DETAILED ACTION
This Office action details a first action on the merits for the above referenced application No. Claims 2-3, 6-7, 10, 13-20, 23, 29, 31, and 33-35 are pending in this application.
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 .
Priority
This application is a 35 USC 371 National Stage filing of international application No. PCT/AU2022/050154 filed on 25 Feb. 2022 and claims benefit under 35 USC 119(a)-(d) to foreign application Nos. AU 2021900532 and AU 2021903428 filed on 26 Feb. 2021 and 26 Oct. 2021, respectively.
Election/Restrictions
Applicant’s election without traverse of Group I, claims 2, 6-8, and 35 in the reply filed on 5 May 2026 is acknowledged.
Claims 3, 10, 13, 13-20, 23, 29, 31, and 33-34 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected Group I, claims 2, 6-8, and 35, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 5 May 2026.
Applicant’s election without traverse of the elected species (see below), claims 2, 6-7, and 35 in the reply filed on 5 May 2026 is acknowledged.
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(formula II), 2-chloro-trityl, PG1=alloc;
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(formula III) Act=1-H-imidazole, PG2=PG3=tBu;
and
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(formula IV).
Information Disclosure Statement
The information disclosure statements (IDS) submitted on 21 Aug. 2023 and 5 Mar. 2026 has been 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.
Claim(s) 2, 6-7, and 35 is/are rejected under 35 U.S.C. 103 as being unpatentable over Eder et al. (Bioconjugate Chem.; published 28 Feb. 2012; see IDS filed on 21 Aug. 2026, in view of Zia et al. (WO 2018/223180 A1; published 13 Dec. 2018; see IDS filed on 21 Aug. 2026).
Eder et al. teach 68Ga-complex lipophilicity and the targeting property of a urea-based PSMA inhibitor for PET imaging (see title). Eder et al. teach the synthesis of Glu-NH-CO-NH-Lys(Ahx)-HBED-CC and Glu-NH-CO-NH-Lys(Ahx)-DOTA (pg. 689). Eder et al. teach the following synthesis scheme
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(scheme 1, pg. 691).
This reads on a method of preparing a compound of formula (IV)
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wherein
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= 2-chloro-trityl resin; PG1=alloc; PG2=PG3=tBu; the method comprising reacting a compound of formula (II)
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with bis(tert-butyl) L-glutamate HCl and wherein the method further comprises selective deprotection of Alloc (PG1) to compound of formula (V)
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.
In the first step, the isocyanate 2 of the glutamyl moiety was generated in situ by adding a mixture of bis(tert-butyl) L-glutamate hydrochloride and DIPEA in DCM. After agitation for 1 h at 25oC, resin immobilized (2-chlorotritylresin) ε-allyloxycarbonyl protected lysine was added in one portion and reacted for 16 h with gentile agitation leading to compound 2. The resin was filtered off and the allyloxy protecting group was removed using tetrakis(triphenyl)palladium and morpholine in DCM for 3 h resulting in compound 4 (pg. 689).
Eder et al. do not teach the claimed method that uses a compound of formula (III)
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wherein X is an activating group such as 1H-imidazole.
Zia et al. teach radiopharmaceuticals, radioimaging agents and uses thereof (see title). Zia et al. teach the synthesis of compounds of the invention and of Sar-PSMA (pg. 24). Zia et al. teach the following synthesis scheme
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(see scheme 1). L-Bis(tBu)Glu HCl and carbonyl diimidazole was added to a mixture of DMF/MsCN. The reaction was stirred at RT and purified by flash chromatography (pg. 26). Zia et al. teach the synthesis of protected KuE on resin (4). The Sar-PSMA ligand was synthesized from the KuE motif on the resin under standard solid phase peptide synthesis conditions (pg. 26). Kia et al. teach the synthesis of CoSar(PSMA)2 where to a flask containing H-Lys(Fmoc)-OtBu was added activated Glu intermediate and DIPEA in DCM and stirred overnight at RT (pg. 28).
It would have been obvious to a person of ordinary skill in the art before the effective filing date to modify the method of Eder et al. (method of preparing the compounds of instant formulas (IV) and (V) wherein PG1=alloc, PG2=PG3=tBu, and
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denotes 2-chlorotrityl) so that a compound of instant formula (III) is used as a reactive L-Bis(tBu)Glu intermediate wherein X=1H-imidazole as taught by Kia et al. because the compound of instant formula (III) used in the method of preparing would have been expected to provide an equivalent reactive intermediate suitable of forming formula (IV) and advantageously enable the use a stable reactive intermediate that can be prepared in advanced and reacted at room temperature under standard solid phase conditions.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SEAN R DONOHUE whose telephone number is (571)270-7441. The examiner can normally be reached on Monday - Friday, 8:00 - 5:00 EST.
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/Michael G. Hartley/Supervisory Patent Examiner, Art Unit 1618
/SEAN R. DONOHUE/
Examiner, Art Unit 1618
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