This application relates to solabegron zwitterion useful for the treatment of lower urinary tract symptoms such as, for example, overactive bladder and prostate disorders. Additionally, this application relates to pharmaceutical compositions and methods of treatment utilizing the solabegron zwitterion for treating lower urinary tract symptoms. This application also relates to methods of preparing solabegron hydrochloride from the solabegron zwitterion.

Provided herein are processes, compounds and compositions for making (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid. Also provided herein a pharmaceutical compositions containing (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid.

Provided herein are processes, compounds and compositions for making (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid. Also provided herein a pharmaceutical compositions containing (S)-3-amino-4-(difluoromethylenyl)cyclopent-1-ene-1-carboxylic acid.

The present invention is related with the obtaining process and use of branched germinal zwitterionic liquids based on either bis-N,N-dialkyl-N-polyether-betaine or bis-N,N-dialkenyl-N-polyether-betaine or bis-N,N-dicycloalkyl-N-polyether-betaine or bis-N,N-diaryl-N-polyether-betaine, to be applied as modifiers of the wettability of rocks such as limestone, dolomite, sandstone, quartz or heteregenous lithologies, under the presence of brines having high content of divalent ions such as calcium, magnesium, barium or strontium, under high temperature and high pressure within enhanced oil recovery processes in order to increase the oil production.

The branched germinal zwitterionic liquids of the present invention have moreover the property to act as viscosity reducers of heavy oils having high content of polar fractions, both for extraction and production, and transport and storage operations, so allowing increase the production level of this oil type. An additional advantage shown by the zwitterionic liquids, derived from their molecular structure, is that they can be handed in such a manner that can be dissolved by water, hydrocarbon or other polar and non-polar solvents.

The present invention is related with the obtaining process and use of branched germinal zwitterionic liquids based on either bis-N,N-dialkyl-N-polyether-betaine or bis-N,N-dialkenyl-N-polyether-betaine or bis-N,N-dicycloalkyl-N-polyether-betaine or bis-N,N-diaryl-N-polyether-betaine, to be applied as modifiers of the wettability of rocks such as limestone, dolomite, sandstone, quartz or heteregenous lithologies, under the presence of brines having high content of divalent ions such as calcium, magnesium, barium or strontium, under high temperature and high pressure within enhanced oil recovery processes in order to increase the oil production.

The branched germinal zwitterionic liquids of the present invention have moreover the property to act as viscosity reducers of heavy oils having high content of polar fractions, both for extraction and production, and transport and storage operations, so allowing increase the production level of this oil type. An additional advantage shown by the zwitterionic liquids, derived from their molecular structure, is that they can be handed in such a manner that can be dissolved by water, hydrocarbon or other polar and non-polar solvents.

The present invention relates to a conjugate salt of N,N-dimethylglycine with metal and organic acid, and a preparation method and use thereof. The conjugate salt of N,N-dimethylglycine with metal and organic acid has a following structural formula: [(CH.sub.3).sub.2NCH.sub.2COO].sub.nM.[Organic acid], wherein, n is 1 or 2; M is selected from an alkali metal ion or a divalent metal ion; the organic acid is selected from an organic polyacid, a C.sub.2-C.sub.18 linear fatty acid or an aromatic acid. The conjugate salt of N,N-dimethylglycine with metal and organic acid is a conjugate acid salt formed by introducing another organic acid with a hydrophobic group into the salt of N,N-dimethylglycine and a metal ion, so as to modify the hygroscopicity of N,N-dimethylglycine by decreasing the affinity of the salt toward water molecules in the air, or decreasing the affinity or attraction of molecular aggregates formed through crystalline behavior of the salt toward water molecules in the air.

Compounds are provided having the following structure: ##STR00001##
or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof, wherein R.sup.1a, R.sup.1b, R.sup.2a, R.sup.2b, R.sup.3a, R.sup.3b, R.sup.4a, R.sup.4b, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, L.sup.1, L.sup.2, a, b, c, d and e are as defined herein. Use of the compounds as a component of lipid nanoparticle formulations for delivery of a therapeutic agent, compositions comprising the compounds and methods for their use and preparation are also provided.

Compounds are provided having the following structure: ##STR00001##
or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof, wherein R.sup.1a, R.sup.1b, R.sup.2a, R.sup.2b, R.sup.3a, R.sup.3b, R.sup.4a, R.sup.4b, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, L.sup.1, L.sup.2, a, b, c, d and e are as defined herein. Use of the compounds as a component of lipid nanoparticle formulations for delivery of a therapeutic agent, compositions comprising the compounds and methods for their use and preparation are also provided.

The present invention relates to a process for preparing 3-(2-hydroxybenzoyloxy)-4-(trimethylammonio)butyrobetaine hydrochloride of formula (I), ##STR00001##
wherein the process comprises reacting 3-hydroxy-4-(trimethylammonio)butyrobetaine or a salt thereof with a 2-alkoxybenzoyl chloride of formula (III), ##STR00002##
and where R is selected from benzyl and branched C3-C6 alkyl groups. The present invention further relates to compounds of formula (II) and salts thereof, where R is selected from benzyl and branched C3-C6 alkyl groups, and to a process for preparing same. ##STR00003##

The present invention relates to a process for preparing 3-(2-hydroxybenzoyloxy)-4-(trimethylammonio)butyrobetaine hydrochloride of formula (I), ##STR00001##
wherein the process comprises reacting 3-hydroxy-4-(trimethylammonio)butyrobetaine or a salt thereof with a 2-alkoxybenzoyl chloride of formula (III), ##STR00002##
and where R is selected from benzyl and branched C3-C6 alkyl groups. The present invention further relates to compounds of formula (II) and salts thereof, where R is selected from benzyl and branched C3-C6 alkyl groups, and to a process for preparing same. ##STR00003##