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 Claims
Claims 1-9 are pending in the instant application.
Priority
This is a 35 U.S.C. 371 National Stage filing of International Application No. PCT/IN2022/050723 filed August 11th, 2022, which claims priority under 35 U.S.C. 119(a-d) to IN202141050378, filed November 2nd, 2021. Receipt is acknowledged of papers submitted under 35 U.S.C. 119(a)-(d)
Maintained Rejections
Applicant's arguments filed July 6th, 2026, with respect to the 35 U.S.C. 103 rejection of claims 1-9 as being unpatentable over Lahm in view of Taylor have been fully considered but they are not persuasive.
See response to remarks.
Response to Remarks
Applicant has traversed the 35 U.S.C. 103 rejection of claims 1-9 over Lahm in view of Taylor. However, Applicant’s arguments are not persuasive for the reasons below.
Applicant begins to traverse the rejection with an argument regarding the improvements of the instant invention compared to the prior art teachings of Lahm. Applicant argues that the instant application provides a process for preparing benzoxazinone compounds of Formula I which involves the single step addition of reacting materials and reagents. Applicant argues that the process of the instant application is simple, less complicated and easy to handle one pot process requiring the addition of the reagent and scavenger only once in the reaction. Specifically, Applicant points to the last line of instant claim 1, “the scavenger in step c and the reagent in step d are added in a single lot”.
In response, Lahm teaches the reaction involves addition of methanesulfonyl chloride in the presence of a tertiary amine such a triethylamine (pages 6-7). As Lahm teaches that the reagent, sulfonyl chloride, is in the presence of the scavenger, triethylamine, one of ordinary skill in the art would be motivated to administer the scavenger and reagent in a single lot.
Applicant then argues that the instant application is carried out at an ambient temperature and pressure hence saves energy. Examiner points out that Lahm teaches that the reaction can be conducted between about 0 and 100 °C, most conveniently near ambient temperature (e.g., about 10 to 40 °C), and more preferably between about 20 and 30 °C (page 13) and that the reaction may be conducted under greater than atmospheric pressure (page 16).
Further, Applicant argues that the instant invention requires less reaction time than the conventional processes. In response, Lahm teaches that the reaction is to be carried out in a reasonable reaction time, preferably less than 8 hours (pages 11-12). One of ordinary skill in the art would look to this disclosure to optimize the method. Further, the instant invention only claims that the reagent is slowly added to the reaction mass for a time period in a range of 1 to 2.5 hours, which fits within the teachings of Lahm, less than 8 hours.
Applicant then argues that the instant invention resulted in a higher yield of Formula I in a range of 80 to 98% and a higher purity in a range of 90 to 99%. In reply, Lahm teaches product yields in a range from 93-95% and also about 0.7% of ether being the only appreciable impurity observed (Examples).
On p. 2-3 of the remarks, Applicant highlights that comparative data addressing Lahm is found in paragraphs [0072]-[0074], as well as Tables 5 and 6 of the instant specification. Applicant argues that this comparison demonstrates the technical advancement achieved over Lahm, especially a higher purity and yield found in the instant disclosure.
Examiner acknowledges the data in the instant specification, but respectfully disagrees that it is sufficient to overcome the obviousness rejection.
Paragraph [0072] and Table 5 of the instant specification are based upon pyridine and methane sulfonyl chloride as the reagent and scavenger. Paragraphs [0074] and Table 6 of the instant specification are based upon 3-picoline and methane sulfonyl chloride as the reagent and scavenger.
Applicant refers to these alleged unexpected, surprising results; however, even if the results were considered unexpected, the results would not be commensurate in scope with the scope of the claims. The results provided do not occur over the entire claimed range (any scavenger or reagent). In the instant Tables and paragraphs, only methane sulfonyl chloride, pyridine and 3-picoline were used. It is unclear how results with a limited number of reagents and scavengers would result across the large number as instantly claimed. Further, no limitations were placed on the amount of reagent or scavenger in the instant claims.
Whether the unexpected results are the result of unexpectedly improved results or a property not taught by the prior art, the “objective evidence of no obviousness must be commensurate in scope with the claims which the evidence is offered to support.” In other words, the showing of unexpected results must be reviewed to see if the results occur over the entire claimed range. In re Clemens, 622 F.2d 1029, 1036, 206 USPQ 289, 296 (CCPA 1980). See MPEP 716.02 (d) and MPEP 716.02 (e).
An affidavit or deceleration under 37 CFR 1.132 must compare the claimed subject matter with the closes prior art to be effective to rebut a prima facie case of obviousness. In re Buckle, 592 F.2d 1175, 201 USPQ 67 (CCPA 1979).
On p. 3 of the remarks, Applicant continues to traverse the rejection, arguing that Taylor teaches away from the claimed invention. However, Taylor was only cited as motivation for optimizing the mole ratio range of a compound of Formula II and III. The motivation to combine the teachings of Lahm and Taylor and arrive at the instantly claimed invention arises out of the fact that Taylor also teaches the production of a fused oxazinone in an isotonic anhydride in the presence of a tertiary amine.
Thus, in light of the above, the 35 U.S.C. 103 rejection of claims 1-9, as being unpatentable over Lahm in view of Taylor is maintained.
Maintained 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 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.
Claim(s) 1-9 stand rejected under 35 U.S.C. 103 as being unpatentable over Lahm et al (WO 2003/015519 A1, published February 27th, 2003, as cited on the IDS) in view of Taylor et al (WO 2004/111030 A1, published December 23rd, 2004, as cited on the IDS).
Determining the scope and contents of the prior art. (See MPEP § 2141.01)
Lahm teaches the preparation of the following compound (Scheme 2, Table 2):
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232
258
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.
This compound is embraced by instant Formula I, wherein X is Cl.
Lahm teaches the following reaction scheme is used to produce the above compound of instant formula I (Scheme 2):
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435
594
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,
wherein R1 is CH3, R2 is Cl, R3 is Br and R5 is Cl.
Compound 4 above is embraced by instant formula III and compound 3 is embraced by instant formula II.
Lahm further teaches that the tertiary amine is compounds such as triethylamine or pyridine (Scheme 2).
Ascertainment of the differences between the prior art and the claims. (See MPEP § 2141.02)
Lahm does not explicitly teach that the compounds of instant formula II and instant formula III are in a mole ratio range of 1:1 to 1.3:1, that the reaction mixtures are cooled and heated and that the solvent is added to the mixture of the compound of instant formula II and instant formula III.
Finding of prima facie obviousness --- rationale and motivation (See MPEP § 2142-2143)
Regarding the limitation of the solvent being added to the mixture, Lahm also teaches an alternative way to prepare benzoxazinones that includes the use of solvents selected from pyridine and acetonitrile (Scheme 3). As such, one of ordinary skill in the art looking to optimize Lahm’s reaction Scheme 2, using the compounds of instant invention, would look to the other benzoxazinones production reactions of Lahm that include using acetonitrile as a solvent.
With regard to the limitation of the heating and cooling of the reaction, Lahm teaches that in the preparation of benzoxazinones that the reaction temperature is typically varied from as low as 0 °C up to the boiling point of the solvent in order to obtain a reasonable reaction time to complete the reaction, preferably, less than 8 hours (pages 11-12). As such, one looking to optimize the reaction of Lahm, would have been motivated by these teachings to adjust the temperature of the reaction.
Regarding the limitation that the compounds of instant formula II and instant formula III are in a mole ratio range of 1:1 to 1.3:1, Taylor teaches the production of a fused oxazinone in an isatoic anhydride in the presence of a tertiary amine. Taylor teaches that the mole ratio of said isatoic anhydride to said carboxylic acid is from about 0.8 to 1.2 (abstract). Formula III of the instant application is the carboxylic acid (See formula 2’). As such, one would look at Taylor for mole ratios of reactants to be used in the production of fused oxazinones. Taylor also teaches that the fused oxazinone is of instant formula I (abstract, Formula (Ia). Thus, one looking to optimize the reaction as taught by Lahm would have looked to Taylor, as the both teach the production of fused oxazinones of instant formula I, for guidance of mole ratio amounts of the reactants.
Further, regarding the optimization of Lahm’s reaction scheme, see MPEP 2144.04: Generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. "[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation." In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955) (Claimed process which was performed at a temperature between 40°C and 80°C and an acid concentration between 25% and 70% was held to be prima facie obvious over a reference process which differed from the claims only in that the reference process was performed at a temperature of 100°C and an acid concentration of 10%.); see also Peterson, 315 F.3d at 1330, 65 USPQ2d at 1382 ("The normal desire of scientists or artisans to improve upon what is already generally known provides the motivation to determine where in a disclosed set of percentage ranges is the optimum combination of percentages."); In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969) (Claimed elastomeric polyurethanes which fell within the broad scope of the references were held to be unpatentable thereover because, among other reasons, there was no evidence of the criticality of the claimed ranges of molecular weight or molar proportions.). For more recent cases applying this principle, see Merck & Co. Inc. v. Biocraft Lab. Inc., 874 F.2d 804, 10 USPQ2d 1843 (Fed. Cir.), cert. denied, 493 U.S. 975 (1989); In re Kulling, 897 F.2d 1147, 14 USPQ2d 1056 (Fed. Cir. 1990); and In re Geisler, 116 F.3d 1465, 43 USPQ2d 1362 (Fed. Cir. 1997); Smith v. Nichols, 88 U.S. 112, 118-19 (1874) (a change in form, proportions, or degree "will not sustain a patent"); In re Williams, 36 F.2d 436, 438 (CCPA 1929) ("It is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions, or degree, or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions."). See also KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398, 416, 82 USPQ2d 1385, 1395 (2007) (identifying "the need for caution in granting a patent based on the combination of elements found in the prior art.").
In view of the above, the reaction of instant claim 1 has been rendered obvious.
Regarding claim 2, as seen above, Lahm teaches the use of acetonitrile as a solvent.
Regarding claim 3, as seen above, Lahm teaches the use of triethyl amine as the scavenger.
Regarding claim 4, as seen above, Lahm teaches the use of methane sulfonyl chloride as the reagent.
Regarding claims 5-7, Lahm teaches that in the preparation of benzoxazinones that the reaction temperature is typically varied from as low as 0 °C up to the boiling point of the solvent in order to obtain a reasonable reaction time to complete the reaction, preferably, less than 8 hours (pages 11-12). Lahm also teaches that the reaction is usually conduction at a temperature between about 0 to 100°C. Further, Lahm teaches that in boiling, temperatures between about 30 to 90 °C are preferred (pages 13-15) Thus, the range taught by Lahm overlaps with the cooling temperature of 0-10°C and heating temperature of 10-20°C , as instantly claimed. As such, one looking to optimize the reaction of Lahm, would have been motivated by these teachings to adjust the temperature of the reaction. See also, MPEP 2144.04 above.
Regarding claim 8, Taylor teaches that the mole ratio of the tertiary amine to carboxylic acid is from about 2.0 to 4.0. Formula III of the instant application is the carboxylic acid as taught by Taylor (see Formula 2’). One of ordinary skill in the art would have been motivated by these teachings to optimize the reaction as taught by Lahm. See also MPEP 2144.04 above.
Regarding claim 9, Lahm teaches that the method of scheme 2 affords good yields of the benzoxazinone (page 7). Lahm also teaches that yields include 90% (example 7) and impurities of only 0.7% (examples 1-7).
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.
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/A.G.K./Examiner, Art Unit 1626
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699
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