Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1985-10-15
1987-08-18
Bond, Robert T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C07D47110
Patent
active
046878521
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to a novel radioactive 2iodospiroperidol and a process for preparing the same.
The compound of this invention is a novel compound not disclosed in any literature. This compound has a strong affinity for dopamine receptor and is very useful as a nuclear medical diagnostic agent of dopamine receptor and as a radioactive medicine.
BACKGROUND ART
It has recently been found that in the pathological state of brain (such as Parkinson's disease or schizophrenia), the amount of dopamine receptor is different from that in the normal person, and attention has become directed to the relation between dopamine receptor and various kinds of brain diseases in the fields of medicine and pharmacology. Under these circumstances, the advent of a nuclear medical diagnostic agent and a radioactive medicine targeting dopamine receptor has been strongly desired.
DISCLOSURE OF INVENTION
The present inventors have made extensive studies aiming at obtaining a dopamine receptor-tropic diagnostic agent and a radioactive medicine having radioactive iodine in its molecule, and have found that the novel iodine compound represented by the formula (I) shown below has a strong affinity for dopamine receptor and can be specifically combined therewith.
According to this invention, there is provided a novel radioactive 2-iodospiroperidol represented by the formula (I): ##STR2## wherein X represents a radioactive iodine atom, and a process for preparing the same. The compound (I) of this invention has a much stronger affinity for dopamine receptor than p-iodospiroperidol which is a known iodine compound disclosed in literature [J. Nuclear Medicine, 23(5), 100 (1982)], and possesses very excellent properties as a dopamine receptor-tropic radioactive diagnostic agent or radioactive medicine.
Therefore, proper application of the compound (I) of this invention makes it possible not only to non-invasively detect the presence of dopamine receptor in the brain and other internal organs and tissues of human beings and animals but also to dynamically measure the change of amount of the receptor, and thus, this compound is greatly useful for the nuclear medical diagnosis and treatment of brain troubles and other diseases. Also, in view of the relevancy of dopamine receptor to cancers such as breast cancer and the like, the compound is also useful in application to this field.
BEST MODE FOR CARRYING OUT THE INVENTION
The method for the preparation of the compound of this invention will be described below.
The compound of this invention represented by the above-mentioned formula (I) can be produced by a conventional method for the synthesis of radioactive iodine compounds. For instance, it can be produced according to either Process A or Process B shown below.
[Process A]
An amino compound represented by the formula (II): ##STR3## is reacted with an alkali metal salt of nitrous acid in a suitable solvent such as tetrahydrofuran, dioxane, acetonitrile or the like in the presence of an acid such as diluted sulfuric acid or diluted hydrochloric acid to form a diazonium salt represented by the formula (III): ##STR4## wherein Z.sup.- represents an anion represented by a halogen ion or the formula HSO.sub.4.sup.-.
Then the compound (III) is reacted with a radioactive iodine metal salt to obtain the compound of the formula (I). The above reactions are carried out at a temperature in a range of -5.degree. to 30.degree. C.
The compound (I) obtained can be purified by a conventional method such as thin layer chromatography (TLC) or high-performance liquid chromatography (HPLC).
[Process B]
A halogeno compound represented by the formula (IV): ##STR5## wherein Y represents a halogen atom is subjected to an exchange reaction with a radioactive iodine metal salt in a suitable solvent such as acetonitrile, dimethylformamide, ethylene glycol, an ether derivative of ethylene glycol, an ether derivative of diethylene glycol, water or the like at a temperature of 50.degree. to 180.degree. C. The compound (I) obtained can be pu
REFERENCES:
patent: 3238216 (1966-03-01), Janssen
Nakatsuka Iwao
Shimizu Hiroshi
Yoshitake Akira
Bond Robert T.
Sumitomo Chemical Company Limited
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