Merck Sharp + Dohme Corp.

Merck + Co., Inc.

Merck Sharpe & Dohme Corp.

Aicuris Anti-infective Cures Gmbh

Werthenstein Biopharma Gmbh

Guy R Humphrey

Ross A Miller

Cheol Keun Chung

Kevin Michael Belyk

Andrew S Thompson

Mark E Scott

John Limanto

Paul Gerard Bulger

Ralph P Volante

Ichiro Shinkai

Nobuyoshi Yasuda

Woo-Baeg Choi

Feng Xu

Paul J Reider

Richard John Varsolona

John Y L Chung

Peter Emmanuel Maligres

Yong-Li Zhong

Zhiguo Jake Song

Tao Wang

Wei Xu

Laura Marie Artino

Bangping Xiang

Yingju Xu

Wilfried Schwab

Younong Yu

David M Tschaen

Hongmei Li

Steven A Weissman

Edward Cleator

James A McCauley

Jeonghan Park

Gregory L Beutner

Kevin Matthew Maloney

Gang Qian

Michael J Zacuto

Cheng Yi Chen

Kallol Basu

Tao Pei

Michel Journet

Ji Qi

Michael Stewart Ashwood

Wenjie Li

Richard Desmond

David R Lieberman

Zhijian Liu

Donald R Gauthier

Burkhard Klenke

Yang Cao

Tetsuji Itoh

Alfred Lee

Peter G Houghton

Jeffrey T Kuethe

Mark McLaughlin

Kelvin Yong

Marjorie See Waters

Carl A Baxter

Feng Peng

Roger N Farr

Andrew L Forman

Timothy James Wright

Benjamin D Sherry

Michael R Luzung

Rebecca T Ruck

Brian Cchristopher Bishop

David M Tellers

Hongming Li

Matthew Thomas Tudge

Hong Ren

Stephen Mark Dalby

Ann M Madar

Tom Moody

Paul F McKenzie

Gareth Brown

David M Lashen

Sean R Holihan

Pascal H Toma

Cynthia Marilyn Hong

Kevin M Maloney

Jongrock Kong

Sarah Dolman

Michael James Di Maso

Siwei Zhang

Steven Weissman

The present invention provides processes for the preparation of 2-fluoroadenine, as well as certain intermediates useful in the preparation of 2′-deoxy-4′-C-ethynyl-2-fluoroadenosine (EFdA): EFdA.

Process for the preparation of 2-fluoroadenine

Disclosed herein is a novel process for preparing Compound A free base, 5-((2,4-diaminopyrimidin-5-yl)oxy)-4-iso-propyl-2-methoxybenzenesulfonamide, and a citrate salt of Compound A with simplified chemistry and a high overall yield: Compound A. In one embodiment, the overall yield from the starting material 2-isopropylphenol to Compound A citrate salt is greater than 50%. In another embodiment, the overall yield is greater than 60%. Also disclosed herein are novel salts and solvates of Compound A.

Process for synthesis of a phenoxy diaminopyrimidine compound

A novel process is provided for the efficient preparation of an asymmetric compound of structural formula I: comprising a copper-catalyzed, carbon-nitrogen cross-coupling step. The process described as part of the present invention can be used to manufacture poly (ADP-ribose) polymerase (PARP) inhibitors, which may be useful for the treatment of cancer. In particular, the present invention describes a process for the manufacture of the PARP inhibitor, 2-{4-[(3S)-piperidin-3-yl]phenyl}-2H-indazole-7-carboxamide.

Regioselective N-2 arylation of indazoles

Disclosed herein is a novel process for preparing substituted quinazoline compounds of formula (I) using a hydrogen bonding catalyst. 

Processes for making substituted quinazoline compounds using hydrogen bonding catalysts

The present invention is directed to a process for making Substituted Quinazoline Compounds of formula (I): which are useful for the treatment and prophylaxis of HCMV infection. The present invention is also directed to compounds that are useful as synthetic intermediates for making the compounds of formula (I). 

Process for making substituted quinazoline compounds

The present invention includes compounds useful as intermediates in the preparation of macrolactams, methods for preparing the intermediates, and methods for preparing macrolactams. One use of the methods and intermediates described herein is in the production of macrolactam compounds able to inhibit HCV NS3 protease activity. HCV NS3 inhibitory compounds have therapeutic and research applications.

Methods and intermediates for preparing macrolactams

The present invention is directed to a novel process for synthesizing 3-(substituted phenoxy)-1-[(5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl])-pyridin-2(1H)-one derivatives. The compounds synthesized by the processes of the invention are HIV reverse transcriptase inhibitors useful for inhibiting reverse transcriptase and HIV replication, and the treatment of human immunodeficiency virus infection in humans.

Process for making reverse transcriptase inhibitors

The present invention includes compounds useful as intermediates in the preparation of macrolactams, methods for preparing the intermediates, and methods for preparing macrolactams from the intermediates. One use of the methods and intermediates described herein is in the production of macrolactam compounds able to inhibit HCV NS3 protease activity. HCV NS3 inhibitory compounds have therapeutic and research applications.

Process and intermediates for preparing macrolactams

An efficient process is disclosed for producing the compound of formula I, which is the CETP inhibitor anacetrapib, which raises HDL-cholesterol and reduces LDL-cholesterol in human patients and may be effective for treating or reducing the risk of developing atherosclerosis: 

Process for synthesizing a CETP inhibitor

The present invention relates to macrolactam compounds, intermediates useful in the preparation of macrolactams, methods for preparing the intermediates, and methods for preparing and modifying macrolactams. One use of the compounds and methods described herein is in the production of macrolactam compounds able to inhibit HCV NS3 protease activity. An example of an HCV inhibitory compound that can be synthesized using the procedures described herein is Compound A and derivative thereof.

A first aspect of the present invention describes a compound selected from group consisting of: wherein R is either H, C(O)R, or C(O)NHCH(X)COOH; provided that X is a C-Calkyl, or a C-Ccycloalkyl and Ris a Calkyl or aryl; These compounds are used to make Compound A 

Processes for preparing certain N-arylalkyl-1-(alkyl or aralkyl)-2-acylaminoalkyl-5-hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxamides are disclosed. In one embodiment, the process comprises acylating the free amine in the corresponding N-arylalkyl-1-(alkyl or aralkyl)-2-aminoalkyl-5-ester protected hydroxy-6-oxo-1,6-dihydropyrimidine-4-carboxamide and then deprotecting the 5-hydroxy by base hydrolysis. The hydroxypyrimidinone carboxamide products of the process are HTV integrase inhibitors which are useful for treating HTV infection, treating AIDS, or delaying the onset or progression of AIDS. Certain esterified N-arylalkyl hydroxypyrimidinone carboxamides that can be employed as process intermediates are also disclosed. 

Process for preparing N-substituted hydroxypyrimidinone carboxamides

The present invention provides an asymmetric hydrogenation process for the preparation of chiral cycloalkanoindole DP receptor antagonists in high enantiomeric excess.

Asymmetric hydrogenation process

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Hillsborough, NJ, United States of America

Guy R Humphrey