Lipomedix Pharmaceuticals LTD. et al.

Patent Trials and Appeals Board

Mar 18, 2021

2020003764 (P.T.A.B. Mar. 18, 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.
15/559,395 09/18/2017 Alberto Gabizon 094893-0026/8003.US00 1096
108547 7590 03/18/2021
McDermott Will & Emery LLP
500 North Capitol Street NW
Washington, DC 20001
EXAMINER
SHOMER, ISAAC
ART UNIT PAPER NUMBER
1612
NOTIFICATION DATE DELIVERY MODE
03/18/2021 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):
mweipdocket@mwe.com
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte ALBERTO GABIZON and PATRICIA OHANA1
Appeal 2020-003764
Application 15/559,395
Technology Center 1600
Before ERIC B. GRIMES, JEFFREY N. FREDMAN, and
ULRIKE W. JENKS, Administrative Patent Judges.
GRIMES, Administrative Patent Judge.
DECISION ON APPEAL
This is an appeal under 35 U.S.C. § 134(a) involving claims to a
method of treating bladder cancer, which have been rejected as obvious.
We have jurisdiction under 35 U.S.C. § 6(b).
We AFFIRM.
STATEMENT OF THE CASE
“The present disclosure is based in part on the finding that folate-
targeted liposomes with a prodrug of mitomycin C are stable in urine for a

1 Appellant identifies the real party in interest as Lipomedix Pharmaceuticals
Ltd. Appeal Br. 1. We use the word “Appellant” to refer to “applicant” as
defined in 37 C.F.R. § 1.42.
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time sufficient for therapy in the bladder.” Spec. ¶ 27. “The prodrug
conjugate is not toxic, and after administration and upon exposure to
endogenous reducing agents or exposure to an exogenous reducing agent,
the conjugate decomposes to yield mitomycin C in its native state and with
biological activity.” Id. ¶ 30.
Claims 1 and 5–11 are on appeal. Claim 1, reproduced below, is
illustrative:
1. A method for treating bladder cancer, comprising:
administering to an individual with bladder cancer
liposomes comprising a folate targeting moiety and a prodrug
of mitomycin C, the liposomes administered in an amount that
yields a therapeutically-effective amount of mitomycin C for
the treatment of bladder cancer,
wherein administering comprises administering via
intravesical instillation,
wherein the prodrug of mitomycin C is a conjugate of
mitomycin C releasably attached to a lipophilic moiety, and is
of the form:

, wherein L is a hydrophobic moiety, R1 represents a
mitomycin C residue, orientation of the –CH2R1 group is
selected from the ortho position and the para position.

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The claims stand rejected as follows:
Claims 1 and 5–11 under 35 U.S.C. § 103 as obvious based on
Zalipsky,2 Gabizon,3 and Dalton4 (Final Action5 3); and
Claims 1 and 5–11 under 35 U.S.C. § 103 as obvious based on
Zalipsky, Li,6 and Dalton (Final Action 7).
OPINION
Obviousness: Zalipsky, Gabizon, and Dalton
All of the claims stand rejected as obvious based on Zalipsky,
Gabizon, and Dalton. The Examiner finds that Zalipsky teaches a method of
treating tumors, including bladder cancer, by administering a prodrug
conjugate of mitomycin C in the form of a liposome composition. Final
Action 3. The Examiner finds that the prodrug conjugate taught by Zalipsky
corresponds to the structure in claim 1. Id. at 5–6.
The Examiner finds that Zalipsky does not teach a folate targeting
moiety, but Gabizon teaches liposome-entrapped drugs targeted to tumor
cells via folate attached to the phospholipids of the liposome. Id. at 3–4. The
Examiner concludes that it would have been obvious “to have attached folic
acid (i.e. folate), as of Gabizon to the liposome lipids in the liposome of

2 Zalipsky et al., US 2004/0161455 A1, published Aug. 19, 2004.
3 Gabizon et al., Tumor cell targeting of liposome-entrapped drugs with
phospholipid-anchored folic acid-PEG conjugates, Advanced Drug Delivery
Reviews, 56:1177–1192 (2004).
4 Dalton et al., Pharmacokinetics of Intravesical Mitomycin C in Superficial
Bladder Cancer Patients, Cancer Research, 51:5144–5152 (1991).
5 Office Action dated June 19, 2019.
6 Li et al., Therapeutic Effect of Folate-Targeted and PEGylated Phytosomes
Loaded with a Mitomycin C-Soybean Phosphatidylcholine Complex,
Molecular Pharmaceutics, 11:3017–3026 (2014).
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Zalipsky” because Zalipsky teaches treating cancer and “Gabizon teaches
that folate is useful for targeting tumors because folate receptor is expressed
on tumor cells.” Id. at 4.
The Examiner acknowledges that Zalipsky and Gabizon do not teach
intravesical instillation, but finds that Dalton teaches intravesical
administration of mitomycin C to treat superficial bladder cancer. Id. at 4–5.
The Examiner concludes that it would have been obvious “to have
administered the liposome comprising mitomycin C prodrug of Zalipsky, as
modified with folate by Gabizon, in an intravesical manner in order to treat
bladder cancer” because “Dalton indicates that mitomycin C may be
administered intravesically to treat bladder cancer.” Id. at 5.
We agree with the Examiner that the cited references support a prima
facie case of obviousness. Zalipsky states that “[m]itomycin is an established
chemotherapeutic agent given for several different types of cancer, including
breast, stomach, gullet and bladder cancer. The agent acts by cross-linking
DNA so the cancer cells are unable to proliferate.” Zalipsky ¶ 3 (emphasis
added).
Zalipsky discloses “a method for reducing the cytotoxicity of
mitomycin C,” by providing the mitomycin C in the form of a “prodrug
conjugate [that] is comprised of a lipid linked to the drug via a cleavable
linkage, the lipid being incorporated into a liposomal formulation.” Id. ¶ 2.
Zalipsky describes
providing mitomycin C in the form of a liposome composition
comprised of a vesicle-forming lipid and . . . a conjugate having
the general form:
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wherein L is a hydrophobic moiety suitable for incorporation
into a liposomal lipid bilayer, R1 is mitomycin C covalently
attached to the dithiobenzyl moiety, and where orientation of
the CH2R1 group is selected from the ortho position and the
para position.
Id. ¶¶ 13–14.
Thus, Zalipsky teaches or suggests a method of treating bladder
cancer comprising administering liposomes comprising the mitomycin C
prodrug recited in Appellant’s claim 1.
Zalipsky does not teach including a folate targeting moiety in its
liposomes, but Gabizon teaches that “[t]argeting of liposomes with
phospholipid-anchored folate conjugates is an attractive approach to deliver
chemotherapeutic agents to folate receptor (FR) expressing tumors.”
Gabizon 1177, Abstract. Gabizon’s Figure 17 is reproduced below:

7 The figure reproduced here is from page 7 of the Answer due to the poor
quality of the figure in the record copy of Gabizon.
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Gabizon’s Figure 1 shows “[a] schematic illustration of the folate
liposome targeting concept.” Id. at 1178, left col. More specifically, the
figure shows “[t]he various steps involved in the targeting process . . .
numerically designated from 1 to 6.” Id. at 1179, legend to Fig. 1. In step
(1), “[l]iposomes with long-circulating properties increase the number of
passages through the tumor microvasculature.” Id. In step (2), “[i]ncreased
vascular permeability in tumor tissue enables . . . liposomes to extravasate
and reach the tumor interstitial fluid.” Id. In step (3), “[d]rug is gradually
released from liposomes . . . and enters tumor cells as free drug to exert a
cytotoxic effect.” Id.
Gabizon states that “[s]teps 1–3 are common to nontargeted and
targeted liposomes. Steps 4–6 are specific to FTL [folate-targeted
liposomes].” Id. In step (4), “liposomes bind to the FR [folate receptor]
expressed on the tumor cell membrane via the folate ligand.” Id. In step (5),
“[l]iposomes are internalized by tumor cells.” Id. In step (6), “[i]nternalized
liposomes release their drug content in the cytosol enabling the drug to exert
its cytotoxic effect.” Id.
That is, with folate-targeted liposomes (FTL), “once liposomes have
penetrated the tumor interstitial fluid, binding of targeted liposomes to FR
may occur thus shifting the intra-tumor distribution from the extracellular
compartment to the tumor cell compartment.” Id. at 1178, right col. Gabizon
states that “the theoretical advantages of FTL over NTL [non-targeted
liposomes] are related to a shift of liposome distribution to the tumor cell
compartment, delivery of liposomal contents to an intra-cellular
compartment in liposome-associated form, and, possibly, prolonged
liposome retention in the tumor.” Id.
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Gabizon concludes that
the current body of data does not support the claim that folate
targeting increases to a sizable extent the overall liposome
concentration in subcutaneously-growing tumor implants.
However, folate targeting may still lead to significant
pharmacodynamic changes with improvement of the therapeutic
index by shifting drug distribution from the extracellular to the
intracellular tumor compartment while systemic toxicity is left
unchanged or even reduced.
Id. at 1190, right col.
Based on Gabizon’s disclosure, it would have been obvious to a
person of ordinary skill in the art to modify the mitomycin C prodrug-
containing liposomes taught by Zalipsky to include phospholipid-anchored
folate conjugates, as taught by Gabizon. Motivation to do so is provided by
Gabizon, which teaches that folate-targeted liposomes (FTL) target folate
receptor-expressing tumors by binding to the folate receptor, being
internalized by the tumor cells, and releasing their drug contents in the
cytosol of the tumor cells. Thus, FTLs “shift[] the intra-tumor distribution
from the extracellular compartment to the tumor cell compartment,” id. at
1178, right col., leading to an “improvement of the therapeutic index.” Id. at
1190, right col.
Neither Zalipsky nor Gabizon specifically teach intravesical
instillation in the treatment of bladder cancer, but Dalton teaches that
“[i]ntravesical mitomycin C (MMC) therapy is used to treat superficial
bladder cancer.” Dalton 5144, Abstract. Dalton teaches, in fact, that
“[t]ransurethral tumor resection and intravesical chemotherapy are the most
commonly used treatment modality for superficial bladder cancer.” Id. at
5144, left col.
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Therefore, it would have been obvious to treat bladder cancer by
administering the mitomycin C prodrug-containing liposomes taught by
Zalipsky, modified to include a folate targeting moiety as suggested by
Gabizon, by intravesical instillation, because Dalton teaches that that method
of administration is the most commonly used treatment modality for treating
superficial bladder cancer.
Appellant argues that “Zalipsky teaches . . . that the liposomal
mitomycin C prodrug exerts its therapeutic effect via extracellular cleavage
of the mitomycin C prodrug to release mitomycin C which is then taken up
by the tumor cells.” Appeal Br. 4. Appellant argues that the Gabizon
Declaration8 states that “neither liposomal mitomycin C prodrug as taught in
Zalipsky nor mitomycin C prodrug itself can be internalized into the cell for
intracellular cleavage of the mitomycin C prodrug to exert cytotoxicity,
whereas “ mitomycin C in free form can be taken up by cancer cell very
quickly.” Id., citing Gabizon Decl. ¶¶ 9, 10.
This argument is unpersuasive. Zalipsky states that its results show
that the disclosed mitomycin C prodrug is less toxic when administered in
vivo than free mitomycin C, and that “multi-drug resistant cells are able to
take up the mitomycin C when administered in the form of the [prodrug]
conjugate.” Zalipsky ¶ 117. The Gabizon Declaration clarifies that Zalipsky
is referring to “uptake of mitomycin C in its free form after the free-form
mitomycin C is extracellularly released from the liposomal mitomycin C
prodrug.” Gabizon Decl. ¶ 8.

8 Declaration under 37 C.F.R. § 1.132 of Alberto A. Gabizon, filed May 20,
2019.
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Zalipsky’s disclosure thus is consistent with the disclosure of the
Gabizon reference, which states that non-targeted liposomes extravasate
from the vasculature in the vicinity of tumor tissues, after which “[d]rug is
gradually released from liposomes remaining in the interstitial fluid and
enters tumor cells as free drug to exert a cytotoxic effect.” Gabizon 1179,
legend to Fig. 1. Gabizon also discloses that folate-targeted liposomes have
the added property of being taken up by tumor cells after they bind to folate
receptors and being internalized; the folate-targeted liposomes then release
their drug contents in the cytosol of the tumor cells. Id. A skilled artisan
therefore would have expected that modification of Zalipsky’s liposomes to
include a folate targeting moiety would result in “a shift of liposome
distribution to the tumor cell compartment, delivery of liposomal contents to
an intra-cellular compartment in liposome-associated form, and, possibly,
prolonged liposome retention in the tumor.” Id. at 1178, right col.
Appellant notes that “Gabizon teaches including a folate receptor
targeting moiety on the liposomal exterior surface . . . so that the liposome is
internalized by the cell.” Appeal Br. 4. Appellant argues, however, that
[a]dding folate targeting ligands as taught by Gabizon to
Zalipsky’s liposomes has the potential outcome that the folate
ligand achieves the desired intracellular uptake of the liposomes
sans a mitomycin C prodrug conjugate due to its release prior to
intracellular uptake. Accordingly, there is no benefit to adding a
folate targeting moiety as an empty, drug-free liposome
delivered intracellularly has no benefit.
Id.
This argument is also unpersuasive. Appellant has pointed to no
evidence showing that modifying Zalipsky’s liposomes to include a folate
targeting moiety, as suggested by Gabizon, would result in the liposomes
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releasing all of their mitomycin C prodrug contents extracellularly, so that
any liposomes taken up by the tumor cells would be empty. Gabizon’s
disclosure is to the contrary. Gabizon states that both non-targeted and
folate-targeted liposomes release some of their contents extracellularly. See
Gabizon 1179, legend to Fig. 1 (“Steps 1–3 are common to nontargeted and
targeted liposomes. . . . (3) Drug is gradually released from liposomes
remaining in the interstitial fluid and enters tumor cells as free drug to exert
a cytotoxic effect.”). Folate-targeted liposomes, however, also have the
property of being taken up by tumor cells and releasing their drug contents
in the tumor cells’ cytosol. See id. (“(5) Liposomes are internalized by tumor
cells. . . . (6) Internalized liposomes release their drug content in the
cytosol.”).
Appellant argues that “Gabizon . . . discloses that in three tumor
models, FTL-Dox and NTL-Dox were equally active. Gabizon cautions that
‘the concept of ligand-mediated active liposome targeting still needs further
experimental proof of validity in animal models and surely in clinical
trials.’” Appeal Br. 5 (citation omitted). Appellant argues that, therefore, a
skilled artisan would not be motivated to add folate to Zalipsky’s liposomes
“because Gabizon indeed teaches that liposomes with or without folate have
similar bio-distribution in tumors and similar anti-tumor activity.” Id.
This argument is also unpersuasive. While Gabizon indicates that
further testing of folate-targeted liposomes was still needed, it also states
that folate-targeted liposomes should provide advantages compared to non-
targeted liposomes. See Gabizon 1178, right col. (“[T]he theoretical
advantages of FTL over NTL are related to a shift of liposome distribution to
the tumor cell compartment, delivery of liposomal contents to an intra-
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cellular compartment in liposome-associated form, and, possibly, prolonged
liposome retention in the tumor.”); id. at 1190, right col. (“[F]olate targeting
may still lead to significant pharmacodynamic changes with improvement of
the therapeutic index by shifting drug distribution from the extracellular to
the intracellular tumor compartment while systemic toxicity is left
unchanged or even reduced.”).
Thus, Gabizon would have provided a skilled artisan with a
reasonable expectation that adding a folate targeting moiety to Zalipsky’s
liposomes would result in an improved therapeutic agent, at least because it
would shift drug distribution from the extracellular to the intracellular tumor
compartment. “Only a reasonable expectation of success, not absolute
predictability, is necessary for a conclusion of obviousness.” In re Longi,
759 F.2d 887, 897 (Fed. Cir. 1985).
Appellant also argues that
[t]he liposomal drugs disclosed in Gabizon are free drugs, NOT
prodrugs. . . . [N]o discussion of administration of folate
targeted liposome encapsulated drugs by intravesical
instillation, hence no discussion of effectiveness of this route of
administration of folate targeted liposome encapsulated drugs,
is provided. Accordingly, there is no reasonable expectation of
success with respect to the claimed method.
Appeal Br. 6. Appellant argues that “[t]here is further lack of expectation of
success in view of the fact that mitomycin C is not stable in urine. Dalton
repeatedly makes the point that mitomycin C degrades in urine.” Id.
Appellant argues that “[r]elease of mitomycin C in the bladder, for treating
bladder cancer, potentially exposes the mitomycin C to urine, where it is
subject to degradation. Accordingly, it is unclear whether the prodrug-
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conjugate liposomes of Zalipsky would be effective to treat bladder cancer.”
Id.
This argument is also unpersuasive. Although Gabizon does not teach
liposome-encapsulated prodrugs, Zalipsky teaches that free mitomycin C is
released from its prodrug under reducing conditions, such as those found in
the vicinity of tumor cells. See Zalipsky ¶ 2 (“The prodrug conjugate is
cleavable under mild thiolytic conditions in vivo for release of mitomycin
C.”); id. ¶ 117 (“The increased level of thioredoxin in tumor cells offers a
unique synergy with the mitomycin C conjugate described here, since a
natural source of a reducing enzyme is concentrated in the target tissue.”).
With regard to the potential degradation of mitomycin C in urine,
Dalton refers to “drug removal by degradation and absorption” during
therapy or during bladder exposure to mitomycin C (MMC). See Dalton
5144, Abstract. However, Dalton also discloses how to minimize such
degradation. See id. at 5150, right col. (“[T]he rate of nonenzymatic
degradation of MMC was 12-fold slower at pH 7 relative to pH 5. It would
be logical to buffer the bladder instillate to pH 7 during therapy in order to
decrease the rate of nonenzymatic degradation.”); id. at 5151, left col.
(“Further enhancement of target site exposure requires . . . more complete
bladder emptying, control of the urine pH for optimal drug activity and
stability, decreased fluid intake prior to and during therapy, increased
instillation periods, and more complete distribution and mixing of the dosing
solution within the bladder during therapy.”). We therefore conclude that the
cited references would have provided a reasonable expectation of success in
combining Gabizon’s folate targeting moiety with Zalipsky’s liposomes, and
administering them via intravesical instillation as suggested by Dalton.
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We affirm the rejection of claim 1 under 35 U.S.C. § 103 based on
Zalipsky, Gabizon, and Dalton. Claims 5–11 fall with claim 1 because they
were not argued separately. 37 C.F.R. § 41.37(c)(1)(iv).
Obviousness: Zalipsky, Li, and Dalton
All of the claims stand rejected as obvious based on Zalipsky, Li, and
Dalton. The Examiner relies on Zalipsky and Dalton for the same
disclosures discussed above. Final Action 7–9. The Examiner finds that Li
teaches “a folate targeted ‘phytosome’ comprising mitomycin C,” where
“[t]he term ‘phytosome’ refers to a liposome with a lower phospholipid
dosage as compared with liposomes.” Id. at 8. The Examiner finds that “Li
teaches folate as a targeting element to target cancer.” Id.
The Examiner concludes that it would have been obvious “to have
attached folic acid (i.e. folate), as of Li, to the liposome lipids in the
liposome of Zalipsky . . . in order to have predictably targeted said liposome
to tumors with a reasonable expectation of success.” Id. at 8–9. The
Examiner also concludes that it would have been obvious “to have
administered the liposome comprising mitomycin C prodrug of Zalipsky, as
modified with folate by Li, in an intravesical manner in order to treat bladder
cancer” because “Dalton indicates that mitomycin C may be administered
intravesically to treat bladder cancer.” Id. at 9.
We agree with, and adopt, the Examiner’s fact-finding and
conclusions. Zalipsky and Dalton are discussed above. Li states that “[a]
mitomycin C (MMC)-soybean phosphatidylcholine complex loaded in
phytosomes was previously reported . . . , but this approach was limited by
rapid elimination from the body and lack of target specificity.” Li 3017,
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Abstract.9 Li reports that, to overcome these issues, the MMC-loaded
phytosomes “were surface-functionalized with folate-PEG (FA-PEG) to
achieve reduced toxicity and a superior MMC-mediated therapeutic effect.”
Id.
Li states that “[t]he remarkable features of FA-PEG-MMC-loaded
phytosomes included increased cellular uptake in HeLa cells and higher
accumulation in H22 tumor-bearing mice over that of the PEG-MMC-loaded
phytosomes.” Id. Further, Li reports that “FA-PEG-MMC-loaded
phytosomes were associated with enhanced cytotoxic activity in vitro and an
improved antitumor effect in vivo compared to that resulting from free
MMC injection.” Id.
Based on these teachings, it would have been obvious to modify
Zalipsky’s liposomes, containing mitomycin C prodrug, by surface-
functionalizing them with folate-PEG, as taught by Li, because Li teaches
that FA-PEG-modified phytosomes have enhanced cytotoxic activity in vitro
and improved antitumor effect in vivo compared to free mitomycin C. It
would also have been obvious to administer the modified liposomes by
intravesical administration to treat bladder cancer, because Zalipsky teaches
that its liposomes can be used to treat bladder cancer and Dalton teaches that
intravesical chemotherapy is a commonly used treatment for bladder cancer.
Thus, the combined disclosures of Zalipsky, Li, and Dalton would have
made obvious the method of claim 1 to a person of ordinary skill in the art.

9 “A phytosome is a type of drug-phospholipid complex-based soft NP
[nanoparticle] that is advantageous for drug delivery because of its lower
phospholipid dosage compared to that of liposomes.” Li 3017, left col.
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Appellant argues that, “[a]ssuming folate ligand attached phytosomes
target tumor cells more than phytosomes without folate ligand attached, a
[s]killed artisan would not be motivated to attach a folate ligand to
liposomes of Zalipsky because liposomes were found to be inferior to
phytosomes according to Li.” Appeal Br. 7.
This argument is unpersuasive. Li teaches that phytosomes are
“advantageous for drug delivery because of [their] lower phospholipid
dosage compared to that of liposomes.” Li 3017, left col. However, Li also
notes that “Zalipsky et al. reported a MMC drug delivery system in which
the liposome acted as a drug carrier.” Id. at 3017, right col. Li does not
indicate that Zalipsky’s liposome-based formulation was ineffective for
delivering mitomycin C, and thus would not have discouraged a skilled
artisan from modifying Zalipsky’s liposomes in the same manner that Li
teaches for its MMC-containing phytosomes.
Appellant also argues that “Li discloses administration route by IV
injection, which is completely different from the claimed intravesical
administration,” and “[a]ny advantages or success associated with IV
injection as disclosed by Li cannot be reasonably expected from intravesical
instillation.” Appeal Br. 7.
These arguments are also unpersuasive. Dalton discloses that
intravesical administration of chemotherapeutic agents is a commonly used
treatment modality for bladder cancer, and therefore an obvious route of
administering the mitomycin C prodrug-containing liposomes made obvious
by the combination of Zalipsky and Li. Appellant has cited no evidence to
show that the advantages disclosed by Li would not also apply to liposomes
administered by intravesical administration, and “[a]ttorneys’ argument is no
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substitute for evidence.” Johnston v. IVAC Corp., 885 F.2d 1574, 1581 (Fed.
Cir. 1989).
We affirm the rejection of claim 1 under 35 U.S.C. § 103 based on
Zalipsky, Li, and Dalton. Claims 5–11 fall with claim 1 because they were
not argued separately. 37 C.F.R. § 41.37(c)(1)(iv).
DECISION SUMMARY
In summary:
Claim(s)
Rejected
35 U.S.C. § Reference(s)/Basis Affirmed Reversed
1, 5–11 103 Zalipsky, Gabizon,
Dalton
1, 5–11
1, 5–11 103 Zalipsky, Li, Dalton 1, 5–11
Overall
Outcome
1, 5–11

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