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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
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`Petitioner
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`v.
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`AKER BIOMARINE ANTARCTIC AS
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`Patent Owner
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`_______________________
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`Case: IPR2018-01730
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`U.S. Patent No. 9,072,752 B1
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`_______________________
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`
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`DECLARATION OF DR STEPHEN J. TALLON
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`U.S. Patent No. 9,072,752 B1
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`TABLE OF CONTENTS
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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 (EXHIBITS) .....................................................12
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`NO FINANCIAL INTEREST IN PROCEEDING ..................................................20
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`QUALIFICATIONS AND RELEVANT EXPERIENCE .......................................20
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`RELEVANT CONSIDERATIONS .........................................................................27
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`CHART I - ‘752 FAMILY CHART .........................................................................31
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`LEVEL OF ORDINARY SKILL IN THE ART & THE POSITA .........................32
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`THE ‘752 PATENT (EXHIBIT 1001) ....................................................................33
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`Priority Claims ..........................................................................................................33
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`‘752 Disclosure .........................................................................................................34
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`Examples 7 and 8 do not rely on the source or processing of the krill in the
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`extraction of krill oil. ...........................................................................................36
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`The ‘752 Patent Claims Summary. ...........................................................................37
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`THE ‘752 PATENT IS ENTITLED TO A PRIORITY ..........................................39
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`DATE NO EARLIER THAN FEBRUARY 12, 2015 .............................................39
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`Ratio of ether PL to PL and AAPC/PC is fairly constant and would require undue
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`experimentation to achieve 55-60% ether PL. .....................................................42
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`Highest ether PL content reported in ‘752 Patent is less than 8%. ...........................44
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`THE ‘752 PATENT IS ENTITLED TO A PRIORITY ..........................................48
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`MOTIVATION TO COMBINE - OVERVIEW .....................................................49
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`CHART II - SEVERAL KRILL COMPONENTS KNOWN TO A POSITA .........59
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`COMPARED WITH ‘752 PATENT EXAMPLE 7* ...............................................59
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`The limited association of certain degraded ether PLs with PAF and PAF-Like
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`Activity does not affect the motivations a POSITA would have had to combine
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`the references discussed herein. ...........................................................................64
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`PAF would not have been a concern to a POSITA extracting PL from krill. ..........67
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`CLAIM TERMS ......................................................................................................78
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`ITC Claim Construction. ...........................................................................................78
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`“krill oil” means “lipids extracted from krill” ..........................................................82
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`“polar krill oil” means “krill oil containing polar lipids” .........................................88
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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: .....................................91
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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.” ........................................................................97
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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” .......................98
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`PRIOR ART ...........................................................................................................102
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`Bottino I (Exhibit 1007) ..........................................................................................102
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`Bottino II (Exhibit 1038) .........................................................................................105
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`Breivik II (Exhibit 1037), Breivik I (Exhibit 1035) and Breivik III (Exhibit 1036)
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` ............................................................................................................................108
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`Catchpole (Exhibit 1009) ........................................................................................125
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`Enzymotec (Exhibit 1048, GRAS Notice No. GRN 000226) ................................138
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`Fricke (Exhibit 1010) ..............................................................................................149
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`Fricke 1984 analysis of omega-3 fatty acids .......................................................158
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`Randolph (Exhibit 1011) .........................................................................................163
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`Sampalis I (Exhibit 1012) .......................................................................................168
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`Sampalis II (Exhibit 1013) ......................................................................................172
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`Tanaka I (Exhibit 1014) ..........................................................................................183
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`Tanaka II (Exhibit 1015) .........................................................................................186
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`Budziński (Exhibit 1008) ........................................................................................190
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`Bunea (Exhibit 1020) ..............................................................................................196
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`Grantham (Exhibit 1032) ........................................................................................199
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`Grynbaum (Exhibit 1039) .......................................................................................206
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`Yoshitomi (Exhibit 1033) .......................................................................................215
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`Mayzaud (Exhibit 1084) .........................................................................................222
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`Neptune Krill Oil (NKO) and Krill Bill NKO (Exhibit 1070, et. al) ......................224
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`Britton (Exhibit 1097) – trans (all-E) form of astaxanthin predominates in nature
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` ............................................................................................................................229
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`Yuan (Exhibit 1098) ................................................................................................232
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`Foss (Exhibit 1102) .................................................................................................234
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`Higuera-Ciapara (Exhibit 1100) ..............................................................................236
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`Lambertsen (Exhibit 1101) .....................................................................................240
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`Tehoharides (Exhibit 1030).....................................................................................241
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`Hoem Presentation (Exhibit 1080) ..........................................................................242
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`THE ‘752 PATENT CLAIM CHART ...................................................................246
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`‘752 PETITION GROUNDS ...............................................................................247
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`GROUND 1 ............................................................................................................248
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`CATCHPOLE ........................................................................................................248
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`CLAIMS 1, 5-6 and 11 ..........................................................................................248
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`GROUND 2 ............................................................................................................251
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`CATCHPOLE and SAMPALIS II .........................................................................251
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`CLAIMS 4, 7 and 12-13 ........................................................................................251
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`Claim 4. ...................................................................................................................251
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`Claim 7. ...................................................................................................................251
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`Claim 12. .................................................................................................................252
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`Claim 13. .................................................................................................................253
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`GROUND 3 ............................................................................................................255
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`CATCHPOLE, GRYNBAUM AND RANDOLPH ..............................................255
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`CLAIMS 8-10 ........................................................................................................255
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`GROUND 4 ............................................................................................................260
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`CATCHPOLE AND ENZYMOTEC .....................................................................260
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`CLAIMS 1-3, 5-6 and 11 .......................................................................................260
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`Claims 1-2. ..............................................................................................................260
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`Claim 3. ...................................................................................................................261
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`Claims 5 and 6. ........................................................................................................262
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`Claim 11. .................................................................................................................263
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`GROUND 5 ............................................................................................................267
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`CATCHPOLE, ENZYMOTEC AND SAMPALIS II ...........................................267
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`CLAIMS 14-16 and 20 ..........................................................................................267
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`Claim 14 ..................................................................................................................267
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`Claims 15 and 16. ....................................................................................................270
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`Claim 20. .................................................................................................................272
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`GROUND 6 ............................................................................................................276
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`CATCHPOLE, ENZYMOTEC, ............................................................................276
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`SAMPALIS II, GRYNBAUM AND RANDOLPH ..............................................276
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`CLAIMS 17-19 ......................................................................................................276
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`CONCLUDING OPINION ....................................................................................282
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`TALLON APPENDIX A .......................................................................................283
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`‘752 PATENT INVALDITY GROUNDS ............................................................283
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`‘752 PATENT CLAIM CHART ...........................................................................284
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`TALLON APPENDIX B ………………………………………………………. 302
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`TALLON APPENDIX C ………………………………………………………. 306
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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. 9,072,752 B1. My Curriculum
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`Vitae is attached hereto as Appendix C.
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`2.
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`I understand that this proceeding involves U.S. Patent No. 9,072,752 B1
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`(“the ‘752 Patent”) entitled “Bioeffective Krill Oil Compositions,” (Exhibit 1001).
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`3.
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`I was asked to review and did review the chain of provisional applications
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`referred to in the ‘752 Patent (Exhibits 1002-1005) for disclosures relating to ether
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`phospholipids (ether PL), a material requirement of all the claims. I have reviewed
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`each of the Provisional Applications, Exhibits 1002-1005, to determine which if
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`any provide written support for any of the claim limitations (elements) of the ‘752
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`Patent which claim any of the various percentages of ether phospholipids by
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`weight of krill oil. Only one of the Provisional Applications disclose ether
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`phospholipids. In my opinion, none of the ‘446, ‘058 and ‘483 Provisional
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`Applications (Exhibits 1003-1005) mention the term ether phospholipid or
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`otherwise discuss or disclose the presence of ether phospholipids. In my opinion,
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`as discussed below, only the ‘072 Application provides any written description
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`regarding any percentage of ether phospholipids by weight of krill oil. The other
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`Provisional Applications, Exhibits 1003-1005, do not disclose or reference the
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`existence of ether phospholipids.
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`4.
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`I was also asked to review the chain of provisional applications and the
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`parent patent, the ‘388 Patent, referred to in the ‘752 Patent, relating to the specific
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`amounts of ether phospholipids as required by the claims of the ‘752 Patent, a
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`material requirement of all the claims. I have reviewed each of the Provisional
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`Applications, Exhibits 1002-1005, the ‘388 Patent (Exhibit 1047) and the ‘388 File
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`History (Exhibit 1024) to determine which if any provide written support for any
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`of the claim limitations (elements) of the ‘752 Patent which claim various
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`percentages of ether phospholipids by weight of krill oil.
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`5.
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`In the ‘752 patent claims, the upper bounds of the claimed ether
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`phospholipid ranges are not explicitly given. For example, claim 1 states: “1. A
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`polar krill oil comprising greater than about 40% phosphatidylcholine w/w of said
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`krill oil and greater than about 5% ether phospholipids w/w of said krill oil.” Thus,
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`the upper limit for ether PL content is 60% w/w krill oil (100%-40%). Other
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`components may reduce that upper limit for ether PL to 55%. It is my opinion
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`explained below that none of the Provisional Applications, Exhibits 1002-1005, the
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`‘388 Patent (Exhibit 1047), or the ‘752 Patent itself provide written, enabling,
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`support for, ether phospholipids in amounts approaching 55% to 60% w/w of said
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`krill oil, and as such, there is no written support for the claimed ranges of ether
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`phospholipid content.
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`6.
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`I have been asked to provide my opinion regarding whether one of ordinary
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`skill in the art at the relevant time would have understood that certain prior art
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`references, alone or in combination, disclose or teach each of the elements and
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`limitations recited in the claims of the ‘752 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
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`“POSITA”) would have been motivated or had a rationale or reason to modify or
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`combine those certain prior art references to arrive at the elements recited in the
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`claims of the ‘752 Patent. In my opinion, as discussed below, the references
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`discussed below disclose or teach each of the elements and limitations recited in
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`the claims of the ‘752 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 (EXHIBITS)
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`7.
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`In forming my opinion, I have relied on my own education, work
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`experiences and knowledge and my review of the following documents:
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`EXHIBIT NO.
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`EXHIBIT DESCRIPTION
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`1001
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`U.S. Patent No. 9,072,752 B1, filed February 12, 2015 (‘752)
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`1002
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`1003
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`1004
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`1005
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`1007
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`1008
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`1009
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`1010
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`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)
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`
`1011
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`1012
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`1013
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`1014
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`1015
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`
`1017
`
`
`1020
`
`
`1024
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`
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`
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`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).
`
`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)
`1024 Part 1 - Pages 1-450
`1024 Part 2 - Pages 451-900
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`1030
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`1032
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`1033
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`1035
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`1036
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`1037
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`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
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`
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`
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`Tehoharides, U.S. Patent Application Publication No.
`US/2006/0013905 A1, “Anti-Inflammatory Compositions For
`Treating Multiple Sclerosis” (Tehoharides)
`
`Grantham, G.J., “The Utilization Of Krill”, UNDP/FAO
`Southern Ocean Fisheries Survey Programme (1977)
`(Grantham).
`
`Yoshitomi, U.S. Patent Application Publication No.
`US/2003/0113432 A1, “Process For Making Dried Powdery
`and Granular Krill” (Yoshitomi).
`
`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).
`
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`1038
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`1039
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`1040
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`1043
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`1044
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`1045
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`1047
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`1048
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`1049
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`1050
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`
`
`
`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).
`
`File History to U.S. Patent No. 9,072,752 B1, Serial No,
`14/620,784 (‘752 File History).
`
`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).
`
`Declaration of Robert S. McQuate.
`
`Declaration of Rakesh Kapoor.
`
`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).
`
`FDA, Agency Response Letter GRAS Notice No. GRN 000226,
`https://www.fda.gov/Food/IngredientsPackagingLabeling/GRA
`S/NoticeInventory/ucm153881.htm, January 3, 2008.
`
`Gaynor, P, “How U.S. FDA's GRAS Notification Program
`Works”, Reprinted with permission of the publishers from Food
`Safety Magazine December 2005/January 2006.
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`1051
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`1052
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`1059
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`1060
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`1061
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`1062
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`1063
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`http://www.fda.gov/Food/IngredientsPackagingLabeling/GRAS
`/ucm083022.htm
`
`Federal Register, Vol. 62, No. 74, pp. 18938-18964, April 17,
`1997.
`
`FDA GRAS Notices, August 05, 2007, listing GRN 226 on
`Internet, “Krill-derived lecithin,” Wayback Machine,
`https://web.archive.org/web/20070805011458/http://www.cfsan
`.fda.gov:80/~rdb/opa-gras.html.
`
`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
`
`Enzymotec website pages (September 25, 2007)
`(https://web.archive.org/web/20070925024350/http://www.enz
`ymotec.com/PageIndex.asp?cc=01020403)
`(https://web.archive.org/web/20070925024521/http://www.enz
`ymotec.com/Page.asp?cc=01020408)
`
`Affidavit of Christopher Butler, Office Manager of Internet
`Archive dated August 22, 2017 regarding FDA GRAS Notices
`and Enzymotec related webpages.
`
`FDA, Freedom of Information Annual Report 2007,
`https://www.fda.gov/RegulatoryInformation/FOI/FOIAAnnual
`Reports/ucm148025.htm.
`
`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
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`1069
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`1070
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`1071
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`1072
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`1075
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`U.S. Patent No. 9,375,453 B2, filed September 6, 2013 (‘453).
`
`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/;
`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).
`
`17
`
`RIMFROST EXHIBIT 1006 Page 0017
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`IPR2018-01730
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`U.S. Patent No. 9,072,752 B1
`
`1076
`
`
`1077
`
`
`1080
`
`
`1084
`
`1089
`
`
`1091
`
`1092
`
`
`
`
`1093
`
`1094
`
`
`
`
`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.
`
`Pure Encapsulations online literature for its Krill-plex NKO™
`product, webpage from August 19, 2004.
`https://web.archive.org/web/20040819183137/www.purecaps.c
`om/itemdy00.asp?T1=KP1.
`
`Hoem, N., “Composition of Antarctic krill oil and methods for
`its harvesting, production and qualitative and quantitative
`analysis”, Aker BioMarine, Newcastle Australia November
`2013 (Hoem).
`
`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
`
`Neptune GRAS Agency Response Letter GRN 000242.
`
`Affidavit of Christopher Butler, Office Manager of Internet
`Archive, dated February 5, 2018, regarding Rimfrost
`Exhibit 1077, Pure Encapsulations online literature for its Krill-
`plex NKO™ product, webpage from August 19, 2004.
`
`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
`18
`
`RIMFROST EXHIBIT 1006 Page 0018
`
`
`
`IPR2018-01730
`
`
`
`
`U.S. Patent No. 9,072,752 B1
`
`
`1095
`
`
`1097
`
`
`1098
`
`
`1099
`
`
`1100
`
`
`1101
`
`
`1102
`
`
`
`
`
`
`
`
`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 Biochemistry and Physiology Part B:
`Comparative Biochemistry, Volume 86, Issue 2, 1987, Pages
`313-314.
`
`
`
`19
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`RIMFROST EXHIBIT 1006 Page 0019
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`NO FINANCIAL INTEREST IN PROCEEDING
`
`8.
`
`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
`
`9.
`
`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
`
`
`
`
`20
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`RIMFROST EXHIBIT 1006 Page 0020
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`IPR2018-01730
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`U.S. Patent No. 9,072,752 B1
`
`range of plant and marine derived extracts, including lipid extracts that are
`
`produced using a supercritical fluid extraction process.
`
`10. 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
`
`and were to a POSITA (see POSITA discussion below) a matter of public
`
`knowledge. My CV is attached as Appendix C.
`
`11.
`
`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.
`
`12. 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
`21
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`RIMFROST EXHIBIT 1006 Page 0021
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`U.S. Patent No. 9,072,752 B1
`
`phosphatidylcholine (PC) and its ether-lipid analogue
`
`alkylacylphosphatidylcholine (AAPC); and phosphatidylethanolamine (PE) and its
`
`ether analogues phosphatidylethanolamine plasmalogen and
`
`alkylacylphosphatidylethanolamine (AAPE).
`
`13. 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 phospholip
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