2-pyridone compounds

• US 8,436,024 B2
• Filed: 10/01/2010
• Issued: 05/07/2013
• Est. Priority Date: 10/02/2009
• Status: Expired due to Fees

• Current Assignee: Astrazeneca AB (Astrazeneca PLC)
• Original Assignee: Astrazeneca AB (Astrazeneca PLC)
• Inventors: Murugan, Andiappan, Bergstrom, Lena Kristina, Kristoffersson, Anna, Ashton, Mark David, Meigh, Jon, Sj, Peter Olof, Lindsj, Martin
• Primary Examiner(s): MCDOWELL, BRIAN E
• Application Number:
  US12/895,995
• Publication Number:
  US 20110082155A1
• Time in Patent Office: 949 Days
• Field of Search: 546/275.4
• US Class Current: 514/341
• CPC Class Codes: A61P 1/00 Drugs for disorders of the alimentary tract or the digestive system
• CPC Class Codes: A61P 11/06 Antiasthmatics
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07D 213/64 attached in position 2 or 6
• 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 403/04 directly linked by a ring-member-to-ring-member bond

Abstract

The invention provides compounds of formula

wherein R¹, R³, R⁴, R⁵, R⁶, R⁷, L, X and Y are as defined in the specification; together with processes and intermediates for their preparation, pharmaceutical compositions containing them and their use in therapy. The compounds are inhibitors of human neutrophil elastase.

Claims

1. The compound 3-(5-(1-(4-cyanophenyl)-1H-pyrazol-5-yl)-6-methyl-2-oxo-1-(3-(trifluoromethyl)phenyl)-1,2-dihydropyridine-3-carboxamido)-N,N,N-trimethylpropan-1-aminium Y;

wherein Y represents a pharmaceutically acceptable anion.

2. The compound as defined in claim 1 which is 3-(5-(1-(4-cyanophenyl)-1H-pyrazol-5-yl)-6-methyl-2-oxo-1-(3-(trifluoromethyl)phenyl)-1,2-dihydropyridine-3-carboxamido)-N,N,N-trimethylpropan-1-aminium benzenesulfonate.

3. A pharmaceutical composition comprising a compound as claimed in claim 1 in association with a pharmaceutically acceptable adjuvant, diluent or carrier.

4. The compound as defined in claim 2 which is 3-(5-(1-(4-cyanophenyl)-1H-pyrazol-5-yl)-6-methyl-2-oxo-1-(3-(trifluoromethyl)phenyl)-1,2-dihydropyridine-3-carboxamido)-N,N,N-trimethylpropan-1-aminium benzenesulfonate Form A, characterized in that said Form A has an X-ray powder diffraction pattern with specific peaks at 4.3, 11.5 and 23.1°

2θ

when measured using CuKα

1 radiation.

5. The compound as defined in claim 2 which is 3-(5-(1-(4-cyanophenyl)-1H-pyrazol-5-yl)-6-methyl-2-oxo-1-(3-(trifluoromethyl)phenyl)-1,2-dihydropyridine-3-carboxamido)-N,N,N-trimethylpropan-1-aminium benzenesulfonate Form B, characterized in that said Form B has an X-ray powder diffraction pattern with specific peaks at 5.8, 7.5 and 17.2°

2θ

when measured using CuKα

1 radiation.