Phenylpyrrole derivatives and their use as dopamine D.sub.3 anta

Details Phenylpyrrole derivatives and their use as dopamine D.sub.3 anta Phenylpyrrole derivatives and their use as dopamine D.sub.3 anta

1996-08-13

1997-06-10

McKane, Joseph

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

514422, 514423, 514427, 514689, 514709, 546208, 548530, 548560, 548561, 568 31, A61K 3140, C07D20732

Patent

active

056376006

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP95/00580 filed Feb. 16, 1995.
The present invention relates to novel pyrrole derivatives, processes for their preparation, pharmaceutical compositions containing them and their use in therapy, in particular as antipsychotic agents.
European Patent Application No. 241053, describes compounds of the formula: ##STR1## wherein A is an unsaturated 5-membered heterocyclic ring, such as 2,5-pyrrolyl, or 3,5- or 1,4- pyrazolyl; X is a nitrogen or carbon atom; R.sub.1, R.sub.2, R.sub.3 are each hydrogen or alkyl; R.sub.4 is aryl, heteroaryl, arylcarbonyl or heteroaryl-carbonyl; R is selected from a variety of substituents and n is 0-4. The compounds are said to have antipsychotic properties.
European Patent Application No. 259930 describes compounds of the formula: ##STR2## wherein A is an unsaturated 5-membered heterocyclic ring, such as 2,5-pyrrolyl, 1,4-pyrazolyl or 2,5-furyl; R is hydrogen, alkyl or optionally substituted phenyl; R.sup.1 is alkyl, alkenyl or forms a ring with the phenyl group; R.sup.2 is hydrogen, hydroxy or alkoxy; R.sup.3 is selected from a variety of substituents and n is 0-3. These compounds are also said to have antipsychotic properties.
European Patent Application No. 539281 describes compounds of the formula: ##STR3## wherein Z is a residue derived from 2-aminomethyl-N-alkyl-pyrrolidine, 2-aminoethyl-N,N-diethylamine, 2-aminoethyl-morpholine, 2-aminoethyl-N,N-dibutylamine, 4-amino-N-butyl (or N-benzyl) piperidine or 2-aminoethyl-pyrrolidine; Y is alkyl or alkenyl; X is H, Cl, Br, amino, aminoalkyl, aminosulphamoyl, S-containing group (eg thiocyanato, alkylthio, alkylsulphinyl, alkylsulphonyl) methoxy, nitro, cyano, or an electron attracting group; and R is H or methoxy. The compounds are said to be dopamine antagonists, acting at the D.sub.3 receptor and to be useful inter alia as antipsychotics.
We have now found novel pyrrole derivatives which have affinity for dopamine receptors and thus have potential as antipsychotic agents.
In a first aspect the present invention provides compounds of formula (I): ##STR4## wherein R.sup.1 represents C.sub.1 -C.sub.4 alkyl; R.sup.6 is an optionally substituted aryl or optionally substituted heteroaryl group, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkoxyC.sub.1-4 alkyl, C.sub.1-4 alkylsulphonyl, trifluoromethylsulphonyl; optionally substituted arylsulphonyl, optionally substituted heteroarylsulphonyl, optionally substituted aralkylsulphonyl, optionally substituted heteroaralkylsulphonyl, nitro, cyano, amino, mono- or di-C.sub.1-4 alkylamino, trifluoromethyl, trifluoromethoxy, hydroxyl, hydroxyC.sub.1-4 alkyl, C.sub.1-4 alkylthio, C.sub.1-4 alkanoyl or C.sub.1-4 alkoxycarbonyl; or be optionally substituted by one or two C.sub.1-4 alkyl groups, and R.sup.3, R.sup.4 and R.sup.5 are as hereinbefore defined; or
R.sup.2 and R.sup.3 together form a phenyl ring, R.sup.4 represents a group R.sup.6 OSO.sub.2 -- as defined above and R.sup.5 represents hydrogen; ##STR5## wherein in group (a): optionally substituted arylC.sub.1-6 alkyl or optionally substituted heteroarylC.sub.1-6 alkyl; cycloalkylC.sub.1-4 alkyl; and cycloalkylC.sub.1-4 alkyl; optionally substituted arylC.sub.1-4 alkyl or optionally substituted heteroarylC.sub.1-4 alkyl; or cycloalkylC.sub.1-4 alkyl, optionally substituted arylC.sub.1-4 alkyl or optionally substituted heteroarylC.sub.1-4 alkyl; and optionally substituted arylC.sub.1-6 alkyl or optionally substituted heteroarylC.sub.1-6 alkyl; substituted heteroaryl group; and CH.dbd.CH(CH.sub.2).sub.w where v and w independently represent 1 to 3; 3; C.sub.3-6 cycloalkylC.sub.1-4 alkyl; and hydrogen, halogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkoxyC.sub.1-4 alkyl, nitro, cyano, trifluoromethyl, trifluoromethoxy, hydroxy, hydroxyC.sub.1-4 alkyl, C.sub.1-4 alkanoyl, C.sub.1-4 alkoxycarbonyl, amino or mono- or -di C.sub.1-4 alkylamino;
In the compounds of formula (I) an alkyl group or moiety may be straight or branched. Alkyl groups which may be employed include methyl, ethyl, n-propyl, n

REFERENCES:
CA 124: 55790S Preparation of . . . antagonists. Johnson, p. 1212. 1996.

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