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)
Information Disclosure Statement
The Information Disclosure Statement (IDS) filed February 6th, 2024 was considered by the Examiner.
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 are 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.
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/A.G.K./Examiner, Art Unit 1626
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699