GB713767A - Improvements relating to substituted quinazolones - Google Patents
Improvements relating to substituted quinazolonesInfo
- Publication number
- GB713767A GB713767A GB20948/51A GB2094851A GB713767A GB 713767 A GB713767 A GB 713767A GB 20948/51 A GB20948/51 A GB 20948/51A GB 2094851 A GB2094851 A GB 2094851A GB 713767 A GB713767 A GB 713767A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methoxy
- acid
- quinazolones
- carbethoxy
- chloro
- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises quinazolones of the general formula <FORM:0713767/IV (b)/1> wherein R represents at least one of the following: halogen atoms, alkoxy, aryloxy, aralkoxy hydroxy, aryl, alkyl, acyl and carboxyl radicals in one or more of the 5, 6, 7 and 8 positions; R1 represents a hydrogen atom or a hydroxy, alkoxy or aryloxy radical. The compounds may be prepared by subjecting quinazolones of the general formula <FORM:0713767/IV (b)/2> (wherein R11 represents -OC2H5; -O.CH2. C6H5; -O.C6H5; C6H5 or substituted phenyl radicals) to acid hydrolysis until the group -COR11 has been replaced by a hydrogen atom, and, where R1 is an alkoxy group, optionally further subjecting the resulting product to dealkylation. The acid hydrolysis is carried out using a strong inorganic acid, e.g. hydrohalic, sulphuric and phosphoric acids. In numerous detailed examples quinazolones of general formula II are refluxed in hydrochloric acid, evaporated to dryness and the products purified from ethanolic hydrogen chloride. For the preparation of compounds in which R1 is hydroxy, the corresponding methoxy derivative is refluxed in hydrobromic acid, evaporated to dryness and purified as above. The preparation is described of formula I compounds in which R1 is -OH or -OCH3 and R is 5-Cl; 6-Cl; 7-Cl; 8-Cl; 5-F; 5-CF3; 5-Br; 5-Me; 6-Me; 7-Me; 8-Me; 5-OMe; 6-OMe; 5-Cl, 8-MeO; 5-Cl, 6-Me; 6 : 8-di-Cl; or 5 : 6-di-Me. Quinazolones of general formula II are prepared by condensation of a 4-quinazolone of the general formula <FORM:0713767/IV (b)/3> with a substituted piperidine having the general formula <FORM:0713767/IV (b)/4> wherein X represents a halogen atom. In an example 6-chloro-4-quinazolone in sodium methoxide is treated with 1-carbethoxy-2-(g -bromoacetonyl)-3-methoxypiperidine to produce 3-[b - keto - g - (1 - carbethoxy - 3 - methoxy - 2-piperidyl) - propyl] - 6 - chloro - 4 - quinazolone. Other formula II quinazolones in which R and R1 represent the radicals listed above and R11 is a carbethoxy group are also described. The requisite 4-quinazolones are prepared from the corresponding anthranilic acids by fusion with formamide, a number of the necessary anthranilic acids being obtained from suitable isonitroso acetanilides by cyclization to the isatins followed by treatment with alkaline hydrogen peroxide. Detailed preparations of 8-chlor, 5-chloro - 8 - methoxy -, 5 - chloro -, 6 : 8 - dichloro-, 5 - bromo -, 5 - chloro - 6 - methyl -, 5 : 6 - dimethyl -, and 5 - trifluoromethyl - 4 - quinazolones are given. 5-Methoxy- and 5-fluoro-4-quinazolone are obtained by cyclization of 2-formylamino-6-methoxybenzamide and by diazotization of 5-amino-4-quinazolone respectively. The necessary substituted piperidines are prepared from 2-piperidones. In a detailed example, 3-chloro-3-carbethoxy-2-piperidone is converted to 3-methoxy-3-carbomethoxy-2-piperidone which upon treatment with acid and then benzyl chlorocarbonate yields 2-methoxy-5-carbobenzoxyaminovaleric acid. Conversion to the acid chloride followed by condensation with ethyl malonate furnishes ethyl (2-methoxy-5-carbobenzoxyamino valeryl) malonate which is hydrogenated to 3-methoxy piperidine-2-malonic ester, which upon hydrolysis and reaction with ethyl chlorocarbonate yields 1-carbethoxy-3-methoxy-2-piperidylacetic acid. This is converted via its acid chloride, treatment with diazomethane and finally hydrobromic acid into 1 - carbethoxy - 2 - [g - bromoacetonyl] - 3 - methoxypiperidine.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US713767XA | 1950-09-09 | 1950-09-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB713767A true GB713767A (en) | 1954-08-18 |
Family
ID=22100910
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB20948/51A Expired GB713767A (en) | 1950-09-09 | 1951-09-05 | Improvements relating to substituted quinazolones |
Country Status (2)
Country | Link |
---|---|
BE (1) | BE505711A (en) |
GB (1) | GB713767A (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2468368A1 (en) * | 1979-08-23 | 1981-05-08 | Hoechst Ag | AGENT FOR THE TREATMENT OF QUINAZOLINONE THEILERIOSES |
US4632926A (en) * | 1982-07-06 | 1986-12-30 | Vetem S.P.A. | Quinazolinone derivatives which are active against coccidiosis |
EP1737831A1 (en) * | 2004-04-02 | 2007-01-03 | Prana Biotechnology Limited | Neurologically-active compounds |
FR2921061A1 (en) * | 2007-09-13 | 2009-03-20 | Idealp Pharma Soc Par Actions | Use of indolone compounds to treat malaria and inhibit the growth of the (non)resistant strains of Plasmodium falciparum, preferably one of the resistant strain to chloroquine |
AU2005229161B2 (en) * | 2004-04-02 | 2011-07-28 | Prana Biotechnology Limited | Neurologically-active compounds |
KR101375074B1 (en) * | 2004-04-02 | 2014-03-17 | 프라나 바이오테크놀로지 리미티드 | Neurologically-active compounds |
US9163018B2 (en) | 2006-04-14 | 2015-10-20 | Prana Biotechnology Inc. | Method of treatment of age-related macular degeneration (AMD) |
-
0
- BE BE505711D patent/BE505711A/xx unknown
-
1951
- 1951-09-05 GB GB20948/51A patent/GB713767A/en not_active Expired
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2468368A1 (en) * | 1979-08-23 | 1981-05-08 | Hoechst Ag | AGENT FOR THE TREATMENT OF QUINAZOLINONE THEILERIOSES |
US4632926A (en) * | 1982-07-06 | 1986-12-30 | Vetem S.P.A. | Quinazolinone derivatives which are active against coccidiosis |
EP1737831A1 (en) * | 2004-04-02 | 2007-01-03 | Prana Biotechnology Limited | Neurologically-active compounds |
JP2007530601A (en) * | 2004-04-02 | 2007-11-01 | プラナ バイオテクノロジー リミティッド | Neurologically active compounds |
EP1737831A4 (en) * | 2004-04-02 | 2009-07-22 | Prana Biotechnology Ltd | Neurologically-active compounds |
AU2005229161B2 (en) * | 2004-04-02 | 2011-07-28 | Prana Biotechnology Limited | Neurologically-active compounds |
US8084459B2 (en) | 2004-04-02 | 2011-12-27 | Prana Biotechnology Ltd | Substituted quinazolinones for treating neurological conditions |
JP4937111B2 (en) * | 2004-04-02 | 2012-05-23 | プラナ バイオテクノロジー リミティッド | Neurologically active compounds |
KR101375074B1 (en) * | 2004-04-02 | 2014-03-17 | 프라나 바이오테크놀로지 리미티드 | Neurologically-active compounds |
US9163018B2 (en) | 2006-04-14 | 2015-10-20 | Prana Biotechnology Inc. | Method of treatment of age-related macular degeneration (AMD) |
FR2921061A1 (en) * | 2007-09-13 | 2009-03-20 | Idealp Pharma Soc Par Actions | Use of indolone compounds to treat malaria and inhibit the growth of the (non)resistant strains of Plasmodium falciparum, preferably one of the resistant strain to chloroquine |
Also Published As
Publication number | Publication date |
---|---|
BE505711A (en) |
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