University of Pittsburgh

University of Kentucky Research Foundation

Fluorous Technologies Inc.

Other

Dennis Patrick Curran

Hubert B Josien

Bom David

Thomas G Burke

Hui C Liu

Zhiyong Luo

David Bom

Billy W Day

Youseung Shin

Sung Bo Ko

Armido Studer

Wu Du

Masahide Hoshino

Hiroyuki Nakamura

Peter Wipf

Roger Wayne Read

Maree Patricia Collis

Raghavan Balachandran

Tiffany Turner

Sabine Hadida Ruah

Patrick Jeger

Rafael Ferritto

Sun-Young Kim

Charitha Madiraju

Marvin Sungwhan Yu

Bruno Linclau

Stephen G Weber

Craig Stephens Wilcox

Oscar De Frutos Garcia

Ilhyong Ryu

Hiroshi Matsubara

Sabine Hadida

Marc Oliver Wende

Ana E Gabarda

Qisheng Zhang

Lifang Sun

Yoji Oderaotoshi

Sivaraman Dandapani

Lori Latus, Legal Representative

Thomas G Burke, Deceased

Yoshikazu Fukui

Arndt Bruckner

John Mancuso

Jean-Hugues Fournier

Masato Matsugi

John Andrew Gladysz

Masahide Hashino

A compound having the formula in racemic form, enantiomerically enriched form or enantiomerically pure form, and pharmaceutically acceptable salts thereof.

Camptothecin analogs and methods of preparation thereof

Analogs of discodermolide and dictyostatin-1, intermediates therefor and methods of synthesis thereof

The present invention provides a method for conducting a chemical reaction in a non-fluorous medium using a fluorous compound in the presence of a solid adsorbant containing a fluorous domain and at least one chemical reactant, comprising contacting the fluorous compound and at least one chemical reactant under conditions that form at least one product.

Recovery method for catalysts, reagents and co-products

A method of separating compounds, includes: a. tagging at least a first organic compound with a first tagging moiety to result in a first tagged compound; b. tagging at least a second organic compound with a second tagging moiety different from the first tagging moiety to result in a second tagged compound, the first tagging moiety and the second tagging moiety including at least one of a common repeat unit, but having a different number of the repeat units therein, the greater the number of repeat units, the greater the polarity of the tagging moiety; and c. separating the first tagged compound from a mixture including at least the second tagged compound using a chromatographic separation technique based upon differences in the number of repeat units between the first tagging moiety and the second tagging moiety.

Separation of compounds using tagging moieties including varying numbers of repeat units

A method of increasing the fluorous nature of a compound includes the step of reacting the compound with at least one second compound having the formula: wherein Rf is a fluorous group, Rs is a spacer group, d is 1 or 0, m is 1, 2 or 3, Ra is an alkyl group and X is a suitable leaving group. A compound has the formula: wherein Rf is a fluorous group, n is an integer between 0 and 6, m is 1, 2 or 3, Ra is an alkyl group and X is a leaving group.

Fluorous tagging compounds and methods of increasing the fluorous nature of compounds

A method of inhibiting topoisomerase I mediated DNA cleavage including administering a pharmaceutically effective amount of a compound having the following formula or a pharmaceutically acceptable salt thereof: wherein Rand Rare independently the same or different and are hydrogen, an alkyl group, an aminoalkyl group, an alkylaminoalkyl group, a haloalkyl group, a hydroxyalkyl group, an alkenyl group, an alkynyl group, an alkoxyl group, an aryloxy group, a carbamoyloxy group, a halogen, a hydroxyl group, a nitro group, a cyano group, an azido group, a formyl group, a hydrazino group, &#x2014;C(O)R, an amino group, an alkylamino group, a dialkylamino group, &#x2014;SR, or Rand Rtogether form a group of the formula &#x2014;O(CH)O&#x2014; wherein n represents the integer 1 or 2; Ris H, F, a halogen atom, a nitro group, an amino group, a hydroxyl group, or a cyano group; or Rand R3 together form &#x2014;O(CH)O&#x2014; (n=1 or 2); Ris H, F, a Calkyl group, a Calkenyl group, a Calkynyl group, or a Calkoxyl group; Ris a Calkyl group, or a propargyl group.

A compound having the formula in racemic form, enantiomerically enriched form or enantiomerically pure form; wherein X is a radical precursor; Ris a Calkyl group, an alkenyl group, an alkynyl group, or a benzyl group; Ris an alkyl group, &#x2014;Si(RRR) or &#x2014;(R)Si(RRR), wherein Ris an alkylene group, an alkenylene group, or an alkynylene group; and R, Rand Rare independently a Calkyl group, a Calkenyl group, a Calkynyl group, an aryl group or a &#x2014;(CH)Rgroup, wherein N is an integer within the range of 1 through 10 and Ris a hydroxy group, an alkoxy group, an amino group, an alkylamino group, a dialkylamino group, a halogen atom, a cyano group, &#x2014;SRor a nitro group; and Ris H, F or &#x2014;CH.

Intermediates in the preparation of homocamptothecin analogs

The present invention provides generally a compound having the following general formula (1): wherein Rand Rare independently the same or different and are hydrogen, an alkyl group, an alkenyl group, a benzyl group, an alkynyl group, an alkoxyl group, an aryloxy group, an acyloxy group, a carbonyloxy group, a carbamoyloxy group, a halogen, a hydroxyl group, a nitro group, a cyano group, an azido group, a formyl group, a hydrazino group, an acyl group, an amino group, &#x2014;SR, wherein, Ris hydrogen, an acyl group, an alkyl group, or an aryl group, or Rand Rtogether form a group of the formula &#x2014;O(CH)O&#x2014; wherein n represents the integer 1 or 2; Ris H, F, a halogen atom, a nitro group, an amino group, a hydroxyl group, or a cyano group; or Rand Rtogether form a group of the formula &#x2014;O(CH)O&#x2014; wherein n represents the integer 1 or 2; Ris H, F, a Calkyl group, a Calkenyl group, a Calkynyl group, or a Calkoxyl group; Ris a Calkyl group, or a propargyl group; and R, Rand Rare independently a Calkyl group, a Calkenyl group, a Calkynyl group, an aryl group or a &#x2014;(CH)Rgroup, wherein N is an integer within the range of 1 through 10 and Ris a hydroxyl group, alkoxy group, an amino group, an alkylamino group, a dialkylamino group, a halogen atom, a cyano group or a nitro group; and pharmaceutically acceptable salts thereof.

A method of separating at least a first non-fluorous compound from a mixture of compounds including at least the first non-fluorous compound and a second fluorous compound includes: charging the of compounds to a non-fluorous solid (stationary) phase and eluting with a fluorous eluting fluid (mobile phase). In one embodiment, the non-fluorous solid phase is polar in nature. The method can further include a second phase elution with a suitable organic solvent. A method conducting a chemical reaction, includes: mixing at least a first fluorous compound and a second compound, the first fluorous compound differing in fluorous nature from the second compound; exposing the first mixture to conditions to convert at least one of the first fluorous compound and the second compound to give a second mixture containing at least a third compound, charging the second mixture to a non-fluorous solid phase; and eluting with a fluorous fluid.

Separation of fluorous compounds

Dictyostatin and its analogs show great promise as new anticancer agents. The present invention provides dictyostatin analogs, synthetic intermediates for the synthesis of dictyostatin analogs, and synthetic methods for the synthesis of such analogs and intermediates. Dictyostatin analogs can have the following structure or its enantiomer wherein Ris H, an alkyl group, an aryl group, an alkenyl group, an alkynyl group, or a halogen atom; Ris H, a protecting group, an alkyl group, a benzyl group, a trityl group, &#x2014;SiRRR, CHOR, or COR; R, Rand Rare independently an alkyl group or an aryl group; Ris an alkyl group, an aryl group, an alkoxylalkyl group, &#x2014;RSiRRRor a benzyl group, wherein Ris an alkylene group; Ris an alkyl group, an allyl group, a benzyl group, an aryl group, an alkoxy group, or &#x2014;NRR, wherein Rand Rare independently H, an alkyl group or an aryl group; Ris (CH)where n is and integer in the range of 0 to 5, &#x2014;CHCH(CH)&#x2014;, &#x2014;CH&#x2550;CH&#x2014;, &#x2014;CH&#x2550;C(CH)&#x2014;, or &#x2014;C&#x2261;C&#x2014;; Ris wherein Ris H, a protecting group, an alkyl group, a benzyl group, a trityl group, &#x2014;SiRRR, CHOR, or COR; Ris H, a protecting group, an alkyl group, a benzyl group, a trityl group, &#x2014;SiRRR, CHOR, or COR, or Rand Rtogether form a portion of six-membered acetal ring incorporating CRR; Rand Rare independently H, an alkyl group, an aryl group or an alkoxyaryl group; and Ris H or OR, wherein Ris H, a protecting group, an alkyl group, an aryl group, a benzyl group, a trityl group, &#x2014;SiRRR, CHOR, or COR; provided that the compound is not dictyostatin 1.

Analogs of dictyostatin, intermediates therefor and methods of synthesis thereof

A compound has the formula in racemic form, enantiomerically enriched form or enantiomerically pure form. Ris preferably &#x2014;Si(RRR) or &#x2014;(R)Si(RRR), wherein Ris an alkylene group, an alkenylene group, or an alkynylene group; and R, Rand Rare independently a Calkyl group, a Calkenyl group, a Calkynyl group, an aryl group or a &#x2014;(CH)Rgroup, wherein N is an integer within the range of 1 through 10 and Ris a hydroxy group, alkoxy group, an amino group, an alkylamino group, a dialkylamino group, a halogen atom, a cyano group, &#x2014;SRor a nitro group. Rcan be broadly substituted. Ris preferably a Calkyl group, an alkenyl group, an alkynyl group, or a benzyl group. Ris preferably H, F or &#x2014;CH. Ris Ris &#x2014;C(O)Ror H. The E-ring (the lactone ring) may be opened. A method of synthesis of compound (1) and intermediates in the synthesis thereof are provided.

A method of obtaining an enantioenriched organic compound comprising the steps of: 1) generating from a starting racemic, non-enantiopure or achiral compound a first mixture comprising at least one fluorous-tagged compound and at least one other non-fluorous tagged compound, at least one of these two compounds being enantioenriched relative to the starting compound; 2) contacting a first non-fluorous phase including the first mixture with a fluorous phase at a first phase interface, the fluorous-tagged compound distributing between the first non-fluorous phase and the fluorous phase; and 3) contacting the fluorous phase with a second non-fluorous phase at a second phase interface. The method further includes the step of having a third compound in the second non-fluorous phase that reacts with the fluorous-tagged compound to produce a second compound and the step of generating the first mixture by chemical or enzymatic kinetic resolution of a racemic or non-enantiopure compound.

Fluorous triphasic reaction and separation processes for the generation of enantioenriched alcohols, amines, carboxylic acids and related compounds

A compound of the following structure: wherein Ris H, an alkyl group, an aryl group, an alkenyl group, an alkynyl group, or a halogen atom;

The present invention relates to novel intermediates and prodrugs of camptothecin and related analogs.

Camptothecin intermediates and prodrugs and methods of preparation thereof

Growing community of inventors

Pittsburgh, PA, United States of America

Dennis Patrick Curran