Eric S. Burak et al.

Patent Trials and Appeals Board

Aug 14, 2019

14630584 - (D) (P.T.A.B. Aug. 14, 2019)

UNITED STATES PATENT AND TRADEMARK OFFICE
UNITED STATES DEPARTMENT OF COMMERCE
United States Patent and Trademark Office
Address: COMMISSIONER FOR PATENTS
P.O. Box 1450
Alexandria, Virginia 22313-1450
www.uspto.gov
APPLICATION NO. FILING DATE FIRST NAMED INVENTOR ATTORNEY DOCKET NO. CONFIRMATION NO.
14/630,584 02/24/2015 Eric S. Burak 2202503.147-US3 9121
83333 7590 08/14/2019
WilmerHale / Rib-X Pharmaceuticals
60 State Street
Boston, MA 02109
EXAMINER
PALLAY, MICHAEL B
ART UNIT PAPER NUMBER
1617
NOTIFICATION DATE DELIVERY MODE
08/14/2019 ELECTRONIC
Please find below and/or attached an Office communication concerning this application or proceeding.
The time period for reply, if any, is set in the attached communication.
Notice of the Office communication was sent electronically on above-indicated "Notification Date" to the
following e-mail address(es):
scott.barrett@wilmerhale.com
whipusptopairs@wilmerhale.com
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
________________

BEFORE THE PATENT TRIAL AND APPEAL BOARD
________________

Ex parte ERIC S. BURAK and DANPING LI1
________________

Appeal 2018-002626
Application 14/630,584
Technology Center 1600
________________

Before FRANCISCO C. PRATS, JOHN G. NEW, and
RACHEL H. TOWNSEND, Administrative Patent Judges.

NEW, Administrative Patent Judge.

DECISION ON APPEAL

1Appellants identify Melinta Therapeutics, Inc. as the real party-in-interest.
App. Br. 2.
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SUMMARY
Appellants file this appeal under 35 U.S.C. § 134(a) from the
Examiner’s Final Rejection of claims 1–3 and 6–21. Specifically, claims 1–
3, 6–8, 10, 11, 13, 14, and 17–21 stand rejected as unpatentable under 35
U.S.C. § 103(a) as being obvious over Hopkins et al. (US 2007/0249577
A1, October 25, 2007) (“Hopkins”).2
Claims 1–3 and 6–21 stand rejected as unpatentable under 35 U.S.C.
§ 103(a) as being obvious over the combination of Hopkins and Pipkin et al.
(US 2007/0020299 A1, January 25, 2007) (“Pipkin”).
Claims 1–3, 6–19, and 21 stand further rejected as unpatentable under
the nonstatutory doctrine of obviousness-type double patenting over the
combination of claims 1–23 of US 7,091,196 B2, August 15, 2006 (the
“’196 patent”), Hopkins and Pipkin.
Claims 1–3, 6–18, and 21 stand further rejected as unpatentable under
the nonstatutory doctrine of obviousness-type double patenting over the
combination of claims 1–111 of US 7,129,259 B2, October 31, 2006 (the
“’259 patent”), Hopkins and Pipkin.
Claims 1–3, 6–19, and 21 stand further rejected as unpatentable under
the nonstatutory doctrine of obviousness-type double patenting over the
combination of claims 1–14 of US 7,456,206 B2, November 25, 2008 (the
“’206 patent”), Hopkins and Pipkin.

2 Appellants also contend that Examiner objected to the abstract of the
disclosure for allegedly failing to comply with the requirements of MPEP §
608.01(b) for use of the phrase: “The present invention relates to,” stating
that this “can be implied.” App. Br. 4 (citing Final Act. 3). We do not
reach this issue, as objections are not within the jurisdiction of the Board.
See 35 U.S.C. § 6(b)(1); 37 C.F.R. § 41.31(a)(1).
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We have jurisdiction under 35 U.S.C. § 6(b).
We AFFIRM.

NATURE OF THE CLAIMED INVENTION
Appellants’ claimed invention is directed to pharmaceutical
compositions useful for administration for treating, preventing, or reducing
the risk of microbial infections. Abstr.

REPRESENTATIVE CLAIM
Claim 1 is representative of the claims on appeal and recites:
1. A pharmaceutical composition comprising:

(a) radezolid or a pharmaceutically acceptable salt,
ester, or prodrug thereof,

(b) a buffer,

(c) a pH modifier, and

(d) a solvent.

App. Br. 50.

ISSUES AND ANALYSES
We adopt the Examiner’s findings, reasoning, and conclusion that the
claims on appeal are prima facie obvious over the cited prior art. We
address the arguments raised by Appellant below.

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A. Rejection of claims 1–3, 6–8, 10–11, 13–14, and 17–21 over Hopkins
Issue
Appellants argue that the Examiner erred because: (1) Examiner failed
to assert a reason why a person of ordinary skill in the art would have been
motivated to modify the cited prior art; (2) the Examiner has articulated no
reasoning as to why a person of ordinary skill in the art would have had a
reasonable expectation of success in practicing the teachings of Hopkins;
and (3) the Examiner erred failed to properly address the scope and content
of the prior art, the differences between the prior art and the rejected claims,
and the level of ordinary skill in the prior art. App. Br. 7–9.

Analysis
Appellants first argue that the Examiner erred by failing to properly
assert a reasoned explanation of why a person skilled in the art would have
been motivated to modify Hopkins so as to arrive at the present claims.
App. Br. 7.
The Examiner finds that Hopkins teaches pharmaceutical
compositions comprising an oxazolidinone, such as linezolid or radezolid or
a pharmaceutically acceptable salt, ester, or prodrug thereof, for use
prophylactically as an antimicrobial compound. Final Act. 5 (citing Hopkins
¶¶ 81 (compound C), 217, 79–82, 216–217). The Examiner also finds that
Hopkins teaches that the compounds can be delivered using a suitable carrier
including solvents/diluents such as water, buffers such as citrates, dextrose
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for tonicity adjustment, and acids or bases for adjusting pH such as
hydrochloric acid or sodium hydroxide. Id. (citing Hopkins ¶¶ 233–235).
The Examiner finds that Hopkins does not expressly teach an
exemplary embodiment of a pharmaceutical composition having an
oxazolidinone as the antimicrobial agent, but concludes that it would have
been prima facie obvious to one of ordinary skill in the art at the time the
invention was made to use an oxazolidinone, such as linezolid or radezolid,
or a pharmaceutically acceptable salt, ester, or prodrug thereof in an
antimicrobial composition with a reasonable expectation of success. Final
Act. 5. The Examiner further reasons that a person of ordinary skill in the
art would have been motivated to do so, given that Hopkins expressly
teaches that the antimicrobial agent can be an oxazolidinone such as
linezolid or radezolid. Id. at 6.
Appellants argue that that the Examiner has failed to sufficiently
articulate a reasoned explanation of why a person having ordinary skill in
the art would have been motivated to modify the examples of Hopkins to
include the compound radezolid. App. Br. 7. Appellants assert that Hopkins
teaches over 30 specific compounds, as well as genera encompassing
“millions” more, that are purported to be useful in preventing or reducing the
risk of infection due to surgical or invasive medical procedures. Id.
According to Appellants, Hopkins also discloses 12 examples of
compositions for these purposes, half of which include the particular
quinolone compound l-(6-amino-3,5-difluoro-2-pyridinyl )-8-chloro-6-
fluoro-l, 4-dihydro-7-(3-hydroxyl-azetidinyl)-4-oxo-3-quinolinecarboxylic
acid (i.e., delafloxacin), the other half of which only generically recite an
“antimicrobial compound.” Id. at 7–8.
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We are not persuaded by Appellants’ argument. Hopkins is directed
to methods for reducing the risk of, or preventing, infection due to surgical
or invasive medical procedures. Hopkins ¶ 2. Hopkins teaches that this
method is practiced: “by administering a prophylactically effective amount
of an antimicrobial compound to the patient prior to the surgical or invasive
procedure.” Id. at ¶¶ 6–10.
Hopkins expressly teaches that: “the antimicrobial compound can be,
for example, an oxazolidinone … or a pharmaceutically acceptable salt,
ester, or prodrug thereof. Hopkins at 79–80. Hopkins also teaches that this
oxazolidinone can be radezolid (i.e., N-[3-(2-Fluoro-4ʹ-{[(3R-[1,2,3]triazol-
4-ylmethyl)-amino]-methyl}-biphenyl-4-yl)-2-oxo-oxazolidin-5-(S)
ylmethyl]-acetamide) (Compound C). Id. at ¶ 81; see also ¶¶ 138, 216–217.
Furthermore, Hopkins expressly teaches that:
A pharmaceutical composition of the invention should be
formulated to be compatible with its intended route of
administration. Solutions or suspensions can include the
following components: a sterile diluent such as water, saline
solution, fixed oils, polyethylene glycols, glycerine, propylene
glycol or other synthetic solvents; antibacterial agents such as
benzyl alcohol or methyl parabens; antioxidants such as ascorbic
acid or sodium bisulfite; chelating agents such as
ethylenediaminetetraacetic acid; buffers such as acetates, citrates
or phosphates and agents for the adjustment of tonicity such as
sodium chloride or dextrose. The pH can be adjusted with acids
or bases, such as hydrochloric acid or sodium hydroxide.

Hopkins ¶ 235. Hopkins thus teaches all of the limitations of the claims, and
teaches that they can be combined. That Hopkins does not expressly provide
an exemplary embodiment specifically containing radezolid is of no
significance: a person of ordinary skill would have been motivated to use
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radezolid as the antimicrobial agent in the pharmaceutical compositions of
Hopkins, because that is precisely what Hopkins teaches the artisan to do.
See Medichem, S.A. v. Rolabo, S.L. Eyeglasses, 437 F.3d 1157, 1166 (Fed.
Cir. 2006) (holding that: “the prior art must be considered as a whole for
what it teaches”); see also Sinclair & Carroll Co. v. Interchemical Corp.,
325 U.S. 327, 335 (1945) (“[r]eading a list and selecting a known compound
to meet known requirements is no more ingenious than selecting the last
piece to put into the last opening in a jig-saw puzzle. It is not invention”).
In other words, it is not necessary for the skilled artisan to “modify” the
teachings of Hopkins; the artisan merely has to follow what the teachings
prescribe. See Merck & Co. Inc. v. Biocraft Labs., Inc., 874 F.2d 804, 807
(Fed. Cir. 1989) (“That the ’813 patent discloses a multitude of effective
combinations does not render any particular formulation less obvious. This
is especially true because the claimed composition is used for the identical
purpose taught by the prior art”). Appellants’ argument is not persuasive of
Examiner error.
Appellants argue further that, because the Examiner has failed to
articulate why a person of ordinary skill would have had a reasonable
expectation of success, the Examiner’s rejection is in error. App. Br. 8–9.
We are not persuaded. A skilled artisan would have had a reasonable
expectation of success in using radezolid in the compositions of Hopkins,
because that is precisely what Hopkins teaches. See, e.g., Hopkins ¶¶ 79, 81
(“The antimicrobial compound can be, for example, an oxazolidinone.… For
example, the oxazolidinone compound can be one of the following
compounds: [radezolid (compound C)]”). Because Hopkins teaches that
radezolid is an effective antimicrobial compound in its compositions, it
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follows that a person of ordinary skill in the art would have had a reasonable
expectation of success in using radezolid. We do not find Appellants’
argument persuasive in this respect.
Third, Appellants argue that the Examiner failed to properly address
the scope and content of the prior art, the differences between the prior art
and the rejected claims, and the level of ordinary skill in the prior art.
We do not agree. To the contrary, and as we have explained supra,
the Examiner has demonstrated that Hopkins teaches each and every
limitation recited by the claims. Appellants point to no limitation of the
claims on appeal that the Examiner has not identified in the teachings of
Hopkins.
Appellants dilate considerably upon these three arguments, but their
arguments are unavailing for the reasons we have explained. See App. Br.
10–28. In short, we agree with the Examiner that Hopkins teaches all of the
limitations of the claims and that a person of ordinary skill, following the
teachings of Hopkins, would have arrived at Appellants’ claimed invention
with a reasonable expectation of success. We consequently affirm the
Examiner’s rejection upon this ground.

B. Rejection of claims 1–3 and 6–21 over Hopkins and Pipkin
Issue
Appellants argue that the Examiner states that: “[t]he teachings of
Hopkins [ ] are relied upon as discussed above with respect to claims 1–3, 6–
8, 10, 11, 13, 14, and 17–21,” but provides no additional analysis with
respect to Pipkin, making the rejection redundant, and that the rejection fails
for the reasons argued by Appellants supra. App. Br. 29.
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Analysis
The Examiner finds that Hopkins teaches sodium citrate, but does not
expressly teach sodium citrate tribasic. Final Act. 8. The Examiner finds
that Pipkin teaches pharmaceutical solutions having citrate buffers of 50 mM
citric acid and 50 mM sodium citrate tribasic, dehydrate. Id. (citing Pipkin
¶ 308, Ex. 13). The Examiner finds that the teachings of Hopkins and
Pipkin are both directed to pharmaceutical solutions having citrate buffers of
citric acid and sodium citrate. Id. The Examiner concludes that it would
have been prima facie obvious to a person of ordinary skill in the art to
combine the teachings of the references by using the sodium citrate tribasic,
dihydrate of Pipkin as the form of the sodium citrate in the composition of
Hopkins. Id. The Examiner reasons that a skilled artisan would have been
motivated to do so, and with a reasonable expectation of success, given that
sodium citrate has only three forms: monobasic, dibasic, and tribasic, and
the tribasic form is used as a buffer in pharmaceutical compositions, such as
those taught by Pipkin. Id. at 8–9.
Appellants repeat their arguments presented supra. App. Br. 28–30.
Appellants additionally argue that the Examiner failed to articulate a reason
to combine the teachings of Hopkins and Pipkin. Id. at 31. Appellants argue
that the Examiner fails to acknowledge that the references are directed to
treating different diseases, using different types of therapeutic agents, in
different chemical classes, by different routes of administration. Id.
Specifically, Appellants contend that Pipkin teaches an inhalable
formulation for the treatment of diseases and disorders of the lungs
containing a corticosteroid and a sulfoalkyl ether cyclodextrin (“SAE-CD”)
that is adapted for administration to a subject by nebulization. App. Br. 31
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(citing Pipkin Abstr.). Appellants assert that Pipkin states that its
composition: “overcomes many of the undesired properties of other known
aqueous inhalable solution or suspension corticosteroid-containing
formulations. By including SAE-CD in an inhalable liquid formulation
containing corticosteroid, the corticosteroid is dissolved. Unexpectedly, the
nebulization of corticosteroid is improved….” Id. at 31–32 (quoting Pipkin
¶ 119). According to Appellants, Pipkin discloses sodium citrate tribasic
only twice, both times in the context of a budesonide formulation. Id. at 32
(citing Pipkin ¶¶ 301, 308). In contrast, argue Appellants, Pipkin repeatedly
discloses the use of citrate buffer in formulations containing budesonide
without specifying that sodium citrate tribasic should be used. Id. (citing
Pipkin ¶¶ 5, 21, 284, 292, 294, 298, 314, 317, 360, 367, 372). Appellants
also assert that Pipkin further discloses a non-limiting list of dozens of
buffering agents for inclusion in the formulations disclosed therein and
includes both sodium citrate anhydrous and dihydrate. Id. (citing Pipkin ¶
250).
In contrast, argue Appellants, the examples in Hopkins are directed to
pharmaceutical compositions for intravenous administration, intramuscular
administration, and tablets for oral administration. App. Br. 32 (citing
Hopkins ¶¶ 258–297). Appellants contend that Hopkins discloses citrate
buffer in a non-limiting list of three possible buffers for use in its
pharmaceutical composition, as well as in examples of intravenous
formulations of antimicrobial compounds generally or, particularly, of
delafloxacin. Id. (citing Hopkins ¶¶ 235, 258–259, 261, 262).
We do not find Appellants’ arguments persuasive. Hopkins teaches
that: “A pharmaceutical composition of the invention should be formulated
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to be compatible with its intended route of administration. Solutions or
suspensions can include the following components … buffers such as
acetates, citrates or phosphates….” Hopkins ¶ 235. Hopkins also teaches
the use of “sodium citrate USP” in several exemplary embodiments. See,
e.g., id. at ¶¶ 258, 261. It is well known in the art that the term “sodium
citrate” can refer to any of the sodium salts of citric acid, including sodium
citrate tribasic (also known as sodium citrate dihydrate, see Millipore Sigma,
Sodium citrate, available at https://www.sigmaaldrich.com/catalog/
substance/sodiumcitrate29410613204311?lang=en®ion=US (last visited
August 5, 2019)). Because Hopkins teaches only “sodium citrate’ as used in
a buffer, we conclude that one of ordinary skill in the art would understand
this to include all of its sodium salts (a buffer is a combination of a weak
acid and its salt).
Pipkin teaches: “As used herein, the term ‘buffering agent’ is intended
to mean a compound used to resist change in pH upon dilution or addition of
acid or alkali. Such compounds include, by way of example and without
limitation, … sodium citrate anhydrous and dihydrate [i.e., tribasic] and
others known to those of ordinary skill in the art.” Pipkin ¶ 250; see also ¶¶
301, 308. We find that it is very well known in the art that citrate buffers are
commonly used in pharmaceutical compositions as a means of resisting
changes in the pH of a composition, and that a person of ordinary skill in the
art would understand that the term “sodium citrate,” when used in a buffer
solution, can include sodium citrate tribasic.
Nor do Appellants make any argument that there is a critical effect or
unexpected result obtained as a result of using sodium citrate tribasic (as
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opposed to mono- or dibasic). We consequently affirm the Examiner’s
rejection upon this ground.

C. Rejection of claims 1–3, 6–19, and 21 over the ’196 patent, Hopkins,
and Pipkin

Issue
Appellants argue that the Examiner erred because a person of ordinary
skill in the art would not have been motivated to combine the references to
arrive at the claimed invention. App. Br. 35.

Analysis
The Examiner finds that, although the claims of the ’196 patent claims
encompass pharmaceutical compositions comprising an oxazolidinone and a
pharmaceutically acceptable carrier, and treating microbial infections with
such compositions, the claims of the ’196 patent do not recite a buffer, a pH
modifier, and a solvent, nor do they recite the claimed amounts of these
ingredients, nor do they recite the specific named ingredients. Final Act. 13.
However, the Examiner finds, all of these missing elements were well
known in the prior art. Id.
Appellants argue that the Examiner’s argument regarding motivation
to combine and reasonable expectation of success is premised on the
incorrect statement that each of the cited references is directed to:
“pharmaceutical compositions comprising oxazolidinones and
pharmaceutically acceptable carriers.” App. Br. 35. Appellants assert that
Pipkin does not disclose oxazolidinone compounds. Id. Appellants also
repeat their arguments supra that Hopkins does not focus on oxazolidinone
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compounds because it does not disclose any exemplary pharmaceutical
compositions comprising oxazolidinone compounds, and all of the
exemplary embodiments provided in Hopkins that teach a specific
antimicrobial compound employ the quinolone compound delafloxacin,
rather than the oxazolidinone compound, radezolid. Id.
We are not persuaded. Appellants acknowledge that the claims of the
’196 patent recite pharmaceutical compositions comprising an oxazolidinone
and a pharmaceutically acceptable carrier. As we have explained, Hopkins
teaches the use of oxazolidinone compound, and specifically radezolid, as
antimicrobial compounds in its claimed pharmaceutical compositions. See
Hopkins ¶¶ 79–81, 138, 216–217. Hopkins also teaches that buffer
(including sodium citrate), solvents, and pH modifiers are included in their
pharmaceutical compositions, and Pipkin teaches the use of sodium citrate
tribasic (specifically) in buffer solutions. See Hopkins ¶¶ ¶¶ 235, 258–259,
261, 262; Pipkin ¶ 250.
We agree with Appellants that the triazole moiety of the ’196 genus is
attached to the rest of the oxazolidinone molecule by a nitrogen, rather than
a carbon on the ring structure, as on radezolid. Appellants point out the
difference but make no argument that this is a critical difference or why the
one position shift on the rings structure would not be an obvious difference
between radezolid and the claimed compound.
We consequently conclude that a person of ordinary skill in the art
would have found Appellants’ claims on appeal to be obvious over the
claims of the ’196 patent and the cited prior art and we affirm the
Examiner’s rejection of the claims.

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D. Rejection of claims 1–3, 6–18, and 21 over the ’259 patent, Hopkins
and Pipkin

Analysis
Appellants contend that claims 1–111 of the ’259 patent recite a genus
of oxazolidinone compounds and pharmaceutical compositions thereof, but
does not include any claim specifically directed to radezolid. App. Br. 36.
Furthermore, argue Appellants, the genus recited by claim 1 of the ’259
patent does not allow for the “M” substituent to be a triazole ring, as is
present in radezolid. Therefore, Appellants assert, the genus of claim 1 of
the ’259 patent completely excludes radezolid. Id.
We are persuaded by Appellants’ argument. Claim 1 of the ’259
patent recites, in relevant part:
1. A compound having the formula:

or a pharmaceutically acceptable salt, ester or prodrug thereof,
wherein:
…

M is selected from the group consisting of:

a) Cl-6 alkyl, b) C2-6 alkenyl, and c) C2-6 alkynyl,
wherein

i) any of a)-c) is substituted with one or more moieties
selected from the group consisting of F, Cl, Br, and I; and

ii) any of a)-c) optionally is further substituted with one or
more R4 groups
…
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R4, at each occurrence, independently is selected from the
group consisting of: a) H, b) F, c) Cl, d) Br, e) I, f) =O, g) =S, h)
=NR5, i) =NOR5, j) =N-NR5R5, k)-CF3 , 1)---OR5, m) -CN, n)
-NO2 , o) -NR5R5, p) --C(O)R5, q) -C(O)OR5, r) --OC(O)R5, s)
-C(O)NR5R5, t) -NR5C(O)R5, u) -OC(O)NR5R5, v)
-NR5C(O)OR5, w)-NR5C(O)NR5R5, x)-C(S)R5, y)--C(S)OR5, z)
-OC(S)R5, aa)-C(S)NR5R5, bb )-NR5C(S)R5, cc) OC(S)NR5R5,
dd)-NR5C(S)OR5, ee)-NR5C(S)NR5R5, ff) -NR5C(NR5)NR5, R5,
gg)-S(O)PR5, and hh) R5;

Radezolid, as depicted by Formula C of Hopkins, has the structure:

See Hopkins ¶ 81. The Examiner does not point to, nor can we discern, any
substituent M in claim 1 of the ’259 patent that constitutes a triazole moiety
at the M position. Nor can we discern any such group recited at the M
position of independent claims 41, 74, or 97 of the ’259 patent. We
conclude that the genera cited in claims 1–111 of the ’259 patent do not
encompass radezolid, and we reverse the Examiner’s rejection upon this
ground.

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D. Rejection of claims 1–3, 6–19, and 21 over the ’206 patent, Hopkins
and Pipkin

Analysis
Appellants acknowledge that claims 1–14 of the ’206 patent recite
radezolid (or a tautomer or a pharmaceutically acceptable salt thereof),
pharmaceutical compositions thereof, and methods of ameliorating a
symptom of a microbial infection in a mammal by administration thereof.
App. Br. 38. Appellants contend that the Examiner erred by: (1) failing to
reasonably articulate a motivation to combine Pipkin and Hopkins with the
claims of the ’206 patent; (2) failing to provide a reasoned explanation of
why a skilled person would be motivated to combine radezolid and the
particular components disclosed in Hopkins and Pipkin in such a way as to
arrive at the compositions of the present claims; and (3) failing to show why
a person of ordinary skill in the art would have had a reasonable expectation
of success in combining the references.
Essentially, Appellants repeat all of the arguments presented above in
Sections A and B of this Decision. Both claims 1–14 of the ’206 patent and
Hopkins teach pharmaceutical compositions of radezolid. We have
explained supra why we find Appellants’ to be not persuasive, and they are
no more persuasive upon repetition. We consequently affirm the Examiner’s
rejection.

DECISION
The Examiner’s rejection of claims 1–3 and 6–21 under 35 U.S.C.
§ 103(a) is affirmed.
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The Examiner’s rejection of claims 1–3, 6–19, and 21 under the
nonstatutory doctrine of obviousness-type double patenting over the ’196
patent and the ’206 patent in combination with Hopkins and Pipkin is
affirmed.
The Examiner’s rejection of claims 1–3, 6–18, and 21 under the
nonstatutory doctrine of obviousness-type double patenting over the ’259
patent in combination with Hopkins and Pipkin is reversed.
No time period for taking any subsequent action in connection with
this appeal may be extended under 37 C.F.R. § 1.136(a)(1)(iv).

AFFIRMED