Daniel J. Pippel
Urbana University
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Publication
Featured researches published by Daniel J. Pippel.
Journal of Medicinal Chemistry | 2015
Michael A. Letavic; Pascal Bonaventure; Nicholas I. Carruthers; Christine Dugovic; Tatiana Koudriakova; Brian Lord; Timothy W. Lovenberg; Kiev S. Ly; Neelakandha S. Mani; Diane Nepomuceno; Daniel J. Pippel; Michele Rizzolio; Jonathan Shelton; Chandra R. Shah; Brock T. Shireman; Lana K. Young; Sujin Yun
The preclinical characterization of novel octahydropyrrolo[3,4-c]pyrroles that are potent and selective orexin-2 antagonists is described. Optimization of physicochemical and DMPK properties led to the discovery of compounds with tissue distribution and duration of action suitable for evaluation in the treatment of primary insomnia. These selective orexin-2 antagonists are proven to promote sleep in rats, and this work ultimately led to the identification of a compound that progressed into human clinical trials for the treatment of primary insomnia. The synthesis, SAR, and optimization of the pharmacokinetic properties of this series of compounds as well as the identification of the clinical candidate, JNJ-42847922 (34), are described herein.
Journal of Organic Chemistry | 2010
Daniel J. Pippel; Lana K. Young; Michael A. Letavic; Kiev S. Ly; Bita Naderi; Aki Soyode-Johnson; Emily M. Stocking; Nicholas I. Carruthers; Neelakandha S. Mani
We have recently completed the synthesis of 1-[2-(4-cyclobutyl-[1,4]diazepane-1-carbonyl)-4-(3-fluoro-phenoxy)-pyrrolidin-1-yl]-ethanone, a hydroxyproline-based H(3) receptor antagonist, on 100 g scale. The synthesis proceeds through four steps and route selection was driven by a desire to minimize the cost-of-goods. Naturally occurring trans-4-hydroxy-L-proline was chosen as the precursor to the targets core, which necessitated an inversion at both stereogenic centers. The inversions were accomplished through strategic employment of La Rosas lactone and a late-stage Mitsunobu reaction. A first generation synthesis that employed N-Boc-homopiperazine was improved in a second generation approach wherein homopiperazine was directly desymmetrized. Finally, the water solubility of a key intermediate necessitated the development of a nonextractive workup for the sodium triacetoxyborohydride reduction.
Journal of Organic Chemistry | 1998
Daniel J. Pippel; Michael D. Curtis; Hua Du; Peter Beak
Archive | 2009
Sergio Cesco-Cancian; Jeffrey S. Grimm; Neelakandha S. Mani; Christopher M. Mapes; David C. Palmer; Daniel J. Pippel; Tong Xiao; Diego Broggini; Susanne Lochner
Organic Process Research & Development | 2011
Daniel J. Pippel; John E. Mills; Chennagiri R. Pandit; Lana K. Young; Hua M. Zhong; Frank J. Villani; Neelakandha S. Mani
Archive | 2009
Luigi Anzalone; Daniel J. Pippel; Neelakandha S. Mani; Penina Feibush; Ilias Konstantinos Dorziotis; Stefan Horns; Frank J. Villani
Archive | 2013
Sergio Cesco-Cancian; セルジオ・セスコ−カンシアン; Jeffrey S. Grimm; ジエフリー・エス・グリム; S Mani Neelakandha; ニーラカンダ・エス・マニ; Christopher M. Mapes; クリストフアー・エム・メイプス; C Palmer David; デイビツド・シー・パルマー; Daniel J. Pippel; ダニエル・ジエイ・ピツペル; Tong Xiao; トン・シアオ; Broggini Diego; デイエゴ・ブロジーニ; Susanne Lochner; スザンヌ・ロフナー
Archive | 2010
Wenying Chai; Michael A. Letavic; Kiev S. Ly; Daniel J. Pippel; Dale A. Rudolph; Kathleen C. Strother; Brad M. Savall; Chandravadan R. Shah; Brock T. Shireman; Akinola Soyode-Johnson; Emily M. Stocking; Devin M. Swanson
Archive | 2010
Wenying Chai; Michael A. Letavic; Kiev S. Ly; Daniel J. Pippel; Dale A. Rudolph; Kathleen C. Sappey; Brad M. Savall; Chandravadan R. Shah; Brock T. Shireman; Akinola Soyode-Johnson; Emily M. Stocking; Devin M. Swanson
Archive | 2009
Nicholas I. Carruthers; Michael A. Letavic; Kiev S. Ly; Neelakandha S. Mani; Daniel J. Pippel; Chandravadan R. Shah; Aki Soyode-Johnson; Emily M. Stocking; Lana Young