Piperazine derivatives and methods for the preparation thereof a

Details Piperazine derivatives and methods for the preparation thereof a Piperazine derivatives and methods for the preparation thereof a

1996-07-15

1998-07-14

Bernhardt, Emily

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

544360, 544364, 544357, A61K 31495, C07D40112, C07D40114

Patent

active

057804729

DESCRIPTION:

BRIEF SUMMARY
THE PRESENT INVENTION RELATES TO NEW PIPERAZINE DERIVATIVES OF THE GENERAL
FORMULA(I) ##STR2## wherein R.sub.1 and R.sub.2 are independently hydrogen, C.sub.1 -C.sub.8 alkyl or optionally substituted C.sub.3 -C.sub.6 membered cycloalkyl containing C.sub.3 -C.sub.8 ; R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 are independently hydrogen, halogen, hydroxy, nitro, C.sub.1 -C.sub.4 lower ester, C.sub.1 -C.sub.4 lower alkyl, C.sub.1 -C.sub.4 lower alkoxy, aryl, arylalkoxy or unsaturated amine; l is an integer of 0-7; m and n are independently an integer of 0-1; W is carbon or nitrogen; X is oxygen, sulfur, optionally substituted imine; Y is nitrogen or oxygen; and Z is hydrogen, C.sub.1 -C.sub.8 alkoxy, aryloxy, C.sub.1 -C.sub.4 alkylamine, cycloamine containing N.sub.1 -N.sub.5 or oxo group.
C.sub.1 -C.sub.8 alkyl means straight or branch alkyl group such as methyl, ethyl, propyl, butyl, isobutyl, tert-butyl, pentyl, iso-pentyl, hexyl, heptyl, octyl, 2-methyl-pentyl or the like.
C.sub.1 -C.sub.4 lower alkyl means methyl, propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl or the like.
Optionally substituted 3-6 membered cycloalkyl containing C.sub.3 -C.sub.8 means substituted or unsubstituted cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, substituted cyclopropyl, substituted cyclopentyl, substituted cyclohexyl or the like.
C.sub.1 -C.sub.4 lower ester means a carboxyl group esterified by lower alkyl group.
C.sub.1 -C.sub.4 lower alkoxy means methoxy, ethoxy, propyloxy, isopropyloxy, butyloxy, isobutyloxy, tert-butyloxy group or the like.
Aryioxy means phenoxy, substituted phenoxy, naphthyloxy or substituted naphthyloxy or the like.
Cycloamine group containing N.sub.1 -N.sub.5 means pyrrolidinyl, pyrrolinyl, imidazolyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, triazolyl, tetrazolyl, piperazinyl or the like.
The general formula(I) compound wherein Z is oxo has the structural formula(I') by tautomerism. ##STR3##
The present inventors had studied to find compounds having intensive antitumor activity for a long time. As the results, we finally found out the facts that the foresaid compounds of the general formula(I) and acid addition salts thereof have not only prominant antitumor activity but very low toxicity. Accordingly, the one object of the present invention is to provide the novel compounds of the general formula(I) and acid addition salts thereof having not only prominent antitumor activity but very low toxicity.
The other object of the present invention is to provide a process for the preparation of the compounds of general formula(I) and acid addition salts thereof.
The compounds of the present invention can be mixed with pharmaceutically acceptable vehicles by a known method to give pharmaceutical compositions and the pharmaceutical compositions can be used to prevent or treat various kinds of tumors of human beings or mammals.
Therefore, another object of the present invention is to provide pharmaceutical compositions containing the compounds of the general formula(I) and acid addition salts thereof as active ingredients.
Acids which can be reacted with the compounds of the general formula(I) to form acid addition salts are pharmaceutically acceptable inorganic or organic acids such as hydrochloric acid, bromic acid, sulfuric acid, phosphoric acid, nitric acid, formic acid, acetic acid, propionic acid, succinic acid, citric acid, maleic acid, malonic acid, glycolic acid, lactic acid, glycine, alanine, valine, luecine, isoleucine, serine, cysteine, cystine, asparaginic acid, glutamic acid, lysine, arginine, tyrosine, proline, methane sulfonic acid, ethane sulfonic acid, benzene sulfonic acid, toluene sulfonic acid or the like.
Vehicles which can be used in the preparation of pharmaceutical compositions containing the compounds of the general formula(I) as active ingredient are sweetening agent, binding agent, dissolving agent, aids for dissolution, wetting agent, emulsifying agent, isotonic agent, adsorbent, degrading agent, antioxident, antiseptics, lubricating age

REFERENCES:
Courant et al, Eur. J. Med. Chem. 28 pp. 821-824, 1993.
Kanoto, Chemical Abstracts, vol. 113, No. 172058 (1990) (Abstract of JP 02/42,770 May 31, 1990).
Ried et al, Liebigs Ann. Chem. pp. 693-698 (1980).

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