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(12) Patent Application Publication (10) Pub. No.: US 2002/0102215 A1 100 Ol US 2002O102215A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2002/0102215 A1 Klaveness et al. (43) Pub. Date: Aug. 1, 2002 (54) DIAGNOSTIC/THERAPEUTICAGENTS (60) Provisional application No. 60/049.264, filed on Jun. 6, 1997. Provisional application No. 60/049,265, filed (75) Inventors: Jo Klaveness, Oslo (NO); Pal on Jun. 6, 1997. Provisional application No. 60/049, Rongved, Oslo (NO); Anders Hogset, 268, filed on Jun. 7, 1997. Oslo (NO); Helge Tolleshaug, Oslo (NO); Anne Naevestad, Oslo (NO); (30) Foreign Application Priority Data Halldis Hellebust, Oslo (NO); Lars Hoff, Oslo (NO); Alan Cuthbertson, Oct. 28, 1996 (GB)......................................... 9622.366.4 Oslo (NO); Dagfinn Lovhaug, Oslo Oct. 28, 1996 (GB). ... 96223672 (NO); Magne Solbakken, Oslo (NO) Oct. 28, 1996 (GB). 9622368.0 Jan. 15, 1997 (GB). ... 97OO699.3 Correspondence Address: Apr. 24, 1997 (GB). ... 9708265.5 BACON & THOMAS, PLLC Jun. 6, 1997 (GB). ... 9711842.6 4th Floor Jun. 6, 1997 (GB)......................................... 97.11846.7 625 Slaters Lane Alexandria, VA 22314-1176 (US) Publication Classification (73) Assignee: NYCOMED IMAGING AS (51) Int. Cl." .......................... A61K 49/00; A61K 48/00 (52) U.S. Cl. ............................................. 424/9.52; 514/44 (21) Appl. No.: 09/765,614 (22) Filed: Jan. 22, 2001 (57) ABSTRACT Related U.S. Application Data Targetable diagnostic and/or therapeutically active agents, (63) Continuation of application No. 08/960,054, filed on e.g. ultrasound contrast agents, having reporters comprising Oct. 29, 1997, now patented, which is a continuation gas-filled microbubbles stabilized by monolayers of film in-part of application No. 08/958,993, filed on Oct. forming Surfactants, the reporter being coupled or linked to 28, 1997, now patented. at least one vector. 256 Gm: 15 62 CW. 34.39 144-1023 18430 (92.2 / ) s 100 Ol FFTClog Patent Application Publication Aug. 1, 2002 Sheet 1 of 2 US 2002/0102215 A1 256 Gm: 15.62 CW. 34.39 144-1023) 18430 (92.2 / ) s Patent Application Publication Aug. 1, 2002 Sheet 2 of 2 US 2002/0102215 A1 18880 (94.4/ ) s FIT Clog F. G. 2. US 2002/0102215 A1 Aug. 1, 2002 DIAGNOSTIC/THERAPEUTICAGENTS 0009. The vector is attached or linked to the reporter moiety in order to bind these moieties to the region/structure 0001) This application claims benefit under 35 U.S.C. to be imaged and/or treated. The vector may bind Specifi 119(e) of provisional applications serial No. 60/049,264 and cally to a chosen target, or it may bind only Selectively, 60/049,265 both filed Jun. 6, 1997; and No. 60/049,268 filed having affinty also for a limited number of other molecules/ Jun. 7, 1997. Structures, again creating possible background problems. 0002 This invention relates to diagnostic and/or thera peutically active agents, more particularly to diagnostic 0010. There is a limited body of prior art relating to and/or therapeutically active agents incorporating moieties targeted ultrasound contrast agents. Thus, for example, U.S. which interact with or have affinity for sites and/or structures Pat. No. 5,531,980 is directed to systems in which the within the body So that diagnostic imaging and/or therapy of reporter comprises an aqueous Suspension of air or gas particular locations within the body may be enhanced. of microbubbles stabilised by one or more film-forming Sur particular interest are diagnostic agents for use in ultrasound factants present at least partially in lamellar or laminar form, imaging, which are hereinafter referred to as targeted ultra said Surfactant(s) being bound to one or more vectors Sound contrast agents. comprising “bioactive species designed for Specific target ing purposes'. It is Stated that the microbubbles are not 0003. It is well known that ultrasound imaging comprises directly encapsulated by Surfactant material but rather that a potentially valuable diagnostic tool, for example in Studies this is incorporated in liquid-filled liposomes which Stabilise of the vascular System, particularly in cardiography, and of the microbubbles. It is will be appreciated that lamellar or tissue microvasculature. A variety of contrast agents has laminar Surfactant material Such as phospholipids present in been proposed to enhance the acoustic images So obtained, such liposomes will inevitably be present in the form of one including Suspensions of Solid particles, emulsified liquid or more lipid bilayers with the lipophilic tails “back-to droplets, gas bubbles and encapsulated gases or liquids. It is back” and the hydrophilic heads both inside and outside (see generally accepted that low density contrast agents which e.g. Schneider, M. on "Liposomes as drug carriers: 10 years are easily compressible are particularly efficient in terms of of research” in Drug targeting, Nyon, Switzerland, Oct. 3-5, the acoustic backScatter they generate, and considerable interest has therefore been shown in the preparation of 1984, Buri, P. and Gumma, A. (Ed), Elsevier, Amsterdam gas-containing and gas-generating Systems. 1984). 0011 EP-A-0727225 describes targeted ultrasound con 0004 Gas-containing contrast media are also known to trast agents in which the reporter comprises a chemical be effective in magnetic resonance (MR) imaging, e.g. as having a Sufficient vapour pressure Such that a proportion of susceptibility contrast agents which will act to reduce MR it is a gas at the body temperature of the Subject. This Signal intensity. Oxygen-containing contrast media also rep chemical is associated with a Surfactant or albumin carrier resent potentially useful paramagnetic MR contrast agents. which includes a protein-, peptide- or carbohydrate-based 0005 Furthermore, in the field of X-ray imaging it has cell adhesion molecule ligand as Vector. The reporter moi been observed that gases Such as carbon dioxide may be eties in Such contrast agents correspond to the phase shift used as negative oral contrast agents or intravascular con colloid systems described in WO-A-9416739; it is now trast agents. recognised that administration of Such phase-shift colloids may lead to generation of microbubbles which grow uncon 0006 The use of radioactive gases, e.g. radioactive iso trollably, possibly to the extent where they cause potentially topes of inert gases Such as Xenon, has also been proposed dangerous embolisation of, for example, the myocardial in Scintigraphy, for example for blood pool imaging. vasculature and brain (see e.g. Schwarz, Advances in Echo 0007 Targeted ultrasound contrast agents may be Contrast 1994(3)], pp. 48-49). regarded as comprising (i) a reporter moiety capable of 0012 WO-A-9320802 proposes that tissue-specific ultra interacting with ultrasound irradiation to generate a detect Sonic image enhancement may be achieved using acousti able signal; (ii) one or more vectors having affinity for cally reflective oligolamellar liposomes conjugated to tis particular target Sites and/or Structures within the body, e.g. Sue-Specific ligands Such as antibodies, peptides, lectins etc. for specific cells or areas of pathology; and (iii) one or more The liposomes are deliberately chosen to be devoid of gas linkers connecting said reporter and vector(s), in the event and So will not have the advantageous echogenic properties that these are not directly joined. of gas-based ultrasound contrast agents. Further references to this technology, e.g. in targeting to fibrin, thrombi and 0008. The molecules and/or structure to which the agent atherOSclerotic areas are found in publications by is intended to bind will hereinafter be referred to as the Alkanonyuksel, H. et al. in J. Pharm. Sci. (1996) 85(5), target. In order to obtain Specific imaging of or a therapeutic 486-490; J. Am. Coll. Cardiol. (1996). 27(2) Suppl A, 298A; effect at a Selected region/structure in the body the target and Circulation, 68 Sci. Sessions, Anaheim Nov. 13-16, must be present and available in this region/structure. Ide 1995. ally it will be expressed only in the region of interest, but usually will also be present at other locations in the body, 0013 There is also a number of publications concerning creating possible background problems. The target may ultrasound contrast agents which refer in passing to possible either be a defined molecular species (i.e. a target molecule) use of monoclonal antibodies as vectors without giving or an unknown molecule or more complex structure (i.e. a Significant practical detail and/or to reporters comprising target structure) which is present in the area to be imaged materials which may be taken up by the reticuloendothelial and/or treated, and is able to bind Specifically or Selectively System and thereby permit image enhancement of organs to a given vector molecule. such as the liver-see, for example WO-A-9300933, WO US 2002/0102215 A1 Aug. 1, 2002 A-94.01140, WO-A-9408.627, WO-A-9428874, U.S. Pat. thrombi and atherosclerotic lesions or for visualising neo No. 5,088,499, U.S. Pat. No. 5,348,016 and U.S. Pat. No. vascularised and inflamed tissue areas. The present inven 5,469,854. tion is particularly Suited to imaging changes which occur in 0.014. The present invention is based on the finding that normal blood vessels situated in areas of tissue necrosis. gas-filled microbubbles stabilised by monolayers of film 0019. In a further embodiment of the present invention, forming Surfactant material are particularly useful reporters one or more vectors may be attached to or included within in targeted diagnostic and/or therapeutic agents. Thus, for the reporter in a manner Such that the vectors are not readily example, the flexibility and deformability of such thin exposed to the target or target receptors. Increased tissue monolayer membranes Substantially enhances the echoge Specificity may therefore be achieved by applying an addi nicity of Such reporters relative to liposome Systems con tional process to expose the vectors, for example by expos taining lipid bilayerS or multiples of Such bilayers.
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