JPH0142267B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the following general formula (In the formula, R ₁ is a halogen atom, a hydrazino group, or a group -NHR ₂ , -OR ₂ , -SR ₂ or

[Formula] is shown. Here, R ₂ means an alkyl group, cycloalkyl group, alkenyl group, alkynyl group, aralkyl group, phenyl group, or pyridyl group having 2 or more carbon atoms, and R ₃ and R ₄ are lower alkyl, and these are also (which may be bonded to each other to form a heterocyclic ring that may contain other oxygen atoms or nitrogen atoms). The compounds represented by the general formula [] not only have anti-inflammatory, analgesic, antithrombotic, or anticancer effects per se, but also include substances that can be used as pharmaceutical intermediates. The compounds of the present invention may be, for example, represented by the following general formula: (In the formula, R ₁ has the same meaning as above, and R' represents a hydrogen atom or a lower alkyl group) and methylamine are subjected to a usual acid amide forming reaction at room temperature to 100°C. It can be obtained by R ₁ in the compound of the general formula [] thus obtained
is a halogen atom, it can be converted into a group other than the halogen atom defined above for R ₁ by reacting it with amines, alcohols or thioalcohols in the presence of a basic auxiliary if desired. be able to. Similarly, a compound in which R ₁ in the general formula [] is an amino group or a hydroxyl group can be converted to the formula
R ₂ X [] (in the formula, R ₂ has the same meaning as above,
The corresponding general formula [] can also be obtained by reacting with a compound represented by (X represents a halogen atom)
can lead to compounds of Example 1 8 g of 4-chloro-2,6-pyridinedicarboxylic acid dimethyl ester was dissolved in 30 ml of methanol and 30 ml of 40% methylamine aqueous solution, left at room temperature for 1 hour, concentrated under reduced pressure, washed the residue with water, and mixed with methanol and water. Recrystallized from a solvent to give 4-
7.1 g of chloro-N,N'-dimethyl-2,6-pyridinedicarboxylic acid amide was obtained. Elemental analysis value Molecular formula: C ₉ H ₁₀ ClN ₃ O ₂ C H N Theoretical value (%) 47.5 1.4 18.5 Actual value (%) 47.2 4.6 18.6 Examples 2 to 5 The compounds in Table 1 were prepared in the same manner as in Example 1. Obtained.

[Table] Example 6 3 g of 4-chloro-N,N'-dimethyl-2,6-pyridinedicarboxylic acid amide and 30 ml of methanol
and 10 g of n-propylamine in a sealed tube at 100°C.
The reaction mixture was heated for 2 days, the reaction solution was concentrated, and the residue was mixed with dilute hydrochloric acid to remove insoluble matter. Potassium carbonate is added to the liquid to make it alkaline, and the precipitated crystals are recrystallized from a methanol-water mixed solvent to give a melting point of 270~
1.8 g of 4-n-propylamino N,N'-dimethyl-2,6-pyridinedicarboxylic acid amide at 272°C
I got it. Elemental analysis value Molecular formula C ₁₂ H ₁₈ N ₄ O ₂ C H N Theoretical value (%) 57.6 7.3 22.4 Actual value (%) 57.7 7.4 22.6 Examples 7 to 10 Compounds in Table 2 were prepared in the same manner as in Example 6. Obtained.

【table】

Claims (1)

[Claims] 1. General formula (In the formula, R ₁ represents a halogen atom, a hydrazino group, a group -NHR ₂ , -OR ₂ , -SR ₂ or [Formula]. Here, R ₂ represents an alkyl group having 2 or more carbon atoms, a cycloalkyl group, or an alkenyl group. , an alkynyl group, an aralkyl group, a phenyl group or a pyridyl group, and R ₃ and R ₄ are lower alkyl, which are also bonded to each other and may contain other oxygen atoms or nitrogen atoms. (may form a ring).