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 .
Status of the Claims
Claims 1-8 are pending in the instant application and subject to examination herein.
Claim Rejections - 35 USC § 112(d)
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 2, 5 and 7-8 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 2 depends from claim 1, which regards a method of preparation of anthranilamides of formula (Ia) or formula (Ib) with certain limitations, including wherein the process is carried out in the absence of an acid scavenger. Claim 2 purports to further limit the method of claim 1, by adding a limitation that “the acid scavenger is an organic amine”. Claim 2 fails to include all the limitations of claim 1 because claim 1 does not allow any acid scavenger to be present in the process, whereas claim 2 requires the presence of an acid scavenger. Claims 7-8 depend from claim 2 and include all the limitations of claim 2, including requiring the presence of an acid scavenger, and therefore do not include the limitation of claim 1 that requires the absence of an acid scavenger in the process of preparing anthranilamides of formula (Ia) or formula (Ib).
Claim 5 depends from claim 4, itself further limiting claim 1 with regard to parameters of temperature and pressure for the distillation of HCl out of the anthranilamide-forming reaction. Claim 5 limits the method of claim 4 to a temperature range of 75-100°C; however, claim 4 already includes the temperature limitation of 75-100°C and therefore claim 5 does not provide any further limitation to the method of claim 4.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Claim Rejections - 35 USC § 102 – Withdrawn
The prior rejection of claim 2 under 35 U.S.C. 102(a)(1) as being anticipated by Yu (CN110028489A)1 is withdrawn in response to Applicant’s amendment of claim 2.
Claim Rejections - 35 USC § 102 – Withdrawn
The prior rejection of claims 1-2 under 35 U.S.C. 102(a)(1) as being anticipated by Yu (CN110028489A)2 is withdrawn in response to Applicant’s amendments to claims 1-3. Applicant has traversed this rejection on the following grounds:
Yu does not explicitly state that HCl is being distilled from the anthranilamide-forming reaction disclosed therein;
The process disclosed by Yu has no mechanism to selectively remove HCl from the reaction mixture by use of reduced pressure;
The process disclosed by Yu does not remove all of the HCl formed in the anthranilamide-forming reaction disclosed therein;
The process disclosed by Yu does not disclose the removal of water during the anthranilamide-forming reaction disclosed therein, whereas the instant disclosure teaches a process wherein water is used to azeotropically remove aromatic solvent along with HCl under reduced pressure;
A person of ordinary skill in the art would not construe the removal of HCl under reduced pressure within Yu’s process as “distillation” but rather as “evaporation” which is distinct and therefore not in scope of the instant claim(s);
Applicant alleges that “At elevated temperatures, acetonitrile can react with HCl to form acetonitrilium chloride (CH3CN·HCl). This is an ionic compound where the acetonitrile nitrogen is protonated , creating a cationic acetonitrilium species (CH3CNH+) and a chloride ion (Cl-). Therefore, HCl could be kept inside the reaction by the ionization/solvation of HCl;
Reflux conditions in the presence of acid (HCl) can cause formation of cyanide ion by degradation of acetonitrile, significantly impacting the toxicity of the process disclosed by Yu;
The process taught by Yu is less efficient than the process of the instant disclosure and provides product of unknown purity.
Applicant’s arguments have been considered, but are not found persuasive, for the following reasons:
As discussed in the prior rejection, a person of ordinary skill in the art would at once recognize that the distillation of hydrogen chloride from the reaction mixture is an inherent aspect of Yu’s method, per the teachings of Brown (Brown, H. C. and Brady, J. D.; Journal of the American Chemical Society, v74, 3570-3582; 1952) that are reviewed in the prior rejection and again herein below, therefore, it is not disqualifying that Yu does not declare that any distillation of HCl is taking place in the process disclosed therein;
Claim 1, as written, does not limit the claimed process to the selective or complete removal of HCl by distillation, therefore it is not relevant that the process of Yu does not disclose the selective or complete removal of HCl from the anthranilamide-forming process disclosed therein;
Claim 1, as written, does not claim any removal of water from an anthranilamide-forming process, therefore it is not relevant that the process of Yu does not disclose the removal of water from the anthranilamide-forming process disclosed therein;
A person of ordinary skill in the art would understand the removal of HCl under reduced pressure within Yu’s process as “distillation”, based both upon the prior art and upon the instant disclosure:
Brown refers to the removal of HCl from various solvents under reduced pressure as “distillation”, even when conducted at -78°C (page 3576);
The instant Specification, on page 9, provides “Example 2”, regarding the synthesis of cyantraniliprole, wherein the precursor benzamide and acyl chloride compounds are combined in toluene, at 80°C, “under vacuum of 400 mbar”, which a person of ordinary skill in the art would understand to be a pressure of 613 mbar, under which condition the instant disclosure states “vacuum distillation occurred” during a reaction that clearly forms HCl as a product. Furthermore, a person of ordinary skill in the art would understand, via the well-known Clausius-Clapeyron relation shown below, that at 80°C and 513 mbar, toluene has an effective boiling point of 93°C, thus the major component being “distilled” from the reaction would be HCl, along with some portion of the toluene:
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(Clausius-Clapeyron Equation: T is the effective boiling point of a liquid at pressure P, while T0 is a known boiling point of the same liquid at corresponding pressure P0, R is the gas constant and l is the latent heat of vaporization – see for example, Brittanica3);
Applicant’s allegations of the sequestration of HCl in acetonitrile as acetonitrilium chloride (CH3CN·HCl) and the formation of cyanide from acetonitrile at reflux are not supported by evidence in the response, nor by reference to known prior art to establish such assertions, and are accordingly afforded no weight. Furthermore, as discussed in the prior rejection, Yu provides for the same process to be conducted in additional solvents, particularly identifying toluene as a suitable solvent;
Yu reports purity of the anthranilamide products as determinted by HPLC analysis – see for example, the synthesis of cyantraniliprole by Yu, in which the “quantitative content of the main product is 87% and the yield is 83%” (paragraph [0051]). Regarding yield differences between the processes of Yu and the instant disclosure, Yu discloses yields of 84% and 83%, respectively, for chlorantraniliprole and cyantraniliprole (paragraphs [0047] and [0051], respectively) while the exemplary syntheses of the instant disclosure give yields of 95%, 51% and 90% (Examples 1, 2 and 3, respectively, pages 9-10). Thus, there is not a consistently superior yield for the instant process vs. the prior art, and in those instances wherein the instant disclosure has reported a higher yield, the difference is not significant. The Examiner notes that each of the instant Examples 1, 2 and 3 differ slightly in terms of temperature, pressure, and/or procedural steps, and thus the disclosure does not provide any repetition of reaction conditions to demonstrate reproducibility of the reported yields, just as Yu does not provide any repetition of results to establish certainty over the efficiency of the results disclosed therein. Thus, there is insufficient evidence in either the prior art or the instant disclosure to establish any superiority of reaction efficiency.
Claim Rejections - 35 USC § 102 – Necessitated by Amendments
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 3 are anticipated by Yu.
Claims 1 and 3 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Yu (CN110028489A)4.
Claim 1 is drawn to a process for preparation of anthranilamides of formula (Ia)5 or (Ib)6, corresponding to the known compounds chlorantraniliprole and cyantraniliprole, respectively, comprising reaction of the precursor compound of formula (II)7, a pyrazolyl acyl chloride, together with either the compound of formula (IIIa)8 or (IIIb)9, each being an amino-benzamide. Structures are shown below. Additional limitations of the claim are that the reaction is carried out in the absence of an acid scavenger and that HCl formed during the reaction is distilled out from the reaction mixture during the process.
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Yu discloses a method for preparing a genus of benzamide-based insecticides of Formula (I), encompassing chlorantraniliprole and cyantraniliprole, comprising reacting the corresponding pyrazole-acyl chloride and amino-benzamide building blocks (paragraphs [0010]-[0011])10.
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[Yu’s Formula (I) synthesis, wherein R1/R4 are methyl, R2 is chlorine or cyano, R3 is hydrogen.]
Yu provides exemplary syntheses of chlorantraniliprole (paragraph [0047]) and cyantraniliprole (paragraph [0052]) that conduct the reaction as described above, conducted in acetonitrile at 50°C and at reduced pressure (-0.04 MPa). No acid scavenging agent is added during either exemplary reaction. Once the reaction is completed, and the desired compound has already been formed (e.g., prepared), Yu adds an aqueous solution of sodium bicarbonate to quench any lingering acid (HCl) in the mixture. While Yu does not specify that HCl formed during the reactions to form chlorantraniliprole and cyantraniliprole is distillled out of the reaction mixture, a person of ordinary skill in the art would at once recognize that the distillation of hydrogen chloride from the reaction mixture is an inherent aspect of Yu’s method, as evidenced by Brown (Brown, H. C. and Brady, J. D.; Journal of the American Chemical Society, v74, 3570-3582; 1952). Brown teaches a study on the solubility of hydrogen chloride (HCl) in the presence of aromatic solvents including toluene, at -78.5°C (Abstract). Brown’s experiments involved cooling toluene or mixtures of other aromatic solvents in toluene or in n-heptane down to -78.5°C and then introducing a controlled quantity of HCl gas into the cooled toluene or solvent mixture and measuring the atmospheric pressure of the sealed solvent/HCl mixture (Experiment Section, pp3580-3581). Brown measured positive pressure of HCl in all samples, and reported Henry’s Law constants for HCl in each solvent/mixture studied11, confirming that HCl partitions between dissolved and free vapor states even at -78.5°C in the presence of toluene. A person of ordinary skill in the art, understanding the evidence of Brown and the basic knowledge of Le Chatelier’s principle of equilibrium, would at once envisage that in the presence of a constant maintained reduced pressure, the free vapor of HCl would be removed from the headspace above a reaction mixture in toluene that is producing HCl, and the vapor HCl would continually be replenished from the quantity of dissolved HCl in the reaction solution, thereby steadily distilling off the HCl.
Thus, claim 1 is anticipated by the disclosure of Yu.
Claim 3 further limits claim 1 to wherein the aromatic solvent is selected from a Markush group that includes toluene.
While Yu conducts the exemplary syntheses of chlorantraniliprole and cyantraniliprole in acetonitrile rather than an aromatic solvent, Yu discloses that the reaction can be conducted in a range of solvents that includes benzene and toluene (paragraph [0021]), and Yu further narrows the range of solvents to just two selected solvents: toluene and acetonitrile (paragraph [0021]). Thus, a person of ordinary skill in the art would readily envisage the preparation of the compounds using toluene as the solvent.
Thus, claim 3 is anticipated by the disclosure of Yu.
Claim Rejections - 35 USC § 103 – Withdrawn
The prior rejection of claims 1-6 is withdrawn in response to Applicant’s amendments to claims 1-3 and 5-6. Applicant has traversed this rejection on the same grounds stated for the traverse of the prior rejection under 35 USC § 102, discussed above. This rejection has been considered, but not found persuasive, based on the reasons discussed above.
Claim Rejections - 35 USC § 103 – Necessitated by Amendments
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 and 3-6 are unpatentable over Yu (CN110028489A) in view of Britannica, PubChem CID 1140 and PubChem CID 6342.
Claims 1-6 are rejected under 35 U.S.C. 103 as being unpatentable over the disclosure of Yu in view of Britannica (“The Clausius-Clapeyron Equation”, Britannica.com)12, PubChem CID 1140 (PubChem CID 1140: toluene)13 and PubChem CID 6342 (PubChem CID 6342: acetonitrile)14.
The limitations of claims 1 and 3 and the disclosure of Yu are discussed in the rejection above and hereby incorporated into the instant rejection.
Claim 4 further limits claim 1 to wherein distillation of HCl is performed within a temperature range of 75-100°C and a pressure range of 380-450 mm Hg.
Claim 5 reiterates the limitation from claim 4 wherein distillation of HCl is performed within a temperature range of 75-100°C (see rejections under 35 USC § 112(d), discussed above).
Claim 6 further limits claim 4 to wherein distillation of HCl is performed within a pressure range of 420-450 mm Hg.
Yu provides a range of suitable (reduced) reaction pressure of -0.01~-0.09, corresponding to 85-460 mm Hg and a range of suitable reaction temperature from 20°C up to the boiling point of the solvent (paragraph [0020]) for the range of solvents disclosed as suitable for the reaction, including solvents as low-boiling as dichloromethane (boiling point 40°C)15 or high-boiling as dimethyl sulfoxide (boiling point 189°C)16, and particularly including toluene (paragraph [0021]). Additionally, as discussed in the rejection above, Yu provides exemplary syntheses of chlorantraniliprole (paragraph [0047]) and cyantraniliprole (paragraph [0052]) in acetonitrile at 50°C and at reduced pressure (-0.04 MPa, corresponding to 460 mm Hg), and the synthesis of the precursor pyrazolyl acyl chloride compound, corresponding to instant Formula (II), in toluene at 50°C and -0.055 MPa, corresponding to 385 mm Hg (paragraph [0046]).
While Yu does not particularly point out narrower pressure ranges of 380-450 mm Hg or 420-450 mm Hg alone or in combination with narrower temperature ranges of 75-100°C or 75-85°C, a person of ordinary skill in the art would have a reasonable expectation of arriving at the claimed temperature/pressure ranges, because these factors represent result-effective parameters for elevating reaction temperature and applying reduced temperature without distilling the solvent out of the reaction vessel, and the determination of these parameters was known in the art at the effective time of filing – see for example, the teachings of Britannica and PubChem (CID 1140 and CID 6342).
Britannica teaches the principles of the Clausius-Clapeyron relation, which provides the relationship between pressure and temperature for a given compound at the phase transition boundary. The Clausius-Clapeyron equation allows a person of ordinary skill in the art to map the pressure/temperature at different parameters given one known set of pressure/temperature for the boiling point of a compound, as well certain necessary constants:
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(Clausius-Clapeyron Equation)
wherein T is the effective boiling point of a liquid at pressure P, while T0 is a known boiling point of the same liquid at corresponding pressure P0 , R is the gas constant (8.314 J·K/mol) and l is the latent heat of vaporization.
PubChem CID 1140 teaches the properties of toluene, including its standard boiling point (110.6°C, or 383.6K at 760 mm Hg – section 3.2.4) and heat of vaporization (38.01 kilojoules/mole (section 3.2.22). PubChem CID 6342 teaches the properties of acetonitrile, including its standard boiling point (179°F, i.e., 82°C) and heat of vaporization (73 x104 J/kg, i.e., 30 KJ/mol given 41.05 g/mol formula weight). A person of ordinary skill in the art, applying the knowledge provided by Britannica and PubChem, could determine the boiling temperature of acetonitrile and toluene at any given pressure, or determine the boiling pressure at any given temperature.
Looking again at Yu’s exemplary reactions and applying the Clausius-Clapeyron equation and the properties of the solvents, the chlorantraniliprole-forming reaction in acetonitrile, at 50°C, is conducted 15 degrees below the effective boiling temperature of 65°C at Yu’s chosen pressure of 460 mm Hg, and the pyrazolyl acyl chloride-forming reaction in toluene, at 50°C, is conducted 39 degrees below the effective boiling temperature of 89°C at Yu’s chosen pressure of 385 mm Hg. Thus, a person of ordinary skill in the art, employing the method of Yu, would understand to use a reaction temperature well below the effective boiling temperature at any given pressure, so as to avoid loss of solvent during the reaction, or face the necessity of requiring additional solvent to compensate for loss of solvent, as found, for example, in the instant “Example 3”, wherein a person of ordinary skill in the art, applying the understanding of the Clausius-Clapeyron equation, can see that the effective boiling point of toluene, at the reported pressure of 450 millibars used in this synthesis of chlorantraniliprole, will be 86°C, and so after 120 minutes of heating the reaction to 80°C at this pressure, the example shows a necessary addition of 50 grams of toluene to the reaction (pages 9-10, bridging paragraph). These principles are well understood in the art.
While Applicant’s claimed pressure ranges of 380-450 mm Hg and 420-450 mm Hg are more narrow than the applicable pressure range provided by Yu, Applicant has not provided any evidence in the instant Specification to indicate the criticality of the more narrow pressure ranges for the instant claimed invention. In cases where claimed ranges overlap or lie inside ranges disclosed by the prior art, a prima facie case of obviousness exists – see MPEP § 2144.05.I.
Applicant’s invention is unpatentable over the disclosure of Yu in view of the teaching of Britannica, PubChem CID 1140 and PubChem CID 6342, because a person of ordinary skill in the art, at the effective time of filing, would have a reasonable expectation of success in employing the method of Yu to synthesize chlorantraniliprole and/or cyantraniliprole, using toluene as the solvent, and arriving at the claimed temperature and pressure ranges, because the claimed temperature/pressure ranges are result-effective variables that accomplish elevated reaction temperature without rapid loss of solvent at reduced pressure, and the determination of boiling temperature/pressures via the Clausius-Clapeyron equation was known in the art per the teaching of Britannica and the physical properties of solvents, for use in the equation, were known in the art per the teaching of PubChem CID 1140 and PubChem 6342.
Thus, the invention was prima facie obvious at the time of filing.
Double Patenting – Withdrawn
The prior provisional rejection of claim 1 on the ground of nonstatutory double patenting as being unpatentable over claim 27 of copending Application No. 19/104,162 (reference application, hereafter referred to as “Suez”) is withdrawn in response to Applicant’s amendment of claim 1.
Double Patenting – Necessitated by Amendment
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.
Claim 1 on the ground of nonstatutory double patenting as being unpatentable over claim 27 of copending Application No. 19/104,162 (reference application, hereafter referred to as “Suez”) in view of Yu (CN110028489A) and Brown (Brown, H. C. and Brady, J. D.; Journal of the American Chemical Society, v74, 3570-3582; 1952).
The limitations of claim 1 and the disclosure of Yu and the teaching of Brown are discussed in the rejection above and hereby incorporated into the instant rejection.
Claim 27 of Suez discloses a method of synthesizing cyantraniliprole using the same amino-benzamide compound as claimed in instant claim 1:
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[Suez’ compound of formula (VII)]
Claim 27 of Suez attempts to further limit the method by requiring that the compound of formula (VII) be prepared by particular methods in separate claims; however, claim 27 of Suez and instant claim 1 are not patentably distinct, because the compound of formula (VII) used in a synthesis of cyantraniliprole is not a different compound as result of any particular method of its preparation. Additionally, while instant claim 1 further limits the process of preparing anthranilamides including cyantraniliprole by requiring that HCl is distilled from the reaction mixture during the reaction, a person of ordinary skill in the art would have a reasonable expectation of success in using the invention of Suez with distillation of HCl during the reaction because it was known in the art, per the disclosure of Yu, that the process of forming cyantraniliprole is successful when the reaction is conducted under reduced pressure, and that, per the teaching of Brown, HCl will continuously equilibrate into the gas phase from solution and thereby be removed under reduced pressure and thereby distill out of the reaction mixture.
Conclusion
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 W. JUSTIN YOUNGBLOOD whose telephone number is (703)756-5979. The examiner can normally be reached on Monday-Thursday from 8am to 5pm. The examiner can also be reached on alternate Fridays.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jeffrey S. Lundgren, can be reached at telephone number (571) 272-5541. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/W.J.Y./Examiner, Art Unit 1629
/JEFFREY S LUNDGREN/Supervisory Patent Examiner, Art Unit 1629
1 Cited in Applicant’s Information Disclosure Statement dated 04/02/2024.
2 Cited in Applicant’s Information Disclosure Statement dated 04/02/2024.
3 “The Clausius-Clapeyron Equation”, Britannica.com; https://www.britannica.com/science/thermodynamics/The-Clausius-Clapeyron-equation, archived by the Internet Wayback Machine on 03Apr2020, retrieved by the Examiner on 09Mar2026.
4 Cited in Applicant’s Information Disclosure Statement dated 04/02/2024.
5 3-Bromo-N-[4-chloro-2-methyl-6-[(methylamino)carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide
6 3-Bromo-1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-[N-methylcarbamoyl]phenyl]-1H-pyrazole-5-carboxamide
7 1-(3-Chloro-2-pyridinyl)-3-bromopyrazole-5-carbonyl chloride
8 2-Amino-5-chloro-N,3-dimethylbenzamide
9 2-Amino-5-cyano-N,3-dimethylbenzamide
10 Paragraph numbers are provided for the original patent (Chinese). Paragraph numbers in machine translated version may be offset from the original.
11 Note that an accurate measure of toluene’s Henry’s Law constant was best determined using a mixture of toluene in n-heptane rather than neat toluene - refer to Browns Table V, p3575. See Brown’s Table II, p3574 for results of other aromatic solvents dissolved in toluene.
12 https://www.britannica.com/science/thermodynamics/The-Clausius-Clapeyron-equation, archived by the Internet Wayback Machine on 03Apr2020, retrieved by the Examiner on 09Mar2026.
13 https://pubchem.ncbi.nlm.nih.gov/compound/Toluene, archived by the Internet Wayback Machine on 02/28/2020, retrieved by the Examiner on 08/27/2025.
14 https://pubchem.ncbi.nlm.nih.gov/compound/6342, archived by the Internet Wayback Machine on 03/07/2020, retrieved by the Examiner on 08/27/2025.
15 Boiling points of common organic solvents are well-known in the art. For dichloromethane, see PubChem CID 6344 - https://pubchem.ncbi.nlm.nih.gov/compound/6344
16 Boiling points of common organic solvents are well-known in the art. For dimethyl sulfoxide, see PubChem CID 679 - https://pubchem.ncbi.nlm.nih.gov/compound/679