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 .
Priority
This application was filed 06/09/2023 and is a 371 of PCT/US21/62538 (12/09/2021) which claims priority to PRO 63/124544 (12/11/2020). Claims 1-20 are before the Examiner.
Claim Rejections - 35 USC § 112
The rejection of claim 20 under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends, as stated in paper dated 09/08/2025 has been overcome by applicant’s amendments and arguments in paper dated 12/03/2025.
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 rejection of claims 1-20 are rejected under 35 U.S.C. 103 as being unpatentable over WO 2011037929 and Zhang, as stated in paper dated 09/08/2025, is upheld.
As previously stated, both references teach Pd(II) catalyzed hydroxlylation of arenes with O2 and a ligand. See pages 2-3 of the WO and Zhang. The rings that are hydroxylated are monocyclic or multiple cyclic rings. WO page 6 through first paragraph of page 7 teach that the rings can be heterocyclic or aromatic. WO teaches the preferred non-nucleophilic base (claim 18) is KOAc. The difference between the processes taught by the WO and Zhang and the instantly claimed process is the identity of the ligand of formula (L). Both Zhang and WO have tertiary amines present in the reaction just not the specified tertiary amine of claim 1. It would have been obvious to one of ordinary skill in the art at the time of the invention to use the same reaction taught by Zhang and the WO with a different tertiary amine with the reasonable expectation of getting the same reaction product. Rationale: It is within the skill of the ordinary artisan to choose a different tertiary amine (ligand) and use it as taught by the prior art with the expectation of getting the expected final reaction product.
Applicant argues in paper dated 12/03/2025, that the palladium catalyst taught by the prior art is different from the instantly claimed catalyst. Claims 1-14 and 17-20, the catalyst claimed is “a source of Pd(II)”. Zhang teaches Pd(oAc)2 and ‘929 teaches Pd(oAc)2. These are both sources of Pd(II). Further, claim 15 is limited to “wherein the source of Pd(II) is a Pd(II) salt”. Claim 16 is further limited to “wherein the Pd(II) salt is at least one…of Pd(OAc)2,…PdCl2”. Both Zhang and ‘929 teach Pd(OAc)2 as the catalyst and ‘929 also teaches PdCl2. This is fully anticipatory of all the instant claims 1-20 including the limited claims 15 and 16.
Applicants further argue that the tertiary amide of a carboxylic acid with oxygen in the presence of a Pd(II) catalyst (see claim 1 of ’929) is not sufficient of a teaching to equate to the instantly claimed Pd(II) in the presence of O2 and a ligand of formula (L) as claimed in the instant claim 1 is not sufficient teaching to obviate the instant L in the instant process. However, the instant process uses tertiary amines as a ligand (L) to make compounds of formula (2) from compound of formula (1). However, the prior art Zhang and ‘929 both teach the making of compound of (2) from (1) with a source of Pd(II) in the presence of O2 and a ligand. The same reactants making the same products in the same conditions. The only difference being the choice of ligands.
This rejection is upheld.
Conclusion
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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to D MARGARET M SEAMAN whose telephone number is (571)272-0694. The examiner can normally be reached M-F 8am-4pm Eastern.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Andrew Kosar can be reached at 571-272-0913. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/D MARGARET M SEAMAN/Primary Examiner, Art Unit 1625
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