GB926038A - Sulphamoyl quinazolinones - Google Patents
Sulphamoyl quinazolinonesInfo
- Publication number
- GB926038A GB926038A GB28757/59A GB2875759A GB926038A GB 926038 A GB926038 A GB 926038A GB 28757/59 A GB28757/59 A GB 28757/59A GB 2875759 A GB2875759 A GB 2875759A GB 926038 A GB926038 A GB 926038A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphamoyl
- chloro
- acid
- carbethoxyamino
- substituted
- 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/90—Oxygen atoms with acyclic radicals attached in position 2 or 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the formula: <FORM:0926038/IV(a)/1> in which R and R3 are hydrogen or C1-C6 alkyl radicals, R1 and R2 are hydrogen, C1-C6 alkyl radicals or aralkyl groups or R1 and R2 together are an oxygen atom and X is a halogen atom, e.g. Cl, Br or F or an alkyl or trihalomethyl, e.g. CF3, group, and comprises also the preparation of these compounds by (a) reacting an anthranilamide <FORM:0926038/IV(a)/2> in an acid medium with a carbonyl compound R1-CO-R2 or an acetal or ketal thereof and if desired alkylating any product in which R and/or R3 are hydrogen; (b) reducing a corresponding quinazolone having a double bond in the 1- or 2-position by means of an alkalimetal boron hydride, or (c) in the case when R1 and R2 together represent an oxygen atom, condensing an appropriate 4-substituted-5-sulphamoyl anthranilic acid or ester thereof with a thiourea R3NH.CS.NHR3 and oxidising the resulting 2-thio-1,2,3,4-tetrahydroquinazolinone-6-sulphonamide to replace the 2-thio-substituent by an oxygen atom. Other exemplified processes also include reaction of 4-chloro-5-sulphamoyl-anthranilic acid with urea or cyanic acid (giving a 2-ureido-4-chloro-5-suphamoyl-benzoic acid intermediate) or with propionaldehyde diethyl acetal and ammonia, ring closure of N-methyl-2-carbethoxyamino-4-chloro-5-sulphamoyl-benzamide, reaction of 4-chloro - 5 - sulphamoyl-anthranilamide with phosgene and reaction of ethyl 2-carbethoxyamino-4-chloro - 5 - sulphamoyl - benzoate with hydroxylamine, giving in each case a 2,4-dioxotetrahydroquinazoline. Intermediates 4-substituted- 5-sulphamoylanthranilic acids such as the 4-chloro-, 4-fluoro-and 4-bromocompounds are made by chlorosulphonating an N-acetyl-5-halo-toluidine, converting the 4-chlorosulphonyl-5-halo-acetyltoluidine obtained into the corresponding sulphonamide with ammonia; oxidising with permanganate to a 4-halo-5-sulphamoyl-acetylanthranilic acid which is then hydrolysed. The 4-trifluoromethyl-5-sulphamoyl-acetylanthranilic acid is made by a similar route. 4-Chloro-5-sulphamoyl- N-propionylanthranilic acid is made by the action of propionic anhydride on 4-chloro-5-sulphamoyl-anthranilic acid. 7-Substituted- 6-sulphamoyl-quinazolinones (used as starting materials in process (b) above) are made by treating a 4-substituted -5-sulphamoyl anthranilic acid or an N-acyl derivative thereof with an appropriate amide compound such as formamide, N-methylformamide, ethyl urethane, isobutyramide and N-methyl-acetamide. N-Methyl- 2-carbethoxyamino- 4-chloro-5-sulphamylbenzamide is made by treating 5-chlorotoluidine with ethyl chloroformate, chlorosulphonating the resulting N-carbethoxy-derivative and reacting with ammonia to form a 4-sulphamoyl-5-chloro N-carbethoxy-toluidine, oxidising to 2-carbethoxyamino-4-chloro - 5 - sulphamoyl - benzoi acid, treating with PCl5 and converting to the amide with methylamine. 4-Chloro- 5-sulphamoyl anthranilamide is made by treating 4-chloro-5-sulphamoylanthranilic acid with a chloroformic ester and then with ammonium hydroxide. Ethyl- 2-carbethoxyamino- 4-chloro- 5-sulphamoyl-benzoate is made by esterifying the free acid. The products of the invention are used pharmaceutically as diuretics.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US78268158A | 1958-12-24 | 1958-12-24 | |
US80456759A | 1959-04-07 | 1959-04-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB926038A true GB926038A (en) | 1963-05-15 |
Family
ID=27120031
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB28757/59A Expired GB926038A (en) | 1958-12-24 | 1959-08-21 | Sulphamoyl quinazolinones |
Country Status (6)
Country | Link |
---|---|
BE (1) | BE582287A (en) |
CH (1) | CH396014A (en) |
ES (1) | ES251905A1 (en) |
GB (1) | GB926038A (en) |
MY (1) | MY6400025A (en) |
OA (1) | OA00634A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3518392A (en) * | 1967-11-02 | 1970-06-30 | Pennwalt Corp | Certain 2-spiro-tetrahydro-halo-sulfamyl-quinazolinones |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103408502B (en) * | 2013-07-16 | 2015-07-22 | 湖南大学 | Synthetic method of quinazolinone compounds |
-
1959
- 1959-08-21 GB GB28757/59A patent/GB926038A/en not_active Expired
- 1959-09-03 BE BE582287A patent/BE582287A/en unknown
- 1959-09-03 CH CH7777359A patent/CH396014A/en unknown
- 1959-09-04 ES ES0251905A patent/ES251905A1/en not_active Expired
-
1964
- 1964-12-04 OA OA50725A patent/OA00634A/en unknown
- 1964-12-31 MY MY196425A patent/MY6400025A/en unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3518392A (en) * | 1967-11-02 | 1970-06-30 | Pennwalt Corp | Certain 2-spiro-tetrahydro-halo-sulfamyl-quinazolinones |
Also Published As
Publication number | Publication date |
---|---|
OA00634A (en) | 1966-07-15 |
BE582287A (en) | 1960-03-03 |
CH396014A (en) | 1965-07-31 |
MY6400025A (en) | 1964-12-31 |
ES251905A1 (en) | 1960-03-01 |
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