Ex Parte Shibata et al

Patent Trial and Appeal Board

Oct 13, 2017

14329356 (P.T.A.B. Oct. 13, 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.
14/329,356 07/11/2014 Yasushi SHIBATA 107929-0127 2361
22428 7590 10/17
Foley & Lardner LLP
3000 K STREET N.W.
SUITE 600
WASHINGTON, DC 20007-5109
EXAMINER
BALASUBRAMANIAN, VENKATARAMAN
ART UNIT PAPER NUMBER
1624
NOTIFICATION DATE DELIVERY MODE
10/17/2017 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):
ipdocketing @ foley. com
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte YASUSHI SHIBATA and TSUTOMUIMAGAWA
Appeal 2017-0036471
Application 14/329,356
Technology Center 1600
Before DONALD E. ADAMS, RICHARD M. LEBOVITZ, and
RYAN H. FLAX, Administrative Patent Judges.
LEBOVITZ, Administrative Patent Judge.
DECISION ON APPEAL
This appeal involves claims directed to a triazine compound and a
process which uses the triazine compound to make a substituted
methylamine compound. The Examiner rejected the claims under 35 U.S.C.
§ 103 as obvious. We have jurisdiction under 35 U.S.C. § 6(b). The
Examiner is affirmed-in-part.
STATEMENT OF THE CASE
Claims 15—31 stand rejected by the Examiner as follows:
1 The Appeal Brief (“Br.”) identifies Nipon Soda Co., Ltd., as the real-party-
in-interest. Br. 1.
Appeal 2017-003647
Application 14/329,356
1. Claims 16—31 under pre-AIA 35 U.S.C. § 103(a) as obvious in
view of JP 08-295670 (“JP ’670”). An English machine translation from the
Japanese Patent Organization (“JPO”) is relied upon by the Examiner in
making the rejection because the original document is in the Japanese
language. Examiner’s Answer (“Ans.”) 3.
2. Claim 15 under pre-AIA 35 U.S.C. § 103(a) as obvious in view
of DE 198 43 383 Al, publ. March 30, 2000 (“Jomaa”). The Examiner
relied upon a machine translation of the original document from the German
language into English. Ans. 4.
3. Claims 16—31 under pre-AIA 35 U.S.C. § 103(a) obvious in
view of Jomaa, WO 2005/123704 Al, publ. Dec. 29, 2005 (“Takano”), and
First Symposium on Chemical-Biological Correlation, May 26—27,
1950, p. 301 (1951) (“First Symposium”). Ans. 9.
4. Claims 16—31 under pre-AIA 35 U.S.C. § 103(a) obvious in
view of Jomaa, Takano, JP ’670, First Symposium, and JP 04021674
(English Abstract only, “Kaku”). Ans. 16.
Claim 16, the only independent process claim on appeal, is
reproduced below:
16. A process for producing a substituted methylamine
compound, said process comprising:
hydrolyzing the N-methylidene-substituted methylamine
oligomer represented by formula (II”) shown below in the
presence of an acid,
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Application 14/329,356
MXv
wherein R represents a hydrogen atom and A represents a
group represented by formula (IV) shown below:
wherein X is as defined above.
Claim 15 is an independent claim directed to the triazine of formula
II”, but defines X differently than claim 16, where X is a halogen atom, or, a
substituted or unsubstituted alkyl group.
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Appeal 2017-003647
Application 14/329,356
1. REJECTION BASED ON JP ’670
Claim 16
Claim 16 is directed to a process for producing a substituted
methylamine compound.
The process has one step which comprises hydrolyzing a compound of
Formula II” in the presence of an acid. The Formula II” compound of claim
16 is reproduced below from the Claim Appendix of the Appeal Brief
(annotations added herein):
trimer”). The claim identifies the Formula II” compound as an “N-
methylidene-substituted methylamine oligomer.” Br. (Claim App’x i).
The X substituent in the pyridine is a halogen atom, or a substituted or
unsubstituted alkyl group.
The acid hydrolysis of the Formula II” compound produces a
substituted methylamine compound of formula (III) which has an alpha
carbon (-C) joined to the substituted pyridine and an amine group (-NEE).
This compound is shown below (as drawn herein based on Formula (III)).
substituted pyridine
The Formula II” compound is a 1,3,5 triazine having three X
substituted pyridines attached to a triazine ring to form a trimer (“triazine
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Appeal 2017-003647
Application 14/329,356
H
C - NH
H
I
Specification
The Specification of the 14/329,356 application, the subject of this
appeal, teaches that the claimed Formula II” trimer is produced by reacting
the following hexamethylenetetraammonium salt with a base, where A is the
substituted pyridine defined above.
The Specification teaches that the preferred A group is a 2-
chloropyridin-5-yl group which is the above-described pyridine where the X
substituent is the halogen, chloride. Id. at 6.
Appellants admit that JP ’670 teaches reacting the same
tetraammonium salt (Formula (6), depicted below) with a base as described
in the Specification. Br. 5. However, Appellants argue that JP ’670 teaches
that the reaction of the tetraammonium salt (Formula (6), depicted below)
with the base results in a monomer having the X-substituted pyridine
(Formula (6), depicted below) and not the trimer of Formula II” as claimed.
(!)
Spec. 4.
JP ’670
5
Appeal 2017-003647
Application 14/329,356
Id. In other words, as explained in more detail below, Appellants contend
that the JP ’670 does not teach the step of hydrolyzing a triazine trimer —but
instead teaches hydrolyzing a monomer.
Appellants provided the following drawing based on JP ’670 to show
that the base reaction (“alkali”) produces the pyridine monomer and not the
pyridine trimer as claimed (id.):
I 7 I-7I
AT
& RJT. aifeal
r7 "V"" •A 7 or 6 hours) •1Of
FomtJa Wi
2-ph/>fo S
Formula (is
5-
The reaction depicted above, based on JP ’670, shows the production
of a monomer of Formula (1), not a trimer of Formula II” as claimed.
Appellants admit that the Formula (1) compound shown above is
hydrolyzed in the presence of acid to produce a Formula (2) compound,
which is the same as the Formula (III) compound recited in claim 16. Id.
This is depicted below.
dydro-iy-vs -fs add;
.X
N-. v*V'''
'-X
F tu
rormAia i’ ?-orriiJisi (3);
-X too-
syrens
6
Appeal 2017-003647
Application 14/329,356
In other words, the process described in JP ’670 produces the same
compound produced in the process recited in claim 16, but by using a
pathway that includes a monomer, not a triazine trimer, as required by the
claim. Compare Formula (2) of JP ’670 with Formula (III) (see, above, in
reproduced claim 16) having an alpha carbon joined to substituted pyridine
and an amine group as drawn above.
Difference between JP ’670 and claimed process
The Specification teaches that the pyridyl tetraammonium salt
produces a triazine trimer (Formula II” compound of claim 16) in the
presence of a base. Spec. 4. Appellants contend that JP ’670 teaches that
the same pyridyl tetraammonium salt produces a monomer in the presence of
a base. Br. 5. Appellants contend that the reason for this difference is that
the conditions utilized in the Specification are different from those utilized
in JP ’670:
Appellant submits that the disclosed intermediate in
JP'670, N-methylidene-2-chloro-5-pyridine methanamine [the
monomer], is produced by the process of that reference at least
due to the difference in the conditions used in the hydrolysis of
the 2-chloro-5-pyridyl-methyl hexamethylene tetraammonium
chloride [the same starting material described in the
Specification], In the Declaration under 37 C.F.R. § 1.132 by Dr.
Osamu Mikuni (“the Mikuni Declaration”) submitted in the
grandparent application (i.e., U.S. Application No., 12/596,950)
on March 26, 2014, Dr. Mikuni explains that the conditions used
in the reaction according to JP'670 provides a higher pH range
for the hydrolysis compared to the instant application. Dr.
Mikuni calculates the pH values of the reaction solutions of
Examples 5, 7 and 8 of JP'670 and concludes that the pH of these
exemplary compositions are all pH 11.6 or higher.
Id. at 6.
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Appeal 2017-003647
Application 14/329,356
Appellants contend that the Examiner “essentially concludes
inherency without providing ‘a basis in fact and/or technical reasoning to
reasonably support that the allegedly inherent characteristic necessarily
flows form the teachings of the prior art.’ Ex parte Levy, 17 USPQ2d 1461,
1464 (Bd. Pat. App. & Inter. 1990).” Id. at 6—7.
Discussion
The Examiner showed that the same starting material (the
tetraammonium salt) described in the Specification as being used to produce
the triazine trimer of Formula II”, as recited in claim 16, was also used in the
process of JP ’670. Final Act. 5. The Examiner also established that the
processes of JP ’670 and claim 16 produce the same final product of
Formula (III). Id. Appellants do not dispute these facts.
Where, as here, the claimed and prior art products are
identical or substantially identical, or are produced by identical
or substantially identical processes, the PTO can require an
applicant to prove that the prior art products do not necessarily
or inherently possess the characteristics of his claimed product.
. . . Whether the rejection is based on “inherency” under 35
U.S.C. § 102, on “prima facie obviousness” under 35 U.S.C.
§ 103, jointly or alternatively, the burden of proof is the same,
and its fairness is evidenced by the PTO’s inability to
manufacture products or to obtain and compare prior art
products.
In re Best, 562 F.2d 1252 (C.C.P.A. 1977).
Based on the identity between the starting materials (the
tetraammonium salt), the products (Formula III of claim 16 and Formula (2)
of JP ’670), and the base (alkali) conditions, the Examiner has established an
adequate technical basis that the same intermediate triazine trimer would be
formed (Formula II” of claim 16), despite the failure of JP ’670 to expressly
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Appeal 2017-003647
Application 14/329,356
show it. Appellants ignore these admitted facts when making the contention
that the Examiner lacked “basis or technical reason” to draw such
conclusion.
Appellants attempt to distinguish the claimed subject matter by
providing a Declaration by Dr. Osamu Mikuni in which he states that “the
pH value (9.5 to 11.5) of the presently claimed invention” is different from
the pH value of JP ’670, which he calculated to be 11.6, 12.5, and 14 in
Examples 5, 7, and 8, respectively. Mikuni Decl. 2—3.
The Declaration is not persuasive.
First, Dr. Mikuni did not state that such difference in pH would
have resulted in the monomer forming rather than the trimer. Such a
statement was made in the Appeal Brief by the attorney. Br. 6. An
argument made by counsel in a brief does not substitute for evidence
lacking in the record. Estee Lauder, Inc. v. L ’Oreal, S.A., 129 F.3d
588, 595 (Fed. Cir. 1997). However, the only evidence provided to
support this argument is the alleged fact that JP ’670 did not show the
trimer. But this alleged insufficiency is made up for by the fact that
the starting materials, products, and alkali conditions are the same in
the reference and in the claimed process.
Secondly, Appellants did not address the broader disclosure in
JP ’670 in which alkali conditions are described generally (Br. 5,
citing || 20, 31—39 of JP ’670) and the reference’s disclosure is not
restricted to the specific conditions of its Examples 5, 7, and 8. That
is, while Example 5, 7, and 8 might have pH conditions that resulted
in the production of a monomer rather than a trimer, JP ’670’s
disclosure is not limited to these conditions. See JP ’670, || 32, 34.
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Appeal 2017-003647
Application 14/329,356
Third, Appellants have not established that a triazine trimer
would be not be produced by JP ’670. For example, JP ’670 discloses
that “alkali makes the reaction of 2-chloro-5-pyridyl methyl
hexamethylene tetra ammonium chloride and water promote, and,
moreover, improves the yield of N-methylidyne-2-chloro-5-
pyridinemethanamine.” JP ’670,34 (emphasis added). Thus, JP
’670 does not exclude that other compounds are produced in addition
to the Formula (1) compound.
In sum, Appellants have not provided sufficient evidence that a
trimer of claim 16 is not formed by the process of JP ’670.
Accordingly, we affirm the rejection of claim 16. Claims 17—31 were
not argued separately and thus fall with claim 16. 37 C.F.R.
41.37(c)(l)(iv).
2. REJECTION BASED ON JOMAA ALONE
The Examiner rejected claim 15 based on Jomaa alone. Claim 15 is a
compound claim. The compound is the Formula II” compound (triazine
trimer) shown and discussed above, where X represents a halogen or a
substituted or unsubstituted alkyl group. The compound of claim 16 (see
claim appendix of Appeal Brief; annotated herein) is reproduced below.
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Appeal 2017-003647
Application 14/329,356
J4, tiiazme
,1
substituted pyridine
The Examiner found that Jomaa describes a triazine trimer substituted
with pyridine as required by claim 15, but not substituted with a halogen or
unsubstituted or substituted alkyl (shown above as the —X position) as
recited in the claim. Ans. 6. The triazine trimer is disclosed by Jomaa as
used to make a final product with the pyridine ring. Id. (citing Jomaa at
Examplw 5 on page 12[). The Examiner found that Jomaa teaches making a
genus of final products having a formula that would include the halogen and
unsubstituted/substituted alkyls. Id. at 6—8. The Examiner found Jomaa
discloses a list of substituents, which includes the claimed halogen and
unsubstituted/substituted alkyls. The Examiner found that it would have
been obvious to one trained in the art “to make the genus of compound[s]
taught by Jomaa with various substituents on Ri such as halogen including
l,3,5-tris(3-pyridinylmethyl-l,3,5-triazine of example 5 with halogen
substituents and alkyl substituents in various positions] including the 5
position of the pyridine ring corresponding to [the] position of [the] instant
[i.e., claimed] X [substituent] and expect these compounds to have [the] use
taught in Jomaa.” Id. at 9.
Appellants contend that the Examiner erred and argue that Jomaa
teaches that the heterocyclic radical, one example of which is a pyridine, can
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Appeal 2017-003647
Application 14/329,356
be substituted or unsubstituted, but that Jomaa does not specifically recite
what substituents can be used. Br. 11. Appellants contend that halogen is
disclosed, but as a replacement for the heterocyclic radical, not as a
substituent on the heterocyclic radical. Id. Appellants contend that the
Examiner has not identified the motivation “to (i) select only the halogen or
the substituted or unsubstituted alkyl for the heterocyclic core, and (ii) that
these specific substituents should be at the 5 position on the ring.” Id. at 12.
Discussion
Appellants have persuasively demonstrated an error in the Examiner’s
determination that claim 15 would have been obvious based on the teachings
in Jomaa.
As argued by Appellants, the Examiner acknowledged that, while
Jomaa describes substituted heterocyclic rings (namely, the claimed pyridine
substituent on the triazine trimer), Jomaa “does not recite [the] choice of
specific substituents for the heterocyclic core.” Final Act. 16. To meet the
requirement of claim 15’s X substituents on the pyridine ring, the Examiner
cited Jomaa’s teaching of substituents on an acyl group on the ring — an acyl
contains a double-bonded oxygen and an alkyl group. Id. The Examiner
found, based on this disclosure of heterocyclic acyl groups, that halogen
would be “permitted” as a substituent for the pyrimidine ring. Id. at 17.
We agree with Appellants that the Examiner’s rationale is not
adequate for making the necessary substitution. The identified substituents,
namely, halogen and substituted or unsubstituted alkyl, are for acyl groups
(double-bonded oxygen and an alkyl group); the Examiner has not pointed to
an adequate reason to utilize the halogen or substituted or unsubstituted alkyl
on the pyridine ring other than it is a “permitted” choice. We agree it is
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Appeal 2017-003647
Application 14/329,356
permitted because there is no limitation on the substituent for a heterocyclic
ring, such as the pyridine ring. However, the fact that the claimed
substituents are one possible choice is not a reason to have picked these
groups from the many disclosed in Jomaa, particularly when they are
disclosed for an acyl group and not a pyridine ring as required by claim 15.
In addition to this, as argued by Appellants, the Examiner has not
given a reason to have substituted the pyridine ring on the 5’ position. There
are three possible carbon atoms in the pyridine ring to which a substituent
can be added; the Examiner did not provide a reason to have selected the 5’
position, and only the 5’ position, to place a halogen or substituted or
unsubstituted alkyl.
For the foregoing reasons, we reverse the rejection of claim 15 as
obvious in view of Jomaa.
3. REJECTION BASED ON JOMAA AND TAKANO
The Examiner rejected claims 16—31 as obvious based on
Jomaa, Takano, and First Symposium. Final Act. 9.
Appellants described the processes disclosed in each of Jomaa
and Takano. The diagrams provided by Appellants summarizing the
prior art processes are based on the disclosures in these publications,
but the diagrams do not appear in the references. However, the
Examiner did not dispute Appellants’ depiction of the processes, and
we find them to be consistent with the evidence in each of the
publications.
Appellants, on page 8 of the Brief, state that Jomaa describes
the following process:
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Appeal 2017-003647
Application 14/329,356
| Pege 2, ime 18, to page 2,
flip® 4; page 4, lines 28-4#;
lEss^pie 5
| compounds of |l| or (SI):
rC
I
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o
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H** P,x
As R<
R~ m
{ Exampio S:
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/=\
0
Vh
o
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//
N*osi
A ,,'V-,«.»»' (■MMiwW'y ,< \ A
k Si H
{ * * CH„
R3 * OH
Rs * OH
vsww>.sw
14
Appeal 2017-003647
Application 14/329,356
Appellants, on page 9 of the Brief, state that Takano describes
the following process:
\ Takano fWQ 2005/1237041j
I Pa§e tine 12 to page 4. line 7
jf *
R1 - H, habgen
R;i - halogen
<%
ft
ft
f
S'^N
W
M
< _ /
V
twdnely^?
SipJCOtiS
{2}
\ /n---J
"\m H,C
Difference between Jomaa and Takano and claim 16
Jomaa describes a triazine trimer containing a pyridine as in
claim 16. However, Jomaa differs from the claimed process in (1)
reacting the triazine trimer under basic conditions (not acid conditions
as required by claim 16); and (2) producing a different product.
Takano describes reacting a triazine trimer with acid as in claim
16, but it is substituted with a thiazole not a pyridine as claimed.
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Appeal 2017-003647
Application 14/329,356
Discussion
The Examiner found that it would have been obvious to have arrived
at the claimed process of claim 16 by replacing the thiazole in Takano’s
trimer with the pyridine in Jomaa’s trimer because “a thiazole group is an
isostere for pyridine group and this is well known in the art,” as evidenced
by First Symposium and the Oxford English Dictionary. Ans. 12—13. The
Oxford English Dictionary teaches “Thiazole and pyridine are another pair
of isoteres said to resemble one another closely in properties.” Id. at 13.
Appellants contend that the Examiner did not establish that the
proposed substitution would result in a molecule with same biological
activity and thus would have had no reason to modify the process in Takano.
Br. 9. Appellants further contend that the Examiner did not provide
motivation to have made the structural change to Takano to have arrived at
the claimed process. Id.
We agree with the Appellants that the Examiner erred in determining
that claim 16 is obvious in view of Jomaa and Takoma. The Examiner did
not adequately establish the equivalence of thiazole and pyridine. First
Symposium discloses:
The isoteric compound formed may have either the same activity as the
original, or more usually it may have an antagonistic effect. In either
case, it is proof that isoteric replacement gives compounds acting by
the same mechanism, that they are truly bio-isoteric.First Symposium,
p. 2.
Assuming that this statement refers to the replacement of a thiazole
with a pyridine, First Symposium would teach that, with an isoteric
replacement, the compound doesn’t necessarily have “same” activity, but it
“more usually” has “antagonistic” activity, namely it does not act as a
16
Appeal 2017-003647
Application 14/329,356
stimulant, but rather antagonizes or turns off activity. The Examiner did not
explain why one of ordinary skill in the art would have wanted to make an
antagonist. Because “more usually” an antagonist is formed, we agree with
Appellants that the Examiner did not establish that the proposed substitution
of Takano with a pyridine would have been reasonably expected to result in
a molecule with the same biological activity.
We also agree with Appellants that the Examiner did not provide
adequate reason to make the substitution of a pyridine ring for a thiazole
ring. Jomaa has little pertinence to Takano because Jomaa does not perform
acid hydrolysis and does not produce the same product. The Examiner did
not explain why one of ordinary skill in the art would have looked to an
entirely different reaction with a different product as reason to modify
Takano’s process.
For the foregoing reasons, we reverse the rejection of claim 16, and
dependent claims 17—31, as obvious in view of Jomaa.
4. REJECTION BASED ON JOMAA, TAKANO, JP ’670
Because this rejection of claims 16—31 is based on JP ’670, we
affirm it for the same reasons set forth above regarding the affirmance
of the rejection of claims 16—31 over JP ’670.
SUMMARY
The rejection of claims 16—31 as obvious in view of JP ’670 is
affirmed.
The rejection of claim 15 as obvious in view of Jomaa is
reversed.
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Application 14/329,356
The rejection of claims 16—31 as obvious in view of Jomaa,
Takoma, and First Symposium is reversed.
The rejection of claims 16—31 as obvious in view of Jomaa,
Takano, JP ’670, First Symposium, and Kaku is affirmed.
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)(l)(iv).
AFFIRMED-IN-PART
18