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 .
Detailed Action
This office action is in response to applicant’s communication filed on 11/12/25.
Claims 1-11 are pending in this application and are being examined in this Office Action.
Priority
The applicant claims benefit as follows:
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Objections
Claims 10 and 11 are objected to because of the following informalities:
Applicant recites “dibutylformamide (DBF)” in claims 10 and 11. The examiner recommends “N,N-dibutylformamide (DBF)” for clarity and consistency with applicant’s specification and examples. Appropriate correction is required.
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 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 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 of this title, 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 1-4, 6-8, and 10 are rejected under 35 U.S.C. 103 as being unpatentable over Zhu et al. (“A particularly convenient synthesis of benzohydroximoyl chlorides,” Journal of Hubei University (Natural Science), Vol. 29, No. 2, June 2007; English translation used herein), in view of Venkanna et al. (“Trichloroisocynuric Acid/DMF as Efficient Reagent for Chlorodehydration of Alcohols Under Conventional and Ultrasonic Conditions,” Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 45:1, 97-103, 2015).
Determination of the Scope and Content of the Prior Art
(MPEP §2141.01)
Zhu et al. teaches a particularly convenient synthesis of benzohydroximoyl chlorides (compound 1) by reacting aldoximes (compound 2) with trichloroisocyanuric acid (TCCA, compound 3) (see scheme below). Zhu et al. teaches that benzohydroximoyl chloride was synthesized by the reaction of readily available trichloroisocyanuric acid and aldoximes, and that the new method has the advantages of high yields and simple reaction and workup (Zhu et al., p. 172, English abstract).
Zhu et al. teaches the reaction of substituted benzaldoximes (compound 2) with TCCA (compound 3) to form corresponding substituted benzohydroximoyl chlorides (compound 1), which corresponds to converting the oxime C-H bond into the oxime C-Cl bond, in the scheme below (Zhu et al., p. 164, reaction scheme; p. 165, general synthesis).
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Zhu et al. exemplifies substituted benzaldoximes where R is 2-ClC6H4, 3-ClC6H4, 4-ClC6H4, 4-FC6H4, 4-CNC6H4, 4-BrC6H4, 4-CH3C6H4, 4-CH3OC6H4, 4-CF3C6H4, and 3-NO2C6H4 (Zhu et al., p. 164, reaction scheme).
Thus Zhu et al. teaches that the TCCA chlorination reaction is applicable to substituted benzaldoximes including halogenated and fluorinated benzaldoximes. Zhu et al. teaches that the optimum condition was aldoxime:TCCA of about 2:1, tetrahydrofuran as solvent, reaction temperature of 0-5°C, and reaction time of 4-6 hours, with yield of benzohydroximoyl chloride of at least 90% (Zhu et al., p. 172, English abstract; p. 166, conclusion).
Zhu et al. also teaches solvent screening and teaches that DMF and THF provided high yields in the TCCA chlorination reaction, with DMF giving 95% yield and THF giving 96% yield (Zhu et al., p. 166, Table 2).
Venkanna et al. teaches TCCA/DMF as an efficient reagent for chlorodehydration of alcohols. Venkanna et al. teaches that a variety of alcohols can be converted smoothly into corresponding alkyl chlorides in high yields under mild conditions with short reaction times (Venkanna et al., p. 97, Abstract).
Venkanna et al. teaches that TCCA/DMF is used as a reagent in dichloromethane and that the mechanism could be explained by interaction of TCCA with DMF to afford a Vilsmeier-Haack type complex in a pre-equilibrium step (Venkanna et al., p. 98, Results and Discussion).
Venkanna et al. further teaches that formation of the TCCA-DMF adduct was confirmed by infrared spectroscopic studies, and that shifts in the infrared spectrum were attributed to interaction of TCCA with DMF (Venkanna et al., p. 100).
Venkanna et al. also teaches preparing TCCA-DMF reagent by adding one mole of each reactant, TCCA and DMF, to CH2Cl2 and stirring for about 3 hours at room temperature (Venkanna et al., p. 102, Synthetic Procedure).
Ascertainment of the Difference Between Scope the Prior Art and the Claims
(MPEP §2141.012)
Zhu et al. teaches the same type of chemical conversion required by claim 1, namely reaction of substituted benzaldoximes with TCCA to obtain corresponding benzohydroximoyl chlorides. Zhu et al. teaches substituted benzaldoxime substrates, including a fluorinated benzaldoxime example, and teaches the claimed temperature ranges because Zhu et al. teaches 0-5°C. Zhu et al. further teaches use of DMF in the TCCA chlorination reaction, although Zhu et al. uses DMF as a solvent rather than expressly as an amide base in an amount of 0.5 to 2 equivalents.
Venkanna et al. cures this deficiency because Venkanna et al. teaches TCCA/DMF as a reagent system in dichloromethane, confirms formation of a TCCA-DMF adduct, and teaches preparing the reagent using one mole of DMF with one mole of TCCA. Thus Venkanna et al. teaches DMF as a reagent component in approximately one equivalent, not merely as a bulk solvent. This reads on applicant’s claimed 0.5 to 2 equivalents of amide base and the amide base species dimethylformamide (DMF).
Finding of Prima Facie Obviousness Rationale and Motivation
(MPEP §2142-2143)
Therefore, 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 TCCA chlorination reaction of Zhu et al. by using DMF as an amide reagent component in a reduced amount, rather than as a bulk solvent, because Venkanna et al. teaches that TCCA and DMF form a reagent/adduct in dichloromethane and that TCCA/DMF functions as a chlorination reagent system.
One of ordinary skill in the art would have had a reasonable expectation of success because Zhu et al. already teaches that TCCA effectively chlorinates substituted benzaldoximes and that DMF is compatible with the TCCA oxime chlorination reaction. With respect to the substituted phenyl limitations of claims 2-4, Zhu et al. teaches that the reaction is not limited to unsubstituted benzaldoxime, but applies to various substituted benzaldoximes including halogenated and fluorinated aryl aldoximes. Thus, the selection of the claimed substituted benzaldoximes would have been an obvious variation of the substituted aryl oxime substrates taught by Zhu et al.
Therefore, claims 1-4, 6-8, and 10 are fully met.
Claim 5 is rejected under 35 U.S.C. 103 as being unpatentable over Zhu et al. in view of Venkanna et al., as applied to claims 1-4, further in view of Xie et al. (“Design, synthesis, and in vitro evaluation of novel antifungal triazoles,” Bioorganic & Medicinal Chemistry Letters 27, 2171-2173, 2017).
Xie et al. teaches the exact 3,5-difluoro substituted benzaldoxime/chlorinated oxime species recited by applicant. See scheme below. (Scheme 1, compound 2(a18) to compound 3(a18), step (ii))
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In particular, Xie et al. teaches that intermediates 3 were prepared by chlorination of benzaldehyde oximes 2, which were obtained by hydroxylamination of substituted benzaldehydes 1 (Xie et al., p. 2171).
Xie et al. further teaches in Scheme 1 that compound 2 is reacted with N-chlorosuccinimide in dimethylformamide at 35°C for 2 hours to form compound 3 (Xie et al., p. 2172, Scheme 1).
Xie et al. identifies compound a18 as R = 3,5-diF (Xie et al., p. 2173, Table 1).
Thus Xie et al. teaches the particular 3,5-difluoro benzaldehyde oxime substrate and the corresponding 3,5-difluoro chlorinated oxime product.
Although Xie et al. uses N-chlorosuccinimide rather than TCCA, Zhu et al. teaches TCCA for the same aldoxime-to-benzohydroximoyl chloride conversion. Therefore, it would have been obvious to one of ordinary skill in the art to apply the TCCA chlorination reaction of Zhu et al. to the 3,5-difluoro benzaldoxime substrate taught by Xie et al. because Zhu et al. teaches that substituted benzaldoximes are converted to corresponding benzohydroximoyl chlorides using TCCA, and Xie et al. teaches that the same 3,5-difluoro benzaldoxime substrate is converted to the corresponding 3,5-difluoro chlorinated oxime product using N-chlorosuccinimide in DMF.
One of ordinary skill in the art would have had a reasonable expectation of success because both references teach halogenation of substituted benzaldoxime substrates to the corresponding chlorinated oxime products.
Therefore, claim 5 is fully met.
Claim 9 is rejected under 35 U.S.C. 103 as being unpatentable over Zhu et al. in view of Venkanna et al., as applied to claim 1, further in view of Daosong et al. (CN 102040546 A, pub date 05/04/2011, the English translation is used herein).
Daosong et al. teaches preparation of oxime halides by halogenation of oximes. Daosong et al. teaches that 4-cyclopropyl-1-naphthaldehyde is reacted with hydroxylamine or a hydroxylamine derivative to obtain 4-cyclopropyl-1-naphthaldehyde oxime, and that the obtained oxime is then added to a halogenating agent for halogenation to obtain the corresponding oxime halide (Daosong et al., paragraphs [0024]-[0026]).
Daosong et al. teaches that the chlorinating agent may be N-chlorosuccinimide, dichlorohydantoin, or trichloroisocyanuric acid (Daosong et al., paragraph [0030], claims 1 and 3).
Daosong et al. further exemplifies dissolving 45 mmol of oxime in acetonitrile and adding 15 mmol of TCCA to obtain the corresponding oxime chloride, thereby teaching about 0.33 equivalents of TCCA based on the oxime substrate (Daosong et al., paragraph [0064]).
Therefore, it would have been obvious to use the claimed amount of TCCA because Daosong et al. teaches about 0.33 equivalents of TCCA in an oxime chlorination reaction, and Zhu et al. teaches the same general aldoxime-to-hydroximoyl chloride conversion with TCCA.
The amount of TCCA is a result-effective variable because TCCA provides active chlorine for conversion of the oxime C-H bond to the oxime C-Cl bond.
Thus, optimizing the amount of TCCA to chlorinate the oxime while avoiding unnecessary excess reagent would have been within the ordinary skill in the art.
Therefore, claim 9 is fully met.
Claim 11 is rejected under 35 U.S.C. 103 as being unpatentable over Zhu et al. in view of Venkanna et al., as applied to claim 10, further in view of Bollyn (“Thermal Hazards of the Vilsmeier-Haack Reaction on N,N-dimethylanilin,” Org. Process Res. Dev. 9(6), 2005).
Bollyn teaches a process safety study of Vilsmeier-Haack chemistry using formamides and a chlorinating reagent. Bollyn teaches that DMF and phosphorous oxychloride are generally used to generate the Vilsmeier-Haack intermediate, and that alternative formamides were investigated (Bollyn, p. 1, Introduction; p. 11, Screening study of formamides).
Bollyn teaches testing N,N-dimethylformamide (DMF), N,N-diethylformamide (DEF), N,N-dibutylformamide (DBF), N-formylpiperidine, and N-formylmorpholine, and teaches that all formamides showed an exothermic reaction on adding OPCl3 (Bollyn, pp. 11-12).
Bollyn further teaches that DBF was selected for further study, that DBF exhibited reaction profiles comparable to DMF and DEF, and that, from a pure thermal point of view, DMF is much more reactive than DEF, which is more reactive than DBF (Bollyn, pp. 17-21).
Therefore, it would have been obvious to substitute DBF for DMF because Bollyn teaches DBF as a known alternative formamide to DMF in chlorinating reagent/formamide chemistry. Bollyn teaches that DBF reacts in the same general formamide/chlorinating reagent system, exhibits comparable reaction profiles, and has lower thermal reactivity than DMF.
Thus one of ordinary skill in the art would have been motivated to use DBF as an alternative to DMF in order to obtain a similar formamide-mediated chlorinating system with improved process safety or reduced thermal reactivity, with a reasonable expectation of success.
Therefore, claim 11 is fully met.
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).
This is a provisional obviousness-type double patenting rejection because the conflicting claims have not in fact been patented.
Claims 1-11 are provisionally rejected on the ground of nonstatutory obviousness-type double patenting as being unpatentable over claims 1-13 of application number 18/865,187 in view of Zhu et al. (“A particularly convenient synthesis of benzohydroximoyl chlorides,” Journal of Hubei University (Natural Science), Vol. 29, No. 2, June 2007; English translation used herein) and Daosong et al. (CN 102040546 A, pub date 05/04/2011, the English translation is used herein).
The claims of application number 18/865,187 are directed to a method for preparing chlorobenzaldehyde oximes of general formula (I) by converting benzaldehyde oxime compounds of general formula (II) with the aid of chlorine gas (Cl2).
The claims of application number 18/865,187 recite the same or overlapping definitions of X2, X3, X4, X5, and X6, including the species wherein X2 is H, X3 is fluorine, X4 is H, X5 is fluorine, and X6 is H.
The claims of application number 18/865,187 further recite adding an amide base, catalytic amounts of an amide base, and amide bases including dimethylformamide (DMF), dibutylformamide (DBF), diethylformamide (DEF), and dimethylacetamide (DMAc).
Thus, the reference claims and instant claims have overlapping product, starting material, substituent, reaction, and amide-base limitations.
The instant claims differ from the claims of application number 18/865,187 at least in that the instant claims recite trichloroisocyanuric acid (TCCA) as the chlorinating agent, whereas the claims of application number 18/865,187 recite chlorine gas (Cl2).
However, Zhu et al. teaches a synthesis of benzohydroximoyl chlorides by reacting aldoximes with trichloroisocyanuric acid (TCCA). Zhu et al. teaches that benzohydroximoyl chloride was synthesized by reaction of readily available TCCA and aldoximes, and that the method provides high yields and simple reaction and workup (Zhu et al., English translation, p. 1, Abstract).
Zhu et al. further teaches the reaction of substituted benzaldoximes with TCCA to form corresponding substituted benzohydroximoyl chlorides, which corresponds to converting the oxime C-H bond into the oxime C-Cl bond (Zhu et al., English translation, p. 1, reaction scheme).
Zhu et al. teaches optimum conditions including an aldoxime:TCCA ratio of about 2:1, tetrahydrofuran as solvent, 0-5°C, and 4-6 hours, with yield of at least 90% (Zhu et al., English translation, p. 1, Abstract; p. 3, Conclusion).
Daosong et al. teaches preparation of oxime halides by halogenation of oximes. Daosong et al. teaches that an oxime is added to a halogenating agent for halogenation to obtain the corresponding oxime halide, wherein the halogenating agent includes a chlorinating agent or brominating agent (Daosong et al., paragraphs [0024]-[0026]).
Daosong et al. teaches that the chlorinating agent may be N-chlorosuccinimide, dichlorohydantoin, or trichloroisocyanuric acid (Daosong et al., paragraph [0030], claims 1 and 3).
Daosong et al. further exemplifies dissolving 45 mmol of oxime in acetonitrile and adding 15 mmol of TCCA to obtain the corresponding oxime chloride, thereby teaching about 0.33 equivalents of TCCA based on the oxime substrate (Daosong et al., paragraph [0064]).
Thus, it would have been obvious to one of ordinary skill in the art at the time of the invention to use TCCA as the chlorinating agent in place of chlorine gas in the oxime chlorination process of application number 18/865,187 because Zhu et al. teaches that TCCA performs the same aldoxime-to-benzohydroximoyl chloride conversion, and Daosong et al. teaches TCCA as a chlorinating agent for oxime halogenation.
One of ordinary skill in the art would have had a reasonable expectation of success because the prior art teaches that TCCA provides active chlorine for converting oximes to the corresponding chlorinated oxime products.
It would also have been obvious to use the claimed amount of TCCA because Daosong et al. teaches about 0.33 equivalents of TCCA in an oxime chlorination reaction.
Also, the amount of chlorinating agent is a result-effective variable because the chlorinating agent provides active chlorine for conversion of the oxime C-H bond to the oxime C-Cl bond.
Thus, optimizing the amount of TCCA to chlorinate the oxime while avoiding unnecessary excess reagent would have been within the ordinary skill in the art.
Therefore, the instant claims are not patentably distinct from claims 1-13 of copending application number 18/865,187.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jennifer Cho Sawyer whose telephone number is (571) 270 1690. The examiner can normally be reached on Monday-Friday 9 AM - 6 PM PST.
If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Renee Claytor can be reached on (571) 272-8394. The fax phone number for the organization where this application or proceeding is assigned is 571-274-1690.
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Jennifer Cho Sawyer
Patent Examiner
Art Unit: 1691
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691
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