GB722704A - Improvements in or relating to the production of meso-substituted aza-acridines - Google Patents
Improvements in or relating to the production of meso-substituted aza-acridinesInfo
- Publication number
- GB722704A GB722704A GB3757/51A GB375751A GB722704A GB 722704 A GB722704 A GB 722704A GB 3757/51 A GB3757/51 A GB 3757/51A GB 375751 A GB375751 A GB 375751A GB 722704 A GB722704 A GB 722704A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenol
- aza
- heated
- amine
- group
- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention comprises aza-acridines of the general formula <FORM:0722704/IV (b)/1> (wherein R represents an alkoxy or aryloxy group, Y represents chlorine, bromine or iodine, and X represents hydrogen, an aryl or aralkyl hydrocarbon group or a group Z.CnH2n-where n is a positive integer greater than one and Z represents hydrogen, a hydroxy or alkoxy group, or a group having one of the general formul R1R2N-, R1R2N. CmH2mO- or <FORM:0722704/IV (b)/2 where R1 and R2 are alkyl groups of 1-4 carbon atoms, m is a positive integer greater than one, and A is -CH2 or -O-), and the manufacture thereof by heating the corresponding 9-halogen compounds (in the presence or absence of an inert solvent) or the corresponding 9-phenoxy or alkylphenoxy compounds with an ammonium salt of a weak acid or with a primary aralkyl or aryl amine or an amine Z.CnH2n.NH2. The 9-phenoxy or alkylphenoxy compounds may be prepared by heating the 9-halogen compound with phenol or an alkylated phenol and may be further reacted with or without isolation, or the 9-halogen compound may simply be heated with the ammonium salt or amine in the presence of phenol or an alkylated phenol. The products are useful pharmaceutically, especially against plasmodia. In examples, (1) 2-methoxy-6 : 9-dichloro-1-aza-acridine is heated with phenol and the product with 5-diethylamino-2-aminopentane; (2) 2 n - butoxy - 6 : 9 - dichloro - 1 - aza - acridine is heated with phenol and the product with b -diethylaminoethylamine; (3) the amine in (2) is replaced by 5-diethylamino-2-aminopentane, (4) by ammonium carbonate, (6) by ethanolamine, (7) by b -ethoxyethylamine, and (8) by b - diethylaminoethoxyethylamine; (5) the amine in (1) is replaced by ammonium carbonate, (10) by b -morpholinoethylamine, (11) by b -piperidinoethylamine, (12) by n-dodecylamine, and (13) by p-toluidine; (9) 2-methoxy-6 : 9 - dichloro - 1 - aza - acridine is heated with benzylamine; (14) 2-phenoxy-6 : 9-dichloro-1-aza-acridine is heated with phenol and the product with ammonium carbonate. A list of additional amines is given. Specification 704,238 is referred to. In the Provisional Specification, the formula of the products shows the halogen atom Y as occupying any position in the Bz ring, and the substituent in the 9-position is defined as an amino or substituted amino group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3757/51A GB722704A (en) | 1951-02-15 | 1951-02-15 | Improvements in or relating to the production of meso-substituted aza-acridines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3757/51A GB722704A (en) | 1951-02-15 | 1951-02-15 | Improvements in or relating to the production of meso-substituted aza-acridines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB722704A true GB722704A (en) | 1955-01-26 |
Family
ID=9764383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3757/51A Expired GB722704A (en) | 1951-02-15 | 1951-02-15 | Improvements in or relating to the production of meso-substituted aza-acridines |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB722704A (en) |
-
1951
- 1951-02-15 GB GB3757/51A patent/GB722704A/en not_active Expired
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