Arylthiadiazole derivative and antiviral agent containing the sa

Details Arylthiadiazole derivative and antiviral agent containing the sa Arylthiadiazole derivative and antiviral agent containing the sa

1997-06-09

1999-09-07

Lambkin, Deborah C.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

548138, C07D285125

Patent

active

059489162

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION

1. Field of the Invention
The present invention relates to arylthiadiazole derivatives and salts thereof having antiviral activity.
2. Description of the Related Art
Thiadiazoles having herbicidal activity are described in JP-A-3-193773, JP-A-4-103575, and JP-A-4-117372. Thiadiazoles useful as an agricultural fungicide are described in JP-A-4-182403, and JP-A-4-182405. On the other hand, acyclovir (antiherpetic medicine), amantadine (antiinfluenzal medicine), azidothymidine (anti-HIV medicine, HIV: human immunodeficiency virus) are known as antiviral medicines.
No medicine is effective against viral diseases at the moment, so that effective antiviral medicines are desired to be developed. In particular, development of anti-HIV medicine is urgent.


DISCLOSURE OF THE INVENTION

After comprehensive investigation, it was found by the inventors of the present invention that arylthiadiazole derivatives have excellent antiviral activity. Based on the findings, the present invention has been accomplished.
The present invention provides arylthiadiazole derivatives represented by ##STR1## where Y.sup.1 is an oxygen atom or a sulfur atom; W is an oxygen atom or a sulfur atom; one of R.sup.1, R.sup.2, and R.sup.3 is an amino group which may be substituted by one or two independent alkyls of 1-6 carbons; a carboxyl group; a carbonyl group which is substituted by an alkoxyl of 1-4 carbons; a carbamoyl group which may be substituted by one or two independent alkyls of 1-6 carbons; a cyano group; or an alkyl group of 1-6 carbons which is substituted by a hydroxyl, an alkoxyl of 1-4 carbons, an alkoxyl of 1-4 carbons (which is further substituted by another alkoxyl of 1-4 carbons), or a silyloxy group (which is substituted by three independent alkyls of 1-6 carbons); the other two of R.sup.1, R.sup.2, and R.sup.3 are independently a hydrogen atom; a halogen atom; an alkyl group of 1-6 carbons which may be substituted by a hydroxyl, an alkoxyl of 1-4 carbons, an alkoxyl of 1-4 carbons (which is further substituted by another alkoxyl of 1-4 carbons), or a silyloxy (which is substituted by three independent alkyls of 1-6 carbons; a trifluoromethyl group; an alkoxyl group of 1-4 carbons; a carboxyl group; a carbonyl group which is substituted by an alkoxyl of 1-4 carbons; a carbamoyl group which may be substituted by one or two independent alkyls of 1-6 carbons; a cyano group; a hydroxyl group; a hydroxymethyl group; a nitro group; or an amino group which may be substituted by one or two independent alkyls of 1-6 carbons; R.sup.4, and R.sup.5 are independently a hydrogen atom, an alkoxyl group of 1-4 carbons, an alkyl group of 1-6 carbons which may be substituted by an alkoxyl of 1-4 carbons, a hydroxyl, a cyano, a carboxyl, a carbamoyl, a carbonyl (substituted by alkoxyl of 1-4 carbons), or a group of ##STR2## or R.sup.4 and R.sup.5 are linked together to form a group of ##STR3## R.sup.6, R.sup.7, and R.sup.8 are independently a hydrogen atom, a halogen atom, an alkyl group of 1-6 carbons, or an alkoxyl group of 1-4 carbons; R.sup.9, and R.sup.10 are independently a hydrogen atom, or an alkyl group of 1-6 carbons; E is a --CH.sub.2 -- or an oxygen atom; and n.sup.1 is an integer of 0 to 2.
The present invention also provides a virucide containing the thereof as an active ingrdient.
The present invention further provides arylthiadiazole derivatives represented by the formulas below, and salts thereof: ##STR4## where n.sup.2 is 1 or 2; n.sup.3 is 0 or 1; halogen atom, an alkyl group of 1 to 6 carbons, a trifluoromethyl group, an alkoxyl group of 1-4 carbons, a hydroxyl group, or a nitro group; group (which may be substituted by a halogen, an alkyl of 1-6 carbons, or an alkoxyl of 1-4 carbons); hydroxyl, a cyano, a carboxyl, a carbamoyl, or a carbonyl substituted by an alkoxyl group of 1-4 carbons; substituted by an alkoxyl of 1-4 carbons; n.sup.1 are the same as mentioned above, provided that, in the last formula, R.sup.11, R.sup.12, and R.sup.13 are not simultaneously a hydrogen atom when n.sup.3

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