Polymorphic forms of (R)-oxybutynin HCl, including three crystalline forms, are prepared and characterized. Uses of the various polymorphic forms of (R)-oxybutynin HCl for Obstructive Sleep Apnea (OSA) treatment are also disclosed.

The present invention discloses a method for resolving cyclohexylphenyl glycolic acid and the preparation of optically active phenylcyclohexyl glycolate esters. More particularly, the invention provides a process for preparation of optically active R-oxybutynin hydrochloride with high enantiomeric purity of greater than 99%.

The present invention discloses a method for resolving cyclohexylphenyl glycolic acid and the preparation of optically active phenylcyclohexyl glycolate esters. More particularly, the invention provides a process for preparation of optically active R-oxybutynin hydrochloride with high enantiomeric purity of greater than 99%.

A method for purifying a composition, the method including a step of dissolving a composition including a compound represented by Formula (1) [in Formula (1), R.sup.1 represents N(R.sup.2)R.sup.2 (R.sup.2 represents a C1 to C4 alkyl group), each R.sup.3 and R.sup.4 represents a C3 to C8 alkanediyl group, R.sup.5 represents a hydroxyl group, R.sup.6 represents R.sup.7OH (R.sup.7 represents a C4 to C12 alkanediyl group) or a hydrogen atom, and n represents an integer of 0 or 1] in an aqueous layer to perform liquid-liquid extraction, in which an oil layer used for the liquid-liquid extraction includes one or more kinds of liquids selected from the group consisting of a ketone-based liquid, an ester-based liquid, and an ether-based liquid, all of which have a solubility parameter (SP value) of 14.8 to 20.5 (MPa.sup.1/2).

A method for purifying a composition, the method including a step of dissolving a composition including a compound represented by Formula (1) [in Formula (1), R.sup.1 represents N(R.sup.2)R.sup.2 (R.sup.2 represents a C1 to C4 alkyl group), each R.sup.3 and R.sup.4 represents a C3 to C8 alkanediyl group, R.sup.5 represents a hydroxyl group, R.sup.6 represents R.sup.7OH (R.sup.7 represents a C4 to C12 alkanediyl group) or a hydrogen atom, and n represents an integer of 0 or 1] in an aqueous layer to perform liquid-liquid extraction, in which an oil layer used for the liquid-liquid extraction includes one or more kinds of liquids selected from the group consisting of a ketone-based liquid, an ester-based liquid, and an ether-based liquid, all of which have a solubility parameter (SP value) of 14.8 to 20.5 (MPa.sup.1/2).

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. ##STR00001##

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. ##STR00001##

The present disclosure relates to a novel ionizable lipid containing a biodegradable ester bond. The ionizable lipid containing an ester bond, according to the present disclosure, stably delivers an anionic drug when prepared into lipid nanoparticles, and exhibits an excellent effect, in particular, in delivering nucleic acids, and thus can be effectively used in related technical fields such as lipid nanoparticle-mediated gene therapy.

The present disclosure relates to a novel ionizable lipid containing a biodegradable ester bond. The ionizable lipid containing an ester bond, according to the present disclosure, stably delivers an anionic drug when prepared into lipid nanoparticles, and exhibits an excellent effect, in particular, in delivering nucleic acids, and thus can be effectively used in related technical fields such as lipid nanoparticle-mediated gene therapy.

A cationic lipid compound, and a preparation method therefor and use thereof are provided. The cationic lipid compound features a hydroxyl group at the head part, and its overall structure resembles a cone with a small head and a large tail. The LNPs prepared using the cationic lipid compounds with the aforementioned optimal structure usually exhibit enhanced biocompatibility and higher in vivo mRNA transfection efficiency, achieving unexpected technical effects. The synthesis route of the cationic lipid compounds is straightforward and practicable, with inexpensive and readily available raw materials, facilitating industrial production. Furthermore, the LNPs produced from the cationic lipid compounds possess a stable nanostructure that can be stored at low temperatures for a long time, thereby prolonging the shelf life of the pharmaceutical products while reducing the transportation requirements.