GB924589A - Azetidine derivatives and process for their preparation - Google Patents
Azetidine derivatives and process for their preparationInfo
- Publication number
- GB924589A GB924589A GB1678861A GB1678861A GB924589A GB 924589 A GB924589 A GB 924589A GB 1678861 A GB1678861 A GB 1678861A GB 1678861 A GB1678861 A GB 1678861A GB 924589 A GB924589 A GB 924589A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- radical
- treating
- alkyl
- represents hydrogen
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises azetidine-2-ones of the general formula: <FORM:0924589/IV(a)/1> wherein R1 represents a hydrocarbon radical which may be substituted in any aromatic nucleus present by halogen and/or alkoxy; R2 represents a cycloalkyl radical or an aryl or aralkyl radical optionally substituted by halogen or alkoxy; R3 represents hydrogen, a lower alkyl or alkenyl radical, or a lower dialkylaminoalkyl radical the alkyl radicals of which may be bound to each other direct or by way of oxygen; and R4 represents hydrogen or a lower alkyl group (the term 'lower' indicates that the group so described contains up to 6 carbon atoms) and the preparation thereof by cyclising a b -aminocarboxylic acid: R3NH,CR1R2,CHR4,COOH or a reactive functional derivative thereof and if desired, treating the compound obtained provided that R3 therein represents hydrogen, with a reactive ester of an alcohol R31OH where R31 represents a radical corresponding to the definition for R3 with the exception of hydrogen, in the presence of an acid binding agent. Ring closure methods are more specifically (a) treating an alkyl ester of the b -amino propionic acid with an alkyl magnesium halide and hydrolysing the metal complex formed; (b) treating the acid chloride with a tertiary organic base; (c) heating, preferably under reduced pressure, an N-alkanoyl derivative of the free acid; and (d) treating the b -aminocarboxylic acid with phosphorus trichloride or with an N,N1-disubstituted carbodiimide. The b -amino propionic acids used as starting materials are prepared by Hofmann degradation of the a ,a -disubstituted-succin-a -amide acid. b -(p-Chlorophenyl)-b - ethyl-b -aminopropionic acid chloride hydrochloride is prepared from the acid and thionyl chloride. Central depressant, soporific and sedative compositions comprise the azetidine-2-ones of the invention in the form of tablets, coated tablets or capsules for peroral administration.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH544360 | 1960-05-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB924589A true GB924589A (en) | 1963-04-24 |
Family
ID=4293657
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1678861A Expired GB924589A (en) | 1960-05-10 | 1961-05-09 | Azetidine derivatives and process for their preparation |
Country Status (3)
Country | Link |
---|---|
BE (1) | BE603661A (en) |
ES (1) | ES267254A1 (en) |
GB (1) | GB924589A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000003982A1 (en) * | 1998-07-17 | 2000-01-27 | Astrazeneca Ab | Cyclisation process |
-
1961
- 1961-05-09 GB GB1678861A patent/GB924589A/en not_active Expired
- 1961-05-09 ES ES0267254A patent/ES267254A1/en not_active Expired
- 1961-05-10 BE BE603661A patent/BE603661A/en unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000003982A1 (en) * | 1998-07-17 | 2000-01-27 | Astrazeneca Ab | Cyclisation process |
US6333418B1 (en) | 1998-07-17 | 2001-12-25 | Astrazeneca Ab | Cyclisation process |
Also Published As
Publication number | Publication date |
---|---|
ES267254A1 (en) | 1961-11-01 |
BE603661A (en) | 1961-11-10 |
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