`UNITED STATES PATENT AND TRADEMARK OFFICE
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`BEFORE THE PATENT TRIAL AND APPEAL BOARD
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`RIMFROST AS
`Petitioner,
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`v.
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`AKER BIOMARINE ANTARCTIC AS
`Patent Owner.
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`Case IPR2018-01179
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`U.S Patent No. 9,375,453
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`Patent Owner’s Sur-Reply to Petitioner’s Reply
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`Mail Stop Patent Board
`Patent Trial and Appeal Board
`U.S. Patent and Trademark Office
`P.O. Box 1450
`Alexandria, VA 22313-1450
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`IPR2018-01179
`U.S. Patent No. 9,375,453
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`TABLE OF CONTENTS
`Introduction ........................................................................................... 1
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`Collateral Estoppel ................................................................................ 1
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`I.
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`II.
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`III. There is no Motivation to Combine the Cited References .................... 2
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`IV. Conclusion ........................................................................................... 10
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`CERTIFICATE OF SERVICE ......................................................................... i
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`I.
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`Introduction
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`IPR2018-01179
`U.S. Patent No. 9,375,453
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`The pending claims are directed to a method of extraction with specific
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`levels of ether phospholipids, total phospholipids, triglycerides and astaxanthin
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`esters (and other components in the dependent claims) from a denatured starting
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`material and then formulating the krill oil for oral consumption. To arrive at the
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`claimed method, Petitioner combines the processing steps and astaxanthin ester
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`range from Breivik II with the ether and total phospholipid ranges from Catchpole
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`and triglyceride range from Bottino II. However, the krill oils described in Breivik
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`II and Catchpole were extracted by very different techniques from that utilized in
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`Bottino. Id. at 6. Bottino utilized a non-selective Folch extraction which is
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`intended to extract total lipids, including both neutral and polar lipids, from the
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`source material. Ex. 1038 at 0001-2. Catchpole and Breivik II utilized selective
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`supercritical fluid extraction methods. As will be shown by the evidence below,
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`the rationale advanced by Petitioner to explain why the ranges for triglycerides
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`from Bottino can be simply combined with the ether phospholipid range from
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`Catchpole is flawed. Thus, a person having ordinary skill in the art (POSITA)
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`would not combine the reference to arrive at the claimed process.
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`II. Collateral Estoppel
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`Petitioner argues that collateral estoppel stemming from the final written
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`decisions in IPR2017-00745, IPR2017-00746, and IPR2018-00295 applies to
`1
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`challenged claims 33-61 and that the claims have “materially identical ranges of
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`IPR2018-01179
`U.S. Patent No. 9,375,453
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`ether phospholipids, triglycerides and astaxanthin esters.” Petitioner’s Reply to
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`Patent Owner’s Response (Paper No. 18; Pet. Reply) at 4-5. For the purposes of
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`this proceeding, Patent Owner will not dispute whether collateral estoppel applies
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`to issues related to the Board’s findings regarding ranges for these components.
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`Patent Owner further notes that while Petitioner argues that while collateral
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`estoppel may apply to Patent Owner’s “no triglycerides” and “PAF teaching away”
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`arguments, Petitioner admits that Patent Owner’s arguments regarding combination
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`of references teaching selective and non-selective lipid extraction procedures is in
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`play.
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`III. There is no Motivation to Combine the Cited References
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`The claims as a whole are directed to using a polar solvent to extract a krill
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`oil with defined lipid components from a denatured krill product. The polar
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`solvent is selective for polar lipids. See, Petition (Paper 2) at 21. A POSITA
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`would not combine lipid component ranges from non-selective lipid extraction
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`techniques such as those used in Bottino with lipid component ranges obtained by
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`selective extraction techniques utilizing polar solvents such as taught in Breivik II
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`and Catchpole. The following chart from Dr. Hoem’s Declaration summarizes the
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`different extraction techniques.
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`2
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`IPR2018-01179
`U.S. Patent No. 9,375,453
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`Reference
`Catchpole
`(Ex. 1009)
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`Bottino II
`(Ex. 1038)
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`Breivik II
`(Ex. 1037)
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`Extraction technique
`Selective - Two-step process - Ex. 1009 at 0024.
`Step 1 – extraction of neutral lipids from freeze
`dried krill powder by SFE with neat CO2 to provide
`a residual powder.
`Step 2 - Extraction of residual powder by SFE with
`CO2 plus 11% ethanol to yield Extract 2 (krill
`phospholipid extract)
`Non-selective – Single step extraction of total
`lipids in a single step process by the method of
`Folch et al. Lipids were extracted by
`homogenizing tissue with 2:1 chloroform-methanol
`(v/v). Ex. 1038 at 0001-2.
`Selective - Two-step process described in examples
`6, 7 and 8 – Ex. 1037 at 0009.
`Step 1 – Ethanol wash of whole krill (heated or
`unheated) with ethanol.
`Step 2 – SFE with CO2 plus ethanol on ethanol
`washed whole krill.
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`Ex. 2001 (Hoem Decl.) ¶86. As summarized by Dr. Hoem:
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`A POSITA would understand that applying different extraction techniques to
`different krill starting materials will produce lipid extracts with different
`profiles depending on the solvents and extraction scheme. Thus, a POSITA
`would not combine ranges for lipid components obtained by different
`extraction techniques.
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`Id. at ¶86.
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`In response, Dr. Tallon opines that: “PO disregards the fact that a POSITA
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`would not even have made the distinction between selective and non-selection
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`extractions, as all extraction are selective by nature, to one extent or another – the
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`aim of extraction is to separate some (i.e., selected) compounds, the soluble ones,
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`3
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`from insoluble ones.” Ex. 1086 ¶107. Petitioner further makes disparaging
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`IPR2018-01179
`U.S. Patent No. 9,375,453
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`accusations that the distinction between selective and non-selective lipid extraction
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`techniques is a “straw-man” and “litigation induced.” Pet. Reply at 14, 15. This
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`could not be further from the truth as evidenced by the deposition testimony of Dr.
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`Tallon where he admits that lipid extractions can be categorized as selective or
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`non-selective.
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`When challenged during his deposition, Dr. Tallon admitted that he had used
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`the term “non-selective” to describe lipid extractions:
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`20 Q Go back to my question.
`21 Have you ever used the term
`22 non-selective to describe an extraction?
`23 MR. CHAKANSKY: Objection. Asked
`24 and answered.
`25 A I am sure I probably have.
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`Ex. 2030, p. 26. Dr. Tallon then later confirmed that the Folch (i.e., the chloroform
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`methanol extraction used in Bottino) is non-selective:
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`19 A Yeah, if you're talking about
`20 solvent systems for all lipids, in the solvent
`21 system like chloroform and methanol, you could
`22 define that as being one that doesn't
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`4
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`IPR2018-01179
`U.S. Patent No. 9,375,453
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`23 differentiate, or it's not selecting between
`24 those different lipid components that are being
`25 extracted.
`Ex. 2030, p. 34. As further stated by Dr. Tallon:
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`7 A chloroform-methanol system is
`8 selective for lipids, and it's non-selective
`9 across those lipids that are being extracted.
`* * *
`16 Now, I have got no issue with the
`17 concept that different solvent systems are going
`18 to extract different -- different -- some of them
`19 will extract subsets of the total that one might
`20 define as the class of lipids, as well as extract
`21 broadly across all of those classes of lipids --
`22 I have got no problem with that.
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`Ex. 2030, p. 35. Dr. Tallon then admitted the following regarding selective solvent
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`systems:
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`4 Q So then would you -- based on what
`5 you just said, would you define -- is it fair to
`6 say that a solvent system that extracts some
`7 lipid components, but not others is selective for
`8 those specific lipid components?
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`5
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`IPR2018-01179
`U.S. Patent No. 9,375,453
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`9 A Yes, that's -- that sounds like a
`10 reasonable -- reasonable way to put it, in fact,
`11 possibly the words that I just used myself a few
`12 minutes ago.
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`Thus, contrary to Dr. Tallon’s testimony in his Declaration, it is reasonable to
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`describe lipid extraction techniques as being selective or non-selective and that a
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`POSITA would expect selective techniques would extract a different subset of
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`lipids than non-selective techniques. This is entirely consistent with Dr. Hoem’s
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`testimony:
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`Ranges for lipid components obtained by different methods cannot be
`combined with any reasonable expectation of success to provide the specific
`krill oil designated in the claims. Extraction with neutral solvents will
`preferentially extract neutral lipids such as triglycerides, diglycerides and
`free fatty acids, while extraction with polar solvents will preferentially
`extract polar lipids such as phospholipids. Likewise, a nonselective
`extraction such as a Folch extraction which uses chloroform and methanol
`together will produce an extract with different properties than extracts
`prepared with neutral or polar solvents.
`Ex. 2001 ¶87.
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`There can be no doubt that the extraction procedures utilized in Catchpole
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`and Breivik are selective extraction techniques. Id. Example 18 of Catchpole
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`clearly states that ether phospholipids are “highly enriched” in extract 2 indicating
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`that the extraction is selective.
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`6
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`Petitioner found a reference that teaches the triglyceride range but failed to
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`IPR2018-01179
`U.S. Patent No. 9,375,453
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`consider that the claims are directed to extraction from a denatured krill material
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`with a polar solvent. Without the benefit of hindsight, a POSITA would not
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`combine lipid ranges from an extract made by a non-selective lipid extraction
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`technique such as the Folch extraction used in Bottino II with lipid ranges obtained
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`by the selective extraction techniques utilizing polar solvents as disclosed in
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`Catchpole and Breivik II.
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`Petitioner’s argument centers on the following allegation:
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`Contrary to PO’s contrived process “selectivity” strawman, properly framed,
`the obviousness question is whether a method of producing polar krill oil
`having the broad ranges of phospholipids, triglycerides and astaxanthin
`esters recited in the challenged claims would have been obvious in view of
`the conventional extraction techniques readily available to a POSITA.
`Pet. Reply at 15. However, this argument ignores the fact that the claims require
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`contacting the denatured krill product with a polar solvent to extract a krill oil
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`with specific properties. Without hindsight, there is no reason for a POSITA to
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`combine a reference utilizing a non-specific lipid extraction technique such as
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`disclosed in Bottino with references utilizing polar solvents such as those disclosed
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`Catchpole and Breivik II. There are many extraction techniques available, but
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`whether a POSITA would combine results from different extraction techniques is a
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`different matter.
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`7
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`Furthermore, the hindsight nature of Petitioner’s combination is
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`IPR2018-01179
`U.S. Patent No. 9,375,453
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`demonstrated by its cherry-picking of data from Bottino. Table 2 of Bottino
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`provides the triglyceride content of two E. superba lipid extracts, one contained 8%
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`triglycerides and the other contained 36 ± 6% triglycerides.
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`No explanation is provided as to why a POSITA would choose the 36% value,
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`which falls within the claimed range, over the 8% value which is well outside the
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`claimed range. See Ex. 2001 (Hoem Decl.) ¶68.
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`Properly viewed, Petitioner’s combinations and arguments are based on
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`hindsight using the Patent Owner’s claims as a guide and fail to consider the
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`claims as a whole. For example, Petitioner argues that “the art that conventional
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`extraction techniques employing different process conditions (e.g., temperatures,
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`pressures, solvents and solvent concentrations) could be predictably modified to
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`8
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`produce krill oil having different percentages of, inter alia, ether phospholipids,
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`IPR2018-01179
`U.S. Patent No. 9,375,453
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`triglycerides and astaxanthin esters.” Pet. Reply at 16. However, this argument
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`does not address why a POSITA would combine the results of different extraction
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`techniques (as Petitioner has done) to provide the lipid components of a krill oil
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`specifically extracted from a denatured krill product with a polar solvent as
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`claimed.
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`Petitioner further argues that “the Board previously credited Dr. Tallon’s
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`testimony that ‘the relative proportions of krill oil constituents could be varied in
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`predictable ways by applying a single solvent or combination of solvents including
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`supercritical fluid extraction to selectively extract specific groups of lipid
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`components based on their different solubility.’ -295 FWD, p. 37.” However, the
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`Board also indicated that there was a distinction between claims to krill oil
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`compositions and methods for making those compositions. IPR2018-00295, Final
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`Written Decision at 36. In that case composition claims were at issue in contrast to
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`the instant case where claims to a specific process using a polar solvent for
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`extraction are at issue.
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`The claims at issue require extraction with a particular solvent system (i.e., a
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`polar solvent system) from a particular starting material (a denatured krill product)
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`to extract a krill oil with defined components. Therefore, the claims present the
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`9
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`different issue of whether a POSITA would combine the references to arrive at a
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`IPR2018-01179
`U.S. Patent No. 9,375,453
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`specific method of producing a defined krill extract. As established above, a
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`POSITA would not be motivated to combine references utilizing selective and non-
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`selective lipid extraction methods to arrive at the claimed method which utilizes a
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`polar solvent to extract a defined krill oil from a denatured krill starting material.
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`IV. Conclusion
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`For the foregoing reasons, Patent Owner submits that the Petition should be
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`denied and that the claims be found patentable.
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`Dated: August 14, 2019 Respectfully submitted,
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`/David A. Casimir / Reg. No. 42,395
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`IPR2018-01179
`U.S. Patent No. 9,375,453
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`CERTIFICATE OF SERVICE
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`The undersigned hereby certifies that on this 14th day of August 2019, a
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`copy of the foregoing Patent Owner’s Sur-Reply to Petitioner’s Reply was
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`served in its entirety electronically (as consented to by Petitioner) to the attorneys
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`of record as follows:
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`James F. Harrington
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`Reg. No. 44,741
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`Hoffmann & Baron, LLP
`jfhdocket@hbiplaw.com
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`Ronald J. Baron
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`Reg. No. 29,281
`Hoffman & Baron, LLP
`rjbdocket@hbiplaw.com
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`453ipr@hbiplaw.com
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`Michael I. Chakansky
`Reg. No. 31,600
`Hoffman & Baron, LLP
`micdocket@hbiplaw.com
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`John T. Gallagher
`Reg. No. 35,516
`Hoffman & Baron, LLP
`jtgdocket@hbiplaw.com
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`By: /David A. Casimir/
`David A. Casimir, Ph.D.
`Registration No. 42,395
`Counsel for Patent Owner
`CASIMIR JONES, S.C.
`2275 Deming Way
`Suite 310
`Middleton, Wisconsin 53562
`(608) 662-1277
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