CH380097A - Verfahren zur Herstellung von neuen Benzolsulfonylbenzylharnstoffen - Google Patents

Verfahren zur Herstellung von neuen Benzolsulfonylbenzylharnstoffen

Info

Publication number: CH380097A
Authority: CH; Switzerland
Prior art keywords: blood sugar; urea; benzenesulfonyl; benzyl; methyl
Prior art date: 1957-12-27

Application number

CH108364A

Other languages

German (de)

English (en)

Inventor

Walter Dr Aumueller

Gerhard Dr Korger

Rudi Dr Weyer

Josef Dr Scholz

Alfred Dr Baender

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.)

1957-12-27

Filing date

1958-12-19

Publication date

1964-07-31

1957-12-27 Priority claimed from DEF24704A external-priority patent/DE1076664B/de

1958-12-19 Application filed by Hoechst Ag filed Critical Hoechst Ag

1964-07-31 Publication of CH380097A publication Critical patent/CH380097A/de

Links

238000000034 method Methods 0.000 title claims description 16
238000002360 preparation method Methods 0.000 title claims description 8
239000008280 blood Substances 0.000 claims description 10
210000004369 blood Anatomy 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
-1 4-methylbenzenesulfonyl Chemical group 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 3
239000004202 carbamide Substances 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
239000011593 sulfur Substances 0.000 claims description 2
239000000047 product Substances 0.000 claims 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
241001465754 Metazoa Species 0.000 claims 4
TYCNEYCZTJHLJI-UHFFFAOYSA-N 1-benzyl-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NCC1=CC=CC=C1 TYCNEYCZTJHLJI-UHFFFAOYSA-N 0.000 claims 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
230000000694 effects Effects 0.000 claims 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
241000282472 Canis lupus familiaris Species 0.000 claims 2
229940100389 Sulfonylurea Drugs 0.000 claims 2
239000003513 alkali Substances 0.000 claims 2
229910001854 alkali hydroxide Inorganic materials 0.000 claims 2
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 2
UCGFRIAOVLXVKL-UHFFFAOYSA-N benzylthiourea Chemical compound NC(=S)NCC1=CC=CC=C1 UCGFRIAOVLXVKL-UHFFFAOYSA-N 0.000 claims 2
230000015572 biosynthetic process Effects 0.000 claims 2
150000004649 carbonic acid derivatives Chemical class 0.000 claims 2
239000003814 drug Substances 0.000 claims 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims 2
238000002844 melting Methods 0.000 claims 2
230000008018 melting Effects 0.000 claims 2
239000003538 oral antidiabetic agent Substances 0.000 claims 2
150000007530 organic bases Chemical class 0.000 claims 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims 2
238000003756 stirring Methods 0.000 claims 2
239000000126 substance Substances 0.000 claims 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 1
RBXRTHONRIMTBL-UHFFFAOYSA-N 1-(4-aminophenyl)sulfonyl-3-benzylurea Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC(=O)NCC1=CC=CC=C1 RBXRTHONRIMTBL-UHFFFAOYSA-N 0.000 claims 1
241000416162 Astragalus gummifer Species 0.000 claims 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
244000265913 Crataegus laevigata Species 0.000 claims 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 claims 1
229920002472 Starch Polymers 0.000 claims 1
JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 claims 1
229920001615 Tragacanth Polymers 0.000 claims 1
229910021529 ammonia Inorganic materials 0.000 claims 1
230000036765 blood level Effects 0.000 claims 1
VDTNNGKXZGSZIP-UHFFFAOYSA-N carbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VDTNNGKXZGSZIP-UHFFFAOYSA-N 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
239000003610 charcoal Substances 0.000 claims 1
230000000973 chemotherapeutic effect Effects 0.000 claims 1
238000001816 cooling Methods 0.000 claims 1
230000007423 decrease Effects 0.000 claims 1
206010012601 diabetes mellitus Diseases 0.000 claims 1
238000002474 experimental method Methods 0.000 claims 1
239000000706 filtrate Substances 0.000 claims 1
238000010438 heat treatment Methods 0.000 claims 1
230000000968 intestinal effect Effects 0.000 claims 1
239000008101 lactose Substances 0.000 claims 1
235000019359 magnesium stearate Nutrition 0.000 claims 1
239000000203 mixture Substances 0.000 claims 1
239000008164 mustard oil Substances 0.000 claims 1
231100000252 nontoxic Toxicity 0.000 claims 1
230000003000 nontoxic effect Effects 0.000 claims 1
231100000926 not very toxic Toxicity 0.000 claims 1
239000002244 precipitate Substances 0.000 claims 1
238000001556 precipitation Methods 0.000 claims 1
235000010288 sodium nitrite Nutrition 0.000 claims 1
VTLHPYXKUOESEM-UHFFFAOYSA-N sodium;(4-methylphenyl)sulfonylazanide Chemical compound [Na+].CC1=CC=C(S([NH-])(=O)=O)C=C1 VTLHPYXKUOESEM-UHFFFAOYSA-N 0.000 claims 1
239000008107 starch Substances 0.000 claims 1
235000019698 starch Nutrition 0.000 claims 1
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 1
239000000454 talc Substances 0.000 claims 1
229910052623 talc Inorganic materials 0.000 claims 1
235000010487 tragacanth Nutrition 0.000 claims 1
239000000196 tragacanth Substances 0.000 claims 1
229940116362 tragacanth Drugs 0.000 claims 1
239000003472 antidiabetic agent Substances 0.000 description 2
230000003178 anti-diabetic effect Effects 0.000 description 1
229940125708 antidiabetic agent Drugs 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
239000002904 solvent Substances 0.000 description 1
150000003672 ureas Chemical class 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/64—Sulfonylureas, e.g. glibenclamide, tolbutamide, chlorpropamide
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K10/00—Animal feeding-stuffs
- A23K10/30—Animal feeding-stuffs from material of plant origin, e.g. roots, seeds or hay; from material of fungal origin, e.g. mushrooms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
- C07C311/57—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
- C07C311/58—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to hydrogen atoms or to acyclic carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Polymers & Plastics (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Epidemiology (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Food Science & Technology (AREA)
Botany (AREA)
Zoology (AREA)
Animal Husbandry (AREA)
Physiology (AREA)
Biotechnology (AREA)
Molecular Biology (AREA)
Mycology (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)

CH108364A 1957-12-27 1958-12-19 Verfahren zur Herstellung von neuen Benzolsulfonylbenzylharnstoffen CH380097A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEF24704A DE1076664B (de)	1957-12-27	1957-12-27	Verfahren zur Herstellung von neuen N-Benzolsulfonyl-N'-benzyl-harnstoffen
DEF0027097		1958-11-22

Publications (1)

Publication Number	Publication Date
CH380097A true CH380097A (de)	1964-07-31

Family

ID=25974088

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CH108364A CH380097A (de)	1957-12-27	1958-12-19	Verfahren zur Herstellung von neuen Benzolsulfonylbenzylharnstoffen
CH6749358A CH388287A (de)	1957-12-27	1958-12-19	Verfahren zur Herstellung von neuen Benzolsulfonylbenzylharnstoffen
CH108264A CH380098A (de)	1957-12-27	1958-12-19	Verfahren zur Herstellung von neuen Benzolsulfonylbenzylharnstoffen

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CH6749358A CH388287A (de)	1957-12-27	1958-12-19	Verfahren zur Herstellung von neuen Benzolsulfonylbenzylharnstoffen
CH108264A CH380098A (de)	1957-12-27	1958-12-19	Verfahren zur Herstellung von neuen Benzolsulfonylbenzylharnstoffen

Country Status (3)

Country	Link
BE (1)	BE574263A (fr)
CH (3)	CH380097A (fr)
SE (1)	SE205151C1 (fr)

1958
- 1958-12-19 CH CH108364A patent/CH380097A/de unknown
- 1958-12-19 CH CH6749358A patent/CH388287A/de unknown
- 1958-12-19 CH CH108264A patent/CH380098A/de unknown
- 1958-12-27 BE BE574263A patent/BE574263A/fr unknown
1962
- 1962-02-28 SE SE223462A patent/SE205151C1/sv unknown

Also Published As

Publication number	Publication date
CH388287A (de)	1965-02-28
CH380098A (de)	1964-07-31
SE205151C1 (sv)	1966-06-07
BE574263A (fr)	1959-06-27

Publication	Publication Date	Title
CH392498A (de)	1965-05-31	Verfahren zur Herstellung von neuen Benzolsulfonyl-cyclohexyl-harnstoffen
CH380097A (de)	1964-07-31	Verfahren zur Herstellung von neuen Benzolsulfonylbenzylharnstoffen
DE2629756C2 (fr)	1987-08-06
AT236976B (de)	1964-11-25	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
AT226729B (de)	1963-04-10	Verfahren zur Herstellung von neuen Sulfonylharnstoffen
AT226725B (de)	1963-04-10	Verfahren zur Herstellung von neuen Sulfonylharnstoffen
CH459978A (de)	1968-07-31	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
CH371108A (de)	1963-08-15	Verfahren zur Herstellung von Sulfonylharnstoffen
CH370766A (de)	1963-07-31	Verfahren zur Herstellung von oral wirksamen Antidiabetika
AT212312B (de)	1960-12-12	Verfahren zur Herstellung von neuen 2-Sulfonamidothiadiazol-Derivaten
AT234114B (de)	1964-06-10	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
AT236397B (de)	1964-10-26	Verfahren zur Herstellung von neuen Azidobenzolsulfonylharnstoffen
AT236410B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonyl-alkylen-semicarbaziden
AT226728B (de)	1963-04-10	Verfahren zur Herstellung von neuen Benzolsulfonyl-cyclohexyl-harnstoffen
AT336032B (de)	1977-04-12	Verfahren zur herstellung von neuen acylaminoalkylbenzolsufonylharnstoffen und deren salzen
AT216521B (de)	1961-08-10	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
AT211310B (de)	1960-10-10	Verfahren zur Herstellung von neuen 2-Sulfonamido-thiadiazol-Derivaten
AT235846B (de)	1964-09-25	Verfaren zur Herstellung von Benzolsulfonyl-semicarbaziden
AT345300B (de)	1978-09-11	Verfahren zur herstellung von neuen 4-(beta-ureidoaethyl)-benzolsulfonylharnstoffen und deren salzen
CH465597A (de)	1968-11-30	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
AT219052B (de)	1962-01-10	Verfahren zur Herstellung von neuen Sulfonylharnstoffen
DE1076664B (de)	1960-03-03	Verfahren zur Herstellung von neuen N-Benzolsulfonyl-N'-benzyl-harnstoffen
AT238218B (de)	1965-01-25	Verfahren zur Herstellung von neuen Benzolsulfonyl-semicarbaziden
CH380717A (de)	1964-08-15	Verfahren zur Herstellung von neuen Sulfonylharnstoffen
AT226730B (de)	1963-04-10	Verfahren zur Herstellung von neuen Sulfonylharnstoffen