Ex Parte Langstrom et al

Board of Patent Appeals and Interferences

Jul 10, 2012

11386973 (B.P.A.I. Jul. 10, 2012)

MOD PTOL-90A (Rev.06/08)

APPLICATION NO./
CONTROL NO.
FILING DATE FIRST NAMED INVENTOR /
PATENT IN REEXAMINATION
ATTORNEY DOCKET NO.
11/386,973 03/22/2006 Langstrom, Bengt

EXAMINER
Amersham Health, Inc.
IP Department
101 Carnegie Center
Princeton, NJ 08540
Schlientz, Leah
ART UNIT PAPER NUMBER
1618
MAIL DATE DELIVERY MODE

07/11/2012 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.

UNITED STATES DEPARTMENT OF COMMERCE
U.S. Patent and Trademark Office
Address : COMMISSIONER FOR PATENTS
P.O. Box 1450
Alexandria, Virginia 22313-1450
www.uspto.gov
UNITED STATES PATENT AND TRADEMARK OFFICE
_____________________________________________________________________________________

UNITED STATES PATENT AND TRADEMARK OFFICE
__________

BEFORE THE BOARD OF PATENT APPEALS
AND INTERFERENCES
__________

Ex parte BENGT LANGSTROM, JULIEN BARLETTA,
FARHAD KARIMI, and HISASHI DOI
__________

Appeal 2011-006207
Application 11/386,973
Technology Center 1600
__________

Before FRANCISCO C. PRATS, MELANIE L. McCOLLUM and
JEFFREY N. FREDMAN, Administrative Patent Judges.

PRATS, Administrative Patent Judge.

DECISION ON APPEAL

This appeal under 35 U.S.C. § 134 involves claims to a method for
synthesizing carbonylated diazo compounds labeled with a carbon isotope.
The Examiner rejected the claims as obvious. We have jurisdiction under
35 U.S.C. § 6(b). We affirm.

Appeal 2011-006207
Application 11/386,973

2

STATEMENT OF THE CASE
Claims 1-7 and 19 stand rejected and appealed (App. Br. 2). Claim 1
is representative and reads as follows:
1. A method for labeling synthesis, comprising:
(g) Providing a high pressure reaction chamber having a liquid inlet
and a gas inlet in a bottom surface thereof,
(h) providing an diazo solution to be labeled mixed with a
transition metal complex and an appropriate reagent, wherein the
appropriate reagent is selected from a list comprising:

wherein R
2
, R
3
, R
4
and R
5
are independently linear or cyclic lower
alkyl or substituted alkyl, hydrogen, aryl or substituted aryl, and may
contain carbonyl, hydroxyl, thiol, halogen, nitrile, isonitrile, cyanate,
isocyanate, thiocyanate, isothiocyanate functional groups.
(i) introducing a carbon-isotope monoxide enriched gas-mixture
into the reaction chamber via the gas inlet,
(j) introducing at high pressure said diazo solution mixed with
transition metal complex and said appropriate reagent into the reaction
chamber via the liquid inlet,
(k) waiting for a predetermined time while the labeling synthesis
occur, and
(l) collecting the labeled compound, wherein the labeled
compound is selected from a list comprising:
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Application 11/386,973

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wherein R
1
is linear or cyclic lower alkyl or substituted alkyl,
hydrogen, aryl or substituted aryl and may contain carbonyl, hydroxy,
thiol, halogen, nitrile, isonitrile, cyanate, isocyanate, thiocyanate,
isothiocyanate functional groups, R
2
, R
3
, R
4
and R
5
are independently
linear or cyclic lower alkyl or substituted alkyl, hydrogen, aryl or
substituted aryl, and may contain carbonyl, hydroxy, thiol, halogen,
nitrile, isonitrile, cyanate, isocyanate, thiocyanate, isothiocyanate
functional groups from the reaction chamber.

The following grounds of rejection are before us for review:
(1) Claims 1-6 and 19 under 35 U.S.C. § 103(a) as obvious over
Tuba,
1
Kihlberg,
2
and Hernandez
3
(Ans. 4-6); and
(2) Claims 1-7 and 19 under 35 U.S.C. § 103(a) as obvious over Tuba,
Kihlberg, Hernandez, and Deydier
4
(Ans. 7).

1
Robert Tuba & Ferenc Ungváry, Octacarbonyl dicobalt-catalyzed selective
transformation of ethyl diazoacetate into organic products containing the
ethoxycarbonyl carbene building block, 203 J. MOL. CATALYSIS 59-67
(2003).
2
WO 02/102711 A1 (published Dec. 27, 2002).
3
L. Hernandez et al., Labelling with diethyl-[ 2-
14
C]-malonate in solvent-
free conditions, 53 CZECH. J. PHYS. A751-A754 (Supp. 2003).
4
Eric Deydier et al., Wolff rearrangement in a transition-metal diazoalkane
complex. Synthesis of the first η
1
-ketenyl rhodium complex
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Application 11/386,973

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DISCUSSION
In rejecting claims 1-6 and 19 as obvious over Tuba, Kihlberg, and
Hernandez, the Examiner cited Tuba as teaching that, “in the presence of
1 mol% octacarbonyl dicobalt, ethyl diazoacetate can be transformed at
room temperature and carbon monoxide pressure in the presence of an
alcohol (methanol, ethanol, t-butanol, phenol) or diethylamine into the
corresponding malonic acid derivatives in high yields” (Ans. 4). In
particular, the Examiner noted that Tuba described optimizing the yield of
diethyl malonate (id. at 5).
The Examiner conceded, however, that Tuba’s process differed from
the claimed process in that Tuba did “not teach using isotopically enriched
carbon monoxide” (id.). To address that deficiency, the Examiner cited
Kihlberg as describing a procedure for synthesizing carbon-isotope
monoxide (id.). Finally, the Examiner found that Hernandez taught the
suitability of using diethyl malonate, radiolabeled with a carbon isotope,
either
14
C or
11
C, as a precursor for producing radiolabeled methyl fatty
acids “which are frequently used as biochemical tracers and
radiopharmaceuticals” (id. at 6).
Based on the references’ teachings, the Examiner concluded that an
ordinary artisan would have considered it obvious “to perform isotopic
labeling of malonic acid derivatives by performing carbonylation reactions
using a diazo compound and reagent such as alcohol using isotopically
labeled carbon monoxide in an automated reactor, when the teaching of
Tuba is taken in view of Kihlberg” (id.). The Examiner reasoned that the

[Rh{C(CO)SiMe3}(CO)(PEt3)2], 458 J. ORGANOMETALLIC CHEM. 225-228
(1993) (abstract only).
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Application 11/386,973

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artisan would have been prompted to “to prepare labeled diethyl malonate
because Hernandez teaches that diethyl-[2-
14
C]-malonate is a useful
precursor in labeling synthesis, such as for preparation of various 2-[11,
14C]-methyl fatty acids, which are frequently used as biochemical tracers
and radiopharmaceuticals” (id.).
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.

As Appellants do not argue the claims subject to this ground of
rejection separately, we select claim 1 as representative of the rejected
claims. See 37 C.F.R. § 41.37(c)(1)(vii).
Appellants’ arguments do not persuade us that a preponderance of the
evidence fails to support the Examiner’s prima facie case of obviousness as
to claim 1. Claim 1 recites a method for synthesizing carbon-isotope labeled
compounds by reacting a mixture containing a diazo compound, a transition
metal complex, and an appropriate reagent – which among other compounds
may be an alcohol – with carbon-isotope monoxide at high pressure.
The Examiner has advanced evidence, in the form of Tuba, that,
except for the isotope-labeled carbon monoxide, it was known in the art to
prepare a number of compounds using that procedure, diethyl malonate
being among those compounds (see Tuba 59-60). The Examiner has also
advance evidence, in the form of Hernandez, that
14
C-labeled diethyl
malonate was itself useful for preparing labeled methyl fatty acids “which
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Application 11/386,973

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are frequently used as biochemical tracers and radiopharmaceuticals”
(Hernandez A751). Given these teachings, we agree with the Examiner that
an ordinary artisan seeking to prepare carbon-isotope labeled diethyl
malonate, as taught by Hernandez, would have considered it obvious to use a
known process of preparing that compound, such as that taught by Tuba, and
in doing so would have used isotope-labeled carbon monoxide, such as that
taught by Kihlberg.
Appellants argue that “Tuba, Kihlberg, or Hernandez do not disclose,
teach, or suggest using the appropriate reagents disclosed in the current
invention for a carbon-isotope labeling synthesis method. This is an
essential feature of the present invention” (App. Br. 5).
Appellants do not, however, explain with any specificity why an
ordinary artisan would have considered the reagents described in the prior
art cited by the Examiner to be inappropriate for generating an isotopically
labeled carbon compound as recited in claim 1. In the absence of some fact-
based explanation as to some error in the Examiner’s reasoning, we do not
find this argument persuasive.
Appellants argue:
[I]t is impermissible within the framework of 35 U.S.C. § 103
to pick and choose from any one reference only so much of it as
will support a given position to the exclusion of other parts
necessary to the full appreciation of what such reference fairly
suggests to one skilled in the art.

(App. Br. 5 (citing Bausch & Lomb, Inc. v. Barnes-Hind/Hydrocurve, Inc.,
796 F.2d 443 (Fed. Cir. 1986))).
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We are not persuaded. Appellants do not point, with any specificity,
to any portion of any of the cited references that the Examiner might have
ignored so as to fail to fully appreciate the references’ teachings.
Appellants similarly argue that “it is well settled in the law that a
reference must be considered not just for what it expressly teaches, but also
for what it fairly suggests to one who is unaware of the claimed invention”
(App. Br. 5 (citing In re Baird, 16 F.3d 380 (Fed. Cir. 1994). Appellants do
not, however, direct us to anything in the record suggesting that the
Examiner somehow misapprehended what the cited references would have
fairly suggested to an ordinary artisan unaware of the claimed invention.
In sum, as Appellants’ arguments do not persuade us that the
Examiner erred in concluding that claim 1 would have been obvious to an
ordinary artisan, we affirm the Examiner’s rejection of that claim over Tuba,
Kihlberg, and Hernandez. As they were not argued separately, claims 2-6
and 19 fall with claim 1. See 37 C.F.R. § 41.37(c)(1)(vii).
The Examiner also rejected claims 1-7 and 19 as obvious over Tuba,
Kihlberg, Hernandez, and Deydier (Ans. 7). The Examiner relied on Tuba,
Kihlberg, and Hernandez for the teachings discussed above, and cited
Deydier as evidence that it was known in the art to use a rhodium complex,
as recited in claim 7, in a “functionally equivalent reaction” to that described
by Tuba (id.). The Examiner reasoned that an ordinary artisan would have
therefore considered it obvious “to substitute a rhodium catalyst for the
cobalt catalyst employed by Tuba” (id.).
We again select claim 1 as representative of the rejected claims. See
37 C.F.R. § 41.37(c)(1)(vii).
Appeal 2011-006207
Application 11/386,973

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As to this rejection, Appellants’ sole argument is that “Tuba,
Kihlberg, Hernandez, or Deydier do not disclose, teach, or suggest using the
appropriate reagents disclosed in the current invention for a carbon-isotope
labeling synthesis method. This is an essential feature of the present
invention” (App. Br. 6).
As discussed above, however, we are not persuaded that the Examiner
erred in concluding that claim 1 would have been obvious in view Tuba,
Kihlberg, and Hernandez, and each of those references is applied against
claim 1 in this rejection as well. Moreover, Appellants do not point, with
any specificity, to any error in the Examiner’s characterization of Deydier,
or to any error in the Examiner’s rationale for combining Tuba, Kihlberg,
and Hernandez with Deydier.
Thus, as Appellants’ arguments do not persuade us that the Examiner
erred in concluding that claim 1 would have been obvious to an ordinary
artisan in view Tuba, Kihlberg, Hernandez, and Deydier, we affirm the
Examiner’s rejection of that claim over those references. As they were not
argued separately, claims 2-7 and 19 fall with claim 1. See 37 C.F.R. §
41.37(c)(1)(vii).
SUMMARY
We affirm the Examiner’s obviousness rejection of claims 1-6 and 19
under over Tuba, Kihlberg, and Hernandez.
We also affirm the Examiner’s obviousness rejection of claims 1-7
and 19 over Tuba, Kihlberg, Hernandez, and Deydier.

Appeal 2011-006207
Application 11/386,973

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TIME PERIOD
No time period for taking any subsequent action in connection with
this appeal may be extended under 37 C.F.R. § 1.136(a).

AFFIRMED

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