`571.272.7822
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` Paper No. 35
` Entered: June 12, 2019
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`UNITED STATES PATENT AND TRADEMARK OFFICE
`_____________
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`____________
`
`RIMFROST AS,
`Petitioner,
`
`v.
`
`AKER BIOMARINE ANTARCTIC AS,
`Patent Owner.
`____________
`
`Case No. IPR2018-00295
`Patent 9,320,765 B2
`____________
`
`
`
`Before TINA E. HULSE, JACQUELINE T. HARLOW,
`and JOHN E. SCHNEIDER, Administrative Patent Judges.
`
`SCHNEIDER, Administrative Patent Judge.
`
`
`
`
`FINAL WRITTEN DECISION
`35 U.S.C. § 318(a) and 37 C.F.R. § 42.73
`
`
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`RIMFROST EXHIBIT 1129 Page 0001
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`IPR2018-00295
`Patent 9,320,765 B2
`
`INTRODUCTION
`
`I.
`A. Background
`Rimfrost AS (“Petitioner”) filed a Petition requesting inter partes
`review of claims 1–48 of U.S. Patent No. 9,320,765 B2 (“the ’765 patent”).
`Paper 1, (“Pet.”). Aker Biomarine Antarctic AS (“Patent Owner”) did not
`file a Preliminary Response. We determined, based on the information
`contained in the Petition that there was a reasonable likelihood that
`Petitioner would prevail in challenging claims 1–48 as unpatentable under
`35 U.S.C § 103(a). Pursuant to 35 U.S.C. § 314, the Board instituted trial on
`June 14, 2018. Paper 9 (“Dec.”).
`Patent Owner filed a Response to the Petition on September 5, 2018.
`Paper 14 (“PO Resp.”). Petitioner filed a Reply on November 26, 2018.
`Paper 19 (“Reply”). Patent Owner filed a Sur-Reply on January 18, 2019.1
`Paper 27 (Sur-Reply”).
`Patent Owner also filed a Motion to Amend on September 5, 2018.
`Paper 16 (“MTA”). Petitioner filed an Opposition to the Motion to Amend
`on November 26, 2018. Paper 20 (“MTA Opp.”). Patent Owner filed a
`Reply on December 27, 2018. Paper 22 (“MTA Reply”). Petitioner filed a
`Sur-Reply to the Motion to Amend on February 1, 2019. Paper 30 (“MTA
`Sur-Reply”).
`On March 12, 2019, the parties presented arguments at an oral
`hearing. The hearing transcript has been entered in the record. Paper 34
`(“Tr.”).
`
`
`1 In an email to the Board dated January 3, 2019, the parties jointly requested
`authorization to file Sur-Replies in lieu of a Motion for Observations and
`Response to the Motion for Observations. The Board granted the request on
`February 4, 2019.
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`2
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`We have jurisdiction under 35 U.S.C. § 6. Petitioner bears the burden
`of proving unpatentability of the challenged claims, and that burden of
`persuasion never shifts to Patent Owner. Dynamic Drinkware, LLC v. Nat’l
`Graphics, Inc., 800 F.3d 1375, 1378 (Fed. Cir. 2015). To prevail, Petitioner
`must prove unpatentability by a preponderance of the evidence. See
`35 U.S.C. § 316(e); 37 C.F.R. § 42.1(d). This Final Written Decision is
`issued pursuant to 35 U.S.C. § 318(a) and 37 C.F.R. § 42.73. For the
`reasons that follow, we determine that Petitioner has shown by a
`preponderance of the evidence that claims 1–48 of the ’765 patent are
`unpatentable. We also find that the proposed amended claims are also
`unpatentable for the reasons that follow. See 35 U.S.C. § 316(e).
`B. Additional Proceedings
`The ’765 patent was the subject of a now-terminated investigation
`before the International Trade Commission: Certain Krill Products and
`Krill Meal for Production of Krill Oil Products, Investigation No. 337-TA-
`1019. Pet. 2; Paper 4, 1; Ex. 1054.
`The following proceedings before the Board involve the same parties
`as the instant inter partes review, and concern patents related to the
`’765 patent: IPR2017-00745 (Paper 24) (finding claims 1–20 of U.S. Patent
`No. 9,078,905 B2 (“the ’905 patent”) unpatentable); IPR2017-00746 (Paper
`23) (finding claims 1–19 of U.S. Patent No. 9,028,877 B2 (“the
`’877 patent”) unpatentable);2 IPR2017-00747 (Paper 24) (finding claims 1–
`20 of the ’905 patent not shown to be unpatentable); IPR2017-00748 (Paper
`23) (finding claims 1–19 of the ’877 patent not shown to be unpatentable);
`
`
`2 On October 12, 2018, Patent Owner filed Notices of Appeal seeking
`review of the final written decisions in IPR2017-000745 and IPR2017-
`000746. Paper 33, 5.
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`3
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`PGR2018-00033 (Paper 9) (declining to institute post grant review of claims
`1–20 of U.S. Patent No. 9,644,170 B2); IPR2018-01178 (Paper 7)
`(instituting inter partes review of claims 1–32 of U.S. Patent No. 9,375,453
`B2); IPR2018-01179 (Paper 7) (instituting inter partes review of claims 33–
`61 of U.S. Patent No. 9,375,453 B2); IPR2018-01730 (Paper 7) (instituting
`inter partes review of claims 1–20 of U.S. Patent No. 9,072,752 B1).
`In addition, the ’877 and ’905 patents are at issue in Aker Biomarine
`v. Olympic Holding AS, Case No. 1:16-CV-00035 LPS-CJB (D. Del.), which
`has been stayed. Paper 33, 5.
`C. The ’765 Patent (Ex 1001)
`The ’765 patent, titled “Bioeffective Krill Oil Compositions” issued
`on April 26, 2016, from U.S. Patent Application No. 14/020,155, filed on
`September 6, 2013. Ex. 1001, at [54], [45], [21], [22]. The ’765 patent is a
`continuation of U.S. Patent Application No. 12/057,775, filed on March 28,
`2008. The ’765 patent claims priority to U.S. Provisional Application No.
`60/920,483, filed on March 28, 2007; U S. Provisional Application No.
`60/975,058, filed on September 25, 2007; U.S Provisional Application No.
`60/983,446, filed on October 29, 2007; and U.S. Provisional Application No.
`61/024,072, filed on January 28, 2008. Id. at col. 1, ll. 6–14.
`The ’765 patent describes extracts from Antarctic krill, small shrimp-
`like animals, that include bioactive fatty acids. Ex. 1001, col. 1, ll. 19–20.
`The ’765 patent teaches krill oil compositions characterized by having “high
`amounts of phospholipids, astaxanthin esters and omega-3 contents.”
`Ex. 1001, Abstract. According to the Specification, the compositions
`disclosed in the ’765 patent are effective “in a number of areas such as anti-
`inflammation, antioxidant effects, improving insulin resistances and
`improving blood lipid profile.” Id. In addition, the ’765 patent recognizes
`
`4
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`that a myriad of health benefits have been attributed to krill oil in the prior
`art. For example, the ’765 patent states that “[k]rill oil compositions have
`been described as being effective for decreasing cholesterol, inhibiting
`platelet adhesion, inhibiting artery plaque formation, preventing
`hypertension, controlling arthritis symptoms, preventing skin cancer,
`enhancing transdermal transport, reducing the symptoms of premenstrual
`symptoms or controlling blood glucose levels in a patient.” Id. at col. 1, ll.
`46–52.
`The ’765 patent acknowledges that krill oil compositions, including
`compositions having up to 60% w/w phospholipid content and as much as
`35% w/w 5,8,11,14,17-eicosapentaenoic acid (EPA)/ 4,7,10,13,16,19-
`docosahexanoic acid (DHA) content, were known in the art at the time of the
`invention. Id. at col. 1, ll. 52–57. The ’765 patent also indicates that
`supercritical fluid extraction with a solvent modifier was known to be a
`useful method for extracting marine phospholipids from salmon roe. Id. at
`col. 1, ll. 65–67.
`According to the ’765 patent, however, the solvent extraction methods
`used in the prior art to isolate krill oil from the krill “rely on the processing
`of frozen krill that are transported from the Southern Ocean to the
`processing site,” which transportation is expensive and may result in the
`degradation of the krill starting material. Id. at col. 2, ll. 3‒6. Such methods
`have included steps of placing the starting material into a ketone solvent,
`such as acetone, to extract the lipid soluble fraction, and recovering the
`soluble lipid fraction from the solid contents using a solvent such as ethanol.
`Id. at col. 1, ll. 32‒40.
`To overcome the above limitations, the ’765 patent discloses
`“methods for processing freshly caught krill at the site of capture and
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`preferably on board a ship.” Id. at col. 10, ll. 18‒20. The ’765 patent
`explains that the krill may be first subject to a protein denaturation step, such
`as a heating step, to avoid the formation of enzymatically decomposed oil
`constituents. Id. at col. 9, ll. 43‒50; col. 10, ll. 26‒31. Subsequently, the
`“oil can be extracted by an optional selection of nonpolar and polar solvents
`including use of supercritical carbon dioxide.” Id. at col. 9, ll. 51‒54.
`In Example 7 of the ’765 patent, “[k]rill lipids were extracted from
`krill meal (a food grade powder) using supercritical fluid extraction with co-
`solvent.” Id. at col. 31, ll. 15‒16.
`Initially, 300 bar pressure, 333°K and 5% ethanol (ethanol:CO2,
`w/w) were utilized for 60 minutes in order to remove neutral
`lipids and astaxanthin from the krill meal. Next, the ethanol
`content was increased to 23% and the extraction was maintained
`for 3 hours and 40 minutes. The extract was then evaporated
`using a falling film evaporator and the resulting krill oil was
`finally filtered.
`
`Id. at col. 31, ll. 17‒23.
`Example 8 of the ’765 patent discloses preparing krill oil using the
`same method described in Example 7, from the same krill meal used in that
`example. Ex. 1001, col. 31, ll. 44‒46. The krill oil was then analyzed using
`31P NMR3 analysis to identify and quantify the phospholipids in the oil. Id.
`at col. 31, ll. 47‒49. Table 224 shows the phospholipid profiles for the raw
`material, the final product, and a commercially available krill oil, Neptune
`Krill Oil (“NKO”). Id. at col. 33, ll. 6‒9. Table 22 is reproduced below:
`
`
`3 Phosphorous Nuclear Magnetic Resonance.
`4 We view reference in the ’765 patent to “table 25” (Ex. 1001, col. 32, ll. 7‒
`10) to be an inadvertent typographical error, as the Specification does not
`include a table 25. We understand Example 8 of the Specification to refer,
`instead, to Table 22, which sets forth the described phospholipid profiles.
`
`6
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`
`
`Id. at col. 32, ll. 17–39.
`The ’765 patent teaches that the “main polar ether lipids of the krill
`meal are alkylacylphosphatidylcholine (AAPC) at 7–9% of total polar lipids,
`lyso-alkylacylphosphatidylcholine (LAAPC) at 1% of total polar lipids
`(TPL) and alkylacylphosphatidyl-ethanolamine (AAPE) at <1% of TPL.”
`Id. at col. 32, ll. 10‒16.
`The ’765 patent teaches that the krill oil compositions can comprise a
`blend of lipid fractions obtained from krill. Ex. 1001, col. 2, ll. 62–63. The
`’765 patent teaches
`In further embodiments, the present invention provides a
`blended krill oil composition comprising: from about 45% to 40
`55% w/w phospholipids; from about 20% to 45% w/w
`triglycerides; and from about 400 to about 2500 mg/kg
`
`7
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`astaxanthin. In some embodiments, the blended krill oil product
`comprises a blend of lipid fractions obtained from E. superba. In
`some embodiments, the composition comprises 45 from about
`25% to 30% omega-3 fatty acids as a percentage of total fatty
`acids and wherein from about 80% to 90% of said omega-3 fatty
`acids are attached to said phospholipids.
`
`Id. at col. 5, ll. 39–48. The ’765 patent also teaches that compositions of the
`invention can be formedby preparing an extract containing neutral lipids and
`another with polar lipids such as ether phospholipids and then blending the
`two extracts together. Id. at col. 12, ll. 3–36.
`D. Illustrative Claim
`Of the challenged claims, claims 1 and 25 are independent. Claims 2–
`24 depend from claim 1 and claims 26–48 depend from claim 25. Claim 1 is
`illustrative of the claimed subject matter and reads as follows:
`1. A krill oil composition comprising E. superba krill oil suitable
`for oral administration, said krill oil comprising greater than
`about 3% ether phospholipids w/w of said krill oil; from about
`27% to 50% non-ether phospholipids w/w of said krill oil so that
`the amount of total phospholipids in the composition is from
`about 30% to 60% w/w of said krill oil; from about 20% to 50%
`triglycerides w/w of said krill oil, and astaxanthan esters in
`amount of greater than about 100 mg/kg of said krill oil.
`Ex. 1001, col. 34, l. 64–col. 35, l. 5. Claim 25 adds the additional limitation
`that the krill oil composition is encapsulated. Ex. 1001, col. 36, ll. 1–11.
`
`8
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`RIMFROST EXHIBIT 1129 Page 0008
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`
`
`Sampalis, Catchpole, Fricke,
`Breivik, and Bottino9
`
`Sampalis, Catchpole, Fricke,
`Breivik, and Randolph10
`
`§ 103(a)
`
`§103(a)
`
`Claims Challenged
`1–4, 7, 9–11, 14, 18–
`20, 25–28, 31, 33–35,
`38, 42–44, and 47
`5, 6, 12, 13, 15, 16, 21–
`23, 29, 30, 36, 37, 39,
`40, 45, and 46
`8, 17, 24, 32, 41, and
`48
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`IPR2018-00295
`Patent 9,320,765 B2
`E. The Asserted Grounds of Unpatentability
`Petitioner contends that the challenged claims are unpatentable on the
`following grounds. Pet. 7.
`References
`Sampalis5, Catchpole6, Fricke7, and
`Breivik8
`
`Basis
`§ 103(a)
`
`
`Petitioner also relies on the Declaration of Stephen J. Tallon, Ph.D.
`Ex 1006. Patent Owner relies on the declaration of Dr. Nils Hoem.
`Ex. 2001.
`
`
`
`
`
`5 Fotini Sampalis et al., Evaluation of the Effects of Neptune Krill Oil™ on
`the Management of Premenstrual Syndrome and Dysmenorrhea, 8 ALT.
`MED. 171–179 (2003) (“Sampalis”) (Ex. 1012).
`6 Catchpole and Tallon, WO 2007/123424 A1, published Nov. 1, 2007
`(“Catchpole”) (Ex. 1009).
`7 Fricke et al. Lipid, Sterol and Fatty Acid Composition of Antarctic Krill, 19
`LIPIDS 821–827 (1984) (“Fricke”) (Ex. 1010).
`8 Harold Breivik, WO 2008/060163 A1, published May 22, 2008 (“Breivik”)
`(Ex. 1037). Breivik claims priority to U.S. Provisional Application No.
`60/859,289, filed Nov. 16, 2006 (Ex. 1037, [30]).
`9 N.R. Bottino, The Fatty Acids of Antarctic Phytoplankton and Euphausiids.
`Fatty Acid Exchange among Trophic Levels in the Ross Sea, 27 MARINE
`BIOL. 197–204 (1974) (“Bottino ”) (Ex. 1007).
`10 Randolph et al., US 2005/0058728 A1, published Mar. 17, 2005
`(“Randolph”) (Ex. 1011).
`
`9
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`
`II. ANALYSIS
`
`A. Priority Date
`Petitioner asserts that each claim of the ’765 patent requires the
`presence of ether phospholipids, and that support for ether phospholipids
`was not introduced until the filing of U.S. Provisional Application No.
`61/024,072 on January 28, 2008. Pet. 8–9.; Ex. 1006 ¶ 40. Petitioner thus
`contends “the earliest effective priority date for the claims of the ’765 patent
`is no earlier than January 28, 2008.” Pet. 8.
`Alternatively, Petitioner argues that none of the applications to which
`the ’765 patent claims priority include written description support for the
`open-ended ether phospholipid ranges recited in the challenged claims. Id.
`at 8–9. Petitioner thus asserts that the ’765 patent is not entitled to a priority
`date earlier than the filing of the date of the application that issued as the
`’765 patent (i.e., September 6, 2013). Id.
`Patent Owner does not contest Petitioner’s assertion that the effective
`filing date of the ’765 patent is no earlier than January 28, 2008. See PO
`Resp. 6.
`We have reviewed the provisional applications that lead to the ’765
`patent and conclude that the earliest effective filing date of the claims of the
`’765 patent is no earlier than January 28, 2008. For purposes of this
`decision, we need not address whether the effective filing date of the claims
`of the ’765 patent is later than January 28, 2008.
`B. Claim Construction
`In an inter partes review, the Board interprets claim terms in an
`unexpired patent according to the broadest reasonable construction in light
`of the specification of the patent in which they appear. 37 C.F.R. § 100(b)
`(2017); Cuozzo Speed Techs., LLC v. Lee, 136 S. Ct. 2131, 2142 (2016)
`
`10
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`(affirming applicability of broadest reasonable construction standard to inter
`partes review proceedings).11 Under that standard, and absent any special
`definitions, we generally give claim terms their ordinary and customary
`meaning, as would be understood by one of ordinary skill in the art at the
`time of the invention. See In re Translogic Tech., Inc., 504 F.3d 1249, 1257
`(Fed. Cir. 2007). Any special definitions for claim terms must be set forth
`with reasonable clarity, deliberateness, and precision. See In re Paulsen,
`30 F.3d 1475, 1480 (Fed. Cir. 1994).
`1. Greater than about 5% w/w ether phospholipids
`Claims 18 and 42 each recite the limitation calling for “greater than
`about 5% w/w ether phospholipids.” Ex. 1001, col. 35, ll. 49–50, col. 36, ll.
`59–61.
`Petitioner contends the term “greater than about 5% w/w” should be
`construed to mean “greater than 4.5% w/w.” Pet. 27. In support of this
`contention Petitioner contends that this is consistent with the Specification in
`that the Specification only recited whole numbers for weight amounts and
`that interpreting the term to extend down to 4.5% would be consistent with
`rounding to the next whole number. Pet. 26. Petitioner relies on Dr.
`Tallon’s testimony that one skilled in the art would understand the term
`“about 5%” to extend down to 4.5% to support its position. Pet. 27 (citing
`Ex. 1002 ¶ 93).
`
`
`11 The Office recently changed the claim construction standard to be
`employed in an inter partes review. See Changes to the Claim Construction
`Standard for Interpreting Claims in Trial Proceedings Before the Patent Trial
`and Appeal Board, 83 Fed. Reg. 51,340 (Oct. 11, 2018). However, based on
`the filing date of the Petition in this proceeding, the applicable claim
`construction standard remains as set forth in 37 C.F.R. § 42.100(b) (2017).
`
`11
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`Patent Owner contends that “greater than about 5%” should be
`construed to mean “greater than 4.95%.” PO Resp. 12–13. In support of
`this contention, Patent Owner points to Dr. Tallon’s testimony
`acknowledging that the values for phospholipids in Examples 7 and 8 of the
`’765 patent are accurate to a tenth of a percent. Id. at 12. Patent Owner
`argues that applying the rationale used by Dr. Tallon in his declaration, one
`skilled in the art would round a value of 4.95% up to 5% and 4.94% down to
`4.9%. Id. at 13.
`“Such broadening usages as ‘about’ must be given reasonable scope;
`they must be viewed by the decision maker as they would be understood by
`persons experienced in the field of the invention. Although it is rarely
`feasible to attach a precise limit to ‘about,’ the usage can usually be
`understood in light of the technology embodied in the invention.” Modine
`Mfg. Co. v. U.S. Int’l Trade Comm’n, 75 F.3d 1545, 1554 (Fed. Cir. 1996).
`After considering the parties’ arguments and reviewing the
`Specification of the ’765 patent, we conclude that Petitioner’s proposed
`construction is consistent with the intrinsic evidence. Although the ’765
`patent does not explicitly address the issue of “about,” the meaning of the
`term can be discerned from a careful reading of the Specification. Example
`8 of the ’765 patent reports the analysis of phospholipid fractions of a
`product of the invention and a commercially available Krill product. Ex.
`1001, col. 31, l, 46–col. 32, l. 42. Table 22, reproduced above, reports the
`calculated values for the various phospholipids in values to a tenth of a
`percent. Id. at col. 32, ll. 18–38. In the discussion of the table, the values
`are rounded to the nearest whole number, not the nearest tenth. Id. at col.
`32, ll. 11–15. This is consistent with the approach advanced by Petitioner.
`
`12
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`For the purposes of this Decision, the term “greater than about 5%
`w/w” shall be construed to mean “greater than 4.5% w/w.”
`2. The remaining claims terms
`Although both Petitioner, Pet. 18–24, and Patent Owner, PO Resp.
`10–12, offer several claim constructions for additional terms, we determine
`that no explicit construction of any additional claim term is necessary for
`purposes of this Decision. In reaching this conclusion, we observe that
`Patent Owner does not contest Petitioner’s proposed constructions of “plant
`phytonutrient” and “astaxanthin esters.” PO Resp. 11. With respect to the
`remaining terms, the parties’ proposed constructions are largely coextensive
`with each other, and to the extent those constructions differ, they do so in
`ways that do not impact our analysis. For example, our analysis below
`remains the same irrespective of whether we apply Petitioner’s construction
`of “krill oil” as meaning “lipids extracted from krill,” Pet. 19, or Patent
`Owner’s interpretation, “mixture of lipids extracted from krill,” PO Resp.
`10.
`
`C. Level of Ordinary Skill in the Art
`The level of ordinary skill in the art is a factual determination that
`provides a primary guarantee of objectivity in an obviousness analysis. Al-
`Site Corp. v. VSI Int’l Inc., 174 F.3d 1308, 1324 (Fed. Cir. 1999) (citing
`Graham v. John Deere Co., 383 U.S. 1, 17–18 (1966); Ryko Mfg. Co. v. Nu-
`Star, Inc., 950 F.2d 714, 718 (Fed. Cir. 1991)).
`Petitioner asserts that a relevant skilled artisan would have possessed
`“an advanced degree in marine sciences, biochemistry, organic (especially
`lipid) chemistry, chemical or process engineering, or associated sciences”
`(Pet. 6), as well as having a complementary understanding of “organic
`chemistry and in particular lipid chemistry, chemical or process engineering,
`
`13
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`marine biology, nutrition, or associated sciences; and knowledge of or
`experience in the field of extraction” (id.), in addition to “at least five years
`applied experience” (id.). Patent Owner has accepted this definition for
`purposes of this Proceeding. PO Resp. 13.
`We agree with Petitioner and Patent Owner and find that Petitioner’s
`description of the level of ordinary skill in the art at the time of invention of
`the ’765 patent is consistent with the type of problems encountered in the
`art, prior art solutions to those problems, rapidity with which innovations are
`made, sophistication of the technology, and educational level of active
`workers in the field. See In re GPAC Inc., 57 F.3d 1573, 1579 (Fed. Cir.
`1995). For purposes of this Decision, therefore, we adopt Petitioner’s
`description. We also note that the applied prior art reflects a level of skill at
`the time of the claimed invention consistent with our determination. See
`Okajima v. Bourdeau, 261 F.3d 1350, 1355 (Fed. Cir. 2001).
`In addition, we recognize each of Petitioner’s and Patent Owner’s
`declarants as qualified to provide the proffered opinions on the level of skill
`and the knowledge of a person of ordinary skill in the art at the time of the
`invention. The relative weight that we assign such testimony, however, is
`subject to additional factors. See, e.g., 37 C.F.R. § 42.65(a) (“Expert
`testimony that does not disclose the underlying facts or data on which the
`opinion is based is entitled to little or no weight.”); Office Patent Trial
`Practice Guide, 77 Fed. Reg. 48,756, 48,763 (Aug. 14, 2012) (same).
`D. Overview of the Prior Art
`Petitioner relies on the combination of Sampalis, Catchpole, Fricke,
`Breivik, Bottino and/or Randolph to support its contention that claims 1–48
`of the ’765 patent would have been obvious. Pet. 7. Patent Owner asserts
`
`14
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`that Prescott12, Zimmerman13, Calder14, Zierenberg15, Blank16, Marathe17,
`Hartvigsen18, and Tanaka I19 support its argument that an ordinarily skilled
`artisan would not have made Petitioner’s proposed combinations and further
`that the prior art teaches away from encapsulation of krill oil with high
`levels of ether phospholipids. See, e.g., PO Resp. 14–26. We provide an
`overview of each reference below.
`1. Sampalis
`Sampalis describes a clinical trial “[t]o evaluate the effectiveness of
`Neptune Krill OilTM (NKOTM) for the management of premenstrual
`syndrome and dysmenorrhea.” Ex. 1012, 1. Sampalis explains that Neptune
`
`
`12Prescott et al., Platelet-Activating Factor and Related Lipid Mediators, 69
`ANNU. REV. BIOCHEM. 419–45 (2000) (“Prescott”) (Ex. 2003).
`13 Zimmerman et al., The Platelet-Activating Factor Signaling System and
`Its Regulators in Syndromes of Inflammation and Thrombosis, 30 CRIT.
`CARE MED. S294–301 (2002) (“Zimmerman”) (Ex. 2004).
`14 P. Calder, n-3 Polyunsaturated fatty acids, inflammation, and
`inflammatory diseases, 83 AM. J. CLIN. NUTR. 1505S–19S (2006) (“Calder”)
`(Ex. 2005).
`15 Zirenberg and Grundy, Intestinal absorption of
`polyenephosphatidylcholine in man, 23 J. LIPID RES. 1136–1142 (1982)
`(“Zirenberg”) (Ex. 2008).
`16 Blank et al., Meats and Fish Consumed in the American Diet Contain
`Substantial Amounts of Ether-Linked Phospholipids, 122 J. NUTR. 1656–61
`(1992) (“Blank”) (Ex. 2009).
`17 Marathe et al., Inflammatory Platelet-activating Factor-like Phospholipids
`in Oxidized Low Density Lipoproteins Are Fragmented Alkyl
`Phosphatidylcholines, 274 J. BIO CHEM. 28395–28404 (1999) (“Marathe”)
`(Ex. 2011).
`18 Hartvigsen et al., 1-O-Alkyl-2-(ω-oxo)-sn-glycerols from Shark Oil and
`Human Milk Fat Are Potential Precursors of PAF Mimics and GBH, 41
`LIPIDS 679–693 (2006) (“Hartvigsen”) (Ex. 2010).
`19 Tanaka et al., Platelet-activating Factor (PAF)-like Phospholipids Formed
`during Peroxidation of Phosphatidylcholines from Different Foodstuffs, 59
`BIOSCI. BIOTECH. BIOCHEM. 1389–1393 (1995) (“Tanaka I”) (Ex. 1014).
`
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`Krill Oil is “extracted from Antarctic krill also known as E. superba. E.
`superba, a zooplankton crustacean, is rich in phospholipids and triglycerides
`carrying long-chain omega-3 polyunsaturated fatty acids, mainly EPA and
`DHA, and in various potent antioxidants including vitamins A and E,
`astaxanthin, and a novel flavonoid.” Id. at 4.
`Sampalis discloses that each patient in the clinical trial was “asked to
`take two 1-gram soft gels of either NKO or omega-3 18:12 fish oil (fish oil
`containing 18% EPA and 12% DHA) once daily with meals during the first
`month of the trial.” Id. Sampalis reports that “[t]he final results of the
`present study suggest within a high level of confidence that Neptune Krill
`Oil can significantly reduce the physical and emotional symptoms related to
`premenstrual syndrome, and is significantly more effective for the
`management of dysmenorrhea and emotional premenstrual symptoms than
`fish oil.” Id. at 8.
`2. Catchpole
`Catchpole discloses “a process for separating lipid materials
`containing phospholipids” (Ex. 1009, 1, ll. 5–6) in order to produce a
`product containing “desirable levels of particular phospholipids” (id. at 3, ll.
`27–28). Catchpole states that phospholipids “have been implicated in
`conferring a number of health benefits including brain health, skin health,
`eczema treatment, anti-infection, wound healing, gut microbiota
`modifications, anti-cancer activity, alleviation of arthritis, improvement of
`cardiovascular health, and treatment of metabolic syndromes. They can also
`be used in sports nutrition.” Id. at 1, l. 29–2, l. 2. Catchpole further
`discloses that products having high levels of particular phospholipids “may
`be employed in a number of applications, including infant formulas, brain
`health, sports nutrition and dermatological compositions.” Id. at 25, ll. 9–13.
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`Catchpole describes, in Example 18, the fractionation of krill lipids
`from krill powder using a process that employs supercritical CO2 in a first
`extraction, and a CO2 and absolute ethanol mixture in a second. Id. at 24, ll.
`1–16. Table 16, reproduced below, reports the phospholipid concentrations
`present in the krill oil extract obtained by Catchpole.
`
`
`
`As shown in Table 16 above, the composition of Extract 2 includes 39.8%
`phosphatidylcholine (“PC”). Id. at Table 16. The ether phospholipids
`alkylacylphosphatidylcholine (“AAPC”) and
`alkylacylphosphatidylethanolamine (“AAPE”) were also present in Extract
`2, representing 4.6% and 0.2%, respectively, of the extracted composition
`for a total of 4.8% ether phospholipids. Id.; Ex 1006 ¶¶ 145, 146. In
`addition, summing each of the reported phospholipid amounts reported for
`Extract 2 yields a total phospholipid concentration of 45.1%. Ex. 1006
`¶ 146.
`
`3. Fricke
`Fricke discloses the “lipid classes, fatty acids of total and individual
`lipids and sterols of Antarctic krill (E. superba Dana) from two areas of the
`Antarctic Ocean” as determined by thin layer chromatography, gas liquid
`chromatography, and gas liquid chromatography/mass spectrometry
`analyses. Ex. 1010, 1.
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`Table 1 of Fricke is reproduced below.
`
`
`Table 1 shows the total lipid content and the lipid composition data for the
`two krill samples analyzed by Fricke. Id. at 2. As indicated in Table 1, the
`krill samples respectively included approximately 33.3% ± 0.5% w/w and
`40.4% ± 0.1% w/w triacylglycerols. Id.
`4. Breivik
`Breivik discloses the preparation of a lipid fraction from fresh krill.
`Ex. 1037, 1. Breivik discloses that krill oil obtained from Neptune
`Biotechnologies and Biosciences contains ≥ 40.0% phospholipids and ≥ 1.0
`mg/g of esterified astaxanthin. Id. at 11.
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`5. Bottino
`Bottino observes that “[t]he study of krill has become intensive in
`recent times, perhaps as a result of its potential importance as food,” and
`explains that “[a] variety of organisms [are] usually included under that
`generic name, but in the Southern Oceans the name E. superba has been
`considered almost a synonym for krill.” Ex. 1007, 1.
`Bottino describes the fatty acid profiles for E. superba, E.
`crystallorophias, and phytoplankton. Ex. 1007, Abstract. Bottino explains
`that, in contrast to prior studies, lipids were extracted from E. superba
`“immediately after capture.” Id. at 2. Euphausiids lipid extraction was
`performed “with a chloroform:methanol (2:1, v/v) mixture,” as previously
`described by Folch, and the fatty acids were analyzed using
`chromatography. Id. at 1.
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`Table 1 of Bottino is reproduced below.
`
`Ex. 1007, Table 1. Table 1 discloses the fatty acid content of E. superba
`obtained from three different locations (i.e., stations) as a weight percent of
`total fatty acids. Id. at 2. Notably, only those fatty acids present at 1% or
`more as a weight percent of total fatty acids are included in Table 1. Id.
`Table 1
`
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`Table 3 of Bottino is reproduced below.
`
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`
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`Ex. 1007, Table 3. Table 3 reports the identity and average amount of each
`fatty acid present in the E. superba samples analyzed as a weight percentage
`of total fatty acids.
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`6. Randolph
`Randolph discloses compositions for modulating cytokines to regulate
`an inflammatory or immunomodulatory response including, inter alia,
`rosehips and krill oil. Ex. 1011 ¶ 8. With regard to rosehips, Randolph
`discloses that the composition may include one or more rosehip ingredients,
`such as “dried rosehips, rosehip oil, and rosehip extracts.” Id. ¶ 24.
`Concerning krill oil, Randolph discloses that
`[a] composition of the invention can include krill oil. Krill oil can
`be obtained from any member of the E. family, for example E.
`superba. Conventional oil producing techniques can be used to
`obtain the krill oil. In addition, krill oil can be obtained
`co