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 .
CONTINUING DATA
This application is a 371 of PCT/EP2022/059801 04/12/2022
FOREIGN APPLICATIONS
EP 21169034.2 04/17/2021
Claims 1-10 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.
Claims 8-10 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 8 is drawn to a method of using a compound of Formula (I), but does not recite any active steps. Attempts to claim a process without setting forth any steps involved in the process generally raises an issue of indefiniteness under 35 U.S.C. 112(b) or pre-AIA 35 U.S.C. 112, second paragraph. MPEP 2173.05(q). Claims 9 and 10 depend from claim 8 and also do not recite any active steps.
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.
Claim(s) 1-10 is/are rejected under 35 U.S.C. 102(a) as being anticipated by Jia (J. Am. Chem. Soc. 2021, 143, 7623-7628, published May 14, 2021, and supporting information).
Jia teaches the following compound on page 7623:
PNG
media_image1.png
116
134
media_image1.png
Greyscale
This is a compound of formula (I) where R1-R8 are all H and X- is triflate. The compound was prepared by reacting formula (II) withj a trifluoromethyl group transfer agent which is triflkic acid anhydride. See page 7624.
PNG
media_image2.png
87
580
media_image2.png
Greyscale
Compound 1 was reacted with an anion exchange reagent NaBF4 to obtain a compound wherein X- is BF4-. Page S11.
PNG
media_image3.png
182
607
media_image3.png
Greyscale
Formula I was reacted with an aliphatic hydrocarbon or aromatic hydrocarbon or heteroaromatic hydrocarbon in Scheme 4.
PNG
media_image4.png
226
983
media_image4.png
Greyscale
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.
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) 1-5 and 7-10 is/are rejected under 35 U.S.C. 103 as being unpatentable over Unemoto (EP0382206A1, 1990, cited on IDS) in view of Ritter (EP3650446A1, 2020, cited on IDS), Liu (J. Phys. Org. Chem. 2001; 14: 81-89, cited on IDS) and Yus (Tetrahedron 59 (2003) 2083-2092).
Unemoto teaches the following compound in Example 15:
PNG
media_image5.png
144
274
media_image5.png
Greyscale
The compound is used for introducing a perfluoroalkyl group into an organic compound (claim 9). Organic compounds into which the perfluoroalkyl group can be introduced include aromatic compounds (page 7, lines 44-46) or compounds containing C=O groups (Table 2). The compound is prepared as in Examples 4, 8, and 15:
PNG
media_image6.png
210
487
media_image6.png
Greyscale
PNG
media_image7.png
215
449
media_image7.png
Greyscale
PNG
media_image8.png
211
674
media_image8.png
Greyscale
Unemoto’s compound contains an oxygen and a sulfur atom, not two sulfur atoms as in the current claims.
Liu teaches the following thianthrenium triflates for reacting with hydrocarbon nucleophiles (page 82 and Table 1):
PNG
media_image9.png
230
360
media_image9.png
Greyscale
Compound 3a was prepared by reaction of Th with methyl formate and triflic acid (page 82, right column).
Ritter teaches the following compound for direct C-H functionalization (see abstract):
PNG
media_image10.png
179
187
media_image10.png
Greyscale
The resulting compound was then used to transfer the aromatic group to a methyl group (page 45) or an aromatic group (page 46). In one example, the triflate salt was converted to the PF6- salt [0106].
It would have been obvious to one of ordinary skill in the art at the time the application was filed to replace the oxygen in Unemoto’s compound with a sulfur in order to obtain a compound useful for transferring a trifluoromethyl group to an organic compound. Simple substitution of S for O would have resulted in the claimed invention, and the results would have been predictable because both Unemoto’s compound and the thianthrene compounds taught by Ritter or Liu are used for C-H functionalization. The skilled artisan would have prepared the thianthrene analog as Unemoto’s compound was prepared, using a thioether analog of the ether starting material. The thioether starting material was known at the art before the application was filed, as illustrated by Yus on page 2084 (compound 14), so the skilled artisan would have had a reasonable expectation of success in preparing the compound. Alternatively, the skilled artisan would have prepared the compound using the same methods used for preparing Liu’s compounds, which would imply the use of trifluoromethyl formate instead of methyl formate.
Claim(s) 6 is/are rejected under 35 U.S.C. 103 as being unpatentable over Unemoto (EP0382206A1, 1990, cited on IDS) in view of Ritter (EP3650446A1, 2020, cited on IDS), Liu (J. Phys. Org. Chem. 2001; 14: 81-89, cited on IDS) and Wang (CCS Chem. 2010, 2, 1710-1717).
Unemoto, Ritter, and Liu teach as set forth above, and Liu teaches preparing the thianthrenium compounds using alkyl formates.
Liu does not teach preparing the thianthrenium compound using triflic acid anhydride as the trifluoromethyl group transfer agent.
Wang teaches trifluoromethylation reagents on page 1710, including triflic acid anhydride.
PNG
media_image11.png
134
599
media_image11.png
Greyscale
It would have been obvious too one of ordinary skill in the art at the time the application was filed to prepare the claimed compounds as set forth in the rejection above, and to prepare the compound using triflic acid anhydride. Liu teaches the use of alkyl formates for preparing the compounds, which implies the use of trifluoromethyl formate. An alternative trifluoromethylation agent is triflic acid anhydride, as taught by Wang. Simple substitution of one trifluoromethylation agent for another would have resulted in the claimed invention, and the results would have been predictable because both agents are used for trifluoromethylation.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to LAYLA D BERRY whose telephone number is (571)272-9572. The examiner can normally be reached 7:00-3:00 CST, M-F.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
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.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/LAYLA D BERRY/Primary Examiner, Art Unit 1693
Prosecution Insights