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Claims for Patent: 4,282,233

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Claims for Patent: 4,282,233

Title: Antihistaminic 11-(4-piperidylidene)-5H-benzo-[5,6]-cyclohepta-[1,2-b]-pyridines
Abstract:11-(4-Piperidylidene)-5H-benzo-[5,6]-cyclohepta-[1,2-b]-pyridines and their 5,6-dihydro derivatives are disclosed. The compounds are useful as antihistamines with little or no sedative effects.
Inventor(s): Vilani; Frank J. (West Caldwell, NJ)
Assignee: Schering Corporation (Kenilworth, NJ)
Application Number:06/160,795
Patent Claims: 1. A compound of the formula ##STR2## wherein the dotted line represents an optional double bond; X is hydrogen or halo; and

wherein 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, phenyl, substituted phenyl, C.sub.7 to C.sub.12 phenylalkyl, C.sub.7 to C.sub.12 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 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.12 phenylalkyl are selected from C.sub.1 to C.sub.6 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 C.sub.1 to C.sub.12 alkyl, phenyl, substituted phenyl, C.sub.7 to C.sub.12 phenylalkyl, C.sub.7 to C.sub.12 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.12 phenylalkyl are selected from C.sub.1 to C.sub.6 alkyl and halo.

2. A compound according to claim 1, wherein Y is --COOR, wherein R is as defined in claim 1, said compound having a single bond between the 5- and 6-carbons.

3. A compound according to claim 1, wherein Y is --SO.sub.2 R, wherein R is as defined in claim 1, said compound having a single bond between the 5- and 6-carbons.

4. A compound according to claim 2, wherein X is hydrogen, said compound having a single bond between the 5- and 6-carbons.

5. A compound according to claim 2, wherein X is 8-chloro, said compound having a single bond between the 5- and 6-carbons.

6. A compound according to claim 3, wherein X is hydrogen, said compound having a single bond between the 5- and 6-carbons.

7. 11-(N-carboethoxy-4-piperidylidene)-8-chloro-6,1 1-dihydro-5H-benzo-[5,6]-cyclohepta-[1,2-b]-pyridine.

8. 11-(N-methanesulfonyl-4-piperidylidene)-6,11-dihyd ro-5H-benzo-[5,6]-cyclohepta-[1,2-b]-pyridine.

9. 11-(N-carboethoxy-4-piperidylidene)-6,11-di hydro-5H-benzo-[5,6]-cyclohepta-[1,2-b]-pyridine.

10. 11-(N-carbomethoxy-4-piperidylidene)-6,11-dih ydro-5H-benzo-[5,6]-cyclohepta-[1,2-b]-pyridine.

11. 11-(N-carbophenoxy-4-piperidylidene)-6,11-di hydro-5H-benzo-[5,6]-cyclohepta-[1,2-b]-pyridine.

12. An antihistaminic pharmaceutical composition comprising an effective amount of a compound as claimed in any one of claims 1-10 and a pharmaceutically acceptable carrier.

13. A method of effecting an anti-allergic response in an animal comprising administering to the animal an effective amount of a compound as claimed in any one of claims 1 to 11.
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