Oregon State University

Other

James David White

Kurt Frederick Sundermann

Rich Garrett Carter

David T Wong

Larrie A Deardurff

Jongtae Yang

Christopher Lincoln

David B Chan

Rajan Juniku

The present disclosure concerns a compound, or a pharmaceutically acceptable salt thereof, having a formula: where at least one of R-Ris a heterocycle, at least one of R-Ris an aryl group coupled to the ring by a linker atom, functional group, or other moiety, or where none of R-Ris an amide, and any and all combinations thereof. Remaining R-Rsubstituents independently are aliphatic, substituted aliphatic, amine, substituted amine, aryl, substituted aryl, cyclic, substituted cyclic, halide, heteroaryl, substituted heteroaryl, heterocyclic, substituted heterocyclic, hydrogen or hydroxyl. A method for treating a subject also is provided comprising administering a disclosed compound or compounds, or a prodrug that is converted into the disclosed compound or compounds, or a composition comprising the compound, compounds, or prodrugs thereof, to a subject. A method for making disclosed compounds also is provided.

Inhibitor(s) of transporters or uptake of monoaminergic neurotransmitters

A method for making epothilones and epothilone analogs is described, as are novel compounds made by the method. One embodiment of the method was used to synthesize epothilone B by a convergent approach that entailed Wittig coupling of an ylide derived from phosphonium bromide with an aldehyde. The former was prepared from propargyl alcohol by a nine-step pathway which installed both trisubstituted double bonds with clean Z configuration. Macrolactonization of a resulting seco acid provided the following intermediate diene epothilone analog. Selective saturation of the 9,10-olefin and subsequent epoxidation provided epothilone B 

Method for synthesizing epothilones and epothilone analogs

A method for making epothilones and epothilone analogs is described, as are novel compounds made by the method. One embodiment of the method was used to synthesize epothilone B by a convergent approach that entailed Wittig coupling of an ylide derived from phosphonium bromide with an aldehyde. The former was prepared from propargyl alcohol by a nine-step pathway which installed both trisubstituted double bonds with clean Z configuration. Macrolactonization of a resulting seco acid provided the following intermediate diene epothilone analog. Selective saturation of the 9,10-olefin and subsequent epoxidation provided epothilone B.

A method for making epothilones and epothilone analogs is described, as are novel compounds made by the method. Exemplary novel compounds include those according to the formula:With respect the formula, G is selected from the group consisting ofRsubstituents independently are selected from the group consisting of H and lower alkyl groups; Z is selected from the group consisting of the halogens and &#x2014;CN; M is selected from the group consisting of O and NR; Ris selected from the group consisting of H, lower alkyl, RCO, ROCO, and RSO; Ris selected from the group consisting of H, lower alkyl, and aryl; T is selected from the group consisting of CH, CO, HCOH and protected derivatives thereof; W is H or OR; and X and Y independently are selected from the group consisting of O, NH, S, CO, and C. Embodiments of the method provide convenient access to analogs of the epothilones, such as those having alternate stereochemistry and those containing an ester, amide, thioester, or alkyne moieties in the macrocycle.

An aqueous ink jet ink is disclosed which comprises an effective amount of an azomethine dye having at least one water solubilizing functional group covalently attached thereto. The water solubilizing functional group can either be directly attached to the azomethine dye and/or can be attached to the azomethine dye through an electrophilic coupling moiety. If an organic spacer group is used to separate the water solubilizing functional group from azomethine dye or the electrophilic coupling moiety, then straight and branched chained alkyl groups having from about 1 to 10 carbon atoms is preferred. Preferred azomethine dyes can be pyrazolone azomethines, pyrazolotriazole azomethines, and combinations thereof. Additionally, an aqueous ink jet ink is disclosed comprising an effective amount of a dye-based colorant and an essentially water soluble spiroindane additive for improving light fastness and stability of the dye-based colorant.

Growing community of inventors

Philomath, OR, United States of America

James David White