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 .
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.
Current Status of 18/549,412
This Office Action is responsive to the amended claims received 21 April 2026.
Claims 1-11 are currently pending.
Priority
Applicant’s claim for the benefit of the prior-filed applications PCT/IB2022/051866 (filed 3 March 2022) and IT 102021000005336 (filed 8 March 2021) under 35 U.S.C. 119(e), 120, 121, 365(c), or 386(c) is acknowledged.
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
The Examiner has determined, for the purposes of the instant action, that the effective filing date of the instant claims is 3 March 2022, at least due to the lack of an English translation of the earlier priority document. Should applicant desire to obtain the benefit of foreign priority under 35 U.S.C. 119(a)-(d) prior to declaration of an interference, a certified English translation of the foreign application must be submitted in reply to this action. 37 CFR 41.154(b) and 41.202(e).
Response to Amendments
The 35 U.S.C. 112 rejections to the claims, present in the previous office action, are hereby withdrawn due to Applicant’s amendments.
The 35 U.S.C. 102(a)(1) and/or 35 U.S.C. 102(a)(2) rejections to the claims, present in the previous office action, are hereby withdrawn due to Applicant’s amendments.
The 35 U.S.C. 103 rejections to the claims, present in the previous office action, are maintained herein, although they have been altered as necessitated by Applicant’s amendments.
The nonstatutory double patenting rejections to the claims, present in the previous office action, are maintained herein, although they have been altered as necessitated by Applicant’s amendments.
Claim Interpretation
The Examiner is interpreting the unit “BarA” within claim 10 to indicate absolute pressure in bar.
Response to Arguments
Applicant's arguments received 21 April 2026 have been fully considered.
Applicant argues against the previous rejections under 35 USC 102. The Examiner has withdrawn those rejections herein.
Applicant argues that the teachings of BADLANI may not be applicable to the instant application, as the reaction used therein is an oxidation reaction, whereas the instant application is not an oxidation reaction and does not use compounds similar to methanol for the desired reaction. Applicant argues that BADLANI does not teach gamma-alumina, zeolites, or silica-aluminas. Applicant argues that the instantly described reaction of Example 2 provides a greater yield in a shorter period of time, as compared to MA.
The title of BADLANI is “Methanol: a “smart” chemical probe molecule”. BADLANI is not necessarily focused on the oxidation of methanol, as Applicant seems to argues, but instead BADLANI uses methanol adsorption as a manner of determining the total number of active sites on the surface of metal oxide catalysts. The Examiner is arguing that one of ordinary skill in the art, having read over the DBU synthesis of MA, would consider swapping out the metal oxide catalyst (antimony trioxide) therein for another metal catalyst to optimize that reaction. And BADLANI provides a list of metal oxide catalysts that would have been known to one of ordinary skill in the art. It would have been obvious to one of ordinary skill in the art to envisage optimizing the antimony trioxide-catalyzed reaction of MA by replacing the metal oxide catalyst with each and every metal oxide catalyst commonly used in the art, using the list of known metal oxide catalysts being shown by BADLANI.
In practical terms, testing these 38 reactions and determining the usefulness of each metal oxide catalyst could likely be accomplished by one of ordinary skill in the art using routine methods and techniques within a week, and this very reasonable amount of effort indicates to the Examiner that this optimization would likely be obvious to try to one of ordinary skill in the art. The Examiner has updated the rejections below, as necessitated by Applicant’s amendments, with the PRINS reference to show that γ-Al2O3 was well known in the art before the instant filing date. The Examiner does not find the secondary considerations discussed by Applicant to overcome the findings of obviousness herein.
Applicant argues that HARMER does not teach the claimed reaction or type of reaction. Applicant argues claim 1 requires a “closed selection of catalysts”.
The Examiner agrees that claim 1 requires a catalyst from a closed list. The sulfonated polystyrene resin of HARMER falls within the list of catalysts of instant claim 1. The Examiner does not rely upon HARMER to teach the same reaction as found in the primary reference, OSTROWSKA. HARMER serves to show that one of ordinary skill in the art would have known that the acid catalyst of OSTROWSKA, being 4-toluenesulfonic acid, could also be found as a terminal group appended to sulfonated polystyrene resin. And because of the purification benefits that are known to come along with heterogeneous catalysts, one of ordinary skill in the art would have been motivated to replace the 4-toluenesulfonic acid of OSTROWSKA with the analogous heterogeneous catalyst.
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.
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 1-3, 6, and 11 are rejected under 35 U.S.C. 103 as being unpatentable over:
MA (CN 1546492A, Publication Date 17 November 2004, Cited by Applicant in IDS of 7 September 2023, the Examiner included a copy with a machine translation herein)
in view of:
BADLANI (Badlani, M.; Wachs, I.E. “Methanol: a ‘smart’ chemical probe molecule” Catalysis Letters Vol. 75, No. 3–4, 2001)
as evidenced by:
AMARASEKARA (Amarasekara, A.S.; Ha, U.; Okorie, N.C. “Renewable Polymers: Synthesis and Characterization of Poly(levulinic acid–pentaerythritol)” JOURNAL OF POLYMER SCIENCE, PART A: POLYMER CHEMISTRY 2018, 56, 955–958)
and as evidenced by:
PRINS (Prins, Roel “On the structure of γ-Al2O3”, Journal of Catalysis 392 (2020) 336–346).
MA teaches, at the bottom of claim 1, that the cycloaddition reaction is performed by combining aminopropyl caprolactam (drawn below) with antimony trioxide.
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MA teaches that the reaction is maintained at 150-160 °C for 20-30 hours until the reaction “no longer produces water” (claim 1 of MA). MA teaches that this reaction yields 1,8-diazabicyclo(5,4,0)-7-undecene (DBU) (claim 1 of MA). Example 1 of MA gives additional details for the same reaction. MA teaches that a reflux condenser and a “water separator” are added to four-neck flask wherein the reaction is performed (example 1). MA teaches that the reaction is performed at 155 °C for 20 hours (example 1). One of ordinary skill in the art would understand the “water separator” referred to by MA to be a Dean-Stark trap.
AMARASEKARA provides evidence that antimony trioxide (Sb2O3) is a Lewis acid. AMARASEKARA refers to Sb2O3 as a Lewis acid catalyst in the first paragraph of page 956 therein.
Neither MA nor AMARASEKARA discuss metal oxide catalysts other than antimony trioxide.
BALDANI generally teaches a method of determining the concentration of active sites on one-component metal oxide catalysts (abstract). The list of metal oxide catalysts taught by BALDANI includes 38 metal oxides, and specifically includes Sb2O3, Al2O3, and La2O3 (abstract). PRINS provides evidence that γ-Al2O3 is a well-known alumina catalyst in the art, and is the most common catalyst support within the art (introduction section). One of ordinary skill in the art would; therefore, understand Al2O3 to be synonymous with γ-Al2O3 or at least would immediately envisage γ-Al2O3 when presented with Al2O3 in a publication.
One of ordinary skill in the art, reading the teachings of MA would wonder if any other catalysts would work for the final DBU synthesis reaction. Specifically, one of ordinary skill in the art would logically think that other metal oxides may be tested to optimize the yield and minimize unwanted products in that reaction. The artisan would have come across lists of metal oxides useful for catalyzing chemical reactions, such as the list taught by BALDANI. It would have been obvious to one of ordinary skill in the art, before the instant effective filing date, to test all of metal oxide catalysts taught by BALDANI within the reaction taught by MA, for the purpose of optimizing the yield and minimizing unwanted products in that reaction. The artisan would have expected success in this trial, because all of the metal oxides within BALDANI are taught to be catalysts.
Regarding claim 6: The teachings of claim 1 of MA do not mention a solvent being present within the DBU formation reaction.
Claims 1-3, 6, and 8-11 are rejected under 35 U.S.C. 103 as being unpatentable over:
MA (CN 1546492A, Publication Date 17 November 2004, Cited by Applicant in IDS of 7 September 2023, the Examiner included a copy with a machine translation herein)
in view of:
BADLANI (Badlani, M.; Wachs, I.E. “Methanol: a ‘smart’ chemical probe molecule” Catalysis Letters Vol. 75, No. 3–4, 2001)
and in view of:
XU (WO 2019/000069 A1; International Publication Date 3 January 2019)
as evidenced by:
AMARASEKARA (Amarasekara, A.S.; Ha, U.; Okorie, N.C. “Renewable Polymers: Synthesis and Characterization of Poly(levulinic acid–pentaerythritol)” JOURNAL OF POLYMER SCIENCE, PART A: POLYMER CHEMISTRY 2018, 56, 955–958)
and as evidenced by:
PRINS (Prins, Roel “On the structure of γ-Al2O3”, Journal of Catalysis 392 (2020) 336–346).
Regarding claim 8: Teachings of MA and BADLANI and evidence provided by AMARASEKARA and PRINS are discussed above. Neither MA nor AMARASEKARA mention tubular reactors, but BADLANI does teach that the temperature programmed-reduction therein was performed with each sample catalyst in a heated quartz tube with a 10 % H2/Ar gas mixture (Pg. 139).
XU teaches the use of a continuous-flow tubular reactor to perform a catalyzed chemical reaction (abstract). XU teaches that continuous tubular reactors allow for large-scale production of materials (Pg. 45, Ln. 6-7). Page 27 of XU teaches that the “weight hourly space velocity” (WHSV) was used as “an indicator of the reactant retention/residence time within the catalyst bed”, and XU teaches how this value is calculated.
Continuous tubular reactors are a known tool within the chemical arts that allow chemical reactions to be scaled up. One of ordinary skill in the art would have been familiar with this tool, as taught by XU and BADLANI. It would have been obvious to one of ordinary skill in the art, before the instant effective filing date, to perform the reaction described by MA within a continuous tubular reactor system (as taught by XU), for the purpose of producing a larger amount of the product DBU. The artisan would have expected success in this combination, because the reaction chemistry was known from MA, and scaling up a reaction using a continuous tubular reactor was a common practice in the art.
Regarding claim 9: It would have been obvious to one of ordinary skill in the art to alter the parameters of the reaction, such as the mass of the catalyst and the feed rate of the starting material to achieve optimum yields with reduced side products.
Regarding claim 10: It would have been obvious to one of ordinary skill in the art to perform the reaction of MA at standard atmospheric pressure of about 1 bar.
Claims 1, 4-5, and 7 are rejected under 35 U.S.C. 103 as being unpatentable over:
OSTROWSKA (N-Alkyl-, N-Aryl-, and N-Hetaryl-Substituted Amidines (Imidamides), Ostrowska, K., Kolasa, A., Science of Synthesis, (2005) 22, 379. DOI: 10.1055/sos-SD-022-00489)
and in view of:
HARMER 2001 (Harmer, M.A.; Sun, Q. “Solid acid catalysis using ion-exchange resins” Applied Catalysis A: General 221 (2001) 45–62).
OSTROWSKA teaches the synthesis of 1,5-diazabicyclo(4.3.0)non-5-ene, which falls within the scope of instant claim 1 and is very similar to DBU, on page 434 therein, as shown below.
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OSTROWSKA teaches the reaction conditions for this exemplary reaction to be refluxing for 12 hours in xylene, with 4-toluenesulfonic acid being present. Xylenes are known to boil at about 140 °C. OSTROWSKA teaches that these reactions are typically performed while simultaneously removing water from the reaction (page 434).
OSTROWSKA does not teach “an acid catalyst” as defined at the bottom of instant claim 1.
HARMER teaches the use of ion-exchange resins, specifically styrene-supported sulfonic acids, as catalysts within various organic reactions (abstract). HARMER teaches that homogeneous catalysts, such as sulfuric acid, can be replaced by heterogeneous resin-based catalysts (Pg. 56, 2nd paragraph). HARMER states that one of the benefits to using a solid (heterogeneous) catalyst is easy isolation of the product (introduction section and Pg. 59, 4th paragraph). A structure of the sulfonated polystyrene resin is provided in Fig. 1 of HARMER.
One of ordinary skill in the art would have seen the reaction taught by OSTROWSKA, and would have been aware that using heterogeneous catalysts, specifically resin-based catalysts, is a known strategy within the chemical arts that allows for easy isolation of a product from a reaction mixture (as is taught by HARMER). It would have been obvious to one of ordinary skill in the art, before the instant effective filing date, to replace the solution-phase acid catalyst taught by OSTROWSKA (4-toluenesulfonic acid) with the heterogeneous resin-based version of the same acid taught by HARMER, for the purpose of increasing the ease of isolating the product from the reaction of OSTROWSKA. The artisan would have expected success in this replacement, because HARMER teaches the benefits of this type of catalyst replacement.
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 and 10-11 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over:
Claims 1, 3, 11, and 13 of copending Application No. 18/549,406 (referred to below as the ‘406 application).
Although the claims at issue are not identical, they are not patentably distinct from each other because: Claim 1 of the ‘406 application teaches the synthesis of a compound of formula (V) from a compound of formula (IV), wherein these formulae are identical to those of the same designation in instant claim 1. Claim 1 of the ‘406 application also teaches that the reaction of formula (IV) is performed with dehydration in the presence of an acid catalyst in step (C) therein. Claim 13 of the ‘406 application specifies the acid catalyst of claim 1 (C) to be selected from aluminum oxide, SiO2-Al2O3, lanthanum oxide, zirconium oxide, and sulfonated resins. Together, claims 1 and 13 of the ‘406 application anticipate instant claims 1-4. Claim 3 of the ‘406 application anticipates instant claim 11, due to the compound of formula (V) being specified as DBU. Claim 11 of the ‘406 application teaches a continuously stirred tank reactor, which anticipates instant claim 8. Claim 13 of the ‘406 application teaches many specific reaction details that anticipate instant claims 5-7 and 10.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1, 3, and 5-11 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over:
Claims 1 and 3-9 of copending Application No. 19-108,987 (referred to below as the ‘987 application).
Although the claims at issue are not identical, they are not patentably distinct from each other because: Claim 1 of the ‘987 application teaches the synthesis of a compound of formula (V) from a compound of formula (IV), wherein these formulae are identical to those of the same designation in instant claim 1. Claim 1 of the ‘987 application also teaches that the reaction of formula (IV) is performed with dehydration in the presence of zirconium oxide. Claim 1 of the ‘987 application anticipates instant claims 1 and 3. Claims 3, 4, 5, 6, 7, 8, and 9 of the ‘987 application anticipate instant claims 5, 6, 7, 8, 9, 10, and 11 respectively.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Conclusion
No claims are currently allowable.
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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JOHN D MCANANY whose telephone number is (571)270-0850. The examiner can normally be reached 8:30 AM - 5:30 PM.
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/JDMc/Examiner, Art Unit 1625 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625
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