Patent EP-0825193-A1 (EP)
Inventor: ALBAUGH PAMELA
IPC: C07D307/84
Filed: 1994-10-26
Abstract: The present invention encompasses structures of the
formula (I)
 
and the pharmaceutically acceptable non-toxic salts thereof
wherein T is halogen, hydrogen, hydroxyl, amino or straight
or branched chain lower alkoxy having 1-6 carbon atoms; X is
hydrogen, hydroxyl or straight or branched chain lower alkyl
having 1-6 carbon atoms; W is phenyl substituted with a 3,4-methylenedioxy,
3,4-ethylenedioxy, or 3,4-isopropylidenedioxy
group, or a 2-naphthyridinyl group which may be substituted
with halogen; and
 
represents
 
wherein Y represents nitrogen or C-R 4 ; Z represents N-R 7  or a 
carbon atom substituted with R 8  and R 9 ,  i.e. , C(R 8 )(R 9 ); n is
1, 2, 3, or 4; R 3  is hydrogen, phenyl, 2, 3 or 4-pyridyl,
straight or branched chain lower alkyl having 1-6 carbon
atoms, or phenylalkyl or 2, 3 or 4-pyridylalkyl where each
alkyl is straight or branched chain lower alkyl having 1-6
carbon atoms; R 4  is halogen or trifluoromethyl; or -OR 10 , -
COR 10 , -CO 2 R 10 , -OCOR 10 , or -R 10 , where R 10  is hydrogen, phenyl,
2, 3 or 4-pyridyl, straight or branched chain lower alkyl
having 1-6 carbon atoms, or phenylalkyl or 2, 3 or 4-pyridylalkyl
where each alkyl is straight or branched chain
lower alkyl having 1-6 carbon atoms; or -CONR 11 R 12  or
-(CH 2 ) m NR 11 R 12 , where m is 0, 1, or 2; R 11  represents hydrogen,
straight or branched chain lower alkyl having 1-6 carbon
atoms; and R 12  is hydrogen, phenyl, 2, 3 or 4-pyridyl,
straight or branched chain lower alkyl having 1-6 carbon
atoms, or phenylalkyl or 2, 3 or 4-pyridylalkyl where each
alkyl is straight or branched chain lower alkyl having 1-6
carbon atoms; or NR 11 R 12  forms a heterocyclic group which is
morpholyl, piperidyl, pyrrolidyl, or N-alkyl piperazyl; R 5  and
R 6  are the same or different and represent hydrogen, halogen,
straight or branched chain lower alkyl having 1-6 carbon
atoms, or straight or branched chain lower alkoxy having 1-6
carbon atoms; R 7  is hydrogen, phenyl, 2, 3 or 4-pyridyl,
straight or branched chain lower alkyl having 1-6 carbon
atoms, or phenylalkyl or 2, 3 or 4-pyridylalkyl where each
alkyl is straight or branched chain lower alkyl having 1-6
carbon atoms; R 8  is hydrogen or straight or branched chain
lower alkyl having 1-6 carbon atoms; and R 9  is -COR 13 , -CO 2 R 13 
or -R 13 , where R 13  is hydrogen, phenyl, 2, 3 or 4-pyridyl,
straight or branched chain lower alkyl having 1-6 carbon
atoms, or phenylalkyl or 2, 3, or 4-pyridylalkyl where each
alkyl is straight or branched chain lower alkyl having 1-6
carbon atoms; or - CONR 14 R 15  or - (CH 2 ) k NR 14 R 15 , where k is 0, 1, 
or 2; R 14  represents hydrogen, straight or branched chain
lower alkyl having 1-6 carbon atoms; and R 15  is hydrogen,
phenyl, 2, 3, or 4-pyridyl, straight or branched chain lower
alkyl having 1-6 carbon atoms, or phenylalkyl or 2, 3 or 4-pyridylalkyl
where each alkyl is straight or branched chain
lower alkyl having 1-6 carbon atoms; or NR 14 R 15  forms a
heterocyclic group which is morpholyl, piperidyl, pyrrolidyl,
or N-alkyl piperazyl; or (b) T and X are as defined above; W
is phenyl, 2 or 3-thienyl, 2, 3, or 4-pyridyl or 6-quinolinyl,
each of which may be mono or disubstituted with
halogen, cyano, hydroxy, straight or branched chain lower
alkyl having 1-6 carbon atoms, amino, mono or dialkylamino
where each alkyl is independently straight or branched chain
lower alkyl having 1-6 carbon atoms, straight or branched
chain lower alkoxy having 1-6 carbon atoms, or NR 1 COR 2 , COR 2 ,
CONR 1 R 2  where R 1  and R 2  are the same or different and represent
hydrogen or straight or branched chain lower alkyl having 1-6
carbon atoms; and
 
represents
 
or a compound of the formula: