonyl 7-1,1-hexamethylene-semicarbazide with m.p. 152-163°C (from methanol), ;from ;N-/_ 4-(3-<3-methoxybenzamido>-ethyl)-benzenesulfonyl-7-methylurethane (m.p. 173-175°C) one obtains ;ar) 4- _/ 4-( g -<3-methoxybenzamido>-ethyl)-benzenesulfonyl 7-1 ,1 -(3-methylpentamethylene)-semicarbazide with m.p. 237-239°C (dec) (of methanol/dimethylformamide), ;of ;N-_/ 4-(g-<2-ethoxybenzamido>-ethyl)-benzenesulfonyl/-methylurethane (m.p. 172-174°C) one obtains ;as) 4-(g-<2-ethoxybenzamido>-ethyl)-benzenesulfonyl/-1,1-pentamethylene-semicarbazide with m.p. 153-154°C (from methanol), ;at) 4-/_ 4-(g-<2-ethoxybenzamido>-ethyl)-benzenesulfonyl/-1,1-hexamethylene-semicarbazide with m.p. 135-137°C (from methanol) and au) 4-/ 4-(g-<2-ethoxybenzamido>-ethyl)-benzenesulfonyl/-1,1-(1-methylpentamethylene)-semicarbazide with m.p. 137-139°C (from methanol), from ;N-_/ 4-(g-<2-propoxybenzamido>-ethyl)-benzenesulfonyl l/-methyluret an (m.p. 159-161°C) you get ; of) k-/_ 4-( g -<2-propoxybenzamido>-ethyl)benzenesulfonyl/-1,1-(3-methylpentamethylene)-semicarbazide with m.p. 171-173°C (from methanol/dimethylformamide), ;of ;N-/<->4-(g-<2-methoxy-5-chlorobenzamido>-ethyl)-benzenesulfonyl7-methylurethane (m.p. 189-192°C ) one obtains ;aw) 4-/^—4- ( g-<2-methoxy-5-chlorobenzamido>-ethyl)-benzenesulfonyl/- 1,1-pentamethylene-semicarbazide with m.p. l64-l66°C (of methanol) and ax) 4-_/ 4-( g -<2-methoxy-5-chlorobenzamido>-ethyl)-benzenesulfonyl7-1,1-hexamethylene-semicarbazide with m.p. l6l-l63°C (from methanol), ;from ;Nt A~4-(g-<2-methoxy-4-chlorobenzamido >-ethyl)-benzdlsulfonyl7-methylurethane (m.p. 178-l80°C) one obtains ay) 4-[4-( g -<2-methoxy-4-chlorobenzamido>-ethyl)-benzenesulfonyl 17-1,1-(3-methylpentamethylene)-semicarbazide with m.p. 177-179°G (from methanol), ;from ;N-/~4-(g-< 2-methoxy-3_chlorobenzamido>-ethyl)-benzenesulfonyl/-methylurethane (m.p. 151-153°C) you get ;az ) 4-_/—4-(g-<2-Methoxy-3-chlorobHnzamido>-ethyl)-benzenesulfonyl 17-1,1-pentamethylene-semicarbazide with m.p. 173-175°C (from methanol), ;of ;N-/~4-( g-< 3-et oxybenzamido-ethyl)-benzenesulfonyl l/-methyl lur et an ;(m.p. 165-167°C) one gets ;ba) 4-/~4-(g-<3-ethoxybenzamido>-ethyl)-benzenesulfonyl 7-1,1-pentamethylene-semicarbazide with m.p. 207-20$°C (dec) (of methanol/dimethylformamide), ;bb) 4-/-4-(g-<3-ethoxybenzamido>-ethyl)-benzenesulfonyl 7-1,1-hexa-methylene-semicarbazide with m.p. . 177-179°C (from methanol/dimethylformamide) and ;bc) 4-/~4-(g-<3-ethoxybenzamido>-ethyl)-benzenesulfonyl7-1,1-(3-methylpentamethylene)-semicarbazide with m.p. 224-226°C (decomposition) ;(from methanol/dimethylformamide), ;from ;N-_/~4-(g-<2-methoxy-5-methylbenzamido>-ethyl)-benzenesulfonyl 17-methylurethane (m.p. 175-177°C) one obtains ;bd) 4-[4-(g-<2-methoxy-5-methylbenzamido>-ethyl)-benzenesulfonyl/-1,1-hexamethylenesemicarbazide with m.p. 155-157°C (from methanol) and be) 4-/.—4-(g-<2-methoxy-5-methylbenzamido>-ethyl)-benzenesulfonyl /1,1-(3-methylpentamethylene)-semicarbazide with m.p. 176-178°C (from methanol), of ;N-/<->4-(g<-><2-g<->methoxyethoxy-benzamido<>->ethyl)-benzenesulfonyl7-methylurethane (m.p. 123- 125°C) one obtains ;bf) 4-/~" 4-(g-<2-g-methoxyethoxybenzamido>-ethyl)-benzenesulfonyl 7-1,1-pentamethylene-semicarbazide (of m.p. 143-145°C) ( of methanol) and bg) 4-/ 4-(g-<2-g-methoxyethoxybenzamido>-ethyl)-benzenesulfonyl 7-1,1-(3_methylpentamethylene)-semicarbazide with mp 157-159°C (from methanol), of ;N-_/ 4-( g-<2-ethoxy-5_chlorobenzamide6>-ethyl)-benzenesulfonyl/-methyl lur et an (m.p. 203-205°C) one obtains ;bh) 4-/~ 4- (g-<2-ethoxy-5-chlorobenzamido>-ethyl)-benzenesulfonyl 7-1,1-pentamethylene-semicarbazide with m.p. 163-165°C. (from methanol) and ;bi) 4-/-4-(g -<2-ethoxy-5_chlorobenzamido>-ethyl)-benzenesulfonyl7-1,1-hexamethylene-semicarbazide with m.p. 164-166°C (from methanol), ;of ;N-/<->4-(g-<2 -methoxy-3-methylbenzamido>-ethyl)-benzenesulfonyl7-methylurethane (m.p. 153-155°C) gives a ;bk) 4-/—4-(g-<2-methoxy-3-methylbenzamido>-ethyl)- benzenesulfonyl 7-1,1-(3-methylpentamethylene)-semicarbazide with m.p. 170-172°C (from methanol l), of ;N-_/ 4-(O-<2-g-methoxyethoxy-5-methylbenzamido>-ethyl)-benzenesulfonyl7-methylurethane (m.p. 160-162°C) one obtains ;bl) 4-_/ 4-( g-<2-0-methoxyethoxy-5_methylbenzamido>-ethyl)-benzenesulfonyl/-1,1-(3-methylpentamethylene)-semicarbazide with .m.p. . 151-153°C ;(from methanol), ;from ;N-/ 4-(g-<3~chlorophenoxyacetamido>-ethyl)-benzenesulfonyl/-methylurethane ;(m.p. 121-123°C) you get bm) 4 -/ 4-(g-<3-chlorophenoxyacetamido>-ethyl)-benzenesulfonyl 7-1,1-(3-methylpentamethylene)-semicarbazide with m.p. 106-108°C (decomposition) ;(of methanol), ;of ;N-_/ 4-( g-<g-4-chlorophenylpropionamido>-ethyl)-benzenesulfonyl7-methyl- ;urethane (m.p. 165-167° C) one obtains ;bn) 4-/~4-(g-<g-4-chlorophenylpropionamido-ethyl)-benzenesulfonyl7-1,1-pentamethylene-semicarbazide with m.p. 179-181°C (decomposition) (of methanol) and ;bo) 4-_/ 4-(g-<g-4-chlorophenylpropionamido>-ethyl)-benzenesulfonyl/- 1,1-(3_methylpentamethylene)-semicarbazide with m.p. . l63-l65°C (from methanol), from ;N-/_ 4-(g-<g-3~chlorophenylpropionamido>-ethyl)-benzenesulfonyl7-methyl- ;urethane (m.p. 128-130°C) one gets ; bp) -4-_/ 4-(g-<g-3-chlorophenylpropionamido>-ethyl)-benzenesulfonyl/- 1,1-hexamethylene-semicarbazide with m.p. l6l-l63°C (from methanol) and bq) 4-_/—4-(g-<g-3-chlorophenylpropionamido>-ethyl)-benzenesulfonyl7-1,1-(3-methylpentamethylene)-semicarbazide with m.p. 137-139°C (from methanol), of ;N-_/ 4-(g-<3,4-tetramethylenethiophene-2-carbonamido>-ethyl)-benzenesulfonyl/- methylurethane (m.p. 194-196°C) gives man ;br) 4-/-4-(g-<3,4-tetramethylenethiophene-2-carbonamido>-ethyl)-benzenesulfonyl/-1,1-pentamethylene-semicarbazide with m.p. 149-151°C (from ;methanol/dimethylformamide) and ;bs) 4-/ 4-(g-<3,4-tetramethylenethiophene-2-carbonamido>-ethyl)-benzenesulfonyl 7-1,1-(3-methylpentamethylene) -semicarbazide with m.p. 168-169°C ;(of methanol), ;of ;N-/<->4-(g-<2-methoxy-3,5-dichlorobenzamido>-ethyl)-benzenesulfonyl/~ure<y>l-methane (m.p. 187-188°C) one obtains ;bt) 4-/~4-(g-<2-methoxy-3,5-dichlorobenzamido>-ethyl)-benzenesulfonyl7-1,1-(3-methylpentamethylene)- semicarbazide with m.p. 161-163°C (from methanol/dimethylformamide), ;of ;N-_/ 4-(g-<2-methoxy-benzamido>-ethyl)-benzenesulfonyl7-ethyl luret an ;(m.p. 168°C) gets man bu) 4-/~4-(g-<2-methoxybenzamido>-ethyl)-benzenesulfonyl 7-(γ-dimethyl-pentamethylene)-semicarbazide, m.p. 155-157°C, ;bv) 4-_/—4-( O-<2-methoxybenzamido>-ethyl)-benzenesulfonyl7-(1-isonor-ganatanyl)-nitrogen, m.p. 170-171°C, ;bw) 4-_/ 4-(g-<2-methoxybenzamido>-ethyl)-benzenesulfonyl 7-1,1-(2,6-dimethylpentamethylene)-semicarbazide, m.p. 203-204°C, ;bx) 4-/-4-(g-<2-methoxybenzamido>-ethyl)-benzenesulfony17-1,1-(g-pentamethylene)-semicarbazide m.p. 175"176°C, ;by) N1~4-_/ 4-(g-<2-methoxybenzamido>-ethyl)-benzenesulfonyl7-N2-_/_norgranatyl-(9_).7-urea, m.p. 190-191 °C, ;bz) N1~4-_/ 4-( g-<2-methoxybenzamido>-ethyl)-benzenesulfonyl7-N2~ /<->nortropanyl-(827-urea, mp 213-2l4°C, ; ca) N1-4-/~4-(g-<2-methoxybenzamido>-ethyl)-benzenesulfonyl7-N2~;(lj2,5,6-tetrahydropyridyl-1)-urea, m.p. 156-157°C; Example 2. ;4- /~ 4-(g-benzamido-ethyl)-benzenesulfony j. 7-1,1-pentamethylene-semicarbazide. a) 14.7 g of 4,4-diphenyl-1,1-pentamethylene-semicarbazide is suspended with 16.3 g of the sodium salt of 4-(g-benzamido-ethyl)-benzenesulfonamide in 100 ml of dimethylformamide and heated for three hours at 100° C. Dilute after cooling with water, make the reaction mixture alkaline with ammonia and remove formed diphenylamine by shaking three times with ether. The aqueous phase is filtered and acidified with glacial acetic acid. The 4-/~4-(g-benzamido-ethyl)-benzenesulfony17-1,1-pentamethylene-semicarbazide formed in crystalline form melts after recrystallization from dimethylformamide/water at 217-218°C. ;In an analogous manner, one obtains: b) 4-/"4-(O-benzamido-ethyl)-benzenesulfonyl 7-1,1-hexamethylenesemicarbazide with m.p. 233-236°C (from dimethylformamide/water). ;Example 3. ; 4-/~ 4-(g-benzamido-ethyl)-benzenesulfonyl7-1,1-pentamethylene-semicarbazide. ;a) 5)9 g of 1-pentamethyleneimino-parabanic acid are suspended in 240 ml of benzene. After the addition of 3 g of trimethylamine, the mixture in solution and mixed with stirring with 9>7 g of 4-(g-benzamido-ethyl)-benzenesulf ochloride. After boiling for 3 hours under reflux, it is allowed to cool and decant from the tough residue. This is digested to remove triethylamine hydrochloride formed with water and brought to crystallization by trituration with alcohol/water. The 4-/-4-(g<->benzamido-ethyl)-benzenesulfonyl-7-3-pentamethylene-iminoparabanic acid thus formed is purified by boiling with methanol and melts at 228°C during cleavage. ;b) 0.5 g of the parabanic acid derivative formed above is heated with 5 ml of sodium hydroxide solution for 10 minutes on a steam bath. After a short time, the salt of 4-/~ crystallizes 4-(g-benzamido-ethyl)-benzenesulfonyl/- 1,1-pentamethylene-semicarbazide out. -When acidified with dilute acetic acid, the free compound with m.p. 2l8°C. Example 4. 4-(g-4-chloro-benzamido-ethyl)-benzenesulfonyl-7-1,1-pentamethylene-semicarbazide. ;9») g of N-_/7T-(g-4-chloro-benzamido-ethyl)-benzenesulfonyl7-urea (m.p. 194-196°C) is heated in 100 ml of dioxane with 5 g of N-aminopiperidine under reflux to cooking. After the formation of a clear solution, solvents are evaporated under reduced pressure, the residue is treated with approx. 1% ammonia, filter and acidify the filtrate with dilute acetic acid. The precipitated 4-[4-(g-4-chloro-benzamido-ethyl)-benzenesulfonyl/-1,1-pentamethylene-semicarbazide is recrystallized from water-dimethylformamide and melts at 220-223°C; with decomposition. ;Example 5- ;4-/ 4-(g-$3-methyl-4-chloro-benzamido>-ethyl)-benzenesulfonyl 7-1,1-pentamethylene- semicarbazide.. a) 16.8 g 4-(g-< 3-Methyl-4-chloro-benzamido>-ethyl)-benzene-sulfonamide-sodium is heated with 11.1 g of 1,1,5,5-bis-pentamethylene carbohydrazide (m.p. 178°C) in a preheated oil bath in 10-15 min. ;at 180 C. The mixture becomes mushy and then solidifies againT;After cooling, it is treated with water, filtered, the filtrate acidified with acetic acid and the reaction product recrystallized from methanol. 4-[4-(3-<3-methyl-4-chloro-benzamido>-ethyl)-benzenesulfonyl<7>-1,1-pentamethylene-semicarbazide melts at 204-206°C. ;B) 4-[4-(3-< 3-methyl-4-chloro-benzamido>-ethyl)-benzenesulfonyl 17-1jl-tetramethylene-semicarbazide with m.p. 174-176°C (of methanol/water); and of 4-(3-<α-methoxy-phenylacetamido>-ethyl)-benzenesulfonamide (m.p. 167-169°C) and 1,1,5,5-bis -pentamethylene carbohydrazide is obtained c) 4-/~4-(3-<ot-methoxy-phenyl lacetamido>-ethyl)-benzenesulfonyl7-1,1-pentamethylene-semicarbazide with m.p. 146-148°C. ;Example 6. ;a)-4-[-4-(3-benzamidoethyl)-benzenesulfonyl-7-1,1-(Y-methyl-pentamethylene)-semicarbazide. ;0.01 mol of N-_/ 4-(3-benzamidoethyl)-benzenesulfonyl-7-methylurethane is heated in 135 ml of toluene with 0.01 mol of 1,1-y-methyl-pentamethylene-hydrazine while stirring at 110-120°C. The methyl alcohol formed is distilled off. After 2-3 hours of heating, it is allowed to cool and sucked off. The residue is reprecipitated from Na^O^/HCl. The formed k-/_ 4-(3-benzamidoethyl)-benzenesulfonyl/-1,1-(γ-methylpentamethylene)-semicarbazide melts at 212°C. ;In an analogous manner, one obtains: ;b) 4-[p-(3-benzamidoethyl)-benzenesulfonyl 7-1-methyl-1-isopropyl-semicarbazide, m.p. 204°C, c) 4-[p-(3-benzamidoethyl)-benzenesulfonyl-7-1,1-(y-methoxy-pentamethylene)-semicarbazide, m.p. 212°C, d) 4-[p-(3-benzamidoethyl)-benzenesulfonyl-7-1,1-(Y-isopropoxy-pentamethylene)-semicarbazide, m.p. 210°C, e) N-L-/-p-(3-benzamidoethyl)-benzenesulfonyl7-N2-/._norgranatanyl-( 9^7-urea, m.p. 229-230°C, f) 4-/~4- (3-acetamidoethyl)-benzenesulfonyl 7-1,1-pentamethylene-semicarbazide, m.p. 203°C, g) 4-/-4-(3-acetamidoethyl)-benzenesulfony 1^7-1 ,1-(γ-methyl-pentamethylene)-semicarbazide, m.p. 187-189°C. ;Example 7 ;4-/~ 4-(3-benzamidoethyl)-benzenesulfonyl 7-1,1-pentamethylene-semicarbazide. ;0.013 mol 4-/~4-(3-aminoethyl)-benzenesulfonyl7-1,1-pentamethylene-semicarbazide (prepared by saponification of 4-/~"4-(3-acetyl-aminoethyl)-benzenesulfonyl7-1,1- pentamethylene semicarbazide, mp 198-199°C, is heated in 15 ml of chloroform with 0.024 ml of pyridine and 0.013 ml of benzoyl chloride for 6 hours at 35°C. The residue is sucked off and re-precipitated from Na^O^/HCl. The compound melts at 216-218° C. Example 8. a) 4-/_ 4-(3-2-Methoxybenzamidoethyl)-benzenesulfonyl-7-1,1-pentamethylene-semicarbazide.; 0.01 mol 4-/~4-(3- aminoethyl)-benzenesulfonyl7-1,1-pentamethylene-semicarbazide is dissolved in 0.01 mol 2-n NaOH and mixed dropwise with stirring with 0.01 mol 2-methoxybenzoyl chloride. For complete reaction, heat for two hours at 40°C. The precipitated substance is suctioned off and the residue is reprecipitated from Na2C0^/HCl. The substance melts at 156° C. ;B) 4-/-4-(3-trimethylacetamidoethyl)-benzenesulfonyl-7-pentamethylene-semicarbazide, m.p. 187-189°C, c) 4-(4-(3-3'-toluylamidoethyl)-benzenesulfonyl 7-1,1-(Y-methylpent α-methylene)-semicarbazide, m.p. 234-1235°C, d) 4-[4-(3-3'-chlorobenzamidoethyl)-benzenesulfonyl-7-1,1-(Y-methyl-pentamethylene)-semicarbazide, m.p. 223-224°C, Example" 9 a) 4-[4-(3-2-methoxybenzamidoethyl)-benzenesulfonyl-7-1,1-(Y-methyl-pentamethylene)-semicarbazide. 0.01 mol 4-_/ -4-(3-aminoethyl)-benzenesulfony 7-1,1-(γ-methyl-pentamethylene)-semicarbazide, mp 187-189°C (prepared by saponification of 4-_/ 4-(3-acetylaminoethyl)-benzenesulf onyl7-1,1-(Y_methyl-pentamethylene)-semicarbazide) is dissolved in 10 ml of pyridine and 0.01 mol of 2-methoxybenzoyl chloride is added dropwise. During heating, a reaction occurs. It is allowed to stand for 12 hours and then heated for 30 minutes on steam bath. After cooling, it is poured onto ice and the precipitate is suctioned off and re-precipitated from Na2C03/HCl. The pure substance melts at 164°C. ;In an analogous way one obtains: ;b) 4-/_ 4-(3- 5'-chloro-2'-methoxybenzamidoethyl)-benzenesulfonyl7-1,1-(Y-methylpentamethylene)-semicarbazide, mp 165-168°C, c ) 4-_/—4-(3-3'-methoxythiophene -2-carbamidoethyl)-benzenesulfonyl7-1,1-(Y-methylpentamethylene)-semicarbazide, m.p. 174-177°C, d) 4-_/ 4-(3-21-ethoxybenzamidoethyl)-benzenesulfonyl7-1, 1-(Y-methyl-pentamethylene)-semi carbazide, m.p. l69-171°C, e) 4-(4-(3-2'-methoxybenzamidoethyl)-benzenesulfonyl7-1,1-YY~ethyl-pentamethylene)-semicarbazide, m.p. 160°C, sintering 166°C. ;Example 10.;*~ L 4-(3-<2-Methoxy-benzamido>-ethyl)-benzenesulfonyl7-1,1-penta-methylenesemicarbazide. a) Hj7 g N-[4-(3-<2-methoxy-benzamido>-ethyl)-benzenesulfonyl7-N'-phenyl-thiourea,
5 g N-amino-piperidin og 5 g of N-amino-piperidine and
200 ml dioksan 200 ml of dioxane
oppvarmes i 1 time under tilbakeløp i kokning. Under nedsatt trykk avdestilleres oppløsningsmidlet og residuet gjenutfelles to ganger av 0j5#-ig vandig ammoniakk og fortynnet eddiksyre. heat for 1 hour at reflux. Under reduced pressure, the solvent is distilled off and the residue is reprecipitated twice with 0.5% aqueous ammonia and dilute acetic acid.
Det i godt utbytte dannede produkt omkrystalliseres fra metanol og smelter véd l60-l62°C under spaltning. The product formed in good yield is recrystallized from methanol and melts at 160-162°C during decomposition.
b) 2 g 4-/~4-($-<2-metoksy-benzamido>-etyl)-benzolsulfonyl7-l,l-pentametylen-tiosemikarbazid bringes i oppløsning i b) 2 g of 4-[4-($-<2-methoxy-benzamido>-ethyl)-benzenesulfonyl-7-1,1-pentamethylenethiosemicarbazide are dissolved in
100 ml 0,5-n natronlut på dampbad. 5 g H202 (30^-ig) tilsettes, deretter oppvarmes i 3 min. på dampbad. Den noe uklare oppløsning hensettes i 10 min. og avkjøles til værelsetemperatur. Deretter surgjør man med fortynnet eddiksyre og frasuger etter noen minutter den krystallinske utfelling. 100 ml 0.5-n caustic soda in a steam bath. 5 g of H 2 O 2 (30^-ig) are added, then heated for 3 min. in a steam bath. The somewhat cloudy solution is allowed to stand for 10 min. and cooled to room temperature. It is then acidified with diluted acetic acid and after a few minutes the crystalline precipitate is suctioned off.
Under anvendelse av kull gjenutfelles det dannede 4-/~ 4-(g-<2-metoksy-benzamido>-etyl)-benzolsulfony17-1,1-pentametylen-semikarbazid fra 0,5%-ig vandig ammoniakk og fortynnet eddiksyre. Omkrystallisert fra metanol smelter produktet ved 157_159°C. Using charcoal, the formed 4-/~ 4-(g-<2-methoxy-benzamido>-ethyl)-benzenesulfonyl 17-1,1-pentamethylene-semicarbazide is reprecipitated from 0.5% aqueous ammonia and dilute acetic acid. Recrystallized from methanol, the product melts at 157-159°C.
Eksempel 11. Example 11.
4-/—<4>-(g-<2-metoks<y->5-klor-benzamido>-et<y>l)-benzolsulfon<y>17-1, 1-pentametylen- semikarbazid.. 4-/—<4>-(g-<2-methoxy<y>5-chloro-benzamido>-et<y>l)-benzenesulfone<y>17-1, 1-pentamethylene-semicarbazide..
7,15 g (0,05 mol) 1,1-pentametyiensemikarbazid oppløses 7.15 g (0.05 mol) of 1,1-pentamethylene semicarbazide is dissolved
i 150 ml abs. benzol. 2,4 g av en 505?-ig olje-suspensjon NaH tilsettes. Deretter oppvarmes i 2 timer under omrøring til kokning. Etter avkjøling tilsetter man langsomt under god omrøring en suspensjon av 9j4 g 4-(8-<<>5-klor-2-metoksy-benzamido>-etyl)-benzolsulfon-klorid i 250 ml abs. benzol og omrører i 3 timer ved koketemperatur. Etter avkjøling blander man med vann og adskiller. Man trekker ut benzoloppløsningen to ganger med fortynnet (o,5-n) NaOH. De forenede alkaliske oppløsninger filtreres og surgjøres. Den dannede utfelling suges fra, oppløses i fortynnet NH^ og utfelles igjen med iseddik. Etter frasugning vaskes det med vann, utrives med CH-jOH, frasuges in 150 ml abs. benzene. 2.4 g of a 505 µg oil suspension of NaH are added. Then heat for 2 hours while stirring until boiling. After cooling, a suspension of 9j4 g of 4-(8-<<>5-chloro-2-methoxy-benzamido>-ethyl)-benzenesulfone chloride in 250 ml abs. benzene and stir for 3 hours at boiling temperature. After cooling, mix with water and separate. The benzene solution is extracted twice with diluted (o.5-n) NaOH. The combined alkaline solutions are filtered and acidified. The formed precipitate is sucked off, dissolved in dilute NH^ and precipitated again with glacial acetic acid. After extraction, it is washed with water, triturated with CH-iOH, and extracted
og tørkes. Etter omkrystallisering fra metanol smelter stoffet ved 167-168°C. and dried. After recrystallization from methanol, the substance melts at 167-168°C.
På analog måte lar det seg fremstille 4-/~4-(3-benz-amidoetyl)-benzolsulfonyl/-l,1-pentametylensemikarbazid. In an analogous manner, it is possible to prepare 4-[4-(3-benz-amidoethyl)-benzenesulfonyl]-1,1-pentamethylenesemicarbazide.
Smp. 224-225°C Temp. 224-225°C
Hvis man går ut fra 1,1-heksametylensemikarbazid får man videre 4-/—4-(B-<2-metoksy-5_klor-benzamido>-etyl)-benzolsulfonyl7-l,l-heksametylensemikarbazid av smp. l62-l64°C og 4-/—4-( 3-benzamido-etyl_)7-benzolsulf onyl semikarbazid med smp. If one starts from 1,1-hexamethylenesemicarbazide, one further obtains 4-(B-<2-methoxy-5_chloro-benzamido>-ethyl)-benzenesulfonyl7-1,1-hexamethylenesemicarbazide of m.p. 162-164°C and 4-(3-benzamidoethyl)7-benzenesulfonyl semicarbazide with m.p.
233-235°C 233-235°C
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19813123535 DE3123535A1 (en) | 1981-06-13 | 1981-06-13 | METHOD FOR HYDROGENATING COAL, HEAVY OIL, BITUMEN AND THE LIKE. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO821844L NO821844L (en) | 1982-12-14 |
| NO162864B true NO162864B (en) | 1989-11-20 |
| NO162864C NO162864C (en) | 1990-02-28 |
Family
ID=6134663
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO821844A NO162864C (en) | 1981-06-13 | 1982-06-03 | PROCEDURE FOR HYDROGENATION OF COAL, LONG OIL, BITUMEN AND LIKE. |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0068231B1 (en) |
| CA (1) | CA1171013A (en) |
| DE (2) | DE3123535A1 (en) |
| NO (1) | NO162864C (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3914057A1 (en) * | 1989-04-28 | 1990-10-31 | Ruhrkohle Ag | STRIPING OF RESIDUES |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB892113A (en) * | 1957-05-08 | 1962-03-21 | Apv Co Ltd | Separation of low boiling point impurities from hydrocarbons |
| GB1527570A (en) * | 1976-12-15 | 1978-10-04 | Texaco Development Corp | Coal liquefaction |
-
1981
- 1981-06-13 DE DE19813123535 patent/DE3123535A1/en not_active Withdrawn
-
1982
- 1982-06-03 NO NO821844A patent/NO162864C/en unknown
- 1982-06-11 DE DE8282105119T patent/DE3276003D1/en not_active Expired
- 1982-06-11 CA CA000405046A patent/CA1171013A/en not_active Expired
- 1982-06-11 EP EP82105119A patent/EP0068231B1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3123535A1 (en) | 1982-12-30 |
| EP0068231A3 (en) | 1984-09-12 |
| EP0068231A2 (en) | 1983-01-05 |
| NO162864C (en) | 1990-02-28 |
| NO821844L (en) | 1982-12-14 |
| EP0068231B1 (en) | 1987-04-08 |
| CA1171013A (en) | 1984-07-17 |
| DE3276003D1 (en) | 1987-05-14 |
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