Paul Savage

Patent Trials and Appeals Board

Apr 30, 2021

2020005084 (P.T.A.B. Apr. 30, 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.
15/481,884 04/07/2017 Paul B. Savage 19250.26.1.1 1075
22913 7590 04/30/2021
Workman Nydegger
60 East South Temple
Suite 1000
Salt Lake City, UT 84111
EXAMINER
BADIO, BARBARA P
ART UNIT PAPER NUMBER
1628
NOTIFICATION DATE DELIVERY MODE
04/30/2021 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):
docketing@wnlaw.com
PTOL-90A (Rev. 04/07)

UNITED STATES PATENT AND TRADEMARK OFFICE
____________

BEFORE THE PATENT TRIAL AND APPEAL BOARD
____________

Ex parte PAUL B. SAVAGE
____________

Appeal 2020-005084
Application 15/481,884
Technology Center 1600
____________

Before DONALD E. ADAMS, TAWEN CHANG, and
RACHEL H. TOWNSEND, Administrative Patent Judges.

ADAMS, Administrative Patent Judge.

DECISION ON APPEAL
Pursuant to 35 U.S.C. § 134(a), Appellant1 appeals from Examiner’s
decision to reject claims 1, 6, 10, 12, 20, 24, 26, 31–42, and 44 (Appeal Br.
3).2 We have jurisdiction under 35 U.S.C. § 6(b).
We REVERSE.

1 We use the word “Appellant” to refer to “applicant” as defined in 37
C.F.R. § 1.42. Appellant identifies the real party in interest as “Brigham
Young University” (Appellant’s March 18, 2020, Appeal Brief (Appeal Br.)
3).
2 Pending claims 2–5, 11, 13–19, 21–23, 25, 27–30, 43, and 46–48 stand
withdrawn from consideration (Appeal Br. 3).
Appeal 2020-005084
Application 15/481,884

2
STATEMENT OF THE CASE
Appellant’s disclosure “relates to the fields of pharmaceutical
chemistry, biochemistry, and medicine. In particular, the present application
relates to certain cationic steroidal antimicrobials (‘CSA compounds’ or
‘ceragenins’)” (Spec.3 ¶ 2). Appellant’s claim 1 is reproduced below:
1. A compound of Formula (I), or a pharmaceutically
acceptable salt thereof:

(I)
wherein
R1 is selected from the group consisting of an optionally
substituted C11-22-alkylamino-Cx-alkyl; an optionally substituted
C11-22-alkylester-Cx-alkyl; and optionally substituted Z1,Z2-
amino-Cx-alkyl;
R2, R3, and R4, are independently selected from the group
consisting of optionally substituted amino-Ca-alkyl and
optionally substituted amino-Ca-alkylcarbonyl;
x is 1-5;
Z1 and Z2 are independently unsubstituted C6-22-alkyl;
and
a is 2-5,
with the proviso that when R2, R3, and R4 are each
unsubstituted amino-C3-alkyl, R1 is not unsubstituted C16-
alkylamino-C3-alkyl, and

3 Appellant’s April 7, 2017, Specification.
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with the proviso that when R2, R3, and R4 are each
unsubstituted amino-C3-alkyl, Z1 and Z2 are not both C8-alkyl.
(Appeal Br. 17.)
In response to Examiner’s January 10, 2018 Requirement for Species
Election, Appellant elected “the species of compounds corresponding to
CSA-144,” having the following formula:

(Appellant’s March 9, 2018 Response to Restriction Requirement 2.) We
limit the scope of our review to Appellants’ elected invention. Ex parte
Ohsaka, 2 USPQ2d 1460, 1461 (BPAI 1987).

Grounds of rejection before this Panel for review:
Claims 1, 6, 10, 12, 20, 24, 26, 31–42, and 44 stand rejected under the
judicially created doctrine of obviousness-type double patenting as being
unpatentable over the claims of Savage ’234. 4
Claims 1, 6, 10, 12, 20, 24, 26, 31–42, and 44 stand rejected under the
judicially created doctrine of obviousness-type double patenting as being
unpatentable over the claims of Savage ’904.5
Claims 1, 6, 10, 12, 20, 24, 26, 31–42, and 44 stand rejected under 35
U.S.C. § 103(a) as unpatentable over Savage ’234.

4 Savage et al., US 7,598,234 B2, issued Oct. 6, 2009.
5 Savage et al., US 6,767,904 B2, issued July 27, 2004.
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FACTUAL FINDINGS (FF)
FF 1. Savage ’234 discloses “steroid derivatives and processes and
intermediates for the preparation of these compounds” (Savage ’234 1:33–
35; see Ans.6 4).
FF 2. Savage ’234’s claim 1 is reproduced below:
1. A method of treating a microbial infection of a host by
administering to the host an effective amount of an
antimicrobial composition comprising a compound according to
formula I

wherein:
fused rings A, B, C, and D are independently saturated or fully
or partially unsaturated; and R1 through R4, R6, R7, R11, R12,
R15, R16, and R17 is each independently selected from the
group consisting of hydrogen, hydroxyl, a substituted
orunsubstituted (C1–C10) alkyl, (C1–C10) hydroxyalkyl,
(C1–C10) alkyloxy-(C1–C10) alkyl, (C1–C10)
alkylcarboxy-(C1–C10) alkyl, (C1–C10) alkylamino-(C1–
C10) alkyl, (C1–C10) alkylamino-(C1–C10) alkylamino,
(C1–C10) alkylamino-(C1–C10) alkylamino-(C1–C10)
alkylamino, a substituted or unsubstituted (C1–C10)
aminoalkyl, a substituted or unsubstituted aryl, a substituted
or unsubstituted arylamino-(C1–C10) alkyl, (C1–C10)
haloalkyl, C2–C6 alkenyl, C2–C6 alkynyl, oxo, a linking
group attached to a second steroid, a substituted or

6 Examiner’s April 27, 2020, Answer.
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unsubstituted (C1–C10) aminoalkyloxy, a substituted or
unsubstituted (C1–C10) aminoalkyloxy-(C1–C10) alkyl, a
substituted or unsubstituted (C1–C10) aminoalkylcarboxy, a
substituted or unsubstituted (C1–C10)
aminoalkylaminocarbonyl, a substituted or unsubstituted
(C1–C10) aminoalkylcarboxamido, H2N–HC(Q5)–C(O)–
O–, H2N–HC(Q5)–C(O)–N(H)–, (C1–C10)azidoalkyloxy,
(C1–C10) cyanoalkyloxy, P.G.–HN–HC(QS)–C(O)–O–,
(C1–C10) guanidinoalkyloxy, (C1–C10)
quaternaryammoniumalkylcarboxy, and (C1–C10)
guanidinoalkylcarboxy, where Q5 is a side chain of any
amino acid, P.G. is an amino protecting group, and
R5, R8, R9, R10, R13, and R14 is each independently:
deleted when one of fused rings A, B, C, or D is unsaturated so
as to complete the valency of the carbon atom at that site, or
selected from the group consisting of hydrogen, hydroxyl, a
substituted or unsubstituted (C1–C10) alkyl, (C1–C10)
hydroxyalkyl, (C1–C10) alkyloxy-(C1–C10) alkyl, a
substituted or unsubstituted (C1–C10) aminoalkyl, a
substituted or unsubstituted aryl, C1–C10 haloalkyl, C2–C6
alkenyl, C2–C6 alkynyl, a linking group attached to a
second steroid, a substituted or unsubstituted (C1–C10)
aminoalkyloxy, a substituted or unsubstituted (C1–C10)
aminoalkylcarboxy, a substituted or unsubstituted (C1–C10)
aminoalkylaminocarbonyl, H2N–HC(Q5)C(O)–O–, H2N–
HC(Q5)–C(O)–N(H)–, (C1–C10) azidoalkyloxy, (C1–C10)
cyanoalkyloxy, P.G.HN–HC(Q5)–C(O)–O–, (C1–C10)
guanidinoalkyloxy, and (C1–C10) guanidinoalkylcarboxy,
where Q5 is a side chain of any amino acid, P.G. is an amino
protecting group, and
provided that at least two of R1 through R14 are independently
selected from the group consisting of a substituted or
unsubstituted (C1–C10) aminoalkyloxy, (C1–C10)
alkylcarboxy-(C1–C10) alkyl, (C1–C10) alkylamino-(C1–
C10) alkylamino, (C1–C10) alkylamino-(C1–C10)
alkylamino-(C1–C10) alkylamino, a substituted or
unsubstituted (C1–C10) aminoalkylcarboxy, a substituted or
unsubstituted arylamino-(C1–C10)alkyl, a substituted or
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unsubstituted (C1–C10) aminoalkyloxy-(C1–C10) alkyl, a
substituted or unsubstituted (C1–C10)
aminoalkylaminocarbonyl, (C1–C10) quaternaryammonium
alkylcarboxy, H2NHC(Q5)–C(O)–O–, H2N–HC(Q5)–
C(O)–N(H)–, (C1–C10) azidoalkyloxy, (C1–C10)
cyanoalkyloxy, P.G.–HN–HC(QS)–C(O)–O–, (C1–C10)
guanidinoalkyloxy, and (C1–C10) guanidinoalkylcarboxy;
or a pharmaceutically acceptable salt thereof.
(Savage ’234 81:7–82:22; see generally id. at 2:1–3:10; Ans. 3–5.)
FF 3. Savage ’234’s Figure 11 is reproduced below:

Savage ’234’s “FIG. 11 is a drawing showing compounds 341-343 and 324-
327 (Savage ’234 8:65–66; see Ans. 3 and 5).
FF 4. Savage ’904’s claim 1 is reproduced below:
1. A compound according to formula I

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wherein:
fused rings A, B, C, and D are independently saturated or
fully or partially unsaturated; and
R1 through R4, R6, R7, R11, R12, R15, R16, and R17 is each
independently selected from the group consisting of
hydrogen, hydroxyl, a substituted or unsubstituted (C1–
C10) alkyl, (C1–C10) hydroxyalkyl, (C1–C10) alkyloxy-
(C1–C10) alkyl, (C1–C10) alkylcarboxy(C1–C10) alkyl,
(C1–C10) alkylamino-(C1–C10) alkyl, (C1–C10)
alkylamino-(C1–C10) alkylamino, (C1–C10) alkylamino-
(C1–C10) alkylamino-(C1–C10) alkylamino, a substituted
or unsubstituted (C1–C10) aminoalkyl, a substituted or
unsubstituted aryl, a substituted or unsubstituted
arylamino-(C1–C10) alkyl, (C1–C10) haloalkyl, C2–C6
alkenyl, C2–C6 alkynyl, oxo, a linking group attached to a
second steroid, a substituted or unsubstituted (C1–C10)
aminoalkyloxy, a substituted or unsubstituted (C1–C10)
aminoalkyloxy-(C1–C10) alkyl, a substituted or
unsubstituted (C1–C10) aminoalkylcarboxy, a substituted
or unsubstituted (C1–C10) aminoalkylaminocarbonyl, a
substituted or unsubstituted (C1–C10)
aminoalkylcarboxamido, H2N–HC(Q5)–C(O)–O–, H2N–
HC(Q5)–C(O)–N(H)–, (C1–C10) azidoalkyloxy, (C1–
C10) cyanoalkyloxy, P.G.–HN–HC(Q5)–C(O)–O–, (C1–
C10) guanidinoalkyl oxy, (C1–C10)
quaternaryammoniumalkylcarboxy, and (C1–C10)
guanidinoalkyl carboxy, where Q5 is a side chain of any
amino acid, P.G. is an amino protecting group, and
R5, R6, R9, R10, R13, and R14 is each independently:
deleted when one of fused rings A, B, C, or D is
unsaturated so as to complete the valency of the carbon
atom at that site, or
selected from the group consisting of hydrogen, hydroxyl,
a substituted or unsubstituted (C1–C10) alkyl, (C1–
C10) hydroxyalkyl, (C1–C10) alkyloxy(C1–C10) alkyl,
a substituted or unsubstituted (C1–C10) aminoalkyl, a
substituted or unsubstituted aryl, C1–C10 haloalkyl,
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C2–C6 alkenyl, C2–C6 alkynyl, a linking group
attached to a second steroid, a substituted or
unsubstituted (C1–C10) aminoalkyloxy, a substituted or
unsubstituted (C1–C10) aminoalkylcarboxy, a
substituted or unsubstituted (C1–C10)
aminoalkylaminocarbonyl, H2N–HC(Q5)–C(O)–O–,
H2N–HC(Q5)–C(O)–N(H)–, (C1–C10) azidoalkyloxy,
(C1–C10) cyanoalkyloxy, P.G.–HN–HC(Q5)–C(O)–
O–, (C1–C10) guanidinoalkyloxy, and (C1–C10)
guanidinoalkylcarboxy, where Q5 is a side chain of any
amino acid, P.G. is an amino protecting group, and
provided that at least two of R1 through R14 are independently
selected from the group consisting of a substituted or
unsubstituted (C1–C10) aminoalkyloxy, (C1–C10)
alkylcarboxy-(C1–C10) alkyl, (C1–C10) alkylamino-(C1–
C10) alkylamino, (C1–C10) alkylamino-(C1–C10) alkyl
amino-(C1–C10) alkylamino, a substituted or unsubstituted
(C1–C10) aminoalkylcarboxy, a substituted or
unsubstituted arylamino-(C1–C10) alkyl, a substituted or
unsubstituted (C1–C10) aminoalkyloxy-(C1–C10) alkyl, a
substituted or unsubstituted (C1–C10)
aminoalkylaminocarbonyl, (C1–C10)
quatemaryammonium alkylcarboxy, H2N–HC(Q5)–C(O) –
O–, H2N–HC(Q5)–C(O)–N(H)–, (C1–C10) azidoalkyloxy,
(C1–C10) cyanoalkyloxy, P.G.–HN–HC(Q5)–C(O)–O–,
(C1–C10) guanidinoalkyloxy, and (C1–C10)
guanidinoalkylcarboxy, and further provided that R12
cannot be hydrogen when all of the fused rings A, B, C,
and D are saturated; or a pharmaceutically acceptable salt
thereof.
(Savage ’904 82:47–83:65; see Ans. 3–4.)

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FF 5. Savage ’904’s Figure 11 is reproduced below:

Savage ’904’s “FIG. 11 is a drawing showing compounds 341–343 and 324–
327” (Savage ’904 9:13–14; see Ans. 3).
FF 6. Examiner finds that Savage ’234 and Savage ’904 both include a
“definition of R17 as (C1-C10 alkylcarboxy-(C1-C10-)alkyl)” (Ans. 3 (citing
Savage ’234 (Fig. 11: compound 342) and Savage ’904 (Fig. 11: compound
342))).
FF 7. Examiner finds that the Savage ’234 fails to exemplify Appellant’s
claimed compound (Ans. 5).
FF 8. Examiner finds that Appellant’s Specification discloses that
“[u]nless otherwise specified, the indicated number of carbon atoms in an
‘alkylcarbonyl’ and in an ‘alkyl ester’ that is an ‘alkylcarboxylic ester’ is
inclusive of the carbonyl carbon” (Ans. 7 (citing Spec. ¶¶ 8 and 100)).
ISSUE
Does the preponderance of evidence on this record support
Examiner’s interpretation of the total number of carbons in the substituents
attached to the fused carbon ring backbone, particularly the R1 substituent of
Appellant’s Formula I?
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ANALYSIS
With respect to the obviousness-type double patenting rejections on
this record, Examiner concludes that Appellant’s claimed invention is not
patentably distinct from the claims of Savage ’234 or Savage ’904 (Ans. 3–
4).
With respect to the obviousness rejection on this record, Examiner
concludes that, at the time Appellant’s invention was made, it would have
been prima facie obvious to utilize “C10alkylcarboxy-C4alkyl as R17” of
Savage ’234, which is R1 of Appellant’s Formula I and, thereby, obtain
Appellant’s claimed compound (Ans. 5). In this regard, Examiner reasons
that a “skilled artisan in the art would have the reasonable expectation
that . . . any of the compounds encompassed by the prior art genus,
including those of the instant claims, would have similar properties as taught
by . . . [Savage ‘’234]” (Id. at 6).
Appellant contends that “[t]he sole issue underlying all rejections [on
this record] is how to properly account for the total number of carbons in the
substituents attached to the fused carbon ring backbone, many of which are
concatenated structures consisting of an alkyl portion and a functional
group” (Appeal Br. 6). We agree with Appellant’s statement of the issue,
which applies to the obviousness and obviousness-type double patenting
rejections and, therefore, consider Appellant’s contentions with respect to
the rejections on this record together.7

7 Appellant contends for “essentially the same reasons given above showing
that the Office Action failed to make a prima facie case of double patenting
over the claims of the Savage patents, . . . the Office also fails to make a
prima facie case of obviousness over the disclosure of Savage ’234” (Appeal
Br. 15–16).
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Examiner reasons that
unlike the present [S]pecification, none of the cited references
sets forth the inclusion of the carbon atom of the carboxy or
carbonyl groups of the prior art substituents in any of the alkyl
groups of said substituents. Therefore, the skilled artisan in the
art would refer to the [R1] position of the Appellant’s elected
compound as C10alkylcarboxyl-C4-alkyl which would be
encompassed by the prior art definition of R17 as (C1-C10)-
alkylcarboxy-(C1-C10)-alkyl.
In short, one cannot employ the definition set forth in . . .
[Appellant’s] [S]pecification to interpret the prior art
substitutents.
(Ans. 7; see FF 8.) As Appellant explains, however:
In every definition for R1-R17 in the reference patents, the
total number of carbons in each listed group (e.g., col. 2, line 21
to col. 3, line 10) is accounted for in the expression “C1-C10”.
In no case is the carbon in any group excluded from the total
number of carbons in “C1-C10.” The term “(C1-C10)
alkylcarboxy-(C1-C10) alkyl” literally means that “C1-C10”
refers to the total number of carbons provided by the entire
“alkylcarboxy” portion, including the alkyloxy and carbonyl
subportions of the ester, and “C1-C10” is the total number of
carbons in the alkyl portion connecting the “alkylcarboxy”
portion to the fused ring. . . .
The term “(C1-C10) alkylcarboxy-(C1-C10) alkyl” defines a
group having only one “alkyl” moiety and one indivisible
“alkylcarboxy moiety” and totaling at most 20 carbons. All
carbons are accounted for and cannot exceed 20 total carbons.
The term “(C1-C10) alkylcarboxy” does not and cannot
embrace “C11-alkylester” having 11 total carbons rather than
groups with a maximum of 10 carbons as specified.
(Appeal Br. 12–13.) On this record, we find that Appellant has the better
position (see generally Appeal Br. 11 (Appellant’s claim 1 “defines a
narrowly tailored subgenus of CSA compounds that excludes the entire
genus of compounds in the Savage patents”)).
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We recognize Examiner’s assertion that “even if one agrees with
Appellant, the elected compound would be [the] corresponding lower
adjacent homolog of the prior art compound when [the prior art’s R17] is
C10-alkylcarboxyl-C4 alkyl (i.e. C10alkylester-C4-alkyl)” (Ans. 7).
When chemical compounds have “very close” structural
similarities and similar utilities, without more a prima facie
case may be made. See for example In re Wilder, 563 F.2d
457 . . . (CCPA 1977) (adjacent homologs and structural
isomers) . . . . When such “close” structural similarity to prior
art compounds is shown, in accordance with these precedents
the burden of coming forward shifts to the applicant, and
evidence affirmatively supporting unobviousness is required.
In re Grabiak, 769 F.2d 729, 731 (Fed. Cir. 1985).
Appellant contends, however, that “Appellant submitted clear
evidence that the claimed CSA compounds possess properties which are not
possessed by the prior art CSA compounds,” (Reply Br.8 3 (citing
Appellant’s August 29, 2018, Amendment); see also Reply Br. 3–12). Such
evidence must be considered before making a conclusion of obviousness.
See In re Sullivan, 498 F.3d 1345, 1352 (Fed. Cir. 2007) (“Whether the
composition would have been obvious cannot be determined without
considering evidence attempting to rebut the prima facie case.”); In re
Rinehart, 531 F.2d 1048, 1052 (CCPA 1976) (“When prima facie
obviousness is established and evidence is submitted in rebuttal, the
decision-maker must start over.”). Examiner failed to respond to
Appellant’s evidence, finding instead that, “Appellant has not provided any
evidence on [this] record of any property possessed by the claimed
compound that is not possessed by the prior art compounds” (Ans. 7–8).

8 Appellant’s June 26, 2020, Reply Brief.
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Regardless of the merits or the sufficiency of the proffered evidence,9
Examiner’s failure to properly acknowledge, consider, and evaluate the
evidence constitutes reversible error. In re Sullivan, 498 F.3d. at 1352–
1353; In re Stepan Co., 660 F.3d 1341, 1344–1345 (Fed Cir. 2011).
CONCLUSION
The preponderance of evidence on this record fails to support
Examiner’s interpretation of the total number of carbons in the substituents
attached to the fused carbon ring backbone, particularly the R17 substituent
of Appellant’s Formula I.
The rejection of claims 1, 6, 10, 12, 20, 24, 26, 31–42, and 44 under
the judicially created doctrine of obviousness-type double patenting as being
unpatentable over the claims of Savage ’234 is reversed.
The rejection of claims 1, 6, 10, 12, 20, 24, 26, 31–42, and 44 under
the judicially created doctrine of obviousness-type double patenting as being
unpatentable over the claims of Savage ’904 is reversed.
The rejection of claims 1, 6, 10, 12, 20, 24, 26, 31–42, and 44 under
35 U.S.C. § 103(a) as unpatentable over Savage ’234 is reversed.

9 We express no opinion as to the sufficiency of the proffered evidence,
leaving that determination in the first instance to the Examiner. In re
Oetiker, 977 F.2d 1443, 1445 (Fed. Cir. 1992) (“[E]xaminer bears the initial
burden, on review of the prior art or on any other ground, of presenting a
prima facie case of unpatentability.”).
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DECISION SUMMARY
In summary:
Claims
Rejected
35 U.S.C. § Reference(s)/Basis Affirmed Reversed
1, 6, 10, 12,
20, 24, 26,
31–42, 44
Obviousness-type
Double Patenting,
Savage ’234
1, 6, 10,
12, 20,
24, 26,
31–42, 44
1, 6, 10, 12,
20, 24, 26,
31–42, 44
Obviousness-type
Double Patenting,
Savage ’904
1, 6, 10,
12, 20,
24, 26,
31–42, 44
1, 6, 10, 12,
20, 24, 26,
31–42, 44
103 Savage ’234 1, 6, 10,
12, 20,
24, 26,
31–42, 44
Overall
Outcome
1, 6, 10,
12, 20,
24, 26,
31–42, 44

REVERSED