CH448055A - Verfahren zur Herstellung von Benzolsulfonylharnstoffen - Google Patents

Verfahren zur Herstellung von Benzolsulfonylharnstoffen

Info

Publication number: CH448055A
Authority: CH; Switzerland
Prior art keywords: benzenesulfonylureas; sulfur; oxygen; preparation; benzenesulfonyl
Prior art date: 1961-06-22

Application number

CH395266A

Other languages

German (de)

English (en)

Inventor

Aumueller Walter

Korger Gerhard

Baender Alfred

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.)

1961-06-22

Filing date

1962-06-20

Publication date

1967-12-15

1962-06-20 Application filed by Hoechst Ag filed Critical Hoechst Ag

1967-12-15 Publication of CH448055A publication Critical patent/CH448055A/de

Links

238000000034 method Methods 0.000 title claims description 14
238000002360 preparation method Methods 0.000 title claims description 6
-1 benzenesulfonyl halides Chemical class 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
229910052717 sulfur Chemical group 0.000 claims description 5
239000011593 sulfur Chemical group 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
150000002357 guanidines Chemical class 0.000 claims description 3
239000004215 Carbon black (E152) Substances 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
150000001875 compounds Chemical class 0.000 claims description 2
229930195733 hydrocarbon Natural products 0.000 claims description 2
150000007530 organic bases Chemical class 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
150000007529 inorganic bases Chemical class 0.000 claims 1
239000008280 blood Substances 0.000 description 6
210000004369 blood Anatomy 0.000 description 6
239000000047 product Substances 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
DMRNUGUDGCPNAG-UHFFFAOYSA-N 1-cycloheptyl-3-[4-(trifluoromethoxy)phenyl]sulfonylurea Chemical compound FC(F)(F)OC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCCC1 DMRNUGUDGCPNAG-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000003472 antidiabetic agent Substances 0.000 description 2
229940125708 antidiabetic agent Drugs 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
206010012601 diabetes mellitus Diseases 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
230000000694 effects Effects 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
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 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
BRSRNTJGTDYRFT-UHFFFAOYSA-N 2-(benzenesulfonyl)guanidine Chemical class NC(N)=NS(=O)(=O)C1=CC=CC=C1 BRSRNTJGTDYRFT-UHFFFAOYSA-N 0.000 description 1
KSMVBYPXNKCPAJ-UHFFFAOYSA-N 4-Methylcyclohexylamine Chemical compound CC1CCC(N)CC1 KSMVBYPXNKCPAJ-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
208000035473 Communicable disease Diseases 0.000 description 1
YBUMZWJAZFFBRG-UHFFFAOYSA-N FC(OC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCCCC1)(F)F Chemical compound FC(OC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCCCC1)(F)F YBUMZWJAZFFBRG-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
XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
RLVJPFWQCRFPMC-UHFFFAOYSA-N OS(C(C=CC=C1C(F)(F)F)=C1S)(=O)=O Chemical class OS(C(C=CC=C1C(F)(F)F)=C1S)(=O)=O RLVJPFWQCRFPMC-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
239000003513 alkali Substances 0.000 description 1
150000001555 benzenes Chemical class 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
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
VXVVUHQULXCUPF-UHFFFAOYSA-N cycloheptanamine Chemical compound NC1CCCCCC1 VXVVUHQULXCUPF-UHFFFAOYSA-N 0.000 description 1
SZGLLXJFYCJRPP-UHFFFAOYSA-N cycloheptylurea Chemical compound NC(=O)NC1CCCCCC1 SZGLLXJFYCJRPP-UHFFFAOYSA-N 0.000 description 1
PSVJDFLPZZXFDU-UHFFFAOYSA-N cyclohexen-1-amine Chemical compound NC1=CCCCC1 PSVJDFLPZZXFDU-UHFFFAOYSA-N 0.000 description 1
NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
OQGVPWWLCUMRCI-UHFFFAOYSA-N cyclopenten-1-amine Chemical compound NC1=CCCC1 OQGVPWWLCUMRCI-UHFFFAOYSA-N 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000010438 heat treatment Methods 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
230000000968 intestinal 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
238000004519 manufacturing process Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 1
DVYAXKVXYQZRTI-UHFFFAOYSA-N n-phenyl-n-(trifluoromethyl)thiohydroxylamine Chemical class FC(F)(F)N(S)C1=CC=CC=C1 DVYAXKVXYQZRTI-UHFFFAOYSA-N 0.000 description 1
231100000957 no side effect Toxicity 0.000 description 1
159000000000 sodium salts Chemical class 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
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000002560 therapeutic procedure Methods 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
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

Landscapes

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

CH395266A 1961-06-22 1962-06-20 Verfahren zur Herstellung von Benzolsulfonylharnstoffen CH448055A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF0034239		1961-06-22

Publications (1)

Publication Number	Publication Date
CH448055A true CH448055A (de)	1967-12-15

Family

ID=7095468

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CH395266A CH448055A (de)	1961-06-22	1962-06-20	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
CH395366A CH448056A (de)	1961-06-22	1962-06-20	Verfahren zur Herstellung neuer Benzolsulfonylharnstoffe
CH744162A CH419090A (de)	1961-06-22	1962-06-20	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CH395366A CH448056A (de)	1961-06-22	1962-06-20	Verfahren zur Herstellung neuer Benzolsulfonylharnstoffe
CH744162A CH419090A (de)	1961-06-22	1962-06-20	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen

Country Status (5)

Country	Link
BE (1)	BE619289A (da)
CH (3)	CH448055A (da)
DK (2)	DK109745C (da)
FR (1)	FR2022M (da)
GB (1)	GB953097A (da)

1962
- 1962-06-20 CH CH395266A patent/CH448055A/de unknown
- 1962-06-20 CH CH395366A patent/CH448056A/de unknown
- 1962-06-20 CH CH744162A patent/CH419090A/de unknown
- 1962-06-21 DK DK388763AA patent/DK109745C/da active
- 1962-06-21 DK DK388663AA patent/DK103072C/da active
- 1962-06-22 BE BE619289A patent/BE619289A/fr unknown
- 1962-06-22 GB GB24183/62A patent/GB953097A/en not_active Expired
- 1962-09-21 FR FR910102A patent/FR2022M/fr active Active

Also Published As

Publication number	Publication date
DK103072C (da)	1965-11-15
FR2022M (fr)	1963-09-16
BE619289A (fr)	1962-12-24
CH419090A (de)	1966-08-31
GB953097A (en)	1964-03-25
DK109745C (da)	1968-06-24
CH448056A (de)	1967-12-15

Publication	Publication Date	Title
DE2238870C3 (de)	1978-09-28	Benzolsulfonylharnstoffe
DE1443911A1 (de)	1969-04-30	Benzolsulfonylharnstoffe und Verfahren zu ihrer Herstellung
CH392497A (de)	1965-05-31	Verfahren zur Herstellung von neuen Benzolsulfonyl-cyclohexyl-harnstoffen
CH448055A (de)	1967-12-15	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
CH459178A (de)	1968-07-15	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
AT238215B (de)	1965-01-25	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
CH374984A (de)	1964-02-15	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
AT236976B (de)	1964-11-25	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
AT226728B (de)	1963-04-10	Verfahren zur Herstellung von neuen Benzolsulfonyl-cyclohexyl-harnstoffen
AT201608B (de)	1959-01-10	Verfahren zur Herstellung von neuen Sulfonylharnstoffen
AT236397B (de)	1964-10-26	Verfahren zur Herstellung von neuen Azidobenzolsulfonylharnstoffen
CH419089A (de)	1966-08-31	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
AT236975B (de)	1964-11-25	Verfahren zur Herstellung von neuen Azidobenzolsulfonylharnstoffen
DE1153357B (de)	1963-08-29	Verfahren zur Herstellung von Azidobenzolsulfonylharnstoffen
AT219052B (de)	1962-01-10	Verfahren zur Herstellung von neuen Sulfonylharnstoffen
AT236974B (de)	1964-11-25	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
CH380717A (de)	1964-08-15	Verfahren zur Herstellung von neuen Sulfonylharnstoffen
AT228797B (de)	1963-08-12	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
AT226727B (de)	1963-04-10	Verfahren zur Herstellung von neuen Benzolsulfonylcyclohexyl-harnstoffen
DE1443898C (de)	1973-03-29	Benzolsulfonylharnstoffe, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate
AT336032B (de)	1977-04-12	Verfahren zur herstellung von neuen acylaminoalkylbenzolsufonylharnstoffen und deren salzen
AT336033B (de)	1977-04-12	Verfahren zur herstellung von neuen acylaminoalkylbenzolsulfonylharnstoffen und deren salzen
AT236413B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
DE1156782B (de)	1963-11-07	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
CH380097A (de)	1964-07-31	Verfahren zur Herstellung von neuen Benzolsulfonylbenzylharnstoffen