Substituted naphthalenes, indoles, benzofurans and benzothiophenes as lipoxygenase inhibitors

Claim 2

A compound of the formula wherein R 1 and R 2 are independently selected from H, C 1-10 alkyl, C 2-10 alkenyl and PhX which represents phenyl optionally substituted by up to 3 substitutents independently selected from C 1-4 alkyl, Cl, F, Br, N0 2 , CF 3 , OH and C l-4 alkoxy; D is -CH=CH-, -N(CH 3 )-, -S- or -O-; and AA is part of an amino-acid of the formula HOOC-AA; with the proviso that R 1 and R 2 are not both phenyl when D is -N(CH 3 )-; or a pharmacologically acceptable acid addition salt thereof.

Claim 3

A compound, for therapeutic use, of the formula wherein R 1 , R 2 and D are as defined in claim 1; and R 3 is H or OCCH 3 ; with the proviso that R 3 is not H when D is -N(CH 3 )-, and that R 1 and R 2 are not both phenyl when D is -N( CH 3 ) -.

Claim 4

A compound of formula I as defined in claim 2, independent of use, with the additional provisos that R 3 is not H when D is -CH=CH-, that R 1 is neither H nor CH 3 when R 2 is H or CH 3 and D is -CH=CH-, and that R 1 is not H when R 2 is phenyl and D is -CH=CH-.

Claim 5

A compound of claim 1, wherein D is -CH= CH - and AA is -(CR 17 R 18 ) m -(CH 2 ) n -NR 14 R 15 , PhX-NH 2 or a naturally-occurring amino-acid minus its carboxylic acid function, in which m is 1, 2, 3 or 4, n is 0, 1, 2, 3, 4 or 5, R 14 and R 15 are independently selected from H, C 1-10 alkyl, (C 1-4 alkyl)carbonyl, -CO-PhX and -PhX, the or each R 17 and the or each R 18 are independently selected from H, C 1-10 alkyl, -CH 2 -PhX and -PhX, and PhX-NH 2 represents PhX ring-substituted by NH 2 , PhX being as defined in claim 1.

Claim 6

A compound of claim 2 or claim 3, wherein D is -CH=CH-.

Claim 7

A compound of any preceding claim, wherein R 1 and R 2 are each ethyl or R 1 is H and R 2 is n-butyl.

Claim 8

4-Methoxy-2,3-diphenyl-1-naphthalenol, acetate, or 7-methoxy-l-methyl-5,6-diphenyl-lH-indol-4-ol, acetate (ester).

Claim 9

4-Methoxy-2,3-diphenyl-1-naphthalenol, acetate, or 7-methoxy-l-methyl-5,6-diphenyl-lH-indol-4-ol, acetate (ester).

Claim 10

A compound selected from 5-butyl-7-methoxy-4-benzofuranol and its acetate, 5-butyl-7-methoxybenzo(b)thiophen-4-ol and its acetate, 5-butyl-7-methoxy-l-methyl-lH-indol-4-ol, acetate (ester), and 5,6-diethyl-7-methoxy-1-methyl-1H-indol-4-ol, acetate (ester).

Claim 11

A compound selected from 5-butyl-7-methoxy-4-benzofuranol and its acetate, 5-butyl-7-methoxybenzo(b)thiophen-4-ol and its acetate, 5-butyl-7-methoxy-l-methyl-lH-indol-4-ol, acetate (ester), and 5,6-diethyl-7-methoxy-1-methyl-1H-indol-4-ol, acetate (ester).

Claim 12

2-Butyl-4-methoxy-l-naphthalenol, acetate, or 2,3-diethyl-4-methoxy-l-naphthalenol, acetate.

Claim 13

2-Butyl-4-methoxy-l-naphthalenol, acetate, or 2,3-diethyl-4-methoxy-l-naphthalenol, acetate.

Claim 14

A compound selected from L-valine, 2,3-diethyl-4-methoxynaphth-1-yl ester and its hydrochloride (preferred), L-alanine, 2,3-diethyl-4-methoxynaphth-1-yl ester, L-phenylalanine, 2,3-diethyl-4-methoxynaphth-1-yl ester, hydrochloride, 3-(N,N-diethylamino)propionic acid, 2,3-diethyl-4-methoxynaphth-1-yl ester, N,N-diethylaminoacetic acid, 2,3-diethyl-4-methoxynaphth-1-yl ester, L-valine, 2-n-butyl-4-methoxynaphth-1-yl ester and its hydrochloride, L-alanine, 2-n-butyl-4-methoxynaphth-1-yl ester and its hydrochloride (preferred), and L-phenylalanine, 2-n-butyl-4-methoxynaphth-1-yl ester, hydrochloride.

Claim 15

A compound selected from L-valine, 2,3-diethyl-4-methoxynaphth-1-yl ester and its hydrochloride (preferred), L-alanine, 2,3-diethyl-4-methoxynaphth-1-yl ester, L-phenylalanine, 2,3-diethyl-4-methoxynaphth-1-yl ester, hydrochloride, 3-(N,N-diethylamino)propionic acid, 2,3-diethyl-4-methoxynaphth-1-yl ester, N,N-diethylaminoacetic acid, 2,3-diethyl-4-methoxynaphth-1-yl ester, L-valine, 2-n-butyl-4-methoxynaphth-1-yl ester and its hydrochloride, L-alanine, 2-n-butyl-4-methoxynaphth-1-yl ester and its hydrochloride (preferred), and L-phenylalanine, 2-n-butyl-4-methoxynaphth-1-yl ester, hydrochloride.