Ex Parte 8124072 et al

Patent Trial and Appeal Board

Feb 2, 2016

95002396 (P.T.A.B. Feb. 2, 2016)

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.
95/002,396 09/15/2012 8124072 16025.5.1.US.10 1051
94740 7590 02/02/2016
Winthrop & Weinstine, P.A.
Capella Tower, Suite 3500
225 South Sixth Street
Minneapolis, MN 55402
EXAMINER
HUANG, EVELYN MEI
ART UNIT PAPER NUMBER
3991
MAIL DATE DELIVERY MODE
02/02/2016 PAPER
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.
PTOL-90A (Rev. 04/07)

UNITED STATES PATENT AND TRADEMARK OFFICE
____________

BEFORE THE PATENT TRIAL AND APPEAL BOARD
____________

JARROW FORMULAS, INC.
Respondent and Requester

v.

SOFT GEL TECHNOLOGIES, INC.
Patent Owner and Appellant
____________

Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2
Technology Center 3900
____________

Before CHUNG K. PAK, RICHARD M. LEBOVITZ, and
JEFFREY B. ROBERTSON, Administrative Patent Judges.

LEBOVITZ, Administrative Patent Judge.

DECISION ON APPEAL
This is a decision on the appeal by Patent Owner from the Patent Examiner’s
final rejection of claims 1–24 in the above-identified inter partes reexamination of
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

2

United States Patent 8,124,072 B2. The Board’s jurisdiction for this appeal is
under 35 U.S.C. §§ 6(b), 134, and 315 (pre-AIA). We affirm.

STATEMENT OF THE CASE
The patent in dispute in this appeal is United States Patent 8,124,072 B2
(“the ’072 patent”) which issued February 28, 2012.
Jarrow Formulas, Inc. (“Requester”) requested inter partes reexamination of
the ’072 patent under 35 U.S.C. §§ 311–318 and 37 C.F.R. §§ 1.902–1.997.
Request for Inter Partes Reexamination dated September 15, 2012 (“Request”).
Reexamination was ordered November 23, 2012. The Action Closing Prosecution
was mailed July 8, 2013, and a Right of Appeal Notice (“RAN”) mailed April 30,
2014 listed pending claims 1–24 as finally rejected.
Patent Owner, Soft Gel Technologies, Inc., who is the real party in interest,
appeals the Examiner’s final rejection of these claims. Appeal Br. 1. Patent
Owner is the Appellant in this appeal. Requester is the Respondent. An oral
hearing was heard on December 9, 2015. A written transcript will be entered into
the record in due course.
There are related appeals and trials. Patent Owner identifies two District
Court actions related to the current reexamination which involves U.S. Patent
7,588,786 (“Khan ’786”) 1: Civil Action No. 2:10-cv-08301-PSG-JCx (C.D. Cal.)
and Civil Action No. 2:11-cv-00164-PSG-JCx (C.D. Cal.). Appeal Br. 1. The
above Civil Actions were consolidated and the District Court granted summary

1 U.S. Patent No. 7,588,786 B2, issued September 15, 2009, to Mansoor A. Khan
and Sami Nazzal. Khan ’786 is the basis of anticipation and obviousness
rejections in this appeal.
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

3

judgment of noninfringement. The decision was appealed to the Federal Circuit
which affirmed the judgment under Fed. Cir. R. 36 (entered Oct. 8, 2014) (2014-
1020, -1033, -1039).
There are also two related inter partes reexaminations, 95/002,411 and
95/002,405, which have been appealed to the Patent Trial and Appeal Board
(“PTAB”). A decision affirming the Examiner in Appeal 2015-004072 of
Reexamination Control 95/002,411, US Patent 8,147,826 B2, was entered Aug. 31,
2015. A decision in the second appeal, 2015-007926, in Reexamination Control
95/002,405 of US Patent 8,105,583, is entered concurrently with the decision in
this appeal. The decisions in this appeal are highly pertinent to the decision in
Appeal 2015-004072 as they involve related issues and the same prior art. For this
reason, we consider our findings and determinations in this appeal applicable,
when relevant, to Appeal 2015-004072.

Claim
Claim 1 is representative of the claims on appeal and reads as follows:
1. A soft gelatin capsule, comprising coenzyme Q-10 solubilized in
limonene to form a solution, wherein the amount of coenzyme Q-10 in
said solution is about 15 percent up to about 60 percent coenzyme Q-
10 by weight, with the proviso that the coenzyme Q-10 solubilized in
the limonene is not in an emulsion, suspension, or elixir.
Rejections
In the Right of Notice of Appeal, the Examiner rejected claims as follows:
1. Claims 1–3, 6–10, 14–20 and 24 under 35 U.S.C. § 102(a) and (e) as
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

4

anticipated by Khan ’786, as evidenced2 by Fenaroli,3 Duetz (Exhibit B),4
Mondello (Exhibit C),5 and IARC (Exhibit D).6 RAN 8.
2. Claims 4, 11, and 21 under 35 U.S.C. § 103(a) as obvious in view of
Khan ’786 and Steele7 as evidenced by Fenaroli, Duetz (Exhibit B), Mondello
(Exhibit C), and IARC (Exhibit D). RAN 10.
3. Claim 12 and 22 under 35 U.S.C. § 103(a) as obvious in view of Khan
’786 and Motoyama,8 Patent Owner’s admission on Motoyama, as evidenced by
Fenaroli, Duetz (Exhibit B), Mondello (Exhibit C), and IARC (Exhibit D). RAN
11.
4. Claim 1–3, 6–10, 14-20 and 24 under 35 U.S.C. § 102(b) as anticipated
by Nazzal as evidenced by Fenaroli, Duetz (Exhibit B), Mondello (Exhibit C), and
IARC (Exhibit D). RAN 12.

2 The Examiner also cited Exhibits E and F, but we have not relied upon them and
therefore do not include them in the ground of rejection or in grounds of rejection
2–9.
3 Giovanni Fenaroli, Fenaroli’s Handbook of Flavor Ingredients, vol. 1, p. 389, 2nd
edition, CRC Press, Inc. 1975.
4 Wouter A. Duetz et al., “Biotransformation of D-Limonene to (+) trans-Carveol
by Toluene-Grown Rhodococcus opacus PWD4 Cells,” 67(6) Applied
Environmental Microbiology 2829–2832 (June 2001)
5 Luigi Mondello et al., “Multidimensional Capillary GC-GC for the Analysis of
Real Complex Samples. 3. Enantiomeric Distribution of Monoterpene
Hydrocarbons and Monoterpene Alcohols of Mandarin Oils,” 46(1) J Agric. Food
Chem. 54-61 (Jan. 19, 1998).
6 World Health Organization, 56 IARC Monographs on the Evaluation of
Carcinogenic Risks to Humans 135-162 (1993).
7 Steele, EP 0 888 774 A2, published Jan. 7, 1999.
8 Moyotama et al., Patent Application Laid-Open Disclosure S57-42616, published
Mar. 10, 1982.
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

5

5. Claims 4, 11, and 21 under 35 U.S.C. § 103(a) as obvious in view of
Nazzal and Steele as evidenced by Fenaroli, Duetz (Exhibit B), Mondello (Exhibit
C), and IARC (Exhibit D). RAN 15.
6. Claims 12 and 22 under 35 U.S.C. § 103(a) as obvious in view of Nazzal
and Motoyama as evidenced by Fenaroli, Duetz (Exhibit B), Mondello (Exhibit C),
and IARC (Exhibit D). RAN 16.
7. Claims 1-3, 5–10, 12–20 and 22–24 under 35 U.S.C. § 103(a) as obvious
in view of Khan ‘786, Nazzal, Motoyama, and Patent Owner’s admission on
Motoyama as evidenced by Fenaroli, Duetz (Exhibit B), Mondello (Exhibit C), and
IARC (Exhibit D). RAN 16.
8. Claims 4, 11, and 21 under 35 U.S.C. § 103(a) as obvious in view of
Khan ‘786, Nazzal, Motoyama, Patent Owner’s admission on Motoyama, and
Steele as evidenced by Fenaroli, Duetz (Exhibit B), Mondello (Exhibit C), and
IARC (Exhibit D). RAN 20.
9. Claim 12 and 22 under 35 U.S.C. § 103(a) as obvious in view of
Khan ‘786, Nazzal, Motoyama, Patent Owner’s admission on Motoyama, and
Davidson9 as evidenced by Fenaroli, Duetz (Exhibit B), Mondello (Exhibit C), and
IARC (Exhibit D). RAN 21.

Background
The ’072 patent teaches that CoQ-10 (coenzyme Q10),10 commonly known
as ubiquinone, is essential for the production of cellular energy. ’072 patent, col.

9 Davidson et al., US 2004/0001874 A1, published Jan. 1, 2004.
10 For brevity, we use the abbreviation “Q10” throughout this decision. The
Examiner also used the abbreviation “Q-10.”
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

6

1, ll. 16–19. The ’072 patent describes clinical studies in which Q10
supplementation has been found to support blood pressure and cholesterol levels
and improve cardiovascular health. Id. at col. 1, ll. 44–48. The ’072 patent
discloses that Q10 is sparingly soluble in most hydrophilic solvents, such as water,
which limits its bioavailability. Id. at col. 1, ll. 51–55. The ’072 patent
characterized the invention as “the surprising discovery that ubiquinone (CoQ-10)
can be readily dissolved in varying concentrations in monoterpenes.” Id. at col. 2,
ll. 46-48. This approach satisfied the “need in the art for an improved
methodology to deliver increased amount of bioavailable CoQ-10 to an individual
in need thereof.” Id. at col. 1, ll. 56–58. The monoterpenes described in the ’072
patent include limonene and carvone. Id. at col. 3, ll. 49–53.

CLAIM INTERPRETATION
Claim 1 is directed to a “soft gelatin capsule” which comprises “co-enzyme
Q-10 solubilized in limonene to form a solution.” The ’072 patent teaches that the
“phrase ‘sufficient quantity of a monoterpene suitable to solubilize coenzyme Q-
10’ is therefore intended to mean that that amount of a monoterpene that will
dissolve CoQ-10 under a given set of conditions, generally, those at ambient
temperature.” ’072 patent, col. 3, ll. 11-16. In this case, the monoterpene is
limonene. We therefore interpret the term “solubilize” as it is used in the claim
means “dissolve.”
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

7

REJECTIONS
4. ANTICIPATION REJECTION BY NAZZAL
Claim 1 is directed to a “soft gelatin capsule” comprising “coenzyme Q-10
solubilized in limonene to form a solution.” The Q10 is present in an amount of
about 15 percent up to about 60 percent coenzyme. The claim contains a “proviso”
that “the coenzyme Q-10 solubilized in the limonene is not in an emulsion,
suspension, or elixir.”
Rejection
The Examiner found that Nazzal describes “a drug delivery system
containing coenzyme Q-10 solubilized in lemon oil that can be filled into a soft
gelatin capsule.” RAN 12. Citing Fenaroli, the Examiner found that lemon oil
contains 90% or more limonene, and of the limonene, “d-limonene constitutes 92-
96% of lemon peel oil (Exhibit B, page 2829), and amounts to 98.1 % (Exhibit C,
page 59, Table 6) or 98-100% of the lemonone [sic, limonene] in lemon oil
(Exhibit D, page 135).” Id. at 12–13. Using these values, the Examiner calculated
that Nazzal describes a Q10-lemon oil binary system comprising “about 36%, 45%
and 54% by weight d-limonene, which is of sufficient quantity to melt and
solubilize coenzyme Q10 to form a solution at about 33°C, 26°C and 24°C
respectively.” Id. at 13. The Examiner also found that Q10 is present in amounts
of 60%, 50%, and 40% by weight in the oily phase of lemon oil, meeting the
weight limitation of claim 1. Id.
Claim 1 also requires the Q10 is solubilized in d-limonene and “not in an
emulsion, suspension, or elixir” in the capsule. The Examiner found that Q10 is
solubilized in lemon oil, and when present in the capsule, no water is present so the
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

8

SNEDDS [self-nanoemulsified drug delivery system] is not an emulsion until
introduced into an aqueous medium. Id. at 9.

Discussion
Emulsion
Patent Owner contends that Nazzal does not anticipate the claims because
Nazzal teaches that the lemon oil and Q10 are combined with a surfactant, co-
surfactant, and other ingredients form an emulsion which is excluded by the claim.
Appeal Br. 28–29. As evidence of this, Patent Owner identified the following
disclosure from Nazzal:
The eutectic-based self-nanoemulsified drug delivery system
(SNEDDS) of CoQ10 was prepared as follow[s]: CoQ10 and lemon oil
at a ratio of 1:1 were accurately weighed into screw-capped glass vial
and melted in water bath at 37°C. Cremophor EL and Capmul MCM-
C8 were added to the oily mix at a final concentration of 26.9%w/w
each. The resultant emulsion was mixed with a stirring bar until a
transparent solution of SNEDDS was obtained. The SNEDDS were
then allowed to cool at ambient temperature for 24 hrs until a viscous
paste was obtained. Nanoemulsion adsorbed granular material was
obtained from a mixture of SNEDDS paste, copolyvidone (Kollidon
VA 64), maltodextrin (Glucidex IT 12), and microcrystalline cellulose
(Avicel) . . .
Nazzal 80.
A eutectic mixture of CoQ10 with lemon oil could be used to produce
stable nanoemulsion in aqueous medium when mixed with a proper
blend of surfactants and cosurfactants.
Id. at 243.
A preponderance of the evidence does not support Patent Owner’s
contention that composition comprising Q10, lemon oil, surfactant Cremophor EL,
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

9

and cosurfactant Capmul MCM-C8 are in the form of an emulsion. The evidence
is outlined below:
1. Nazzal expressly teaches that a self-emulsifying drug delivery system is
not a microemulsion:
Self-emulsifying drug delivery systems (SEDDS) and self-
microemulsifying drug delivery systems (SMEDDS) are not
microemulsions, although they may be considered to be a closely
related system. The key difference between the two preparations is the
optical clarity and the finer droplet size achieved when SMEDDS are
dispersed into the aqueous phase . . . A SMEDDS typically comprises
a mixture of surfactant, oil and drug (known as the concentrate) which
when introduced into the body is rapidly dispersed to form droplets of
approximately the same size range as those observed in
microemulsion systems . . . Once dispersed, such systems would be
expected to self-emulsify rapidly in the aqueous contents of the
stomach and to behave in vivo much the same way as oil-in-water
(o/w) microemulsions. . . . . SEDDS and SNEDDS can therefore be
defined as “isotropic solutions of oil, surfactant, co-surfactant, and
drug which form o/w (micro) emulsions when introduced into
aqueous phases under gentle agitation.”
Id. at 19–20 (internal citations omitted) (emphasis added).
As the passage reproduced above shows, Nazzal teaches that the self-
microemulsifying drug delivery systems “are not microemulsions.” Id. Rather,
when “dispersed” in an aqueous phase, the SNEDDS self-emulsifies to form an oil-
in-water emulsion. Id. This description is consistent with the description on pages
71–72 of Nazzal, and elsewhere, where he describes stirring formulations of Q10,
oil, surfactant, and co-surfactant in water, and observing that a spontaneous
transparent emulsion is formed. Id. at 27-34; 121–132.
2. Nazzal distinguishes between microemulsions and self-emulsifying
vehicles, indicating that the SNEDDS is not in the form of a microemulsion:
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

10

The delivery of cyclosporine A via microemulsion formulations and
the superiority of the Neoral® microemulsion preconcentrate . . . has
been demonstrated on several occasions . . .
To date, microemulsion and self-emulsifying vehicles have
been shown to be able to protect labile drug, control drug release,
increase drug solubility, increase bioavailability and reduce PK and
PD response variability.
Id. at 26.
3. Despite the mention of forming an emulsion on page 80, other parts of
Nazzal refer to melting Q10, the essential oil, and surfactant, and specifically at
body temperature before being dispersed into an emulsion in the body’s aqueous
environment. Id. at 121, 132. For example, in Nazzal’s description of making an
HPMC capsule, he describes adding the surfactant and cosurfactant to an oily mix
of the Q10 and lemon, and “[w]hile molten,” filling the HPMC capsules. Id. at 71.
Nazzal further describes introducing the “pre-melted” formulation into water,
gently stirring, and then observing the “tendency to spontaneously form a
transparent emulsion.” Id. at 72. Thus, these sections refer to an emulsion when
the formulation is introduced into water, but not before. Similarly, the section on
page 243 of Nazzal cited by Patent Owner states the formulation produces a “stable
nanoemulsion in aqueous medium” (emphasis added), but makes no mention of the
formulation, itself, being in the form of an emulsion prior to contact with the water.
4. The Examiner’s definition of “emulsion” does not support the finding
that mixture of Q10, volatile oil, surfactant, and cosurfactant is an emulsion. The
Examiner adopted the following definition of emulsion:
A substantially permanent mixture of two or more liquids which do
not normally dissolve in each other but which are held in suspension,
one in the other. The suspension is usually stabilized by small
amounts of additional substances known as emulsifiers.
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

11

RAN 4.
As discussed in detail below, a preponderance of the evidence indicates that
Q10 dissolves in lemon oil dissolve. Consequently, there does not appear to be
“two or more liquids” present “which do not normally dissolve in each other.” On
the other hand, when SNEDDS is introduced into an aqueous environment, the
lemon oil/Q10 and water serve as two liquids which do not dissolve in each other,
but rather form an emulsion by self-emulsification as described in Nazzal.
Consistent with this definition are the statements made during the
prosecution of the ’072 patent when the proviso was added excluding an
“emulsion”:
In contrast to the presently claimed method, the Examiner
points out that “Garti et al. disclose compositions, nano-scale
emulsions.” Office Action, p. 3 and 5. Garti does not contradict the
Examiner’s characterization, rather Garti more precisely describes the
emulsion as “nano-sized structured concentrates.., of at least two
immiscible liquids (water and oil) with the aid of a surfactant, co-
surfactant and co-solvent.” . . . Thus, Garti’s invention is a multi-
component formulation of the type expressly proviso’d out in present
claims 14 [present claim 1] and 22.
Remarks 7 (Oct. 19, 2009) (emphasis added)
In other words, the term “emulsion¨ requires two immiscible liquids, but
there is inadequate evidence that two immiscible liquids are present in the
formulation comprising Q10, lemon oil, surfactant, and co-surfactant because as
explained in more detail below, the evidence supports the finding that Q10
dissolves in lemon oil. Consequently, Nazzal’s use of the term “emulsion” on
page 80, when the surfactant and co-surfactant are added to the oily mix of Q10
and lemon oil appears to be in a different context than the definition adopted by the
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

12

Examiner and proposed by Patent Owner when the term was added to claim 1 by
amendment.

“coenzyme Q-10 solubilized in limonene to form a solution”
The claims all require the coenzyme Q10 to be “solubilized in limonene to
form a solution.”
The Examiner found that Nazzal describes “a drug delivery system
containing coenzyme Q-10 solubilized in lemon oil that can be filled into a soft
gelatin capsule,” where the lemon oil “contains 90% or more limonene (Fenaroli,
page 389), which is mostly or all d-limonene,” constituting “92-96% of lemon peel
oil (Exhibit B, page 2829), and amounts to 98.1 % (Exhibit C, page 59, Table 6) or
98-100% of the limonene in lemon oil (Exhibit D, page 135).” RAN 12–13. The
Examiner found that Nazzal “shows that as the relative amount of lemon oil is
increased, the temperature at which the coenzyme Q10 melts and solubilizes in
solution can be reduced from about 51°C (melting temperature of coenzyme Q10)
to below room temperature (pages 112–115).” Id. at 13.
The Examiner acknowledged that Nazzal describes melting the Q10 in
lemon oil, but stated that the recited language in the claims does “not exclude
solubilizing or dissolving via melting.” Id. at 22. The Examiner further stated that
Patent Owner has not demonstrated “any difference between the prior art binary
mixtures of coenzyme Q10 and lemon oil (d-limonene) and the claimed
composition comprising coenzyme Q10 and d-limonene.”11 Id.

11 The Examiner referred to d-limonene, but the claims are not limited to this form,
but rather recite “limonene” which would include both the d- and l-forms.
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

13

The following findings of fact (“FF”) are pertinent to the Examiner’s
determination that Nazzal anticipates the claimed subject matter:
FF1. Nazzal teaches that Q10 and a volatile essential oil (L-menthol,
spearmint oil, lemon oil and anise oil) were mixed and then heated to different
temperatures to determine the temperature at which the mixture melted. Nazzal
112–115; Figures 4.8–4.12.
FF2. Specifically, Fig. 4.13 of Nazzal shows a temperature range, of about
15°C to about 50°C, over which Q10 was melted with the essential oil using
different weight/weight ratios of Q10 to essential oil.
FF3. Figs. 4.8–4.12 of Nazzal show the differential scanning calorimetry
(DSC) thermograms of various volatile essential oils and Q10. The data in these
figures was used to construct the graph in Fig. 4.13. Id. at 112-115. Fig. 4.11
shows the DSC thermogram for Q10 and lemon. Each point in Fig. 4.13 was
determined from a DSC thermogram of Q10 and a specific amount of the essential
oil.
FF4. The data in Figs. 4.8 to 4.13 show that the binary combination of Q10
and essential oil (such as lemon oil) formed a melted composition at a specific
temperature for a specific ratio of Q10 to oil.

Issue
The issue is whether Nazzal’s teaching of a melted composition of Q10 and
lemon oil anticipates the claimed “coenzyme Q-10 solubilized in limonene to form
a solution.” In other words, does melting Q10 in lemon oil (FF1) result in a
composition in which Q10 is solubilized, namely dissolved, in the limonene?
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

14

Since Nazzal does not expressly teach that the Q10 dissolves in limonene,
the rejection is based on “inherency,” that is, while Nazzal does not describe its
composition with the same terms recited in the claim, the claimed composition
would be a necessary result of making the composition described in Nazzal.
[A] prior art reference may anticipate when the claim limitation or
limitations not expressly found in that reference are nonetheless
inherent to it. . . . Inherency is not necessarily coterminous with the
knowledge of those of ordinary skill in the art. Artisans of ordinary
skill may not recognize the inherent characteristics or functioning of
the prior art.
MEHL/Biophile Int’l Corp. v. Milgraum, 192 F.3d 1362, 1365 (Fed. Cir. 1999).
Anticipation does not require the skilled worker to have recognized that the
Q10 was dissolved in the d-limonene as long as it would happen each time the
directions in Nazzal were followed.

Discussion
Patent Owner contends that Nazzal does not anticipate the claimed
“solubilized coenzyme Q-10 composition” comprising limonene because Nazzal
“does not disclose that [coenzyme] Q-10 can be dissolved in lemon oil, and instead
teaches melting point reduction as an alternative way to liquefy coQ-10 precisely
because it is difficult to dissolve.” Appeal Br. 24. Patent Owner argues that
Nazzal does not provide “a solution in which coenzyme Q-10 is dissolved,” but
rather “states that the ‘poor water solubility’ of coQ-10 is overcome by reducing
the melting point of coQ10, so that it becomes a liquid at or below 30°C.” Id. at
25. To support this position, Patent Owner cites the following disclosure from
Nazzal:
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

15

FF5
Due to the limited solubility of CoQ-10 in fixed oils and triglycerides,
the melting point depression method using essential oils provides an
attractive alternative for the preparation of an emulsified formulation.
Nazzal 115.
Patent Owner further argues that Nazzal “distinguishes between melting and
dissolving and states that melting is an attractive alternative to traditional
approaches that unsuccessfully sought to dissolve coenzyme Q-10.” Appeal Br.
25. To support this position, Patent Owner points to the following disclosure in
Nazzal:
FF6
In a eutectic-based self-nanoemulsifying, the melting point depression
method allows the oil phase containing the drug itself to melt at body
temperature from its semisolid consistency and disperse to form
emulsion droplets in nanometer size range.
Id. at 112.
Patent Owner also cites a District Court Order (“Dist. Ct. Order”) in an
infringement action in the United States District Court Central District of
California (CV 10-8301 PSG) asserting Khan ’786 against, inter alia, Patent
Owner. See 2012 WL 3186576 (2012). In the District Court Order, the court
rejected the position that melting as used in Khan ’786 is “synonymous” with
dissolving. Dist. Ct. Order 11. The District Court decision was affirmed by the
Federal Circuit under Fed. Cir. R.36 (Oct. 8, 2014, 2014-1020, -1033, -1039).
Nazzal is the Ph.D. dissertation of one of the co-inventors of Khan ’786.
According to Patent Owner, Nazzal’s dissertation “resulted in the Khan patent
application.” Appeal Br. 23. Patent Owner states the “relevant disclosure of
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

16

Nazzal is the same as the disclosure in the Khan patent, and thus suffers from the
same disclosure deficiencies as Khan.” Id. Patent Owner did not distinguish
between the disclosure in Khan ’786 and Nazzal, but rather appears to have made
the same arguments for both publications. Id. at 24-29. Consequently, we find
that the District Court’s findings regarding Khan ’786 are applicable to Nazzal.
The Order construed “melting” to be “’a phase transition from solid to
liquid’ through the application of heat.” Dist. Ct. Order 10. The district court,
however, did not provide a definition of “dissolve.”
FF7. Because no definition is of record for us to consider, we have
consulted a general chemistry textbook to determine the meaning of “dissolve” and
“dissolving.” “Dissolve” is defined in the following manner: “When a solute
dissolves, the individual particles of solute become surrounded by solvent
particles” to produce a “solution.”12 A “solution” is a homogeneous combination
of solute and solvent particles. General Chemistry – Principles, Patterns, and
Applications13 1172 (hereinafter, “General Chemistry.”) See also RAN 4 (“A true
solution is a homogeneous mixture of two or more substances.”)
The Examiner found that melting is “closely related” to dissolving because
both involve energy changes. RAN 23. The Examiner did not cite support for this

12 The Basics of General, Organic, and Biological Chemistry (2011), v. 1.0, Ball,
David, W., Hill, John W., and Scott, Rhonda, J., Section 9.3, “The Dissolution
Process,” Flat World Education, Inc. (2015). Accessed at
http://catalog.flatworldknowledge.com/bookhub/reader/2547?e=gob-ch09_s03
(Dec. 11, 2015). Hereinafter, “Chemistry Basics.”
13 Averill B. and Eldredge, P. (2011)
http://www.saylor.org/site/textbooks/General%20Chemistry%20Principles,%20Pat
terns,%20and%20Applications.pdf
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

17

statement apparently because the statement reflects well known principles in
chemistry. The Examiner’s finding is factually supported as follows:
FF8
Physical changes, such as melting or vaporization, and chemical
reactions, in which one substance is converted to another, are
accompanied by changes in enthalpy [energy change]. Two other
kinds of changes that are accompanied by changes in enthalpy are the
dissolution of solids and the dilution of concentrated solutions.
General Chemistry 444.
FF9. When a solute dissolves in a solvent, “energy is required to overcome
the intermolecular interactions in a solute.” Id. at 1173. Similarly, the “melting
point” is when the ions or atoms in a solid have enough energy to overcome the
intermolecular attractive forces which hold them together. Id. at 684, 795, 981,
985, 1029, 1071.
Thus, as found by the Examiner, “melting” is closely related to “dissolving”
because of the change in energy when the intermolecular interactions between the
atoms in the solid are overcome as the solid melts or as the solute particles in the
solid dissolve in the solvent. A key difference between melting and dissolving is
that melting involves only a change in state of the solid into a liquid when the
intermolecular forces that hold the atoms in the solid together are overcome, while
dissolving involves overcoming the attractive forces between the atoms in the solid
and mingling the solid atoms homogenously with solvent particles. When a solid
dissolves in the solvent, it could just as well be said that it “melts” because, as with
the melting process, the intermolecular forces that hold the solid atoms together are
overcome allowing it to become dispersed in solvent.
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

18

The next question is whether the Q10 forms a solution when it melts in the
presence of the lemon oil. The Examiner’s position is that it does because of the
close relationship between melting and dissolving, i.e., melting results in
overcoming the intermolecular interactions of the atoms in the solid, permitting
them to disperse within the lemon oil solvent as would happen when the
intermolecular forces are overcome in dissolving. The Examiner’s reasoning is
supported by Dr. Nazzal’s testimony in his declaration in which he describes his
work reported in the Khan ’786 patent. RAN 26–28. Dr. Nazzal testified
(emphasis added):
4. The ’786 Patent [Khan] describes and teaches the surprising and
unexpected discovery that a sufficient amount of volatile essential oil
reduces the melting point of CoQ10 to 37°C or below to thereby
liquefy and solubilize the CoQ10 at or below body temperature.
5. At the time of our invention, I was not aware of any CoQ10
formulation in commercial use or in the literature that contained
CoQ10 that was solubilized with a volatile essential oil or solubilized
with a sufficient amount of a volatile essential oil that would reduce
CoQ10’s melting temperature.
Dr. Nazzal thus explains when the Q10 is melted to a liquid it is
“solubilized,” namely dissolved in the essential oil (see “Claim Interpretation”
above finding that solubilize means dissolve).
In sum, a preponderance of the evidence supports the conclusion that when
the Q10 and lemon oil form a mixture upon heating (FF1–FF4), the Q10 melts and
dissolves in the lemon oil.
Patent Owner’s argument that Khan ’786’s use of the term “solubilize” is
not the same as “dissolve” is unavailing. Appeal Br. 10–13. Patent Owner
contends that Khan ’786 and Nazzal distinguish between “dissolve” and
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

19

“solubilize.” Rebuttal Br. 2. Specifically, Patent Owner argues that “solubilize” is
used in Khan ’786 in the context of utilizing surfactants. Id. at 3.
In our opinion, it is not clear cut that Khan ’786 and Nazzal use the terms
“dissolve” and “solubilize” in all instances to mean different chemical processes.
For example, in the passage reproduced below, Nazzal refers to dissolving Q10 in
acetone and then to “solubilized” Q10 in acetone, suggesting that in this instance
the terms are used in the same way.
To eliminate the effect of temperature on the integrity CoQ10, stock
solution (0.1 mg ml-1, 0.1% Cremophor EL) was prepared by
dissolving 100 mg of CoQ10 in 3 ml of acetone. One gram of
Cremophor EL was added and mixed with the solution and
subsequently diluted to 1 liter with distilled water. Similarly, to
evaluate the effect of Cremophor EL concentration on CoQ10 analysis,
a stock solution (0.1 mg ml-1, 1% Cremophor EL) was prepared by
mixing solubilized CoQ10 in acetone with 10 grams of Cremophor EL.
Assay validation was performed as described above.
Nazzal 67 (emphasis added).
Although Patent Owner attempts to establish that “solubilize” requires the
presence of solubilizing agents (Appeal Br. 13), Dr. Nazzal does not refer to the
presence of a solubilizing agent in his statements in paragraphs 4 and 5 of his
declaration. Moreover, Patent Owner has not explained why “solubilizing” a drug
with a “solubilizing agent” would not result in the drug being dissolved in the
solubilizing agent. Patent Owner has largely focused on word definitions, and
perhaps the imprecise and loose use of the words, without explaining the actual
chemical processes that occur when a compound is dissolved or solubilized.
Nonetheless, the rejection is based on inherency, and even if Khan ’786 and
Nazzal use the terms “dissolve” and “solubilize” to mean different chemical
processes, the issue is not whether the two publications described Q10 dissolved in
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

20

lemon oil, and its main constituent limonene, but whether, when Khan ’786 and
Nazzal are followed, would the necessary result be Q10 dissolved in limonene.
Patent Owner also contends that the “mechanism” by which “one gets to a
liquid solution . . . cannot be ignored.” Appeal Br. 13. The Examiner has not
ignored this step. As explained, when heat is applied to the binary combination of
lemon oil and Q10, the attractive forces in the atoms are overcome in the Q10 and
it dissolves in the lemon oil. Patent Owner denies that dissolving occurs, but has
offered no alternative explanation as to what happens to the atoms of Q10 and
lemon oil upon the application of heat.
The District Court Order is not inconsistent with the conclusion that the Q10
dissolves in the lemon oil. The District Court distinguished melting from
dissolving, a finding that does not exclude there from being similarities between
the two processes as discussed above. Moreover, the District Court in the Order
acknowledged that the melting point reduction process in Khan ’786 in which a
eutectic was formed resulted in the Q10 dissolved in lemon oil: “The fact that the
melting point reduction is used as a means to solubilize or dissolve and as a basis
for distinguishing traditional methods indicates that melting is distinct from
dissolving or solubilizing.” Dist. Ct. Order 13 (emphasis added). In other words,
while the District Court recognized that the “melting point reduction” method is
different from dissolving because a reduction in melting temperature is observed in
the former and results in “a change in the physical properties” of Q10, it
specifically stated the melting point reduction method was a “means to solubilize
or dissolve” the Q10. Id. The mechanisms may be different, but it is the result
which is claimed, not the mechanism, which is relevant to the claims at issue, as
there is no temperature limitation set forth in the claims.
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

21

limonene
FF10. The Examiner found that lemon oil contains 90% or more limonene
(citing Fenaroli on page 389), which “is mostly or all d-limonene (Exhibits B-
F).”14 RAN 12.
FF11. The Examiner further found that “Lemon oil contains 90% or more
limonene (Fenaroli, page 389), which is mostly or all d-limonene (Exhibits B-F).
Indeed, d-limonene constitutes 92-96% of lemon peel oil (Exhibit B, page 2829),
and amounts to 98.1 % (Exhibit C, page 59, Table 6) or 98-100% of the limonene
in lemon oil (Exhibit D, page 135.” Id. at 12–13. The Examiner’s findings
regarding these publications are factually supported.
Based on these values, the Examiner found that the binary composition of
Q10 and lemon oil as shown in Nazzal’s Fig. 4.13, contains “about 36%, 45% and
54% by weight d-limonene (in 40%, 50% and 60% by weight lemon oil) in a
mixture with 60%, 50% and 40% by weight of coenzyme Q10 respectively.” Id. at
29. The Examiner concluded that in the binary composition “coenzyme Q10 melts
and solubilizes at about 33°C, 26°C and 24°C respectively, indicating that
d-limonene (lemon oil) is suitable for dissolving coenzyme Q10 at ambient
temperature or below.” Id.
Patent Owner disputes the Examiner’s finding that lemon oil is always
necessarily15 d-limonene or 90% d-limonene, citing the Lota and Steuer
publications as evidence. Appeal Br. 15-16. Patent Owner states:

14 We have not considered Exhibits E and F.
15 “[A] prior art reference may anticipate without disclosing a feature of the
claimed invention if that missing characteristic is necessarily present, or inherent,
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

22

Patent Owner has submitted evidence that the amount of limonene in
lemon oil is less than 40%. See Lota at 797, Table 1 (Ex. V).
Accordingly, Exhibits B, C and D, in view of Lota and Steuer, do not
meet the Office’s burden to show anticipation by inherency; they do
not “make clear” that lemon oil is always “necessarily” d-limonene or
90% d-limonene
Id. at 16.
While we have concluded that Q10 dissolves in lemon oil when melted, the
claim requires that Q10 be dissolved in the limonene present in the lemon oil. The
Examiner’s reasoning for finding that it is the limonene that dissolves the Q10
appears to be based on the fact that limonene is the main constituent of lemon oil
containing as much as 90%. Specifically, Exhibits B, C, and D support the
Examiner’s position. FF10, FF11. Patent Owner’s countervailing evidence is that
the amount of limonene in lemon oil can be less than 90%, depending on the
source.
Even if it true that the content of limonene is than the 90% value relied upon
by the Examiner, this does not answer the issue in this rejection, i.e., whether the
limonene in Nazzal’s lemon oil dissolves the Q10 when the lemon oil and Q10 are
melted together. Thus, even if the amount of limonene present in the lemon
oil/Q10 mixture described in Nazzal is less than the lower limit of 36% by weight
calculated by the Examiner (RAN 13), there still must be evidence that such lower
amounts would or would not dissolve Q10.

in the single anticipating reference.” SmithKline Beecham Corp. v. Apotex Corp.,
403 F.3d 1331, 1343 (Fed. Cir. 2005) (citing Continental Can Co. v. Monsanto
Co., 948 F.2d 1264, 1268 (Fed. Cir. 1991)).

Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

23

The Examiner had basis to find that the Q10 dissolves in the limonene
because, as discussed above, the Q10 dissolves in the lemon oil and a significant
amount of limonene is present in the lemon oil. Patent Owner argues about the
content of limonene in lemon oil, but fails to provide evidence that, if the particular
species or strain which is said to contain less limonene than the 90% value
assumed by the Examiner had been used in Nazzal,16 the amounts of d-limonene
would have been insufficient to dissolve the recited amounts of Q10.
In our opinion, this controversy about the amounts of limonene and
limonene in lemon oil that has occupied the Examiner, Patent Owner, and
Requester begs the question of how much limonene is necessary to dissolve the
recited amounts of Q10. On this pivotal question, the evidence is that 1) lemon oil
solubilizes and dissolves Q10, and 2) limonene is principal component of it, giving
the Examiner reasonable factual basis to conclude that even lemon oils with less
than 90% limonene would have sufficient d-limonene present to dissolve Q10.
The lower value of 38.1% identified in one species in Lota (Table 1, “Bor”)
is still about a third of the higher values; indeed, there is no evidence that this
species of lemon oil peel was available to Nazzal.
Under In re Best, 562 F.2d 1252 (CCPA 1977), Patent Owner has the burden
to prove that the recited amounts of Q10 would not be dissolved in the lemon oil of
Nazzal.
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

16 Lemon peel oils: “Limonene was always the main constituent (38.1-95.8%) of
all oils.” Lota, page 799.
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

24

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.
Best, 562 F.2d at 1255 (CCPA 1977) (footnote omitted). Patent Owner did not
meet this burden.
In sum, the fact that Nazzal’s lemon oil was not necessarily 90% limonene
(Appeal Br. 13–14) does not undermine the Examiner’s finding that Nazzal
anticipates the claimed subject matter. In view of this evidence, we conclude that a
preponderance of the evidence supports the Examiner’s finding that Nazzal
necessarily and inherently disclosed Q10 dissolved in limonene.

Khan (2004)
Patent Owner argues that a subsequent publication by Khan – Khan (2004)17
– demonstrates that the lemon in Nazzal “was not d-limonene or 90% d-limonene.”
Appeal Br. 15. According to Patent Owner, Khan (2004) is “a separate study
analyzing d-limonene and its ability to reduce the melting point of coenzyme
Q10.” Id at 15. Patent Owner contends:
If the lemon oil used in Khan and Nazzal were d-limonene or 90% d-
limonene, then there would be no reason for Dr. Khan subsequently to

17 Anitha Palamakula, Mahmoud Soliman, Indra K. Reddy, and Mansoor A. Khan,
“Preparation and In Vitro characterization of Self-Nanoemulsified Drug Delivery
Systems of Coenzyme Q10 Using Chiral Essential Oil Components,”
Pharmaceutical Technology 74–88 (October 2004).
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

25

study and publish findings on whether d-limonene could be used to
reduce the melting point of coenzyme Q10.
Id.
Patent Owner has not provided adequate evidence that subsequent work by
Khan’s group using d-limonene rather than lemon oil reasonably means that Khan
did not believe the lemon oil in the Nazzal was not predominantly limonene. Khan
(2004) states that the reason for its study was “to study natural substance such as
chiral components of essential oils for solubilizing drug compounds.” Khan
(2004) 74. Khan (2004) further states that limonenes exist in two chiral
conformations and the R-(+) form, also known as d-limonene. Id. Furthermore,
Khan states that that “[r]esearch in the food industry has demonstrated R-(+)-
limonene in microemulsions as vehicles to enhance the solubilization of natural
food supplements,” but acknowledges that the “available literature is scare . ..
about using these components to prepare SNEDDS.” Id. Thus, it appears Khan
(2004)’s reason for studying d-limonene was its interest in chiral component.

Dependent claims
Patent Owner did not provide separate reasons for the patentability of claims
2, 6–10, and 15. Appeal Br. 21. Thus, these claims fall with independent claim 1.
37 C.F.R. § 41.67(c)(vii).

5. OBVIOUSNESS REJECTION OVER NAZZAL AND STEELE
The Examiner found that Nazzal does not disclose rice bran oil as a carrier
as specified in claims 4, 11 and 21. RAN 15. However, the Examiner found that
rice bran oil as a carrier in a coenzyme Q10 soft gelatin formulation was known in
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

26

the art at the time of the invention as specifically described by Steele (abstract;
page 3, lines 4-5). Id. Accordingly, the Examiner concluded it would have been
obvious to include the rice bran oil as a carrier in Nazzal’s solubilized coenzyme
Q10 formulation to arrive at the claimed invention with a reasonable expectation of
success. Id.
Patent Owner argues that Steele does not “remedy the deficiencies of
Nazzal.” Appeal Br. 29. Because we determined that these arguments are
unpersuasive, the rejection of claims 4, 11, and 21 are affirmed for the reasons set
forth by the Examiner.

6. OBVIOUSNESS REJECTION OVER NAZZAL AND MOTOYAMA
The Examiner found that Nazzal does not disclose fish oil as a carrier as
recited in claims 12 and 22. RAN 16. However, the Examiner found that including
fish oil in a coenzyme Q 10 formulation was known in the art at the time of the
invention as described by Motoyama (page 1, right col.; page 5,
right col.). Id. Accordingly, the Examiner concluded it would have been obvious
to include fish oil in Nazzal's solubilized coenzyme Q10 formulation to arrive at
the claimed invention with a reasonable expectation of success. Id.
Patent Owner argues that Motoyama does not “remedy the deficiencies of
Nazzal.” RAN 30. Because we determined that these arguments are unpersuasive,
the rejection of claims 12 and 22 are affirmed for the reasons set forth by the
Examiner.

7-9. OBVIOUSNESS REJECTIONS BASED ON MOTOYAMA
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

27

The Examiner found that Motoyama describes a soft gelatin capsule
comprising Q10 dissolved in carvone, which includes l-carvone derived from
spearmint oil and peppermint oil and d-carvone from caraway seed oil. RAN 16-
17. The Examiner stated that it would have been obvious to have utilized
limonene18 instead of a carvone-containing oil because both were known to be
effective in solubilizing Q10 as demonstrated by Khan ’786. Id. at 18.
In this case, we find there is adequate evidence that one of ordinary skill in
the art would have had reason to try limonene to dissolve Q10 with a reasonable
expectation of success.19 The following facts are pertinent to this determination:
FF12. Motoyama teaches that carvone, a monoterpene (’072 patent, col. 4,
ll. 52-56), dissolves Q10. Motoyama 5 (col. 2) (“[C]arvone is a particularly
preferred oil due to good solubility for ubiquinone and the property of dissolving
an equal weight of ubiquinone at room temperature.”).
FF13. Motoyama teaches that “refined oils that contain carvone (such as
peppermint oil, spearmint oil, or the like) are preferred for the present invention
due to the ability to dissolve ubiquinone well.” Id.
FF14. Khan ’786 discloses that essential oils, such as menthol, peppermint
oil, spearmint oil, and lemon oil lower the melting temperature of Q10, making

18 Both the Examiner and Patent Owner in their arguments refer to “d-limonene.”
However, the claims do not require d-limonene.
19 To decide whether a composition would have been obvious in light of the prior
art, it must be determined whether, at the time of invention, “a person of ordinary
skill in the art would have had reason to attempt to make the . . . [composition], . . .
and would have had a reasonable expectation of success in doing so.”
PharmaStem Therapeutics, Inc. v. ViaCell, Inc., 491 F.3d 1342, 1360 (Fed. Cir.
2007).
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

28

them useful in a delivery system for Q10. Khan ’786, col. 6, ll. 24–27, col. 6, l. 65
to col. 7, l. 35.
FF15. D-limonene is a monoterpene (’072 patent, col. 4, ll. 52-56) and the
main constituent of lemon peel oil (Duetz 2829 (Exhibit B)(“D-Limonene is the
main constituent of orange and lemon peel oil (92 to 96%) . . .”)); (IARC 135
(Exhibit D) (“the d form [of limonene] comprises 98-100% of the limonene in
most citrus oils (family Rustaceae)”)); Mondello, Table 6 (Exhibit C )(“limonene
(4R)(+) 98.1”))
FF16. Nazzal recommended for future studies that “[c]hemical components
of essential oils such as limonene, menthone, and carvone can be evaluated for
their potency in exerting a eutectic effect.” Nazzal 246.

Discussion
A preponderance of the evidence supports the Examiner’s determination that
one of ordinary skill in the art would have had reason to utilize limonene to
dissolve Q10.
First, Motoyama teaches that another monoterpene dissolves Q10 and
teaches that some of the same oils (spearmint, peppermint) described as effective
by Khan ’786 are preferred for their ability to dissolve Q10.20 FF12–FF14.

20 The ’072 patent described its invention as “the surprising discovery that
ubiquinone (CoQ-10) can be readily dissolved in varying concentrations in
monoterpenes.” ’072 patent, col. 1, ll. 62-64 or 2:46-48. However, it appears that
Motoyama had at least already discovered the Q10 could dissolve in the
monoterpene carvone, providing the same solution to the problem identified in the
’072 patent of delivering increased amounts of bioavailable Q10. Id. at col. 1, ll.
55–58.
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

29

Because of the overlap in disclosure of essential oils between Motoyama and Khan
’786, one of ordinary skill in the art would have had reason to have used Khan
’786’s oils in Motoyama’s method in amounts sufficient to dissolve Q10, with a
reasonable expectation that they would work. That is, since Motoyama teaches
that spearmint and peppermint oil dissolve Q10, and Khan ’786 teaches using these
same oils in conjunction with Q10, the skilled worker would have had basis to
believe that Khan ’786’s lemon oil, when used in a sufficient amount, would work
in Motoyama’s method to dissolve Q10.
Second, while Khan ’786 does not identify limonene as a component of
lemon oil, limonene is a main constituent of lemon peel oil. FF11, FF12.
The skilled worker would have had reason to use limonene in Motoyama’s
method because it is a monoterpene like Motoyama’s carvone (FF13, FF15), and
Nazzal explicitly suggested d-limonene for future studies (FF16). Nazzal also
suggested evaluating carvone for its potency in exerting a eutectic effect when
combined with Q10 (FF16), further indicating the interchangeability of carvone
and d-limonene, or at least the reasonable belief that they would have similar
properties.
Patent Owner argues that Khan ’786 does not teach that lemon oil or
d-limonene can be used to dissolve Q10. Appeal Br. 31–32. Patent Owner argues
that, “[o]n the contrary, [] Khan teach[es] melting point reduction as an alternative
. . . approach to liquefying CoQ-10, precisely because it is difficult to dissolve.”
Id. at 30-31. Furthermore, Patent Owner contends there would be no reasonable
expectation of success since Khan ’786 is “directed to reducing the melting point
of coenzyme Q-10, not dissolving it.” Id. Patent Owner states that Khan ’786
“teaches away” from utilizing d-limonene to dissolve Q10 because Khan ’786 uses
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

30

“melting point reduction because coenzyme Q-10 is difficult to dissolve.” Id. at
32.
Patent Owner argues that Khan ’786’s subsequent publication, Khan (2004),
investigating d-limonene is evidence of nonobviousness:
If it was obvious at the time of the ’072 patent application, that
d-limonene could be used to reduce the melting point of CoQ-10, then
Khan himself [in Khan 2004], would not have been investigating
subsequently whether d-limonene could be so-used. Similarly, if it
was obvious that d-limonene could be substituted for Motoyama’s
carvone, then Khan would not have been teaching melting point
reduction as an alternative to address the fact that CoQ-10 is difficult
to dissolve.
Id. at 33.
Patent Owner’s arguments are not supported by adequate evidence of record.
Even if the disclosed mechanisms are different – where Khan ’786 describes
“melting” Q10 and Motoyama describes “dissolving” Q10 – Motoyama
specifically teaches that spearmint and peppermint oils dissolve Q10 (FF13) and
these same oils are described by Khan ’786 as depressing the melting temperature
of Q10 (FF14). Consequently, in view of Motoyama, the skilled worker would
have recognized that certain oils that depress the melting temperature of Q10 also
dissolve it when an adequate amount of such oil is used for a given amount of Q10.
Based on this, the skilled worker would have had reason to use lemon oil and its
main constituent d-limonene in Motoyama’s method with a reasonable expectation
that it would work because other oils shown to depress the melting temperature of
Q10 were shown in Motoyama’s experiments to dissolve it.
We do not agree that that Khan ’786’s later experiments with d-limonene is
evidence of nonobviousness. Nazzal expressly suggested evaluating d-limonene
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

31

(FF16), providing explicit evidence that one of ordinary skill in the art had reason
to use it at the time of the invention. In view of this explicit suggestion in Nazzal,
one of ordinary skill in the art would had reason to use d-limonene in Motoyama’s
method, as well, since d-limonene is a monoterpene like carvone which had been
shown to dissolve Q10. Indeed, it was later shown by Khan (2004) that
d-limonene dissolves Q10. Khan (2004) states “CoQ is fairly soluble in
monoterpenes, R-limonene [d-limonene] (571.6 ± 5.03 mg/mL).” Khan (2004) 78.
As held in KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398, 421(2007):
When there is a design need or market pressure to solve a problem
and there are a finite number of identified, predictable solutions, a
person of ordinary skill has good reason to pursue the known options
within his or her technical grasp. If this leads to the anticipated
success, it is likely the product not of innovation but of ordinary skill
and common sense.
There is no persuasive evidence of record that one of ordinary skill in the art
would have had “to vary all parameters or try each of numerous possible choices
until one possibly arrived at a successful result, where the prior art gave either no
indication of which parameters were critical or no direction as to which of many
possible choices is likely to be successful.” In re O’Farrell, 853 F.2d 894, 903
(Fed. Cir. 1988); Bayer Schering Pharma AG v. Barr Labs., Inc., 575 F.3d 1341,
1347 (Fed. Cir. 2009).
For the foregoing reasons, we conclude that a preponderance of the evidence
supports the Examiner’s determination that claim 1 is obvious in view of
Motoyama, Khan ’786, Fenaroli, Exhibits B, C, and D, and Nazzal. Claims 2, 3,
5–10, 12–20, and 22–24 were not argued separately and thus fall with claim 1.

Claims 4, 11, 12, 21, and 22
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

32

Claims 4, 11, 12, 21, and 22 are further rejected based on the Steele and
Davidson. RAN 20-21. Patent Owner argues the claims are patentable for the
same reasons that the claims are not obvious in view of Motoyama, Khan ’786, and
Nazzal. Appeal Br. 33–34. Because we determined that these arguments are
unpersuasive, the rejections of claims 4, 11, 12, 21, and 22 are affirmed for the
reasons set forth by the Examiner.

TIME PERIOD FOR RESPONSE
In accordance with 37 C.F.R. § 41.79(a)(1), the “[p]arties to the appeal may
file a request for rehearing of the decision within one month of the date of: . . .
[t]he original decision of the Board under § 41.77(a).” A request for rehearing
must be in compliance with 37 C.F.R. § 41.79(b). Comments in opposition to the
request and additional requests for rehearing must be in accordance with 37 C.F.R.
§ 41.79(c), (d), respectively. Under 37 C.F.R. § 41.79(e), the times for requesting
rehearing under paragraph (a) of this section, for requesting further rehearing under
paragraph (d) of this section, and for submitting comments under paragraph (c) of
this section may not be extended.
An appeal to the United States Court of Appeals for the Federal Circuit
under 35 U.S.C. §§ 141-144 and 315 and 37 C.F.R. § 1.983 for an inter partes
reexamination proceeding “commenced” on or after November 2, 2002 may not be
taken “until all parties’ rights to request rehearing have been exhausted, at which
time the decision of the Board is final and appealable by any party to the appeal to
the Board.” 37 C.F.R. § 41.81. See also MPEP § 2682 (8th ed., Rev. 7, July
2008).
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

33

In the event neither party files a request for rehearing within the time
provided in 37 C.F.R. § 41.79, and this decision becomes final and appealable
under 37 C.F.R. § 41.81, a party seeking judicial review must timely serve notice
on the Director of the United States Patent and Trademark Office. See 37 C.F.R.
§§ 90.1 and 1.983.
AFFIRMED
Appeal 2015-007397
Reexamination Control 95/002,396
Patent 8,124,072 B2

34

Patent Owner:

WINTHROP & WEINSTINE, P.A.
Capella Tower, Suite 3500
225 South Sixth Street
Minneapolis, MN 55402

Third Party Requester:

McCARTER & ENGLISH LLP, HARTFORD
CITYPLACE 1
185 Asylum Street
Hartford, CT 06103

lb