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`_________________________________
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`BEFORE THE PATENT TRIAL AND APPEAL BOARD
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`_________________________________
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`
`RIMFROST AS
`Petitioner,
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`v.
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`AKER BIOMARINE ANTARCTIC AS
`Patent Owner.
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`____________________________
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`Case IPR2018-01178
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`U.S Patent No. 9,375,453
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`_______________________
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`PATENT OWNER’S REPLY TO PETITIONER’S OPPOSITION
`TO MOTION TO AMEND CLAIMS
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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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`IPR2018-01178
`U.S. Patent No. 9,375,453
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`TABLE OF CONTENTS
`Introduction ........................................................................................... 1
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`The claims are supported by an adequate written description .............. 2
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`I.
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`II.
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`III. The contingent amended claims are not obvious .................................. 4
`There is no motivation to utilize the Yoshitomi krill
`A.
`powder for extraction and no reasonable expectation of success
`to extract the defined krill oil from the powder .................................... 4
`The cited references do not teach of suggest the 100 to
`B.
`700 mg/kg astaxanthin ester range ...................................................... 10
`CERTIFICATE OF SERVICE ......................................................................... i
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`I.
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`IPR2018-01178
`U.S. Patent No. 9,375,453
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`Introduction
`Petitioner asserts that contingent amended claims 62-74 are not supported by
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`an adequate written description and that the claims are obvious over the
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`combination of seven references: Yoshitomi (Ex. 1033), Catchpole (Ex. 1009),
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`Bottino II (Ex. 1038), Sampalis I (Ex. 1012), Randolph (Ex. 1011), Sampalis II
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`(Ex. 1013), and NKO. Petitioner’s Opposition to Contingent Motion to Amend
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`(Paper 19; “Oppo.”) Petitioner proposes four new grounds of unpatentability of the
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`contingent amended claims. Each of the grounds is based on the same combination
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`of references. Below, Patent Owner (“PO”) addresses the proposed ground of
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`rejection as applied to independent contingent amended claim 62. The arguments
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`with respect to amended claim 62 apply equally to the other grounds of rejection
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`which are directed to claims dependent on claim 62.
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`The claims as amended require extraction of a phospholipid-rich krill oil
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`with a defined lipid profile from a krill meal made by grinding, cooking and drying
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`fresh krill and subsequently formulating the extracted krill oil with a carrier for
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`oral consumption. The amendments forced Petitioner to abandon Breivik II as the
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`lead reference and substitute Yoshitomi in combination with six other references.
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`Petitioner argues that “Simply specifying that the claimed treating step includes
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`‘grinding, cooking and drying’ is not new, and therefore, not patentable.” Oppo.
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`1
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`at 4. However, this argument does not address the claims as a whole. As shown
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`U.S. Patent No. 9,375,453
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`below, the data in Yoshitomi demonstrates that the lipids in the Yoshitomi krill
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`powder were subject to both hydrolytic and oxidative degradation and also had an
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`abnormally low lipid content. This is consistent with teachings in the prior art that
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`krill meal is not suitable for extraction of a phospholipid-rich krill meal as claimed.
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`Petitioner’s expert, who has no experience with krill meal processing on board a
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`ship (See Ex. 2026, p. 7, l. 7-23), failed to consider this data in Yoshitomi and its
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`impact on motivation to combine and reasonable expectation of success.
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`II. The claims are supported by an adequate written description
`Petitioner alleges that there is no written description support for the method
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`steps of grinding, cooking and drying krill to provide the krill meal that is
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`extracted. Oppo. at 5-6. The level of detail required to satisfy the written
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`description requirement varies depending on the nature and scope of the claims and
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`on the complexity and predictability of the relevant technology. Ariad Pharm., Inc.
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`v. Eli Lilly & Co., 598 F.3d 1336, 1340, 94 USPQ2d 1161, 1167 (Fed. Cir. 2010 en
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`banc)(setting forth factors for evaluating the adequacy of the disclosure, including
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`“the existing knowledge in the particular field, the extent and content of the prior
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`art, the maturity of the science or technology, [and] the predictability of the aspect
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`at issue.”)
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`2
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`Petitioner’s arguments are devoid of analysis and fail to consider factors
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`relevant to written description such as those discussed in Ariad. Proper application
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`of those factors leads to a conclusion that the claims are supported by an adequate
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`written description. Ex. 2025, Hoem Reply Decl., ¶6. The specification
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`specifically teaches the use of krill meal as a source material for extraction. Id.,
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`see, e.g., Ex. 2012 at p. 6, l. 9-21; p. 15, l. 5-21; p. 44, Example 6). The
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`specification specifically describes production of the meal by steps including
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`grinding, cooking and drying. Id. Petitioner’s expert admits that these steps were
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`known in the art. Tallon Reply Decl. Ex. 1086, ¶¶253-259. Thus, given the
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`existing knowledge in the field and the content of the prior art, a person of ordinary
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`skill in the art (“POSITA”) would readily recognize that the inventors were in
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`possession of a method of making krill meal by cooking, grinding and drying and
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`ten using that krill meal for extraction of krill oil as claimed. Ex. 2025, Hoem
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`Reply Decl., ¶6.1
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`1 Petitioner alleges in a footnote that claims are indefinite but provides no
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`supporting arguments as to why the claims are indefinite in light of the
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`specification. Claims with similar amendments relating to the ether phospholipid
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`content and total phospholipid content were found to be not indefinite. IPR2018-
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`3
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`III. The contingent amended claims are not obvious
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`U.S. Patent No. 9,375,453
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`There is no motivation to utilize the Yoshitomi krill powder for
`A.
`extraction and no reasonable expectation of success to extract the defined krill
`oil from the powder
`When analyzing obviousness, the claims must be considered as a whole.
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`The claims as amended are directed to a process whereby a phospholipid-rich krill
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`oil with a defined ether phospholipid, total phospholipid, triglyceride and
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`astaxanthin ester content is extracted from a meal made by grinding, cooking and
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`drying fresh krill and then formulated for oral consumption. A POSITA would not
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`combine Yoshitomi with the other six references to arrive at the claimed process
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`because: 1) the data in Yoshitomi demonstrate that the lipids in the Yoshitomi krill
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`powder (“YKP”) were subject to hydrolytic and oxidative degradation; 2) the lipids
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`in YKP were present at abnormally low levels; and 3) the prior art teaches away
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`from using krill meal made by grinding, cooking and drying for extraction of
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`phospholipid rich krill oils as claimed.
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`Yoshitomi states that its krill powder has all the components of fresh krill
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`and that no anti-oxidant is needed to prevent lipid degradation. Ex. 1033 at [0002].
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`However, the data in Yoshitomi is not consistent with this statement. The data
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`00295, Final Written Decision (Paper 35) at 57. That holding would be controlling
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`under Petitioner’s collateral estoppel theory.
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`4
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`demonstrates that the lipids in YKP are subject to both hydrolytic and oxidative
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`degradation to a similar extent as convention krill meal. Ex. 2025 (Hoem Reply
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`Decl.), ¶15. Specifically, Table III of Yoshitomi shows that the acid value of YKP
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`immediately after manufacture was 18.1 with no anti-oxidant added and 19.2 with
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`anti-oxidant added. Acid value is a general indicator of hydrolytic rancidity of
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`lipids which in krill can be caused by both enzymatic and non-enzymatic
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`processes. Id. These acid values are consistent with hydrolytic degradation of the
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`lipids in YKP and are similar to or higher than conventional krill meals such as
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`those described in Yamaguchi. Id., see also Ex. 2002 (Yamaguchi) at 2.
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`Table 3 of Yoshitomi also provides data on peroxide value, which is an early
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`indicator of oxidative degradation. Ex. 2025, ¶15. The starting peroxide value in
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`reported in Table 3 is 1.8 with the antioxidant and 4.1 without the antioxidant.
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`These values are high for a product that has just been manufactured and
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`demonstrate that the lipids in YKP were subject oxidative degradation. Id. By
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`comparison, the NKO GRAS submission (Ex. 1075) which has been relied on
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`Petitioner in these proceedings, indicates that the peroxide value of Neptune Krill
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`Oil is less than 0.1. Ex. 1075 at 0010, Table 2. This is over 18 times lower than
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`the value reported in Table 3 of Yoshitomi. Ex. 2025, ¶15. When the Yoshitomi
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`data is considered as a whole, a POSITA would recognize that the Yoshitomi
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`5
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`process does not improve lipid quality as compared to conventional krill meals
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`such as those disclosed in Yamaguchi.2 Id.
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`As provided in Table 5, the YKP also has an abnormally low crude fat
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`content. Ex. 2025, ¶16. In contrast, the freeze-dried krill powder of Catchpole has a
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`lipid content (i.e., crude fat content) of 21.4%. Ex. 1009, p. 0024. The 21.4% lipid
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`content of the freeze-dried krill powder of Catchpole is consistent with the average
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`lipid content of both freeze-dried krill powder and krill meals. Ex. 2025, ¶16. The
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`abnormally low lipid content of the Yoshitomi krill powder is consistent with lipid
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`degradation. Id.
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`According to Dr. Hoem, due both to the presence of lipids that have been
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`subjected to hydrolytic and oxidative degradation and the abnormally low lipid
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`content of YKP, a POSITA would not choose to combine Yoshitomi with the other
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`cited references for production of a krill oil with the lipid profile defined in the
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`claims and which is then formulated for human consumption or encapsulated. In
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`fact, a comparison of the starting materials for krill oil extraction in the references
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`2 As discussed by Dr. Hoem, Table 4 lists starting peroxide values of 0. No reason
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`is provided for the inconsistency between the starting values in tables 3 and 4. A
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`POSITA would consider the data as a whole and conclude that YKP is subject to
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`significant levels of hydrolytic and oxidative degradation. Ex. 2025, ¶16.
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`6
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`in the proposed grounds of unpatentability indicates that all of the references in the
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`proposed combination except Yoshitomi used freeze dried, fresh or frozen krill for
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`extraction of the described krill oils. Ex. 2025, ¶¶18-19. This is clear evidence that
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`a POSITA at the time of the invention would not utilize a krill meal such as YKP
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`as a starting material for extraction and instead would use fresh, freeze-dried or
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`frozen krill. Id.
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`This analysis is consistent with the fact that the prior art teaches away from
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`utilization of krill meals made by grinding, cooking and drying for extraction of
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`phospholipid-rich oils. Ex. 2025, ¶11. Yamaguchi teaches that supercritical fluid
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`extraction with carbon dioxide should be used to extract neutral krill oil from krill
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`meal to exclude “phospholipids that interfere with the utilization of krill oils.” Ex.
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`2002, abstract. Yamaguchi further reported that extraction from krill meal yielded
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`one-third less neutral krill oil than extraction from a freeze-dried krill powder. Id.
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`at p. 905, col. 2. As stated by Yamaguchi: “The lower yields from meal oil are
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`probably attributable to the fact that that the oil of the krill meal was in part
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`deteriorated by oxidation or polymerization to such an extent that only limited
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`extraction occurred with SC-CO2.” Id. Yamaguchi then states: “Judging from this
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`result we think that SC-CO2 extraction is suitable method to obtain undenatured
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`oils from meals of marine origin.” Id. Thus, Yamaguchi is teaching using SC-CO2
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`to remove neutral lipids and to leave phospholipids and other degraded and
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`7
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`oxidized lipids in the meal. Ex. 2025, ¶12. Finally, Petitioner’s argument that
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`Breivik teaches that cooking denatures krill lipases thus allowing grinding without
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`hydrolysis (Oppo. at 8) is not supported by the cited passage in Breivik, which
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`actually distinguishes meals made by conventional processes which would be
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`understood by a POSITA to include grinding, cooking and drying. See Ex. 2025
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`(Hoem Decl.) ¶16.
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`There is also no reasonable expectation of success provided by the combined
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`references. As discussed by Dr. Hoem, YKP presents a very different matrix for
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`extraction than, for example, the freeze-dried krill powder utilized in Catchpole.
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`Ex. 2025, ¶¶22-23. Yamaguchi provided a direct comparison between neat SFE
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`CO2 extraction from a freeze-dried krill powder and krill meal and found the
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`extraction yield of lipids from the krill meal was one third of that obtained from the
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`freeze-dried krill powder and concluded that the difference was to oxidized and
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`polymerized lipids in the krill meal. Id.
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`Taking the ether and total phospholipid limitations as an example, a
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`POSITA would not recognize that YKP could be used in a process to provide a
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`krill oil containing 4-8% ether phospholipids or from 30 to 60% total
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`phospholipids. Ex. 2025, ¶27. Petitioner relies on Extract 2 of Catchpole which
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`reportedly contains 4.8% ether phospholipids to provide the ether phospholipid
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`range. However, that content of ether phospholipids was obtained from an
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`extraction of a freeze-dried krill powder containing 21.4% lipids. YKP is made by
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`a grinding, cooking and drying process and has only a 7% lipid content and would
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`be recognized by a POSITA to contain oxidized and polymerized phospholipids.
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`Yamaguchi specifically teaches that extraction from krill meals (i.e., meals made
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`by cooking and drying) resulted in yields of only one third of those observed from
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`a freeze-dried krill powder due in part to polymerized and oxidized lipid products.
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`There is no basis for a POSITA to expect that an oil containing 4 to 8% ether
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`phospholipids (or for that matter 30 to 60% total phospholipids) could be extracted
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`from a starting material such as YKP.
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`Petitioner’s discussion of motivation to combine and reasonable expectation
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`of success fail to consider the different properties of YKP as compared to the fresh,
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`frozen or freeze-dried extraction materials utilized in the remainder of the cited
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`references. Petitioner’s arguments regarding motivation to combine and
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`expectation of success are general in nature. See Oppo. at 20-21, Tallon Reply
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`Decl. ¶¶115, 216-221. However, that cited testimony provides no specific analysis
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`as to why there would be a motivation to start with the YKP in a process in which
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`the specifically defined krill oil is extracted, or why a POSITA would start with
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`YKP when all of the other cited references utilize fresh, frozen or freeze-dried
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`krill. Dr. Tallon’s analysis further fails to consider the low lipid content and high
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`acid and peroxide values YKP. The issue is whether a POSITA would start with
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`YKP in a process to extract a krill oil with the defined lipid content in the claims
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`and then formulate that oil for oral consumption. Petitioner’s arguments fail to
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`address the claims and the prior art as a whole.
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`The cited references do not teach or suggest the 100 to 700 mg/kg
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`astaxanthin ester range
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`Petitioner relies on NKO, Randolph and Sampalis II to provide the claim
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`limitation of from 100 to 700 mg/kg astaxanthin esters.3 With respect to NKO, the
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`PTAB has already found that NKO does not provide the claimed range of 100 to
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`700 mg/kg astaxanthin esters. IPR2018-00295, Paper 35 at 66-67. References
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`cited by Petitioner clearly establish that NKO contained greater than 1500 mg/kg
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`astaxanthin esters. Ex. 2025, ¶28; see Ex. 1070, 1071 and 1075, p. 0010.
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`Moreover, obviousness cannot be predicated on what is not known at the time an
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`invention is made, even if the inherency of a certain feature is later
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`established. See, In re Newell, 891 F.2d 899, 901 (Fed. Cir. 1989). The alleged
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`admission was not known to a POSITA. There can be no motivation to combine
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`the astaxanthin ester ranges from Patent Owner’s own specification with the other
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`3 Patent Owner notes that a Request for Rehearing is pending in IPR2018-00295 in
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`regard to the contingent motion to amend claims with respect to the astaxanthin
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`ester limitation and that collateral estoppel may apply depending on the outcome.
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`10
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`cited references, let alone for achieving the ranges of each of the claimed
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`components.
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`Randolph also does not provide the astaxanthin ester range as discussed in
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`detail by Dr. Hoem. Ex. 2025, ¶¶29-31. First, the passages relied on by Petitioner
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`teach that a composition can contain any amount of astaxanthin, not that krill oil
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`can contain any amount of astaxanthin. Id. The compositions of Randolph can
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`contain more than 25 ingredients, one of which can be krill oil, and further indicate
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`that astaxanthin can come other sources. Id., See Ex. 1013 at [0021]. The krill oil
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`content in listed in [0040] of Randolph (i.e., 300 mg and about 3000 mg of a krill
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`oil ingredient) is not related to the astaxanthin content of the composition as a
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`whole listed in [0044] Randolph (i.e., 0.5 mg and about 50 mg of an astaxanthin
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`ingredient). Id. Second, even assuming those ranges can be combined, Dr.
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`Tallon’s calculations cherry pick the high end of the first range (3000 mg krill oil)
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`and the low end of second range (0.5 mg astaxanthin) in order to arrive at the
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`claimed range. A POSITA would not combine the ranges in this manner. Ex.
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`2025, ¶31.
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`Finally, as detailed by Dr. Hoem, a POSITA would not derive the claimed
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`astaxanthin ester range from Sampalis II. Ex. 2025, ¶¶32-34. First, the first
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`passage relied on by Petitioner at l. 1-7, p. 0032 of Sampalis II refers to the content
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`of antioxidants in general and states that they can be present at levels greater than
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`20 or 200 mg/ml. This passage does not state that astaxanthin is present at those
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`levels. Second, the astaxanthin values listed in Table 5 of Sampalis II would be
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`discredited by a POSITA. Ex. 2025, ¶33. Table 5 lists both canthaxanthin and
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`flavonoids as being present in the krill extract. A POSITA would recognize that
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`this is impossible because as disclosed in Grynbaum, which has been cited by
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`Petitioner in these proceedings, the only carotenoid present in krill is astaxanthin.
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`Ex. 1039 at 0008. This would indicate to a POSITA that however those values
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`were determined, they cannot be trusted because of the inclusion of compounds
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`that cannot be present in a krill extract. Ex. 2025, ¶33. Third, Sampalis II
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`discloses that the claimed product is NKO and discloses the same production
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`process as used in the NKO GRAS submission (Ex. 1075) which would be
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`understood to provide at least 1500 mg/kg astaxanthin esters. Id. at ¶¶28, 34.
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`It is respectfully submitted that the contingent amended claims are
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`patentable.
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`Dated: August 14, 2019
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`Respectfully submitted,
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`Casimir Jones S.C.
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`By: /David A. Casimir/
`David A. Casimir, Ph.D.
`Registration No. 42,395
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`IPR2018-01178
`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 REPLY TO PETITIONER’S
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`OPPOSITION TO MOTION TO AMEND CLAIMS, Exhibit List, and
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`Exhibits 2012, 2025 and 2026 were served in their entirety electronically (as
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`consented to by Petitioner) to the attorneys 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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`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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`453ipr@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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