CRODA INTERNATIONAL PLC

Patent Trials and Appeals Board

Sep 3, 2020

15565983 - (D) (P.T.A.B. Sep. 3, 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.
15/565,983 10/12/2017 Roberta Ondei CDA-181US 3305
23122 7590 09/03/2020
RATNERPRESTIA
2200 Renaissance Blvd
Suite 350
King of Prussia, PA 19406
EXAMINER
SONG, JIANFENG
ART UNIT PAPER NUMBER
1613
NOTIFICATION DATE DELIVERY MODE
09/03/2020 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):
PCorrespondence@ratnerprestia.com
PTOL-90A (Rev. 04/07)

UNITED STATES PATENT AND TRADEMARK OFFICE
_________________

BEFORE THE PATENT TRIAL AND APPEAL BOARD
_________________

Ex parte ROBERTA ONDEI and EDNA FERNANDES
_________________

Appeal 2020-000556
Application 15/565,983
Technology Center 1600
_________________

Before RICHARD M. LEBOVITZ, JASON V. MORGAN, and
DEBORAH KATZ, Administrative Patent Judges.

KATZ, Administrative Patent Judge.

DECISION ON APPEAL
Appellant1 seeks our review2, under 35 U.S.C. § 134(a), of the
Examiner’s decision to reject claims 1, 3–10 and 15. Claims 2 and 12 were
canceled and claims 11, 13, and 14 were withdrawn. We have jurisdiction
under 35 U.S.C. § 6(b). We REVERSE.

1 We use the word “Appellant” as defined in 37 C.F.R. § 1.42. Appellant
identifies the real party in interest as Croda International PLC. (Appeal Br.
1.)
2 We consider the Final Office Action issued December 26, 2018 (“Final
Act.”), the Appeal Brief filed July 26, 2019 (“Appeal Br.”), the Examiner’s
Answer issued on October 7, 2019 (“Ans.”), the Reply Brief filed November
1, 2019 (“Reply Br.”).
Appeal 2020-000556
Application 15/565,983

2
Appellant’s Specification is directed to emulsifiers for injectable
water in oil emulsions, particularly for use in veterinary vaccines. (Spec.
1:3–4.)
Appellant’s claim 1 recites:
1. A vaccine formulation comprising a water-in-oil
emulsion and at least one vaccine antigen, oil, and water, where
said emulsion comprises an emulsifier having a general
structure (I):

R1·[(AO)n–R2]m (I)

wherein

R1 is the residue of a polyol or polyamine, each said
polyol or polyamine having m active hydrogen atoms, where m
is an integer of at least 2;
AO is an oxyalkylene group;

each n independently represents an integer in the
range from 1 to 100;

each R2 independently represents hydrogen, or an
acyl group represented by -C(O)R3 wherein each R3
independently represents a residue of polyhydroxyalkyl
carboxylic acid, polyhydroxyalkenyl carboxylic acid,
hydroxyalkyl carboxylic acid, hydroxyalkenyl carboxylic
acid, oligomer of hydroxyalkyl carboxylic acid, or
oligomer of hydroxyalkenyl carboxylic acid; and

wherein on average at least two R2 groups per
molecule are alkanoyl groups as defined.

(Appeal Br. 8.)

Appeal 2020-000556
Application 15/565,983

3
The Examiner rejects Appellant’s claims 1, 3–10, and 15 under 35
U.S.C. § 103 as obvious over Brancq3 and Garti.4 (See Final Act. 3–6.)
As the Examiner finds, Brancq teaches an injectable vaccine
comprising an oily adjuvant and an emulsifier. (See Brancq Abstract; see
Ans. 3.) Brancq teaches that the emulsifier can be obtained by condensing a
fatty acid, such as linoleic and ricinoleic acids, with a sugar, such as
mannitol, glucose, sucrose, or with glycerol. (See Brancq 5:65–6:2; see Ans.
3.) Brancq teaches that the hydrophilicity of the ester can be modified by
grafting hydrophilic groups such as ethylene oxide or propylene oxide. (See
Brancq 6:7–10; see Ans. 3.)
Brancq teaches that it was known that the injectibility of oily vaccines
could be improved by incorporating a small proportion of the hydrophilic
emulsifier, such as polysorbate 80, in an antigen medium. (Brancq 3:4–8.)
But Brancq also teaches that it was known that polysorbate 80 attacks the
cell wall and so is potentially toxic. (See id. at 3:11–13.)
The Examiner finds that Brancq does not teach an integer n for
oxyalkylene with an MW 3000–8000. (See Final Act. 4.)
Garti teaches microemulsion pharmaceutical compositions that have
enhanced permeability and extended release properties. (See Garti Abstract;
see Ans. 4.) Garti lists PEG-40 and PEG-80, among other surfactants, for
use in the disclosed pharmaceutical compositions. (See Garti ¶ 53; see Ans.
4.)

3 Brancq, US Patent US 5,422,109, issued June 6, 1995.
4 Garti et al., US Patent Application Publication 2010/0143462 A1,
published June 10, 2010.
Appeal 2020-000556
Application 15/565,983

4
According to the Examiner, the amount of PEG on polyoxyethylene
mannitol ricinoleate could have been optimized through routine
experimentation. (See Ans. 4.) The Examiner finds that because Garti
teaches PEG (40–80) sorbitan fatty acid ester it would have been obvious to
one of ordinary skill to have polyoxyethylene mannitol ricinoleate with 40–
80 PEG as a surfactant and that there would have been a reasonable
expectation of success in achieving the claimed vaccine formulation. (See
Ans. 4–5.)
Appellant argues that the Examiner erred because claim 1 requires at
least two R2 groups per molecule are alkanoyl groups, but that the
polyoxyethylene mannitol ricinoleate with 40–80 PEG proposed by the
Examiner is a monoester. (See Appeal Br. 5.) Thus, Appellant argues that
the polyoxyethylene mannitol ricinoleate with 40–80 PEG proposed by the
Examiner does not fall within the scope of claim 1. (See id.) Appellant
argues further that Brancq fails to teach how or where the hydrophilic
groups are grafted, how many hydrophilic groups are grafted, or that at least
two alkanoyl groups are present, as specified in claim 1 of the present
application. (See Ans. 6.)
The Examiner asserts that mono-ricinoleate, di-ricinoleate, and tri-
ricinoleate will normally form when PEG groups are grafted on to mannitol
ricinoleate. (See Ans. 9.) According to the Examiner, Brancq teaches
surfactant mannitol, glucose ester with ricinoleic modified with ethylene
oxide, but does not expressly indicate how mannitol (glucose) ricinoleate is
modified with ethylene oxide. (See Ans. 7.) The Examiner finds, though,
that because polysorbate 80 was a commonly known surfactant from
sorbitan monooleate that could be modified by grafting polyoxyethylene
Appeal 2020-000556
Application 15/565,983

5
(PEG) between the hydroxyl of sugar and acyl group, it would have been
obvious for one of ordinary skill in the art to modify mannitol (glucose)
ricinoleate by similarly grafting PEG between hydroxyl of sugar and acyl
group to produce polyoxyethylene mannitol (glucose) ricinoleate. (See Ans.
7–8.) The Examiner asserts that because polysorbate 80 was a commonly
known surfactant it teaches how PEG groups can be grafted to produce
polyoxyethylene mannitol (glucose) ricinoleate and renders it obvious in
view of Brancq. (See Ans. 8.) The Examiner provides three different
example structures of PEG mannitol ricinoleate, which are reproduced
below.

(Ans. 9.) Three structures of PEG mannitol ricinoleate are depicted, having
either one, two, or three ricinoleate residues.
The Examiner fails to explain, though, why one of ordinary skill in the
art would have made the asserted modifications of the compounds taught in
Brancq. The Examiner states that “[o]ne of ordinary skill in the art would
have been motivated to have polyoxyethylene mannitol ricinoleate with 40-
80 PEG because the amount of PEG is adjustable and optimizable under
prior art condition or through routing experimentation.” (Ans. 4.) Not only
Appeal 2020-000556
Application 15/565,983

6
does the Examiner fail to cite support for the optimization of PEG and how
such optimization would be achieved, but the Examiner’s statement fails to
explain why one would undertake such optimization, given that Brancq does
not teach at least two R2 alkanoyl groups. Brancq teaches condensing a fatty
acid with a sugar or glycerol and modifying the esters obtained by grafting a
hydrophilic group, but the Examiner does not cite to a teaching of how to
optimize, control or otherwise achieve any specificity in such reactions.
(See Brancq 5:65–6:10.)
The Examiner cites to Example 1 of Appellant’s Specification to show
that an esterification reaction of PEG-50 sorbitol and poly-12-hydroxystearic
acid results in sorbitol poly-12-hydroxystearic acid ester that includes di- or
tri-ester of PEG-50 sorbitol, but the Appellant’s Specification cannot be used
as evidence of a reason to make such modifications without resorting to
improper hindsight. (See Ans. 9.) Furthermore, we agree with Appellant
that Example 1 does not teach using ricinoleate diesters or triesters modified
with oxyalkylene groups and, thus, fails to show that modification of the
compounds of Brancq would necessarily lead to the structure recited in
claim 1. (See Appeal Br. 6.)
We agree with Appellant that Brancq fails to teach or suggest
modification of polyoxyethylene mannitol ricinoleate with 40–80 PEG to
achieve a compound with at least two R2 alkanoyl groups per molecule as
required in claim 1. (See Appeal Br. 5.) We also agree with Appellant that
the mere listing of 40 PEG and 80 PEG in Garti fails to cure this deficiency.
(See Appeal Br. 6.)
Furthermore, Bracq does not identify the position of the oxyalkylene
group when grafted to the mannitol group. The Examine states the it would
Appeal 2020-000556
Application 15/565,983

7
be obvious to place it between the sugar and acyl group, but does not
provide an adequate reason for doing so. See Ans. 7–8.
Accordingly, we are persuaded by Appellant’s arguments that the
Examiner fails to show that the combination of Brancq and Garti renders the
vaccine formulation of claim 1 obvious. Because claims 3–10 and 15
depend on claim 1, we are also persuaded that the Examiner fails to show
that these claims are obvious.
CONCLUSION
Upon consideration of the record and for the reasons given, we
reverse the Examiner’s rejection.
In summary:
Claims
Rejected
35 U.S.C. § References Affirmed Reversed
1, 3–10, 15 103 Brancq, Garti 1, 3–10, 15

REVERSED