CH427794A - Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden - Google Patents

Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden

Info

Publication number: CH427794A
Authority: CH; Switzerland
Prior art keywords: benzenesulfonyl; methyl; pentamethylene; formula; semicarbazide
Prior art date: 1961-10-05

Application number

CH1164362A

Other languages

German (de)

English (en)

Inventor

Ruschig Heinrich

Aumueller Walter

Korger Gerhard

Haack Erich

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.)

1961-10-05

Filing date

1962-10-03

Publication date

1967-01-15

1962-10-03 Application filed by Hoechst Ag filed Critical Hoechst Ag

1967-01-15 Publication of CH427794A publication Critical patent/CH427794A/de

Links

238000000034 method Methods 0.000 title claims description 17
LSNDGFYQJRXEAR-UHFFFAOYSA-N benzenesulfonamidourea Chemical class NC(=O)NNS(=O)(=O)C1=CC=CC=C1 LSNDGFYQJRXEAR-UHFFFAOYSA-N 0.000 title claims description 6
238000002360 preparation method Methods 0.000 title claims description 6
150000001875 compounds Chemical class 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
239000004202 carbamide Substances 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
-1 alkyl radical Chemical group 0.000 description 32
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 12
239000000047 product Substances 0.000 description 10
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
229910021529 ammonia Inorganic materials 0.000 description 6
239000008280 blood Substances 0.000 description 6
210000004369 blood Anatomy 0.000 description 6
150000008331 benzenesulfonamides Chemical class 0.000 description 5
239000003610 charcoal Substances 0.000 description 5
239000012948 isocyanate Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
235000013877 carbamide Nutrition 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
UAHWWAIVYPJROV-UHFFFAOYSA-N 2,6-dimethylpiperidin-1-amine Chemical compound CC1CCCC(C)N1N UAHWWAIVYPJROV-UHFFFAOYSA-N 0.000 description 2
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 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
150000005840 aryl radicals Chemical class 0.000 description 2
ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical class OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 description 2
238000001816 cooling 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
238000004519 manufacturing process Methods 0.000 description 2
UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
150000003672 ureas Chemical class 0.000 description 2
MPDPQMOPXOQMOO-UHFFFAOYSA-N (2-methylphenyl)sulfonylcarbamic acid Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(O)=O MPDPQMOPXOQMOO-UHFFFAOYSA-N 0.000 description 1
FHTLRVQASCAGSZ-UHFFFAOYSA-N (2-methylphenyl)sulfonylurea Chemical compound CC1=CC=CC=C1S(=O)(=O)NC(N)=O FHTLRVQASCAGSZ-UHFFFAOYSA-N 0.000 description 1
MRACKHRIKKBQSU-UHFFFAOYSA-N (3-ethylphenyl)sulfonylurea Chemical compound C(C)C=1C=C(C=CC1)S(=O)(=O)NC(=O)N MRACKHRIKKBQSU-UHFFFAOYSA-N 0.000 description 1
XALUBUYAUFYTQY-UHFFFAOYSA-N (3-methylphenyl)sulfonylcarbamic acid Chemical compound CC1=CC=CC(S(=O)(=O)NC(O)=O)=C1 XALUBUYAUFYTQY-UHFFFAOYSA-N 0.000 description 1
TYMBLCCPQXGEHE-UHFFFAOYSA-N (3-methylphenyl)sulfonylurea Chemical compound CC1=CC=CC(S(=O)(=O)NC(N)=O)=C1 TYMBLCCPQXGEHE-UHFFFAOYSA-N 0.000 description 1
KWCHZHVQTBXUSJ-UHFFFAOYSA-N (3-propan-2-ylphenyl)sulfonylurea Chemical compound C(C)(C)C=1C=C(C=CC1)S(=O)(=O)NC(=O)N KWCHZHVQTBXUSJ-UHFFFAOYSA-N 0.000 description 1
ASRMWYDEZPXXBA-UHFFFAOYSA-N (sulfonylamino)urea Chemical class NC(=O)NN=S(=O)=O ASRMWYDEZPXXBA-UHFFFAOYSA-N 0.000 description 1
NMBWXBWFDHVLGS-UHFFFAOYSA-N 2-ethylbenzenesulfonamide Chemical compound CCC1=CC=CC=C1S(N)(=O)=O NMBWXBWFDHVLGS-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
YCMLQMDWSXFTIF-UHFFFAOYSA-N 2-methylbenzenesulfonimidic acid Chemical compound CC1=CC=CC=C1S(N)(=O)=O YCMLQMDWSXFTIF-UHFFFAOYSA-N 0.000 description 1
UHHFUGFMQDIJKM-UHFFFAOYSA-N 2-methylpiperidin-1-amine Chemical compound CC1CCCCN1N UHHFUGFMQDIJKM-UHFFFAOYSA-N 0.000 description 1
RWOLPAKHWCBBKC-UHFFFAOYSA-N 3-(2-methylpropyl)benzenesulfonamide Chemical compound CC(C)CC1=CC=CC(S(N)(=O)=O)=C1 RWOLPAKHWCBBKC-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
IDAXFFOLDRMEAO-UHFFFAOYSA-N 3-ethylbenzenesulfonamide Chemical compound CCC1=CC=CC(S(N)(=O)=O)=C1 IDAXFFOLDRMEAO-UHFFFAOYSA-N 0.000 description 1
NVZINPVISUVPHW-UHFFFAOYSA-N 3-methylbenzenesulfonamide Chemical compound CC1=CC=CC(S(N)(=O)=O)=C1 NVZINPVISUVPHW-UHFFFAOYSA-N 0.000 description 1
BNWXZHIYRPWHDT-UHFFFAOYSA-N 3-propan-2-ylbenzenesulfonamide Chemical compound CC(C)C1=CC=CC(S(N)(=O)=O)=C1 BNWXZHIYRPWHDT-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-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
MXWBOVVYTCHHJB-UHFFFAOYSA-N CC1=C(C=CC=C1)S(=O)(=O)NC(=O)NC(C)=O Chemical compound CC1=C(C=CC=C1)S(=O)(=O)NC(=O)NC(C)=O MXWBOVVYTCHHJB-UHFFFAOYSA-N 0.000 description 1
HZBPFJOYUOCDSE-UHFFFAOYSA-N CC1=CC=CC(S(N(C)C(O)=O)(=O)=O)=C1 Chemical compound CC1=CC=CC(S(N(C)C(O)=O)(=O)=O)=C1 HZBPFJOYUOCDSE-UHFFFAOYSA-N 0.000 description 1
XEXMQGBWQVABFC-UHFFFAOYSA-N CCC1=CC=CC=C1S(=O)(=O)NC(=O)N Chemical compound CCC1=CC=CC=C1S(=O)(=O)NC(=O)N XEXMQGBWQVABFC-UHFFFAOYSA-N 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
241001465754 Metazoa Species 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-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
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000003472 antidiabetic agent Substances 0.000 description 1
229940125708 antidiabetic agent Drugs 0.000 description 1
239000002585 base Substances 0.000 description 1
GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 1
150000001714 carbamic acid halides Chemical class 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000155 melt Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
POYCLYKKWFWAKO-UHFFFAOYSA-N methyl n-(3-methylphenyl)sulfonylcarbamate Chemical compound COC(=O)NS(=O)(=O)C1=CC=CC(C)=C1 POYCLYKKWFWAKO-UHFFFAOYSA-N 0.000 description 1
239000000203 mixture Substances 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
229940072033 potash Drugs 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/28—Nitrogen atoms
- C07D295/32—Nitrogen atoms acylated with carboxylic or carbonic acids, or their nitrogen or sulfur analogues

Landscapes

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

CH1164362A 1961-10-05 1962-10-03 Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden CH427794A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF0035064		1961-10-05

Publications (1)

Publication Number	Publication Date
CH427794A true CH427794A (de)	1967-01-15

Family

ID=7095838

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CH1164362A CH427794A (de)	1961-10-05	1962-10-03	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden
CH1781066A CH438303A (de)	1961-10-05	1962-10-03	Verfahren zur Herstellung von Benzolsulfonyl-semicarbaziden
CH1780966A CH438302A (de)	1961-10-05	1962-10-03	Verfahren zur Herstellung von Benzolsulfonyl-semicarbaziden

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CH1781066A CH438303A (de)	1961-10-05	1962-10-03	Verfahren zur Herstellung von Benzolsulfonyl-semicarbaziden
CH1780966A CH438302A (de)	1961-10-05	1962-10-03	Verfahren zur Herstellung von Benzolsulfonyl-semicarbaziden

Country Status (3)

Country	Link
CH (3)	CH427794A (da)
DK (7)	DK102798C (da)
GB (1)	GB980116A (da)

1962
- 1962-09-28 DK DK329663A patent/DK102798C/da active
- 1962-09-28 DK DK329963A patent/DK102800C/da active
- 1962-09-28 DK DK422562A patent/DK102740C/da active
- 1962-09-28 DK DK329563A patent/DK102797C/da active
- 1962-09-28 DK DK330063A patent/DK102742C/da active
- 1962-09-28 DK DK329763A patent/DK102799C/da active
- 1962-09-28 DK DK329863A patent/DK103019C/da active
- 1962-10-03 CH CH1164362A patent/CH427794A/de unknown
- 1962-10-03 CH CH1781066A patent/CH438303A/de unknown
- 1962-10-03 CH CH1780966A patent/CH438302A/de unknown
- 1962-10-04 GB GB3757862A patent/GB980116A/en not_active Expired

Also Published As

Publication number	Publication date
DK103019C (da)	1965-11-08
GB980116A (en)	1965-01-13
DK102740C (da)	1965-10-04
DK102797C (da)	1965-10-11
CH438303A (de)	1967-06-30
DK102799C (da)	1965-10-11
DK102742C (da)	1965-10-04
DK102800C (da)	1965-10-11
CH438302A (de)	1967-06-30
DK102798C (da)	1965-10-11

Publication	Publication Date	Title
DE1185180B (de)	1965-01-14	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
DE1493672B2 (de)	1973-09-27	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
AT236402B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonyl-semicarbaziden
DE1181208B (de)	1964-11-12	Verfahren zur Herstellung von N-Benzolsulfonyl-N'-cyclohexyl-harnstoffen
CH427794A (de)	1967-01-15	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden
CH474490A (de)	1969-06-30	Verfahren zur Herstellung neuer Benzolsulfonylharnstoffe
AT236404B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonyl-alkylen-semicarbaziden
AT235845B (de)	1964-09-25	Verfahren zur Herstellung von neuen Benzolsulfonylsemicarbaziden
AT238216B (de)	1965-01-25	Verfahren zur Herstellung von neuen Benzolsulfonyl-semicarbaziden
EP0031088A1 (de)	1981-07-01	Benzolsulfonylharnstoffe, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen sowie ihre Verwendung
AT236401B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonyl-semicarbaziden
AT216521B (de)	1961-08-10	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
AT236399B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonyl-alkylen-semicarbaziden
AT226725B (de)	1963-04-10	Verfahren zur Herstellung von neuen Sulfonylharnstoffen
AT228797B (de)	1963-08-12	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
AT234109B (de)	1964-06-10	Verfahren zur Herstellung von neuen Benzolsulfonylsemicarbaziden
AT236400B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonylsemicarbaziden
DE1793111C3 (de)	1976-07-01	Acylaminoäthylbenzolsulfonyl-delta hoch 2-cyclohexenyl-harnstoffe, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
CH459978A (de)	1968-07-31	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
AT228798B (de)	1963-08-12	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
AT248452B (de)	1966-07-25	Verfahren zur Herstellung von neuen Benzolsulfonylcyclohexylharnstoffen
DE1245380B (de)	1967-07-27	Verfahren zur Herstellung von Benzolsulfonyl-semicarbaziden
CH438263A (de)	1967-06-30	Verfahren zur Herstellung von Hydroxybenzolsulfonylharnstoffen
AT235848B (de)	1964-09-25	Verfahren zur Herstellung von neuen Benzolsulfonylalkylensemicarbaziden
DE1165012B (de)	1964-03-12	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden