GB600851A - Production of substituted propyldiamines and particularly their acridine compounds - Google Patents
Production of substituted propyldiamines and particularly their acridine compoundsInfo
- Publication number
- GB600851A GB600851A GB20032/45A GB2003245A GB600851A GB 600851 A GB600851 A GB 600851A GB 20032/45 A GB20032/45 A GB 20032/45A GB 2003245 A GB2003245 A GB 2003245A GB 600851 A GB600851 A GB 600851A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- hydroxy
- propylamino
- substituted
- 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
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
2 - Methoxy - 6 - chloro - 9 - [21 - substituted-31-(disubstituted-amino)propylamino] acridines of the general formula <FORM:0600851/IV(b)/1> wherein R and R1 represent different, non-tertiary, saturated hydrocarbon radicals and the sum of their carbon atoms does not exceed 10, and R11 represents hydrogen or the methyl radical, are prepared by condensing 2-methoxy-6 : 9-dichloroacridine with a diamine of the general formula <FORM:0600851/IV(b)/2> where R, R1 and R11 have the significance indicated above. The bases may be converted to their salts by the addition of acids. In examples (1) to (5), 2-methoxy-6 : 9-dichloroacridine is condensed with 21-hydroxy-21-methyl - 31 - (methyl - n - propylamino) -, 21-hydroxy - 31 - (n - propyl - iso - propylamino)-, 21 - hydroxy - 31 - (n - butylethylamino)-, 21-hydroxy - 31 - (methyl - n - propylamino)-, and 21 - hydroxy - 21 - methyl - 31 - (ethylcyclopentylamino) - propylamines and the substituted acridines are converted into their dihydrohalides; (8) the substituted acridines prepared as in (1) to (5) are converted into their dihydrobromides, sulphates, nitrates, phosphates, lactates or propionates. Diamines of the general formula <FORM:0600851/IV(b)/3> where R, R1 and R11 have the above significance, are prepared (i) when R11 is hydrogen by reacting a secondary amine with 1-chloro-2 : 3-epoxypropane in a solvent, e.g. methoxyethanol and adding potassium phthalimide and sodium iodide and hydrolysing the resulting substituted propylphthalimide and (ii) when R11 represents the methyl radical, 1-chloro-2-methyl-2 : 3-epoxypropane is reacted as in (1). In examples (1) to (5), the preparation of the following diamines is described: 2 - hydroxy - 2 - methyl - 3 - (methyl - n - propylamino) -, 2-hydroxy - 3 - (n - propyl - iso - propylamino) -, 2 - hydroxy - 3 - (n - butylethylamino)-, 2-hydroxy - 3 - (methyl - n - propylamino)-, and 2 - hydroxy - 2 - methyl - 3 - (ethylcyclopentylamino)-propylamines. Ethylcyclopentylamine is prepared by reducing a mixture of ethylamine and cyclopentanone with hydrogen in the presence of Raney nickel catalyst and under heat and pressure.ALSO: 2-Methoxy-6-chloro-9-[21-substituted-31-(disubstituted -amino) propylamino]-acridines of the general formula <FORM:0600851/IV (c)/1> wherein R and R1 represent different, non-tertiary, saturated hydrocarbon radicals and the sum of their carbon atoms does not exceed 10, and R11 represents hydrogen or the methyl radical, are prepared by condensing 2-methoxy-6 : 9-dichloroacridine with a diamine of the general formula <FORM:0600851/IV (c)/2> where R, R1 and N11 have the significance indicated above. The bases may be converted to their salts by the addition of acids. In examples (1) to (5), 2-methoxy-6 : 9-dichloroacridine is condensed with 21-hydroxy-21-methyl - 31 - (methyl - n - propylamino)-, 21-hydroxy-31-(n-propyl-iso-propylamino)-, 21-hydroxy-31-(n-butylethylamino)-, 21-hydroxy-31-(methyl-n-propylamino)-, and 21-hydroxy-21-methyl-31-(ethylcyclopentylamino) -propylamines and the substituted acridines are converted into their dihydrohalides; (8) the substituted acridines prepared as in (1) to (5) are converted into their dihydrobromides, sulphates, nitrates, phosphates, lactates or propionates.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US600851XA | 1944-08-07 | 1944-08-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB600851A true GB600851A (en) | 1948-04-21 |
Family
ID=22027242
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB20032/45A Expired GB600851A (en) | 1944-08-07 | 1945-08-03 | Production of substituted propyldiamines and particularly their acridine compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB600851A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9221760B2 (en) | 2011-05-09 | 2015-12-29 | Van Andel Research Institute | Autophagy inhibitors |
-
1945
- 1945-08-03 GB GB20032/45A patent/GB600851A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9221760B2 (en) | 2011-05-09 | 2015-12-29 | Van Andel Research Institute | Autophagy inhibitors |
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