US 5,922,887 A · Diaryldiamine derivatives and their use as delta opiod (ANT)-agonists

Abstract

A compound, or solvate or salt thereof, of formula (I) ##STR1## in which, R.sub.1 and R.sub.2, are, independently hydrogen, linear or branched C.sub.1-6 alkyl, C.sub.3-7 cycloalkyl, C.sub.3-7 cycloalkenyl, or C.sub.3-6 alkenyl, or together form a C.sub.3-7 alkyl; R.sub.3 and R.sub.4 are, independently, hydrogen, linear or branched C.sub.1-6 alkyl, or R.sub.4 is oxygen forming with the carbon atom to which is attached a C.dbd.O group; R.sub.5 is hydrogen, hydroxy, or C.sub.1-3 alkoxy; R.sub.6 is halogen, NH.sub.2 or a para or meta --COR-8 group, in which R.sub.8 is C.sub.1-8 -alkyl, C.sub.1-8 -alkoxy or NR.sub.9 R.sub.10, wherein R.sub.9 and R.sub.10, are, independently, hydrogen, straight or branched C.sub.1-6 alkyl, C.sub.3-7 cycloalkyl or phenyl; or R.sub.6 is a para or meta group ##STR2## in which R.sub.11 and R .sub.12 are, independently, hydrogen or straight or branched C .sub.1-6 and, R.sub.7 is hydrogen, or straight or branched C.sub.1-8 alkyl; is provided. The present compound is useful as a delta opiod modulator.

Claims10

Dependent claims

A compound, or solvate or salt thereof, of formula (I) ##STR16## in which, R.sub.1 and R.sub.2, are, independently hydrogen, linear or branched C.sub.1-6 alkyl, C.sub.3-7 cycloalkyl, C.sub.3-7 cycloalkenyl, or C.sub.3-6 alkenyl, or together form a C.sub.3-7 alkyl ring;

R.sub.3 and R.sub.4 are, independently, hydrogen, linear or branched C.sub.1-6 alkyl, or R.sub.4 is oxygen forming with the carbon atom to which is attached a C.dbd.O group;
R.sub.5 is hydrogen, hydroxy, or C.sub.1-3 alkoxy;
R.sub.6 is halogen, NH.sub.2 or a para or meta --COR-8 group, in which R.sub.8 is C.sub.1-8 -alkyl, C.sub.1-8 -alkoxy or NR.sub.9 R.sub.10, wherein R.sub.9 and R.sub.10, are, independently hydrogen, straight or branched C.sub.1-6 alkyl, C.sub.3-7 cycloalkyl or phenyl;
or R.sub.6 is a para or meta ##STR17## group in which R.sub.11 and R.sub.12 are, independently, hydrogen or straight or branched C.sub.1-6 alkyl and,
R.sub.7 is hydrogen, or straight or branched C.sub.1-8 alkyl.

2 more elements

A compound selected from:

(-)-3-N-(3-pyrrolidinoprop-2-yl) phenylamino!-N-propylbenzamide;
(.+-.)-N-(4-bromophenyl)-N-(3-hydroxyphenyl)-.alpha.-methyl-1-pyrrolidinoet hanamine;
(.+-.)-N-(4-bromophenyl)-N-(3-methoxyphenyl)-.alpha.-methyl-1-pyrrolidinoet anamine;
(.+-.)-N,N-(4)-N,N-diethyl-4-N-(3-methoxyphenyl)-N-(3-pyrrolidinoprop-2-y l)!amino!benzamide;
(.+-.)-N,N-diethyl-4-N-(3-hydroxyphenyl)-N-(3-pyrrolidinoprop-2-yl)!amino !benzamide;
N-(4-bromophenyl)-N-(3-hydroxyphenyl)-1-pyrrolidinoethanamine;
N,N-diethyl-4-N-(2-dimethylaminoethyl)-N-(3-hydroxyphenyl)!amino!benzamid e;
(.+-.)-N,N-diethyl-4-N-(2-dimethylaminoprop-1-yl)-N-(3-hydroxyphenyl)!ami no!benzamide;
(.+-.)-N,N-diethyl-4-N-(3-dimethylaminoprop-2-yl)-N-(3-hydroxyphenyl)!ami no!benzamide;
N,N-diethyl-4-N-(3-hydroxyphenyl)-N-(2-pyrrolidinoethyl)!amino!benzamide;
N,N-diethyl-4-N-(3-methoxyphenyl)-N-(2-pyrrolidinoethyl)!amino!benzamide;
N,N-diethyl-4-N-(2-dimethylaminoethyl)-N-(3- methoxyphenyl)!amino!benzamide;
N,N-diethyl-4-N-(2-dimethylaminoethyl)-N-(3-methoxyphenyl)!amino!benzamid e;
(.+-.)-N.sup.2 -(4-biphenylyl)-N.sup.1,N.sup.1 -dimethyl-N.sup.2 -(3-hydroxyphenyl)-1,2-propandiamine;
(.+-.)-N.sup.1 -(4-biphenylyl)-N.sup.2,N.sup.2 -dimethyl-N.sup.1 -(3-hydroxyphenyl)-1,2-propandiamine;
(.+-.)-N.sup.2 -(4-biphenylyl)-N.sup.1,N.sup.1 -dimethyl-N.sup.2 -(3-methoxyphenyl)-1,2-propandiamine;
(.+-.)-N.sup.1 -(4-biphenylyl)-N.sup.2,N.sup.2 -dimethyl-N.sup.1 -(3-methoxyphenyl)-1,2-propandiamine;
N,N-diethyl-4-N-(dimethylaminoacetyl)-N-(3-methoxyphenyl)!amino!benzamide
(.+-.)-1-4-N-(3-dimethylaminoprop-2-yl)-N-(3-methoxyphenyl)!amino!benzoy l!pyrrolidine;
(.+-.)-1-4-N-(2-dimethylaminoprop-1-yl)-N-(3-methoxyphenyl)!amino!benzoy l!pyrrolidine;
(.+-.)-1-4-N-(3-dimethylaminoprop-2-yl)-N-(3-hydroxyphenyl)!amino!benzoy l!pyrrolidine;
(.+-.)-1-4-N-(2-dimethylaminoprop-1-yl)-N-(3-hydroxyphenyl)!amino!benzoy l!pyrrolidina;
(.+-.)-N,N-diethyl-3-N-(3-dimethylaminoprop-2-yl)-N-(3-hydroxyphenyl)!ami no!benzamide;
(.+-.)-N,N-diethyl-3-N-(2-dimethylaminoprop-1-yl)-N-(3-hydroxyphenyl)!ami no!benzamide;
(.+-.)-N,N-diisopropyl-4-N-(3-dimethylaminoprop-2-yl)-N-(3-hydroxyphenyl) !amino!benzamide;
(.+-.)-N,N-diisopropyl-4-N-(2-dimethylaminoprop-1-yl)-N-(3-hydroxyphenyl) !amino!benzamide;
(.+-.)-N,N-diethyl-3-N-(3-hydroxyphenyl)-N-(3-pyrrolidinoprop-2-yl)!amino !benzamide;
(.+-.)-N,N-diethyl-3-N-(3-hydroxyphenyl)-N-(2-pyrrolidinoprop-1-yl)! amino!benzamide;
(.+-.)-N,N-diethyl-4-N-(3-hydroxyphenyl)-N-(1-pyrrolidinyl-2-butyl) amino!benzamide;
(.+-.)-N,N-diethyl-4-N-(3-hydroxyphenyl)-N-(2-pyrrolidinyl-1-butyl)!amino !benzamide;
(.+-.)-N,N-diethylN-(2-dimethylaminoprop-1-yl)-N-(3-methoxyphenyl)!amino! benzamide;
(.+-.)-N,N-diethyl-4-N-(3-dimethylaminoprop-2-yl)-N-(3-methoxyphenyl)!ami no!benzamide;
(.+-.)-N,N-diethyl-3-N-(3-dimethylaminoprop-2-yl)-N-(3-methoxyphenyl)!ami no!benzamide;
(.+-.)-N,N-diethyl-3-N-(2-dimethylaminoprop-1-yl)-N-(3-methoxyphenyl)!ami no!benzamide;
(.+-.)-N,N-diisopropyl-4-N-(3-dimethylaminoprop-2-yl)-N-(3-methoxyphenyl) !amino!benzamide;
(.+-.)-N,N-diisopropyl-4-N-(2-dimethylaminoprop-1-yl)-N-(3-methoxyphenyl) !amino!benzamide;
(.+-.)-N,N-diethyl-3-N-(3-methoxyphenyl)-N-(3-pyrrolidinoprop-2-yl)!amino !benzamide;
(.+-.)-N,N-diethyl-3-N-(3-methoxyphenyl)-N-(2-pyrrolidinoprop-1-yl)!amino !benzamide;
(.+-.)-N,N-diethylN-(3-methoxyphenyl)-N-(1-pyrrolidinyl-2-butyl)!amino!be nzamide;
(.+-.)-N,N-diethyl-4-N-(3-methoxyphenyl)-N-(2-pyrrolidinyl-1-butyl)!amino !benzamide;
(.+-.) 4-N-1-(N-allyl-N-methyl)amino-2-propyl!-N-(3-hydroxyphenyl)amino!-N, N-diethylbenzamide;
(.+-.)-4-N-2-(N-allyl-N-methyl)amino-1-propyl!-N-(3-hydroxyphenyl)amino!- N, N-diethylbenzamide;
N,N-diethyl-4N-(dimethylaminoacetyl)-N-(3-hydroxyphenyl)!amino!benzamide;
(.+-.)-N-4-N-(3-methoxyphenyl)-N-1-methyl-2-( 1-pyrrolidinyl) ethyl!!amino!phenyl!-2-methylpropanamide;
(.+-.)-N-4-N-(3-hydroxyphenyl)-N-1-methyl-2-(1-pyrrolidinyl) ethyl!!amino!phenyl!-2-methylpropanamide;
(-)-N,N-diethyl-4-N-(3-dimethylaminoprop-2-yl)N-(3-;
hydroxyphenyl)!amino!benzamide;
(+)-N,N-diethyl-4-N-(3-dimethylaminoprop-2-yl)-N-(3-hydroxyphenyl)!amino! benzamide;
N,N-diethyl-4-N-(diethylaminoacetyl)-N-(3-hydroxyphenyl)!amino!benzamide;
N,N-diethyl-4-N-(3-hydroxyphenyl)-N-(pyrrolidin-1-ylacetyl)!amino!benzami de;
N,N-diisopropyl-4N-(dimethylaminoacetyl)-N-(3-hydroxyphenyl)!amino!benzam ide;
4-N-(N-allyl-N-methyl)amino!acetyl-N-(3-hydroxyphenyl)!amino!-N,N-dieth ylbenzamide;
N,N-diethyl-4-N-(3-hydroxyphenyl)-N-(methylaminoacetyl)!amino!benzamide;
N,N-diisopropyl-4-N-aminoacetyl-N-(3-hydroxyphenyl)!amino!benzamide;
(.+-.)-4(N-1-(N-allyl-N-methyl)amino-2-propyl!-N-(3-methoxyphenyl)amino!-N ,N,-diethylbenzamide;
(.+-.)-4-N-2-(N-allyl-N-methyl)amino-1-propyl!-N-(3-methoxyphenyl)amino!- N,N-diethylbenzamide;
N,N-diethyl-4-N-(diethylaminoacetyl)-N-(3-methoxyphenyl)!amino!benzamide;
N,N-diethyl-4-N-(3-methoxyphenyl)-N-(pyrrolidin-1-ylacetyl)!amino!benzami de;
N,N-diisopropyl-4-N-(dimethylaminoacetyl)-N-(3-methoxyphenyl)!amino!benza mide;
4-N-(N-allyl-N-methyl)amino!acetyl!-N-(3-methoxyphenyl)!amino!-N,N-diet hylbenzamide;
N,N-diethyl-4-N-(3-methoxyphenyl)-N-(methylaminoacetyl)!amino!benzamide;
N,N-diisopropyl-4-N-aminoacetyl-N-(3-methoxyphenyl)!amino!benzamide;
(.+-.)-N-(4-aminophenyl)-N-(3-methoxyphenyl)-.alpha.-methyl-1-pyrrolidinoet anamine.

60 more elements

Dependencies are inferred from the claim text.

Diaryldiamine derivatives and their use as delta opiod (ANT)-agonists

Life of this patent

Diaryldiamine derivatives and their use as delta opiod (ANT)-agonists

Life of this patent

Abstract

Claims10