throbber
w
`b TEADYMED VS UNITED THERAPEUTICS CORPORATION
`
` W"T.T."AMS, ROBER'l‘ on 08/26/2016
`
`Page 169
`
`Fm
`
`elts at 104, and 1 think the Phares melts the 107.
`
`So I'm not certain.
`
`Q
`
`Okay.
`
`Now,
`
`the Phares reference,
`
`that's —— that's a patent application written by
`
`people at United Therapeutics; right?
`
`A
`
`Q
`
`Yes.
`
`Okay. Did you ask anyone at United
`
`Therapeutics: Hey, do you have information about
`
`that particular Form B that you made in the Phares
`
`patent?
`
`A
`
`Q
`
`NO.
`
`But you knew they —— if anyone had that
`
`information, it would be United Therapeutics; right?
`
`A
`
`Q
`
`Presumably.
`
`Right.
`
`You don't think I‘m going to have
`
`that information; right?
`
`A
`
`Q
`
`No.
`
`Right. And if they were different ‘—
`
`right? mm if the Form B in the Phares reference and
`
`the Form B in the ‘393 patent —— if they were
`
`different, don‘t you think that your counsel would
`
`have given you documents showing that they were
`
`different crystal forms?
`
`A
`
`All I know is whatgs stated in the
`
`
`
`
`
`
`
`
`documents.
`
`UT'EXAZO 9
`
`United Therapeuti
`SteadyMed v.
`[3.169
`EPRZOiBDDO B
`
`
`Elisa Dreier Reporting Corp., U.S. Legal Support Company
`950 Third Avenue, New York, NY
`10022
`
`(212)557—5558
`
`|PR2020-00769
`
`United Therapeutics EX2006
`Page 2297 of 7113
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`lb
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`19
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`Page 2297 of 7113
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`

`

`STEADYMED VS UN:TED THERAPEUTZCS CORPORA‘LL'ION
`
`WTLLIAMS, ROBERT on 08/26/2016
`
`n
`
`Page 170
`
`Q
`
`A
`
`That you received.
`
`Yes.
`
`
`
`And you didn‘t ask for any fiurther
`Q
`information on this issue?
`
`A
`
`No. No.
`
`i didn't think there was a need
`
`to.
`
`Q
`
`So we were looking at the patentr
`
`Exhibit 1001, also known as "Williams Deposition
`
`Exhibit 3.”
`
`I want to go to the next paragraph that
`
`1
`
`2
`
`3
`4
`
`5
`
`01
`
`x]
`
`8
`
`9
`
`:0
`
`begins with,
`
`"At this stage .
`
`,
`
`."
`
`
`
`:1
`
`12
`
`13
`
`14
`
`15
`
`Do you see that paragraph?
`
`In column 12.
`
`Okay.
`
`Column 12 and mm where —— okay.
`
`It‘s about line 53.
`
`Hmm—hmm.
`
`I'll read it into the record so we know
`
`A
`
`Q
`
`A
`
`Q
`
`gi
`
`
`
`E
`
`16
`
`where we are?
`
`l?
`
`18
`
`19
`
`20
`
`2]
`
`22
`
`23
`
`24
`
`25
`
`A
`
`Q
`
`Okay.
`
`It says,
`
`“At this stage,
`
`if the melting
`
`point of the treprostinil diethanolamine salt is
`
`more than 104 degrees C, it was considered polymorph
`
`B.“
`
`A
`
`Q
`
`Did I read that correctly?
`
`That's what it says.
`
`Okay.
`
`So if you're in the ‘393 patent,
`
`
`UTEx209
`they are identifying whether a treprostinil
`SteadyMed v. United Therapeuti s
`P170
`1PR2016-ODG 5
`
`Elisa Dreier Reporting Corp., U.S. Legal Support Company (212)557—5558
`950 Third Avenue, New York, NY
`10022
`
`IPR2020-00769
`
`United Therapeutics EX2006
`Page 2298 of 7113
`
`IPR2020-00769
`United Therapeutics EX2006
`Page 2298 of 7113
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`\0
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`STEADYMED VS UNITED THERAPEUTICS CORPORATION
`
`WILLIAMS, ROhERT on 08/26/2016
`Page 171
`
`diethanolamine salt is Form B by its melting point;
`
`right?
`
`A
`
`Q
`
`Yes.
`
`Okay. And if the melting point is
`
`greater than 104,
`
`that indicates that it must be the
`
`Form B; correct?
`
`A
`
`Your question again?
`
`Let‘s just put it this way:
`Q
`point is a signature for Form B.
`
`The melting
`
`A
`
`It‘s one characteristic, physical
`
`property, yes.
`
`Q
`
`They're not just saying it's one
`
`characteristic property;
`
`they're saying it is the
`
`property which tells you it's Form 3.
`
`Isn't that
`
`what that sentence says?
`
`A
`
`Well,
`
`its X ray defraction pattern is
`
`going to be much more diagnostic.
`Q
`Okay.
`I'm just asking: What does this
`sentence say?
`
`"At this stage if melting
`Well, it says,
`A
`point of the treprostinil diethanolamine salt is
`
`more than 104 degrees, it was considered polymorph
`
`B." That‘s what it says.
`
`Q
`
`Okay. Let me ask you this:
`
`The people
`
`i
`‘
`
`
`
`
`i
`5
`
`g
`i
`
`at United Therapeutics,
`UTExZOQ
`they know how to take PXRDS;
`[3.171
`SteadyMed v. United Therapeuti s
`|PR2018mODD B
`
`Elisa Dreier Reporting Corp., U.S. Legal Support Company (212)557—5558
`950 Third Avenue, New York, NY
`10022
`
`|PR2020-00769
`
`United Therapeutics EX2006
`Page 2299 of 7113
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`Page 2299 of 7113
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`

`

`
`vs
`
`
`STEADYMED
`UNlTEJ THERAPEUTICS CORPORATION
`
`Page 172
`WILLIAMS,
`ROBERT 01 08/26/2016
`
`right?
`
`MS. HASPER:
`
`Objection.
`
`Speculation.
`
`(A)
`
`THE WITNESS:
`
`I'm not sure if they do
`
`the: in in—houee,
`
`or if they contract that out to
`
`
`
`ano:her lab that has deep expertise in this or not.
`
`I don‘t know if they do it in—house or not.
`
`
`I
`
`don‘t
`
`know.
`
`BY MR. POLLACK:
`
`Q
`
`Okay.
`
`They have access
`
`to the technique;
`
`right?
`
`A
`
`Q
`
`Sure.
`
`We saw in the Phares reference,
`
`they have
`
`a PXRD for Form B; right?
`
`A
`
`Q
`
`Yes.
`
`So presumably,
`
`they did a PXRD of what
`
`they did here in the
`
`’393 patent,
`
`Exhibit 1001;
`
`right?
`
`MS. HASPER:
`
`Same objection.
`
`THE WTTNRSS:
`
`You‘re asking me presumably
`
`they did a PXRD?
`
`BY MR. POLLACK:
`
`Q
`
`A
`
`Yeah.
`
`I don't know if there was data on that or
`
`not
`
`in here.
`
`
`
`g
`
`Q
`
`There‘s no data in here.
`P.172
`
`
`
`UTEx.209
`SteadyMed V. United Therapeuti
`1P.R_2.QJ§:.QDQ5
`
`Elisa Dreier Reporting Corp,, U.S. Legal Support Company [212) 57 555 8
`950 Third Avenue, New York, NY
`10022
`
`IPR2020-00769
`
`United Therapeutics EX2006
`Page 2300 of 7113
`
`
`
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`
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`Page 2300 of 7113
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`

`

`STEADYMED VS UNITED THERAPEUTICS CORPORATION
`
`Page 173
`
`WILLIAMS, ROBERT on 08f26/2016
`
`Let me ask it to you this way:
`
`Do you
`
`think that the people at United Therapeutics would
`
`have reported that this is Form B without do doing a
`
`PXRD?
`
`Is that your opinion?
`
`A
`
`Q
`
`I don‘t have an opinion.
`
`One way or the other?
`
`the people at United
`I mean,
`Okay.
`I
`1 Therapeutics,
`they're not amateurs at these
`!
`techniques; right?
`:
`MS. HASPER: Objectionl
`
`Scope.
`
`BY MR. POLLACK:
`
`Q
`A
`
`Q
`
`A
`
`You don't know?
`I don‘t know.
`
`Okay.
`
`We’ve been going for another an hour,
`
`could we possibly have a break?
`
`THE VIDEOGRAPEER: This ends media NO.
`
`2
`
`
`
`in the deposi:ion of Robert M. Williams, Ph.D.
`
`We're off the record at 2:45 P.M.
`
`(Off the record}
`THE VIDEOGRAPEER: This begins Media
`in the deposition of Robert M. Williams, Ph.D.
`
`No.
`
`3
`
`The time is 2:57 P.M.
`We are back on the record.
`MR. POLLACK:
`I'm going to mark as
`
`
`
`
`i
`i
`
`i
`%
`
`;
`
`;
`E
`
`UTExzog
`Williams Deposition Exhibit 18, a Guidance for
`P173
`SteadyMed v. United Therapeuti s
`iPRZDiS-ODO 6
`
`Elisa Dreier Reporting Corp., U.S. Legal Support Company (212)557—5558
`950 Third Avenue, New York, NY
`10022
`
`|PR2020-00769
`
`United Therapeutics EX2006
`Page 2301 of 7113
`
`(TI
`
`10
`
`ll
`
`13
`
`14
`
`15
`
`16
`
`17
`
`18
`
`19
`
`20
`
`21
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`23
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`24
`
`25
`
`IPR2020-00769
`United Therapeutics EX2006
`Page 2301 of 7113
`
`

`

`
`STEADYMED VS UNrTEJ THERAPEUTICS CORPORATION
`
`
`
`WlLLlAMS, ROBERT 01 OBHZE/ZOlE
`Page 174
`
`
`
`Industry from the FDA titled,
`
`”ANDAs:
`
`Pharmaceutical Solid Polymorphism.”
`
`(Exhibit 18 marked)
`
`BY MR. PCLLACK:
`
`(H
`
`to
`
`
`
`21
`
`22
`
`23
`
`24
`
`Q
`
`I‘m going to represent to you,
`
`this
`
`wasn't attached to your report. But
`
`I‘m wondering
`
`if you've reviewed this document
`
`in the past in the
`
`i course of your various ANDA litigations or
`
`i consulting?
`
`
`
`A
`
`Q
`
`Not that I can recall.
`
`Okay. This is um well, can you explain
`
`to me what is —— what this document
`
`is?
`
`A
`
`Q
`
`A
`
`Q
`
`No.
`
`Okay.
`
`I've never seen it before.
`
`Sure.
`
`Do yOu know what a Guidance for
`
`Industry is —— I mean —— From the FDA?
`
`A
`
`I‘ve seen FDA guidance things.
`
`These are
`
`things the FDA puts out to help pharmaceutical
`
`companies jump through all the hoops with the FDA to
`
`get approval.
`
`Q
`
`Okay. And I'm right —— this one is about
`
`i pharmaceutical solid polymorphism?
`
`MS. HASPER: Objection.
`
`THE WITNESS: That‘s what it says.
`P.174
`
`
`UTEX2D§9
`SteadyMed v. United Therapeuthis
`IPR201s—oood6
`
`Elisa Dreier Reporting Corp., U.S. Legal Support Company (212)557—5558
`950 Third Avenue, New York, NY
`10022
`
`IPR2020-OO769
`
`United Therapeutics EX2006
`Page 2302 of 7113
`
`IPR2020-00769
`United Therapeutics EX2006
`Page 2302 of 7113
`
`

`

`Lu
`
`0.]
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`\O
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`10
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`21
`
`25
`
`
`22
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`23
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`24
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`
`STEADYMED vs UNITED rHsRAPEUTICS CORPORATION
`
`WILLIAMS, ROBERT on 08/26/2016
`Page 175
`F—“’—“
`“I
`
`
`
`MS. HASPER:
`
`Scope.
`
`BY MR. POLLACK:
`
`Q
`
`Okay. And in simple language,
`
`that‘s
`
`about different crystal forms of drugs; right?
`
`MS. HASPER:
`
`Same objection.
`
`THE WITNESS: Yes.
`
`BY MR. POLLACK:
`
`Q
`
`Okay.
`
`MS. HASPER: Counsel,
`
`if I could Clarify:
`
`You said this was a —— Exhibit 18.
`
`I
`
`thought
`
`the
`
`previous exhibit was 18.
`
`THE REPORTER; No,
`
`the last one was 17.
`
`MS. HASPER:
`
`Thank you.
`
`I'll correct
`
`that,
`
`then.
`
`BY MR. POLLACK:
`
`Q
`
`Let me ask you: Are you familiar with
`
`any guidances from either the FDA or —— are you
`
`familiar with the ICH?
`
`A
`
`I‘m trying to remember what the acronym
`
`stands for.
`
`I don't remember now.
`
`Q
`
`A
`
`Okay.
`
`But, yes, I've seen —— I‘ve seen each
`
`before.
`
`I was trying to remember what the acronym
`
`is.
`
`Q
`
`
`UTExZOQ
`Have you looked at any either :CH or FDA
`[3.175
`SteadyMed v. United Therapeuti s
`|PR2018~000 6
`
`
`Elisa Dreier Reporting Corp., U.S. Legal Support Company (212)557—5558
`950 Third Avenue, New York, NY
`l0022
`
`|PR2020-00769
`
`United Therapeutics EX2006
`Page 2303 of 7113
`
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`United Therapeutics EX2006
`Page 2303 of 7113
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`

`STEADYMED vs UNITED THERAPEUTICS CORPORATION
`
`WILLIAMS, ROBERT on 08/26/2016
`
`Page 176
`
`
`
`documents concerning polymorphism in the past?
`
`MS. HASPER: Objection. Relevance.
`
`Scope.
`
`THE WITNESS: Not that
`
`I can think of.
`
`BY MR. POLLACK:
`
`Q
`
`Okay. Let me ask you just to turn to
`
`page 9 of Exhibit 18. You see here this is a w— a
`
`guidance setting forth specifications for polymorphs
`
`in drug substances Ior solid, oral, and suspension
`
`dosage—form products.
`
`And you see that in the first square,
`
`the
`
`question is:
`
`Ts there a polymorph specification in
`
`the USP —n
`
`the USP "u that's the United States
`
`Pharmacopeia?
`
`A
`
`Q
`
`A
`
`Pharmacopeia.
`
`What is the United States Pharmacopeia?
`
`Oh,
`
`it‘s a compendium of drug substances
`
`that is indexed and catalogued by this organization.
`
`Q
`
`Okay. And the organization which is
`
`known as the "USP";
`
`is that right?
`
`A
`
`Q
`
`E think so, yes.
`
`The USP puts in specifications for each
`
`drug substance,
`
`including things like purity,
`
`crystal form, melting point —— is that your
`
`understanding?
`
`UT'EX.2O 9
`SteadyMed v. United Therapeuticis
`P176
`
`EPRZDTB~GGDQG
`
`Elisa Dreier Reporting Corp., U.S. Legal Support Company
`950 Third Avenue, New York, NY
`10022
`
`(212)557—5558
`
`IPR2020-OO769
`
`United Therapeutics EX2006
`Page 2304 of 7113
`
`U1
`
`0\
`
`
`
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`
`18
`
`19
`
`2D
`
`21
`
`22
`
`23
`
`24
`
`25
`
`IPR2020-00769
`United Therapeutics EX2006
`Page 2304 of 7113
`
`

`

`
`STEADYMED VS UNlTED THERAPEUTICS CORPORAT:ON
`
`Page 177
`
`WILLIAMS, ROBERT on 08/26/2016
`
`i
`
`A,
`
`I don‘t recall off the top of my head
`
`I exactly what data's in there.
`
`Q
`
`A
`
`Q
`
`Okay. You've used the USP; right?
`
`I have.
`
`Okay. What do you recall from your use
`
`of it? What that —— what is in there?
`
`A
`
`It‘s been a while since I
`
`looked at one,
`
`so I don't exactly remember.
`
`one?
`
`Q
`
`A
`
`Q
`
`A
`
`Okay. About how long did you look at
`
`I don't remember.
`
`More than a year ago?
`
`Well, you know, my father was a
`
`pharmacist, and he has a whole bunch of old ones
`
`that we just had to move from one place to another.
`
`I looked at those, but
`those are ancient.
`Q
`Okay. Have you ever looked at
`
`the
`
`E
`
`
`
`i
`i
`
`E
`g
`I
`
`
`
`17
`
`18
`
`19
`
`2O
`
`21
`
`22
`
`23
`
`
`
`—— you understand there will be a USP monograph
`: U.S.
`I
`for treprostinil?
`A
`Yeah.
`
`Q
`
`And there's also one for treprostinil
`
`diethanolamine salt; correct?
`
`A
`
`I guess so.
`
`I‘ll take your
`
`representation.
`
`Q
`
`Okay.
`
`You haven‘t
`
`looked?
`P177
`
`UTEx209
`SteadyMed v, United Therapeuti 5
`[PR2DiB-DUD 5
`
`Elisa Dreier Reporting Corp., U.S. Legal Support Company
`950 Third Avenue, New York, NY
`10022
`
`(212)557-5558
`
`|PR2020-00769
`
`United Therapeutics EX2006
`Page 2305 of 7113
`
`IPR2020-00769
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`Page 2305 of 7113
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`

`

`
`STEADYMED vs UNITED THERAPEUTICS CORPORATION
`Page 178
`WILLIAMS, ROBERT on 08/26/2016
`
`
`
`
`
`x]
`
`KD
`
`{ O
`
`A
`
`Q
`
`No.
`
`Okay. Now, you see here, one of the
`
`things that the FDA asks the ANDA applicant to do is
`
`to look if there's a polymorph specification in the
`
`USP, and then it says, for example, "melting point."
`
`Do you see that?
`
`A
`
`Yeah,
`
`I see that.
`
`MS. HASPER: Objection.
`
`Scope.
`
`BY MR. POLLACK:
`
`Q
`
`So melting point is one of the things the
`
`FDA calls out.
`
`In fact, it's the only thing in here
`
`that they give as an example as associated with a
`
`polymorph.
`
`Do you see that?
`
`MS. HASPER:
`
`Same objection.
`
`THE WITNESS:
`
`It says, ”example.“
`
`"For
`
`example."
`
`BY MR. POLLACK:
`
`Q
`
`A
`
`Q
`
`There's other things; right?
`
`Certainly.
`
`Right. But melting point is the one that
`
`they gave in this document?
`
`A
`
`As an example.
`
`Ms. HASPER:
`
`Same objection.
`
`BY MR. POLLACK:
`
`Q
`
`
`m
`
`UTEXZUQ
`Because melting point is something that
`R178
`SteadyMed v. United Therapeuti s
`lPRZOiG—OOO 8
`
`Elisa Dreier Reporting Corp., U.S. Legal Support Company
`950 Third Avenue, New York, NY
`10022
`
`(212)557—3558
`
`|PR2020-00769
`
`United Therapeutics EX2006
`Page 2306 of 7113
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`

`STEADYMED VS UNLTED THERAPEUTICS CORPORATION
`
`Page 179
`
`WILLIAMS, ROBERT on 08/26/2916
`
`uniquely identifies a polymorph; right?
`
`
`
`2
`2
`g
`
`5
`3
`
`R]
`
`(A)
`
`MS. HASPER:
`
`Same objection.
`
`Mischaracterizes the underlying document.
`
`THE WITNESS:
`
`I would not necessarily
`
`agree with that.
`
`MR. POLLACK: Let me mark as Williams
`
`Deposition Exhibit 19 a document that's been called
`
`”Exhibit 2030“ in this case.
`
`It's an article by ——
`
`rather than try to say the name,
`
`it‘s an article
`
`that appeared in the International Journal of
`
`Pharmaceutics in 2006.
`(Exhibit 19 marked)
`BY MR. POLLACK:
`
`Is Williams Deposition
`Let me ask you:
`Q
`Exhibit 19 an article you relied upon in your
`Declaration?
`
`A
`
`Q
`
`Yes.
`
`Okay.
`
`Do you have any idea how to
`
`pronounce the author‘s first name?
`
`A
`
`Q
`
`article?
`
`A
`
`Q
`
`"Adhiyaman."
`
`Okay. We'll call this the Adhiyaman
`
`Okay.
`
`Okay.
`
`Now,
`
`in the Adhiyaman article, we
`
`see —— I think my understanding of this —u or at
`UTExZUQ
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`STEADYMED VS UNITED THERAPEUTICS CORPORATION
`
`Page 180
`
`WILLIAMS, ROBERT on 08/26/2016
`
`1
`
`2
`
`3
`
`4
`
`b
`
`5
`7
`
`8
`
`9
`
`least of your opinion of it —— is that there are a
`
`number of crystals of certain chemical called
`
`”dipyridamole“?
`
`Is that a decent pronunciation of
`
`it, or how would you pronounce that?
`
`A
`
`"Dipyridamole "
`
`Q
`solvents;
`
`Okay. And they're all made in different
`is that fair?
`
`A
`
`Q
`
`Yes.
`
`Okay. And each of them has a different
`
`TO
`
`PXRD pattern;
`
`is that fair?
`
`
`
`g
`i
`
`5
`
`5
`
`E
`g
`g
`i
`
`
`
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`12
`;3
`14
`
`;5
`
`"6
`
`17
`
`18
`
`L9
`
`20
`
`21
`
`22
`
`23
`
`24
`
`2 S
`
`A
`I
`think that's what they're illustrating
`in the article, yes.
`Q
`Okay.
`Isn't it correct that a different
`PXRD pattern means that the crystal has a different
`
`three—dimensional structure in a solid form?
`
`A
`
`O
`
`Yes.
`
`Okay.
`
`So each of these is really a
`
`different crystal form of the same drug;
`
`is that
`
`fair?
`
`A
`
`Q
`
`I
`
`think that’s fair.
`
`Okay.
`
`So what we learned about
`
`in this
`
`article is sometimes when you use different
`
`solvents, you get different crystal forms of the
`
`
`
`same drug; right?
`
`A
`
`Yes -
`
`UT Ex. 205:9
`SteadyMed v. United Therapeuti is
`P180
`
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`h)
`
`(A)
`
`(.11
`
`Ch
`
`
`
`2O
`
`21
`
`22
`
`23
`
`24
`
`25
`
`
`STEADYMED VS UNiTED THERAPEUTICS CORPORATION
`Page 181
`WILLIAMS, ROBERT on 08/26/2016
`
`
`
`Q
`
`Okay.
`
`So there‘s nothing in here saying
`
`that two crystals that have the same crystal form
`
`and same PXRD structure made from different solvents
`
`are different?
`
`MS. HASPER: Objection. Mischaracterizes
`
`the document.
`
`THE WITNESS:
`
`Please state your question
`
`one more time?
`
`BY MR. POLLACK:
`
`Q
`
`Sure.
`
`Sure.
`
`So there are no —— let me make the
`
`following clear: There are no examples in Williams
`
`Deposition Exhibit 19 of two crystals having the
`
`same PXRD pattern but which are different crystal
`
`forms.
`
`A
`
`Q
`
`You'll have to ask me that one more Lime.
`
`Sure. There are no examoles in Williams
`
`Deposition Exhibit 19 of two crystals, made with
`
`different solvents, having the same PXRD pattern but
`
`different —— but are different crystal forms?
`
`A
`
`Irm not sure I can come to that
`
`Conclusion.
`
`And what I did cite from this article is
`
`that the conclusion, which I quoted in my
`
`Declaration, and it's also based on my experience of
`Unfied'Therapeufi
`R181
`SteadyMed V.
`lPR2016—ODD 0')
`
`
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`

`
`STEADYMED vs UNITED THERAPEUTICS CORPORATION
`Page 182
`WILLIAMS, ROBERT on 08/26/2016
`
`crystallizing the same compound on different days
`
`from different solvents under slightly different
`
`conditions, you can get a different melting point.
`
`And it depends on the scale and lots of things.
`
`Q
`
`Okay. But could you get a different
`
`melting point because you‘ve gotten a different
`
`crystal form.
`
`isn't that the issue?
`
`A
`
`Q
`
`Not necessarily.
`
`So your testimony today is,
`
`I can have —~
`
`let me ask you this:
`
`Tf I have two crystals that
`
`have the same PXRD pattern, can I get two different
`
`melting points?
`
`A
`
`Q
`
`Yes.
`
`Okay. And what is the reason for that in
`
`your opinion?
`
`MS. HASPER: Objection.
`
`Scope.
`
`THE WITNESS:
`
`SO the way these melting
`
`points, which are done typically today with this
`
`differential scanning calorimetry,
`
`the melting
`
`ranges can depend on the rate of heating,
`
`the sample
`
`size, and even the individual
`
`instrument that‘s
`
`used. There can be variability.
`
`BY MR. POLLACK:
`
`to
`
`E
`
`17
`
`18
`
`19
`
`20
`
`21
`
`22
`
`23
`
`
`
`Q
`
`Sure. You're saying there can be errors
`
`25
`
`in the measurement?
`
`
`
`P482
`
`UT'EX.2059
`SmadyMedV‘UnfledThaepemfis
`|PR2016—ODO 6
`
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`950 Third Avenue, New York, NY
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`

`STEADYMED VS UNITED THERAPEUTICS CORPORATION
`
`
` WILLIAMS, ROBERT on 08f26/2016 Page 183
`
`l
`
`2
`
`LU
`
`4
`
`5
`
`6
`
`A
`
`Q
`
`Yes.
`
`Fair enough.
`
`okays
`
`But assuming that the appropriate scan
`
`rate is used and appropriate sample size is used and
`
`all of those things are the case, will two crystals
`
`which have the same PXRD pattern have the same
`
`7 melting point?
`
`8
`
`LD
`
`10
`
`Ll
`
`;2
`
`13
`
`;4
`
`15
`
`LE
`
`i7
`
`
`
`A
`
`i don't know if that‘s ubiquitously true.
`
`I wouldn't agree with that.
`
`Q
`
`Do you not know, or do you formally
`
`disagree with that?
`
`A
`
`Q
`
`I disagree.
`
`Okay.
`
`Do you have any —— is there
`
`anything in this article that supports your opinion?
`
`A
`
`Well,
`
`the conclusion is that
`
`-— it says
`
`right here, ”In conclusion, it can be said that the
`
`crystallization conditions" ~—
`
`Q
`
`A
`
`Read that slowly.
`
`Sorry.
`
`”In conclusion, it can be said that the
`
`crystallization conditions and the medium used have
`
`a major effect on dipyridamole crystals habit
`
`
`
`5
`
`
`
`i
`
`é
`
`18
`
`19
`
`20
`
`21
`
`22
`
`23 modification under ambient conditions.
`
`The crystals
`
`24
`
`showed significant changes in the shape, size,
`
`UTEx209
`25 melting points, dissolution rate, XRD patterns and
`{3.183
`SteadyMed v. United Therapeuti s
`|PR2015~ODO 5
`
`Elisa Dreier Reporting Corp., U.S. Legal Support Company (212)557w5558
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`10022
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`

`STEADYMED VS UNITED THERAPEUTICS CORPORATION
`
`WILLlAMS, ROBERT O? 08/26/2016
`Page 184
`
`[\)
`
`(AJ
`
`U]
`
`\D
`
`
`
`
`
`DSC curves.”
`
`And I quoted that in my ——
`
`Q
`
`But here,
`
`they pointed out they all had
`
`different XRD patterns, right?
`
`A
`
`Q
`
`Okay.
`
`Right?
`
`And,
`
`in fact,
`
`that‘s what
`
`the data shows
`
`in here.
`
`They all had different XRD patterns?
`
`A
`
`Q
`
`Hmm—hmm.
`
`Right.
`
`I‘m asking about
`
`two crystals
`
`having the same XRD pattern.
`
`A
`
`So in my own research, we do a lot of
`
`x—ray crystallography‘ And I work pretty closely
`
`with an expert crystallographer, Orrin Anderson.
`
`And we've had crystals that had the exact same XRD
`
`pattern that were produced on different days that
`had slightly different melting points.
`So I‘ve seen
`
`this myself.
`Q
`Okay.
`A
`So what you‘re trying to say is just
`
`simply not ubiquitously true.
`
`Q
`
`Okay.
`
`Do you have any literature or any
`
`papers mm other than your own personal anecdotal
`
`experience, do you have any scientific literature or
`
`i
`
`
`
`E
`:
`
`g
`g
`I
`
`papers that support that opinion?
`
`
`
`13.134
`
`UTExZDQ
`SteadyMed v. United Therapeuti s
`1PR201600006
`
`Elisa Dreier Reporting Corp., U,S. Legal Support Company
`950 Third Avenue, New York, NY
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`
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`Page 2312 of 7113
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`STEADYMED VS UNITED THERAPEUTICS CORPORATION
`
`WILLIAMS, ROBERT on 08/26/2016
`
`
`Page 185
`
`E
`E
`
`i
`
`g
`é
`
`ii
`
`3
`
`
`
`i
`E
`g
`g
`
`A
`
`Okay .
`
`P185
`
`UT Ex. 20 9
`Steadleed v. United Therapeuti e
`_..|.PR2016.~.DOG 5
`
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`
`A
`
`I'm sure I could find it if I was asked
`
`to, but that was based on my own experience.
`
`Okay.
`Q
`And that‘s —— it happened not just once.
`A
`It‘s happened numerous times.
`
`Lu
`
`U]
`
`Q
`
`Okay. But as part of this proceeding,
`
`you didn‘t look for any papers that supported that
`
`Opinion?
`
`A
`
`Well,
`
`I think the main point here is that
`
`you can't compare the polymorph form and Phares to
`
`what*s in the ‘393. That was the main underlying
`
`theme here.
`
`Q
`
`Right. But your opinion on that was
`
`based on the idea that the same polymorph could have
`
`two different melting points; correct?
`
`MS. HASPER: Objection. Mischaracterizes
`
`the document and the testimony.
`
`THE WITNESS:
`
`I mean, what's
`
`characterized is the same polymorph —— or what's
`called —— but
`there wasn't enough information to
`ascertain that that was the case.
`BY MR. POLLACK:
`
`Q
`
`The people who called it the same
`
`polymorph, that's United Therapeutics?
`
`
`
`
`
`2U
`
`21
`
`22
`
`23
`
`24
`
`25
`
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`Page 2313 of 7113
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`

`STEADYMED VS UNITED THERAPEUTICS CORPORATION
`
`WILLIAMS, ROBERT on 08/26/2016
`Page 186
`
`O
`
`A
`
`Q
`
`A
`
`Q
`
`A
`
`Q
`
`
`The people you’re working for; right?
`
`That doesn‘t mean they're infallible.
`
`Okay.
`
`It wasn't —— it wasn't me; right?
`
`No.
`
`
`It wasn‘t Drv Winkler?
`
`No.
`
`NO?
`
`
`
`And —— okay.
`
`You think maybe they made a
`
`mistake in identifying the polymorphs?
`
`MS. HASPER: Objection.
`
`Mischaracterizes —— testimony.
`
`THE WITNESS: Yeah.
`
`I was addressing
`
`Dr. Winkler‘s analysis.
`
`BY MR. POLLACK:
`
`Q
`
`That's not what E asked you.
`
`I said, do you think they made a mistake
`
`in identifying the polymorphs 0E each of those
`
`papers? United Therapeutics made a mistake?
`
`MS. HASPER: Objection. Mischaraoterizes
`
`testimony. Asked and answered.
`
`THE WITNESS:
`
`I cannot be 100 percent
`
`certain.
`
`BY MR. POLLACK:
`
`Q
`
`Okay.
`
`You didn‘t do anything to
`
`
`
`i
`
`I
`
`[PR2016000 5
`
`investigate whether they made a mistake in
`13.185
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`U"!
`
`01
`
`x}
`
`01?
`
`10
`
`11
`
`12
`
`13
`
`14
`
`16
`
`17
`
`18
`
`19
`
`2O
`
`21
`
`read.
`
`A
`
`Q
`
`No.
`
`I just have the documents as the‘
`
`And the documents called both of those
`
`"polymorphs Form B”?
`
`A
`
`Yes. Made under different conditions,
`
`and Phares doesn't provide any information on
`
`solvent that was used, scale, source of the
`
`treprostinil, and so on.
`
`So it's just not enough
`
`there.
`
`Q
`
`You know, you've brought up the term
`
`"scale” several
`
`times in this deposition.
`
`Looking
`
`back at Exhibit 1001r
`
`is there anything ——
`
`A
`
`Q
`
`What‘s Exhibit 1001?
`
`Exhibit 1001 is the '393 patent.
`
`It‘s
`
`also known as "Williams Deposition Exhibit 3."
`
`A
`
`Okay.
`
`Q
`
`I'd like you to look at claims in the
`
`'393 patent.
`
`Do you see anything in there that says
`
`what scale the reaction is being carried out at?
`
`NO.
`
`Okay.
`
`So the reaction covers any scale;
`
`
`
`2
`
`a
`i
`
`
`
`STEADYMED VS UNITED THERAPEUTICS CORPORATION
`
`WELLIAMS, ROBERT on 08/26/2016 Page 187
`
`identifying those two polymorphs?
`
`A
`
`Q
`
`right?
`
`A
`
`Q
`
`Certainly.
`
`Could be bench;
`
`__
`
`UTEx2059
`like
`laboratory reaction,
`P187
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`iPR2016—00096
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`

`STEADYMED vs UNITED THERAPEUTICS CORPORATION
`?age 188
`WILLIAMS, ROBERT on 08/25/2015
`
`Moriarty did in his Journal of Organic Chemistry
`
`article?
`,
`
`A
`
`Q
`
`Yes.
`
`That could be included w» and it could be
`
`in
`
`a large clinical batch; correct?
`
`A
`
`Q
`
`Yes.
`
`Okay. Let me go back to the Phares
`
`reference, Exhibit 1005, known as "Williams
`
`Deposition Exhibit 16.“
`
`If you'COuld turn to
`
`page 42. And we have a not of page 425 here,
`
`so let
`
`me be a little more specific.
`
`
`
`Page 42 in the lower right—hand corner or
`
`the document, original page 40 of the reference ——
`
`A
`
`Q
`
`Yes.
`
`I'm there.
`
`Okay.
`
`w
`
`I was wondering if you could
`
`help me understand some of the chemistry in —- you
`
`see there's a synthesis at the top of page; right?
`
`A
`
`Q
`
`Yes.
`
`Okay. Here's what
`
`I was not fully
`
`understanding: There‘s ~~ if you go to this
`
`synthesis scheme,
`
`there's a structure on the lower
`
`right—hand corner in the scheme. And next to it,
`
`there's an arrow, and there's a letter “L“ above it.
`
`Do you see that?
`
`A
`
`Yes.
`
`
`
`10
`
`ll
`
`12
`
`
`
`20
`
`21
`
`22
`
`23
`
`25
`
`U.S. Legal Support Company
`Elisa Dreier Reporting Corp.,
`950 Third Avenue, New York, NY
`10022
`
`P188
`
`smadyMedv.
`
`
`
`UT'EX.2D 9
`
`United Therepe uti >5
`[PRZOlfiflflDQS
`
`{212)557e5558
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`|PR2020-00769
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`

`

`PagemlBB
`
`g
`2
`g
`i
`%
`
`E
`é
`g
`5
`2
`gI
`
`STEADYMED V5 UNITED THERAPEU‘l'iCS CORPORA‘I‘ION
`
`WILLIAMS, ROBERT on 08/26/2016
`m_mm
`Q
`Okay. And now, what's ~~ to the right of
`the arrow with the letter ”L,” that's the mirror
`image of the —— some of the compounds that are shown
`in claim 9 of the '393 patent;
`is that right?
`A
`So which —— which structures are you
`
`O'\
`
`asking me to compare?
`
`Q
`
`Yeah. Let's take a look at ~e there's a
`
`structure called ”5” in claim 9.
`A
`Okay. That‘s the so~called ”benzindine
`triol."
`Hmm—hmm. And is that structure and
`Q
`claim 5 —— is that the mirror image of the structure
`
`on page 42 also known as “40,” in the lower
`
`rightwhand corner?
`
`A
`
`That would be ll—B where R is H. That
`
`would be the mirror image of the henzindine triol.
`
`Q
`
`Okay. Thanks.
`
`And then in step (1),
`
`if you look down in
`
`the paragraph, it tells you what step (1)
`
`is. And
`
`step (1)
`
`seems to have two parts to it; is that
`
`fair?
`
`There's a little (i) and then a two
`
`
`
`little (ii) part?
`
`A
`
`Yes.
`
`UTEx2m%
`Those are two separate steps in
`Okay.
`Q
`R189
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`

`STEADYMED vs UNITED THERAPEUTICS CORPORATION
`WILLIAMS, ROBERT on 08/26/2016 Page 190
`
`
`
`(1); right?
`
`‘
`!
`g
`
`Yes.
`A
`Okay. And the first step —— the
`Q
`letter —— single (i) step where it says,
`“CL,"
`
`”CH2," ”CN,” and then it says "K2," ”C03“
`
`—— is that
`
`the —— is that the alkylating step like is done in
`
`
`step (a) of claim 9, except for the mirroruimage
`
`compound?
`
`A
`
`Q
`
`Yes.
`
`Okay. And then there‘s a step where it
`
`says "KOHCH3DH reflux 83 percent."
`
`Is that the
`
`hydrolyzing step of —— which is called "step (b)" in
`
`the '393 patent being applied to the mirror—image
`
`compound?
`
`A
`
`Q
`
`Yes.
`
`Okay.
`
`So what we see here is there's an
`
`alkylating step (a) and a hydrolyzing step (b) on
`
`
`page 42 of the Phares reference.
`
`A
`
`Yes.
`
`MR. POLLACK:
`
`I'm going to mark as
`
`Williams Deposition Exhibit 20 an excerpt
`
`from
`
`Exhibit 1002, and it’s a small section from that
`
`exhibit which was the prosecution history. And it's
`
`called the ”Declaration of David Walsh.”
`
`E
`
`
`
`
`UTExZOQ
`{Exhibit 20 marked)
`3
`SteadyMed v. United Thetapeuti s
`P190
`
`IPR2016—DDG 6
`5
`
`Elisa Dreier Reporting Corp., U.S. Legal Support Company (212)557—5558
`950 Third Avenue, New York, NY
`10022
`
`IPR2020-00769
`
`United Therapeutics EX2006
`Page 2318 of 7113
`
`10
`
`ll
`
`l2
`
`13
`
`14
`
`15
`
`l6
`
`l7
`
`18
`
`19
`
`21
`
`22
`
`23
`
`24
`
`25
`
`IPR2020-00769
`United Therapeutics EX2006
`Page 2318 of 7113
`
`

`

`STEADYMED vs UNlTED THERAPEUTlCS CORPORATION
`
`Page 191
`
`WILLEAMS, ROBERT on 08/26/2016
`
`m_A
`
`BY MR. PCLLACK:
`
`Q
`
`You've reviewed this document in
`
`preparation for this deposition and for —— in
`
`preparing your Declaration; correct?
`
`A
`
`Q
`
`Yes.
`
`I think we discussed earlier that
`
`according to this document ~e if we turn to the
`
`document called “Page 348" in the lower right—hand
`
`corner.
`I
`think we discussed earlier how for the
`treprostinil diethanolamine salt,
`that‘s what’s
`
`presented at the top of the page —— the salt?
`
`acid?
`
`A
`
`Q
`
`A
`
`Q
`
`Yes‘
`
`Okay. And then below that is the free
`
`Yes.
`
`Okay. And we see in the free acid,
`
`the
`
`impurities are 0.2 percent; right? Total related
`
`substances.
`
`A
`
`Q
`
`No.
`
`Oh,
`
`I'm sorry. What is the impurities by
`
`HPLC for total related substances for the
`
`treprostinil free acid on the Welsh Declaration?
`
`A
`
`Oh, you were asking me about
`
`the salt,
`
`
`
`11
`
`12
`
`13
`
`14
`
`16
`
`17
`
`18
`
`21
`
`22
`
`23
`
`24
`
`
`
`E
`I
`
`5
`2
`i
`
`.e
`
`which is .1 pertinence.
`
`Q
`
`I'm sorry. Misspoke,
`
`then.
`P1193
`
`UTExEDéQ
`_
`-—
`I was not
`SteadyMed v. Unlted Therapeuties
`|PR201B—OOEE8
`
`Elisa Dreier Reporting Corp., U.S. Legal Support Company
`950 Third Avenue, New York, NY
`10022
`
`(212)557~5558
`
`|PR2020-00769
`
`United Therapeutics EX2006
`Page 2319 of 7113
`
`IPR2020-00769
`United Therapeutics EX2006
`Page 2319 of 7113
`
`

`

`STEADYMED VS UNITED THERAPEUTICS CORPORATION
`
`Page 192
`
`WILLIAMS, ROBERT on 08/26/2016
`
`
`
`
`
`
`
`
`
`
`okay.
`
`acid?
`
`Want
`
`to do the salt first or the free
`
`A
`Q
`A
`Q
`A
`Q
`
`You‘re asking the questions.
`Okay.
`You pick the order.
`All right. Let's do the free acid.
`Okay.
`Am I correct that the total related
`
`é
`i
`5
`i
`g
`g
`g
`g
`3
`
`
`
`,
`
`substances for the free acid is 0.2 percent?
`
`A
`
`Q
`
`Yes.
`
`And for the treprostinil diethanolamine
`
`salt,
`
`the total related substances is 0.1 percent?
`
`A
`
`Q
`
`Yes.
`
`Okay.
`
`So,
`
`let me ask you this:
`
`in fact,
`
`there are —— well,
`
`The treprostinil free acid,
`
`
`
`it's made the same way as the diethanolamine salt,
`
`except step (d)
`
`is then executed;
`
`is that correct?
`
`A
`
`Q
`
`That's correct.
`
`Okay. And so when step (d) was executed,
`
`the amount of total related substances actually
`
`increased; correct?
`
`A
`
`Q
`
`Yes.
`
`And,
`
`in fact,
`
`the spec, even, for
`
`I l\
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`
`treprostinil free acid made using the step (d)
`UTExZOQ
`is
`P192
`SEadyMedv.UnhedTheepeufls
`EPR201B—OOO 6
`
`
`
`Elisa Dreier Reporting Corp., U.S. Legal Support Company (212)557—5558
`950 Third Avenue, New York, NY
`10022
`
`|PR2020-00769
`
`United Therapeutics EX2006
`Page 2320 of 7113
`
`IPR2020-00769
`United Therapeutics EX2006
`Page 2320 of 7113
`
`

`

`STEADYMED vs UNllED THERAPEUTICS CORPORATION
`Page 193
`WILLIAMS, ROBERT on 08/26/2016
`
`
`
`actually set to not more than 3 percent.
`
`Do you see
`
`that?
`
`UJ
`
`A
`
`Q
`
`Yes.
`
`And for the salt,
`
`the level of impurities
`
`is set to only not more than 1—1/2 percent.
`
`
`Do we
`
`see that?
`
`A
`
`Q
`
`Yes.
`
`So carrying out an additional step,
`
`step (d), on the treprostinil diethanolamine salt
`
`actually increases the impurity level of the
`
`product; right?
`
`MS. HASPER: Objection. Mischaracterizes
`
`the document.
`
`THE WITNESS:
`
`So what‘s going on here ——
`
`this is actually fairly easy to understand.
`
`BY MR. POLLACK:
`
`Q
`
`A
`
`Okay.
`
`—— is that the salt, which is incredibly
`
`pure.
`
`Seven to eight impurities is not present.
`
`The only thing that‘s detectable is an tiny amount
`
`of the enantiomer 3AU90. All
`
`the others have been
`
`eliminated. And when you treat the salt with acid,
`
`the impurities that now come back are the two
`
`dimers:
`
`750W93, 751W93; and the ethyl ester.
`
`ll
`
`12
`
`13
`
`
`
`
`UT'zx.20§9
`And that‘s because those are formed by
`
`RWS seawmwvimmdne

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