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Last Updated: September 22, 2021

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Claims for Patent: 4,816,464

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Summary for Patent: 4,816,464
Title: 10-Substituted benzo[b][1,6]naphthyridines as inhibitors of interleukin 1
Abstract:There is disclosed a method for the treatment of inflammatory conditions and of collagenase-induced tissue destruction which comprises the administration of a therapeutically effective amount of a compound of the formula ##STR1## wherein R.sup.1 is lower alkyl or lower alkenyl or any of the foregoing optionally substituted with fluoro, carboxy, lower alkoxycarbonyl, OR.sup.2, N(R.sup.2).sub.2, SR.sup.2 CON(R.sup.2).sub.2, SO.sub.2 R.sup.2, cyano, nitro or trifluoromethyl; R.sup.2 is hydrogen, lower alkyl or phenyl; R.sup.3 is halo, morpholino, 4-methylpiperazino, R.sup.4 NNHR.sup.5, NR.sup.4 R.sup.5, OR.sup.5, SR.sup.5, ##STR2## R.sup.4 is hydrogen or lower alkyl; R.sup.5 is hydrogen, lower alkyl, lower alkanoyl, lower cycloalkyl or phenyl; and R.sup.6 and R.sup.7 are each independently, hydrogen, halo, nitro, lower alkoxy, lower alkyl or trifluoromethyl; which compounds, by virtue of their ability to inhibit interleukin 1, are useful as antiinflammatory agents and in treatment of disease states involving enzymatic tissue destruction, and are also intermediates in the preparation of other compounds which possess identical activities.
Inventor(s): Gilman; Steven C. (Berwyn, PA), Skotnicki; Jerauld S. (Chadds Ford, PA)
Assignee: American Home Products Corporation (New York, NY)
Application Number:07/065,211
Patent Claims:1. A method for the treatment of inflammatory conditions and of collagenase-induced tissue destruction in warm-blooded animals which comprises the administration thereto of an anti-inflammatory/collagenase inhibitory amount of a compound having the formula ##STR7## wherein R.sup.1 is lower alkyl or lower alkenyl or any of the foregoing optionally substituted with fluoro, carboxy, lower alkoxycarbonyl, OR.sup.2, N(R.sup.2).sub.2, SR.sup.2, CON(R.sup.2).sub.2, SO.sub.2 R.sup.2, cyano, nitro or trifluoromethyl;

R.sup.2 is hydrogen, lower alkyl or phenyl;

R.sup.3 is halo, R.sup.4 NNHR.sup.5, NR.sup.4 R.sup.5, OR.sup.5, SR.sup.5, R.sup.4 NCH.sub.2 CH.sub.2 OCH.sub.3 or SCH.sub.2 CH.sub.2 CH.sub.2 NH.sub.2 ;

R.sup.4 is hydrogen or lower alkyl;

R.sup.5 is hydrogen, lower alkyl, lower alkanoyl, lower cycloalkyl or phenyl; and

R.sup.6 and R.sup.7 are each independently, hydrogen, halo, nitro, lower alkoxy, lower alkyl or trifluoromethyl

2. The method of claim 1, wherein the compound administered is 2-butyl-7,10-dichloro-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridine.

3. The method of claim 1, wherein the compound administered is 7,10-dichloro-1,2,3,4-tetrahydro-2-octylbenzo[b][1,6]naphthyridine.

4. The method of claim 1, wherein the compound administered is 7,10-dichloro-1,2,3,4-tetrahydro-2-(2-propenyl)benzo[b][1,6]naphthyridine.

5. The method of claim 1, wherein the compound administered is 7,10-dichloro-1,2,3,4-tetrahydro-2-(4-pentenyl)benzo[b][1,6]naphthyridine.

6. The method of claim 1, wherein the compound administered is 7,10-dichloro-1,2,3,4-tetrahydro-2-methylbenzo[b][1,6]naphthyridine.

7. The method of claim 1, wherein the compound administered is 8,10-dichloro-1,2,3,4-tetrahydro-2-methylbenzo[b][1,6]naphthyridine.

8. The method of claim 1, wherein the compound administered is 1-(7-chloro-1,2,3,4-tetrahydro-2-methylbenzo[b][1,6]naphthyridin-10-yl)-2- phenylhydrazine.

9. The method of claim 1, wherein the compound administered is 2-butyl-7-chloro-1,2,3,4-tetrahydro-10-(2-phenylhydrazino)benzo[b][1,6]nap hthyridine.

10. The method of claim 1, wherein the compound administered is 7-chloro-1,2,3,4-tetrahydro-2-octyl-10-(2-phenylhydrazino)benzo[b][1,6]nap hthyridine.

11. The method of claim 1, wherein the compound administered is 7-chloro-1,2,3,4-tetrahydro-10-(2-phenylhydrazino)-2-(2-propenyl)benzo[b][ 1,6]naphthyridine.

12. The method of claim 1, wherein the compound administered is 7-chloro-1,2,3,4-tetrahydro-2-(4-pentenyl)-10-(2-phenylhydrazino)benzo[b][ 1,6]naphthyridine.

13. The method of claim 1, wherein the compound administered is 7-chloro-1,2,3,4-tetrahydro-N-(2-methoxyethyl)-2-methylbenzo[b][1,6]naphth yridin-10-amine.

14. The method of claim 1, wherein the compound administered is 10-anilino-7-chloro-1,2,3,4-tetrahydro-2-methylbenzo[b][1,6]naphthyridine.

15. The method of claim 1, wherein the compound administered is 7-chloro-1,2,3,4-tetrahydro-2-methyl-10-phenoxybenzo[b][1,6]naphthyridine.

16. The method of claim 1, wherein the compound administered is 8-chloro-1,2,3,4-tetrahydro-2-methyl-10-phenoxybenzo[b][1,6]naphthyridine.

17. The method of claim 1, wherein the compound administered is 10-anilino-8-chloro-1,2,3,4-tetrahydro-2-methylbenzo[b][1,6]naphthyridine.

18. The method of claim 1, wherein the compound adminstered is (8-chloro-1,2,3,4-tetrahydro-2-methylbenzo[b][1,6]naphthyridin-10-yl)hydra zine.

19. The method of claim 1, wherein the compound administered is 10-(3-aminopropylthio)-8-chloro-1,2,3,4-tetrahydro-2-methylbenzo[b][1,6]na phthyridine.

20. The method of claim 1, wherein the compound administered is 7-chloro-1,2,3,4-tetrahydro-2-methyl-10-thiophenylbenzo[b][1,6]naphthyridi ne.

Details for Patent 4,816,464

Applicant Tradename Biologic Ingredient Dosage Form BLA Number Approval Date Patent No. Assignee Estimated Patent Expiration Status Orphan Source
Smith And Nephew SANTYL collagenase OINTMENT;TOPICAL 101995 001 1965-06-04 ⤷  Free Forever Trial American Home Products Corporation (New York, NY) 2039-03-29 RX search
>Applicant >Tradename >Biologic Ingredient >Dosage Form >BLA >Number >Approval Date >Patent No. >Assignee >Estimated Patent Expiration >Status >Orphan >Source

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