Ex Parte Naguib et al

Patent Trial and Appeal Board

Jan 5, 2017

13589155 (P.T.A.B. Jan. 5, 2017)

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.
13/589,155 08/19/2012 YOUSRY M.A. NAGUIB 9806
7590 01/06/2017
Yousry Naguib
19 E. Newman Ave
Arcadia, CA 91006
EXAMINER
JARRELL, NOBLE E
ART UNIT PAPER NUMBER
1625
MAIL DATE DELIVERY MODE
01/06/2017 PAPER
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.
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
__________

BEFORE THE PATENT TRIAL AND APPEAL BOARD
__________

Ex parte YOUSRY M.A. NAGUIB,
ASHRAF NAGUIB, and AHMED NAGUIB1
__________

Appeal 2016-002033
Application 13/589,155
Technology Center 1600
__________

Before FRANCISCO C. PRATS, JEFFREY N. FREDMAN, and
RYAN H. FLAX, Administrative Patent Judges.

PRATS, Administrative Patent Judge.

DECISION ON APPEAL

This appeal under 35 U.S.C. § 134(a) involves claims to methods of
forming complexes composed of a radioisotope of fluorine and a cryptand.
The Examiner rejected the claims for obviousness.
We have jurisdiction under 35 U.S.C. § 6(b). We affirm.
However, because our affirmance relies on somewhat different
reasoning than the Examiner’s, we designate our affirmance a new ground of
rejection.

1 Appellants state that the “real party in interest is YOUSRY NAGUIB, et
al.” App. Br. 3.
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STATEMENT OF THE CASE
The sole rejection before us for review is the Examiner’s rejection of
claims 1, 4, 9, and 12 under 35 U.S.C. § 103(a) for obviousness over
Naguib2 and Prenant.3 Ans. 2–4.
Claim 1 is representative and reads as follows (App. Br. 14):
1. A method of complexing [18F]fluoride anion comprising
combining [18F]fluoride anion with diaryl and aryl fused
[2.2.2]cryptand and potassium carbonate.

OBVIOUSNESS
The Examiner’s Rejection
The Examiner cites Naguib as disclosing compound VIII, a
[2.2.2] cryptand encompassed by claim 1. Ans. 2. The chemical structure of
compound VIII is shown in Naguib at 3602, as follows:

The Examiner cites Prenant as teaching that “Kryptofix 222 can be
radiolabelled with 18F in the presence of potassium carbonate (page 4,
paragraph [0060]). This synthetic step is one step of other[s] to use

2 Yousry M.A. Naguib, Synthesis of a [2.2.2] Cryptand Containing Reactive
Functional Groups, 14 Molecules 3600-3609 (2009).
3 US 2008/0274046 A1 (published Nov. 6, 2008).
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[18F]-Fluoroacetadehyde in positron emission tomography (PET) (example
2, page 5, paragraphs [0073][0077]).” Id. at 3.
The Examiner finds a “reasonable expectation of success is present
that compound VIII of Naguib can be radiolabeled with 18F because
kryptofix 222 is a cryptand too. Since both of these compounds are
cryptands, it is expected that they would react similarly.” Id.
The Examiner concludes, therefore, that based on the reasonable
inferences drawn from the cited references, “the subject matter defined by
the instant claims would have been obvious within the meaning of 35 USC
[§] 103(a).” Id. The Examiner notes in particular that in KSR Int’l v.
Teleflex Inc., 550 U.S. 398 (2007) the Supreme Court provided a number of
rationales that support a conclusion of obviousness. Id. at 4.
Analysis
As stated in In re Oetiker, 977 F.2d 1443, 1445 (Fed. Cir. 1992):
[T]he examiner bears the initial burden . . . of presenting a
prima facie case of unpatentability. . . .
After evidence or argument is submitted by the applicant
in response, patentability is determined on the totality of the
record, by a preponderance of evidence with due consideration
to persuasiveness of argument.

Appellants do not argue any of the rejected claims separately. We
select claim 1 as representative of the rejected claims. 37 C.F.R.
§ 41.37(c)(iv). Appellants’ arguments do not persuade us that a
preponderance of the evidence fails to support the Examiner’s conclusion
that the process recited in claim 1 would have been prima facie obvious to
an ordinary artisan in view of Prenant and Naguib.
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Prenant discloses methods of producing 18F-labeled
fluoroacetaldehyde, which can be used to radiolabel proteins, which, in turn,
are useful in Positron Emission Tomography (PET) imaging. See Prenant
¶¶ 1–11.
Prenant discloses that producing 18F-labeled fluoroacetaldehyde first
requires formation of a complex between an alkali metal salt of the
[18F]fluoride anion, and a chelating agent. Id. at ¶ 29 (“[I]t is preferred that a
chelating agent is incorporated in the solution containing the alkali metal
fluoride. Subsequently water may be evaporated to provide the dry,
complexed alkali metal fluoride for use in the subsequent steps of the
procedure.”).
Prenant discloses that suitable chelating agents include cryptands,
such as “Kryptofix® 222,” which is “more suitable for potassium cation” of
the fluoride salts (Prenant ¶ 32), and also discloses that the “preferred alkali
metal employed for the purposes of the synthesis of the aldehydes is
potassium” (id. at ¶ 33).
In the example identified by the Examiner, Prenant discloses a process
in which [18F]fluoride anion is combined with the cryptand Kryptofix 222
and potassium carbonate. See Prenant ¶ 60:
The aqueous [18F]fluoride solution . . . was added to an
open 3 mL conical vial containing potassium carbonate . . . and
Kryptofix® 222 . . . . After addition of 1 mL of acetonitrile the
mixture was dried under argon at 100° C. This drying step was
repeated twice with 1 mL of acetonitrile.

Thus, as required by Appellants’ claim 1, Prenant’s exemplified
complexing process combines [18F]fluoride anion, a cryptand, and potassium
carbonate. Prenant’s exemplified complexing process, therefore, differs
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from the process of Appellants’ representative claim 1 only in that Prenant
does not use the diaryl and aryl fused [2.2.2] cryptand required by claim 1.
As the Examiner finds, however, and Appellants do not dispute,
Naguib describes a compound, compound VIII, which is a diaryl and aryl
fused [2.2.2] cryptand encompassed by claim 1. Naguib 3601, 3602.
Naguib explains that cryptands “are cavities containing
macromolecules which form stable complexes with alkali metal ions. For a
given cation, the stability constant is largest for the cation which fits best
into the cavity of the ligand. Thus stability maxima are found for Li[2.1.1]+,
Na[2.2.1]+, and K[2.2.2]+, respectively.” Naguib 3601. Naguib further
describes compound VIII as “a potential potassium ionophore.” Id. at 3608.
Because Prenant discloses that preferred chelating agents in its
[18F]fluoride complexing process include cryptands which are specific for
potassium ions, and because Naguib’s compound VIII was a known [2.2.2]
cryptand which, as taught in Naguib, provides maximal potassium complex
stability, thus suggesting its use as a “potential potassium ionophore” (id.),
we agree with the Examiner (Ans. 5) that an ordinary artisan had a good
reason for, and a reasonable expectation of success in, using Naguib’s
compound VIII as the cryptand in Prenant’s [18F]fluoride complexing
process. We, therefore, also agree with the Examiner that the process recited
in Appellants’ claim 1 would have been prima facie obvious to an ordinary
artisan.
Appellants’ arguments do not persuade us to the contrary.
Appellants contend that the Examiner erroneously characterized
Prenant’s process of forming Kryptofix 222/[18F]fluoride anion complexes
as radiolabeling the Kryptofix 222. App. Br. 6–8; see also Reply Br. 6–7.
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Appellants contend that Naguib’s compound VIII acts as a metal
complexing agent, which would not be labeled with 18F. App. Br. 9–11.
Appellants appear to contend also that the Examiner’s allowance of certain
claims is inconsistent with the conclusion of obviousness as to other claims.
App. Br. 12–13; see also Reply Br. 9.
That the Examiner may have used the term “radiolabelling” to
describe Prenant’s [18F]fluoride complexing process (Ans. 3), or that the
Examiner’s treatment of representative claim 1 might be inconsistent with
the treatment of other claims, does not persuade us that an ordinary artisan
lacked a reason for, or a reasonable expectation of success in, using
Naguib’s compound VIII as the cryptand complexing agent in Prenant’s
process.
As the Supreme Court explained in KSR, “when a patent claims a
structure already known in the prior art that is altered by the mere
substitution of one element for another known in the field, the combination
must do more than yield a predictable result.” 550 U.S. at 416; see also id.
at 417 (“[W]hen a patent ‘simply arranges old elements with each
performing the same function it had been known to perform’ and yields no
more than one would expect from such an arrangement, the combination is
obvious.”) (quoting Sakraida v. Ag Pro, Inc., 425 U.S. 273 (1976)).
In the present case, as discussed above, Prenant discloses that
potassium-complexing cryptands are useful in its process, and compound
VIII, disclosed by Naguib, was a known [2.2.2] cryptand that an ordinary
artisan would have recognized as useful for complexing potassium ions.
Appellants’ arguments (Reply Br. 5–8), therefore, do not persuade us that
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the cited references would have failed to suggest using Naguib’s compound
VIII as the cryptand in Prenant’s complexing process.
That neither reference stated expressly that Naguib’s compound VIII
should be used as the cryptand in Prenant’s complexing process does not
demonstrate that the references fail to suggest using Naguib’s cryptand in
Prenant’s process. See KSR, 550 U.S. at 418 (“[T]he [obviousness] analysis
need not seek out precise teachings directed to the specific subject matter of
the challenged claim, for a court can take account of the inferences and
creative steps that a person of ordinary skill in the art would employ.”); see
also id. at 421 (“A person of ordinary skill is . . . a person of ordinary
creativity, not an automaton.”). Because, as discussed, an ordinary artisan
would have recognized that Naguib’s compound VIII was a potassium-
complexing cryptand, an ordinary artisan would have reasonably inferred
that compound VIII would be useful in Prenant’s complexing processes,
based on Prenant’s teaching that potassium-complexing cryptands were
useful in its processes.
Moreover, that an ordinary artisan might have lacked absolute
certainty as to whether Naguib’s compound VIII would be useful in
Prenant’s processes (see Reply Br. 4, 7–8), does not persuade us that the
artisan lacked a reasonable expectation in that regard. See In re O’Farrell,
853 F.2d 894, 903-04 (Fed. Cir. 1988) (“Obviousness does not require
absolute predictability of success. . . . For obviousness under § 103, all that
is required is a reasonable expectation of success.”). To the contrary, given
Naguib’s disclosure that [2.2.2] cryptands provide maximal potassium
complex stability (Naguib 3601), and Naguib’s disclosure that compound
VIII (a [2.2.2] cryptand) is “a potential potassium ionophore” (id. at 3608),
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both of which are properties understood from Prenant as being desired in its
complexing processes (see Prenant ¶¶ 32–33), we are not persuaded that the
cited references fail to provide a reasonable expectation of success.
Lastly, Appellants do not explain persuasively why removal of the
term “novel” from the claims during prosecution (see Reply Br. 10–11)
demonstrates that the cited references fail to suggest the process recited in
representative claim 1.
In sum, for the reasons discussed, Appellants’ arguments do not
persuade us that a preponderance of the evidence fails to support the
Examiner’s conclusion that representative claim 1 would have been prima
facie obvious to an ordinary artisan in view of Prenant and Naguib. Because
Appellants do not advance persuasive secondary evidence of
nonobviousness, we affirm the Examiner’s rejection of claim 1 under 35
U.S.C. § 103(a). Because they were not argued separately, claims 4, 9, and
12 fall with claim 1. 37 C.F.R. § 41.37(c)(iv).
We note that, in affirming the rejection of claim 1, our analysis differs
somewhat from the Examiner’s in that it includes several findings of fact
different than the findings advanced by the Examiner. We, therefore,
designate our affirmance a new ground of rejection under 37 C.F.R.
§ 41.50(b).
SUMMARY
For the reasons discussed, we affirm the Examiner’s rejection of
claims 1, 4, 9, and 12 under 35 U.S.C. § 103(a) for obviousness over Naguib
and Prenant. Because our rationale for affirming the rejection differs
somewhat from the Examiner’s, we designate our affirmance a new ground
of rejection under 37 C.F.R. § 41.50(b).
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TIME PERIOD FOR RESPONSE
This decision contains a new ground of rejection pursuant to
37 C.F.R. § 41.50(b) (effective September 13, 2004, 69 Fed. Reg. 49960
(August 12, 2004), 1286 Off. Gaz. Pat. Office 21 (September 7, 2004)).
37 C.F.R. § 41.50(b) provides “[a] new ground of rejection pursuant to this
paragraph shall not be considered final for judicial review.
37 C.F.R. § 41.50(b) also provides that the appellant, WITHIN TWO
MONTHS FROM THE DATE OF THE DECISION, must exercise one of
the following two options with respect to the new ground of rejection to
avoid termination of the appeal as to the rejected claims:
(1) Reopen prosecution. Submit an appropriate
amendment of the claims so rejected or new evidence relating
to the claims so rejected, or both, and have the matter
reconsidered by the examiner, in which event the proceeding
will be remanded to the examiner . . . .

(2) Request rehearing. Request that the proceeding be
reheard under § 41.52 by the Board upon the same record . . . .

AFFIRMED, 37 C.F.R. § 41.50(b)