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
- 125000000641 acridinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 title 1
- 150000001251 acridines Chemical class 0.000 abstract 5
- 150000004985 diamines Chemical class 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 abstract 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 abstract 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 abstract 2
- 229910019142 PO4 Inorganic materials 0.000 abstract 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 abstract 2
- 150000003893 lactate salts Chemical class 0.000 abstract 2
- 150000002823 nitrates Chemical class 0.000 abstract 2
- 235000021317 phosphate Nutrition 0.000 abstract 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 abstract 2
- 125000006308 propyl amino group Chemical group 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 2
- WXPTXNXCUXXTMO-UHFFFAOYSA-N 1-amino-3-[cyclopentyl(ethyl)amino]-2-methylpropan-2-ol Chemical class NCC(C)(O)CN(CC)C1CCCC1 WXPTXNXCUXXTMO-UHFFFAOYSA-N 0.000 abstract 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 abstract 1
- VNCXFTKLWWHXSB-UHFFFAOYSA-N 4-propylisoindole-1,3-dione Chemical class CCCC1=CC=CC2=C1C(=O)NC2=O VNCXFTKLWWHXSB-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- SRTHFWNTKVOSBA-UHFFFAOYSA-N n-ethylcyclopentanamine Chemical compound CCNC1CCCC1 SRTHFWNTKVOSBA-UHFFFAOYSA-N 0.000 abstract 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 abstract 1
- 150000003335 secondary amines Chemical class 0.000 abstract 1
- 235000009518 sodium iodide Nutrition 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
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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