CH475963A - Verfahren zur Herstellung neuer Benzolsulfonylsemicarbazide - Google Patents

Verfahren zur Herstellung neuer Benzolsulfonylsemicarbazide

Info

Publication number: CH475963A
Authority: CH; Switzerland
Prior art keywords: semicarbazide; methyl; chlorobenzenesulfonyl; toluenesulfonyl; diethyl
Prior art date: 1962-03-23

Application number

CH358463A

Other languages

German (de)

English (en)

Inventor

Adolf Dr Hagedorn

Ruth Dr Heerdt

H Dr Schmidt Felix

Rudi Dr Weyer

Original Assignee

Boehringer Mannheim Gmbh

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.)

1962-03-23

Filing date

1963-03-21

Publication date

1969-07-31

1963-03-21 Application filed by Boehringer Mannheim Gmbh filed Critical Boehringer Mannheim Gmbh

1969-07-31 Publication of CH475963A publication Critical patent/CH475963A/de

Links

238000000034 method Methods 0.000 title claims description 6
LSNDGFYQJRXEAR-UHFFFAOYSA-N benzenesulfonamidourea Chemical class NC(=O)NNS(=O)(=O)C1=CC=CC=C1 LSNDGFYQJRXEAR-UHFFFAOYSA-N 0.000 title claims description 4
238000002360 preparation method Methods 0.000 title claims description 4
-1 p-toluenesulfonyl Chemical group 0.000 claims description 16
150000001875 compounds Chemical class 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims description 4
WLVXGFFAKHILRP-UHFFFAOYSA-N butylaminourea Chemical compound CCCCNNC(N)=O WLVXGFFAKHILRP-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
230000003178 anti-diabetic effect Effects 0.000 claims description 2
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
239000004202 carbamide Substances 0.000 claims description 2
238000009833 condensation Methods 0.000 claims description 2
230000005494 condensation Effects 0.000 claims description 2
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
GEDZVLUHPSRLOQ-UHFFFAOYSA-N 1-(diethylamino)-3-(4-ethylphenyl)sulfonylurea Chemical compound C(C)C1=CC=C(C=C1)S(=O)(=O)NC(NN(CC)CC)=O GEDZVLUHPSRLOQ-UHFFFAOYSA-N 0.000 claims 1
IESHAVTXTQLOID-UHFFFAOYSA-N 1-(dimethylamino)-3-(4-methylphenyl)sulfonylurea Chemical compound CN(C)NC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 IESHAVTXTQLOID-UHFFFAOYSA-N 0.000 claims 1
GQSPOPATCHBWOC-UHFFFAOYSA-N 1-(dipropylamino)-3-(4-propan-2-ylphenyl)sulfonylurea Chemical compound C(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC(NN(CCC)CCC)=O GQSPOPATCHBWOC-UHFFFAOYSA-N 0.000 claims 1
PZXXJRGSIHRRNP-UHFFFAOYSA-N BrC1=CC=C(C=C1)S(=O)(=O)NC(NN(C(C)C)C)=O Chemical compound BrC1=CC=C(C=C1)S(=O)(=O)NC(NN(C(C)C)C)=O PZXXJRGSIHRRNP-UHFFFAOYSA-N 0.000 claims 1
UETRZTRMCMEFAY-UHFFFAOYSA-N CCCN(CCC)NC(NS(C1=CC=C(C)C=C1)(=O)=O)=O Chemical compound CCCN(CCC)NC(NS(C1=CC=C(C)C=C1)(=O)=O)=O UETRZTRMCMEFAY-UHFFFAOYSA-N 0.000 claims 1
WGTZIWPPVVGWHO-UHFFFAOYSA-N CCCN(CCC)NC(NS(C1=CC=C(CC)C=C1)(=O)=O)=O Chemical compound CCCN(CCC)NC(NS(C1=CC=C(CC)C=C1)(=O)=O)=O WGTZIWPPVVGWHO-UHFFFAOYSA-N 0.000 claims 1
239000003472 antidiabetic agent Substances 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
235000013877 carbamide Nutrition 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000008280 blood Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
206010012601 diabetes mellitus Diseases 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
150000002513 isocyanates Chemical class 0.000 description 2
239000000203 mixture Substances 0.000 description 2
150000003672 ureas Chemical class 0.000 description 2
VPOUCJRZXHAWLT-UHFFFAOYSA-N 1-(4-azidophenyl)sulfonyl-3-(dipropylamino)urea Chemical compound N(=[N+]=[N-])C1=CC=C(C=C1)S(=O)(=O)NC(NN(CCC)CCC)=O VPOUCJRZXHAWLT-UHFFFAOYSA-N 0.000 description 1
ISEHNXSZGYMKOP-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-3-(dimethylamino)urea Chemical compound CN(C)NC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 ISEHNXSZGYMKOP-UHFFFAOYSA-N 0.000 description 1
DTSDWMLIENHEDW-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-3-(dipropylamino)urea Chemical compound ClC1=CC=C(C=C1)S(=O)(=O)NC(NN(CCC)CCC)=O DTSDWMLIENHEDW-UHFFFAOYSA-N 0.000 description 1
USZHDHKFIRVDTC-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-3-[methyl(2-methylpropyl)amino]urea Chemical compound ClC1=CC=C(C=C1)S(=O)(=O)NC(NN(CC(C)C)C)=O USZHDHKFIRVDTC-UHFFFAOYSA-N 0.000 description 1
VPKFROWDHBAPEG-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-3-[methyl(3-methylbutyl)amino]urea Chemical compound ClC1=CC=C(C=C1)S(=O)(=O)NC(NN(CCC(C)C)C)=O VPKFROWDHBAPEG-UHFFFAOYSA-N 0.000 description 1
QEPWUDJOUYBQKN-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-(dimethylamino)urea Chemical compound CN(C)NC(=O)NS(=O)(=O)C1=CC=CC=C1 QEPWUDJOUYBQKN-UHFFFAOYSA-N 0.000 description 1
DVWYNPADZDHBSJ-UHFFFAOYSA-N 1-methyl-1-(2-methylpropyl)hydrazine Chemical compound CC(C)CN(C)N DVWYNPADZDHBSJ-UHFFFAOYSA-N 0.000 description 1
ITNSLFCSKQNHHZ-UHFFFAOYSA-N BrC1=CC=C(C=C1)S(=O)(=O)NC(NN(CC)CC)=O Chemical compound BrC1=CC=C(C=C1)S(=O)(=O)NC(NN(CC)CC)=O ITNSLFCSKQNHHZ-UHFFFAOYSA-N 0.000 description 1
MEUMVRMLFJFUFJ-UHFFFAOYSA-N CC(C)N(C)NC(NS(C(C=C1)=CC=C1Cl)(=O)=O)=O Chemical compound CC(C)N(C)NC(NS(C(C=C1)=CC=C1Cl)(=O)=O)=O MEUMVRMLFJFUFJ-UHFFFAOYSA-N 0.000 description 1
CCUMNELZMFAQKX-UHFFFAOYSA-N CC1=CC=C(C=C1)S(=O)(=O)NC(NN(CC(C)C)C)=O Chemical compound CC1=CC=C(C=C1)S(=O)(=O)NC(NN(CC(C)C)C)=O CCUMNELZMFAQKX-UHFFFAOYSA-N 0.000 description 1
SNPJLIJATLSIKD-UHFFFAOYSA-N CCN(C(C)C)NC(NS(C(C=C1)=CC=C1Cl)(=O)=O)=O Chemical compound CCN(C(C)C)NC(NS(C(C=C1)=CC=C1Cl)(=O)=O)=O SNPJLIJATLSIKD-UHFFFAOYSA-N 0.000 description 1
DBPMSCMXUOUKJF-UHFFFAOYSA-N CCN(CC)NC(NS(C(C=CC=C1)=C1Cl)(=O)=O)=O Chemical compound CCN(CC)NC(NS(C(C=CC=C1)=C1Cl)(=O)=O)=O DBPMSCMXUOUKJF-UHFFFAOYSA-N 0.000 description 1
PMDRTRRGWGALOJ-UHFFFAOYSA-N CCN(CC)NC(NS(C1=CC=CC=C1)(=O)=O)=O Chemical compound CCN(CC)NC(NS(C1=CC=CC=C1)(=O)=O)=O PMDRTRRGWGALOJ-UHFFFAOYSA-N 0.000 description 1
BQVQGTPYWGFXIX-UHFFFAOYSA-N ClC1=CC=C(C=C1)S(=O)(=O)NC(NN(C1CCCCC1)C)=O Chemical compound ClC1=CC=C(C=C1)S(=O)(=O)NC(NN(C1CCCCC1)C)=O BQVQGTPYWGFXIX-UHFFFAOYSA-N 0.000 description 1
KKPAPEDVDIBOLB-UHFFFAOYSA-N ClC1=CC=C(C=C1)S(=O)(=O)NC(NN(CC)CC)=O Chemical compound ClC1=CC=C(C=C1)S(=O)(=O)NC(NN(CC)CC)=O KKPAPEDVDIBOLB-UHFFFAOYSA-N 0.000 description 1
JKBKMYGEEPDCKU-UHFFFAOYSA-N ClC1=CC=C(C=C1)S(=O)(=O)NC(NN(CCCC)C)=O Chemical compound ClC1=CC=C(C=C1)S(=O)(=O)NC(NN(CCCC)C)=O JKBKMYGEEPDCKU-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001714 carbamic acid halides Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000004069 differentiation Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
ZENNVMNSMQKAGY-UHFFFAOYSA-N ethyl n-[2-(4-chlorophenyl)sulfonylethyl]carbamate Chemical compound CCOC(=O)NCCS(=O)(=O)C1=CC=C(Cl)C=C1 ZENNVMNSMQKAGY-UHFFFAOYSA-N 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229940127017 oral antidiabetic Drugs 0.000 description 1
RPDJEKMSFIRVII-UHFFFAOYSA-N oxomethylidenehydrazine Chemical group NN=C=O RPDJEKMSFIRVII-UHFFFAOYSA-N 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003349 semicarbazides Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000243 solution 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
BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07C311/48—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 having nitrogen atoms of sulfonamide groups further bound to another hetero atom
- C07C311/49—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 having nitrogen atoms of sulfonamide groups further bound to another hetero atom to nitrogen atoms
- 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH358463A 1962-03-23 1963-03-21 Verfahren zur Herstellung neuer Benzolsulfonylsemicarbazide CH475963A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEB66503A DE1170930B (de)	1962-03-23	1962-03-23	Verfahren zur Herstellung von Benzolsulfonyl-semicarbaziden

Publications (1)

Publication Number	Publication Date
CH475963A true CH475963A (de)	1969-07-31

Family

ID=6975159

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH358463A CH475963A (de)	1962-03-23	1963-03-21	Verfahren zur Herstellung neuer Benzolsulfonylsemicarbazide

Country Status (5)

Country	Link
AT (1)	AT242707B (da)
CH (1)	CH475963A (da)
DE (1)	DE1170930B (da)
DK (1)	DK113218B (da)
GB (1)	GB965386A (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4237062A (en)	1979-05-21	1980-12-02	Henkel Corporation	Sulfonylthiosemicarbazides, metal complexes thereof, and solutions containing such compounds for use in extraction of metal values

1962
- 1962-03-23 DE DEB66503A patent/DE1170930B/de active Pending
1963
- 1963-03-20 GB GB1106563A patent/GB965386A/en not_active Expired
- 1963-03-20 DK DK127563A patent/DK113218B/da unknown
- 1963-03-21 CH CH358463A patent/CH475963A/de not_active IP Right Cessation
- 1963-03-21 AT AT224863A patent/AT242707B/de active

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4237062A (en)	1979-05-21	1980-12-02	Henkel Corporation	Sulfonylthiosemicarbazides, metal complexes thereof, and solutions containing such compounds for use in extraction of metal values

Also Published As

Publication number	Publication date
DK113218B (da)	1969-03-03
AT242707B (de)	1965-10-11
DE1170930B (de)	1964-05-27
GB965386A (en)	1964-07-29

Legal Events

Date	Code	Title	Description
1972-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE3037105C2 (de)	1986-11-20	Oxazolidon- und Thiazolidon-Derivate, Verfahren zu deren Herstellung und ihre Verwendung
DE1191826B (de)	1965-04-29	Verfahren zur Herstellung neuer Benzolsulfonylsemicarbazide und ihrer Salze
DE1443911C3 (de)	1974-12-05	Benzolsulfonylharnstoffe, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
DE1201337B (de)	1965-09-23	Verfahren zur Herstellung von Benzol-sulfonylharnstoffen
CH419140A (de)	1966-08-31	Verfahren zur Herstellung neuer Benzolsulfonyl-semicarbazide
CH510029A (de)	1971-07-15	Verfahren zur Herstellung von Benzolsulfonylsemicarbaziden
DE2512702C2 (de)	1982-09-23	Substituierte 1-Amino-3-phenyl-indole, deren Salze und Verfahren zu ihrer Herstellung
DE1168415B (de)	1964-04-23	Verfahren zur Herstellung neuer Benzolsulfonyl-semicarbazide
AT219052B (de)	1962-01-10	Verfahren zur Herstellung von neuen Sulfonylharnstoffen
AT204050B (de)	1959-06-25	Verfahren zur Herstellung von neuen, antidiabetisch wirksamen Sulfonylharnstoffen
CH370765A (de)	1963-07-31	Verfahren zur Herstellung von oral wirksamen Antidiabetika
DE1206914B (de)	1965-12-16	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
AT236398B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
DE1170930B (de)	1964-05-27	Verfahren zur Herstellung von Benzolsulfonyl-semicarbaziden
DE1167816B (de)	1964-04-16	Verfahren zur Herstellung von N-p-Tosyl-N'-ª-methylsulfinylaethyl-harnstoff
AT233009B (de)	1964-04-25	Verfahren zur Herstellung neuer Sulfonylsemicarbazide
DE1157211B (de)	1963-11-14	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
AT214937B (de)	1961-05-10	Verfahren zur Herstellung von neuen N-Arylsulfonyl-N'-tetramethylenharnstoffen
AT226725B (de)	1963-04-10	Verfahren zur Herstellung von neuen Sulfonylharnstoffen
DE2045907B2 (de)	1978-03-16	Biscarbamate und Herbizide, die sie als Wirkstoff enthalten
AT345299B (de)	1978-09-11	Verfahren zur herstellung von neuen 4-(beta-ureidoaethyl)-benzolsulfonylharnstoffen und deren salzen
AT231461B (de)	1964-01-27	Verfahren zur Herstellung neuer Benzolsulfonyl-semicarbazide
AT200155B (de)	1958-10-25	Verfahren zur Herstellung von neuen Sulfonylharnstoffen
DE1233872B (de)	1967-02-09	Verfahren zur Herstellung von Benzolsulfonyl-semicarbaziden
CH353348A (de)	1961-04-15	Verfahren zur Herstellung von oral wirksamen Antidiabetika

CH475963A - Verfahren zur Herstellung neuer Benzolsulfonylsemicarbazide - Google Patents

Info

Links

Classifications

Landscapes

Applications Claiming Priority (1)

Publications (1)

Family

ID=6975159

Family Applications (1)

Country Status (5)

Cited By (1)

Cited By (1)

Also Published As

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