Detailed Action
The present office action is in response to the amendments filed 06 Aug 2025.
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
Claims 1-8, 10-16, and 18-20 of the pending application have been examined on the merits. Acknowledgement is made of the amendments filed 06 Aug 2025. Acknowledgement is made of the cancelation of claims 9 and 17.
Priority
The instant application, App. No. 17/049,623 filed October 22, 2020, is a National Stage Entry of International Application No. PCT/EP2019/059598, filed April 15, 2019, which claims priority to Foreign Application No. EP18169142.9, filed April 25, 2018.
Response to Arguments
Examiner acknowledges the arguments filed 06 Aug 2025.
The rejections of claim 9 have been rendered moot following applicant’s cancelation of claim 9.
Regarding the rejection of claims 1-8, 10-16, and 18-20 under 35 U.S.C. § 103, applicant arguments filed 06 Aug 2025 have been fully considered but are not persuasive.
Claims 1-8, 10-16, and 18-20 stand rejected under 35 U.S.C. § 103 over JP 2016113426 (provided in IDS 11/22/23), hereinafter ‘426, further in view of Vorbruggen et al. (Synthesis, 1979, 1:35; provided in the office action mailed 20 Feb 2025), hereinafter Vorbruggen, Xu et al. (Synthetic Comm, 2006, 37:3095-3104; abstract provided in the office action mailed 20 Feb 2025), hereinafter Xu, and Cantillo et al. (J Am Chem Soc, 2011, 133:4465-4475; provided in the office action mailed 20 Feb 2025), hereinafter Cantillo. In the remarks filed 06 Aug 2025, applicant first argues that the claimed process is not taught by '426 at least in that:
The step of reacting an isocyanate compound with an azide salt is performed in the presence in the presence of a silicon derivative
The silicon derivative has the general formula (II)
The silicon derivative is employed in a molar amount of less than 0.5 equivalent, relative to the isocyanate compound (pg. 6)
Examiner notes that attacking references individually cannot be used to show nonobviousness. In this case, the obviousness analysis uses '426, Vorbruggen, Cantillo, and Xu to teach all the limitations of the instant claims. See MPEP § 2145(IV).
Applicant argues that Vorbruggen discloses several products formed through the use of the in situ generated TMSN3, but that Vorbruggen is entirely silent about the formation of tetrazolinones via the use of in situ generated TMSN3 (pg. 6).
Examiner notes that Vorbruggen is relevant for teaching that TMSN3 does not require separate preparation and that TMSCl and NaN3 generate TMSN3 in situ. Applicant has not provided evidence showing Vorbruggen teaches away from the combination of references. Arguments cannot take the place of evidence in the record. See MPEP § 2145(I).
Applicant argues that a person skilled in the art would understand that the teaching of Vorbruggen is not readily applicable to the disclosure of '426, especially for the formation of a tetrazolinone. Further, applicant argues that there would be no reason to initiate experimentation to determine the effect of Vorbruggen's teachings on the disclosure of '426.
Vorbruggen is cited for teaching the in situ generation of TMSN3 from TMSCl and NaN3 (pg. 6). Applicant has not provided evidence which shows Vorbruggen teaches away from the combination of references. Arguments cannot take the place of evidence in the record. See MPEP § 2145(I).
Applicant further argues that Vorbruggen does not disclose the use of such TMSN3 in a catalytic amount (pg. 7).
This is not persuasive because the use of TMSN3 in a catalytic amount is gleaned from disclosures of '426, Vorbruggen, Cantillo, and Xu. Vorbruggen is cited for teaching the in situ generation of TMSN3 by reacting TMSCl and NaN3. Examiner notes that attacking references individually cannot be used to show nonobviousness. See MPEP § 2145(IV).
Applicant argues that Cantillo's teachings that stoichiometric amounts of expensive TMSN3 can be replaced by stoichiometric amounts of inexpensive NaN3 and catalytic amounts of TMSN3 or TMSCl corresponds to a specific catalysis condition and that the purpose and chemical context of Cantillo significantly differ from those of '426 (pg. 7).
Cantillo was cited for disclosing the use of catalytic amounts of TMSN3 or TMSCl and stoichiometric amounts of NaN3 to afford TMSN3 in a cyclization reaction. Applicant has not provided evidence showing Cantillo teaches away from the combination of references. Arguments cannot take the place of evidence in the record. See MPEP § 2145(I).
Applicant argues that adapting the teachings of Cantillo to the disclosure of '426 would require experimental investigation which the artisan would have no incentive to conduct (pg. 7).
Examiner notes that arguments cannot take the place of evidence in the record. See MPEP § 2145(I).
Applicant argues that Cantillo does not disclose or suggest That TMSN3 is employed in a molar amount of less than 0.1 equivalent relative to the isocyanate compound (pg. 7).
This is unpersuasive because applicant is arguing a limitation which is not claimed (i.e., that TMSN3 or TMSCl is employed in a molar amount of less than 0.1 equivalents relative to the isocyanate compound). See MPEP § 2145(VI).
Applicant argues that an artisan would understand that the teaching is not directly applicable to the subject matter of '426 because Xu relates to specific condition reactions separate from the disclosure of '426 (pgs. 7-8).
Xu is cited for teaching that TMSCl is a Lewis acid. Applicant has not provided evidence showing Xu teaches away from the combination of references. Arguments cannot take the place of evidence in the record. See MPEP § 2145(I).
Applicant argues that while TMSCl may be classified as a Lewis acid, the artisan would understand this is chemically distinct than the Lewis acids cited in the disclosure of '426 (pg. 8).
Applicant has provided no evidence showing the artisan would understand the Lewis acids to be chemically distinct from each other. Arguments cannot take the place of evidence in the record. See MPEP § 2145(I).
Applicant argues that '426 does not disclose TMSCl or provide any indication that the molar range for the Lewis acids mentioned is applicable to all Lewis acids (pg. 8).
Examiner notes that attacking references individually cannot be used to show nonobviousness. In this case, the obviousness analysis uses '426, Vorbruggen, Cantillo, and Xu to teach all the limitations of the instant claims. See MPEP § 2145(IV).
Applicant argues Xu fails to teach or suggest reacting TMSCl with an azide salt to form TMSN3 for use in a subsequent cycloaddition reaction (pg. 8).
Xu is cited to teach TMSCl is a Lewis acid. It was not previously argued by examiner that Xu teaches TMSCl with an azide salt to form TMSN3 for use in a subsequent cycloaddition reaction. Examiner notes that attacking references individually cannot be used to show nonobviousness. See MPEP § 2145(IV).
In light of the discussion above, the rejection of claims 1-8, 10-16, and 18-20 is under 35 U.S.C. § 103, as obvious over ‘426, Vorbruggen, Cantillo, and Xu is maintained for the reasons of record and restated below.
Regarding the rejection of claims 1-8, 10-16, and 18-20 under anticipatory-type nonstatutory double patenting, Applicant's arguments filed 06 Aug 2025 have been fully considered but they are not persuasive.
Claims 1-8, 10-16, and 18-20 stand provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-13 of copending Application No. 17/047,671, hereinafter ‘671, and claims 1-14 of copending Application No. 17/766,286, hereinafter ‘286. Applicant argues that the provisional nonstatutory double-patenting should be withdrawn because the claims of ‘671 and ‘286 have not been patented. This argument is unpersuasive for the following reasons. MPEP § 804(I)(B)(1)(b)(i-ii) states:
“If a provisional nonstatutory double patenting rejection is the only rejection remaining in an application having the earlier patent term filing date, the examiner should withdraw the rejection in the application having the earlier patent term filing date and permit that application to issue as a patent, thereby converting the provisional nonstatutory double patenting rejection in the other application into a nonstatutory double patenting rejection upon issuance of the patent…If both the application under examination and the reference application have the same patent term filing date, the provisional nonstatutory double patenting rejection made in each application should be maintained until it is overcome. Provisional nonstatutory double patenting rejections are subject to the requirements of 37 CFR 1.111(b). Thus, applicant can overcome a provisional nonstatutory double patenting rejection by filing a reply that either shows that the claims subject to the rejection are patentably distinct from the claims of the reference application, or includes a compliant terminal disclaimer under 37 CFR 1.321 that obviates the rejection. If the reply is sufficient, the examiner will withdraw the nonstatutory double patenting rejection in the application in which it was submitted.”
The application under examination claims benefit to the filing date of Foreign Application No. EP18169142.9, filed April 25, 2018. ‘671 also claims benefit to the filing date of Foreign Application No. EP18169142.9, filed April 25, 2018. ‘286 claims the benefit to the filing date of Foreign Application No. EP19205137.3, filed 24 Oct 2019. The patent term filing date for both the instant and ‘671 patent applications is therefore April 25, 2018 and MPEP § 804(I)(B)(1)(b)(ii) applies. To overcome the nonstatutory double-patenting rejection, applicant may file a reply that either shows the claims subject to the rejection are patentably distinct from the claims of the reference application or includes a terminal disclaimer that obviates the rejection. The patent term filing date for the instant patent application is earlier than the patent term filing date for ‘286 and MPEP § 804(I)(B)(1)(b)(i) applies. However, ‘286 is not the only rejection remaining in the application and so the rejection stands.
In light of the discussion above, the provisional NSDP rejections of claims 1-8, 10-16, and 18-20 over claims 1-13 of ‘671 and claims 1-14 of ‘286 are maintained for the reasons of record and restated below.
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 text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
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) 1-8, 10-11, 15-16, and 18-19 is/are rejected under 35 U.S.C. 103 as being unpatentable over '426, and further in view of Vorbruggen, Xu, and Cantillo.
'426 teaches a method for making a tetrazolinone (pg. 4, Compound 6) from an isocyanate (pg. 4, Compound 5):
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'426 teaches using an azidizing agent to cyclize Compound 5 normally carried out in a solvent, where the possible solvents include N,N-dimethylformamide and N-methylpyrrolidone (pg. 8, paragraph [0019]). '426 additionally teaches the azidizing agents may compounds which include sodium azide or TMSN3 (pg. 8, paragraph [0019]). '426 teaches that a Lewis acid may be added to the reaction, used in a preferable amount of 0.01 to 0.5 moles relative to moles of Compound 5. '426 further teaches that when the solvent, the Lewis acid, and the azidation agent are mixed and then Compound 5 is added, the temperature at which the Lewis acid and the azidation agent are mixed is usually in the range of -20 to 100 °C. However, '426 does not teach the Lewis acid as a silicon derivative or making the silicon derivative in situ.
Vorbruggen teaches the use of trimethylsilyl azide as a reagent does not require its separate preparation prior to the reaction with substrates such as aldehydes, ketones, or isothiocyanates and that it may be generated in situ from trimethylchlorosilane and sodium azide (pg. 35, column 1).
Xu teaches that trimethylchlorosilane is an effective silicon Lewis acid catalyst (Abstract, lines 1-2).
Cantillo teaches that stoichiometric amounts of the expensive TMSN3 can be replaced by stoichiometric amounts of inexpensive NaN3 and catalytic amounts of TMSN3 or even TMSCl which readily affords TMSN3 in the presence of the azide ion (pg. 4470, column 1).
It would be obvious to one having ordinary skill in the art to combine the teachings of '426, Vorbruggen, Xu, and Cantillo to create Compound 6 from Compound 5 by creating the azidizing reagent TMSA in situ from catalytic amounts of the Lewis acid, TMSCl, and azidizing reagent, NaN3, all while reacting in a solvent of DMA or NMP at a temperature between -20 and 100 °C.
A person having ordinary skill in the art would be motivated to form TMSA in situ using catalytic amounts of TMSCl and stoichiometric amounts of NaN3 because stoichiometric TMSA is an expensive reagent and replacing stoichiometric TMSA with catalytic TMSCl and cheap NaN3 would reduce costs. Additionally, the artisan would be motivated to form TMSA in situ due to the added convenience generated by forming reagents in situ.
Furthermore, the selection of a reaction temperature is a result effective variable that would have been routinely determined and optimized in the pharmaceutical art, as exemplified by ‘426 which teaches a widely variable reaction temperature of -20 °C to 100 °C. It is noted that no criticality has been demonstrated in the instant specification with regard to the claimed reaction temperatures.
To summarize the teachings above:
Vorbruggen and Cantillo teach NaN3 reacts with catalytic amounts of TMSCl to form TMSA in situ which read on instant claims 1-2, 4-8, and 16.
'426 teaches DMF and NMP are amide solvents which reads on instant claims 1, 3, and 15.
'426 and Xu teach using 0.01-0.5 molar equivalents of the Lewis acid, TMSCl, which reads on instant claims 9 and 18.
'426 teaches Compound 5 as an aryl isocyanate and Compound 6 as an aryl tetrazolinone which reads on instant claim 10.
'426 teaches a reaction temperature between -20 and 100 °C which reads on instant claims 11 and 19.
A reference is good not only for what it teaches by direct anticipation but also for what one of ordinary skill in the art might reasonably infer from the teachings. (In re Opprecht 12 USPQ 2d 1235, 1236 (Fed Cir. 1989); In re Bode 193 USPQ 12 (CCPA) 1976). In light of the foregoing discussion, the Examiner concludes that the subject matter defined by the instant claims would have been obvious within the meaning of 35 USC 103. From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
Claim(s) 1-8, 10-16, and 18-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over '426, Vorbruggen, Xu, and Cantillo as applied to claims 1-8, 10-11, 15-16, and 18-19 above.
'426, Vorbruggen, Xu, and Cantillo teach a method of preparing Compound 6 (above) by reacting 0.01 to 0.5 molar equivalents of TMSCl with NaN3 to create TMSA which in turn reacts with Compound 5 to create Compound 6. This reaction is performed in a solvent, preferably DMF, at a temperature between -20 °C and 100 °C.
'426 also teaches that after performing a reaction to create Compound 6, the mixture can be cooled, with a mixture of sodium nitrite and hydrochloric acid added dropwise (pg. 13, paragraph [0027]. ‘426 teaches the reaction was cooled and hydrochloric acid was added, after which water was added to the mixture followed by cooling and filtering (pg. 13, paragraph [0027]). ‘426 also teaches that sodium nitrite is an oxidizing agent that decomposes excess azidation agent (pg. 8, paragraph [0019]). ‘426 teaches that excess azidation agent may also be removed and Compound 6 isolated by performing post-treatment operations such as washing, extraction, concentration, filtration, and drying. However, '426 does not teach the steps of purifying the tetrazolinone compound prior to treating with NaNO2 and acid.
It would be prima facie obvious to one having ordinary skill in the art to try variations of washing, extraction, concentration, filtration, drying, and treating with NaNO2 and acid to ensure that any excess azidation reagent is removed. For instance, while ‘426 teaches treating the reaction to form Compound 6 with NaNO2 and acid followed by isolation of Compound 6 by filtration, an artisan would find it obvious to try filtering Compound 6 followed by treating with NaNO2 and acid in order to determine the best order of operations for removing excess azidation reagent. Furthermore, the artisan would be motivated to try different isolation and purification methods to ensure the highest possible yield of Compound 6.
To summarize the teachings above:
‘426 and ‘339 teach a method of first isolating a tetrazolinone compound following by treating the compound with NaNO2 and HCl which reads on claims 12-14 and 20.
A reference is good not only for what it teaches by direct anticipation but also for what one of ordinary skill in the art might reasonably infer from the teachings. (In re Opprecht 12 USPQ 2d 1235, 1236 (Fed Cir. 1989); In re Bode 193 USPQ 12 (CCPA) 1976). In light of the foregoing discussion, the Examiner concludes that the subject matter defined by the instant claims would have been obvious within the meaning of 35 USC 103. From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
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, 10-16, and 18-20 are provisionally rejected on the ground of anticipatory nonstatutory double patenting as being unpatentable over claims 1-5, 7-15, and 17-20 of copending Application No. 17/047,671, hereinafter ‘671. The previous provisional nonstatutory double patenting rejection in the office action filed December 27, 2023 is maintained and restated below.
Although the claims at issue are not identical, they are not patentably distinct from each other because the claimed process of ‘671 simply represents a specific example of the currently-claimed process carried out under closely analogous conditions. ‘671 claims a process for the preparation of a tetrazolinone (1-(2-methoxymethyl-3-methylphenyl)4H-tetrazolin-5-one) comprising reacting an isocyanate (2-methoxymethyl-3-methylphenylisocyanate) with an azide salt in a solvent in the present of a trialkylsilyl azide as a catalyst and where a tetrazolinone salt is obtained after reacting isocyanate with the azide salt and the tetrazolinone salt is treated with an acid to obtain the tetrazolinone compound (ref claim 1). Furthermore, ‘671 teaches the azide salt is sodium azide (ref claim 2); the solvent is DMF, DMAc, or NMP (ref claim 14); there is an intermediate purification step prior to treating with sodium nitrite (ref claim 20); the acid treatment occurs after the treatment with sodium nitrite (ref claim 13); the trialkylsilyl azide is employed in molar amounts less than 0.1 equivalents relative to the isocyanate compound (ref claim 17); the reaction temp is at least 100 °C (ref claim 19); and the trialkylsilyl azide is prepared by reacting a trialkylsilyl halide compound with an azide salt (ref claim 5) where the trialkylsilyl halide compound is trialkylsilyl chloride (ref claim 7).
Therefore, the process of claims 1-5, 7-15, and 17-20 of ‘671 anticipates the currently claimed process of claims 1-16 and 18-20, rendering these claimed processes patentably indistinct.
This is a provisional nonstatutory double patenting rejection.
Claims 1-8, 10-16, and 18-20 provisionally rejected on the ground of anticipatory nonstatutory double patenting as being unpatentable over claims 1-14 of copending Application No. 17/766,286, hereinafter ‘286.
Although the claims at issue are not identical, they are not patentably distinct from each other because the claimed process of ‘286 simply represents a specific example of the currently-claimed process carried out under closely analogous conditions. ‘286 teaches a process for making a compound of formula (2) by reacting an azide compound with a compound of formula (1) (ref claim 1):
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In a dipolar aprotic solvent comprising DMF, DMAc, or NMP (ref claim 4) in the presence of a Lewis acid where the Lewis acid is trimethylchlorosilane (ref claim 12) or trimethylsilylazide (ref claim 13).
Therefore, the process of claims 1-14 of ‘286 anticipates the currently claimed process of claims 1-16 and 18-20, rendering these claimed processes patentably indistinct.
This is a provisional nonstatutory double patenting rejection.
Conclusion
No claim is allowed. THIS ACTION IS MADE FINAL. 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.
Correspondence
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jonathan D. Mahlum whose telephone number is (703)756-4691. The examiner can normally be reached 8:30 AM - 5:00 PM ET, M-F.
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/J.D.M./Examiner, Art Unit 1625 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625