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`UNITED STATES PATENT AND TRADEMARK OFFICE
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`PAPER 30
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`BEFORE THE PATENT TRIAL AND APPEAL BOARD
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`RIMFROST AS
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`Petitioner
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`v.
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`AKER BIOMARINE ANTARCTIC AS
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`Patent Owner
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`Case No.: IPR2018-01179
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`U.S. Patent No. 9,375,453
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`Issue Date: June 28, 2016
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`Title: Bioeffective Krill Oil Compositions
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`PETITIONER’S SUR-REPLY TO PATENT OWNER’S
`MOTION TO AMEND
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`Inter Partes Review Case No.: IPR2018-01179
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`U.S. Patent No. 9,375,453
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`TABLE OF CONTENTS
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`I.
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`INTRODUCTION .............................................................................................. 1
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`II. THE PROPOSED CLAIMS FAIL TO COMPLY WITH SECTION 112 ........ 1
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`III. THE PROPOSED CLAIMS ARE UNPATENTABLE ..................................... 3
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`A. A POSITA Would Have Motivated To Use The “Grinding, Cooking
`And Drying” Process Described In Yoshitomi ..................................... 3
`B. NKO, Randolph And Sampalis II Each Disclose Krill Oil Satisfying
`The 100-700 mg/kg Astaxanthin Esters Limitation .............................. 8
`IV. CONCLUSION ................................................................................................12
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`i
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`Inter Partes Review Case No.: IPR2018-01179
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`U.S. Patent No. 9,375,453
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`I.
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`INTRODUCTION
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`
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`Patent Owner does not dispute that the steps of “grinding, cooking and
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`drying” krill were known in the art. Nor does Patent Owner dispute that Yoshitomi
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`expressly discloses these steps, and teaches the benefits of denaturing krill.
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`Nevertheless, by pointing to three values taken from Yoshitomi’s specification,
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`and relying on Dr. Hoem’s unsupported speculation regarding acid and peroxide
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`values, Patent Owner attempts to limit Yoshitomi’s disclosure to a single krill
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`powder it names “YKP.” Patent Owner also tries to rewrite the proposed claims to
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`recite a method of producing a “phospholipid-rich krill oil” extracted from krill
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`meal that is not subjected to any hydrolytic or oxidative degradation. Contrary to
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`Patent Owner’s arguments, Yoshitomi expressly discloses and teaches grinding,
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`cooking and drying fresh krill which, in combination with the other prior art of
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`record, renders claims 75-84 unpatentable.1
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`II. THE PROPOSED CLAIMS FAIL TO COMPLY WITH SECTION 112
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`It is not contested that the term “grinding” can only be found in a single
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`sentence, branded as one of over 175 so-called “embodiments” supposedly
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`1 Patent Owner refuses to address why Yoshitomi was not mentioned in its MTA or
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`why that omission did not violate its duty of candor. 37 C.F.R. § 42.11; see
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`Petitioner’s Opposition (Paper 19) (“Opp.”), p. 2, n.2.
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`1
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`Inter Partes Review Case No.: IPR2018-01179
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`U.S. Patent No. 9,375,453
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`described in the ‘162 application. The only reason Patent Owner offers why this
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`isolated reference satisfies the written description requirement of Section 112 is
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`that the proposed “grinding, cooking and drying” steps were known in the art. PO
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`Reply, 3. That the steps of “grinding, cooking and drying” krill were known and
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`obvious, however, is insufficient to satisfy Section 112’s written description
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`requirement. Ariad Pharm., Inc. v. Eli Lilly & Co., 598 F.3d 1336, 1352 (Fed. Cir.
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`2010) (“a description that merely renders the invention obvious does not satisfy”
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`the written description requirement). Patent Owner has failed to meet its burden
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`with respect to the written description requirement and the proposed “grinding,
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`cooking and drying” limitation. Patent Owner’s MTA should be denied.
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`Patent Owner feigns uncertainty as to why the proposed claims are also
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`indefinite under Section 112. PO Reply, 3, n.1.2 Since the recited ether
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`phospholipid and non-ether phospholipid values only add up to a minimum of 31%
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`and a maximum of 58% (i.e., 4-8% ether phospholipids + 27-50% non-ether
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`phospholipids), it is mathematically impossible to achieve either the minimum or
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`maximum total phospholipid limitation. The proposed claims are also indefinite.
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`2 Patent Owner wrongly avers that collateral estoppel bars Petitioner from arguing
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`that proposed claims 75-84 are indefinite. Petitioner, however, never raised, and
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`the Board never addressed, the issue of indefiniteness in IPR2018-00295.
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`2
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`Inter Partes Review Case No.: IPR2018-01179
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`U.S. Patent No. 9,375,453
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`III. THE PROPOSED CLAIMS ARE UNPATENTABLE
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`A. A POSITA Would Have Motivated To Use The “Grinding,
`Cooking And Drying” Process Described In Yoshitomi
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`Patent Owner tries to limit the scope of Yoshitomi’s disclosure to a single
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`“krill powder” it names “YKP,” and then maintains that YKP is an unacceptable
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`product because it was purportedly subject to excessive hydrolytic and oxidative
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`degradation and has an abnormally low level of lipids, relying on Dr. Hoem’s
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`unsupported suppositions regarding the acid and peroxide values and “course fat”
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`values found in Tables 3 and 5, respectively; values that are acceptable for
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`commercial krill oil products. PO Reply, 4; infra, p. 7. Patent Owner concludes
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`that a “POSITA would not choose to combine Yoshitomi with the other cited
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`references for the production of a krill oil.” PO Reply, 6. Patent Owner’s
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`arguments are meritless.
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`Yoshitomi repeatedly and unambiguously describes grinding (i.e., chopping
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`or coarsely crushing), cooking (i.e., heating) and drying fresh Euphausia superba
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`krill to produce a denatured krill powder containing “all the components” of fresh
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`krill. See, e.g., Exhibit 1033, Abstract; ¶¶ 0009, 0021-0023, 0025, 0029, 0032-
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`0034, 0037, 0041, 0049, 0051, 0055. It is noted that excessive cooking and drying
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`temperatures “reduces astaxanthin . . . present in krill, reduces vitamins and
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`oxidizes lipids.” Id., ¶ 0034. Yoshitomi, however, discloses that one of the
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`benefits associated with grinding or chopping krill into smaller pieces is improved
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`U.S. Patent No. 9,375,453
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`thermal efficiency during the subsequent denaturing (i.e., cooking and drying)
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`steps. Id., ¶ 0032. Because of the improved thermal efficiency associated with a
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`ground krill starting material, Yoshitomi discloses that the cooking and drying
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`steps need not be performed “at overly high temperatures [or] for an overly long
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`time,” resulting in an “improvement in product quality.” Id., ¶ 0037.3
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`“A reference must be considered for everything it teaches by way of
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`technology and is not limited to the particular invention it is describing and
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`attempting to protect.” EWP Corp. v. Reliance Universal Inc., 755 F.2d 898, 907
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`(Fed. Cir. 1985); see Medichem, S.A. v. Rolabo, S.I., 437 F.3d 1157, 1165 (Fed.
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`Cir. 2006) (“[a] given course of action often has simultaneous advantages and
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`disadvantages and this does not necessarily obviate motivation to combine”).
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`Yoshitomi unequivocally discloses grinding, cooking and drying fresh
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`Euphausia superba krill to produce a denatured krill product with “all the
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`components” of fresh krill. Supra, pp. 3-4. Ignoring this clear mandate, Patent
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`Owner asserts that the acid and peroxide values reported in Table 3 and the course
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`fat value in Table 5 of Yoshitomi demonstrate that grinding results in a krill
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`product having unacceptable levels of hydrolytic and oxidative degradation. PO
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`3 Catchpole also discloses that grinding feed material improves the efficiency of
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`solvent extraction. See Exhibit 1009, p. 0011, lines 30-32.
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`4
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`Reply, 5-6. Patent Owner’s argument, however, is predicated on the very
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`antithesis of Yoshitomi’s stated purpose; producing a denatured krill product in
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`which “the enzymes in krill [are] perfectly disabled.” Exhibit 1033, ¶ 0022; supra,
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`pp. 3-4. Notably, Dr. Hoem could not identify a single reference supporting his
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`conclusion that the specific acid and peroxide values reported in Table 3 disclose
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`that a krill product was subjected to unacceptable levels of hydrolytic and
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`oxidative degradation. See, e.g., Hoem Dep. (Exhibit 1151), 50:14-24; 82:9-83:24.
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`Patent Owner’s attempt to dismiss the entirety of Yoshitomi’s disclosure based on
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`three values from Tables 3 and 5 fails for a number of reasons.
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`As an initial matter, Patent Owner’s arguments based on its comparison of
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`the specific krill meal identified in Yamaguchi and the denatured krill products
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`encompassed by Yoshitomi are inapt. In particular, Patent Owner asserts that
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`Yamaguchi teaches away from grinding krill because the specific krill meal in
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`Yamaguchi “was deteriorated by oxidation or polymerization,” and that two values
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`from Table 3 indicates all products encompassed by Yoshitomi have a quality
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`similar to “conventional krill meals such as disclosed in Yamaguchi.” PO Reply,
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`7-9. However, other than noting the krill meal was purchased, Yamaguchi
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`provides absolutely no details regarding, inter alia, how the krill meal was
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`processed or the meal’s acid and peroxide values; precluding even the most
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`cursory comparison with Yoshitomi. See Yamaguchi (Exhibit 2002), p. 1. The
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`5
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`U.S. Patent No. 9,375,453
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`irrelevance of Patent Owner’s strained comparison is further underscored by the
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`fact that Yoshitomi describes a process to denature and perfectly disable the
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`enzymes present in fresh krill. Supra, pp. 3-4. In contrast, the krill meal used by
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`Yamaguchi produced an “undenatured oil.” Exhibit 2002, at p. 2. As Dr. Hoem
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`confirmed, once a product is denatured, the product stays denatured. Hoem Dep.
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`(Exhibit 1151), 139:10-19. Thus, it would be impossible to extract “undenatured
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`oil” from Yoshitomi’s denatured krill product. Patent Owner’s arguments,
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`predicated on its attempt to infer from Yamaguchi’s krill meal that the denatured
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`krill product described in Yoshitomi has poor lipid quality should be rejected.
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`Patent Owner’s comparison of the peroxide values from Table 3 of
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`Yoshitomi and the NKO GRAS Notice is also a non-starter. PO Reply, 5-6.
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`Patent Owner’s attempt to draw a distinction between the peroxide values of the
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`denatured krill powders or meals encompassed by Yoshitomi and a commercial
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`krill oil product is “comparing apples to oranges.” See Hoem Dep. (Exhibit 1151),
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`48:5-9. Even if such a comparison was appropriate, Enzymotec’s GRAS reports
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`that acceptable peroxide values for krill extracts are less than 5. Exhibit 1048, p. 7;
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`see Tallon Decl. (Exhibit 1006), ¶ 55, n.3. This is consistent with peroxide values
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`of 1.8 and 4.1 reported in Table 3. In fact, Dr. Hoem admitted that krill oil with
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`peroxide values less than 5 is acceptable. Hoem Dep. (Exhibit 1151), 19:4-11; see
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`17:14-21:2.
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`6
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`Inter Partes Review Case No.: IPR2018-01179
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`U.S. Patent No. 9,375,453
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`Patent Owner’s “acid value” argument also fails to detract from Yoshitomi’s
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`disclosure of grinding, cooking and drying fresh krill. Dr. Hoem conceded the acid
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`value of a krill extract equals about twice the extract’s free fatty acid content. Id.,
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`6:21-7:19. Notably Table 2 of the ‘453 patent reports that krill meal produced in
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`accordance with the patent’s teachings had a free fatty acid content of 9.0. Exhibit
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`1001, 18:48-65. Based on Dr. Hoem’s testimony, this corresponds to an acid value
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`of 18 which is comparable to the acid values in Table 3 of Yoshitomi (e.g., 18.1
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`and 19.2). Dr. Hoem even confirmed that the acceptable acid value for krill oil
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`pursuant to a current “Codex” standard is less than 45; twice the values reported in
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`Table 3. Hoem Dep. (Exhibit 1151), 42:9-22; 44:23-45:16; see Exhibit 1147.4
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`Patent Owner’s naked assertion that the course fat content 7% in Table 5 of
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`Yoshitomi was abnormal and was consistent with lipid degradation is unavailing.
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`PO Reply, 6. For example, other than the documents disclosed in his declaration,
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`Dr. Hoem could not point to any document expressly disclosing that 7% fat or lipid
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`content evidenced lipid degradation. Hoem Dep. (Exhibit 1151), 82:9-83:24.
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`4 Dr. Hoem testified that krill has a higher free fatty acid content than fish. Exhibit
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`1151, 6:21-7:19; 49:10-50:13; 136:9-18. A POSITA would have expected that the
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`acid value for a quality krill product would have been higher than that for fish oil
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`which Dr. Hoem seems to have been referencing. See Exhibit 1147, §§ 3.3.1-3.3.2.
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`7
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`Inter Partes Review Case No.: IPR2018-01179
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`U.S. Patent No. 9,375,453
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`Tellingly, Dr. Hoem agreed that phospholipids and neutral lipids could be
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`extracted from Yoshitomi’s 7% course fat krill product. Id., 108:7-109:16.
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`Finally, Yoshitomi emphatically discloses that the recited grinding, cooking
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`and drying steps results in a denatured krill product, and further describes the
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`benefits associated with grinding fresh krill. Supra, pp. 5-6. This unambiguous
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`disclosure cannot be disregarded, even assuming Yoshitomi’s grinding, cooking
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`and drying steps results in a krill product with some degree of hydrolytic and
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`oxidative degradation as proposed by Patent Owner. See Winner Int’l Royalty
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`Corp. v. Wang, 202 F.3d 1340, 1349 n.8 (Fed. Cir. 2000) (“that the motivating
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`benefit comes at the expense of another benefit, however, should not nullify its use
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`as a basis to modify the disclosure of one reference with the teachings of another”).
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`B. NKO, Randolph And Sampalis II Each Disclose Krill Oil
`Satisfying The 100-700 mg/kg Astaxanthin Esters Limitation
`Patent Owner’s argument regarding the specific commercial NKO krill oil
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`formulation identified in the ‘453 patent is factually and legally wrong.
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`Petitioner has never argued that every commercial NKO formulation
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`inherently possessed 100-700 mg/kg astaxanthin esters as Patent Owner suggests.
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`PO Reply, 10. Rather, Petitioner has steadfastly maintained that the specific NKO
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`formulation identified in Table 16 of the ‘453 patent that Patent Owner admitted
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`had 472 mg/kg astaxanthin esters and represented was the “closest prior art,”
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`8
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`U.S. Patent No. 9,375,453
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`satisfies the proposed astaxanthin esters limitation. See, e.g., Petitioner’s Opp., 13;
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`Tallon Reply/Opp. (Exhibit 1086), ¶¶ 303-304.
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`Additionally, Patent Owner’s argument that these admissions were “not
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`known to a POSITA,” and therefore cannot be considered by the Board in
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`accessing the patentability of the proposed clams is legally wrong. PO Reply, 10.
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`Specifically, the Federal Circuit has held “[a]dmissions in the specification
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`regarding the prior art are binding on the patentee for purposes of a later inquiry
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`into obviousness.” Pharmastem Therapeutics v. Viacell, 491 F.3d 1343, 1362
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`(Fed. Cir. 2007); see, e.g., In re Nomiya, 509 F.2d 566, 570-71 (CCPA 1975)
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`(representations in specification are admissions for purposes of obviousness).
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`While both of these cases were cited by Petitioner, Opp., 13, Patent Owner chose
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`to ignore this controlling precedent. In sum, Patent Owner cannot run from its
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`“binding admissions” that a specific prior art NKO formulation with 472 mg/kg
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`astaxanthin esters was the “closest prior art.” This NKO formulation, in
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`combination with the prior art of record, renders claims 75-84 obvious.
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`Patent Owner maintains that Randolph’s disclosure of compositions
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`containing “any amount” of astaxanthin, and in particular, 0.5-50 mg, is “not
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`related to,” and somehow inapplicable to the krill oil compositions disclosed in
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`Randolph. Patent Owner further contends that the proposed astaxanthin esters
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`limitation is obtained by “cherry picking” the ranges disclosed in Randolph. PO
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`9
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`U.S. Patent No. 9,375,453
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`Reply, 11. It cannot be legitimately disputed that Randolph expressly teaches
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`compositions containing “between about 0.5 mg and about 50 mg” of astaxanthin,
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`and “between about 300 mg and about 3000 mg [.003 kg]” of krill oil. Randolph,
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`Exhibit 1011, ¶¶ 0040, 0044 (emphasis added). Dr. Tallon used the endpoint
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`values for astaxanthin and krill oil and calculated that Randolph discloses krill oil
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`compositions having 167 mg/kg of astaxanthin (i.e., 0.5 mg/.003 kg), which is
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`equivalent to 158 mg/kg astaxanthin esters. Tallon Reply/Opp. (Exhibit 1086), ¶¶
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`306-311. Relying on Dr. Tallon’s calculation, the Board previously found that
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`Randolph describes compositions with amounts of astaxanthin esters that “overlap
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`with the range recited in the substitute claims.” IPR2018-00295 (Paper 35)
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`(Exhibit 1129), 67-68; In re Peterson, 315 F.3d 1325, 1329 (Fed. Cir. 2003).
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`“A reference must be considered for everything it teaches.” In re Applied
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`Materials, Inc., 692 F.3d 1289, 1298 (Fed. Cir. 2012). Patent Owner ignores both
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`this fundamental precept and the breadth of Sampalis II’s disclosure in arguing that
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`a “POSITA would not derive the claimed astaxanthin range from Sampalis II.” PO
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`Reply, 11. Sampalis II is directed to phospholipid extracts “from a marine or
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`aquatic biomass.” Exhibit 1013, p. 1 (Abstract); p. 3, lines 9-12; p. 5, lines 1-3.
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`Sampalis II also states the recited extracts are preferably extracted from krill, such
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`as Euphausia superba, id., p. 0027, lines 2-9, and notes that antioxidants, such as
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`astaxanthin esters are present in amounts of at least 20 mg/100 ml. Id., p. 0032,
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`10
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`U.S. Patent No. 9,375,453
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`lines 1-7; Tallon Reply/Opp. (Exhibit 1086), ¶¶ 312-316. Dr. Hoem confirmed 20
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`mg/100 ml astaxanthin is equivalent to 200 mg/kg astaxanthin and 190 mg/kg
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`astaxanthin esters. Hoem Dep. (Exhibit 1128), 207:13-209:9.
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`Patent Owner’s suggestion that a POSITA would “discredit” Sampalis II’s
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`disclosure and teachings of krill extracts having at least 200 mg/kg astaxanthin
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`because Table 5 lists components found in both marine and aquatic biomass
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`extracts is meritless. First, Patent Owner asserts that a POSITA would recognize
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`that it is “impossible” for a krill extract to contain canthaxaxanthin by
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`misrepresenting Grynbaum as confirming “the only carotenoid present in krill is
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`astaxanthin.” PO Reply, 12. While Grynbaum notes that its analysis shows that
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`“astaxanthin was the sole carotenoid identified,” the very next sentence states:
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`“This is also inconsistent with the literature.” Exhibit 1039, p. 0008. With that
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`important caveat, a POSITA would not “discredit” the teachings of Sampalis II as
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`averred by Patent Owner. Second, since Sampalis II is directed to phospholipid
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`extracts “from a marine or aquatic biomass,” it is not surprising that Table 5
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`identifies flavonoids as being present in the various extracts encompassed by the
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`teachings of Sampalis II. Finally, Patent Owner’s assertion that Sampalis II
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`“discloses the same production process as used in the NKO GRAS submission” is
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`simply unsupported attorney argument. PO Reply, 12.
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`11
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`Inter Partes Review Case No.: IPR2018-01179
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`U.S. Patent No. 9,375,453
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`At bottom, the astaxanthin esters disclosures of NKO, Randolph or Sampalis
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`II in combination with the prior art of record renders claims 75-84 obvious.
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`IV. CONCLUSION
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`A preponderance of evidence demonstrates that claims 75-84 are disclosed
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`and taught by the prior art of record and are unpatentable.
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`Dated: September 23, 2019
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`Respectfully submitted,
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`/james f. harrington/
`James F. Harrington
`jfhdocket@hbiplaw.com
`Registration No. 44,741
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`HOFFMANN & BARON, LLP
`6900 Jericho Turnpike
`Syosset, New York 11791
`(516) 822- 3550
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`Attorney for Petitioner
`Rimfrost AS
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`12
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`Inter Partes Review Case No.: IPR2018-01179
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`U.S. Patent No. 9,375,453
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`CERTIFICATE OF SERVICE
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`I hereby certify that on this 23rd day of September, 2019, PETITIONER’S
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`SUR-REPLY TO PATENT OWNER’S MOTION TO AMEND was served in
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`its entirety on the following counsel of record by e-mail at the address provided in
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`the Patent Owner’s Mandatory Notice Information as set forth below:
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`
`David A. Casimir, Ph.D.
`J. Mitchell Jones, Ph.D.
`CASIMIR JONES S.C.
`2275 Deming Way, Suite 310
`Middleton, WI 53562
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`dacasimir@casimirjones.com
`jmjones@casimirjones.com
`docketing@casimirjones.com
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`By:
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`/james f. harrington/
`James F. Harrington
`jfhdocket@hbiplaw.com
`Registration No. 44,741
`
`HOFFMANN & BARON, LLP
`6900 Jericho Turnpike
`Syosset, New York 11791
`(516) 822-3550
`
`
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