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US 4,879,296 AGranted
Xanthine derivatives
AssigneeBurroughs Wellcome Co.
InventorsSusan M. Daluge, Harry J. Leighton
Life of this patent
Estimating the term…
Abstract
The present invention relates to certain novel 8-phenylxanthines substituted in the 3 or 4 position of the phenyl group by an alkenylene, alkenyleneoxy, alkynylene or alkynyleneoxy bearing a terminal acidic grouping, and to their use in human and veterinary therapy, particularly for conditions associated with the cell surface effects of adenosine.
Claims19
A compound of formula (I):
- ##STR15## wherein:
- X.sub.1 and X.sub.2 are the same or different and are hydrogen, C.sub.1-6 alkyl, C.sub.2-6 alkenyl or C.sub.7-12 aralkyl optionally substituted in the aryl ring by at least one substituent selected from C.sub.1-6 alkyl, C.sub.1-6 alkoxy, hydroxy, halo, nitro, amino, azido and cyano, provided that both X.sub.1 and X.sub.2 are not hydrogen;
- one of X.sub.3 and X.sub.4 is hydrogen, C.sub.1-6 alkyl, trifluoromethyl, C.sub.1-6 alkoxy, halo, nitro, amino, C.sub.1-6 alkoxycarbonyl or carboxy and the other is a group -Y-Z where Y is C.sub.2-6 alkenylene, or C.sub.3-6 alkenylenoxy, C.sub.2-6 alkynylene or C.sub.3-6 alkynyleneoxy and Z is carboxy, sulphonyl or pohosphonyl or a C.sub.1-9 alkyl ester, a C.sub.7-12 aralkyl ester or a C.sub.6-12 aryl ester thereof, or is 5-tetrazolyl;
- and
- X.sub.5 and X.sub.6 are the same or different and are oxygen or sulphur;
- pharmaceutically acceptable thereof.
3 more elements
A compound selected from the following compounds:
- (E)-4-(1,2,3,6-tetrahydro-1,3,-dimethyl-2,6-dioxo-9H-purin-8-yl)cinnamic acid,
- (E)-4-(1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-1-propyl-9H-purin-8-yl)cinnami c acid,
- (E)-4-(1,3-diethyl-1,2,3,6-tetrahydro-2,6-dioxo-9H-purin-8-yl)cinnamic acid,
- (E)-4-(1,3-diallyl-1,2,3,6-tetrahydro-2,6-dioxo-9H-purin-8-yl)cinnamic acid,
- (E)-4-(1,2,3,6-tetrahydro-2,6-dioxo-1,3-dipropyl-9H-purin-8-yl)cinnamic acid,
- (E)-4-(1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-9H-purin-8-yl)cinnamic acid,
- (E)-4-(3-ethyl-1,2,3,6-tetrahydro-2,6-dioxo-9H-purin-8-yl)cinnamic acid,
- (E)-4-(1,2,3,6-tetrahydro-2,6-dioxo-3-propyl-9H-purin-8-yl)cinnamic acid,
- (E)-4-(1,2,3,6-tetrahydro-3-isobutyl-2,6-dioxo-9H-purin-8-yl)cinnamic acid,
- (E)-4-(1,2,3,6-tetrahydro-1-methyl-2,6-dioxo-3-propyl-9H-purin-8-yl)cinnami c acid,
- (E)-4-(1,2,3,6-tetrahydro-3-isobutyl-1-methyl-2,6-dioxo-9H-purin-8-yl)cinna mic acid,
- (E)-4-(1-ethyl-1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-9H-purin-8-yl)cinnamic acid,
- (E)-4-(1,3-dibutyl-1,2,3,6-tetrahydro-1,6-dioxo-9H-purin-8-yl)cinnamic acid,
- (E)-4-(1,3-dibenzyl-1,2,3,6-tetrahydro-2,6-dioxo-9H-purin-8-yl)cinnamic acid,
- (E)-4-(3-butyl-1,2,3,6-tetrahydro-1-methyl-2,6-dioxo-9H-purin-8-yl)cinnamic acid,
- (E)-4-(1-butyl-1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-9H-purin-8-yl)cinnamic acid,
- (E)-4-(3-benzyl-1,2,3,6-tetrahydro-1-methyl-2,6-dioxo-9H-purin-8-yl)cinnami c acid,
- (E)-4-(1,2,3,6-tetrahydro-1,3-diisobutyl-2,6-dioxo-9H-purin-8-yl)cinnamic acid,
- (E)-4-(1,2,3,6-tetrahydro-1,3-dimethyl-6-oxo-2-thio-9H-purin-8-yl)cinnamic acid,
- (E)-4-[3-(4-cyanobenzyl)-1,2,3,6-tetrahydro-1-methyl-2,6-dioxo-9H-purin-8-y l]cinnamic acid,
- (E)-4-[3-(3-cyanobenzyl)-1,2,3,6-tetrahydro-1-methyl-2,6-dioxo-9H-purin-8-y l]cinnamic acid,
- 3-[4-(1,2,3,6-tetrahydro-2,6-dioxo-1,3-dipropyl-9H-purin-8-yl)phenyl]propio lic acid,
- (E)-4-[1-(4-cyanobenzyl)-1,2,3,6-tetrahydro-3-methyl-2,6-dioxo-9H-purin-8-y l]cinnamic acid,
- (E)-4-(1-benzyl-1,2,3,6-tetrahydro-2,6-dioxo-3-propyl-9H-purin-8-yl)cinnami c acid, and
- (E)-4-(3-benzyl-1,2,3,6-tetrahydro-2,6-dioxo-1-propyl-9H-purin-8-yl)cinnami c acid.
22 more elements
Dependencies are inferred from the claim text.