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US 12,673,940 B2Granted
Methods of manufacture and synthesis of fluorescent dye compounds and uses thereof
AssigneeOn Target Laboratories, LLC
InventorsSumith A. Kularatne, Pravin Gagare
Life of this patent
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Abstract
The present disclosure relates to synthesizing and utilizing fluorescent dye compounds or pharmaceutically acceptable salts thereof. Conjugation of amino acid groups to the fluorescent dyes increase specificity and detection of the compound. Methods of manufacture and synthesis of the compounds for use thereof in diagnostic imaging are contemplated.
Claims13
A method for synthesizing a compound of the formula selected from the group consisting of:
- wherein:
- R1 is (CH2)n and n is 1, 2, or 3;
- R2 is a halogen- or X-R3, wherein X is (CH2)m, NH, O, S, or Se;
- m is 0, 1, 2, or 3;
- R3 is [CH2]pCH(R4)COOH or C6H4—[CH2]pCH(R4)COOH or (CH2)pCOOH or (CH2)pNH2 and p is 0, 1, 2, or 3;
- R4 is H or NHR5;
- R5 is H or alkyl group;
- R6, R7 are independently selected from the group consisting of CH2, O, and a combination thereof;
- R8 is (CH2)qSO3H and q is 0, 1, 2, or 3;
- and
- A is a counter cation selected from the group consisting of sodium, potassium, calcium, magnesium, lithium, cholinate, lysinium, ammonium, and hydrogen;
- comprising the steps of:
- (a) reacting a compound of a formula:
- with a compound of a formula:
- in the presence of an acetate salt to generate a compound of the formula:
- (b) reacting the resulting compound with a compound of the formula:
- in the presence of a non-polar solvent to generate a compound of the formula:
- (c) reacting a compound of the formula:
- in the presence of DMF, POCl3, and aniline to generate a compound of the formula:
- (d) reacting the compound of the formula:
- with a
- compound of the formula:
- in the presence of an acetate salt to generate a compound of Formula II:
20 more elements
Dependencies are inferred from the claim text.