Method for preparing 6-aminohexyl lactoside-NOTA conjugate
US10081653B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | Jul 20, 2016 |
| Grant date | Sep 25, 2018 |
| Priority date | — |
| Expiry date | May 9, 2037 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07H1/00
- WIPO fieldPharmaceuticals
- WIPO sectorChemistry
Abstract
The present invention provides a method for preparing a 6-aminohexyl lactoside-NOTA conjugate. The preparation method comprises brominating perbenzoylated lactose with hydrobromic acid; glycosylating 6-azidohexanol to obtain 6-azidohexyl perbenzoyl lactoside; and deprotecting this precursor in two steps to obtain 6-aminohexyl lactoside and conjugating 6-aminohexyl lactoside to NCS-benzyl-NODA GA (i.e. 2,2′-(7-(1-carboxy-4-((4-isothiocyanate benzyl) amino)-4-oxobutyl)-1,4,7-triazonane-1,4-diyl) diacetic acid) in triethyl amine as an alkaline solvent, to obtain a 6-aminohexyl lactoside-NCS-benzyl-NODA GA conjugate. In this novel preparation method, no deglycosylated side product is produced, such that the yield is considerably increased to 46%. Therefore, the method is suitable for future massive production since the requirement for repeated preparations for massive production is reduced, and the impurities produced in the previously scaled-up preparation process are not present.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.