Provided herein are compounds, compositions, and methods useful for modulating the integrated stress response (ISR) and for treating related diseases, disorders and conditions.

The present invention relates to a phytic acid ester derivative and a use thereof. The phytic acid ester derivative of the present invention has a structure of the following formula I:

##STR00001## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, R.sup.11 and R.sup.12 are each independently selected from the group consisting of H, the following formula II:

##STR00002## wherein —CH.sub.2— is optionally substituted by one or two substituents, the following formula III:

##STR00003## wherein —CH.sub.2—C.sub.6H.sub.4— is optionally substituted by one or more substituents, and the following formula IV:

##STR00004## wherein —CH.sub.2—CH.sub.2— is optionally substituted by one or more substituents, provided that a compound where all of R.sup.1 to R.sup.12 are H is excluded.

The present invention relates to novel hydroxyl compounds, compositions comprising hydroxyl compounds, and methods useful for treating and preventing a variety of diseases and conditions such as, but not limited to aging, Alzheimer's Disease, cancer, cardiovascular disease, diabetic nephropathy, diabetic retinopathy, a disorder of glucose metabolism, dyslipidemia, dyslipoproteinemia, hypertension, impotence, inflammation, insulin resistance, lipid elimination in bile, obesity, oxysterol elimination in bile, pancreatitis, pancreatitius, Parkinson's disease, a peroxisome proliferator activated receptor-associated disorder, phospholipid elimination in bile, renal disease, septicemia, metabolic syndrome disorders (e.g., Syndrome X), thrombotic disorder. Compounds and methods of the invention can also be used to modulate C reactive protein or enhance bile production in a patient. In certain embodiments, the compounds, compositions, and methods of the invention are useful in combination therapy with other therapeutics, such as hypocholesterolemic and hypoglycemic agents.

The present invention relates to novel hydroxyl compounds, compositions comprising hydroxyl compounds, and methods useful for treating and preventing a variety of diseases and conditions such as, but not limited to aging, Alzheimer's Disease, cancer, cardiovascular disease, diabetic nephropathy, diabetic retinopathy, a disorder of glucose metabolism, dyslipidemia, dyslipoproteinemia, hypertension, impotence, inflammation, insulin resistance, lipid elimination in bile, obesity, oxysterol elimination in bile, pancreatitis, pancreatitius, Parkinson's disease, a peroxisome proliferator activated receptor-associated disorder, phospholipid elimination in bile, renal disease, septicemia, metabolic syndrome disorders (e.g., Syndrome X), thrombotic disorder. Compounds and methods of the invention can also be used to modulate C reactive protein or enhance bile production in a patient. In certain embodiments, the compounds, compositions, and methods of the invention are useful in combination therapy with other therapeutics, such as hypocholesterolemic and hypoglycemic agents.

The present invention provides a compound of formula (II): an inhibitor of indoleamine 2,3-dioxygenase (IDO), which may be used as medicaments for the treatment of proliferative disorders, such as cancer, viral infections and/or autoimmune diseases. Its prodrugs are disclosed.

##STR00001##

The present invention relates to a compound having a structure according to formula (I) or a salt thereof, wherein: R.sub.1 is a branched or linear alkyl, acyl, alkenyl, hydroxyalkyl, hydroxyalkenyl, or hydroxy-alkinyl residue comprising 6 to 30 carbon atoms, R.sub.2 is selected from the group consisting of: a) an alkyl residue comprising 1 to 10 carbon atoms and comprising a terminal or cyclic quaternary ammonium, b) an alkyl residue comprising 1 to 10 carbon atoms and comprising a terminal amino group and/or 1 to 3 hydroxyl groups, c) an amino acid residue, d) a five or six carbon sugar and e) H, R.sub.3 is a residue selected from the group consisting of an alkyl, alkenyl, prostanyl-dialkyl, furanyl-dialkyl, cyclobutyl-dialkyl, cycloalkyl and aryl group of 2 to 40 carbon atoms length and comprising at least one keto group, epoxy group, aldehyde group, peroxy group, hydroperoxy group, hydroxyl group or a free carboxyl group, L1 is selected from the group consisting of O, NH, S, CH.sub.2, (aa), (bb), (cc), (dd), (ee), (ff), (gg), (hh), (ii), (jj), (kk), (ll), (mm), or (nn), L2 is an amide group or an ether group, X and Z are independently O, S or CH.sub.2, and Y is selected from the group consisting of O and S. ##STR00001##

The present invention relates to a compound having a structure according to formula (I) or a salt thereof, wherein: R.sub.1 is a branched or linear alkyl, acyl, alkenyl, hydroxyalkyl, hydroxyalkenyl, or hydroxy-alkinyl residue comprising 6 to 30 carbon atoms, R.sub.2 is selected from the group consisting of: a) an alkyl residue comprising 1 to 10 carbon atoms and comprising a terminal or cyclic quaternary ammonium, b) an alkyl residue comprising 1 to 10 carbon atoms and comprising a terminal amino group and/or 1 to 3 hydroxyl groups, c) an amino acid residue, d) a five or six carbon sugar and e) H, R.sub.3 is a residue selected from the group consisting of an alkyl, alkenyl, prostanyl-dialkyl, furanyl-dialkyl, cyclobutyl-dialkyl, cycloalkyl and aryl group of 2 to 40 carbon atoms length and comprising at least one keto group, epoxy group, aldehyde group, peroxy group, hydroperoxy group, hydroxyl group or a free carboxyl group, L1 is selected from the group consisting of O, NH, S, CH.sub.2, (aa), (bb), (cc), (dd), (ee), (ff), (gg), (hh), (ii), (jj), (kk), (ll), (mm), or (nn), L2 is an amide group or an ether group, X and Z are independently O, S or CH.sub.2, and Y is selected from the group consisting of O and S. ##STR00001##

Methods of isolating phenols from phenol-containing media. The methods include combining a phospholipid-containing composition with the phenol-containing medium to generate a combined medium, incubating the combined medium to precipitate phenols in the combined medium and thereby form a phenol precipitate phase and a phenol-depleted phase, and separating the phenol precipitate phase and the phenol-depleted phase. The methods can further include extracting phenols from the separated phenol precipitate phase. The extracting can include mixing the separated phenol precipitate phase with an extraction solvent to solubilize in the extraction solvent at least a portion of the phenols originally present in the phenol precipitate phase.

A limonene-based flame-retardant compound, a method of making a flame-retardant polymer, and an article of manufacture comprising a material that includes a limonene-based flame-retardant compound are provided. In an embodiment, the method includes forming a limonene-based derivative; forming a phosphorus-based flame-retardant molecule; reacting the limonene-based derivative with the phosphorus-based flame-retardant molecule to form a limonene-based flame-retardant compound; and forming a flame-retardant polymer from the limonene-based flame-retardant compound. In some embodiments, the limonene-based flame-retardant compound has variable functionality including vinyl, epoxide, methylene bridges, and thioethers.

A limonene-based flame-retardant compound, a method of making a flame-retardant polymer, and an article of manufacture comprising a material that includes a limonene-based flame-retardant compound are provided. In an embodiment, the method includes forming a limonene-based derivative; forming a phosphorus-based flame-retardant molecule; reacting the limonene-based derivative with the phosphorus-based flame-retardant molecule to form a limonene-based flame-retardant compound; and forming a flame-retardant polymer from the limonene-based flame-retardant compound. In some embodiments, the limonene-based flame-retardant compound has variable functionality including vinyl, epoxide, methylene bridges, and thioethers.