Ex Parte Pleschke et al

Patent Trial and Appeal Board

Aug 22, 2017

12681843 (P.T.A.B. Aug. 22, 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.
12/681,843 04/06/2010 Axel Pleschke 13779-576 7789
45473 7590 08/22/2017
BGL/Research Triangle Park
P.O. BOX 110285
RESEARCH TRIANGLE PARK, NC 27709
EXAMINER
BALASUBRAMANIAN, VENKATARAMAN
ART UNIT PAPER NUMBER
1624
MAIL DATE DELIVERY MODE
08/22/2017 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 AXEL PLESCHKE, THOMAS SCHMIDT,
JOACHIM GEBHARDT, SANDRA LOEHR, MICHAEL KEIL,
and JAN HENDRIK WEVERS
____________

Appeal 2016-006432
Application 12/681,8431
Technology Center 1600
____________

Before JEFFREY N. FREDMAN, RACHEL H. TOWNSEND, and DAVID
COTTA, Administrative Patent Judges.

COTTA, Administrative Patent Judge.

DECISION ON APPEAL

This is an appeal under 35 U.S.C. § 134 involving claims to a process
for preparing a sulfuric diamide. The Examiner rejected the claims on
appeal under 35 U.S.C. § 103(a) as obvious.
We REVERSE.

1 According to Appellants, the real party in interest is BASF SE. App. Br.
3.

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Application 12/681,843

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STATEMENT OF THE CASE
The Specification discloses: “Processes for preparing sulfuric
diamides of the formula I [R1R2N-S(O)2-NH2] have been known in principle
for some time” Spec. 1. Each of these known processes, however, suffers
from drawbacks, including that “the reaction proceeds only incompletely,”
that “hydrogen chloride [is] released in the first step,” that “yields . . . are
unsatisfactory,” that the components of the process are “comparatively
costly,” and that the process is “comparatively complicated owing to the
multitude of steps.” Id. at 1–2. The Specification discloses: “It is thus an
object of the present invention to provide an easily performable process for
preparing sulfuric diamides of the general formula I designated above, which
provides these compounds in good yields and which can be carried out with
inexpensive starting materials.” Id. at 2. The Specification asserts that
“[t]his object is surprisingly achieved by the process defined.” Id.
Claims 1, 2, 4–6, 8, and 9 are on appeal. Claim 1 is illustrative and
reads as follows:
1. A process for preparing a sulfuric diamide of the formula (I)

R1R2N-S(O)2-NH2 (I)
in which R1 and R2 are each independently a primary alkyl
radical having from 1 to 8 carbon atoms, a secondary alkyl
radical having from 3 to 8 carbon atoms or a cycloalkyl
radical having from 5 to 8 carbon atoms, comprising
i) reacting a secondary amine of the formula (II)

R1R2NH (II)

with sulfuryl chloride in an inert organic solvent in the
presence of a tertiary amine to give a sulfamoyl chloride of
the formula (III)

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R1R2N-S(O)2Cl (III)

wherein the tertiary amine is present in amount of from 1.05
to 1.5 equivalents, based on the secondary amine of formula
(II); and wherein the secondary amine of the formula (II) and
sulfuryl chloride are used in a molar ratio of from 1:1.1 to
1.1:1; and
ii) reacting the sulfamoyl chloride of the formula (III)
obtained in step i) with gaseous ammonia, wherein the
reaction is performed at temperatures in the range of from
30 to 80°C,

the sulfamoyl chloride of the formula (III) being used in step
ii) in the form of the solution obtained in step i) in the inert
organic solvent.

The Examiner rejected claims 1, 2, 4–6, 8 and 9 under 35 U.S.C.
§ 103(a) as obvious over the combination of Vandi,2 Wheeler,3 Houlihan,4
and Adkison.5
ANALYSIS
In finding claims 1, 2, 4–6, 8 and 9 obvious, the Examiner found that
Vandi and Wheeler both disclose a two-step process for making sulfonamide
by reacting a secondary amine with sulfuryl chloride in the presence of an
inert organic solvent, such as chloroform, benzene or ether, and reacting the

2 Vandi et al., Synthesis and Properties of Some N-Substituted Sulfamides,
26(4) J. ORG. CHEM. 1136–1138 (1961) (“Vandi”).
3 Wheeler et al., Preparation and Properties of Certain Derivatives of
Sulfamide,” 66(8) J. AM. CHEM. SOC. 1242–1243 (1944) (“Wheeler”).
4 Houlihan, US Patent No. 3,709,677, issued Jan. 9, 1973.
5 Adkison et al., Semicarbazone-Based Inhibitors of Cathepsin K, Are they
Prodrugs for Aldehyde Inhibitors? 16 BIORGANIC & MEDICINAL CHEMISTRY
LETTERS 978–983 (2006) (“Adkison”).
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resulting product with ammonia. Final Act. 3;6 see also Ans. 10, 12, 13.
The Examiner found that Houlihan disclosed “the preparation [of] various
N-substituted sulfamoyl compounds” using “inert solvent and tertiary amine
as required by step (i) of the claimed invention.” Final Act. 3. The
Examiner similarly found that Adkison demonstrated that “[t]he use of inert
solvent and tertiary amine is well known in the art.” Final Act. 4; see also
Ans. 3 The Examiner concluded that persons of ordinary skill in the art
would have combined the teachings of Vandi, Wheeler, Houlihan and
Adkison and arrived at the claimed process because they “would have
expected the analogous material . . . to obtain a result consistent with the
teachings of the [prior] art.” Ans. 4; see also Final Act. 4.
With respect to the requirement of claim 1 that the product of the first
process step be reacted with “gaseous ammonia” at a temperature “in range
of from 30 to 80°C,” the Examiner concluded that “changing liquid
ammonia to gaseous ammonia is an obvious variant and is not patentably
distinct [in the] absence of any evidence to show otherwise.” Ans. 10–11;
see also Final Act. 7. In support of this position, the Examiner notes that the
Specification “recites ammonia in general thereby permitting use of liquid
ammonia as well and only recites gaseous ammonia as preferred
embodiment.” Ans. 15; see also Final Act. 9. The Examiner thus concludes
that there is “no critical requirement of gaseous ammonia as per instant
specification.” Id. at 15.
Appellants argue, inter alia, that “the Examiner has not provided any
reasons or rationale as to why the skilled artisan would combine the cited
references and modify the combined teachings by making the changes

6 Office Action mailed April 8, 2014 (“Final Act.”).
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necessary to arrive at Applicants invention.” App. Br. 14. More
specifically, with respect to the requirement for gaseous ammonia,
Appellants argue that Vandi and Wheeler each disclose the use of liquid
ammonia, and that this suggests that using “liquid ammonia is the
conventional way of conducting an ammoniolysis reaction.” Id. at 15.
Appellants contend that the “Examiner’s reference to the Applicants’
specification . . . [suggests] that the Examiner is admitting to using
impermissible hindsight (i.e. the Applicants’ own specification) to support
the Examiner’s conclusion of obviousness.” Id. at 16.
Appellants have persuaded us that the Examiner has not carried the
burden of establishing that the claimed invention would have been obvious
over the cited art.
In finding that it would have been obvious to carry out the claimed
ammoniolysis reaction using gaseous ammonia, the Examiner simply asserts
gaseous ammonia is an obvious variant of liquid ammonia and places the
burden on Appellants to demonstrate otherwise. Ans. 10–11; see also Final
Act. 7. As an initial matter, the Examiner appears to have misallocated the
burden of proof. As stated in In re Oetiker, 977 F.2d 1443, 1445 (Fed. Cir.
1992) (“[T]he [E]xaminer bears the initial burden . . . of presenting a prima
facie case of unpatentability.”). Accordingly, it was not Appellants’ burden
to demonstrate the non-obviousness of using gaseous ammonia, rather it was
the Examiner’s burden to establish that it would have been obvious to
replace liquid ammonia with gaseous ammonia.
The Examiner does not identify, and we do not find, any evidence in
the record to support the Examiner’s assertion that gaseous ammonia is an
“obvious variant” of liquid ammonia. Indeed, the only evidence of record
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with respect to the interchangeability of liquid and gaseous ammonia
suggests that there may be significant differences between liquid and
gaseous ammonia, at least with respect to commercial scale manufacturing
processes. Cortes Decl.7 3 (Reporting results of comparative testing of
processes employing gaseous and liquid ammonia and concluding, “[i]n
view of these facts, the use of pressurized ammonia at moderate temperature
has significant commercial advantages over the use of liquid ammonia at
low temperatures.”). Similarly, the Specification teaches the prior art
reaction of Behrend was incomplete with gaseous ammonia (see Spec. 1:22–
29), yet the Specification still prefers gaseous ammonia (see Spec. 7:35).
Thus, the Specification does not establish that the prior art recognized
gaseous and liquid ammonia as equivalents for the claimed reaction, instead
suggesting that the inventors recognized gaseous ammonia as preferred (see
Spec. 7:30–42).
We recognize that our reviewing court has held
while an analysis of obviousness always depends on evidence
that supports the required Graham factual findings, it also may
include recourse to logic, judgment, and common sense
available to the person of ordinary skill that do not necessarily
require explication in any reference or expert opinion.
Perfect Web Technologies, Inc. v. Infousa, Inc., 587 F.3d 1324, 1329 (Fed.
Cir. 2009). In “Perfect Web[, however,] common sense was invoked to
supply a limitation that was admittedly missing from the prior art, [where]
the limitation in question was unusually simple and the technology
particularly straightforward.” Arendi S.A.R.L. v. Apple Inc., 832 F.3d 1355,

7 Declaration of Dr. David Cotes under 37 C.F.R. § 1.132, signed January
15, 2014 (“Cortes Decl.”).
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1362 (Fed. Cir. 2016). The same is not true of the technology before this
Panel for review. See generally Eisai Co. v. Dr. Reddy’s Ltd., 533 F.3d
1353, 1359 (Fed. Cir. 2008) (“To the extent an art is unpredictable, as the
chemical arts often are, KSR’s focus on these ‘identified, predictable
solutions’ may present a difficult hurdle because potential solutions are less
likely to be genuinely predictable.”).
Further, although the Board has subject matter expertise,

the Board cannot accept general conclusions about what is
“basic knowledge” or “common sense” as a replacement for
documentary evidence for core factual findings in a
determination of patentability. . . . To hold otherwise would be
to embark down a slippery slope which would permit the
examining process to deviate from the well-established and
time-honored requirement that rejections be supported by
evidence. It would also ultimately “render the process of
appellate review for substantial evidence on the record a
meaningless exercise.”
K/S Himpp v. Hear-Wear Technologies, LLC, 751 F.3d 1362, 1366 (Fed.
Cir. 2014), quoting In re Zurko, 258 F.3d 1379, 1385-86 (Fed. Cir. 2001).
As the Examiner’s conclusion of obviousness relies upon the unsupported
assertion that gaseous ammonia is an obvious variant of liquid ammonia
with respect to reacting sulfamoyl chloride to obtain a sulfuric diamide of
the formula recited, we reverse the Examiner’s rejection of claims 1, 2, 4–6,
8, and 9.

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SUMMARY
For the reasons set forth herein, we reverse the Examiner’s rejection
of claims 1, 2, 4–6, 8 and 9 under 35 U.S.C. § 103(a) as obvious over the
combination of Vandi, Wheeler, Houlihan, and Adkison.

REVERSED