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US 11,896,969 B2Granted
Anionic exchange-hydrophobic mixed mode chromatography resins
AssigneeBio-Rad Laboratories, Inc.
InventorsChristopher Belisle, Xuemei He, Hong Chen, Yueping Xu, Jiali Liao
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Abstract
Chromatography resins having anionic exchange-hydrophobic mixed mode ligands and methods of using such resins are provided.
Claims12
A chromatography matrix covalently linked to a ligand having the following formula:
- Chromatography matrix-(X)—N(R1)—(R2-L)n-Ar
- or an anionic salt thereof,
- wherein:
- X is a spacer;
- R1 is hydrogen or C1 to C6 alkyl optionally substituted with an —OH;
- R2 is C2 to C6 alkyl or C4 to C6 cycloalkyl;
- L is NR4, O, or S;
- n=1 or 2;
- and
- Ar is a 6-10 membered ring and:
- if Ar is aryl, the aryl is optionally substituted with up to five C1 to C3 unsubstituted alkyl, C3 to C6 branched alkyl, unsubstituted aryl, or fluorine groups;
- or
- if Ar is heteroaryl, the heteroaryl is optionally substituted with up to four unsubstituted alkyl groups,
- with the proviso that when R1 is hydrogen, R2 is C2 alkyl, L is NR4 or O, and n is 1, Ar is not phenyl.
11 more elements
A chromatography resin prepared by reacting a ligand with a chromatography support comprising an aldehyde group, epoxide group, or an azalactone group, said ligand being selected from the group consisting of:
- 2-(p-Tolyloxy)ethylamine;
- 2-(o-Tolyloxy)ethylamine;
- 2-(m-Tolyloxy)ethylamine;
- 3,5-dimethylphenoxyethanamine;
- 4-ethylphenoxy ethanamine;
- 4-isopropylphenoxy ethanamine;
- 4-t-butylphenoxy ethanamine;
- 4-phenylphenoxy ethanamine;
- 1-naphthalenoxy ethanamine;
- 3-flourophenoxy ethanamine;
- 4-flourophenoxy ethanamine;
- 3,5-diflourophenoxy ethanamine;
- 2,5-diflourophenoxy ethanamine;
- 3,4-diflourophenoxy ethanamine;
- 3,4,5-triflourophenoxy ethanamine;
- perflourophenoxy ethanamine;
- 4-pyridinylethanamine;
- 3-pyridinylethanamine;
- 4-(2,6-dimethylpyridinyl)ethanamine;
- Phenoxypropylamine;
- 2-phenoxycyclobutylamine;
- 2-phenoxycyclopentylamine;
- 4-phenoxycyclohexylamine;
- 2-(2-phenoxyethoxy)ethanamine;
- N-methyl-2-phenoxyethan-1-amine;
- N-methyl-3-phenoxypropan-1-amine;
- N-methyl(2-phenoxy cyclobutyl)amine;
- N-methyl(2-phenoxy cyclopentyl)amine;
- N-methyl(4-phenoxy cyclohexyl)amine;
- N-methyl-2-(p-tolyloxy)ethan-1-amine;
- 2-(3,5-dimethylphenoxy)-N-methylethan-1-amine;
- 2-(4-ethylphenoxy)-N-methylethan-1-amine;
- 2-(4-isopropylphenoxy)-N-methylethan-1-amine;
- 2-(4-(tert-butyl)phenoxy)-N-methylethan-1-amine;
- 2-([1,1′-biphenyl]-4-yloxy)-N-methylethan-1-amine;
- N-methyl-2-(naphthalen-1-yloxy)ethan-1-amine;
- 2-((2-phenoxyethyl)amino)ethan-1-ol;
- 2-(3-fluorophenoxy)-N-methylethan-1-amine;
- 2-(4-fluorophenoxy)-N-methylethan-1-amine;
- 2-(2,5-difluorophenoxy)-N-methylethan-1-amine;
- 2-(3,4-difluorophenoxy)-N-methylethan-1-amine;
- 2-(3,5-difluorophenoxy)-N-methylethan-1-amine;
- N-methyl-2-(3,4,5-trifluorophenoxy)ethan-1-amine;
- N-methyl-2-(perfluorophenoxy)ethan-1-amine;
- N-methyl-2-(pyridin-4-yloxy)ethan-1-amine;
- N-methyl-2-(pyridin-3-yloxy)ethan-1-amine;
- 2-((2,6-dimethylpyridin-4-yl)oxy)-N-methylethan-1-amine;
- and
- N-methyl-2-(2-phenoxyethoxy)ethan-1-amine.
46 more elements
Dependencies are inferred from the claim text.