Thienoimidazoppyridone derivatives

Details Thienoimidazoppyridone derivatives Thienoimidazoppyridone derivatives

1993-08-06

1994-08-30

Rotman, Alan L.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

546 83, C07D49112, A61K 3144

Patent

active

053428439

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to novel thienoimidazopyridone derivatives which possess excellent antiathsmatic (bronchodilator) activity and immunoregulatory activity and have a 1H, 5H- or 3H,5H-thieno[2,3-b]or [3,2-b]imidazo[4,5-d]pyridine-4-one skeleton.


PRIOR ART

A thienoimidazopyridine derivative represented by the formula: ##STR2## wherein Q is phenyl or a 5- or 6-membered heterocyclic group and Q.sup.1, Q.sup.2 and Q.sup.3 are each independently hydrogen, halogen, alkyl or haloalkyl, Unexamined Patent Application No. 99069/1988 (EP-A-223420)].


DISCLOSURE OF THE INVENTION

The present invention relates to a thienoimidazopyridone derivative represented by the Formula (I): ##STR3## wherein A and B independently represent --S-- or --CH.dbd., X-Y-Z represents --N(R.sup.2)--CH.dbd.N-- or --N.dbd.CH--N(R.sup.2)-- wherein R.sup.2 is hydrogen, lower alkyl or --CH(R.sup.3)--(CH.sub.2).sub.n --R.sup.4 wherein R.sup.4 is phenyl, n is 0 or 1, and R.sup.3 is hydrogen or lower alkyl, and R.sup.1 represents lower alkyl, or a pharmaceutically acceptable salt thereof.
In the definition of each group in Formula (I), the lower alkyl means a straight-chain or branched alkyl group having 1 to 6 carbon atoms, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, neopentyl, and hexyl.
The pharmaceutically acceptable salt of Compound (I) may be any pharmaceutically acceptable acid addition salt, for example, an inorganic acid salt such as hydrochloride, sulfate, and phosphate, or an organic acid salt such as acetate, maleate, fumarate, tartrate, and citrate.
Hereinafter, a compound represented by the Formula (I) is referred to as Compound (I), and the same shall apply to the compounds represented by other formulas.
The process for preparing Compound (I) is shown below.
Compound (I) wherein R.sup.2 is hydrogen may exist as either tautomer Compound (I-1) or Compound (I-2), and hereafter, each of Compound (I-1) and Compound (I-2) is referred to as Compound (I-1). ##STR4##


Method 1

Compound (IA), Compound (I) wherein X-Y-Z is --N(R.sup.2)--CH.dbd.N--, may be obtained by the following reaction steps.
The starting Compound (II) may be synthesized by the method described in References 1-1) to 1-4). ##STR5## wherein A, B, R.sup.1 and R.sup.2 have the same meanings as defined above.


Step 1

Compound (III) may be obtained by reacting Compound (II) with amine (VI) represented by the formula in the absence of a solvent and, if necessary, in the presence of a base.
The bases used in the reaction include alkali metal carbonates such as potassium carbonate, and sodium carbonate; alkali metal hydrides such as sodium hydride; alkyl metal alkoxides such as sodium methoxide, sodium ethoxide; and alkylamines such as triethylamine.
As the solvent, any solvent may be used, as long as it is inert to the reaction. For example, an ether such as tetrahydrofuran, and dioxane, an amide such as dimethylformamide, an alcohol such as methanol, and ethanol, a hydrocarbon such as xylene, toluene, n-hexane, and cyclohexane, a haloalkane such as chloroform, and carbontetrachloride, or dimethylsulfoxide may be used singly or in combination. The reaction is carried out at 0.degree.-100.degree. C., and is completed in 5 minutes to 24 hours.


Step 2

Compound (IV) may be obtained by reducing Compound (III) in a solvent. As the reduction method, catalytic reduction using palladium/carbon and platinum oxide, or reduction using a metal sulfur derivative such as sodium hydrosulfite, may be employed.
As the solvent, any solvent may be used, as long as it is inert to the reaction. For example, an ether such as tetrahydrofuran, and dioxane, an amide such as dimethylformamide, an alcohol such as methanol, and ethanol, an acid such as hydrochloric acid, acetic acid, and sulfuric acid, or water may be used singly or in combination. The reaction is carried out at 0.degree.-100.degree. C., and is completed in 5 minutes to 24 hours.


Step 3

Compound (V) may be obtained by reacting Compound (IV) with formic

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