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United States Patent (19) 11 Patent Number: 6,106,806 Klaveness Et Al

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United States Patent (19) 11 Patent Number: 6,106,806 Klaveness Et Al USOO6106806A United States Patent (19) 11 Patent Number: 6,106,806 Klaveness et al. (45) Date of Patent: *Aug. 22, 2000 54) MICROBUBBLE-CONTAINING CONTRAST 5,141,738 8/1992 Rasor et al. ........................... 424/9.52 AGENTS HAVING ANON-PROTEINACEOUS 5,271,928 12/1993 Schneider et al.. CROSSLINKED OR POLYMERISED 5,425,366 6/1995 Reinhardt et al.. 5,469,854 11/1995 Unger et al.. AMPHIPHILIC SHELL 5,501,863 3/1996 Rössling et al.. 75 Inventors: Jo Klaveness; Hanno Priebe; Pál 552. SEC E. et al. 424/9.52 Rongved; Lars Stubberud; Roald 2- Y/ u-a- - - 1 - - - - - www1. - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - Skurtveit; Harald Dugstad, all of FOREIGN PATENT DOCUMENTS Oslo, Norway 0327490 8/1989 European Pat. Off.. 0441468 8/1989 European Pat. Off.. 73 Assignee: Nycomed Imaging AS, Oslo, Norway 0327490 9/1989 European Pat. Off. ....... A61K 49/00 * Notice:- - - This patent is Subject to a terminal dis- 0458745WO-A- 11/1991 European Pat. Off.. claimer. 9204392 3/1992 WIPO. WO-A- 21 Appl. No.: 08/478,733 ". 9/1994 WIPO. 22 Filed: Jun. 7, 1995 942878O 12/1994 WIPO. WO-A- Related U.S. Application Data 9506518 3/1995 WIPO. 63 Continuation-in-part of application No. 08/119,217, Oct. 29, OTHER PUBLICATIONS 1993, Pat. No. 5,536,490, which is a continuation of appli Juliano et al., STN File Server, File Biosis & Biological cation No. PCT/EP92/00715, Mar. 28, 1992. Abstracts, vol. 79, 1985. 30 Foreign Application Priority Data Primary Examiner Jose' G. Dees Mar. 28, 1991 GB United Kingdom ................... 9106673 Assistant Examiner Michael G. Hartley (51) Int. Cl." ..................................................... A61K 49/04 Attorney, Agent, or Firm-Kenyon & Kenyon 52 U.S. Cl. ............................................................. 424/9.52 57 ABSTRACT 58 Field of Search .................................. 424/9.52, 9.51, 424/9.5, 450, 489, 493, 501, 502; 128/662.02; Ultrasound contrast agents having microbubbles of gas or a 600/458 gas precursor encapsulated by non-proteinaceous crosslinked or polymerised amphiphilic moieties, e.g. in the 56) References Cited form of micelles, exhibit good Stability in Vivo upon admin istration and may if desired incorporate biodegradable link U.S. PATENT DOCUMENTS ages So as to possess particular desired levels of biodegrad 4,265,251 5/1981 Tickner. ability. 4,900,540 2/1990 Ryan et al.. 5,088,499 2/1992 Unger ................................. 128/662.02 31 Claims, No Drawings 6,106,806 1 2 MICROBUBBLE-CONTAINING CONTRAST “vesicle' is used herein to denote all Such microbubble AGENTS HAVING ANON-PROTEINACEOUS Structures prior to or after crosslinking or polymerisation. It CROSSLINKED OR POLYMERISED should be noted that under Some conditions irregularly AMPHIPHILIC SHELL shaped structures may be formed, e.g. microtubles which may join with or even entrap spherical Structures. This application is a continuation-in-part of application Thus according to one aspect of the present invention Ser. No. 08/119,217 filed on Oct. 29, 1993, U.S. Pat. No. there are provided contrast agents for use in diagnostic 5,536,490, which is of 371 of PCT/EP92/00715 dated Mar. ultrasound Studies comprising microbubbles of gas or a gas 28, 1992. precursor encapsulated by non-proteinaceous crosslinked or This invention relates to novel contrast agents, more polymerised amphiphilic moieties. particularly to new gas-containing or gas-generating con The term “crosslinked' is used herein to denote that the trast agents of use in diagnostic ultrasonic imaging. amphiphilic moieties are chemically linked to each other, It is well known that ultraSonic imaging comprises a e.g. to form a polymeric Structure which may incorporate potentially valuable diagnostic tool, for example in Studies one or more polymer Systems (including copolymers), and of the vascular System, particularly in cardiography, and of 15 includes Systems prepared by reaction with So-called Zero tissue microvasculature. A variety of contrast agents has crosslinking agents. The terms “polymerised' and “poly been proposed to enhance the acoustic images So obtained, meric Structure” as used herein embrace low molecular including Suspensions of Solid particles, emulsified liquid weight polymer Systems. Such as dimers and other oligomers. droplets, gas bubbles and encapsulated gases or liquids. It is A major advantage of contrast agents according to the generally accepted that low density contrast agents which invention is that they may be designed to a particular desired are easily compressible are particularly efficient in terms of level of biodegradability in Vivo by Selecting appropriate the acoustic backScatter they generate, and considerable biodegradable linkages at appropriate positions. It will be interest has therefore been shown in the preparation of appreciated that in order to be effective the contrast agents gas-containing and gas-generating Systems. must be stable throughout the ultraSonic examination but are Initial Studies involving free gas bubbles generated in 25 preferably metabolised or removed safely from the circula Vivo by intracardiac injection of physiologically acceptable tion System shortly thereafter. Contrast agents in accordance Substances have demonstrated the potential efficiency of with the invention should thus preferably have a half-life in Such bubbles as contrast agents in echocardiography; Such vivo of not more than 48 hours, for example 1-12 hours. techniques are Severely limited in practice, however, by the Biodegradable linkages which may be present in contrast short lifetime of the free bubbles. Interest has accordingly agents according to the invention include amide, imide, been shown in methods of stabilising gas bubbles for imine, ester, anhydride, acetal, carbamate, carbonate, car echocardiography and other ultraSonic Studies, for example bonate ester and disulphide groups. At least one Such group using emulsifiers, oils, thickeners or SugarS. should preferably be present in the amphiphilic moiety, in WO 80/02365 discloses the use of gelatin-encapsulated the hydrophilic and/or lipophilic portion, it may be advan gas microbubbles for enhancing ultraSonic images. Such 35 tageous to position the group in the hydrophilic part to microbubbles do not, however, exhibit adequate stability at facilitate enzymic interaction in Vivo. It is further preferred the dimensions preferred for use in echocardiography (1-10 that biodegradable linkages be present in the polymer back pum) in view of the extreme thinness of the encapsulating bone to ensure substantial breakdown of the polymer in the coating. body. U.S. Pat. No. 4,774,958 discloses the use of microbubble 40 Any biocompatible gas may be employed in the contrast dispersions Stabilised by encapsulation in denatured protein, agents of the invention, for example air, nitrogen, oxygen, e.g. human Serum albumin. Such Systems permit the pro hydrogen, nitrous oxide, carbon dioxide, helium, argon, duction of microbubble Systems having a size of e.g. 2-5 um Sulphur hexafluoride, low molecular weight optionally flu but still do not permit efficient visualisation of the left heart orinated hydrocarbons Such as methane, acetylene, carbon and myocardium. 45 tetrafluoride and other perfluoroalkane S Such as EP-A-0327490 discloses, inter alia, ultrasonic contrast perfluoropropane, perfluorobutane and perfluoropentane, agents comprising a microparticulate Synthetic biodegrad and mixture of any of the foregoing. The term “gas' as used able polymer (e.g. a polyester of a hydroxy carbonic acid, a herein includes any Substances, including mixtures, in gas polyalkyl cyanoacrylate, a polyamino acid, a polyamide, a eous or vapour form at 37 C. In general the gas may be free polyacrylated Saccharide or a polyorthoester) containing a 50 within the microbubbles, advantageously in the form of a gas or volatile fluid (i.e. having a boiling point below 60° C.) gas-filled “microballoon' Since the echogenicity of Such in free or bonded form. Emulsifiers may be employed as products may be enhanced by virtue of their relatively Stabilisers in the preparation of Such agents, but Such emul flexible nature. Alternatively the gas may be trapped or sifiers do not chemically interact with the polymer. entrained within a containing Substance. We have now found that particularly effective ultrasonic 55 Gas precursors include carbonates and bicarbonates, c.g. contrast agents may be obtained by encapsulating gas Sodium or ammonium bicarbonate and aminomalonate bubbles or gas generating Systems with polymers containing esters. The term "gas precursor as used herein also chemically linked Surface active, i.e. amphiphilic, moieties. embraces Substances Such as volatile hydrocarbons which Thus the Surface active properties of the amphiphilic groups may initially be encapsulated but thereafter are partially or Stabilise the microbubble System by reducing Surface tension 60 completely removed from the vesicles, e.g. by evaporation at the gas-liquid interfaces, e.g. by forming monolayerS or or freeze-drying, to be replaced by gas. one or more bilayers (alternatively known by the terms For applications in echocardiography, in order to permit micelles, vesicles, liposomes and niosomes) at said free passage through the pulmonary System and to achieve interfaces, while the linking of the groups through the resonance with the preferred imaging frequency of about polymer system generates further stability. Flexibility of the 65 0.1-15 MHz, it may be convenient to employ microbubbles encapsulating
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