Substituted aromatic compounds

• US 4,602,017 A
• Filed: 02/27/1984
• Issued: 07/22/1986
• Est. Priority Date: 06/01/1979
• Status: Expired due to Term

• Current Assignee: Smithkline Beecham Corporation (GlaxoSmithKline PLC)
• Original Assignee: Alistair A. Miller, David A. Sawyer, Martin G. Baxter
• Inventors: Sawyer, David A., Miller, Alistair A., Baxter, Martin G.
• Primary Examiner(s): Brust, Joseph Paul
• Application Number:
  US06/583,286
• Time in Patent Office: 876 Days
• Field of Search: 544/182, 424/249, 514/242
• US Class Current: 514/242
• CPC Class Codes: A61P 25/08 Antiepileptics; Anticonvulsants
• CPC Class Codes: A61P 25/18 Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
• CPC Class Codes: C07C 255/00 Carboxylic acid nitriles cyanogen or compounds thereof C01C3/00
• CPC Class Codes: C07C 281/18 the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones
• CPC Class Codes: C07C 51/15 by reaction of organic compounds with carbon dioxide, e.g. Kolbe-Schmitt synthesis
• CPC Class Codes: C07C 51/363 by introduction of halogen; by substitution of halogen atoms by other halogen atoms
• CPC Class Codes: C07C 63/70 Monocarboxylic acids
• CPC Class Codes: C07D 253/075 Two hetero atoms, in positions 3 and 5

Abstract

The present invention provides compounds of the formula (III): ##STR1## or an acid addition salt thereof, wherein R⁶ is chlorine, bromine, iodine, C_1-4 alkyl or trifluoromethyl, or R⁶ and R⁷ from a --CH═CH--CH═CH-- group optionally substituted by a halogen atom or a C_1-4 alkyl or trifluoromethyl group, R⁸ is hydrogen, bromine, iodine, C_1-4 alkyl or trifluoromethyl, R⁹ is hydrogen, halogen, C_1-4 alkyl or trifluoromethyl, R¹⁰ is hydrogen, methyl or fluorine and R¹¹ is amino, C_1-10 acylamino or di-substituted aminomethyleneamino provided that, at most, only two of R⁷ -R¹⁰ are other than hydrogen and that R⁷ -R¹⁰ are not all hydrogen when R⁶ is chlorine. Also provided are pharmaceutical compositions containing compounds of the formula (III), the first medical use of compounds of the formula (III), a process for preparing such compounds and intermediates through which this process proceeds.

Claims

1. 3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine.

2. A pharmaceutically acceptable salt of 3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine.

3. A pharmaceutical composition comprising an effective anticonvulsant amount of 3,5-Diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier therefor.

4. The composition of claim 3 in a form for oral or parenteral administration.

5. The composition of claim 3 in the form of a sterile injectable solution.

6. The composition of claim 3 in the form of a tablet or capsule.

7. A method of treating convulsions in a mammal comprising administering to said mammal an effective anticonvulsant treatment amount of the compound 3,5-Diamino-6-(2,3-dichlorophenyl)1,2,4-triazine or a pharmaceutically acceptable salt thereof.

8. The method of treating convulsions according to claim 7 in which the compound is administered.

9. The method of treating convulsions according to claim 7 in which the compound or salt is administered in a pharmaceutically acceptable carrier in a form suitable for oral or parenteral administration.

10. A method of treating epilepsy in a human comprising administering to said human an effective epilepsy treatment amount of the compound 3,5-Diamino-6-(2,3-dichlorophenyl)1,2,4-triazine or a pharmaceutically acceptable salt thereof.

11. The method of claim 10 in which the compound is administered.

12. The method of claim 10 in which the compound or salt is administered in a pharmaceutically acceptable carrier in a form suitable for oral or parenteral administration.