Bis-(aminoalkoxy)-phenyl, pyridyl ketones, and use as immunologi

Details Bis-(aminoalkoxy)-phenyl, pyridyl ketones, and use as immunologi Bis-(aminoalkoxy)-phenyl, pyridyl ketones, and use as immunologi

1982-07-28

1984-08-14

Jiles, Henry R.

Drug, bio-affecting and body treating compositions

Antigen, epitope, or other immunospecific immunoeffector

Bacterium or component thereof or substance produced by said...

42424858, 424250, 424263, 424267, 544121, 544124, 544257, 544360, 546187, 546194, 546283, 546290, 546298, 546300, 546301, A61K 3144, C07D21364

Patent

active

044656815

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD AND DISCLOSURE OF THE INVENTION

This invention relates to novel pyridine derivatives which are useful as medicines and are represented by the formula: ##STR3## and salts thereof.
In the above formula, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different and each represents hydrogen atom or lower alkyl group such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl, or R.sup.1 and R.sup.2, or R.sup.3 and R.sup.4 together with the adjacent nitrogen atom form a hetereocycle such as pyrrolidine, piperidine, piperazine, 4-methylpiperazine, 4-(hydroxyethyl)piperazine, morpholine or imidazole, A.sup.1 and A.sup.2 are the same or different and each represents straight or branched alkylene group such as methylene, ethylene, propylene, trimethylene or tetramethylene or hydroxy-substituted alkylene group such as 2-hydroxytrimethylene, Y.sup.1 and Y.sup.2 are the same or different and each represents oxygen or sulfur atom, and Z is --CO--, --CH.sub.2 --, --CH(OH)-- or --C(.dbd.NOH)--.
The pyridine derivatives of the present invention can be produced by the following methods, for example.


METHOD 1

This method, to be applied for the production of compounds of formula (I) wherein Z is --CO--, comprises reacting a compound of the formula: ##STR4## wherein X.sup.1 and X.sup.2 are the same or different and each represents halogen atom such as fluorine, chlorine or iodine, with a compound of the formula: ##STR5## wherein each symbol is as defined above.
The reaction proceeds in a solvent such as dimethylformamide, dimethyl sulfoxide, hexamethylphosphoramide, toluene, xylene, lower alkanol or pyridine at -10.degree. C. to 150.degree. C. Moreover, the reaction is preferably carried out by using a starting material (III) of which the active hydrogen atom is converted into the alkali metal salt by the use of sodium hydride, sodium amide, sodium alkoxide, sodium hydroxide, potassium hydroxide or the like, or in the presence of an acid acceptor such as potassium carbonate or sodium carbonate.
When the reaction is carried out by one step, compounds of formula (I) wherein (R.sup.1)(R.sup.2)N--A.sup.1 --Y.sup.1 -- and (R.sup.3)(R.sup.4)N--A.sup.2 --Y.sup.2 -- are identical are obtained. However, it is possible to obtain compounds wherein both the groups are different each other by carrying out the reaction stepwise under the reaction conditions suitably selected. For instance, the reaction of 2-chloro-3(4-fluorobenzoyl)pyridine of the formula: ##STR6## with an equimolecular amount of a compound of formula (III) in toluene gives a compound of the formula: ##STR7## and the said reaction in dimethylformamide gives a compound of the formula: ##STR8##
Compound (IV) or (V) is reacted with a compound which is different to compound (III) and has the formula: ##STR9## wherein each symbol is as defined above, under the conditions mentioned above to give compound (I). It goes without saying that a compound (IV) or (V) can be reacted, after or without isolation, with the same starting material (III).
When a compound (III) or (VI) wherein A represents a hydroxy-substituted alkylene is used as a starting material in all of the above reactions, it is desirable that the compound of which the hydroxy group is protected by an acyl group such as acetyl, propionyl, pivaloyl or benzoyl or by forming an oxazolidine ring (e.g. as a compound (III), the compound of the formula: ##STR10## is used in the reaction, and then the final reaction product is hydrolyzed to eliminate the protecting group by an acid or alkali such as hydrochloric acid, sulfuric acid, potassium carbonate or sodium hydroxide.


METHOD 2

This method, to be applied for the production of compounds of formula (I) wherein Z is --CH.sub.2 -- or --CH(OH)--, comprises reducing a compound of formula (I) wherein Z is --CO--.
The reduction is carried out by a conventional method such as reduction with a complex metal hydride (e.g. sodium borohydride or lithium aluminium hydride), reduction with sodium amalgam, Clemmensen reduction, Wolff-Kish

REFERENCES:
Chemical Abstracts, vol. 96, 3509v, (1982).
Central Patent Index, Abstract No. 70795 D/39.

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