Certain 2-methyl-3-phenyl-(4)3h-quinazolones
Novel compounds of the general formula in which Z represents a benzene ring which may be substituted, if desired, by at least one alkyl or alkoxy group containing 1 to 3 carbon atoms, R1 and R2 represent hydrogen atoms or alkyl groups containing 1 to 3 carbon atoms, and R3, R4, R5 and R6, which may...
Gespeichert in:
Hauptverfasser: | , |
---|---|
Format: | Patent |
Sprache: | eng |
Schlagworte: | |
Online-Zugang: | Volltext bestellen |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | |
---|---|
container_issue | |
container_start_page | |
container_title | |
container_volume | |
creator | ZEILE KARL HEUSNER ALEX |
description | Novel compounds of the general formula in which Z represents a benzene ring which may be substituted, if desired, by at least one alkyl or alkoxy group containing 1 to 3 carbon atoms, R1 and R2 represent hydrogen atoms or alkyl groups containing 1 to 3 carbon atoms, and R3, R4, R5 and R6, which may be the same or different, represent hydrogen or halogen atoms or alkyl or alkoxy groups containing 1 to 3 carbon atoms, at least one of R3, R4, R5 and R6 being other than a hydrogen atom, and acid addition salts thereof, are prepared (a) where R1 and R2 are both hydrogen, by reduction of the corresponding nitro or nitroso compound; (b) by condensing a substituted acetylanthranilic acid with a phenylenediamine in the presence of a dehydrating agent; (c) where R1 and R2 are both hydrogen, by removal of a protecting group from the corresponding amine protected compound, e.g. hydrolysis of an acyl amino group; or (d) by heating a substituted acetylanthranil with a phenylenediamine. 2 - Methyl - 3 - (nitrophenyl) - 3H - 4 - quinazolones are prepared by condensing a substituted acetylanthranilic acid or a substituted acetylanthranil with a compound of the formula H2N-Z-NO2, if necessary in the presence of a dehydrating agent. Acylaminoquinazolones of the above general formula wherein one of R1 or R2 is acyl and the other hydrogen are prepared by condensing a substituted acetylanthranilic acid or a substituted acetylanthranil with a compound of the formula H2N-Z-A, wherein A is an acylamino group. 3,5 - Dimethyl - acetylanthranilic acid is prepared in conventional manner by acetylation of the corresponding dimethyl anthranilic acid. 2 - Methyl - 3 - (2 - methyl - 4 - aminophenyl)-8-chloro-3H - 4 - quinazolone is prepared by permanganate oxidation of 3 - chloro - 2 - acetamido-toluene. 2 - Methyl - 3 - (2 - methyl - 4 - aminophenyl) 5,6 - dichloro - 3H - 4 - quinazolone is prepared by chlorination of 6-chloro-acetylanthranilic acid in glacial acetic acid. Pharmaceutical compositions, having sedative and anti-convulsant activity, for oral, rectal or parenteral administration, preferably in unit dosage form in the form of tablets, coated tablets, capsules, ampoules or suppositories, comprise a compound of the first general formula above and at least one pharmaceutical carrier or excipient. |
format | Patent |
fullrecord | <record><control><sourceid>epo_EVB</sourceid><recordid>TN_cdi_epo_espacenet_US3418319A</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>US3418319A</sourcerecordid><originalsourceid>FETCH-epo_espacenet_US3418319A3</originalsourceid><addsrcrecordid>eNrjZNBxTi0qSczMUzDSzU0tyajM0TXWLchIzQMyNEw0jTN0C0sz8xKr8nPy81KLeRhY0xJzilN5oTQ3g7yba4izh25qQX58anFBYnJqXmpJfGiwsYmhhbGhpaMxYRUAepooDg</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>patent</recordtype></control><display><type>patent</type><title>Certain 2-methyl-3-phenyl-(4)3h-quinazolones</title><source>esp@cenet</source><creator>ZEILE KARL ; HEUSNER ALEX</creator><creatorcontrib>ZEILE KARL ; HEUSNER ALEX</creatorcontrib><description>Novel compounds of the general formula <FORM:1055843/C2/1> in which Z represents a benzene ring which may be substituted, if desired, by at least one alkyl or alkoxy group containing 1 to 3 carbon atoms, R1 and R2 represent hydrogen atoms or alkyl groups containing 1 to 3 carbon atoms, and R3, R4, R5 and R6, which may be the same or different, represent hydrogen or halogen atoms or alkyl or alkoxy groups containing 1 to 3 carbon atoms, at least one of R3, R4, R5 and R6 being other than a hydrogen atom, and acid addition salts thereof, are prepared (a) where R1 and R2 are both hydrogen, by reduction of the corresponding nitro or nitroso compound; (b) by condensing a substituted acetylanthranilic acid with a phenylenediamine in the presence of a dehydrating agent; (c) where R1 and R2 are both hydrogen, by removal of a protecting group from the corresponding amine protected compound, e.g. hydrolysis of an acyl amino group; or (d) by heating a substituted acetylanthranil with a phenylenediamine. 2 - Methyl - 3 - (nitrophenyl) - 3H - 4 - quinazolones are prepared by condensing a substituted acetylanthranilic acid or a substituted acetylanthranil with a compound of the formula H2N-Z-NO2, if necessary in the presence of a dehydrating agent. Acylaminoquinazolones of the above general formula wherein one of R1 or R2 is acyl and the other hydrogen are prepared by condensing a substituted acetylanthranilic acid or a substituted acetylanthranil with a compound of the formula H2N-Z-A, wherein A is an acylamino group. 3,5 - Dimethyl - acetylanthranilic acid is prepared in conventional manner by acetylation of the corresponding dimethyl anthranilic acid. 2 - Methyl - 3 - (2 - methyl - 4 - aminophenyl)-8-chloro-3H - 4 - quinazolone is prepared by permanganate oxidation of 3 - chloro - 2 - acetamido-toluene. 2 - Methyl - 3 - (2 - methyl - 4 - aminophenyl) 5,6 - dichloro - 3H - 4 - quinazolone is prepared by chlorination of 6-chloro-acetylanthranilic acid in glacial acetic acid. Pharmaceutical compositions, having sedative and anti-convulsant activity, for oral, rectal or parenteral administration, preferably in unit dosage form in the form of tablets, coated tablets, capsules, ampoules or suppositories, comprise a compound of the first general formula above and at least one pharmaceutical carrier or excipient.</description><language>eng</language><subject>CHEMISTRY ; HETEROCYCLIC COMPOUNDS ; METALLURGY ; ORGANIC CHEMISTRY</subject><creationdate>1968</creationdate><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=19681224&DB=EPODOC&CC=US&NR=3418319A$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,780,885,25564,76547</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=19681224&DB=EPODOC&CC=US&NR=3418319A$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>ZEILE KARL</creatorcontrib><creatorcontrib>HEUSNER ALEX</creatorcontrib><title>Certain 2-methyl-3-phenyl-(4)3h-quinazolones</title><description>Novel compounds of the general formula <FORM:1055843/C2/1> in which Z represents a benzene ring which may be substituted, if desired, by at least one alkyl or alkoxy group containing 1 to 3 carbon atoms, R1 and R2 represent hydrogen atoms or alkyl groups containing 1 to 3 carbon atoms, and R3, R4, R5 and R6, which may be the same or different, represent hydrogen or halogen atoms or alkyl or alkoxy groups containing 1 to 3 carbon atoms, at least one of R3, R4, R5 and R6 being other than a hydrogen atom, and acid addition salts thereof, are prepared (a) where R1 and R2 are both hydrogen, by reduction of the corresponding nitro or nitroso compound; (b) by condensing a substituted acetylanthranilic acid with a phenylenediamine in the presence of a dehydrating agent; (c) where R1 and R2 are both hydrogen, by removal of a protecting group from the corresponding amine protected compound, e.g. hydrolysis of an acyl amino group; or (d) by heating a substituted acetylanthranil with a phenylenediamine. 2 - Methyl - 3 - (nitrophenyl) - 3H - 4 - quinazolones are prepared by condensing a substituted acetylanthranilic acid or a substituted acetylanthranil with a compound of the formula H2N-Z-NO2, if necessary in the presence of a dehydrating agent. Acylaminoquinazolones of the above general formula wherein one of R1 or R2 is acyl and the other hydrogen are prepared by condensing a substituted acetylanthranilic acid or a substituted acetylanthranil with a compound of the formula H2N-Z-A, wherein A is an acylamino group. 3,5 - Dimethyl - acetylanthranilic acid is prepared in conventional manner by acetylation of the corresponding dimethyl anthranilic acid. 2 - Methyl - 3 - (2 - methyl - 4 - aminophenyl)-8-chloro-3H - 4 - quinazolone is prepared by permanganate oxidation of 3 - chloro - 2 - acetamido-toluene. 2 - Methyl - 3 - (2 - methyl - 4 - aminophenyl) 5,6 - dichloro - 3H - 4 - quinazolone is prepared by chlorination of 6-chloro-acetylanthranilic acid in glacial acetic acid. Pharmaceutical compositions, having sedative and anti-convulsant activity, for oral, rectal or parenteral administration, preferably in unit dosage form in the form of tablets, coated tablets, capsules, ampoules or suppositories, comprise a compound of the first general formula above and at least one pharmaceutical carrier or excipient.</description><subject>CHEMISTRY</subject><subject>HETEROCYCLIC COMPOUNDS</subject><subject>METALLURGY</subject><subject>ORGANIC CHEMISTRY</subject><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>1968</creationdate><recordtype>patent</recordtype><sourceid>EVB</sourceid><recordid>eNrjZNBxTi0qSczMUzDSzU0tyajM0TXWLchIzQMyNEw0jTN0C0sz8xKr8nPy81KLeRhY0xJzilN5oTQ3g7yba4izh25qQX58anFBYnJqXmpJfGiwsYmhhbGhpaMxYRUAepooDg</recordid><startdate>19681224</startdate><enddate>19681224</enddate><creator>ZEILE KARL</creator><creator>HEUSNER ALEX</creator><scope>EVB</scope></search><sort><creationdate>19681224</creationdate><title>Certain 2-methyl-3-phenyl-(4)3h-quinazolones</title><author>ZEILE KARL ; HEUSNER ALEX</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-epo_espacenet_US3418319A3</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>eng</language><creationdate>1968</creationdate><topic>CHEMISTRY</topic><topic>HETEROCYCLIC COMPOUNDS</topic><topic>METALLURGY</topic><topic>ORGANIC CHEMISTRY</topic><toplevel>online_resources</toplevel><creatorcontrib>ZEILE KARL</creatorcontrib><creatorcontrib>HEUSNER ALEX</creatorcontrib><collection>esp@cenet</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>ZEILE KARL</au><au>HEUSNER ALEX</au><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>Certain 2-methyl-3-phenyl-(4)3h-quinazolones</title><date>1968-12-24</date><risdate>1968</risdate><abstract>Novel compounds of the general formula <FORM:1055843/C2/1> in which Z represents a benzene ring which may be substituted, if desired, by at least one alkyl or alkoxy group containing 1 to 3 carbon atoms, R1 and R2 represent hydrogen atoms or alkyl groups containing 1 to 3 carbon atoms, and R3, R4, R5 and R6, which may be the same or different, represent hydrogen or halogen atoms or alkyl or alkoxy groups containing 1 to 3 carbon atoms, at least one of R3, R4, R5 and R6 being other than a hydrogen atom, and acid addition salts thereof, are prepared (a) where R1 and R2 are both hydrogen, by reduction of the corresponding nitro or nitroso compound; (b) by condensing a substituted acetylanthranilic acid with a phenylenediamine in the presence of a dehydrating agent; (c) where R1 and R2 are both hydrogen, by removal of a protecting group from the corresponding amine protected compound, e.g. hydrolysis of an acyl amino group; or (d) by heating a substituted acetylanthranil with a phenylenediamine. 2 - Methyl - 3 - (nitrophenyl) - 3H - 4 - quinazolones are prepared by condensing a substituted acetylanthranilic acid or a substituted acetylanthranil with a compound of the formula H2N-Z-NO2, if necessary in the presence of a dehydrating agent. Acylaminoquinazolones of the above general formula wherein one of R1 or R2 is acyl and the other hydrogen are prepared by condensing a substituted acetylanthranilic acid or a substituted acetylanthranil with a compound of the formula H2N-Z-A, wherein A is an acylamino group. 3,5 - Dimethyl - acetylanthranilic acid is prepared in conventional manner by acetylation of the corresponding dimethyl anthranilic acid. 2 - Methyl - 3 - (2 - methyl - 4 - aminophenyl)-8-chloro-3H - 4 - quinazolone is prepared by permanganate oxidation of 3 - chloro - 2 - acetamido-toluene. 2 - Methyl - 3 - (2 - methyl - 4 - aminophenyl) 5,6 - dichloro - 3H - 4 - quinazolone is prepared by chlorination of 6-chloro-acetylanthranilic acid in glacial acetic acid. Pharmaceutical compositions, having sedative and anti-convulsant activity, for oral, rectal or parenteral administration, preferably in unit dosage form in the form of tablets, coated tablets, capsules, ampoules or suppositories, comprise a compound of the first general formula above and at least one pharmaceutical carrier or excipient.</abstract><oa>free_for_read</oa></addata></record> |
fulltext | fulltext_linktorsrc |
identifier | |
ispartof | |
issn | |
language | eng |
recordid | cdi_epo_espacenet_US3418319A |
source | esp@cenet |
subjects | CHEMISTRY HETEROCYCLIC COMPOUNDS METALLURGY ORGANIC CHEMISTRY |
title | Certain 2-methyl-3-phenyl-(4)3h-quinazolones |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-06T07%3A05%3A26IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-epo_EVB&rft_val_fmt=info:ofi/fmt:kev:mtx:patent&rft.genre=patent&rft.au=ZEILE%20KARL&rft.date=1968-12-24&rft_id=info:doi/&rft_dat=%3Cepo_EVB%3EUS3418319A%3C/epo_EVB%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true |