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 .
Election/Restrictions
Applicant's election with traverse of Group I, claims 2-13 and 17-18 in the reply filed on 6/9/2026 is acknowledged. The traversal is on the ground(s) that the claimed catalysts are common among the pending claims and area special technical feature under the rules for unity of invention practice. This is not found persuasive because even though the catalyst is present in all Groups, this technical feature is not a special technical feature as it does not make a contribution over the prior art in view of Anguo (“Michael Addition of Methylene Active Compounds to Chalcones with Novel Task-specific Ionic Liquids as Catalysts under Solvent-free Conditions”, Chinese Journal of Organic Chemistry, 2011, p. 1312, of record in the IDS filed on 10/30/2023). Therefore, the groups of inventions listed do not relate to a single general inventive concept under PCT Rule 13.1 because, under PCT Rule 13.2, they lack the same or corresponding special technical features. See p. 4-5 of the OA dated 4/9/2026. The Applicant does not provide any objective evidence that the catalysts claimed are structurally distinct from those of Anguo, only arguing that the catalysts perform well in the claimed reaction. "[E]ven though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process." In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985). See MPEP 2113.
The requirement is still deemed proper and is therefore made FINAL.
Claims 14-16 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Claim Status
Claims 2-18 are pending, claims 14-16 stand withdrawn, and claims 2-13, 17, and 18 are under examination.
Priority
The instant application was filed on 10/30/2023 and claims the benefit of priority to:
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See filing receipt dated 9/5/2024. Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Specification
The disclosure is objected to because of the following informalities: the chemical structures in [0010 and 0012] are blurry and difficult to read.
There also appears to be an error in [0079]. Line 1 recites “Comparative examples 3 and 4 are similar to Embodiment 2”. Embodiment 2, as described in [042-0043] is inventive and uses an ionic liquid. However, Table 6 in [0080], which compares the results of comparative examples 2 to 4, indicates that only the nitrogen-heterocycle is present in the mixture. Therefore, it is believed that he phrase “Embodiment 2” in line 1 of [0079] should be deleted and replaced by “Comparative example 2”.
Appropriate correction is required.
Claim Objections
Claims 2, 5, 6, 8, and 17 are objected to because of the following informalities:
In line 8 of claim 2, the phrase “the nitrogen-containing” should be deleted and replaced by “a nitrogen-containing” as this is the first mention of the heterocyclic compound in claim 2.
In line 3 of claim 5, the limitation “R1COOH or” should be deleted and replaced by “R1COOH and”.
In line 4 of claim 5, the word “fluorophosphates” should be singular “fluorophosphate”.
In line 3 of claim 6, the phrase “or oxalate” should be deleted and replaced by “and oxalate”.
In line 4 of claim 6, the word “or” should be deleted and replaced by “and”.
In the final line of claim 8, the word “and” should be inserted before the word “combinations”.
In line 5 of claim 17, the phrase “or oxalate” should be deleted and replaced by “and oxalate”.
In line 6 of claim 17, the word “or” at the end of the line should be deleted and replaced by “and”.
In line 7 of claim 17, the word “fluorophosphates” should be singular “fluorophosphate”.
In line 9 of claim 17, the word “and” should be inserted before the phrase “the mass”.
Appropriate correction is required.
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) 2-6, 10-13, and 17 is/are rejected under 35 U.S.C. 103 as being unpatentable over Nagasawa (JP2013133330A, published on 7/8/2013, of record with an English translation in the IDS filed on 6/9/2026) in view of Anguo (“Michael Addition of Methylene Active Compounds to Chalcones with Novel Task-specific Ionic Liquids as Catalysts under Solvent-free Conditions”, Chinese Journal of Organic Chemistry, 2011, p. 1312, of record in the IDS filed on 10/30/2023 and English translation of record in the IDS filed on 6/9/2026).
Applicant claims a synthetic method for preparing 3-(3-oxo-2-pentyl)cyclopentyl dimethyl malonate comprising reacting 2-pentyl-2-cyclopentenone and dimethyl malonate in the presence of a basic ionic liquid catalyst comprising a nitrogen-containing heterocyclic compound and an aliphatic carboxylate, hydroxyl aliphatic carboxylate, or fluorophosphate and having a pH of greater than or equal to 10.
Nagasawa teaches a process for producing a compound of formula (III) by reacting a cyclopentenone compound of formula (I) with a malonate of formula (II) via a Michael addition:
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See claim 1. R1 is a hydrocarbon group having 1 to 10 carbon atoms, R2 is an alkyl group having 1 to 4 carbon atoms, and R3 is an alkyl group or alkoxy group having 1 to 4 carbon atoms. In examples 1-4, Nagasawa teaches the reaction between 2-pentyl-2-cyclopentenone (compound I above, wherein R1 is pentyl, a C5 alkyl) and dimethyl malonate (compound II above, wherein R2 is methyl, a C1 alkyl, and R3 is OMe, a C1 alkoxy) to produce dimethyl 2-(3-oxo-2-pentylcyclopentyl)malonate (compound III above, wherein R1 to R3 are as above). Therefore, the inventive reactions of Nagasawa teach the instantly claimed reactants (compounds 1 and 2 of Nagasawa) and product (compound 3 of Nagasawa).
Nagasawa teaches that the Michael addition is carried out in the presence of a solid base catalysts containing a phosphazene base or a guanidine base. See abstract. The phosphazene base is a compound of formula (IV):
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, wherein Z is an alkyl or aryl group, Y is a dialkylamino group, a pyrrolidino group, a morpholino group, a piperazino group, a tridialkylaminophosphine amino group, or a trispyrrolidinophosphine imino group. See [0023] or the original patent and discussion of “phosphazene” base on p. 4-5 of the translation. The guanidine base is a compound of formula (V):
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, wherein X is N or C and n and m are independently 1 to 4. See [0027] of original patent and discussion of “guanidine base” on p. 5 of the translation. Nagasawa teaches that the bases are strong organic bases, preferably supported on a solid carrier including organic polymers, silica, alumina, silica alumina, titania, zirconia, diatomaceous earth, and activated carbon. See discussion of “solid base catalyst” on p. 4 of the translation. Examples 1-4 teach the use of P-BEMP, a phosphazene base supported on a polystyrene resin of formula (IV-1):
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or Jandajel®-TBD, a guanidine base supported on a Jandajel® polymer of formula (IV-2):
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. See examples and [0025 and 0030] of the original patent.
Nagasawa teaches that the solid bases are advantageous because, in addition to being efficient catalysts for the reaction, they can be easily recovered from the reaction mixture and reused. See examples, wherein 2 and 3 teach catalysts recycling, and the Table on p. 13 of the patent, which shows that the yields of compound (III) are higher using the inventive catalysts than others including homogeneous catalysts, inorganic heterogeneous catalysts, and anion exchange resins (described in the comparative examples).
Nagasawa does not explicitly teach the reaction can be carried out with a basic ionic liquid with a pH value of greater than or equal to 10 comprising a nitrogen-containing heterocyclic compound and an aliphatic carboxylate, hydroxyl aliphatic carboxylate, or fluorophosphate prepared by mixing the two components and stirring.
Anguo teaches basic ionic liquids as catalysts for the Michael addition of methylene active compounds to chalcones under solvent-free conditions. See abstract. Anguo teaches that the ionic liquids are based on DBU (1,8-diazabicyclo[5.4.0]undec-7-ene-claim 4), a compound of formula (V) of Nagasawa, wherein X is C, m is 2, and n is 3. Anguo exemplifies the following ionic liquids:
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. See Figure 1 on p. 1313. Thus, the ionic liquids comprise the nitrogen-containing heterocyclic compound (DBU-claim 4) and an aliphatic carboxylate (TFa, Ac, n-Pr, and n-Bu) or a hydroxyl aliphatic carboxylate (Lac). TFa, Ac, n-Pr, and n-Bu correspond to trifluoroacetate, acetate, propionate, and butylate (claim 6), which are compounds of instant formula R1COOH of claim 5, wherein R1 is C1-4 alkyl. Lac corresponds to hydroxypropionate (claim 6), a compound of instant formula OHR3COOH in claim 5, wherein R3 is an ethylene (C2) group. Anguo does not explicitly teach a method of preparing the catalysts, however Anguo discusses that ionic liquids and their preparation are well-known in the art in the translation of the introduction section. As the ionic liquid is derived from an acid base reaction between DBU and an organic acid and comprises no other components, it would be obvious for the skilled artisan to predictably arrive at the claimed ionic liquid by mixing DBU and the aliphatic carboxylate or hydroxyl carboxylate with stirring to facilitate the mixing. Further the ionic liquid preparation limitation in claim 2 is drafted in a “wherein” clause and is written in a passive voice, as compared to all of the other actively required process steps. Therefore, though the step is obvious in view of Anguo, it does not appear to be required other than to define the structure of the ionic liquid.
Anguo tested a series of catalysts, the influence of catalysts loading, and the influence of solvent in the following reaction:
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. See p. 1313. The best performing catalyst was [DBU][Ac]. Also see discussion of Table 1 in the translation. Anguo teaches that when DBU was used as the sole catalyst (entry 4 above) that “the ketone disappeared, but byproducts, appeared, possibly due to its excessive alkalinity; additionally organic bases are volatile when used as catalysts and may cause problems during operation”. The problems are overcome using a DBU containing ionic liquid. As evidenced by [0037] of the specification as filed, [DBU][Ac] has a pH of 13.2, which falls within the range of claims 2, 3, and 17. Also see MPEP 2144.05.
Angua applied the optimized conditions ([DBA][Ac] in 0.2 mmol in the absence of solvent) to the following reaction, which varied the nucleophile:
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. Entry 7 corresponds to the use of diethyl malonate, a one carbon homolog of the claimed dimethyl malonate, and provides the desired product in 94% yield. See p. 1314. Anguo also teaches a series of reactions in Table 4 on p. 1315, which varies the nitrogen-heterocycle and anion of the ionic liquids to show the superiority of DBU based [DBU][Ac] as compared to imidazolium and guanidinium basic ionic liquids. Also see discussion of Tables 2 and 4 in the translation. Anguo further teaches that the recyclability of the DBU ionic liquids is excellent as demonstrated by Table 5 on p. 1316 (also see discussion thereof in the translation and abstract).
It would have been prima facie obvious to combine the teachings of Nagasawa and Anguo to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to substitute the best performing basic ionic liquid [DBU][Ac] of Anguo, which inherently possesses the claimed pH value of 13.2 as evidenced by the specification as filed, for the catalysts of Nagasawa because both sets of catalysts comprise strong organic nitrogen heterocyclic bases which are known to catalyze Michael additions. Therefore, replacing the base of Nagasawa with the base of Anguo will predictably result in the claimed process. Further, Anguo teaches that the basic ionic liquids can improve the selectivity of the reaction products as compared to the organic base alone, while still retaining the benefits of Nagasawa, namely ease of separation of the catalyst and recyclability of the catalyst.
Further regarding claims 10-12 and 17, Anguo teaches that the optimized reaction conditions comprise reacting 1.0 mmol (0.21 g) of the chalcone of Tables 1 and 2 (analogous to the claimed 2-pentyl-2-cyclopentenone) with 2.0 mmol (0.13g) of the malononitrile (analogous to the claimed dimethylmalonate) in the presence of 0.2 mmol [DBU][Ac] at room temperature (about 20-25°C) from 5 to 600 min. See Tables and the representative experimental procedure in section 2.2 translation. The representative experimental procedure also recites that the chalcone and methylene compound are first combined with stirring, and that the ionic liquid is then added and the mixture is stirred until completion as indicated by TLC. See translation. Therefore the molar ratio of chalcone (2-pentyl-2-cyclopentenone) : methylene compound (dimethyl malonate) is 1 : 2, which falls within the range of claims 10 and 17. Further, the temperature of reaction of Anguo (r.t./about 20-25°C) falls within both ranges of claim 12. Anguo teaches that the reaction time can run from about 5 to 600 minutes or 10 hours, which overlaps with both ranges of claim 12. See Tables and MPEP 2144.05.
Anguo does not explicitly teach the order of reaction or an extended addition time of the 2-methyl-2-cyclopentenone dropwise into the mixture for 1 to 10 hours as required by claims 11 and 12. However, the selection of any order of mixing ingredients and/or performing process steps is prima facie obvious. See MPEP 2144.04(IV)(C). Further, it would be obvious to the skilled artisan to modify the order and speed of addition and/or lower the temperature of the reaction if the process selectivity was low and was producing too many by-products.
Further regarding claims 10 and 17, Anguo teaches that the mass of the ionic liquid is 0.04 g and the mass of malononitrile (analogous to dimethyl malonate) is 0.13 g. Therefore, the mass ratio is 0.04 to 0.13 or 1 : 3.25. This falls outside of the claimed range of 1: (10-50). However, routine optimization is standard practice in the art and if the ionic liquid catalyst is producing by-products and/or exotherms at the claimed concentration it would be prima facie obvious to dilute it with further with the reactant that is already in excess. Also see MPEP 2144.05.
Regarding claim 13, Anguo teaches that the reaction solution was extracted three times with ethyl acetate, combined, and subjected to phase separation, presumably with water. See translation of section 2.2. Anguo does not explicitly teach adding water to the reaction system for static stratification (phase separation) after the reaction is completed. However, Anguo does teach isolation by phase separation and pulls the product into the ethyl acetate layer which is extracted from the ionic liquid. Therefore, it would be obvious that the reverse could also be carried out. Namely, introducing an aqueous solvent that would dissolve the ionic liquid and leave the product as an organic layer and separating those two layers. Therefore, this is an obvious modification of the process of Anguo. Also see MPEP 2144.05.
Claim(s) 7-9 and 18 is/are rejected under 35 U.S.C. 103 as being unpatentable over Nagasawa (JP2013133330A, published on 7/8/2013, of record with an English translation in the IDS filed on 6/9/2026) in view of Anguo (“Michael Addition of Methylene Active Compounds to Chalcones with Novel Task-specific Ionic Liquids as Catalysts under Solvent-free Conditions”, Chinese Journal of Organic Chemistry, 2011, p. 1312, of record in the IDS filed on 10/30/2023 and English translation of record in the IDS filed on 6/9/2026), as applied to claims 2-6, 10-13, and 17 above, and further in view of Gimbert (“Michael additions catalyzed by phosphines. An overlooked synthetic method” Tetrahedron, 2005, p. 8598, of record in the IDS filed on 6/9/2026).
Neither Nagasawa nor Anguo teach the use of a monodentate phosphine ligand as required by claims 7-9 and 18.
Gimbert is directed toward Michael additions catalyzed by phosphines. See abstract. Gimbert teaches that monodentate phosphine ligands triphenylphosphine (claims 7 and 8) and tributylphosphine are excellent catalysts for Michael additions, which can promote reaction between many beta-dicarbonyl compounds and electron-poor olefins, including sterically demanding partners. See abstract and Tables 1 and 2. Gimbert teaches that the catalysts can be used in 10 mol% and that they can be used at room temperature like the basic ionic liquids of Anguo. See Table 2. Gimbert does not explicitly teach that the phosphine ligands can be paired with a basic ionic liquid catalyst.
It would have been prima facie obvious to combine the teachings of Nagasawa, Anguo, and Gimbert to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to include a monodentate phosphine ligand of Gimbert in the combined process of Nagasawa and Anguo because Gimbert teaches that said ligands are catalysts in their own right. Therefore, combining two known Michael addition catalysts which are known to work in the same temperature range will result in a predictable reaction for obtaining the claimed product. Also see MPEP 2144.06(I). Further regarding the molar ratio of phosphine: basic ionic liquid of claim 9, it would be obvious for the skilled artisan to employ routine optimization to arrive at the ratio for the system. One of the main benefits of the basic ionic liquids of Anguo is the ease of separation and recyclability of the catalyst, therefore the skilled artisan would be motivated to use only as much of the phosphine ligand as required to obtain the optimal results. Also see MPEP 2144.05. Further regarding claim 18, see the arguments with respect to claim 11 above, which also apply to this claim. Also see MPEP 2144.04(IV)(C).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMY C BONAPARTE whose telephone number is (571)272-7307. The examiner can normally be reached 11-7.
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/AMY C BONAPARTE/Primary Examiner, Art Unit 1692
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