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 .
Response to Remarks and Amendments
Applicants’ response and amendments filed January 28, 2026 have been entered. All rejections and objections not explicitly maintained herein are withdrawn. The rejections below constitute the full set of rejections being applied to the instant claims.
With regard to the rejection of claims 1-7 (now 1-4 and 7) under 35 USC 102(a)(1) as being anticipated by Kallepalli et al., Applicants traverse the rejection on the grounds that the claim amendments are sufficient to overcome the finding of anticipation. The examiner respectfully disagrees. Although acetic anhydride was deleted from the scope of claim 6 (effectively overcoming the rejection with respect to dependent claim 6), claim 1 (and dependent claims 2-4 and 7) were amended only to require the presence of at least one of Chemical Formulae 2 – 4 in the reaction mixture. Although Chemical Formula 1 was removed from the scope of the claims, acetic anhydride still reads on Chemical Formula 3 where one of R5 and R6 is methyl and the other is (C=O)-methyl. Accordingly, the rejection is maintained herein.
With regard to the rejection of claims 1-7 (now claims 1-5 and 7) for nonstatutory double patenting, Applicants argue that the rejections are no longer valid in view of the claim amendments. However, this argument is not persuasive for substantially the same reasons as described with respect to the anticipation rejection above (since the rejection over the claims of 18/017,732 is in view of the Kallepalli reference). Further, the rejection over the claims of 18/017,716 stands on its own as it was not in view of any additional reference and, as noted in the original rejection, conflicting claim 5 recites trifluoromethanesulfonic anhydride, trifluoroacetic anhydride, acetic anhydride, methanesulfonic anhydride, methyl acetate, ethyl acetate and dimethylacetamide as the organic compound which can be hydrolyzed by heavy water. All of these substances are still included in amended claim 1, and most are still recited in amended claim 6. Accordingly, the rejections are maintained herein.
Status of Claims
Currently, claims 1-4, 6-11, and 13-19 are pending in the instant application. Claims 8-11 and 13-19 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention there being no allowable generic or linking claim.
Claims 1-4 and 6-7 read on the elected invention/species and are therefore under consideration herein.
Claim Rejections – 35 USC § 102
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) 1-4 and 7 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Kallepalli et al.
Regarding claim 1, the prior art teaches a deuterated reaction of an aromatic compound (3-chloro-N,N-dimethylaniline) in a solution with heavy water (D2O), an organic compound which can be hydrolyzed by heavy water (acetic anhydride, referred to as Ac2O in the prior art, as recited by instant dependent claim 6) and an organic solvent (1,2-dimethoxyethane, referred to as DME in the prior art, as recited in instant dependent claim 4). Finally, regarding instant dependent claim 7, the prior art teaches performing the deuterated reaction by heating the solution to 150°C. See p. 8348, left column, “3-Chloro-N,N-dimethylaniline-5-d” section. Thus, since the prior art teaches all required features of the instantly claimed invention, the claims are anticipated.
Claims 1-4 and 6-7 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Sandip Kumar Das et. al. (“Ir-Catalyzed Intramolecular Transannulation/C(sp2)-H Amination of 1,2,3,4-Tetrazoles by Electrocyclization”, Supporting Information, Journal of the American Chemical Society, 140, 27, 2018).
At Page S17, DAS teaches the following reaction:
PNG
media_image1.png
182
429
media_image1.png
Greyscale
This reaction reads on the limitations recited at instant Claim 1 and all dependent claims, as p-toluidine (
PNG
media_image2.png
100
52
media_image2.png
Greyscale
) reads on the limitation of an aromatic compound comprising one or more aromatic rings. Trifluoroacetic anhydride reads on the limitation of an organic compound which can be hydrolyzed by heavy water, Das teaches the reaction was performed in heavy water, and further diethyl ether is added to the mixture, which reads on the required organic solvent.
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 obviousness-type 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); and 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 a nonstatutory double patenting ground provided the conflicting application or patent either is shown to be commonly owned with this application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement.
Effective January 1, 1994, a registered attorney or agent of record may sign a terminal disclaimer. A terminal disclaimer signed by the assignee must fully comply with 37 CFR 3.73(b).
Claims 1-4 and 6-7 are provisionally rejected under the judicially created doctrine of obviousness-type double patenting as being unpatentable over claims 1-16 of US Patent Application 18/017,716. Note that the rejection is provisional in nature since the conflicting claims have not, in fact, been patented.
An obviousness-type double patenting rejection is appropriate where the conflicting claims are not identical, but an examined application claim is not patentably distinct from the reference claim(s) because the examined 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).
Although the conflicting claims are not identical, they are not patentably distinct from each other because the method of the conflicting claims recites performing a deuterated reaction of an aromatic compound including one or more hydrocarbon aromatic rings using a solution comprising heavy water, an organic compound which can be hydrolyzed by the heavy water, the aromatic compound, and an organic solvent. Accordingly, the conflicting claims are identical to the process recited in the instant claims, but recite a narrower subset of compounds by requiring the aromatic rings to be hydrocarbon rather than unlimited as in the instant claims. Thus, the conflicting claims anticipate the instantly claimed method. Conflicting claim 3 limits the solvent to
PNG
media_image3.png
143
629
media_image3.png
Greyscale
while conflicting claim 5 limits the organic compound which can be hydrolyzed by the heavy water to trifluoromethanesulfonic anhydride, trifluoroacetic anhydride, acetic anhydride, methanesulfonic anhydride, methyl acetate, ethyl acetate and dimethylacetamide. Conflicting claims 6-7 recite the claimed process where the deuterated reaction is performed by heating the solution as required by instant claim 7. Since the conflicting claims encompass all the required features of the instant claims, with dependent claims reciting examples which anticipate the instantly claimed invention, a double patenting rejection is appropriate.
Claims 1-4 and 7 are provisionally rejected under the judicially created doctrine of obviousness-type double patenting as being unpatentable over claims 1-20 of US Patent Application 18/017,732, in view of Kallepalli et al. Note that the rejection is provisional in nature since the conflicting claims have not, in fact, been patented.
An obviousness-type double patenting rejection is appropriate where the conflicting claims are not identical, but an examined application claim is not patentably distinct from the reference claim(s) because the examined 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).
Although the conflicting claims are not identical, they are not patentably distinct from each other because the method of the conflicting claims recites performing a deuterated reaction of an aromatic compound using a solution comprising heavy water, an organic compound which can be hydrolyzed by the heavy water, and the aromatic compound. Accordingly, the conflicting claims are identical to the process recited in the instant claims, except that they are silent as to the presence of an organic solvent. Thus, the conflicting claims overlap with the instantly claimed method. Conflicting claim 5 limits the organic compound which can be hydrolyzed by the heavy water to trifluoromethanesulfonic anhydride, trifluoroacetic anhydride, acetic anhydride, and methanesulfonic anhydride. Conflicting claim 8 recites the claimed process where the deuterated reaction is performed by heating the solution as required by instant claim 7. With respect to the requirement of an organic solvent in the instantly claimed process, which is encompassed by the conflicting claims but the claims are silent regarding this feature, conducting the process of the conflicting claims in the presence of such a solvent would have been obvious to a person of ordinary skill in the art since. Performing deuteration reactions on an aromatic compound with heavy water, acetic anhydride, and 1,2-dimethoxyethane (DME) is taught by Kallepalli et al. and would not have been considered inventive. In the Kallepalli process, the deuteration in a solution with organic solvent provides for a 93% yield and was therefore known at the time of filing to result in successful deuteration of aromatic compounds with high yield. Since the conflicting claims encompass all the required features of the instant claims, with the prior art teaching the feature to which the conflicting claims are silent, a double patenting rejection is appropriate.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Alicia L. Otton whose telephone number is (571)270-7683. The examiner can normally be reached on Monday - Thursday, 8:00-6:00.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Mr. Fereydoun Sajjadi can be reached on 571-272-3311. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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.
Information regarding the status of an application may be obtained from the Patent Application Information Retrieval (PAIR) system. Status information for published applications may be obtained from either Private PAIR or Public PAIR. Status information for unpublished applications is available through Private PAIR only. For more information about the PAIR system, see http://pair-direct.uspto.gov. Should you have questions on access to the Private PAIR system, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative or access to the automated information system, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/ALICIA L OTTON/Primary Examiner, Art Unit 1699
Prosecution Insights