Radiolabeled amine compounds and their use

Drug – bio-affecting and body treating compositions – Radionuclide or intended radionuclide containing; adjuvant... – Molecular bilayer structure

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564 84, 564 85, 424 9, A61K 4900, A61K 4300

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044068751

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BRIEF SUMMARY
The present invention relates generally to radiolabeled amine compounds and to methods for preparing these compounds. The invention further relates to diagnostic compositions containing the radiolabeled amine compounds and to the use of these compositions in conducting radiodiagnostic examinations.
Compounds labeled with radioisotopes are useful in medical diagnostic examinations, for example, in examinations for deviations in the shape or function of internal organs. In these examinations, a composition containing the radioactive compound is administered to a patient, for example, as an injected liquid. Then, by observing the radiation emitted from the body of the patient with a suitable detection apparatus such as an external scintillation scanner or camera, an image can be obtained which indicates, for example, the organ or the pathological process in which the radioactive compound is incorporated.
For example, it is known from the article by K. A. Krohn and L. C. Knight, Seminars of Nuclear Medicine; Vol. VII, No. 3 (July 1977), p. 219-228, that fibrinogen labeled with a radioactive isotope may be useful in determining the location and extent of an occurring blood clotting process. Knowledge of the location of an occurring blood clotting process is extremely important in the clinical treatment of patients prone to undesirable blood clot formations. With sufficient knowledge of the location of occurring blood clot, successful treatment may be undertaken to counteract potential life-threatening situations caused by the occurring blood clot.
The mechanism of blood clotting or coagulation is quite complex. In accordance with fairly generally acceptable hypotheses, the normal mechanism of blood coagulation can be separated into three phases: a first phase wherein thromboplastin is formed by the interaction between certain factors in the blood, a second phase during which the prothrombin of the blood is converted to thrombin during enzymatic action of a factor activated by the thromboplastin, and a third phase in which the thrombin, a proteolytic enzyme, converts fibrinogen, a complex albumin in blood plasma, to fibrin, whereupon a solid coagulum is formed. This conversion of the fibrinogen to fibrin is believed to proceed in two steps: (1) fibrinogen, through the influence of the thrombin, loses two short chain polypeptides, and (ii) aggregation of the molecules to the positions where the two peptides were lost, to form long fibrous complexes in the form of soft aggregates, which under the influence of Factor XIII are then converted into insoluble coagulums through the formation of intermolecular amide linkages. The corpuscles of the blood then become entangled in the coagulums thereby forming a blood clot.
The initial formation of thromboplastin is activated at locations in blood vessels where damage has occurred. However, this thromboplastin, called intrinsic thromboplastin or plasma thromboplastin, can be replaced by an active product, designated extrinsic thromboplastin which is formed under the influence of a factor in the vascular tissues. The entire coagulation sequence is a series of enzymatic reactions, wherein various factors successively activate one another.
When radiolabeled fibrinogen is administered a patient for diagnostic purposes so as to determine the location of an occurring blood clotting process, the quantity of radiolabeled fibrinogen is necessarily small with respect to the large quantity of natural fibrinogen present in the circulating blood. Therefore, the quantity of radiolabeled fibrinogen which is incorporated into the fibrin network when a clot occurs is also small. As a consequence, a clot does not clearly stand out from its surroundings during an image-forming procedure in the radiodiagnostic examination.
In Rhodes et al., Radiopharmaceuticals (Soc. Nucl. Med. Inc., N.Y., N.Y. 1970) p. 521, it is suggested that radiolabeled amines might be used to label occurring blood clots. However, no specific example of any suitable radiolabeled amine was set forth in this publication.
In

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