CH419089A - Verfahren zur Herstellung von Benzolsulfonylharnstoffen - Google Patents

Verfahren zur Herstellung von Benzolsulfonylharnstoffen

Info

Publication number: CH419089A
Authority: CH; Switzerland
Prior art keywords: endomethylene; benzenesulfonyl; formula; urea; methyl
Prior art date: 1961-06-03

Application number

CH659362A

Other languages

German (de)

English (en)

Inventor

Korger Gerhard

Aumueller Walter

Haack Erich

Ludwig Wilhelm

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.)

1961-06-03

Filing date

1962-05-30

Publication date

1966-08-31

1962-05-30 Application filed by Hoechst Ag filed Critical Hoechst Ag

1966-08-31 Publication of CH419089A publication Critical patent/CH419089A/de

Links

238000000034 method Methods 0.000 title claims description 17
238000002360 preparation method Methods 0.000 title claims description 6
239000004202 carbamide Substances 0.000 claims description 15
150000001875 compounds Chemical class 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
-1 alicyclic radical Chemical class 0.000 description 34
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 18
235000013877 carbamide Nutrition 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
150000001412 amines Chemical class 0.000 description 12
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
239000000047 product Substances 0.000 description 11
239000008280 blood Substances 0.000 description 9
210000004369 blood Anatomy 0.000 description 9
150000003839 salts Chemical class 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
241000283973 Oryctolagus cuniculus Species 0.000 description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
150000003672 ureas Chemical class 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
239000012948 isocyanate Substances 0.000 description 4
150000002513 isocyanates Chemical class 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000012360 testing method Methods 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000008331 benzenesulfonamides Chemical class 0.000 description 3
150000001714 carbamic acid halides Chemical class 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
BAEROHOXEQUTSU-UHFFFAOYSA-N BrC1=CC=C(C=C1)S(=O)(=O)CCNC(=O)OCC Chemical compound BrC1=CC=C(C=C1)S(=O)(=O)CCNC(=O)OCC BAEROHOXEQUTSU-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 2
GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 2
206010012601 diabetes mellitus Diseases 0.000 description 2
239000003814 drug Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
BZSZSGLQJIWVGD-UHFFFAOYSA-N ethyl n-(4-chlorophenyl)sulfonyl-n-ethylcarbamate Chemical compound CCOC(=O)N(CC)S(=O)(=O)C1=CC=C(Cl)C=C1 BZSZSGLQJIWVGD-UHFFFAOYSA-N 0.000 description 2
238000001990 intravenous administration 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
UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
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
JGHDVROWMPBQSR-UHFFFAOYSA-N 4-chloro-n-(oxomethylidene)benzenesulfonamide Chemical compound ClC1=CC=C(S(=O)(=O)N=C=O)C=C1 JGHDVROWMPBQSR-UHFFFAOYSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
XSJCSHIXSQNGOH-UHFFFAOYSA-N C(C)N(C(=O)OCC)S(=O)(=O)C1=CC=C(C=C1)Br Chemical compound C(C)N(C(=O)OCC)S(=O)(=O)C1=CC=C(C=C1)Br XSJCSHIXSQNGOH-UHFFFAOYSA-N 0.000 description 1
YYYYQTRZTAKNRB-UHFFFAOYSA-N C(C)N(C(=O)OCC)S(=O)(=O)C1=CC=C(C=C1)OCC Chemical compound C(C)N(C(=O)OCC)S(=O)(=O)C1=CC=C(C=C1)OCC YYYYQTRZTAKNRB-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
208000035473 Communicable disease Diseases 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229940100389 Sulfonylurea Drugs 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 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
230000003178 anti-diabetic effect Effects 0.000 description 1
239000003472 antidiabetic agent Substances 0.000 description 1
229940125708 antidiabetic agent Drugs 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical class OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
CEHNDPXHFFJGHW-UHFFFAOYSA-N ethyl N-(4-chlorophenyl)sulfonyl-N-methylcarbamate Chemical compound CN(C(=O)OCC)S(=O)(=O)C1=CC=C(C=C1)Cl CEHNDPXHFFJGHW-UHFFFAOYSA-N 0.000 description 1
UTLABMWLBRDNAM-UHFFFAOYSA-N ethyl n-[(4-methylphenyl)sulfonylmethyl]carbamate Chemical compound CCOC(=O)NCS(=O)(=O)C1=CC=C(C)C=C1 UTLABMWLBRDNAM-UHFFFAOYSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
150000002357 guanidines Chemical class 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000007774 longterm Effects 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
231100000957 no side effect Toxicity 0.000 description 1
231100000926 not very toxic Toxicity 0.000 description 1
239000003538 oral antidiabetic agent Substances 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
235000020075 ouzo Nutrition 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 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
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1

Classifications

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

Landscapes

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

CH659362A 1961-06-03 1962-05-30 Verfahren zur Herstellung von Benzolsulfonylharnstoffen CH419089A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF0034081		1961-06-03

Publications (1)

Publication Number	Publication Date
CH419089A true CH419089A (de)	1966-08-31

Family

ID=7095404

Family Applications (4)

Application Number	Title	Priority Date	Filing Date
CH659362A CH419089A (de)	1961-06-03	1962-05-30	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
CH395566A CH457415A (de)	1961-06-03	1962-05-30	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
CH395666A CH442287A (de)	1961-06-03	1962-05-30	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
CH395466A CH465597A (de)	1961-06-03	1962-05-30	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen

Family Applications After (3)

Application Number	Title	Priority Date	Filing Date
CH395566A CH457415A (de)	1961-06-03	1962-05-30	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
CH395666A CH442287A (de)	1961-06-03	1962-05-30	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
CH395466A CH465597A (de)	1961-06-03	1962-05-30	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen

Country Status (7)

Country	Link
AT (2)	AT239251B (fr)
BE (1)	BE618512A (fr)
CH (4)	CH419089A (fr)
DK (4)	DK104565C (fr)
FR (2)	FR1998M (fr)
GB (1)	GB1007018A (fr)
SE (1)	SE307350B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL294761A (fr) *	1962-07-02

1962
- 1962-05-30 CH CH659362A patent/CH419089A/de unknown
- 1962-05-30 CH CH395566A patent/CH457415A/de unknown
- 1962-05-30 CH CH395666A patent/CH442287A/de unknown
- 1962-05-30 CH CH395466A patent/CH465597A/de unknown
- 1962-06-01 DK DK278363AA patent/DK104565C/da active
- 1962-06-01 DK DK246062AA patent/DK105527C/da active
- 1962-06-01 AT AT903263A patent/AT239251B/de active
- 1962-06-01 DK DK278563AA patent/DK106669C/da active
- 1962-06-01 AT AT226964A patent/AT247870B/de active
- 1962-06-01 GB GB21310/62A patent/GB1007018A/en not_active Expired
- 1962-06-01 DK DK278663AA patent/DK103667C/da active
- 1962-06-04 BE BE618512A patent/BE618512A/fr unknown
- 1962-09-03 FR FR908453A patent/FR1998M/fr active Active
- 1962-09-03 FR FR908454A patent/FR1999M/fr active Active
1964
- 1964-03-04 SE SE2648/64A patent/SE307350B/xx unknown

Also Published As

Publication number	Publication date
SE307350B (fr)	1969-01-07
DK104565C (da)	1966-06-06
FR1999M (fr)	1963-09-02
BE618512A (fr)	1962-12-14
AT239251B (de)	1965-03-25
DK105527C (da)	1966-10-10
CH465597A (de)	1968-11-30
CH442287A (de)	1967-08-31
AT247870B (de)	1966-06-27
FR1998M (fr)	1963-09-02
GB1007018A (en)	1965-10-13
DK106669C (da)	1967-03-06
CH457415A (de)	1968-06-15
DK103667C (da)	1966-02-07

Publication	Publication Date	Title
DE1518874B2 (de)	1974-07-18	Benzolsulfonylharnstoffe und Verfahren zu ihrer Herstellung
DE1181208B (de)	1964-11-12	Verfahren zur Herstellung von N-Benzolsulfonyl-N'-cyclohexyl-harnstoffen
DE1198354B (de)	1965-08-12	Verfahren zur Herstellung von Benzol-sulfonylharnstoffen
CH419089A (de)	1966-08-31	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
CH518912A (de)	1972-02-15	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
DE2238870B2 (de)	1978-02-16	Benzolsulfonylharnstoffe
AT238215B (de)	1965-01-25	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
DE1157211B (de)	1963-11-14	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
CH374984A (de)	1964-02-15	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
DE1153357B (de)	1963-08-29	Verfahren zur Herstellung von Azidobenzolsulfonylharnstoffen
CH370766A (de)	1963-07-31	Verfahren zur Herstellung von oral wirksamen Antidiabetika
AT201608B (de)	1959-01-10	Verfahren zur Herstellung von neuen Sulfonylharnstoffen
AT236397B (de)	1964-10-26	Verfahren zur Herstellung von neuen Azidobenzolsulfonylharnstoffen
AT219052B (de)	1962-01-10	Verfahren zur Herstellung von neuen Sulfonylharnstoffen
DE1251753B (de)	1967-10-12	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
AT228797B (de)	1963-08-12	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
AT216521B (de)	1961-08-10	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
AT226727B (de)	1963-04-10	Verfahren zur Herstellung von neuen Benzolsulfonylcyclohexyl-harnstoffen
DE1618402C3 (de)	1977-04-07	Benzolsulfonylharnstoffe, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
DE1443890C (de)	1973-08-30	Benzolsulfonyl Harnstoffe und Verfahren zu ihrer Herstellung
CH448055A (de)	1967-12-15	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
AT228798B (de)	1963-08-12	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
CH504418A (de)	1971-03-15	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
AT248452B (de)	1966-07-25	Verfahren zur Herstellung von neuen Benzolsulfonylcyclohexylharnstoffen
AT236976B (de)	1964-11-25	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen