Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1998-07-08
2000-06-27
Kight, John
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514457, 549399, 549400, 549401, 549404, 549406, A61K 3135, C07D31104, C07D31174
Patent
active
060807806
DESCRIPTION:
BRIEF SUMMARY
FIELD OF INVENTION
The present invention relates to flavonoids which have been found to have anxiolytic properties (i.e. anxiety reducing) without corresponding depression of the central nervous system which is commonly also found in known sedatives such as benzodiazepines. In particular, the present invention relates to flavonoids comprising nitro groups located on the phenyl ring and analogues thereof.
BACKGROUND
Co-pending patent application WO 95/05169 (Strathclyde University) relates to flavonoids and their use in methods of treating anxiety in patients. The flavonoids of WO 95/05169 are described as having anxiolytic properties without associated depression of the central nervous system (e.g. sedative and muscle relaxant effects) commonly found with benzodiazepines. The compounds of WO 95/05169 fall under a general formula: ##STR2## wherein
R.sup.1, R.sup.2, R.sup.3 and R.sup.4, R.sup.5 and R.sup.8 are independently selected from H, OH, R, NO.sub.2, halo, OR, NH.sub.2, NHR, NR.sub.2, COOR, COOH, CN, or a sugar group;
R.sup.6 and R.sup.7 are both H, or R.sup.6 and R.sup.7 together form a single bond;
R is C.sub.1-6 alkyl or alkenyl; or dimers thereof.
Preferred compounds of WO 95/05169 are described in halo derivatives, in particular where R.sup.5 is halo at the 2' position of the above general formula.
It has now been found that certain compounds falling within the generic formula of WO 95/05169 exhibit unexpectedly good anxiolytic activity without associated depression of the central nervous system (e.g. sedative and muscle relaxant effects) commonly found with benzodiazepines, when the flavone nucleus and/or phenyl ring comprises at least one NO.sub.2 substituent. Thus, patients may be treated for anxiety without inducing sedative or myorelaxant side-effects.
It has also been found that compounds of the present invention display a substantially reduced or no anti-convulsant effect, and that memory is apparently not adversely affected, side-effects commonly found with benzodiazepines.
STATEMENT OF INVENTION
According to the present invention there is provided a method of treating anxiety in a patient which comprises administering to the patient an effective non-toxic amount of a flavonoid of general formula (I): ##STR3## wherein
R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 are independently selected from NO.sub.2 and H;
R.sup.6 and R.sup.7 are independently selected from Br, Cl, F, and H or R.sup.6 and R.sup.7 together form a single bond;
R.sup.8, R.sup.10 and R.sup.11 are independently selected from H, --OH, --R, --NO.sub.2, Br, Cl, F, --OR, --NH.sub.2, --NHR, --NR.sub.2, --COOR, --COOH, --CN or a sugar group;
R.sup.9 is selected from H, NO.sub.2, Br, Cl, or F;
R is C.sub.1 -C.sub.6 alkyl or alkenyl;
with the proviso that at least one of R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 is NO.sub.2 and with the exception that when R.sup.9 is H, R.sup.5 is H.
or the administration of an effective non-toxic amount of a bi-flavonoid which is a dimer of a compound of general formula (I) and wherein R.sup.1 to R.sup.11 and R have the meanings given for general formula (I).
The sugar group may be any of the known sugars, including monosaccharides, disaccharides and polysaccharides; and may in particular be glycosyl, galactopyranosyl or mannopyranosyl.
Preferred compounds of Formula I include compounds wherein
R.sup.1, R.sup.2 and R.sup.5 are independently selected from NO.sub.2 and H;
R.sup.8, R.sup.10 and R.sup.11 are all hydrogen;
R.sup.9 is selected from H, NO.sub.2, Br, Cl and F; with the proviso that at least one of R.sup.1, R.sup.1 and R.sup.5 is NO.sub.2 with the exception that when R.sup.9 is H, R.sup.5 is H.
More preferred compounds of Formula (I) are those wherein
R.sup.1, R.sup.2 and R.sup.5 are independently selected from H and NO.sub.2 ;
R.sup.6 and R.sup.7 together form a single bond;
R.sup.8, R.sup.10 and R.sup.11 are all hydrogen;
R.sup.9 is selected from H, NO.sub.2, Br, Cl and F; with the proviso that at least one of R.sup.1, R.sup.2 and R.sup.5 is NO.sub.2 with the exception that
REFERENCES:
Shah et al, Chemical Abstract vol. 95 No. 97521, "Flavones, flavonols and flavanones derived from 2'--hydroxy-4'-n-propoxy-5'-nitrochalcones" (1980).
Flammang et al, Chemical Abstract vol. 89 No. 146720, "Effects of the mature and the position of substituents in a novel synthesis method of B-flavanols" (1978).
Philippe, Chemistry Abstract vol. 78 No. 136075, "Hypotensive and analgesic 7-hydroxychromauones and semicarbazone derivatives", (1973).
Medina Jorge Horacio
Paladini Alejandro Constantino
Covington Raymond
Kight John
University of Strathclyde
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