The disclosure provides ionizable amine lipids and salts thereof (e.g., pharmaceutically acceptable salts thereof) useful for the delivery of biologically active agents, for example delivering biologically active agents to cells to prepare engineered cells. The ionizable amine lipids disclosed herein are useful as ionizable lipids in the formulation of lipid nanoparticle-based compositions.

A compound having Formula (I) or Formula (II):

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or a mixture thereof,

in which R is —H; —CH.sub.3; —CH—(CH.sub.3).sub.2; —CH.sub.2—CH—(CH.sub.3).sub.2; —CH—(CH.sub.3)—CH.sub.2—CH.sub.3; —CH.sub.2—(C.sub.6H.sub.5); —CH.sub.2—(3-indole); —CH.sub.2—CH.sub.2—S—CH.sub.3; —CH.sub.2—OH; —CH—(CH.sub.3)—OH; —CH.sub.2—SH; —CH.sub.2-(p-C.sub.6H.sub.40H); —CH.sub.2—CH.sub.2—CH.sub.2—CH.sub.2—NH.sub.2; —CH.sub.2—CO—NH.sub.2; —CH.sub.2—CH.sub.2—CO—NH.sub.2; —CH.sub.2—CH.sub.2—COOH; —CH.sub.2—COOH; or —CH.sub.2—CH.sub.2—NH—C═NH.sub.2(NH.sub.2);

and X is a suitable non-interfering anion, a process for making the compound having Formula (I) or Formula (II), and a process for reacting the compound having Formula (I) or Formula (II) or a mixture thereof with a (poly)saccharide to form a cationized (poly)saccharide.

A compound having Formula (I) or Formula (II):

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or a mixture thereof,

in which R is —H; —CH.sub.3; —CH—(CH.sub.3).sub.2; —CH.sub.2—CH—(CH.sub.3).sub.2; —CH—(CH.sub.3)—CH.sub.2—CH.sub.3; —CH.sub.2—(C.sub.6H.sub.5); —CH.sub.2—(3-indole); —CH.sub.2—CH.sub.2—S—CH.sub.3; —CH.sub.2—OH; —CH—(CH.sub.3)—OH; —CH.sub.2—SH; —CH.sub.2-(p-C.sub.6H.sub.40H); —CH.sub.2—CH.sub.2—CH.sub.2—CH.sub.2—NH.sub.2; —CH.sub.2—CO—NH.sub.2; —CH.sub.2—CH.sub.2—CO—NH.sub.2; —CH.sub.2—CH.sub.2—COOH; —CH.sub.2—COOH; or —CH.sub.2—CH.sub.2—NH—C═NH.sub.2(NH.sub.2);

and X is a suitable non-interfering anion, a process for making the compound having Formula (I) or Formula (II), and a process for reacting the compound having Formula (I) or Formula (II) or a mixture thereof with a (poly)saccharide to form a cationized (poly)saccharide.

The present document describes compounds, or pharmaceutically acceptable salt thereof, of a core formula (I) where R.sub.1 features an amine group, particularly useful in the formulation of lipid particles including nucleic acid therapeutic agents, or proteins, or both, and for delivery of nucleic acid and protein therapeutics to cells in vivo or ex vivo, including anticancer and vaccine applications.

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The application relates to a process for drying a composition comprising an alkali metal salt of a compound of general formula (I) R.sup.1R.sup.2N—CHR.sup.3—COOM or formula (II) R.sup.1R.sup.2N—CHR.sup.3CHR.sup.3—COOM, in particular N,N-dimethyl glycinate salt, and the use thereof. In the process, the composition, in particular the N,N-di methyl glycinate salt, is dried by feeding the composition into a fluidized bed dryer and subjecting the composition to a heat treatment by contacting the composition in the fluidized bed dryer with a drying gas stream, and during the heat treatment a solution or dispersion of the composition is sprayed onto at least a portion of the composition present in the fluidized bed dryer, or alternatively or in addition the composition, in particular N,N-dimethyl glycinate salt, is fed into a fluidized bed dryer and subjected to heat treatment in the fluidized bed dryer by contacting the composition with a drying gas stream, and the temperature of the composition in the fluidized bed during the heat treatment does not exceed 50° C.

The application relates to a process for drying a composition comprising an alkali metal salt of a compound of general formula (I) R.sup.1R.sup.2N—CHR.sup.3—COOM or formula (II) R.sup.1R.sup.2N—CHR.sup.3CHR.sup.3—COOM, in particular N,N-dimethyl glycinate salt, and the use thereof. In the process, the composition, in particular the N,N-di methyl glycinate salt, is dried by feeding the composition into a fluidized bed dryer and subjecting the composition to a heat treatment by contacting the composition in the fluidized bed dryer with a drying gas stream, and during the heat treatment a solution or dispersion of the composition is sprayed onto at least a portion of the composition present in the fluidized bed dryer, or alternatively or in addition the composition, in particular N,N-dimethyl glycinate salt, is fed into a fluidized bed dryer and subjected to heat treatment in the fluidized bed dryer by contacting the composition with a drying gas stream, and the temperature of the composition in the fluidized bed during the heat treatment does not exceed 50° C.

The application relates to a process for drying a composition comprising an alkali metal salt of a compound of general formula (I) R.sup.1R.sup.2N—CHR.sup.3—COOM or formula (II) R.sup.1R.sup.2N—CHR.sup.3CHR.sup.3—COOM, in particular N,N-dimethyl glycinate salt, and the use thereof. In the process, the composition, in particular the N,N-di methyl glycinate salt, is dried by feeding the composition into a fluidized bed dryer and subjecting the composition to a heat treatment by contacting the composition in the fluidized bed dryer with a drying gas stream, and during the heat treatment a solution or dispersion of the composition is sprayed onto at least a portion of the composition present in the fluidized bed dryer, or alternatively or in addition the composition, in particular N,N-dimethyl glycinate salt, is fed into a fluidized bed dryer and subjected to heat treatment in the fluidized bed dryer by contacting the composition with a drying gas stream, and the temperature of the composition in the fluidized bed during the heat treatment does not exceed 50° C.

A nitrogen-containing derivative of substituted phenol hydroxyl acid ester is represented by formula (I). A salt of the compound of formula (I) has good water solubility, and in vivo, can rapidly and completely release substituted phenols having a pharmacological effect, which can improve the water solubility of substituted phenols, rapidly exert the pharmacological effects of substituted phenols in vivo, and has good safety. The method for preparing the above-mentioned compound is provided. This compound can also be used in the preparation of drugs that produce anaesthesia and/or sedative and hypnotic effects on humans and animals.

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A nitrogen-containing derivative of substituted phenol hydroxyl acid ester is represented by formula (I). A salt of the compound of formula (I) has good water solubility, and in vivo, can rapidly and completely release substituted phenols having a pharmacological effect, which can improve the water solubility of substituted phenols, rapidly exert the pharmacological effects of substituted phenols in vivo, and has good safety. The method for preparing the above-mentioned compound is provided. This compound can also be used in the preparation of drugs that produce anaesthesia and/or sedative and hypnotic effects on humans and animals.

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Free-standing non-fouling polymers and polymeric compositions, monomers and macromonomers for making the polymers and polymeric compositions, objects made from the polymers and polymeric compositions, and methods for making and using the polymers and polymeric compositions.