*DETAILED ACTION*
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Applicant's response dated September 28, 2026 is acknowledged.
Priority
This application is a 371 of PCT/US2022/074903 filed on 08/12/2022, and claims benefit
in provisional application 63/233,163 filed on 08/13/2021.
Claim Status
Claims 1-3, 5-9, 19, 21-23, 25, 34, 42, and 45-48 are pending. Claims 4, 10-18, 20, 24,
26-33, 35-41, 43, and 44 were canceled. Claims 1-3, 5, 6, 21, and 45-47 were amended. Claims 3, 8, 9, 19, 21-23, 25, 34, 42, and 45-48 remain withdrawn. Claims 1, 2, and 5-7 are examined.
Information Disclosure Statement
The citation for foreign document cited under number 1 was corrected because the foreign document number does not match the information of the document that was submitted.
Non-patent literature document 8 was not considered because it missing the date when the online registry was accessed or obtained, it is missing the number of pages. The last CAS number in the registry is also missing the date it was entered. All other cited CAS numbers also recite the date the number of entered.
Maintained Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness
rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35
U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the
claims the examiner presumes that the subject matter of the various claims was commonly
owned as of the effective filing date of the claimed invention(s) absent any evidence to the
contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and
effective filing dates of each claim that was not commonly owned as of the effective filing date
of the later invention in order for the examiner to consider the applicability of 35 U.S.C.
102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
In the event the determination of the status of the application as subject to AIA 35 U.S.C.
102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the
statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a
new ground of rejection if the prior art relied upon, and the rationale supporting the rejection,
would be the same under either status.
Claims 1, 2, and 5-7 are rejected under 35 U.S.C. 103 as being unpatentable over
Delehanty (US 2013/0129627 Published May 23, 2013 - of record in PTO-892 dated December
2, 2025).
The claims encompass a compound of formula
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109
342
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.
Delehanty teaches a compound of formula
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70
214
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wherein
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(Figure 10). The compound
is formed by covalently attaching a palmitoyl group to diaminopropionic acid (Dap) residue
(paragraphs 0098 and 0136). A synthetic palmitic acid group ((Pal)Dap) is for cell membrane
association and insertion and vesicle escape (paragraph 0026). A vesicle escape domain
preferably comprises a non-hydrolysable lipid moiety. Such a lipid moiety includes at least eight
carbons. In one embodiment, the lipid moiety is palmitate (palmitic acid). One of ordinary skill
in the art would recognize that another lipid moiety might be used to obtain the desired cell
membrane association, insertion, and/or vesicle escape. Such moieties include stearic acid
(paragraph 0121).
It would have been prima facie obvious to a person of ordinary skill in the art before the
effective filing date of the claimed invention to have modified the compound "a" by replacing
the palmitoyl group with stearoyl group, with a reasonable expectation of success because
Delehanty teaches that stearic acid may be used instead of palmitic acid to obtain the compound.
Stearic acid and palmitic acid are equally useful for making the compound and replacing one
equivalent with another to obtain predictable results supports obviousness. It is apparent from
paragraph 0121 that the source of the lipid moiety is a fatty acid. The skilled artisan would have
recognized that -CH2-NH- segment in "a" was derived from NH2-CH2- portion of the Dap. The
difference between the claimed compound and compound "a" as modified above is stereochemistry at the chiral center. The claimed enantiomer would have been obvious over the
prior art enantiomer because the skilled artisan would have understood that diaminopropionic
acid has two enantiomers and both would have been equally obvious. Figure 10 is the only place
in Delehanty where stereochemistry of Dap is shown. The reference does not teach as to why the
Dap having the stereochemistry depicted in Figure 10 was selected and there is no evidence that
stereochemistry is critical. Similarly, instant application was reviewed and there is no evidence
that the stereochemistry of the claimed compound is critical. In view of the lack of criticality, it
would have been obvious to modify Delehanty by replacing the enantiomer of Dap shown in
Figure 10 with the instantly claimed enantiomer to arrive at the claimed invention because the
two enantiomers would have been equally obvious to use in Delehanty's invention. The elected
species is obvious over compound "a" having the palmitoyl group replaced with stearoyl group
and stereochemistry of the claimed compound.
Response to Arguments
Applicant’s arguments submitted in the remarks dated September 28, 2026 were fully considered but are not persuasive for the following reasons.
Arguments related to Delehanty’s intended use are not persuasive because Delehanty’s compound could been used for the same purpose as described in applicant’s specification because a compound and its properties are inseparable. It is also noted that instant claims do not even recite an intended use, thus the applicant is arguing limitations that are not claimed.
Arguments that Delehanty does not teach the claimed compound per se are not persuasive because Figure 10 depicts a whole a compound “a” that is not a part of any other compound, therefore it would have been reasonable to interpret the reference as teaching compound “a” as a complete and whole compound that is not a moiety within another compound. Referring to compound “a” as a moiety indicates that the compound becomes a moiety or a residue in a peptide chain after solid state peptide synthesis. It is irrelevant that Delehanty also teaches incorporating compound “a” with another compound and that compound “a” becomes a moiety when incorporated within another compound.
There is no teaching in the reference that would have lead a person skilled in the art to conclude that compound “a” as drawn in Figure 10 would not have been obvious to make. The examiner disagrees with applicant’s statement “meaning that the moiety would have never been the isolated compound, and would always be a part of a larger molecule, e.g., Boc-protected Dap(Pal)” because in order to arrive at a larger molecule such as Boc-protected Dap(Pal), the skilled artisan would have to make Dap(Pal) first and then protect it with the Boc. Paragraph 0136 teaches that the peptide is synthesized using Boc-solid phase peptide synthesis. A person skilled in the art would have understood that an amino acid would first have to be protected with a Boc group, followed by reacting the Boc-protected amino acid with a terminal amino acid residue on a growing peptide chain that is attached to the solid surface. Prior to protecting the amino acid with the Boc group, the amino acid would have been in its unprotected form, meaning it is just an amino acid. For example, see “Overview of Solid Phase Peptide Synthesis (SPPS)” (Accessed from https://www.peptide.com/resources/solid-phase-peptide-synthesis/overview-of-solid-phase-peptide-synthesis-spps/, Accessed on October 6, 2026, pages 1-7). Page 1 describes the SPPS process and teaches that the alpha amino group and reactive side chains are protected in order to prevent polymerization of the amino acid. Therefore, a person skilled in the art reading Delehanty would have understood that compound “a” would have to be synthesized first as compound “a” depicted in Figure 10, then protected with a Boc group to obtain a Boc-protected compound “a”, which would subsequently be used in a method of making a peptide via solid state peptide synthesis. According to SciFinder Scholar data on the Delehanty reference, the Dap-Pal has CAS Registry Number 1436861-51-6, and it is the S isomer having the following chemical structure
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.
A CAS registry number is assigned to every completely identified chemical substance in scientific literature, patent applications, and patents. This is further evidence that Delehanty’s teachings encompass compound “a” as drawn in Figure 10, and not merely as a moiety that is a part of another compound.
Applicant’s argument that a person skilled in the art would not have been motivated to make Dap-Pal is not persuasive because in order to form a peptide comprising a moiety or residue of Dap-Pal, the skilled artisan would have recognized that Dap-Pal would have to be synthesized first, protected by Boc, then reacted with a terminal amino acid residue on a growing peptide chain to incorporate the Dap-Pal into the peptide chain. In order to make a peptide comprising Dap-Pal residues or moieties, the skilled artisan would have to make the Dap-Pal first. Even applicant used “Boc-protected Dap(Pal)” as an example where Dap(Pal) is a part of a larger molecule, however in order to arrive at “Boc-protected Dap(Pal)” one of skill in the art would have to start with Dap(Pal), which provides motivation to make Dap(Pal).
It would have been obvious to have formed Dap-stearate by replacing the palmitoyl group with the stearoyl group in Dap-palmitate because Delehanty teaches that one of ordinary skill in the art would recognize that another lipid moiety might be used to obtain the desired cell membrane association, insertion, and/or vesicle escape and specifically teaches stearic acid. It would have been obvious to have selected stearic acid because it is listed as a suitable lipid. Replacing one equivalent with another to obtain a predictable result supports obviousness.
Arguments related to the beneficial properties of the claimed compound are not sufficient to overcome the rejection because beneficial properties are not claimed limitations, and in the event that applicant amends the claims to recite the beneficial properties such amendment would not be sufficient to overcome the rejection because prior art teaches the same compound as claimed. The specification was reviewed and the applicant has not provided evidence of unexpected results as required by MPEP 716.02.
Conclusion
No claims are allowed.
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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/ALMA PIPIC/Primary Examiner, Art Unit 1617
