GB794043A - New quinoline derivatives - Google Patents
New quinoline derivativesInfo
- Publication number
- GB794043A GB794043A GB1594555A GB1594555A GB794043A GB 794043 A GB794043 A GB 794043A GB 1594555 A GB1594555 A GB 1594555A GB 1594555 A GB1594555 A GB 1594555A GB 794043 A GB794043 A GB 794043A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- phenylquinoline
- methochloride
- chloro
- compound
- 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
- C07D401/02—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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention comprises quinoline derivatives, which are quaternary salts, of the general formula <FORM:0794043/IV (b)/1> (wherein R and R1 may be the same or different and represent alkyl radicals, R2 represents a phenyl radical optionally bearing halogen, alkyl or alkoxy substituents, R3 and R4 both represent hydrogen or one hydrogen and the other an alkyl radical, R5 represents hydrogen, R6 hydrogen or an alkyl radical of not more than 4 carbon atoms and X an anion), and the manufacture thereof by (a) (when R=R1) treating a compound of the general formula <FORM:0794043/IV (b)/2> with a quaternary salt-forming agent RX, or (b) interaction of a compound of the formula <FORM:0794043/IV (b)/3> with a compound of the formula <FORM:0794043/IV (b)/4> (wherein Y represents a halogen atom), or (c) replacing anions other than X by X by the action of a mineral acid or salt containing the anion X. The products are useful as chemotherapeutic agents, especially for treating babesiasis. In examples: (1) 2-amino-4-chloro-6-methylpyrimidine 1-methiodide is refluxed in water with 4:6 - diamino - 2 - phenylquinoline methochloride hydrochloride and the product is treated with hydrochloric acid to give 4-amino-6 - (21 - amino - 61 - methylpyrimidyl - 41 - amino) - 2 - phenylquinoline 1:11 - dimethochloride; (2) 4-amino-6-(21-amino-61-methylpyrimidyl - 41 - amino) - 2 - phenylquinoline is heated with dimethyl sulphate in nitrobenzene to produce its 1:11-dimethosulphate, which is converted to the product of (1) by treatment with aqueous sodium chloride solution; (3) 4-amino - 6 - (21 - aminopyrimidyl - 41 - amino) - 2 - phenylquinoline is similarly converted to its dimethosulphate, which is treated with sodium iodide to produce the dimethiodide; (4) 2-amino - 4 - chloro - 6 - methylpyrimidine 1 - methiodide and 6 - amino - 4 - methylamino - 2 - phenylquinoline methochloride are refluxed in dilute hydrochloric acid to produce 4-methylamino - 6 - (21 - amino - 61 - methylpyrimidyl - 41 - amino) - 2 - phenylquinoline 1:11 - dimethochloride; (5) 4:6 - diamino - 2 - p - chlorophenylquinoline methochloride hydrochloride and 2 - amino - 4 - chloro - 6 - methylpyrimidine 1 - methiodide are refluxed in water and the reaction mixture is poured into saturated aqueous sodium chloride solution to precipitate 4-amino-6-(21-amino-61-methylpyrimidyl-41-amino) - 2 - p - chlorophenylquinoline 1:11 - dimethochloride; (6) similarly, except that hydrochloric acid is used instead of sodium chloride solution, 4:6 - diamino - 2 - p - methoxyphenylquinoline methochloride hydrochloride yields the corresponding p-methoxy compound. Starting materials. Pyrimidylaminoquinolines of the second general formula above are obtainable by interaction of the corresponding 6-aminoquinoline compounds with the corresponding 4-halopyrimidine compounds in an aqueous acid medium. The 6-aminoquinoline compounds may be prepared by ring-closing the condensation product of a p-acylaminoaniline with a compound of the formula R2.COCH2-COOR7 (where R7 is a lower alkyl radical) to form a 6-acylamino-4-hydroxyquinoline, replacing the hydroxy group by a halogen atom, e.g. by means of POCl3, reacting the product with ammonia or a monoalkylamine and subjecting the resulting 6-acylaminoquinoline compound to acid hydrolysis. The preparation of the starting materials of Examples (2) and (3) is described in detail. 4:6-Diamino-2-phenylquinoline methochloride hydrochloride is obtained by the action of dimethyl sulphate, followed by refluxing with dilute hydrochloric acid, from 6 - acetamido - 4 - amino - 2 - phenylquinoline, itself prepared as indicated above from the condensation product of p-aminoacetanilide and ethyl benzoylacetate. 6-Amino-4-methylamino-2-phenylquinoline methochloride is similarly prepared from the analogously obtained 6-acetamido - 4 - methylamino - 2 - phenylquinoline. Ethyl p-chloro- and p-methoxy-benzoylacetate similarly yield 4:6-diamino-2-p-chloro- and -p-methoxy-phenylquinoline methochloride hydrochlorides via 6-acetamido-4-hydroxy- and -4-amino-2-p-chloro- and -p-methoxyphenylquinoline.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1594555A GB794043A (en) | 1955-06-03 | 1955-06-03 | New quinoline derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1594555A GB794043A (en) | 1955-06-03 | 1955-06-03 | New quinoline derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB794043A true GB794043A (en) | 1958-04-30 |
Family
ID=10068383
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1594555A Expired GB794043A (en) | 1955-06-03 | 1955-06-03 | New quinoline derivatives |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB794043A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002036586A1 (en) * | 2000-11-06 | 2002-05-10 | Astrazeneca Ab | N-type calcium channel antagonists for the treatment of pain |
WO2002036567A1 (en) * | 2000-11-06 | 2002-05-10 | Astrazeneca Ab | N-type calcium channel antagonists for the treatment of pain |
WO2003018021A1 (en) * | 2001-08-22 | 2003-03-06 | Amgen Inc. | 2,4-disubstituted pyrimidinyl derivatives for use as anticancer agents |
-
1955
- 1955-06-03 GB GB1594555A patent/GB794043A/en not_active Expired
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002036586A1 (en) * | 2000-11-06 | 2002-05-10 | Astrazeneca Ab | N-type calcium channel antagonists for the treatment of pain |
WO2002036567A1 (en) * | 2000-11-06 | 2002-05-10 | Astrazeneca Ab | N-type calcium channel antagonists for the treatment of pain |
US6815447B2 (en) | 2000-11-06 | 2004-11-09 | Astrazeneca Ab | N-type calcium channel antagonists for the treatment of pain |
US7189714B2 (en) | 2000-11-06 | 2007-03-13 | Astrazeneca Ab | N-type calcium channel antagonists for the treatment of pain |
US7348340B2 (en) * | 2000-11-06 | 2008-03-25 | Astrazeneca Ab | N-type calcium channel antagonists for the treatment of pain |
WO2003018021A1 (en) * | 2001-08-22 | 2003-03-06 | Amgen Inc. | 2,4-disubstituted pyrimidinyl derivatives for use as anticancer agents |
US6939874B2 (en) | 2001-08-22 | 2005-09-06 | Amgen Inc. | Substituted pyrimidinyl derivatives and methods of use |
AU2002336390B2 (en) * | 2001-08-22 | 2005-10-20 | Amgen Inc. | 2,4-disubstituted pyrimidinyl derivatives for use as anticancer agents |
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