GB1149391A - Benzenesulphonyl-ureas and process for their manufacture - Google Patents
Benzenesulphonyl-ureas and process for their manufactureInfo
- Publication number
- GB1149391A GB1149391A GB33416/66A GB3341666A GB1149391A GB 1149391 A GB1149391 A GB 1149391A GB 33416/66 A GB33416/66 A GB 33416/66A GB 3341666 A GB3341666 A GB 3341666A GB 1149391 A GB1149391 A GB 1149391A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzenesulphonyl
- acid
- benzamido
- chloro
- methoxy
- 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)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (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
1,149,391. Benzenesulphonyl-ureas and process for their manufacture. FARBWERKE HOECHST A.G. 25 July, 1966 [27 July, 1965], No. 33416/66. Heading C2C. Novel compounds of the general formula and their physiologically tolerable salts with bases, for example sodium salts, wherein X represents a chlorine or bromine atom or a methyl group linked to the 4- or 5-position with respect to the carboxylic amide group, preferably a chlorine atom, and Y represents a hydrogen atom or a methyl group are prepared by one of the following methods: (a) Reacting a benzenesulphonyl-isocyanate, -carbamic acid ester, -thiolcarbamic acid ester, -urea, -semi-carbazide or -semicarbazone carrying the substituent of formula in the p-position with an amine carrying the substituent of Formula III or a salt thereof; (b) reacting a sulphonamide of the formula or a salt thereof with an isocyanate, carbamic acid ester, thiolcarbamic acid ester, carbamic acid halide or urea carrying the substituent of Formula III (c) hydrolysing a correspondingly substituted benzenesulphonyl-isourea ether, -isourea ester, -isothiourea ether, -parabanic acid or -haloformic acid amidine; (d) adding water on to a correspondingly substituted carbodiimide; (e) replacing the sulphur atom in a correspondingly substituted benzene-sulphonyl-thiourea by an oxygen atom; (f) hydrogenating a corresponding benzenesulphonyl-urea containing, in the molecule, an unsaturated linkage; and (g) introducing by acylation the radical of formula into a benzenesulphonyl-urea of the formula and, if desired, converting the resulting compound into a physiologically tolerable salt thereof by reaction with a base. N - [4 - (beta - <2 - methoxy 5 - chloro - benzamido > - ethyl) - benzenesulphonyl] - N<SP>1</SP> - acetylurea is prepared by acylation with acetic acid anhydride of the amine. N,N<SP>1</SP> - bis - 4 - [beta - < - 2 - methoxy - 5- chloro - benzamido > - ethyl) - benzenesulphonyl]- urea is prepared by treatment of the corresponding carbamic acid with ammonia in the presence of the corresponding sulphonamide. N - [4 - (beta - < 2 - methoxy - 5 - chloro - benzamido > - ethyl) - benzenesulphonyl] - 3 - cyclohexyl-parabanic acid is prepared by reaction of N - cyclohexyl - parabanic acid and 4 - (beta- [2 - methoxy - 5 - chloro - benzamido] - ethyl)- benzenesulphochloride. N - [4 - beta - < 2 - methoxy - 5 - chloro - benzamido > ethyl) - benzenesulphonyl] - N<SP>1</SP> - cyclohexyl-isothiourea methyl ether is prepared by reaction of cyclohexylamine and N<SP>1</SP>[4-(beta-<2- methoxy - 5 - chloro - benzamido > ethyl) - benzenesulphonyl] - imino - dithiocarbonic acid dimethyl ester which is itself prepared by reaction of dimethyl sulphate on the potassium salt of the corresponding dithiocarbonic acid. Pharmaceutical compositions in conventional form for oral or parenteral administration useful in treating diabetes comprise an above novel compound and a suitable pharmaceutical carrier.
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 |
|---|---|
| GB1149391A true GB1149391A (en) | 1969-04-23 |
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 Before (1)
| 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 |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS526985B1 (en) |
| AT (11) | AT279638B (en) |
| BE (2) | BE684652A (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) | IN139501B (en) |
| IS (2) | IS756B6 (en) |
| IT (2) | IT1043760B (en) |
| LU (2) | LU51616A1 (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 LU51616D patent/LU51616A1/xx unknown
- 1966-07-22 IS IS1581A patent/IS756B6/en unknown
- 1966-07-22 LU LU51617D patent/LU51617A1/xx unknown
- 1966-07-23 ES ES0329462A patent/ES329462A1/en not_active Expired
- 1966-07-25 AT AT08244/68A patent/AT279638B/de not_active IP Right Cessation
- 1966-07-25 GB GB33285/66A patent/GB1153272A/en not_active Expired
- 1966-07-25 AT AT708166A patent/AT274830B/en active
- 1966-07-25 AT AT708266A patent/AT275541B/en active
- 1966-07-25 AT AT824368A patent/AT278032B/en not_active IP Right Cessation
- 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 AT711068A patent/AT274840B/en active
- 1966-07-25 GB GB33416/66A patent/GB1149391A/en not_active Expired
- 1966-07-25 AT AT710968A patent/AT274839B/en active
- 1966-07-25 AT AT710868A patent/AT274838B/en active
- 1966-07-25 AT AT711268A patent/AT274842B/en active
- 1966-07-26 DK DK388766AA patent/DK123652B/en unknown
- 1966-07-26 IT IT17340/66A patent/IT1043761B/en active
- 1966-07-26 NO NO164067A patent/NO123569B/no unknown
- 1966-07-26 IS IS1582A patent/IS822B6/en unknown
- 1966-07-26 MC MC636A patent/MC601A1/en unknown
- 1966-07-26 SE SE10158/66A patent/SE328566B/xx unknown
- 1966-07-27 BE BE684652D patent/BE684652A/xx not_active IP Right Cessation
- 1966-07-27 CH CH1086166A patent/CH478103A/en not_active IP Right Cessation
- 1966-07-27 NL NL6610580A patent/NL6610580A/xx unknown
- 1966-07-27 BE BE684654D patent/BE684654A/xx not_active IP Right Cessation
- 1966-07-27 JP JP41049301A patent/JPS526985B1/ja active Pending
- 1966-07-27 BR BR181609/66A patent/BR6681609D0/en unknown
- 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 ES344044A patent/ES344044A1/en not_active Expired
- 1967-08-11 ES ES344048A patent/ES344048A1/en not_active Expired
- 1967-08-11 ES ES344046A patent/ES344046A1/en not_active Expired
- 1967-08-11 ES ES344049A patent/ES344049A1/en not_active Expired
- 1967-08-11 ES ES344045A patent/ES344045A1/en not_active Expired
- 1967-08-11 ES ES344047A patent/ES344047A1/en not_active Expired
-
1968
- 1968-06-26 ES ES355481A patent/ES355481A1/en not_active Expired
- 1968-06-26 ES ES355478A patent/ES355478A1/en not_active Expired
- 1968-06-26 ES ES355474A patent/ES355474A1/en not_active Expired
- 1968-06-26 ES ES355480A patent/ES355480A1/en not_active Expired
- 1968-06-26 ES ES355475A patent/ES355475A1/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 ES355477A patent/ES355477A1/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 IN1912/CAL/74A patent/IN139501B/en unknown
- 1974-08-24 IN IN1914/CAL/74A patent/IN139503B/en unknown
- 1974-08-24 IN IN1917/CAL/74A patent/IN139506B/en unknown
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