Dinesh Mistry et al.

Patent Trials and Appeals Board

Sep 5, 2019

11631993 - (D) (P.T.A.B. Sep. 5, 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.
11/631,993 01/09/2007 Dinesh Mistry 32471/22363 1554
4743 7590 09/05/2019
MARSHALL, GERSTEIN & BORUN LLP
233 SOUTH WACKER DRIVE
6300 WILLIS TOWER
CHICAGO, IL 60606-6357
EXAMINER
POPA, ILEANA
ART UNIT PAPER NUMBER
1633
NOTIFICATION DATE DELIVERY MODE
09/05/2019 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):
mgbdocket@marshallip.com
PTOL-90A (Rev. 04/07)

UNITED STATES PATENT AND TRADEMARK OFFICE
__________

BEFORE THE PATENT TRIAL AND APPEAL BOARD
__________

Ex parte DINESH MISTRY and JATINDER SINGH KULLAR
__________

Appeal 2019-002221
Application 11/631,993
Technology Center 1600
__________

Before DEMETRA J. MILLS, JEFFREY N. FREDMAN, and
DAVID COTTA, Administrative Patent Judges.

MILLS, Administrative Patent Judge.

DECISION ON APPEAL

This is an appeal under 35 U.S.C. § 134(a). The Examiner has rejected
the claims for obviousness, and obviousness-type double patenting. We have
jurisdiction under 35 U.S.C. § 6(b).
We affirm.
Appeal 2019-002221
Application 11/631,993

2
STATEMENT OF CASE

The following claim is representative.
1. A process of preparing an ethylenically unsaturated
amide from the corresponding ethylenically unsaturated nitrile
for use of preparing a high molecular weight water-soluble or
water-swellable polymer, in which the nitrile is subjected to a
hydration reaction in an aqueous medium in the presence of a
biocatalyst, which biocatalyst is a microorganism of the
Rhodococcus genus that is capable of producing a nitrile
hydratase,
wherein the nitrile contains above 2 ppm acrolein and up
to 500 ppm and the amide contains less than 2 ppm acrolein;
wherein the ethylenically unsaturated amide is formed in
the aqueous medium at a concentration ranging from 30 wt.%
to 55 wt.%; and
wherein a step of separately removing acrolein from the
ethylenically unsaturated nitrile is avoided.

Appeal Br. 22 (Claims Appendix).
Cited References
Pierce US 5,863,750 Jan. 26, 1999
Armitage et al. ‘106 US 7,816,106 B2 Oct. 19, 2010
Armitage et al. ‘969 US 9,434,969 B2 Sept. 6, 2016
Kawakami JP 401125353A May 17, 1989

Nagasawa et al., “Microbial Production of Commodity Chemicals,”
67(7) Pure and Appl. Chem. 1241–1256 (1995).

Yamada et al., “Nitrile Hydratase and Its Application to Industrial
Production of Acrylamide,” 60 (9) Biosci. Biotech. Biochem. 1391–
1400 (1996).

Appeal 2019-002221
Application 11/631,993

3
Hughes et al., “Application of whole cell rhodococcal biocatalysts in
acrylic polymer manufacture,” 74 Antonie van Leeuwenhoek
107–118 (1998).

Grounds of Rejection
1. Claims 1, 6–8, 13–15, and 17–19 are rejected on the ground of
nonstatutory double patenting as being unpatentable over claims 1–
7 of U.S. Patent No. 9,434,969, in view of both Yamada and
Pierce.
2. Claims 1, 6–8, 13–15, and 17–19 are rejected on the ground of
nonstatutory double patenting as being unpatentable over claims 1–
5 of U.S. Patent No. 7,816,106, in view of both Yamada et al. and
Pierce.
3. Claims 1, 6–8, 13–15, 17–18, 23, 24, 26, 27, and 29–33 are
rejected under pre-AIA 35 U.S.C. §103(a) as being unpatentable
over Nagasawa in view of each Pierce, Kawakami, and Hughes.

FINDINGS OF FACT
The Examiner’s findings of fact are set forth in the Answer at pages 3-
22.
We reference our prior Decisions in this case dated November 21,
2012, and April 21, 2017.

PRINCIPLES OF LAW
In making our determination, we apply the preponderance of the
evidence standard. See, e.g., Ethicon, Inc. v. Quigg, 849 F.2d 1422, 1427
Appeal 2019-002221
Application 11/631,993

4
(Fed. Cir. 1988) (explaining the general evidentiary standard for proceedings
before the Office).
“The combination of familiar elements according to known methods
is likely to be obvious when it does no more than yield predictable results.”
KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398, 416 (2007).

Obviousness-type Double Patenting
Rejections 1 and 2
The Examiner rejects claims 1, 6–8, 13–15, and 17–19 on the ground
of nonstatutory double patenting as being unpatentable over claims 1–7 of
Armitage (US 9,434,969), in view of both Yamada and Pierce.
The Examiner finds that the pending claims and the Armitage ‘969
patented claims are not patentably distinct from each other
because both claim sets are drawn to the same method of
using Rhodococcus rhodochrous to prepare an ethylenically
unsaturated amide from the corresponding nitrile. The patent
claims do not recite accumulating the amide at 30-55 wt%.
Yamada et al. teach that adding urea to the culture medium as
recited in the patent claims increases the levels of nitrile
hydrolase leading to amide accumulating at 56 w/v % . . . when
the acrylonitrile is provided at 6% (while Yamada et al. teach
w/v and not w/w%, absent evidence to the contrary, the values
taught by Yamada et al. fall within the claimed ranges), and
also that the reaction could take place at a temperature below
10ºC for 3 days (Table II and paragraph bridging p. 1394 and
1395). The instant claims do not recite urea. However, based
on the teachings of Yamada et al., it would have been obvious
to one of skill in the art to modify the instant claims by adding
urea to the growth medium and conduct the reaction for 3 days
at 10ºC to achieve the predictable result of obtaining enhanced
levels of ethylenically unsaturated amides . . . Pierce teaches
that Rhodococci are capable of completely removing acrolein
Appeal 2019-002221
Application 11/631,993

5
during the process of converting nitrile to amide, wherein the
starting nitrile preparation comprises high acrolein
concentrations, such as 54 ppm acrolein (see column 10, lines
20-27; Example 9 on column 36, lines 38-60; Fig. 3).

Ans. 6. See also, Armitage ‘106 rejection. Ans. 4.

The Examiner concludes that,

one of skill in the art would have reasonably expected
that the use of Rhodococci as recited in the patent claims would
also efficiently remove acrolein from preparations during the
process of amide preparation when any amount of acrolein was
present in the starting material of nitrile, and would have found
it an obvious part of the process recited by patent claims with
any starting preparation (i.e. any acrolein amount in the starting
nitrile starting material). While the patent claims did not recite
the removal of acrolein from a reaction mixture, clearly this
would have been a consequence in the recited methods of using
Rhodococci as described and demonstrated by Pierce (i.e.,
wherein a separate step of removing acrolein is avoided).

Ans. 6.

Appellants contend that, the combination of Pierce with the methods
of Armitage I and Armitage II,
could potentially address the acrolein limitation, if
Pierce’s waste stream were used as the “nitrile” in the two
recited methods of Armitage I and Armitage II. Even in such
cases, however, the Armitage I/Armitage II and Pierce
combinations do not result in the recited limitation that the
concentration of the formed ethylenically unsaturated amide
monomer ranges from 30 wt.% to 55 wt.%.
Yamada is cited by the action for its disclosure related to
urea addition, nitrile hydrolase levels, and reaction temperature,
and it does not otherwise address the deficiency of Armitage
Appeal 2019-002221
Application 11/631,993

6
I/Armitage II and Pierce with respect to the formed
ethylenically unsaturated amide monomer concentration range.

App. Br. 19.

ANALYSIS

We agree with the Examiner’s fact finding, statement of the rejection
and responses to Appellants’ arguments as set forth in the Answer. We find
that the Examiner has provided evidence to support a prima facie case of
obviousness-type double patenting. We provide the following additional
comment to the Examiner’s argument set forth in the Final Rejection and
Answer.
Claim 1 of Armitage ‘969 reads as follows:
1. A method of producing an amide from the
corresponding nitrile comprising the following steps,
i) providing a microorganism of the genus Rhodococcus
capable of producing a nitrile hydratase biocatalyst,
ii) culturing the microorganism in a growth medium,
iii) storing the microorganism,
iv) contacting the nitrile with the microorganism in an
aqueous medium and thereby converting the nitrile to
the amide,
wherein the microorganism is retained in the growth
medium and the microorganism is not recovered from the
original fermentation medium and stored without further
downstream processing steps at a temperature above the
freezing point to 25° C. as non-actively growing free
cells in the growth medium that comprises water and urea
or a urea derivative.

Claim 1 of Armitage ‘106 reads as follows:

1. A method of producing an amide from the
corresponding nitrile comprising the following steps,
Appeal 2019-002221
Application 11/631,993

7
i) providing a microorganism capable of producing a
nitrile hydratase biocatalyst,
ii) culturing the microorganism in a growth medium ,
iii) storing the microorganism in a storage medium that
comprises water and the growth medium in step ii),
iv) contacting the nitrile with the microorganism in the
storage medium of step iii) without recovery of the
microorganism using centrifugation or filtration and
thereby converting the nitrile to the amide,
wherein the microorganism is stored in step iii) as a non-
actively growing culture in the storage medium and the
term non-actively growing culture means that the
metabolism in the microorganism cells is substantially
zero and the microorganism is Rhodococcus rhodochrous
NCIMB 41164.

We consider both of the obviousness-type double patenting rejections
together, as they present similar issues on related cited prior art (Armitage
‘969/Armitage ‘106, Yamada, and Pierce).
Appellants contend that, “the Armitage I [‘969]/Armitage II [‘106]
and Pierce combinations do not result in the recited limitation that the
concentration of the formed ethylenically unsaturated amide monomer
ranges from 30 wt.% to 55 wt.%.” App. Br. 20. We are not persuaded.
The Examiner provided evidence that the prior art at the time of the
invention, Yamada, discloses a method of obtaining a concentration of the
formed ethylenically unsaturated amide monomer ranges from about 30
wt.% to 56 wt.%. In particular, Yamada discloses that adding urea to the
culture medium increases the levels of nitrile hydrolase leading to amide
accumulating at about 56 w/v % as recited in the patent claims, when the
acrylonitrile is provided at 6%. Yamada, 1394–95; Ans. 6. While there is a
1% difference in the claimed amount of amide formed from acrylonitrile as
Appeal 2019-002221
Application 11/631,993

8
compared to Yamada (55% vs. v 56%), In re Patel recognized that prima
facie rejections may be appropriate “where there is a teaching in the prior art
that the end points of the prior art range are approximate, or can be flexibly
applied.” In re Patel, 566 Fed.Appx. 1005, 1010 (2014). Appellants claim a
broad range of ethylenically unsaturated amide formed without a specific
disclosure in the Specification of a standard of measurement error. Yamada
discloses that the acrylamide accumulation may be influenced by
temperature (p. 1395) and reaction conditions.1 Therefore, we find that the
there is a teaching in the prior art that the end points of the prior art range are
approximate, or can be flexibly applied, and that the claimed amount of
amide formed is obvious over Yamada when combined with the cited prior
art. Modifying the process of Armitage I (‘969)/ II (‘106) with the method
of Yamada would have resulted in the recited limitation that the
concentration of the formed ethylenically unsaturated amide monomer
ranges from 30 wt.% to 55 wt.%.
We agree with the Examiner that it would have been obvious to one of
ordinary skill in the art at the time of the invention desiring to increase the
amide product, to modify the method of producing an amide from the
corresponding nitrile disclosed in Armitage ‘969, using the known method
of Yamada of adding urea to the culture medium to increase the levels of
nitrile hydrolase, leading to ethylenically unsaturated amide accumulating at
about 56 w/v % with an unspecified standard of error. According to
Yamada, “all microorganisms degrade nitriles to their corresponding

1 It is also well known in the art that the amount of reactant used in a
chemical process influences the amount of final product.
https://www.middleschoolchemistry.com/lessonplans/chapter6/lesson2
Appeal 2019-002221
Application 11/631,993

9
carboxylic acids and ammonia with or without producing amides as an
intermediate,” therefore the product of the method would be ethylenically
unsaturated. Yamada, 1391. Therefore, the instant claims are obvious
variants of the method of the two Armitage patent claims in combination
with the cited prior art.
The Examiner has provided a prima facie case of obviousness-type
double patenting for rejections 1 and 2, which has not been convincingly
rebutted by Appellants. The two obviousness-type double patenting
rejections are affirmed for the reasons of record.

Obviousness Rejection 3
The Examiner rejected claims 1, 6–8, 13–15, 17–18, 23, 24, 26, 27,
and 29–33 under U.S.C. §103(a) as being unpatentable over Nagasawa in
view of each Pierce, Kawakami, and Hughes.
According to the Examiner,
Nagasawa et al. teach a method of producing acrylamide (i.e.,
preparing an ethylenically unsaturated amide) from acrylonitrile (i.e.,
the corresponding ethylenically unsaturated nitrile) in an aqueous
medium (such as water) in the presence of an immobilized
microorganism belonging to the Rhodococcus genus capable of
producing nitrile hydratase, wherein the acrylonitrile is subjected to
hydration by the produced nitrile hydratase; one of the
microorganisms successfully used is Rhodococcus rhodochrous J1.
Nagasawa et al. teach feeding acrylonitrile to maintain a concentration
of 60g/L and also obtaining acrylamide accumulation in the medium
at a concentration of 40% g/L (claims 1, 6, 8, 13, and 23) (p. 1244-
1247). While Nagasawa et al. teach w/v and not w/w percentages
(claims 1, 23, 30, and 32), absent evidence to the contrary, the values
taught by Nagasawa et al. fall within the claimed ranges. Final Act.
6.

Appeal 2019-002221
Application 11/631,993

10
The Examiner further finds that:

[O]ne of skill in the art would have found obvious to use routine
experimentation and vary the amount of acrylonitrile that is fed to the
medium with the purpose of optimizing the acrylamide yield.
Nagasawa et al. teach that Rhodococcus rhodochrous J1 also produces
nitrilase and thus is used to produce acrylic and methacrylic acid from
acrylonitrile and methacrylonitrile, respectively (p. 1248).

Final Act. 6. The Examiner relies on Pierce to show that, “Rhodococci are
capable of completely removing acrolein during the process of converting
acrylonitrile to acrylamide, wherein the starting acrylonitrile preparation
comprises high acrolein concentrations, such as 54 ppm acrolein (see Pierce,
column 10, lines 20-27; Example 9 on column 36, lines 38-60; Fig. 3).”
Final Act. 7. Even though Nagasawa et al. did not describe the removal of
acrolein from a reaction mixture, the Examiner finds that removal of
acrolein would have been “a consequence in the described methods of using
Rhodococci as described and demonstrated by Pierce (i.e., wherein a
separate step of removing acrolein is avoided).” Final Act. 7. Kawakami is
relied on for the disclosure of using Rhodococcus to produce
methacrylamide from methacrylonitrile (Abstract). Final Act. 8.
Appellants contend that:
The proposed combination of references does not
disclose, teach, or suggest all recited limitations, in particular
the limitation that the ethylenically unsaturated nitrile reactant
(e.g., acrylonitrile) contains above 2 ppm acrolein and upto 500
ppm acrolein. Specifically:

Nagasawa does not does not disclose, teach, or suggest
that its acrylonitrile feed stream contains above 2 ppm and up to
500 ppm acrolein. The failure of Nagasawa to disclose, teach,
Appeal 2019-002221
Application 11/631,993

11
or suggest acrolein content of its acrylonitrile feed stream is
acknowledged by the Final Action (p. 7) and was likewise
found by the Board in the PTAB Decision (p. 11).

Pierce’s disclosure of acrolein in its waste stream at a
particular concentration is not part of the current obviousness
rejection. Pierce is only cited as providing evidence that
Rhodococci are capable of removing acrolein. Final Action, pp.
10-11.

Kawakami and Hughes are cited for features unrelated
to any potential acrolein content of a feed stream.

More specifically, Nagasawa’s base process addresses
the limitations of nitrile-to-amide conversion in terms of (i) the
30-55 wt.% concentration of the ethylenically unsaturated
amide as a formed reaction product in the aqueous medium and
(ii) the 3-6 wt.% feed concentration of ethylenically unsaturated
nitrile monomer, but Nagasawa does not address the 2-500 ppm
acrolein limitation for the ethylenically unsaturated nitrile.
Likewise, although Pierce’s waste stream includes acrolein, the
action does not rely on Pierce’s waste stream acrolein content to
meet the 2-500 ppm acrolein limitation.

App. Br. 15–16.
ANALYSIS
The claimed process involves subjecting a nitrile starting material to a
hydration reaction using a microorganism catalyst to obtain an ethylenically
unsaturated amide product. Claim 1. The claim requires that the nitrile,
starting material, contain above 2 ppm acrolein and up to 500 ppm, and that
the resulting amide product contain less than 2 ppm acrolein. The Examiner
relies on Pierce for the disclosure that Rhodococci are capable of removing
acrolein from an amide preparation. Final Action 10–11; Pierce col. 1.
Appeal 2019-002221
Application 11/631,993

12
In response to Appellants arguments, the Examiner explains that it
was known in the art, Schmitt (GB 2114118) and Denicola et al. (EP
0110861), that acrolein is typically found as an impurity at levels of 2 to 20
ppm in the acrylonitrile materials used to obtain acrylamide. Ans. 15. Thus,
the Examiner has provided evidence that one of ordinary skill in the art
would have understood that nitrile starting material of Nagasawa was known
to contain above 2 ppm acrolein at the time of the invention, as required by
claim 1. The Examiner further finds that these references teach
the necessity of using additional steps for removing acrolein
from acrylonitrile before converting it to acrylamide because
the presence of acrolein in acrylamide preparations interferes
with acrylamide polymerization, leading to polymers having
unsatisfactory reduced molecular weight (see Schmitt, p. 1; see
Denicola et al., p. 1-2). Thus, one of skill in the art would have
known that the acrylonitrile materials used to prepare
acrylamide contain acrolein and that acrolein must be removed
from acrylonitrile materials.

Ans. 15. The Examiner finds that because Rhodococci are capable of
removing acrolein from an amide preparation, that a preliminary acrolein
removal step is not required, and that the process of Nagasawa would result
in acrolein removal from the reaction mixture, e.g., an amide product
containing less than 2ppm of acrolein. Ans. 15.
Appellants further contend that
even if the acrolein were removed, the acrylonitrile materials
would be expected to contain other impurities that would not be
removed along with acrolein in forming acrylamide. Such
impurities other than acrolein present with acrylamide render
the acrylamide unsuitable for its intended use to form a
corresponding polyacrylamide.

Appeal 2019-002221
Application 11/631,993

13
Reply Br. 3.

We are not persuaded by Appellants’ arguments. We first note that
we interpret the term “in which” in claim 1 as being open to additional
ingredients, like a “comprising” claim, including other impurities in the
reactant. Claim 1 does not require specific levels of, or the removal of
ketones, aldehydes, and similar carbonyl impurities in addition to acrolein.
Appellants do not contest that it is well known in the art that acrolein
is typically found as an impurity at levels of 2 to 20 ppm in the acrylonitrile
starting materials used to obtain acrylamide. Ans. 15. The Examiner has
provided evidence that acrolein would be removed (less than 2 ppm) by an
amide production process using Rhodococci. Appellants have not shown
error in the Examiner’s prima facie case of obviousness.
The obviousness rejection is affirmed for the reasons of record.

CONCLUSION OF LAW
The cited references support the Examiner’s obviousness rejection,
which is affirmed for the reasons of record. The two obviousness-type
double patenting rejections are also affirmed. All pending, rejected claims
fall.

AFFIRMED