Derivatives of 3,3-diphenylpropylamines

• US 8,338,478 B2
• Filed: 06/15/2011
• Issued: 12/25/2012
• Est. Priority Date: 05/12/1998
• Status: Expired due to Fees

• Current Assignee: UCB Pharma GmbH (UCB SA)
• Original Assignee: UCB Pharma GmbH (UCB SA)
• Inventors: Meese, Claus, Sparf, Bengt
• Primary Examiner(s): JARRELL, NOBLE E
• Application Number:
  US13/161,049
• Publication Number:
  US 20110294882A1
• Time in Patent Office: 559 Days
• Field of Search: None
• US Class Current: 514/506
• CPC Class Codes: A61P 1/00 Drugs for disorders of the alimentary tract or the digestive system
• CPC Class Codes: A61P 1/04 for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
• CPC Class Codes: A61P 13/00 Drugs for disorders of the urinary system
• CPC Class Codes: A61P 13/02 of urine or of the urinary tract, e.g. urine acidifiers
• CPC Class Codes: A61P 13/10 of the bladder
• CPC Class Codes: A61P 21/00 Drugs for disorders of the muscular or neuromuscular system
• CPC Class Codes: A61P 25/02 for peripheral neuropathies
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07C 217/48 the carbon skeleton being unsaturated and containing rings
• CPC Class Codes: C07C 217/62 linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
• CPC Class Codes: C07C 219/28 having amino groups bound to acyclic carbon atoms of the carbon skeleton
• CPC Class Codes: C07C 229/34 the carbon skeleton containing six-membered aromatic rings
• CPC Class Codes: C07C 271/44 to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
• CPC Class Codes: C07C 271/52 to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
• CPC Class Codes: C07C 307/02 Monoamides of sulfuric acids or esters thereof, e.g. sulfamic acids

Abstract

The invention concerns novel derivatives of 3,3-diphenyl-propylamines, methods for their preparation, pharmaceutical compositions containing the novel compounds, and the use of the compounds for preparing drugs. More particularly, the invention relates to novel prodrugs of antimuscarinic agents with superior pharmacokinetic properties compared to existing drugs such as oxybutynin and tolterodine, methods for their preparation, pharmaceutical compositions containing them, a method of using said compounds and compositions for the treatment of urinary incontinence, gastrointestinal hyperactivity (irritable bowel syndrome) and other smooth muscle contractile conditions.

Claims

1. 3,3-Diphenylpropylamines of the formula

2. The 3,3-Diphenylpropylamines of claim 1 where R⁸ and R⁹ are each independently C₁-C₆ alkyl.

3. The 3,3-Diphenylpropylamines of claim 1 where X is selected from the group consisting of:

4. The 3,3-Diphenylpropylamines of claim 1 where R¹ is hydrogen and R² is C₁-C₆ alkylcarbonyl.

5. The 3,3-Diphenylpropylamines of claim 1 where R¹ is C₁-C₆ alkylcarbonyl and R² is hydrogen.

12. A pharmaceutical composition comprising an effective amount of a 3,3-Diphenylpropylamine according to any one of claims 1-5 and a pharmaceutically acceptable carrier.

6. A method of treating urinary incontinence in a patient in need thereof, the method comprising administering to the patient an effective amount of a 3,3-Diphenylpropylamine of the formula

7. The method of claim 6 where R⁸ and R⁹ are each independently C₁-C₆ alkyl.

8. The method of claim 6 where X is selected from the group consisting of:

9. The method of claim 6 where R¹ is hydrogen and R² is C₁-C₆ alkylcarbonyl.

10. The method of claim 6 where R¹ is C₁-C₆ alkylcarbonyl and R² is hydrogen.

11. The method of claim 6, where the 3,3-Diphenylpropylamine is administered to the patient in the form of a pharmaceutical composition comprising a pharmaceutically acceptable carrier.