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 .
Status of the Claims
The amendment filed on 11/19/2025 has been entered. Claims 5 and 8. Thus claims 5-11, 13-14 and 18-20 are currently pending, claim 18 has been withdrawn from further consideration and claims 5-11, 13-14 and 19-20 are under examination.
Withdrawn Objections and Rejections
The objection to the specification has been withdrawn in view of the amended specification filed on 11/19/2025.
Claim 8 has been amended to obviate the indefinite language and thus the 112(b) rejection has been withdrawn.
Claim 5 has been amended to now recite the new limitation “wherein the nitrosylsulphuric acid comprises 10% to 40% by weight nitrosylsulphuric acid in sulphuric acid”. The combination of CN108947765A (CN’765), Sigma-Aldrich (“2,4,5-trifluoroaniline” Deposit and available date Jul. 12, 2007) and Sanchez (Sanchez, J. P. et al. “New 8-(Trifluoromethyl)-Substituted Quinolones. The Benefits of the 8-Fluoro Group with Reduced Phototoxic Risk” J. Med. Chem. 1992, 35, 361-367) fails to teach or suggest the newly recited limitation. As such, the 103 rejection of the record has been withdrawn.
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.
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.
Claims 5-11, 13-14 and 19-20 are rejected under 35 U.S.C. 103 as being unpatentable over Patent number CN107312353A (CN’353; citations will be from the machine translation attached herein) in view of Patent application publication number US2010/0137612A1 (US’612), Sigma-Aldrich (“2,4,5-trifluoroaniline” Deposit and available date Jul. 12, 2007; cited in PTO-892 08/05/2025) and Sanchez (Sanchez, J. P. et al. “New 8-(Trifluoromethyl)-Substituted Quinolones. The Benefits of the 8-Fluoro Group with Reduced Phototoxic Risk” J. Med. Chem. 1992, 35, 361-367; cited in PTO-892 08/05/2025).
Regarding claims 5 step (a) and 21, CN’353 teaches a similar process as instantly claimed in the preparation of diazonium salt by reacting an aniline with nitrosyl sulfuric acid and sulfuric acid (Examples 1-2):
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The amounts used are 50 g of sulfuric acid and 32.6 g of nitrosyl sulfuric acid (Example 1) and 60 g of sulfuric acid and 32.6 g of nitrosyl sulfuric acid (Example 2), which are equivalent to 39.5 wt% and 35.2 wt%, respectively, of nitrosyl sulfuric acid in sulfuric acid.
Regarding claim 8, CN’353 teaches that the molar ratio of the aniline to nitrosyl sulfuric acid ranges 1.5 to 4.0 ([0012]).
Regarding claim 20, the reaction is conducted at a temperature of -10 to 25° C for 4-5 hrs ([0014]-[0015]).
Regarding claims 5 step (b) and 19, CN’353 fails to teach or suggest of further brominating the azo product with a brominating agent. However, in the same field of endeavor, US’612 teaches brominating an azo starting material (4-acetyl-2-methylbenzenediazonium sulfate) with copper bromide and HBr ([0257]).
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Regarding claim 5, neither CN’353 nor US’612 teaches the preparation of 1-bromo-2,4,5-trifluorobenzene from 2,4,5-trifluoroaniline or a sulfate salt thereof. The deficiencies are cured as follows.
Sigma-Aldrich teaches the commercial availability of 2,4,5-trifluoroaniline prior to the effective filing date of the instant invention.
Furthermore, Sanchez teaches that 1-bromo-2,4,5-trifluorobenzene is a key intermediate in the synthesis of antibacterial 8-(trifluoromethyl)-substituted quinolone compounds (Scheme I).
As such, a skilled artisan would have been motivated in replacing the aniline starting material of CN’353 with the commercially available 2,4,5-trifluoroaniline of Sigma-Aldrich and in conducting the two step reactions of CN’353 (obtaining the azo product) and US’612 (brominating the azo product) with a reasonable expectation of success in preparing 1-bromo-2,4,5-trifluorobenzene that is a useful intermediate.
Regarding claim 6, US’612 teaches purifying the crude bromo product to obtain the bromo product at a purity of 99.1% ([0257]).
Regarding claim 7, US’612 teaches the use acetonitrile and water (from the aqueous azo starting material) ([0257]).
Regarding claims 10-11, the claims appear to be further limiting in-situ generated metal bromide of claim 5. It is noted though that the in-situ generated metal bromide is recited in claim 5 as an alternative limitation of the brominating agent of claim 5. Since US’612 teaches the other alternative specie of brominating agent, metal bromide, of claim 5, the in-situ generated metal bromide of claim 5 and any other limitations that further limit the in-situ generated metal bromide, as in claims 10-11, are not given patentable weight.
Regarding claims 13-15, since the purity of the crude bromo product after purification is 99.1%, a skilled artisan would expect that the purity of the crude bromo product prior to purification to be less than 99.1%.
Thus, all the parameters, molar ratios, weight percent, reaction temperatures, purity etc. of claims 6-8, 11, 13-14 and 20-21 would have been obvious in view of the rationale provided above, i.e. by replacing the aniline of CN’353 with 2,4,5-trifluoroaniline of Sigma-Aldrich and conducting the two steps reaction taught in CN’353 and US’612.
Regarding claim 9, the combination of the above references does not suggest the claimed weight percent of metal bromide with respect to 2,4,5-trifluoroaniline. However, such a determination of the weight percent of reagents used in a chemical reaction would be within the purview of a skilled artisan. In this instance, since there is only one functional group in 2,4,5-trifluoroaniline, the amine group, that ultimately gets replaced - via a two-step process – by one bromo group in the brominating agent, a skilled artisan would start by using 1:1 equivalents of the 2,4,5-trifluoroaniline and the brominating agent. From this starting point, a skilled artisan would have been motivated in improving and determining, via routine optimization, the optimum workable weight percent ranges and would arrive at the instantly claimed weight percent of metal bromide with respect to 2,4,5-trifluoroaniline.
It would thus have been prima facie obvious to the skilled artisan before the effective filing date of the instant invention in conducting a process for the preparation of 1-bromo-2,4,5-trifluorobenzene comprising the steps of: a) forming 2,4,5-trifluorophenyl diazonium salt by reacting 2,4,5-trifluoroaniline or a sulfate salt thereof with nitrosyl sulfuric acid, wherein the nitrosyl sulfuric acid comprises 10% to 40% by weight nitrosyl sulfuric acid in sulfuric acid; and b) brominating the 2,4,5-trifluorophenyl diazonium salt using a brominating agent in the presence of a metal bromide or in-situ generated metal bromide to obtain crude 1-bromo-2,4,5-trifluorobenzene in view of the combination of CN’353, US’612, Sigma-Aldrich and Sanchez.
Conclusion
Claims 5-11, 13-14 and 19-20 are rejected and no claims are allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MEDHANIT W BAHTA whose telephone number is (571)270-7658. The examiner can normally be reached Monday-Friday 8am-5pm.
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/MEDHANIT W BAHTA/Primary Examiner, Art Unit 1692
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