Radioiodinated benzamines method of their use as radioimaging agents

• US 5,154,913 A
• Filed: 05/28/1991
• Issued: 10/13/1992
• Est. Priority Date: 11/19/1987
• Status: Expired due to Fees

• Current Assignee: Vanderbilt University
• Original Assignee: Vanderbilt University
• Inventors: de Paulis, Tomas, Janowsky, Aaron, Kessler, Robert M., Smith, Howard E., Clanton, Jeffrey A.
• Primary Examiner(s): Stoll, Robert L.
• Assistant Examiner(s): SAYALA, CHHAYA D
• Application Number:
  US07/708,110
• Time in Patent Office: 504 Days
• Field of Search: 424/1.1, 548/567, 514/359, 514/428
• US Class Current: 424/1.85
• CPC Class Codes: C07D 207/09 Radicals substituted by nitrogen atoms, not forming part of a nitro radical

Abstract

Novel, substituted benzamides in radioiodinated form are useful in radiopharmaceutical compositions in nuclear medicine as imaging agents to detect, visualize, and analyze the distribution and function of the dopamine D-2 receptor in the mammalian brain. The substituted benzamides and their racemic mixtures or their optically resolved enantiomers can be made by reacting a trialyltin substituted benzamide with an acid in the presence of radioactive iodine, generated by in situ oxidation of an appropriate iodide nuclide salt.

Claims

1. [¹²³ I](S)-N-[(1-ethyl-2-pyrrolidinylmethyl]-5-iodo-2-methoxybenzamide.

2. [¹²³ I](R)-N-[(1-4fluorobenzyl-2-pyrrolidinyl)methyl]-5-iodo-2-methoxybenzamide

3. [¹²³ I](S)-N-[1-ethyl-2-pyrrolidinyl)methyl]-5-chloro-3-iodo-6-methoxysalicylamide.

4. [¹²³ I](R)-N-[1-(4-fluorobenzyl)-2-pyrrolidinyl)methyl]5-iodo-2,3-dimethoxybenzamide.

5. [¹²³ I](S)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-iodo-2,3-dimethoxybenzamide.

6. [¹²³ I](S)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-3-iodo-5,6-dimethoxysalicylamide.

7. A method of radioimaging a human brain comprising the steps of:

(a) systematically applying a radioiodinated substituted benzamine selected from the group consisting of [¹²³ I](S)-N-[(1-ethyl-2-pyrrolidinylmethyl]-5-iodo-2-methoxy-benzamide;

(¹²³ I](R)-N-[1-ethyl-2-pyrrolidinyl)methyl]-5-iodo-2-methoxy-benzamide;

[¹²³ I](S)-5-chloro-N-[1-ethyl-2-pyrrolidinyl)methyl]-3-iodo-6-methoxysalicylamide;

[¹²³ I](R)-N-[(1-(4-fluorophenyl-2-pyrrolidinyl)methyl]-5-iodo-2-methoxybenzamide; and

[¹²³ I](S)-N-[(1-ethyl-2-pyrrolidinyl)methyl]-3-iodo-5,6-dimethoxysalicylamide;

[¹²³ I](R)-N-[(1-ethyl-w-pyrrolidinyl)methyl]-5-iodo-2,3-dimethoxy-benzamide.