Pharmaceutical compositions and methods of using thiadiazolo pyrimidinone compounds

Claim 2

A pharmaceutical drug composition useful as an immunostimulant for a mammal comprising a pharmaceutically acceptable carrier and, in an amount effective to cause an immune response in the mammal, the compound of the formula ##STR17## in which R is hydrogen or C 1 to C 5 alkyl; R 4 " and R 2 " which are the same or different, are selected from the group consisting of hydrogen, C 1 to C 5 alkyl, benzyl, phenyl ethyl, phenyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 -C 4 in the alkyl, with the proviso that R 1 " and R 2 " cannot represent at the same time hydrogen, C 1 to C 5 alkyl, unsubstituted phenyl or a heterocyclic group; or a pharmaceutically acceptable salt of such a compound.

Claim 3

The pharmaceutical drug composition of claim 1 wherein the amount of the compound in the composition useful as an immunostimulant is from about 5 to about 1000 mg.

Claim 4

A pharmaceutical drug composition of claim 2 wherein the amount of the compound in the composition useful as an immunostimulant is from about 10 to about 250 mg.

Claim 5

A pharmaceutical drug composition for treating virus infections or useful as an immunostimulant which comprises anti-virully effective or immunostimulant amount of the compound 3-phenyl-7H-thiazolo-[3,2-a]-pyrimidin-7-one-5-carboxylic acid or an ester of the acid with an alkanol of 1 to 5 carbons atoms or a pharmaceutically acceptable salt of this compound, with a pharmaceutically effective carrier.

Claim 6

A pharmaceutical drug composition for treating virus infections or useful as an immunostimulant which comprises anti-virully effective or immunostimulant amount of the compound 3-phenyl-7H-thiazolo-[3,2-a]-pyrimidin-7-one-5-carboxylic acid or an ester of the acid with an alkanol of 1 to 5 carbons atoms or a pharmaceutically acceptable salt of this compound, with a pharmaceutically effective carrier.

Claim 7

A pharmaceutical drug composition for treating virus infections or useful as an immunostimulant which comprises an anti-virully effective or immunostimulant amount of the ester of the acid of claim 4 with an alkanol of 1 to 5 carbon atoms, with a pharmaceutically effective carrier.

Claim 8

A anti-viral pharmaceutical composition which comprises an effective amount for treating virus infections of mammals of a compound of the formula ##STR18## in which R is hydrogen or C 1 to C 5 alkyl; R" 1 and R" 2 which are the same or different are selected from the group consisting of hydrogen, C 1 to C 5 alkyl, benzyl, phenyl ethyl, phenyl, thienyl, pyridyl, C 5 and C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 -C 4 in the alkyl, with the proviso that R" 1 and R" 2 cannot represent at the same time hydrogen, C 1 to C 5 alkyl, unsubstituted phenyl, or a heterocyclic group; or a pharmaceutically acceptable salt of such a compound, in combination with a pharmaceutically acceptable carrier.

Claim 9

A anti-viral pharmaceutical composition which comprises an effective amount for treating virus infections of mammals of a compound of the formula ##STR18## in which R is hydrogen or C 1 to C 5 alkyl; R" 1 and R" 2 which are the same or different are selected from the group consisting of hydrogen, C 1 to C 5 alkyl, benzyl, phenyl ethyl, phenyl, thienyl, pyridyl, C 5 and C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 -C 4 in the alkyl, with the proviso that R" 1 and R" 2 cannot represent at the same time hydrogen, C 1 to C 5 alkyl, unsubstituted phenyl, or a heterocyclic group; or a pharmaceutically acceptable salt of such a compound, in combination with a pharmaceutically acceptable carrier.

Claim 10

The method of inducing an immune response in a warm-blooded mammal which comprises administering to the mammal an effective amount to induce an immune response of a composition of claim 1.

Claim 11

The method of claim 7 wherein the compound is administered in a dosage of about 5 to 1000 mg.

Claim 12

The method of claim 8 wherein the compound is administered in a dosage of about 10 to 250 mg.

Claim 13

A pharmaceutical drug composition for treating virus infections or useful as an immunostimulant which comprises an anti-virally effective or immunostimulant amount of a compound of the formula: ##STR19## in which R is selected from the group consisting of hydrogen or C 1 to C 5 alkyl; R 1 is selected from the group consisting of benzyl, phenyl, ethyl, thienyl, pyridyl, C 5 and C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; and R 2 is selected from the group consisting of hydrogen, C 1 to C 5 alkyl, benzyl, phenyl ethyl, phenyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; the halogen in R 1 and R 2 being selected from chloro, bromo and fluoro; with the proviso that R 1 and R 2 cannot at the same time represent a heterocyclic group; and the pharmaceutically acceptable salts thereof; and a pharmaceutically effective carrier.

Claim 14

A pharmaceutical drug composition for treating virus infections or useful as an immunostimulant which comprises an anti-virally effective or immunostimulant amount of a compound of the formula: ##STR19## in which R is selected from the group consisting of hydrogen or C 1 to C 5 alkyl; R 1 is selected from the group consisting of benzyl, phenyl, ethyl, thienyl, pyridyl, C 5 and C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; and R 2 is selected from the group consisting of hydrogen, C 1 to C 5 alkyl, benzyl, phenyl ethyl, phenyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; the halogen in R 1 and R 2 being selected from chloro, bromo and fluoro; with the proviso that R 1 and R 2 cannot at the same time represent a heterocyclic group; and the pharmaceutically acceptable salts thereof; and a pharmaceutically effective carrier.

Claim 15

A method for treating a virus infection of a mammal comprising administering an effective amount of the drug composition of claim 10 to said mammal.

Claim 16

A method of inducing an immune response in a mammal comprising administering an effective amount of the drug composition of claim 10 to said mammal.

Claim 17

A pharmaceutical drug composition for treating virus infections or useful as an immunostimulant high comprises an anti-virally effective or immunostimulant amount of a compound of the formula: ##STR20## in which R is selected from the group consisting of hydrogen, or C 1 to C 5 alkyl; R 1 is selected from the group consisting of hydrogen, C 1 to C 5 alkyl, benzyl, phenyl ethyl, phenyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl, ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; and R 2 is selected from the group consisting of benzyl, phenyl ethyl, thienyl, pyridyl, C 5 to C 7 cylcoalkyl and benzyl, phenyl ethyl, phenyl thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; the halogen in R 1 and R 2 being selected from chloro, bromo and fluoro; with the proviso that R 1 and R 2 cannot at the same time represent a heterocyclic group, and the pharmaceutically acceptable salts thereof and a pharmaceutically effective carrier.

Claim 18

A pharmaceutical drug composition for treating virus infections or useful as an immunostimulant high comprises an anti-virally effective or immunostimulant amount of a compound of the formula: ##STR20## in which R is selected from the group consisting of hydrogen, or C 1 to C 5 alkyl; R 1 is selected from the group consisting of hydrogen, C 1 to C 5 alkyl, benzyl, phenyl ethyl, phenyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl, ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; and R 2 is selected from the group consisting of benzyl, phenyl ethyl, thienyl, pyridyl, C 5 to C 7 cylcoalkyl and benzyl, phenyl ethyl, phenyl thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; the halogen in R 1 and R 2 being selected from chloro, bromo and fluoro; with the proviso that R 1 and R 2 cannot at the same time represent a heterocyclic group, and the pharmaceutically acceptable salts thereof and a pharmaceutically effective carrier.

Claim 19

A method for treating a virus infection of a mammal comprising administering an effective amount of the drug composition of claim 13 to said mammal.

Claim 20

A method of inducing an immune response in a mammal comprising administering an effective amount of the drug composition of claim 13 to said mammal.

Claim 21

A pharmaceutical drug composition for treating virus infections or useful as an immunostimulant which comprises an anti-virally effective or immunostimulant amount of a compound of the formula: ##STR21## in which R 1 is selected from the group consisting of hydrogen, C 1 to C 5 alkyl, benzyl, phenyl ethyl, phenyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; and R 2 is selected from the group consisting of hydrogen, C 1 to C 5 alkyl, benzyl, phenyl ethyl, phenyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; the halogen in R 1 and R 2 being selected from chloro, bromo and fluoro; with the proviso that R 1 and R 2 cannot represent at the same time hydrogen, C 1 to C 5 alkyl, unsubstituted phenyl, or a heterocyclic group, and the pharmaceutically acceptable salts thereof; and a pharmaceutically effective carrier.

Claim 22

A pharmaceutical drug composition for treating virus infections or useful as an immunostimulant which comprises an anti-virally effective or immunostimulant amount of a compound of the formula: ##STR21## in which R 1 is selected from the group consisting of hydrogen, C 1 to C 5 alkyl, benzyl, phenyl ethyl, phenyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; and R 2 is selected from the group consisting of hydrogen, C 1 to C 5 alkyl, benzyl, phenyl ethyl, phenyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; the halogen in R 1 and R 2 being selected from chloro, bromo and fluoro; with the proviso that R 1 and R 2 cannot represent at the same time hydrogen, C 1 to C 5 alkyl, unsubstituted phenyl, or a heterocyclic group, and the pharmaceutically acceptable salts thereof; and a pharmaceutically effective carrier.

Claim 23

A method for treating a virus infection of a mammal comprising administering an effective amount of the drug composition of claim 16 to said mammal.

Claim 24

A method of inducing an immune response in a mammal comprising administering an effective amount of the drug composition of claim 16 to said mammal.

Claim 25

A pharmaceutical drug composition for treating virus infections or useful as an immunostimulant which comprises an anti-virally effective or immunostimulant amount of a compound of the formula: ##STR22## in which R is selected from the group consisting of hydrogen, or C 1 to C 5 alkyl; R 1 is selected from the group consisting of benzyl, phenyl ethyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; and R 2 is selected from the group consisting of benzyl, phenyl ethyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; the halogen in R 1 and R 2 being selected from chloro, bromo and fluoro; with the proviso that R 1 and R 2 cannot at the same time represent a heterocyclic group; and the pharmaceutically acceptable salts thereof; and a pharmaceutically effective carrier.

Claim 26

A pharmaceutical drug composition for treating virus infections or useful as an immunostimulant which comprises an anti-virally effective or immunostimulant amount of a compound of the formula: ##STR22## in which R is selected from the group consisting of hydrogen, or C 1 to C 5 alkyl; R 1 is selected from the group consisting of benzyl, phenyl ethyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; and R 2 is selected from the group consisting of benzyl, phenyl ethyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; the halogen in R 1 and R 2 being selected from chloro, bromo and fluoro; with the proviso that R 1 and R 2 cannot at the same time represent a heterocyclic group; and the pharmaceutically acceptable salts thereof; and a pharmaceutically effective carrier.

Claim 27

A method for treating a virus infection of a mammal comprising administering an effective amount of the drug composition of claim 11 to said mammal.

Claim 28

A method of inducing an immune response in a mammal comprising administering an effective amount of the drug composition of claim 19 to said mammal.

Claim 29

A pharmaceutical drug composition for treating virus infections or useful as an immunostimulant which comprises an anti-virally effective or immunostimulant amount of a compound of the formula: ##STR23## in which R 1 is selected from the group consisting of benzyl, phenyl ethyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; and R 2 is selected from the group consisting of hydrogen, C 1 to C 5 alkyl, benzyl, phenyl ethyl, phenyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; the halogen in R 1 and R 2 being selected from chloro, bromo and fluoro; with the proviso that R 1 and R 2 cannot at the same time represent a heterocyclic group; and the pharmaceutically acceptable salts thereof; and a pharmaceutically effective carrier.

Claim 30

A pharmaceutical drug composition for treating virus infections or useful as an immunostimulant which comprises an anti-virally effective or immunostimulant amount of a compound of the formula: ##STR23## in which R 1 is selected from the group consisting of benzyl, phenyl ethyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; and R 2 is selected from the group consisting of hydrogen, C 1 to C 5 alkyl, benzyl, phenyl ethyl, phenyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; the halogen in R 1 and R 2 being selected from chloro, bromo and fluoro; with the proviso that R 1 and R 2 cannot at the same time represent a heterocyclic group; and the pharmaceutically acceptable salts thereof; and a pharmaceutically effective carrier.

Claim 31

A method for treating a virus infection of a mammal comprising administering an effective amount of the drug composition of claim 22 to said mammal.

Claim 32

A method for treating a virus infection of a mammal comprising administering an effective amount of the drug composition of claim 22 to said mammal.

Claim 33

A pharmaceutical drug composition for treating virus infections or useful as an immunostimulant which comprises an anti-virally effective or immunostimulant amount of a compound of the formula: ##STR24## in which R 1 is selected from the group consisting of hydrogen, C 1 to C 5 alkyl, benzyl, phenyl ethyl, phenyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; and R 2 is selected from the group consisting of benzyl, phenyl ethyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; the halogen in R 1 and R 2 being selected from chloro, bromo and fluoro; with the proviso that R 1 and R 2 cannot at the same time represent a heterocyclic group, and the pharmaceutically acceptable salts thereof; and a pharmaceutically effective carrier.

Claim 34

A pharmaceutical drug composition for treating virus infections or useful as an immunostimulant which comprises an anti-virally effective or immunostimulant amount of a compound of the formula: ##STR24## in which R 1 is selected from the group consisting of hydrogen, C 1 to C 5 alkyl, benzyl, phenyl ethyl, phenyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; and R 2 is selected from the group consisting of benzyl, phenyl ethyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; the halogen in R 1 and R 2 being selected from chloro, bromo and fluoro; with the proviso that R 1 and R 2 cannot at the same time represent a heterocyclic group, and the pharmaceutically acceptable salts thereof; and a pharmaceutically effective carrier.

Claim 35

A method for treating a virus infection of a mammal comprising administering an effective amount of the drug composition of claim 25 to said mammal.

Claim 36

A method of inducing an immune response in a mammal comprising administering an effective amount of the drug composition of claim 25 to said mammal.

Claim 37

A pharmaceutical drug composition for treating virus infections or useful as an immunostimulant which comprises an anti-virally effective or immunostimulant amount of a compound of the formula: ##STR25## in which R 1 is selected from the group consisting of benzyl, phenyl ethyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; and R 2 is selected from the group consisting of benzyl, phenyl ethyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; the halogen in R 1 and R 2 being selected from chloro, bromo and fluoro; with the proviso that R 1 and R 2 cannot at the same time represent a heterocyclic group and the pharmaceutically acceptable salts thereof; and a pharmaceutically effective carrier.

Claim 38

A pharmaceutical drug composition for treating virus infections or useful as an immunostimulant which comprises an anti-virally effective or immunostimulant amount of a compound of the formula: ##STR25## in which R 1 is selected from the group consisting of benzyl, phenyl ethyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; and R 2 is selected from the group consisting of benzyl, phenyl ethyl, thienyl, pyridyl, C 5 to C 7 cycloalkyl and benzyl, phenyl ethyl, phenyl, thienyl or pyridyl substituted by a halogen, alkyl or alkoxy with C 1 to C 4 in the alkyl; the halogen in R 1 and R 2 being selected from chloro, bromo and fluoro; with the proviso that R 1 and R 2 cannot at the same time represent a heterocyclic group and the pharmaceutically acceptable salts thereof; and a pharmaceutically effective carrier.

Claim 39

A method for treating a virus infection of a mammal comprising administering an effective amount of the drug composition of claim 28 to said mammal.

Claim 40

A method of inducing an immune response in a mammal comprising administering an effective amount of the drug composition of claim 28 to said mammal.

Claim 41

A pharmaceutical composition useful as an immunostimulant which comprises a pharmaceutically acceptable carrier and a thiazolo compound of the formula ##STR26## wherein R is methyl or ethyl, R 1 is hydrogen, methyl or phenyl and R 2 is bromophenyl.

Claim 42

A pharmaceutical composition useful as an immunostimulant which comprises a pharmaceutically acceptable carrier and a thiazolo compound of the formula ##STR26## wherein R is methyl or ethyl, R 1 is hydrogen, methyl or phenyl and R 2 is bromophenyl.

Claim 43

The pharmaceutical composition useful as an immunostimulant of claim 31 wherein R is methyl and R 1 is methyl.

Claim 44

A method of treating a virus infection of a mammal which comprises administering an effective amount of the composition of claim 31.

Claim 45

A method of treating a virus infection of a mammal which comprises administering an effective amount of the composition of claim 32.