IP Library Granted Patent US 8,158,821
Granted Patent B2
US 8,158,821 · App. 12/302,378 · Granted Apr 17, 2012

Crystal of 5-aminolevulinic acid phosphate and process for producing the same

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Quick Facts
Patent No.
US 8,158,821
App. No.
12/302,378
Granted
Apr 17, 2012
Kind
B2
Abstract

To provide a novel crystal of 5-aminolevulinic acid phosphate having a high thermal stability, a high melting point, and an excellent moisture absorption resistance as well as a process for producing the same. A crystal of 5-aminolevulinic acid phosphate, which shows characteristic peaks at 7.9°±0.2°, 15.8°±0.2°, 18.9°±0.2°, 20.7°±0.2°, 21.1°±0.2°, 21.4°±0.2°, 22.9°±0.2°, 33.1°±0.2°, and 34.8±0.2° as diffraction angles 2θ in a powder X-ray diffraction, and a process for producing the same.

Claims (11)

1. A crystal of 5-aminolevulinic acid phosphate, which shows characteristic peaks at 7.9°±0.2°, 15.8°±0.2°, 18.9°±0.2°, 20.7°±0.2°, 21.1°±0.2°, 21.4°±0.2°, 22.9°±0.2°, 33.1°±0.2°, and 34.8±0.2° as diffraction angles 2θ in powder X-ray diffraction measured with a wavelength of 1.54 Å (Cu Kα),

wherein the crystal has a melting point of 129 to 131° C.

2. A process for producing the crystal according to claim 1 , wherein a salt of 5-aminolevulinic acid, phosphoric acid, and a basic nitrogen-containing compound are dissolved in a first solvent and then a second solvent having a lower solubility for 5-aminolevulinic acid phosphate as compared with the first solvent is added thereto to precipitate the crystal,

wherein the salt of 5-aminolevulinic acid is hydrochloride, hydrobromide, sulfonate, sulfate, or nitrate, and

the amount of the basic nitrogen-containing compound is 0.1 to 5 molar equivalents to that of the salt of 5-aminolevulinic acid.

3. The process according to claim 2 , wherein the basic nitrogen-containing compound is a pyridine represented by the following formula (1):

wherein R 1 represents a hydrogen atom, a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, or an amino group which may have a substituent,

or an amine represented by the following formula (2):

NH m R 2 3-m   (2)

wherein m represents an integer of 0 to 3 and R 2 represents a hydrogen atom or a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent.

4. The process according to claim 2 , wherein the second solvent having a lower solubility for 5-aminolevulinic acid phosphate as compared with the first solvent is at least one selected from methanol, ethanol, n-propanol, isopropanol, acetone, γ-butyrolactone, 1,4-dioxane, methoxyethanol, tetraethylene glycol dimethyl ether, and triethylene glycol dimethyl ether.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 26, 2016
From: COSMO OIL CO., LTD.
To: COSMO ALA CO., LTD.
Reel/Frame 038723/0661 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 25, 2008
From: TACHIYA, NAOHISA
To: COSMO OIL CO., LTD.
Reel/Frame 021887/0993 →