RU98114487A - SUBSTITUTED 6-R-1,3,4-TIADIAZIN-2-AMINES, THEIR USE AS ANESTHETIC, CARDIOVASCULAR AND HYPOMETABOLIC DRUGS AND CONTAINING THEIR PHARMACEUTICAL CHEMICALS - Google Patents

Claims (6)

1. Substituted 6-R-1,3,4-thiadiazin-2-amines of the general formula:

where Ar is phenyl or phenyl substituted by one or more chlorine, bromine, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkyl groups; each of R ¹ and R ² is, independently, a hydrogen atom or a C ₁ -C ₄ alkyl residue; and R ³ and R ^{4 are} independently selected from C ₁ -C ₄ alkyl groups; and their pharmaceutically acceptable salts.  2. Substituted 6-R-1,3,4-thiadiazin-2-amines according to claim 1, selected from the following row: 2-N-methyl-N- (1-phenyl-2,3-dimethylpyrazole-5-one -4-yl) amino-5-phenyl-6H-1,3,4-thiadiazine; 2-N-methyl-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5- (4-bromophenyl) -6H-1,3,4-thiadiazine; 2-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5-phenyl-6H-1,3,4-thiadiazine; 2-N-methyl-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5-phenyl-6H-6-ethyl-1,3,4-thiadiazine; 2-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5-phenyl-6H-6-ethyl-1,3,4-thiadiazine; 2-N-methyl-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5- (4-ethoxyphenyl) -6H-1,3,4-thiadiazine; 2-N-methyl-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5- (4-chlorophenyl) -6H-1,3,4-thiadiazine; 2-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5- (3-bromophenyl) -6H-1,3,4-thiadiazine; 2-N-methyl-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5- (3-bromophenyl) -6H-1,3,4-thiadiazine; and their pharmaceutically acceptable salts. 3. The use of substituted 6-R-1,3,4-thiadiazin-2-amines as described in claim 1, of the formula

where Ar is phenyl or phenyl substituted by one or more chlorine, bromine, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkyl groups; each of R ¹ and R ² is, independently, a hydrogen atom or a C ₁ -C ₄ alkyl residue; and R ³ and R ^{4 are} independently selected from the C ₁ -C ₄ alkyl group; and their pharmaceutically acceptable salts as anesthetic, cardiovascular and hypometabolic agents.  4. The use according to claim 3, wherein the substituted 6-R-1,3,4-thiadiazin-2-amines are selected from the following row: 1) 2-N-methyl-N- (1-phenyl-2,3- dimethylpyrazol-5-one-4-yl) amino-5-phenyl-6H-1,3,4-thiadiazine; 2) 2-N-methyl-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5- (4-bromophenyl) -6H-1,3,4-thiadiazine; 3) 2-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5-phenyl-6H-1,3,4-thiadiazine; 4) 2-N-methyl-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5-phenyl-6H-6-ethyl-1,3,4-thiadiazine; 5) 2-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5-phenyl-6H-6-ethyl-1,3,4-thiadiazine; 6) 2-N-methyl-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5- (4-ethoxy-phenyl) -6H-1,3,4- thiadiazine; 7) 2-N-methyl-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5- (4-chlorophenyl) -6H-1,3,4-thiadiazine; 8) 2-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5- (3-bromophenyl) -6H-1,3,4-thiadiazine; 9) 2-N-methyl-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5- (3-bromophenyl) -6H-1,3,4-thiadiazine; and their pharmaceutically acceptable salts. 5. A pharmaceutical composition comprising an effective amount of the active agent and a pharmaceutically acceptable excipient, diluent and / or other excipients, characterized in that the composition contains at least one of the compounds of the general formula as an active agent.

where Ar is phenyl or phenyl substituted by one or more chlorine, bromine, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkyl groups; each of R ¹ and R ² is, independently, a hydrogen atom or a C ₁ -C ₄ alkyl residue; and R ³ and R ^{4 are} independently selected from C ₁ -C ₄ alkyl groups; and their pharmaceutically acceptable salts.  6. The pharmaceutical composition according to claim 5, characterized in that, as the active agent, it contains a substituted 6-R-1,3,4-thiadiazin-2-amine, as defined in claim 1, selected from the following row: 2-N -methyl-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5-phenyl-6H-1,3,4-thiadiazine; 2-N-methyl-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5- (4-bromophenyl) -6H-1,3,4-thiadiazine; 2-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5-phenyl-6H-1,3,4-thiadiazine; 2-N-methyl-N- (1-phenyl-2,3-dimethyl-pyrazol-5-one-4-yl) amino-5-phenyl-6H-6-ethyl-1,3,4-thiadiazine; 2-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5-phenyl-6H-6-ethyl-1,3,4-thiadiazine; 2-N-methyl-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5- (4-ethoxyphenyl) -6H-1,3,4-thiadiazine; 2-N-methyl-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5- (4-chlorophenyl) -6H-1,3,4-thiadiazine; 2-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5- (3-bromophenyl) -6H-1,3,4-thiadiazine; 2-N-methyl-N- (1-phenyl-2,3-dimethylpyrazol-5-one-4-yl) amino-5- (3-bromophenyl) -6H-1,3,4-thiadiazine; and their pharmaceutically acceptable salts.