Bp Corporation North America Inc.

Merck Sharp + Dohme Corp.

The University of British Columbia

Lu Yang

Joseph B Binder

Liang Song

Christopher Phillips

Erin Imsand

Nobuyoshi Yasuda

Raymond John Andersen

Kevin Campos

Artis Klapars

David Williams

Gerald Krystal

Christopher J Ong

Zhijian Liu

Mikhail Reibarkh

Alice Mui

Kevin R Campos

A method is provided of preparing a compound of formula II: where: Rand Rare independently selected from —CHOR', —CHO, —COOR′ and —H, the compounds of formulas I and II being optionally in the form of a salt. The method comprises dehydrating the compound of formula I at: a pH in the range of from 0 to 6 or 8 to 11.5; and a temperature in the range of from 10 to 80° C. The method is particularly useful for synthesizing substituted furans from compounds derived from sugars.

Synthesis of substituted furans

A method is provided of preparing a compound of formula II: where: Rand Rare independently selected from &#x2014;CH2OR', &#x2014;CHO, &#x2014;COOR&#x2032; and &#x2014;H, provided that Rand Rare not both &#x2014;H; and R&#x2032; is selected from &#x2014;H and Chydrocarbyl groups, from a compound of formula I: the compounds of formulas I and II being optionally in the form of a salt. The method comprises dehydrating the compound of formula I at: a pH in the range of from 0 to 6 or 8 to 11.5; and a temperature in the range of from 10 to 80&#xb0; C. The method is particularly useful for synthesizing substituted furans from compounds derived from sugars. 

The present invention relates to processes for preparing compounds of Formula I. Such compounds include interme-diates in the manufacture of 7-oxo-1,6-diazabicyclo[3.2.1 ]octane-2-carboxamide beta-lactamase inhibitors such as (2S,5R)-7-oxo-N-5 piperidin-4-yl-6-(sulfoxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide. The present invention also relates to novel intermediates formed i these processes. The present invention relates to a process for preparing a compound of Formula I or a pharmaceutically acceptable salt thereof.

Process for the preparation of tert-butyl 4-((2S ,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamido)piperidine-1-carboxylate and analogs thereof

The present invention includes the use of pelorol, related compounds and pharmaceutical compositions thereof as modulators of SHIP 1 activity. This invention also provides novel terpene compounds capable of modulating SHIP 1 activity and methods of synthesis thereof.

Ship 1 modulators

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San Diego, CA, United States of America

Lu Yang