GB873018A - Substituted phenylcyclopropylamines - Google Patents
Substituted phenylcyclopropylaminesInfo
- Publication number
- GB873018A GB873018A GB26376/59A GB2637659A GB873018A GB 873018 A GB873018 A GB 873018A GB 26376/59 A GB26376/59 A GB 26376/59A GB 2637659 A GB2637659 A GB 2637659A GB 873018 A GB873018 A GB 873018A
- Authority
- GB
- United Kingdom
- Prior art keywords
- isomer
- trans
- case
- cis
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Abstract
The invention comprises compounds of the general formula <FORM:0873018/IV (b)/1> (wherein R represents a bromine, chlorine or fluorine atom or a trifluoromethyl group and Z an amino or mono- or di-methylamino group) and their non-toxic pharmaceutically acceptable acid addition salts, and the preparation thereof by the processes of the examples, which may be summarized as follows: an R-substituted styrene is condensed with ethyl diazoacetate to form the correspondingly-substituted ethyl 2-phenylcyclopropanecarboxylate; saponification and separation into cisand trans-isomers follow in either order; the cis- and trans-acids are converted into their azides (preferably via the methyl ester and the hydrazide in the case of the cis-isomer and via the acid chloride in the case of the trans-isomer); the azides are converted into the primary amines of the general formula above (Z = NH2) (preferably via the methylurethane in the case of the cis-isomer and via the isocyanate in the case of the trans-isomer); finally, if desired, the products are monomethylated by reaction with benzaldehyde and treatment of the resulting benzalamine with methyl iodide in a sealed container at 100-105 DEG C., or dimethylated with aqueous formaldehyde and formic acid. The monomethylated compounds can also be prepared by LiAlH4 reduction of the isocyanates or of the N-carbethoxy derivatives obtained by reacting the primary amines with ethyl chloroformate. The products are useful as ataractic, antidepressant and hypotensive agents.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US873018XA | 1958-09-22 | 1958-09-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB873018A true GB873018A (en) | 1961-07-19 |
Family
ID=22204353
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB26376/59A Expired GB873018A (en) | 1958-09-22 | 1959-07-31 | Substituted phenylcyclopropylamines |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB873018A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4705807A (en) * | 1975-05-08 | 1987-11-10 | Lilly Industries Limited | Amine derivatives |
US5961987A (en) * | 1996-10-31 | 1999-10-05 | University Of Iowa Research Foundation | Ocular protein stimulants |
JP2003535072A (en) * | 2000-06-02 | 2003-11-25 | アストラゼネカ アクチボラグ | Method for preparing cyclopropylcarboxylic acid ester and derivative |
-
1959
- 1959-07-31 GB GB26376/59A patent/GB873018A/en not_active Expired
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4705807A (en) * | 1975-05-08 | 1987-11-10 | Lilly Industries Limited | Amine derivatives |
US5961987A (en) * | 1996-10-31 | 1999-10-05 | University Of Iowa Research Foundation | Ocular protein stimulants |
JP2003535072A (en) * | 2000-06-02 | 2003-11-25 | アストラゼネカ アクチボラグ | Method for preparing cyclopropylcarboxylic acid ester and derivative |
EP1760066A2 (en) * | 2000-06-02 | 2007-03-07 | AstraZeneca AB | Processes for the preparation of cyclopropyl carboxylic acid derivatives and intermediates provided by these processes |
EP1760066A3 (en) * | 2000-06-02 | 2008-09-10 | AstraZeneca AB | Processes for the preparation of cyclopropyl carboxylic acid derivatives and intermediates provided by these processes |
US7906662B2 (en) | 2000-06-02 | 2011-03-15 | Astrazeneca Ab | Process for the preparation of cyclopropyl carboxylic acid esters and derivatives |
EP2292591A3 (en) * | 2000-06-02 | 2011-11-02 | AstraZeneca AB | Process for the preparation of cyclopropyl derivatives |
EP2292582A3 (en) * | 2000-06-02 | 2011-11-02 | AstraZeneca AB | 2-substituted 1-(3,4-difluorophenyl)cyclopropane derivatives |
US8183412B2 (en) | 2000-06-02 | 2012-05-22 | Astrazeneca Ab | Process for the preparation of cyclopropyl carboxylic acid esters and derivatives |
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