`UNITED STATES PATENT AND TRADEMARK OFFICE
`
`
`
`
`
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`
`
`
`
`
`
`
`RIMFROST AS
`Petitioner,
`
`v.
`
`AKER BIOMARINE ANTARCTIC AS
`Patent Owner.
`
`
`
`
`Case IPR2018-01730
`
`U.S Patent No. 9,072,752
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`Patent Owner’s Sur-Reply to Petitioner’s Reply
`
`
`
`Mail Stop Patent Board
`Patent Trial and Appeal Board
`U.S. Patent and Trademark Office
`P.O. Box 1450
`Alexandria, VA 22313-1450
`
`
`
`
`
`
`
`IPR2018-01730
`U.S. Patent No. 9,072,752
`
`CONTENTS
`Collateral Estoppel ................................................................................ 1
`
`Claims 5 and 6 are not anticipated by Catchpole .................................. 2
`
`I.
`
`II.
`
`III. Claims 5, 6, 15 and 16 are not obvious ................................................. 7
`
`IV. Conclusion ........................................................................................... 10
`
`CERTIFICATE OF SERVICE ......................................................................... i
`
`i
`
`
`
`
`
`
`
`
`
`IPR2018-01730
`U.S. Patent No. 9,072,752
`
`Collateral Estoppel
`Petitioner argues that collateral estoppel stemming from the final written
`
`
`
`I.
`
`
`decisions in IPR2017-00745, IPR2017-00746, and IPR2018-00295 applies to
`
`challenged claims 1-20 and that the claims have “materially identical ranges of
`
`ether phospholipids, triglycerides and astaxanthin.” Petitioner’s Reply to Patent
`
`Owner’s Response (Pet. Reply) at 4-5. For the purposes of this proceeding, Patent
`
`Owner will not dispute whether collateral estoppel applies to issues related to the
`
`Board’s findings regarding the claims requiring greater than about 5% ether
`
`phospholipids. However, Patent Owner specifically notes that the pending and
`
`potential appeal of the Final Written Decisions of the identified IPRs may render
`
`the collateral estoppel arguments of Petitioner moot and therefore specifically
`
`reserves the right to assert and/or appeal the arguments presented in its Patent’s
`
`owner Response (“POR,” Paper 13) with respect to those claims.
`
`
`
`Patent Owner does not agree that the claims limited to either greater than
`
`about 6% ether phospholipids (claims 5 and 15) and greater than about 7% ether
`
`phospholipids (claims 6 and 16) are subject to collateral estoppel based on the
`
`previous IPR Final Decisions. Specifically, the ‘295 IPR relied on the fact that the
`
`4.8% ether phospholipid content of Catchpole Extract 2 was “adjacent” to the
`
`
`
`1
`
`
`
`
`claimed range of 5 to 8% ether phospholipids. IPR2018-00295, Final Written
`
`IPR2018-01730
`U.S. Patent No. 9,072,752
`
`Decision, (Paper 35)(“-295 FWD”). Under Petitioner’s claim construction, “about
`
`greater than 6%” means greater than 5.5% and “about greater than 7%” means
`
`greater than 6.5%. Neither of these ranges are adjacent to 4.8%. An ether
`
`phospholipid content of 5.5% represents a 12.7% increase over an ether
`
`phospholipid content of 4.8% and an ether phospholipid content of 6.5% represents
`
`a 26.2% increase over an ether phospholipid content of 4.8%. The issue of
`
`whether Catchpole provides the claim limitations of greater than 6% and 7% ether
`
`phospholipids was not addressed in the previous IPRs.
`
`II. Claims 5 and 6 are not anticipated by Catchpole
`
`Claims 5 and 6 require greater than about 6% and 7% ether phospholipids,
`
`respectively. The Board indicated in the Institution Decision that Petitioner had
`
`not established by a preponderance of the evidence that Catchpole anticipates
`
`claims 5 and 6. Institution Decision at 6. It is undisputed that the only specific
`
`example of a krill oil in Catchpole is in Table 16 which discloses that Extract 2
`
`contains 4.8% ether phospholipids. That is the maximum amount of ether
`
`phospholipids in any oil or extract described in any example in Catchpole. It is
`
`also undisputed that the statements in Catchpole that refer to greater than 5% or
`
`
`
`2
`
`
`
`
`10% alkylacylphospholipids refer to generic compositions and not to krill oils as
`
`IPR2018-01730
`U.S. Patent No. 9,072,752
`
`claimed.
`
`
`
`Petitioner argues that krill oils containing greater than 5% or 10% ether
`
`phospholipids could be obtained by applying the process conditions disclosed in
`
`Catchpole. Pet. Reply at 7, 9. At best this is an anticipation by inherency
`
`argument. However, the data in Catchpole clearly demonstrates that the various
`
`extraction conditions disclosed in Catchpole would not necessarily produce krill oil
`
`with the greater than about 6% or 7% ether phospholipids. Specifically, Petitioner
`
`argues that Catchpole discloses three marine animals to be used as feed materials
`
`for extracting ether phospholipids, Hoki head, green-lipped mussel and krill. Id. at
`
`7. Petitioner further argues that “a POSITA desiring an extract with having greater
`
`than 10% ether phospholipids, or at least greater than about 6 or 7%, would have
`
`selected a marine animal, such as krill, and applied Catchpole’s recited extraction
`
`methodology.” Id. at 9. According to Petitioner, increasing the solvent
`
`concentration to at least 20% will increase the percentage of extracted
`
`phospholipids. Id. at 8-9.
`
`As a preliminary matter, the “three marine animals” in Catchpole are Hoki
`
`head lipid extract (Example 12, Ex. 1009 at 20), green-lipped mussel lipid extract
`
`(Example 17, Ex. 1009 at 23), and freeze-dried krill powder (Example 18, Ex.
`
`
`
`3
`
`
`
`
`1009 at 24). The Hoki head example utilized 31% ethanol in the second extraction
`
`IPR2018-01730
`U.S. Patent No. 9,072,752
`
`step and produced an extract containing 1.6% ether phospholipids. Id. at 21, Table
`
`11). The green-lipped mussel example used 30.5% ethanol in the second extraction
`
`step and produced an extract containing 0.9% ether phospholipids. Id. at 23, Table
`
`15. The krill example used 11% ethanol in the second extraction step and produced
`
`an extract containing 4.8% ether phospholipids. Id. at 24, Table 16. Both the Hoki
`
`head and green-lipped mussel examples, which used feed materials having a
`
`higher AAPC content than the krill feed material, used levels of ethanol in excess
`
`of 20% and obtained extracts with levels of ether phospholipids much lower than
`
`the claimed about greater than about 6 or 7%. In fact, while the Hoki head
`
`example used 31% ethanol and a feed material with higher starting levels of PC
`
`and AAPC as compared to the krill feed material, the resulting Koki head extract
`
`had lower levels of PC and AAPC than the krill Extract 2 as can be seen by
`
`comparing Tables 11 (Hoki head extract) and 16 (Krill Extract 2). These data
`
`certainly cast doubt on whether increasing the ethanol co-solvent to above 20% in
`
`the krill extraction would actually increase the amount ether phospholipids to the
`
`claimed amounts of greater than about 6 or 7% and underscores the
`
`unpredictability of the methodology.
`
`
`
`The data relied on by Petitioner is also flawed. Examples 11 (egg lecithin)
`
`and 12 (Hoki head) disclose that the ethanol co-solvent extract and residue material
`
`
`
`4
`
`
`
`
`contained more PC (phosphatidylcholine) and AAPC (alkylacylPC) on a mass
`
`IPR2018-01730
`U.S. Patent No. 9,072,752
`
`basis than the feed material. For the Hoki head example, the PC content of the
`
`feed material is (25g) X (.092) = 2.3 g PC. The PC content of the extract is (25g)
`
`X (.72) X (.142) = 2.56 g PC. The PC content of the residue is (25g) X (.27) X
`
`(.143) = .96 g PC. The amount of PC in the extract and residue equals 3.52 grams
`
`which is approximately 50% greater than the amount of PC reported in the feed
`
`material (2.3 g). The same calculations for AAPC demonstrate that the feed
`
`material contained 2.75 g AAPC while the extract contained 2.88% AAPC. As
`
`testified by Dr. Tallon, having more phospholipid in the extract than is present in
`
`the feed material is not possible. Tallon Depo, Ex. 2026, 21:22-22:4; 23:7-22.
`
`Exhibit 11 has the same “impossible” results. These problems are systemic in
`
`Catchpole and would lead a POSITA to doubt the results in any example.
`
`Petitioner further relies on Examples 7 and 8 of Catchpole for the
`
`proposition that increasing ethanol co-solvent concentration to greater than 20%
`
`“will increase the percentage of extracted phospholipids, such as
`
`phosphatidylcholine.” Pet. Reply at 9. Examples 7 and 8 describe extractions from
`
`“dairy lipid extract B” using either 10% or 30% ethanol in the second step
`
`following a first step using neat CO2 to extract neutral lipids. Ex. 1009 at 18-19.
`
`The amount of phosphatidylcholine extracted with 30% ethanol in Example 8
`
`
`
`5
`
`
`
`
`(22.5%, Table 8) was greater than that obtained with 10% ethanol in Example 7
`
`IPR2018-01730
`U.S. Patent No. 9,072,752
`
`(4.5%, Table 7).
`
`However, other examples in Catchpole are not consistent. Example 10
`
`describes a similar extraction on a different source material, egg yolk lecithin,
`
`using 25% ethanol in the second extraction step following a first step using neat
`
`CO2 to extract neutral lipids. Ex. 1009 at 19-20. The feed material contained
`
`56.4% phosphatidylcholine while the extract contained using 25% ethanol
`
`contained 43.5% phosphatidylcholine. Ex. 1009 at 20, Table 9. Thus, in direct
`
`contrast to Example 8, the percentage amount of phosphatidylcholine in the 25%
`
`ethanol extract actually decreased as compared to the feed material. Thus, it not
`
`clear that increasing the ethanol co-solvent concentration to a level above 20% will
`
`result in an increased extraction of phospholipids.
`
`These data, especially when considered in conjunction with the Hoki head
`
`and green-lipped mussel examples, clearly indicate to a POSITA that the effect of
`
`increasing the co-solvent concentration does not necessarily increase the weight
`
`percentage of phospholipids such as phosphatidylcholine and ether phospholipids
`
`in extracts. Instead, these data demonstrate to a POSITA that the effect of
`
`changing extraction conditions such as co-solvent percentage with respect to a feed
`
`material is completely unpredictable. Claims 5 and 6 are not anticipated by
`
`Catchpole.
`
`
`
`6
`
`
`
`
`III. Claims 5, 6, 15 and 16 are not obvious
`Petitioner admits that the obviousness rejections of claims 5 and 6 over the
`
`IPR2018-01730
`U.S. Patent No. 9,072,752
`
`combination of Catchpole and Enzymotec (Ground 4) and claims 15 and 16 over
`
`the combination of Catchpole, Enzymotec and Sampalis II (Ground 5) rely on
`
`Catchpole and not Enzymotec for the ether phospholipid limitation. Pet. Reply at
`
`18, 24. Petitioner relies on the same arguments presented at pages 5-9 (and
`
`discussed above in detail in relation to anticipation of claims 5 and 6 by Catchpole)
`
`of its Reply to support its contention that Catchpole provides the claim elements of
`
`greater than about 6 or 7% ether phospholipids. Pet. Reply at 19.
`
`Since Petitioner has clarified that it is relying only on Catchpole for the ether
`
`phospholipid limitation and relies on the same arguments identified for anticipation
`
`by Catchpole, Patent Owner submits that the examples and data discussed by
`
`Petitioner related to Catchpole establish 1) that there is a missing element because
`
`the combined references do not teach the claimed ether phospholipid limitations
`
`for krill oil and 2) that increasing ether phospholipid content in any extract, much
`
`less a krill lipid extract, is completely unpredictable and therefore there is no
`
`reasonable expectation of success. As discussed above: 1) Example 12 of
`
`Catchpole (Hoki head extract) demonstrates that when a 31% ethanol co-solvent
`
`was used to extract a feed material with higher starting levels of PC and AAPC
`
`than the krill feed material, lower levels of PC and AAPC were obtained as
`
`
`
`7
`
`
`
`
`compared to the krill Extract 2; 2) in contrast to Examples 7 and 8 (extraction from
`
`IPR2018-01730
`U.S. Patent No. 9,072,752
`
`Dairy Lipid Extract B with 10% or 30% ethanol co-solvent, respectively), Example
`
`10 shows that PC content of the extract is decreased as compared to the PC content
`
`of the feed material when extraction is with a 25% ethanol co-solvent; and 3) there
`
`is an apparent systemic problem in the data reported in Catchpole.
`
`Petitioner’s arguments that a POSITA could manipulate extraction
`
`conditions to arrive at the claimed range of ether phospholipids are based on
`
`hindsight and undercut by the data in Catchpole which demonstrates that there is
`
`no reasonable expectation of success for arriving at greater than about 6% or 7%
`
`ether phospholipid ranges based on the combined references. Without the benefit
`
`of hindsight, viewing this data as a whole indicates to a POSITA that there is no
`
`reasonable expectation of success in arriving at the claimed ether phospholipid
`
`range from the three marine animals exemplified in Catchpole, much less the krill
`
`feed material. Both the Hoki head and green-lipped mussel examples used levels
`
`of ethanol in excess of 20% and obtained extracts levels of ether phospholipids
`
`much lower than was obtained with an 11% ethanol co-solvent on the krill feed
`
`material. Moreover, Example 10 (egg yolk lecithin), Example 12 (Hoki head) and
`
`18 (freeze dried krill powder) all used the extraction pressure (300 bar) and similar
`
`temperatures (60o C for Examples 11 and 12 and 313 K (40o C) for Example 18).
`
`
`
`8
`
`
`
`These data would clearly indicate to a POSITA that the effect of increasing
`
`IPR2018-01730
`U.S. Patent No. 9,072,752
`
`
`
`the co-solvent concentration does not necessarily increase the weight percentage of
`
`phospholipids such as phosphatidylcholine and ether phospholipids in extracts.
`
`Instead, these data demonstrate to a POSITA that the effect of changing extraction
`
`conditions such as co-solvent percentage with respect to a feed material is
`
`unpredictable. The only way that a POSITA would arrive at the conclusion that the
`
`claimed ether phospholipid range could be achieved by changing conditions such
`
`as co-solvent concentration is via hindsight. The hindsight bias of Petitioner is
`
`further confirmed by its inappropriate reliance on data from the ‘752 patent itself
`
`for results obtained with a 23% ethanol co-solvent. Pet. Reply at 9.
`
`Petitioner’s hindsight bias is further demonstrated by statements in Dr.
`
`Tallon’s Reply Declaration (Ex. 1086). Dr. Tallon presents a number of
`
`calculations intended to show that the neutral lipid content of the krill extract
`
`described in Catchpole could be manipulated to increase the ether phospholipid
`
`content of Extract 2. For example, Dr. Tallon states that using 3% ethanol in place
`
`of neat CO2 would increase neutral lipid extraction in step 1 and thus increase ether
`
`phospholipid content in Extract 2. Example 9 indicates that conducting a first step
`
`with 3% ethanol resulted in extraction of 90% neutral lipids. However, Dr. Tallon
`
`admitted that step 1 of Example 18 (krill) removed 88% of neutral lipids. Tallon
`
`Depo., Ex. 2026 at 26:5-22. It is not believable that the 2% difference would have
`
`
`
`9
`
`
`
`
`a meaningful impact on ether phospholipid content of Extract 2. This is especially
`
`IPR2018-01730
`U.S. Patent No. 9,072,752
`
`true given Dr. Tallon’s admission that when doing these types of calculations,
`
`small variables can lead to large amounts of unaccounted for material. See Ex.
`
`1086 at ¶69 (“[]POSITA would recognize that small variations, within the natural
`
`and known variation of the krill lipid composition, would create massive variations
`
`in the calculated difference, rendering these calculations meaningless.”). It is
`
`hindsight to use the types of calculations used by Dr. Tallon to goal seek particular
`
`claimed ranges and ignore calculation that do not support his position.
`
`Accordingly, Claims 5 and 6 are not obvious over the combination of
`
`Catchpole and Enzymotec and claims 15 and 16 are not obvious over the
`
`combination of Catchpole, Enzymotec and Sampalis II because there is both a
`
`missing element and furthermore there is no reasonable expectation of success in
`
`achieving the claimed ether phospholipid ranges of greater than about 6 and 7%.
`
`IV. Conclusion
`
`For the foregoing reasons, Patent Owner submits that at least claims 5, 6, 15
`
`and 16 should be found patentable.
`
`Dated: October 18, 2019 Respectfully submitted,
`
`
`
`
`
`
`
`
`
`
`
`
`
`/David A. Casimir / Reg. No. 42,395
`
`10
`
`
`
`
`
`
`
`
`
`IPR2018-01730
`U.S. Patent No. 9,072,752
`
`CERTIFICATE OF SERVICE
`
`The undersigned hereby certifies that on this 18th day of October 2019, a
`
`copy of the foregoing Patent Owner’s Sur-Reply to Petitioner’s Reply, Exhibit
`
`List and Ex. 2026 were served in their entirety electronically (as consented to by
`
`Petitioner) to the attorneys of record as follows:
`
`
`James F. Harrington
`
`Reg. No. 44,741
`
`Hoffmann & Baron, LLP
`jfhdocket@hbiplaw.com
`
`
`
`Ronald J. Baron
`
`
`Reg. No. 29,281
`Hoffman & Baron, LLP
`rjbdocket@hbiplaw.com
`
`453ipr@hbiplaw.com
`
`
`
`
`
`
`
`
`
`
`
`Michael I. Chakansky
`Reg. No. 31,600
`Hoffman & Baron, LLP
`micdocket@hbiplaw.com
`
`John T. Gallagher
`Reg. No. 35,516
`Hoffman & Baron, LLP
`jtgdocket@hbiplaw.com
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`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
`
`i
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
Accessing this document will incur an additional charge of $.
After purchase, you can access this document again without charge.
Accept $ Charge
Still Working On It
This document is taking longer than usual to download. This can happen if we need to contact the court directly to obtain the document and their servers are running slowly.
Give it another minute or two to complete, and then try the refresh button.
A few More Minutes ... Still Working
It can take up to 5 minutes for us to download a document if the court servers are running slowly.
Thank you for your continued patience.
This document could not be displayed.
We could not find this document within its docket. Please go back to the docket page and check the link. If that does not work, go back to the docket and refresh it to pull the newest information.
Your account does not support viewing this document.
You need a Paid Account to view this document. Click here to change your account type.
Your account does not support viewing this document.
Set your membership
status to view this document.
With a Docket Alarm membership, you'll
get a whole lot more, including:
- Up-to-date information for this case.
- Email alerts whenever there is an update.
- Full text search for other cases.
- Get email alerts whenever a new case matches your search.
One Moment Please
The filing “” is large (MB) and is being downloaded.
Please refresh this page in a few minutes to see if the filing has been downloaded. The filing will also be emailed to you when the download completes.
Your document is on its way!
If you do not receive the document in five minutes, contact support at support@docketalarm.com.
Sealed Document
We are unable to display this document, it may be under a court ordered seal.
If you have proper credentials to access the file, you may proceed directly to the court's system using your government issued username and password.
Access Government Site
