Piperazine derivatives and pharmaceuticals containing the same

Details Piperazine derivatives and pharmaceuticals containing the same Piperazine derivatives and pharmaceuticals containing the same

1993-12-30

1995-07-11

Bernard, Emily

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

514218, 514252, 544364, 544365, 544366, 544379, 544397, 540575, A61K 31495, A61K 3155, C07D295155, C07D24308

Patent

active

054321794

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/JP92/00833 filed Jul. 2,1992.
1. Technical Field
The present invention relates to novel piperazine derivatives and pharmaceuticals containing the same.
2. Background Art
Numerous piperazine derivatives have heretofore been synthesized and studied for various pharmacological effects. Among them, those having both antiallergic and antihistamic effects are known.
For example, compounds having the diphenylmethylpiperazine skeleton are disclosed in Japanese Patent Laid-Open Nos. 32474/1981, 149282/1982, 11072/1991 and the like. These compounds, however, are accompanied by one or more drawbacks such that their pharmacological effects are still insufficient and/or they are questionable in safety.
With a view toward preparing a compound having still better antiallergic and antihistamic effects and in addition, having a high degree of safety, the present inventors have carried out an extensive investigation. As a result, they have completed the present invention.


DISCLOSURE OF THE INVENTION

The present invention relates to a piperazine derivative represented by the following formula (I): ##STR2## wherein B represents a phenyl or pyridinyl group, m stands for an integer of 2 or 3, p stands for an integer of 1 or 2, R.sup.1 represents a hydrogen or halogen atom, A represents --COOR.sup.2, --Y--(CH.sub.2).sub.n , --R.sup.3, ##STR3## in which R.sup.2 represents a hydrogen atom or a lower alkyl group, Y represents a sulfur or oxygen atom, NH or .rarw.CONH-- (.rarw. indicates a bond with a (CH.sub.2).sub.m group), n stands for an integer of 0 to 3, R.sup.3 represents a cyano, amino, hydroxymethyl, 1H-tetrazole, 1-imidazolylcarbonyl, --CO--COOR.sup.4, --(CH.sub.2).sub.1 --COOR.sup.4 or --(CH.sub.2).sub.1 --CONH--R.sup.5 group (R.sup.4 : hydrogen atom or lower alkyl group, l: integer of 0 to 3; and R.sup.5 : 1H-tetrazole, thiazol-2-yl, thiazolin-2-yl, triazol-5-yl, trimethoxyphenyl or 3,5-dimethyl-4-hydroxyphenyl group), X represents CH or a nitrogen atom and R.sup.6 represents a hydrogen atom or a lower alkoxyl group, ##STR4## with the proviso that either case where R.sup.1, B, p, m and A represent a hydrogen atom, a phenyl group, 1, 2 and --NH--C.sub.6 H.sub.4 --COOR.sup.4, respectively, or where R.sup.1, B, p, m and A represent a chlorine atom, a phenyl group, 1, 2 and --O--CH.sub.2 COOH, respectively is excluded; or a salt thereof.
In addition, the present invention also relates to an antihistamic agent and an antiallergic agent each containing the piperazine derivative (I) as an active ingredient.
In the formula (I), examples of the lower alkyl group represented by R.sup.2 or R.sup.4 include C.sub.1-4 linear or branched alkyl groups, those of the lower alkoxyl group represented by R.sup.6 include C.sub.1-4 linear or branched alkyl groups, and those of the halogen atom represented by R.sup.1 include chlorine, bromine, fluorine and iodine atoms.
The piperazine derivative (I) according to the present invention can be converted to a pharmaco-logically-acceptable salt thereof, for example, an acid-addition salt such as the hydrochloride, nitrate, sulfate, maleate, fumarate, oxalate, citrate, hydrobromate, succinate, sulfaminate, mandelate, malonate and phosphate or a base salt such as the sodium salt, potassium salt, lithium salt or calcium salt.
The compounds (I) according to the present invention may have stereoisomers such as optical isomers because they may contain an asymmetric carbon atom. It is to be noted that these isomers are all embraced by the present invention.
The compounds (I) according to the present invention have excellent antihistamic and antiallergic effects and also a high degree of safety as will be described later, so that they are effective as therapeutic agents for various allergic diseases, for example, as anti-inflammatory agents, therapeutics for nephritis, hepatitis or pancreatitis, preventives and/or therapeutics for respiratory diseases, and anti-asthmatic drugs.


BEST MODES FOR CARRYING OUT THE INVENTION

The compound (I) of this invention can be prepared

REFERENCES:
patent: 4918073 (1990-04-01), Ruger et al.
Abstract for JP 3-246287 (Nov. 1, 1991).

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