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Waters Corp. v. Agilent Technologies Inc.

United States District Court, D. Delaware

September 20, 2019


          Karen L. Pascale, Robert M. Vrana, Young Conaway Stargatt & Taylor LLP, Wilmington, DE; Matthew M. Wolf, David McMullen, Jennifer A. Sklenar, Katie J.L. Scott, Arnold & Porter Kaye Scholer LLP – attorneys for Plaintiffs.

          Chad M. Shandler, Travis S. Hunter, Richards, Layton & Finger, P.A., Wilmington, DE; Anne Elise Herold Li, James K. Stronski, Mark Jansen, Molly Jones, Chiemi Suzuki, Crowell & Moring LLP – attorneys for Defendants September 20, 2019 Wilmington, Delaware



         Presently before the Court is the motion of Plaintiffs Waters Corporation and Waters Technologies Corporation (collectively, “Plaintiffs” or “Waters”) for preliminary injunction seeking to enjoin Defendant “Agilent [Technologies Inc. (“Defendant” or “Agilent”)] and their officers, partners, agents, servants, employees, parents, subsidiaries, divisions, affiliate corporations, other related business entities and all other persons acting in concert, participation, or in privity with them” from “any commercial manufacture, use, offer to sell, or sale within the United States, or importation into the United States, of the InstantPC glycan reagent, and any product that is similar to or only colorably different from that product.” (D.I. 7). Defendant opposes the motion. (D.I. 18). The Court has reviewed the briefing, declarations and exhibits (e.g., D.I. 7, 8, 9, 10, 11, 12, 13, 18, 19, 20, 21, 23, 24, 27, 36, 37, 38, 41, 71, 72, 73, 77, 78, 81) and held oral argument on December 21, 2018. For the reasons set forth below, the Court DENIES Plaintiffs’ motion. This opinion constitutes the Court’s findings of fact and conclusions of law pursuant to Federal Rule of Civil Procedure 52(a).

         I. BACKGROUND

         Plaintiffs develop “analytical solutions . . . to support its customers’ scientific discoveries, operations, performance, and regulatory compliance.” (D.I. 12 at ¶ 8). In particular, Plaintiffs sell the “GlycoWorks RapiFluor-MS N-Glycan Kit” (“GlycoWorks Kit”) which they assert “enables unprecedented fluorescent and mass spectrometric performance for glycan detection while also improving the speed and simplicity of N-glycan sample preparation.” (D.I. 8 at 3 (citing D.I. 12 at ¶¶ 10-11)). The chemical structure of the labeling reagent in the GlycoWorks Kit is (D.I. 13 at ¶ 16):

         (Image Omitted)

         Plaintiffs' GlycoWorks kits make up approximately 75 to 80% of the market for such products. (D.I. 11 at ¶ 8; D.I. 12 at ¶ 14). Plaintiffs also sell mass spectrometry reagents and instruments to be used in conjunction with the Glyco Works Kit. (D.I. 12 at ¶ 11).

         Defendant, through its 2018 acquisition of a company called ProZyme, manufactures products containing InstantPC glycan reagents, which like the GlycoWorks Kit, are used to assist in the detection and labeling of compounds, including for identification of glycosylated proteins during the development of biopharmaceuticals or biologies. (D.I. 18 at 4). The chemical structure of the labeling reagent in InstantPC is (Id.; see also D.I. 19 at¶10):

         (Image Omitted)

         ProZyme announced its development of InstantPC in May of 2015, [1] and began selling InstantPC in October of 2015. (D.I. 19 at ¶¶ 10, 14). As of December of 2018, ProZyme's InstantPC reagent products had approximately 20 to 25% of the market. (D.I. 11 at ¶ 8; D.I. 12 at ¶ 14). Defendant sells mass spectrometry reagents and instruments, which according to Plaintiffs will be marketed and used in conjunction with InstantPC. (See D.I. 12 at ¶¶17-18).

         On January 14, 2013, Plaintiffs obtained the exclusive license (“Patent License Agreement”) to U.S. Patent No. 9, 658, 234 (“the ’234 Patent”)[2] from Ajinomoto Co., Inc. (“Ajinomoto”) of Tokyo, Japan. (Id. at ¶ 13). The ‘234 Patent, a continuation of patent applications filed by Ajinomoto, issued on May 23, 2017. (D.I. 8 at 4). On August 7, 2018, Ajinomoto assigned its rights and interests in the ’234 Patent to Waters Technologies Corporation. (D.I. 8 at 4). On September 18, 2018, Plaintiffs filed this patent infringement action, alleging infringement of the ’234 patent by Agilent “via the manufacture, use, sale, offer to sell, exportation, and/or importation, in whole or in part, of Agilent’s InstantPC reagent.” (D.I. 1 at ¶ 2).


         Preliminary injunctive relief is an “extraordinary” remedy appropriate only in “limited circumstances.” Kos Pharm., Inc. v. Andrx Corp., 369 F.3d 700, 708 (3d Cir. 2004); see also Intel Corp. v. ULSI Sys. Tech., Inc., 995 F.2d 1566, 1568 (Fed. Cir. 1993) (“[A] preliminary injunction is a drastic and extraordinary remedy that is not to be routinely granted.”). A preliminary injunction may be granted only if the moving party shows (1) a likelihood of success on the merits, (2) irreparable harm is likely if an injunction is not granted, (3) the balance of equities tips in favor of the moving party, and (4) an injunction is in the public interest. See Winter v. Nat. Res. Def. Council, Inc., 555 U.S. 7, 20 (2008); see also Osorio-Martinez v. Attorney Gen. United States of Am., 893 F.3d 153, 178 (3d Cir. 2018); Altana Pharma AG v. Teva Pharm. USA, Inc., 566 F.3d 999, 1005 (Fed. Cir. 2009). “These factors, taken individually, are not dispositive; rather, the district court must weigh and measure each factor against the other factors and against the form and magnitude of the relief requested.” Hybritech, Inc. v. Abbott Labs., 849 F.2d 1446, 1451 (Fed. Cir. 1988). The Court, however, cannot grant a preliminary injunction unless the moving party establishes both a likelihood of success on the merits and the existence of irreparable harm without the injunctive relief., Inc. v., Inc., 239 F.3d 1343, 1350 (Fed. Cir. 2001). “[A]ll findings of fact and conclusions of law at the preliminary injunction stage are subject to change upon the ultimate trial on the merits.” Purdue Pharma L.P. v. Boehringer Ingelheim GmbH, 237 F.3d 1359, 1363 (Fed. Cir. 2001).


         Plaintiffs assert that “Agilent is infringing several claims of the ’234 Patent, ” but for purposes of its motion, it has focused on “independent claims 1 and 6.” (D.I. 8 at 7).[3] The Court begins its analysis by addressing the first preliminary injunction factor – i.e., likelihood of success on the merits – in the context of the asserted claims and defenses.

         A. Likelihood of Success

         “With regard to the first factor – establishing a likelihood of success on the merits – the patentee seeking a preliminary injunction in a patent infringement suit must show that it will likely prove infringement, and that it will likely withstand challenges, if any, to the validity of the patent.” Titan Tire Corp. v. Case New Holland, Inc., 566 F.3d 1372, 1376 (Fed. Cir. 2009); see also, 239 F.3d at 1350. In evaluating whether Plaintiffs are likely to succeed in proving infringement of the asserted claims, the Court employs the same two-step process used to determine infringement on summary judgment or at trial. See Oakley, Inc. v. Sunglass Hut Int’l, 316 F.3d 1331, 1339 (Fed. Cir. 2003). First, the Court must determine the meaning and scope of the asserted claims. Markman v. Westview Instruments, Inc., 52 F.3d 967, 976 (Fed. Cir. 1995), affd, 517 U.S. 370 (1996). Second, the Court must compare the accused product (InstantPC glycan reagent) to the claims as properly construed. Id. Similarly, in assessing whether Plaintiffs are likely to withstand validity challenges involving prior art, the Court compares the asserted claims as construed to the asserted prior art. See Oakley, 316 F.3d at 1339. The Court should not grant a preliminary injunction if Defendant “raises a substantial question concerning either infringement or validity.”, 239 F.3d at 1350; see also Tate Access Floors, Inc. v. Interface Architectural Res., Inc., 279 F.3d 1357, 1365 (Fed. Cir. 2002) (“substantial question” means assertion of a defense that patentee cannot prove “lacks substantial merit”).

         1. Infringement

         The ’234 Patent, titled “Method For Analysis Of Compounds With Amino Group And Analytical Reagent Therefor, ” is generally directed to carbamate compounds and methods of labeling and analysis with those compounds, which can be used for N-glycan detection. See ’234 Patent at 1:22-30. According to Plaintiffs’ expert:

         the carbamate compounds have a strong fluorescent signal due to an aromatic carbocyclic or heterocyclic group, a strong mass spectrometry signal due to an electronically isolated amino group, and readily react with nitrogen-containing compounds, such as amino acids and proteins. Thus, the claimed carbamate compounds can be used for improved N-glycan labeling, detection, and analysis, including with mass spectrometry.

(D.I. 13 at ¶ 21).

         Asserted claims 1 and 6 of the ’234 Patent recite, in pertinent part (D.I. 1, Ex. A):

         1. A carbamate compound represented by formula (1):

         (Image Omitted)

         wherein Ar is an aromatic carbocyclic group or an aromatic heterocyclic group residue, wherein said aromatic carbocyclic group or said aromatic heterocyclic group residue has a substituent; and

         wherein, in the bond between Ar and the nitrogen atom of the carbamate group, a carbon atom within the ring of Ar is bound to the nitrogen atom of the carbamate group, a carbon atom within the ring of Ar is bound to the nitrogen atom of the carbamate group, whereby said carbamate compound may be in a form of a salt, and

         wherein said substituent contains a sulfonic acid group, a phosphoric acid group, a guanidyl group, a dialkylamino ...

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