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CepheidCepheid is a global leader in molecular diagnostics, dedicated to improving healthcare by developing, manufacturing, and marketing automated, easy-to-use molecular systems and tests. Their mission is to provide rapid, accurate, and actionable genetic testing for a wide range of infectious diseases, oncology, and human genetics. Cepheid's flagship GeneXpert System delivers scalable, sample-to-answer PCR testing for institutions of any size, supporting both centralized and decentralized care. The company is committed to expanding access to high-quality diagnostics worldwide, supporting public health initiatives, driving innovation in molecular testing, and advancing sustainability and responsible business practices.
Cepheid is a global leader in molecular diagnostics, dedicated to improving healthcare by developing, manufacturing, and marketing automated, easy-to-use molecular systems and tests. Their mission is to provide rapid, accurate, and actionable genetic testing for a wide range of infectious diseases, oncology, and human genetics. Cepheid's flagship GeneXpert System delivers scalable, sample-to-answer PCR testing for institutions of any size, supporting both centralized and decentralized care. The company is committed to expanding access to high-quality diagnostics worldwide, supporting public health initiatives, driving innovation in molecular testing, and advancing sustainability and responsible business practices.
Publication Number
US-12428388-B2
Publication Date
2025-09-30
Expiration Date
Abstract
Non-ionic polyether surfactants with improved resistance to hydrolysis are provided.
Core Innovation
Non-ionic polyether surfactants with improved resistance to hydrolysis are provided. In one aspect, the disclosure provides a compound of Formula (I), or an isomer, a hydrate, a solvate, or a tautomer thereof, wherein R is an optionally substituted C6-C70 alkyl or optionally substituted C6-C70 alkenyl; w is an integer ranging from 0 to 20, x is an integer ranging from 0 to 20, y is an integer ranging from 0 to 20, and z is an integer ranging from 0 to 20.
The background identifies that polysorbates are amphiphilic, nonionic surfactants widely used as research reagents and in protein pharmaceuticals to stabilize proteins, and that the main disadvantage of polysorbates is their susceptibility to hydrolysis due to the presence of an ester bond; thus, a need exists for a nonionic surfactant that would not be easily hydrolysable. The disclosure provides polysorbate ether compounds that can be useful as nonionic surfactants in applications where nonionic surfactants such as polysorbate 20 or polysorbate 80 are employed.
The disclosure also provides a method of synthesis of a compound of Formula (I) by converting a compound of Formula (II) so as to reduce the ester group of the compound of Formula (II) to the corresponding ether group, thereby providing polysorbate ether compounds with improved hydrolytic stability. Based on the available documentation, information is insufficient.
Claims Coverage
The patent includes one independent claim directed to a method of preparing a compound of Formula (I) with multiple inventive features.
Method of preparing a compound of Formula (I)
A method of preparing of a compound of Formula (I), or an isomer, a hydrate, a solvate, or a tautomer thereof, wherein R is an optionally substituted C6-C70 alkyl or optionally substituted C6-C70 alkenyl; w, x, y, and z are integers ranging from 0 to 20 (with z ranging from 1 to 20 in the method claim).
Formation of a trimethylsilyl protected derivative
Forming a trimethylsilyl protected derivative of a compound of Formula (II).
Reduction of ester to ether
Contacting the trimethylsilyl derivative of compound of Formula (II) with a suitable reducing agent and gallium tribromide to reduce the ester group of the compound of Formula (II) to the corresponding ether group.
The independent claim covers a method to produce compounds of Formula (I) by protecting a compound of Formula (II) and effecting reduction of an ester to an ether in the presence of a reducing agent and gallium tribromide, with the compound defined by R and integer ranges for w, x, y, and z.
Stated Advantages
Improved resistance to hydrolysis compared to polysorbates.
Resistance to enzymatic hydrolysis (lipase and esterase) as demonstrated in the examples.
Stability under basic conditions as demonstrated in the examples (remained clear in 2M NaOH for at least one month).
Documented Applications
Use as nonionic surfactants in applications where nonionic surfactants such as polysorbate 20 or polysorbate 80 are employed.
Use as research reagents.
Use in protein pharmaceuticals to stabilize the proteins against interface-induced aggregation and to minimize surface adsorption of proteins.
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