GB815833A - Phenanthridine compounds - Google Patents
Phenanthridine compoundsInfo
- Publication number
- GB815833A GB815833A GB2945456A GB2945456A GB815833A GB 815833 A GB815833 A GB 815833A GB 2945456 A GB2945456 A GB 2945456A GB 2945456 A GB2945456 A GB 2945456A GB 815833 A GB815833 A GB 815833A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- methyl
- pyrimidylamino
- nitrophenyl
- radical
- 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
- 150000005053 phenanthridines Chemical class 0.000 title 1
- 150000001450 anions Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000000047 product Substances 0.000 abstract 2
- SWLVFNYSXGMGBS-UHFFFAOYSA-N Ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 abstract 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 1
- RDOWQLZANAYVLL-UHFFFAOYSA-N Phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 abstract 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M Silver chloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229940077484 ammonium bromide Drugs 0.000 abstract 1
- 235000019270 ammonium chloride Nutrition 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000007859 condensation product Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- -1 m-nitrophenyl Chemical group 0.000 abstract 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N monochloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000002690 trypanocidal agent Substances 0.000 abstract 1
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
- C07D401/02—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 two hetero rings
- C07D401/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention comprises compounds of general formula <FORM:0815833/IV (b)/1> (wherein R2 is an m-nitrophenyl or m-aminophenyl radical, R2, R3, R4 are alkyl groups which may be the same or different, and X is an anion), and the preparation thereof by condensing a phenanthridine of general formula <FORM:0815833/IV (b)/2> (wherein Y is an anion which may be the same as X) with a halopyrimidine of general formula <FORM:0815833/IV (b)/3> (wherein A is a halogen atom and Z an anion which may be the same as X), and if Y and Z are not identical with X they may be converted into X after the condensation. If in the starting material R2 is a m-nitrophenyl radical, the initial condensation product may be reduced to convert the m-nitrophenyl radical into a m-aminophenyl radical. The products are trypanocidal agents with prophylactic properties. In examples: (1) 2 : 7-diamino-9-m-nitrophenyl-10 - methyl - phenanthridinium chloride is treated with 2-amino-4-chloro-1 : 6-dimethyl pyrimidinium iodide followed by silver chloride, then ammonium chloride, to give 2-amino-7-(21 - amino - 61 - methyl - 41 - pyrimidylamino)-9 - m - nitrophenylphenanthridinium 10 : 11 - dimethochloride; (2) the above compound after reduction and treatment with ammonium bromide gives 2-amino-7-(21-amino-61-methyl-41-pyrimidylamino) - 9 - m - aminophenylphenanthridinium 10 : 11 - dimethobromide. Similarly prepared are: 2 - amino - 7 -(21 - amino-61-methyl - 41 - pyrimidylamino) - 9 - m - nitrophenylphenanthridine - 10 - ethochloride - 11-methochloride, and 2 - amino - 7 - (21 - amino-61 - methyl - 41 - pyrimidylamino) - 9 - m-aminophenylphenanthridine - 10 - ethobromide-11-methobromide. In Example (5) the product of (2) is made by reacting 2 : 7-diamino-9-m-aminophenyl - 10 - methylphenanthridinium bromide with 2 - amino - 4 - chloro - 1 : 6 - dimethylpyrimidinium bromide.
Publications (1)
Publication Number | Publication Date |
---|---|
GB815833A true GB815833A (en) | 1959-07-01 |
Family
ID=1741592
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2945456A Expired GB815833A (en) | 1956-09-26 | Phenanthridine compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB815833A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2230527A (en) * | 1989-04-21 | 1990-10-24 | Ici Plc | 4-(substituted amino)-pyrimidinium derivatives as cardiovascular agents |
US5252567A (en) * | 1989-12-22 | 1993-10-12 | Imperial Chemical Industries Plc | Diazine derivatives |
US5328910A (en) * | 1990-10-18 | 1994-07-12 | Imperial Chemical Industries Plc | Sino-atrial node modulating pyrrolopyrimidines |
US5654298A (en) * | 1990-04-19 | 1997-08-05 | Imperial Chemical Industries | Amine derivatives |
-
1956
- 1956-09-26 GB GB2945456A patent/GB815833A/en not_active Expired
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB2230527A (en) * | 1989-04-21 | 1990-10-24 | Ici Plc | 4-(substituted amino)-pyrimidinium derivatives as cardiovascular agents |
GB2230527B (en) * | 1989-04-21 | 1993-05-05 | Ici Plc | Aminopyrimidine derivatives useful for treating cardiovascular disorders |
US5223505A (en) * | 1989-04-21 | 1993-06-29 | Imperial Chemical Industries Plc | Pyrimidine derivatives |
US5252567A (en) * | 1989-12-22 | 1993-10-12 | Imperial Chemical Industries Plc | Diazine derivatives |
US5654298A (en) * | 1990-04-19 | 1997-08-05 | Imperial Chemical Industries | Amine derivatives |
US5328910A (en) * | 1990-10-18 | 1994-07-12 | Imperial Chemical Industries Plc | Sino-atrial node modulating pyrrolopyrimidines |
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