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 .
Election/Restrictions
Claims 1-9 and 17-22 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 6/1/2026. The invention of claims 23-26 and 28 is under examination.
The following election of species is also acknowledged:
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The elected fluorinated compound (pf) is a compound of the following formula:
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, as evidenced by the SciFinder CAS® entry for the instant application (AN:2022:2505761). The species election encompasses claims 23-26 and 28.
This species was found to be free from the prior art, therefore the scope of the reaction was extended to those discussed in the rejections below.
Claim Status
Claims 23-26 and 28 are under examination and claims 1-9 and 17-22 are withdrawn.
Priority
The instant application was filed on 9/25/2023 and claims the benefit of priority to:
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See filing receipt dated 10/5/2023.
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Claim Rejections - 35 USC § 102
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 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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claim(s) 23 and 24 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Shishimi (“BrF3-KHF2: An air-stable fluorinating reagent” Journal of Fluorine Chemistry, 2014, p. 55).
Shishimi teaches the following reaction to produce a fluorinated organic compound (2a):
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See Table 2 on p. 56. Compound (2a) is obtained in an isolated and purified yield of 99%. Also see procedure 4.3. on p. 58-59. If any sulfur-containing substance from the starting material (1d) is present, which is not taught by Shishimi, then its concentration must fall within the claimed range of 10000 ppm (1 wt%) or less because the yield of the purified compound is 99%. Also see MPEP 2131.
Claim(s) 23 and 24 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Kanie (“A Facile Synthesis of Trifluoromethylamines by Oxidative Desulfurization-Fluorination of Dithiocarbamates” Bull. Chem. Soc. Jpn, 1998, p. 1973).
Kanie teaches the following reaction on p. 1974 to produce fluorinated organic compounds of formula (3):
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. See Table 1. Entries 6, 13, 15 of Table 1 teach purified compounds of formula (3) (3b and 3e) which are obtained in isolated purified yields of 99%. Also see preparation of compounds (3b) and (3e) on p. 1983-1984. If any sulfur-containing substance from the starting material (2) is present, which is not taught by Kanie, then its concentration must fall within the claimed range of 10000 ppm (1 wt%) or less because the yield of the purified compound is 99%. Also see MPEP 2131.
Claim(s) 23 and 24 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Yoneda (US 2003/0176747, published on 9/18/2003).
Yoneda teaches the following reaction in Table 3 on p. 19 to produce a fluorinated organic compound in 99% isolated purified yield:
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. Also see description of “Method A” in [0131-0132]. If any sulfur-containing substance from the starting material is present, which is not taught by Yoneda, then its concentration must fall within the claimed range of 10000 ppm (1 wt%) or less because the yield of the purified compound is 99%. Also see MPEP 2131.
Claim(s) 23-26 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Malik (US2003/0153774, published on 8/14/2003).
Malik teaches the production of fluorinated organic compound Citalopram·HBr of the following structure:
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. Malik teaches that “quality specifications for pharmaceutical quality Citalopram are extremely stringent and require material with a purity in excess of 99.7%. Malike teaches an example wherein Citalopram is obtained with an HPLC purity of 99.8% and is silent regarding the presence of any type of compound or substance comprising sulfur:
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. See [0149-0156]. Therefore, all pharmaceutical quality Citalopram, including that above, anticipates the instantly claimed composition. The claimed range of “10000 ppm by mass or less in terms of sulfur” includes the range of 0 ppm sulfur. Further, even sulfur is present, its concentration can be no greater than 0.2 wt% (2000 ppm). Also see MPEP 2131.
Claim(s) 23-26 and 28 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Komatsubara (US 2002/0035848, published on 3/28/2002).
Komatsubara teaches a refrigerant composition comprising:
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. See claims. Tetrahydrothiophene is a sulfur-containing substance and the fluorinated organic compound is a hydrocarbon fluoride having 1 to 4 carbon atoms. Tetrahydrothiophene is present in the range of 10 wt ppm to 0.5 wt % (5000 ppm) or nor more than 0.1 wt ppm. Because the full genus of “a hydrocarbon having 1 to 4 carbon atoms, or a flammable hydrocarbon fluoride derived by substituting one or more hydrogen atoms of the hydrocarbon with fluorine atoms” is at once envisaged, the refrigerant of claims 2-4 of Komatsubara anticipates claims 23-26 and 28. Also see MPEP 2131.
Claim Rejections - 35 USC § 102/103
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 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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
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) 23-26 and 28 is/are 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 Yoneda (US 2003/0176747, published on 9/18/2003).
Applicant claims a composition comprising a fluorinated organic compound (pf) and a sulfur- containing substance with the proviso that the fluorinated organic compound is excluded from the sulfur-containing substance, wherein the content of the sulfur-containing substance is 10000 ppm by mass or less in terms of sulfur.
Yoneda discloses a method for producing fluorinated organic compounds using a fluorinating agent comprising IF5 and at least one member selected from the group consisting of acids, bases, salts, and additives. See abstract. Yoneda teaches that the fluorinated organic compounds can be obtained by substituting a sulfur atom in a sulfide (thioether) or thiocarbonyl (including thioketone, thioester, thiocarbonic acid, thioamide, dithiocarboxylate, and dithiocarbamate) with a fluoride atom. See [0035-0037] and [0060-0064]. Yoneda specifically teaches the following examples:
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820
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See Tables 1-6.
Yoneda teaches that compounds prepared by Methods A to E and H to J have been isolated and purified by column chromatography and analyzed by NMR, IR, and MS. See [0131-0154]. Yoneda is silent regarding the presence of any “sulfur-containing substances” in the final purified and isolated products. Yoneda further teaches that the fluorinating agent is preferably IF5/Et3N-3HF and that the reactions contain the organic solvents shown in the Tables. The reactions are carried out at room temperature (r.t.) for the period of time set forth in the examples, though the reactions can also be carried out at temperatures above 40°C. See [0123]. Yoneda additionally teaches that after completion of the reaction, the mixture is contacted with aqueous sodium carbonate followed by 10% sodium thiosulphate aqueous solution. Yoneda teaches that the treatment with the aqueous solutions takes place at reaction temperature, including those at 40°C and above. See [0131-0132] and examples 2, 3, 6-10, 14, 24, 25, 27, 41-43, and 50-63 in the Tables.
Regarding the rejection with respect to 35 USC 102:
The reaction products of Yoneda are presumed to inherently possess the claimed purity levels because the process for producing the compounds is substantially identical to that claimed and described in the specification as filed for producing the claimed compositions. See examples in [0118-0133] of the specification as filed. The instant specification teaches that when any of the exemplified organic sulfur compound is fluorinated with IF5/Et3N-3HF in an organic solvent, even under elevated temperature, and treated with an aqueous nucleophile, that the resulting crude product possesses sulfur concentration within the claimed ranges. Therefore, products from substantially identical processes should also be substantially identical. Also see MPEP 2112.
Regarding the rejection with respect to 35 USC 103:
It would have been prima facie obvious to arrive at the instantly claimed process based on the teachings of Yoneda with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to obtain the fluorinated organic compounds of Yoneda with the low sulfur substance levels claimed because purified compounds are always desirable. Yoneda explicitly teaches that the compounds can be purified via column chromatography, therefore if the level of an impurity in the product, including those containing sulfur, is too high then it would prima facie obvious to further purity the product to remove the contaminants. Further, the process of Yoneda substantially overlaps with that discussed in the specification as filed for producing said compositions. Therefore, it is reasonable to conclude that the products produced by Yoneda should have similar, if not identical, purity profiles to those claimed. Further, the process variables of Yoneda overlap with those claimed, therefore routine optimization of the process disclosed in Yoneda would lead the skilled artisan to the claimed products with a reasonable expectation of success. Also see MPEP 2144.05.
Subject Matter free from the Prior Art
The claimed composition comprising the following compound as the fluorinated organic compound is free from the prior art:
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. The closest prior art is Milcent (“Part V: Nitrogen-Linked Fluorine-Containing Motifs” Emerging Fluorinated Motifs: Synthesis, Properties, and Applications, 2020). Milcent teaches the production and use of N-fluoro organic compounds, but there is no motivation to produce the compound above, let alone a composition comprising said compound.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMY C BONAPARTE whose telephone number is (571)272-7307. The examiner can normally be reached 11-7.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/AMY C BONAPARTE/ Primary Examiner, Art Unit 1692
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