TH626A - The process for preparing pyridazine-based compounds replaced with bases and the use of these compounds. - Google Patents

Abstract

The process for preparing base-substituted pyridazine compounds has the general formula as shown in Formula 1 (chemical formula), where R1, R2, and R3 independently refer to the following radicals: hydrogen, halogen, hydroxyl, nitrotrifluoromethyl, alkyl, alkoxyalkyl, alkenil, alkynil, cycloalkyl, cycloalkenil, phenyl, alkoxyhydroxyalkoxy-alkoxy, alkenilloxy, alkinilloxy, cycloalkoxyphenalkoxy, alkanoyyl, acylomino, and the -NH-CO-R9 radical, where R9 substitutes for morpholino, piperidino, or 1-pyrrolidinil, or a selectively substituted ureido radical; R4 refers to hydrogen or low molecular weight alkyl, and W represents hydrogen, chlorine, or bromine, and the acidic salts of these compounds.

Claims (9)

1. The process for preparing base-substituted pyridazine compounds has the general formula as shown in Formula 1 (chemical formula), where R1, R2, and R3 independently represent the following radicals: hydrogen, halogen, hydroxyl, nitrotrifluoromethyl, alkyl, alkoxyalkyl, alkenil, alkynil, cycloalkyl, cycloalkenil, phenyl, alkoxyhydroxyalkoxy-alkoxyalkenilloxyalkinilloxyalkinilloxycycloalkoxyphenalkoxyalkanoyl acylomino, and the -NH-CO-R9 radical, where R9 substitutes for morpholino, piperidino, or 1-pyrrolidinil, or a selectively substituted ureido radical; and R4 represents hydrogen or low molecular weight alkyl, and W represents hydrogen, chlorine, or bromine, and the acidic salts of these compounds. This is characterized by two possibilities: A. A reaction between a substance with the general formula 5 (chemical formula), where z represents (chemical formula) or (chemical formula) and Hal means halogen, and a substance with the general formula 4 (chemical formula), where R1, R2, R3, R4, and W have the meanings described above, and Y represents hydrogen or a radical that can be eliminated by hydrogenolysis. The eliminated Y radical by hydrogenolysis is removed from the resulting substance. The resulting substance is then reacted with an acid to obtain an acid-additive salt, if appropriate. Alternatively, B. A reaction between a substance with the general formula 6 (chemical formula), where R4 and W have the meanings described above, and T is chlorine or bromine, and a substance with the general formula 9 (chemical formula), where R1, R2, and R3 have the meanings described above. The resulting substance is then reacted with an acid to obtain an acid-additive salt, if appropriate. 2. The process described in claim 1 is unique in that W represents chlorine or bromine. 3. The process for preparing base-substituted pyridazine compounds, with the general formula 1a (chemical formula), where W is hydrogen and R1, R2, R3, and R4 have the meanings as stated in claim 1, is characterized by the base-substituted pyridazine compound with the general formula 1a (chemical formula), where R1, R2, R3, and R4 have the meanings as stated in claim 1, and where W represents bromine and Y represents hydrogen or radicals that can be removed by hydrogenolysis using a known method in a solvent or dispersing agent with the presence of a hydrogenating catalyst. 4. The process described in claim 3 is characterized by the use of a substance with the formula 1a, where Y is hydrogen. 5. A process according to any of the methods of claims 1-4, characterized by the use of starting materials with formulas 1a, 5, or 9, where R1, R2, and R3 independently refer to the following radicals: hydrogen, fluorine, chlorine, bromine, hydroxyl, nitro, trifluoromethyl, alkyls with 1 to 8 carbon atoms, alkoxyalkyls with 2 to 6 carbon atoms, alkenyls with up to 6 carbon atoms, alkynyls with up to 6 carbon atoms, cycloalkyls with a ring size of 5 to 8 carbon atoms, cycloalkenyls with a size of... The ring size of 5 to 8 carbon atoms includes: phenyl alkoxy with 1 to 8 carbon atoms, hydroxyalkoxy with 2 to 6 carbon atoms, alkoxyalkoxy with a total of 8 carbon atoms, alkeniloxy with no more than 6 carbon atoms, alkiniloxy with no more than 6 carbon atoms, cycloalkoxy with a ring size of 5 to 8 carbon atoms, benzyloxy, phenethoxyalkanoyl with 1 to 6 carbon atoms, and acylomino with no more than 11 carbon atoms in the acyl radical portion, the -NH-CO-R9 radical where R9 replaces morpholino, piperidino, or 1-pyrrolidinyl. The uriido is replaced at position 3 by a single cycloalkyl radical with 5 to 6 carbon atoms. The position 3 is replaced by an alkyl containing 1 to 6 carbon atoms and/or an alkhenil containing 3 to 6 carbon atoms, with just one or two radicals. 6. A process according to one of the methods of claims 1-5, which is characterized by the use of starting material formulas 1a, 5, or 9, in which among substituents R1, R2, and R3 there is only one non-hydrogen group. 7. Any process according to the methods of claims 1 through 6 that is characterized by the use of starting materials formulas 1a, 4, or 6, where R4 is hydrogen. 8. The process according to any of the methods of claims 1-7 is characterized by the use of starting materials formulas 1a, 4, or 6 where one substituent group R1, R2, or R3 represents a halogen and the other two groups represent hydrogen. 9. Any process under the method of claims 1-8 is characterized by the use of starting materials formula 1a, 5, or 9, where R1 is 2-chlorine, R2 is hydrogen, and R3 is hydrogen, and by the use of starting materials formula 1a, 4, or 6, where R4 is hydrogen. (Clause 9, 4 pages, 0 images)