GB1153272A - Benzenesulphonyl-Ureas and Process for their manufacture - Google Patents
Benzenesulphonyl-Ureas and Process for their manufactureInfo
- Publication number
- GB1153272A GB1153272A GB33285/66A GB3328566A GB1153272A GB 1153272 A GB1153272 A GB 1153272A GB 33285/66 A GB33285/66 A GB 33285/66A GB 3328566 A GB3328566 A GB 3328566A GB 1153272 A GB1153272 A GB 1153272A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzenesulphonyl
- prepared
- ureas
- cyclohexyl
- 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
Classifications
-
- 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
-
- 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
- C07C303/40—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 by reactions not involving the formation of sulfonamide groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/14—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,153,272. Benzenesulphonyl ureas. FARBWERKE HOECHST A.G. 25 July, 1966 [27 July, 1965], No. 33285/66. Heading C2C. Novel compounds of the formula (wherein R is C 1-4 alkyl or C 2-4 alkenyl; X is halogen, C 1-4 alkyl or C 1-4 alkoxy; and R<SP>1</SP> is cyclohexyl, methyl- or ethyl-cyclohexyl or endomethylene - (cyclohexyl or cyclohexenyl)- methyl) and salts thereof are prepared (1) by the action of amines NH 2 R<SP>1</SP> on the appropriately substituted benzenesulphonyl isocyanates, benzenesulphonyl carbamic or thiocarbamic acid esters, benzenesulphonyl carbamic acid halides or benzenesulphonyl ureas; or (2) by the action of R<SP>1</SP>-substituted isocyanates, carbamic acid esters, thiocarbamic acid esters, carbamic acid halides or ureas on appropriately substituted benzenesulphonamides; or (3) by reacting R<SP>1</SP>-substituted ureas, isourea or isothiourea ethers, or parabanic acids with appropriately substituted benzenesulphonyl halides and hydrolysing the products; or (4) by replacing the sulphur atom in appropriately substituted benzenesulphonyl-thioureas by an oxygen atom; or (5) by oxidizing appropriately substituted benzene-sulphinyl ureas or benzene-sulphenyl ureas; or (6) by acylating the corresponding #-aminoethyl compounds. Variations on the above methods are also referred to. N - {4 - [# - (2 - methoxy - 5 - methyl - benzamido) - ethyl] - benzenesulphonyl} - N<SP>1</SP> - (2,5- endomethylenecyclohexylmethyl) - isourea - methyl ether is prepared by reacting the corresponding thiourea (prepared from 2,5-endomethylenecyclohexylmethylisothiocyanate and the appropriately substituted benzene sulphonamide) with methanol in presence of mercury oxide at 50-55‹ C. The corresponding isothiourea methyl ether is prepared from the same starting materials in the presence of methyl iodide at reflux. N - {4 - [# - (2 - methoxy - 5 - chlorobenzamido) - ethyl] - benzenesulphonyl} - N<SP>1</SP>- (2,5 - endomethylene - cyclohexylmethyl) - thiourea is prepared as for the 5-methyl compound. N- {4 - [# - (2 - methoxy - 5 - chloro - benzamido)- ethyl] - benzenesulphonyl} - N<SP>1</SP> - cyclohexyl - isothiourea methyl ether is prepared by reacting the appropriately substituted benzenesulphonamide with CS 2 and KOH in DMF and water to give the corresponding benzenesulphonyl iminodithio carbonic acid potassium salt, reacting this with dimethyl sulphate in the presence of NaOH to give the dimethyl ester of the free acid, and reacting this with cyclohexylamine. N- {4-[#- (2- methoxy - 5 - chlorobenzamido) - ethyl] - benzenesulphonyl} - 3 - cyclohexyl - parabanic acid is prepared from the corresponding benzenesulphochloride and 1-cyclohexyl-parabanic acid. N - {4 - [# - (2 - methoxy - benzamido) - ethyl]- benzenesulphonyl] - N<SP>1</SP> - (4 - methylcyclohexyl)- urea is prepared by acylation of the corresponding #-aminoethyl compound with 2-methoxybenzoyl chloride; on bromination it gives the 5- bromo compound, a product of the invention. The benzenesulphonyl-ureas of the invention, which are stated to have a strong and longlasting hypoglycemic action, may be made up into pharmaceutical compositions for the treatment of diabetes mellitus with suitable carriers.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF46721A DE1301812B (en) | 1965-07-27 | 1965-07-27 | Process for the preparation of benzenesulfonylureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1153272A true GB1153272A (en) | 1969-05-29 |
Family
ID=7101195
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB33285/66A Expired GB1153272A (en) | 1965-07-27 | 1966-07-25 | Benzenesulphonyl-Ureas and Process for their manufacture |
| GB33416/66A Expired GB1149391A (en) | 1965-07-27 | 1966-07-25 | Benzenesulphonyl-ureas and process for their manufacture |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB33416/66A Expired GB1149391A (en) | 1965-07-27 | 1966-07-25 | Benzenesulphonyl-ureas and process for their manufacture |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS526985B1 (en) |
| AT (11) | AT274838B (en) |
| BE (2) | BE684654A (en) |
| BR (2) | BR6681115D0 (en) |
| CH (1) | CH478103A (en) |
| CY (2) | CY534A (en) |
| DE (1) | DE1301812B (en) |
| DK (2) | DK117419B (en) |
| ES (15) | ES329462A1 (en) |
| FI (1) | FI45959C (en) |
| FR (1) | FR5943M (en) |
| GB (2) | GB1153272A (en) |
| IL (2) | IL26016A (en) |
| IN (3) | IN139503B (en) |
| IS (2) | IS756B6 (en) |
| IT (2) | IT1043760B (en) |
| LU (2) | LU51617A1 (en) |
| MC (1) | MC601A1 (en) |
| MY (2) | MY7000111A (en) |
| NL (1) | NL6610580A (en) |
| NO (2) | NO121834B (en) |
| SE (1) | SE328566B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670901A1 (en) * | 1967-08-09 | 1971-03-18 | Hoechst Ag | Process for the preparation of benzenesulfonylureas |
| DE3833439A1 (en) * | 1988-10-01 | 1991-09-12 | Hoechst Ag | METHOD FOR MICRONIZING GLIBENCLAMIDE |
-
1965
- 1965-07-27 DE DEF46721A patent/DE1301812B/en active Pending
-
1966
- 1966-04-25 NO NO162726A patent/NO121834B/no unknown
- 1966-06-22 IL IL26016A patent/IL26016A/en unknown
- 1966-07-08 BR BR181115/66A patent/BR6681115D0/en unknown
- 1966-07-13 DK DK364466AA patent/DK117419B/en unknown
- 1966-07-14 FI FI661889A patent/FI45959C/en active
- 1966-07-14 IT IT15327/66A patent/IT1043760B/en active
- 1966-07-21 IL IL26194A patent/IL26194A/en unknown
- 1966-07-22 LU LU51617D patent/LU51617A1/xx unknown
- 1966-07-22 LU LU51616D patent/LU51616A1/xx unknown
- 1966-07-22 IS IS1581A patent/IS756B6/en unknown
- 1966-07-23 ES ES0329462A patent/ES329462A1/en not_active Expired
- 1966-07-25 AT AT710868A patent/AT274838B/en active
- 1966-07-25 AT AT708266A patent/AT275541B/en active
- 1966-07-25 AT AT08244/68A patent/AT279638B/de not_active IP Right Cessation
- 1966-07-25 AT AT711068A patent/AT274840B/en active
- 1966-07-25 AT AT824368A patent/AT278032B/en not_active IP Right Cessation
- 1966-07-25 GB GB33285/66A patent/GB1153272A/en not_active Expired
- 1966-07-25 AT AT710968A patent/AT274839B/en active
- 1966-07-25 AT AT711268A patent/AT274842B/en active
- 1966-07-25 GB GB33416/66A patent/GB1149391A/en not_active Expired
- 1966-07-25 AT AT711168A patent/AT274841B/en active
- 1966-07-25 AT AT08242/68A patent/AT278031B/en not_active IP Right Cessation
- 1966-07-25 AT AT708166A patent/AT274830B/en active
- 1966-07-26 DK DK388766AA patent/DK123652B/en unknown
- 1966-07-26 SE SE10158/66A patent/SE328566B/xx unknown
- 1966-07-26 MC MC636A patent/MC601A1/en unknown
- 1966-07-26 NO NO164067A patent/NO123569B/no unknown
- 1966-07-26 IT IT17340/66A patent/IT1043761B/en active
- 1966-07-26 IS IS1582A patent/IS822B6/en unknown
- 1966-07-27 BE BE684654D patent/BE684654A/xx not_active IP Right Cessation
- 1966-07-27 CH CH1086166A patent/CH478103A/en not_active IP Right Cessation
- 1966-07-27 BR BR181609/66A patent/BR6681609D0/en unknown
- 1966-07-27 BE BE684652D patent/BE684652A/xx not_active IP Right Cessation
- 1966-07-27 NL NL6610580A patent/NL6610580A/xx unknown
- 1966-07-27 JP JP41049301A patent/JPS526985B1/ja active Pending
- 1966-08-31 AT AT08241/68A patent/AT279637B/en not_active IP Right Cessation
- 1966-10-26 FR FR81659A patent/FR5943M/fr not_active Expired
-
1967
- 1967-08-11 ES ES344046A patent/ES344046A1/en not_active Expired
- 1967-08-11 ES ES344045A patent/ES344045A1/en not_active Expired
- 1967-08-11 ES ES344049A patent/ES344049A1/en not_active Expired
- 1967-08-11 ES ES344048A patent/ES344048A1/en not_active Expired
- 1967-08-11 ES ES344044A patent/ES344044A1/en not_active Expired
- 1967-08-11 ES ES344047A patent/ES344047A1/en not_active Expired
-
1968
- 1968-06-26 ES ES355475A patent/ES355475A1/en not_active Expired
- 1968-06-26 ES ES355477A patent/ES355477A1/en not_active Expired
- 1968-06-26 ES ES355480A patent/ES355480A1/en not_active Expired
- 1968-06-26 ES ES355474A patent/ES355474A1/en not_active Expired
- 1968-06-26 ES ES355481A patent/ES355481A1/en not_active Expired
- 1968-06-26 ES ES355476A patent/ES355476A1/en not_active Expired
- 1968-06-26 ES ES355479A patent/ES355479A1/en not_active Expired
- 1968-06-26 ES ES355478A patent/ES355478A1/en not_active Expired
-
1970
- 1970-04-07 CY CY53470A patent/CY534A/en unknown
- 1970-05-22 CY CY54070A patent/CY540A/en unknown
- 1970-12-31 MY MY1970111A patent/MY7000111A/en unknown
- 1970-12-31 MY MY197086A patent/MY7000086A/en unknown
-
1974
- 1974-08-24 IN IN1914/CAL/74A patent/IN139503B/en unknown
- 1974-08-24 IN IN1912/CAL/74A patent/IN139501B/en unknown
- 1974-08-24 IN IN1917/CAL/74A patent/IN139506B/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1518874C3 (en) | Benzenesulfonylureas and process for their preparation | |
| GB1153272A (en) | Benzenesulphonyl-Ureas and Process for their manufacture | |
| DE1543564C3 (en) | Benzenesulfonylureas, processes for their preparation and pharmaceutical preparations containing them | |
| US3005022A (en) | Process for the production of sulfonylureas | |
| GB1127672A (en) | Benzenesulphonyl-ureas and process for their manufacture | |
| US3504026A (en) | Benzenesulfonyl-ureas | |
| US3754030A (en) | N - (4-(beta-<2-methoxy-5-chloro-benzamido>-ethyl) - benzenesulfonyl)-n'-cyclopentyl-urea and process for its manufacture | |
| US3709908A (en) | Benzenesulfonyl ureas having hypoglycemic activity | |
| GB1132098A (en) | Benzenesulphonyl-ureas and process for preparing them | |
| NO165846B (en) | VINYL CHLORIDE MATERIAL, AND PROCEDURE FOR THE PREPARATION OF SUCH A. | |
| GB1096032A (en) | Benzenesulphonyl-ureas and process for preparing them | |
| US3097240A (en) | Novel sulfonyl-ureas | |
| US3439033A (en) | Benzene-sulfonyl ureas | |
| US3927088A (en) | Sulfonyl ureas and process for preparing them | |
| GB1472127A (en) | Phenyl-thiadiazolyl-thiourea | |
| US3435116A (en) | The treatment of diabetes mellitus with benzenesulfonyl ureas | |
| DE2021828C3 (en) | Benzenesulfonylureas and their pharmacologically non-toxic salts and processes for their preparation and blood sugar-lowering agents containing them | |
| GB1203425A (en) | Benzenesulphonyl ureas and process for their manufacture | |
| DE1443878C (en) | Process for the production of benzene = sulfonylureas | |
| DE1110152B (en) | Process for the preparation of sulfonamides | |
| US3984416A (en) | Substituted quinoline-8-carboxamido ethyl benzene-sulfonyl N-cyclopentylmethyl urea | |
| US2597988A (en) | Production of thiocarbamyl thiazyl monosulfides | |
| CH374984A (en) | Process for the preparation of benzenesulfonylureas | |
| US3169138A (en) | 1-chloro-n-sulfonyl-formamidines and process for their manufacture | |
| DE1443890C (en) | Benzenesulfonyl ureas and process for their preparation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE | Patent expired |