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 Claims
Claims 1-14, 16, and 18-20 are pending in the instant application.
Claims 15 and 17 have been canceled.
Election/Restriction
This action is in response to an election from a restriction requirement filed January 28th, 2026. There are 18 claims pending and 8 claims under consideration. Claims 9-14, 16, and 18-20 have been withdrawn as claims drawn to a non-elected invention. This is the first action on the merits. The present invention relates to a method comprising performing a deuterated reaction of an aromatic compound.
Applicant’s election without traverse of Group I, Claims 1-8 in the reply filed March 25th, 2026 is acknowledged. Applicant traversed the requirement for elections of Species A and B as detailed in the restriction requirement failed January 28th, 2026. Upon further consideration, the examiner withdraws the requirement for an election of species. Therefore this restriction is considered proper and thus made FINAL.
Priority
Acknowledgement is made of Applicant’s claim for foreign priority based on the KR10-2020-0108194 application filed in the Republic of Korea on August 27th, 2020.
Information Disclosure Statement
The Information Disclosure Statements filed on January 24th, 2023, January 22nd, 2024, and February 27th, 2024 have been fully considered by the examiner, except where marked with a strikethrough.
Specification
The abstract of the disclosure is objected to because the abstract lacks a description of the general nature of the instantly disclosed compounds and/or compositions and does not describe the use thereof. A corrected abstract of the disclosure is required and must be presented on a separate sheet, apart from any other text. See MPEP § 608.01(b).
Applicant is reminded of the proper content of an abstract of the disclosure.
In chemical patent abstracts for compounds or compositions, the general nature of the compound or composition should be given as well as its use, e.g., “The compounds are of the class of alkyl benzene sulfonyl ureas, useful as oral anti-diabetics.” Exemplification of a species could be illustrative of members of the class. For processes, the type of reaction, reagents and process conditions should be stated, generally illustrated by a single example unless variations are necessary.
The specification has not been checked to the extent necessary to determine the presence of all possible minor errors. Applicant’s cooperation is requested in correcting any of the errors of which Applicant may become aware of in the specification.
Claim Objections
Claim 5 is objected to because of the following informalities:
Claim 5 presently reads “… comprises at least one of the compound of Chemical Formula 3 and the compound of Chemical Formula 4…” As Chemical Formula 4 is not drawn to a single compound, the examiner has interpreted this to mean “… comprises at least one of the compound of Chemical Formula 3 and at least one of the compound of Chemical Formula 4…”.
Appropriate correction is required.
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 1-8 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 1 is rendered indefinite, as it is drawn to a method comprising the steps of “performing a deuterated reaction of an aromatic compound comprising one or more aromatic rings using a solution comprising the aromatic compound, heavy water, and an organic compound which can be hydrolyzed by the heavy water.” The objective and/or outcome of this method is not recited. Further, the term “deuterated reaction” is indefinite, and has not been sufficiently defined in the specification such that a person having ordinary skill in the art would reasonably ascertain the metes and bounds of this limitation. No concrete steps have been provided as limitations instructing how said reaction is to be performed, nor is it clear the intended result of such a reaction. Additionally, the recitation of the limitation of “an organic compound which can be hydrolyzed by the heavy water” renders the claim indefinite, as it is unclear whether the compound is hydrolyzed in the reaction, or if it simply must be capable of doing so.
Dependent Claims 2-8 do not fully resolve the indefiniteness of the aforementioned limitations, and are therefore also rendered indefinite.
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.
(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.
Claims 1 and 7-8 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Charlton et. al. (“The Synthesis of Specifically Deuterated Anthracenes”, Canadian Journal of Chemistry, 51, 11, Pages 1852-1856, 1973; cited on Applicant’s Information Disclosure Statement filed February 27th, 2024; hereinafter referred to as Charlton).
At page 1854, Second Column, Third Paragraph, Charlton teaches a method reading on the limitation recited at Claim 1 of performing a deuterated reaction of an aromatic compound using a solution comprising the aromatic compound, heavy water, and an organic compound which can be hydrolyzed by the heavy water.
Specifically, Charlton teaches anthracene is refluxed in a solution employing benzene as a solvent containing p-toluene sulfonyl chloride and D2O (heavy water). Ultimately, the product of this reaction is anthracene-9,10-d2. p-Toluene sulfonyl chloride reads on the limitation of a compound which can be hydrolyzed by heavy water.
For clarity of the record, anthracene is a compound of the structure:
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270
683
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Therefore, anthracene reads on the limitation recited in Claim 1 of an aromatic compound comprising one or more aromatic rings.
Anthracene-9,10-d2 has the structure:
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202
273
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Greyscale
Regarding Claim 7, Charlton teaches this reaction in the absence of a metal catalyst.
Regarding Claim 8, Charlton teaches the reaction is conducted at reflux, and therefore reads on the limitation of “performing the deuterated reaction of the aromatic compound by heating the solution.”
Claims 1-4 and 6-8 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; cited on Applicant’s Information Disclosure Statement filed February 27th, 2024; hereinafter referred to as Das).
At Page S17, DAS teaches the following reaction:
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182
429
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This reaction reads on the limitations recited at instant Claim 1, as p-toluidine (
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100
52
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) 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, and Das teaches the reaction was performed in heavy water.
Regarding Claim 2, trifluoroacetic anhydride (
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139
266
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) reads on a compound of Chemical Formula 1, wherein R1 and R2 are each CF3.
Regarding Claim 3, R1 ad R2 are the same as each other, and are an alkyl group substituted with a halogen group.
Regarding Claim 4, R1 and R2 are the same as each other, and are a substituent of Chemical Formula 5, wherein l is 0, m is 0, and n is 1.
Regarding Claim 6, the organic compound which can be hydrolyzed by the heavy water comprises trifluoracetic anhydride.
Regarding Claim 7, Das teaches the reaction is performed in the absence of a metal catalyst.
Regarding Claim 8, as shown in the scheme above, Das teaches the reaction is heated to 120oC.
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 1-8 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-4 and 6-7 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 they are both drawn to a method comprising performing a deuterated reaction of an aromatic compound comprising one or more aromatic rings using a solution comprising the aromatic compound, heavy water, and an organic compound which can be hydrolyzed by the heavy water.
The reference claims differ from the instant claims in that the reference claims recite the limitation of including an organic solvent in the deuterated reaction. The additional limitation of including an organic solvent do not render the claims patentably distinct because the instant claims use the transitional phrase “comprising”. Per MPEP 2111.03, I., “The transitional term "comprising", which is synonymous with "including," "containing," or "characterized by," is inclusive or open-ended and does not exclude additional, unrecited elements or method steps. See, e.g., Mars Inc. v. H.J. Heinz Co., 377 F.3d 1369, 1376, 71 USPQ2d 1837, 1843 (Fed. Cir. 2004) ("[L]ike the term ‘comprising,’ the terms ‘containing’ and ‘mixture’ are open-ended."). Invitrogen Corp. v. Biocrest Manufacturing, L.P., 327 F.3d 1364, 1368, 66 USPQ2d 1631, 1634 (Fed. Cir. 2003).” Therefore, practicing the reference claims reads on the instant claims, even in view of the additional limitation of the reaction comprising an organic solvent.
Further, chemical formulae 2, 3, and 4 as recited at the reference application’s Claim 1 are the same as chemical formulae 2, 3, and 4 as recited at instant Claim 2. Reference claim 6 further limits the organic compound which can be hydrolyzed by heavy water to at least one of trifluoromethanesulfonic anhydride, trifluoroacetic anhydride, and methanesulfonic anhydride, all of which are recited instantly at Claim 6.
Taken together, practice of the reference claims 1-4 and 6-7 reads on the limitations recited at the instant Claims 1-8.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1-8 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-7 of copending Application No. 18/017,716 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because they are both drawn to a method comprising performing a deuterated reaction of an aromatic compound comprising one or more aromatic rings using a solution comprising the aromatic compound, heavy water, and an organic compound which can be hydrolyzed by the heavy water.
The reference claims differ from the instant claims in that the reference claims recite the limitation of including an organic solvent in the deuterated reaction. The additional limitation of including an organic solvent do not render the claims patentably distinct because the instant claims use the transitional phrase “comprising”. Per MPEP 2111.03, I., “The transitional term "comprising", which is synonymous with "including," "containing," or "characterized by," is inclusive or open-ended and does not exclude additional, unrecited elements or method steps. See, e.g., Mars Inc. v. H.J. Heinz Co., 377 F.3d 1369, 1376, 71 USPQ2d 1837, 1843 (Fed. Cir. 2004) ("[L]ike the term ‘comprising,’ the terms ‘containing’ and ‘mixture’ are open-ended."). Invitrogen Corp. v. Biocrest Manufacturing, L.P., 327 F.3d 1364, 1368, 66 USPQ2d 1631, 1634 (Fed. Cir. 2003).” Therefore, practicing the reference claims reads on the instant claims, even in view of the additional limitation of the reaction comprising an organic solvent.
Further, chemical formulae 1 to 4 as recited at the reference Claim 4 are identical to chemical formulae 1 to 4 as recited instantly at Claim 2. Reference claim 5 further limits the organic compound which can be hydrolyzed by the heavy water to at least one of a list of compounds including trifluoromethanesulfonic anhydride, trifluoroacetic anhydride, acetic anhydride, and methanesulfonic anhydride, all of which are instantly recited at Claim 6.
Taken together, practice of the reference claims 1-7 reads on the limitations recited at the instant Claims 1-8.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Conclusion
Claims 1-8 are rejected.
No claim is allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DANIEL JOHN BURKETT whose telephone number is (703)756-5390. The examiner can normally be reached Monday - Friday.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jeffrey Murray can be reached at (571) 272-9023. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/D.J.B./Examiner, Art Unit 1624
/JEFFREY H MURRAY/Supervisory Patent Examiner, Art Unit 1624
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