CRYSTALLINE 3',5'-CYCLIC DIGUANYLIC ACID

• US 20190315795A1
• Filed: 06/14/2019
• Published: 10/17/2019
• Est. Priority Date: 03/03/2014
• Status: Active Grant

• Current Assignee: Yamasa Corporation
• Original Assignee: Yamasa Corporation
• Inventors: TANAKA, Hisaki, ISHIGE, Kazuya
• Granted Patent: US 10,787,479 B2
• Time in Patent Office: Days
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: A61P 35/00 Antineoplastic agents
• CPC Class Codes: A61P 37/02 Immunomodulators
• CPC Class Codes: C07H 1/00 Processes for the preparation of sugar derivatives
• CPC Class Codes: C07H 19/207 the phosphoric or polyphosphoric acids being esterified by a further hydroxylic compound, e.g. flavine adenine dinucleotide or nicotinamide-adenine dinucleotide
• CPC Class Codes: C07H 19/213 containing cyclic phosphate

Abstract

A crystal of free acid of 3′,5′-cyclic diguanylic acid containing no metal salt with cobalt, magnesium or the like is provided. A method is sought for obtaining said crystal in a large amount and with ease. By a manufacturing method comprising a step of adding acid to an aqueous solution of 3′,5′-cyclic diguanylic acid so as to lower pH to 1 to 3, crystals of 3′,5′-cyclic diguanylic acid can be obtained in a large amount with ease. Said crystals are free acid crystals which do not contain a metal salt with cobalt, magnesium or the like.

Claims

1. A crystal of 3′

,5′

-cyclic diguanylic acid, wherein characteristic peaks are observed around 8.1, 8.3, 10.8, 11.8, 16.9, 19.1, 19.5, 22.4, 25.0, 26.7, 27.0 and 27.7(°

) in diffraction angle (2θ

) in X-ray powder analysis.

2. The crystal of claim 1 having purity of 97% or more as measured by high-performance liquid chromatography.

3. The crystal of claim 1 having purity of 99% or more as measured by high-performance liquid chromatography.

4. The crystal of claim 1, wherein approximately 4 to 6 molecules of water bond or attach to one molecule of 3′

,5′

-cyclic diguanylic acid.

5. The crystal of claim 1, wherein an endothermic peak is observed at 213 to 217°

C. as measured by a thermogravimetric measurement/differential thermal analysis (TG/DTA) apparatus.

6. The crystal of claim 1, wherein characteristic peaks are observed around 3163, 1712, 1637, 1601, 1530, 1470, 1386 and 1339 (cm⁻

1) when an infrared absorption spectrum is measured.

7-9. -9. (canceled)