US 5,393,753 AGranted

Substituted imidazobenzazepines

AssigneeSchering Corporation

InventorRichard J. Friary

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Abstract

Compounds of the formula ##STR1## wherein R.sup.1 is H, C.sub.1 -C.sub.7 alkyl, C.sub.3 -C.sub.7 cycloalkyl, CF.sub.3, aryl, substituted aryl, heteroaryl, -O-C.sub.1 -C.sub.7 alkyl, or -O-C.sub.3 -C.sub.7 cycloalkyl; R.sup.2 and R.sup.3 are each independently H, C.sub.1 -C.sub.7 alkyl, C.sub.3 -C.sub.7 cycloalkyl, CF.sub.3, NO.sub.2, halogen, OR.sup.7, NR.sup.8 R.sup.9 or S(O).sub.m R.sup.10, wherein m is 0, 1 or 2; R.sup.4 is H, C.sub.1 -C.sub.7 alkyl, arylmethyl, or substituted arylmethyl; R.sup.5 and R.sup.6 are each independently H, C.sub.1 -C.sub.7 alkyl, C.sub.3 -C.sub.7 cycloalkyl, aryl, substituted aryl, heteroaryl, arylmethyl, substituted arylmethyl, or taken together constitute a chain of (CH.sub.2).sub.k groups, wherein k is 3, 4, or 5; R.sup.7, R.sup.8 and R.sup.9 are each independently H, C.sub.1 -C.sub.7 alkyl, -C(.dbd.O)-(C.sub.1 -C.sub.7 alkyl), -C(.dbd.O)-aryl, or -(C.dbd.O)heteroaryl; R.sup.10 is C.sub.1 -C.sub.7 alkyl, C.sub.3 -C.sub.7 cycloalkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, arylmethyl, or substituted arylmethyl; one and only one of the dotted lines, a, b, c, and d, represents a carbon-carbon bond; n is 0, 1, 2 or 3; Z is O or S, Q is CH, N, or NO, with the proviso that Z is not S when Q is NO, or a pharmaceutically acceptable acid addition salt thereof, are described. These compounds are useful as agents in the treatment of asthma and other allergic diseases and in the treatment of inflammation.

A compound of the formula ##STR32## wherein R.sup.1 is H, C.sub.1 -C.sub.7 alkyl, C.sub.3 -C.sub.7 cycloalkyl, CF.sub.3, aryl having from 6 to 14 carbon atoms, substituted aryl, heteroaryl having at least one O, S and/or N interrupting a carbocyclic ring structure with the aromatic heterocyclic group having from 2 to 14 carbon atoms, -O-C.sub.1 -C.sub.7 alkyl, or -O-C.sub.3 -C.sub.7 cycloalkyl;

R.sup.2 and R.sup.3 are each independently H, C.sub.1 -C.sub.7 alkyl, C.sub.3 -C.sub.7 cycloalkyl, CF.sub.3, NO.sup.2, halogen, OR.sup.7, NR.sup.8 R.sup.9 or S(O).sub.m R.sup.10, wherein m is 0, 1 or 2;
R.sup.4 is H, C.sub.1 -C.sub.7 alkyl, arylmethyl with the aryl portion having from 6 to 14 carbon atoms, or substituted arylmethyl;
R.sup.5 and R.sup.6 are each independently H, C.sub.1 -C.sub.7 alkyl, C.sub.3 -C.sub.7 cycloalkyl, aryl having from 6 to 14 carbon atoms, substituted aryl, heteroaryl having at least one O, S and/or N interrupting a carbocyclic ring structure with the aromatic heterocyclic group having from 2 to 14 carbon atoms, arylmethyl with the aryl portion having from 6 to 14 carbon atoms, or substituted arylmethyl;
R.sup.7, R.sup.8 and R.sup.9 are each independently H, C.sub.1 -C.sub.7 alkyl, -C(.dbd.O)-(C.sub.1 -C.sub.7 alkyl), -C(.dbd.O)- aryl having from 6 to 14 carbon atoms, or -(C.dbd.O)heteroaryl having at least one O, S and/or N interrupting a carbocyclic ring structure with the aromatic heterocyclic group having from 2 to 14 carbon atoms;
R.sup.10 is C.sub.1 -C.sub.7 alkyl, C.sub.3 -C.sub.7 cycloalkyl, aryl having from 6 to 14 carbon atoms, substituted aryl, heteroaryl having at least one O, S and/or N interrupting a carbocyclic ring structure with the aromatic heterocyclic group having from 2 to 14 carbon atoms, substituted heteroaryl, arylmethyl with the aryl portion having from 6 to 14 carbon atoms, or substituted arylmethyl;
one and only one of the dotted lines, a, b, c, and d, represents a carbon-carbon bond;
n is 0, 1, 2 or 3;
Z is O or S, Q is CH or a pharmaceutically acceptable acid addition, salt thereof.

5 more elements

Abstract

Claims14