UNITED STATES PATENT AND TRADEMARK OFFICE
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`1
`
`ADAMA MAKHETSHIM, LTD.,
`
`Petitioner
`
`vs.
`
`FINCHIMICA S.P.A.,
`
`Patent Owner.
`
`CASE IPR2016-00577
`
`EXAMINATION of GORDON GRIBBLE, PH.D. as taken
`
`by and before BETH J. SPINNER, a Certified
`
`Shorthand Reporter and Notary Public of the State
`
`of New York at the law offices of COOPER & DUNHAM,
`
`LLP, 30 Rockefeller Plaza, 20th Floor, New York,
`
`New York on Wednesday, August 3, 2016, commencing
`
`at 11:00 a.m.
`
`FINCHIMICA EXHIBIT 2021
`ADAMA MAKHTESHIM v. FINCHIMICA
`CASE IPR2016-00577
`
`
`BEFORE THE PATENT TRIAL AND APPEAL BOARD
`
`1
`
`ADAMA MAKHETSHIM, LTD.,
`
`Petitioner
`
`vs.
`
`FINCHIMICA S.P.A.,
`
`Patent Owner.
`
`CASE IPR2016-00577
`
`EXAMINATION of GORDON GRIBBLE, PH.D. as taken
`
`by and before BETH J. SPINNER, a Certified
`
`Shorthand Reporter and Notary Public of the State
`
`of New York at the law offices of COOPER & DUNHAM,
`
`LLP, 30 Rockefeller Plaza, 20th Floor, New York,
`
`New York on Wednesday, August 3, 2016, commencing
`
`at 11:00 a.m.
`
`FINCHIMICA EXHIBIT 2021
`ADAMA MAKHTESHIM v. FINCHIMICA
`CASE IPR2016-00577
`
`
`
`2
`
`A P P E A R A N C E S
`ROTHWELL FIGG
`BY:
`E. ANTHONY FIGG, ESQ.,
`SETH E. COCKRUM, PH.D., ESQ.
`607 14th Street, N.W.
`Suite 800
`Washington DC 20005
`Attorney for Finchimica S.P.A., Patent Owner.
`COOPER & DUNHAM, LLP.
`BY:
`GARY J. GERSHIK, ESQ.
`30 Rockefeller Plaza
`20th Floor
`New York, New York 10112
`Attorney for Adama Makhteshim Ltd., Petitioner.
`
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`3
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`WITNESS
`GORDON GRIBBLE
`By Mr. Figg
`
`I N D E X
`DIRECT CROSS REDIRECT RECROSS
`
`5
`
`E X H I B I T S
`DESCRIPTION
`Material Safety Data Sheet
`For trichloroacetic acid
`Material Safety Data Sheet
`For trichloroacetic acid
`Material Safety Data Sheet
`For dichloroacetic acid
`Declaration
`
`IDENT.
`2016
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`2017
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`2018
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`2019
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`PAGE
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`50
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`4
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`IT IS HEREBY STIPULATED, by and between
`the attorneys for the respective parties hereto,
`that:
`
`All rights, including that right to object
`to any question, except as to form, or to move to
`strike any testimony at this examination is
`reserved; and in addition, the failure to object
`to any question or to move to strike any
`testimony at this examination shall not be a bar
`or waiver to make such motion at, and is reserved
`to, the trial of this action.
`This deposition may be sworn to by the
`witness being examined before a notary public,
`other than the notary public before whom this
`examination was begun. But the failure to do so
`or to return the original of the deposition to
`counsel, shall not be deemed a waiver of rights.
`The filing of the original of this
`deposition is waived.
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`5
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`A.
`
`Gribble - direct
`G R I B B L E, having a
`G O R D O N
`W A Y N E
`business residence at Dartmouth College, having
`been duly sworn, testified as follows:
`DIRECT EXAMINATION BY MR. FIGG:
`Q.
`Good morning Professor Gribble.
`Good morning, Mr. Figg.
`Q.
`So we have done this before, I think
`perhaps three times, so you know the rules, the
`ground rules but I will go over them briefly.
`As you know I represent Finchimica
`who is the patent owner in the IPR that is
`involved in this case.
`My colleague Seth Cochran
`also represents Finchimica.
`And, as you know, the court reporter
`is making a verbatim transcript of today's
`proceedings so it is important that you give
`audible responses to my questions and that you
`and I try to allow the other person to finish
`before we start talking which makes life easier
`for the reporter.
`So I assume that is all okay with
`
`you?
`A.
`
`Yes, that is fine.
`Q.
`And if I should ask a question today
`that you don't understand, please ask me to
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`Gribble - direct
`clarify it and I will do my best to do so.
`A.
`I will.
`Q.
`Okay.
`And Mr. Gershik today may from time
`to time object to questions that I ask which is
`his right to preserve his objections for the
`record.
`
`You understand that you are to
`respond to my questions to the best of your
`ability subject to his objections unless he gives
`you instructions not to answer?
`A.
`I do.
`All right.
`Q.
`and get started.
`I am going to put a couple of
`documents in front of you that I believe you are
`familiar with.
`They are Exhibit 1002 and Exhibit
`1004.
`Just for the record, Exhibit 1002 is a
`copy of the European patent specification EP 0
`295 117 B1.
`
`Why don't we go ahead
`
`And Exhibit 1004 is a copy of
`international patent publication WO 2007/122440
`A1.
`
`And I think we all have referred to
`them in these proceedings as the EP '117 patent
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`Gribble - direct
`and the WO '440 patent application.
`A.
`Yes, that is correct.
`Q.
`You are familiar with these
`documents, correct?
`A.
`Yes, I am.
`Q.
`I'd like to just see the extent to
`which we can agree on what the disclosures of
`these patent applications or these documents are.
`The EP '117 patent application Exhibit 1002
`describes a process for making fipronil and
`related compounds by oxidizing a sulfide
`precursor, correct?
`A.
`I believe that is correct, yes.
`Q.
`And the oxidant used in the process
`that is described in that patent is
`meta-chloroperbenzoic acid, correct?
`A.
`With regard to example one, that is
`correct, yes.
`Q.
`The WO '440 patent application,
`Exhibit 1004, also describes a method for
`producing fipronil and related compounds by
`oxidizing the sulfide precursor, correct?
`A.
`That is correct, yes.
`Q.
`And the oxidant that is used in the
`process described in the WO '440 application is
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`Gribble - direct
`trichloroperacetic acid, correct?
`A.
`That's one of two acids that are mentioned
`in example one and example two -- example one,
`sorry.
`
`The patent application itself
`Q.
`identifies trichloroperacetic acid or TCPA as the
`oxidant, does it not?
`A.
`As it forms from hydrogen peroxide it is
`identified as, in my opinion, one of the two
`oxidants, yes.
`Q.
`Let's focus on what the patent
`itself identifies as the oxidant.
`A.
`Can you show me where it says that
`exactly.
`If you look at page eight of
`Yes.
`Q.
`the document in the bottom part of that page
`starting around line 21.
`A.
`It does say that trichloroperacetic acid
`is the reactive species that's formed in situ
`from hydrogen peroxide and trichloroacetic acid.
`Q.
`Going back to Exhibit 1002, the EP
`'117 patent, example one in that reference
`employs a reaction solvent, correct?
`A.
`The solvent in example one of the 117 is
`dichloromethane.
`
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`Gribble - direct
`Q.
`That is the reaction solvent, is
`that correct?
`A.
`In example one, that is the reaction
`solvent, yes.
`Q.
`Just so the record is clear, I think
`there are various names by which that solvent is
`known, dichloromethane, methylene chloride,
`methylene dichloride.
`When we see those names,
`those are all the same thing, right?
`A.
`They are all the same thing, yes, often
`abbreviated DCM.
`Q.
`Yes.
`Am I correct that in example one the
`function of the dichloromethane is to dissolve
`the fipronil sulfide precursor and the oxidant
`meta-chloroperbenzoic acid.
`A.
`That is the function of a solvent.
`this case that is the function of DCM.
`Q.
`This EP '117 patent was filed by
`Rhone-Poulenc, correct?
`A.
`I believe it is a French patent, yes,
`filed in the late '80s, I believe.
`Q.
`Do you see that Rhone-Poulenc is
`identified there as the applicant for the patent?
`A.
`I do see that on page one, yes.
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`And in
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`A.
`
`Gribble - direct
`Q.
`Do you have an understanding as to
`whether or not this is the, we might call it the
`basic patent on fipronil or the initial patent
`covering fipronil and methods for its production?
`A.
`I don't know that.
`Q.
`You don't know?
`No.
`Now meta-chloroperbenzoic acid is a
`Q.
`peracid, correct?
`A.
`It is a peracid, yes.
`Q.
`And it is a solid at room
`temperature, correct?
`A.
`It is a solid, but as it turns out, it has
`to be treated with water to prevent its
`detonation.
`It does explode in the dry state.
`So commercial meta-chloroperbenzoic acid is
`always sold with 25 to 30 percent water.
`Q.
`The meta-chloroperbenzoic acid
`itself is a solid material, correct?
`A.
`It is a solid but it does contain water
`that is used presumably in this example one.
`Q.
`The example doesn't indicate that
`water is used or that a water solution is used,
`does it?
`A.
`It does not.
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`Gribble - direct
`Q.
`And do you know the melting point of
`meta-chloroperbenzoic acid?
`A.
`According to the specification from
`Thermal Scientific, I believe, it is 42 to 44
`degrees.
`Q.
`
`Why don't we take a look at Exhibit
`
`1020.
`
`I will hand you a copy of Exhibit
`I think this is an exhibit that you
`1020.
`referred to in the declaration that you filed in
`this action.
`Do you recognize it?
`A.
`I do recognize this, yes.
`Q.
`Do you see under "typical
`properties" there is a value there for melting
`point?
`A.
`
`I see that, 92 to 94 degrees.
`Q.
`So the melting point of
`meta-chloroperbenzoic acid is 92 to 94 degrees
`Centigrade?
`A.
`Correct.
`Q.
`Do you know what the melting point
`of trichloroperacetic acid is?
`A.
`Offhand I do not.
`Q.
`Do you know whether
`trichloroperacetic acid exists as a solid that
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`A.
`
`Gribble - direct
`can be isolated?
`A.
`I do know that it is an unstable solid,
`that peracid we are talking about.
`The peracid,
`I think you said?
`Q.
`Correct.
`Is an unstable solid.
`Q.
`Is it a solid or a liquid?
`I am not sure but it is an unstable
`A.
`substance.
`It is unstable so we probably don't
`Q.
`get a bottle of that and weigh it out, right?
`A.
`Correct.
`Q.
`Now, if you take a look at page
`eleven of Exhibit 1002, the EP '117 patent, that
`has a formula there for the oxidants that can be
`used for oxidizing the fipronil sulfide precursor
`to fipronil, correct?
`A.
`I see that on line 18, I guess, or 10 or
`20.
`
`And that formula includes three
`Q.
`compounds, correct?
`A.
`As stated it does, yes.
`Q.
`Those three compounds are hydrogen
`peroxide, trifluoroperacetic acid and
`meta-chloroperbenzoic acid, correct?
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`Gribble - direct
`A.
`That is correct.
`Q.
`And the meta-chloroperbenzoic acid
`is identified as the preferred oxidant in the
`process of that patent, correct?
`A.
`On line 22, that's correct.
`Q.
`It does not identify
`dichloroperacetic acid as an oxidant, does it?
`A.
`That is not one of the three compounds
`that are listed there.
`Q.
`In fact the EP '117 patent does not
`mention dichloroacetic acid or dichloroperacetic
`acid anywhere, correct?
`A.
`I would have to read the patent, I think.
`Q.
`You have read it.
`Do you recall
`having seen reference to either of those
`compounds in this patent?
`A.
`I don't recall.
`Q.
`Why don't you take a look at Exhibit
`1004 which is the WO '440 application and I would
`like to focus your attention at page one around
`lines 15 through 19.
`At the time this application was
`filed the known commercial process for making
`fipronil used trifluoroacetic acid, correct?
`A.
`That is what this states, yes.
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`Gribble - direct
`Q.
`And do you have any reason to doubt
`
`that?
`A.
`
`I don't.
`Q.
`And again on page one the stated
`goal of the WO '440 inventors was to successfully
`substitute the corrosive and expensive solvent
`trifluoroacetic acid with an inexpensive and
`easily available but effective alternative
`solvent, do you see that?
`A.
`I do.
`And the alternative solvent that
`Q.
`these inventors chose was trichloroacetic acid,
`correct?
`You may want to go over to the next
`page.
`Again, trichloroacetic acid is a solid at
`A.
`room temperature so you would need a melting
`point depressant or co-solvent.
`Q.
`Well, my point was, you are kind of
`jumping ahead of me here anticipating questions I
`might ask down the road.
`But my only point was, on the first
`page they say their goal is to successfully
`substitute the expensive and corrosive
`trifluoroacetic acid with an inexpensive and
`easily available alternative solvent, right?
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`Gribble - direct
`A.
`That is what I see, yes.
`Q.
`And if you turn to the next page,
`the alternative solvent that they've chose was
`trichloroacetic acid, correct?
`A.
`Again, that is not a solvent, so that
`sentence really doesn't connect with the previous
`sentence.
`It is a related compound but it is not
`a solvent like trifluoroacetic acid is.
`Q.
`Well, it does say on line four that
`trichloroacetic acid can be made to be an
`effective solvent for the proposed manufacturing
`process, right?
`A.
`It does say that but I would disagree that
`it ever becomes a solvent.
`It is dissolved in
`another solvent.
`But
`Q.
`I know that is your contention.
`I am really trying to focus on what the authors
`of this patent have told us.
`And they identify
`it as a solvent which is an alternative to
`trichloroacetic acid, do they not?
`A.
`That is what they call it, an effective
`solvent, but I would disagree that it is a
`solvent.
`Q.
`
`I understand.
`Now, so as you point out in that
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`16
`
`Gribble - direct
`paragraph at the top of page two, the WO '440
`application tells us that trichloroacetic acid
`was initially considered to be unsuitable because
`it is not a liquid at room temperature, right?
`A.
`That is what it says, yes.
`Q.
`And do you have an understanding
`that it was desirable to conduct these oxidation
`reactions at lower temperatures, room temperature
`or below, that there was a general desire in the
`field to keep the reaction temperature low?
`A.
`I believe that is the case, yes.
`Q.
`What was your understanding of why
`the scientists in this area wanted to keep the
`reaction temperatures low?
`One is to
`A.
`I think there are two reasons.
`preclude formation of the sulfide which is, as
`you know, the second reaction after the sulfoxide
`forms.
`And at higher temperatures these
`haloacetic acids actually decompose.
`In fact,
`trichloroperacetic acid decomposes to phosgene
`which is very toxic water gas, as you may know,
`extremely toxic.
`So lower temperatures then prevents
`that decomposition as well as formation of the
`sulfide.
`
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`
`Gribble - direct
`Q.
`And so the general desire was to
`keep the reaction temperature somewhere around
`room temperature or even somewhat below that, is
`that right?
`Also from a cost
`A.
`That would be ideal.
`standpoint one doesn't have to heat the reaction
`mixture, to carry it out at room temperature.
`Q.
`So the WO '440 patent application
`tells us in that paragraph at the top of page two
`that trichloroacetic acid could be made an
`effective solvent through the use of a compatible
`melting point suppressant that does not adversely
`affect the process, right?
`A.
`This is how it reads, yes.
`Q.
`Now by the way, trifluoroacetic acid
`is a liquid at room temperature, correct?
`A.
`Yes, it is.
`Q.
`And so there was no reason to use a
`melting point suppressant with trifluoroacetic
`acid?
`No, but of course it has other
`A.
`disadvantages as I think we are all aware.
`Q.
`Right.
`And dichloroacetic acid is a liquid
`at room temperature, correct?
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`Seven,
`
`Gribble - direct
`A.
`Yes, it is.
`Q.
`Now in that same paragraph the
`inventors on the WO '440 patent identify some
`exemplary melting point depressants.
`Do you see
`that?
`A.
`
`On page two?
`Q.
`Yes, around line seven.
`eight, nine.
`A.
`Right, these are all solvents that are
`called melting point depressants by the authors
`of the '440.
`The authors of the '440 patent
`Q.
`application called them melting point
`depressants, correct?
`A.
`Which is what I just said, yes, you are
`correct.
`And those are monochloroacetic acid,
`Q.
`dichloroacetic acid, methylene dichloride,
`ethylene dichloride, monochlorobenzene or a
`haloalkane, right?
`A.
`That is what it says, yes.
`Q.
`And if you turn over to page four of
`the WO '440 application, there is actually a
`reference to the EP '117 patent, correct?
`A.
`On line 14.
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`A.
`
`Gribble - direct
`Q.
`Yes.
`I do see that.
`Q.
`And the WO '440 application explains
`that the EP '117 patent also describes the
`preparations of compounds of Formula I which
`would be fipronil and related compounds, right?
`A.
`Yes, I see that.
`Q.
`He says that they prepare them using
`3-chloroperbenzoic acid, right?
`A.
`On line 15, yes.
`Q.
`That is the same thing as
`meta-chloroperbenzoic acid, right?
`A.
`It is the same thing, yes.
`Q.
`And the WO '440 application points
`out that the EP '117 patent process does not use
`the same oxidation route as the invention in the
`WO '440 application, right?
`A.
`It does say that, yes.
`Q.
`Now, if you turn to page five of the
`WO '440 application, Exhibit 1004, do you see
`that there is a discussion of trifluoroacetic
`acid starting around line 16?
`A.
`I see that, yes.
`Q.
`And it says that trifluoroacetic
`acid has been reported to be a good medium for
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`Gribble - direct
`effecting the oxidation, do you see that?
`A.
`On line 16 and 17, yes.
`Q.
`And when the WO '440 patent is
`referring to "the oxidation" in that sentence, do
`you have an understanding of what oxidation it is
`referring to?
`A.
`They are talking about the oxidation of
`the sulfide precursor to fipronil.
`It is the
`only oxidation in the '440.
`Q.
`They refer to it there as "the
`oxidation," correct?
`A.
`The oxidation, yes.
`Q.
`Then Gharda goes on in the next
`sentence to explain that trichloroacetic acid has
`not been reported as a medium due to its high
`melting point, right?
`A.
`That is correct.
`Q.
`And around page nine the Gharda WO
`'440 application explains that the composition of
`the mixture is chosen so as to depress the
`melting point of the trichloroacetic acid
`sufficiently, usually to less than ten degrees
`Centigrade, do you see that?
`A.
`That is what it says, beginning on line
`14.
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`Q.
`And Gharda WO '440 application
`explains that the purpose of adding
`dichloroacetic acid is only to sufficiently
`depress the melting point of the trichloroacetic
`acid, right?
`A.
`That is what I read, but again it is a
`solvent.
`The melting point consideration is
`really moot because we are actually dissolving
`the solid before it has a chance to melt.
`Q.
`I understand that is your
`contention, Doctor.
`But I am trying to focus on
`what this patent actually tells the person
`skilled in the art at the time it was published.
`And it tells the reader that the
`only purpose of adding dichloroacetic acid was to
`sufficiently depress the melting point of
`trichloroacetic acid, right?
`A.
`On that page it says that, but certainly
`later on in example one, I believe, it talks
`about the fact that dichloroacetic acid also
`functions as an oxidant with hydrogen peroxide
`but it is not as good.
`Q.
`Wait a minute.
`that in example one?
`A.
`May I take a look?
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`You think it says
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`
`It is on page nine before the
`
`Gribble - direct
`Q.
`Yes.
`I am sorry.
`A.
`examples.
`Is the paragraph you referred to in
`Q.
`prior declarations and I think even in the
`declaration submitted in this IPR, that says
`dichloroacetic acid is a poor medium for
`oxidation, right?
`A.
`That is what it says and I interpret that
`as the reaction that is occurring, it is giving
`finite product but just not as good.
`Q.
`I understand that is your
`contention.
`
`Incidentally, it doesn't say there,
`remember when we were looking at the part of the
`patent that referred to trifluoroacetic acid, it
`indicated that trifluoroacetic acid is a good
`medium for the oxidation, right?
`A.
`Back on an earlier page?
`Q.
`Yes.
`But that is again not related to this
`A.
`patent.
`I am just trying to draw a
`Q.
`When it talks about trifluoroacetic
`distinction.
`acid, it said it is a good medium for "the
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`oxidation," right?
`A.
`It does say that, yes.
`Q.
`But when it refers to dichloroacetic
`acid, it just says it is a poor medium for
`oxidation, right?
`A.
`But there is only one oxidation involved
`in the '440 patent.
`Q.
`I understand that is your
`contention.
`Let's just agree that it doesn't
`refer to "the oxidation" on this page, does it?
`A.
`It doesn't say that but I believe it is
`referring to the only oxidation in the '440.
`Q.
`That is a contention that you have
`made previously in the interference proceeding,
`right?
`A.
`
`I believe I have, yes.
`Q.
`While we are on page nine -- so
`Gharda, and let me make sure the record is clear,
`Gharda is the inventor and the applicant on the
`WO '440 application, right?
`A.
`Yes, he is or she is, yes.
`Q.
`So sometimes I'll refer to Gharda
`and sometimes I'll refer to it as the number.
`But you understand we are talking about the same
`thing?
`
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`A.
`I do.
`So Gharda explains on page nine that
`Q.
`the reaction is most preferably carried out at
`about 20 degrees Centigrade, right?
`A.
`Line nine, I do see that.
`Q.
`That goes back to what you and I
`were discussing just a few minutes ago, the
`desire to keep the reaction temperature
`relatively low?
`A.
`Exactly, yes.
`Q.
`And so Gharda explains that the
`composition is selected so that the melting point
`is depressed usually to less than ten degrees
`Centigrade, do you see that?
`A.
`I do see that, yes.
`Q.
`And to accomplish this purpose
`Gharda states that adding 20 percent to 30
`percent by weight of dichloroacetic acid to
`trichloroacetic acid is generally sufficient,
`right?
`A.
`
`It also says that on page nine, yes.
`Q.
`Yes, that is what I was referring
`
`to.
`
`So he is basically saying add a
`minor amount of DCA to TCA for the purpose of
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`bringing its melting point down to about ten
`degrees Centigrade?
`A.
`It doesn't say minor amount.
`is not a minor amount in my opinion.
`Q.
`Okay.
`It is one-third of the amount
`of DCA as TCA, approximately, you will agree with
`that, won't you?
`A.
`I would agree with that.
`Q.
`Now, in general the melting point of
`a solvent is depressed by dissolving a solute in
`that solvent, correct?
`A.
`Solvent doesn't have a melting point, so
`you have to restate the question.
`Q.
`Water can be a solvent, can't it?
`It can be a solvent, right.
`Q.
`And water has a melting point,
`doesn't it?
`A.
`Not at the same temperature.
`Q.
`No, I understand.
`I am just asking
`you a general question.
`A.
`You have to rephrase the question.
`Q.
`Let's say there is a solvent that
`can exist in both liquid and solid form.
`A.
`Okay.
`Q.
`
`And the point at which it
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`Gribble - direct
`transitions from liquid to solid or solid to
`liquid is the melting point, right?
`A.
`That is correct.
`Q.
`And to depress the melting point of
`a solvent, generally one must dissolve a solute
`in that solvent, correct?
`A.
`Again, you are not -- you can't depress a
`melting point when you have a solution, when you
`have a liquid.
`Q.
`My point is this --
`What you would have to do would be to
`A.
`freeze the compound, then add the solute to see
`if that melting point would be further depressed.
`Q.
`But you are making it more
`complicated perhaps than my question intends.
`My point is, a melting point
`depressant to function as a melting point
`depressant has to be soluble in the material
`whose melting point is being depressed, right?
`A.
`Not necessarily.
`You can mix two solids
`together and the melting point of each will be
`depressed.
`I didn't say it has to be dissolved.
`Q.
`What I said is it has to be soluble.
`So, for
`example, we make ice cream, we add salt to water,
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`
`A.
`
`A.
`
`And you put salt in the ice?
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`Gribble - direct
`right?
`Is that right?
`A.
`Or salt to the ice cream, yes.
`Q.
`I don't add salt to my ice cream.
`I don't eat ice cream.
`Q.
`You are familiar with ice cream
`freezers, right, where you put the ice cream
`mixture in a container of ice?
`A.
`Okay.
`Q.
`Right.
`And the function of the salt is to
`Q.
`depress the melting point of water, right?
`A.
`Right.
`And it does that because the salt is
`Q.
`soluble in the water and disrupts the crystalline
`structure of the water, correct?
`A.
`I am not sure that is the mechanism, but I
`will go along with what you said.
`Q.
`The only point I was trying to
`establish is you couldn't depress the melting
`point of water by adding sand or something that
`is completely insoluable in water, right?
`A.
`I am not so sure.
`Again, if you take two
`solids together and simply mix them together they
`are not dissolved together but the melting point
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`will be lowered.
`Q.
`Okay.
`Well, I think we better move on
`
`then.
`
`Now the melting point of
`trichloroacetic acid is around 52 to 58 degrees,
`is that your understanding?
`A.
`I can't recall exactly but I will take
`your word for that.
`Q.
`Let me show you a document, Dr.
`Gribble that we have asked be marked as Exhibit
`2016.
`Do you recognize this as a material safety
`data sheet for trichloroacetic acid?
`A.
`I do, yes.
`Q.
`And usually these are abbreviated
`MSDS, right, often times?
`A.
`They, yes.
`Q.
`Usually MSDS documents are
`authoritative sources of physical properties of
`compounds, right?
`A.
`I would say for the most part, yes.
`Q.
`Do you see that under the physical
`properties of trichloroacetic acid it identifies
`the melting point as being 52 to 58 degrees
`Centigrade?
`
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`A.
`Yes, I see that.
`Q.
`And you don't have any reason to
`disagree with that, do you?
`A.
`No.
`And so the Gharda patent tells us
`Q.
`that dichloroacetic acid is effective to reduce
`the melting point of trichloroacetic acid to
`somewhere around ten degrees or less than 20
`degrees when it is dissolved in the TCA at a
`concentration of 20 to 30 percent, right?
`A.
`It does say that.
`But how can you take a
`melting point of a liquid?
`How did it get to ten
`degrees?
`We'll debate that another time.
`Q.
`I don't see.
`To me it is simply a
`A.
`solvent.
`You are dissolving the TCA.
`Q.
`I understand that is the point you
`want to make.
`You have made it several times
`already.
`
`Now, the fact is if you have a
`liquid TCA that's been heated to above its
`melting point and you add 25 percent DCA to it,
`you now have a liquid, right?
`If you
`A.
`You have a liquid to start with.
`are melting the TCA that is a liquid and you are
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`adding another liquid.
`And you can then
`Q.
`That is right.
`determine what the melting point or freezing
`point is of that liquid, can't you?
`A.
`I suppose you could do that, yes.
`Q.
`And what Gharda tells us that if you
`do that its melting point is reduced to below 20
`degrees Centigrade, right?
`Objection.
`MR. GERSHIK:
`And I don't see
`It doesn't say that.
`A.
`where they make that measurement in the '440.
`Q.
`You don't understand that that is
`what the point of Gharda is, when Gharda says
`that DCA is effective in reducing the melting
`point to less than 20 degrees when its
`concentration is 20 to 30 percent?
`That is not
`how you understand that teaching of Gharda?
`A.
`Well, on page nine it says below ten
`degrees.
`Okay, ten degrees.
`Q.
`That is what it says.
`Okay.
`Now, example two of the Gharda WO
`Q.
`'440 application indicates that the melting point
`of the TCA is reduced to below 20 degrees when 20
`percent dichloromethane is incorporated into the
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`
`Gribble - direct
`TCA, correct?
`A.
`On page eleven, example two?
`Q.
`Yes.
`Again that is not anything to do with a
`A.
`melting point.
`It is simply they are carrying
`out this reaction example two at 20 degrees.
`Q.
`Let's see what we can agree that
`they are doing.
`They have TCA in there as a reaction
`medium, correct?
`As a solid that is then
`A.
`That is the acid.
`added to methylene dichloride.
`Q.
`Then they add 20 percent
`dichloromethane to that material, correct?
`A.
`It doesn't say 20 percent.
`They are
`adding 300 milliliters of methylene dichloride.
`Q.
`And how many milliliters of TCA were
`
`there?
`I would have to know the density of TCA.
`A.
`It is 1.5 kilograms of TCA.
`Q.
`Okay.
`Fair enough.
`They add 300 milliliters of
`dichloromethane or what they refer to here as
`methylene dichloride to 1500 grams of
`trichloroacetic acid, right?
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`A.
`That is what it says, yes.
`Q.
`That is something on the order of 20
`percent depending on the density of the
`trichloroacetic acid, is that your point?
`A.
`That is my point.
`Q.
`And then they add the sulfide
`precursor to that which then dissolves in that
`mixture, correct?
`A.
`That is what it says, yes.
`Q.
`And the reaction is conducted at 20
`degrees Centigrade?
`A.
`Yes.
`So your understanding of this would
`Q.
`be that that reaction mixture is a liquid
`reaction mixture, correct?
`A.
`Everything is in solution, yes, so that is
`a liquid mixture.
`Q.
`As we have discussed earlier the EP
`'117 patent, Exhibit 1002, describes the use of
`meta-chloroperbenzoic acid as the oxidant, right?
`A.
`Yes, that is correct.
`Q.
`And do you know whether
`dichloroacetic acid is soluble in
`meta-chloroperbenzoic acid at a concentration of
`20 to 30 percent?
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`
`A.
`
`Gribble - direct
`A.
`I do not.
`Q.
`Do you know whether the melting
`point of meta-chloroperbenzoic acid would be
`reduced from 92 to 94 degrees to a value of ten
`degrees if 20 to 30 percent dichloroacetic acid
`were added to it?
`I believe it
`A.
`I have no way to know that.
`would be a solution.
`I believe the DCA would
`actually dissolve the meta-chloroperbenzoic acid.
`Q.
`You have not tested that, have you?
`I have not tested that.
`Q.
`And you have not looked up a
`reference which tells you whether it would
`dissolve that material at that concentration or
`not, have you?
`A.
`I have not.
`Q.
`And in July of 2010 to know the
`answers to those questions a person skilled in
`the art would have to actually conduct
`experiments, right?
`A.
`One thing I could say --
`Q.
`Could you answer my question first?
`You have to repeat, I am sorry.
`Q.
`So in July of 2010 to know whether
`the melting point of meta-chloroperbenzoic acid
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`
`Gribble - direct
`would be reduced to a value of around ten degrees
`Centigrade by the addition of dichloroacetic acid
`at a concentration of 20 to 30 percent, a person
`of ordinary skill in the art would have to
`conduct an experiment to measure that, right?
`A.
`I would suppose so, yes.
`Q.
`The same would be true with regard
`to methylene chloride, right?
`In other words, in
`July of 2010 for a person of ordinary skill in
`the art to know whether you could reduce the
`melting point of meta-chloroperbenzoic acid to a
`value of ten degrees Centigrade or so, by adding
`20 percent methylene chloride, that person of
`ordinary skill would have to conduct an
`experiment and test that, right?
`A.
`Perhaps not because that is actually
`reported in example one, the fact that you get a
`solution of the sulfide precursor with
`meta-chloroperbenzoic acid --
`Q.
`At what concentration?
`-- and dichloromethane.
`Roughly ten.
`Q.
`How much meta-chloroperbenzoic acid
`is used in example one?
`A.
`Ten gram -- four and a half grams.
`Q.
`How much methylene chloride is used?
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`
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`A.
`100 mils.
`Q.
`So there is a large excess of
`methylene chloride used in example one, correct?
`A.
`As it is stated there, yes.
`That doesn't
`mean that a more concentrated solution could be
`achieved.
`But to know whether you could
`Q.
`achieve that or not you would have to do an
`experiment, wouldn't you?
`A.
`You would, yes.
`Q.
`Meta-chloroperbenzoic acid is not
`the reaction solvent in the EP '117 patent,
`correct?
`A.
`It is the oxidant, it is not the reaction
`solvent.
`Methylene chloride or
`Q.
`dichloromethane, that is the r
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