Claims
- 1. A compound of formula I ##STR16## 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;
- Y is >CH--CH.sub.2 -- or >C.dbd.CH-- wherein only the underscored atom participates in the ring system;
- X is --C(R.sup.6 R.sup.7)--, --CH.sub.2 CH.sub.2 --, --CH.dbd.CH--CH.sub.2 --, --CH.sub.2 --CH.dbd.CH--, --CH.sub.2 --(C.dbd.O)--, --(C.dbd.O)--CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.dbd.CH--, --CH(R.sup.10)CH.sub.2 --, --CH.sub.2 CH(R.sup.10)-- or --(C.dbd.O)--, wherein R.sup.6 and R.sup.7 independently are hydrogen or C.sub.1-6 -alkyl; and wherein R.sup.10 is C.sub.1-6 -alkyl or phenyl;
- r is 1, 2 or 3; and
- Z is selected from ##STR17## wherein R.sup.3 is --(CH.sub.2).sub.p COOH wherein p is 2, 3, 4, 5 or 6; or
- a pharmaceutically acceptable salt thereof.
- 2. A compound of claim 1 wherein R.sup.1 and R.sup.2 independently are hydrogen, halogen, trifluoromethyl or C.sub.1-6 -alkyl.
- 3. A compound of claim 1, wherein X is --CH.sub.2 CH.sub.2 -- or --CH.dbd.CH--.
- 4. A compound of claim 1, wherein Y is >C.dbd.CH--.
- 5. A compound of claim 1 wherein Z is selected from ##STR18## wherein R.sup.3 is --(CH.sub.2).sub.p COOH and p is 2, 3, 4, 5 or 6.
- 6. A compound of claim 1 wherein p is 2 or 3.
- 7. A compound of claim 1 selected from the following:
- 3-(1-(3-(10,11-Dihydrodibenzo[a,d]cyclohepten-5-ylidene)-1-propyl)piperidin-3-yl)propionic acid,
- 3-(1-(2-(10,11-Dihydrodibenzo[a,d]cyclohepten-5-ylidene)ethyl)piperidin-4-yl)propionic acid, and
- 3-(1-(3-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propyl)piperidin-4-yl)-propionic acid,
- or a pharmaceutically acceptable salt thereof.
- 8. A compound of claim 1 selected from the following:
- 4-(1-(3-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propyl)piperidin-4-yl)-butyric acid,
- 3-(1-(3-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propyl)piperidin-2-yl)-propionic acid, and
- 3-(1-(3-(1-Bromo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propyl)piperidin-4-yl)propionic acid,
- or a pharmaceutically acceptable salt thereof.
- 9. A method of preparing a compound of claim 1, comprising: reacting a compound of formula II ##STR19## wherein W is a suitable leaving group, with a compound of formula III
- HZ (III)
- to form a compound of formula I.
- 10. A pharmaceutical composition comprising a compound of claim 1 together with a pharmaceutically acceptable carrier or diluent.
- 11. The pharmaceutical composition of claim 10 comprising between 0.5 mg and 1000 mg of the compound per unit dose.
- 12. A method of treating insulin resistance comprising administering to a subject in need thereof an effective amount of a compound of claim 1.
- 13. A method of treating insulin resistance comprising administering to a subject in need thereof a pharmaceutical composition of claim 10.
- 14. A method of treating neurogenic inflammation comprising administering to a subject in need thereof a therapeutically effective amount of a compound of claim 1.
- 15. A method of treating neurogenic inflammation comprising administering to a subject in need thereof a pharmaceutical composition of claim 10.
- 16. A method of treating neurogenic inflammation associated with neuropathy or rheumatoid arthritis comprising administering to a subject in need thereof a therapeutically effective amount of a compound of claim 1.
- 17. A method of treating neurogenic inflammation associated with neuropathy or rheumatoid arthritis comprising administering to a subject in need thereof a pharmaceutical composition of claim 10.
Priority Claims (1)
Number |
Date |
Country |
Kind |
0751/97 |
Jun 1997 |
DKX |
|
CROSS-REFERENCE TO RELATED APPLICATIONS
This application claims priority under 35 U.S.C. 119 of Danish application 0751/97 filed Jun. 25, 1997 and U.S. Provisional application 60/051,833 filed Jul. 7, 1997, the contents of which are fully incorporated herein by reference.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
5595989 |
Andersen et al. |
Jan 1997 |
|
Foreign Referenced Citations (1)
Number |
Date |
Country |
WO 9518793 |
Jul 1995 |
WOX |