Trials@uspto.gov
`§71-272-7822
`
`Paper 7
`Entered: January 14, 2019
`
`UNITED STATES PATENT AND TRADEMARK OFFICE
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`RIMFROSTAS,
`Petitioner,
`
`Vv.
`
`AKER BIOMARINE ANTARCTIC AS,
`Patent Owner.
`
`Case IPR2018-01179
`Patent 9,375,453 B2
`
`Before ERICA A. FRANKLIN, TINA E. HULSE,and
`JOHN E. SCHNEIDER,Administrative Patent Judges.
`
`FRANKLIN,Administrative Patent Judge.
`
`DECISION
`Institution of Inter Partes Review
`35 U.S.C. § 314(a)
`
`

`

`IPR2018-01179
`Patent 9,375,453 B2
`
`I.
`
`INTRODUCTION
`
`Rimfrost AS(‘Petitioner’) filed a Petition requesting an inter partes
`
`review of claims 33-61 of U.S. Patent No. 9,375,453 B2 (Ex. 1001, “the
`
`°453 patent”). Paper 2 (“Pet.’””). Aker Biomarine Antarctic AS (“Patent
`Owner”) declinedto file a Preliminary Response to the Petition.
`
`Wehaveauthority to determine whetherto institute an inter partes
`review. 35 U.S.C. § 314(b); 37 C.F.R. § 42.4(a). Upon considering the
`Petition, we determine that Petitioner has shown a reasonablelikelihoodthat
`
`it would prevail in showing the unpatentability of at least one challenged
`claim. Accordingly, weinstitute an inter partes review ofall challenged
`
`claims based uponall groundsraised in the Petition.
`
`A,
`
`Related Proceedings
`
`Petitioner and Patent Owner provide notice that two related patents,
`U.S. Patent Nos. 9,028,877 B2 (“the ’877 patent’’) and 9,078,905 B2 (“the
`"905 patent”), have been asserted in Aker Biomarine Antarctic AS v. Olympic
`Holding AS, Case No. 1:16-CV-00035-LPS-CJB (D. Del.) (stayed). Pet. 2;
`Paper 4, 1. The parties note that the 453 patent wasasserted, along with
`related patents, in In the Matter of Certain Krill Oil Products and Krill Meal
`for Production ofKrill Oil Products, Investigation No. 337-TA-1019
`(USITC). Jd. According to the parties, that matter has been “effectively
`
`terminated.” Jd.
`
`The Board has issued Final Written Decisions addressing challenges
`to claims ofthe ’877 patent (1PR2U17-00746, Paper 23, claims 1-19 shown
`to be unpatentable; IPR2017-00748, Paper 23, claims 1-19 not shownto be
`unpatentable), and challenges to claims of the ’905 patent (IPR2017-00745,
`
`

`

`IPR2018-01179
`Patent 9,375,453 B2
`
`Paper 24, claims 1-20 shownto be unpatentable; IPR2017-00747, Paper 24,
`claims 1-20 not shown to be unpatentable).
`Petitioner has concurrently filed a petition for inter partes review of
`
`claims 1-32 of the ’453 patent in IPR2018-01178.
`
`B.
`
`The ’453 Patent
`
`The °453 patent describes extracts from Antarctic krill that include
`bioactive fatty acids. Ex. 1001, 1:19-20. The Specification states that the
`patent“discloses novel krill oil compositions having characterized by
`containing high levels of astaxanthin, phospholipids,includ[ing] enriched
`quantities of ether phospholipids, and omega-3 fatty acids.” Jd. at 9:28-31.
`The ’453 patent explains 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 symptomsof premenstrual symptoms or
`controlling blood glucose levels in a patient.” Ex. 1001, 1:46-52. In
`addition, the ’453 patent recognizes that krill oil compositions, including
`compositions having up to 60% w/w phospholipid content and as much as
`35% w/w EPA/DHAcontent, were knownintheart prior to the time of
`
`invention. Jd. at 1:52-57. The ’453 patent also indicates that supercritical
`fluid extraction with solvent modifier was knownto be a useful method for
`
`extracting marine phospholipids from salmonroe. Jd. at 1:65—67.
`According to the 453 patent, the solvent extraction methodsusedin
`the priorart to isolate krill oil from the krill “rely on the processing offrozen
`krill that are transported from the Southern Oceanto the processingsite,”
`which transportation is expensive and mayresult in the degradation of the
`
`3
`
`

`

`IPR2018-01179
`Patent 9,375,453 B2
`
`krill starting material. Jd. at 2:3-6. Such methods have includedsteps of
`placing the 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. Jd. at 1:32-40. To overcome the
`
`abovelimitations, the ’453 patent discloses “methods for processing freshly
`
`caughtkrill at the site of capture and preferably on board a ship.” Jd. at
`
`10:18-20. The challenged claims do notrecite any limitations directed
`
`toward processing the krill at the site of capture.
`
`The °453 patent describes producingkrill oil by first subjecting the
`
`krill to a protein denaturation step to avoid the formation of enzymatically
`
`decomposedoil constituents.
`
`/d. at 9:43-50. The Specification explainsthat
`
`the inventionis “not limited to any particular method of protein
`
`denaturation. In some embodiments, the denaturation is accomplished by
`
`application of chemicals, heat, or combinations thereof.” Jd. at 10:26-31.
`
`The Specification describes an embodiment wherein the krill oil is
`subsequently extractedusing,e.g., a polar solvent and use ofsupercritical
`
`carbon dioxide. Jd. at 9:51-54.
`
`In Example 7 of the ’453 patent, “[k]rill lipids were extracted from
`
`krill meal (a food grade powder) using supercritical fluid extraction with
`
`co-solvent.” Jd. at 31:45-46.
`
`ethanol
`5%_
`333°K and
`pressure,
`bar
`300
`Initially,
`(ethanol:CO2, w/w) were utilized for 60 minutes in order to
`removeneutral lipids and astaxanthin from the krill meal. Next,
`the ethanol content wasincreased 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 wasfinally filtered.
`
`Id. at 31:47-53.
`
`

`

`IPR2018-01179
`Patent 9,375,453 B2
`
`Example 8 of the ’453 patent prepared krill oil using the same method
`described in Example 7, from the samekrill meal used in that example.
`Ex. 1001, 32:16-17. The krill oil was then analyzed using *'P NMR
`
`/d. at 32:17-
`analysis to identify and quantify the phospholipidsin the oil.
`19. Table 22' showsthe phospholipid profiles for the raw material, the final
`product, and a commercially available krill oil, Neptune Krill Oil (“NKO”).
`Id. at 32:44-47. Table 22is reproducedbelow:
`
`)
`TABLE 22
`
`Phospholipid profiles
`
`Type B krill
`powder
`
`NKO
`
` Kril) Oil obtained in Example 7
`
`PC
`AAPC
`PI
`1LPC
`PS
`2LPC
`. LAAPC
`’ PE
`AAPE
`SM
`GPC
`DHSM
`NAPE
`CL
`LPE
`LCL
`% PL in
`powder or
`lipid sample
`
`66.0
`12.0
`
`1.2
`
`7.4
`2.2
`6.0
`
`5.3
`
`8.3
`
`.
`
`.
`
`68.6
`7.0
`
`1.3
`
`13.8
`1.2
`3.4
`
`L3
`
`3.4
`
`30.0
`
`75.3
`13.0
`
`OA |
`
`29
`0.9
`34
`1.5
`
`2.1
`0.5
`
`479
`
`Td. at 32:15-39.
`
`The 453 patent teaches that the “main polarether lipids of the krill
`meal are alkylacylphosphatidylcholine (AAPC) at 7-9% oftotal polarlipids,
`
`,
`
`| A reference in Example 8 of the ’453 patent to “table 25” (Ex. 1001, 32:45)
`appearsto be a typographicalerror, as the Specification doesnot include a
`Table 25. We understand that reference to “table 25” to instead mean
`“Table 22,” which sets forth the relevant phospholipid profiles.
`
`5
`
`

`

`IPR2018-01179
`Patent 9,375,453 B2
`
`lyso-alkylacylphosphatidylcholine (LAAPC)at 1% of total polar lipids
`(TPL) and alkylacylphosphatidyl-ethanolamine (AAPE)at <1% of TPL.”
`
`Id. at 32:47-S2.
`
`C.
`
`Illustrative Claim
`
`Of the challenged claims, claim 33, reproduced below,is the only
`
`independentclaim andis illustrative of the claimed subject matter.
`
`A method of production of polar krill oil from Euphausia
`33.
`superba comprising:
`a)
`treating the Euphasia superba to denature lipases and
`phospholipases to provide a denatured krill product,
`b) contacting the denatured krill product with a polar solvent to
`extract a polar krill oil comprising phospholipids, and said polar
`krill oil comprises greater than about 3% ether phospholipids
`w/w ofsaid polar krill oil; from about 27% to 50% non-ether
`phospholipids w/w of said polar krill oil so that the amount of
`total phospholipids is from about 30% to 60% w/w ofsaid polar
`krill oil; from about 20% to 50% triglycerides w/w ofsaid polar
`krill oil, and astaxanthin esters in amount greater than about 100
`mg/kg of said polar krill oil; and
`c) encapsulating said polarkrill oil in a soft gel capsule.
`
`D.
`
`The Asserted Grounds of Unpatentability
`
`Petitioner challenges the patentability of claims 33-61 of the ’453
`
`patent on the following grounds:
`
`

`

`XQ
`
`IPR2018-01179
`Patent 9,375,453 B2
`
`Claim(s)
`
`33-38, 40-43, 46-49, 51-52, 55-58, 60
`
`39
`
`44,50, 53, 59
`
`45,54, 61
`
`Petitioner also relies upon the Declaration of Stephen J. Tallon, Ph.D.
`
`(Ex. 1006).
`
`Il. ANALYSIS
`
`A.
`
`Claim Construction
`
`In an inter partes review, the Board interprets claim termsin 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.
`
`pa
`
`2 Breivik, WO 2008/060163 Al, published May 22, 2008 (“Breivik II”’)
`(Ex. 1037).
`3 Catchpole, WO 2007/123424, published Nov. 1, 2007 (““Catchpole) (Ex.
`1009).
`4 Bottino, Lipid Composition of Two Species ofAntarctic Krill: Euphausia
`superba and E. crystallorophias, 50B COMP. BIOCHEM. PHYSIOL. 479-484
`(1975) (“Bottino IT’) (Ex. 1038).
`5 Sampalis et al., Evaluation ofthe Effects ofNeptune Krill Oil™on the
`ManagementofPremenstrual Syndrome and Dysmenorrhea, 8(2) ALT.
`MED. REV. 171-179 (2003) (‘““Sampalis I’’) (Ex. 1012).
`° Sampalis, WO 03/011873 A2, published Feb. 13, 2003 (“Sampalis IT) (Ex.
`1013).
`7 Frickeet al., Lipid, Sterol and Fatty Acid Composition ofAntarctic Krill
`(Euphausia superba Dana), 19(11) LIPIDS 821-827 (1984)(“Fricke”)
`(Ex. 1010).
`8 Randolph, US 2005/0058728 Al, published Mar. 17, 2005 (“Randolph”)
`(Ex. 1011).
`
`

`

`IPR2018-01179
`Patent 9,375,453 B2
`
`.
`
`.
`
`‘
`
`§ 42.100(b); Cuozzo Speed Techs., LLC v. Lee, 1368S, Ct. 2131, 2142 (2016)
`(affirming applicability of broadest reasonable construction standardto inter
`partes review proceedings).° Under that standard, and absent any special
`definitions, we give claim termstheir ordinary and customary meaning, as
`would be understood by oneofordinary skill in the art at the time of the
`. invention. Jn re Translogic Tech., Inc., 504 F.3d 1249, 1257 (Fed. Cir.
`2007); Trivascular, Inc. v. Samuels, 812 F.3d 1056, 1062 (Fed. Cir. 2016)
`(“Undera broadest reasonable interpretation, wordsofthe claim must be
`giventheir plain meaning, unless such meaningis inconsistent with the
`specification and prosecution history.”’).
`Anyspecial definitions for claim terms mustbe set forth with
`reasonableclarity, deliberateness, and precision. Jn re Paulsen, 30 F.3d
`
`1475, 1480 (Fed.Cir. 1994).
`Petitioner asserts proposed claim constructions for a numberof claim
`terms. Pet. 16-32. We determinethat construction of those claim terms are
`
`not necessary for purpose of this Decision. See Vivid Techs., Inc. v. Am. Sci.
`& Eng’g, Inc., 200 F.3d 795, 803 (Fed. Cir. 1999) (only termsthat are in
`controversy need to be construed, andonly to the extent necessary to resolve
`the controversy).
`
`*
`
`° The Office recently changed the claim construction standardto be
`employed in an inter partes review. See Changes to the Claim Construction
`Standardfor Interpreting Claims in Trial Proceedings Before the Patent
`Trial and Appeal Board, 83 Fed. Reg. 51340 (October 11, 2018). However,
`based on the filing date of the Petition in this proceeding, the applicable
`claim construction standard remainsas set forth in 37 C.F.R. § 42.100(b):
`(2016).
`
`

`

`IPR2018-01179
`Patent 9,375,453 B2
`
`B.
`
`Level of Ordinary Skill in the Art
`
`Thelevel of skill in the art is a factual determination that provides a
`
`primary guarantee of objectivity in an obviousness analysis. A/-Site Corp.v.
`VSI Int’! 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)).
`|
`Accordingto Petitioner, a person of ordinary skill in the art at the time
`
`of the invention 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
`through education or experience, of
`organic chemistry andin 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 havehadatleast five
`years applied experience.
`Pet. 6 (citing Ex. 1006 {J 30-31).
`
`At this stage in the proceeding, we determinethat Petitioner’s
`description ofthe level of ordinary skill in the art is sufficiently supported by
`the current record. Moreover, we have reviewed the credentials of Dr.
`
`Tallon and, at this stage in the proceeding, consider him to be qualified to
`provide his opinion onthelevel of skill and the knowledge of a person of
`ordinary skill in the art at the time of the invention. Wealso note that the
`applied prior art reflects the appropriate level ofskill at the time of the
`claimed invention. See Okajima v. Bourdeau, 261 F.3d 1350, 1355 (Fed.
`
`Cir. 2001).
`
`

`

`IPR2018-01179
`Patent 9,375,453 B2
`
`C._Obviousness over Breivik II, Catchpole, Bottino II, and Sampalis I
`
`Petitioner asserts that claims 33-38, 40-43, 46-49, 51-52, 55-58, 60
`
`would have been obvious over the combined teachings of BreivikI,
`
`Catchpole, Bottino II, and Sampalis I. Pet. 33-56.
`
`1. Breivik IT
`
`BreivikII “relates to a process for preparing a substantially total lipid
`
`fraction from fresh krill, and a process for separating phospholipids from the
`other lipids.” Ex. 1037, 1:8-10.'° According to Breivik II, approximately
`50% of the lipids in E. superba are phospholipids, and oil extracted from E.
`superba contains lower amounts of environmental pollutants than traditional
`fish oils. Jd. at 1:32-33, 2:3-4. Breivik II explainsthat krill lipases remain
`
`active after the krill is dead, and, thus, krill oil may contain an undesired
`
`amountoffree fatty acids, makingit desirable to use a process that will
`provide for a low degree of hydrolysisof the krill lipids. Jd. at 2:6-13.
`Breivik II teaches that its extraction process provides a substantially
`total lipid fraction from fresh krill, without using organic solvents like
`acetone. Jd. at 3:29-31. That lipid fraction containstriglycerides,
`astaxanthin and phospholipids. Id. at 3:19-20. According to BreivikII, the
`process includes anoptionalheat pre-treatmentofthe krill to inactivate
`enzymatic decomposition ofthe lipids, ensuring a product with a low level
`
`of free fatty acids. Jd. at 4:3-6.
`
`Breivik II describes an extraction process in whichfresh krill is
`
`washed with ethanol, and the ethanol washedkrill is then extracted with
`
`10 Unless otherwise noted, the cited page numbersrefer to those supplied by
`the original reference, and not the page numbers added byPetitioner.
`
`10
`
`

`

`IPR2018-01179
`Patent 9,375,453 B2
`
`supercritical CO2 containing 10% ethanol. Jd. at 7:31-8:3 (Example 2).
`Breivik II also discloses a process in which the raw material is pre-treated
`with heated at 80°C for 5 minutes before the first wash with ethanol. Jd.
`
`9:5-11 (Example 6). Accordingto BreivikII, “heat-treatment gives an
`increased yield oflipids comparedto the same treatment with no heating.”
`
`Td. at 9:33-34.
`
`Breivik II explains that “[a] lipid fraction or lipid product, derived
`from the processing according to the invention may have someadditional
`advantagesrelated to quality compared to knownkrill oil products
`(produced by conventional processes), such as for instance a krill oil from
`Neptune Biotechnologies & Bioresources extracted from a Japanese krill
`source (species not specified)” having > 40.0% total phospholipids and > 1.0
`mg/g esterified astaxanthin. Jd. at 11:23-36. Breivik II states that a lipid
`fraction or product according to the invention would be expected, among
`other things, to “contain substantially less hydrolysed and/or oxidised lipids
`than lipid produced by conventional processes” and have “less deterioration
`ofthe krill lipid antioxidants from conventional processing.” Jd. at 12:1-9.
`2. Catchpole
`Catchpole discloses “a process for separating lipid materials
`containing phospholipids,” Ex. 1009, 1:5—6, in order to produce a product
`containing “desirable levels of particular phospholipids,” id. at 3:27—28.
`Catchpole states that phospholipids “have been implicated in conferring a
`uuuiber 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
`
`11
`
`

`

`IPR2018-01179
`Patent 9,375,453 B2
`
`sports nutrition.” Jd. at 1:29-2:2. Catchpole further discloses that products
`having high levels of particular phospholipids “may be employedin a
`numberofapplications, including infant formulas, brain health, sports
`nutrition and dermatological compositions.” Jd. at 25:9-13.
`Catchpole describes, in Example 18,the fractionation ofkrill lipids
`from krill powder using a process that employs supercritical COzinafirst
`extraction, and a CO2 and absolute ethanol mixture in a second. Jd. at 24:1-
`16. Table 16, reproduced below,reports the phospholipid concentrations
`presentin the krill oil extract obtained by Catchpole. Jd. at Table 16.
`
`Table 16
`
`
`
`|betTaTeTaebobse
`
`
`
`_}|AAPC} AAPE
`CL
`PS
`PI
`PC
`% of feed)
`Feed|0.0|0.0[04|0.1|
`
`||6.6 :
`
`
`extract2|43[398|0.0[00|03|02|:
`
`Residue[79.2[3.6|0.0|00[03|0.2|
`As shownin Table 16, the composition of Extract 2 includes 39.8%
`
`Composition, %
`
`phosphatidylcholine (“PC”). Jd. The ether phospholipids
`alkylacylphosphatidylcholine (*AAPC”) and alkylacylphosphatidyl-
`ethanolamine (“AAPE”) were also present in Extract 2, representing 4.6%
`and 0.2%, respectively, of the extracted composition. Jd.
`In addition,
`summing each ofthe reported phospholipid amounts reported for Extract 2
`yields a total phospholipid concentration of 45.1%. Id.
`3. Bottino II
`
`Bottino II characterizes the lipids of two Antarctic euphausiids,
`Euphasia supercar and Euphasia Crystallorophias. Bottino II explains,
`“when onerefers to Antarctic krill, one generally means Euphausia superba,
`
`which is the most abundant andfar better known speciesofkrill in the
`
`Antarctic Oceans.” Ex. 1038, 479.
`
`12
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`

`

`IPR2018-01179
`Patent 9,375,453 B2
`
`Bottino II explains that the Euphausiids were collected and, once on
`board the ship, the samples were rapidly sorted by hand and extracted with a
`“chloroform:methanol (2:1, v/v) mixture.” Jd. Fatty acid compositions were
`
`determined by gas-liquid chromatography. Jd. at 480.
`
`Table 1 of Bottino II is reproduced below.
`
`Table 1. Fatty acids of Antarctic krill*
`
`E. superba
`E. erystallorophias
`
`
`
`Fatty acid Station 8 Station 11 Station 13 Station 16
`
`0-3
`14-9
`03
`0-5
`21:2
`0-7
`0-1
`0-3
`tr
`9-0
`0-7
`18-2
`0-6
`0-3
`26
`
`0-2
`14-3
`0-2
`0-2
`27
`1-4
`0-1
`0-2
`0-1
`8-9
`0°3
`21-7
`09
`0-1
`2:0
`
`weight %
`02
`2:3
`0-1
`0-2
`13-8
`1:2
`
`8-4
`0-4
`475
`0:2
`
`3-3
`0-1
`0-2
`0-9
`0-5
`1S
`
`12:0
`14:0
`15:0 brt
`15:0
`16:0
`18:0
`22:0
`14:1 (n— 2)
`15;1 (a— %)
`16:1 (n—7)
`17:1 (#—8)
`18:1 (n-—9)
`20:1 (n—9)
`18:2 (n—6)
`18:2 (#~ 3)
`20:2 (n— 3)
`02
`053
`18:3(n-6)
`1-0
`1-1
`18:3 (n—3)
`0°5
`0-6
`20:3 (n—3)
`3-3
`2-2
`18:4 (n—3)
`0-4
`0-5
`20:4 (n— 6)
`0-2
`0-5
`20:4 (n— 3)
`03
`0-2
`22:4 (n— 6)
`11-8
`11-4
`16-0
`20:5 (n- 3)
`O1
`0-1
`0-3
`22:5 (n—3)
`
`
`
`
`8-6 73 7322:6 (n— 3) 5-5
`
`tr
`2-4
`
`01
`14:8
`1-3
`
`10:8
`0-4
`45:2
`Os
`
`27
`
`0:3
`0-9
`
`o9
`0-7
`0-1
`
`13-4
`
`* Data from Bottino (1974).
`t br, Branched-chain fatty acids.
`
`Ex. 1038, Table 1. Table 1 discloses the fatty acid content of E. superba and
`
`E. crystallorophias obtained from different locations(i.e., stations) as a
`
`weight percentoftotal fatty acids. Id. at 480.
`
`13
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`

`

`IPR2018-01179
`Patent 9,375,453 B2
`
`Table 2 of Bottino II is reproduced below.
`u
`
`Table 2. The lipids of Antarctickrill
`E. superba
`E. erystallorophias
`
`
`
`Station 8(1)* Station 13 (4)—_Station 16 (2)Station 11(2)
`
`
`
`_-
`Waxes
`_
`Steroid esters
`3646
`Triglycerides
`4+5
`Diglycerides
`58+ 14
`Complex lipids
`48
`PCt
`8
`PEt
`1
`Lyso PC
`_
`1
`PGT
`
`
`
`21 2422 1+2Unknown§ T+1
`
`weight %
`444 10f
`243
`—
`—_—
`53+8
`46
`6
`1
`
`20+1
`274+9
`_—
`441
`42+8
`
`_
`—
`8
`17
`54
`
`
`
`,
`
`* Number of determinations in parentheses.
`+ PC, Phosphatidylcholine; PE, phosphatidylethanolamine; PG, phosphatidylglycerol.
`t Weight per cent plus or minus the standard deviation.
`§ R, between those oftriglycerides and diglycerides. The recovered amountofthis fraction was too
`small for further characterization.
`
`Ex. 1038, Table 2. Table 2 reports the identity and amountof eachlipid
`present in the E. superba and E. crystallorophias samples analyzed as a
`weight percentoftotal lipids. Jd. at 480-481.
`
`‘4. Sampalis I
`Sampalis I describesa clinicaltrial “[t]o evaluate the effectiveness of
`NeptuneKrill Oil™ (NKO™)for the managementof premenstrual
`syndrome and dysmenorrhea.” Ex. 1012, 171. Sampalis I explains that
`NKOis “extracted from Antarctic krill also known as Euphausia superba.
`Euphausia superba, a zooplankton crustacean,is rich in phospholipids and
`triglycerides carrying long-chain omega-3 polyunsaturated fatty acids,
`mainly EPA and DHA,andin various potent antioxidants including vitamins
`A and E,astaxanthin, and a novelflavonoid.” Jd. at 174.
`|
`Sampalis I discloses that each patient in the clinicaltrial 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)oncedaily with meals during the first
`
`14
`
`

`

`IPR2018-01179
`Patent 9,375,453 B2
`
`monthofthetrial.” Jd. Sampalis Ireports 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 symptomsrelated to
`premenstrual syndrome,andis significantly more effective for the
`management of dysmenorrhea and emotional premenstrual symptoms than
`fish oil.” Id. at 178.
`
`5. Analysis
`
`A patent claim is unpatentable under 35 U.S.C. § 103(a)if the
`
`differences between the claimed subject matter and the priorart are suchthat
`
`the subject matter, as a whole, would have been obviousat the time the
`invention was madeto a person having ordinary skill in the art to which said
`
`subject matter pertains. KSR Int’l Co.v. Teleflex Inc., 550 U.S. 398, 406
`(2007). “An obviousness determination requires finding both ‘that a skilled
`artisan would have been motivated to combinethe teachingsof the prior art
`
`references to achieve the claimed invention, and that the skilled artisan
`
`would have had a reasonable expectation of success in doing so.’” CRF'D
`
`Research, Inc. v. Matal, 876 F.3d 1330, 1340 (Fed. Cir. 2017) (quoting
`Intelligent Bio-Sys., Inc. v. Illumina Cambridge Ltd., 821 F.3d 1359, 1367-
`1368 (Fed. Cir. 2016)). “The reasonable expectation of success requirement
`
`refers to the likelihood of success in combining references to meetthe
`
`limitations of the claimed invention.” Intelligent Bio-Sys., Inc., 821 F.3d at
`
`1367. A reasonable expectation of success “does not require absolute
`
`predictability of success .. . all that is required is a reasonable expectation
`ofsuccess.” In re Kubin, 561 F.3d 1351, 1360 (Fed. Cir. 2009) (quoting /n
`
`re O'Farrell, 853 F.2d 894, 903-904 (Fed. Cir. 1988)).
`
`15
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`

`IPR2018-01179
`Patent 9,375,453 B2
`
`Petitioner asserts that method of independent claim 33 would have
`been obvious to a person ofskill in the art over the combined teachings of
`Breivik II, Catchpole, BottinoII, and Sampalis I. Pet. 33-43. To begin,
`Petitioner asserts that Breivik II teaches a method of producing polar krill oil
`from E. superba becausethereferenceis directed to “preparing a
`substantially total lipid extract from fresh krill,” and explainsthat “[t]he
`current greatest potential for commercial utilisation is the Antarctic
`Euphausia superba.” Pet. 34 (quoting Ex. 1037, 1:25—28). Petitioner also
`references an examplein Breivik II describing the extraction of lipids from
`
`.
`
`fresh E. superba. Id. at 36-37 (citing Breivik II Example6).
`Petitioner asserts that Breivik II describes the “application of heat to
`
`denature krill” to provide a denatured krill product, as required by claim 33,
`by teaching, amongother things, an “optional pre-treatment involvingshort-
`term heatingofthe fresh krill will also give an inactivation of enzymatic
`decomposition ofthe lipids, thus ensuring a product with very low levels of
`‘free fatty acids.” Jd. at 35 (citing Ex. 1037, 4:3—6, 9:5—6, 10:6-8 and 11—
`12). Dr. Tallon explainsthat, in Brevik II, heating the fresh krill inactivates
`the krill’s enzymes, includinglipases, thereby preventing decomposition of
`
`the krill lipids. Ex. 1006 { 196.
`As for the next claimed step of contacting the denatured krill product
`with a polar solvent to extract polarkrill oil, Petitioner asserts that such
`process was well knownin theart at the time of the invention and Breivik I
`expressly discloses this processing step for E. superba by teaching an
`extraction step at supercritical pressure using COcontaining 10% ethanol,
`and isolating the lipid fraction from the ethanol. Pet. 35—36 (citing Ex.
`1037, 4:28-33). As further support, Petitioner also refers to Breivik II’s
`
`16
`
`

`

`IPR2018-01179
`Patent 9,375,453 B2
`
`example using a “[s]upercritical fluid extraction with CO2 containing 10%
`
`ethanol.” /d. at 36 (quoting Ex. 1037, 9:5-8).
`Forthelast step of the claimed method requiring encapsulating the
`polar krill oil in a soft gel capsule, Petitioner asserts that “[t]he priorart
`expressly discloses the formulation ofkrill oil in capsule andsoft get capsule
`dosage formssuitable for oral administration.” Pet. 37. Specifically,
`Petitioner refers to a disclosure in Sampalis I of administering krill oil to
`
`patients in the form ofasoft gel. /d. at 37-38 (citing Ex. 1012, 4).
`With respectto the recited composition of the extracted krill oil in
`claim 33, Petitioner and Dr. Tallon assert that “each of the recited
`constituents is naturally presentin live krill, and were knowntobepresent in
`lipid fractions extracted from krill using conventional extraction techniques
`and solvents.” Pet. 38 (citing Ex. 1006 J 102, 106, and 110). In support of
`that position, Petitioner and Dr. Tallon refer to Catchpole. In particular, for
`the recitation that the polar krill oil comprises “greater than about 3% ether
`phospholipids,” Petitioner and Dr. Tallon assert that Catchpole is directed to
`methodsfor separating lipid materials from materials, including krill, and
`describes the extracted phospholipidsas being “implicated in conferring a
`numberof health benefits.” Jd. at 38-39 (citing Ex. 1006 ff 214-225, Ex.
`1009, 1:29-2:2, 7:5-6, 24:1-9).
`|
`Moreparticularly, Petitioner and Dr. Tallon rely upon Catchpole’s
`disclosure in Example 18 of the fractionation ofkrill lipids from krill
`powder, and the reported concentrations of extracted phospholipidsin Table
`16. Pet. 39 (citing Ex. 1006 {J 219-225, Ex. 1009, 24:1-19). Dr. Tallon
`explains that the ether phospholipids fractions analyzed were alkylacyl-
`phosphatidylcholine (AAPC)and alkylacylphospatidylethanolamine
`
`17
`
`

`

`IPR2018-01179
`Patent 9,375,453 B2
`
`(AAPE). Ex. 1006 9] 221-222; Ex. 1009, 14:7-11. Petitioner and Dr.
`Tallon draw ourattention to the composition of Extract 2 in Table 16
`reported as having 4.8% ether phospholipids (4.6% AAPC and 0.2%
`AAPE), thus comprising greater than about 3% ether phospholipids as
`
`required by claim 33. Pet. 40.
`Petitioner and Dr. Tallon also refer to Catchpole’s Extract 2 in
`
`Example 18 as disclosing “from about 27% to 50% w/w non-ether
`phospholipids so that the amount oftotal phospholipids in the krill oil is
`from about 30% to 60% [w/w],” as required in claim 33. Pet. 41 (citing Ex.
`
`1006 Ff 219-225, 414, Ex. 1009, 24). Specifically, they rely upon
`Catchpole’s disclosure in Table 16 that Extract 2 has 45.1% total
`phospholipids (39.8% PC,0.3% PE, 0.2% CL, 4.6% AAPC,0.2% AAPE),
`and thus, has 40.3% non-ether phospholipids by deduction,i.e., total
`phospholipids (45.1%) minusether phospholipids (4.8%). Jd. (citing Ex.
`
`1006 4 212-225, 414).
`Concerning the claim 33 recitation that the krill extract include “from
`about 20% to 50% triglycerides w/w ofsaid polarkrill oil,” Petitioner asserts
`that “[i]t would have been recognizedthat triglycerides represent one ofthe
`most abundant constituents in krill oil, and a POSITA would have [] looked
`to otherpolar krill extracts for the relative amountpresent.” Pet. 41 (citing
`Ex. 1006 {f 100, 414). As an example of such relative amounts, Petitioner
`and Dr. Tallon refer to the details provided in Bottino II’s study ofthe lipids
`
`extracted frum two species of Antarctic krill, including £. superba, using a
`polar solvent. /d. (citing Ex. 1038, 479-482). According to Petitioner and
`Dr. Tallon, Bottino’s report that “in Euphausia superba the complex lipids
`were mostly phosphatidylcholine at 48-49%, followed bytriglycerides at
`
`18
`
`

`

`IPR2018-01179
`Patent 9,375,453 B2
`
`36%” demonstrates that it was knownin theart at the timeof the invention
`
`that “oil extracted from krill using conventional solvent extraction
`techniques and solvents containedtriglyceride levels within 20%-50% the
`limitation of claim [33].” Jd. at 42 (quoting Ex. 1006 4] 182-187 andciting
`
`Ex. 1038, 481 (Table 2) and 479-482)).
`Claim 33 also requires “astaxanthin esters in amountof greater than
`about 100 mg/kg ofsaid polar krill oil.” For this element, Petitionerrelies
`upon Breivik II’s disclosure that “Neptune’s commercialkrill oil product has
`> 40% total phospholipids and > 1.0 mg/g esterified astaxanthin (1.e., > 1000
`mg/kg).” Pet. 42. Based on that disclosure, Petitioner asserts that “the
`astaxanthin element of claim 33 is expressly disclosed in the prior art.” Id.
`Accordingto Petitioner, the ordinary artisan would have had a reason
`to combinethe teachings of Breivik II, Catchpole, Bottino II and Sampalis I
`because ofthey each relate to the samefield of endeavor, i.e., extracting krill
`oil using conventionalpolar solvents and extraction techniques,
`characterizing krill oil components, and discussing health benefits associated
`with such components. See Pet. 53-56. For example, Petitioner notesthat
`Breivik II and Catchpole disclose methodsof such extraction, Catchpole
`discloses phospholipid and triglyceride contents ofpolar krill oil, Bottino II
`discloses the esterified astaxanthin content of a commercialkrill oil, and
`
`Sampalis I discloses polar krill oil formulated for oral consumption. Jd.
`According to Petitioner,
`Thus, a POSITA,following the treatment and extraction steps
`taught by Breivik II, would have been motivatedto look to
`other references such as Catchpole and BottinoII to ascertain
`the other constituents naturally present in the krill oil extracts
`and their respective amounts, and to administerthe resulting
`
`19
`
`

`

`IPR2018-01179
`Patent 9,375,453 B2
`
`polar krill oil as a nutritional supplementin the form ofa soft-
`gel capsule, as taught by Sampalis I.
`
`Pet. 56 (citing Ex. 1006 §§ 85-110, 438). Based on theprior art teachings,
`Petitioner asserts that the ordinarily skilled artisan would have also had a
`“reasonable expectation of producing a polarkrill oil having the percentage
`
`of constituents as recited in the claims.” Jd. at 53.
`
`Likewise, Dr. Tallon testifies that a person of ordinary skill in the art
`
`“would have knownthatthe relative proportionsof the naturalkrill and
`
`hencethe natural krill oil constituents could be varied in predictable ways by
`
`. to selectively
`applying a single solvent or combinationofsolvents. .
`extract specific groups oflipid components. .
`., and by blending these
`selective extracts in known and predictable ways to producea desired krill
`oil composition,” indicating that an ordinarily skilled artisan would have had
`a reason to combine the teachings of the cited references and a reasonable
`expectation of success in doing so in a mannerthat yields the claimed
`
`invention. Ex. 1006 { 104.
`Based upon our review ofthe current record, we determinethat
`Petitioner’s characterization of Breivik II, Catchpole, Bottino I, and
`SampalisI, as well as Dr. Tallon’s testimony as to the knowledgein the art
`are adequately supported in terms of demonstrating that Breivik II teaches or
`suggests the claimed methodsteps for producingpolar krill oil from £.
`superba by providing a denaturedkrill product and extracting polar krill oil
`from that product using a polar solvent, Catvhpole disclosed the components
`of polarkrill oil and the amountsthereof, Bottino II discloses the triglyceride
`content ofpolar krill oil, and Sampalis I disclosespolar krill oil formulated
`as a soft gel capsule.
`
`20
`
`

`

`TPR2018-01179
`Patent 9,375,453 B2
`
`Based on the current record, we do not agree with Petitioner’s
`assertion that Breivik II “expressly disclosed” the claim element requiring
`

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