GB896303A - Improvements in and relating to sulphonylureas and the manufacture thereof - Google Patents
Improvements in and relating to sulphonylureas and the manufacture thereofInfo
- Publication number
- GB896303A GB896303A GB3496058A GB3496058A GB896303A GB 896303 A GB896303 A GB 896303A GB 3496058 A GB3496058 A GB 3496058A GB 3496058 A GB3496058 A GB 3496058A GB 896303 A GB896303 A GB 896303A
- Authority
- GB
- United Kingdom
- Prior art keywords
- arylsulphonyl
- reacting
- alkyl
- chloride
- ethyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 sulphonyl ureas Chemical class 0.000 abstract 13
- 235000013877 carbamide Nutrition 0.000 abstract 4
- 150000001412 amines Chemical class 0.000 abstract 2
- 239000004202 carbamide Substances 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000012948 isocyanate Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- JVPKRFXSEHQJRU-UHFFFAOYSA-N (4-propan-2-ylphenyl)sulfonylcarbamic acid Chemical class C(C)(C)C1=CC=C(C=C1)S(=O)(=O)NC(O)=O JVPKRFXSEHQJRU-UHFFFAOYSA-N 0.000 abstract 1
- FHMRJRSOWRCSKA-UHFFFAOYSA-N 4-fluoro-n-(oxomethylidene)benzenesulfonamide Chemical class FC1=CC=C(S(=O)(=O)N=C=O)C=C1 FHMRJRSOWRCSKA-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000004421 aryl sulphonamide group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 230000002218 hypoglycaemic effect Effects 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- DOQQTKLDEQSKIE-UHFFFAOYSA-N silver;isocyanate Chemical compound [Ag+].[N-]=C=O DOQQTKLDEQSKIE-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises sulphonyl ureas of the formula <FORM:0896303/IV (b)/1> in which A is an alkyl group of 1-3 carbon atoms, e.g. methyl, ethyl or isopropyl, or a methoxy group or a halogen atom, e.g. Cl or F, and R1 and R2 together form a 5 or 6 carbon atom, straight or branched, alkylene chain such as pentamethylene, hexamethylene or 1-methylpentamethylene, and salts thereof. The products are prepared by known methods for the preparation of sulphonyl ureas, e.g. by (a) reacting an arylsulphonyl isocyanate, an arylsulphonyl carbamoyl chloride or an N-alkoxycarbonyl-arylsulphonamide with an amine HNR1R2; (b) reacting an N1-unsubstituted arylsulphonyl urea or an N : N1-bis-(arylsulphonyl)-urea with an amine HNR1R2 and decomposing the resulting salt, or (c) reacting an arylsulphonyl chloride with an N-disubstituted-O-alkyl-isourea and hydrolysing the resulting N-arylsulphonyl-O-alkyl-isourea. Arylsulphonyl carbamates. The ethyl esters of p - methyl - and p - isopropyl - benzenesulphonyl - carbamic acids are made by the action of ethyl chloroformate on the arylsulphonamide. Arylsulphonyl isocyanates p-Methoxy-, p-chloro-and p-fluoro, benzenesulphonyl isocyanates are made by the action of silver cyanate on the arylsulphonyl chloride. Pharmaceutical preparations having hypoglycaemic activity comprise the above sulphonyl ureas in known pharmaceutical forms, such as tablets or solutions. The Provisional Specification also describes products wherein NR1R2 is a pyrrolidino group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3496058A GB896303A (en) | 1957-10-31 | 1957-10-31 | Improvements in and relating to sulphonylureas and the manufacture thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3496058A GB896303A (en) | 1957-10-31 | 1957-10-31 | Improvements in and relating to sulphonylureas and the manufacture thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB896303A true GB896303A (en) | 1962-05-16 |
Family
ID=10372128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3496058A Expired GB896303A (en) | 1957-10-31 | 1957-10-31 | Improvements in and relating to sulphonylureas and the manufacture thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB896303A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023114366A3 (en) * | 2021-12-16 | 2023-07-27 | The United States Of America, As Represented By The Secretary, Dept. Of Health And Human Services | N-((adamantan-1-yl)carbamoyl)-benzenesulfonamide derivatives as soluble epoxide hydrolase inhibitors for the treatment of hypertension |
-
1957
- 1957-10-31 GB GB3496058A patent/GB896303A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023114366A3 (en) * | 2021-12-16 | 2023-07-27 | The United States Of America, As Represented By The Secretary, Dept. Of Health And Human Services | N-((adamantan-1-yl)carbamoyl)-benzenesulfonamide derivatives as soluble epoxide hydrolase inhibitors for the treatment of hypertension |
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