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 – 20 are pending.
Clams 1 – 15 and 18 – 20 are rejected.
Claims 16 and 17 are objected.
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 – 15 and 18 – 20 are rejected under 35 U.S.C. 103 as being unpatentable over Su et al. (US 2017/0369412) in view of Gharda et al. (US 2020/0031767) and Hagen (US 5,424,481).
The rejected claims cover, inter alia, a process for the preparation of 2-nitro-4-(methylsulfonyl)benzoic acid (NMSBA), said process comprising the following steps: a) reacting 1 -chloro-2-nitro-4-methyl sulfonyl benzene (chioro NMSB) with a compound of Formula II by using a base in a fluid medium at a first predetermined temperature to obtain a compound of Formula III; wherein, R1 is selected from -CONH2, and -COOR3, wherein R3 is selected from C1- C4 alkyl; and R2 is a cyano group (-CN); b) reacting said compound of Formula III with an oxidizing agent optionally in the presence of a catalyst under stirring to obtain a mixture; c) optionally passing a predetermined amount of air trough said mixture; and d) heating said mixture to a second predetermined temperature for a predetermined time period to obtain a product mixture comprising 2- Nitro-4-(methyl sulfonyl)benzoic acid, wherein a yield of 2-Nitro-4-(methyl sulfonyl)benzoic acid is greater than 75% and a purity is greater than 90 %.
Dependent claims 2 and 3 further limit the compound of Formula II. Dependent claims 4 and 5 further limit the base used in step a). Dependent claim 6 further limits the fluid medium of step a). Dependent claim 7 further limits Formula III. Dependent claim 8 and 9 further limit the first temperature of step a). Dependent claims 10, 11 and 12 further limit the oxidizing agent. Dependent claim 13 further limits the catalyst. Dependent clams 14 and 15 further limit the predetermined amount air for step c). Dependent claim 18 further limits the product yield.
Dependent claim 19 covers, inter alia, the process as claimed in claim 1, wherein said process comprises the following steps: a) reacting 1-chloro-2-nitro-4-methyl sulfonyl benzene (chloro NMSB) with methyl cyano acetate (Formula II) by using a base in a fluid medium at a first predetermined temperature to obtain methyl-2-cyano-2-(4-(methyl sulfonyl)-2-nitrophenyl)acetate (Formula III); b) reacting methyl-2-cyano-2-(4-(methyl sulfonyl)-2-nitrophenyl)acetate with an oxidizing agent optionally in the presence of a catalyst under stirring to obtain a mixture; c) optionally passing a predetermined amount of air through said mixture; and d) heating said mixture to a second predetermined temperature for a predetermined time period to obtain a product mixture comprising 2- Nitro-4-(methyl sulfonyl)benzoic acid.
Dependent claim 20 covers, inter alia, the process as claimed in claim 1, wherein said process comprises the following steps: a) reacting 1-chloro-2-nitro-4-methyl sulfonyl benzene (chloro NMSB) with cyano acetamide by using a base in a fluid medium at a first predetermined temperature to obtain 2-cyano-2-(4-methylsulfonyl)-2- nitro-phenyl acetamide; b) reacting methyl-2-cyano-2-(4-(methyl sulfonyl)-2-nitrophenyl)acetate with an oxidizing agent optionally in the presence of a catalyst under stirring to obtain a mixture; c) optionally passing a predetermined amount of air through said mixture; and d) heating said mixture to a second predetermined temperature for a predetermined time period to obtain a product mixture comprising 2- Nitro-4-(methyl sulfonyl)benzoic acid.
However, Su discloses the process for the preparation of 2-nitro-4-methanesulfonylphenyl methyl cyanoacetate by reaction of 1-chloro-2-nitro-4-methyl sulfonyl benzene (chloro NMSB) with methyl cyanoacetate in the presence of NaOH in DMSO at a temperature of less than 60°C for 1 hour (pp. 4, [0041], Example 10). In particular, Su discloses the addition of 1.015 moles of methyl cyanoacetate per mole of 1-chloro-2-nitro-4-methyl sulfonyl benzene.
Also, Su discloses the process for the preparation of 2-nitro-4-(methylsulfonyl)benzoic acid by oxidation of methyl-2-cyano-2-(4-(methyl sulfonyl)-2-nitrophenyl)acetate, compound of formula (Ill) when R1 = COOCH3 and R2 = CN, with hydrogen peroxide (30%) at 40°C for 2 hours under stirring (pp. 3, [0032], Example 3). In particular, Su discloses the addition of about 3.7 mole of H202 per mole of compound of formula (Ill). After purification, the yield of the product is 97%.
The difference between Su and the claimed invention is that it does not teach the invention with particularity so as to amount to anticipation (See M.P.E.P. §2131: "[t]he identical invention must be shown in as complete detail as is contained in the ...claim." Richardson v. Suzuki Motor Co., 868 F.2d 1226, 1236, 9 USPQ2d 1913, 1920 (Fed. Cir. 1989). The elements must be arranged as required by the claim, but this is not an ipsissimis verbis test, i.e., identity of terminology is not required. In re Bond, 910 F.2d 831, 15 USPQ2d 1566 (Fed. Cir. 1990).).
However, based on the above, Su teaches the elements of the claimed invention with sufficient guidance, particularity, and with a reasonable expectation of success, that the invention would be prima facie obvious to one of ordinary skill (the prior art reference teaches or suggests all the claim limitations with a reasonable expectation of success. (see M.P.E.P. § 2143).
The difference between the instantly claimed invention and Su is as follows: oxidizing agent being nitric acid; the catalyst being vanadium pentoxide; predetermined amount of air in the range of 15 to 25 liters per hour per mole of Formula III or 20 liters per hour per mole of Formula III.
However, with regard to oxidizing agent being nitric acid; the catalyst being vanadium pentoxide; predetermined amount of air, the Examiner turns to the teaching of Gharda. Gharda discloses a process for preparing 2-nitro-4-methlsulfonylbenzoic acid from 2-nitro-4-methylsulfonyl toluene. (pp. 4, [0062]). The process of Gharda uses nitric acid as an oxidizing agent and vanadium pentoxide as the catalyst. (pp. 6, [0107]). According to Gharda the reaction temperature is 145°C with air passing. The reaction takes place over a period of 8 hours to obtain a reaction mass. At the completion of the reaction and the reaction mass wat purified obtaining 2-nitro-4-methylsulfonylbenzoic acid with a HPLC purity of 99%.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the instantly claimed invention to prepare 2-nitro-4-(methylsulfonyl)benzoic acid as disclosed in the teaching of Su and modify the process when a catalyst and air is use according to the teaching of Gharda, wherein it is disclosed that the oxidizing agent of nitric acid is in use with the vanadium pentoxide catalyst with air passing in a reaction that produces 2-nitro-4-(methylsulfonyl)benzoic acid. Motivation can be found in the fact that both Su and Gharda were seeking methods to produce 2-nitro-4-(methylsulfonyl)benzoic acid.
Therefore, all the claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination would have yielded predictable results to one of ordinary skill in the art before the effective filing date of the instantly claimed invention. KSR International Co. v. Teleflex Inc., 550 U.S. 398, 82 USPQ2d 1385 (U.S. 2007).
Regarding oxidizing agent being nitric acid; the catalyst being vanadium pentoxide; predetermined amount of air in the range of 15 to 25 liters per hour per mole of Formula III or 20 liters per hour per mole of Formula III, Examiner turns to the teaching of Hagen. The prior art of Hagen discloses the preparation of 4-methylsulfonyl-2-nitrobenzoic acid. (col. 3 ln 62 – col. 4, ln 11). The process comprising 45 g of 4-methylsulfonyl-2-nitrotoluene and 1 g of vanadium pentoxide were dissolved in 375 ml of 70% strength by weight sulfuric acid. The reaction mixture was heated to 145 °C while air was passed into it at a rate of 100 l/h. Once at that temperature of 145 °C the metered addition was commenced of 65% strength by weight nitric acid at a rate of 0.25 ml/min. A total of 135 ml of nitric acid were added over 9 hours. At the same time 120 ml of 35% strength by weight nitric acid were distilled out of the reaction mixture. The reaction mixture was then cooled down to 20 °C and the precipitate was filtered off with suction and washed with water. This yielded 44 g (83% of theory) of 4-methylsulfonyl-2-nitrobenzoic acid (melting point 204-206 °C)
It would have been obvious to one of ordinary skill in the art before the effective filing date of the instantly claimed invention to prepare 2-nitro-4-(methylsulfonyl)benzoic acid as disclosed in the teaching of Su and modify the process when a catalyst and air is use according to the teaching of Hagen, wherein it is disclosed that the oxidizing agent of nitric acid is in use with the vanadium pentoxide catalyst with air passing in a reaction at a rate of 100l/h producing 2-nitro-4-(methylsulfonyl)benzoic acid. Motivation can be found in the fact that both Su and Hagen were seeking methods to produce 2-nitro-4-(methylsulfonyl)benzoic acid.
Therefore, all the claimed elements were known in the prior art and one skilled in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination would have yielded predictable results to one of ordinary skill in the art before the effective filing date of the instantly claimed invention. KSR International Co. v. Teleflex Inc., 550 U.S. 398, 82 USPQ2d 1385 (U.S. 2007).
Regarding claim 19, The Examiner turns to the teaching of Su. The prior art of Su, discloses all the steps for the preparation of 2-nitro-4-(methylsulfonyl)benzoic acid (NMSBA), comprising (i) the reaction of 1-chloro-2-nitro-4-methyl sulfonyl benzene with methyl cyano acetate in the presence of a base in a fluid medium at a first predetermined temperature (ii) reacting methyl-2-cyano(4-(methyl sulfonyl)-2-nitrophenyl)acetate with an oxidizing agent and (iii) heating the mixture to a second predetermined temperature for a predetermined time period (see the detailed argumentation for claim 1 in para. 12 above; Examples 3 and 10 of Su).
The difference between Su and the claimed invention 19 is that it does not teach the invention with particularity so as to amount to anticipation (See M.P.E.P. §2131: "[t]he identical invention must be shown in as complete detail as is contained in the ...claim." Richardson v. Suzuki Motor Co., 868 F.2d 1226, 1236, 9 USPQ2d 1913, 1920 (Fed. Cir. 1989). The elements must be arranged as required by the claim, but this is not an ipsissimis verbis test, i.e., identity of terminology is not required. In re Bond, 910 F.2d 831, 15 USPQ2d 1566 (Fed. Cir. 1990).).
However, based on the above, Su teaches the elements of the claimed invention with sufficient guidance, particularity, and with a reasonable expectation of success, that the invention would be prima facie obvious to one of ordinary skill (the prior art reference teaches or suggests all the claim limitations with a reasonable expectation of success. (see M.P.E.P. § 2143).
Regarding claim 20, Su does not disclose a process for the preparation of 2-nitro-4-(methylsulfonyl)benzoic acid (NMSBA) by oxidation of 2-cyano-2-(4-(methyl sulfonyl)-2-nitrophenyl)acetamide.
However, as describe in paragraph 12 above, the reaction with methyl cyanoacetate is disclosed, and, in view of the structural similarity, it would be obvious to the person skilled in the art to substitute the reactant accordingly. Where 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).
Allowable Subject Matter
Claims 16 and 17 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter: None of the prior art of record teaches or suggest that process step d) be carried out in a second predetermined temperature in the range of 95 to 100 °C during the predetermined time period. Nor is there teaching of the second predetermined temperature being 98 °C and the predetermined time period is 1 hour.
Conclusion
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/YATE' K CUTLIFF/Primary Examiner, Art Unit 1692
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