Claims
- 1. A method of opening ATP-regulated potassium channels in a subject, said method comprising administration to the subject in need thereof an effective amount of a compound selected from the group consisting of:3-[3,5-bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile, 3-[3,5-bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-cyclopentylamino-2-propenenitrile, 3-[3,5-bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-isopropylamino-2-propenenitrile, 3-[3,5-bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-cyclobutylamino-2-propenenitrile, 3-[3,5-bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-propylamino-2-propenenitrile, 2-(4-Chlorophenylsulfonyl)-3-(pyridin-3-ylamino)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile, 2-(4-Chlorophenylsulfonyl)-3-(3,5-dichlorophenylamino)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile, 3-(Benzo[1,3]dioxol-5-ylamino)-2-(4-chloro-phenylsulfonyl)-3-(1,2,2-trimethyl-propylamino)- propenenitrile, 3-(3,5-Bis(trifluoromethyl)phenylamino)-2-methylsulfonyl-3-(1,2,2-trimethylpropylamino)-propenenitrile, 2-(4-Chlorophenylsulfonyl)-3-(3,5-dimethoxyphenylamino)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile, 3-[N-(3,5-bis(trifluoromethyl)phenyl)-N-methylamino]-2-(4-chlorophenylsulfonyl)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile, (1′S,2′S)-3-[2-Benzyloxycyclopentylamino]-3-[3,5-bis(trifluoromethyl)phenylamino]-2-(4chlorophenylsulfonyl)-2-propenenitrile, (1′R,2′R)-3-[2-Benzyloxycyclopentylamino]-3-[3,5-bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-2-propenenitrile, (S)-3-[3,5-Bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile, (S)-3-[3,5-Bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-(1,2-dimethylpropylamino)-2-propenenitrile, (R)-3-[3,5-Bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-(1,2-dimethylpropylamino)-2-propenenitrile, 3-[3,5-Bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-(1,1-dimethylpropylamino)-2-propenenitrile, 3-[3,5-Bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-(5-cyclopropyl-2-methyl-2H-pyrazol-3-ylamino)-2-propenenitrile, (R)-3-[3,5-bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile, 3-(3,5-Bis(trifluoromethyl)phenylamino)-3-isopropylamino-2-methylsulfonyl-propenenitrile, (R)-3-[3,5-bis(trifluoromethyl)phenylamino]-2-methanesulfonyl-3-(1,2,2-trimethylpropylamino)-2-propenenitrile, (S)-3-[3,5-bis(trifluoromethyl)phenylamino]-2-methanesulfonyl-3-(1,2,2-trimethylpropylamino)-2-propenenitrile, 2-(4-Chlorophenylsulfonyl)-3-(3,5-dimethoxyphenylamino)-3-(1,1-dimethylpropylamino)-2-propenenitrile, 2-(4-Chlorophenylsulfonyl)-3-(3,5-dimethoxyphenylamino)-3-cyclobutylamino-2-propenenitrile, 3-(3,5-dimethoxyphenylamino)-2-methanesulfonyl-3-(1,2,2-trimethylpropylamino)-propenenitrile 3-(3,5-dimethoxyphenylamino-3-isopropyl-2-methanesulfonyl-propenenitrile, 3-(Benzo[1,3]dioxol-5-ylamino)-3-(1,1-dimethyl-propylamino)-2-(4-chloro-phenylsulfonyl)-propenenitrile, 3-(Benzo[1,3]dioxol-5-ylamino)-3-cyclobutylamino-2-(4-chloro-phenylsulfonyl)-propenenitrile, 2-(4-Chlorophenylsulfonyl)-3-(3,5-dichlorophenylamino)-3-(1,1-dimethylpropylamino)-2-propenenitrile, 2-(4-Chlorophenylsulfonyl)-3-cyclobutylamino-3-(3,5-dichlorophenylamino)-2-propenenitrile, 3-sec-Butylamino-2-(4-chlorophenylsulfonyl)-3-(3,5-dichlorophenylamino)-2-propenenitrile, 2-Methylsulfonyl-3-(3-methoxy-5-trifluoromethyl-phenylamino)-3-(1,2,2-trimethylpropylamino)-propenenitrile, 3-(3-Fluoro-5-trifluoromethyl-phenylamino)-2-methylsulfonyl-3-(1,2,2-trimethylpropylamino)-propenenitrile, 3-(4-Chlorophenylamino)-2-methylsulfonyl-3-(1,2,2-trimethylpropylamino)-acrylonitrile, 3-(Benzothiazol-6-ylamino)-3-(1,1-dimethyl-propylamino)-2-methylsulfonyl-propenenitrile, 3-(Benzo[1,3]dioxol-5-ylamino)-2-(2,2-dimethyl-propionyl)-3-(1,1-dimethyl-propylamino)-propenenitrile, 2-(4-Chlorophenylsulfonyl)-3-(3-cyanophenylamino)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile, 2-(4-Chlorophenylsulfonyl)-3-(3-cyanophenylamino)-3-cyclopentylamino-2-propenenitrile, 2-(4-Chlorophenylsulfonyl)-3-(3-cyanophenylamino-3-(1,2-dimethylpropylamino)-2-propenenitrile, 3-(3,5-Bis(trifluoromethyl)phenylamino)-2-isopropylsulfonyl-3-(1,2,2-trimethylpropylamino)-propenenitrile, 3-(3,5-Bis(trifluoromethyl)phenylamino)-2-isopropylsulfonyl-3-cyclopentylamino-2-propenenitrile, 3-(3,5-Bis(trifluoromethyl)phenylamino)-3-cyclobutylamino-2-isopropylsulfonyl-2-propenenitrile, 3-(3,5-Bis(trifluoromethyl)phenylamino)-2-isopropylsulfonyl-3-(2-methyl)propylamino)-2-propenenitrile, 2-Isopropylsulfonyl-3-(3-methoxyphenylamino)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile, 3-Cyclopentylamino-2-isopropylsulfonyl-3-(3-methoxy)phenylamino-2-propenenitrile, 3-Cyclobutylamino-2-isopropylsulfonylamino-3-(3-methoxy)phenylamino-2-propenenitrile, 2-Isopropylsulfonyl-3-(3-methoxy)phenylamino-3-(2-methyl)propylamino)-2-propenenitrile, 3-(1,1-Dimethyl)propylamino)-2-isopropylsulfonyl-3-(3-methoxy)phenylamino-2-propenenitrile, 2-Isopropylsulfonyl-3-(3-methoxy)phenylamino-3-tert.-butylamino-2-propenenitrile, and 3-(Benzo[1,3]dioxol-5-ylamino)-3-(1,1-dimethylpropylamino)-2-methanesulfonyl-2-propenenitrile, or a pharmaceutically acceptable salt thereof.
- 2. A method of treating diabetes or hyperinsulinemia in a subject, said method comprising administering to the subject in need thereof an effective amount of a compound selected from the group consisting of:3-[3,5-bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile, 3-[3,5-bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-cyclopentylamino-2-propenenitrile, 3-[3,5-bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-isopropylamino-2-propenenitrile, 3-[3,5-bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-cyclobutylamino-2-propenenitrile, 3-[3,5-bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-propylamino-2-propenenitrile, 2-(4-Chlorophenylsulfonyl)-3-(pyridin-3-ylamino)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile 2-(4-Chlorophenylsulfonyl)-3-(3,5-dichlorophenylamino)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile, 3-(Benzo[1,3]dioxol-5-ylamino)-2-(4-chloro-phenylsulfonyl)-3-(1,2,2-trimethyl-propylamino)-propenenitrile, 3-(3,5-Bis(trifluoromethyl)phenylamino)-2-methylsulfonyl-3-(1,2,2-trimethylpropylamino)-propenenitrile, 2-(4-Chlorophenylsulfonyl)-3-(3,5-dimethoxyphenylamino)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile, 3-[N-(3,5-bis(trifluoromethyl)phenyl)-N-methylamino]-2-(4-chlorophenylsulfonyl)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile, (1′S,2′S)-3-[2-Benzyloxycyclopentylamino]-3-[3,5-bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-2-propenenitrile, (1′R,2′R)-3-[2-Benzyloxycyclopentylamino]-3-[3,5-bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-2-propenenitrile, (S)-3-[3,5-Bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile, (S)-3-[3,5-Bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-(1,2-dimethylpropylamino)-2-propenenitrile, (R)-3-[3,5-Bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-(1,2-dimethylpropylamino)-2-propenenitrile, 3-[3,5-Bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-(1,1-dimethylpropylamino)-2-propenenitrile, 3-[3,5-Bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-(5-cycloproply-2-methyl-2H-pyrazol-3-ylamino)-2-propenenitrile, (R)-3-[3,5-bis(trifluoromethyl)phenylamino]-2-(4-chlorophenylsulfonyl)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile, 3-(3,5-Bis(trifluoromethyl)phenylamino)-3-isopropylamnino-2-methylsulfonyl-propenenitrile, (R)-3-[3,5-bis(trifluoromethyl)phenylamino]-2-methanesulfonyl-3-(1,2,2-trimethylpropylamino)-2-propenenitrile, (S)-3-[3,5-bis(trifluoromethyl)phenylamino]-2-methanesulfonyl-3-(1,2,2-trimethylpropylamino)-2-propenenitrile, 2-(4-Chlorophenylsulfonyl)-3-(3,5-dimethoxyphenylamino)-3-(1,1-dimethylpropylamino)-2-propenenitrile, 2-(4-Chlorophenylsulfonyl)-3-(3,5-dimethoxyphenylamino)-3-cyclobutylamino-2-propenenitrile, 3-(3,5-dimethoxyphenylamino)-2-methanesulfonyl-3-(1,2,2-trimethylpropylamino)-propenenitrile 3-(3,5-dimethoxyphenylamino)-3-isopropyl-2-methanesulfonyl-propenenitrile, 3-(Benzo[1,3]dioxol-5-ylamino)-3-(1,1-dimethyl-propylamino)-2-(4-chloro-phenylsulfonyl)-propenenitrile, 3-(Benzo[1,3]dioxol-5-ylamino)-3-cyclobutylamino-2-(4-chloro-phenylsulfonyl)-propenenitrile, 2-(4-Chlorophenylsulfonyl)-3-(3,5-dichlorophenylamino)-3-(1,1-dimethylpropylamino)-2-propenenitrile, 2-(4-Chlorophenylsulfonyl)-3-cyclobutylamino-3-(3,5-dichlorophenylamino)-2-propenenitrile, 3-sec-Butylamino-2-(4-chlorophenylsulfonyl)-3-(3,5-dichlorophenylamino)-2-propenenitrile, 2-Methylsulfonyl-3-(3-methoxy-5-trifluoromethyl-phenylamino)-3-(1,2,2-trimethylpropylamino)-propenenitrile, 3-(3-Fluoro-5-trifluoromethyl-phenylamino)-2-methylsulfonyl-3-(1,2,2-trimethylpropylamino)-propenenitrile, 3-(4-Chlorophenylamino)-2-methylsulfonyl-3-(1,2,2-trimethylpropylamino)-acrylonitrile, 3-(Benzothiazol-6-ylamino)-3-(1,1-dimethyl-propylamino)-2-methylsulfonyl-propenenitrile, 3-(Benzo[1,3]dioxol-5-ylamino)-2-(2,2-dimethyl-propionyl)-3-(1,1-dimethyl-propylamino)-propenenitrile, 2-(4-Chlorophenylsulfonyl)-3-(3-cyanophenylamino)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile, 2-(4-Chlorophenylsulfonyl)-3-(3-cyanophenylamino)-3-cyclopentylamino-2-propenenitrile, 2-(4-Chlorophenylsulfonyl)-3-(3-cyanophenylamino-3-(1,2-dimethylpropylamino)-2-propenenitrile, 3-(3,5-Bis(trifluoromethyl)phenylamino)-2-isopropylsulfonyl-3-(1,2,2-trimethylpropylamino)-propenenitrile, 3-(3,5-Bis(trifluoromethyl)phenylamino)-2-isopropylsulfonyl-3-cyclopentylamino-2-propenenitrile, 3-(3,5-Bis(trifluoromethyl)phenylamino)-3-cyclobutylamino-2-isopropylsulfonyl-2-propenenitrile, 3-(3,5-Bis(trifluoromethyl)phenylamino)-2-isopropylsulfonyl-3-(2-methyl)propylamino)-2-propenenitrile, 2-Isopropylsulfonyl-3-(3-methoxyphenylamino)-3-(1,2,2-trimethylpropylamino)-2-propenenitrile, 3-Cyclopentylamino-2-isopropylsulfonyl-3-(3-methoxy)phenylamino-2-propenenitrile, 3-Cyclobutylamino-2-isopropylsulfonylamino-3-(3-methoxy)phenylamino-2-propenenitrile, 2-Isopropylsulfonyl-3-(3-methoxy)phenylamino-3-(2-methyl)propylamino)-2-propenenitrile, 3-(1,1-Dimethyl)propylamino)-2-isopropylsulfonyl-3-(3-methoxy)phenylamino-2-propenenitrile, 2-Isopropylsulfonyl-3-(3-methoxy)phenylamino-3-tert.-butylamino-2-propenenitrile, and 3-(Benzo[1,3]dioxol-5-ylamino)-3-(1,1-dimethylpropylamino)-2-methanesulfonyl-2-propenenitrile, or a pharmaceutically acceptable salt thereof.
Priority Claims (1)
Number |
Date |
Country |
Kind |
1998 01427 |
Nov 1998 |
DK |
|
CROSS-REFERENCE TO RELATED APPLICATIONS
This application is a divisional application Ser. No. of 09/433,264 filed Nov. 4, 1999 now abandoned, and claims priority under 35 U.S.C. 119 of U.S. provisional application No. 60/108,728 filed on Nov. 17, 1998 and of Danish application PA 1998 01427 filed on Nov. 5, 1998, the contents of which are fully incorporated herein by reference.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
5955548 |
Dorwald et al. |
Sep 1999 |
A |
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Country |
0 413 343 |
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WO 9850344 |
Nov 1998 |
WO |
Non-Patent Literature Citations (2)
Entry |
W.-D. Rudorf, Tetrahedron, vol. 36, pp. 1791-1799 (1980). |
Abstract of article by Augustin et al., Synthesis and reactivity of phenylsulfonylcyanoketene-S, S-acetals (1977). |
Provisional Applications (1)
|
Number |
Date |
Country |
|
60/108728 |
Nov 1998 |
US |