Crystalline forms and processes for the preparation of phenyl-pyrazoles useful as modulators of the 5-HT2A serotonin receptor

• US 9,783,502 B2
• Filed: 10/23/2015
• Issued: 10/10/2017
• Est. Priority Date: 05/18/2006
• Status: Active Grant

• Current Assignee: Arena Pharmaceuticals Incorporated (Pfizer Inc.)
• Original Assignee: Arena Pharmaceuticals Incorporated (Pfizer Inc.)
• Inventors: Gharbaoui, Tawfik, Sengupta, Dipanjan, Krishnan, Ashwin, Shah, Nainesh, Hart, Ryan M., Macias, Mark, Lally, Edward A.
• Primary Examiner(s): Otton, Alicia L
• Application Number:
  US14/921,651
• Publication Number:
  US 20160272591A1
• Time in Patent Office: 718 Days
• Field of Search: None
• CPC Class Codes: A61P 11/06 Antiasthmatics
• 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 25/20 Hypnotics; Sedatives
• CPC Class Codes: A61P 25/22 Anxiolytics
• CPC Class Codes: A61P 25/30 for treating abuse or dependence
• 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 3/10 for hyperglycaemia, e.g. antidiabetics
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: A61P 7/00 Drugs for disorders of the blood or the extracellular fluid
• CPC Class Codes: A61P 7/02 Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
• CPC Class Codes: A61P 9/00 Drugs for disorders of the cardiovascular system
• CPC Class Codes: A61P 9/10 for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
• CPC Class Codes: A61P 9/12 Antihypertensives
• CPC Class Codes: C07D 231/12 with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Abstract

The present invention relates to processes for preparing phenyl-pyrazoles of Formula (I) and salts and pharmaceutical compositions thereof, useful as modulators of 5-HT_2A serotonin receptor activity.

The present invention also relates to intermediates used in the processes, and their preparation. The present invention also relates to crystalline forms of 5-HT_2A serotonin receptor modulators, compositions thereof and methods of using the same.

Claims

1. A hydrochloride salt of a compound of Formula (I):

2. The hydrochloride salt of claim 1, wherein R¹ is methoxy and X is O.

3. The hydrochloride salt of claim 1, wherein R¹ is fluoro and X is NC(O)CH₃.

7. A composition comprising a salt of claim 1.

8. The composition of claim 7, further comprising a pharmaceutically acceptable carrier.

4. An oxalate salt of a compound of Formula (I):

5. The oxalate salt of claim 4, wherein R¹ is methoxy and X is O.

6. The oxalate salt of claim 4, wherein R¹ is fluoro and X is NC(O)CH₃.

9. A composition comprising a salt of claim 4.

10. The composition of claim 9, further comprising a pharmaceutically acceptable carrier.