`UNITED STATES PATENT AND TRADEMARK OFFICE
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`Paper 31
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`BEFORE THE PATENT TRIAL AND APPEAL BOARD
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`RIMFROST AS
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`Petitioner
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`v.
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`AKER BIOMARINE ANTARCTIC AS
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`Patent Owner
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`Case No.: IPR2018-01730
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`U.S. Patent No. 9,072,752
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`Issue Date: July 7, 2015
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`Title: Bioeffective Krill Oil Compositions
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`PETITIONER’S SUR-REPLY TO PATENT OWNER’S
`MOTION TO AMEND
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`Inter Partes Review Case No.: IPR2018-01730
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`U.S. Patent No. 9,072,752
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`TABLE OF CONTENTS
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`I.
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`INTRODUCTION .............................................................................................. 1
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`II. PROPOSED CLAIMS 21-29 ARE UNPATENTABLE ................................... 2
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`A.
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`B.
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`Catchpole Discloses And Claims Compositions Satisfying The
`Proposed “From 6% To 10% Ether Phospholipids” Limitation ........... 2
`Dr. Tallon’s Unrebutted Testimony Demonstrates
`That Enzymotec’s Grade B Krill Extract Satisfies The
`Proposed “6% To 10% Ether Phospholipids” Limitation ..................... 6
`NKO, Randolph And Sampalis II Each Disclose
`Krill Oil Compositions Satisfying The Proposed
`100-700 mg/kg Astaxanthin Esters Limitation ..................................... 8
`III. CONCLUSION ................................................................................................12
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`C.
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`Inter Partes Review Case No.: IPR2018-01730
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`U.S. Patent No. 9,072,752
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`I.
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`INTRODUCTION
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`Petitioner argues that the “ether phospholipid disclosures” of Catchpole
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`and/or Enzymotec and the “astaxanthin ester disclosures” of NKO, Randolph
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`and/or Sampalis II, in combination with the prior art of record, renders claims 21-
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`29 obvious. Responding to Petitioner’s arguments, Patent Owner ignores that:
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`(1) Catchpole expressly describes and claims compositions containing
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`greater than 5% and 10% ether phospholipids;
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`(2) the Board previously found that, based on Catchpole, it would have been
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`obvious to prepare krill oil compositions with greater than 5% ether phospholipids;
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`(3) Catchpole discloses and teaches that extraction conditions (e.g.,
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`duration, temperature, pressure, solvents and co-solvent concentration) could be
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`readily varied by a POSITA in predictable ways with a reasonable expectation of
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`success of obtaining a desired lipid profile;
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`(4) Examples 7 and 8 of Catchpole demonstrate that, with the same feed
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`material, increasing the co-solvent concentration increases the percentage of
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`phospholipids in the resulting extract; and
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`(5) the lipid profiles of extracts from the different feed materials described
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`in Catchpole, such as dairy extract and krill, would be expected to be different.
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`Instead of refuting this evidence, Patent Owner proffers meaningless
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`comparisons of disparate examples from Catchpole and repackages some of the
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`U.S. Patent No. 9,072,752
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`same arguments that have been previously rejected by the Board.
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`II. PROPOSED CLAIMS 21-29 ARE UNPATENTABLE
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`A. Catchpole Discloses And Claims Compositions Satisfying The
`Proposed “From 6% To 10% Ether Phospholipids” Limitation
`Patent Owner’s claim that Catchpole does not disclose and teach krill oil
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`compositions satisfying the proposed “from 6% to 10% ether phospholipids”
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`limitation cannot withstand scrutiny. See PO Reply, 2-8.
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`First, Catchpole expressly discloses and claims compositions having greater
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`than 5% and 10% ether phospholipids (see, e.g., Exhibit 1009, p. 0009, lines 18-
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`21; p. 0035, lines 11-14; Tallon Decl. (Exhibit 1006), ¶¶ 212-216), and also
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`teaches how to obtain high levels of ether phospholipids. See, e.g., Exhibit 1009,
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`p. 0012, lines 13-16; Tallon Decl. (Exhibit 1006), ¶ 222.
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`Second, the Board found that: (1) based on Catchpole, a POSITA “would
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`have been motivated to create a krill oil composition containing greater than about
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`5%” ether phospholipids; (2) “Catchpole teaches that it is desirable to prepare such
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`a composition;” and (3) “it would have been obvious to prepare krill oil
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`compositions having from greater than 5% to 8% ether phospholipids.” IPR2018-
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`00295, Final Written Decision (Paper 35) (Exhibit 1129) (“-295 FWD”), 49-50, 65.
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`Third, the different feed materials described in Catchpole necessarily have
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`different lipid profiles, including different percentages of, inter alia,
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`phosphatidylcholine and ether phospholipids. This is illustrated by comparing the
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`lipid profiles of the feed materials of the examples Patent Owner relies on:
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`Examples 7 and 8 (dairy lipid extract B); Example 9 (dairy lipid extract A);
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`Example 10 (egg yolk lecithin); Example 12 (Hoki head); Example 17 (green-
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`lipped muscle); and Example 18 (krill). Additionally, extracts derived from these
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`different feed materials, using different extraction conditions, will likewise have
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`different lipid profiles. Notably Patent Owner’s Chief Scientist and expert, Dr.
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`Hoem, conceded as much when he testified, “a comparison” of the results reported
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`in Catchpole’s examples “is confounded by the differences in the feed materials.”
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`Hoem Reply (Exhibit 2025), ¶ 4; see Tallon Reply/Opp. (Exhibit 1086), ¶ 41.
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`Nevertheless, based on a comparison of the percentages of phospholipids
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`extracted from different feed materials described in Catchpole, Patent Owner
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`erroneously posits that these comparisons “cast doubt on whether increasing the
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`ethanol co-solvent [concentration] in the krill extraction would actually increase
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`the amount [of] ether phospholipids.” PO Reply, 4. For example, Patent Owner
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`argues that a comparison of the extracts in Examples 8 and 10, derived from
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`different feed materials (dairy lipid extract B versus egg yolk lecithin) extracted
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`with different co-solvent concentrations (30% versus 25% ethanol), “demonstrates
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`to a POSITA that the effect of changing extraction conditions . . . is
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`unpredictable.” PO Reply, 5. However, in making this argument, Patent Owner
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`ignores data in Examples 7 and 8 that shows when the same feed material is used,
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`increasing the ethanol concentration from 10% to 30% results in almost a five-fold
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`increase in the percentage of phosphatidylcholine extracted. Exhibit 1009, pp.
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`0018-0019; see p. 0012, lines 1-3; p. 0011, lines 11-17; Tallon Reply/Opp. (Exhibit
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`1086), ¶¶ 33-49. This is also consistent with the following excerpt from Catchpole:
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`We have found that co-solvent concentrations below about 10% produce
`very little extract of phospholipids. . . . At higher concentrations the rate
`of material extracted increases rapidly. We have found the co-solvent
`concentrations of at least 20%, and more preferably 30% achieve high
`levels of extraction of PC [phosphatidylcholine], . . . ALP
`[alkylacylphospholipid], PP [phospholipid]. . . .
`Exhibit 1009, p. 0012, lines 13-17; Tallon Reply/Opp. (Exhibit 1086), ¶¶ 39-40.1
`Based on Catchpole’s disclosure and teachings, a POSITA would have
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`understood that increasing co-solvent concentration would increase the
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`phospholipids, including ether phospholipids, present in the resulting extract.
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`Tallon Decl. (Ex. 1006), ¶ 222; Tallon Reply/Opp. (Ex.1086), ¶¶ 33-49, 57, 313.
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`Relying on Dr. Hoem, Patent Owner tries to disparage Catchpole by arguing
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`the data in Examples 11 and 12 is “seriously flawed” and a “POSITA would not
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`1 Confirming Catchpole’s teachings, Example 8 and corresponding Table 22 of the
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`‘752 patent report that 23% ethanol co-solvent resulted in a krill extract with 7-9%
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`ether phospholipids. Exhibit 1001, 31:45-32:44. Notably, Dr. Tallon, Dr.
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`Catchpole and other individuals from Industrial Research Limited performed the
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`work reported in Example 8 and Table 22. Tallon Decl. (Exhibit 1006), ¶ 20.
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`trust any of the results reported in Catchpole.” PO Reply 7-8. This argument is
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`unavailing for at least two reasons.
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`First, assuming arguendo that Dr. Hoem’s comments regarding Examples 11
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`and 12 are valid, the remainder of Catchpole’s disclosure and teachings cannot be
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`dismissed as Patent Owner proposes. See Beckman Instruments v. LKB Produkter
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`AB, 892 F.2d 1547, 1551 (Fed. Cir. 1989) (“Even if a reference discloses an
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`inoperative device, it is prior art for all that it teaches.”); Purdue Pharma Prods.
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`L.P. v. Par Pharm., Inc., 377 Fed. Appx. 978, 982 (Fed. Cir. 2010) (“a prior art
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`reference need not itself be enabled but is prior art for all that it discloses.”).
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`Second, over the past two (2) years, Dr. Hoem submitted six (6) declarations
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`addressing Catchpole: IPR2017-00745, -00746, -00747 and -00748 (Ex. 2001);
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`IPR2018-00295 (Ex. 2001 & 2013); IPR2018-01178, -01179 (Ex. 2001 & 2025);
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`IPR2018-01730 (Ex. 2001). Curiously, it was not until his seventh declaration, a
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`reply declaration in this proceeding, that Dr. Hoem avers for the first time “a
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`POSITA would not trust the results reported in Catchpole.” Ex. 2025, ¶ 11; see PO
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`Reply, 8. Given the suspect timing of this new attack -- after the Federal Circuit’s
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`decision in Aker Biomarine Antarctic AS v. Rimfrost AS, Case Nos. 2019-1078,
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`2019-1097, 2019 U.S. App. LEXIS 29656 (Fed. Cir. Oct. 3, 2019) (Ex. 1154) and
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`the Board’s Final Written Decisions in IPR2017-00745 (Ex. 1103), IPR2017-
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`00746 (Ex. 1104) and IPR2018-00295 (Ex. 1129)-- Dr. Hoem’s belated and post-
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`hoc assertions regarding Catchpole’s results should be afforded no weight.
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`Finally, Patent Owner’s citation to the Institution Decision is misplaced. PO
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`Reply, 2. The cited excerpt addressed the Board’s “anticipation analysis” of
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`original claims 5 and 6. Institution Decision (Paper 7), 10-12. Petitioner’s
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`arguments regarding proposed claims 21-29, however, are each predicated on
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`obviousness. Petitioner’s Opposition (Paper 19) (“Pet. Opp.”), 16-25.2
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`Patent Owner’s arguments based on its misplaced comparisons of
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`Catchpole’s extracts derived from different non-krill feed materials (most not
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`containing ether phospholipids) is simply immaterial. See, e.g., PO Reply, 3-7.
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`B. Dr. Tallon’s Unrebutted Testimony Demonstrates
`That Enzymotec’s Grade B Krill Extract Satisfies The
`Proposed “6% To 10% Ether Phospholipids” Limitation
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`Patent Owner’s contention that Enzymotec fails to disclose and teach a krill
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`oil composition having 8.0-9.7% ether phospholipids is meritless. PO Reply, 8-
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`10.3 First, Patent Owner’s “inherency argument” misses the mark. Petitioner’s
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`2 Dr. Hoem did testify that a high amount of co-solvent (31%) resulted in the
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`complete extraction of ether phospholipid from Hoki. See Hoem Dep., 72:7-74:8,
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`Exhibit 1153.
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`3 In addition to Enzymotec, Petitioner alternatively relies on Catchpole to satisfy
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`the “from 6% to 10% ether phospholipids” limitation. Pet. Opp., 24-25.
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`argument is based on Dr. Tallon’s unrebutted testimony detailing that a POSITA
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`would have understood that Enzymotec’s Grade B krill extract, having total
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`phospholipid and phosphatidylcholine contents of 70-95% and 60-85%,
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`respectively, also contained 8.0-9.7% ether phospholipids. See Tallon Reply/Opp.
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`(Exhibit 1086), ¶¶ 53-61; Tallon Decl. (Exhibit 1006), ¶¶ 237-242. Additionally,
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`Patent Owner’s assertion that “there is no basis for a POSITA to conclude that the
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`ether phospholipid levels observed in Catchpole Extract 2 could be used to
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`estimate the ether phospholipid levels of Enzymotec Grade B krill lecithin” (PO
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`Reply, 9) is likewise repudiated by Dr. Tallon’s unrebutted testimony. Tallon
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`Reply/Opp. (Exhibit 1086), ¶ 61; Tallon Dec. (Exhibit 1006), ¶¶ 241-242.
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`Further, Patent Owner’s criticism of Dr. Tallon’s use of the 10.6% ether
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`phospholipids/phospholipids (“ether PL/PL”) ratio from Catchpole Example 18 to
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`ascertain the percentage of ether phospholipids in Enzymotec’s Grade B krill
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`extract is contrived. First, Dr. Hoem testified that processes that extract
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`phospholipids also extract ether phospholipids. Hoem Dep. (Exhibit 1145), 91:13-
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`18, 117:7-13. Second, Patent Owner’s U.S. Patent No. 8,372,812 describes a krill
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`product with a phosphatidylcholine (PC) content of 19% (16.5 + .7+ .28 + .52), a
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`total phospholipid (PL) content of 23.23% and an ether phospholipid content of
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`1.98% (1.7 + .28). Thus, this krill product had an ether PC/PC ratio of 10.4%
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`(1.98/19) and an ether PL/PL ratio of 8.5% (1.98/23.23). Exhibit 1126, 45:1-15.
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`Finally, Patent Owner’s suggestion “[t]here is no evidence that the extraction
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`methods used by Enzymotec . . . would result in similar concentration” as that
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`described in Catchpole (PO Reply, 9) mistakenly focuses on extraction methods,
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`while claims 21-29 are composition claims. Tellingly, the Board found that a
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`POSITA “would have understood how to achieve the desired levels of components
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`by selectively extracting the different components and blending the extracts in
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`‘known and predictable ways to produce a desired krill oil composition.’” -295
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`FWD, 38-39; see Tallon Reply/Opp. (Exhibit 1086), ¶¶ 55, 115, 310-313.
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`Patent Owner has not refuted Dr. Tallon’s testimony, or offered any reason
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`why Enzymotec’s Grade B extract, with such high levels of phospholipids and
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`phosphatidylcholine, would not contain ether phospholipid levels falling within the
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`proposed amended claim range.
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`C. NKO, Randolph And Sampalis II Each Disclose
`Krill Oil Compositions Satisfying The Proposed
`100-700 mg/kg Astaxanthin Esters Limitation
`Admitted prior art NKO krill oil, Randolph and Sampalis II each satisfy the
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`proposed astaxanthin esters limitation.
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`Patent Owner’s argument that the specific NKO krill oil formulation
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`identified in the ‘752 patent should not be considered by the Board is meritless.
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`First, Dr. Tallon’s testimony that commercial NKO krill oil products were
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`available in different formulations stands unrebutted. Tallon Reply/Opp. (Exhibit
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`1086), ¶ 265. In addition, Petitioner has not argued that each of those commercial
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`NKO formulations inherently possessed 100-700 mg/kg astaxanthin esters. Rather,
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`Petitioner has maintained that the proposed astaxanthin esters limitation is satisfied
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`by the specific NKO formulation in Table 16 of the ‘752 patent that Patent Owner
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`admitted (1) had 472 mg/kg astaxanthin esters and (2) was the “closest prior art.”
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`See, e.g., Pet. Opp., 13; Tallon Reply/Opp. (Exhibit 1086), ¶¶ 247-249.
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`Patent Owner’s suggestion that these admissions were purportedly “not
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`known to a POSITA,” and therefore cannot be considered by the Board in
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`accessing the patentability of the proposed clams is legally erroneous. PO Reply,
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`10. Specifically, the Federal Circuit has held “[a]dmissions in the specification
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`regarding the prior art are binding on the patentee for purposes of a later inquiry
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`into obviousness.” Pharmastem Therapeutics v. Viacell, 491 F.3d 1343, 1362
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`(Fed. Cir. 2007); see Sanofi-Aventis v. Mylan Pharm. Inc., Nos. 2019-1368, 2019-
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`1369, slip op. at 9-10 (Fed. Cir. Nov. 19, 2019) (the Board’s use of a patent
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`specification for its teachings about prior art “did not rest on legal error”).
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`Finally, Patent Owner’s attempt to liken this case to In re Newell is
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`misplaced. PO Reply, 10-11. In Newell, the Federal Circuit determined that there
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`was no motivation to combine the prior art other than the inventor’s discovery of a
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`previous unknown problem, and found it was improper to rely on the inherency of
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`a problem to find an invention obvious. 891 F.2d 899, 901-02 (Fed. Cir. 1989). In
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`contrast, Petitioner is not using inherency as a hindsight substitute for motivation;
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`astaxanthin was already a well-known constituent of krill oil compositions. See
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`Tallon Reply Opp. (Exhibit 1086), ¶¶ 264-265, 312; Tallon Decl. (Exhibit 1006),
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`¶¶ 81, 86-87, 89, 286-287, 304, 334, 384.
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`Patent Owner incorrectly argues that Randolph’s disclosure of compositions
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`with “any amount” of astaxanthin, and in particular, 0.5-50 mg, is “not related to”
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`the krill oil compositions disclosed in Randolph, and that Dr. Tallon engaged in
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`improper “cherry picking” of the ranges disclosed in Randolph. PO Reply, 11. In
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`fact, Patent Owner’s reference to Randolph’s disclosure of 1% astaxanthin citing to
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`Tallon Dec. ¶ 284, Ex. 1006, is cherry picking and disregards that same
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`paragraph’s disclosure of 50 mg/kg and greater. Hoem Dep. 91:24-92:17, Exhibit
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`1153. It is undisputed that Randolph describes compositions with “between about
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`0.5 mg and about 50 mg” of astaxanthin, and “between about 300 mg and about
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`3000 mg [0.003 kg]” of krill oil. Ex. 1011, ¶¶ 0040, 0044 (emphasis added). Dr.
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`Tallon correctly used the endpoint values for astaxanthin and krill oil to calculate
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`that Randolph discloses krill oil compositions having 167 mg/kg of astaxanthin
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`(i.e., 0.5 mg/0.003 kg), which is equivalent to 158 mg/kg astaxanthin esters.
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`Tallon Reply/Opp. (Ex. 1086), ¶ 256. Relying on Dr. Tallon’s calculation, the
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`Board found that Randolph describes compositions with amounts of astaxanthin
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`esters that “overlap with the [100-700] range recited in the substitute claims.” -295
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`FWD, 67-68; see In re Peterson, 315 F.3d 1325, 1329 (Fed. Cir. 2003).
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`Patent Owner’s criticisms of Sampalis II’s disclosure of krill oil containing
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`at least 20 mg/100 ml [200 mg/kg] astaxanthin esters are baseless. PO Reply, 11.
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`First, Sampalis II is directed to phospholipid extracts “from a marine or
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`aquatic biomass.” Exhibit 1013, p. 1 (Abstract); p. 3, lines 9-12; p. 5, lines 1-3.
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`Sampalis II states the recited extracts are preferably extracted from krill, such as
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`Euphausia superba (id., p. 0027, lines 2-9), and notes that antioxidants, such as
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`astaxanthin esters, are present in amounts of “at least” 20 mg/100 ml. Id., p. 0032,
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`lines 1-7; Tallon Reply/Opp. (Exhibit 1086), ¶¶ 312-316. Dr. Hoem confirmed 20
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`mg/100 ml astaxanthin is equivalent to 200 mg/kg astaxanthin and 190 mg/kg
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`astaxanthin esters. Hoem Dep. (Exhibit 1128), 207:13-209:9.
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`Second, Patent Owner’s suggestion that a POSITA would “discredit”
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`Sampalis II’s disclosure and teachings of krill extracts having at least 200 mg/kg
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`astaxanthin because Table 5 lists components found in both marine and aquatic
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`biomass extracts is disingenuous. For example, while Patent Owner asserts that a
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`POSITA would recognize that it is “impossible” for a krill extract to contain
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`canthaxaxanthin (PO Reply, 12), the ‘752 patent acknowledges that prior art krill
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`extracts contained canthaxaxanthin. Exhibit 1001, 1:31-45. Further, Patent
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`Owner’s suggestion that Grynbaum confirms “the only carotenoid present in krill
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`is astaxanthin” is misleading. PO Reply, 12. Although Grynbaum notes
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`“astaxanthin was the sole carotenoid identified,” the next sentence states: “This is
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`also inconsistent with the literature.” Exhibit 1039, p. 0008. Finally, the prior art
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`expressly disclosed that krill oil compositions contained “a novel flavonoid.” See,
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`e.g., Sampalis I (Exhibit 1012), p. 0004; Bunea (Exhibit 1020), p. 0007; see Tallon
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`Decl. (Exhibit 1006), ¶¶ 287, 334. Thus, contrary to Patent Owner’s allegation, it
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`is not at all surprising that Table 5 identifies flavonoids as being present in the
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`extracts encompassed by the teachings of Sampalis II. Accordingly, a POSITA
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`would not “discredit” the teachings of Sampalis II as averred by Patent Owner.
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`III. CONCLUSION
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`A preponderance of evidence demonstrates that the “ether phospholipid
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`disclosures” of Catchpole and/or Enzymotec and the “astaxanthin ester disclosures”
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`of NKO, Randolph and/or Sampalis II render proposed claims 21-29 obvious.
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`Dated: November 20, 2019
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`Respectfully submitted,
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`HOFFMANN & BARON, LLP
`6900 Jericho Turnpike
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`Syosset, New York 11791
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`(516) 822- 3550
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`/james f. harrington/
`James F. Harrington
`jfhdocket@hbiplaw.com
`Registration No. 44,741
`Lead Counsel for Petitioner
`Rimfrost AS
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`CERTIFICATE OF SERVICE
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`I hereby certify that on this 20th day of November, 2019, PETITIONER’S SUR-
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`REPLY TO PATENT OWNER’S MOTION TO AMEND was served in its
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`entirety on the following counsel of record by electronic service by email at the
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`email addresses as set forth below in accordance with the consent set forth in
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`Patent Owner’s Mandatory Notices Pursuant to 37 C.F.R. § 42.8 (Paper No. 4).
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`David A. Casimir
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`J. Mitchell Jones
`CASIMIR JONES S.C.
`2275 Deming Way, Suite 310
`Middleton, WI 53562
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`docketing@casimirjones.com
`dacasimir@casimirjones.com
`jmjones@casimirjones.com
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`By:
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`/Michael I. Chakansky/
`Michael I. Chakansky (Reg. No. 31,600)
`Hoffmann & Baron, LLP
`4 Century Drive
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`Parsippany, N.J. 07054
`mchakansky@hbiplaw.com
`Tel: 973.331.1700
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