Process for preparation of isosulfan blue

Organic compounds -- part of the class 532-570 series – Organic compounds – Sulfonic acids or salts thereof

Reexamination Certificate

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C562S059000

Reexamination Certificate

active

07662992

ABSTRACT:
A process for the preparation of isosulfan blue (Active Pharmaceutical Ingredient) is provided. A process is also provided for preparation of the intermediate, 2-chlorobenzaldehyde-5-sulfonic acid, sodium salt of formula (2), used in the preparation thereof and a procedure for the isolation of benzaldehyde-2,5-disulfonic acid, di-sodium salt of the formula (3). Also provided is a process for the preparation of an isoleuco acid of formula (4), which upon mild oxidation gives rise to isosulfan blue of pharmaceutical grade which can be used for preparation of pharmaceutical formulations. The isolation and purification procedures provided in the process provide substantially pure isosulfan blue with HPLC purity 99.5% or greater.

REFERENCES:
patent: 1531507 (1925-03-01), Rosenbaum
patent: 1805925 (1931-05-01), Schmidt
patent: 1878530 (1932-09-01), Kyrides
patent: 2422445 (1947-06-01), Stryker
patent: 2726252 (1955-12-01), Balon
patent: 4330476 (1982-05-01), Hermann
patent: 4710322 (1987-12-01), Metz
patent: 5659053 (1997-08-01), Gessner et al.
patent: 2006/0224003 (2006-10-01), Kulkarni et al.
Rodd's Chemistry of Carbon Compounds by S. Coffey, 1974 2nd Edition vol. III Part F 110-113.
International Search and Written Opinion of Apr. 23, 2003 of International Application No. PCT/US07/84051.

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