Imidazonaphthyridine derivatives

Details Imidazonaphthyridine derivatives Imidazonaphthyridine derivatives

1994-08-31

1996-01-16

Ivy, C. Warren

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D47114

Patent

active

054849241

DESCRIPTION:

BRIEF SUMMARY
This application is the National phase of PCT/JP 92/10532 filed on Nov. 24, 1992.


TECHNICAL FIELD

The present invention relates to novel imidazonaphthridine derivatives showing anti-allergic, anti-inflammatory and anti-asthmatic activities.


BACKGROUND ART

U.S. Pat. No. 4,994,468 discloses certain 4-thioimidazo[4,5-c]quinoline derivative showing bronchodilatory and anti-allergic activities. However, 4-thio- or 4-substituted mercaptoimidazo[4,5-c][1,8]naphthyridine derivatives are unknown.


DISCLOSURE OF THE INVENTION

The present invention relates to imidazonaphthridine derivatives represented by Formula (I): ##STR2## wherein X-Y-Z represents ##STR3## wherein R represents hydrogen, lower alkyl or --CH.sub.2 R.sup.1 (wherein R.sup.1 represents phenyl or pyridyl)] and pharmaceutically acceptable salts thereof.
Compounds (I) wherein R is hydrogen can exist in the form of tautomers, namely Compounds (Ia), (Ia1) and/or (Ia2). All the tautomers are included in the scope of the present invention, and they are collectively referred to as Compound (Ia) in the following description. ##STR4##
In the definitions of the groups in Formula (I), 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 salts of Compounds (I) include acid addition salts, metal salts, ammonium salts, organic amine addition salts, amino-acid addition salts.
As the pharmaceutically acceptable acid addition salts of Compound (I), inorganic acid addition salts such as hydrochloride, sulfate and phosphate, and organic acid addition salts such as acetate, maleate, fumarate, tartrate and citrate may be mentioned. As the pharmaceutically acceptable metal salts, alkali metal salts such as sodium salt and potassium salts, alkaline earth metal salts such as magnesium salt and calcium salt, aluminum salt, and zinc salt may be mentioned. As the pharmaceutically acceptable organic amine addition salts, salts with morpholine and piperidine are mentioned. As the pharmaceutically acceptable amino acid addition salts, salts with lysine, glycine, and phenylalanine may be mentioned.
The processes for preparing Compounds (I) are described below.
In the following processes, when the defined group is changed under the experimental condition or is inappropriate for practicing the processes, the processes can be readily carried out by applying the conventional manner in organic synthetic chemistry, for example, protection of functional groups and elimination of protecting groups.
Compound (I) can be obtained by the following reaction steps. ##STR5##
In the formulae, L.sup.a and L.sup.b represents a leaving group; R.sup.2 represents the same groups as those defined in R above excluding hydrogen; R.sup.3 represents hydrogen or lower alkyl; and R.sup.4 represents lower alkyl.
Lower alkyl represented by R.sup.3 and R.sup.4 means straight-chain and branched alkyl groups having 1 to 6 carbon atoms. Examples of the leaving group represented by L.sup.a and L.sup.b include a halogen atom such as chlorine, bromine and iodine, alkylsulfonyloxy such as methanesulfonyloxy, and arylsulfonyloxy such as phenylsulfonyloxy and p-toluenesulfonyloxy.
The starting Compound (II) can be synthesized according to a known method, as described in J. Org. Chem., 39, 1803 (1974), or by a similar method.
Compound (III) can be obtained by reacting Compound (II) with phosgene, triphosgene or trichloromethyl chloro formate (TCF), if necessary, in a reaction solvent.
The reaction solvent includes for example, ethers such as tetrahydrofuran and dioxane, hydrocarbons such as toluene and hexane, and halogenated hydrocarbons such as 1,2-dichloroethane and chloroform, etc. These solvents are inert to the reaction and are used alone or in combination. The reaction is carried out at 0.degree. to 200.degree. C. and completed in 5 minutes to 24 hours.
Compound (IV) can be obtained by reacting Compound (III) with Compound (IX)

REFERENCES:
patent: 4994468 (1991-02-01), Suzuki et al.
patent: 5364859 (1994-11-01), Suzuki

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