Claims
- 1. A compound of formula I ##STR9## or an N-oxide, or a pharmaceutically acceptable salt where Z is S(O)q where q is 0, 1 or 2,
- m is0-5;
- R is C.sub.1 to C.sub.20 -aliphatic, unsubstituted or substituted phenyl C.sub.1 to C.sub.10 -aliphatic where substituted phenyl has one or more radicals selected from the group consisting of lower alkoxy, lower alkyl, trihalomethyl, and halo, or R is C.sub.1 to C.sub.20 -aliphatic-O-, or R is unsubstituted or substituted phenyl C.sub.1 to C.sub.10 -aliphatic-O- where substituted phenyl has one or more radicals selected from the group consisting of lower alkoxy, lower alkyl, trihalomethyl, and halo;
- R.sub.1 is -(C.sub.1 to C.sub.5 aliphatic)R.sub.4, -(C.sub.1 to C.sub.5 aliphatic)CHO, -(C.sub.1 to C.sub.5 aliphatic) CH.sub.2 OR.sub.8, -R.sub.4, -CH.sub.2 OH, or CHO;
- R.sub.2 is H, halo, lower alkyl, lower alkoxy, -CN, -(CH.sub.2).sub.n R.sub.4, -CH(NH.sub.2)(R.sub.4), or -(CH.sub.2).sub.n R.sub.9 where n is 0-5 and where R.sub.9 is -N(R.sub.7).sub.2 where each R.sub.7 is independently H, or an aliphatic group of 1 to 10 carbon atoms, or acyl of 1-6 carbon atoms, or a cycloalkyl-(CH.sub.2).sub.n - group of 4 to 10 carbons where n is 0-3, or both R.sub.7 groups form a ring having 4 to 6 carbons; or
- R.sub.3 is hydrogen, lower alkyl, lower alkoxy, halo, -CN, R.sub.4, NHCONH.sub.2, or OH;
- each R.sub.4 group is independently -COR.sub.5 where R.sub.5 is -OH, a pharmaceutically acceptable ester-forming group -OR.sub.6, or -OX where X is a pharmaceutically acceptable cation, or R.sub.5 is -N(R.sub.7).sub.2 where each R.sub.7 is independently H, or an aliphatic group of 1 to 10 carbon atoms, or a cycloalkyl-(CH.sub.2).sub.n - group of 4 to 10 carbons where n is 0-3, or both R.sub.7 groups form a ring having 4 to 6 carbons, or R.sub.4 is a sulfonamide, or tetrazol-5-yl; and
- R.sub.8 is hydrogen, C.sub.1 to C.sub.6 alkyl, or C.sub.1 to C.sub.6 -acyl,
- excluding those compounds where R.sub.2 and R.sub.3 are other than hydrogen and are substituted in the 2 and 6 positions.
- 2. A compound of claim 1 where m is 0 or 1.
- 3. A compound of claim 2 where R is alkoxy of 8 to 15 carbon atoms or unsubstituted or substituted pheny-C.sub.1 to C.sub.10 -alkyl-O- where substituted phenyl is substituted with fluoro, trifluoromethyl or methoxy and R.sub.1 is R.sub.4 CH.dbd.CH- or R.sub.4 CH.sub.2 CH.sub.2 -.
- 4. A compound of claim 3 which is
- 3- [1 -thia-2-[2-(E-2-carboxyethenyl)-3-[8-(4-methoxyphenyl)octyloxy]-6-pyridyl]ethyl]benzoic acid;
- 3-[1-oxythia-2-[2-(E-2-carboxyethenyl)-3-[8-(4-methoxyphenyl) octyloxy]-6-pyridyl]ethyl]benzoic acid;
- 3-[1-dioxythia-2-[2-(E-2-carboxyethenyl)-3-[8-(4-methoxyphenyl)octyloxy]-6-pyridyl]ethyl]benzoic acid; or
- a pharmaceutically acceptable salt thereof.
- 5. A compound of claim 3 which is
- 2-[1-oxythia-2-[2-(E-2-carboxyethenyl)-3-dodecyloxy-6-pyridyl]ethyl]benzoic acid;
- 3-[1-thia-2-[2-(E-2-carboxyethenyl)-3-dodecyloxy-6-pyridyl]ethyl]benzoic acid;
- 3-[1-oxythia-2-[2-(E-2-carboxyethenyl)-3-dodecyloxy-6-pyridyl]ethyl]benzoic acid;
- 3-[1-dioxythia-2-[2-(E-2-carboxyethenyl)-3-dodecyloxy-6-pyridyl]ethyl]benzoic acid;
- N-[3-[1-thia-2-[2-(E-2-carboxyethenyl)-3-dodecyloxy-6-pyridyl]ethyl]phenyl]trifluoromethanesulfonamide;
- N-[3-[1-thia-2-[2-(E-2-carboxyethenyl)-3-(8-(4-methoxyphenyl)octyloxy)-6-pyridyl]ethyl]phenyl]trifluoromethane sulfonamide;
- N-[3-[1-oxythia-2- [2-(E-2-carboxyethenyl)-3-(8-(4-methoxyphenyl)octyloxy)-6-pyridyl]ethyl]phenyl]trifluoromethanesulfonamide;
- N-[3-[1-oxythia-2-[2-(E-2-carboxyethenyl)-3-(8-(4-methoxyphenyl)octyloxy)-6-pyridyl]ethyl]phenyl]phenylsulfonamide;
- N-[3-[1-thia-2-[2-(E-2-carboxyethenyl)-3-(8-(4-methoxyphenyl)octyloxy)-6-pyridyl]ethyl]phenyl]phenylsulfonamide,
- a pharmaceutically acceptable salt thereof.
- 6. A compound of claim 3 where m is 1 which is
- 4-[2-thia-3-[2-(E-2-carboxyethenyl)-3-[8-(4-methoxyphenyl)octyloxy]-6-pyridyl]propyl]benzoic acid;
- 4-[2-thia-3-[2-(E-2-carboxyethenyl)-3-[4-(4-methoxyphenyl)butyloxy]-6-pyridyl]propyl]benzoic acid,
- 3-[2-thia-3-[2-(E-2-carboxyethenyl)-3-[8-(4-methoxyphenyl)octyloxy]-6-pyridyl]propyl]benzoic acid;
- 3-[2-thia-3-[2-(E-2-carboxyethenyl)-3-[4-(4-methoxyphenyl)butyloxy]-6-pyridyl]propyl]benzoic acid;
- 3-[2-thia-3-[2-(2-carboxyethanyl)-3-[8-(4-methoxyphenyl)octyloxy]-6-pyridyl]propyl]benzoic acid;
- 3-[2-thia-3-[2-(E-2-carboxyethenyl)-3-[8-(4-methoxyphenyl)octyloxy]-6-pyridyl]propyl]-N,N-dimethylbenzamide, lithium salt;
- 3-[2-thia-3-[2-(E-2-carboxyethenyl)-3-(4-(4-methoxyphenyl)butyloxy)-6-pyridyl]propyl]-N,N-dimethylbenzamide, lithium salt;
- 3-[2-thia-3-[2-(E-2-carboxyethenyl)-3-[4-phenylbutyloxy]-6-pyridyl]propyl]benzoic acid, dilithium salt;
- 3-[2-thia-3-[2-(E-2-carboxyethenyl)-3-[8-phenyloctyloxy]-6-pyridyl]propyl]benzoic acid, dilithium salt;
- 3-[2-thia-3-[2-(2-carboxyethanyl)-3-[4-(4-methoxyphenyl)butyloxy]-6-pyridyl]propyl]benzoic acid, dilithium salt; or
- 4-[2-thia-3-[2-(E-2-carboxyethenyl)-3-[8-(4-methoxyphenyl)octyloxy]-6-pyridyl]propyl]phenylacetic acid,
- 4-[2-oxythia-3-[2-(E-2-carboxyethenyl)-3-[8-(4-methoxyphenyl)octyloxy]-6-pyridyl]propyl]benzoic acid;
- 3-[2-oxythia-3-[2-(E-2-carboxyethenyl)-3-[8-(4-methoxyphenyl)octyloxy]-6-pyridyl]propyl]benzoic acid; or
- 3-[2-dioxythia-3-[2-(E-2-carboxyethenyl)-3-[8-(4-methoxyphenyl)octyloxy]-6-pyridyl]propyl]benzoic acid;
- 4-[2-oxythia-3-[2-(E-2-carboxyethenyl)-3 -[8-(4-methoxyphenyl)octyloxy]-6-pyridyl]propyl]phenylacetic acid;
- 5-[3-[2-thia-3-[2-(E-2-carboxyethenyl)-3-[8-(4-methoxyphenyl)octyloxy]-6-pyridyl]propyl]phenyl]tetrazole, dilithium salt;
- 3-[2-thia-3-[2-(E-2-carboxyethenyl)-3-[4-(4-methoxyphenyl)butyloxy]-6-pyridyl]propyl]benzene, lithium salt;
- 3-[2-thia-3-[2-(2-carboxyethanyl)-3-[4-(4-methoxyphenyl)butyloxy]-6-pyridyl]propyl]benzene, lithium salt; or
- 3-[1-thia-2-[2-(2-carboxyethanyl)-3-[4-(4-methoxyphenyl)butyloxy]-6-pyridyl]ethyl]benzene, lithium salt a pharmaceutically acceptable salt thereof.
- 7. A compound of claim 2 where R.sub.2 is -(CH.sub.2).sub.n R.sub.9 where n is 0, 1 or 2.
- 8. A compound of claim 7 which is
- 3-[1-thia-2-[2-(E-2-carboxyethenyl)-3-(8-(4-methoxyphenyl)octyloxy)-6-pyridyl]ethyl]aniline, lithium salt;
- 3-[1-thia-2-[2-(E-2-carboxyethenyl)-3-(4-(4-methoxyphenyl)butyloxy)-6-pyridyl]ethyl]aniline, lithium salt;
- 3-[1-thia-2-[2-(E-2-carboxyethenyl)-3-(8-(4-methoxyphenyl)octyloxy)-6-pyridyl]ethyl]-N,N-dimethylaniline, lithium salt;
- 3-[1-thia-2-[2-(E-2-carboxyethenyl)-3-(8-(4-trifluoromethylphenyl)octyloxy)-6-pyridyl]ethyl]aniline, lithium salt;
- 3-[thia-2-[2-(E-2-carboxyethenyl)-3-(8-phenyloctyloxy)-6-pyridyl]ethyl]aniline, lithium salt; or
- 3-[2-thia-3-[2-(E-2-carboxyethenyl)-3-(8-(4-methoxyphenyl)octyloxy)-6-pyridyl]propyl]-N,N-dimethylaniline, lithium salt,
- 3-[1-oxythia-2-[2-(E-2-carboxyethenyl)-3-(4-(4-methoxyphenyl)butyloxy)-6-pyridyl]ethyl]aniline, lithium salt;
- 3-[1-oxythia-2-[2-(E-2-carboxyethenyl)-3-(8-(4-trifluoromethylphenyl)octyloxy)-6-pyridyl]ethyl]aniline, lithium salt;
- 3-[1-oxythia-2-[2-(E-2-carboxyethenyl)-3-(8-(4-fluorophenyl)octyloxy)-6-pyridyl]ethyl]aniline, lithium salt;
- 3-[1-oxythia-2-[2-(E-2-carboxyethenyl)-3-(8-(4-methoxyphenyl)octyloxy)-6-pyridyl]-ethyl]aniline, lithium salt, or
- 3-[1-oxythia-2-[2-(E-2-carboxyethenyl)-3-(8-phenyloctyloxy)-6-pyridyl]ethyl]aniline, lithium salt;
- 3-[1-oxythia-2-[2-(E-2-carboxyethenyl)-3-(8-(4-methoxyphenyl)octyloxy)-6-pyridyl]ethyl]-N,N-dimethylaniline, lithium salt;
- 3-[1-dioxythia-2-[2-(E-2-carboxyethenyl)-3-(4-(4-methoxyphenyl)butyloxy)-6-pyridyl]ethyl]aniline, lithium salt;
- 3-[1-dioxythia-2-[2-(E-2-carboxyethenyl)-3-(8-(4-methoxyphenyl)octyloxy)-6-pyridyl]ethyl]aniline, lithium salt or the acid thereof or another pharmaceutically acceptable salt.
- 9. A pharmaceutical composition comprising an effective amount of a compound of formula I according to claim 1 and a pharmaceutically acceptable excipient.
- 10. The composition of claim 9 for use in treating psoriasis.
Parent Case Info
This is a continuation of application Ser. No. 08/211,063, filed Jul. 18, 1994, abandoned.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
5109009 |
Nielsen et al. |
Apr 1992 |
|
Non-Patent Literature Citations (2)
Entry |
Chemical Abstracts, vol. 116(23), abst.No. 116:235,400w,Jun . 8, 1992. |
Chemical Abstracts, Vo. 120,(21),270,117a,May 23, 1994. |
Continuations (1)
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Number |
Date |
Country |
Parent |
211063 |
Jul 1994 |
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