A method to reduce the aldehyde content of a pine chemical composition is disclosed. The pine chemical composition is selected from gum turpentine, gum rosin, CST BLS, CTO, depitched CTO, DTO, TOH, TOR, TOP, TOFA, fractionated TOFA, TOFA dimer, TOFA trimer, TOFA monomer, isostearic acid, stearic acid, and ester- and amide derivatives thereof. The pine chemical composition is treated with an aldehyde scavenger such as anthranilamide at a temperature between 20 C. to 300 C., for 1 minute to 5 hours.

Disclosed are compounds of Formulas (I), (II), (III), (IV), and (V):

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and/or a salt thereof, wherein R.sub.1 is OH or OP(O)(OH).sub.2, and X.sub.1, X.sub.2, X.sub.3, R.sub.2, R.sub.2a, R.sub.a, R.sub.b, and R.sub.c are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P.sub.1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

Disclosed are compounds of Formulas (I), (II), (III), (IV), and (V):

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and/or a salt thereof, wherein R.sub.1 is OH or OP(O)(OH).sub.2, and X.sub.1, X.sub.2, X.sub.3, R.sub.2, R.sub.2a, R.sub.a, R.sub.b, and R.sub.c are defined herein. Also disclosed are methods of using such compounds as selective agonists for G protein-coupled receptor S1P.sub.1, and pharmaceutical compositions comprising such compounds. These compounds are useful in treating, preventing, or slowing the progression of diseases or disorders in a variety of therapeutic areas, such as autoimmune diseases and vascular disease.

The present invention relates to a process for synthesis of a compound according to Formula (A): wherein R.sub.1 is a substituted or unsubstituted aryl having 6 to 20 carbon atoms; preferably substituted or unsubstituted phenyl; R.sub.2 is a straight or branched alkyl having 1 to 12 carbon atoms; and R.sub.3 is a straight or branched alkyl having 1 to 12 carbon atoms; starting from a di-keto compound according to Formula (B) wherein R.sub.3 is as shown above, which compound is converted into a ketoenamine compound according to Formula (C) wherein R.sub.2 and R.sub.3 are as shown above, which ketoenamine compound is then reduced to an amino alcohol according to Formula (D), wherein R.sub.2 and R.sub.3 are as shown above, that is subsequently converted into a compound according to Formula (A): characterized in that the ketoenamine is reduced into an amino alcohol using a nickel aluminium alloy in an aqueous solution of an inorganic base. ##STR00001##

The present invention relates to a process for synthesis of a compound according to Formula (A): wherein R.sub.1 is a substituted or unsubstituted aryl having 6 to 20 carbon atoms; preferably substituted or unsubstituted phenyl; R.sub.2 is a straight or branched alkyl having 1 to 12 carbon atoms; and R.sub.3 is a straight or branched alkyl having 1 to 12 carbon atoms; starting from a di-keto compound according to Formula (B) wherein R.sub.3 is as shown above, which compound is converted into a ketoenamine compound according to Formula (C) wherein R.sub.2 and R.sub.3 are as shown above, which ketoenamine compound is then reduced to an amino alcohol according to Formula (D), wherein R.sub.2 and R.sub.3 are as shown above, that is subsequently converted into a compound according to Formula (A): characterized in that the ketoenamine is reduced into an amino alcohol using a nickel aluminium alloy in an aqueous solution of an inorganic base. ##STR00001##

Disclosed herein is a compound of formula (I), or a pharmaceutically acceptable salt thereof: (Formula (I)). Also disclosed herein are uses of a compound disclosed herein in the potential treatment or prevention of an IDO-associated disease or disorder. Also disclosed herein are compositions comprising a compound disclosed herein. Further disclosed herein are uses of a composition in the potential treatment or prevention of an IDO-associated disease or disorder.

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The modified graphene includes a structure represented by the following formula (I), wherein the modified graphene has a ratio (g/d) of an intensity g of a G band to an intensity d of a D band of 1.0 or more in a Raman spectroscopy spectrum thereof:

Gr1-Ar1-X1-(Y1).sub.n1(I)

in the formula (I), Gr1 represents a single-layer graphene or a multilayer graphene, Ar1 represents an arylene group having 6 to 18 carbon atoms, X1 represents a single bond, a linear, branched, or cyclic alkylene group having 1 to 20 carbon atoms, or a group obtained by substituting at least one carbon atom in a linear, branched, or cyclic alkylene group having 1 to 20 carbon atoms with at least one structure selected from the group consisting of O, NH,

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CO, COO, CONH, and an arylene group.

The modified graphene includes a structure represented by the following formula (I), wherein the modified graphene has a ratio (g/d) of an intensity g of a G band to an intensity d of a D band of 1.0 or more in a Raman spectroscopy spectrum thereof:

Gr1-Ar1-X1-(Y1).sub.n1(I)

in the formula (I), Gr1 represents a single-layer graphene or a multilayer graphene, Ar1 represents an arylene group having 6 to 18 carbon atoms, X1 represents a single bond, a linear, branched, or cyclic alkylene group having 1 to 20 carbon atoms, or a group obtained by substituting at least one carbon atom in a linear, branched, or cyclic alkylene group having 1 to 20 carbon atoms with at least one structure selected from the group consisting of O, NH,

##STR00001##

CO, COO, CONH, and an arylene group.

Compounds of general formula IA, IB and IC outlined below, including pharmaceutically acceptable salts, solvates and hydrates thereof. Such compounds and pharmaceutical compositions comprising them may be used in medical conditions involving Ran GTPase.

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Disclosed is a fluorination method comprising providing an aryl fluorosulfonate and a fluorinating reagent to a reaction mixture; and reacting the aryl fluorosulfonate and the fluorinating reagent to provide a fluorinated aryl species.

Also disclosed is a fluorination method comprising providing , a salt comprising a cation and an aryloxylate, and SO.sub.2F.sub.2 to a reaction mixture; reacting the SO.sub.2F.sub.2 and the ammonium salt to provide a fluorinated aryl species.

Further disclosed a fluorination method comprising providing a compound having the structure Ar-OH to a reaction mixture; where Ar is an aryl or heteroaryl; providing SO.sub.2F.sub.2 to the reaction mixture; providing a fluorinating reagent to the reaction mixture; reacting the SO.sub.2F.sub.2, the fluorinating reagent and the compound having the structure Ar-OH to provide a fluorinated aryl species having the structure Ar-F.