throbber
UNITED STATES PATENT AND TRADEMARK OFFICE
`_____________________________
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`BEFORE THE PATENT TRIAL AND APPEAL BOARD
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`_____________________________
`
`ARGENTUM PHARMACEUTICALS LLC, MYLAN PHARMACEUTICALS
`INC., BRECKENRIDGE PHARMACEUTICAL, INC., AND ALEMBIC
`PHARMACEUTICALS, LTD.,
`Petitioners,
`
`v.
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`RESEARCH CORPORATION TECHNOLOGIES, INC.,
`Patent Owner.
`
`_____________________________
`
`IPR2016-002041
`Patent RE 38,551
`_____________________________
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`
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`PETITIONERS’ RESPONSE TO MOTION FOR OBSERVATIONS
`REGARDING THE CROSS-EXAMINATION OF DR. BINGHE WANG
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`1 Case IPR2016-01101, Case IPR2016-01242, and Case IPR2016-01245 have been
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`joined with this proceeding.
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`IPR2016-00204
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`Petitioners file this Response to Patent Owner’s Motion for Observations on
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`Cross-examination of Dr. Binghe Wang (Paper 65) by Due Date 5 (Papers 20, 50).
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`Petitioners respectfully disagree that Patent Owner’s Observations are relevant or
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`demonstrate inconsistency. Several of Observations are argumentative. Petitioners
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`respectfully reserve their right to respond during oral hearing.
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`Observation 1: Patent Owner’s Observation omits relevant testimony.
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`Ex.2194, 237:14-247:1. Dr. Wang testified: “So based on what Dr. Roush has in
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`there and then he had a pKa value of minus .068, and then he had a pKa value of
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`minus .068 for [compound] 3l and pKa of 6.14 for 3a, which is an amino
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`compound. So if you take those two numbers as a reference point, then the
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`separation is about 7. And separation of 7 is, of course, a very large number and
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`that will certainly take it into the territory under normal physiologic conditions,
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`one would not consider that basic.” Id. at 241:12-22 (emphasis added). At 192:9-
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`19, he testified that “in some cases, having a basic functional group at [the] alpha
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`position indeed helped to improve activity. However, that’s not to say that’s the
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`only thing that would improve activity. And there is other modification there that
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`also helped to improve activity.” Dr. Wang continued: “the key question right now
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`here is that is it a reasonable thing to go from NH to a CH at alpha position . . .
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`[T]here is enough evidence to suggest that that position having an amino group
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`is beneficial and having a methyl group there is beneficial and maybe wouldn’t
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`tolerate anything else.” Id. at 197:2-17 (emphasis added).
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`Observation 2: Patent Owner’s counsel did not ask Dr. Wang to review his
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`entire declaration during cross-examination. Ex.2194, 152:9-16 (“Q: And you have
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`reviewed your first declaration, Exhibit 1002, correct? . . . THE WITNESS: By
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`looking through the table of contents and my memory as to how they’re cross-
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`referenced.” (emphasis added)). When asked if a citation to ¶¶ 44-49, 123
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`indicated those were “the only paragraphs in your first declaration discussing the
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`’301 patent,” he replied “[t]hat’s not what it means”; he would “have to look into
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`detail” to identify other areas of the declaration in which the ’301 patent was
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`discussed. Id. at 149:9-150:11. Dr. Wang then “look[ed] through the table of
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`contents,” cross-referencing to review pages 24-26, and responded, “From what I
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`can see here, that’s true.” Id. at 149:15-150:11, 151:22-152:22.
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`Observation 3: Asked if the methoxyamino group has “a basic nitrogen,”
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`Dr. Wang stated “the strength of that [nitrogen] in terms of it being a base of the
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`amino group is different from the strength of ... an amino group itself.... [A] basic
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`nitrogen in the alpha position could contribute to good anticonvulsant activities but
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`other functional groups could also do the same. However, the [basicity of a]
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`methoxyamino group is different from an amino itself.” Ex.2194, 193:9-22.
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`Observation 4: Dr. Wang did not testify that a methoxyimino group (with
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`an “i”) and a methoxyamino group (with an “a”) “have minor structural
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`differences.” He testified: “I would say in this particular case, if you look at the
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`structure itself and then when it has a double bunt [sic, double bond] or not, it does
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`affect the property tremendously and as well the stability. So these two functional
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`groups in this kind of comparison can be very different.” Ex.2194, 115:22-116:20.
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`Dr. Wang affirmed that “[i]n this particular case” of the methoxyimino group with
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`the double bond in cefuroxime, “looking at the differences between functional
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`groups is important.” Id. at 117:6-118:12, Dr. Wang continued “[i]f we extrapolate
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`that to isosteric replacement, I would refer to the Silverman book as to how that
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`should be guided,” but “in this particular case” (referring to ¶42 of his second
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`declaration), the methoxyimino in cefuroxime is “indeed different” from the
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`methoxyamino in compound 3l.
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`Observation 5: Dr. Wang testified: “It would be proper to predict this in
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`such a way to say that if they have a prediction number that could range from 6 to
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`19 and then calculate a how-many-fold increase use in that range and then use in
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`the range that one would see with 107. And so that would be the calculation one
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`would want to do. That’s what I wanted to do.” Ex.2194, 180:7-13. He further
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`testified: “The range actually would be larger with the calculation based on 107d
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`and the predicted racemic lacosamide ED50.” Id. at 180:19-21. Dr. Wang testified:
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`I did not intend to use that number. . . . So if I look at paragraph 141,
`so the predicted activity would be 7.6. So I use 7.6 to do the
`calculations. And then -- so that gives you a range of 13 to 39. So
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`that’s what it is. I did double-check this and I double-checked this and
`I said these numbers are slightly off. However, they’re predicting
`numbers that doesn’t make a whole lot of difference in terms of what
`the specific numbers are based on approximation. So in that
`particular case, and then as it says, it’s an approximate number
`where you’re using predicted numbers to predict the outcome. And
`then it’s an approximation and that’s in the same general range.
`Id. at 181:8-22 (emphasis added).
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`Observation 6: Patent Owner’s Observation omits relevant testimony.
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`Regarding estimated ED50 values of 6.2 and 7.6, Dr. Wang testified “short of very
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`extensive statistical analysis and significance, one would consider them to be
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`essentially the same in terms of meanings.” Ex.2194, 157:17-158:14. When asked
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`whether “the ED50 for compound 2g is essentially the same as the ED50 of
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`compound 3c based upon the same logic” used in ¶109 of Ex.1002, Dr. Wang
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`responded: “I will look at them somewhat differently in the sense that the first one,
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`we were doing estimations as to what they mean because they have calculated
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`numbers to discuss. In this case, they’re experimental numbers. . . . When you try
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`to estimate things by doing calculations, then you don’t hold the same standard as
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`if you do experimental studies. And with that said, I do not know specifically what
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`kind of statistical analysis they did[.]” Id. at 162:10-163-14.
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`Observation 7: Dr. Wang testified: “If you look at the specifics, so even if
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`you consider the small, and then there is not much of a difference and then they
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`will still essentially say similar things, that is, the unsubstituted ones have good
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`activities. There will be no reason to do the substitutions in order to optimize those
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`compounds.” Ex.2194, 166:5-10.
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`Observation 8: Patent Owner’s Observation omits relevant testimony. Dr.
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`Wang testified: “[T]he Lilly letter indicated liver toxicity that was indeed with
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`furan compounds.” Ex.2194, 63:4-5. Dr. Wang testified: “Heteroaromatics are
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`commonly used, but they also present some common problems for the reason that
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`the -- so if you read the literature and there are promiscuity issues with many
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`heteroaromatic compounds and sometimes that leads to toxicity. But that’s correct,
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`the literature do use heteroaromatic compounds.” Id. at 63:14-20. Dr. Wang
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`testified Ex.1104 states that compounds 3c, 3b and 30 have PIs over 10, that
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`compounds 3l and 3n have protective indexes of 7.4 and 7.5, that these compounds
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`“have a higher protective index than compound[s] that have been approved for
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`clinical applications,” and that compound 3c had “the largest numerical value” of
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`compounds listed in Ex.1104. Ex.2194, 168:1-169:1. Dr. Wang testified, “I think in
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`the drug discovery process, labeling something best is a very tricky process that is
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`not as simple as taking a numerical number, and then one has to consider many,
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`many factors. And I certainly see that these compounds are good compounds, but it
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`doesn’t change the fact that 3l is a good lead compound as well.” Id. at 170:4-17
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`(emphasis added).
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`Observation 9: Patent Owner’s Observation omits relevant testimony. Dr.
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`Wang agreed that “compound 1m is a functionalized amino acid with a fluoro-
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`substituted benzyl group” and that “compound 1a in table 6, that is a direct
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`comparator compound with an unsubstituted benzyl group.” Ex.2194, 204:5-21.
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`Dr. Wang agreed compound 1m “has a higher number in terms of protective
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`index” than compound 1a. Id. at 204:22-205:8. Regarding Compounds 1a and 1m
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`in Ex.2004, Dr. Wang “put this in context because this was a 1987 publication and
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`then since then, that counts, in their own research, that the work has largely
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`been focused on modifications at alpha position. And I can see many reasons
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`that one would want to do that.” Id. at 206:8-207:4 (emphasis added). He
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`continued, “there are later publications, ’91, ’93 and I think they had a ’90 and ’94
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`and then the patent themselves, and I think they collectively should form the base
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`for making decisions.” Id.
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`Observation 10: Dr. Wang explained differences between levetiracetam and
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`Dr. Kohn’s FAA compounds:
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`The general question is are there reasons to look at functionalized
`amino acid in this line of research, and so that provides another
`example. However, if you look at specific structures, there are many
`places that are different. And this is also true within the same general
`class of a compound, that you can point out to structural differences as
`well. But what you said is correct, that the structure is different. . . . I
`would say that levetiracetam is a functionalized amino acid but it’s a
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`different functionalized amino acid from the Kohn functionalized
`amino acids, but they’re all functionalized amino acids.
`Ex.2194, 130:17-133:2 (emphasis added). Dr. Wang testified: “Again, I want to
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`say that has no bearing on how you would optimize a different class of
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`functionalized amino acid.” Id. at 136:14-17.
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`Observation 11: Dr. Wang testified:
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`So in the world of drug discovery, you could have multiple lead
`compounds. They may each have different structural scaffold. And
`then what this one says, functionalized amino acid can serve as
`promising lead, but it does not necessarily by itself impact the
`research project, a different class of functionalized amino acid that
`they can be optimized individually and then they should be because
`you never know, if you have different functionalized amino acid, how
`they would work and their mechanisms of actions and whether they
`would target on the same, whether it’s receptor enzymes or whatever
`the target might be. So, you know, on one hand, it is true that’s one
`promising lead compound. On the other hand, you cannot draw an
`inference from that as to what the impact will be on the other classes
`of functionalized amino acid as to how you would optimize them,
`unless you see a specific reason to do so.
`Ex.2194, 134:22-135:19.
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`Observation 12: Dr. Wang stated that structural optimization occurs “within
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`the same general structural class . . . However, I wouldn’t go across structural
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`classes to say that would be a lead compound as well for this particular project.
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`So no, that would not be a lead compound.” Id. at 154:10-19 (emphasis added).
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`Observation 13: Dr. Wang did not confirm that a “racemic compound” is
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`hallucinogenic whereas the S-isomer is not; Counsel asked about “racemic
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`mixture.” Ex.2194, 146:12-13. Dr. Wang explained: “We provided a detailed
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`analysis of the relationship between racemic forms and the two enantiomeric
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`forms, and then a key question is that a racemic mixture is not a unique molecule, a
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`unique compound, and I don’t think anyone going into an organic chemistry
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`classroom will say a racemic mixture is a unique molecule. And it’s composed of
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`two individual compounds.” Id. at 143:2-9.
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`Observation 14: Dr. Wang was asked: “Q. And the first two sentences of
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`that paragraph read, "Dr. Roush asserts that Eli Lilly declined to pursue compound
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`3l but his conclusions are not supported by the record. Exs. 2066 and 2067 do not
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`state that Eli Lilly ever declined to pursue compound 3l." Do you see that? A. Yes,
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`I do.” Ex.2194, 45:10-16. Dr. Wang testified: “[T]here’s evidence of a compound
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`that has a furan substitution in two positions that has toxicity. It does not indicate,
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`in a formal fashion, that 3l would have the same problem.” Id. at 51:8-15. Dr.
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`Wang stated: “[T]hey terminate a program for many reasons but they don’t
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`necessarily tell everyone why they terminate a program.” Id. at 52:17-19. Dr.
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`Wang acknowledged that Ex.2125 states that Lilly terminated license agreement
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`Numbers 1873 and 1874, and stated, “It does not indicate, in a formal fashion,
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`that 3l would have the same problem.... It sure does not change the fact that,…
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`how I assessed compound 3l[.]” Id. at 50:20-51:22 (emphasis added).
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`Observation 15: Dr. Wang testified that he viewed the hepatic toxicity of
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`furan-containing LY274959 described in unpublished correspondence (Exs. 2125,
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`2066, 2069) “as an idiosyncratic toxicity problem,” and observed that “quite often,
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`toxicity issues are idiosyncratic” unless one “can demonstrate that within the same
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`class, they all have the same type of toxicity.” Ex.2194, 50:20-51:15, 232:4-13.
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`Dr. Wang further testified: “I remember seeing this and then thinking that the
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`toxicity in [the] one particular compound does not impact the develop[-]ability of a
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`different one within the same class. . . . [E]vidence of a compound that has a
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`furan substitution in two positions that has toxicity [ ] does not indicate, in a
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`formal fashion, that 3l would have the same problem.” Id. at 50:20-51:15
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`(emphasis added). Additional testimony is at ¶98 of Ex.1084; Dr. Wang relied on
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`the ’301 patent, which was filed and published after the private correspondence in
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`Exs. 2125, 2066, and 2069, to confirm that many of the compounds disclosed
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`therein “exhibited excellent side-effect profiles” compared to available AEDs, and
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`that the purpose of the disclosed compounds was to be useful in the treatment of
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`epilepsy. Dr. Wang’s conclusion that the hepatic toxicity associated with a furan-
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`substituted compound was idiosyncratic to that substitution conforms with his
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`statement that a “POSA would expect from reading this prior art reference” that
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`the compounds disclosed in the ’301 patent “would exhibit excellent side effect
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`profiles” and “satisfactory toxicity profiles,” even without specific toxicity data for
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`each compound disclosed in the patent. Ex.1084, ¶98.
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`Observation 16: In Ex.2194, 53:15-55:19, Dr. Wang confirmed that ¶144 of
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`Ex.1084 begins by stating, “As explained in my opening declaration,” and that
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`¶144 does not cite a specific “paragraph or page” in his opening declaration. Dr.
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`Wang’s SAR discussion beginning at ¶144 discusses the Kohn 1991 reference
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`(Ex.1012), which was discussed in Dr. Wang’s opening declaration at least in the
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`State of the Art (¶¶27-30), and in Ground 2A-B, 3A-B, and 4A-B. Ex.1002 at iii.
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`In Grounds 3A-B, Dr. Wang repeatedly invoked his prior discussion of Kohn 1991,
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`and focused his discussion on matters specific to the combination of references in
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`Ground 3A-B instead of repetitively reciting material from Kohn 1991 that were
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`applicable to multiple grounds involving the same Kohn 1991 reference. See, e.g.,
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`Ex.1002, ¶¶110, 112, 115-16, 118.
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`Observation 17: Dr. Wang did not testify that his scientific arguments in
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`¶¶40, 151-53 and 167 lacked support in the scientific literature. He testified that
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`the statements in question were non-controversial or commonly accepted assertions
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`(including a compound’s structure), for which he could provide references, but did
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`not believe doing so was necessary. Ex.2194, 57:7-16 (“We did not cite a specific
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`example of a reference because these things are general knowledge in the field.”);
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`id. at 58:10-12 (same); id. at 61:20-62:1 (same), id. at 73:15-19 (same); id. at 59:1-
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`10 (same; “We could provide reference to some things like this.”); id. at 64:15-16
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`(“We could have cited a reference.”); id. at 71:4-5 (same); id. at 114:21-115:5
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`(structure of cefuroxime in ¶40).
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`Observation 18: Dr. Wang agreed his Reply declaration noted the “lability
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`associated with the methoxyamino group would be viewed as a strong contributor
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`to potential toxicity, including liver toxicity,” creating “a significant risk for
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`adverse effects including toxicity.” Ex.2194, 59:17-60:17 (emphasis added). Dr.
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`Wang stated “[O]ne would look at this as a point that can be improved and
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`optimized upon to avoid potential toxicity uses and to give [a] compound that will
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`maintain the same potency or improved potency but optimize away from the
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`toxicity issues.” Id. at 60:12-17 (emphasis added).
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`Observation 19: In Ex.2194, 75:14-77:7, Dr. Wang did not agree with Dr.
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`Roush’s statement that the enantiomers of compound 3l had not been prepared in a
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`racemic mixture or that there is a typo in his response declaration. He confirmed
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`that “Dr. Roush indeed state[s] there are no disclosures of the enantiomers of
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`compound 3l had been prepared.” Id. He confirmed his own “statement”
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`describing Dr. Roush’s argument “is true,” and that he was merely “quoting Dr.
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`Roush,” not intending “Ex.2066 on page 2” to prove the accuracy of his quotation
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`of Dr. Roush. Id. at 76:10-21. Dr. Wang testified that Dr. Roush’s statement that
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`the enantiomers had not been prepared was “imprecise” because “[w]hat he
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`intended to state was that the enantiomers of Compound 3l were not isolated or
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`prepared separately.” Ex.1084 at ¶88 (emphasis added), Dr. Wang’s testimony is
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`supported by Ex.2066 at 2, stating: “[S]everal new compounds have been
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`prepared,” including a “racemate” of L246385, which has the same structure as
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`compound 3l, as depicted in Ex.1002, ¶21. Patent Owner waived any objection to
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`¶144 by failing to identify ¶144 in Paper 57.
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`Observation 20: Dr. Wang repeatedly responded that he did not remember
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`whether levetiracetam was discussed in his first declaration or in Dr. Roush’s
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`declaration. Petitioner was not obligated to discuss long-felt need prior to Patent
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`Owner’s production of evidence regarding this alleged secondary indicia and is not
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`obligated to limit his discussion of long-felt need to the compounds identified by
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`Dr. Roush. Ex.2194, 118:22-121:13, 124:17-125:2.
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`Observation 21: Patent Owner’s Observation is incomplete as it omits
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`relevant testimony from Dr. Wang’s testimony. Dr. Wang noted that, while
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`Ex.1155 is “copyrighted for 2013 for the 8th edition . . . the portion of the contents
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`we’re discussing hasn’t changed since that time [of 1996]. . . . We do not provide
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`the version that’s dated before 1996. However, again, the simple chemistry we’re
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`discussing remains the same.” Ex.2194, 141:11-142:14 (emphasis added).
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`Observation 22: Dr. Wang testified that a POSA would “want to look for [a]
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`promising compound.” Ex.2194, 188:19-20. Dr. Wang continued:
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`[C]ompound[s] that have MES, ED50 that’s below 10, they would
`constitute, in terms of potency, as [a] potentially promising lead. But
`then you also want to look at all the other features as well to see
`whether you specifically work on that particular lead or not, and
`whether you see problems or whether there are specific features that
`you think you can easily modify to move from there. But if you look
`at simple potency data itself and then you will go for numbers below
`or about 10.”
`Id. at 188:19-189:9 (emphasis added). He stated that three compounds in the ’729
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`patent, Table 1 had potencies of less than 10 mg/kg, noting the others “may inform
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`SAR to help you focus your next steps. . . [N]ot only [will] you make active
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`compound[s], but you also make other compound[s] that may or may not
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`necessarily be very active but it informs the researcher the structure-activity
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`relationship and therefore that will help you focus later effort.” Id. at 189:11-
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`190:12. Dr. Wang stated: “Dr. Roush has not identified any skepticism of using the
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`claimed compounds for treating CNS disorders”; “the ‘301 and ‘729 patents taught
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`and claimed the use of FAA compounds for treating CNS disorders, such anxiety
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`and epilepsy”; and a POSA “would have read those patents and reasonably
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`expected compounds within the scope of the ‘301 and ‘729 patent to be effective
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`for CNS disorders.” Ex.1084, ¶213.
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`Observation 23: Dr. Wang was asked if the majority of the compounds in
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`the ’729 patent, Table 1 have MES values of 10 or less; he answered: “[T]he
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`percentage of compound that’s very potent is low. If I look at some of these
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`numbers and I see some aromatic compounds that are -- tend to be low.” Ex.2194,
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`189:17-190:12. He did not characterize the potency of nonaromatic compound
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`here, and did not confirm Dr. Roush’s statement.
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`Observation 24: Regarding the quoted testimony, Dr. Wang stated that Dr.
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`Kohn’s “work has largely been focused on modifications at alpha position. And I
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`can see many reasons that one would want to do that. . . . there are later
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`publications, ’91, ’93 and I think they had a ’90 and ’94 and then the patent
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`themselves, and I think they collectively should form the base for making
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`decisions.” Id. at 205:12-207:4.
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`Observation 25: Dr. Wang explained: “drugs frequently have
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`heteroaromatic groups in them,” clarifying: “[h]eteroaromatics are commonly
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`used, . . . they also present some common problems . . . so if you read the
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`literature and there are promiscuity issues with many heteroaromatic compounds
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`and sometimes that leads to toxicity.” Ex.2194 at 63:7-20 (emphasis added).
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`Observation 26: When asked if “some heterocycles increase
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`hydrophilicity,” Dr. Wang said, “Relative to the rest of [the] molecule and
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`heteroatom[s], a ring structure could help to improve solubility or decrease
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`hydrophobicity. It depends on what the relative point is.” Ex.2194, 68:21-69:7
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`(emphasis added). Dr. Wang continued: “[O]ne need[s] to look at the specific
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`situation to be able to say exactly what the influence would be by including a
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`heterocycle,” id. at 69:16-70:7 (emphasis added), but agreed that “a heterocycle
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`could increase hydrophobicity in certain circumstances,” id. at 70:9-11, consistent
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`with his testimony that a POSA would avoid aromatic FAAs because “[l]arge
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`aromatic rings increase hydrophobicity beyond acceptable levels.” Ex.1084, ¶167.
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`Observation 27: Dr. Wang testified that the predicted racemic lacosamide
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`ED50 values of 6 to about 19 were calculated using the ED50 values of compound
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`2d and compound 3k from Kohn 1991 (Ex.1012), discussed in his opening
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`declaration (¶¶27-30), ¶¶92-93, and in Ground 2A-B, 3A-B, and 4A-B. Ex.1002 at
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`iii. In Grounds 3A-B, he repeatedly invoked his prior discussion of Kohn 1991
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`and focused on matters specific to the combination of references in Ground 3A-B
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`instead of repeating material from Kohn 1991 applicable to multiple grounds
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`involving the same Kohn 1991 reference. See Ex.1002, ¶¶110, 112, 115-16, 118.
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`Date: January 6, 2017
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`Respectfully,
`
`
`
`/ Matthew J. Dowd/
`Matthew J. Dowd
`Reg. No. 47,534
`Dowd PLLC
`1717 Pennsylvania Avenue, NW
`Suite 1025
`Washington, D.C. 20006
`
`-15-
`
`

`
`
`
`IPR2016-00204
`
`mjdowd@dowdpllc.com
`
`William G. Jenks
`Reg. No. 48,818
`Jenks IP Law
`1050 17th ST NW
`Suite 800
`Washington, D.C. 20036
`Phone: (202) 412-7964
`wjenks@jenksiplaw.com
`
`Counsel for Argentum
`
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`-16-
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`

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`IPR2016-00204
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`
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`CERTIFICATE OF SERVICE
`37 CFR §42.6(e)
`
`I certify that, on January 6, 2016, this PETITIONERS’ RESPONSE TO
`MOTION FOR OBSERVATIONS REGARDING THE CROSS-EXAMINATION
`OF DR. BINGHE WANG was served on Research Corporation Technologies at
`the following service electronic addresses:
`
`
`
`Andrea G. Reister
`
` areister@cov.com
`
`Jennifer L. Robbins
`
` jrobbins@cov.com
`
`Enrique D. Longton
`
`elongton@cov.com
`
`
`
`/ Matthew J. Dowd /
`Matthew J. Dowd, Reg. No. 47,534
`
`
`Dated: 6 January 2017
`
`
`
`
`
`
`
`-17-

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