Trials@uspto.gov
`Tel: 571-272-7822
`
`
`
`
`Paper 18
`Entered: July 9, 2014
`
`UNITED STATES PATENT AND TRADEMARK OFFICE
`_______________
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`_______________
`
`ENZYMOTEC LTD. and ENZYMOTEC USA, INC.
`Petitioner
`
`v.
`
`NEPTUNE TECHNOLOGIES & BIORESSOURCES, INC.
`Patent Owner
`____________
`
`Case IPR2014-00556
`Patent 8,278,351
`_______________
`
`
`Before LORA M. GREEN, JACQUELINE WRIGHT BONILLA, and
`SHERIDAN K. SNEDDEN, Administrative Patent Judges.
`
`SNEDDEN, Administrative Patent Judge.
`
`
`
`DECISION
`Institution of Inter Partes Review
`37 C.F.R. § 42.108
`
`
`
`
`
`
`
`

`

`IPR2014-00556
`Patent 8,278,351
`
`
`I. INTRODUCTION
`
`Petitioners Enzymotec Ltd. and Enzymotec USA, Inc. (collectively,
`
`“Enzymotec”) filed a Petition (Paper 1; “Pet.”) requesting an inter partes review of
`
`claims 16, 9, 12, 13, 1929, 32, 35, 36, and 4246 of U.S. Patent No. 8,278,351
`
`(“the ’351 patent”). Neptune Technologies and Bioressources, Inc. (“Neptune”)
`
`filed a Patent Owner Preliminary Response. Paper 11 (“Prelim. Resp.”).
`
`We have jurisdiction under 35 U.S.C. § 314. The standard for instituting an
`
`inter partes review is set forth in 35 U.S.C. § 314(a), which states:
`
`THRESHOLD.—The Director may not authorize an inter
`partes review to be instituted unless the Director
`determines that the information presented in the petition
`filed under section 311 and any response filed under
`section 313 shows that there is a reasonable likelihood
`that the petitioner would prevail with respect to at least 1
`of the claims challenged in the petition.
`
`Upon consideration of the above-mentioned Petition and Preliminary
`
`Response, we conclude that Enzymotec has established that there is a reasonable
`
`likelihood that it would prevail with respect to at least one of the challenged
`
`claims. We grant the Petition and institute an inter partes review as to claims 16,
`
`9, 12, 13, 1929, 32, 35, 36, and 4246.
`
`A. Related Matters
`
`The ’351 patent is also the subject of an inter partes review in IPR2014-
`
`00003. Aker Biomarine AS (“Aker”) is the Petitioner in IPR2014-00003.
`
`Enzymotec filed a Motion for Joinder (Paper 4) requesting joinder of the current
`
`proceeding with IPR2014-00003. We have granted Enzymotec’s Motion for
`
`Joinder in an Order decided concurrently with this Decision.
`
` 2
`
`
`
`
`
`

`

`IPR2014-00556
`Patent 8,278,351
`
`B. The ’351 Patent (Ex. 1001)
`
`Phospholipids are made up of two chains of fatty acids attached to a
`
`chemical backbone made up of phosphoric acid, glycerol and nitrogenous bases
`
`(e.g., choline). Ex. 1001, col. 4, ll. 41–56. Phospholipids having choline as the
`
`nitrogenous base are referred to as phosphatidylcholines. Id.
`
`The ’351 patent relates to certain phospholipids and compositions containing
`
`phospholipids. The ’351 patent discloses a phospholipid including two fatty acids
`
`chains of eicosapentanoic acid (“EPA”) and docosahexanoic acid (“DHA”)
`
`simultaneously. The general formula for the phospholipid is:
`
`,
`
`wherein X represents a moiety normally found in a phospholipid such as
`
`phosphatidylcholine (PC), phosphatidylethanolamine (PE) and
`
`phosphatidylinositol (PI). Id. at col. 2, l. 46 to col. 3, l. 2 and col. 21, ll. 1–25.
`
`The phospholipids are derived from natural marine or aquatic sources. Id. at
`
`col. 1, ll. 1922. Krill is described as the preferred source of the disclosed
`
`phospholipids, which includes krill found in the Antarctic Ocean (Euphasia
`
`superba) and in the Pacific Ocean (Euphasia pacifica). Id. at col. 15, ll. 821.
`
`The ’351 patent describes the preparation of krill extracts that preferably contain
`
`40% weight per weight (w/w) phospholipid. Id. at col. 15, ll. 4245.
`
`Polyunsaturated fatty acids, in particular omega-3 fatty acids, preferably make up
`
`at least 15% w/w of the total lipids in the extract. Id. at col. 16, ll. 4751. DHA or
`
`EPA may account for at least 32% w/w of the total lipid content of the extract. Id.
`
` 3
`
`
`
`
`
`

`

`IPR2014-00556
`Patent 8,278,351
`
`at col. 16, ll. 5154
`
`C. Illustrative Claims
`
`Claims 1 and 24 are the only independent claims among the challenged
`
`claims and are reproduced below:
`
`1. A krill extract comprising:
`a phospholipid of the general formula (I),
`
`
`wherein R1 and R2, each together with the respective carboxyl
`groups to which each is attached, each independently represents a
`docosahexaenoic acid (DHA) or an eicosapentanoic acid (EPA)
`residue, and X is —CH2CH2NH3, —CH2CH2N(CH3)3, or
`
`
` and wherein the extract is suitable for human consumption.
`
`24. A capsule, tablet, solution, syrup, or suspension comprising
`a krill extract comprising:
`a phospholipid of the general formula (I),
`
` 4
`
`
`
`
`
`

`

`IPR2014-00556
`Patent 8,278,351
`
`
`
`wherein R1 and R2, each together with the respective carboxyl
`groups to which each is attached, each independently represents a
`docosahexaenoic acid (DHA) or an eicosapentanoic acid (EPA)
`residue, and X is —CH2CH2NH3, —CH2CH2N(CH3)3, or
`
`
`and wherein the extract is suitable for human consumption.
`
`Claims 26, 9, 12, 13, and 1923 depend from claim 1, either directly or
`
`indirectly. Claims 2529, 32, 35, 36, and 4246 depend from claim 24, either
`
`directly or indirectly.
`
`D. The Prior Art and Supporting Evidence
`
`Enzymotec relies on the following prior art:
`
`Beaudoin et al., WO 00/23546 A1, published April 27, 2000 (Ex. 1002)
`(“Beaudoin I”).
`
`Fricke et al., Lipid, Sterol and Fatty Acid Composition of Antarctic Krill
`(Euphausia superba Dana), 19(11) LIPIDS 821827 (1984) (Ex. 1006)
`(“Fricke”).
`
`Itano Refrigerated Food Co., Ltd., Bio & High Technology Announcement
`
` 5
`
`
`
`
`
`

`

`IPR2014-00556
`Patent 8,278,351
`
`
`and Natural Astaxanthin & Krill Lecithin, pp. 116 (on or before December
`28, 1994) (Ex. 1009) (“Itano”).
`
`Ichira Yasawa et al., JP H8-231391, published September 10, 1996 (Ex.
`1015) (“Yasawa”).
`
`Lipid Biochemical Preparations, L. D. Bergelson (ed.), Elsevier/North-
`Holland Biomedical Press (1980) (Ex. 1017) (“Bergelson”).
`
`Bulletin of the World Health Organization, “WHO News and activities,”
`73(4):547551 (1995) (Ex. 1018) (“the WHO Bulletin”).
`
`
`Enzymotec further relies on declarations from the following witnesses: Drs.
`
`Richard B. Van Breemen (“Van Breemen” Ex. 1040); J. Thomas Brenna
`
`(“Brenna” Ex. 1042); Ivar Storrø (“Storrø” Ex. 1046); Suzanne Budge (“Budge”
`
`Ex. 1041); Theodore F. Welch (“Welch” Ex. 1043); Jeff D. Moore (“Moore” Ex.
`
`1044); Albert C. Lee (“Lee” Ex. 1045); Bjørn Ole Haugsgjerd (“Haugsgjerd” Ex.
`
`1047, Ex. 1048, and Ex. 1080); and Thomas Gundersen (“Gundersen” Ex. 1049
`
`and Ex. 1050).
`
`E. The Asserted Grounds
`
`Enzymotec challenges claims 16, 9, 12, 13, 1929, 32, 35, 36, and 4246
`
`of the ’351 patent on the following grounds under 35 U.S.C. § 102(b) and § 103(a).
`
`Pet. 1527.
`
`Reference[s]
`
`Beaudoin I
`
`Fricke, Bergelson, Yasawa,
`Itano, the WHO Bulletin
`
`Basis
`
`Claims challenged
`
`§ 102(b)
`
`§ 103(a)
`
`16, 9, 12, 13, 1929, 32,
`35, 36, and 4246
`16, 9, 12, 13, 1929, 32,
`35, 36, and 4246
`
` 6
`
`
`
`
`
`
`
`

`

`IPR2014-00556
`Patent 8,278,351
`
`
`A. Claim Interpretation
`
`II. DISCUSSION
`
`Consistent with the statute and legislative history of the America Invents Act
`
`(“AIA”), the Board interprets claims using the “broadest reasonable construction
`
`in light of the specification of the patent in which [they] appear[].” 37 C.F.R.
`
`§ 42.100(b); see also Office Patent Trial Practice Guide, 77 Fed. Reg. 48,756,
`
`48,766 (Aug. 14, 2012).
`
`Under the broadest reasonable construction standard, claim terms are given
`
`their ordinary and customary meaning, as would be understood by one of ordinary
`
`skill in the art at the time of the invention. In re Translogic Tech., Inc., 504 F.3d
`
`1249, 1257 (Fed. Cir. 2007). “Absent claim language carrying a narrow meaning,
`
`the PTO should only limit the claim based on the specification . . . when [it]
`
`expressly disclaim[s] the broader definition.” In re Bigio, 381 F.3d 1320, 1325
`
`(Fed. Cir. 2004). “Although an inventor is indeed free to define the specific terms
`
`used to describe his or her invention, this must be done with reasonable clarity,
`
`deliberateness, and precision.” In re Paulsen, 30 F.3d 1475, 1480 (Fed. Cir. 1994).
`
`With one exception, Enzymotec contends that the claim terms take on the
`
`ordinary and customary meaning that the terms would have to one of ordinary skill
`
`in the art. Pet. 9. Enzymotec sets forth what it considers the broadest reasonable
`
`interpretation of the following claim terms: 1) “krill extract;” 2) “suitable for
`
`human consumption;” and 3) “solution.” Id. at 910. Neptune has not disputed
`
`Enzymotec’s proposed constructions of these claim terms. See generally Prelim.
`
`Resp. We have considered Enzymotec’s proposed constructions, taking into
`
`account the plain meaning of the terms and their usage in the specification, and
`
`have concluded that determination of the issues presented in Enzymotec’s Petition
`
` 7
`
`
`
`
`
`

`

`IPR2014-00556
`Patent 8,278,351
`
`does not require explicit construction of these terms at this time.
`
`Regarding the one exception, Enzymotec contends that the specification of
`
`the ’351 patent gives special meaning to the term “about.” Id. We agree.
`
`Specifically, the specification of the ’351 patent, at column 21, lines 6163,
`
`expressly defines the term “about” by stating that “in the claims, where the term
`
`‘about’ is used with a numerical value, the numerical value may vary by at least
`
`± 50%.” Ex. 1001, 21:6163. Thus, unless a claim otherwise recites that “about”
`
`has a specific value (see, e.g., claim 2, reciting “about 40% w/w, wherein about
`
`represents ± 10%”), we interpret the term “about” to mean that the numerical value
`
`just after the term “about” may vary by at least ± 50% (see, e.g., claim 5 reciting
`
`“about 5% w/w”). For example, “about 5%” means “0% to 55%” and about
`
`“about 95%” means “45% to 100%.”
`
`B. Asserted Grounds of Unpatentability
`
`1. Anticipation of Claims 16, 9, 12, 13, 1929, 32, 35, 36, and 4246 by
`Beaudoin I (Ex. 1002)
`
`a. Summary of Beaudoin I
`
`Beaudoin I relates to the extraction of lipid fractions from marine and
`
`aquatic animals such as krill. Ex. 1002, 1, ll. 56. Lipids are extracted from
`
`freshly collected marine and aquatic material with a ketone, such as acetone. Id. at
`
`4, ll. 2930. Beaudoin I discloses that krill lipid fractions have various uses,
`
`including medical and nutritional applications. Id. at 1, ll. 1126.
`
`Beaudoin I provides a description of the general extraction method used to
`
`prepare extracts from marine and aquatic animal material. Ex. 1002, 5, l. 21 to 6, l.
`
`20. Beaudoin I discloses that the starting material is subjected to acetone
`
`extraction, under inert atmosphere, and at a temperature of about 5° C or less for
`
` 8
`
`
`
`
`
`

`

`IPR2014-00556
`Patent 8,278,351
`
`about two hours, and preferably overnight. Id. Table 19 of Beaudoin I is
`
`reproduced below.
`
`
`
`Id. at 28. Table 19 provides the suggested procedure and optimal conditions for
`
`lipid extraction of aquatic animal tissues.
`
`Beaudoin I discloses the preparation of krill oil using various solvents. Id. at
`
`8, ll. 419; see also id. at 21, ll. 3955 (Table 12). The characteristics of certain
`
`lipid fractions of the krill oil were analyzed. The krill oil fractions were heated to
`
`about 125° C for about 15 minutes to remove traces of solvents. Id. at 10, ll. 620.
`
`The inventor of Beaudoin I, Dr. Adrien Beaudoin, ingested lipid fractions of
`
` 9
`
`
`
`
`
`

`

`IPR2014-00556
`Patent 8,278,351
`
`krill, and disclosed that no side effect profile was observed. Id. at 12, ll. 1314.
`
`b. Analysis
`
`(1) Claims 1 and 24
`
`Claims 1 and 24 are directed to a krill extract and solution, respectively,
`
`containing a phospholipid of the general formula (I) that is suitable for human
`
`consumption. Enzymotec argues that Beaudoin I discloses lipid extracts from krill
`
`that necessarily contain the phospholipids in claim 1. Pet. 1718. While Beaudoin
`
`I does not identify the lipid composition of the E. pacifica krill extracts,
`
`Enzymotec relies on extensive declaration evidence, related to the reproduction
`
`and testing of krill extracts made according to the disclosure of Beaudoin I, to
`
`show that the E. pacifica krill extracts disclosed in Beaudoin I necessarily
`
`contained the claimed phospholipids. Id. (citing van Breemen (Ex. 1040), ¶¶
`
`7385 and 9398; Budge (Ex. 1041), ¶¶ 710; Haugsgjerd (Ex. 1048), ¶¶ 25).
`
`The van Breemen Declaration, in particular, provides mass spectrometry evidence
`
`that E. pacifica krill acetone extracts contained PC-EPA/EPA, PC-DHA/DHA, and
`
`PC-EPA/DHA. Ex. 1040, ¶¶ 7385 and 9398.
`
`With regard to the suitability-for-human-consumption element of claims 1
`
`and 24, Enzymotec contends that Beaudoin I discloses that the extract fractions
`
`were consumed with no side effect. Id. (citing Ex. 1002, 12, ll. 1314).
`
`With regard to the recitation of a krill solution in claim 24, Enzymotec
`
`argues that the Beaudoin I krill oil extracts are solutions encompassed by claim 24
`
`as the phospholipids and other components are dissolved in the extracts. Id. (citing
`
`Ex. 1042, ¶ 202).
`
`We conclude that the analysis and information presented by Enzymotec
`
`tends to demonstrate that the E. pacifica krill extract disclosed in Beaudoin I
`
`
`
`10
`
`
`
`

`

`IPR2014-00556
`Patent 8,278,351
`
`comprised at least one phospholipid defined by the general formula of claims 1 and
`
`24 and was suitable for human consumption, as required by claims 1 and 24.
`
`Accordingly, we determine that there is a reasonable likelihood that Enzymotec
`
`would prevail in demonstrating unpatentability of claims 1 and 24 as anticipated by
`
`Beaudoin I.
`
`(2) Claims 2, 3, 25, and 26
`
`Dependent claims 2 and 25 require the claimed extract or solution to
`
`comprise a total phospholipid concentration in an amount of about 40% w/w,
`
`wherein “about represents ±10%.” Dependent claims 3 and 26 require the claimed
`
`extract or solution to have a total phospholipid concentration in an amount of about
`
`45% w/w, wherein about represents ±20%.
`
`Enzymotec contends that Beaudoin I discloses 54.1±6.1% phospholipids and
`
`polar material w/w in Fraction I extracts, which falls within or touches the claimed
`
`ranges. Pet. 1819 (citing Ex. 1002, 23 (Table 14)). Beaudoin I’s description of
`
`concentration percentages of “[p]hospholipids or other polar material” in Table 14,
`
`however, does not disclose explicitly a total phospholipid concentration, as recited
`
`in the challenged claims. Rather, Table 14 in Beaudoin I describes percentages, in
`
`krill oil Fractions I and II, of material having phospholipids (at some undisclosed
`
`concentration) plus “other polar material” (at some undisclosed concentration).
`
`Thus, Enzymotec does not explain sufficiently in its Petition how one can ascertain
`
`the total phospholipid concentration of Fraction I by looking at Table 14 or
`
`elsewhere in Beaudoin I.
`
`Enzymotec further directs our attention to the testimony of Neptune’s
`
`declarant, Dr. Yeboah. Id. at 19. Enzymotec contends that Dr. Yeboah has
`
`explained that the Beaudoin I extracts tested by Dr. White contain about 40%
`
`
`
`11
`
`
`
`

`

`IPR2014-00556
`Patent 8,278,351
`
`phospholipids. Id. (citing Ex. 1054, ¶ 36). Dr. Yeboah, however, makes no such
`
`statement in the cited paragraph. Rather, in the passage relied on by Enzymotec,
`
`Dr. Yeboah refers to general teachings in the scientific literature that discuss the
`
`phospholipid content of oil extracted from E. superba, which is not the same
`
`species of krill examined in Beaudoin I. Ex. 1054, n. 7. Accordingly, we do not
`
`consider the statement of Dr. Yeboah to be material to the phospholipid
`
`concentration of the krill oil compositions disclosed by Beaudoin I.
`
`Enzymotec also relies on declarations from Drs. Budge, Moore, and Brenna
`
`to demonstrate that the E. pacifica krill extracts disclosed in Beaudoin I necessarily
`
`contained the phospholipids concentrations recited in claims 2, 3, 15 and 26. Pet.
`
`1819 (citing Budge (Ex. 1041), ¶ 10; Moore (Ex 1044) at Exhibit A, Table 11;
`
`Brenna (Ex. 1042), ¶¶ 18081). Dr. Budge testifies that he prepared acetone
`
`extracts of E. pacifica krill following the method of Beaudoin I in all relevant
`
`steps, and sent the samples to Dr. Moore. Ex. 1041, 4-7 (citing Ex. 1002, 5-6 and
`
`Table 19). Dr. Moore conducted compositional analysis on the samples. Ex. 1044.
`
`The information presented by Enzymotec indicates that each of the E. pacifica krill
`
`extracts prepared by Dr. Budge (SB1-8/19/2013-BEA-P0, SB5-8/19/2013-BEA-
`
`P1, and SB9-8/19/2013-BEA-P2) and tested by Dr. Moore contained phospholipids
`
`concentrations (31.02 ± 0.07 %, 31.51 ± 0.12 %, and 44.40 ± 0.48 %, respectively)
`
`within the ranges recited in claims 2, 3, 25 and 26. Based on this information,
`
`there is a reasonable likelihood that Enzymotec would prevail in showing that the
`
`E. pacifica krill extracts disclosed in Beaudoin I inherently contain the claimed
`
`total phospholipid concentrations.
`
`In view of the above, we are persuaded that there is a reasonable likelihood
`
`that Enzymotec would prevail in demonstrating the unpatentability of claims 2, 3,
`
`25 and 26 of the ’351 patent based on anticipation by Beaudoin I.
`
`
`
`
`
`12
`
`
`
`

`

`IPR2014-00556
`Patent 8,278,351
`
`
`(3) Claims 4, 5, 27, and 28
`
`Claims 4 and 5 depend directly from claim 1. Claims 27 and 28 depend
`
`directly from claim 24. Dependent claims 4 and 27 require the claimed extract or
`
`solution to have an additional lipid, such as a free fatty acid. Dependent claims 5
`
`and 28 require a concentration of free fatty acids of about 5% w/w of the lipids in
`
`the extract. Enzymotec contends that the Beaudoin I extracts contained free fatty
`
`acids at a concentration of 23.7 ±1.1% and 20.3±0.3%. Pet. 19(citing Ex. 1002, 23
`
`(Table 14)). Enzymotec contends further that 23.7 ±1.1% is within the range of
`
`“about 5%,” as defined in the ’351 patent. Id.; see also Ex. 1001, col. 21, ll. 62-64.
`
`As noted above, unless the claim requires otherwise, the term “about” refers to at
`
`least ± 50%. Claims 4 and 27 do not define the term “about,” and, therefore,
`
`“about 5%” encompasses 23.7±1.1%, the concentration of free fatty acids in the
`
`extracts disclosed in Beaudoin I.
`
`In view of the evidence presented by Enzymotec, we conclude that there is a
`
`reasonable likelihood that Enzymotec would prevail in demonstrating
`
`unpatentability of claims 4, 5, 27, and 28 as anticipated by Beaudoin I.
`
`(4) Claims 6, 9, 29, and 32
`
`Dependent claims 6 and 29 require the claimed extract or solution to have
`
`polyunsaturated fatty acids (PUFAs) at a concentration of at least 15% w/w.
`
`Dependent claims 9 and 32 require the PUFAs to be omega-3 fatty acids.
`
`Enzymotec contends that the Beaudoin I extracts contain 54.4% PUFAs.
`
`Pet. 20 (citing Ex. 1002, 2324 (Table 15)).
`
`In view of the information and argument presented by Enzymotec, we
`
`conclude that there is a reasonable likelihood that Enzymotec will prevail in
`
`demonstrating unpatentability of claims 6, 9, 29, and 32 for anticipation by
`
`
`
`13
`
`
`
`

`

`IPR2014-00556
`Patent 8,278,351
`
`Beaudoin I.
`
`(5) Claims 12, 13, 35 and 36
`
`Dependent claims 12 and 35 require the claimed extract or solution to
`
`comprise a metal. Dependent claims 13 and 36 require the metal to be zinc,
`
`selenium, or a mixture thereof. Enzymotec relies on testimony from Drs. Brenna,
`
`Budge, and Lee to demonstrate that E. pacifica extracts inherently contain metal
`
`such as zinc. Pet. 20 (citing Ex. 1042, ¶¶ 191192; Ex. 1045, Exhibit A (Table 7)).
`
`Dr. Lee confirmed the presence of zinc in the unheated sample of an E. pacifica
`
`acetone extract prepared by Dr. Budge. Ex. 1045, Exhibit A (Sample “S6,”
`
`corresponding to sample “SB2 8/19/2013 BEA-P0” prepared by Dr. Budge (Ex.
`
`1041)).
`
`In view of evidence presented by Enzymotec, we conclude that there is a
`
`reasonable likelihood that Enzymotec would prevail in demonstrating
`
`unpatentability of claims 12, 13, 35, and 36 as anticipated by Beaudoin I.
`
`(6) Claims 19, 20, 21, 42, 43, and 44
`
`Dependent claims 19, 20, 21, 42, 43, and 44 require the claimed extract to
`
`have PC-EPA/DHA (claims 19 and 42), PC-EPA/EPA (claims 20 and 43), and PC-
`
`DHA/DHA (claims 21 and 44). Enzymotec relies on testimony from Drs. Brenna,
`
`Haugsgjerd, and van Breemen to demonstrate that E. pacifica extracts inherently
`
`contain the recited EPA and DHA species. Pet. 20. Dr. Haugsgjerd prepared
`
`acetone extractions of E. pacifica and sent the samples to Dr. van Breemen, of the
`
`University of Illinois, for analysis. Ex. 1048, ¶¶ 23. Enzymotec contends that
`
`Dr. van Breemen detected the presence of all of the species (PC-EPA/EPA, PC-
`
`DHA/DHA, and PC-EPA-DHA) in the tested E. pacifica extracts. Pet. 20; Ex.
`
`1040, ¶¶ 57, 73, 93.
`
`
`
`
`
`
`
`14
`
`

`

`IPR2014-00556
`Patent 8,278,351
`
`
`In view of evidence presented by Enzymotec, we conclude that there is a
`
`reasonable likelihood that Enzymotec would prevail in demonstrating
`
`unpatentability of claims 19, 20, 21, 42, 43, and 44 as anticipated by Beaudoin I.
`
`(7) Claims 22, 23, 45, and 46
`
`Dependent claims 22, 23, 45, and 46 require the claimed extract to have an
`
`antioxidant such as astaxanthin. Enzymotec indicates that Beaudoin I expressly
`
`discloses that the extracts described in that reference contain astaxanthin. Pet. 20
`
`(citing Ex. 1002, 27 (Table 18)).
`
`In view of the evidence presented by Enzymotec, we conclude that there is a
`
`reasonable likelihood that Enzymotec would prevail in demonstrating
`
`unpatentability of claims 22, 23, 45, and 46 as anticipated by Beaudoin I.
`
`2. Obviousness of Claims 16, 9, 12, 13, 1929, 32, 35, 36, and 4246
`Over the Combination of Fricke (Ex. 1006), Bergelson (Ex. 1017),
`Yasawa (Ex.1015), Itano (Ex. 1009), and the WHO Bulletin (Ex. 1018)
`
`a. Summary of Fricke
`
`Fricke discloses the preparation of lipid extractions from Antarctic krill (E.
`
`superba). Ex. 1006, 821. Table 1 of Fricke is reproduced below.
`
`
`
`15
`
`
`
`

`

`IPR2014-00556
`Patent 8,278,351
`
`
`Id. at 822 (Table 1). Table 1 discloses the total lipid content and the lipid
`
`composition data of two krill samples obtained from krill caught in December
`
`
`
`1977 and March 1981. Id.
`
`Table 6 of Fricke is reproduced below.
`
`
`
`16
`
`
`
`

`

`IPR2014-00556
`Patent 8,278,351
`
`
`Id. at 826 (Table 6). Table 6 discloses the fatty acid positional analysis in
`
`phosphatidylcholine (PC) and phosphatidylethanolamine (PE) detected in the
`
`
`
`December 1977 E. superba sample. Id.
`
`b. Analysis
`
`(1) Claims 1, 19, 20, 21, 24, 42, 43, and 44
`
`Claims 1 and 24 are directed to a krill extract and solution, respectively,
`
`containing a phospholipid of the general formula (I) that is suitable for human
`
`consumption. Dependent claims 1921 and 4244 require the claimed extract to
`
`have PC-EPA/DHA (claims 19 and 42), PC-EPA/EPA (claims 20 and 43) and PC-
`
`DHA/DHA (claims 21 and 44).
`
`Enzymotec contends that Fricke discloses lipid extracts or solutions from E.
`
`superba, an Antarctic krill. Pet. 2225 (citing Ex. 1006, 821822, Table 1).
`
`Enzymotec contends further that Fricke specifically teaches that krill phospholipids
`
`
`
`17
`
`
`
`

`

`IPR2014-00556
`Patent 8,278,351
`
`have EPA (20:5 n-3 in Table 6 of Fricke) and DHA (22:6 n-3 in Table 6 of Fricke)
`
`at both sn-1 and sn-2 positions of PC. Id. at 23 (citing Ex. 1006, 826 (Table 6)).
`
`According to Enzymotec, Fricke prepared lipid extracts according to the Folch
`
`method. Id. at 22 (citing Ex. 1006, 82122). Enzymotec contends that Le
`
`Grandois (Ex. 1013) demonstrates that krill oil extracted by the Folch method
`
`contains PC-EPA/EPA, PC-DHA/DHA, and PC-EPA/DHA. Id. at 23 (citing Ex.
`
`1013, 6018 (Table 2)). The conclusions of Le Grandois are further supported by
`
`the declaration of Dr. van Breemen, which supports a determination that PC-
`
`EPA/EPA, PC-DHA/DHA, and PC-EPA/DHA are found in E. superba extracts.
`
`Ex. 1040, ¶ 93.
`
`With regard to suitability for human consumption, Enzymotec relies on
`
`Yasawa (Ex. 1015), Itano (Ex. 1009), and the WHO Bulletin (Ex. 1018) for
`
`teaching the desirability of krill phospholipid compositions for human
`
`consumption. Pet. 2527. Itano, for example, describes krill extract as a
`
`seasoning for food. Ex. 1009, 7. Enzymotec further contends that Bergelson (Ex.
`
`1017) teaches removal of chloroform/methanol solvents from lipids by rotary
`
`evaporation. Pet. 25. Thus, Enzymotec points to information tending to show that
`
`a process for preparing krill extracts suitable for human consumption was known
`
`in the art. Id. Enzymotec also contends that a person of ordinary skill in the art
`
`would have had reason to combine the different teachings of these references
`
`because together they taught methods for extraction and concentration of krill
`
`phospholipids for human consumption. Pet. 2627.
`
`We conclude that the information and arguments presented by Enzymotec
`
`are sufficient to show that there is a reasonable likelihood that Enzymotec would
`
`prevail in its challenge of claims 1, 19, 20, 21, 24, 42, 43, and 44 as obvious over
`
`the combination of Fricke, Bergelson, Yasawa, Itano, and the WHO Bulletin.
`
`
`
`18
`
`
`
`

`

`IPR2014-00556
`Patent 8,278,351
`
`
`(2) Claims 2, 3, 25, and 26
`
`Dependent claims 2 and 25 require the claimed extract or solution to have a
`
`total phospholipid concentration in an amount of about 40% w/w, wherein about
`
`represents ±10%. Dependent claims 3 and 26 require the claimed extract or
`
`solution to have a total phospholipid concentration in an amount of about 45%
`
`w/w, wherein “about” represents ± 20%.
`
`Enzymotec contends that Fricke discloses krill extracts containing 39.6% to
`
`42.5% phospholipids, which falls within the range recited in claims 2, 3, 25, and
`
`26. Pet. 24 (citing Ex. 1006, 822 (Table 1)).
`
`In view of the meaning of the term “about,” as discussed above, as well as
`
`the evidence presented by Enzymotec, we conclude that there is a reasonable
`
`likelihood that Enzymotec would prevail in its challenge of claims 2, 3, 25, and 26
`
`as obvious over the combination of Fricke, Bergelson, Yasawa, Itano, and the
`
`WHO Bulletin.
`
`(3) Claims 4, 5, 27, and 28
`
`Dependent claims 4 and 27 require the claimed extract or solution to have an
`
`additional lipid, such as a free fatty acid. Dependent claims 5 and 28 require a
`
`concentration of free fatty acids of about 5% w/w of the lipids in the extract.
`
`Enzymotec contends that Fricke discloses krill extracts containing from
`
`8.5% to 16.1% free fatty acids, which is encompassed by about 5% as defined in
`
`the ’351 patent. Pet. 24 (citing Ex. 1006, 822 (Table 1)).
`
`In view of the meaning of the term “about,” as discussed above, as well as
`
`the evidence presented by Enzymotec, we conclude that there is a reasonable
`
`likelihood that Enzymotec will prevail in its challenge of claims 4, 5, 27, and 28 as
`
`obvious over the combination of Fricke, Bergelson, Yasawa, Itano, and the WHO
`
`
`
`19
`
`
`
`

`

`IPR2014-00556
`Patent 8,278,351
`
`Bulletin.
`
`(4) Claims 6, 9, 29 and 32
`
`Dependent claims 6 and 29 require the claimed extract or solution to
`
`comprise polyunsaturated fatty acids (PUFAs) at a concentration of at least 15%
`
`w/w. Dependent claims 9 and 32 require the PUFAs to be omega-3 fatty acids.
`
`Enzymotec contends that Fricke discloses krill extracts containing 21.42%
`
`omega-3 fatty acids. Pet. 24 (citing Ex. 1006, 823 (sum of n-3s in Table 2)).
`
`In view of the information and argument presented by Enzymotec, we
`
`conclude that there is a reasonable likelihood that Enzymotec will prevail in its
`
`challenge of claims 6, 9, 29 and 32 as obvious over the combination of Fricke,
`
`Bergelson, Yasawa, Itano, and the WHO Bulletin.
`
`(5) Claims 12, 13, 35 and 36
`
`Dependent claims 12 and 35 require the claimed extract or solution to have a
`
`metal. Dependent claims 13 and 36 require the metal to be zinc, selenium , or a
`
`mixture thereof.
`
`Enzymotec contends that it is well known that krill contain zinc and
`
`selenium and that krill extracts disclosed in the prior art would inherently contain
`
`zinc and selenium. Pet. 26 (citing Ex. 1018, 551, col. 2). Enzymotec further relies
`
`on the WHO Bulletin for teaching the usefulness of Antarctic krill for a variety of
`
`purposes, including as a source of zinc and selenium, thereby suggesting a
`
`preparation of krill extracts that retain zinc and selenium. Id. at 2627 (citing Ex.
`
`1042, ¶ 399). Enzymotec contends that a person of ordinary skill in the art would
`
`have had a reasonable expectation of success in formulating krill extracts suitable
`
`for human consumption and retaining useful components inherently present in
`
`krill. Id. This conclusion is supported by the declaration of Dr. Lee, which
`
`
`
`20
`
`
`
`

`

`IPR2014-00556
`Patent 8,278,351
`
`presents evidence that zinc and selenium may be successfully extracted from E.
`
`superba. Ex. 1045, Exhibit A (Samples “S9,” “S10,” “S18,” “S19,” “S20,” and
`
`corresponding samples prepared by Dr. Budge (Ex. 1041)).
`
`In view of the evidence presented by Enzymotec, we conclude that there is a
`
`reasonable likelihood that Enzymotec will prevail in its challenge of claims 12, 13,
`
`35, and 36 as obvious over the combination of Fricke, Bergelson, Yasawa, Itano,
`
`and the WHO Bulletin.
`
`(6) Claims 22, 23, 45, and 46
`
`Dependent claims 22, 23, 45, and 46 require the claimed extract or solution
`
`to have an antioxidant such as astaxanthin. Enzymotec contends that Fricke
`
`discloses krill extracts containing carotenoids, which are antioxidants. Pet. 2526
`
`(citing Ex. 1006, 821 (Table 1, note b)).
`
`In view of the evidence presented by Enzymotec, we conclude that there is a
`
`reasonable likelihood that Enzymotec will prevail in its challenge of claims 22, 23,
`
`45, and 46 as obvious over the combination of Fricke, Bergelson, Yasawa, Itano,
`
`and the WHO Bulletin.
`
`III. CONCLUSION
`
`We institute an inter partes review of claims 16, 9, 12, 13, 1929, 32, 35,
`
`36, and 4246 based on the following grounds:
`
`(1) Anticipation of claims 16, 9, 12, 13, 1929, 32, 35, 36, and 4246 by
`
`Beaudoin I; and
`
`(2) Obviousness of claims 16, 9, 12, 13, 1929, 32, 35, 36, and 4246 over
`
`the combination of Fricke, Bergelson, Yasawa, Itano, and the WHO Bulletin.
`
`
`
`21
`
`
`
`

`

`IPR2014-00556
`Patent 8,278,351
`
`
`For the reasons given, it is
`
`IV. ORDER
`
`
`
`ORDERED that the Petition is granted as to claims 16, 9, 12, 13,
`
`1929, 32, 35, 36, and 4246 of the ’351 patent with respect to the following
`
`alleged grounds:
`
`1. Claims 16, 9, 12, 13, 1929, 32, 35, 36, and 4246 of the ’351
`
`patent under 35 U.S.C. § 102 as anticipated by Beaudoin I; and
`
`2. Claims 16, 9, 12, 13, 1929, 32, 35, 36, and 4246 of the ’351
`
`patent under 35 U.S.C. § 103 as obvious over the combination
`
`Fricke, Bergelson, Yasawa, Itano, and the WHO Bulletin.
`
`
`
`FURTHER ORDERED that pursuant to 35 U.S.C. § 314(a), inter
`
`partes review of the ʼ351 patent is hereby instituted commencing on the entry date
`
`of this Order, and pursuant to 35 U.S.C. § 314(c) and 37 C.F.R. § 42.4, notice is
`
`hereby given of the institution of a trial.
`
`
`
`FURTHER ORDERED that the trial is limited to the grounds listed in
`
`the Order. No other grounds are authorized.
`
`
`
`
`
`
`
`
`
`
`
`22
`
`

`

`IPR2014-00556
`Patent 8,278,351
`
`PETITIONER:
`
`Elizabeth J. Holland
`Kenyon & Kenyon LLP
`One Broadway
`New York, NY 10004-1007
`eholland@kenyon.com
`
`Cynthia Lambert Hardman
`Kenyon &Kenyon LLP
`One Broadway
`New York, NY 10004-1007
`chardman@kenyon.com
`
`
`
`
`
`
`PATENT OWNER:
`
`Stephen L. Altieri
`Cooley LLP
`ATTN: Patent Group
`1299 Pennsylvania Ave., NW
`Suite 700
`Washington, DC 20004
`saltieri@cooley.com
`
`
`J. Dean Farmer
`Cooley LLP
`ATTN: Patent Group
`1299 Pennsylvania Ave., NW
`Suite 700
`Washington, DC 20004
`dfarmer@cooley.com
`
`
`
`
`
`
`
`
`
`
`
`
`23
`
`