Naphthalene anti-psoriatic agents

Claim 2

A compound of the formula ##STR13## wherein: R 1 is lower alkoxy of one to six carbon atoms or phenoxy optionally substituted by one or two substituents chosen from lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms and halo; R 2 is the same as R 1 , or R 2 is hydrogen, lower alkyl of one to six carbon atoms, phenyl or phenyl-lower-alkyl, wherein the phenyl ring of the phenyl or phenyl-lower-alkyl group is optionally substituted by one or two substituents chosen from lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms and halo; R 3 is hydrogen, halo, lower alkyl of one to six carbon atoms, lower alkoxy of one to six carbon atoms, phenyl, phenyl-lower-alkyl or phenyl-lower-alkoxy, wherein the phenyl ring of the phenyl, phenyl-lower-alkyl or phenyl-lower-alkoxy group is optionally substituted by one or two substituents chosen from lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms and halo; m is 1 or 2; and both X groups are the same and X is --C(O)OR 4 or --C(O)NR 5 R 6 , wherein R 4 is alkyl of one or seven carbon atoms, phenyl or benzyl, wherein the phenyl ring of the phenyl or benzyl group is optionally substituted by one or two substituents chosen from lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms and halo; and R 5 and R 6 are independently hydrogen, lower alkyl of one to six carbon atoms, cycloalkyl of five to eight carbon atoms or phenyl optionally substituted with one or two substituents chosen from lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms and halo.

Claim 3

The compound of claim 1, wherein X is --C(O)OR 4 .

Claim 4

The compound of claim 2, wherein R 1 and R 2 are the same and are methoxy, ethoxy, n-propoxy or phenoxy.

Claim 5

The compound of claim 3, wherein R 4 is methyl, ethyl, n-propyl or phenyl.

Claim 6

The compound of claim 4, wherein R 3 is hydrogen or chloro.

Claim 7

The compound of claim 5, wherein R 1 and R 2 are both methoxy, R 3 is hydrogen and R 4 is methyl, namely 2,3-dimethoxy-1,4-di(methoxycarbonyloxy)naphthalene.

Claim 8

The compound of claim 5, wherein R 1 and R 2 are both methoxy, R 3 is hydrogen and R 4 is ethyl, namely 2,3-dimethoxy-1,4-di(ethoxycarbonyloxy)naphthalene.

Claim 9

The compound of claim 5, wherein R 1 and R 2 are both phenoxy, R 3 is hydrogen and R 4 is methyl, namely 2,3-diphenoxy-1,4-di(methoxycarbonyloxy)naphthalene.

Claim 10

The compound of claim 5, wherein R 1 and R 2 are both methoxy, R 3 is 6-chloro and R 4 is methyl, namely 2,3-dimethoxy-1,4-di(methoxycarbonyloxy)-6-chloronaphthalene.

Claim 11

The compound of claim 5, wherein R 1 and R 2 are both methoxy, R 3 is 6-chloro and R 4 is ethyl, namely 2,3-dimethoxy-1,4-di(ethoxycarbonyloxy)-6-chloronaphthalene.

Claim 12

The compound of claim 5, wherein R 1 and R 2 are both methoxy, R 3 is 6-chloro and R 4 is phenyl, namely 2,3-dimethoxy-1,4-di(phenoxycarbonyloxy)-6-chloronaphthalene.

Claim 13

The compound of claim 2, wherein R 1 is lower alkoxy of one to six carbon atoms or optionally substituted phenoxy and R 2 is hydrogen, lower alkyl of one to six carbon atoms, optionally substituted phenyl or optionally substituted phenylalkyl.

Claim 14

The compound of claim 12, wherein R 1 is methoxy, ethoxy, n-propoxy or phenoxy.

Claim 15

The compound of claim 13, wherein R 2 is hydrogen, methyl, ethyl or n-propyl.

Claim 16

The compound of claim 14, wherein R 4 is methyl, ethyl or n-propyl.

Claim 17

The compound of claim 15, wherein R 3 is hydrogen or chloro.

Claim 18

The compound of claim 16, wherein R 1 is methoxy, R 2 and R 3 are both hydrogen and R 4 is methyl, namely 2-methoxy-1,4-di(methoxycarbonyloxy)naphthalene.

Claim 19

The compound of claim 16, wherein R 1 is methoxy, R 2 is methyl, R 3 is hydrogen and R 4 is methyl, namely 2-methoxy-3-methyl-1,4-di(methoxycarbonyloxy)naphthalene.

Claim 20

The compound of claim 1, wherein X is --C(O)NR 5 R 6 .

Claim 21

The compound of claim 19, wherein R 1 and R 2 are the same and are methoxy, ethoxy, n-propoxy or phenoxy.

Claim 22

The compound of claim 20, wherein R 5 and R 6 are independently hydrogen, methyl, ethyl, n-propyl or phenyl.

Claim 23

The compound of claim 21, wherein R 3 is hydrogen or chloro.

Claim 24

The compound of claim 22, wherein R 1 and R 2 are both methoxy, R 3 and R 5 are both hydrogen and R 6 is methyl, namely 2,3-dimethoxy-1,4-di(methylcarbamoyloxy)naphthalene.

Claim 25

The compound of claim 22, wherein R 1 and R 2 are both methoxy, R 3 and R 5 are both hydrogen and R 6 is ethyl, namely, 2,3-dimethoxy-1,4-di(ethylcarbamoyloxy)naphthalene.

Claim 26

The compound of claim 22, wherein R 1 and R 2 are both phenoxy, R 3 and R 5 are both hydrogen and R 6 is methyl, namely 2,3-diphenoxy-1,4-di(methylcarbamoyloxy)naphthalene.

Claim 27

The compound of claim 22, wherein R 1 and R 2 are both methoxy, R 3 is 6-chloro, R 5 is hydrogen and R 6 is methyl, namely 2,3-dimethoxy-1,4-di(methylcarbamoyloxy)-6-chloronaphthalene.

Claim 28

The compound of claim 22, wherein R 1 and R 2 are both methoxy, R 3 is 6-chloro, R 5 is hydrogen and R 6 is ethyl, namely 2,3-dimethoxy-1,4-di(ethylcarbamoyloxy)6-chloronaphthalene.

Claim 29

The compound of claim 19, wherein R 1 is lower alkoxy of one to six carbon atoms or optionally substituted phenoxy and R 2 is hydrogen, lower alkyl of one to six carbon atoms, optionally substituted phenyl or optionally substituted phenylalkyl.

Claim 30

The compound of claim 28, wherein R 1 is methoxy, ethoxy, n-propoxy or phenoxy.

Claim 31

The compound of claim 29, wherein R 2 is hydrogen, methyl, ethyl or n-propyl.

Claim 32

The compound of claim 30, wherein R 5 and R 6 are independently hydrogen, methyl, ethyl, n-propyl or phenyl.

Claim 33

The compound of claim 31, wherein R 3 is hydrogen or chloro.

Claim 34

The compound of claim 32, wherein R 1 is methoxy, R 2 , R 3 and R 5 are each hydrogen and R 6 is methyl, namely 2-methoxy-1,4-di(methylcarbamoyloxy)naphthalene.

Claim 35

The compound of claim 32, wherein R 1 is methoxy, R 2 is methyl, R 3 and R 5 are both hydrogen and R 6 is methyl, namely 2-methoxy-3-methyl-1,4-di(methylcarbamoyloxy)naphthalene.

Claim 36

A composition in a form suitable for topical administration for treating the condition of psoriasis which composition comprises a pharmaceutically acceptable, non-toxic carrier and a psoriasis relieving amount of a compound of the formula ##STR14## wherein: R 1 is lower alkoxy of one to six carbon atoms or phenoxy optionally substituted by one or two substituents chosen from lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms and halo; R 2 is the same as R 1 , or R 2 is hydrogen, lower alkyl of one to six carbon atoms, phenyl or phenyl-lower-alkyl, wherein the phenyl ring of the phenyl or phenyl-lower-alkyl group is optionally substituted by one or two substituents chosen from lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms and halo; R 3 is hydrogen, halo, lower alkyl of one to six carbon atoms, lower alkoxy of one to six carbon atoms, phenyl, phenyl-lower-alkyl or phenyl-lower-alkoxy, wherein the phenyl ring of the phenyl, phenyl-lower-alkyl or phenyl-lower-alkoxy group is optionally substituted by one to two substituents chosen from lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms and halo; m is 1 or 2; and both X groups are the same and X is --C(O)OR 4 or --C(O)NR 5 R 6 , wherein R 4 is alkyl of one to seven carbon atoms, phenyl or benzyl, wherein the phenyl ring of the phenyl or benzyl group is optionally substituted by one or two substituents chosen from lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms and halo; and R 5 and R 6 are independently hydrogen, lower alkyl of one to six carbon atoms, cycloalkyl of five to eight carbon atoms or phenyl optionally substituted with one or two substituents chosen from lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms and halo.

Claim 37

A composition in a form suitable for topical administration for treating the condition of psoriasis which composition comprises a pharmaceutically acceptable, non-toxic carrier and a psoriasis relieving amount of a compound of the formula ##STR14## wherein: R 1 is lower alkoxy of one to six carbon atoms or phenoxy optionally substituted by one or two substituents chosen from lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms and halo; R 2 is the same as R 1 , or R 2 is hydrogen, lower alkyl of one to six carbon atoms, phenyl or phenyl-lower-alkyl, wherein the phenyl ring of the phenyl or phenyl-lower-alkyl group is optionally substituted by one or two substituents chosen from lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms and halo; R 3 is hydrogen, halo, lower alkyl of one to six carbon atoms, lower alkoxy of one to six carbon atoms, phenyl, phenyl-lower-alkyl or phenyl-lower-alkoxy, wherein the phenyl ring of the phenyl, phenyl-lower-alkyl or phenyl-lower-alkoxy group is optionally substituted by one to two substituents chosen from lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms and halo; m is 1 or 2; and both X groups are the same and X is --C(O)OR 4 or --C(O)NR 5 R 6 , wherein R 4 is alkyl of one to seven carbon atoms, phenyl or benzyl, wherein the phenyl ring of the phenyl or benzyl group is optionally substituted by one or two substituents chosen from lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms and halo; and R 5 and R 6 are independently hydrogen, lower alkyl of one to six carbon atoms, cycloalkyl of five to eight carbon atoms or phenyl optionally substituted with one or two substituents chosen from lower alkyl of one to four carbon atoms, lower alkoxy of one to four carbon atoms and halo.