DETAILED ACTION
STATUS OF THE APPLICATION
Receipt is acknowledged of Applicants’ Amendments and Remarks, filed 19 December 2023, in the matter of Application No. 18/571,761. Said documents have been entered on the record. The Examiner further acknowledges the following:
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claims 14-26 are pending.
No claims have been amended.
Claims 1-13 have been cancelled.
Claims 14-26 have been newly added.
Thus, claims 14-26 represent all claims currently under consideration.
Priority
Acknowledgment is made of Applicant’s claim for foreign priority under 35 U.S.C. 119 (a)-(d). The certified copy has been filed in the present application filed 19 December 2023 and in parent Application No. PCT/EP2022/065792, filed on 10 June 2022. Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55. Applicant claims foreign priority to Application No. EP 21180528.8, filed on 21 June 2021.
Domestic Priority data as claimed by applicant:
This application is a 371 of PCT/EP2022/065792 (06/10/2022)
Foreign Applications:
EUROPEAN PATENT 21180528.8 (06/21/2021)
Information Disclosure Statement (IDS)
The information disclosure statements submitted on 27 December 2023 and 10 March 2024 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the Examiner.
Claim Objections
Claim 16 is objected to because of the following informalities:
In lines 1-2, “…formula I or II… should read “…formula (I) or (II)…”
In line 23, formula (III) and formula (IV) are blurry and it is difficult to read the variables and numbers associated with them.
In line 24, “…m, q are…” should read “…where m, q are…”
In line 45, “…Y1, Y2, Y3 are…” should read “…Y1, Y2, Y3 are…”
Claim 17 is objected to because of the following informalities:
In line 2, “…according formula V…” should read “…according to formula (V)…”
A period is missing at the end of the sentence of the claim.
Claim 18 is objected to because of the following informalities:
In line 2, “…during the reaction of the formaldehyde with acetylene…” should read “…during the reaction of formaldehyde with acetylene …”
Claim 19 is objected to because of the following informalities:
A period is missing at the end of the sentence of the claim.
Claim 21 is objected to because of the following informalities:
In line 1, “…the reaction mixture…” should read “…the process…”
Claim 22 is objected to because of the following informalities:
In line 1, “…the reaction…” should read “…the process…”
Claim 23 is objected to because of the following informalities:
In line 1, “…the reaction…” should read “…the process…”
Claim 24 is objected to because of the following informalities:
In line 1, “…the reaction…” should read “…the process…”
Claim 26 is objected to because of the following informalities:
In line 2, “…organic phase is reused as catalyst…” should read “…organic phase and is reused as catalyst…”
In line 2, “…the alkynylation reaction…” should read “…the process…”
Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 17-18 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 17 recites formula V, however there are no corresponding definitions for the variables Y1 and Y2. Therefore, the scope of the claimed genus is unclear, and this ambiguity renders the instant claim indefinite. Further clarification is required. The Examiner notes that adequately addressing this ambiguity would ameliorate this claim rejection. For the purposes of examination, the definition of variables Y1 and Y2 will be interpreted as defined in instant claim 16 and the written description (Specification; page 6, lines 1-6).
Claim 18 recites the limitation “the copper complex” in line 1. There is insufficient antecedent basis for this limitation in the claim. Further clarification is required. The Examiner notes that correcting any suspected typographical error(s) regarding the claim language would ameliorate this claim rejection.
Allowable Subject Matter
Claims 14-15, 20, and 25 are allowed.
Claims 16-19, 21-24, and 26 would be allowable if rewritten or amended to overcome the objections to claims 16-19, 21-24, and 26 and the rejections of claims 17-18 under 35 U.S.C. 112(b)/35 U.S.C. 112 (pre-AIA ), second paragraph, set forth in this Office Action.
The following is a statement of reasons for the indication of allowable subject matter:
The prior art of record does not teach or suggest a process to produce propargylic alcohol comprising reacting acetylene with formaldehyde in a liquid phase in the presence of a copper catalyst and at least one phosphine, as recited in independent claim 14.
The closest prior art to the claimed invention is Vicari et al. (US 2007/0112226 A1; IDS of 12-27-2023; hereinafter “Vicari”) and Asano et al. (“Enantioselective Addition of Terminal Alkynes to Aromatic Aldehydes Catalyzed by Copper(I) Complexes with Wide-Bite-Angle Chiral Bisphosphine Ligands: Optimization, Scope, and Mechanistic Studies”; Organometallics 2008, 27, 5984-5996; hereinafter “Asano”).
Vicari teaches a method for the production of propargyl alcohol comprising reacting an aqueous formaldehyde solution and acetylene over a copper acetylide catalyst (Vicari; Title; Abstract; claim 1).
Vicari fails to teach a process to produce propargylic alcohol comprising at least one phosphine.
Asano teaches the addition of terminal alkynes to aldehydes in the presence of a Cu-phosphine complex to afford propargyl alcohols (Asano; Title; Abstract). Asano further teaches that wide bite angles of bisphosphine ligands are important for the activation of Cu catalysis toward the addition of terminal alkynes and aldehydes via deaggregation of Cu acetylides (Asano; Abstract; page 5985, Col. 1, paragraph 1). In addition, Asano demonstrates the catalytic activity of a Cu(I) complex with DBEPhos, Xantphos, DTBM-Xantphos, (S,S)-(R,R)Fc-Ph-TRAP, and (R,R)-i-Pr-DuPhos bisphosphine ligands for the addition of phenylacetylene to benzaldehyde in toluene solvent to afford the corresponding propargylic alcohol (Asano; page 5985; Table 1 and Figure 1, Col. 1, paragraph 3 and Col. 2, paragraph 1; page 5991, Col. 2, Conclusions paragraph).
Asano fails to explicitly teach a method for the production of propargyl alcohol comprising reacting acetylene with formaldehyde.
Although Vicari and Asano reside in the closely overlapping technical field of Cu-catalyzed addition reactions of terminal alkynes to aldehydes, the method of Asano utilizing Cu-phosphine catalysts does not disclose that formaldehyde is a viable substrate for the transformation, nor does Asano utilize acetylene as a reactant in the disclosed transformation. Of particular note, Asano teaches that the substrate scope is limited to aromatic aldehydes, and reports a 0% yield for non-aromatic aldehydes (Asano; page 5989, Table 7, entries 14-15). Thus, it would not be predictable for one of ordinary skill in the art to apply the catalytic system of Asano to the process of Vicari, because teaches away from the use of non-aromatic aldehydes as viable reactants. As such, the skilled artisan would not be sufficiently motivated to substitute the copper acetylide catalyst of Vicari with the Cu-phosphine catalyst of Asano with a reasonable expectation of success to arrive at the process of claim 14. Therefore, the claims are free from the prior art for the reasons of record and the reasons set forth above. Also see MPEP § 2143(B)(I).
Conclusion
Any inquiry concerning this communication or earlier communications from the Examiner should be directed to Derek Rhoades whose telephone number is (703)-756-5321. The Examiner can normally be reached Monday–Thursday, 7:30 am–5:00 pm EST; Friday, 7:30 am–4:00 pm EST.
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/D.R./Examiner, Art Unit 1692
/AMY C BONAPARTE/Primary Examiner, Art Unit 1692
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