N-acyl-cycloalkylamine derivatives as melatonergics

• US 5,596,019 A
• Filed: 06/07/1995
• Issued: 01/21/1997
• Est. Priority Date: 06/07/1995
• Status: Expired due to Term

• Current Assignee: Bristol-Myers Squibb Company
• Original Assignee: Bristol-Myers Squibb Company
• Inventors: Parker, Michael F., Mattson, Ronald J., Johnson, Graham, Keavy, Daniel J.
• Primary Examiner(s): Kumar, Shailendra
• Application Number:
  US08/487,306
• Time in Patent Office: 594 Days
• Field of Search: 514/625, 514/627, 514/629, 564/192, 564/204, 564/207, 564/218, 564/217
• US Class Current: 514/629
• CPC Class Codes: C07C 233/13 with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
• CPC Class Codes: C07C 233/18 having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
• CPC Class Codes: C07C 233/60 having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
• CPC Class Codes: C07C 235/08 having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
• CPC Class Codes: C07C 255/60 at least one of the singly-bound nitrogen atoms being acylated
• CPC Class Codes: C07C 2601/02 with a three-membered ring
• CPC Class Codes: C07C 2601/04 with a four-membered ring
• CPC Class Codes: C07C 2601/08 the ring being saturated
• CPC Class Codes: C07C 2601/14 The ring being saturated
• CPC Class Codes: C07C 275/24 containing six-membered aromatic rings
• CPC Class Codes: C07C 275/26 having nitrogen atoms of urea groups bound to carbon atoms of rings other than six-membered aromatic rings
• CPC Class Codes: C07C 323/60 with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
• CPC Class Codes: C07D 213/30 Oxygen atoms

Abstract

Certain N-acyl-cycloalkylamine derivatives are useful as melatonergic agents.

Claims

1. A melatonergic compound of Formula I ##STR9## wherein:

X is halogen or OR₅ wherein R₅ is C_1-20 alkyl, C_3-20 alkenyl, C_3-20 alkynyl, C_9-20 aralkyl, C_9-20 aralkenyl or C_9-20 aralkynyl;

X'"'"' is hydrogen or halogen;

n is an integer from 0 to 3;

R'"'"' is hydrogen, C_1-4 alkyl or benzyl; and

R" is C_1-6 alkyl, C_2-6 alkenyl, C_3-6 cycloalkyl, C_2-4 alkoxyalkyl or C_2-4 alkylthioalkyl.

2. The compound of claim 1 wherein R'"'"' is hydrogen and R" contains no nitrogen, oxygen or sulfur atoms.

3. The compound of claim 2 wherein R" is C_1-4 alkyl.

4. The compound of claim 3 wherein X" is hydrogen.

5. The compound of claim 4 wherein X is OR₅ and R₅ is methyl.

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

(cis)-N-[3-(3-methoxyphenyl)cyclohexyl]acetamide;

(cis)-N-[3-(3-methoxyphenyl)cyclohexyl]-2-methyl-propanamide;

(cis)-N-[3-(3-methoxyphenyl)cyclohexyl]butanamide; and

N-[3-(3-methoxyphenyl)cyclopentyl]butanamide.

7. The compound of claim 1, (cis)-N-[3-(3-methoxyphenyl)cyclohexyl]acetamide.

8. The compound of claim 1, (cis)-N-[3-(3-methoxyphenyl)cyclohexyl]-2-methyl-propanamide.

9. The compound of claim 1, (cis)-N-[3-(3-methoxyphenyl)cyclohexyl]butanamide.

10. The compound of claim 1, N-[3-(3-methoxyphenyl)cyclopentyl]butanamide.

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

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