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`UNITED STATES PATENT AND TRADEMARK OFFICE
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`_______________________
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`BEFORE THE PATENT TRIAL AND APPEAL BOARD
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`_______________________
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`RIMFROST AS
`
`Petitioner
`
`v.
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`AKER BIOMARINE ANTARCTIC AS
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`Patent Owner
`
`_______________________
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`Case Nos.
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`IPR2018-01178
`IPR2018-01179
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`U.S. Patent No. 9,375,453 B1
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`_______________________
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`DECLARATION OF DR STEPHEN J. TALLON
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`TABLE OF CONTENTS
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`DECLARATION OF DR STEPHEN J. TALLON .............................................. 1
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`TABLE OF CONTENTS ........................................................................................... 2
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`AGREEMENT TO PROVIDE EXPERT TESTIMONY .......................................... 9
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`BASES FOR OPINIONS GIVEN ...........................................................................12
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`NO FINANCIAL INTEREST IN PROCEEDING ..................................................19
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`QUALIFICATIONS AND RELEVANT EXPERIENCE .......................................19
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`RELEVANT CONSIDERATIONS .........................................................................25
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`LEVEL OF ORDINARY SKILL IN THE ART & THE POSITA .........................30
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`THE ‘453 PATENT (EXHIBIT 1001) ....................................................................31
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`Priority Claims ..........................................................................................................31
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`‘453 Family Chart .....................................................................................................32
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`‘453 Disclosure .........................................................................................................32
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`‘453 Patent issued over prior art based on not relevant claim by Patent Owner of
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`PAF-like activity of ether phospholipids relying on Marathe (Exhibit 1094) and
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`Tanaka I (Exhibit 1014). ......................................................................................36
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`PAF would not have been a concern to a POSITA extracting PL from krill. ..........39
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`THE ‘453 PATENT IS ENTITLED TO A PRIORITY ..........................................48
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`DATE NO EARLIER THAN JANUARY 28, 2008 ...............................................48
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`THE ‘453 PATENT IS ENTITLED TO A PRIORITY ..........................................49
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`DATE NO EARLIER THAN SEPTEMBER 6, 2013 .............................................49
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`MOTIVATION TO COMBINE - OVERVIEW .....................................................63
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`SEVERAL KRILL COMPONENTS KNOWN TO A POSITA ..............................73
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`COMPARED WITH ‘453 PATENT EXAMPLE 7 .................................................73
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`CLAIM TERMS ......................................................................................................79
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`ITC Claim Construction. ...........................................................................................79
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`“krill oil” means “lipids extracted from krill” .........................................................83
`
`“polar krill oil” means “krill oil containing polar lipids” .........................................89
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`“astaxanthin” means “the astaxanthin molecule having the structure shown below
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`and includes both cis- and trans forms of the molecule: .....................................93
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`“astaxanthin esters” means “astaxanthin molecules in which one or both of the
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`hydroxyl groups are replaced by a fatty acid tail connected to the astaxanthin
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`molecule through an ester bond.” ........................................................................98
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`“about” means “approximately” and, at a minimum extends the number it modifies
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`to include the range provided by rounding, means “a range about the number it
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`modifies which when rounded provides the number it modifies” .......................99
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`“plant phytonutrient” means “plant-derived compound that has a positive impact on
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`human health or nutrition” .................................................................................102
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`“polar solvent” means “solvent or mixtures of solvents capable of extracting polar
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`lipids comprising phospholipids” ......................................................................104
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`“to denature lipases and phospholipases” means “to alter the conformational
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`structure of lipases and phospholipases to reduce lipid and phospholipid
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`decomposition” ..................................................................................................107
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`PRIOR ART ...........................................................................................................113
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`Bottino I (Exhibit 1007) ..........................................................................................113
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`Bottino II (Exhibit 1038) .........................................................................................116
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`Breivik II (Exhibit 1037), Breivik I (Exhibit 1035) and Breivik III (Exhibit 1036)
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` ............................................................................................................................119
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`Catchpole (Exhibit 1009) ........................................................................................134
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`Enzymotec (Exhibit 1048, GRAS Notice No. GRN 000226) ................................141
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`Fricke (Exhibit 1010) ..............................................................................................152
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`Fricke 1984 analysis of omega-3 fatty acids .......................................................161
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`Randolph (Exhibit 1011) .........................................................................................166
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`Sampalis I (Exhibit 1012) .......................................................................................170
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`Sampalis II (Exhibit 1013) ......................................................................................174
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`Tanaka I (Exhibit 1014) ..........................................................................................184
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`Tanaka II (Exhibit 1015) .........................................................................................187
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`Budziński (Exhibit 1008) ........................................................................................191
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`Bunea (Exhibit 1020) ..............................................................................................197
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`Grantham (Exhibit 1032) ........................................................................................201
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`Grynbaum (Exhibit 1039) .......................................................................................208
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`Yoshitomi (Exhibit 1033) .......................................................................................217
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`Mayzaud (Exhibit 1084) .........................................................................................224
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`Neptune Krill Oil (NKO) and Krill Bill NKO (Exhibit 1070, et. al) ......................226
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`Britton (Exhibit 1097) – trans (all-E) form of astaxanthin predominates in nature
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` ............................................................................................................................231
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`Yuan (Exhibit 1098) ................................................................................................234
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`Foss (Exhibit 1102) .................................................................................................236
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`Higuera-Ciapara (Exhibit 1100) ..............................................................................238
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`Lambertsen (Exhibit 1101) .....................................................................................242
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`Tehoharides (Exhibit 1030).....................................................................................243
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`THE ‘453 PATENT CLAIM CHART ...................................................................245
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`‘453 PETITION GROUNDS ...............................................................................246
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`GROUND 1 ............................................................................................................247
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`BREIVIK II, CATCHPOLE, BOTTINO II, AND SAMPALIS I .........................247
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`CLAIMS 1-3, 5-10, 12, 14-17, 19-20, 23-26, 28, 30-38, 40-43, 46-49, 51-52, 55-
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`58, and 60 ..........................................................................................................247
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`Claims 1, 5, 6, 12 and 33. ........................................................................................247
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`Claims 2, 3, 37 and 38 .............................................................................................253
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`(greater than about 40% and 45% phosphatidylcholine) ........................................253
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`Claims 14, 23, 46, and 55 ........................................................................................255
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`(greater than about 4% and 5% ether phospholipids ) ............................................255
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`Claims 7, 8, 9, 15, 16, 19, 24, 25, 28, 40, 41, 42, 47, 48, 51, 56, 57, and 60 .........256
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`(greater than about 200, 300 and 400 mg/kg astaxanthin esters ) ..........................256
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`Claims 10, 17, 20, 26, 43, 49, 52, 58 ......................................................................259
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`(from about 20% to 35% omega-3 fatty acids as a percentage of total fatty acids)
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` ............................................................................................................................259
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`Claims 30, 31, 32, 34, 35, and 36 ............................................................................261
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`(on the ship, heat treatment of freshly caught Euphausia superba) .......................261
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`GROUND 2 ............................................................................................................265
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`BREIVIK II, CATCHPOLE, BOTTINO II, ..........................................................265
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`SAMPALIS I, AND SAMPALIS II ......................................................................265
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`CLAIMS 4 and 39 ..................................................................................................265
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`Claims 4 and 39 .......................................................................................................265
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`(at least 36% omega-3 fatty acids as a percentage of total fatty acids) ..................265
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`GROUND 3 ............................................................................................................268
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`BREIVIK II, CATCHPOLE, BOTTINO II, ..........................................................268
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`SAMPALIS I, AND FRICKE ................................................................................268
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`CLAIMS 11, 18, 21, 27, 44, 50, 53, and 59 ...........................................................268
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`Claims 11, 18, 21, 27, 44, 50, 53, and 59 ...............................................................268
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`(from about 70% to 95% of omega-3 fatty acids are attached to phospholipids) ..268
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`GROUND 4 ............................................................................................................272
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`BREIVIK II, CATCHPOLE, BOTTINO II, ..........................................................272
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`SAMPALIS I, AND RANDOLPH ........................................................................272
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`CLAIMS 13, 22, 29, 45, 54, and 61 .......................................................................272
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`Claims 13, 22, 29, 45, 54, and 61 ............................................................................272
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`(combining with a plant phytonutrient) ..................................................................272
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`CONCLUDING OPINION ....................................................................................277
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`TALLON APPENDIX A .......................................................................................278
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`‘453 PATENT INVALDITY GROUNDS ............................................................278
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`‘453 PATENT CLAIM CHART ...........................................................................279
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`TALLON APPENDIX B……………………………………………………….. 324
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`TALLON APPENDIX C……………………………………………………….. 328
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`I, Dr Stephen J. Tallon, do hereby make the following declaration:
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`AGREEMENT TO PROVIDE EXPERT TESTIMONY
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`1.
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`I have agreed to provide expert testimony in support of Rimfrost AS’s
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`Petition for Inter Partes Review of U.S. Patent No. 9,375,453 B2. My Curriculum
`
`Vitae is attached hereto as Appendix C.
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`2.
`
`I understand that this proceeding involves U.S. Patent No. 9,375,453 B2
`
`(“the ‘453 Patent”) entitled “Methods for Producing Bioeffective Krill Oil
`
`Compositions,” (Exhibit 1001).
`
`3.
`
`I was asked to review and did review the chain of provisional applications
`
`referred to in the ‘453 Patent for disclosures relating to ether phospholipids, a
`
`material requirement of all the claims. I have reviewed each of the Provisional
`
`Applications, Exhibits 1002-1005, to determine which if any provide written
`
`support for any of the claim limitations (elements) of the ‘453 Patent which claim
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`any of the various percentages of ether phospholipids by weight of krill oil. Only
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`one of the Provisional Applications disclose ether phospholipids. In my opinion,
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`none of the ‘446, ‘058 and ‘483 Provisional Applications (Exhibits 1003-1005)
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`mention the term ether phospholipid or otherwise discuss or disclose the presence
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`of ether phospholipids. In my opinion, as discussed below, only the ‘072
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`Application provides any written description regarding any percentage of ether
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`phospholipids by weight of krill oil. The other Provisional Applications, Exhibits
`
`1003-1005, do not disclose or reference the existence of ether phospholipids.
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`4.
`
`I was also asked to review the chain of provisional applications and the
`
`parent patent, the ‘388 Patent, referred to in the ‘453 Patent, relating to the specific
`
`amounts of ether phospholipids as required by the claims of the ‘453 Patent, a
`
`material requirement of all the claims. I have reviewed each of the Provisional
`
`Applications, Exhibits 1002-1005, the ‘388 Patent (Exhibit 1047) and the ‘388 File
`
`History (Exhibit 1024) to determine which if any provide written support for any
`
`of the claim limitations (elements) of the ‘453 Patent which claim various
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`percentages of ether phospholipids by weight of krill oil. In the ‘453 patent claims
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`the upper bounds of the claimed ether phospholipid ranges are not explicitly given,
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`however for all claims except claims 2, 3, 37 and 38, the upper bounds are
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`inherently limited to a maximum of about 33% w/w krill oil because of the ranges
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`of other claimed components that are in the same composition. As for claims 2, 3,
`
`37 and 38, the inherent upper limit is at least 19.7% or 29.2% ether PL w/w krill
`
`oil. See discussion below. Finally, in my opinion, none of the Provisional
`
`Applications, Exhibits 1002-1005, the ‘388 Patent (Exhibit 1047), or the ‘453
`
`Patent itself provide written, enabling, support for, ether phospholipids in amounts,
`10
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`for example, greater than about 8% w/w of said krill oil, and as such, there is no
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`written support for the claimed ranges of ether phospholipid content.
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`5.
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`I have been asked to provide my opinion regarding whether one of ordinary
`
`skill in the art at the relevant time would have understood that certain prior art
`
`references, alone or in combination, disclose or teach each of the elements and
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`limitations recited in the claims of the ‘453 Patent. I have also been asked to
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`provide my opinion regarding whether a person of ordinary skill in the art (a
`
`“POSITA”) would have been motivated or had a rationale or reason to modify or
`
`combine those certain prior art references to arrive at the elements recited in the
`
`claims of the ‘453 Patent. In my opinion, as discussed below, the references
`
`discussed below disclose or teach each of the elements and limitations recited in
`
`the claims of the ‘453 Patent and a POSITA would have had a strong rationale to
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`combine them.
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`BASES FOR OPINIONS GIVEN
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`6.
`
`In forming my opinion, I have relied on my own education, work
`
`experiences and knowledge and my review of the following documents:
`
`EXHIBIT NO.
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`EXHIBIT DESCRIPTION
`
`1001
`
`
`
`U.S. Patent No. 9,375,453 B2, filed September 6, 2013 (‘453).
`
`1002
`
`
`1003
`
`
`1004
`
`
`1005
`
`
`1007
`
`
`1008
`
`
`1009
`
`
`1010
`
`
`
`
`
`
`U.S. Provisional Patent Application No. 61/024,072, filed
`January 28, 2008 (‘072 Provisional).
`
`U.S. Provisional Patent Application No. 60/983,446, filed
`October 29, 2007 (‘446 Provisional).
`
`U.S. Provisional Patent Application No. 60/975,058, filed
`September 25, 2007 (‘058 Provisional).
`
`U.S. Provisional Patent Application No. 60/920,483, filed March
`28, 2007 (‘483 Provisional).
`
`Bottino, N.R., “The Fatty Acids of Antarctic Phytoplankton and
`Euphausiids. Fatty Acid Exchange among Trophic Levels of the
`Ross Sea,” 1974, Marine Biology, 27, 197-204 (Bottino I).
`
`Budziński, E., P. Bykowski and D. Dutkiewicz, 1985,
`Possibilities of processing and marketing of products made from
`Antarctic krill. FAO Fish.Tech. Pap., (268):46, (Budzinski).
`
`Catchpole and Tallon, WO 2007/123424, published November
`1, 2007, “Process for Separating Lipid Materials,” (Catchpole).
`
`Fricke et al., “Lipid, Sterol and Fatty Acid Composition of
`Antarctic Krill (Euphausia superba Dana),” LIPIDS 19(11):821-
`827 (1984) (Fricke).
`
`12
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`1011
`
`
`1012
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`
`1013
`
`
`1014
`
`
`1015
`
`
`1017
`
`
`1018
`
`
`1020
`
`
`1024
`
`
`
`
`Randolph, et al., U.S. Patent Application Publication No.
`US/2005/0058728 A1, “Cytokine Modulators and Related
`Method of Use” (Randolph).
`
`Sampalis [I] et al., “Evaluation of the Effects of Neptune Krill
`Oil™ on the Management of Premenstrual Syndrome and
`Dysmenorrhea” Altern. Med. Rev. 8(2):171-179
`(2003)
`(Sampalis I).
`
`Sampalis [II] et al.,WO 2003/011873, published February 13,
`2003, “Natural Marine Source Phospholipids Comprising
`Flavonoids, Polyunsaturated Fatty Acids
`and Their
`Applications” (Sampalis II).
`
`Tanaka [I] et al., “Platelet – Activating Factor (PAF) – Like
`Phospholipids
`Formed
`During
`Peroxidation
`of
`Phosphatidylcholines
`from Different Foodstuffs”, Biosci.
`Biotech. Biochem., 59(8) 1389-1393 (1995) (Tanaka I).
`
`Tanaka (II) et al., “Extraction of Phospholipids from Salmon Roe
`with Supercritical Carbon Dioxide and an Entrainer”, Journal of
`Oleo Science Vol. 53 (2004) No. 9, p.17-424 (Tanaka II).
`
`Folch et al., “A simple method for the isolation and purification
`of total lipides from animal tissues”, J. Biol. Chem. (1957) 226:
`497-509 (Folch).
`
`to Improving
`Kochian et al, “Agricultural Approaches
`Phytonutrient Content in Plants: An Overview”, Nutrition
`Reviews, Vol. 57, No. 9, September 1999: S13-S18.
`
`Bunea, et al., “Evaluation Of The Effects Of Neptune Krill Oil
`On The Clinical Course Of Hyperlipidemia”, Altern Med Rev.
`2004; 9:420–428 (Bunea).
`
`File History to U.S. Patent No. 9,034,388 B2, Serial No,
`12/057,775 (‘388 File History)
`13
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`1027
`
`
`1028
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`
`1030
`
`
`1031
`
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`1032
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`
`
`1033
`
`
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`
`
`
`1024 Part 1 - Pages 1-450
`1024 Part 2 - Pages 451-900
`1024 Part 3 - Pages 901-1350
`1024 Part 4 - Pages 1351-1800
`1024 Part 5A - Pages 1801-2025
`1024 Part 5B - Pages 2026-2250
`1024 Part 6 - Pages 2251-2700
`1024 Part 7 - Pages 2701-3083
`1024 Part 8 - Pages 3084-3223.
`
`Saether et al., “Lipolysis post mortem in North Atlantic krill”.
`Comp. Biochem. Physiol. Vol. 83B, No. 1, pp. 51-55, 1986
`(Saether).
`
`
`
`
`
`Hawley’s Condensed Chemical Dictionary, p. 893, 13th ed.,1997
`(Hawley’s).
`
`Tehoharides, U.S. Patent Application Publication No.
`US/2006/0013905 A1, “Anti-Inflammatory Compositions For
`Treating Multiple Sclerosis” (Tehoharides).
`
`to Develop
`“Neptune-Degussa Deal
`Jess,
`Halliday,
`Phospholipids, Adapt Krill Oil,” http://www.nutraingredients-
`usa.com/Suppliers2/Neptune-Degussa-deal-to-develop-
`phospholipids-adapt-krill-oil, December 12, 2005 (Neptune-
`DeGussa).
`
`Grantham, G.J., “The Utilization Of Krill”, UNDP/FAO
`Southern Ocean Fisheries Survey Programme
`(Grantham).
`
`(1977)
`
`Yoshitomi, U.S. Patent Application Publication No.
`US/2003/0113432 A1, “Process For Making Dried Powdery and
`Granular Krill” (Yoshitomi).
`
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`1035
`
`
`1036
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`
`1037
`
`
`1038
`
`
`1039
`
`
`1043
`
`
`1047
`
`1048
`
`
`
`
`
`
`Breivik, U.S. Patent Application Publication No. US
`2010/0143571 A1, “Process for Production of Omega-3 Rich
`Marine Phospholipids from Krill” (Breivik I).
`
`Breivik, U.S. Provisional Patent Application No. 60/859,289,
`“Processes for production of omega-3 rich marine phospholipids
`from krill”, filed November 16, 2006 (Breivik ‘289 Provisional,
`Breivik III).
`
`Breivik, WO 2008/060163 A1, “Process for Production of
`Omega-3 Rich Marine Phospholipids from Krill,” International
`filing date November 15, 2007 (Breivik II).
`
`Bottino, N.R., “Lipid Composition of Two Species of Antarctic
`Krill: Euphausia Superba and E. Crystallorophias”, Comp.
`Biochem. Physiol., 1975, Vol. 50B, pp. 479 to 484 (Bottino II).
`
`Grynbaum, M., et al. “Unambiguous detection of astaxanthin
`and astaxanthin fatty acid esters in krill (Euphausia superba
`Dana)”, J. Sep. Sci., 28, 1685–1693 (2005).
`
`Bruheim, U.S. Patent Application Publication No.
`US2008/0274203 A1, published November 6, 2008 (this is the
`publication of patent application serial no. 12/057,775 which
`issued as U.S. Patent No. of 9,034,388).
`
`U.S. Patent No. 9,034,388 B2, filed May 28, 2008 (‘388 Patent).
`
`Enzymotec, GRAS Notice No. GRN 000226 for “Krill-based
`Lecithin
`in
`Food”
`and
`“Krill-derived
`lecithin”
`https://www.fda.gov/downloads/Food/Ingredients
`PackagingLabeling/GRAS/NoticeInventory/ucm263930.pdf,
`dated May 26, 2007 and filed by the FDA May 31, 2007, see
`Exhibit 1049 (Enzymotec).
`
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`1049
`
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`1055
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`
`
`1059
`
`
`1063
`
`
`
`
`
`
`1069
`
`1070
`
`
`1071
`
`
`
`
`FDA, Agency Response Letter GRAS Notice No. GRN 000226,
`https://www.fda.gov/Food/IngredientsPackagingLabeling/GRA
`S/NoticeInventory/ucm153881.htm, January 3, 2008.
`
`File History to U.S. Patent No. 9,375,453 B2, Serial No,
`14/020,162 (‘453 File History)
`
`1055 Part 1 - Pages 1-400
`1055 Part 2 - Pages 401-800
`1055 Part 3 - Pages 801-1109.
`
`Markman Order (Public Version), Order 13, U.S. International
`Trade Commission, In the Matter of Certain Krill Oil Products
`and Krill Meal for Production of Krill Oil Products, Inv. No.
`337-TA-1019, dated April 13, 2017.
`
`File History to U.S. Patent No. 9,644,170 B2, Serial No,
`15/180,439 (‘170 File History)
`
`1063 Part 1 - Pages 1-400
`1063 Part 2 - Pages 401-800
`1063 Part 3 – Pages 801-1107.
`
`Krill Bill Bottle and Capsules from IRL.
`
`Krill Bill Online Purchase Order and Specification Pages from
`2006
`(https://web.archive.org/web/20060715103715/http://www.krill
`bill.com:80/purchase.htm;
`https://web.archive.org/web/20060715103809/http://www.krillb
`ill.com/profile.htm).
`
`Antarctica Select Krill Oil Online Literature and Purchase Order
`Form
`and
`linked
`FDA webpage
`from
`2006
`(https://web.archive.org/web/20060816050841/http://www.aqu
`asourceproducts.com:80/store/;
`
`16
`
`RIMFROST EXHIBIT 1006 Page 0016
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`U.S. Patent No. 9,375,453 B2
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`https://web.archive.org/web/20060816051010/http://www.aqua
`sourceproducts.com:80/krill_oil.html;
`https://web.archive.org/web/20060506115548/
`http://www.aquasourceproducts.com:80/resources.html?osCsid
`=aee4bb3df08470be3a75bc598448dabc;
`https://web.archive.org/web/20060513152744/http://vm.cfsan.f
`da.gov/~dms/ds-oview.html).
`
`Chen, U.S. Patent Application Publication No. US
`2008/0021000 A1, for “Mixtures of and Methods of Use for
`Polyunsaturated Fatty Acid-Containing Phospholipids and Alkyl
`Ether Phospholipids Species”, filing date July 19, 2006,
`publication date January 24, 2008.
`
`Neptune, GRAS Notice [No. GRN 000242] for “High
`Phospholipid Krill Oil”
`https://www.fda.gov/downloads/Food/IngredientsPackagingLab
`eling/GRAS/NoticeInventory/ucm269133.pdf, dated January
`18, 2008 and filed by the FDA February 4, 2008 (Neptune
`GRAS).
`
`Affidavit of Christopher Butler, Office Manager of Internet
`Archive, dated November 8, 2017, for Rimfrost Exhibits 1070
`and 1071, regarding Krill Bill, Aquasource and FDA related
`webpages from 2006.
`
`Mayzaud et al, “Changes in lipid composition of the Antarctic
`krill Euphausia superba in the Indian sector of the Antarctic
`Ocean: influence of geographical location, sexual maturity stage
`and distribution among organs” Marine Ecology Progress
`Series, Vol. 173: 149-162 (1998) (Mayzaud).
`
`Aker GRAS [No. GRN 000371], “Notification of GRAS
`Determination
`of Krill Oil”, December
`14,
`2010.
`https://www.accessdata.fda.gov/scripts/fdcc/index.cfm?set=GR
`ASNotices&id=371.
`
`17
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`RIMFROST EXHIBIT 1006 Page 0017
`
`
`1072
`
`
`1075
`
`
`1076
`
`
`1084
`
`1089
`
`
`
`
`
`
`
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`
`1093
`
`1094
`
`
`1095
`
`
`1097
`
`
`1098
`
`
`1099
`
`
`1100
`
`
`1101
`
`
`1102
`
`
`
`
`
`
`U.S. Patent No. 9,644,170 B2, filed June 13, 2016 (‘170).
`
`Marathe, et al., Inflammatory Platelet-activating Factor-like
`Phospholipids in Oxidized Low Density Lipoproteins Are
`Fragmented Alkyl Phosphatidylcholines, J Biol Chem. 1999 Oct
`1;274(40):28395-28404.
`
`Stremler, et al., Human Plasma Platelet-activating Factor
`Acetylhydrolase - Oxidatively Fragmented Phospholipids As
`Substrates, (1991) J. Biol. Chem. 266, 11095–11103.
`
`Britton, G., Structure and properties of carotenoids in relation
`to function, FASEB J, 9, 1551-1558,1995.
`
`Yuan, “Characteristics and chromatographic separation of
`astaxanthin and its esters from the microalga Haematococcus
`pluvialos,” Doctoral Thesis, The University of Hong Kong, 1999
`(http://dx.doi.org/10.5353/th_b3123971).
`
`Mimoun-Benarroch, et al., The Bioavailability of Astaxanthin is
`Dependent on both the Source and the Isomeric Variants of the
`molecule, Bulletin of University of Agricultural Sciences and
`Veterinary Medicine Cluj-Napoca: Food Science and
`Technology, Volume 73, Number 2, 2016, pp. 61-69(9).
`
`Higuera-Ciapara, et al., Astaxanthin: A Review of its Chemistry
`and Applications, Crit Rev Food Sci Nutr. 2006;46(2):185-96.
`
`Lambertsen, et al., Method of Analysis of Astaxanthin and its
`Occurrence in some Marine Products, J. Sci. of Food and
`Agriculture, 1971, Vol. 22, February.
`
`Foss, et al., Natural occurrence of enantiomeric and Meso
`
`astaxanthin 7∗-crustaceans including zooplankton, Comparative
`
`and Physiology Part B: Comparative
`Biochemistry
`Biochemistry, Volume 86, Issue 2, 1987, Pages 313-314.
`
`
`18
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`NO FINANCIAL INTEREST IN PROCEEDING
`
`7.
`
`For my work related to this Inter Partes Review, my employer, Callaghan
`
`Innovation, receives compensation for my time. I am not directly compensated by
`
`either Hoffmann and Baron, LLP or the Petitioner. I have no financial interest in
`
`this proceeding, and the potential for any future financial benefit is unaffected by
`
`the content of my testimony or the outcome of this proceeding. My compensation
`
`from my employer, Callaghan Innovation, is not in any way related to the outcome
`
`of the case.
`
`QUALIFICATIONS AND RELEVANT EXPERIENCE
`
`8.
`
`I am currently employed as Team Manager of the Processing Team within
`
`the Integrated Bioactive Technologies Group of Callaghan Innovation, at the
`
`Gracefield Research Centre in Lower Hutt, New Zealand (an agency of the
`
`Government of New Zealand). The Integrated Bioactive Technologies group
`
`specializes in near to market research and development in the field of processing of
`
`biologically-derived raw materials to make high value nutraceuticals, food
`
`ingredients and biopharmaceuticals. My research and expertise has helped to
`
`enable a number of industries in New Zealand to make such products, including a
`
`
`
`
`19
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`range of plant and marine derived extracts, including lipid extracts that are
`
`produced using a supercritical fluid extraction process.
`
`9.
`
`Consequently, I have knowledge and expertise regarding methods of making
`
`or extracting oils from crustaceans such as krill, including lipid oils, and of their
`
`composition, including various extraction methods involving the use of
`
`supercritical fluids both with, and without, polar solvents; and the polar solvent
`
`extraction of marine biomasses to achieve the same aims. These methods are now
`
`a matter of public knowledge. See my CV attached Appendix C.
`
`10.
`
`I began developing supercritical CO2 + polar co-solvent extraction and
`
`fractionation processes around 2003 with my colleague Dr Catchpole, and applied
`
`them to biomasses containing phospholipids around 2004, and in particular to
`
`marine and dairy biomasses. Around this time, I also investigated the use of
`
`dimethyl ether (DME) for extracting phospholipids, again mainly from marine and
`
`dairy biomasses.
`
`11. Around this time, 2003-2004, Dr Andrew Mackenzie, also part of the
`
`Integrated Bioactive Technologies group, developed an NMR-based method for
`
`analyzing and quantifying phospholipids, based on the 31P isotope. This analysis
`
`method was able to distinguish between very closely related phospholipids, such as
`
`phosphatidylcholine (PC) and its ether-lipid analogue
`20
`
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`alkylacylphosphatidylcholine (AAPC); and phosphatidylethanolamine (PE) and its
`
`ether analogues phosphatidylethanolamine plasmalogen and
`
`alkylacylphosphatidylethanolamine (AAPE).
`
`12. Prior to the use of 31P NMR to determine the ether phospholipid content of
`
`phospholipid lipids, and though other methods for analyzing same were available,
`
`it was common industry practice to report only the total phospholipid content for
`
`the phosphatidylcholine (PC) and phosphatidylethanolamine (PE) lipid
`
`components. Thus, when the amount of the PC lipid component was reported, the
`
`number reported included not only PC, but its ether-lipid analogue
`
`alkylacylphosphatidylcholine (AAPC). The total then reported being the sum of the
`
`non-ether phospholipids and ether phospholipids. In a like manner, when the
`
`amount of the phosphatidylethanolamine (PE) component was reported, the
`
`number reported included not only PE, but its ether analogues
`
`phosphatidylethanolamine plasmalogen (PE plasmalogen) and
`
`alkylacylphosphatidylethanolamine (AAPE) as well.
`
`13. When the industry began to accept the 31P NMR standard for the first time
`
`the ether-phospholipid components started to be consistently reported as separate
`
`constituents.
`
`
`
`
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`14.
`
`In 2006 the Integrated Bioactive Technologies group of Callaghan
`
`Innovation (of which I am a part), began to work collaboratively with Nutrizeal
`
`Ltd (found
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