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Details for Patent: 4,831,042

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Details for Patent: 4,831,042

Title: Tricyclic-substituted piperidine antihistamines
Abstract:Antihistamines of the formula ##STR1## wherein ##STR2## is a 5 or 6 membered ring which is phenyl or heterocyclic ##STR3## is a six membered ring which is 2,3, or 4 pyridyl or is phenyl or substituted phenyl, with the proviso that is ##STR4## is a nitrogen containing ring ##STR5## must be phenyl; Z is an alkylene chain having 0 to 2 carbon atoms in the chain, said 2 carbon chain optionally having one double bond, said chain optionally having either a carbonyl oxygen, or a hydroxy group as a substituent; W is defined hereinbelow.
Inventor(s): Villani; Frank J. (West Caldwell, NJ)
Assignee: Schering Corporation (Kenilworth, NJ)
Filing Date:Apr 25, 1984
Application Number:06/603,797
Claims:1. A compound having the structural formula ##STR13## wherein ring ##STR14## is a 5- or 6-membered, aromatic, non-nitrogen containing heterocycle; ring ##STR15## is ortho-phenylene or orthophenylene substituted with halo; Z represents a bond or an alkylene chain having 1 to 2 carbon atoms in the chain, said 2 carbon chain optionally having one double bond, said chain optionally having either a carbonyl oxygen or a hydroxy group as a substituent; W is ##STR16## wherein n is 1 or 2, R.sub.2 is hydrogen or C.sub.1 to C.sub.3 alkyl, and the dotted line represents an optional double bond, R.sup.2 being absent if the double bond is present, and Y is --COOR or --SO.sub.2 R, with the proviso that when Y is --COOR, R is C.sub.1 to C.sub.12 alkyl, substituted C.sub.1 to C.sub.12 alkyl, C.sub.2 to C.sub.12 alkenyl, substituted C.sub.2 to C.sub.12 alkenyl, phenyl, substituted phenyl, C.sub.7 to C.sub.10 phenylalkyl, C.sub.7 to C.sub.10 phenylalkyl wherein the phenyl moiety is substituted, or R is -2, -3, or -4 piperidyl or N-substituted piperidyl, wherein the substituents on said substituted C.sub.1 to C.sub.12 alkyl and on said substituted C.sub.2 to C.sub.12 alkenyl are selected from amino or substituted amino and the substituents on said substituted amino are selected from C.sub.1 to C.sub.6 alkyl, the substituents on said substituted phenyl and on said substituted phenyl moiety of the C.sub.7 to C.sub.10 phenylalkyl are selected from C.sub.1 to C.sub.4 alkyl and halo, and the substituent on said N-substituted piperidyl is C.sub.1 to C.sub.4 alkyl, and with the proviso that when Y is SO.sub.2 R, R is selected from C.sub.1 to C.sub.12 alkyl, C.sub.2 to C.sub.12 alkenyl, phenyl, substituted phenyl, C.sub.7 to C.sub.10 phenylalkyl, C.sub.7 to C.sub.10 phenylalkyl wherein the phenyl moiety is substituted, wherein the substituents on said substituted phenyl and said substituted phenyl moiety of the C.sub.7 to C.sub.10 phenylalkyl are selected from C.sub.1 to C.sub.4 alkyl and halo.

2. A compound defined in claim 1 wherein ring A is a thiophene ring.

3. A compound having the structural formula ##STR17## wherein ring ##STR18## is a 5 or 6-membered, aromatic, non-nitrogen containing heterocycle; ring ##STR19## is ortho-phenylene or ortho-phenylene substituted with halo; Z represents a bond or an alkylene chain having 1 to 2 carbon atoms in the chain; said chain having either a carbonyl oxygen or an hydroxy group as a substituent; W is ##STR20## wherein n is 1 or 2, R.sub.2 is hydrogen or C.sub.1 to C.sub.3 alkyl, and the dotted line represents an optional double bond, R.sub.2 being absent if the double bond is present, and Y is --COOR or --SO.sub.2 R, with the proviso that when Y is --COOR, R is C.sub.1 to C.sub.12 alkyl, substituted C.sub.1 to C.sub.12 alkyl, C.sub.2 to C.sub.12 alkenyl, substituted C.sub.2 to C.sub.12 alkenyl, phenyl, substituted phenyl, C.sub.7 to C.sub.10 phenylalkyl, C.sub.7 to C.sub.10 phenylalkyl wherein the phenyl moiety is substituted, or R is -2, -3, or -4 piperidyl or N-substituted piperidyl, wherein the substituents on said substituted C.sub.1 to C.sub.12 alkyl and on said substituted C.sub.2 to C.sub.12 alkenyl are selected from amino or substituted amino and the substituents on said substituted amino are selected from C.sub.1 to C.sub.6 alkyl, the substituents on said substituted phenyl and on said substituted phenyl moiety of the C.sub.7 to C.sub.10 phenylalkyl are selected from C.sub.1 to C.sub.4 alkyl and halo, and the substituent on said N-substituted piperidyl is C.sub.1 to C.sub.4 alkyl, and with the proviso that when Y is SO.sub.2 R, R is selected from C.sub.1 to C.sub.12 alkyl, C.sub.2 to C.sub.12 alkenyl, phenyl, substituted phenyl, C.sub.7 to C.sub.10 phenylalkyl, C.sub.7 to C.sub.10 phenylalkyl wherein the phenyl moiety is substituted, wherein the substituents on said substituted phenyl and said substituted phenyl moiety of the C.sub.7 to C.sub.10 phenylalkyl are selected from C.sub.1 to C.sub.4 alkyl and halo.

4. A compound defined in claim 3 having the structural formula: ##STR21##

5. A compound having the structural formula ##STR22## wherein n is 1 or 2, and Y is --COOR or --CO.sub.2 R, with the proviso that when Y is --COOR, R is C.sub.1 to C.sub.12 alkyl, substituted C.sub.1 to C.sub.12 alkyl, C.sub.2 to C.sub.12 alkenyl, substituted C.sub.2 to C.sub.12 alkenyl, phenyl, substituted phenyl, C.sub.7 to C.sub.10 phenylalkyl wherein the phenyl moiety is substituted, or R is -2, -3, or -4 piperidyl or N-substituted piperidyl, wherein the substituents on said substituted C.sub.1 to C.sub.12 alkyl and on said substituted C.sub.2 to C.sub.12 alkenyl are selected from amino or substituted amino and the substituents on said substituted amino are selected from C.sub.1 to C.sub.6 alkyl, the substituents on said substituted phenyl and on said substituted phenyl moiety of the C.sub.7 to C.sub.10 phenylalkyl are selected from C.sub.1 to C.sub.4 alkyl and halo, and the substituent on said N-substituted piperidyl is C.sub.1 to C.sub.4 alkyl and with the proviso that when Y is SO.sub.2 R, R is selected from C.sub.1 to C.sub.12 alkyl, C.sub.2 to C.sub.12 alkenyl, phenyl, substituted phenyl, C.sub.7 to C.sub.10 phenylalkyl, C.sub.7 to C.sub.10 phenylalkyl wherein the phenyl moiety is substituted, wherein the substituents on said substituted phenyl and said substituted phenyl moiety of the C.sub.7 to C.sub.10 phenylalkyl are selected from C.sub.1 to C.sub.4 alkyl and halo.

6. A compound defined in claim 5 having the structural formula ##STR23##

7. A compound defined in claim 6 wherein Y is COOR.

8. The compound defined in claim 7 wherein R is C.sub.2 H.sub.5.

9. A pharmaceutical composition which comprises an anti-allergic effective amount of a compound having the structural formula ##STR24## in combination with a pharmaceutically acceptable carrier, wherein ring ##STR25## is a 5 or 6-membered, aromatic, non-nitrogen containing heterocycle; ring ##STR26## is ortho-phenylene or orthophenylene substituted with halo; Z represents a bond or an alkylene chain having 1 to 2 carbon atoms in the chain, said 2 carbon chain optionally having one double bond, said chain optionally having either a carbonyl oxygen or an hydroxy group as a substituent; W is ##STR27## wherein n is 1 or 2, R.sub.2 is hydrogen or C.sub.1 to C.sub.3 alkyl, and the dotted line represents an optional double bond, R.sup.2 being absent if the double bond is present, and Y is --COOR or --SO.sub.2 R, with the proviso that when Y is --COOR, R is C.sub.1 to C.sub.12 alkyl, substituted C.sub.1 to C.sub.12 alkyl, C.sub.2 to C.sub.12 alkenyl, substituted C.sub.2 to C.sub.12 alkenyl, phenyl, substituted phenyl, C.sub.7 to C.sub.10 phenylalkyl, C.sub.7 to C.sub.10 phenylalkyl wherein the phenyl moiety is substituted, or R is -2, -3, or -4 piperidyl or N-substituted piperidyl, wherein the substituents on said substituted C.sub.1 to C.sub.12 alkyl and on said substituted C.sub.2 to C.sub.12 alkenyl are selected from amino or substituted amino and the substituents on said substituted amino are selected from C.sub.1 to C.sub.6 alkyl, the substituents on said substituted phenyl and on said substituted phenyl moiety of the C.sub.7 to C.sub.10 phenylalkyl are selected from C.sub.1 to C.sub.4 alkyl and halo, and the substituent on said N-substituted piperidyl is C.sub.1 to C.sub.4 alkyl, and with the proviso that when Y is SO.sub.2 R, R is selected from C.sub.1 to C.sub.12 alkyl, C.sub.2 to C.sub.12 alkenyl, phenyl, substituted phenyl, C.sub.7 to C.sub.10 phenylalkyl, C.sub.7 to C.sub.10 phenylalkyl wherein the phenyl moiety is substituted, wherein the substituents on said substituted phenyl and said substituted phenyl moiety of the C.sub.7 to C.sub.10 phenylalkyl are selected from C.sub.1 to C.sub.4 alkyl and halo.

10. A method of effecting an anti-allergic response in a mammal which comprises administering to said mammal an anti-allergic effective amount of a composition comprising a compound having the structural formula ##STR28## in combination with a pharmaceutically acceptable carrier, wherein ring ##STR29## is a 5 or 6-membered, aromatic, non-nitrogen containing heterocycle; ring ##STR30## is ortho-phenylene or ortho-phenylene substituted with halo; Z represents a bond or an alkylene chain having 1 or 2 carbon atoms in the chain, said 2 carbon chain optionally having one double bond, said chain optionally having either a carbonyl oxygen or an hydroxy group as a substituent; W is ##STR31## wherein n is 1 or 2, R.sub.2 is hydrogen or C.sub.1 to C.sub.3 alkyl, and the dotted line represents an optional double bond, R.sup.2 being absent if the double bond is present, and Y is --COOR or --SO.sub.2 R, with the proviso that when Y is --COOR, R is C.sub.1 to C.sub.12 alkyl, substituted C.sub.1 to C.sub.12 alkyl, C.sub.2 to C.sub.12 alkenyl, substituted C.sub.2 to C.sub.12 alkenyl, phenyl, substituted phenyl, C.sub.7 to C.sub.10 phenylalkyl, C.sub.7 to C.sub.10 phenylalkyl wherein the phenyl moiety is substituted, or R is -2, -3, or -4 piperidyl or N-substituted piperidyl, wherein the substituents on said substituted C.sub.1 to C.sub.12 alkyl and on said substituted C.sub.2 to C.sub.12 alkenyl are selected from amino or substituted amino and the substituents on said substituted amino are selected from C.sub.1 to C.sub.6 alkyl, the substituents on said substituted phenyl and on said substituted phenyl moiety of the C.sub.7 to C.sub.10 phenylalkyl are selected from C.sub.1 to C.sub.4 alkyl and halo, and the substituent on said N-substituted piperidyl is C.sub.1 to C.sub.4 alkyl, and with the proviso that when Y is SO.sub.2 R, R is selected from C.sub.1 to C.sub.12 alkyl, C.sub.2 to C.sub.12 alkenyl, phenyl, substituted phenyl, C.sub.7 to C.sub.10 phenylalkyl, C.sub.7 to C.sub.10 phenylalkyl wherein the phenyl moiety is substituted, wherein the substituents on said substituted phenyl and said substituted phenyl moiety of the C.sub.7 to C.sub.10 phenylalkyl are selected from C.sub.1 to C.sub.4 alkyl and halo.
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