DETAILED ACTION
This office action is in response to applicant’s filing dated May 13, 2026.
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 .
Notice of Change of Examiner
Please note that the Examiner prosecuting this application has been changed to Examiner Elena Vishnyakova of Art Unit 1691. Please address all future correspondences to Examiner Vishnyakova.
Status of claims
Claims 8, 10-15, 17-21, 23-28 and 31-33 are pending in the instant application. Acknowledgment is made of Applicant’s amendments filed May 13, 2026. Acknowledgment is made of Applicant’s addition of a new claim 33.
Election/Restrictions
Applicant’s election of Group III, claims 21 and 23-26, drawn to a compound of Formula III, in the reply filed on May 13, 2026 is acknowledged. Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)). Claims 8, 10-15, 17-20 and 27-33 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on May 13, 2026.
Applicant’s election without traverse of compound 2-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)ethan-1-amine as a single species of compound of Formula III in the reply filed on May 13, 2026 is acknowledged. Since invention of Group IV, claim 27, drawn to compounds recited in claim 27, recites the elected species, compound 2-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)ethan-1-amine, the examination will expand to include, Group IV invention, claim 27. Upon performing the search of prior art Examiner detected compounds, related to non-elected inventions or species. Hence, the examination will expand to include Group I invention, compound of Formula I (claims 8, 10 - 14) and a Group II invention, compound of Formula II (claims 15 and 17 - 20).
Claims 8, 10 - 15, 17 - 21 and 23-27 are presently under examination, as they relate to elected species compound 2-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)ethan-1-amine and expanded species, compound of Formula I and compound of Formula II.
Priority
The present application is a 371 of PCT/US2022/072102, filed May 4, 2022, and claims the benefits of priority to U.S. provisional application No. 63/183,894, filed on May 4, 2021.
Information Disclosure Statement
The information disclosure statements (IDS) submitted on 12/05/2023, 04/24/2026 and 05/15/2026 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
Claim Rejections - 35 USC § 103
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.
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.
Claims 8, 10 - 15, 17 - 21 and 23-27 are rejected under 35 U.S.C. 103 as being unpatentable over Tang et al (J. Am. Chem. Soc. 2017, 139, 8547−8551, herein after Tang) in view of Adams et al (WO 2008/063300 A2, cited in IDS, filed 12/05/2023, hereinafter Adams).
Instant claims are drawn to a compound of Formula I:
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, Formula II:
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, or Formula III:
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, where X is a boronic acid group and a boronic acid pinacol ester group, L is a linker, selected from carbamate or ether; S is a spacer selected from of C1-C20 alkylenyl and -[-O-CH2CH2-]n-, wherein n is 1-12, and, s is 0-10 or s is 1-10, and Y is a chemically linkable end group, such as halo, amino, carboxyl, C2-C10 alkynyl, hydroxyl, C1-C10 alkoxy or azido. Instant claims are further drawn to the compound of Formula I, II or III, which is further comprising a molecule conjugated to the chemically linkable end group, wherein the conjugated molecule is selected from drugs, probes, dyes, peptides, proteins, drug candidates and natural products. One of the examples of compounds of Formula III is 2-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)ethan-1-amine (
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), (specification, page 25, Ex. 5).
Tang teaches benzylboronate chemical motif, that provides highly efficient active targeting of proteins to the cell nucleus. Tang teaches eGFP (green fluorescent protein) modified with three BB tags of structure:
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(page 8549, Fig. 2 (a)). The benzylboronate chemical tag taught by Tang falls within the scope of the instant genus compounds of Formula I and II. The whole structure above (GFP tagged with benzylboronate) also demonstrates the molecule of protein conjugated with tag (compound of Formula I or II), and falls within the scope of instant claims 13, 14, 19, 20, 25 and 26. Tang further teaches that the boronate moiety is the key component driving nuclear transport, with some synergy observed with aromatic functionality, as evidenced by comparing nuclear accumulation of nonboronated benzyl modified eGFP (eGFP-B) and GFP tagged with benzylboronate (page 8548, left column).
Thus, Tang teaches benzylboronate tags, which have a structure identical or similar to the instantly claimed compounds of Formula I or II, and which effectively deliver proteins to the cell nucleus.
Tang does not teach where Y is a chemically linkable end group, such as halo, amino, carboxyl, C2-C10 alkynyl, hydroxyl, C1-C10 alkoxy or azido. Tang does not teach compounds of instant Formula III.
However, Adams teaches compounds of formula (III-a):
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(page 5, [0017]) where Z1 and Z2 are both H (page 21, [0058]) or Z1 and Z2 form a 5-membered ring
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(page 21, [0066]); R1 is halogen, -OR, -CF3, -CN etc., n is 0 (page 4, [0011]); X is –(CH2)rO(CH2)q, q is 0 - 4, r is 0 – 1 (page 37, [00122]); RA is halogen, -OH, -OR, -CF3, -CO2R, -N3, or-N(R’)2, R and R’ is hydrogen or an optionally substituted C1-6 group.
Compound of formula (III-a), taught by Adams is equivalent to the instantly claimed compound of Ex. 5 if Z1 and Z2 form a 5-membered ring
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; X is –(CH2)rO(CH2)q, r=1 and q=2; and RA is NH2. Although Adams does not explicitly teach where the molecule, such as a drug molecule, is conjugated to the chemically linkable end group, such as NH2 group, it is presumed that the properties (such as ability to bind certain molecules) of compounds taught by Adams are correspondingly similar to instantly claimed compounds, since Adams teaches compounds of identical or similar structure, and "products of identical chemical composition cannot have mutually exclusive properties”. MPEP 2112.01 states: Where the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, claimed properties or functions are presumed to be inherent.
Thus, since Tang and Adams teach compounds where all the structural elements are equivalent to instantly claimed compounds, it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the present invention to modify known compounds and make various structural analogs, by selecting and combining known structural fragments, to arrive at claimed compounds. The one of ordinary skills would be motivated to do so in search of a nuclear targeting tags, having a structure of derivative of aromatic boronate, to effectively deliver molecules of interest (e.g. protein) to the cell nucleus with the reasonable expectation of success. Especially, since prior art teaches the boronate moiety is the key component driving nuclear transport.
Therefore, the invention as a whole is prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
Conclusion
Claims 8, 10 - 15, 17 - 21 and 23-27 are rejected. No claim is allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ELENA V VISHNYAKOVA whose telephone number is (571)272-3781. The examiner can normally be reached 7:30am - 5pm ET.
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/E.V.V./ Examiner, Art Unit 1691
/RENEE CLAYTOR/ Supervisory Patent Examiner, Art Unit 1691
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