Claims
- 1. A compound of formula I ##STR28## wherein R.sup.1 and R.sup.2 independently are hydrogen, halogen, trifluoromethyl, hydroxy, C.sub.1-6 -alkyl or C.sub.1-6 -alkoxy; and
- X is --OCH.sub.2 O--, --S--CH.sub.2 --, --CH.sub.2 --S--; and
- Y is >CH--CH.sub.2 --, >C.dbd.CH--, >CH--O-- wherein only the underscored atom participates in the ring system; and
- r is 1, 2 or 3; and
- Z is selected from ##STR29## wherein M, and M.sub.2 independently are CH or N; and R.sup.5 is hydrogen, C.sub.1-6 -alkyl, phenyl or benzyl; and
- R.sup.3 is hydrogen, halogen, trifluoromethyl, nitro or cyano; and
- R.sup.4 is halogen, trifluoromethyl, nitro, cyano, (CH.sub.2).sub.m COR.sup.11, (CH.sub.2).sub.m OH or (CH.sub.2).sub.m SO.sub.2 R.sup.11 wherein R.sup.11 is hydroxy, C.sub.1-6 alkoxy or NHR.sup.12, wherein R.sup.12 is hydrogen or C.sub.1-6 -alkyl; and m is 0, 1 or 2;
- or a pharmaceutically acceptable salt thereof.
- 2. A compound according to claim 1 wherein R.sup.1 and R.sup.2 independently are hydrogen, halogen, trifluoromethyl or C.sub.1-6 alkyl.
- 3. A compound according to claim 1 wherein Y is >C.dbd.CH-- or >CH--O-- wherein only the underscored atom participates in the ring system.
- 4. A compound according claim 1 wherein r is 1.
- 5. A compound according to claim 1 wherein Z is selected from ##STR30## wherein M.sub.1 and M.sub.2 independently are CH or N.
- 6. A compound according to claim 1 wherein R.sup.3 is hydrogen, trifluoromethyl, nitro or cyano.
- 7. A compound according to claim 1 wherein R.sup.4 is trifluoromethyl, nitro, cyano or (CH.sub.2).sub.m COR.sup.11.
- 8. A compound according to claim 7 wherein m is 0 or 1.
- 9. A compound according to claim 1 wherein R.sup.11 is hydroxy.
- 10. A compound according to claim 1 selected from the following:
- 2-(4-(3-(12H-Dibenzo�d,g!�1,3!dioxocin-12-ylidene)-1-propyl)piperazin-1-yl)-3-pyridinecarboxylic acid;
- 2-(4-(3-(2,10-Dichloro-12H-dibenzo�d,g!�1,3!dioxocin-12-ylidene)-1-propyl)-piperazin-1-yl)-3-pyridinecarboxylic acid;
- 2-(4-(2-(6,11-Dihydro-dibenzo�b,e!thiepin-11-ylidene)ethyl)piperazin-1-yl)-3-pyridinecarboxylic acid;
- 2-(4-(3-(6,11-Dihydrodibenzo�b,e!thiepin-11-ylidene)-1-propyl)-1-piperazinyl)-3-pyridinecarboxylic acid;
- 2-(4-(2-(6,11-Dihydrodibenzo�b,e!thiepin-11-yloxy)ethyl)-1-piperazinyl)-3-pyridinecarboxylic acid;
- or a pharmaceutically acceptable salt thereof.
- 11. A method of preparing a compound according to claim 1, comprising:
- a) reacting a compound of formula II ##STR31## wherein R.sup.1, R.sup.2, X, Y, and r are as defined in claim 1 and W is a suitable leaving group, with a compound of formula III ##STR32## wherein Z is as defined in claim 1 to form a compound of formula I.
- 12. A pharmaceutical composition comprising as an active component a compound according to claim 1 together with a pharmaceutically acceptable carrier or diluent.
- 13. The pharmaceutical composition according to claim 12 comprising between 0.5 mg and 1000 mg of the compound.
- 14. A method of treating neurogenic inflammation in a subject in need of such treatment comprising administering to said subject an effective amount of a compound according to claim 1.
- 15. A method of treating neurogenic inflammation in a subject in need of such treatment comprising administering to said subject a pharmaceutical composition according to claim 13.
- 16. A method of treating neurogenic inflammation associated with neuropathy, rheumatoid arthritis, migraine or itching comprising administering to a subject in need thereof an effective amount of a compound of claim 1.
- 17. A method of treating neurogenic inflammation associated with neuropathy, rheumatoid arthritis, migraine or itching comprising administering to a subject in need thereof a pharmaceutical composition of claim 12.
- 18. A method of treating insulin resistance relating to non-insulin-dependent diabetes mellitus (NIDDM) or ageing-associated obesity comprising administering to a subject in need thereof an effective amount of a compound of claim 1.
- 19. A method of treating insulin resistance relating to non-insulin-dependent diabetes mellitus (NIDDM) or ageing-associated obesity comprising administering to a subject in need thereof a pharmaceutical composition of claim 12.
Priority Claims (1)
Number |
Date |
Country |
Kind |
1090/96 |
Oct 1996 |
DKX |
|
CROSS-REFERENCE TO RELATED APPLICATIONS
This application claims priority under 35 U.S.C. 119 of Danish application 1090/96 filed Oct. 4, 1996, the contents of which are fully incorporated herein by reference.
US Referenced Citations (4)
Foreign Referenced Citations (2)
Number |
Date |
Country |
WO 9518793 |
Jul 1995 |
WOX |
WO 9631498 |
Oct 1996 |
WOX |
Non-Patent Literature Citations (1)
Entry |
Sindelar et al., Collection Czech. Chem. Commun., vol. 59, pp. 667-674 (1994). |