GB926038A - Sulphamoyl quinazolinones - Google Patents

Sulphamoyl quinazolinones

Info

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
Application number
GB28757/59A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB926038A publication Critical patent/GB926038A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72Quinazolines; Hydrogenated quinazolines
    • C07D239/86Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
    • C07D239/88Oxygen atoms
    • C07D239/90Oxygen atoms with acyclic radicals attached in position 2 or 3
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72Quinazolines; 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.
GB28757/59A 1958-12-24 1959-08-21 Sulphamoyl quinazolinones Expired GB926038A (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Cited By (1)

* Cited by examiner, † Cited by third party
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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