ES340953A1 - Benzenesulfonyl Ureas and process for their manufacture - Google Patents
Benzenesulfonyl Ureas and process for their manufactureInfo
- Publication number
- ES340953A1 ES340953A1 ES340953A ES340953A ES340953A1 ES 340953 A1 ES340953 A1 ES 340953A1 ES 340953 A ES340953 A ES 340953A ES 340953 A ES340953 A ES 340953A ES 340953 A1 ES340953 A1 ES 340953A1
- Authority
- ES
- Spain
- Prior art keywords
- radical
- group
- prepared
- methyl
- benzenesulphonyl
- 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
-
- 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
- C07C311/59—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 carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/50—Spiro compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
- C07C2603/66—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing five-membered rings
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Silicon Compounds (AREA)
Abstract
Novel benzenesulphonyl-ureas (including salts thereof) of the general formula wherein R is alkyl or phenylalkyl radical or preferably hydrogen, R1 represents (a) a cyclohexyl radical containing a methyl group and an alkoxy group containing 1 or 2 carbons, (b) a chlorocyclohexyl group, (c) a spiro-(5,5)-undecyl-(3) group, (d) an exo-tricyclo-(3,2,1,02,4) octane group, (e) a 4-methylcyclohexenyl group or (f) a dimethyl- or 4,4-diethylcyclohexyl group X represents (a) a phenyl radical carrying in any desired positions the substituents Z and Z1 which may be identical or different in which Z is a hydrogen or halogen atom or an alkyl, alkenyl, alkoxy, alkenoxy, haloalkoxy, alkoxyalkoxy, phenylalkoxy, phenylalkyl, cycloalkoxy, phenyl, phenoxy, acyl, acyloxy, or a benzoyl radical, or a -CF 3 , -OH, -CN or -NO 2 group, Z1 represents a hydrogen or halogen atom or an alkyl, alkoxy, alkoxyalkoxy or acyloxy radical or a hydroxyl group, (b) a naphthyl radical which may be mono- or di-substituted by a halogen atom or an alkyl or alkoxy radical or a hydroxyl group, (c) a tetrahydronaphthyl radical or an indanyl radical, (d) a thienyl radical which may be mono- or di-substituted by alkyl, phenylalkyl, alkoxy, alkoxyalkoxy, alkenoxy, phenylalkoxy and aryl radicals and halogen atoms or (e) a tetramethylene- or trimethylene-thienyl radical and Y represents a hydrocarbon chain of 1-3 carbon atoms and wherein the phenylene group may be substituted by one or more halogen, alkyl or alkoxy, are prepared utilizing standard methods. 1 - [4 - (# - [2 - Methoxy - 5 - chlorobenzamido]- ethyl) - benzenesulphonyl] - 3 - (4 - chlorocyclohexyl)-parabanic acid is prepared by the interaction of 4-chlorocyclohexyl-parabanic acid and the appropriately substituted benzene-sulphochloride. N - [4 - (# - [2 - Methoxy - 5 - chlorobenzamido] - ethyl) - benzenesulphonyl] - N1 - (4, 4-dimethylcyclohexyl)-thiourea is obtained by reacting 4,4-dimethylcyclohexylisocyanate with the appropriately substituted benzenesulphonamide. Treatment of this thiourea with HgO/ MeOH yields the corresponding isourea methyl ether and N - [4 - (# - [2 - methoxy - 5 - chlorobenzamido] - ethyl) - benzenesulphonyl] - N1 - 2- chlorocyclohexyl-isourea methyl ether is similarly prepared from the corresponding thiourea. N,N1 - Bis - 4 - [# - (benzamido - ethyl) - benzenesulphonyl]-urea is obtained by reacting 4-(#- benzamidoethyl ) -benzenesulphonamide sodium with 4 - (# - benzamidoethyl) - benzenesulphonyl-carbamic acid methyl ester. 4,4-Dimethylcyclohexyl parabanic acid is prepared by the interaction of 4,4-dimethylcyclohexyl-urea and oxalyl chloride. Exo - tricyclo - [3,2,1,02,4] - octane - 3 - antiisocyanate and 4 - methyl - #3 - cyclohexenylisocyanate are prepared by heating the corresponding acid azides which are in turn prepared from the corresponding acids. 4,4 - Diethyl - cyclohexyl - isocyanate is obtained by reacting 4,4-diethyl-cyclohexylamine with phosgene. 4 - Methyl - 3 - methoxy - (or 3 - ethoxy)- cyclohexylamine (the 3-methoxy compound being isolated as the acetate) are obtained by hydrogenating the corresponding benzene compounds. 4 - Methyl - #3 - cyclohexenylamine is prepared by treating 4-methyl-#3-cyclohexenyl-isocyanate with acetic acid. 4-Chloro-cyclohexylamine is obtained by the interaction of 4-aminocyclohexanol and PCl 5 . Pharmaceutical preparations having hypoglycaemic activity comprise the above novel compounds in admixture or conjunction with a carrier, preferably in a form adapted to oral administration, e.g. tablets.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1966F0049329 DE1252201B (en) | 1966-05-28 | 1966-05-28 | Process for the preparation of benzenesulfonylureas |
| DE1967F0052152 DE1618402B2 (en) | 1966-05-28 | 1967-04-18 | BENZENE SULFONYL UREA, METHOD OF MANUFACTURING AND PHARMACEUTICAL PREPARATIONS THEREOF |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES340953A1 true ES340953A1 (en) | 1968-10-01 |
Family
ID=25977218
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES340953A Expired ES340953A1 (en) | 1966-05-28 | 1967-05-24 | Benzenesulfonyl Ureas and process for their manufacture |
| ES353814A Expired ES353814A1 (en) | 1966-05-28 | 1968-05-11 | Benzenesulfonyl Ureas and process for their manufacture |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES353814A Expired ES353814A1 (en) | 1966-05-28 | 1968-05-11 | Benzenesulfonyl Ureas and process for their manufacture |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS5133903B1 (en) |
| AR (3) | AR192396A1 (en) |
| AT (2) | AT324349B (en) |
| BE (1) | BE699134A (en) |
| CH (7) | CH502320A (en) |
| CY (1) | CY567A (en) |
| DE (1) | DE1618402B2 (en) |
| DK (1) | DK129414B (en) |
| ES (2) | ES340953A1 (en) |
| FI (1) | FI46155C (en) |
| FR (2) | FR1524754A (en) |
| GB (1) | GB1182694A (en) |
| IL (1) | IL28034A (en) |
| IS (1) | IS734B6 (en) |
| LU (1) | LU53740A1 (en) |
| MC (1) | MC654A1 (en) |
| MY (1) | MY7100059A (en) |
| NL (2) | NL157592B (en) |
| NO (1) | NO122921B (en) |
| OA (1) | OA03625A (en) |
| SE (1) | SE336331B (en) |
| SU (3) | SU407445A3 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7200696A (en) * | 1971-01-23 | 1972-07-25 | ||
| WO2018215818A1 (en) | 2017-05-24 | 2018-11-29 | The University Of Queensland | Novel compounds and uses |
-
1967
- 1967-04-18 DE DE1967F0052152 patent/DE1618402B2/en active Granted
- 1967-05-22 DK DK266367AA patent/DK129414B/en unknown
- 1967-05-23 FI FI671459A patent/FI46155C/en active
- 1967-05-24 ES ES340953A patent/ES340953A1/en not_active Expired
- 1967-05-24 IS IS1648A patent/IS734B6/en unknown
- 1967-05-24 IL IL28034A patent/IL28034A/en unknown
- 1967-05-24 LU LU53740D patent/LU53740A1/xx unknown
- 1967-05-25 CH CH1948869A patent/CH502320A/en not_active IP Right Cessation
- 1967-05-25 CH CH1948669A patent/CH502318A/en not_active IP Right Cessation
- 1967-05-25 CH CH1948769A patent/CH502319A/en not_active IP Right Cessation
- 1967-05-25 CH CH979571A patent/CH533091A/en not_active IP Right Cessation
- 1967-05-25 CH CH739467A patent/CH503709A/en not_active IP Right Cessation
- 1967-05-25 CH CH1948569A patent/CH533090A/en not_active IP Right Cessation
- 1967-05-25 CH CH1948469A patent/CH502998A/en not_active IP Right Cessation
- 1967-05-26 AT AT493767A patent/AT324349B/en not_active IP Right Cessation
- 1967-05-26 NL NL6707340.A patent/NL157592B/en unknown
- 1967-05-26 AT AT375674A patent/AT326682B/en active
- 1967-05-26 SE SE07405/67A patent/SE336331B/xx unknown
- 1967-05-26 MC MC694A patent/MC654A1/en unknown
- 1967-05-27 SU SU1443576A patent/SU407445A3/ru active
- 1967-05-27 NO NO168334A patent/NO122921B/no unknown
- 1967-05-27 OA OA52951A patent/OA03625A/en unknown
- 1967-05-27 SU SU1443578A patent/SU465783A3/en active
- 1967-05-28 SU SU1444380A patent/SU468403A3/en active
- 1967-05-29 JP JP42034115A patent/JPS5133903B1/ja active Pending
- 1967-05-29 BE BE699134D patent/BE699134A/xx unknown
- 1967-05-29 FR FR108207A patent/FR1524754A/en not_active Expired
- 1967-05-30 GB GB24852/67A patent/GB1182694A/en not_active Expired
- 1967-08-25 FR FR119022A patent/FR6497M/fr not_active Expired
-
1968
- 1968-05-11 ES ES353814A patent/ES353814A1/en not_active Expired
-
1970
- 1970-04-10 AR AR228019A patent/AR192396A1/en active
- 1970-11-26 CY CY56770A patent/CY567A/en unknown
-
1971
- 1971-12-30 MY MY59/71A patent/MY7100059A/en unknown
-
1972
- 1972-12-28 AR AR245895A patent/AR193007A1/en active
- 1972-12-31 AR AR245611A patent/AR192829A1/en active
-
1978
- 1978-02-10 NL NL7801563A patent/NL7801563A/en unknown
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