Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent
Patent
1994-10-11
1996-12-24
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Chalcogen in the nitrogen containing substituent
544230, 546 15, 546 16, 540466, 540543, 548408, 514409, C07D22120, C07D40106, C07D20954, A61K 3140
Patent
active
055874797
DESCRIPTION:
BRIEF SUMMARY
This application is a 35 U.S.C. .sctn. 371 case of PCT/EP93/00842, filed Apr. 6, 1993. The subject of the present invention is basic derivatives of glutamic acid and aspartic acid which can be represented by the general formula indicated below: ##STR1## and in which r is 1 or 2;
R.sub.1 is selected independently from:
unsubstituted phenyl mono- or di-substituted phenyl groups in which the substituents are selected from the halogens (chloro, fluoro, and bromo), linear or branched C.sub.1 -C.sub.4 alkyl groups, and nitro, cyano, methoxy, and trifluoromethyl groups; an unsubstituted phenylamino group; phenylamino groups mono- or di-substituted as described above for the phenyl group; the 2(beta)-naphthyl group; heterocyclic, monocyclic or dicyclic groups selected from an unsubstituted pyridyl group, pyridyl groups mono- or di-substituted with methyl, chloro, furyl (2- or 3-yl), indolyl (2- or 3-yl), isoindolyl (3-yl), benzofuranyl (2- or 3-yl) quinolinyl (2- or 3-yl) or isoquinolinyl (3-yl);
R.sub.2 is selected independently from:
1) a heterocyclic spiro group represented by: ##STR2## in which m and n are selected independently and may have values of between 1 and 3, provided that the ring formed consists of at least 5 atoms, X and Y are selected independently from (CH--R.sub.4).sub.z, TCH.sub.2 and CH.sub.2 T in which T is O or S, and in which R.sub.4 is a group selected independently from H, linear and branched C.sub.1 -C.sub.4 alkyl groups, OCH.sub.3, and OH, and z may have values of from 0 to 3, provided that the ring formed consists of at least 3 atoms;
2) an aminoalkyladamantyl group represented by: ##STR3## in which z and R.sub.4 have the meanings given above and Ad is adamantyl (1- or 2-yl);
3) an alkylamino group represented by: ##STR4## in which R.sub.5 is a linear or branched alkyl chain containing from 4 to 10 carbon atoms or a C.sub.5 -C.sub.10 cycloaklyl group, or a linear or branched alkoxyalkyl group containing from 4 to 7 carbon atoms, and R.sub.6 is selected independently from H, alkyl groups, linear and branched alkoxyalkyl groups containing from 4 to 7 carbon atoms, and C.sub.5 -C.sub.10 cycloalkyl groups;
4) a C.sub.4 -C.sub.10 cycloalkylamine;
5) a dicyclic amino group (condensed) represented by: ##STR5## and in which m, n, X, Y, and R.sub.4 have the meanings given above;
R.sub.3 is H, CH.sub.3 or C.sub.2 H.sub.5 ;
A is a bond or a linear or branched alkylene group comprising from 1 to 4 carbon atoms;
W may be:
1) a tertiary amino group represented by: ##STR6## in which R.sub.7 and R.sub.8 are, independently, hydrogen or a linear or branched alkyl group comprising from 1 to 5 carbon atoms, provided that R.sub.7 and R.sub.8 are not both hydrogen;
2) a heterocyclic group represented by: ##STR7## in which R.sub.3, m and n have the meanings given above and Q may be a bond, CH.sub.2, oxygen, sulphur or nitrogen, N-substituted with R.sub.9, R.sub.9 being a group selected independently from H, linear and branched C.sub.1 -C.sub.4 alkyl groups, phenyl and benzyl groups, of which the aromatic groups may be unsubstituted or mono- or di-substituted as described for the phenyl group in R.sub.1 ;
3) a heterocyclic group represented by: ##STR8## in which m1 and m2 are selected independently and may have values of between 0 and 3 and R.sub.3 and R.sub.9 have the meanings given above;
4) a heterocyclic group represented by: ##STR9## in which m, m1, m2 and R.sub.3 have the meanings given above;
t is always 1; it may also have a value or u, but only if W is a heterocyclic group selected from group 2, in which Q is N--R.sub.9.
The stereochemistry of the compounds claimed at the chiral centre marked with an asterisk in formula (I) may be racemic (R, S), R (rectus), or S (sinister), r is preferably 2, and R.sub.3 is preferably hydrogen.
According to the nature of the substituents at R.sub.1, R.sub.2, A and W, the compounds of the present invention have been shown to have a potent antagonistic effect on gastrin (anti-CCK-B activity) and on cholecystokinin (anti-CCK-A activity) and can thus be used to advantag
REFERENCES:
Diago-Meseguer, J. et al. Synthesis, pp. 547-551.
Makovec Francesco
Rovati Lucio C.
Rovati Luigi A.
Rotta Research Laboratorium S.p.A.
Shah Mukund J.
Wong King Lit
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