IP Library › Granted Patent US 10,385,081
Granted Patent B2
US 10,385,081 · App. 15/872,321 · Granted Aug 20, 2019

Crystal of cyclic phosphonic acid sodium salt and method for manufacturing same

Inventors: Hiroaki Yuasa (Tokushima, JP); Hiroki Okazaki (Tokushima, JP)
Assignee: OTSUKA CHEMICAL CO., LTD.
C07F9/657163A61P19/00A61P29/00A61P35/00C07F9/65742C07F9/657181A61K31/665C07B2200/13
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Quick Facts
Patent No.
US 10,385,081
App. No.
15/872,321
Granted
Aug 20, 2019
Kind
B2
Abstract

An object of the present invention is to provide a crystal of a cyclic phosphonic acid sodium salt (2ccPA) with high purity and excellent storage stability and a method for producing the crystal. The present invention provides a crystal of a cyclic phosphonic acid sodium salt (2ccPA) represented by formula (1):

Claims (219)

1. A method for producing a crystal of phosphonic acid sodium salt (2ccPA) represented by formula (1):

the method comprising

step (H) of reacting a cyclic phosphonic acid ester represented by formula (9):

wherein R 1 represents alkyl, arylalkyl, or aryl with a sodium halide in an organic solvent to obtain 2ccPA, and

step (I) of concentrating a solution containing the 2ccPA obtained in step (H) under reduced pressure, or cooling the solution containing the 2ccPA obtained in step (H) to precipitate the crystal.

2. The method according to claim 1 , wherein the crystal has an X-ray powder diffraction spectrum comprising a expressed in degrees 2θ at 15° to 17°.

3. The method according to claim 1 , wherein the crystal has an X-ray powder diffraction spectrum comprising a peak expressed in degrees 2θ at 9° to 10°.

4. The method according to claim 1 , wherein the crystal has X-ray powder diffraction spectrum comprising peaks expressed in degrees 2θ at 3° to 5°.

5. The method according to claim 1 , wherein the crystal has an X-ray powder diffraction spectrum obtained with monochromated copper radiation of λ=1.54059 Å comprising a peak at lattice spacing (d) of 15.7684 to 16.1724.

6. The method according to claim 1 , wherein the crystal has an X-ray powder diffraction spectrum obtained with monochromated copper radiation of λ=1.54059 Å comprising peaks at the following lattice spacings (d):

15.7684 to 16.1724

9.5425 to 9.6675

4.8282 to 4.9403

4.4802 to 4.8335

4.1641 to 4.2070

3.7263 to 3.8140.

7. The method according to claim 1 , wherein the crystal has an X-ray powder diffraction spectrum obtained with monochromated copper radiation of λ=1.54059 Å with lattice spacing (d) satisfying any one of the requirements (a) to (y):

(a) Lattice spacing (d)

16.1724

9.6675

4.9186

4.8335

4.5164

4.1835

3.7921

(b) Lattice spacing (d)

15.9390

9.5838

4.9294

4.7972

4.4982

4.1913

3.7953

(c) Lattice spacing (d)

15.8817

9.5631

4.9186

4.7869

4.4937

4.1835

3.7794

(d) Lattice spacing (d)

15.8817

9.5631

4.9294

4.7920

4.4982

4.1874

3.8017

(e) Lattice spacing (d)

15.8817

9.5631

4.9186

4.7869

4.4937

4.1874

3.7921

(f) Lattice spacing (d)

15.8248

9.5425

4.9078

4.7920

4.4937

4.1796

3.7762

(g) Lattice spacing (d)

16.0548

9.6046

4.9294

4.8075

4.5073

4.2070

3.7857

(h) Lattice spacing (d)

15.9967

9.6046

4.9349

4.8023

4.5073

4.1913

3.8017

(i) Lattice spacing (d)

15.8817

9.5631

4.9294

4.7920

4.4982

4.1913

3.8017

(j) Lattice spacing (d)

15.9967

9.6046

4.9024

4.8075

4.5027

4.1835

3.7636

(k) Lattice spacing (d)

16.0548

9.6255

4.9403

4.8023

4.5073

4.1992

3.7985

(l) Lattice spacing (d)

16.0548

9.6255

4.9349

4.8075

4.5073

4.1952

3.7857

(m) Lattice spacing (d)

15.9390

9.5631

4.9186

4.7972

4.4982

4.1874

3.7953

(n) Lattice spacing (d)

15.939

9.5838

4.9132

4.7920

4.4937

4.1874

3.7762

(o) Lattice spacing (d)

15.9967

9.6046

4.9024

4.8075

4.4982

4.1719

3.7293

(p) Lattice spacing (d)

16.0548

9.6255

4.9349

4.8075

4.5073

4.1992

3.8145

(q) Lattice spacing (d)

15.7684

9.5425

4.8282

4.4802

4.1757

3.7263

(r) Lattice spacing (d)

15.9390

9.5838

4.9132

4.8023

4.4937

4.1641

3.7730

(s) Lattice spacing (d)

15.9390

9.5838

4.9186

4.7920

4.4937

4.1835

3.7921

(t) Lattice spacing (d)

15.9390

9.5838

4.9240

4.7920

4.4982

4.1874

3.7921

(u) Lattice spacing (d)

16.0548

9.6255

4.9186

4.7920

4.4982

4.1835

3.7985

(v) Lattice spacing (d)

16.0548

9.6255

4.9294

4.7972

4.5073

4.1874

3.7985

(w) Lattice spacing (d)

16.0548

9.6255

4.9186

4.8075

4.4982

4.1835

3.8049

(x) Lattice spacing (d)

15.9967

9.6046

4.9240

4.8023

4.4982

4.1874

3.7985

(y) Lattice spacing (d)

15.9390

9.5838

4.9186

4.7869

4.4937

4.1796

3.7985.

8. The method according to claim 1 , the method further comprising

step (J) of dissolving the crystal obtained in step (I) in water and/or an organic solvent to obtain a solution, and

step (K) of adding a poor solvent to the solution obtained in step (J) to perform recrystallization.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 23, 2020
From: OTSUKA CHEMICAL CO., LTD
To: OTSUKA CHEMICAL CO., LTD.; SANSHO CO., LTD.
Reel/Frame 053012/0915 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 17, 2018
From: YUASA, HIROAKI; OKAZAKI, HIROKI
To: OTSUKA CHEMICAL CO., LTD.
Reel/Frame 044642/0227 →
Priority Claims (1)
JP 2014-164423 · Aug 12, 2014 · national
Continuity (2)
Division 15501525
Related Publication 20180208614A1 · Jul 26, 2018