CH465597A - Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen - Google Patents

Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen

Info

Publication number: CH465597A
Authority: CH; Switzerland
Prior art keywords: methyl; endomethylene; benzenesulfonyl; cyclohexen; urea
Prior art date: 1961-06-03

Application number

CH395466A

Other languages

German (de)

English (en)

Inventor

Korger Gerhard

Aumueller Walter

Haack Erich

Richard Peschke Wilhel Andreas

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

1968-11-30

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

1968-11-30 Publication of CH465597A publication Critical patent/CH465597A/de

Links

238000000034 method Methods 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title claims description 5
-1 benzenesulfonyl isourea ethers Chemical class 0.000 claims description 19
150000001875 compounds Chemical class 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
BRSRNTJGTDYRFT-UHFFFAOYSA-N 2-(benzenesulfonyl)guanidine Chemical class NC(N)=NS(=O)(=O)C1=CC=CC=C1 BRSRNTJGTDYRFT-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
239000008280 blood Substances 0.000 description 10
210000004369 blood Anatomy 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 7
241000283973 Oryctolagus cuniculus Species 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
150000003839 salts Chemical class 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 3
JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
GHDLZGOOOLEJKI-UHFFFAOYSA-N benzenesulfonylurea Chemical class NC(=O)NS(=O)(=O)C1=CC=CC=C1 GHDLZGOOOLEJKI-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000203 mixture Substances 0.000 description 3
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
239000003472 antidiabetic agent Substances 0.000 description 2
229940125708 antidiabetic agent Drugs 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
206010012601 diabetes mellitus Diseases 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
150000002357 guanidines Chemical class 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
239000000155 melt Substances 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
MJJCZWPYKMGQHU-UHFFFAOYSA-N methylparabanic acid Chemical compound CN1C(=O)NC(=O)C1=O MJJCZWPYKMGQHU-UHFFFAOYSA-N 0.000 description 2
XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
241000416162 Astragalus gummifer Species 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
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
244000265913 Crataegus laevigata Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
229920002472 Starch Polymers 0.000 description 1
229940100389 Sulfonylurea Drugs 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
239000003513 alkali Substances 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000008331 benzenesulfonamides Chemical class 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
238000009835 boiling Methods 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
239000003610 charcoal Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004679 hydroxides Chemical class 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
239000008101 lactose Substances 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
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 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
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
230000020477 pH reduction Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000717 retained effect Effects 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
239000002904 solvent Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 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
230000001225 therapeutic effect Effects 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)
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)

CH395466A 1961-06-03 1962-05-30 Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen CH465597A (de)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
CH465597A true CH465597A (de)	1968-11-30

Family

ID=7095404

Family Applications (4)

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

Family Applications After (3)

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

Country Status (7)

Country	Link
AT (2)	AT239251B (da)
BE (1)	BE618512A (da)
CH (4)	CH465597A (da)
DK (4)	DK105527C (da)
FR (2)	FR1998M (da)
GB (1)	GB1007018A (da)
SE (1)	SE307350B (da)

Families Citing this family (1)

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

1962
- 1962-05-30 CH CH395466A patent/CH465597A/de unknown
- 1962-05-30 CH CH659362A patent/CH419089A/de unknown
- 1962-05-30 CH CH395666A patent/CH442287A/de unknown
- 1962-05-30 CH CH395566A patent/CH457415A/de unknown
- 1962-06-01 DK DK246062AA patent/DK105527C/da active
- 1962-06-01 GB GB21310/62A patent/GB1007018A/en not_active Expired
- 1962-06-01 AT AT903263A patent/AT239251B/de active
- 1962-06-01 AT AT226964A patent/AT247870B/de active
- 1962-06-01 DK DK278663AA patent/DK103667C/da active
- 1962-06-01 DK DK278563AA patent/DK106669C/da active
- 1962-06-01 DK DK278363AA patent/DK104565C/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
GB1007018A (en)	1965-10-13
BE618512A (fr)	1962-12-14
DK104565C (da)	1966-06-06
FR1998M (fr)	1963-09-02
CH457415A (de)	1968-06-15
SE307350B (da)	1969-01-07
DK105527C (da)	1966-10-10
CH419089A (de)	1966-08-31
AT239251B (de)	1965-03-25
CH442287A (de)	1967-08-31
AT247870B (de)	1966-06-27
FR1999M (fr)	1963-09-02
DK106669C (da)	1967-03-06
DK103667C (da)	1966-02-07

Publication	Publication Date	Title
CH629781A5 (de)	1982-05-14	Verfahren zur herstellung von benzolsulfonylharnstoffen.
CH440251A (de)	1967-07-31	Verfahren zur Herstellung von Benzolsulfonyl-cyclohexylharnstoffen
DE1695104A1 (de)	1971-03-18	Aktive Sulfonamide
DE1198354B (de)	1965-08-12	Verfahren zur Herstellung von Benzol-sulfonylharnstoffen
AT238215B (de)	1965-01-25	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
AT226728B (de)	1963-04-10	Verfahren zur Herstellung von neuen Benzolsulfonyl-cyclohexyl-harnstoffen
CH370766A (de)	1963-07-31	Verfahren zur Herstellung von oral wirksamen Antidiabetika
CH459178A (de)	1968-07-15	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
AT236975B (de)	1964-11-25	Verfahren zur Herstellung von neuen Azidobenzolsulfonylharnstoffen
CH419089A (de)	1966-08-31	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
AT335463B (de)	1977-03-10	Verfahren zur herstellung von neuen benzolsulfonylharnstoffen und deren salzen
AT212312B (de)	1960-12-12	Verfahren zur Herstellung von neuen 2-Sulfonamidothiadiazol-Derivaten
CH374984A (de)	1964-02-15	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
AT236397B (de)	1964-10-26	Verfahren zur Herstellung von neuen Azidobenzolsulfonylharnstoffen
AT226729B (de)	1963-04-10	Verfahren zur Herstellung von neuen Sulfonylharnstoffen
AT228797B (de)	1963-08-12	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
AT228798B (de)	1963-08-12	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
CH380717A (de)	1964-08-15	Verfahren zur Herstellung von neuen Sulfonylharnstoffen
AT236405B (de)	1964-10-26	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
AT236976B (de)	1964-11-25	Verfahren zur Herstellung von neuen Benzolsulfonylharnstoffen
CH504418A (de)	1971-03-15	Verfahren zur Herstellung von Benzolsulfonylharnstoffen
AT226727B (de)	1963-04-10	Verfahren zur Herstellung von neuen Benzolsulfonylcyclohexyl-harnstoffen
AT211310B (de)	1960-10-10	Verfahren zur Herstellung von neuen 2-Sulfonamido-thiadiazol-Derivaten
AT333298B (de)	1976-11-10	Verfahren zur herstellung von neuen acylaminoalkylbenzolsulfonylharnstoffen und deren salzen
AT248452B (de)	1966-07-25	Verfahren zur Herstellung von neuen Benzolsulfonylcyclohexylharnstoffen