Abstract: The present invention is related to the synthesis of huperzine A. The synthesis includes a variety of process steps that increase productivity, reduce safety concerns, and allow for increasing production of compounds of desired optical isomer. The inventive methods may encompass a single improved reaction step that may be incorporated into a known reaction process for synthesizing huperzine A or a derivative thereof to improve the overall reaction. The inventive methods also encompass complete synthesis methods for preparing huperzine A or a derivative thereof.

Abstract: Disclosed are enantiomers diastereomers, salts, solvates, hydrates and mixtures thereof, of formula I: ##STR1## The core moiety is non-cyclic or at least one five- to seven-membered ring, n is an integer from about 4 to about 16, R.sub.1 and R.sub.2 are hydrogen, halogen or C.sub.1-12 alkyl or alkenyl, and (CH.sub.2).sub.n may be substituted by a hydroxyl, halogen, oxygen, a (C.sub.1-4) alkyl group or a dimethylamino group. The compounds and pharmaceutical composition thereof are useful in methods for treating an individual having a disease or treatment-induced toxicity, mediated by second messenger activity.

Abstract: Therapeutic compounds, including resolved enantiomers and/or diastereomers, hydrates, salts, solvates and mixtures thereof, having a formula: ##STR1## wherein R.sub.0 is selected from the group consisting of hydrogen, halo, hydroxyl, amino, substituted or unsubstituted C.sub.(1-10) alkyl, C.sub.(2-10) alkenyl, cyclic or heterocyclic groups, wherein the substituents of substituted C.sub.(1-10) alkyl, C.sub.(2-10) alkenyl are other than halo; n is an integer from one to sixteen; R.sub.1, R.sub.2, and R.sub.3 are independently selected from the group consisting of a halo; haloacetoxy; hydrogen; hydroxy; oxo; --N.dbd.C.dbd.S; --N.dbd.C.dbd.O; --0--C.tbd.N; --C.tbd.N; --N.dbd.N.dbd.N; and --C--(R.sub.5).sub.3, R.sub.5 being independently a halo or hydrogen, at least one R.sub.5 being halo, at least one of R.sub.1, R.sub.2, and R.sub.3 being halo, cyano, isocyano, isothiocyano, azide or haloacetoxy group; R.sub.4 is hydrogen, C.sub.(1-6) alkyl, C.sub.(1-6) alkenyl, cyclo C.sub.

Abstract: Disclosed are enantiomers, diastereomers, salts, solvates, hydrates and mixtures thereof, of formula I: ##STR1## The core moiety is a monocyclic ring structure having five to six ring atoms and two nitrogen atoms at the 1 and 3 positions, n is an integer from 4 to 16, R.sub.1 and R.sub.2 are hydrogen, halogen or C.sub.1-12 alkyl or alkenyl, and (CH.sub.2).sub.n may be optionally substituted by a hydroxyl, halogen, oxygen, a C.sub.1-4 alkyl group or a dimethylamino group. The compounds and pharmaceutical composition thereof are useful in methods for treating an individual having a disease or treatment-induced toxicity mediated through a second messenger.

Abstract: There is disclosed a pharmaceutical composition comprising 1-(5-oxohexyl)-3-methylxanthine in admixture with a pharmaceutically acceptable excipient, wherein the pharmaceutical composition is useful for treating an immune disorder. There is also disclosed a method to modulate the response of a target cell to a stimulus, which method comprises contacting said cell with an amount of 1-(5-oxohexyl)-3-methylxanthine or a pharmaceutical composition thereof, wherein said amount effects a diminution in elevated levels of unsaturated, non-arachidonate phosphatidic acid (PA) and diacylglycerol (DAG) derived from said PA in said cells wherein said elevated levels are stimulated by an agent capable of elevating levels of said PA and said DAG, said diminution being equal to or greater than the diminution effected by treating said cells with pentoxifylline (PTX) at a concentration of 0.5 mmol, thereby modulating the response of said target cell.

Abstract: Acetal-and ketal-substituted compounds and pharmaceutical compositions thereof have the following formula:CORE MOIETY--(R).sub.j,including resolved enantiomers and/or diastereomers, hydrates, salts, solvates and mixtures thereof. j is an integer from one to three, the core moiety is non-cyclic or cyclic a monocyclic moiety having at least one nitrogen atom within the ring and R may be selected from among hydrogen, halogen, hydroxyl, amino, substituted or unsubstituted alkyl C.sub.(1-6), alkenyl C.sub.(2-6), cyclic or heterocyclic groups, and groups having a structure prescribed by formula I. At least one R has the formula I:--(CH.sub.2).sub.n --C--(R.sub.1).sub.3 Iwherein n is an integer from three to twenty; R.sub.1 is selected from among hydrogen; halogen; hydroxide; substituted or unsubstituted C.sub.(1-6) alkyl, C.sub.(1-6) alkoxy, C.sub.2-6) alkenyl, cyclic or heterocyclic group; --OR.sub.2, R.sub.2 being hydrogen or a substituted or unsubstituted C.sub.(1-6) alkyl, C.sub.

Abstract: There is disclosed a compound having the formula: ##STR1## wherein n is an integer from 5 to 9, wherein the core moiety is a heterocylic moiety wherein C.sub.a, C.sub.b, and C.sub.c are an R or S enantiomer or racemic mixture and the C.sub.a, C.sub.b, and C.sub.c carbon atoms are bonded together by a single bond, double bond, ether or ester linkages, wherein R.sub.1, R.sub.2 and R.sub.3 are independently halo, hydroxy, hydrogen, keto, isothiocyano, azide or haloacetoxy with the proviso that at least one of R.sub.1, R.sub.2 or R.sub.3 must be a halo, isothiocyano, azide or haloacetoxy group, wherein R.sub.4 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkenyl, cyclo C.sub.4-6 alkyl, or phenyl, and wherein halo refers to fluoro, chloro, bromo and iodo and salts thereof and pharmaceutical compositions thereof.

Abstract: There is disclosed an olefin-substituted compound having the formula:R--(core moiety),wherein R is a straignt chain hydrocarbon having at least one double bond and a carbon chain length of from about 6 to about 18 carbon atoms, wherein multiple double bonds are separated from each other by at least three carbon atoms, wherein the closest double bond to the core moiety is at least five carbon atoms from the core moiety, and wherein the hydrocarbon chain may be substituted by a hydroxyl, halo, keto or dimethylanimo group and/or interrupted by an oxygen atom and salts thereof and pharmaceutical compositions thereof.

Abstract: There is disclosed compounds and pharmaceutical compositions comprising compounds of the formula: ##STR1## wherein each of one or two R is independently ##STR2## wherein n is an integer from 7 to 20, at least one of X or Y is --OH and if one of X or Y is --OH then the other X or Y is H, CH.sub.3, CH.sub.3 --CH.sub.2, CH.sub.3 --(CH.sub.2).sub.2 --, or (CH.sub.3).sub.2 --CH.sub.2 --, and W.sub.1, W.sub.2, and W.sub.3 is independently H, CH.sub.3, CH.sub.3 --CH.sub.2, CH.sub.3 --(CH.sub.2).sub.2 --, or (CH.sub.3).sub.2 --CH.sub.2 --, and wherein the alkyl groups may be substituted by a hydroxyl, halo or dimethylamino group and/or interrupted by an oxygen atom, H or alkyl (1-4C), including resolved enantiomers and/or diastereomers, salts and mixtures thereof. In particular, the compounds lower elevated levels of unsaturated, non-arachidonate phosphatidic acid (PA) and diacylglycerol (DAG) derived from said PA within seconds of the primary stimulus and their contact with said cells.

Abstract: There is disclosed compounds and pharmaceutical compositions having a xanthine core of the formula: ##STR1## wherein each of one or two R is independently ##STR2## wherein n is an integer from about 3 to about 18 forming a hydrocarbon chain, wherein the hydrocarbon chain may have one or more double bonds (preferably in a cis configuration), and may be substituted by a hydroxyl, halo or dimethylamino group and/or interrupted by an oxygen atom. The compounds lower elevated levels of unsaturated, non-arachidonate phosphatidic acid (PA) and diacylglycerol (DAG) derived from said PA within seconds of the primary stimulus and their contact with cells. The modulatory effect depends on the nature of the target cell and the stimulus applied.

Abstract: There is disclosed compounds and pharmaceutical compositions having a xanthine core and one or two hydrocarbon side chains bonded to a ring nitrogen atom, wherein the hydrocarbon side chains are independently a straight chain hydrocarbon having at least one double bond in a carbon chain length of from about 4 to about 18 carbon atoms in length, wherein multiple double bonds are separated from each other by at least three carbon atoms, and wherein the hydrocarbon chain may be substituted by a hydroxyl, halo or dimethylamino group and/or interrupted by an oxygen atom. The compounds lower elevated levels of unsaturated, non-arachidonate phosphatidic acid (PA) and diacylglycerol (DAG) derived from said PA within seconds of the primary stimulus and their contact with cells. The modulatory effect depends on the nature of the target cell and the stimulus applied.

Abstract: Compounds of the formula ##STR1## wherein each of one or two R is independently ##STR2## wherein n is an integer from 4 to 18, each R.sub.1 ' and R.sub.2 ' is independently H, alkyl (1-4C) or alkenyl (1-4C); and R.sub.3 ' and R.sub.4 ' are independently H or CH.sub.3 ; and wherein the alkyl or alkenyl may be substituted by a hydroxyl, halo or dimethylamino group and/or interrupted by an oxygen atom, H or alkyl (1-4C), including resolved enantiomers and/or diastereomers and mixtures thereof. Preferably, n is from 6 to 10, R.sub.1 ' and R.sub.2 ' are independently H or methyl and R.sub.3 ' and R.sub.4 ' are H. In particular, the compounds lower elevated levels of unsaturated, non-arachidonate phosphatidic acid (PA) and diacylglycerol (DAG) derived from said PA within seconds of the primary stimulus and their contact with said cells. The modulatory effect depends on the nature of the target cell and the stimulus applied.