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US 5,856,503 AGranted
Aminoalkyl-substituted benzo-heterocyclic compounds
AssigneeHoffmann-La Roche Inc.
InventorsJohannes Aebi, Henrietta Dehmlow, Jacques Himber, Hans-Peter Marki, Hans Lengsfeld, Olivier Morand, Gerard Schmid, Yu-Hua Ji
Life of this patent
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Abstract
Aminoalkyl-substituted benzo-heterocyclic compounds of the formula ##STR1## wherein M, Q, R and T are as defined in the specification, as well as acid addition salts thereof. These compounds are useful as cholesterol level lowering agents and as antimycotic agents.
Claims30
A compound of the formula:
- ##STR30## wherein R is either a group of the formula:
- ##STR31## T is H, C.sub.1 -C.sub.6 alkyl, halogen, N(R.sup.2,R.sup.21), CONH.sub.2, CN, NO.sub.2, CF.sub.3, OH, C.sub.1 -C.sub.6 alkyl(O), or C.sub.1 -C.sub.6 alkyl(S),
- R.sup.2 and R.sup.21 are independently C.sub.1 -C.sub.6 alkyl or H, and
- Q is C.sub.3 -C.sub.6 cycloalkyl, phenyl substituted by R.sup.3, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkenyl substituted by OH, C.sub.4 -C.sub.6 alkadienyl, or C.sub.4 -C.sub.6 alkadienyl substituted by OH,
- or wherein one of R and T is halogen or H, and the other of R and T is H, C.sub.1 -C.sub.6 alkyl, halogen, N(R.sup.2,R.sup.21), CONH.sub.2, CN, NO.sub.2, CF.sub.3, OH, C.sub.1 -C.sub.6 alkyl(O), or C.sub.1 -C.sub.6 alkyl(S), and
- Q is a group of the formula:
- ##STR32## A.sup.1 is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 alkenyl, and A.sup.2 is C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 cycloalkyl-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkyl substituted by R.sup.4, C.sub.2 -C.sub.6 alkenyl, or C.sub.2 -C.sub.6 alkenyl substituted by R.sup.4, or
- A.sup.1 and A.sup.2 together are a C.sub.2 -C.sub.5 alkylene, a C.sub.2 -C.sub.5 alkylene substituted by R.sub.4, C.sub.4 -C.sub.5 alkenylene, or a C.sub.4 -C.sub.5 alkenylene substituted by R.sup.4 group A.sup.1 -A.sup.2,
- R.sup.4 is OH, C.sub.1 -C.sub.6 alkyl(O) or C.sub.1 -C.sub.6 alkyl(S) bonded to a saturated C atom of A.sup.2 or of A.sup.1 -A.sup.2, whereby a C atom substituted by R.sup.4 or an unsaturated C atom present in A.sup.1, A.sup.2 or A.sup.1 -A.sup.2 is bonded in a position other than the a-position to N(A.sup.1 -A.sup.2),
- L.sup.1 is a group L bonded to the benzo group directly or via O, NH, N(C.sub.1 -C.sub.6 alkyl), or N(C.sub.1 -C.sub.6 alkanoyl),
- L.sup.2 is a group L bonded to the phenyl group via O, NH, N(C.sub.1 -C.sub.6 alkyl), or N(C.sub.1 -C.sub.6 alkanoyl),
- L is a C.sub.4 -C.sub.11 alkylene, C.sub.3 -C.sub.11 alkenylene, or (C.sub.3 -6-cycloalkylene)-(C.sub.1 -C.sub.13 alkylene) bonded to the methylene group via its cycloalkylene group,
- R.sup.3 is independently H, C.sub.1 -C.sub.6 alkyl, halogen, N(R.sup.5,R.sup.51), CONH.sub.2, CN, NO.sub.2, CF.sub.3, OH, C.sub.1 -C.sub.6 alkyl(O), or C.sub.1 -C.sub.6 alkyl(S),
- R.sup.5 and R.sup.51 are C.sub.1 -C.sub.6 alkyl or H;
- ----- is a single bond or a double bond:
- M is a two-membered grouping having a first member selected from the group consisting of S, SO, and SO.sub.2, and a second member selected from the group consisting of N and N(R.sup.6);
- R.sup.6 is H or C.sub.1 -C.sub.6 alkyl;
- and physiologically useful acid addition salts thereof.
15 more elements
A compound of the formula:
- ##STR37## wherein A.sup.100 is C.sub.1 -C.sub.6 alkyl or C.sub.3 -C.sub.6 alkenyl;
- A.sup.200 is C.sub.3 -C.sub.6 cycloalkyl, C.sub.3 -C.sub.6 cycloalkyl-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkyl substituted with OH or O(C.sub.1 -C.sub.6 alkyl), C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkenyl substituted with OH or O(C.sub.1 -C.sub.6 alkyl), or CH.sub.2 CH.sub.2 SCH.sub.3 ;
- L.sup.100 is C.sub.4 -C.sub.11 alkylene, C.sub.3 -C.sub.11 alkenylene, or (C.sub.3 -C.sub.6 cycloalkylene)-(C.sub.1 -C.sub.13 alkylene) bonded to the methylene group via its cycloalkyl group;
- P is O or 1;
- G is O, NH, N(C.sub.1 -C.sub.6 alkyl) or N(C.sub.1 -C.sub.6 alkanoyl);
- T.sup.100 is H, C.sub.1 -C.sub.6 alkyl, halogen, NH.sub.2, NH(C.sub.1 -C.sub.6 alkyl), N(C.sub.1 -C.sub.6 alkyl).sub.2, CONH.sub.2, CN, NO.sub.2, CF.sub.3, OH, C.sub.1 -C.sub.6 alkyl-O, or C.sub.1 -C.sub.6 alkyl-S;
- X is S or SO.sub.2 ;
- Y is N;
- and
- Q.sup.100 is C.sub.3 -C.sub.6 cycloalkyl, C.sub.2 -C.sub.6 alkenyl, C.sub.2 -C.sub.6 alkenyl substituted with OH, C.sub.4 -C.sub.6 alkadienyl, C.sub.4 -C.sub.6 alkadienyl substituted with OH, or phenyl substituted with at least one substituent selected from the group consisting of H, C.sub.1 -C.sub.6 alkyl, halogen, NH.sub.2, NH(C.sub.1 -C.sub.6 alkyl), N(C.sub.1 -C.sub.6 alkyl).sub.2, CONH.sub.2, CN, NO.sub.2, CF.sub.3, OH, C.sub.1 -C.sub.6 alkyl-O and C.sub.1 -C.sub.6 alkyl-S, or when X is not oxygen, then Q.sup.100 can be C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkyl substituted with OH;
- and
- physiologically useful acid addition salts thereof.
9 more elements
Dependencies are inferred from the claim text.