Thermal Stability Assessment of Peptide Coupling Reagents Commonly Used in Pharmaceutical Manufacturing

被引：92

作者：

Sperry, Jeffrey B. ^{[1
]}

Minteer, Christopher J. ^{[1
]}

Tao, JingYa ^{[1
]}

Johnson, Rebecca ^{[2
]}

Duzguner, Remzi ^{[1
]}

Hawksworth, Michael ^{[2
]}

Oke, Samantha ^{[2
]}

Richardson, Paul. F. ^{[3
]}

Barnhart, Richard ^{[1
]}

Bill, David R. ^{[1
]}

Giusto, Robert A. ^{[1
]}

Weaver, John D., III ^{[1
]}

机构：

[1] Pfizer Chem Res & Dev, Proc Safety Labs, 558 Eastern Point Rd, Groton, CT 06340 USA

[2] Pfizer Chem Res & Dev, Proc Safety Labs, Ramsgate Rd, Sandwich CT13 9NJ, Kent, England

[3] PfizerWorldwide Med Chem, 10770Sci Ctr Dr, San Diego, CA 92121 USA

来源：

ORGANIC PROCESS RESEARCH & DEVELOPMENT | 2018年 / 22卷 / 09期

关键词：

thermal stability; peptide coupling reagent; differential scanning calorimetry; explosivity; LARGE-SCALE SYNTHESIS; CHEMOKINE RECEPTOR ANTAGONIST; AMIDE BOND FORMATION; SCALABLE SYNTHESIS; KILOGRAM-SCALE; PROTEASE INHIBITOR; ENANTIOSELECTIVE SYNTHESIS; BENZIMIDAZOLE SYNTHESIS; ASYMMETRIC-SYNTHESIS; EXPLOSIVE PROPERTIES;

D O I：

10.1021/acs.oprd.8b00193

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Amide couplings are one of, if not the most common chemical reactions performed in the pharmaceutical industry. Many amide bonds are generated with the help of highly active peptide coupling reagents. These reagents have garnered wide use in the pharmaceutical industry, but many contain high-energy functional groups. As a result, significant time is spent assessing the thermal stability of these reagents before scale-up commences. This paper assesses the thermal stability of 45 common peptide coupling reagents by differential scanning calorimetry and accelerating rate calorimetry. Those compounds which flagged as potentially impact-sensitive or potentially explosive were tested by drop hammer and explosivity screening techniques. The data are presented in an effort to drive the development of these reactions toward the use of one of the more thermally stable reagents.

引用

页码：1262 / 1275

页数：14

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