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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 01/30/2026 has been entered.
Amended claims 1-4, 6-12 are pending.
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.
Previously presented rejection of claims 1-4, 6-10 (and new claims 11 and 12) are 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 is maintained.
Applicant is not responsive to all issues raised. For example applicant is silent with respect to citation noted in the previous action.
Base claim is drawn to chemical process, that while reciting one of the participant in the reaction (the base) does not define the starting material(s) are products(s). In addition critical factors such as amount of base, solvent and solvent (argued by the applicant as distinguishing from prior art elsewhere in the Remarks) are defined in broad terms such that the metes and bounds of the claim limitations of process parameters are unclear.
In addition the language ‘sum to 1’ relating to the molar ratio of the reactants while finding reference in the specification does not find support in the actual working examples where in the ratio is not 1:!.
One of skill in the art at once would recognize that conversion of starting materials and amount of products formed are inexorably linked to process parameters such as temperature and duration of the reaction. Consider for example the phrase ‘constant temperature’ (claim 2). A reaction that can occur only at 100oC just cannot provide a product at -10oC. Compare Fig 1 of specification in this regard. Critical process parameters are not found in the base claim. The implication that any and all SNAr reactions can happen at any ‘constant temperature’ would produce 80% SNAr product contradicts fundamental principles of chemistry. It is one of commonsense to anticipate that process parameters such as temperature, pressure, mixing (grinding/crushing/pulverizing/shearing), the presence or absence of solvent and what solvent etc., are important factors in chemical process including mechanochemical reactions. For example, as taught by Andersen (Insights into Mechanochemical Reactions at Targetable and Stable, Sub-ambient Temperatures Angew. Chem. Int. Ed. 2018, 57, 13062 –13065), recently the “Hot Spot Theory,” which suggested that the pulverizing and grinding action induced localized, extremely high temperatures that allowed reactions to proceed, was supplanted by a simple theory involving mixing rates and thermal energy-essentially unifying the energetics of solution-based chemistry with mechanochemistry.
Further, the phrase ‘additional solvent’ is also confusing because it is unclear if the claimed process is ‘solvent-free’ or one of the reactants act as ‘solvent’.
Note that in general, a process should at least recite a positive, active step and any process parameters necessitated by the specification so that the claim will "clearly set out and circumscribe a particular area with a reasonable degree of precision and particularity” In re Moore, 169 USPQ 236, and make it clear what subject matter the claim encompasses, as well as make clear the subject matter from others would be precluded.
Further, although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993). Also see, In re Zletz, 13 USPQ2d 1320, 1322. “An essential purpose of patent examination is to fashion claims that are precise, clear, correct and unambiguous.”
Dependent claims do not solve the problem of the base claim 1. As such all claims are rejected.
Claim Rejections - 35 USC § 102
Claim Rejections - 35 USC § 103
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 following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Previously presented rejection of claims 1-4, 6-10 (and new claims 11 and 12) rejected under 35 U.S.C. 102 (a)(1)) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Dushkin, Synthetic Communications (2001), 31(7), 1041-1045; Otles, Solid-Phase mechanochemical synthesis of fluoroaromatic compounds Dissertation Universite de Toulouse, 11 December 2008 Entirety of document, in particular, page 43, paragraph 4. Page 44, paragraph 3-4; Cao, Green Chemistry 2018, 20, 443-4447, Translating solid state organic synthesis from a mixer mill to a continuous twin screw extruder; and Khoa, Planetary Ball Mill Process in Aspect of Milling Energy, J.Kor.Powd.Met.Inst. 21(2), 2014. 155-164 and Aksenov, Journal of Fluorine Chemistry (1985), 28(1), 73-87 is maintained.
Applicants arguments are not persuasive. New reference Aksenov added in view of amendments to claims and augment previously presented rejection.
With respect to Dushkin, Applicant states that Dushkin does not demonstrate operation at constant temperature. Applicant points to disclosure with respect to ‘constant temperature’ and emphasizes that in 2001 maintaining ‘constant temperature’ was not possible/viable Among other outcome such as yield,
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This contrast, Applicant argues that as per disclosure [0028], concentration beyond 1.0M resulted in ‘inhibitory effect’
Likewise, Aksenov reaction examples are under controlled conditions and is not ‘without solvent’ as instant process.
Other references Otles, Cao and Khoa, applicant argues, are not as limited by the claims.
Response:
Applicants arguments are not persuasive. Applicant noted process parameters, for example, constant temperature (in claim 2) is not found in the base claim. The argument that
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is confusing in that yield in Example 1 and Example 2 provide yield comparable to reactions that are run at 1:! molar ratio. Further these Examples 1 and 2 do relate to the new dependent claim 11. The process parameters in Working Examples in general, molar ratio, speed of mixing, etc. while having parameters argued by the Applicant as distinguishing from the cited prior art references, and critical are not found in the base claim. Further these parameters as per the working examples are specific to reactants.
The claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993).
Suggestion:
Recite in claims, process parameters as found in the working examples 1-7, thus including starting materials (reactants), base, stoichiometry, constant temperature and mixing equipment.
Following is from previous office action filed 07/30/2025
Previously presented rejection of claim(s) 1-4, 6-10 rejected under 35 U.S.C. 102 (a)(1)) as anticipated by or, in the alternative, under 35 U.S.C. 103 as obvious over Dushkin, Synthetic Communications (2001), 31(7), 1041-1045; Otles, Solid-Phase mechanochemical synthesis of fluoroaromatic compounds Dissertation Universite de Toulouse, 11 December 2008 Entirety of document, in particular, page 43, paragraph 4. Page 44, paragraph 3-4; Cao, Green Chemistry 2018, 20, 443-4447, Translating solid state organic synthesis from a mixer mill to a continuous twin screw extruder; and Khoa, Planetary Ball Mill Process in Aspect of Milling Energy, J.Kor.Powd.Met.Inst. 21(2), 2014. 155-164 and Aksenov, Journal of Fluorine Chemistry (1985), 28(1), 73-87.
Applicants arguments are not persuasive. New reference Aksenov added in view of amendments to claims and augment previously presented rejection.
According to Applicant, Dushkin reaction is not SNAr reaction and further the conversion rate is <75%. These are not in line with the claim limitations.
Further, Cao reaction, like Dushkin is not a SNAr reaction. These factors alone, Applicant argues, is enough to overcome the rejection, that is, Applicant need not argue over the additional references cited by the Examiner. However, Applicant would present arguments if requested by the Examiner.
Response:
First of all, Examiner requests that Applicant place on record arguments with regards to all references of record.
As to the whether Dushkin reaction is SNAr reaction:
The position taken by the Examiner is that Dushkin reaction is a SNAr reaction. As pointed out in the previous action (see page 3), Dushkin at page 1041 teaches
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Commonly understood meaning of the letters S, N and Ar correspond to the S N AND Ar in SNAr. Dushkin starting material octachloronaphthalene, has the electron withdrawing groups (halogens) necessary for ‘addition-elimination mechanistic’ detail inherent to SNAr reactions.
Examiner invokes additional examples of Aksenov in support of the above:.
Aksenov teaches many examples of mechanochemical processes, see Table 5 at page 79. Following is an example. With the electron withdrawn functionalities NO2 and Cl for the substitution of Cl with F.
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The same functionalities are in the instant working example SNAr reactions.
As to the argument that the claim limitation of 80% plus conversion is not found in the prior art is not persuasive because, one of skill in the art would understand that the outcome of any organic reaction for example with respect to yield/conversion, depends on multiple reaction parameters. For example, disclosure (working examples) itself is supportive of the fact that different chemical partners provide different yield/conversion.
The instant working example 3, provides 81% yield, while other working examples (with different starting materials) provide 90% plus conversions.
Multiple references placed on record (invoked and not invoked for rejection) clearly show that mechanochemical process is not applicants invention. In this regard see In re Moore, 169 USPQ 236 cited above under section -35 USC § 112.
Also see below noted post-filing articles for leading references in this area.
The art made of record and not relied upon is considered pertinent to applicant's disclosure.
Dushkin, Khimiya v Interesakh Ustoichivogo Razvitiya (2001), 9(5), 625-630
Kubota, Trends in Chemistry Mechanochemical Cross-Coupling Reactions, Volume 2, Issue 12, December 2020, Pages 1066-1081.
(Inventor) Anderson1, Rate and Yield Enhancements in Nucleophilic Aromatic Substitution Reactions via Mechanochemistry J.Org.Chem. 2021, 86, 13983-13989.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to NIZAL S CHANDRAKUMAR whose telephone number is (571)272-6202. The examiner can normally be reached M-F 8-5 EST.
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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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/NIZAL S CHANDRAKUMAR/Primary Examiner, Art Unit 1625