Inter Partes Review Case No.: lPR2017-00746
`
`U.S. Patent No. 9,028,877
`
`Rimfrost USA, LLC, Rimfrost New Zealand Limited and Bioriginal Food & Science
`
`Corp. (Exhibit 1023). On January 27, 2017, Petitioner filed lPR2017-0745 and
`
`IPR2017-0747 seeking inter partes review of Claims 1-20 of U.S. Patent No.
`
`9,078,905.
`
`C.
`
`Counsel (37 C.F.R. §§ 42.8(b)(3) and 42.10(a))
`
`Petitioner designates the following individuals as its lead counsel and back-
`
`up lead counsel:
`
`Lead Counsel
`
`Back—up Lead Counsel
`
`James F. Harrington
`Reg. No. 44,741
`Hoffmann & Baron, LLP
`
`jfhdocket@hbiplaw.com
`(516)822-3550
`
`Michael I. Chakansky
`Reg. No. 31,600
`Hoffmann & Baron, LLP
`
`micdocket@hbilglaw.com
`(973)331-1700
`
`Ronald J. Baron
`
`Reg. No. 29,281
`Hoffmann & Baron, LLP
`
`rjbdocket@hbiplaw.com
`(516)822-3550
`
`John T. Gallagher
`Reg. No. 35,516
`Hoffmann & Baron, LLP
`
`jtgdocket@hbilglaw.com
`(516)822-3550
`
`RIMFROST EXHIBIT 1063
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`RIMFROST EXHIBIT 1063 page 0801
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`page 0801
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`
`
`U.S. Patent No. 9,028,877
`
`Rimfrost USA, LLC, Rimfrost New Zealand Limited and Bioriginal Food & Science
`
`Corp. (Exhibit 1023). On January 27, 2017, Petitioner filed lPR2017-0745 and
`
`IPR2017-0747 seeking inter partes review of Claims 1-20 of U.S. Patent No.
`
`9,078,905.
`
`C.
`
`Counsel (37 C.F.R. §§ 42.8(b)(3) and 42.10(a))
`
`Petitioner designates the following individuals as its lead counsel and back-
`
`up lead counsel:
`
`Lead Counsel
`
`Back—up Lead Counsel
`
`James F. Harrington
`Reg. No. 44,741
`Hoffmann & Baron, LLP
`
`jfhdocket@hbiplaw.com
`(516)822-3550
`
`Michael I. Chakansky
`Reg. No. 31,600
`Hoffmann & Baron, LLP
`
`micdocket@hbilglaw.com
`(973)331-1700
`
`Ronald J. Baron
`
`Reg. No. 29,281
`Hoffmann & Baron, LLP
`
`rjbdocket@hbiplaw.com
`(516)822-3550
`
`John T. Gallagher
`Reg. No. 35,516
`Hoffmann & Baron, LLP
`
`jtgdocket@hbilglaw.com
`(516)822-3550
`
`RIMFROST EXHIBIT 1063
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`RIMFROST EXHIBIT 1063 page 0801
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`page 0801
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`Inter Partes Review Case N0.: IPR2017-00746
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`US. Patent No. 9,028,877
`
`D.
`
`Service information (37 C.F.R. §42.8(b)(4))
`
`Service on Petitioner may be made electronically by using the following
`
`email address: 877ipr1@hbiplaw.com and the email addresses above. Service on
`
`Petitioner may be made by Postal Mailing or Hand-delivery addressed to Lead and
`
`Back-up Lead Counsel at the following address, but electronic service above is
`
`requested:
`
`Hoffmann & Baron, LLP
`
`6900 Jericho Turnpike
`Syosset, New York 11791
`
`This document, together with all exhibits referenced herein, has been served
`
`on the patent owner at its corporate headquarters, Oskenoyveien 10 N0—1327,
`
`1366 Lysaker, Norway, as well as the correspondence address of record for the
`
`‘877 patent: Casimir Jones, SC, 2275 Deming Way, Suite 310, Middleton,
`
`Wisconsin 53562, and the address of Patent Owner’s litigation counsel: Andrew
`
`F. Pratt, Esq. Venable LLP, 575 Seventh Street NW, Washington, DC 20004.
`
`111.
`
`PAYMENT OFFICE FEES
`
`Pursuant to 37 C.F.R. §§ 42.103 and 42.15(a), the requisite filing fee of
`
`$24,600 (request fee of $9,000, post-institution fee of $14,000 and excess Claims
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`page 0802
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`Inter Partes Review Case No.: IPR2017-00746
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`U.S. Patent No. 9,028,877
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`fee of $1,600) for a Petition for Inter Partes Review is submitted herewith.
`
`Claims 1-19 of the ‘877 patent are being reviewed as part of this Petition. The
`
`undersigned further authorizes payment from Deposit Account No. 08-2461 for
`
`any additional fees or refund that may be due in connection with the Petition.
`
`IV. ADDITIONAL REQUIREMENTS FOR INTER PARTES REVIEW
`
`A.
`
`Grounds for Standing (37 C.F.R. § 42.104(a))
`
`Petitioner hereby certifies that the ‘877 patent is available for Inter Partes
`
`Review and that Petitioner is not barred or estopped from requesting Inter Partes
`
`Review challenging the claims of the ‘877 patent on the grounds identified herein.
`
`This Petition is timely filed under 35 U.S.C. §315(b) because it is filed within one
`
`year of the service of the Complaint alleging infringement of the ‘877 patent by
`
`Aker. See Exhibits 1021-1022.
`
`B. Level or Ordinary Skill in the Art
`
`As of the earliest priority date the ‘877 Patent is entitled to, (i.e., January
`
`28, 2008), a POSITA would have held an advanced degree in marine sciences,
`
`biochemistry, organic (especially lipid) chemistry, chemical or process
`
`engineering, or associated sciences with complementary understanding, either
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`Inter Partes Review Case No.: IPR2017-00746
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`US. Patent No. 9,028,877
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`through education or experience, of organic chemistry and in particular lipid
`
`chemistry, chemical or process engineering, marine biology, nutrition, or
`
`associated sciences; and knowledge of or experience in the field of extraction. In
`
`addition, a POSITA would have had at least five years’ applied experience.
`
`(Tallon Decl. ‘][27).
`
`C.
`
`Identification of Challenge and Relief Requested
`(37 C.F.R. § 42.104(b) and 37 C.F.R. § 42.22(a)(1))
`
`The precise relief requested by Petitioner is that Claims 1-19 are found
`
`unpatentable and cancelled from the ‘877 patent.
`
`1.
`
`Claims for which Inter Partes Review is Requested(37
`C.F.R. §42.104(b)(2))
`
`Petitioner requests Inter Partes Review of Claims 1-19 of the ‘877 patent.
`
`2.
`
`Specific Statutory Grounds on which the Challenge is
`Based (37 C.F.R. § 42.104(b)(2))
`
`The specific statutory grounds for the challenge are as follows:
`
`15 and 17-18 2
`
`1
`
`Breivik, Catchpole,
`and Fricke
`
`35 U.S.C. §103(a)
`
`1-3, 6, 8-9, 11-12,
`
`Breivik, Catchpole, Fricke,
`and Bottino
`
`35 U.S.C. §103(a)
`
`4-5 and 13-14
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`Inter Partes Review Case No.: IPR2017-00746
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`US. Patent No. 9,028,877
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`Basis
`
`Claims Challenged
`
`Breivik, Catchpole, Fricke,
`and Samalis I
`
`35 U.S.C. §103(a)
`
`7 and 16
`
`Ground
`
`3
`
`4
`
`and Sampalis II
`
`Breivik, Catchpole, Fricke,
`
`35 U.S.C. §103(a)
`
`10 and 19
`
`Petitioner also relies on the expert declaration of Dr. Stephen Tallon
`
`(Exhibit 1006).
`
`3.
`
`Earliest Effective Priority Date
`
`All of the issued claims in the ‘877 patent require the element that the krill
`
`oil comprise from about 3% to about 10% w/w ether phospholipids. Support for
`
`the claim element “ether phospholipid” was not introduced until the filing of US.
`
`Application No. 61/024,072, filed on January 28, 2008. (See Exhibits 1002-1005).
`
`Consequently, the earliest effective priority date for the claims of the ‘877 patent
`
`is January 28, 2008. (See Tallon Dec. ‘][ 34).
`
`4.
`
`Prior Art References
`
`Other than Catchpole and Breivik, all prior art references utilized herein
`
`were published more than one year prior to the earliest possible priority date of
`
`January 28, 2008, and, therefore, qualify as prior art under 35 U.S.C. §102(b).
`
`Catchpole has an international filing date of April 20, 2007 and was published on
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`page 0805
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`November 1, 2007 and, therefore, qualifies as a prior art reference under 35
`
`U.S.C. §102(e)1. Breivik claims priority to US. provisional application No.
`
`60/859,289 (Exhibit 1036) filed November 16, 2006 and was filed as a PCT
`
`application on November 15, 2007 (Exhibit 1037).
`
`§102(b) Reference
`
`Publication Date
`
`Exhibit N0.
`
`Fricke
`
`April 30, 1984
`
`Sampalis I
`
`May 2003
`
`Bottino
`
`June 28, 1974
`
`Sampalis 11
`
`February 13, 2003
`
`1010
`
`1012
`
`1007
`
`1013
`
`
`
`
`1035
`
`§102(e) Reference
`
`Effective Filing Date
`
`Exhibit No.
`
`Catchpole
`
`April 20, 2007
`
`1009
`
`November 16, 2006
`
`1 Catchpole is also a prior art reference under 35 U.S.C. § 102(a).
`
`8
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`Inter Partes Review Case No.: IPR2017-00746
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`US. Patent No. 9,028,877
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`D.
`
`Claim Construction - Broadest Reasonable Interpretation
`(“BRI”) (37 C.F.R. § 42.104(b)(3))
`
`In an inter partes review, Claim terms are interpreted according to their
`
`broadest reasonable construction in light of the specification of the patent in which
`
`they appear. 37 C.F.R. § 42.100(b); Office Patent Trial Practice Guide, 77 Fed.
`
`Reg. 48756 and 48766 (Aug. 14, 2012).
`
`Solely for this proceeding, the Section V. D. contains the proposed terms
`
`for construction and Petitioner's proposed constructions. All other terms, not
`
`presented below, should be given their plain and ordinary meaning. Petitioner
`
`reserves the right to address any Claim construction issue raised by Patent Owner.
`
`V.
`
`SUMMARY OF THE ‘877 PATENT (EXHIBIT 1001)
`
`A.
`
`State of the Art
`
`All of the claims issued in the ‘877 Patent are directed to methods of
`
`producing krill oil. The steps of the methods include providing and treating krill
`
`(e.g., by heating) to denature lipases and phospholipases and extracting oil using a
`
`polar solvent. Independent Claim 1 requires the denaturation step to be performed
`
`“on a ship,” while independent Claim 11 requires the denaturation be performed
`
`on “freshly harvested krill.” However, such steps were well known in the art as of
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`the earliest effective filing date.
`
`For example, Budzinski (Exhibit 1008) recognized the need to process
`
`freshly harvested krill to ensure the optimum product quality. “Due to its
`
`technological properties, the raw material should be processed as soon as possible
`
`after capture. The only way to meet this requirement is to install processing
`
`facilities on board the vessel.” (Exhibit 1008, p. 0031, sec. 4.9, lines 2-4.) (Tallon
`
`Decl. ‘][ 81.).
`
`Budzinski further discloses cooking and pressing krill on board the ship to
`
`produce a denatured product—krill meal. (Exhibit 1008, p. 002620, sec. 4.5.1,
`
`lines 1-2, 6-8, 15-17, and 21-23.) (See Tallon Decl. ‘][ 84). Budzinski also
`
`discloses extracting oil with a polar solvent (“[k]rill oil was only obtained by
`
`extraction with the help of various organic solvents.” (Exhibit 1008, p. 0030, sec.
`
`4.7, line 12.) (Tallon Decl., ‘][ 86).
`
`Similarly, Grantham discloses the problem of krill’s instability after
`
`catching and describes methods for processing (cooking) on board the ship before
`
`extracting krill lipids. (Exhibit 1032, p. 0026, section 3.1; pp. 0033-0034, section
`
`3.4.4; p. 0035, section 3.4.5; p. 0036, sec. 3.4.6.; p. 0039, section 3.4.8). (Tallon
`
`10
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`Decl., ‘][‘][ 158—166).
`
`The claims of the ‘877 patent also specify percentages of components in the
`
`resulting krill oil. However, the krill oil components were well known to be
`
`naturally present in krill oil in the amounts specified using standard extraction
`
`techniques. (See, e.g., Section VI, infra; Exhibit 1034, Kolakowska (1991)).
`
`B.
`
`Background of ‘877 Patent
`
`The ‘877 patent “provides methods of production of krill oil comprising: a)
`
`providing fresh krill; b) treating said fresh krill to denature lipases and
`
`phospholipases in said fresh krill to provide a denatured krill product; and c)
`
`extracting oil from said denatured krill product,” wherein steps (a) and (b) are
`
`performed on board a ship. (Exhibit 1001, col. 4, lines 47-52). The Patentee of
`
`the‘877 patent also states that, “The present invention provides a Euphausia
`
`superba krill oil composition comprising: from about 30% to 60% w/w
`
`phospholipids; from about 20% to 50% triglycerides; from about 400 to about
`
`2500 mg/kg astaxanthin; and from about 20% to 35% omega-3 fatty acids as a
`
`percentage of total fatty acids in said composition, wherein from about 70% to
`
`95% of said omega-3 fatty acids are attached to said phospholipids.” (Exhibit
`
`11
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`1001, col. 5, lines 49-56).
`
`However, as acknowledged in the Background of the Invention:
`
`In order to isolate the krill oil from the krill, solvent
`
`extraction methods have been used. See, e.g., WO
`
`00/23546. Krill lipids have been extracted by placing the
`
`material in a ketone solvent (e.g. acetone) in order to
`
`extract the lipid soluble fraction. This method involves
`
`separating the liquid and solid contents by evaporation.
`
`Further
`
`processing
`
`steps
`
`include
`
`extracting
`
`and
`
`recovering by evaporation the remaining soluble lipid
`
`fraction from the solid contents by using a solvent such
`
`as ethanol. See e.g., WO 00/23546.”
`
`(Exhibit 1001, 1:31-40).
`
`Patentee also acknowledges that, “[t]he methods described above rely on the
`
`processing of frozen krill that are transported from the Southern Ocean to the
`
`processing site. This transportation is both expensive and can result in
`
`degradation of the krill starting material.” (Exhibit 1001, col. 2, lines 3-6).
`
`Patentee also states, “[s]upercritical fluid extraction with solvent modifier
`
`has previously been used to extract marine phospholipids from salmon roe, but
`
`12
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`has not been previously used to extract phospholipids from krill meal. See, e.g.,
`
`Tanaka et al., J. Oleo. Sci. (2004), 53(9), 417-424.” (Exhibit 1001, col. 1, line 65
`
`to col. 2, line 2). However, this statement is demonstrably false in view of the
`
`disclosure of Catchpole (Exhibit 1009 ) discussed further below. See also,
`
`Halliday, Jess, “Neptune-Degussa Deal to Develop Phospholipids, Adapt Krill
`
`Oil,” http://www.nutraingredients-usa.com/Suppliers2/Neptune-Degussa-deal-to-
`
`develop-phospholipids-adapt-krill-oil, December 12, 2005. (Exhibit 1031, p.
`
`0002, “Degussa is renowned for its expertise in supercritical C02 extraction.”).
`
`With regard to krill compositions, Patentees admit, “[a] krill oil
`
`composition has been disclosed comprising a phospholipid and/or a flavonoid.
`
`The phospholipid content in the krill lipid extract could be as high as 60% w/w
`
`and the EPA/DHA content as high as 35% (w/w). See, e.g., WO 03/011873.”
`
`(Exhibit 1001, col. 1, lines 53-56).
`
`The analysis of the extracted krill oil is disclosed in the ‘877 patent in
`
`Table 21, which shows the amount of phospholipids, triglycerides and omega-3
`
`fatty acids in the extract. Tables 22 and 23 provide the only ether phospholipid
`
`data in the entire specification. Example 8 of the ‘877 patent concludes:
`
`13
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`The main polar ether
`
`lipids of the krill meal are
`
`alkylacylphosphatidylcholine (AAPC) at 7-9% of total
`
`polar lipids, lysoalkylacylphosphatidylcholine (LAAPC)
`
`at
`
`1%
`
`of
`
`total
`
`polar
`
`lipids
`
`(TPL)
`
`and
`
`alkylacylphosphatidyl-ethanolamine (AAPE) at <1% of
`
`TPL.
`
`(Tallon Decl. ‘][ 210).
`
`All of the issued claims include the “from about 3% to about 10% w/w”
`
`ether phospholipid limitation and it appears to be the element that Patentee relies
`
`upon for novelty. However, as demonstrated herein, krill oil containing ether
`
`phospholipid levels between about 3% and about 10% was known in the prior art.
`
`C.
`
`Prosecution History of the ‘877 Patent
`
`The ‘877 patent issued on May 12, 2015 from US. Application No.
`
`14/490,176, filed September 18, 2014. The ‘877 patent is a continuation of US.
`
`Patent Application No. 12/057,775, filed on March 28, 2008 and claims the
`
`benefit of four US. provisional applications: 61/024,072, filed on January 28,
`
`2008; 60/983,446, filed on October 29, 2007; 60/975,058, filed on September 25,
`
`2007; and 60/920,483, filed on March 28, 2007. Support for the claim element
`
`14
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`“ether phospholipid” — required by each ‘877 claim — was not introduced until the
`
`filing of the U.S. Application No. 61/024,072. (See Exhibits 1002-1005).
`
`Consequently, “the earliest priority date” for the claims of the ‘877 patent is
`
`January 28, 2008.
`
`During the prosecution of the ‘877 patent (Exhibit 1025), a final Office
`
`Action was mailed on January 13, 2015 in which all of the claims were rejected.
`
`Exhibit 1025, Part 1, pp. 0091-0097. After a telephone interview with the
`
`Applicant’s attorney on March 13, 2015, the Examiner issued a Notice of
`
`Allowance on April 6, 2015 with an Examiner’s Amendment. In the Examiner’s
`
`Amendment, claim 1 was amended to require steps (a) and (b) of the method to be
`
`performed on board a ship. Prior to the Examiner’s Amendment, Claim 1 did not
`
`require step (a) (providing krill) and step (b) (treating the krill) to be performed on
`
`board a ship. Thus, the Examiner only found Claim 1 to be allowable over the
`
`prior art if steps (a) and (b) were performed on board a ship. (Exhibit 1025, Part
`
`1, pp. 0011-0017).
`
`All of the claims of the ‘877 patent have the claim limitation of “from about
`
`3% to about 10% w/w ether phospholipids.” Applicant relied on this limitation in
`
`15
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`asserting patentability of the claims.
`
`In parent application no. 12/057,775, which issued as U.S. Patent No.
`
`9,034,388, Applicant amended the claims to add the limitation “about 3% to about
`
`10% ether phospholipid” and argued that the cited references do not teach
`
`extraction of a krill oil having the amended limitations.
`
`(See Response to Office
`
`Action dated September 7, 2012.) The claims are directed to “a method of
`
`producing krill oil. . ..from about 3% to about 10% w/w ether phospholipids”.
`
`(Exhibit 1024, Part 2, pp. 00633-0650).
`
`Furthermore, it is noted that in the prosecution history of US. Patent
`
`Application No. 9,078,905 (U.S. Patent Application No. 14/490,221), Applicants
`
`rely on the limitation of ether phospholipid levels in asserting patentability of the
`
`claims therein.
`
`(See Exhibit 1026).
`
`In particular, a Non-Final Office Action was mailed November 17, 2014
`
`(Exhibit 1026, part 1, pp. 0168-0177) that rejected all the as-filed claims. The
`
`Examiner asserted two United States Patents as prior art arguing that the
`
`disclosures these patents made the as-filed claims obvious: Beaudoin (Exhibit
`
`1016); and Porzio (Exhibit 1019). Beaudoin was characterized as disclosing krill
`
`16
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`oil components including phospholipids and triglycerides at similar concentrations
`
`as presented in the claims. This was combined with Porzio, which teaches how to
`
`encapsulate lipid compositions. A Response to the Non-Final Office Action was
`
`filed on December 19, 2014 (Exhibit 1026, part 1, pp. 0242-0251) with no claim
`
`amendments. The cited art was distinguished on the basis that it did not disclose a
`
`krill oil comprising “from about 3% - 15% ether phospholipids.” It was argued
`
`that Beaudoin’s ‘299 patent extraction method was Virtually identical to the NKO
`
`(Neptune Krill Oil) extraction process and would therefore be less than 3%.
`
`An analysis was presented of the NKO composition in the ‘877 patent
`
`(Example 8 and Table 22), showing that NKO has 7% AAPC and 1.2% LAAPC,
`
`i.e., a total ether phospholipid content of 8.2% of total phospholipids. It was
`
`argued that this percentage corresponded to an actual 2.46% value2 when relative
`
`to the krill oil (e.g., based upon a 30% measurement of total NKO phospholipids).
`
`It was argued, “[a]pplicant respectfully submits that this demonstrates that krill oil
`
`made by the Beaudoin method does not contain the claimed range of 3% to 15%
`
`2 This is an admission that Beaudoin describes krill oil haVing just below 3%
`
`ether phospholipids.
`
`17
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`U.S. Patent No. 9,028,877
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`ether phospholipids as a percentage of the total krill oil composition.” (Exhibit
`
`1026, part 1 pp. 0242 - 0251).
`
`A Final Rejection was mailed on February 17, 2015 (Exhibit 1026, part 1,
`
`pp. 0168 - 0177) where the non-statutory double patenting and obViousness
`
`rejections were maintained. The Examiner maintained that the calculated 2.46%
`
`ether phospholipid concentration in Beaudoin was close enough to the claimed
`
`range such that it would be obVious for one of ordinary skill in the art to optimize
`
`the extraction process through routine means to increase the ether phospholipid
`
`content to the claimed 3% concentration because of the known health benefits of
`
`ether phospholipids.
`
`A Response to the Final Office Action was filed on April 16, 2015 (Exhibit
`
`1026, part 1, pp. 0159 - 0164) with no claim amendments. Instead, an argument
`
`concerning alleged unexpected results was made in which the Applicants directed
`
`the examiner’s attention to Example 9 and some selected figures referred to
`
`therein that allegedly compares the claimed krill oil (designated Superba or PL2)
`
`to prior art krill oil (designated NKO or PL1).
`
`While Applicants relied on the above-quoted statement that “greater than
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`RIMFROST EXHIBIT 1063 page 0816
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`page 0816
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`U.S. Patent No. 9,028,877
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`3% ether phospholipids have superior activity,” there is no evidence of superior
`
`activity art and, in fact, the only disclosure of ether phospholipid amounts is in
`
`Table 22 and Table 23. (Tallon Decl. ‘][ 165). Moreover, the claims specify
`
`“about 3%” — not “greater than 3%.” Nevertheless, it appears that this “superior
`
`results” argument convinced the Examiner, since a Notice of Allowance followed
`
`on May 20, 2015 (with no written reasons for the allowance).
`
`Accordingly, throughout the prosecution of the ‘877 patent family,
`
`Applicants repeatedly stressed the importance of krill oil compositions with
`
`greater than 3% ether phospholipids in gaining allowance of the claims.
`
`D.
`
`Construction of the ‘877 Patent Claim Terms
`
`As discussed above, a claim in inter partes review is given the “broadest
`
`reasonable construction in light of the specification.” See 37 C.F.R. § 42.100(b).
`
`Petitioner sets forth herein its recommended interpretation of certain claim
`
`terms, the scope of the claims being unclear on their face.
`
`1. Claims 1 and 11 - “krill oil”
`
`The term “krill oil” is found in all of the independent claims, i.e., Claims 1
`
`and 11. The meaning of “krill oil” can be determined from the specification. The
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`RIMFROST EXHIBIT 1063 page 0817
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`page 0817
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`Inter Partes Review Case No.: IPR2017-00746
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`U.S. Patent No. 9,028,877
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`‘877 specification states:
`
`In order to isolate the krill oil from krill, solvent extraction
`
`methods have been used. See, e.g., WO 00/23564. Krill lipids
`
`have been extracted by placing the material in a ketone solvent
`
`(e.g., acetone) in order to extract the lipid soluble fraction.
`
`(Exhibit 1001, Col. 1, lines 31-34).
`
`Accordingly, patentees equate krill oil with the lipids extracted from krill.
`
`The ‘877 Patent further describes “krill oil” is a lipid-rich extract of krill.
`
`This extract can primarily include phospholipids and neutral lipids in varying
`
`proportions. The abstract of the ‘877 Patent describes the “actual krill oils” as the
`
`oil extracted using a polar solvent after using a non-polar solvent to remove
`
`neutral lipids: “The krill oils are obtained from krill meal using supercritical fluid
`
`extraction in a two stage process. Stage 1 removes the neutral lipid by extracting
`
`with neat supercritical C02 or C02 plus approximately 5% of a co-solvent. Stage 2
`
`extracts the actual krill oils by using supercritical C02 in combination with
`
`approximately 20% ethanol” (Exhibit 1001, Abstract, emphasis added). The ‘877
`
`patent therefore also discloses krill oil as a phospholipid rich extract produced by
`
`removing some or much of the triglyceride and other neutral oils. In addition, the
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`20
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`RIMFROST EXHIBIT 1063 page 0818
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`page 0818
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`U.S. Patent No. 9,028,877
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`‘877 Patent describes “combining said polar extract and said neutral extract to
`
`provide Euphausia superba krill oil...” (Exhibit 1001, Col. 5, line 55- Col. 6, line
`
`11; see also Tallon Dec. ‘][ 37).
`
`Additionally, in the context of the ‘877 Patent, “krill oil” is a lipid-rich
`
`extract of krill that comprises phospholipids, as well as a lipid-rich extract of krill
`
`that comprises blends of polar lipids (phospholipids) and neutral lipids in varying
`
`proportions. The ‘877 Patent repeatedly refers to the krill oil composition as
`
`comprising blend of lipid fractions. “In some embodiments, krill oil composition
`
`comprises a blend of lipid fractions obtained from krill” (‘877 Patent, 3:26-27,
`
`Exhibit 1001, p. 0025). “In some embodiments, the blended krill oil product
`
`comprises a blend of lipid fractions obtained from Euphausia superba” (‘877
`
`Patent, 5:43-45 and 6:50-52, Exhibit 1001, p. 0027; Exhibit 1001, 7:18-20, p.
`
`0028).
`
`(See Tallon Decl. ‘][‘][ 35-48).
`
`Thus, the proper construction of “krill oil” is “lipids extracted from krill.”
`
`(See Tallon Decl. ‘][ 48.)
`
`2. Claims 1 and 11 — “denature lipases and phospholipases”
`
`Claims 1 and 11 include the step of treating “to denature lipases and
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`21
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`RIMFROST EXHIBIT 1063 page 0819
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`page 0819
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`US. Patent No. 9,028,877
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`phospholipases in said krill.” The term “denature” is not expressly defined in the
`
`specification, but is described.
`
`In the Detailed Description of the ‘877 patent, patentees explain,
`
`The present invention provides methods to avoid decomposition
`
`of glycerides and phospholipids in krill oil and compositions
`
`produced by those methods. ...The solution to the problem is to
`
`incorporate a protein denaturation step on fresh krill prior to use
`
`of any extraction technology. Denaturation can be achieved by
`
`thermal stress or by other means. After denaturation the oil can
`
`be extracted by an optional selection of non-polar and polar
`
`solvents including use of supercritical carbon dioxide.
`
`(Exhibit 1001, 9: 44-54).
`
`Patentees also explain:
`
`In some preferred embodiments, freshly caught krill is first
`
`subjected to a protein denaturation step. The present invention
`
`is not limited to any particular method of protein denaturation.
`
`In some embodiments,
`
`the denaturation is accomplished by
`
`application of chemicals, heat, or combinations thereof.
`
`In
`
`some embodiments, freshly caught krill is wet pressed to obtain
`
`oil and meal.
`
`In some embodiments, the meal is then heated to
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`22
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`RIMFROST EXHIBIT 1063 page 0820
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`page 0820
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`U.S. Patent No. 9,028,877
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`a temperature of about 50°C to about 100°C for about 20
`
`minutes to about an hour, preferably about 40 minutes to
`
`denature the proteins.
`
`In some embodiments, this material is
`
`then pressed to yield a pressed cake. When this method is used
`
`on krill, only a small amount of oil is released. Most of the oil
`
`is still present in the denatured meal.
`
`(Exhibit 1001, 10:26-40).
`
`This disclosure is consistent with the extrinsic evidence. Hawley’s
`
`Condensed Chemical Dictionary defines “denaturation” as “a change in the
`
`molecular structure of globular proteins that may be induced by bringing a protein
`
`solution to its boiling point or by exposing it to acids or alkalies, or to various
`
`detergents. . ..It involves rupture of hydrogen bonds so that the highly ordered
`
`structure of the native protein is replaced by a looser and more random
`
`structure. ...” (Exhibit 1028, pp. 003-004.) (Tallon Decl. ‘][ 58).
`
`Proteins are like ribbons that coil to form more stable structures, for
`
`example, alpha helices and pleated sheets. The final three-dimensional structure of
`
`the protein is formed by non-covalent interactions between the amino acids of the
`
`protein. A quaternary structure is formed when multiple three-dimensional
`
`23
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`RIMFROST EXHIBIT 1063 page 0821
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`page 0821
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`proteins bind to form a single larger protein. (Tallon Decl. ‘][ 59). Thus, the
`
`“looser and more random structure” from denaturation causes proteins, such as
`
`enzymes, to lose their activity because the substrates can no longer bind to the
`
`active site of the enzyme. (Tallon Decl. ‘][ 60).
`
`It is well known that active lipases and phospholipases, enzymes present in
`
`krill, if not deactivated, will cause triglycerides (triacylglycerols) and glycerol-
`
`based phospholipids (phosphoglycerides) present in the krill to decompose and
`
`form free fatty acids. (See for example, Saether, p. 51, Exhibit 1027, p. 0001 .)
`
`(Tallon Decl. ‘][ 60). It is also well known that an effective method to denature
`
`enzymes is to apply heat.
`
`(See, e.g., Yoshitomi, Exhibit 1033, p. 0001, Abstract,
`
`“The [krill] product is produced by a process including only heating as means for
`
`denaturing protein and disabling the proteolytic enzymes originally contained in
`
`krill materials.”) (Tallon Decl. ‘][ 167).
`
`Thus, “to denature lipases and phospholipases” means “to alter the
`
`conformational structure of lipases and phospholipases to reduce lipid and
`
`phospholipid decomposition.” (Tallon Decl. ‘][‘][ 55-62).
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`RIMFROST EXHIBIT 1063 page 0822
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`page 0822
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`Inter Partes Review Case No.: IPR2017-00746
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`U.S. Patent No. 9,028,877
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`3. Claims 1 and 11 — “polar solvent”
`
`The element of “polar solvent” as set forth in Claim 1 and 11 is not
`
`explicitly defined in the specification, but is described. In the Krill Processing
`
`section of the Detailed Description, applicants disclose methods of making a
`
`Euphausia superba krill oil by contacting a Euphausia superba preparation, such
`
`as Euphausia superba krill meal with a polar solvent, such as ethanol to extract
`
`lipids. (Exhibit 1001, col. 12, lines 24-36). (Emphasis supplied). Applicants also
`
`disclose, “In some embodiments, krill oil is extracted from denatured krill meal.
`
`In some embodiments, the krill oil is extracted by contacting the krill meal with
`
`ethanol.” (Exhibit 1001, Col. 11, lines 3-5).
`
`In the Background of the Invention, patentees admit:
`
`In order to isolate the krill oil from the krill, solvent extraction
`
`methods have been used.
`
`See, e.g., WO 00/23546. Krill
`
`lipids have been extracted by placing the material in a ketone
`
`solvent (e.g., acetone) in order to extract the lipid soluble
`
`fraction.
`
`Further processing steps include extracting and
`
`recovering by evaporation the remaining soluble lipid fraction
`
`from the contents by using a solvent such as ethanol. See,
`
`e.g., WO 00/23546.
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`RIMFROST EXHIBIT 1063 page 0823
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`page 0823
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`
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`Inter Partes Review Case No.: IPR2017-00746
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`U.S. Patent No. 9,028,877
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`(Exhibit 1001, 1: 31-40).
`
`In the Detailed Description, patentees disclose:
`
`In some embodiments, krill oil is extracted from the denatured
`
`krill meal.
`
`In some embodiments, the krill oil is extracted by
`
`contacting the krill meal with ethanol.
`
`In some embodiments,
`
`krill is then extracted with a ketone solvent such as acetone.
`
`In other embodiments, the krill oil is extracted by one or two
`
`step supercritical fluid extraction.
`
`In some embodiments, the
`
`supercritical fluid extraction uses carbon dioxide and neutral
`
`krill oil is produced.
`
`In some embodiments, the supercritical
`
`fluid extraction uses carbon dioxide with the addition of a
`
`polar entrainer, such as ethanol, to produce a polar krill oil. In
`
`some embodiments, the krill oil meal is first extracted with
`
`carbon dioxide followed by carbon dioxide with a polar
`
`entrainer, or Vice versa.
`
`In some embodiments, the krill meal
`
`is first extracted with C02 supplemented with a low amount of
`
`a polar co-solvent
`
`(e.g.,
`
`from about 1% to about 10%,
`
`preferably about 5%) such a C1-C3 monohydric alcohol,
`
`preferably ethanol,
`
`followed by
`
`extraction with C02
`
`supplemented with a high amount of a polar co-solvent (from
`
`about 10% to about 30%, preferably about 23%) such as such
`
`a C1-C3 monohydric alcohol, preferably ethanol, or Vice versa.
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`26
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`RIMFROST EXHIBIT 1063 page 0824
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`page 0824
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`Inter Partes Review Case No.: IPR2017-00746
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`US. Patent No. 9,028,877
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`(Exhibit 1001, 1123-24).
`
`Thus, the ‘877 Patent contemplates extraction with a polar solvent or supercritical
`
`C02 in the presence of a polar solvent or entrainer. (See Tallon Decl. ‘][ 52.)
`
`The solvent must also be able to extract lipids that include phospholipids.
`
`The ‘877 patent explains, “[i]n some embodiments, the present invention provides
`
`a method of making a Euphausia superba krill oil composition comprising
`
`contacting Euphausia superba with a polar solvent to provide an polar extract
`
`comprising phospholipids.” (Exhibit 1001, Col. 6, lines 12-16). Typical polar
`
`organic solvents (pure or mixtures) used in industrial practice that meet these
`
`criteria include alcohols (e.g., methanol, ethanol, and isopropyl alcohol), ketones
`
`(particularly acetone), and esters (e. g. ethyl acetate). (See Tallon Decl. ‘][ 53.)
`
`Thus, the proper construction of “polar solvent” is “solvent or a mixture of
`
`solvents capable of extracting polar lipids comprising phospholipids.” (Tallon
`
`Decl. ‘][‘][ 49-54).
`
`4.
`
`Claims 3 and 11 - “freshly harvested krill”
`
`The specification does not includ
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