Ex parte Hemprecht

Board of Patent Appeals and Interferences

Sep 14, 2000

08102752 (B.P.A.I. Sep. 14, 2000)

1
Paper No. 20
The opinion in support of the decision being entered today was
not written for publication and is not binding precedent of
the Board.
UNITED STATES PATENT AND TRADEMARK OFFICE
_______________
BEFORE THE BOARD OF PATENT APPEALS
AND INTERFERENCES
_______________
Ex parte GERHARD HEMPRECHT
______________
Appeal No. 1997-2195
Application 08/102,752
_______________
ON BRIEF
_______________
Before KIMLIN, PAK, and OWENS, Administrative Patent Judges.
OWENS, Administrative Patent Judge.
DECISION ON APPEAL
This is an appeal from the examiner’s final rejection of
claims 2-7 and refusal to allow claim 1 as amended after final
rejection. These are all of the claims remaining in the
application.
THE INVENTION
Appellant claims substituted 2-amino(fluoroalkoxy)-
pyrimidines having a recited formula, and a process for making
Appeal No. 1997-2195
Application 08/102,752
Citations herein to this reference are to the English1
translation thereof which is of record.
2
them. Appellant states that these pyrimidines are especially
useful as intermediates for making crop protection agents.
Claims 1 and 2 are illustrative and are appended to this
decision.
THE REFERENCES
Meyer et al. (Meyer) 4,518,776 May 21,
1985
Lachhein 4,831,138 May 16,
1989
Hamprecht (Hamprecht ‘927) 5,011,927 Apr. 30,
1991
(filed Dec. 18,
1989)
Hamprecht (Hamprecht ‘332) 5,283,332 Feb. 1,
1994
Lachhein et al. (Lachhein) 279,366 Aug. 24,1
1988
(European patent publication)
THE REJECTIONS
Claims 2-5 stand rejected under the judicially created
doctrine of obviousness-type double patenting over claims 2-5
of each of Hamprecht ‘143 and Hamprecht ‘332. Claims stand
Appeal No. 1997-2195
Application 08/102,752
A rejection of claim 1 under 35 U.S.C. § 102(b) over2
Lachhein is withdrawn in the answer (page 2).
3
rejected under 35 U.S.C. § 103 as follows: claim 1 over Lachhein;
claims 1, 6 and 7 over Hamprecht ‘927 in view of Lachhein;
claims
1, 6 and 7 over Meyer; and claims 2-5 over Hamprecht ‘927.2
OPINION
Appellant does not challenge the obviousness-type double
patenting rejections (brief, page 5). We therefore summarily
affirm these rejections.
As for the rejections under 35 U.S.C. § 103, we have
carefully considered all of the arguments advanced by appellant
and the examiner and agree with appellant that these rejections
are not well founded. Accordingly, we reverse the rejections
under 35 U.S.C. § 103.
Rejection of claim 1 over Lacchein
Lacchein discloses pyrimidines which are useful as
intermediates in the production of sulfonylureas which have a
herbicidal effect (page 3). The pyrimidines have hydrogen at the
Appeal No. 1997-2195
Application 08/102,752
4
5-position, can have an amino group at the 2-position, and a halo
(C -C )alkoxy group at the 4- and 6-positions (page 2). In a1 4
table of substituents of pyrimidines which Lacchein states can be
produced, the substituent at the 4- and 6-positions is
trifluoromethoxy (pages 9-10).
The examiner argues that it would have been obvious to one
of ordinary skill in the art to select from Lacchein’s generic
disclosure of halo(C -C )alkoxy substituents at the 4- and 1 4
6-positions, appellant’s chlorodifluoromethoxy substituent at the
4-position and trifluoromethoxy substituent at the 6-position
(answer, page 3).
Appellant argues, in reliance upon a declaration by
Hamprecht (filed December 12, 1991 in Application No. 07/663,975,
Paper No. 9), that producing appellant’s pyrimidines by the
method in U.S. 4,831,138 to Lacchein (col. 1, lines 52-58), which
is the method disclosed in the Lacchein reference relied upon by
the examiner (page 3), requires trifluoromethanol as a reagent
(declaration, pages 5-6). Hamprecht argues, in reliance upon
published technical articles, that because trifluoromethanol is
Appeal No. 1997-2195
Application 08/102,752
Appellant prepares his pyrimidines by a method which3
does not use trifluoromethanol (specification, page 6, lines
10-14).
5
extremely unstable, it could not have been used to make
appellant’s pyrimidines. 3
The examiner argues that the Hamprecht declaration is not
persuasive because Lachhein’s halo(C -C )alkoxy group encompasses1 4
appellant’s chlorodifluoromethoxy group (answer, page 7). The
examiner, however, does not address Hamprecht’s reasoning as to
why appellant’s trifluoromethoxy substituent could not be formed
using Lacchein’s method.
Because Hamprecht presents supported technical reasoning as
to why appellant’s pyrimidines could not have been made by one of
ordinary skill in the art from Lacchein’s disclosure, and the
examiner has presented no evidence or technical reasoning to the
contrary, we conclude that the examiner has not carried the
burden of establishing a prima facie case of obviousness of
appellant’s claimed invention over Lacchein.
Rejection of claims 1, 6 and 7 over
Hamprecht ‘927 in view of Lacchein
Appeal No. 1997-2195
Application 08/102,752
6
Hamprecht ‘927 discloses pyrimidines which are useful as
intermediates for crop protecting agents (col. 6, lines 65-68).
These pyrimidines differ from those of appellant in that at the
6-position, the Hamprecht ‘927 pyrimidines have an -OR group,2
where R is alkyl, alkenyl, alkynyl, cycloalkyl, phenyl or benzyl2
(col. 1, lines 5-21), rather than having appellant’s
trifluoromethoxy group.
The examiner argues that it would have been obvious to one
of ordinary skill in the art to substitute a trifluoromethoxy
group for the methoxy group in Hamprecht’s example 1 because
Lacchein (table, page 10) teaches the equivalence of methoxy and
trifluoromethoxy substituents in a pyrimidine in an analogous art
(answer, page 4). The examiner, however, does not explain how
one of ordinary skill in the art would have formed the
trifluoromethoxy substituent. As discussed above, the Hamprecht
declaration indicates that one of ordinary skill in the art could
not have formed such a substituent using Lacchein’s method, and
the examiner has presented no evidence or technical reasoning to
the contrary. Accordingly, we conclude that the examiner has not
established a prima facie case of obviousness of appellant’s
Appeal No. 1997-2195
Application 08/102,752
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claimed invention over the combined teachings of Hamprecht ‘927
and Lacchein.
Rejection of claims 1, 6 and 7 over Meyer
Meyer discloses pyrimidines which are useful as
intermediates for making sulfonylureas having a herbicidal action
(col. 1, lines 4-7; col. 2, lines 36-47). Meyer’s pyrimidines
can have a halo(C -C )alkoxy substituent at the 6-position1 4
(col. 1, lines 49-52; col. 2, lines 36-47). One of the preferred
substituents at the 6-position is difluoromethoxy (col. 3,
lines 1-6). The only disclosure by Meyer regarding how to make
the pyrimidines is that they can be made by known methods
(col. 4, lines 1-3).
The examiner argues that it would have been obvious to one
of ordinary skill in the art to select trifluoromethoxy as
Meyer’s halo(C -C )alkoxy substituent (answer, page 6). The1 4
examiner does not explain, however, in response to the Hamprecht
declaration, how one of ordinary skill in the art would have
formed the trifluoromethoxy substituent. Consequently, we
conclude that the examiner has not established a prima facie case
Appeal No. 1997-2195
Application 08/102,752
8
of obviousness of appellant’s claimed invention over Meyer.
Rejection of claims 2-5 over Hamprecht ‘927
Hamprecht ‘927 discloses reacting a pyrimidine having
fluorine at the 2-position with an amine to substitute an amino
group for the fluoro substituent (col. 4, lines 20-53). At the
6-position, the Hamprecht ‘927 pyrimidine has an -OR group,2
where R is alkyl, alkenyl, alkynyl, cycloalkyl, phenyl or benzyl2
(col. 1, lines 5-21).
The examiner argues, in reliance upon a number of cases
including In re Durden, 763 F.2d 1406, 226 USPQ 359 (Fed. Cir.
1985), that “the mere use of different starting materials,
whether novel or known, in a conventional process to produce the
product one would expect therefrom does not render the process
unobvious” (answer, page 8).
The examiner reached his conclusion of obviousness of
appellant’s claimed invention based on a per se rule that use of
a new starting material in a prior art process would have been
obvious to one of ordinary skill in the art. As stated by the
Federal Circuit in In re Ochiai, 71 F.3d 1565, 1572, 37 USPQ2d
Appeal No. 1997-2195
Application 08/102,752
9
1127, 1133 (Fed. Cir. 1995), “reliance on per se rules of
obviousness is legally incorrect and must cease.” The court
further stated:
Mere citation of Durden, Albertson, or any other
case as a basis for rejecting process claims that
differ from the prior art by their use of
different starting materials is improper, as it
sidesteps the fact-intensive inquiry mandated by
section 103. In other words, there are not
“Durden obviousness rejections” or “Albertson
obviousness rejections,” but rather only section
103 obviousness rejections.
Ochiai, 71 F.3d at 1570, 37 USPQ2d at 1132.
When an examiner is determining whether a claim should be
rejected under 35 U.S.C. § 103, the claimed subject matter as a
whole must be considered. See Ochiai, 71 F.3d at 1569, 37 USPQ2d
at 1131. The subject matter as a whole of process claims
includes the starting materials and product made. When the
starting and/or product materials of the prior art differ from
those of the claimed invention, the examiner has the burden of
explaining why the prior art would have motivated one of ordinary
skill in the art to modify the materials of the prior art process
so as to arrive at the claimed invention. See Ochiai, 71 F.3d
at 1570, 37 USPQ2d at 1131. The examiner has not provided such
Appeal No. 1997-2195
Application 08/102,752
10
an explanation or explained why, even if one of ordinary skill in
the art had been motivated by Hamprecht ‘927 to form a
trifluoromethoxy substituent, the reference would have enabled
such a person to do so. The examiner, therefore, has not carried
the burden of establishing a prima facie case of obviousness of
appellant’s claimed process over Hamprecht ‘927.
DECISION
The rejections of claims 2-5 under the judicially created
doctrine of obviousness-type double patenting over claims 2-5 of
each of Hamprecht ‘143 and Hamprecht ‘332 are affirmed. The
rejections under 35 U.S.C. § 103 of claim 1 over Lachhein,
claims 1, 6 and 7 over Hamprecht ‘927 in view of Lacchein,
claims 1, 6 and 7 over Meyer, and claims 2-5 over Hamprecht ‘927,
are reversed.
Appeal No. 1997-2195
Application 08/102,752
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No time period for taking any subsequent action in
connection with this appeal may be extended under 37 CFR
§ 1.136(a).
AFFIRMED-IN-PART
Edward C. Kimlin )
Administrative Patent Judge )
)
)
)
Chung K. Pak ) BOARD OF PATENT
Administrative Patent Judge ) APPEALS AND
) INTERFERENCES
)
)
Terry J. Owens )
Administrative Patent Judge )

TJO/cam
Appeal No. 1997-2195
Application 08/102,752
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Keil & Weinkauf
1101 Connecticut Avenue, N.W.
Suite 620
Washington, DC 20036
Appeal No. 1997-2195
Application 08/102,752
13
APPENDIX
1. A substituted 2-amino(fluoroalkoxy)pyrimidine of the
formula I
I
where
R is hydrogen, C -C -alkyl, C -C -alkenyl or C -C -alkynyl,1 1 4 3 4 3 4
R is hydrogen, halogen, C -C -haloalkyl, chlorodifluoromethoxy,2 1 4
R is hydrogen, halogen or C -C -haloalkyl and3 1 4
n is 0.
2. A process for preparing a 2-
amino(fluoroalkoxy)pyrimidine of formula I
I
where
R is hydrogen, C -C -alkyl, C -C -alkenyl or C -C -alkynyl, 1 1 4 3 4 3 4
R is hydrogen, halogen, C -C -haloalkyl, trifluoromethoxy or2 1 4
chlorodifluoromethoxy,
Appeal No. 1997-2195
Application 08/102,752
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R is hydrogen, halogen or C -C -haloalkyl and 3 1 4
n is 0,
which comprises reacting a 2-halopyrimidine of
the formula II
II
where Hal is fluorine, chlorine, bromine or iodine, and R , R and2 3
n have the abovementioned meanings, with an amine of the formula
III
H-NH-R III1
where R has the abovementioned meaning, in the presence or1
absence of an organic base.