Chemical compound useful as intermediate for preparing a catechol-O-methyltransferase inhibitor

• US 9,630,955 B2
• Filed: 07/31/2015
• Issued: 04/25/2017
• Est. Priority Date: 12/13/2011
• Status: Active Grant

• Current Assignee: BIAL Portela & Ca, SA
• Original Assignee: BIAL Portela & Ca, SA
• Inventors: Russo, Domenico, Kiss, Laszlo Erno, Wahnon, Jorge Bruno Reis, Learmonth, David Alexander, Eszenyi, Tibor, Zimmermann, Axel, Schlummer, Bjoern, Kreis, Michael, Reiter, Klaus
• Primary Examiner(s): REESE, HEIDI L
• Application Number:
  US14/814,603
• Publication Number:
  US 20160009700A1
• Time in Patent Office: 634 Days
• Field of Search: None
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 25/16 Anti-Parkinson drugs
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07D 413/04 directly linked by a ring-member-to-ring-member bond

Abstract

There is disclosed a methylated intermediate which may be demethylated to provide an inhibitor of catechol-O-methyltransferase useful in the treatment of Parkinson'"'"'s disease. Also disclosed are methods of making and using said intermediate.

Claims

1. A crystalline compound of formula (II)

2. A compound according to claim 1, wherein the microparticulate form is prepared by ball milling or by micronisation through spiral jet mills.

3. A compound according to claim 1, wherein the compound in the microparticulate form has a particle size specification with D10 equivalent circle diameter not less than 5 μ

m.

4. A compound according to claim 1, wherein the compound in the microparticulate form has a particle size specification with D50 equivalent circle diameter being 15-30 μ

m.

5. A compound according to claim 3, wherein the compound in the microparticulate form has a particle size specification with D50 equivalent circle diameter being 15-30 μ

m.

10. A compound according to claim 1, wherein the compound in the microparticulate form has a particle size specification with D10 equivalent circle diameter not less than 6μ

m.

11. A compound according to claim 1, wherein the compound in the microparticulate form has a particle size specification with D50 equivalent circle diameter not less than 20-25 μ

m.

12. A compound according to claim 3, wherein the compound in the microparticulate form has a particle size specification with D50 equivalent circle diameter not less than 20-25 μ

m.

6. A pharmaceutical composition in unit dosage form for oral administration comprises a compound of the formula (II)

7. A pharmaceutical composition according to claim 6, wherein the unit dosage form is a tablet or a capsule.

8. A method of treating Parkinson'"'"'s disease in a patient suffering therefrom comprises administering to the patient an effective amount of a pharmaceutical composition according to claim 6.

9. A method according to claim 8, wherein the unit dosage form is a tablet or a capsule.