` BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`1
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` ---------------------------------x
` STEADYMED LTD.,
` Petitioner,
` vs.
` UNITED THERAPEUTICS CORPORATION,
` Patent Owner.
` ---------------------------------x
`
` VIDEOTAPED DEPOSITION OF
` JEFFREY D. WINKLER, Ph.D.
` New York, New York
` June 14, 2016
` 9:33 a.m.
`
`
`Reported by:
`Jennifer Ocampo-Guzman, CRR, CLR
`JOB NO. 44975
`
` P. 1
`
`UT Ex. 2051
`SteadyMed v. United Therapeutics
`IPR2016-00006
`
`
`
`2
`
` June 14, 2016
` 9:33 a.m.
`
` Videotaped Deposition of
` JEFFREY D. WINKLER, Ph.D., held at
` the offices of DLA Piper LLP (US),
` 1251 Avenue of the Americas, New
` York, New York, pursuant to notice,
` before Jennifer Ocampo-Guzman, a
` Certified Real-Time Shorthand
` Reporter and a Notary Public of the
` State of New York.
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`DAVID FELDMAN WORLDWIDE, INC.
`450 Seventh Avenue - Ste 500, New York, NY 10123 1.800.642.1099
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`UT Ex. 2051
`SteadyMed v. United Therapeutics
`IPR2016-00006
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`3
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` A P P E A R A N C E S:
`
` Attorneys for Petitioner
` DLA PIPER, LLP (US)
` 1251 Avenue of the Americas
` New York, New York 10020-1104
` (212) 335-4964
` BY: STUART E. POLLACK, ESQ.
` stuart.pollack@dlapiper.com
`
` Attorneys for Patent Owner
` WILSON, SONSINI, GOODRICH & ROSATI
` 900 South Capital of Texas Highway
` Las Cimas IV, Fifth Floor
` Austin, Texas 78746-5546
` (512) 338-5432
` BY: BOBBY DELAFIELD, ESQ.
` bdelafield@wsgr.com
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`DAVID FELDMAN WORLDWIDE, INC.
`450 Seventh Avenue - Ste 500, New York, NY 10123 1.800.642.1099
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`UT Ex. 2051
`SteadyMed v. United Therapeutics
`IPR2016-00006
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` APPEARANCES (Continued):
`
` Attorneys for Patent Owner
` FOLEY & LARDNER, LLP
` Washington Harbour
` 3000 K Street, N.W., Suite 600
` Washington, DC 20007-5109
` (202) 672-5569
` BY: STEPHEN B. MAEBIUS, ESQ.
` smaebius@foley.com
`
` ALSO PRESENT:
` JOSE RIVERA, VIDEOGRAPHER
` SHAUN SNADER, ESQ. (UNITED
` THERAPEUTICS)
`
`DAVID FELDMAN WORLDWIDE, INC.
`450 Seventh Avenue - Ste 500, New York, NY 10123 1.800.642.1099
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`UT Ex. 2051
`SteadyMed v. United Therapeutics
`IPR2016-00006
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`5
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` (Winkler Exhibit 1, Curriculum
` Vitae of Jeffrey David Winkler,
` [SteadyMed-Exhibit 1010], marked
` for identification, this date.)
` (Winkler Exhibit 2,
` Declaration of Jeffrey D. Winkler
` in Support of Petition for Inter
` Partes Review of Claims 1-22 of
` U.S. Patent No. 8,497,393,
` [SteadyMed-Exhibit 1009], marked
` for identification, this date.)
` (Winkler Exhibit 3, Copy of
` U.S. Patent No. 8,497,393,
` [SteadyMed-Exhibit 1001], marked
` for identification, this date.)
` THE VIDEOGRAPHER: This is
` media unit number 1 in the video
` deposition of Jeffrey D. Winkler in
` the matter of SteadyMed Limited,
` petitioner, versus United
` Therapeutics Corporation, patent
` owner.
` This deposition is being held
` at DLA Piper LLP, 1251 Avenue of
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`DAVID FELDMAN WORLDWIDE, INC.
`450 Seventh Avenue - Ste 500, New York, NY 10123 1.800.642.1099
`
` P. 5
`
`UT Ex. 2051
`SteadyMed v. United Therapeutics
`IPR2016-00006
`
`
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`6
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` the Americas, New York, New York on
` June 14, 2016, at approximately
` 9:33 a.m.
` My name is Jose Rivera from
` the firm of David Feldman Worldwide
` and I am the legal video
` specialist. The court reporter is
` Jennifer Ocampo-Guzman in
` association with David Feldman
` Worldwide, located at 450 Seventh
` Avenue, New York, New York.
` For the record, will counsels
` please introduce themselves.
` MR. DELAFIELD: Bobby
` Delafield of Wilson Sonsini
` Goodrich & Rosati representing
` patent owner, United Therapeutics
` Corporation.
` MR. MAEBIUS: Stephen Maebius,
` Foley & Lardner, representing
` patent owner, United Therapeutics
` Corporation.
` MR. SNADER: Shaun Snader,
` United Therapeutics, Washington,
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`DAVID FELDMAN WORLDWIDE, INC.
`450 Seventh Avenue - Ste 500, New York, NY 10123 1.800.642.1099
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` P. 6
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`UT Ex. 2051
`SteadyMed v. United Therapeutics
`IPR2016-00006
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` DC, for patent owner, United
` Therapeutics.
` MR. POLLACK: Stuart E.
` Pollack from DLA Piper LLP (US) on
` behalf of Professor Winkler and on
` behalf of SteadyMed Limited.
` THE VIDEOGRAPHER: Now will
` the court reporter please swear in
` the witness.
` J E F F R E Y D. W I N K L E R,
` called as a witness, having been duly
` sworn, was examined and testified as
` follows:
` EXAMINATION BY
` MR. DELAFIELD:
` Q. Good morning, Dr. Winkler.
` A. Good morning.
` Q. Could you please state and
` spell your full name for the record?
` A. Jeffrey David Winkler,
` J-E-F-F-R-E-Y, D-A-V-I-D, W-I-N-K-L-E-R.
` Q. Have you been deposed before?
` A. Yes, I have.
` Q. About how many times?
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`DAVID FELDMAN WORLDWIDE, INC.
`450 Seventh Avenue - Ste 500, New York, NY 10123 1.800.642.1099
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` P. 7
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`UT Ex. 2051
`SteadyMed v. United Therapeutics
`IPR2016-00006
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` A. About ten or 12 times.
` Q. Okay. Well, you probably know
` all the ground rules, but I just want to
` go over a few just to refresh your
` memory. I'll be asking a series of
` questions and you need to provide an
` answer, unless your counsel instructs you
` not to do so.
` Because this is being
` recorded, the answers need to be in
` verbal form, and so no head shakes or
` nods, because it won't be recorded by the
` stenographer.
` You are reminded your
` testimony is under oath, so your answers
` need to be truthful and full to the best
` of your knowledge.
` I might ask a confusing
` question, and if so, feel free to ask me
` to clarify, if you have any issues with
` my question.
` Also, the stenographer has to
` record everything we say, so I'm asking
` if you could not speak over me or vice
`
`DAVID FELDMAN WORLDWIDE, INC.
`450 Seventh Avenue - Ste 500, New York, NY 10123 1.800.642.1099
`
` P. 8
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`UT Ex. 2051
`SteadyMed v. United Therapeutics
`IPR2016-00006
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` versa, so that she can record both of
` what we're saying.
` Also, if you need a break at
` any time, feel free to just tell me, and
` we can take a break, as long as a
` question isn't pending.
` Is there any reason you can
` think of why you will not be able to
` answer my questions today fully and
` accurately?
` A. No.
` Q. Are you taking any medication
` or drugs of any kind that might make it
` difficult for you to understand and
` answer my questions?
` A. No.
` Q. Okay. So you've provided a
` declaration regarding the '393 patent in
` this case; is that correct?
` A. Yes, it is.
` Q. So I want to go ahead and hand
` you three exhibits.
` (Discussion off the record.)
` MR. POLLACK: Thank you.
`
`DAVID FELDMAN WORLDWIDE, INC.
`450 Seventh Avenue - Ste 500, New York, NY 10123 1.800.642.1099
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` P. 9
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`UT Ex. 2051
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`IPR2016-00006
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` Q. So if you turn to Exhibit 1,
` can you tell me what that exhibit is?
` A. Exhibit 1 is my curriculum
` vitae.
` Q. Is that a true and accurate
` copy of your CV?
` A. Yes, it is.
` Q. Can you briefly summarize your
` educational background?
` A. So I was an undergraduate at
` Harvard College. I graduated with honors
` in 1977, and I then pursued graduate
` studies at Columbia University, under the
` direction of the Professor Gilbert Stork,
` where I received an MA and MPhil and
` finally a Ph.D. degree in 1981. I stayed
` at Columbia as an American Cancer Society
` post-doctoral fellow in the laboratory of
` Professor Ronald Breslow from 1982 to
` 1983.
` And that was the end of my
` formal education.
` Q. Okay. So looking at page 1 of
` your CV, it lists your professional
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`DAVID FELDMAN WORLDWIDE, INC.
`450 Seventh Avenue - Ste 500, New York, NY 10123 1.800.642.1099
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` experience. Is that a complete listing
` of your professional experience since
` getting your Ph.D.?
` A. Yes, it is.
` Q. So you've never worked as a
` chemist outside of academia; is that
` correct?
` A. Well, actually I spent a year
` long sabbatical at Bristol-Myers Squibb
` in Lawrenceville, New Jersey, in about
` 2000 or 2001. And I've consulted with a
` number of pharmaceutical and chemical
` companies over the course of my career.
` Q. Okay. But other than the
` sabbatical, you've never been employed
` full time at a chemical company apart
` from your job as a --
` MR. DELAFIELD: Strike that.
` Q. Apart from the year long
` sabbatical, your full-time employment has
` been with universities; is that correct?
` MR. POLLACK: Objection to
` form.
` You can answer.
`
`DAVID FELDMAN WORLDWIDE, INC.
`450 Seventh Avenue - Ste 500, New York, NY 10123 1.800.642.1099
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`IPR2016-00006
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` A. Well, as I stated, my -- I've
` been involved with companies over the
` course of my career full time, only
` during that year at BMS.
` Q. And what did you do during
` that year at BMS?
` MR. POLLACK: I'm just, don't
` reveal any confidential information
` that belongs to BMS, but if it's
` not confidential, you can reveal
` that now.
` A. So during the year at BMS, I
` was part of I think two different
` research teams investigating various
` aspects of drug development, and then I
` also taught a course to BMS scientists
` that was ongoing throughout the course of
` the year.
` Q. Have you ever formulated a
` drug product?
` MR. POLLACK: Objection,
` objection to form, vague.
` A. I'm sorry. What do you mean
` by "formulated a drug product"?
`
`DAVID FELDMAN WORLDWIDE, INC.
`450 Seventh Avenue - Ste 500, New York, NY 10123 1.800.642.1099
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` Q. Have you ever worked in a lab
` for a pharmaceutical company to make a
` drug product?
` A. Well, I guess I would say that
` in my time during the sabbatical year, I
` was working with two teams on the
` development of drug products.
` Q. Have you ever synthesized a
` drug substance?
` A. I'm sorry, I don't understand
` what you mean by that.
` Q. Well, have you ever personally
` or directed others to actually synthesize
` a drug substance that was used in a
` commercially available drug product?
` A. Yes, I have.
` Q. And what was that?
` A. For a while, in the 1990s, my
` laboratory was involved in the synthesis
` of Ritalin, of -- of 30, P-H-R-E-O,
` Phenidate, P-H-E-N-I-D-A-T-E, which is
` the API in Ritalin, R-I-T-A-L-I-N.
` Q. And so was that API actually
` used in a commercial product?
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`DAVID FELDMAN WORLDWIDE, INC.
`450 Seventh Avenue - Ste 500, New York, NY 10123 1.800.642.1099
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` MR. POLLACK: Objection to
` form.
` You can answer.
` A. I don't know the answer to
` that question.
` Q. Have you ever submitted a
` filing to the FDA regarding any drug
` product or drug substance?
` A. No, I have not.
` Q. Have you ever corresponded
` with the FDA at all about any drug?
` A. No, I have not.
` Q. Have you ever developed a
` protocol for evaluating the impurity
` profile of a drug?
` A. Well, my laboratory is
` routinely involved in the purification
` and the assay of the substances that we
` create in our laboratory.
` Q. Sorry. Maybe you
` misunderstood my question.
` Have you ever developed an
` impurity profile for a drug product?
` MR. POLLACK: Objection to
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`DAVID FELDMAN WORLDWIDE, INC.
`450 Seventh Avenue - Ste 500, New York, NY 10123 1.800.642.1099
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` form.
` A. I'm afraid I don't understand
` your question.
` Q. Well, you understand that to
` have a drug substance or a drug product
` you must submit an impurity profile to
` the FDA. Do you understand that?
` A. I have never submitted a drug
` impurity profile to the FDA.
` Q. Okay. Have you ever developed
` the impurity profile for someone else to
` submit to the FDA?
` A. Not that I can think of
` sitting here now.
` Q. Do you have any experience
` synthesizing prostaglandins?
` A. I have certainly studied the
` synthesis of prostaglandins and taught
` the synthesis of prostaglandins.
` Q. And you have or people working
` for you ever synthesized prostaglandins?
` A. My laboratory has worked on
` the development of the methodology,
` synthetic methodology that could be
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`DAVID FELDMAN WORLDWIDE, INC.
`450 Seventh Avenue - Ste 500, New York, NY 10123 1.800.642.1099
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` applicable to the synthesis of
` prostaglandins.
` Q. But you or your lab haven't
` actually synthesized prostaglandins; is
` that correct?
` A. Sitting here I can't think of
` an example where we have synthesized
` prostaglandins.
` Q. Do you have any experience
` manufacturing --
` A. Excuse me. Although, I should
` add that my laboratory has synthesized
` compounds that are certainly related to
` the prostaglandins.
` Q. Okay. Do you have any prior
` experience synthesizing or analyzing
` treprostinil or any of its derivatives?
` Prior to this case?
` MR. POLLACK: Objection to
` form, compound.
` A. Prior to this case, I have not
` had -- I'm sorry, could you repeat the
` question, please?
` Q. Prior to this case, did you
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`DAVID FELDMAN WORLDWIDE, INC.
`450 Seventh Avenue - Ste 500, New York, NY 10123 1.800.642.1099
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` have any experience synthesizing or
` analyzing treprostinil?
` A. Prior to this case, I have not
` had experience with treprostinil,
` specifically.
` Q. Do you have any experience
` scaling up drug substances from lab scale
` to industrial scale?
` A. In my role as a consultant in
` the pharmaceutical industry, I certainly
` have had experience with the scale up of
` reactions in the pharmaceutical industry.
` Q. When you say you have
` experience with reactions, what do you
` mean by that?
` A. Excuse me. In saying that I
` have experience with scale up, that means
` that as part of my association with
` pharmaceutical companies, I've had the
` opportunity to consult on and discuss
` with pharmaceutical scientists and advise
` pharmaceutical scientists on large scale
` reactions.
` Q. Have you or your lab performed
`
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` any large scale reactions?
` A. I'm afraid I don't understand
` exactly what you mean by "large scale
` reactions."
` Q. Well, you just mentioned that
` you had advised and mentioned the term
` "large scale reactions," and so I guess
` to put a number on it, have you or your
` lab performed any syntheses on a kilogram
` scale?
` A. I would have to go back to the
` lab notebooks in my research group to
` know whether we had done reactions on
` that scale.
` So sitting here, I can't
` really answer that.
` Q. But sitting here today, you
` can't remember anything specific on that
` scale, or larger; is that correct?
` MR. POLLACK: Objection to
` form.
` A. I can't remember having done
` reactions on kilogram scale, but I
` certainly can't remember not having done
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`DAVID FELDMAN WORLDWIDE, INC.
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` them on kilogram scale.
` Q. Are you familiar with the FDA
` guidelines regarding impurity profiles
` for a drug?
` A. No, I am not.
` Q. Do you know what is required
` in order to change a drug specification
` with the FDA?
` A. No, I do not.
` Q. Are you familiar with
` published guidances from the FDA
` regarding changes to new drug
` applications or abbreviated new drug
` applications?
` A. I'm sorry, could you repeat
` the question?
` Q. Are you familiar with
` published guidances from the FDA
` regarding changes to new drug
` applications or abbreviated new drug
` applications?
` A. No, I am not familiar with
` that.
` Q. You had mentioned you had been
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`450 Seventh Avenue - Ste 500, New York, NY 10123 1.800.642.1099
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`IPR2016-00006
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` deposed several times. Do you recall how
` many patent litigations you've worked on?
` A. I don't remember exactly, no.
` Q. So let's look at Exhibit 3,
` which is the '393 patent. Do you
` recognize this document?
` A. Yes, I do.
` Q. And this is the '393 patent
` that is at issue in this case, correct?
` A. That's my understanding, yes.
` Q. If you could turn to column
` 2 -- actually, column 3, I'm sorry.
` And do you see in column 3
` structure Roman numeral (IV)?
` A. Yes, I do.
` Q. Do you recognize that
` structure?
` A. I do, yes.
` Q. And what is that structure?
` A. That is the chemical structure
` of treprostinil.
` Q. Would you agree that
` treprostinil has five chiral centers?
` A. Yes, I would, five chiral
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`IPR2016-00006
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` centers or 5 stereo centers, yes.
` Q. So if a molecule has five
` chiral centers, that means that it has 32
` possible stereoisomers; is that right?
` A. Two to the five, that's
` correct.
` Q. Is it fair to say that
` treprostinil is a complex molecule?
` MR. POLLACK: Objection to
` form.
` A. I think that's a difficult
` question for me, because the question
` would be, complex relative to what?
` Q. Well, just your experience as
` a chemist, would you consider
` treprostinil to be complex compared to
` other chemicals that you've since
` synthesized?
` MR. POLLACK: Objection to
` form.
` A. We've synthesized compounds in
` my laboratory that are much more complex
` than treprostinil, and we've synthesized
` some molecules that are less complex than
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`450 Seventh Avenue - Ste 500, New York, NY 10123 1.800.642.1099
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`IPR2016-00006
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` treprostinil.
` Q. You've reviewed the synthesis
` for treprostinil for the '393 patent,
` correct?
` A. Yes, I have.
` Q. And you've reviewed some of
` the prior art that had other syntheses
` for treprostinil; is that right?
` A. Yes, I have.
` Q. And the total synthesis is, I
` believe, roughly 20 steps, depending on
` which synthesis, but it's a multi-step
` process; is that correct?
` MR. POLLACK: Objection to
` form.
` A. I'm sorry, I don't understand
` the question.
` Q. You would agree that the
` synthesis for treprostinil is
` approximately 20 steps?
` A. I actually haven't counted the
` number of steps in the synthesis.
` Q. Would you consider the
` synthesis of treprostinil to be complex?
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`450 Seventh Avenue - Ste 500, New York, NY 10123 1.800.642.1099
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` MR. POLLACK: Objection to
` form.
` A. Again, the problem that I
` would have in answering that question is:
` Complex to relative to what? There are
` things that are much more complex than
` treprostinil, and there are things that
` are decidedly less complex.
` Q. Well, would you expect, let's
` say, undergraduate students to be
` synthesizing treprostinil or structures
` similar to treprostinil in their lab?
` A. That's a very difficult
` question for me to answer, because it
` would depend on the level and skill of
` the undergraduate student.
` Q. Well, just as a matter of
` course, within the courses you teach, for
` example, are you aware of any syntheses
` that are multiple steps that have --
` MR. DELAFIELD: Strike that.
` Q. Do you teach organic
` chemistry?
` A. Yes, I do.
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` Q. And in your experience in
` teaching organic chemistry, do students
` typically synthesize structures that have
` five or more chiral centers from
` commercially available starting
` materials?
` A. I don't know the answer to
` that.
` Q. But sitting here today, you
` can't think of any?
` A. I'm sorry, I don't understand
` the question.
` Q. Sitting here today, you are
` not aware of any syntheses that your
` students perform synthesizing molecules
` with five or more chiral centers?
` A. Sitting here today, I can't
` think of any examples.
` Q. Do your undergraduate students
` typically perform kilogram scale
` reactions?
` A. I'm afraid I don't understand
` the question.
` Q. Well, you teach undergraduate
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` chemistry, correct?
` A. That is correct.
` Q. And in those classes and labs,
` they perform experiments, right?
` A. The students in the
` laboratories, in the teaching
` laboratories certainly do perform
` experiments, yes.
` Q. And are you aware if those
` students perform syntheses on a kilogram
` scale?
` A. I am not --
` MR. POLLACK: Objection to
` form.
` A. I am not aware.
` Q. Do you know if the lab
` equipment in undergraduate labs is even
` capable of synthesizing kilogram scale
` reactions?
` A. I do not know.
` Q. Would it surprise you if they
` didn't?
` MR. POLLACK: Objection to
` form.
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` A. I'm sorry, I don't understand
` your question.
` Q. Well, you're aware of the
` equipment used in undergraduate
` laboratories, correct?
` A. No, I am not.
` Q. So you're not aware of what
` laboratory equipment is used in the
` undergraduate courses that you teach?
` A. Well, the undergraduate
` courses that I teach are lecture courses,
` so they don't have laboratory components
` to them.
` Q. So you don't teach the lab
` courses?
` A. I do not.
` Q. If you could look at
` Exhibit 2, which is a copy of your
` declaration -- well, first, is that a
` true and correct copy of your
` declaration?
` A. Yes, it is.
` Q. Are you aware of any errors in
` your declaration?
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` A. I am.
` Q. And what are those errors?
` A. There's a citation to Phares,
` Exhibit 1005, at the bottom of page 14
` that continues on to page 15, and it
` cites Exhibit 1005, page 24, bottom
` paragraph, and that number should
` actually be page 22.
` Q. Okay. Are you aware of any
` other errors?
` A. No, I am not.
` Oh, excuse me. There is one
` other error, I guess. There appears to
` be a duplicate signature page at the end
` of the report. I'm not sure what the
` reason is for that.
` Q. So if we could take a look at
` paragraph 14 in your declaration, do you
` see that?
` A. Yes, I do.
` Q. And paragraph 14 says, "Given
` the high education level of the
` scientists actually working in this
` field, a person of ordinary skill in the
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` art ('POSA') of chemistry at the time of
` the alleged invention would have a
` master's degree or a Ph.D. in medicinal
` or organic chemistry, or a closely
` related field. Alternatively a person of
` ordinary skill would include a bachelor's
` degree and at least five years of
` practical experience in medicinal or
` organic chemistry." Do you see that?
` A. Yes, I do.
` Q. And you agree with that
` definition of person of ordinary skill
` with regard to the '393 patent?
` A. Yes, I do.
` Q. So do you recall how you came
` up with that definition?
` A. I came up with that definition
` as a function in large measure of looking
` at the inventors of the patent and what
` their level of expertise and training
` was.
` Q. Did you do anything else to
` determine what the level of ordinary
` skill would be?
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` A. I think my opinion was formed
` based on the background of the inventors
` and on my own reading of the patent.
` Q. So when you say your own
` reading of the patent, what informed your
` decision to choose that level of skill
` based on your reading of the patent?
` A. I formed that opinion based on
` the science, the chemistry that was in
` the patent.
` Q. And so you would agree that to
` understand the science and chemistry of
` the patent, you would need this level of
` skill in the art?
` A. Yes, that is my opinion.
` Q. Okay. So let's turn back to
` paragraph 3 in your report.
` And the last full sentence
` says, "The technology of the '393" --
` MR. DELAFIELD: Strike that.
` Q. -- "The technology of the '393
` patent involves nothing more than basic
` organic chemistry techniques-in my view,
` 'organic chemistry 101'-all of which were
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` well-known in the art prior to
` December 17, 2007."
` Do you see that?
` A. Yes, I do.
` Q. So do you disagree with that
` statement then?
` A. No, I do not.
` Q. Well, I believe you just said
` that you agree that to understand the
` science and chemistry of the '393 patent
` you would need that level of skill in the
` art being a Ph.D. or master's with
` experience in medicinal or organic
` chemistry, correct?
` A. I'm sorry, could you repeat
` that, please?
` Q. I believe you just previously
` answered that you would need the level of
` skill in the art that you list in
` paragraph 14 to understand the chemistry
` of the '393 patent, correct?
` A. I don't think that's really
` what I said. I think what I said was
` that a person of ordinary skill in the
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` art at the time of the invention would
` have a master's degree or a Ph.D.
` Alternatively, the person of ordinary
` skill would include an individual with a
` bachelor's degree and at least five years
` of practical experien