GB920019A - 2-substituted sulphanilamidoquinazolines and process - Google Patents

2-substituted sulphanilamidoquinazolines and process

Info

Publication number
GB920019A
GB920019A GB14271/61A GB1427161A GB920019A GB 920019 A GB920019 A GB 920019A GB 14271/61 A GB14271/61 A GB 14271/61A GB 1427161 A GB1427161 A GB 1427161A GB 920019 A GB920019 A GB 920019A
Authority
GB
United Kingdom
Prior art keywords
quinazoline
alkoxy
methyl
treating
methoxy
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
GB14271/61A
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.)
Mead Johnson and Co LLC
Original Assignee
Mead Johnson and Co LLC
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
Priority claimed from US93035A external-priority patent/US3155650A/en
Application filed by Mead Johnson and Co LLC filed Critical Mead Johnson and Co LLC
Publication of GB920019A publication Critical patent/GB920019A/en
Expired legal-status Critical Current

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
    • C07D239/94—Nitrogen atoms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B22—CASTING; POWDER METALLURGY
    • B22D—CASTING OF METALS; CASTING OF OTHER SUBSTANCES BY THE SAME PROCESSES OR DEVICES
    • B22D19/00—Casting in, on, or around objects which form part of the product
    • B22D19/04—Casting in, on, or around objects which form part of the product for joining parts
    • 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
    • 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
    • C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4

Abstract

The invention comprises a compound having the formula: <FORM:0920019/IV(a)/1> wherein R2 contains up to 6 carbon atoms and is an alkyl mercapto, alkenoxy, alkoxy, alkoxysubstituted alkoxy, monovalent aliphatic or alkoxy-substituted monovalent aliphatic radical, R1 contains up to 6 carbon atoms and is a hydrogen atom or an aliphatic acyl group, R5 is a methyl or methoxy group, or a chlorine atom; and the pharmaceutically acceptable metal salt thereof and a process for the preparation thereof by reaction according to the equation: <FORM:0920019/IV(a)/2> wherein X is an alkoxy, alkenoxy, alkoxysubstituted alkoxy or alkyl mercapto group, and R2, R4, and R5 are as previously defined, in the presence of a polar organic diluent at a temperature 80 DEG C.-155 DEG C. If desired the sulphanilamidoquinazoline derivative thus obtained is reacted with a base to obtain a salt or may be acylated to obtain the corresponding N4-acyl substituted sulphanilamidoquinazoline derivative. 2,4-Dichloroquinazoline is obtained from the corresponding hydroxy compound with POCl3. 6-Methyl-quinazoline-2,4-dione is obtained by treating 5-methyl anthranilic acid with potassium cyanate. 2,4-Dichloro-6-methyl quinazoline is obtained by treating 6 - methyl-quinazoline-2,4-dione with POCl3. 2-Chloro-4-methoxy-quinazoline is obtained by treating 2,4 - dichloroquinazoline with sodium in absolute methanol. 2,4-Dimethoxy-quinazoline is obtained by treating 2-chloro-4-methoxyquinazoline with sodium in absolute methanol. 2-Methyl-4-methylthioquinazoline by treating 2-methyl-4-mercaptoquinazoline with dimmthyl sulphate. 2-Ethyl-4-mercaptoquinazoline is obtained by treating 2-ethyl-4-quinazolone with phosphorus pentasulphide. 7-Methoxy-quinazoline-2,4-dione is obtained by treating 4-methoxy-anthranilic acid with potassium cyanate. In a similar manner, the following compounds are obtained, 2,4dichloro-7-methoxy-quinazoline, 2,4-dimethoxy6-chloro-quinazoline, 2,4,7-trimethoxy-quinazoline, and 2,4-dimethoxy-6-methyl-quinazo-line.ALSO:Compositions useful in the treatment of infections caused by micro-organisms and containing compounds of the formula <FORM:0920019/VI/1> wherein R2 contains up to six carbon atoms and is alkyl mercapto, alkenoxy, alkoxy, alkoxy-substituted alkoxy, monovalent aliphatic, or alkoxy-substituted monovalent aliphatic radical, R4 contains up to six carbon atoms and is a hydrogen atom or an aliphatic acyl group, R5 is a methyl or methoxy group or chlorine atom, or a pharmaceutically acceptable metal salt thereof, together with antibiotics, penicillins, tetracyclines, anti-inflammatory or antipyretic drugs, are administered orally or parenterally as tablets, capsules, elixirs, suspensions or solutions.
GB14271/61A 1960-05-12 1961-04-20 2-substituted sulphanilamidoquinazolines and process Expired GB920019A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US2852260A 1960-05-12 1960-05-12
US93035A US3155650A (en) 1961-03-03 1961-03-03 2-substituted-4-sulfanilamidoquinazolines and process

Publications (1)

Publication Number Publication Date
GB920019A true GB920019A (en) 1963-03-06

Family

ID=26703793

Family Applications (1)

Application Number Title Priority Date Filing Date
GB14271/61A Expired GB920019A (en) 1960-05-12 1961-04-20 2-substituted sulphanilamidoquinazolines and process

Country Status (6)

Country Link
BE (1) BE603719A (en)
CH (1) CH422803A (en)
ES (1) ES266752A1 (en)
FR (1) FR1132M (en)
GB (1) GB920019A (en)
SE (1) SE311364B (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4640920A (en) * 1984-06-14 1987-02-03 John Wyeth & Brother Limited 4-(cinnolinylamino or quinazolinylamino)benzenesulphonamides and intermediates therefor
WO2001072720A1 (en) * 2000-03-29 2001-10-04 Celltech Chiroscience Limited Bicyclic amine derivatives as inhibitors of class 1 receptor tyrosine kinases
WO2003055866A1 (en) * 2001-12-21 2003-07-10 Bayer Pharmaceuticals Corporation Quinazoline and quinoline derivative compounds as inhibitors of prolylpeptidase, inducers of apoptosis and cancer treatment agents

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4640920A (en) * 1984-06-14 1987-02-03 John Wyeth & Brother Limited 4-(cinnolinylamino or quinazolinylamino)benzenesulphonamides and intermediates therefor
WO2001072720A1 (en) * 2000-03-29 2001-10-04 Celltech Chiroscience Limited Bicyclic amine derivatives as inhibitors of class 1 receptor tyrosine kinases
US7012076B2 (en) 2000-03-29 2006-03-14 Celltech R&D Limited Bicyclic amine derivatives as inhibitors of class 1 receptor tyrosine kinases
WO2003055866A1 (en) * 2001-12-21 2003-07-10 Bayer Pharmaceuticals Corporation Quinazoline and quinoline derivative compounds as inhibitors of prolylpeptidase, inducers of apoptosis and cancer treatment agents

Also Published As

Publication number Publication date
ES266752A1 (en) 1961-09-16
SE311364B (en) 1969-06-09
BE603719A (en) 1961-11-13
FR1132M (en) 1962-02-19
CH422803A (en) 1966-10-31

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