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Generated: July 23, 2017

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Claims for Patent: 5,856,529

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Claims for Patent: 5,856,529

Title: Benzofuran and dihydrobenzofuran melatonergic agents
Abstract:Novel derivatives of benzofuran and dihydrobenzofuran 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)
Application Number:08/987,478
Patent 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;

Y is CR.sup.3, CR.sup.3 R.sup.4 or (CH.sub.2).sub.n, with n=1;

Z is oxygen and X is CH.sub.2 or CH; or X is oxygen and Z is CH.sub.2 or CH;

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

m is 1 or 2;

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;

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

R.sup.3 and R.sup.4 each are independently 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 CH.sub.2 and Z is oxygen.

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

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

(-)-(trans)-N-[[2-(2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl]methyl]acetami de;

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

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

(-)-(trans)-N-[[2-(2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl]methyl]cyclopr opanecarboxamide;

(-)-(trans)-N-[[2-(2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl]methyl]trifluo roacetamide;

(trans)-N-[[2-(2,3-dihydro-2,2-dimethyl-benzofuran-4-yl)cycloprop-1-yl]meth yl]propanamide;

(trans)-N-[[2-(2,3-dihydro-2,2-dimethyl-benzofuran-4-yl)cycloprop-1-yl]meth yl]butanamide;

(+)-(trans)-N-[[2-(2-methyl-2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl]methy l]acetamide;

(+)-(trans)-N-[[2-(2-methyl-2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl]methy l]propanamide;

(+)-(trans)-N-[[2-(2-methyl-2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl]methy l]butanamide;

(+)-(trans)-N-[[2-(2-methyl-2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl]methy l]cyclopropane carboxamide;

(+)-(trans)-N-[[2-(2-methyl-2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl]methy l]-2-methylpropanamide;

(+)-(trans)-N-[[2-(2-methyl-2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl]methy l]chloroacetamide;

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

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

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

(-)-(trans)-N-[[2-(2-methyl-2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl]methy l]methoxyacetamide;

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

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

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

(-)-(trans)-N-[[2-(2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl]methyl]propana mide;

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

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

(trans)-N-[[2-(2,3-dihydro-5,7-diiodobenzofuran-4-yl)cyclopropyl]methyl]pro panamide;

(trans)-N-[[2-(2,3-dihydro-5-iodobenzofuran-4-yl)cyclopropyl]methyl]propana mide.

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

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

(-)-(trans)-N-[[2-(2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl]methyl]acetami de;

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

(-)-(trans)-N-[[2-(2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl]methyl]cyclopr opanecarboxamide

(+)-(trans)-N-[[2-(2-methyl-2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl]methy l]acetamide;

(+)-(trans)-N-[[2-(2-methyl-2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl]methy l]propanamide;

(+)-(trans)-N-[[2-(2-methyl-2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl]methy l]butanamide;

(+)-(trans)-N-[[2-(2-methyl-2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl]methy l]cyclopropane carboxamide;

(+)-(trans)-N-[[2-(2-methyl-2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl]methy l]chloroacetamide;

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

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

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

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

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

(-)-(trans)-N-[[2-(2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl]methyl]propana mide;

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

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

(trans)-N-[[2-(2,3-dihydro-5,7-diiodobenzofuran-4-yl)cyclopropyl]methyl]pro panamide; and

(trans)-N-[[2-(2,3-dihydro-5-iodobenzofuran-4-yl)cyclopropyl]methyl]propana mide.

7. The compound of claim 6, which is (trans)-N-[[2-(2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl]methyl]propanamid e.

8. The compound of claim 6, which is (-)-(trans)-N-[[2-(2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl]methyl]propan amide.

9. The compound of claim 3 wherein X is CH, Y is CR.sup.3 and Z is oxygen.

10. The compound of claim 9 selected from the group consisting of:

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

(-)-(trans)-N-[[2-(benzofuran-4-yl)cycloprop-1-yl]methyl]propanamide;

(trans)-N-[[2-(2-methyl-benzofuran-4-yl)cycloprop-1-yl]methyl]acetamide;

(trans)-N-[[2-(2-methyl-benzofuran-4-yl)cycloprop-1-yl]methyl]-propanamide;

(trans)-N-[[2-(2-methyl-benzofuran-4-yl)cycloprop-1-yl]methyl]-butanamide;

(trans)-N-[[2-(benzofuran-4-yl)cycloprop-1-yl]methyl]acetamide;

(trans)-N-[[2-(benzofuran-4-yl)cycloprop-1-yl]methyl]propanamide;

(trans)-N-[[2-(benzofuran-4-yl)cycloprop-1-yl]methyl]butanamide;

(trans)-N-[[2-(benzofuran-4-yl)cycloprop-1-yl]methyl]-2-methylpropanamide; and

(trans)-N-[[2-(benzofuran-4-yl)cycloprop-1-yl]methyl]cyclopropane carboxamide.

11. The compound of claim 10 selected from the group consisting of:

(trans)-N-[[2-(2-methyl-benzofuran-4-yl)cycloprop-1-yl]methyl]acetamide;

(trans)-N-[[2-(2-methyl-benzofuran-4-yl)cycloprop-1-yl]methyl]-propanamide;

(trans)-N-[[2-(2-methyl-benzofuran-4-yl)cycloprop-1-yl]methyl]-butanamide; and

(trans)-N-[[2-(benzofuran-4-yl)cycloprop-1-yl]methyl]propanamide.

12. 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.

13. 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.

14. 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.

15. 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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