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 .
This Office action is in response to the amendment filed August 13, 2026, which amends claims 1, 3, 8, and 10 and cancels claims 2, 9, 11, 13, 15, and 16. Claims 1, 3-8, and 10 are pending.
Response to Amendment
Applicant’s amendment of the claims, filed August 13, 2026, caused the withdrawal of the rejection of claims 11, 13, 15, and 16 under 35 U.S.C. 102(a)(1) as being anticipated by Meng et al. (US 2011/0095273) as set forth in the Office action mailed May 28, 2026.
Applicant’s amendment of the claims, filed August 13, 2026, caused the withdrawal of the rejection of claims 1-10 under 35 U.S.C. 103 as being unpatentable over Stipanovic et al. (Journal of Labelled Compounds and Radiopharmaceuticals-Vol. XXIV, No. 6 pages 741-743) in view of Giles et al. (Tetrahedron Letters 2015, 56, 747-749) as set forth in the Office action mailed May 28, 2026.
Applicant’s amendment of the claims, filed August 13, 2026, caused the withdrawal of the rejection of claims 2 and 9 on the ground of nonstatutory double patenting as being unpatentable over copending Application No. 17/779,920 as set forth in the Office action mailed May 28, 2026.
Response to Arguments
Applicant’s arguments with respect to claim(s) 1, 3-8, and 10 have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
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 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.
Claim(s) 1, 3-8, and 10 is/are rejected under 35 U.S.C. 103 as being unpatentable over Stipanovic et al. (Journal of Labelled Compounds and Radiopharmaceuticals-Vol. XXIV, No. 6 pages 741-743) (hereafter “Stipanovic”) in view of Giles et al. (Tetrahedron Letters 2015, 56, 747-749) (hereafter “Giles”) and Prechtl et al. (Angew. Chem. Int. Ed. 2007, 46, 2269–2272) (hereafter “Prechtl”).
Regarding claims 1, 3-8, and 10, Stipanovic teaches the method of deuterating an aromatic compound by using the acid exchange method (page 741 summary). Stipanovic teaches that the to perform the acid exchange method, the aromatic compound is in a solution with heavy water, trifluoroacetic acid (catalyst), and tetrahydrofuran (THF) as the solvent and the solution is heated to 75 C (page 741 summary).
Stipanovic does not teach where the solution contains an anhydride which is a compound that could be hydrolyzed by the heavy water and where the temperature of the reaction is between 80 C and 150 C.
Giles teaches a method of deuterating aromatic compound using a deuterated trifluoroacetic acid exchange method (page 747 second and third paragraphs). Giles teaches that deuterated trifluoroacetic acid can be prepared quantitatively from trifluoroacetic anhydride and heavy water in essentially anhydrous fashion (page 747 third paragraph). Giles teaches that the acid catalyzed method can be done at a temperature between 80 C and 150 C, such as 110 C (page 748 Scheme 1).
Prechtl teaches a method of deuterating aromatic compounds using a deuterium/hydrogen exchange reaction where heavy water is the deuterium source (Title and page 2270 left column Scheme 3). Prechtl teaches that solvent used for the reaction is cyclohexane (page 2270 left column Scheme 3).
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the method of Stipanovic to replace trifluoroacetic acid with trifluoracetic anhydride as taught by Giles. The motivation would have been to do in the reaction in essentially an anhydrous fashion.
Furthermore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to try to increase the reaction temperature in the method of Stipanovic to a temperature between 80 C and 150 C, such as 110 C as taught by Giles. Since Giles teaches acid catalyzed exchange reactions can occur at 110 C it would have been obvious to try to increase the reaction temperature to find the best reaction temperature to perform the reaction.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to solvent used for the exchange reaction of Stipanovic, THF, with cyclohexane, as taught by Prechtl. The substitution would have been solvent for deuterium/hydrogen exchange reaction where heavy water is used as the deuterium source for another solvent. One ordinary skill in the art would expect that cyclohexane can be used as a solvent for the reaction with aromatic compounds.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1, 3-6, 8 and 10 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-4 and 6-11 of copending Application No. 17/779,920 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because the claims are copending Application No. 17/779,920 are a species of the claimed invention and anticipated the claims of the instant application.
Claim 1 of copending Application No. 17/779,920 corresponds to claims 1 and 4 of the instant application.
Claim 3 of copending Application No. 17/779,920 corresponds to claim 3 of the instant application.
Claim 5 of copending Application No. 17/779,920 corresponds to claim 6 of the instant application.
Claim 6 of copending Application No. 17/779,920 corresponds to claim 6 of the instant application.
Claim 8 of copending Application No. 17/779,920 corresponds to claim 8 of the instant application.
Claim 10 of copending Application No. 17/779,920 corresponds to claim 11 of the instant application.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Conclusion
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 ANDREW K BOHATY whose telephone number is (571)270-1148. The examiner can normally be reached Monday-Friday 7am-4pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Curtis Mayes can be reached at (571)272-1234. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/ANDREW K BOHATY/Primary Examiner, Art Unit 1759
