SYMRISE AG

Patent Trials and Appeals Board

Dec 7, 2021

2021001207 (P.T.A.B. Dec. 7, 2021)

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.
15/553,638 08/25/2017 Oskar KOCH 085158-577949 2491
30678 7590 12/07/2021
POLSINELLI PC
(DC OFFICE)
PO Box 140310
Kansas City, MO 64114-0310
EXAMINER
MURESAN, ANA Z
ART UNIT PAPER NUMBER
1622
NOTIFICATION DATE DELIVERY MODE
12/07/2021 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):
patentdocketing@polsinelli.com
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
__________

BEFORE THE PATENT TRIAL AND APPEAL BOARD
__________

Ex parte OSKAR KOCH and MARCUS RUDOLF GÖTZ
__________

Appeal 2021-001207
Application 15/553,638
Technology Center 1600
__________

Before DONALD E. ADAMS, JEFFREY N. FREDMAN, and
ULRIKE W. JENKS, Administrative Patent Judges.

FREDMAN, Administrative Patent Judge.

DECISION ON APPEAL
This is an appeal1 under 35 U.S.C. § 134 involving claims to a
crystalline cannabidivarin. The Examiner rejected the claims as anticipated
and as obvious. 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 the Real Party in Interest as SYMRISE
AG (see Appeal Br. 2). We have considered the Specification filed Aug. 25,
2017 (“Spec.”); Final Rejection of Sept. 3, 2019 (“Final Act.”); Appeal Brief
filed Apr. 28, 2020 (“Appeal Br.”); and Examiner’s Answer filed Sept. 11,
2020 (“Ans.”).
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Statement of the Case
Background
“Since the discovery of the endogenous cannabinoid system and its
functional relevance for regulating and modulating the immune as well as
nervous system, a constant need for natural and synthetic canabinoids exists
for its selective pharmaceutical control” (Spec. 3:10–12). “Known
compounds, that demonstrably show an affinity to the above-mentioned
receptors CB1 and CB2, are cannabidiol (CBD) originating inter alia from
representatives of the female cannabis Cannabis saliva and Cannabis indica
as well as certain chemical derivates thereof” (id. at 4:31–34).
The Claims
Claims 21, 22, and 24 are on appeal.2 Claim 21 is an independent
claim, is representative, and reads as follows:
21. Crystalline cannabidivarin of formula (V)

2 The Examiner finds claim 25 is withdrawn from prosecution (see Ans. 3).
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The Rejections
A. The Examiner rejected claims 21, 22 and 24 under 35 U.S.C. § 102(b)
as anticipated by Shoyama et al. (Cannabis. X1The Isolation and Structures
of Four New Propyl, Cannabinoid Acids, Tetrahydrocannabivarinic Acid,
Cannabidivarinic Acid, Cannabichromevarinic Acid and
Cannabigerovarinic Acid, from Thai Cannabis, 'Meao Variant', Chem.
Pharm. Bull. Vol. 25 (2306−11)(1977) (Final Act. 11–13).
B. The Examiner rejected claims 21, 22, and 24 under 35 U.S.C. § 103(a)
as obvious over Shoyama (Final Act. 13–17).

A. 35 U.S.C. § 102(b) over Shoyama
The Examiner finds Shoyama teaches “compound IIa CBDV which
corresponds to cannabidivarin of instant claims and discuss decarboxylation
IIb gave a neutral cannabinoid, IIa, C19H26O2, mp 115~118°, which was
identified by the comparison (UV, IR and NMR data) with CBDV i.e.
cannabidivarin” (Final Act. 12). The Examiner finds the compound is
identical to that claimed, citing In re Best, 562 F.2d 1252 (CCPA 1977) to
shift the burden of proving otherwise to Appellant.
Appellant responds “Shoyama describes the recovery of
cannabidivarin (referred to as Compound IIa), but does not describe the
formation of crystalline cannabidivarin. Instead, Shoyama obtains
cannabidivarin in the form of a colorless oil” (Appeal Br. 7). Appellant cites
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contends Shoyama also relates to a racemic mixture and does not describe a
purity of 99% as required by claim 22.
The issue with respect to this rejection is: Does a preponderance of the
evidence of record support the Examiner’s conclusion that Shoyama teaches
a crystalline cannabidivarin of formula V of claim 21?

Findings of Fact
1. Shoyama teaches “neutral propyl cannabinoids, cannabidivarin
(CBDV, IIa) . . . have been isolated from the south Asian Cannabis”
(Shoyama 2306).
2. Structure IIa of Shoyama is reproduced below:

Structure IIa as shown in figure 1 of Shoyama (Shoyama 2306).
3. Shoyama teaches “[u]pon decarboxylation IIb gave a neutral
cannabinoid, IIa, C19H26O2, mp 115–118°, which was identified by the
comparison (UV, IR and NMR) with CBDV” (Shoyama 2307–8).
4. Shoyama specifically teaches that a cannabinoid fraction was
“purified by silica gel column chromatography” and then “recrystallized
from hexane-CHCl3 to give IIb (213 mg), colorless needles, mp 102–105°”
after which the purified “IIb was decarboxylated to give IIa which was
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identified by the direct comparison (mp, UV, IR, NMR and MS) with an
authentic sample” (Shoyama 2310).
5. Shoyama teaches that every crystallized compound has a
melting point: “to give IIb (213 mg), colorless needles, mp 102–105°”; “to
give IId, colorless needles, mp 102–106°”; “IIe (8 mg) was [recrystallized]
from hexane CHCl3 mixture to give colorless needles , mp 116–118°”;
“CBVA (107 mg), from (1:1) eluate, which was then recrystallized from
hexane-CHCl3 to give colorless prisms, mp 129–133°”; “CBVA was
methylated to give CBVA methyl ester which was then recrystallized from
MeOH to give colorless prisms; mp 104–107°”; “CBGV (110 mg), Fr. 8-9;
IV (30 mg) was crystallized from hexane-CHC13 to give colorless needles,
mp 66-68°” (Shoyama 2310–11).
Principles of Law
[W]here the Patent Office has reason to believe that a
functional limitation asserted to be critical for establishing
novelty in the claimed subject matter may, in fact, be an
inherent characteristic of the prior art, it possesses the authority
to require the applicant to prove that the subject matter shown
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to be in the prior art does not possess the characteristic relied
on….
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.

Best, 562 F.2d at 1254–55.
Analysis
We find that the balance of the evidence of record better supports the
Examiner’s position. Every instance in Shoyama where a crystalline
composition is identified, whether as needles or prisms, Shoyama
immediately follows with the recitation of a melting point (FF 5). And
every instance in Shoyama where a compound in the form of a colorless
syrup is identified, Shoyama does not recite a melting point (FF 6). This
supports the Examiners finding that “melting point by definition is the
temperature at which a solid will melt” (Ans. 12).
When Shoyama discusses compound IIa that is identical to the
cannabidivarin of formula V recited in claim 21, Shoyama states “IIa which
was identified by the direct comparison (mp . . .)” (FF 4; cf. FF 3). That
Shoyama states compound IIa has a melting point reasonably supports the
Examiner’s position that compound IIa is inherently in a crystalline form.
We appreciate that “[i]nherency . . . may not be established by probabilities
or possibilities.” MEHL/Biophile Int’l. Corp. v. Milgraum, 192 F.3d 1362,
1365 (Fed. Cir. 1999). However, here Shoyama shows that every time a
melting point is mentioned, the compound is crystalline and every time
melting point is not mentioned, the compound is a colorless syrup. The
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evidence as it currently stands therefore satisfies the necessary standard.
Appellant provides no evidence, as opposed to argument, to the contrary
demonstrating that compound IIa is not a crystalline solid. See In re
Pearson, 494 F.2d 1399, 1405 (CCPA 1974) (“Attorney’s argument in a
brief cannot take the place of evidence.”).
That a different reference, Vollner,3 obtaining the compound a
different way results in a different form does not evidence otherwise,
because the issue is not whether the compound of Vollner anticipates but
rather whether the compound of Shoyama anticipates, and Vollner does not
address Shoyama’s IIa compound synthesized by decarboxylation of
compound IIb (FF 4).
We have also considered the Winkler Declarations,4 submitted to
overcome the rejection of the claims as drawn to a product of nature (see
Winkler Decl. I ¶ 2). The Winkler Decl. II does show that the melting point
of crystalline cannabidiarin was 116–120 °C, a value very similar to the
115–118 °C melting point of compound IIa as measured by Shoyama (FF 3).
We are not persuaded by Appellant’s arguments regarding the
allegation that Shoyama is a racemic mixture and is not 99% pure. The
Examiner finds that the crystals of Shoyama are the same enantiomer as that
recited in claim 21 and are 99% pure (Ans. 15). The Examiner finds “the
cannabinoid compounds IIa-IIe listed on page 2306 of Shoyama, of which
IIa corresponds to CBDV, are shown as stereoisomers and characterized by

3 Vollner et al., CANNABIDIVARIN, ein neuer Haschisch-
Inhaltsstoffannabidivarin, 3 Tetrahedron Letters 145–47 (1969).
4 Declaration I of Dr. Matthias Winkler, dated Sept. 16, 2019; Declaration II
of Dr. Matthias Winkler, dated Feb. 6, 2020.
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optical rotation on experimental page 2309” (id.). The Examiner also points
to optical rotation of the compound in Table I of Shoyama (id.). The
Examiner finds the narrow melting point of compound IIa “is an indication
of the high purity of the compound, therefore one of ordinary skills in the art
would understand the compound is in solid and pure form” (id. at 16).
We agree with the Examiner that a crystallized compound would be
expected to be pure and that there is no indication in Shoyama that the
enantiomeric biological starting material was racemized during the
purification or decarboxylation steps.
The Examiner has therefore provided a significant amount of evidence
establishing that compound IIa is crystallized, is pure, and is enantiomeric
and therefore reasonable establishes a prima facie case of obviousness.
Brandt explains that “it is important for the examiner to have a few
procedural tools to aid her efforts to issue as patents only those claims that
meet the requirements of the Patent Act . . . One of these procedural tools is
the prima facie case, an evidentiary burden-shifting device available to the
examiner.” In re Brandt, 86 F.3d 1171, 1176 (Fed. Cir. 2018).
Appellant provides no specific evidence showing that the compound
disclosed in Shoyama is not a crystalline solid, is not pure, and is not the
same enantiomer as recited in claim 21 and therefore has not shifted the
burden of production back to the Examiner.
Conclusion of Law
A preponderance of the evidence of record supports the Examiner’s
conclusion that Shoyama teaches a pure crystalline cannabidivarin of
formula V of claims 21, 22, and 24.

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B. 35 U.S.C. § 103(a) over Shoyama
We found above that Shoyama anticipates claims 21, 22, and 24.5 “It
is well settled that ‘anticipation is the epitome of obviousness.’” In re
McDaniel, 293 F.3d 1379, 1385 (Fed. Cir. 2002). Therefore, we also
necessarily affirm the obviousness rejection over Shoyama. We note that to
the extent relevant for the purity limitation of claim 22:
Ordinarily, one expects a concentrated or purified ingredient to
retain the same properties it exhibited in a mixture, and for
those properties to be amplified when the ingredient is
concentrated or purified; isolation of interesting compounds is a
mainstay of the chemist's art. If it is known how to perform
such an isolation, doing so “is likely the product not of
innovation but of ordinary skill and common sense.”
Aventis Pharma Deutschland Gmbh v. Lupin, Ltd, 499 F.3d 1293, 1302
(Fed. Cir. 2007) (citing KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398, 421
(2007)).
DECISION SUMMARY
In summary:
Claims
Rejected
35
U.S.C. §
Reference(s)/Basis Affirmed Reversed
21, 22, 24 102(a)(1) Shoyama 21, 22, 24
21, 22, 24 103(a) Shoyama 21, 22, 24
Overall
Outcome
21, 22, 24

5 We note that the Examiner inadvertently listed claims 20, 21, and 24 in the
statement of rejection (see Ans. 7), but this inadvertent error does not alter
the pending claims or the result.
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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