Inter Partes Review of US 10,010,567
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`IN THE UNITED STATES PATENT AND TRADEMARK OFFICE
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`BEFORE THE PATENT TRIAL AND APPEAL BOARD
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`
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`RIMFROST AS
`Petitioner
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`v.
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`AKER BIOMARINE ANTARCTIC AS
`Patent Owner
`
`
`CASE IPR: IPR2020-01534
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`U.S. Patent No. 10,010,567 B2
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`PATENT OWNER’S SUR-REPLY TO PETITIONER’S REPLY
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`Mail Stop “PATENT BOARD”
`Patent Trial and Appeal Board
`United States Patent and Trademark Office
`P.O. Box 1450
`Alexandria, VA 22313-1450
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`1
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`IN THE UNITED STATES PATENT AND TRADEMARK OFFICE
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`
`
`RIMFROST AS
`Petitioner
`
`v.
`
`AKER BIOMARINE ANTARCTIC AS
`Patent Owner
`
`
`CASE IPR: IPR2020-01534
`
`U.S. Patent No. 10,010,567 B2
`
`
`
`
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`
`
`
`PATENT OWNER’S SUR-REPLY TO PETITIONER’S REPLY
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`
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`
`
`
`
`
`
`Mail Stop “PATENT BOARD”
`Patent Trial and Appeal Board
`United States Patent and Trademark Office
`P.O. Box 1450
`Alexandria, VA 22313-1450
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`1
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`Inter Partes Review of US 10,010,567
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`TABLE OF CONTENTS
`INTRODUCTION AND SUMMARY OF ARGUMENT ..............................................3
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`COLLATERAL ESTOPPEL DOES NOT APPLY ........................................................4
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`I.
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`II.
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`III. GROUND 1 SHOULD BE DENIED ................................................................................5
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`V.
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`GROUNDS 2, 3 AND 4 SHOULD BE DENIED ...........................................................18
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`VI. CERTIFICATE OF COMPLIANCE ............................................................................19
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`VII. CONCLUSION AND PRECISE RELIEF REQUESTED ...........................................19
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`CERTIFICATE OF SERVICE ..................................................................................................20
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`Inter Partes Review of US 10,010,567
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`INTRODUCTION AND SUMMARY OF ARGUMENT
`All of the asserted Grounds rely on Bottino II for the “less than 3% w/w free
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`I.
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`fatty acids” limitation, including Ground 1 which is the Ground asserted against
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`both independent claims (claims 1 and 15). The combined references in the
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`Grounds fail to provide this claim element. As a result, Petitioner has failed to
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`present any Grounds which establish a prima facie case of obviousness.
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`Petitioner continues to allege that the “unknown” fraction of the Station 11
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`krill extract of Bottino II (Ex. 1038) contained free fatty acids. Petitioner’s Reply
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`(“Reply”; Paper 14). There is no dispute that Bottino II discloses that the
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`“unknown” fraction included unidentified lipids that migrate between diglycerides
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`and triglycerides in the thin layer chomatography (TLC) method utilized by
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`Bottino II. However, in continuing to make this argument, Petitioner ignores the
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`the irrefutable evidence that in the TLC method used by Bottino II, based on the
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`method of Freeman and West (Ex. 2002), free fatty acids do not have an Rf
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`between that of diglycerides and triglcyerides. Based on the only relevant
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`evidence, the “unknown” fraction does not include free fatty acids.
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`In an attempt to direct attention away from this irrefutable evidence,
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`Petitioner points to a number of other cherry-picked references that disclose TLC
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`methods where free fatty acids do have an Rf between that of diglycerides and
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`triglycerides. However, this approach is not scientifically valid as none of those
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`3
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`references use solvent systems that are the same as or similar to Bottino II or
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`Freeman and West. Further, Petitioner and its expert have provided no supporting
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`literature references or experimental evidence that shows that the slight changes
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`between the Bottino II method and the Freeman and West method (i.e., deletion of
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`0.2 parts acetic acid in solvent system 1 and use of a different silica gel) would
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`have any impact on how free fatty acids migrate in relation to diglycerides and
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`triglycerides as specifically disclosed in Freeman and West. Dr. Tallon’s
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`speculative expert testimony on this issue is unsupported by any evidence or record
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`and should be ignored.
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`II. COLLATERAL ESTOPPEL DOES NOT APPLY
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`Petitioner briefly addresses collateral estoppel at p. 4 of its Reply, alleging
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`that the references in the Grounds had previously been considered by the Board. In
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`making this argument, Petitioner for some reason focuses on the cholesterol
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`limitation appearing in two of the dependent claims. This is an attempt to side-step
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`the issue raised by Patent Owner in its Response (Paper 9; “PO Response”) that
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`both independent claims of the ‘567 patent include the limitation of “less than 3%
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`w/w free fatty acids” which had not been previously addressed in any decision by
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`the Board. PO Response at 10-12. As explained in the PO Response, this is a
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`completely new claim element that has not been previously adjudicated and which
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`4
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`materially alters the question of invalidity. Id. at 11. Petitioner’s attempt to
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`redirect the Board’s attention to a different claim limitation in the dependent
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`claims regarding cholesterol both ignores Patent Owner’s arguments which
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`specifically apply the relevant standards for collateral estoppel and evidences a
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`misunderstanding of the law of collateral estoppel. Indeed, Petitioner has made no
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`attempt to address PO’s arguments in its Response regarding the applicable
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`elements for establishing whether collateral estoppel exists.
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`III. GROUND 1 SHOULD BE DENIED
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`The Ground 1 combination of Sampalis II, Bottino II and Randolph
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`does not teach or suggest the claim limitation of “less than 3% w/w free fatty
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`acids” as required by both independent claims. As a result, Petitioner has failed to
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`meet its burden of establishing a prima facie case of obviousness.
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`It cannot be disputed that Bottino II teaches that the data for the Station II
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`krill lipid extract reported in Table 2 was obtained by TLC using the method of
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`Freeman and West with three slight modifications: 1) the silica gel Adsorbosil-5
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`was used instead of silica gel-G; 2) 0.2 parts of acetic acid was eliminated from
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`solvent mixture 1; and 3) gravimetry was used for quantitation of the spots
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`5
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`instead of colorimetry.1 Further, it cannot be disputed that Bottino II discloses
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`that the “unknown” fraction of the Station 11 krill lipid extract contained lipids
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`that had Rf values between diglycerides and triglycerides (i.e., the “unknown”
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`lipids migrated between diglycerides and triglycerides). Finally, it cannot be
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`disputed that Freeman and West discloses that when its two solvent system is
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`used for TLC, free fatty acids do not have an Rf between that of diglycerides and
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`triglycerides as demonstrated in panel C of Figure 1 of Freeman and West,
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`reproduced below. When deposed, Dr. Tallon was forced to admit this fact. Ex.
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`2020 (Tallon Depo.) p. 0042, l. 5 – 0043, l. 10). As previously argued by Patent
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`Owner, these facts establish that a POSITA would conclude that the 2 ± 22%
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`“unknown” fraction in the Station 11 extract in Table 2 of Bottino II could not
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`and did not contain free fatty acids. PO Response at 12-16; Ex. 2001 (Jaczynski
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`Decl.) at ¶¶26-28.2
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`1 Only the first two changes are related to the how actual TLC process was
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`performed. The third change to the use of gravimetry applies only to quantitation
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`of the resolved lipids after the TLC process was performed.
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`2 The Board should ignore Petitioner’s assertions regarding Fricke 1984 (Ex. 1010)
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`as it was not included in an instituted Ground and there are no arguments of record,
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`for example on motivation to combine with the other references or reasonable
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`expectation of success. As held by the Supreme Court, the petitioner is the “master
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`of its complaint,” SAS Inst., Inc. v. Iancu, 138 S. Ct. 1348, 1355 (2018). As such,
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`“[i]t is of the utmost importance that petitioners . . . adhere to the requirement that
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`the initial petition identify ‘with particularity’ the ‘evidence that supports the
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`grounds for the challenge to each claim.’” Intelligent Bio-Systems, Inc. v. Illumina
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`Cambridge Ltd., 821 F.3d 1359, 1369 (Fed. Cir. 2016) (citing 35 U.S.C. §
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`312(a)(3)).
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`In spite of this evidence, Petitioner has doubled-down on its assertion that
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`the “unknown” fraction of Station 11 extract in Table 2 of Bottino II has to
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`contain free fatty acids. Petitioner’s arguments are not supported by any credible
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`evidence, nor can they meet the required burden of proof.
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`Petitioner’s expert admits that “[t]he Rf values observed in one analysis
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`cannot be directly compared to Rf values used with different solvent systems,
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`different adsorbent, different equipment, and different operating conditions. That
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`is why reference standards are used to calibrate the analysis.” Ex. 1086 (Tallon
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`Decl.) ¶21. However, Dr. Tallon and Petitioner then inexplicably go on to do
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`exactly that by arguing that:
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`a POSITA would have understood, when analyzed by TLC, free fatty acids
`will typically have an Rf value between the Rf values of triglycerides and
`diglycerides as described in the footnote to Table 2 of Bottino II. Tallon
`Reply, ¶¶ 9, 24-28, 31-37.
`Reply at 8; see also 12-13. As support for this argument, Petitioner cites specific
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`paragraphs from Dr. Tallon’s Declaration that discuss a number of other TLC
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`experiments, none of which use the same solvent system as Bottino II or
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`Freeman and West much less the same absorbent, equipment or operating
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`conditions. These references include Ex. 1177 (Zamora and Hidalgo), Ex. 1176
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`(Blank et al.), Ex. 1162 (Yamaguchi), Ex. 1172 (Tsuyuki), and Ex. 1174
`8
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`(Showman et al.). As shown in the following Table, most of these references
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`used a single solvent mixture as opposed to a dual solvent system and none of the
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`references used a solvent mixture containing ethanol.
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`Reference TLC Solvents
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`Thin layer Two-
`step?
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`Ethanol?
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`Solvent mixture 1:
`Diethyl ether-
`benzene-ethanol-
`acetic acid
`40:50:2:0.2
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`Solvent mixture 2:
`Diethyl ether-
`hexane 6:94
`Freeman and West
`(1966), Acetic
`acid removed from
`solvent mixture 1
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`Solvent mixture 1:
`Diethyl ether-
`benzene-ethanol
`40:50:2
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`Solvent mixture 2:
`Diethyl ether-
`hexane 6:94
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`Comparison of
`several different
`solvent systems
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`Freeman
`and West
`Ex. 2002
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`Bottino II
`Ex. 1038
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`Zamora
`and
`Hidalgo
`Ex. 1177
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`
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`Silica gel-
`G
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`Yes
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`Yes
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`Adsorbosil-
`5
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`Yes
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`Yes
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`Not
`described
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`9
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`Do FFA
`have Rf
`between
`TG and
`DG?
`No
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`Not
`disclosed;
`does not
`provide a
`picture of
`the TLC
`plate
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`Depends
`on solvent
`system
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`Yamaguchi
`Ex. 1162
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`Tsuyuki
`Ex. 1172
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`Showman
`Ex. 1174
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`1. petroleum ether-
`diethyl ether-
`acetic acid
`2. hexane-diethyl
`ether-formic acid
`3. toluene-diethyl
`ether – ethyl
`acetate-acetic acid
`4. isopropyl ether-
`acetic acid; then
`petroleum ether-
`diethyl ether-
`acetic acid
`5. petroleum ether-
`diethyl ether-
`acetic acid
`6. heptane-
`isopropyl ether-
`acetic acid
`7. Toluene; then
`hexane-
`chloroform-
`methanol
`Petroleum ether-
`diethylether-acetic
`acid
`Petroleum ether-
`diethyl ether-
`acetic acid
`(85:15:1)
`Hexane-diethyl
`ether-acetic acid
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`Inter Partes Review of US 10,010,567
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`1. No
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`2. No
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`3. No
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`4. Yes
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`5. No
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`6. No
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`7. Yes
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`1. No
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`2. No
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`3. No
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`4. No
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`5. No
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`6. No
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`7.Methanol
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`1. Yes
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`2. Yes
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`3. No
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`4. Yes
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`5. Yes
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`6. Yes
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`7. No
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`Silica gel
`60F
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`No
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`No
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`Silica gel G No
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`No
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`Yes
`
`Yes
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`Silica gel
`60
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`No
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`No
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`Yes
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`None of the references relied on by Petitioner and its expert utilize a
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`solvent system that is similar to that utilized by Freeman and West, or as modified
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`10
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`by Bottino II. Thus, according to Petitioner’s own reasoning, it is not
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`scientifically credible to utilize these references to try to establish that the slight
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`changes made to the method of Freeman and West by Bottino II would result in
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`the free fatty acids suddenly having an Rf between diglycerides and triglycerides
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`as is required for Petitioner’s prima facie case of obviousness.3 The simple fact is
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`that the closest TLC system to that used by Bottino II is Freeman and West and
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`in that system the free fatty acids did not have an Rf value between that of
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`diglycerides and triglycerides. Petitioner’s argument that “Dr. Tallon confirmed
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`that the “unknown” fraction includes any free fatty acids in the krill sample
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`analyzed and, as a result, the Station 11 krill extract included no more than 2%
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`free fatty acids” is not supported by credible evidence. See Reply at 8.
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`In fact, Dr. Tallon’s own analysis of Table 11 of Zamora and Hidalgo
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`establishes that in two of the seven TLC procedures the Rf of free fatty acids is
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`not between diglycerides and triglycerides. Dr. Tallon provided the following
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`highlighted table in ¶27 of his Declaration (Ex. 1086):
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`3 Dr. Tallon also admitted that there is no indications of what, if any, standards
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`Bottino II utilized. Ex. 2020 (Tallon Depo.) p. 0051, l. 5 –16).
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`11
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`The Rf of free fatty acids did not fall between those of diglycerides and
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`triglycerides in the TLC methods summarized in columns 3 and 7.4 This evidence
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`directly undermines Petitioner’s argument that “free fatty acids will typically have
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`an Rf value between the Rf values of triglycerides and diglycerides. . . .” See
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`Reply at 8.
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`Petitioner further argues that:
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`4 It is noted that the only other solvent system the utilizes an alcohol (the first
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`solvent mixture used by Bottino II and Freeman and West used ethanol) is the two
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`solvent system in Column 7 of Table 11 of Zamora and Hidalgo. Ex. 1177 at 0020.
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`This solvent system used toluene as the first solvent and then a mixture of hexane,
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`chloroform and methanol. In this system, the Rf of free fatty acids is not between
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`that of diglycerides and triglycerides.
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`[I]t is undisputed that the TLC methodologies, as well as the samples
`analyzed in Bottino II and Freeman & West were different making any
`comparison of the resulting Rf values inapt. Tallon Reply, ¶¶19-29. In
`particular, Bottino II expressly states that its TLC method differed from the
`method used in Freeman and West in at least three (3) ways, including
`differences in the solvent system and adsorbent used. Exhibit 1038, p.
`0002.
`Reply at 11. Of course, this argument is completely contradictory to Petitioner’s
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`argument that the results of even less similar TLC methods can be used to show
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`that free fatty acids have an Rf value between that of diglycerides and
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`triglycerides.
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`In any event, it is undisputed that Bottino II modified the method of
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`Freeman and West by deleting 0.2 parts of acetic acid from the first solvent
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`mixture and by using Adsorbosil-5 instead of silica gel-G. Petitioner argues that:
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`“Because the solvent system and absorbent significantly influence Rf values and
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`the distance individual components travel on a TLC plate, Patent Owner’s
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`comparison of the results reported in Table 2 of Bottino II and Freeman & West’s
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`chromatograph is unavailing.” Reply at 12. However, Petitioner has presented no
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`evidence, other than Dr. Tallon’s unsupported testimony, that these minor
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`changes to Freeman and West would suddenly cause free fatty acids to have an Rf
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`between that of diglycerides and triglycerides.
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`Specifically, Petitioner and its expert have not presented any evidence,
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`experimental or from the scientific literature, that examines the effect of removing
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`0.2 parts of acetic acid from any solvent mixture or on any differences between
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`the use of Adsorbosil-5 and silica gel-G. Indeed, Dr. Tallon admitted when
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`deposed that he could not quantify what differences in Rf values could be
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`expected by these changes. Ex. 2020 (Tallon Depo.) p. 0035, l. 22 – 0036, l. 14
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`and p. 0038, l. 10-20). Thus, Petitioner has failed to provide evidence to support
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`its assertion that the changes made by Bottino II would cause free fatty acids to
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`have an Rf value between that of diglycerides and triglycerides, let alone that a
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`POSITA would believe so.
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`Petitioner next argues that the sum of the weight percentages of the Station
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`II extract equals 100% and asks the question: “If the “unknown” fraction does not
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`include free fatty acids, in which lipid class of the Station 11 extract are the free
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`fatty acids found?” Reply at 14. First, it is not Patent Owner’s burden of proof to
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`show what percentage of free acids the Station II extract contained or identify
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`where the free fatty acids are – they are definitely not in the unknown fraction as
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`discussed above. Second, the most likely explanation is that the free fatty acid
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`content was simply not reported in Table 2, for example due to poor resolution.
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`See Ex. 2001 (Jaczynski Decl.) ¶29.
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`Furthermore, when deposed, Dr. Tallon admitted that the TLC methods of
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`references such as Tsuyuki and Yamaguchi identified components of krill lipids
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`including cholesterol, cholesterol esters, pigments and monoglycerides. Ex. 2020
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`(Tallon Depo.) 0023, l. 13 – 0025, l. 7). In fact, Tsuyuki quantified these
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`components by TLC and found that krill lipids contained 2.2% monoglycerides,
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`4.7% sterols, 0.8% sterol esters, and 4.1% pigments. See Ex. 1172 at 0005 (Table
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`1) and Ex. 2020 (Tallon Depo.) 0064, l. 23 – 0065, l. 19. Bottino II fails to report
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`any of these lipid classes, which do not migrate between diglycerides and
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`triglycerides in the method of Tsuyuki. Of course, it is not known where these
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`lipids would have migrated in the method of Bottino II, but the fact that they were
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`not reported indicates that Bottino II simply did not report the values for some
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`lipid classes. Indeed, when deposed Dr. Tallon admitted that Bottino II “hasn’t
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`gone to the trouble to quantify” free cholesterol levels. Ex. 2020 (Tallon Depo.) at
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`0053, l. 20-24. Tsuyuki reported free cholesterol levels (sterols in Table 2 of
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`Tsuyuki) to be present at 4.7%. Id. at 0065, l. 7-10. There is no evidence that
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`Bottino II also simply did not go to the trouble to quantify free fatty acids.
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`Petitioner next attempts to address the fact that the value reported for the
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`“unknown” fraction contains a very large standard deviation of ± 22. Petitioner
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`argues that a POSITA would understand this to be a “percentage variation” of
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`22% of 2% or ± 0.44 wt%. The only support for this argument is Dr. Tallon’s
`15
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`hindsight-based calculations. First, those calculations are at best highly
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`speculative as the underlying data in Table 2 of Bottino II is not reported and
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`without that data or a more detailed description in Bottino II there can be no way
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`to recalculate to the standard deviation.5 Petitioner and Dr. Tallon have offered
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`no evidence from any other publication using an approach similar to that utilized
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`by Dr. Tallon. Second, Petitioner’s arguments that a standard deviations cannot
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`encompass negative values is incorrect. This can happen in non-normally
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`distributed data.
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`Finally, Petitioner asserts that Patent Owner’s inherency argument is
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`unpersuasive, arguing that it is “directly refuted by Dr. Tallon’s testimony that
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`any free fatty acids in the Station 11 krill extract reported in Bottino II are found
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`5 Based on Dr. Tallon’s calculations, Petitioner asserts that a POSITA would have
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`understood that Station 11’s “unknown” fraction was 1.56 to 2.44%. Reply at 16.
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`However, since the results in Table 2 were presented as whole numbers with no
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`decimals and only one or two significant figures it is not appropriate to use those
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`numbers to calculate values with three significant figures. Indeed, spurious digits,
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`introduced by calculations resulting in a number with a greater precision than the
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`precision of the used data in the calculations, or in a measurement reported to a
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`greater precision than the measurement resolution, are not significant figures.
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`16
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`in the “unknown” fraction. Thus, the Station 11 Euphausia superba krill extract
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`contains at most 1.56 - 2.44% free fatty acids, and therefore necessarily less than
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`3% as recited in the challenged claims. Tallon Reply, ¶¶ 9, 16, 48-52; Tallon
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`Decl., ¶¶ 174, 459.” Reply at 18. Dr. Tallon’s speculative, unsupported
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`testimony alone cannot establish that the “unknown” fraction contained free fatty
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`acids. Indeed, when deposed Dr. Tallon admitted that there is no direct reference
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`to free fatty acids in Table 2 of Bottino or anywhere else. Ex. 2020 (Tallon Depo.)
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`p. 0074, l. 6-23 ). Therefore, the TLC method used by Bottino II does not provide
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`“direct measurement of the free fatty acids found in the Station II extract” as
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`argued by Petitioner. See Reply at 9. At best, Petitioner and Dr. Tallon are
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`arguing that the “unknown” fraction, which by its own description is unknown,
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`would have necessarily contained free fatty acids. This is the very definition of
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`an inherency argument. And here it fails because Petitioner has failed in its
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`burden to prove that the “unknown” fraction necessarily contained free fatty
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`acids. As discussed in detail above, it much more probable based on the data in
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`Freeman and West that the free fatty acids do not have an Rf between diglycerides
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`and triglycerides in the solvent systems used by Bottino II. Petitioner has
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`presented no credible evidence that the minor changes made by Bottino II to the
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`method of Freeman and West would suddenly cause the Rf values of the free fatty
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`acids, diglycerides and triglycerides to substantially change. Thus, Petitioner is
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`relying on an inherency argument and has failed to carry its burden.
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`In summary, the combined references in Ground 1 fail to teach element of
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`independent claims 1 and 15. Petitioner has failed to establish a prima facie case
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`of obviousness with respect to the independent claims and the claims dependent
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`thereon. Ground 1 must be denied.
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`V. GROUNDS 2, 3 AND 4 SHOULD BE DENIED
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` Under Ground 2, Petitioner that claims 6, 14, and 20 are obvious over the
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`combination of Sampalis I, Bottino II, Randolph, and Breivik II. Under Ground 3,
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`Petitioner asserts that claims 12 and 18 are obvious over the combination of
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`Sampalis I, Bottino II, Randolph, and Bottino I. Under Ground 4, Petitioner
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`asserts that claims 13 and 19 are obvious over the combination of Sampalis I,
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`Bottino II, Randolph, Yamaguchi, Hardardottir, and Fricke. In each of these
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`Grounds, Petitioner relies on Bottino II to provide the claim element of “less than
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`3% w/w free fatty acids” in the underlying independent claims. Grounds 2, 3, and
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`4 thus fail because Bottino II does not provide the claim element of “less than 3%
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`w/w free fatty acids” as discussed above.
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`18
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`Inter Partes Review of US 10,010,567
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`VI. CERTIFICATE OF COMPLIANCE
`Pursuant to 37 C.F.R. § 42.24(d), the undersigned certifies that this Petition
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`complies with the type-volume limitation of 37 C.F.R. § 42.24(a). The word count
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`application of the word processing program used to prepare this Petition indicates
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`that the Petition contains 3,349 words, excluding the parts of the brief exempted by
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`37 C.F.R. § 42.24(a) (that is, the word count does not include the table of contents,
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`the exhibit list, certificate of compliance, conclusion, or the certificate of service).
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`VII. CONCLUSION AND PRECISE RELIEF REQUESTED
`For the foregoing reasons, Petitioner has failed to meet its burden to show
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`that the claims of the ’567 Patent are unpatentable over the combined art in the
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`Grounds upon which trial was instituted. Accordingly, Patent Owner requests
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`that the Board confirm the patentability of Claims 1-20 of the ’567 patent.
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` Respectfully submitted,
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`Dated: December 16, 2021
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`CASIMIR JONES SC
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`By /John Mitchell Jones/
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` John Mitchell Jones, Reg. No, 44,174
`Email: jmjones@casimirjones.com
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`David Casimir, Reg. No. 42,395
`Email: dacasimir@casimirjones.com
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`Attorneys for Patent Owner
`Aker Biomarine Antarctic AS
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`19
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`Inter Partes Review of US 10,010,567
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`CERTIFICATE OF SERVICE
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`The undersigned hereby certifies that on this 16th day of December 2021, a
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`copy of the foregoing Patent Owner’s Sur-Reply to Petitioner’s Reply, Patent
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`Owner’s Updated Exhibit List and Exhibit 2020 were served in their entirety
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`electronically (as consented to by Petitioner) to the attorneys of record as follows:
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`567ipr@hbiplaw.com
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`James F. Harrington
`jfhdocket@hbiplaw.com
`Hoffmann & Baron, LLP
`6900 Jericho Turnpike
`Syosset, NY 11791
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`Michael I. Chakansky
`micdocket@hbiplaw.com
`Hoffmann & Baron, LLP
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`John T. Gallagher
`jtgdocket@hbiplaw.com
`Hoffmann & Baron, LLP
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`By: /John Mitchell Jones/
`John Mitchell Jones, Ph.D.
`Registration No. 44,174
`Counsel for Patent Owner
`CASIMIR JONES, S.C.
`2275 Deming Way, Suite 310
`Middleton, Wisconsin 53562
`(608) 662-1277
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`20
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