Imperial Chemical Industries Limited

Walter Hepworth

Edward D Brown

David R Brittain

Gilbert J Stacey

Ian T Kay

David J Collins

Terence Lewis

David J Gilman

Stephen Collyer Smith

Harjinder S Bansal

Michael R Bartley

Raymond L Sundley

George Richard Birchall

A method of killing or controlling unwanted plants by applying to the plant on to a locus thereof an effective amount of a compound of formula (I) ##STR1## or a salt thereof: wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are independently selected from hydrogen, hydroxy, alkyl, alkoxy, alkylcarbonyl, halogen, cyans, nitro, haloalkyl and haloalkoxy; R.sup.6 is hydrogen, hydroxy, amino, lower alkyl, halogen, cyano, haloalkyl, nitro, aryl, or a group C(O).sub.m R.sup.10, wherein R.sup.10 is hydrogen, alkyl, alkenyl, alkynyl or phenyl any of which may be optionally substituted and m is 1 or 2; R.sup.7 is hydrogen, lower alkyl, haloalkyl, C(O).sub.m R.sup.10 or halogen; or R.sup.6 and R.sup.7 together form an optionally substituted alkylene chain of 2 or 3 carbon atoms; R.sup.8 is hydrogen, lower alkyl or halogen or the group R.sup.7 or R.sup.8 together form an oxo group; and the group CZR.sup.9 is carboxy or an ester thereof, or R.sup.9 is a group SR.sup.10 or NR.sup.11 R.sup.12 wherein R.sup.11 is hydrogen or alkyl and R.sup.12 is hydrogen, alkyl, S(O).sub.n R.sup.10 wherein n is 0, 1 or 2; or R.sup.9 is a group NR.sup.11 NR.sup.13 R.sup.14 wherein R.sup.11, R.sup.13 and R.sup.14 are independently selected from hydrogen or alkyl; or R.sup.9 is a group --N.sup..sym. R.sup.11 NR.sup.13 R.sup.14 R.sup.20 x.sup..crclbar. wherein R.sup.11, R.sup.13, R.sup.14 and R.sup.20 are each hydrogen or alkyl, and x.sup.- is an agricultrually acceptable anion, and Z is oxygen or sulphur. Herbicidal compositions containing compounds of formula (I) are also claimed together with certain novel sub groups of compounds of formula (I) and processes for their preparation.

Herbicidal compositions

Novel 1,2-dihydro-2-oxoquinol-4-ylalkanoic acid derivatives bearing a variety of substituents on the quinoline nucleus but including, at position 1, an aromatic radical linked directly or through a C.sub.1-4 -alkylene or a C.sub.2-4 -alkenylene radical. Representative compounds of the invention are 1-(3,4-dichlorobenzyl)-3-methyl-1,2-dihydro-2-oxoquinol-4-ylacetic acid and .alpha.-(1-benzyl-1,2-dihydro-2-oxoquinol-4-yl)propionic acid. The compounds possess anti-inflammatory or analgesic properties, or are inhibitors of the enzyme aldose reductase.

1,2-Dihydro-2-oxoquinol-4-ylacetic acid derivatives and pharmaceutical

The invention concerns pharmaceutical compositions having analgesic, and in some cases, in addition anti-inflammatory properties, for use in the treatment of painful inflammatory joint disease, which compositions contain as active ingredient a new or old 1-alkyl (or cycloalkyl)-4-(N-alkanoyl)substituted-amino-tetrahydro-1,3,5-triazine-2,6- dione of the formula: ##STR1## or a base-addition salt thereof. Many of the compounds of formula I are previously known as herbicides, and a representative example of such a compound which has now been surprisingly found to have useful analgesic properties is 1-isopropyl-4-(N-acetyl)isopropylamino-tetrahydro-1,3,5-triazine-2,6-dione . However certain of the compounds of formula I and the base-addition salts thereof are novel, a representative example being 1-isopropyl-4[(N-acetyl)pent-3-ylamino]-tetrahydro-1,3,5-triazine-2,6-dion e, and are provided as a further feature of the invention, together with analogy processes for their manufacture.

Pharmaceutical compositions

Analgesic compositions containing 1,2-dihydro-2-oxoquinol-4-ylpropionic

Alkanoic acid 2-quinoline derivatives

1-(Heterocyclic)-indol-3-ylacetic acid derivatives, processes for their preparation, and pharmaceutical compositions comprising them. An illustrative compound of the invention is 1-(7-chloroquinazolin-4-yl)-5-methoxy-2-methylindol-3-ylacetic acid. The compounds have anti-inflammatory, analgesic and antipyretic activity. This application is a continuation-in-part of Ser. No. 296,202, filed Oct. 10, 1972, now U.S. Pat. No. 3,884,919.

Indole derivatives for providing analgesic and anti-inflammatory effects

Growing community of inventors

Macclesfield, United Kingdom

Walter Hepworth