SYMRISE AG

Patent Trials and Appeals Board

Jul 6, 2020

2019006457 (P.T.A.B. Jul. 6, 2020)

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.
13/645,871 10/05/2012 Emilie Singer 1507-62 4409
28249 7590 07/06/2020
DILWORTH & BARRESE, LLP
Dilworth & Barrese, LLP
1000 WOODBURY ROAD
SUITE 405
WOODBURY, NY 11797
EXAMINER
RODRIGUEZ, RAYNA B
ART UNIT PAPER NUMBER
1628
NOTIFICATION DATE DELIVERY MODE
07/06/2020 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):
usptomail@dilworthbarrese.com
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
__________

BEFORE THE PATENT TRIAL AND APPEAL BOARD
__________

Ex parte EMILIE SINGER and BERND HÖLSCHER
__________

Appeal 2019-006457
Application 13/645,871
Technology Center 1600
__________

Before FRANCISCO C. PRATS, ULRIKE W. JENKS, and
RACHEL H. TOWNSEND, Administrative Patent Judges.

PRATS, Administrative Patent Judge.

DECISION ON APPEAL

Pursuant to 35 U.S.C. § 134(a), Appellant1 appeals from the
Examiner’s decision to reject claims 7–9. We have jurisdiction under
35 U.S.C. § 6(b).
We AFFIRM.

1 We use the word “Appellant” to refer to “applicant” as defined in 37
C.F.R. § 1.42. Appellant identifies SYMRISE AG as the real party in
interest. Appeal Br. 1.
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STATEMENT OF THE CASE
The following rejections are before us for review:
(1) Claims 7 and 9, under 35 U.S.C. § 103(a) as being unpatentable
over Winter2 and Skouroumounis3 (Ans. 3–10); and
(2) Claim 8, under 35 U.S.C. § 103(a) as being unpatentable over
Winter, Skouroumounis, and Krause4 (Ans. 8–14).
Appellant’s claim 7, the sole independent claim on appeal, is
representative and reads as follows:
7. A fragrance preparation comprising a compound of
formula (Ia)

and a compound of formula (Ib)

wherein the amount of the compounds of formula (Ia) and (Ib)
is in the range from 0.0001 to 40 wt.% relative to the total
weight of the fragrance preparation.

2 US 6,376,458 B1 (issued Apr. 23, 2002).
3 G. Skouroumounis et al., Synthesis of 1,3,4,5-Tetrahydro-2-benzoxepin
Derivatives as Conformationally Restricted Analogues of
Cyclamenaldehyde-Type Compounds and as Intermediates for Highly
Odour-Active Homologues, 79 HELVETICA CHIMICA ACTA 1095–1109
(1996).
4 WO 2011/029743 A1 (published Mar. 17, 2011).
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Appeal Br. 25.
DISCUSSION
The Examiner’s Prima Facie Case
In rejecting Appellant’s representative claim 7, the Examiner cited
Winter as describing a synthetic fragrance/perfuming compound,
“Compound B,” that differs from the compounds recited in claim 7 only in
that, in Compound B, “the cyclohexene ring is substituted with a tert-butyl
moiety instead of an isopropyl moiety.” Ans. 6.
The Examiner cited Skouroumounis as evidence that, in synthetic
fragrance compounds having structures and odors similar to Compound B of
Winter, “an isopropyl and tert-butyl are interchangeable at the para position
on the ring to produce compounds with lily of the valley characteristics.”
Ans. 6.
Based on the references’ combined teachings, the Examiner reasoned
that a skilled artisan would have considered it obvious to
1) select compound B as a lead compound, motivated by
the fact that this compound is exemplified [by Winter] as a
preferred compound for use as a perfuming ingredient for the
preparation of perfuming compositions, to which it imparts
odor notes of the lily of the valley type and . . .
2[]) substitute the tert-butyl substituent for an isopropyl
substituent and to utilize the modified compound in a fragrance
preparation. The motivation to substitute the tert-butyl
substituent would have been the establishment by
Skouroumounis that either an isopropyl or tert-butyl moiety is
suitable in producing compounds that impart an odor note of
lily of the valley. The motivation to make the instantly claimed
compounds derives from the expectation that structurally
similar compounds would possess similar activity (i.e. they
would impart an odor note of lily of the valley).
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Ans. 6–7 (paragraphing added); see also id. at 8 (“In this case, it is expected
that compounds differing only by one methyl group, would have similar
chemical, physical and biochemical properties.”).
The Examiner reasoned further that a skilled artisan would have
considered the amounts of compounds (Ia) and (Ib) in the composition of
Appellant’s claim 7 obvious in view of the amounts of fragrance compounds
disclosed in Winter for its compositions. Ans. 8.
Analysis
As stated in In re Oetiker, 977 F.2d 1443, 1445 (Fed. Cir. 1992):
[T]he examiner bears the initial burden . . . of presenting a
prima facie case of unpatentability. . . .
After evidence or argument is submitted by the applicant in
response, patentability is determined on the totality of the
record, by a preponderance of evidence with due consideration
to persuasiveness of argument.
Having carefully considered all of the arguments and evidence
advanced by Appellant and the Examiner, Appellant does not persuade us
that a preponderance of the evidence fails to support the Examiner’s
conclusion of obviousness as to Appellant’s representative claim 7.
In particular, Appellant does not persuade us that the Examiner erred
in determining that a skilled artisan would have considered it obvious to
select the compound in Winter, designated by the Examiner as Compound B,
as a lead compound for further modification. As the Examiner found,
Winter describes Compound B as the preferred compound of its invention,
for a number of reasons:
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3-(4-Tert-butyl-1-cyclohexen-1-yl)propanal[5] is a
preferred compound according to the invention. The latter
presents an odor of the aldehydic, flowery-lily of the valley,
fatty type with a Lilial®/Bourgeonal® connotation, but its odor
is definitely more floral, more white flower than that of Lilial
®. It is also more powerful than the latter, more substantive on
the linen, which property presents a distinct advantage for the
perfuming of products such as detergents and fabric softeners.
Moreover, the odor of this preferred compound of the invention
has a surprising slight anisic tone, providing thus a novel odor
nuance to the perfumer’s palette.
Winter 2:37–47.
Given the desirable properties of Compound B disclosed in Winter,
we are not persuaded that the Examiner erred in determining that a skilled
artisan would have considered Compound B a useful lead compound,
suitable for further efforts in developing additional fragrance compounds.
See Eisai Co. Ltd. v. Dr. Reddy’s Labs., Ltd., 533 F.3d 1353, 1359 (Fed. Cir.
2008) (“A lead compound is a compound in the prior art that would be ‘a
natural choice for further development efforts.’”) (quoting Altana Pharma
AG v. Teva Pharms. USA, Inc., 566 F.3d 999, 1008 (Fed. Cir. 2009).
Moreover, the fact that other useful lead compounds for developing
lily of the valley fragrance substances might have been known in the art (see
Appeal Br. 9–10) does not persuade us that the Examiner erred in finding
that Compound B would have been a suitable lead compound, given
Winter’s teachings noted above. See Daiichi Sankyo Co. v. Matrix Labs.,
Ltd., 619 F.3d 1346, 1354 (Fed. Cir. 2010) (“The lead compound analysis

5 Appellant does not dispute that the compound designated by the Examiner
as Compound B (see Ans. 5) is 3-(4-Tert-butyl-1-cyclohexen-1-yl)propanal,
which Winter describes as its preferred compound. See Winter 2:37–47.
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must, in keeping with KSR[ Int'l v. Teleflex Inc., 550 U.S. 398 (2007)], not
rigidly focus on the selection of a single, best lead compound . . . .”).
Appellant also does not persuade us that the Examiner erred in
determining that a skilled artisan had sufficient motivation for modifying
Compound B of Winter to arrive at the compounds recited in Appellant’s
representative claim 7. Specifically, it is undisputed that the two compounds
recited in representative claim 7, which are isomers of each other, differ
from Winter’s Compound B only in that, instead of the tert-butyl moiety on
the cyclohexene ring of Compound B, the cyclohexene ring in Appellant’s
claim 7 is substituted with an isopropyl moiety.
As the Examiner found, however, Skouroumounis discloses that
compounds having lily of the valley fragrance, and structures similar to
those of Winter’s Compound B, have both tert-butyl and isopropyl moieties
at the para position of the six-membered ring. See Skouroumounis 1095
(compounds 1–4).
Indeed, we note that, in experimenting with similar molecules to
uncover relationships between structure and fragrances of the lily of the
valley type, Skouroumounis describes testing both tert-butyl and isopropyl
moieties at that position. See Skouroumounis 1097 (“We next decided to
reduce the bulkiness of the alkyl group on the aromatic ring, thereby also
diminishing the molecular weight and enhancing the volatility, and thus
prepared the analogues 10b–d by using the same methodology as employed
for 10a (see Scheme 1); id. at 1098–1099 (Schemes 1–4 showing tert-butyl
and isopropyl as alternative substituents in a number of synthesized
compounds).
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Thus, based on the teachings Skouroumounis, it was known in the art
that compounds having lily of the valley fragrance, and structures similar to
those of Winter’s Compound B, have both tert-butyl and isopropyl moieties
at the para position of the compounds’ six-membered ring. And, based on
the teachings in Skouroumounis, it was known in the art to interchangeably
employ tert-butyl and isopropropyl moieties at the para position of those
compounds’ six-membered rings, when investigating their fragrant
properties. Appellant does not persuade us, therefore, that a skilled artisan
lacked motivation, or an adequate methodology, for substituting an isopropyl
moiety, as recited in Appellant’s representative claim 7, for the tert-butyl
moiety at the para position of the cyclohexenyl ring of Winter’s Compound
B. See Appeal Br. 12–13. As explained by our reviewing court:
The “reason or motivation” need not be an explicit teaching that
the claimed compound will have a particular utility; it is
sufficient to show that the claimed and prior art compounds
possess a “sufficiently close relationship . . . to create an
expectation,” in light of the totality of the prior art, that the new
compound will have “similar properties” to the old.
Aventis Pharma Deutschland GmbH v. Lupin, Ltd., 499 F.3d 1293, 1301
(Fed. Cir. 2007) (quoting In re Dillon, 919 F.2d 688, 692 (Fed. Cir. 1990)).
Appellant also does not persuade us that a skilled artisan lacked a
reasonable expectation of success in substituting an isopropyl moiety for the
tert-butyl moiety of Winter’s Compound B, to arrive at the compounds of
Appellant’s representative claim 7. See Appeal Br. 14–22; see also First
Hölscher Declaration6 ¶¶ 7–27 (citing Sell7).

6 Declaration of Bernd Hölscher, signed September 7, 2017. Mr. Hölscher is
one of the inventors of the application on Appeal, and is employed by the
real party in interest. First Hölscher Declaration ¶ 1.
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It is well settled that “[o]bviousness does not require absolute
predictability of success. . . . For obviousness under § 103, all that is
required is a reasonable expectation of success.” In re Kubin, 561 F.3d
1351, 1360 (Fed. Cir. 2009) (quoting In re O’Farrell, 853 F.2d 894, 903–04
(Fed. Cir. 1988) (emphasis removed).
We acknowledge that performing an isopropyl for tert-butyl
substitution, or similar modification, on fragrance compounds having
structures similar to Winter’s Compound B has been shown to change the
character of the compounds’ odor. See Sell 6256 (disclosing that a tert-butyl
for isopropyl substitution “has a major effect on the odor [of compound 23],
taking it from muguet[8]to sandalwood [in compound 24]” and that
“[s]imilarly, substitution of the tert-butyl group of [compound] 22 by an
isobutyl group to give 25 changes the odor from sweet and woody to a harsh
raspberry character”).
However, performing an equivalent or similar substitution on
fragrance compounds having structures similar to Winter’s Compound B can
also result in little or no change to the compounds’ odor, independent of
whether the six membered ring is aromatic or cyclohexyl. See Sell 6256
(disclosing that in its compounds 21 and 22 “there is little effect on the odor
upon changing an isopropyl group for a tert-butyl substituent” and that a
tert-butyl for isobutyl substitution “has little effect on the muguet character

7 C.S. Sell, On the Unpredictability of Odor, 45 ANGEW. CHEM. INT. ED.
6254–6261 (2006).
8 “Muguet” odor tonality is described in Skouroumounis as being lily of the
valley odor tonality. See Skouroumonis 1095 (describing its compounds 1–
3 as “widely used synthetic odorants of the floral class, having the
appreciated lily-of-the-valley (‘muguet’) tonality”).
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of Lilial (13), whose isobutyl analogue Silvial (26) has a similar muguet
odor”).
And, as discussed above, Skouroumonis discloses that lily of the
valley fragrance compounds with structures closely similar to Winter’s
Compound B can have either an isopropyl or ter-butyl moiety at the para
position of the six-membered ring. See Skouroumounis 1095 (compounds
1–4).
While Sell thus provides evidence that a skilled artisan could not
predict with absolute certainty whether the isopropyl for tert-butyl
substitution of Winter’s Compound B posited by the Examiner would result
in a useful fragrance compound, absolute predictability is not the standard
for showing obviousness. See Kubin, 561 F.3d at 1360. To the contrary, as
seen above, both Skouroumonis and Sell teach that making the substitution
posited by the Examiner in compounds similar to Winter’s Compound B
results in useful fragrances. We therefore agree with the Examiner that,
although the result was not absolutely predictable, a skilled artisan had a
reasonable expectation of success in making the posited isopropyl for tert-
butyl substitution of Winter’s Compound B, which is all that is required to
show obviousness. See id. For similar reasons, based on the totality of the
teachings in Skouroumonis and Sell, Appellant does not persuade us that
Skouroumonis teaches away from the substitution posited by the Examiner.
See Appeal Br. 20–21.
To summarize, Appellant does not persuade us that the Examiner
erred in determining that Winter and Skouroumounis would have provided a
skilled artisan with a good reason for, and a reasonable expectation of
success in, preparing a fragrance composition having the compounds recited
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in Appellant’s representative claim 7. Appellant does not persuade us,
moreover, that it has advanced objective evidence of nonobviousness
sufficient to outweigh the evidence of prima facie obviousness presented by
the Examiner.
In particular, we do not find Appellant’s contentions regarding long
felt need persuasive. See Appeal Br. 8–9.
Establishing long-felt need “requires objective evidence that an art-
recognized problem existed in the art for a long period of time without
solution.” Ex Parte Jellá, 90 USPQ2d 1009, 1019 (BPAI 2008)
(precedential; emphasis added); see also Graham v. John Deere Co., 383
U.S. 1, 17–18 (1966) (secondary considerations include “long felt but
unsolved needs”) (emphasis added). In the present case, given the presence
in the prior art of useful lily of the valley fragrance compounds disclosed by
both Skouroumounis and Winter, Appellant does not persuade us that the
need for such compounds was unsolved.
Appellant also does not persuade us that it has advanced evidence of
unexpected results sufficient to outweigh the prior art evidence of prima
facie obviousness presented by the Examiner. See Appeal Br. 22–28; see
also Second Hölscher Declaration9 and Third Hölscher Declaration.10

9 Declaration of Bernd Hölscher, signed September 26, 2017.
10 Declaration of Bernd Hölscher, signed May 29, 2018.
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The Third Hölscher Declaration presents the results of a direct
comparison between the compounds of Appellant’s claim 7 and Winter’s
Compound B. Third Hölscher Declaration ¶¶ 5–7.11
This Declaration explains that fifteen scent experts evaluated the two
compounds as to five scent notes: (i) sweet, (ii) floral, (iii) aldehyde, (iv)
initial intensity and (v) substantivity (intensity 10 minutes after rubbing an
impregnated cotton ball over the inside of the wrist). Third Hölscher
Declaration ¶ 5. The Declaration explains, and it is undisputed, that “[u]sing
scent experts to score different scents is an accepted methodology in the
field.” Id. ¶ 6.
The Third Hölscher Declaration presents the results of the experiment
in the following spider graph and table:

11 The Third Hölscher Declaration presents the results of the same
experiments described in the Second Hölscher Declaration, but provides
additional explanation. See Third Hölscher Declaration ¶¶ 4–6.
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Third Hölscher Declaration ¶ 7.
The Declaration states that “[t]he results clearly demonstrate
superiority of the claimed compounds.” Third Hölscher Declaration ¶ 6; see
also id. ¶ 9 (“The results clearly demonstrate that the compounds according
to the present invention provide superior performance and exhibit
unpredictable better results when compared to the prior art.”).
It is well settled that, to be persuasive of nonobviousness, an expert’s
opinion must be supported by objective evidence. See Ashland Oil, Inc. v.
Delta Resins & Refractories, Inc., 776 F.2d 281, 294 (Fed. Cir. 1985) (“Lack
of factual support for expert opinion going to factual determinations . . . may
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render the testimony of little probative value in a validity determination.”)
(citing In re Altenpohl, 500 F.2d 1151, 1158 (CCPA 1974)).
As to evaluating declarations of experts, MPEP § 716.01(c).III
provides as follows:
In assessing the probative value of an expert opinion, the
examiner must consider the nature of the matter sought to be
established, the strength of any opposing evidence, the interest
of the expert in the outcome of the case, and the presence or
absence of factual support for the expert’s opinion.” Ashland
Oil, Inc. v. Delta Resins & Refractories, Inc., 776 F.2d 281, 227
USPQ 657 (Fed. Cir. 1985), cert. denied, 475 U.S. 1017 (1986).
As to unexpected results, our reviewing court has explained that
“[m]ere improvement in properties does not always suffice to show
unexpected results. . . . [W]hen an applicant demonstrates substantially
improved results . . . and states that the results were unexpected, this should
suffice to establish unexpected results in the absence of evidence to the
contrary.” In re Soni, 54 F.3d 746, 751 (Fed. Cir. 1995).
In the present case, while the declarant (and co-inventor) Bernd
Hölscher qualifies as an expert with over 40 years of experience (see Third
Hölscher Declaration ¶ 2), we are not persuaded that the Second and Third
Hölscher Declarations provide sufficient objective evidence to support the
declarant’s opinion that the compounds of representative claim 7 show
substantially improved results as compared to Winter’s Compound B.
We acknowledge that the compounds of Appellant’s claim 7 show
higher numbers as to intensity, substantivity, and sweet notes, and a lower
number as to aldehyde notes, as compared to Winter’s Compound B, in the
spider graph and table reproduced above from the Third Hölscher
Declaration. However, neither the Second nor Third Hölscher Declaration
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explains anything specific about the scale employed in the analysis, or the
methodology used to arrive at the numbers shown in the graph and table.
For example, it is unclear whether the numbers shown are the sums of the all
of the scores provided by the testers, or an average of the scores provided by
the testers, and what the variation among the testers was.
As to the scale of the numbers, we note that the highest number shown
in the graph and table is 40, but it is unclear whether that number (or the
differences between the numbers shown) is objectively meaningful, given
that the declarations provide no indication of the overall scale employed in
the evaluation. Also as to scale, we note that Appellant’s Specification
evaluates intensity on a scale “from 1 = odorless to 9 = very strong” (Spec.
85), which contrasts with the highest number of 40 shown in the graph and
table in the Second and Third Hölscher Declarations.
Thus, given the absence of any specific explanation as to the meaning
of the numbers shown in the graph and table in the Second and Third
Hölscher Declarations, we are not persuaded that there is sufficient objective
evidence, on this record, to support the declarant’s opinion that the
compounds of representative claim 7 show substantially improved results as
compared to Winter’s Compound B. Appellant does not persuade us,
therefore, that the Examiner erred in finding that the evidence of unexpected
results was not sufficient to outweigh the evidence of prima facie
obviousness in the cited prior art.
In sum, for the reasons discussed, based on the totality of the record,
Appellant does not persuade that the preponderance of the evidence fails to
support the Examiner’s conclusion that the composition of Appellant’s
representative claim 7 would have been obvious. We therefore affirm the
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Examiner’s rejection of claim 7 for obviousness over Winter and
Skouroumounis. Claim 9 falls with claim 7. See 37 C.F.R. 41.37(c)(1)(iv).
In rejecting claim 8 over Winter, Skouroumounis, and Krause, the
Examiner cited Winter and Skouroumounis for the teachings discussed
above, and cited Krause as evidence that it would have been obvious to add
an additional lily of the valley fragrance compound to the composition
suggested by Winter and Skouroumounis. See Ans. 8–14. Because
Appellant does not specifically address the Examiner’s rationale for
combining Krause with Winter and Skouroumounis, nor does Appellant
assert specific error in the Examiner’s obviousness rationale as to claim 8,
we affirm the Examiner’s rejection of claim 8 as well.

CONCLUSION
In summary:
Claims
Rejected
35 U.S.C.
§
Reference(s)/Basis Affirmed Reversed
7, 9 103(a) Winter,
Skouroumounis
7, 9
8 103(a) Winter,
Skouroumounis,
Krause
8
Overall
Outcome
7–9

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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). See 37 C.F.R.
§ 1.136(a)(1)(iv).

AFFIRMED