GB929737A - Improvements in or relating to n-phenethyl-2-phenylcyclopropylamine derivatives - Google Patents
Improvements in or relating to n-phenethyl-2-phenylcyclopropylamine derivativesInfo
- Publication number
- GB929737A GB929737A GB23976/61A GB2397661A GB929737A GB 929737 A GB929737 A GB 929737A GB 23976/61 A GB23976/61 A GB 23976/61A GB 2397661 A GB2397661 A GB 2397661A GB 929737 A GB929737 A GB 929737A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cis
- acid
- trans
- prepared
- phenylcyclopropylamine
- 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises N-phenethyl-2-phenylcyclopropylamine derivatives of the general formula <FORM:0929737/IV(a)/1> (wherein R1 and R2 are phenyl, chlorophenyl, fluorophenyl, trifluoromethylphenyl, lower alkoxyphenyl, lower alkylphenyl, dichlorophenyl, di-lower alkylphenyl, di-lower alkoxyphenyl or methylenedioxyphenyl, R3 is hydrogen, lower alkyl or hydroxyethyl, and R4 is lower alkyl) and non-toxic, pharmaceutically acceptable, acid addition salts thereof, and their preparation by the processes of the examples which may be summarized by the following reaction scheme:- <FORM:0929737/IV(a)/2> (wherein R3 is lower alkyl or hydroxyethyl), optionally followed by salt formation. The "lower alkyl" and "lower alkoxy" groups are defined as those containing from 1 to 4 carbon atoms. These compounds may be the cis- and transisomers and the resolved d-, l-, d1- and l1-isomers prepared by using the appropriate starting material, followed by resolution), or mixtures of cis-trans, dl- and d1l1-isomers. The compounds are anorexigenic agents, anti-depressants, ataractics and monoamine oxidase inhibitors. The cis-, trans- and cis-trans-2-phenylcyclopropylamine starting materials may be prepared by the following process: <FORM:0929737/IV(a)/3> The acid may be converted to the azide via the acid chloride. Alternatively, the acid may be converted to the amine via the methyl ester, hydrazide, azide and methyl urethane. The separation of the cis- and transisomers may be effected at the ethyl ester or acid stage. The benzyl alkyl ketone starting materials may be prepared by reacting the appropriate phenylacetic acid with an excess of the appropriate acid anhydride in the presence of a basic catalyst. 4-Trifluoromethylphenylacetic acid is prepared from 4-bromobenzotrifluoride via 4- trifluoromethylbenzaldehyde, 4- trifluoromethylbenzyl alcohol, 4-trifluoromethylbenzyl bromide and 4-trifluoromethylbenzyl cyanide. d-cis, l-cis, d-trans- and l-trans-2-Phenylcyclopropylamine are prepared from dl-cis-and dl-trans-2-phenylcyclopropylamine via the tartrates.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56363A US3106578A (en) | 1960-09-16 | 1960-09-16 | Nu-phenethyl-2-phenylcyclopropylamine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB929737A true GB929737A (en) | 1963-06-26 |
Family
ID=22003899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23976/61A Expired GB929737A (en) | 1960-09-16 | 1961-07-03 | Improvements in or relating to n-phenethyl-2-phenylcyclopropylamine derivatives |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3106578A (en) |
| GB (1) | GB929737A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1133395B (en) * | 1960-11-12 | 1962-07-19 | Hoechst Ag | Process for the production of phenylalkylamines with cardiovascular effects |
| US3197507A (en) * | 1963-03-21 | 1965-07-27 | American Home Prod | Substituted 3-p-fluorobenzoylpropylphenylalkylamines and method for making the same |
| US3226440A (en) * | 1963-06-07 | 1965-12-28 | Sahyun | Beta-loweralkoxy-trifluoromethyl-phenethylamines |
| US3171858A (en) * | 1963-08-30 | 1965-03-02 | Parke Davis & Co | alpha-ethylamino-o-methylisobutyrophenone |
| NL128365C (en) * | 1963-11-05 | |||
| TWI229674B (en) | 1998-12-04 | 2005-03-21 | Astra Pharma Prod | Novel triazolo[4,5-d]pyrimidine compounds, pharmaceutical composition containing the same, their process for preparation and uses |
| WO2010043721A1 (en) | 2008-10-17 | 2010-04-22 | Oryzon Genomics, S.A. | Oxidase inhibitors and their use |
| US8993808B2 (en) | 2009-01-21 | 2015-03-31 | Oryzon Genomics, S.A. | Phenylcyclopropylamine derivatives and their medical use |
| CA2812683C (en) | 2009-09-25 | 2017-10-10 | Oryzon Genomics S.A. | Lysine specific demethylase-1 inhibitors and their use |
| WO2011042217A1 (en) | 2009-10-09 | 2011-04-14 | Oryzon Genomics S.A. | Substituted heteroaryl- and aryl- cyclopropylamine acetamides and their use |
| US9616058B2 (en) | 2010-02-24 | 2017-04-11 | Oryzon Genomics, S.A. | Potent selective LSD1 inhibitors and dual LSD1/MAO-B inhibitors for antiviral use |
| WO2011106573A2 (en) | 2010-02-24 | 2011-09-01 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with hepadnaviridae |
| DK2560947T3 (en) | 2010-04-19 | 2016-11-21 | Oryzon Genomics Sa | LYSINE-SPECIFIC demethylase-1 INHIBITORS AND THEIR USE |
| LT2598482T (en) | 2010-07-29 | 2018-07-10 | Oryzon Genomics, S.A. | Arylcyclopropylamine based demethylase inhibitors of lsd1 and their medical use |
| WO2012013727A1 (en) | 2010-07-29 | 2012-02-02 | Oryzon Genomics S.A. | Cyclopropylamine derivatives useful as lsd1 inhibitors |
| US9061966B2 (en) | 2010-10-08 | 2015-06-23 | Oryzon Genomics S.A. | Cyclopropylamine inhibitors of oxidases |
| WO2012072713A2 (en) | 2010-11-30 | 2012-06-07 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for diseases and disorders associated with flaviviridae |
| EP2712315B1 (en) | 2011-02-08 | 2021-11-24 | Oryzon Genomics, S.A. | Lysine demethylase inhibitors for myeloproliferative disorders |
| BR112014009306B1 (en) | 2011-10-20 | 2021-07-20 | Oryzon Genomics S.A. | (HETERO)ARIL CYCLOPROPILAMINE COMPOUNDS AS LSD1 INHIBITORS |
| WO2013057322A1 (en) | 2011-10-20 | 2013-04-25 | Oryzon Genomics, S.A. | (hetero)aryl cyclopropylamine compounds as lsd1 inhibitors |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2195076A (en) * | 1936-10-24 | 1940-03-26 | Gen Aniline & Film Corp | Process of replacing halogen in cyclic halogen compounds and product thereof |
| US2542460A (en) * | 1945-06-29 | 1951-02-20 | Frank W Baukus | Cutter and housing with magnifying glass |
| US2476264A (en) * | 1947-01-18 | 1949-07-12 | Rohm & Haas | Araliphatic nitriles |
| US2597445A (en) * | 1948-12-23 | 1952-05-20 | Wyeth Corp | Nu-alkylamino-methyl-phenyl-propane and method of preparing same |
-
1960
- 1960-09-16 US US56363A patent/US3106578A/en not_active Expired - Lifetime
-
1961
- 1961-07-03 GB GB23976/61A patent/GB929737A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US8183412B2 (en) | 2000-06-02 | 2012-05-22 | Astrazeneca Ab | Process for the preparation of cyclopropyl carboxylic acid esters and derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| US3106578A (en) | 1963-10-08 |
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