from the United States District Court for the District of
Delaware in Nos. 1:14-cv-00915-RGA, 1:14-cv-00916-RGA, Judge
Richard G. Andrews.
Jessica Lynn Ellsworth, Hogan Lovells U.S. LLP, Washington,
DC, argued for plaintiff-appellant. Also represented by
Catherine Emily Stetson; Joseph D. Eng, Tony Valentine
Pezzano, Michael P. Dougherty, Nitya Anand, New York, NY;
Gerard M. Devlin, Jr., Alysia A. Finnegan, Raynard Yuro,
Merck & Co., Inc., Rahway, NJ.
J. Meloro, Willkie Farr & Gallagher LLP, New York, NY,
argued for defendant-appellee. Also represented by Michael
NEWMAN, LOURIE, and HUGHES, Circuit Judges.
LOURIE, CIRCUIT JUDGE.
Sharp & Dohme Corp. ("Merck") appeals from the
decision of the United States District Court for the District
of Delaware concluding, after a bench trial, that claims
21-34 ("the asserted claims") of U.S. Patent 6,
486, 150 ("the '150 patent") are invalid under
35 U.S.C. § 103 (2006). See Merck Sharp & Dohme
Corp. v. Hospira Inc., No. CV 14-915-RGA, 2016 WL
5872620, at *21 (D. Del. July 10, 2016) (Decision).
Because the district court did not err in its conclusion of
obviousness, we affirm.
owns the '150 patent, which is directed to a process for
preparing a stable formulation of ertapenem, an antibiotic
compound, shown below:
is known to be unstable because of two degradation
reactions-hydrolysis of the lactam nitrogen (highlighted by a
red circle) and dimerization via the pyrrolidine nitrogen
(highlighted by a blue square).
prior art taught that ertapenem can be stabilized from
dimerization by reacting the pyrrolidine nitrogen
with carbon dioxide to form a "carbon dioxide
adduct." The method of the '150 patent claims a
manufacturing process for a final formulation of the
antibiotic that purportedly minimizes both
dimerization and hydrolysis degradation pathways.
See Appellant's Br. 12-14. Claim 21 is
representative and reads as follows:
21. A process for preparing a final formulation product of a
compound of formula la, (IMAGE OMITTED)
or its pharmaceutically acceptable salt, or hydrates wherein,
R4, R5, and R6 are independently:
(b) (C1-C6)-alkyl, or
(c) alkali-metal or alkali earth-metal wherein the
alkali-metal or alkali earth-metal is sodium, potassium,
lithium, cesium, rubidium, barium, calcium or magnesium;
comprising the steps of:
(1) charging a solution of carbon dioxide source having a pH
range of about 6.0 to about 12.0 into a reaction vessel;
(2) adding an effective amount of a mole ratio of a base and
an active ingredient into the reaction vessel containing the
solution of carbon dioxide source to maintain pH at about 6.0
to about 9.0 and a temperature range of about -3° C. to
about 15° C.; [and]
(3) lyophilizing the solution of Step (2) to yield the final
formulation product of a compound of formula Ia with less