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 --CH.sub.2 CH.sub.2 --; and
- Y is >N--CH.sub.2 -- 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.sub.1 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, nitro or cyano in the six-membered rings and hydrogen, halogen, trifluoromethyl, nitro or cyano in the five-membered rings; and
- R.sup.4 is 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 in the six-membered rings and hydrogen, 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 in the five-membered rings, 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 r is 1 or 2.
- 4. A compound according claim 1 wherein Z is selected from ##STR30## wherein M.sub.1 and M.sub.2 independently are CH or N.
- 5. A compound according to claim 1 wherein R.sup.3 is hydrogen, nitro or cyano in the six-membered rings and hydrogen, trifluoromethyl, nitro or cyano in the five-membered rings.
- 6. A compound according to claim 1 wherein R.sup.4 is 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 in the six-membered rings and hydrogen, trifluoromethyl, nitro, cyano or (CH.sub.2).sub.m COR.sup.11 in the five-membered rings.
- 7. A compound according to claim 1 wherein m is 0 or 1.
- 8. A compound according to claim 1 wherein R.sup.11 is hydroxy.
- 9. A compound according to claim 1 selected from the following:
- 2-(4-(2-(10,11-Dihydro-5H-dibenz[b,f]azepin-5-yl)-1-ethyl)-1-piperazinyl)-3-pyridinecarboxylic acid;
- 6-(4-(3-(10,11-Dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propyl)-1-piperazinyl)-2-pyridinecarboxylic acid;
- 2-(4-(3-(10,11-Dihydro-5H-dibenz[b,f]azepin-5-yl)-1-propyl)-1-piperazinyl)-3-pyridinecarboxylic acid;
- 2-(4-(3-(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)-1-propyl)-1-piperazinyl)-5-pyridinecarboxylic acid;
- 2-(4-(3-(3-Chloro-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-1-propyl)-1-piperazinyl)3-pyridinecarboxylic acid; and
- 2-(4-(3-(3-Methyl-10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)-1-propyl)-1-piperazinyl)-3-pyridinecarboxylic acid;
- or a pharmaceutically acceptable salt thereof.
- 10. A pharmaceutical composition comprising as an active component an effective amount of a compound according to claim 1 together with a pharmaceutically acceptable carrier or diluent.
- 11. The pharmaceutical composition according to claim 10 comprising between 0.5 mg and 1000 mg of the compound.
- 12. A method of treating neurogenic inflammation comprising administering to a subject in need thereof an effective amount of a compound according to claim 1.
- 13. A method of treating neurogenic inflammation comprising administering to a subject in need thereof a pharmaceutical composition according to claim 10.
- 14. 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.
- 15. 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 10.
- 16. A method of treating insulin resistance in 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.
- 17. A method of treating insulin resistance in non-insulin-dependent diabetes mellitus (NIDDM) or ageing-associated obesity comprising administering to a subject in need thereof a pharmaceutical composition of claim 10.
Priority Claims (1)
Number |
Date |
Country |
Kind |
1090/96 |
Oct 1996 |
DKX |
|
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a divisional of application Ser. No. 08/943,726 filed Oct. 3, 1997 now U.S. Pat. No. 5,916,889 and claims priority under 35 U.S.C. 119 of Danish application 1090/98 filed Oct. 4, 1996, the contents of which are fully incorporated herein by reference.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
3780035 |
Nakanishi et al. |
Dec 1973 |
|
Foreign Referenced Citations (3)
Number |
Date |
Country |
2186249 |
Jan 1974 |
FRX |
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). |
Divisions (1)
|
Number |
Date |
Country |
Parent |
943726 |
Oct 1997 |
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