# US 2019/0315795 A1 · Crystalline 3',5'-cyclic diguanylic acid

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- Number: US 2019/0315795 A1
- Document ID: US20190315795A1
- Status: Published application
- Kind: A1
- Application number: 16/441,484
- Filed: 2019-06-14
- Published: 2019-10-17
- Earliest claimed: 2014-03-03
- Assignees: Yamasa Corporation
- Applicants: Yamasa Corporation
- Inventors: Hisaki TANAKA; Kazuya ISHIGE
- Web page: https://patentgrep.com/patent/US20190315795A1

## CPC

- C07H 19/207: the phosphoric or polyphosphoric acids being esterified by a further hydroxylic compound, e.g. flavine adenine dinucleotide or nicotinamide-adenine dinucleotide
- A61P 31/12: Antivirals
- A61P 35/00: Antineoplastic agents
- A61P 37/02: Immunomodulators
- C07H 1/00: Processes for the preparation of sugar derivatives
- C07H 19/213: containing cyclic phosphate
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## 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

### Claim 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.

### Claim 2 (depends on 1)

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

### Claim 3 (depends on 1)

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

### Claim 4 (depends on 1)

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.

### Claim 5 (depends on 1)

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.

### Claim 6 (depends on 1)

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.

### Claim at position 7

7-9. (canceled)