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US 2022/0289671 A1Published application
Method for the preparation of diarylmethane dyes and triarylmethane dyes including isosulfan blue
AssigneeNj Biopharmaceuticals LLC
InventorsBram Pieter Karsten, Stephen David Kozuch, Nareshkumar Jain
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Abstract
Disclosed herein is a method for the preparation of diarylmethane dyes and triarylmethane dyes, such as Isosulfan Blue, using electrochemistry. Further disclosed is Isosulfan Blue prepared from a process employing electrochemistry, compositions comprising the same, and use of the prepared Isosulfan Blue as an imaging agent.
Claims35
A process of preparing Isosulfan Blue, comprising:
- oxidizing 2-[bis-(4-diethylamino-phenyl)-methyl]-benzene-1,4-disulfonic acid in an electrochemical process.
(canceled)
Isosulfan Blue having one or more of the following properties:
- free of metal;
- contains 0 ppb metal;
- contains a metal below the detectable limit as measured by Atomic Absorption spectrometry (flame or electrothermal), Inductively Coupled Plasma (ICP), or ICP Mass Spectrometry (ICP-MS);
- pure as determined by CHN analysis;
- a purity as measured by HPLC that is greater than 99%;
- a purity as measured by LC-MS that is greater than 95%;
- and
- a purity as measured by MS/MS that is greater than 98%.
5 more elements
A process of preparing a diarylmethane dye or a triarylmethane dye, comprising:
- oxidizing a compound of formula IIa or formula IIb in an electrochemical process:
- wherein each R1, R2, R3 and R4 independently is a substituted or unsubstituted C1-C8 alkyl, a substituted or unsubstituted phenyl, or a substituted or unsubstituted C1-C4 alkylphenyl, wherein the substitution can be a halogen, a C1-C8 alkyl, an amino, a C1-C6-mono- or dialkylamino, a mono- or diphenylamino, hydroxyl, C1-C8 alkoxy, or hydroxysulfonyl;
- each R5 and R6 are independently hydrogen or C1-C2 alkyl;
- Y is hydrogen, substituted or unsubstituted phenyl, or substituted or unsubstituted naphthyl;
- each R7 independently is a halogen, a C1-C8 alkyl, an amino, a C1-C6-mono- or dialkylamino, a mono- or diphenylamino, hydroxyl, C1-C8 alkoxy, or hydroxysulfonyl;
- and
- m is 1, 2, 3, or 4.
4 more elements
Dependencies are inferred from the claim text.