`
`
`UNITED STATES PATENT AND TRADEMARK OFFICE
`____________
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`____________
`
`RIMFROST AS,
`Petitioner,
`
`v.
`
`AKER BIOMARINE ANTARCTIC AS,
`Patent Owner.
`____________
`
`Cases:
`IPR2017-00745 (Patent 9,078,905 B2)
`IPR2017-00746 (Patent 9,028,877 B2)
`IPR2017-00747 (Patent 9,078,905 B2)
`IPR2017-00748 (Patent 9,028,877 B2)
`____________
`
`Record of Oral Hearing
`Held: April 24, 2018
`____________
`
`
`
`
`Before LORA M. GREEN, ERICA A. FRANKLIN, and JACQUELINE T.
`HARLOW, Administrative Patent Judges.
`
`
`
`
`
`
`
`IPR2017-00745 (Patent 9,078,905 B2)
`IPR2017-00746 (Patent 9,028,877 B2)
`IPR2017-00747 (Patent 9,078,905 B2)
`IPR2017-00748 (Patent 9,028,877 B2)
`
`
`
`APPEARANCES:
`
`ON BEHALF OF THE PETITIONER:
`
`
`JAMES F. HARRINGTON, ESQ.
`Hoffman & Baron LLP
`6900 Jericho Turnpike
`Syosset, New York 11791-4407
`
`and
`
`MICHAEL I. CHAKANSKY, ESQ.
`Hoffman & Baron LLP
`6 Campus Drive
`Parsippany, New Jersey 07054-4406
`
`
`ON BEHALF OF THE PATENT OWNER:
`
`
`DAVID A. CASIMIR, J.D., Ph.D.
`J. MITCHELL JONES, J.D., Ph.D.
`Casimir Jones
`2275 Eming Way, Suite 310
`Middleton, Wisconsin 53562
`
`
`
`
`The above-entitled matter came on for hearing on Tuesday, April 24,
`
`2018, commencing at 1:00 p.m., at the U.S. Patent and Trademark Office,
`600 Dulany Street, Alexandria, Virginia.
`
`
`
`
`2
`
`
`
`IPR2017-00745 (Patent 9,078,905 B2)
`IPR2017-00746 (Patent 9,028,877 B2)
`IPR2017-00747 (Patent 9,078,905 B2)
`IPR2017-00748 (Patent 9,028,877 B2)
`
`
`P R O C E E D I N G S
`- - - - -
`JUDGE GREEN: Please be seated. Let me know when you're
`
`ready.
`
`Good afternoon, everybody. We are on the record. Please make
`sure that all cell phones are turned off, as they can interfere with the
`microphones.
`This is the final oral hearing in IPR 2017-00745, -00746, -00747,
`and -00748. Judge Franklin is in the hearing room with us, she is on my
`right; and Judge Harlow is attending remotely from Denver.
`At this time, we would like counsel to introduce yourselves and
`your colleagues, beginning with Petitioner.
`MR. HARRINGTON: Yes, James Harrington, lead counsel for
`Petitioner Rimfrost AS. I am here with my partner, Michael --
`JUDGE HARLOW: Counsel, I'm sorry. I believe your
`microphone is off, and I cannot hear you in Denver.
`JUDGE GREEN: Is the green light on?
`(Pause in the proceedings.)
`JUDGE GREEN: You can start over again, Mr. Harrington.
`MR. HARRINGTON: Okay, James Harrington, lead counsel for
`Petitioner Rimfrost AS --
`JUDGE HARLOW: I'm sorry, Mr. Harrington. The sound is gone
`
`again.
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`(Pause in the proceedings.)
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`IPR2017-00745 (Patent 9,078,905 B2)
`IPR2017-00746 (Patent 9,028,877 B2)
`IPR2017-00747 (Patent 9,078,905 B2)
`IPR2017-00748 (Patent 9,028,877 B2)
`
`
`MR. HARRINGTON: Judge Harrington, lead counsel for
`Petitioner Rimfrost AS. I am here with my partner Michael Chakansky, first
`backup counsel.
`JUDGE GREEN: Okay, thank you.
`And Patent Owner?
`MR. CASIMIR: David Casimir, lead counsel for Aker Biomarine,
`with John Mitchell Jones, my co-counsel.
`JUDGE GREEN: Okay, thank you. Welcome to the Board.
`Consistent with our previous order, Patent Owner and Petitioner
`each have 60 minutes to present their arguments. Petitioner will proceed
`first to present its case in chief as to the challenged claims and may reserve
`rebuttal time to respond to the arguments made by Patent Owner.
`Thereafter, Patent Owner will respond to Petitioner's case.
`As Judge Harlow is attending remotely, the parties are reminded to
`identify which slide they are on or, if you are using the record, to identify
`where in the record you are, in order to allow Judge Harlow to follow along.
`The parties are also reminded that, as we stated in our order,
`demonstratives are only an aid to oral hearing and not evidence of record.
`Counsel for Petitioner, you may proceed. How much time would
`you like to reserve for rebuttal?
`MR. HARRINGTON: I'd like to reserve 20 minutes, if I could.
`JUDGE GREEN: Okay. And I will just say that rebuttal is only to
`respond to what Patent Owner says. You can't bring in new argument at that
`time.
`
`MR. HARRINGTON: Understood. Thank you.
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`IPR2017-00745 (Patent 9,078,905 B2)
`IPR2017-00746 (Patent 9,028,877 B2)
`IPR2017-00747 (Patent 9,078,905 B2)
`IPR2017-00748 (Patent 9,028,877 B2)
`
`
`JUDGE GREEN: So Whenever you're ready.
`MR. HARRINGTON: Okay, thank you. Good afternoon. We're
`here to discuss four different petitions that we brought against two different
`patents. The first we refer to as the '905 patent; the second we refer to as the
`'877 patent. Both patents relate to the production of lipids from krill to
`obtain a krill oil composition.
`And moving to slide 2, the first thing we wanted to note is that
`we're dealing with natural lipid components of krill. This is a slide
`presentation or a slide from a presentation from Patent Owner's expert,
`Dr. Hoem, who is also their chief scientist, and this slide indicates that the
`lipids extracted from krill naturally contain 44 percent phospholipids, 34
`percent triglycerides, and if we look to the right there, shaded in blue, that
`indicates the different subcomponents of the phospholipids, two of which are
`phosphatidylcholine at 38 percent and phosphatidylethanolamine at 2.6
`percent.
`And what we will see later is the ether variety of what we call the
`PC and the PE will show up later. So later on we'll see reference to AAPC,
`that's the alkylacylphosphatidylcholine, and AAPE, that the
`akylacylphosphatidylethanolamine, both prominent ether-phospholipids that
`are intrinsic to the extraction of the general phospholipid extraction.
`So moving on to slide 4 and the '905 patent, we wanted to note that
`the earliest effective filing date is January 2008, since that is the first
`disclosure of ether-phospholipid content, which is an element relied upon to
`obtain allowance of the claims, and we just wanted to note up front that both
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`IPR2017-00745 (Patent 9,078,905 B2)
`IPR2017-00746 (Patent 9,028,877 B2)
`IPR2017-00747 (Patent 9,078,905 B2)
`IPR2017-00748 (Patent 9,028,877 B2)
`
`the '905 and the '877 patent claim priority to the same parent application, so
`the specifications there are the same.
`Moving on to slide 7, representative claim 1 relates to an
`encapsulated krill oil that includes from about 3 percent to about 15 percent
`weight/weight ether-phospholipids.
`Moving on to slide 8, claim 12 introduces some additional
`elements. It narrows the ether-phospholipid level from 3 to 15 to 3 to 10. It
`also introduces an amount of nonether-phospholipids, so those two
`components can be added simply to obtain the total phospholipid content.
`And it also includes the triglyceride amount from 20 percent to 50 percent
`weight/weight triglycerides.
`Moving on to slide 9, claim 18 introduces a couple of additional
`elements, the krill being Antarctic krill, and a soft gel capsule for
`administration.
`Moving forward to slide 14, we see claim 1 of the '877 patent. The
`'877 patent relates to methods of producing krill oil, and it includes three
`well known steps of providing krill oil, treating the krill to denature lipases
`and phospholipases to provide a denatured krill product, and extracting the
`krill using polar solvents to obtain the same krill oil composition that we just
`referred to in the '905 patent.
`JUDGE GREEN: Did you argue anywhere in your petition that
`this can be analogized to a product-by-process claim, that the product that's
`claimed and those percentages are a natural result of the method steps?
`MR. HARRINGTON: Yes. That is in our petition in the '877
`
`patent.
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`IPR2017-00745 (Patent 9,078,905 B2)
`IPR2017-00746 (Patent 9,028,877 B2)
`IPR2017-00747 (Patent 9,078,905 B2)
`IPR2017-00748 (Patent 9,028,877 B2)
`
`
`JUDGE GREEN: And can you tell me where that is?
`You can have your co-counsel do it and then tell me later, but I just
`wanted to make sure.
`MR. HARRINGTON: Okay, yeah. And that will come up when
`we discuss some of the prior art that I'll get to in a minute.
`So on slide 16, we just put together just a graphical representation
`of the '905, which is the composition claims, and the '877, which includes
`the process claims, again, both resulting in the same krill oil composition,
`but the '877 patent including the steps of treating fresh krill to obtain a
`denatured krill product and extracting krill oil with a polar solvent.
`Moving to slide 17, I just wanted to touch on a couple of points in
`the prior art, and I think it will address some of your question. Starting with
`the Catchpole reference on slide 19, we just wanted to highlight that
`Catchpole discloses a process for separating lipid material containing
`phospholipids; discloses phospholipids having been implicated in conferring
`a number of health benefits; and importantly -- and I think this goes to your
`question a little bit -- it discloses the use of supercritical extraction using an
`ethanol -- an ethanol entrainer, a polar solvent, which they disclose as being
`more natural -- the CO2 and the ethanol being a more natural solvent than
`some of the more -- other organic solvents that were used.
`JUDGE GREEN: But Catchpole is not relied on in all four IPRs
`before us, correct, just two?
`MR. HARRINGTON: That's correct. That's correct. It's relied on
`in the '745 and the '746 petitions.
`MR. CHAKANSKY: '47.
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`IPR2017-00745 (Patent 9,078,905 B2)
`IPR2017-00746 (Patent 9,028,877 B2)
`IPR2017-00747 (Patent 9,078,905 B2)
`IPR2017-00748 (Patent 9,028,877 B2)
`
`
`MR. HARRINGTON: Moving on to slide 20, again, we just
`wanted to highlight what Catchpole is doing in Example 18, which is their
`example for the fractionation of krill lipids. They disclose essentially the
`same process that is disclosed in the -- in both the '905 and '877 patents.
`They use a neat CO2 supercritical extraction to first extract a first extraction
`containing mainly neutral lipids. Then they use a supercritical CO2 with an
`ethanol entrainer to obtain the phospholipids since it was well known to use
`polar solvents to extract the phospholipid fraction.
`And in Table 16, we see that it results in 4.8 percent
`ether-phospholipids, which is within the 3 to 10 percent range claimed. As I
`mentioned before when we referred to slide 2, you'll see reference to the
`AAPC and the AAPE. Again, those are the ether variety, essentially, of the
`PCs and the PEs, both adding up to 4.8 percent.
`Catchpole also indicates 53 percent other -- 53.7 percent other
`compounds, and Dr. Tallon has indicated that -- Dr. Tallon actually was a
`co-inventor on the Catchpole patent, and he indicates in his declaration that
`the majority of the 53 percent there would be triglycerides.
`Okay, moving on to slide 21, again, looking at that same Table 16
`from Catchpole, adding up the different phospholipid components, we see it
`adds up to 45 percent phospholipid, and we also note that the
`ether-phospholipid to total phospholipid ratio there is 10.6 percent, and
`Catchpole analyzed that same ratio in the feed, and we can see that that also
`is around 10 percent. So, again, this supports the notion that the
`ether-phospholipids are being extracted due to their association with the
`overall phospholipid extraction.
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`IPR2017-00745 (Patent 9,078,905 B2)
`IPR2017-00746 (Patent 9,028,877 B2)
`IPR2017-00747 (Patent 9,078,905 B2)
`IPR2017-00748 (Patent 9,028,877 B2)
`
`
`Okay. Moving forward to slide 37, I think to address a little bit of
`your question in terms of the process, we wanted to highlight the Breivik
`reference, which, again, discloses all of the method steps that are claimed in
`the '877. It discloses a process for preparing a substantially total lipid
`fraction from fresh krill. It discloses heating in order to inactivate the
`enzymes that cause decomposition of the lipids.
`Moving on to slide 39, they disclose extracting again using
`supercritical CO2 with an ethanol entrainer. And moving to slide 40, they
`again disclose fresh krill heating in order to avoid the deterioration such as
`hydrolysis or oxidation of the lipids; the use of fresh superba; the use of,
`again, supercritical CO2 with ethanol; and, importantly, they utilized NMR
`to determine the components obtained in the krill oil, and we see there that
`they obtained a fraction that was rich in phospholipids and also contained
`triglycerides and the antioxidant astaxanthin.
`So, yes, we feel that using the same process, in this case a
`supercritical CO2 with ethanol entrainer, you would -- you would obtain a
`composition that would be within the claims -- the claim limits.
`JUDGE GREEN: No, I understand that. I was just trying to figure
`out where that was, that argument was specifically made in your briefs.
`MR. HARRINGTON: Okay, okay. We will try to find that for
`
`you.
`
`And moving to slide 44, we just wanted to highlight the Grantham
`reference, which also discloses all of the method steps: heat treating to
`inactivate the lipases and phospholipases that would degrade the oil; solvent
`extraction.
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`IPR2017-00745 (Patent 9,078,905 B2)
`IPR2017-00746 (Patent 9,028,877 B2)
`IPR2017-00747 (Patent 9,078,905 B2)
`IPR2017-00748 (Patent 9,028,877 B2)
`
`
`And moving on to slide 46, this is just sort of a graphical
`representation provided by Grantham where they show fresh-caught krill
`being washed and then quickly heated, again, in order to deactivate the
`lipases and phospholipases that would degrade the oil, and then it can move
`on to the solvent extraction process.
`And even Dr. Hoem, moving to slide 47, has acknowledged that
`the heat treating to inactivate those lipases was well known. That's why they
`did it.
`
`Okay. So on slides 50 through 55, I don't want to spend much time
`on that other than to just highlight that those are there, and they sort of
`summarize the different pieces of prior art that we're utilizing for the various
`claim limitations, and to point out that they are in dispute, other than
`arguably the -- sort of what we call the Tanaka-Fricke combination
`disclosing the ether-phospholipid content. There's no dispute that the
`references that we're relying upon actually do disclose the elements that we
`say they disclose.
`JUDGE GREEN: Well, I think that the Patent Owner's argument
`is a little bit broader than that, that the Tanaka-Fricke combination shows the
`unpredictability and why one would not have been motivated to combine
`these references at all.
`MR. HARRINGTON: Correct, correct. Yep.
`And so for the motivation to combine, we think it is demonstrated
`by what's disclosed in the prior art. It was well known that krill was a good
`source of phospholipids, the krill oil contained high levels of phospholipids;
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`IPR2017-00745 (Patent 9,078,905 B2)
`IPR2017-00746 (Patent 9,028,877 B2)
`IPR2017-00747 (Patent 9,078,905 B2)
`IPR2017-00748 (Patent 9,028,877 B2)
`
`that the phosphatidylcholine and the omega-3 fatty acids within the
`phospholipids conferred various health benefits.
`It was known that the omega-3s in krill oil were attached to the
`phospholipid components as opposed to the triglycerides in fish oil, which
`make them more bioavailable; and, again, it was well known, the various
`extraction techniques available to obtain a high phospholipid fraction. It
`was also well known to utilize soft gel capsules as a convenient form of
`administration.
`So, together, we think a person of ordinary skill in the art using the
`conventional extraction techniques available would be motivated to obtain a
`krill oil with a high phospholipid content and its attendant other
`subcomponents, such as the ether- phospholipids and the triglycerides.
`Okay. So moving to slide 63, we get to the two unavailing
`arguments that the Patent Owner puts forward to argue against the
`motivation to combine. The first is what we call the PAF argument, the
`platelet activating factor argument. There the argument is that due to the
`ether-phospholipids that are present in krill oil, there would be a concern that
`they could somehow act as precursors for platelet activating factor, which
`has been implicated in inflammation. We think that argument fails for three
`reasons.
`Number one, it's a completely different molecule. The
`ether-phospholipid molecule found in krill oil is completely different from
`the PAF molecule that is allegedly a concern. The Patent Owner's own
`references discuss a completely different process than what they argue, and
`the real world evidence shows that a PAF was not a concern, and this is
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`IPR2017-00745 (Patent 9,078,905 B2)
`IPR2017-00746 (Patent 9,028,877 B2)
`IPR2017-00747 (Patent 9,078,905 B2)
`IPR2017-00748 (Patent 9,028,877 B2)
`
`shown most clearly by the fact that there were krill oil products out in the
`market years before 2008 and were being sold without incident.
`The second argument that the Patent Owner puts forward is what
`we call the Fricke II argument, stating that because of the unusually low
`level of ether-phospholipids disclosed in Fricke II, that one could not be sure
`that the ether-phospholipid level in the oil attained in Fricke I would actually
`be within, you know, the claimed range. And that argument fails also for
`three reasons.
`Fricke II is a very old reference, goes back to 1986, and it was very
`difficult back then to accurately measure ether-phospholipids, and what they
`did is used a method that required successive degradation to the point where
`what they were measuring wasn't even ether-phospholipid anymore. Even
`Dr. Hoem admitted he's never seen ether-phospholipids that low, as
`disclosed in Fricke II, with a krill oil having at least 40 percent total
`phospholipids.
`JUDGE GREEN: But that's a little bit of an overstatement of that
`testimony. He just said he hasn't seen it in the Neptune or the Aker
`products, but that he hasn't looked for it otherwise.
`MR. HARRINGTON: He hadn't looked for it. That's true.
`JUDGE GREEN: Okay.
`MR. HARRINGTON: And by 2008, there were better standards --
`namely, NMR -- that showed krill oil having at least 40 percent total
`phospholipids, had much higher levels than that disclosed in Fricke II, and I
`can go through these arguments in a little bit more detail.
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`IPR2017-00745 (Patent 9,078,905 B2)
`IPR2017-00746 (Patent 9,028,877 B2)
`IPR2017-00747 (Patent 9,078,905 B2)
`IPR2017-00748 (Patent 9,028,877 B2)
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`
`Okay, so beginning with the PAF argument, Dr. Tallon has
`explained that the ether-phospholipid molecule that is present in krill oil is a
`different molecule than the PAF molecule that is supposedly a concern.
`Moving on to slide 66, we see Dr. Tallon explaining that ether
`phospholipids in krill and krill oil possess a much longer acyl chain at the
`sn-2 position on the glyceral backbone of the phospholipid molecule, and
`those acyl chains are typically between 14 and 25 carbon atoms.
`Moving to slide 67, this is demonstrated in the Patent Owner's --
`the patents, the '877 and '905 patents, where in Table 23 we see those fatty
`acid chains ranging between 14 and 24. There is no indication there that
`there's anything shorter.
`Moving to slide 68, we see that the PAF activity only exists if that
`acyl group is substantially shorter, typically one to two carbon atoms, three
`or four at the most. Beyond that, there really is no PAF activity. And this is
`graphically depicted in slide 69, where we see again, in that second sn-2
`position, the different lengths of the carbon atoms.
`Moving to slide 70, the references relied upon by the Patent
`Owner, Tanaka, Zimmerman, and Prescott, all discuss a completely different
`oxidation process. Tanaka I extracted phosphatidylcholine from various
`food sources, krill oil being one of them, and purposefully subjected the
`phosphatidylcholine to a very harsh peroxidation process in order to
`purposefully try to create PAF-like molecules.
`And even Tanaka I, at the end of their article, indicates that, you
`know, the question of whether the PAF molecules exist in food is just -- is
`pure speculation. Zimmerman and Prescott discuss oxidation of
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`IPR2017-00745 (Patent 9,078,905 B2)
`IPR2017-00746 (Patent 9,028,877 B2)
`IPR2017-00747 (Patent 9,078,905 B2)
`IPR2017-00748 (Patent 9,028,877 B2)
`
`phosphatidylcholine within the cell. Namely, in the cell wall, the
`phosphatidylcholine is present, and that can be oxidative. But there, again,
`is no disclosure in Zimmerman or Prescott, no suggestion at all to avoid krill
`oil or any foods that might contain phospholipids or ether-phospholipids due
`to this so-called PAF concern.
`Okay, moving forward to slide 78, we see Dr. Hoem's testimony
`that any measurable level of ether-phospholipids would have raised concerns
`about PAF for a POSITA, and we know -- again, from the real world
`experience of what was actually happening in terms of krill oil in 2008 --
`that that is just simply not true.
`Going back to slide 75, we see Dr. Hoem's testimony where he
`acknowledges in claim 22 of the patents the analysis of the NKO oil -- that's
`Neptune krill oil, which was a prior art oil being sold years before the 2008
`filing date -- and through the calculation, adding up the AAPC and the
`LAAPC, multiplying it by the 30 percent phospholipid content that they
`have there, he acknowledged that that would calculate to a 2.46
`ether-phospholipid level.
`And moving to slide 77, we see an advertisement here for the NKO
`oil being sold under the name Krill Bill years before the earliest effective
`filing date. They advertise a total phospholipid content of greater than 40,
`not 30, and they provide the fatty acid content. They also provide -- they
`also indicate that astaxanthin is present, a known antioxidant. And this krill
`oil was being sold, you know, without incident.
`And moving to slide 78 again, Dr. Hoem testified that the only way
`to really be sure that krill oil would not be a concern would be to do some
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`IPR2017-00745 (Patent 9,078,905 B2)
`IPR2017-00746 (Patent 9,028,877 B2)
`IPR2017-00747 (Patent 9,078,905 B2)
`IPR2017-00748 (Patent 9,028,877 B2)
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`clinical testing, and they did some clinical testing, and on slide 79, we show
`that his testimony indicated that their clinical testing did not include any
`testing for PAF-like activity. So this is further evidence that PAF was really
`not a concern.
`Instead, moving to slide 80, what the Patent Owner did when they
`submitted their notification, their GRAS notification requesting the FDA
`recognize the krill oil as generally recognized as safe, they relied upon
`published clinical studies, one of which was Sampalis I, the same reference
`that we rely on for obviousness. And in Sampalis I -- I believe that goes
`back to 2002 or 2003 -- and Sampalis I was a study of NKO oil, and they
`demonstrated that the NKO oil was effective in reducing the symptoms of
`PMS -- namely, inflammation -- through the administration of that krill oil.
`So, again, this is evidence that the Patent Owner is using to demonstrate the
`safety of krill oil.
`Okay. Moving on to slide 2 [sic], we would like to address a little
`bit further the Fricke II --
`MR. CHAKANSKY: Restate the slide number.
`MR. HARRINGTON: Slide 82.
`-- what we refer to as the Fricke II argument. And if we move to
`slide 84, we can see Dr. Tallon's explanation that due to the successive
`degradation that was required in the Fricke 82 [sic] method, it resulted in a
`severely degraded remnant that included no phospholipid head group, no
`acyl group, no ether group, so -- and that degradation causes a loss in
`quantifiable product, and that's one reason why the Fricke II method is just
`not reliable and resulted in an anomalous result.
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`IPR2017-00745 (Patent 9,078,905 B2)
`IPR2017-00746 (Patent 9,028,877 B2)
`IPR2017-00747 (Patent 9,078,905 B2)
`IPR2017-00748 (Patent 9,028,877 B2)
`
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`JUDGE HARLOW: But, Counsel, taking that into account,
`Dr. Tallon gives us a calculation for the amount of ether-phospholipid that
`Fricke II would be reporting, and that was still below the claimed range.
`Isn't that correct?
`MR. HARRINGTON: Yes. There he was showing that due to the
`difference in molecular weight, that was one part of the error. The other part
`was this loss of quantifiable product. So even not considering the loss of
`quantifiable product, you still get to 1.5 percent. Then you add on to that
`this loss of quantifiable product due to the successive degradation, and you
`get the much lower numbers, numbers that, again, Dr. Hoem has not seen in
`a 40 percent ether-phospholipid composition.
`JUDGE HARLOW: On the topic of loss of quantifiable product,
`my recollection is that Dr. Tallon lists some reasons why product might have
`been lost, but I don't recall seeing a detailed discussion of what would be
`lost when and why. Perhaps you could walk us through that in a little bit
`more detail.
`MR. HARRINGTON: Yeah. I think Dr. Tallon was trying to
`explain that because of the fact that the ether-phospholipid molecules are
`degraded to the point that what you're actually looking for no longer exists,
`it makes it much more difficult to actually find and quantify. So it's causing
`an anomalous result and much lower than what was seen by later, more
`accurate results and test methods; namely, NMR.
`JUDGE HARLOW: On the topic of what we were looking for in
`Fricke II, perhaps you could elaborate on that a little bit. So is it Dr. Tallon's
`position that because some of the product might not be fully degraded to
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`IPR2017-00745 (Patent 9,078,905 B2)
`IPR2017-00746 (Patent 9,028,877 B2)
`IPR2017-00747 (Patent 9,078,905 B2)
`IPR2017-00748 (Patent 9,028,877 B2)
`
`reach the point of what we're trying to detect we have lost, or is something
`else going on? I was hoping for a bit more detail on that.
`MR. HARRINGTON: Yeah. No, I think what he's saying is we
`have the ether-phospholipid molecule that naturally exists in krill oil, and
`it includes the structure that we saw before with the ether group at the sn-1
`position, the acetyl group, those long chains, at the sn-2, and the phosphate
`group at sn-3. And because of the successive degradation required by the
`Fricke II method, all three of those components are being stripped away, so
`that all you have is the glycerol backbone.
`And Dr. Tallon is saying that because that's all that you have left, it
`becomes very difficult to identify how much of the ether-phospholipid was
`originally there, as opposed to the NMR method, where you are actually
`measuring directly the ether-phospholipid molecules that are actually present
`in the krill.
`JUDGE HARLOW: Thank you.
`And one more question about Fricke II and this process. Am I
`recalling correctly -- and I believe you might have mentioned this earlier in
`your presentation -- that in IPRs '745 and '746, you do not rely on Fricke I to
`support your contention that the claimed amount of ether-phospholipid is
`known in the art?
`MR. HARRINGTON: That's --
`MR. CHAKANSKY: '745 and '747 is Catchpole, so those are the
`
`ones.
`
`(Counsel conferring.)
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`IPR2017-00746 (Patent 9,028,877 B2)
`IPR2017-00747 (Patent 9,078,905 B2)
`IPR2017-00748 (Patent 9,028,877 B2)
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`MR. HARRINGTON: So, yes, you are correct. We rely on
`Catchpole for the ether-phospholipid levels in those two petitions, not on
`what we call the Tanaka/Fricke combination.
`JUDGE HARLOW: And did either you or Patent Owner address
`in your filings whether the Fricke II either phospholipid calculation or data
`affects the disclosure by Fricke I of -- I believe you -- were you relying on
`Fricke I for the triglycerides in those two IPRs?
`MR. HARRINGTON: Yes. Yes, and that's -- yes, and that's one
`of the points that we wanted to make, is if we go to slide 29, this shows the
`extraction obtained in Fricke I, and here we have -- they study two different
`samples, both showing 45 and 44 percent total phospholipids;
`phosphatidylcholine levels of 35 and 33 percent. And so there has been no
`explanation from the Patent Owner as to how you can have total
`phospholipids and phosphatidylcholine at that level and have such an
`anomalously low reading for the ether-phospholipids that would be
`intrinsically present in that extraction.
`So -- and, yes, to answer your question, the Fricke I discloses the
`triglycerides as well, and that is relied upon in both of the petitions that you
`referenced.
`JUDGE HARLOW: And there's no argument that Fricke I's
`disclosure regarding the triglycerides is somehow suspect in view of Fricke
`II. Is that correct?
`MR. HARRINGTON: That's correct. That's correct. There's
`been -- there's been no dispute from the Patent Owner on that point.
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`IPR2017-00745 (Patent 9,078,905 B2)
`IPR2017-00746 (Patent 9,028,877 B2)
`IPR2017-00747 (Patent 9,078,905 B2)
`IPR2017-00748 (Patent 9,028,877 B2)
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`
`JUDGE HARLOW: And while we're on those first two petitions --
`actually, that's fine. Please proceed.
`MR. HARRINGTON: Okay. So moving on to slide 87 --
`JUDGE GREEN: You have about 6 1/2 minutes left.
`MR. HARRINGTON: Okay, thank you.
`Moving on to slide 87, we just wanted to note that, again, Fricke II
`utilizes -- goes back to 1986, and back then it was very difficult to identify
`the ether-phospholipid subcomponents in phospholipid. And in 2003, 2004,
`NMR became the preferred method for analyzing the subcomponents, and
`that was work done by Dr. Catchpole. Again, Dr. Tallon was part of that
`work, and they worked with their colleague Dr. Andrew Mackenzie to
`develop the NMR method that is presently used to identify these
`subcomponents in krill.
`And, frankly, this is what we think has happened in terms of the
`Patent Owner being able to gain the allowance of these claims. It wasn't that
`the ether-phospholipids were not there. It was just that they were able to be
`measured as of, you know, 2003, 2004 using this more improved method,
`and that's why there is very little prior art out there in terms of the
`ether-phospholipid content that, not surprisingly, was the element that they
`utilized to gain allowance of their claims.
`So moving on to slide 89, we see that Catchpole used NMR to
`identify their ether-lipid subcomponents. Again, we saw before those
`totaled 4.8 percent with a 45 percent total phospholipid content. And even
`Dr. Hoem has acknowledged in an article -- this is slide 90 -- in an article
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`IPR2017-00745 (Patent 9,078,905 B2)
`IPR2017-00746 (Patent 9,028,877 B2)
`IPR2017-00747 (Patent 9,078,905 B2)
`IPR2017-00748 (Patent 9,028,877 B2)
`
`that he co-authored that NMR is the preferred method for analyzing the
`subcomponents.
`And moving to --
`JUDGE HARLOW: But that article is not prior
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