US 9,120,818 B2Granted

Process and intermediates for preparing macrolactams

AssigneeMerck Sharp & Dohme Corp.

InventorsCheng Chen, Jongrock Kong, Guy Humphrey, Sarah Dolman, Hongmei Li, Matthew T. Tudge, Kelvin Yong, Bangping Xiang, Michael Zacuto

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Abstract

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.

Claims20

Dependent claims

A compound selected from the group consisting of:

or a salt thereof;
and
or a salt thereof;
wherein R1 is either a C1-6 alkyl, C3-C8 cycloalkyl, or Aryl;
R2 and R3 are each either H, C1-6 alkyl, C3-C8 cycloalkyl, or Aryl;
R1a, R2a, and R3a are each either C1-6 alkyl or C3-C8 cycloalkyl;
n is 0-5;
Aryl is either phenyl, substituted phenyl, naphthyl, or substituted naphthyl, provided that substituted phenyl and substituted naphthyl each have 1 to 5 substituents independently selected from the group consisting of:
(1) C1-6 alkyl,
(2) C1-6 alkyl substituted with OH, O—C1-6 alkyl, O—C1-6 haloalkyl, CN, NO2, N(RA)RB, C(O)N(RA)RB, C(O)RA, CO2RA, SRA, S(O)RA, SO2RA, SO2N(RA)RB, N(RA)C(O)RB, N(RA)CO2RB, N(RA)SO2RB, N(RA)SO2N(RA)RB, OC(O)N(RA)RB, N(RA)C(O)N(RA)RB, or N(RA)C(O)C(O)N(RA)RB,
(3) O—C1-6 alkyl,
(4) C1-6 haloalkyl,
(5) O—C1-6 haloalkyl,
(6) OH,
(7) halogen,
(8) CN,
(9) NO2,
(10) N(RA)RB,
(11) C(O)N(RA)RB,
(12) C(O)RA,
(13) C(O)—C1-6 haloalkyl,
(14) C(O)ORA,
(15) OC(O)N(RA)RB,
(16) SRA,
(17) S(O)RA,
(18) SO2RA,
(19) SO2N(RA)RB,
(20) N(RA)SO2RB,
(21) N(RA)SO2N(RA)RB,
(22) N(RA)C(O)RB,
(23) N(RA)C(O)N(RA)RB,
(24) N(RA)C(O)C(O)N(RA)RB, or
(25) N(RA)CO2RB;
and
RA and RB are each independently H or C1-6 alkyl.

32 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/993,541Filed 13 Dec 2011 · us provisional application
Priority: 14 Dec 2010
Published: US 2013/0274463 A117 Oct 2013
Granted: 1 Sep 2015
Term ends: Not estimatedThe source records don’t support an estimate.

Classification20 codes

C07D 498/16
In which the condensed system contains three hetero rings: peri-condensed systems
A61P 31/14
Antivirals: for RNA viruses
A61P 43/00
Drugs for specific purposes, not provided for in groups a61p1/00-a61p41/00
C07C 271/22
With the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms: to carbon atoms of hydrocarbon radicals…