Heterocyclic compounds suitable for treating disorders that respond to modulation of the serotonin 5HT6 receptor

• US 8,497,273 B2
• Filed: 04/18/2007
• Issued: 07/30/2013
• Est. Priority Date: 04/19/2006
• Status: Active Grant

• Current Assignee: Abbvie Deutschland GmbH & Company KG (Abbvie Incorporated)
• Original Assignee: Abbott GmbH & Company KG (Abbott Laboratories Incorporated)
• Inventors: Grandel, Roland, Braje, Wilfried Martin, Haupt, Andreas, Turner, Sean Colm, Lange, Udo, Drescher, Karla, Unger, Liliane
• Primary Examiner(s): BERNHARDT, EMILY A
• Application Number:
  US12/297,328
• Publication Number:
  US 20100048582A1
• Time in Patent Office: 2,295 Days
• Field of Search: None
• US Class Current: 514/253.01
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 25/18 Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
• CPC Class Codes: A61P 25/28 for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07D 401/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 401/14 containing three or more hetero rings
• CPC Class Codes: C07D 413/14 containing three or more hetero rings
• CPC Class Codes: C07D 417/14 containing three or more hetero rings

Abstract

The invention relates to compounds of the formula (I)

wherein the variables have meanings given in the claims and the description.

The invention also relates to the use of a compound of the formula I or a pharmaceutically acceptable salt thereof for preparing a medicament for the treatment of a medical disorder susceptible to the treatment with a 5HT₆ receptor ligand.

Claims

1. A compound of the formula (I)

2. The compound as claimed in claim 1, wherein

R¹ is H, C₁-C₆-alkyl, C₁-C₆-alkyl substituted by C₃-C₆-cycloalkyl, C₁-C₆-hydroxyalkyl, fluorinated C₁-C₆-alkyl, C₃-C₆-cycloalkyl, fluorinated C₃-C₆-cycloalkyl, C₃-C₆-alkenyl, fluorinated C₃-C₆-alkenyl, formyl, acetyl or propionyl.

3. The compound of claim 1, wherein R¹ is hydrogen, methyl, ethyl, n-propyl, 2-fluoroethyl, 3-fluoropropyl, 3-hydroxypropyl, cyclo-propylmethyl or allyl.

4. The compound as claimed in claim 3, wherein R¹ is n-propyl or allyl.

5. The compound of claim 1, wherein R², R^2′

, R³, R⁴ and R^4′

are H.

6. The compound of claim 1, wherein A is 2,4-pyridylene or 3,5-pyridylene, which is optionally substituted by one or more substituents selected from halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, fluorinated C₁-C₄-alkyl and fluorinated C₁-C₄-alkoxy.

7. The compound as claimed in claim 6, wherein A is 3,5-pyridylene, which is optionally substituted by one or more substituents selected from halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, fluorinated C₁-C₄-alkyl and fluorinated C₁-C₄-alkoxy.

8. The compound of claim 1, wherein R^a is selected from fluorinated C₁-C₄-alkoxy.

9. A compound according to claim 1 that is 3-difluoromethoxy-N-[2-(4-methyl-piperazin-1-yl)-pyridin-4-yl]-benzene sulfonamide.

10. A method for treating depression, obesity, and cognitive dysfunctions associated with Alzheimer'"'"'s disease and schizophrenia, said method comprising administering an effective amount of at least one compound of claim 1 to a subject in need thereof.

11. A pharmaceutical composition comprising at least one compound according to claim 1 and at least one physiologically acceptable carrier and/or auxiliary substance.