PHTHALAZINONE DERIVATIVE

• US 20090270617A1
• Filed: 07/10/2009
• Published: 10/29/2009
• Est. Priority Date: 10/17/2006
• Status: Active Grant

• Current Assignee: Kudos Pharmaceuticals Limited (Astrazeneca PLC)
• Original Assignee: Kudos Pharmaceuticals Limited (Astrazeneca PLC)
• Inventors: Menear, Keith Allan, Laffan, David Dermot Patrick, Jones, Martin Francis, Mulholland, Keith Raymond, Pittam, John David, Cherryman, Janette Helen, Londesbrough, Derek John, Ottridge, Anthony Peter, Ashworth, Ian Woodward, Hallett, Michael Raymond
• Granted Patent: US 8,247,416 B2
• Time in Patent Office: Days
• US Class Current: 544/237
• CPC Class Codes: A61P 25/00 Drugs for disorders of the nervous system
• CPC Class Codes: A61P 31/00 Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
• CPC Class Codes: A61P 31/04 Antibacterial agents
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: A61P 7/04 Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
• 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: C07D 237/32 with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring

Abstract

4-[3-(4-cyclopropanecarbonyl-piperazine-1-carbonyl)-4-fluoro-benzyl]-2H-phthalazin-1-one as crystalline Form A.

Claims

1. 4-[3-(4-cyclopropanecarbonyl-piperazine-1-carbonyl)-4-fluoro-benzyl]-2H-phthalazin-1-one as crystalline Form A.

2. The compound of claim 1 having the following characteristic peaks in a powder X-ray diffraction pattern:

2θ

°

(±

0.1°

) Peak (λ

= 1.5418 Å

) 1 12.0 2 17.8 3 21.1 4 22.3 5 29.2

3. The compound of claim 1 having the following characteristic peaks in a powder X-ray diffraction pattern:

2θ

°

(±

0.1°

) Peak (λ

= 1.5418 Å

) 1 12.0 2 17.8 3 21.1 4 22.3 5 29.2 6 10.5 7 14.0 8 21.7 9 24.3 10 26.1

4. The compound of claim 1, which begins melting at 210.1°

C.±

1°

C. when heated from 25°

C. to 325°

C. at 1020 C. per minute in differential scanning calorimetry.

5. 4-[3-(4-cyclopropanecarbonyl-piperazine-1 -carbonyl)-4-fluoro-benzyl]-2H-phthalazin-1 -one as crystalline Form A which is substantially free of solvent.

6. A method of synthesising 4-[3-(4-cyclopropanecarbonyl-piperazine-1-carbonyl)-4-fluoro -benzyl]-2H-phthalazin-1-one from 2-fluoro-5-(4-oxo-3,4-dihydro-phthalazin-1-ylmethyl)-benzoic acid comprising reacting 2-fluoro-5-(4-oxo-3,4-dihydro-phthalazin-1-ylmethyl)-benzoic acid with 1-(cyclopropylcarbonyl)piperazine or a mineral acid salt thereof in the presence of an amide coupling agent.