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 .
Claim Status
Claims 1-2 were filed in a preliminary amendment on 04/01/2024. Claim 1 has been amended.
Claims 1-2 are currently pending and under examination.
Priority
The instant application is a national stage application of PCT/JP2022/039135 filed on 10/20/2022, which claims foreign priority to Japanese application no. 2021-173044 filed on 10/22/2021.
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Should applicant desire to obtain the benefit of foreign priority under 35 U.S.C. 119(a)-(d) prior to declaration of an interference, a certified English translation of the foreign application must be submitted in reply to this action. 37 CFR 41.154(b) and 41.202(e).
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 04/01/2024 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement has been considered by the examiner.
Claim Objections
Claim 1 is objected to because of the following informalities: The structures provided on line 13 of claim 1 are illegible. As an example, the subscripts in the structures are difficult to discern without the claim text. Appropriate correction is required.
Claim Rejections - 35 USC § 112(b)
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 1-2 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 1 recites the limitation "in the step (I)" in the second paragraph of the body of the claim. Claim 1 does not include a limitation of “a step (I). Therefore, there is insufficient antecedent basis for this limitation in the claim.
Claim 2, which depends on claim 1, is also rejected for the same reasoning.
For the purposed of applying prior art, the limitation of “in the step (I)” will be interpreted as the step of obtaining an intermediate represented by General Formula (d0-p) as recited in claim 1.
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.
Claims 1-2 are rejected under 35 U.S.C. 103 as being unpatentable over Fujiwara et al. (US20210188770A1, published 06/24/2021, IDS dated 4/01/2024) in view of Jones et al. (NPL, published 1924, PTO-892) and as evidenced by PubChem et al. (NPL, published 09/15/2025, PTO-892).
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Fujiwara et al. teaches synthesis of acid diffusion inhibitor Q-1 (shown below and see 0217-0222).
Fujiwara et al. differs from that of the instantly claimed invention in that Fujiwara et al. does not teach starting from a carboxylic acid, the acid dissociation constant (pKa) of 0.50 or more for the carboxylic acid used, and wherein Mpm’+ has an octanol/water partition coefficient (logPow) of 4.8 or less.
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Jones et al. teaches the velocity of saponification of methyl esters by potassium hydroxide in methyl alcohol-water mixtures was studied (general scheme shown below). Jones et al. teaches both methyl and ethyl esters in the saponification reaction (see introduction). The work has been extended to a study of the effects caused by a change in the base ; lithium hydroxide, barium hydroxide, and tetramethyl ammonium hydroxide were chosen in order that a comparison might be made with the effects observed. Jones et al. further teaches the equilibrium tables of the reaction between tetramethylammonium hydroxide and methyl n-butyrate as well as tetramethylammonium hydroxide and methyl o-chlorobenzoate (see page 2593 and 2594 for equilibrium tables of the reactions). The chemical equations of the reactions with tetramethylammonium hydroxide are shown below based on the general scheme (drawn by the
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examiner).
PubChem et al. teaches the calculated logP of benzyltrimethylammonium is 2.2 (see section 3.1).
Regarding the limitation of starting from a carboxylic acid, it would have been obvious before the effective filing date of the claimed invention to modify the teachings of Fujiwara et al. by alternatively starting the reaction, as taught by Fujiwara et al., with a carboxylic acid to arrive at the instantly claimed invention. It would have been prima facie obvious for one of ordinary skill in the art to start the reaction with a carboxylic acid because reacting an ethyl ester with tetramethyl ammonium hydroxide, as taught by Fujiwara et al., would naturally flow into saponifying the ester, as taught by Jones et al., to form a carboxylate intermediate in situ. One of ordinary skill in the art would have a reasonable expectation of success in alternatively starting the reaction with a carboxylic acid because the ethyl ester under basic conditions using tetramethyl ammonium hydroxide will naturally flow into a carboxylate, as taught by Jones et al., in the reactions as taught by Fujiwara et al., and therefore, go through a similar process with predictable results.
Regarding the limitation of logP, while PubChem et al. is post-art, PubChem et al. teaches evidence that the calculated logP of benzyltrimethylammonium, corresponding to the instant Mpm’+, is 2.2 which one of ordinary skill in the art would have expected the compound to possess prior to the effective filing date because logP is a functional property of the compound.
Regarding the limitation of pKa, the prior art does not teach a pKa of the carboxylic acid modified from SM2. However, pKa is a functional property that naturally flows from the structure of the compound. Therefore, because the modified SM2 compound corresponds to the instant general formula (d0-1), the limitation of a pKa of 0.50 or more would naturally flow from the structure of the compound and is obvious. Furthermore, mere recognition of latent properties in the prior art does not render nonobvious an otherwise known invention (see MPEP 2145(II)).
Regarding instant claim 1, Fujiwara et al. teaches SM2, which as taught by Jones et al., forms a carboxylate in situ when the ester reacts with tetramethylammonium hydroxide, corresponding to the instant carboxylic acid represented by General Formula (d0-1) wherein X0 is iodine, nb1 is 3, nb2 is 0, nb1 + nb2 is 3, and Yd is a divalent linking group. The modified SM2 is reacted with tetramethyl ammonium hydroxide, corresponding to the instant nitrogen-containing base compound and benzyl trimethyl ammonium chloride, corresponding to the instant onium compound. This reaction produces SM3, corresponding to the instant intermediate represented by General Formula (d0-p) wherein X0 is iodine, nb1 is 3, nb2 is 0, Yd is a divalent linking group, Mpm’+ is benzyltrimethylammonium which is an organic ammonium cation having a logPow of 4.8 or less, and m’ is 1. SM3 is then reacted with triphenyl sulfonium methyl sulfate, corresponding to the instant compound represented by General Formula (c0) wherein X- is methyl sulfate, Mm+ is triphenyl sulfonium which is an onium cation, and m is 1. This reaction produces Q-1, corresponding to the instant compound represented by General Formula (d0) wherein X0 is iodine, nb1 is 3, nb2 is 0, nb1 + nb2 is 3, Yd is a divalent linking group, Mm+ is triphenyl sulfonium which is an onium cation, and m is 1.
Regarding instant claim 2, Fujiwara et al. teaches triphenyl sulfonium, corresponding to the instant Mm+ being a sulfonium cation.
Conclusion
No claim is found allowable.
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/KRISTEN W BRADY/Examiner, Art Unit 1692
/SCARLETT Y GOON/Supervisory Patent Examiner
Art Unit 1693
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