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Details for Patent: 5,981,571

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Details for Patent: 5,981,571

Title: Benzodioxa alkylene ethers as melatonergic agents
Abstract:Novel derivatives of benzodioxa alkylene ethers are provided which are useful as melatonergic agents.
Inventor(s): Catt; John D. (Southington, CT), Johnson; Graham (Madison, CT), Keavy; Daniel J. (Killingworth, CT), Mattson; Ronald J. (Meriden, CT), Parker; Michael F. (Middletown, CT), Takaki; Katherine S. (Middletown, CT), Yevich; Joseph P. (Southington, CT)
Assignee: Bristol-Myers Squibb Company (Princeton, NJ)
Filing Date:Oct 09, 1998
Application Number:09/169,784
Claims:1. A compound of Formula I or a pharmaceutically acceptable solvate thereof having the Formula: ##STR28## wherein Q.sup.1 and Q.sup.2 each are independently hydrogen or halogen;

X is oxygen;

Y is (CH.sub.2).sub.n, with n=1-4;

Z is oxygen;

R is hydrogen, halogen or C.sub.1-4 alkyl in both cases;

m is 1 or2;

R.sup.1 is C.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, C.sub.1-3 haloalkyl, C.sub.1-6 alkylamino, C.sub.2-6 alkenyl, C.sub.1-4 alkoxy(C.sub.1-4)alkyl, C.sub.1-4 alkylthio(C.sub.1-4)alkyl or C.sub.1-4 trifluoromethylalkyl; and

R.sup.2 is hydrogen or C.sub.1-4 alkyl.

2. The compound of claim 1 wherein Q.sup.1 and Q.sup.2 are independently hydrogen or iodo and m is 1.

3. The compound of claim 2 wherein R.sup.1 is C.sub.1-6 alkyl, C.sub.3-4 cycloalkyl, C.sub.1-3 haloalkyl, C.sub.2-3 alkenyl, C.sub.1-2 alkoxy(C.sub.1-2)alkyl or C.sub.1-2 trifluoromethylalkyl and R.sup.2 is hydrogen.

4. The compound of claim 3 wherein X is oxygen, Y is (CH.sub.2)n in which n is 1or 2 and Z is oxygen.

5. The compound of claim 4, selected from the group consisting of:

(trans)-N-[[2-(1,3-benzodioxol-4-yl)cycloprop-1-yl]methyl]acetamide;

(-)-(trans)-N-[[2-(1,3-benzodioxol-4-yl)cycloprop-1-yl]methyl]acetamide;

(trans)-N-[[2-(1,3-benzodioxol-4-yl)cycloprop-1-yl]methyl]propanamide;

(-)-(trans)-N-[[2-(1,3-benzodioxol-4-yl)cycloprop-1-yl]methyl] propanamide;

(trans)-N-[[2-(1,3-benzodioxol-4-yl)cycloprop-1-yl]methyl]butanamide;

(-)-(trans)-N-[[2-(1,3-benzodioxol-4-yl)cycloprop-1-yl]methyl] butanamide;

(trans)-N-[[2-(1,3-benzodioxol-4-yl)cycloprop-1-yl]methyl]cyclopropane carboxamide;

(-)-(trans)-N-[[2-(1,3-benzodioxol-4-yl)cycloprop-1-yl]methyl] cyclopropane carboxamide;

(trans)-N-[[2-(1,3-benzodioxol-4-yl)cycloprop-1-yl]methyl]-2-methylpropanam ide;

(-)-(trans)-N-[2-(1,3-benzodioxol-4-yl)cycloprop-1-yl]methyl]-2-methylpropa namide;

(-)-(trans)-N-[[2-(2,3-dihydro-1,4-benzodioxin-5-yl)cycloprop-1-yl]methyl]p ropanamide;

(-)-(trans)-N-[[2-(2,3-dihydro-1,4-benzodioxin-5-yl)cycloprop-1-yl]methyl]a cetamide;

(-)-(trans)-N-[[2-(2,3-dihydro-1,4-benzodioxin-5-yl)cycloprop-1-yl]methyl]c yclopropanecarboxamide;

(-)-(trans)-N-[[2-(2,3-dihydro-1,4-benzodioxin-5-yl)cycloprop-1-yl]methyl]b utanamide;

(+)-(trans)-N-[[2-(2,3-dihydro-1,4-benzodioxin-5-yl)cycloprop-1-yl]methyl]p ropenamide;

(-)-(trans)-N-[[2-(2,3-dihydro-1,4-benzodioxin-5-yl)cycloprop-1-yl]methyl]t rifluoroacetamide;

(-)-(trans)-N-[[2-(2,3-dihydro-1,4-benzodioxin-5-yl) cycloprop-1-yl]methyl]-3,3,3-trifluoropropanamide;

(+)-(trans)-N-[[2-(2,3-dihydro-1,4-benzodioxin-5-yl)cycloprop-1-yl]methyl]p ropanamide;

(trans)-N-[[2-(2,3-dihydro-1,4-benzodioxin-5-yl)cycloprop-1-yl]-methyl]acet amide;

(trans)-N-[[2-(2,3-dihydro-1,4-benzodioxin-5-yl)cycloprop-1-yl]-methyl]prop anamide;

(trans)-N-[[2-(2,3-dihydro-1,4-benzodioxin-5-yl)cycloprop-1-yl]-methyl]buta namide;

(trans)-N-[[2-(2,3-dihydro-1,4-benzodioxin-5-yl)cycloprop-1-yl]methyl]-2-me thylpropanamide; and

(trans)-N-[[2-(2,3-dihydro-1,4-benzodioxin-5-yl)cycloprop-1-yl]-methyl]cycl opropane carboxamide.

6. The compound of claim 5, selected from the group consisting of:

(trans)-N-[[2-(1,3-benzodioxol-4-yl)cycloprop-1-yl]methyl]acetamide;

(-)-(trans)-N-[[2-(1,3-benzodioxol-4-yl)cycloprop-1-yl]methyl]acetamide;

(trans)-N-[[2-(1,3-benzodioxol-4-yl)cycloprop-1-yl]methyl]propanamide;

and (-)-(trans)-N-[[2-(1,3-benzodioxol-4-yl)cycloprop-1-yl]methyl] propanamide.

7. The compound of claim 5, selected from the group consisting of:

(-)-(trans)-N-[[2-(2,3-dihydro-1,4-benzodioxin-5-yl)cycloprop-1-yl]methyl]p ropanamide;

(-)-(trans)-N-[[2-(2,3-dihydro-1,4-benzodioxin-5-yl)cycloprop-1-yl]methyl]a cetamide;

(-)-(trans)-N-[[2-(2,3-dihydro-1,4-benzodioxin-5-yl)cycloprop-1-yl]methyl]c yclopropanecarboxamide; and

(-)-(trans)-N-[[2-(2,3-dihydro-1,4-benzodioxin-5-yl)cycloprop-1-yl]methyl]b utanamide.

8. A method of treating sleep disorders in a patient in need of such treatment comprising administering to said patient a therapeutic amount of a compound of claim 1.

9. A composition useful for treating sleep disorders comprising a therapeutic amount of a compound of claim 1 and a suitable amount of a pharmaceutically acceptable carrier.

10. A method of treating circadian rhythm-related disorders in a patient in need of such treatment comprising administering to said patient a therapeutic amount of a compound of claim 1.

11. A composition useful for treating circadian rhythm-related disorders comprising a therapeutic amount of a compound of claim 1 and a suitable amount of a pharmaceutically acceptable carrier.
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