DCT
1:18-cv-01450
Waters Corp v. Agilent Tech Inc
I. Executive Summary and Procedural Information
- Parties & Counsel:
- Plaintiff: Waters Corporation and Waters Technologies Corporation (Delaware)
- Defendant: Agilent Technologies Inc. (Delaware)
- Plaintiff’s Counsel: Young Conaway Stargatt & Taylor LLP; Arnold & Porter Kaye Scholer LLP
- Case Identification: 1:18-cv-01450, D. Del., 09/18/2018
- Venue Allegations: Venue is alleged to be proper in the District of Delaware because Defendant is incorporated in Delaware and therefore resides in the district.
- Core Dispute: Plaintiff alleges that Defendant’s InstantPC reagent, used for preparing samples for mass spectrometry, infringes a patent covering specific carbamate compounds and their use in analytical methods.
- Technical Context: The technology relates to analytical chemistry, specifically the use of labeling reagents to enable highly sensitive detection and quantification of biomolecules like glycans and proteins via mass spectrometry.
- Key Procedural History: The complaint notes that the patent-in-suit was originally assigned to Ajinomoto Co., Inc. Plaintiff Waters Technologies Corporation was granted an exclusive license on January 14, 2013, and subsequently received a full assignment of the patent on August 7, 2018. The complaint also alleges that Defendant Agilent acquired ProZyme, Inc., the original developer of the accused products, on August 1, 2018, after having been notified by Plaintiff of the patent-in-suit.
Case Timeline
| Date | Event |
|---|---|
| 2002-02-14 | ’234 Patent Priority Date |
| 2013-01-14 | Waters granted exclusive license to the ’234 Patent |
| During 2015 | Waters launches its GlycoWorks RapiFluor-MS N-Glycan Kit |
| During 2015 | ProZyme launches products containing the accused InstantPC reagent |
| 2017-05-23 | ’234 Patent Issue Date |
| 2018-06-29 | Waters allegedly informs Agilent of its exclusive license to the ’234 Patent |
| 2018-08-01 | Agilent completes acquisition of ProZyme |
| 2018-08-07 | ’234 Patent assigned to Waters Technologies Corporation |
| 2018-09-18 | Complaint Filing Date |
II. Technology and Patent(s)-in-Suit Analysis
U.S. Patent No. 9,658,234 - "Method For Analysis Of Compounds With Amino Group And Analytical Reagent Therefor"
- Issued: May 23, 2017
The Invention Explained
- Problem Addressed: The patent's background section describes the challenge of accurately quantifying compounds with amino groups (such as amino acids and peptides) that are present in very small amounts within biological samples. (’234 Patent, col. 1:30-40). Conventional labeling reagents used to make these compounds detectable often suffer from low sensitivity, and the reagents themselves or their byproducts can interfere with the analysis, frustrating accurate measurement. (’234 Patent, col. 2:5-21).
- The Patented Solution: The invention is a new class of carbamate compounds used as labeling reagents specifically engineered for mass spectrometry. These reagents attach to the target molecule and possess a chemical structure that both enhances ionization (making the molecule easier to detect) and creates a predictable fragmentation pattern when analyzed. (’234 Patent, Abstract; col. 11:20-34). This allows the mass spectrometer to selectively detect the signal from the labeled compound while ignoring background noise, improving both sensitivity and selectivity.
- Technical Importance: This technology provided a method to analyze trace amounts of biomolecules with higher sensitivity and accuracy, a critical need in fields like medicine, biochemistry, and pharmaceutical science where such analysis informs research and diagnostics. (’234 Patent, col. 1:35-52).
Key Claims at a Glance
- The complaint asserts independent claims 1, 6, and 15.
- Independent Claim 1 (Compound Claim): A carbamate compound with a specific chemical structure defined by Formula (1), which includes:
- An aromatic carbocyclic or heterocyclic group residue ("Ar").
- A substituent on the "Ar" group.
- A specific bond between a carbon atom in the "Ar" ring and the nitrogen of the carbamate group.
- The substituent must contain one of a select group of chemical moieties: a sulfonic acid group, a phosphoric acid group, a guanidyl group, a dialkylamino group, or a trialkyl ammonium group.
- Independent Claim 6 (Method Claim): A method for analyzing a compound with an amino group by labeling it with the compound of claim 1 and subjecting the result to mass spectrometry.
- Independent Claim 15 (Method Claim): A method for labeling a compound with an amino group, suitable for mass spectrometry, by reacting it with the compound of claim 1.
III. The Accused Instrumentality
Product Identification
The primary accused instrumentality is Agilent's "InstantPC reagent" (Compl. ¶2). The complaint also lists numerous product kits sold under the Gly-X, GlykoPrep, and ProZyme brand names that contain the InstantPC reagent (Compl. ¶18, ¶27).
Functionality and Market Context
The InstantPC reagent is a chemical dye used for labeling N-glycans (a type of carbohydrate attached to a protein) to allow for their subsequent detection by mass spectrometry (Compl. ¶18). The complaint alleges that Agilent is a major competitor to Waters in the protein labeling and characterization market and that consumers use the InstantPC reagent with mass spectrometry devices to perform glycan analysis (Compl. ¶22). The complaint includes a chemical diagram of the accused InstantPC reagent. (Compl. ¶19). This diagram depicts the alleged chemical structure of Agilent's InstantPC reagent.
IV. Analysis of Infringement Allegations
’234 Patent Infringement Allegations
| Claim Element (from Independent Claim 1) | Alleged Infringing Functionality | Complaint Citation | Patent Citation |
|---|---|---|---|
| A carbamate compound represented by formula (1): [structural formula] | The complaint alleges that the InstantPC reagent is a carbamate compound with a structure identical to that depicted in formula (1) of the patent. | ¶37 | col. 28:20-28 |
| wherein Ar is an aromatic carbocyclic group or an aromatic heterocyclic group residue... [and] has a substituent | The complaint alleges that in the InstantPC reagent, "Ar is a six-sided ring with a substituent" and that this ring is an "aromatic carbocyclic compound residue." The complaint provides a highlighted diagram to illustrate this element. | ¶37 | col. 28:31-35 |
| 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 | The complaint alleges that in the InstantPC reagent, a carbon atom in the six-sided ring is bound to the nitrogen atom of the carbamate group, providing a highlighted diagram. | ¶37 | col. 28:36-40 |
| wherein said substituent contains a sulfonic acid group, a phosphoric acid group, a guanidyl group, a dialkylamino group or a trialkyl ammonium group | The complaint alleges that the substituent on the InstantPC reagent's aromatic ring "contains a dialkylamino group." This is illustrated with a highlighted diagram showing the accused chemical group. | ¶37 | col. 28:41-45 |
- Identified Points of Contention:
- Factual Question: The infringement theory for claim 1 relies heavily on the allegation that the chemical structure of Agilent's commercial InstantPC reagent is exactly as depicted in the complaint (Compl. ¶19, ¶37). A primary point of contention will be whether discovery and testing confirm this alleged structure.
- Scope Question: For method claims 6 and 15, which require using the claimed compound, the analysis will turn on whether Agilent's customers are directly infringing and whether Agilent's actions meet the standards for indirect infringement. The complaint cites product guides (Exhibits E and F, not attached to the public filing) as evidence that customers using the ProZyme kits perform all steps of the claimed methods (Compl. ¶38, ¶39). This raises the question of whether use of the InstantPC reagent as instructed by Agilent necessarily results in performing every limitation of the asserted method claims.
V. Key Claim Terms for Construction
- The Term: "dialkylamino group"
- Context and Importance: This term is one of the five options for the mandatory "substituent" in claim 1. The complaint's infringement theory hinges on the allegation that the InstantPC reagent contains this specific group (Compl. ¶37). The definition of this term will be critical to determining literal infringement. Practitioners may focus on this term because its precise scope—for example, the size and nature of the "alkyl" groups—is essential for the infringement analysis.
- Intrinsic Evidence for Interpretation:
- Evidence for a Broader Interpretation: The patent repeatedly refers to the purpose of the polar substituents as enhancing detection sensitivity, suggesting that any structure serving this function could fall within the scope. Claim 3 specifies that the alkyl groups have 1 to 5 carbon atoms, which implies that without this limitation (as in claim 1), "alkyl" could be interpreted more broadly. (’234 Patent, col. 7:23-30; col. 29:43-46).
- Evidence for a Narrower Interpretation: The specification provides specific examples of such groups, such as "p-dialkylaminophenyl group" and "1-(3-dialkylamino)naphthyl group." A party could argue these examples limit the term to simple, unbranched alkyl chains directly attached to the nitrogen atom, as shown in the patent's examples and the complaint's diagrams. (’234 Patent, col. 7:35-39).
VI. Other Allegations
- Indirect Infringement: The complaint alleges active inducement of method claims 6 and 15, stating that Agilent provides instructions, marketing materials, product manuals, and videos that encourage and instruct customers on how to use the InstantPC reagent in an infringing manner (Compl. ¶40). It also alleges contributory infringement, asserting that the InstantPC reagent is a material part of the invention, is known by Agilent to be specially made for use in an infringing manner, and is not a staple article of commerce suitable for substantial non-infringing use (Compl. ¶41).
- Willful Infringement: The complaint alleges that Agilent's infringement is and will be willful. The basis for this allegation is pre-suit knowledge, stemming from a June 29, 2018 phone call in which a Waters representative allegedly informed Agilent's in-house patent counsel that Waters held an exclusive license to the ’234 Patent and was aware of Agilent's plans to acquire ProZyme (Compl. ¶31). The complaint alleges Agilent proceeded with the acquisition and accused activities despite this notice (Compl. ¶31, ¶42).
VII. Analyst’s Conclusion: Key Questions for the Case
- A key evidentiary question will be one of structural identity: will discovery confirm that the chemical structure of Agilent's commercially sold InstantPC reagent is the same as the structure depicted in the complaint, which appears to map directly to the limitations of claim 1 of the ’234 Patent?
- A central issue of indirect infringement will be whether Agilent’s product documentation and marketing materials instruct or encourage customers to use the InstantPC reagent in a manner that performs all steps of the asserted method claims (claims 6 and 15), thereby making Agilent liable for inducing its customers' infringement.
- The court will likely examine the question of willfulness based on the specific pre-suit notice alleged in the complaint. The determination will depend on the evidence presented regarding the June 29, 2018 phone call and whether Agilent’s actions following that alleged notice were objectively reckless.