Amide Beverage Co LLC v. Amazon.com Inc

I. Executive Summary and Procedural Information

• Parties & Counsel:
  • Plaintiff: Amide Beverage Company, LLC (Delaware)
  • Defendant: Amazon.com, Inc. (Delaware), and 17 other entities
  • Plaintiff’s Counsel: DEVLIN LAW FIRM LLC
• Case Identification: 4:24-cv-01022, E.D. Tex., 01/17/2025
• Venue Allegations: Plaintiff alleges venue is proper for each defendant on the grounds that they have committed acts of patent infringement within the Eastern District of Texas and maintain regular and established places of business in the district.
• Core Dispute: Plaintiff alleges that Defendants’ sale of Bang® energy drinks containing the ingredient "Creatyl-L-Leucine" infringes a patent directed to chemically stabilized creatine derivatives.
• Technical Context: The technology concerns novel chemical compounds of creatine designed to improve its stability and solubility in aqueous solutions, a significant issue for its use in nutritional supplements and beverages.
• Key Procedural History: The complaint details a complex history for the asserted patent and the accused products. The patent’s previous owner, ThermoLife International, engaged in prior litigation against the now-defunct manufacturer of Bang®, Vital Pharmaceuticals. The asserted patent survived an ex parte reexamination that confirmed the patentability of its key claims. A separate patent previously marked on the accused products was invalidated. During Vital's bankruptcy, an adversary proceeding established a potential reasonable royalty rate for the asserted patent, though the final settlement was for a lesser amount due to the bankruptcy circumstances. Plaintiff Amide Beverage acquired the patent in late 2024.

Case Timeline

Date	Event
2008-11-21	'077 Patent Priority Date
2013-01-08	'077 Patent Issue Date
2014-04-01	Prior litigation involving '077 Patent initiated
2018-01-12	'077 Patent Reexamination Certificate Issued
2018	Accused Bang® products established in the market
2022-10-10	Bang® manufacturer (Vital) Bankruptcy Petition Date
2024-11-04	Plaintiff Amide Beverage acquires '077 Patent
2025-01-17	Complaint Filing Date

II. Technology and Patent(s)-in-Suit Analysis

U.S. Patent No. 8,350,077 - "Amides of Creatine, Method of Their Preparation, and Remedy Possessing a Neuroprotective Activity"

The Invention Explained

• Problem Addressed: The patent addresses the known drawbacks of conventional creatine supplements, which exhibit "poor solubility and instability in aqueous media" and are poorly absorbed from the gastrointestinal tract, often causing side effects (Compl. ¶73; ’077 Patent, col. 2:30-40).
• The Patented Solution: The invention is a new class of creatine derivatives created by forming an amide bond between creatine and an amino acid. This new molecule is then combined with a low-molecular-weight organic or mineral acid (or water) to form a salt-like compound (’077 Patent, Abstract). The patent asserts that this chemical modification results in compounds with "an enhanced solubility and stability in aqueous solutions" compared to prior art creatine forms (’077 Patent, col. 3:20-23). The stated object is to obtain novel creatine derivatives with "a higher stability and a wider spectrum of biological actions" (’077 Patent, col. 3:51-53).
• Technical Importance: By creating a more stable and soluble form of creatine, the invention aimed to provide a more effective and palatable vehicle for delivering creatine in nutritional products, overcoming a key technical barrier to its widespread use (Compl. ¶¶ 75, 77).

Key Claims at a Glance

• The complaint asserts independent claim 1 and dependent claim 5 (Compl. ¶110, ¶145).
• Independent Claim 1 is directed to:
  • Amides of Creatine having a general formula: NH=C(NH2)-N(CH3)-CH2-CO-NH-R*X,
  • wherein R is an amino acid residue of an aliphatic L-amino acid (or other specified amino acids or their derivatives), and
  • X is a low-molecular-weight organic or mineral acid or water.
• The complaint notes that Plaintiff reserves the right to assert additional claims (Compl. ¶111).

III. The Accused Instrumentality

Product Identification

• Bang® and Bang® energy drink products that contain the ingredient "Creatyl-L-Leucine" (also marketed as "Super Creatine") (Compl. ¶¶ 59, 79).

Functionality and Market Context

• The accused products are water-based energy drinks (Compl. ¶147). The complaint alleges they contain "Creatyl-L-Leucine" (CLL), which it identifies as an amide of creatine and L-leucine, along with at least one low-molecular-weight organic or mineral acid, such as citric acid (Compl. ¶¶ 110, 118).
• The nutrition label for the accused products, included in the complaint, describes "SUPER CREATINE®" as "Creatyl-L-Leucine [Creatine bonded to L-Leucine]" (Compl. ¶81; Ex. E, p. 28). This visual evidence from the product label explicitly links the marketing term "Super Creatine" to the specific chemical structure alleged to infringe.
• The complaint alleges significant market success for the accused products, noting that by April 2022, Bang® was the third best-selling energy drink in the United States (Compl. ¶78).

IV. Analysis of Infringement Allegations

'077 Patent Infringement Allegations

Claim Element (from Independent Claim 1)	Alleged Infringing Functionality	Complaint Citation	Patent Citation
Amides of Creatine having a general formula: NH=C(NH2)-N(CH3)-CH2-CO-NH-R*X,	The accused products contain "Creatyl-L-Leucine" (CLL), which is alleged to be an amide of creatine covalently bonded to an L-leucine residue, thereby forming the NH=C(NH2)-N(CH3)-CH2-CO-NH-R portion of the claimed formula. The complaint provides an annotated chemical structure to illustrate this mapping.	¶¶ 112, 116	col. 16:36-38
wherein R is amino acid residue of aliphatic L-amino acid...or derivatives...	The "L-Leucine" component of the ingredient Creatyl-L-Leucine is alleged to be the "amino acid residue of aliphatic L-amino acid" required by the claim.	¶¶ 111, 120	col. 16:38-43
and X is low-molecular-weight organic or mineral acid or water.	The accused drinks are water-based and contain other ingredients, including acids such as citric acid, which are alleged to be the "low-molecular-weight organic or mineral acid" that non-covalently bonds (denoted by the * in the formula) with the CLL molecule to form an equilibrium salt product in the beverage.	¶¶ 117-119, 147	col. 16:43-44

Identified Points of Contention

• Scope Questions: A primary dispute may arise over whether the mixture of ingredients in the final beverage product constitutes the claimed compound. The complaint alleges that Creatyl-L-Leucine (CLL) and an acid (X) form an "equilibrium product" in the can that meets the "R*X" limitation (Compl. ¶121). This raises the question: does the claim term "Amides of Creatine having a general formula..." read on a mixture of separately added ingredients in a solution, or is it limited to a pre-synthesized, isolated salt compound? The complaint itself notes the original manufacturer, Vital, previously denied that such an equilibrium product formed (Compl. ¶125).
• Technical Questions: The complaint anticipates the defense that the CLL and acid components exist merely as dissociated ions in the aqueous solution, not the claimed non-covalently bonded structure. To counter this, it pleads infringement under the doctrine of equivalents, arguing the dissociated ions are insubstantially different (Compl. ¶¶ 127-128, 141). This raises the evidentiary question of whether the dissociated ions in the accused drink perform substantially the same function (enhancing stability) in substantially the same way to achieve substantially the same result as the claimed "R*X" compound taught in the patent.

V. Key Claim Terms for Construction

• The Term: "Amides of Creatine having a general formula: NH=C(NH2)-N(CH3)-CH2-CO-NH-R*X"
• Context and Importance: The construction of this entire formula, particularly the meaning of the non-covalent bond represented by "*X", is central to the dispute. The case hinges on whether a beverage containing the constituent parts (the creatine-amino acid amide R and an acid X) is the same as the claimed compound.
• Intrinsic Evidence for Interpretation:
  • Evidence for a Broader Interpretation: The patent's stated purpose is to create derivatives with enhanced stability "in aqueous solutions" (’077 Patent, col. 3:21-22). Further, reexamined claim 5 explicitly covers "[t]he compound of claim 1, wherein the compound is in an aqueous solution" (’077 Patent, Reexam. Cert., col. 2:26-27). Plaintiff may argue this evidence shows the inventors contemplated the compound existing as claimed within a liquid like the accused energy drinks.
  • Evidence for a Narrower Interpretation: The patent’s detailed examples describe the synthesis and crystallization of specific, solid compounds, such as "creatinyl-L-phenylalanine amide hydrate" and "creatinyl-tyrosine amide succinate" (’077 Patent, col. 5:48-49, col. 6:1-3). A defendant may argue that this focus on synthesized, isolated salts implies the claim is limited to such discrete compounds and does not cover an in situ mixture of potentially dissociated ions in a beverage.

VI. Other Allegations

• Indirect Infringement: The complaint focuses on direct infringement by the defendants for "using, selling, or offering to sell" the accused products (Compl. ¶110). It does not plead a separate count for indirect infringement.
• Willful Infringement: While the complaint does not contain an explicit count for willful infringement, it lays a detailed factual predicate that could support such a claim. It alleges that at least one defendant, GNC, has "known of its infringement of the '077 patent for many years" due to prior litigation (Compl. ¶89). The complaint also extensively documents the patent's litigation and reexamination history, as well as the manufacturer's bankruptcy proceedings where the patent was a key issue, suggesting that the infringement was known throughout the industry (Compl. ¶¶ 86-107).

VII. Analyst’s Conclusion: Key Questions for the Case

• A core issue will be one of chemical identity: Do the ingredients listed on the Bang® energy drink label, when combined in an aqueous solution, form the specific, non-covalently bonded molecular structure defined by the formula in claim 1, or do they exist merely as a mixture of dissociated components?
• A key alternative issue will be one of technical equivalency: If the product is found to contain primarily dissociated ions rather than the claimed bonded compound, does the complaint's theory of equivalence hold? Specifically, is the function of providing enhanced aqueous stability achieved in substantially the same way by dissociated ions as it is by the claimed salt-pair structure?
• A central damages question will be the impact of prior proceedings: How will the "reasonable royalty" rate of 8-10% discussed during the manufacturer's bankruptcy proceeding—a rate that was explicitly noted as not being the basis for the final bankruptcy settlement—influence the damages calculation against these downstream retailers?