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(12) United States Patent (10) Patent No.: US 7,357,835 B2 Mccausland Et Al

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(12) United States Patent (10) Patent No.: US 7,357,835 B2 Mccausland Et Al USOO7357835B2 (12) United States Patent (10) Patent No.: US 7,357,835 B2 McCausland et al. (45) Date of Patent: Apr. 15, 2008 (54) PRODUCTION OF CRYSTALLINE (56) References Cited MATERALS BY USING HIGH INTENSITY U.S. PATENT DOCUMENTS ULTRASOUND 1,347,350 A * 7, 1920 Moore ......................... 117/68 (75) Inventors: Linda Jane McCausland, Abingdon 2,876,083 A * 3/1959 Prietl ....................... 23,295 R (GB); John Patrick Perkins, Ilminster 3,892,539 A * 7/1975 Midler, Jr. ................... 23,301 (GB) 4,990.216 A * 2/1991 Fujita et al. .................. 117/68 (73) Assignee: Accentus PLC, London (GB) (*) Notice: Subject to any disclaimer, the term of this (Continued) patent is extended or adjusted under 35 FOREIGN PATENT DOCUMENTS U.S.C. 154(b) by 235 days. EP O611589 8, 1994 (21) Appl. No.: 10/514,883 EP 1256.558 11 2002 (22) PCT Filed: May 13, 2003 (Continued) (86). PCT No.: Primary Examiner Yogendra N Gupta S 371 (c)(1), Assistant Examiner Seyed Masoud Malekzadeh (2), (4) Date: Nov. 17, 2004 (74) Attorney, Agent, or Firm—William H. Holt (87) PCT Pub. No.: WO03/101578 (57) ABSTRACT PCT Pub. Date: Dec. 11, 2003 A crystalline material Sufficiently pure for use in pharma (65) Prior Publication Data ceuticals may be made by forming a saturated Solution of the material, changing the temperature of the solution so it US 2005/O188913 A1 Sep. 1, 2005 becomes Supersaturated, and Subjecting the Solution to irra diation by high intensity ultrasound, the frequency of the (30) Foreign Application Priority Data ultrasound being scanned over a range of frequencies. For May 31, 2002 (GB) ................................. O212626.6 example the ultrasound may be varied between 19.5 and Feb. 5, 2003 (GB) ................................. O3O2555.8 20.5 kHz, and this variation may be sinusoidal. Preferably the ultrasound is provided only briefly, say for less than 5s, (51) Int. Cl. before allowing the solution to cool gradually without BOLD 9/00 (2006.01) further irradiation. The ultrasound may be applied using a C3OB I/O (2006.01) vessel with an array of ultrasonic transducers attached to a (52) U.S. Cl. ............................... 117/68; 11772; 117/69; wall, so each transducer radiates no more than 3 W/cm yet 117/206: 117/207; 23/293 R; 23/295 R; 23/301; the power dissipation within the vessel is between 25 and 426/238; 600/439;562/.447 150 W/litre. This method can reduce the metastable Zone (58) Field of Classification Search .................. 117/68, width to less than 10 K. It is applicable in particular to 117/206, 207, 69; 23/295 R, 301, 293 R: aspartame. 426/238; 600/439; 562/.447 See application file for complete search history. 8 Claims, 1 Drawing Sheet 10 22 6 8 US 7,357,835 B2 Page 2 U.S. PATENT DOCUMENTS FOREIGN PATENT DOCUMENTS 5,830,418 A 11/1998 König ..................... 422,245.1 GB 22 76567 10, 1994 6,506,250 B1 1/2003 Breitenstein ................. 117.13 WO 96.O7461 3, 1996 6,821,339 B2 * 1 1/2004 Eriksson et al. ... 117,68 WO OO?33366 6, 2000 6,958,040 B2 * 10/2005 Oliver et al. ............... 600,439 WO OO35579 6, 2000 6.966,947 B2 * 1 1/2005 Furuya ........................ 117/68 WO O2/O5921 1, 2002 6,992.216 B2 * 1/2006 Bechtel et al. .............. 562/.447 WO O2/O89.942 11 2002 2002fOO31577 A1 3/2002 Arends ....................... 426,238 2006/0048699 A1* 3/2006 D'Evelyn et al. ............. 117/68 * cited by examiner US 7,357,835 B2 1. 2 PRODUCTION OF CRYSTALLINE growth of the crystals formed during the ultrasonic MATERALS BY USING HIGH INTENSITY insonation. Hence this method enables large crystals to be ULTRASOUND grOWn. In an alternative approach, Such briefbursts of ultrasound This invention relates to a method for crystallisation of 5 may be applied at intervals throughout the cooling of the materials that may be Suitable for use in pharmaceuticals. Solution; this is appropriate if the crystals tend to agglom The use of high intensity ultrasound to trigger nucleation erate, as the briefbursts of ultrasound break up the agglom in a Supersaturated solution, so that crystallisation occurs, is erations. Alternatively the ultrasound may be applied con known, and an apparatus for this purpose is for example tinuously during cooling; this will tend to cause nucleation described in GB 2 276 567 A. The benefits of triggering 10 and so lead to the formation of very Small crystals. nucleation in this fashion are of particular relevance when The ultrasound may be applied to the Supersaturated very pure crystalline products are to be formed in a sterile Solution in a vessel using a multiplicity of ultrasonic trans environment, as the purity of the Solution and the cleanliness ducers attached to a wall of the vessel in an array extending of the vessel Surfaces means that crystallisation nuclei are both circumferentially and longitudinally, each transducer not otherwise present. Certain compounds would be desir 15 being connected to a signal generator so that the transducer able for use in pharmaceuticals, but have been found par radiates no more than 3 W/cm, the transducers being ticularly difficult to crystallise; this relates in particular to sufficiently close together and the number of transducers disaccharides such as D-glucose or D-Xylose. Similar-prob being sufficiently high that the power dissipation within the lems arise with other organic compounds Such as aspartic vessel is between 25 and 150 W/litre. The values of power acid, and the compound alpha-L-aspartyl-L-phenylalanine given here are those of the electrical power delivered to the methyl ester (aspartame). It has often been found necessary transducers, as this is relatively easy to determine. Such an to add crystal modifiers to a saturated Solution of Such irradiation vessel is described in WO 00/35579. Surprisingly compounds to encourage the formation of crystals, as a it has been found that with such a vessel there is no saturated solution may have to be cooled considerably below cavitation at the surface of the wall, so that there is no the Saturation temperature before crystallisation occurs; with 25 erosion of the wall and consequently no formation of Small Some organic materials this under-cooling may be as much particles of metal. The crystalline material made by this as 100° C. That is to say, a supersaturated solution may method can be very pure, as additives are not required and remain in a metastable state for a prolonged period, which the crystallisation procedure does not introduce contami may be many months. The use of an immersed ultrasonic nants, so that it would be suitable both for food use and for probe or horn to Subject a saturated Solution to ultrasound is 30 pharmaceutical use. commonly used, but it has been found that some cavitation It is desirable to ensure no focusing of the ultrasound occurs at the Surface of the horn, this causing slight erosion occurs, and this may be achieved by energising groups of of the horn and consequential generation of very small metal adjacent transducers in Succession. Where the vessel is particles (say about 0.1 mm in diameter); consequently this cylindrical it is particularly preferable to avoid energising process would not be acceptable for generating crystalline 35 diametrically opposite transducers at the same time. The material for use as a pharmaceutical ingredient. non-focusing can also be achieved by energising adjacent transducers, or adjacent groups of transducers, at different Accordingly the present invention provides a method for frequencies; and in particular varying the frequency at which production of crystalline material, the method comprising each transducer or group of transducers is energized over a forming a saturated solution of the material, changing the 40 limited range, for example between 19.5 kHz and 20.5 kHz, temperature of the Solution so it becomes Supersaturated, thus provides this benefit. and Subjecting the solution to irradiation by high intensity The invention will now be further and more particularly ultrasound, the frequency of the ultrasound being Scanned described, by way of example only, and with reference to the over a range of frequencies. accompanying drawing which shows a cross-sectional view For example the ultrasound may be generated by trans 45 of a batch crystallisation irradiator. ducers activated to generate signals at a frequency that Referring to the drawing, a batch crystallisation irradiator varies between 19.5 and 20.5 kHz, and the signals from 10 includes a stainless-steel vessel 12 of internal diameter different transducers may vary independently of each other. 0.31 m and of wall thickness 2 mm. To the outside of the The frequency may vary sinusoidally (with time) between wall are attached sixty transducer modules 14 closely Such limits, or may vary in a sawtooth fashion. The fre 50 packed in a square array. Each transducer module 14 com quency of this modulation may for example lie between 2 prises a 50W piezoelectric transducer 16 which resonates at and 50 Hz, typically between 5 and 15 Hz. Varying the 20 kHz, attached to a conically flared titanium coupling frequency of the ultrasonic waves has been found to improve block 18 by which it is connected to the wall, the wider end the crystallisation process. of each block being of diameter 63 mm. The transducer Preferably the ultrasound is applied only while the solu 55 modules define five circumferential rings each of twelve tion is Supersaturated, and is applied only until crystals are modules 14, the centres of the coupling blocks 18 being on formed, the crystals in the solution then being allowed to a square pitch of 82 mm.
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