Ex Parte Stangl et al

Patent Trial and Appeal Board

Oct 19, 2016

11991017 (P.T.A.B. Oct. 19, 2016)

UNITED STA TES p A TENT AND TRADEMARK OFFICE
APPLICATION NO. FILING DATE
111991,017 06/06/2008
23117 7590 10/21/2016
NIXON & V ANDERHYE, PC
901 NORTH GLEBE ROAD, 11 TH FLOOR
ARLINGTON, VA 22203
FIRST NAMED INVENTOR
Jochen Stangl
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
ATTORNEY DOCKET NO. CONFIRMATION NO.
ES-4662-742 3729
EXAMINER
0 DELL, DAVID K
ART UNIT PAPER NUMBER
1625
NOTIFICATION DATE DELIVERY MODE
10/21/2016 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):
PTOMAIL@nixonvan.com
pair_nixon@firsttofile.com
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte JOCHEN STANGL and CLAUDE STRITT 1
Appeal 2015-000141
Application 11/991,017
Technology Center 1600
Before ERIC B. GRIMES, JOHN E. SCHNEIDER, and
RY ANH. FLAX Administrative Patent Judges.
SCHNEIDER, Administrative Patent Judge.
DECISION ON APPEAL
This is an appeal under 35 U.S.C. § 134(a) involving claims to a
method for preparing an epoxy compound which have been rejected as
obvious. We have jurisdiction under 35 U.S.C. § 6(b).
We affirm.
STATEMENT OF THE CASE
The present invention is directed to "a process comprising a
condensation step wherein a starting aldehyde or ketone is made to react
with an ester of an a-haloacid to form an epoxy compound, in particular a
1 Appellants identify the Real Party in Interest as DSM IP Assets B.V. Br. 3.
Appeal2015-000141
Application 11/991,017
glycidic ester." Spec. 1. The process is used to form an intermediate in the
preparation of vitamin A. Id. The process is carried out using a dipolar
aprotic diluent selected from the group consisting of 1-methyl-2-pyrrolidone
(NMP), 1,3-dimethyltetrahydro-2(1H)-pyrimidinone (DMPU) and 1,1,3,3-
tetramethylurea (TMU). Spec. 6-7.
Claims 1--4, 6, and 9--13 are on appeal. Claim 1 is illustrative and
reads as follows:
1. A process comprising a condensation step wherein a starting
aldehyde or ketone is made to react with an ester of an a-
haloacid, which is selected from the group consisting of
methylchloroacetate, ethylchloroacetate, propylchloroacetate
and butylchloroacetate to form an epoxy compound, which is a
glycidic ester, whereby the reaction is carried out in the
presence of a dipolar aprotic compound selected from the group
consisting of 1-methyl-2-pyrrolidone (NMP), 1,3-
dimethyltetrahydro-2( 1 H)-pyrimidinone (D MPU) and 1, 1,3 ,3-
tetramethylurea (TMU);
\~1herein the starting ketone is B-ionone and \~1herein the
starting aldehyde is benzaldehyde and wherein the molar ratio
in the condensation step between the dipolar aprotic compound
and the starting aldehyde or ketone lies between 0.05 and 2.
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Appeal2015-000141
Application 11/991,017
The claims stand rejected as follows:
Claims 1--4, 6, and 9--13 stand rejected under 35 U.S.C. § 103(a) as
unpatentable over Isler2 and Lomjansky3 and Petrovic4 in view of
Reichardt. 5
DISCUSSION
Issue
In rejecting the pending claims as obvious, the Examiner finds that
Isler teaches a process for producing vitamin A that includes the Darzen
condensation of an a-haloketone with B-ionone to form an intermediate
epoxide, which is then converted to an aldehyde via saponification. Final
Act. 5. The Examiner goes on to find that both Lomjansky and Petrovic
teach the use of dipolar aprotic solvents for the condensation reaction
resulting in increased yields. Id. The Examiner also finds that Reichardt
discloses that important dipolar aprotic solvents include acetonitrile,
dimethylformamide, l-methylpyrrolidin-2-one, 1, 1,3,3-tetramethylurea, and
"tetrasubstituted cyclic ureas such as 3,4,5,6-tetrahydro-l ,3-dimethyl-
pyrimidin-2-(lH)-one (dimethyl propylene urea, DMPU)." Final Act. 7.
The Examiner concludes that:
2 Isler et al., Synthesis of Vitamin A, 30 Helvetica Chimica Acta 1911-1927
(1947) ("Isler"). Our citations are to the English translation of record.
3 Lomjansky et al., CS 167108 Bl, published Nov. 22, 1974 ("Lomjansky").
Our citations are to the English translation of record.
4 Petrovic et al., CS 262772 Bl, published June 15, 1989 ("Petrovic"). Our
citations are to the English translation of record.
5 Christian Reichardt, SOL VENTS AND SOL VENT EFFECTS IN ORGANIC
CHEMISTRY 82 (3rd ed. 2003) ("Reichardt").
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Appeal2015-000141
Application 11/991,017
[s]ince at least two of these known dipolar aprotic solvents had
been used, acetonitrile and dimethylformamide, by Lomjansky
et al. and Petrovic et al. to give improved yields, little more can
be expected from picking an alternative solvent (NMP 1-
methylpyrrolidin-2-one, ... , TMU 1,3,3-tetramethylurea or
DMPU dimethyl propylene urea) than the same or very similar
results .... This is a situation where there existed a finite
number of dipolar aprotic solvents available to use in the
reaction of the prior art, at least two of which had been used
before. It would have been prima facie obvious to one of
ordinary skill in the art at the time the invention was made to
use an alternative dipolar aprotic solvent.
Final Act. 7-8.
Appellants contend that the references do not teach or suggest
the use of the claimed solvents. Br. 11-12. Appellants argue that
Isler teaches the use of a solvent-free system. Br. 12. Appellants go
on to argue that Lomjansky does not teach the use of dipolar aprotic
solvent and that the yields in Lomjansky are lo\~1er than those
achieved by the present invention. Br. 12-13. With respect to
Petrovic, Appellants argue that while Petrovic discloses the use of
dipolar aprotic solvents, the process of Petrovic has the disadvantages
of "difficult accessibility, high cost and energetically demanding
regeneration of the used solvents." Br. 13. Appellants also argue that
the process of Petrovic produces lower yields than the present
invention. Br. 14.
With respect to claim 11, Appellants argue that the use of the
solvents recited in the claim results in yields unexpectedly higher that
that achieved by the prior art. Br. 18.
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Appeal2015-000141
Application 11/991,017
The issue with respect to this rejection is whether the Examiner has
established by a preponderance of the evidence that claims 1--4, 6, and 9--13
would have been obvious over Isler combined with Lomjansky, Petrovic,
and Reichardt under 35 U.S.C. § 103(a).
Findings of Fact
We adopt as our own the Examiner's findings and analysis. The
following findings are included for emphasis and reference convenience.
FF 1. Isler teaches a process for making vitamin A which includes
condensation of an ester of an a-haloacid (ClCH2COOC2Hs, or
ethylchloroacetate) with B-ionone (formula II) to form an intermediate
epoxide, which is a glycidic ester. Isler 8, see also id. at 20.
FF2. The epoxide in Isler is then saponified to form an aldehyde
(formula III). Id. at 8-9, see also id. at 20-21.
FF3. The reaction of ethylchloroacetate with B-ionone in Isler is
performed in the absence of a solvent. Id. at 8-9, 20-21.
FF4. Lomjansky discloses an improvement of the process of Isler
using an organic solvent for the condensation reaction. Lomjansky 3.
FF5. Lomjansky teaches that dimethyl formamide can be used as a
solvent in the process. Id.
FF6. Petrovic teaches that condensation ofbeta-ionone with a
monochloroacetic acid ester is carried out "most frequently in the presence
of an organic solvent such as dimethylformamide, pyridine, picoline."
Petrovic 2. Petrovic teaches carrying out the reaction in a solvent mixture of
acetonitrile with methanol, ethanol, or isobutanol. Id.
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Appeal2015-000141
Application 11/991,017
FF7. Petrovic achieved yields of 86% for acetonitrile alone and up to
91.1 % for acetonitrile mixed with alcohol. Petrovic 3--4 (example 1 ), 5
(example 5).
FF8. The Specification teaches that the claimed process produces
yields of from 84.4 % to 90.5%. Spec. 11-13.
FF9. Reichardt states that "the most important dipolar aprotic
solvents" include acetonitrile, N,N-dimethylformamide, 1-methylpyrrolidin-
2-one, 1, 1,3,3-tetramethylurea, and "tetrasubstituted cyclic ureas such as
3 ,4,5 ,6-tetrahydro-1,3-dimethyl-pyrimidin-2-(IH)-one (dimethyl propylene
urea, DMPU)." Reichardt 82.
Principles of Law
"[W]hen a patent claims a structure already known in the prior art that
is altered by the mere substitution of one element for another known in the
field, the combination must do more than yield a predictable result." KSR
Int'! Co. v. Teleflex Inc., 550 U.S. 398, 416 (2007)(citing United States v.
Adams, 383 U.S. 39, 50-51 (1966)).
"To be particularly probative, evidence of unexpected results must
establish that there is a difference between the results obtained and those of
the closest prior art, and that the difference would not have been expected by
one of ordinary skill in the art at the time of the invention." Bristol-Myers
Squibb Co. v. Teva Pharms. USA, Inc., 752 F.3d 967, 977 (Fed. Cir. 2014).
"[J]ust because better alternatives exist in the prior art does not mean
that an inferior combination is inapt for obviousness purposes." In re
Mouttet, 686 F.3d 1322, 1334 (Fed. Cir. 2012).
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Appeal2015-000141
Application 11/991,017
Analysis
Claim 1 is representative of the rejected claims and is directed to a
process comprising a condensation step used to make a precursor for vitamin
A wherein the condensation reaction is performed in the presence of one of
three specific dipolar aprotic solvents.
We agree with the Examiner's determination that the subject matter of
claim 1 would have been obvious to one skilled in the art. Isler teaches the
formation of an aldehyde by condensation of ethylchloroacetate with B-
ionone followed by saponification. FFl and 2. Lomjansky and Petrovic
teach the use of dimethylformamide or acetonitrile as a solvent in the
condensation step. FF5 and 6. Reichardt teaches that acetonitrile,
dimethylformamide, 1-methylpyrrolidin-2-one, DMPU, and 1, 1,3,3-
tetramethylurea are among "the most important dipolar aprotic solvents."
FFlO. We agree with the Examiner's determination that it would have been
obvious to one skilled in the art to substitute one dipolar aprotic solvent
(NMP, DMPU, or TMU) for another (acetonitrile or dimethylformamide).
Appellants argue that neither Isler nor Lomjansky teaches or suggests
the use of dipolar aprotic solvents. Br. 11-12. We are unpersuaded.
Although Lomjansky uses pyridine as a solvent in its examples, it
specifically teaches the use of dimethyl formamide as a solvent. FF5.
Next Appellants argue that Petrovic states that solvents such as
dimethyl formamide are difficult to access, high cost and energetically
demanding to regenerate. Br. 13. Again we are unpersuaded. The fact that
Petrovic presented its mixed solvent system as a better alternative to the
known use of dimethyl formamide as a solvent does not preclude a finding
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Appeal2015-000141
Application 11/991,017
of obviousness. In re Mouttet, 686 F .3d at 1334. Since use of a dipolar
aprotic solvent in the claimed process was known, it would have been
obvious to substitute another known dipolar aprotic solvent.
Appellants next argue that evidence of unexpected results overcomes
any possible prima facie case of obviousness. Br. 14. We agree with the
Examiner's determination that the results achieved by the present invention
are not persuasive. Petrovic discloses yields ranging from 86% for
acetonitrile alone and up to 91.1 % for acetonitrile mixed with alcohol. FF7.
The yields for the instant invention range from 84.4 % to 90.5%. FF8. The
results appear to be about the same, and Appellants have not provided
evidence to show that the Specification's results would be considered
unexpectedly superior by a skilled artisan.
With respect to claim 11, Appellants argue that the use of the specific
solvents recited in the claims yield unexpected results rendering the claim
nonobvious. Br. 15-18. For the reasons stated above, we find the evidence
of unexpected results to be unpersuasive.
Conclusion of Law
We conclude that the Examiner has established by a preponderance of
the evidence that claims 1 and 11 would have been obvious over Isler in
combination with Lomjansky, Petrovic, and Reichardt under 35 U.S.C.
§ 103(a).
Claims 2--4, 6, 9, 10, 12, and 13 have not been argued separately and
therefore fall with claim 1. 37 C.F.R. § 41.37(c)(l)(iv).
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Application 11/991,017
SUMMARY
We affirm the rejection based on 35 U.S.C. § 103(a).
TIME PERIOD FOR RESPONSE
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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