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
Claims 1, 4-11 of Y. Tasaki, et al., US 18/488,978 (10/17/2023) are pending, under examination on merits and are rejected.
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55. However, a certified English translation of the foreign application has not been filed. 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). Failure to provide a certified translation may result in no benefit being accorded for the non-English application.
Withdrawal Claim Rejections - 35 USC § 103
Rejection of claims 1-2 and 5-9 under 35 USC § 103 Rejection over a combination of R. J. D. Feo, et al, 28.10 The Journal of Organic Chemistry 2915-2917(1963)(“Feo”), Chem Service, Inc.-Pesticide & Metabolite Standards Catalog (2006)(“Chem Service”) and N.G. Anderson, Practical Process & Research Development (2000) (“Anderson”); and rejection of claims 10-11 are rejected as applied above for the rejection of claim 1 further in view of D. I. Hoz, et al, 34.2 Chemical Society Reviews 164-178 (2005)(“Hoz”) or N. G. Anderson, 16.5, Organic Process Research & Development 852-869(2012)(“Anderson-1”) are withdrawn because the instant claim 1 has been amended with a new limitation of
wherein the reaction catalyst is at least one of a Lewis acid, a Broensted acid, a metal oxide, or a phosphorus oxide compound,
wherein the phosphorus oxide compound is diphosphorus pentoxide
which cannot be met by the recited prior art or their combination. Applicant also argues on this issue in the reply filed on 07/14/2026. See Discussion of Claim Rejections under 35 U.S.C. 103 at page 6-7 in the Remarks filed on 07/14/2026.
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.
Maintained 35 USC § 103 Rejection
Rejection of claims 1 and 4-9 under 35 USC § 103 over J. R. Merchant, et al, 48.1 Current Science 13-15 (1979)(“Merchant”) is maintained evidenced with W. Qiu, et al, 18 ChemSusChem, e202500100 (2025)(Qiu).
J. R. Merchant, et al, 48.1 Current Science 13-15 (1979)(“Merchant”)
Merchant teaches a reaction between halogenoaniline with acrylic or methyl acrylic in the presence of PPA1 at 100-140ºC for 3-7 hr. Merchant at page 13, right col. paragraph 2, line 1-4.
Per Table 1, Merchant teaches that the reaction between p-chloroaniline and α-methyl-acrylic acid forms product 4-chloro-α-methyl-acrylanilide. Merchant at page 14, Table 1. Examiner schematically summarize the Merchant method as below:
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The Merchant α-methyl-acrylic acid maps the general Formula (1) in the instant claims 1 and 8 as R1 is methyl and R2 is hydrogen atom; the Merchant p-chloroaniline maps the general Formula (2) in the instant claims 1, 7 and 9 as R3 is chloride that is an electron withdrawing group2, m is 1, n is 0, and Ar is benzene.
Difference between Merchant and Claims 1,4-9
The Merchant method differs from the instant claims 1,4-9 only in that the reaction temperature is not the claimed temperature.
Claims 1,4-9 are Obviousness
In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. MPEP 2144.05. I. Herein, the claimed temperature (higher than 120ºC, 130ºC or higher, 140ºC or higher) overlaps with the prior art temperature of 100-140ºC, therefore, a prima facie case of obviousness exists, thus, claims 1, 5-9 are obvious.
Claim 4 is also obvious because the Merchant catalyst polyphosphoric acid (PPA) is a Broensted acid, which is evidenced with Qiu at page 2 of 6, right col. line 4-6.
Applicant’s Arguments
Applicant argues the 103 rejection on the ground that:
Specifically, according to the disclosure of Merchant, Merchant merely teaches the use of polyphosphoric acid (PPA) as a catalyst. However, Merchant does not teach or suggest using diphosphorus pentoxide as the phosphorus oxide compound catalyst. Clearly, Merchant fails to disclose the technical feature of "wherein the reaction catalyst is at least one of a Lewis acid, a Broensted acid, a metal oxide, or a phosphorus oxide compound, wherein the phosphorus oxide compound is diphosphorus pentoxide recited in the amended claim 1.
The last paragraph at page 6 of the Remarks filed on 07/14/2026.
This argument is not persuasive because as mentioned above in the rejection that polyphosphoric acid (PPA) is a Broensted acid which can be evidenced by Qiu.
New 35 USC § 103 Rejections
Claim 10 is rejected under 35 USC § 103 Rejection over J. R. Merchant, et al, 48.1 Current Science 13-15 (1979)(“Merchant”) as applied above for the rejection of claim 1 further in view of Kazushi, et al, JPS63110205A (1988)(“Kazushi”) and S. Gadhwal, et al. 37 INDIAN JOURNAL OF CHEMISTRY SECTION B, 725-727 (1998)(“Gadhwal”) evidenced with L. Peng, et al. 4.3 Nature materials 216-219 (2005)(“Peng”).
J. R. Merchant, et al, 48.1 Current Science 13-15 (1979)(“Merchant”)
As mentioned in the rejection above that Merchant teaches a method meeting each and every limitation of claim 1.
Difference between Merchant and Claim 10
The Merchant method differs from the instant claim 10 in that Merchant does not teach the reaction temperature is controlled by microwave irradiation.
Kazushi, et al, JPS63110205A (1988)(“Kazushi”)
Kazushi is published in Japanese, a copy of machine translation is attached as the second part of Kazushi, thus, the full reference has a page of 10, the format for the citation of Kazushi is XX/10.
Kazushi teaches that the compound of the follows formula can be used as a monomer to prepare heat resistant resin. Kazushi at title, Claim 1 at page 01/10, line 16-18 at page 02/10, and line 16-18 at page 07/10.
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Per Example 9, Kazushi teaches that resin made from N-4-chlorophenylmethacrylamide has excellent heat resistance, fluidity, transparency and colorability. Kazushi at table 2, Example 9, and the last sentence at left col of page 10/10.
CA abstract indicates that the Kazushi N-4-chlorophenylmethacrylamide (RN # 2918-77-6) has the same chemical structure as that of the Merchant 4-chloro-α-methyl-acrylanilide. Thus, Kazushi provides a motivation for one of ordinary skill in the art to synthesize the Merchant 4-chloro-α-methyl-acrylanilide.
It should be noted that after comparing of the structures of the monomers taught by Kazushi with the method/product taught by Merchant, one ordinary skill in the art would be appraised that the Kazushi monomers including N-4-chlorophenylmethacrylamide can be synthesized with the method taught by Merchant.
S. Gadhwal, et al. 37 INDIAN JOURNAL OF CHEMISTRY SECTION B, 725-727 (1998)(“Gadhwal”)
Gadhwal teaches a method for conversion of carboxylic acid including unsaturated carboxylic acid to amides with zeolite-HY as a catalyst under microwave irradiations as indicated in Scheme I. Gadhwal at title and Scheme I at page 725.
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Gadhwal teaches that:
zeolite-HY effects the formation of various saturated and unsaturated amides in excellent yields under microwave irradiation and with an extremely simple work-up, which makes it a reagent of practical synthetic value. The reaction is fairly general, facile and efficient and is devoid of any side products emanating from functional groups present.
Gadhwal at page 725, left col. the last second sentence to right col. line 3, emphasis added.
Gadhwal teaches that:
In a typical case, zeolite-HY was added to a mixture of acetic acid and aniline in an Erlenmeyer flask and placed in a commercial microwave oven operating at 2450 MHz frequency and irradiated for 40 min. The reaction mixture was allowed to attain room temperature, treated with methanol and filtered off.
Gadhwal at page 725, right col. line 4-9, emphasis added.
Thus, Gadhwal fairly teaches one ordinary skill in the art the reaction is conducted at a heating condition.
L. Peng, et al. 4.3 Nature materials 216-219 (2005)(“Peng”)
The evidence from Peng indicates that zeolite-HY is a Brønsted acid. Peng at title and abstract.
Obviousness Rationales of Claim 10
One ordinary skill in the art would arrive at the claimed invention before the effective filling date of the instant application in view of the teachings from Merchant, Kazushi and Gadhwal evidenced with Peng.
One ordinary skill in the art seeking to use the Merchant 4-chloro-α-methyl-acrylanilide as a monomer for heat resistant resin is motivated to prepare the compound through modification the Merchant method by:
(i) using zeolite-HY as a catalyst;
(ii). setting up the reaction temperature at 100-140ºC; and
(iii). controlling the reaction temperature by a microwave oven irradiation.
thus arrive at a method meeting each and every limitation of claims 10 except the temperature of the reaction differs from the claimed temperature. [I]n the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. MPEP 2144.05. I. Herein, the claimed temperature (higher than 120ºC) overlaps with the prior art temperature of (100-140ºC), therefore, a prima facie case of obviousness exists, thus, claim 10 is obvious.
One ordinary skill in the art has a motivation to do so with a reasonable expectation of success because
(i). Gadhwal teaches that with zeolite-HY as a catalyst under microwave irradiation various saturated and unsaturated amides can be formed in excellent yields by reacting of various acid with various amine, and the reaction is fairly general, facile and efficient and is devoid of any side products emanating from functional groups present;
(ii). Gadhwal teaches that his method is conducted at a heating condition; and
(iii). Merchant teaches that 4-chloro-α-methyl-acrylanilide can be formed by reacting of p-chloroaniline with α-methyl-acrylic acid at a temperature of 100-140ºC.
Claim 11 is rejected under 35 USC § 103 Rejection over a combination of J. R. Merchant, et al, 48.1 Current Science 13-15 (1979)(“Merchant”), Kazushi, et al, JPS63110205A (1988)(“Kazushi”), S. Gadhwal, et al. 37 INDIAN JOURNAL OF CHEMISTRY SECTION B, 725-727 (1998)(“Gadhwal”) evidenced with L. Peng, et al. 4.3 Nature materials 216-219 (2005)(“Peng”), further in view of N. G. Anderson, 16.5, Organic Process Research & Development 852-869(2012) (“Anderson-1”).
The combination of Merchant, Kazushi and Gadhwal
As detail discussed above that the combination of Merchant, Kazushi and Gadhwal teaches a method meeting each and every limitation of claim 1.
Difference between the Combination and Claim 11
The method taught by the combination differs from the instant claim 11 in that none of the recited prior art teaches to carry out the reaction by a flow-type reaction.
N. G. Anderson, 16.5, Organic Process Research & Development 852-869(2012) (“Anderson-1”)
Anderson-1 teaches that:
Multikilogram amounts of drug candidates are needed in drug development, increasing from perhaps 10 kg needed for phase 2 studies up to manufacturing batches that may be hundreds of kilograms. Batch operations, routinely used in the pharmaceutical and fine chemicals industries, are not always easy to scale-up.
Anderson-1 at page 852, left col. paragraph 1, line 1-5, emphasis added.
Anderson-1 teaches that:
In continuous operations, or flow operations, process streams flow through reactors where mixing, temperature, and other parameters can be tightly controlled. Continuous operations can use energy efficiently and produce materials with less waste, an approach to processing which has been termed process intensification.
Anderson-1 at page 852, left col. paragraph 2, line 1-6.
Anderson-1 teaches that the follows five considerations primarily drive the development of continuous processes:
First, by efficiently mixing process streams and controlling reaction temperatures, side products from micromixing and temperature excursions can be minimized, possibly reducing the number of rejected batches in manufacturing.
Second, continuous operations can be applied economically for both cryogenic and high-temperature processes. Sometimes processes requiring cryogenic temperatures in batch mode can be carried out using higher temperatures with short contact times; such operations may eliminate the need for expensive reactors for cryogenic temperatures.
Third, reactive species can be separated, thus minimizing side products and raising yields.
Fourth, by continuously circulating reaction streams past an energy source such as a lamp or a sonic horn, or through a bed of an immobilized catalyst, the forced contact can ensure rapid reactions.
Finally, the above characteristics of continuous operations may be applied to develop safe processes.
Anderson-1 at page 852, line 4 to page 853, left col. paragraph 2.
Obviousness Rationale of Claim 11
One ordinary skill in the art would arrive at the claimed invention before the effective filling date of the instant application in view of the teachings from Merchant, Kazushi and Gadhwal and Anderson-1.
Claim 11 is obvious because one ordinary skill is also motivated to further modify the proposed method by conducting of the reaction in a flow type reaction because Anderson-1 teaches that flow-type reaction not only improves energy efficiency, but also improves safety, aids scale-up; and many reactions have been successfully scaled-up through flow-type production.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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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/FRANK S. HOU/Examiner, Art Unit 1692
/AMY C BONAPARTE/Primary Examiner, Art Unit 1692
1 Polyphosphoric acid
2 See International Union of Pure and Applied Chemistry, Compendium of Chemical Terminology (IUPAC), Gold Book, page 605 (2014) (“Gold Book”) at page 103, apicophilicity.
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