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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination (RCE) under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 04 February 2026 has been entered.
Priority
This application is a 371 of PCT/IT2020/050245 which claims the benefit of IT 102019000018488 with an effective filing date of 10 October 2019 as reflected in the filing receipt mailed on 28 November 2023.
Status of the Claims
Claims 1-3, 5, 8, 10, 11, and 13-18 are pending.
Claims 13-18 are currently new.
Claims 1, 8, and 11 are currently amended.
Claims 6, 7, and 12 are currently cancelled.
Claim 4 was previously cancelled.
Response to Amendments
Applicant’s amendments filed 04 February 2026 are acknowledged.
Claim Rejections - 35 USC § 103
Applicant’s amendments to claims 1 and 11 adding the catalyst is Ru((R)-BINAP)Cl2 not taught by Birkhahn and cancellation of claims, are sufficient to overcome the rejection of claims 1-3, 5-7, 11, and 12 under 35 U.S.C. 103 as being unpatentable over US 5,693,850 A to Birkhahn et al. (hereinafter Birkhahn), in IDS, in view of US 2016/0272608 A1 to Rawat et al. (hereinafter Rawat). Due to the amendments to claims 1 and 11 adding the catalyst is Ru((R)-BINAP)Cl2 not taught by Birkhahn and cancellation of claims, the rejection is withdrawn and a new ground(s) of rejection is/are provided below.
Applicant’s amendment to claim 1 adding the catalyst is Ru((R)-BINAP)Cl2 not taught by Birkhahn and cancellation of claim 9, are sufficient to overcome the rejection of claims 8-10 under 35 U.S.C. 103 as being unpatentable over US 5,693,850 A to Birkhahn et al. (hereinafter Birkhahn), in IDS, in view of US 2016/0272608 A1 to Rawat et al. (hereinafter Rawat) and US 2015/0361073 A1 to Allan et al. (hereinafter Allan). Due to the amendment to claim 1 adding the catalyst is Ru((R)-BINAP)Cl2 not taught by Birkhahn and cancellation of claim 9, the rejection is withdrawn and a new ground(s) of rejection is/are provided below.
Response to Arguments
Applicant’s arguments filed 04 February 2026 have been fully considered but they are either not persuasive or moot.
Applicant argues that Birkhahn, Rawat, and Allan do not disclose the limitations as recited in amended claims 1 and 11. These arguments have been considered but are not persuasive for the reasons set forth in the new grounds of rejection below and the response to arguments below or are moot.
Applicant’s submission on 18 December 2025 of Lopez et al. (“Transesterification of Glycerol Triacetate with Methanol and Acid Base Catalysts”) is acknowledged.
In response to applicant’s arguments throughout the remarks submitted on 04 February 2026 that Birkhahn does not teach the Ru((R)-BINAP)Cl2 catalyst, Birkhahn does not teach the % stereoselectivity, that a person of ordinary skill in the art would not be motivated to modify the catalysts of Birkhahn with the catalyst of Rawat, and the opinions of Professor Forzato in the affidavit submitted on 17 July 2025, have all been considered but are moot because the new ground of rejection does not rely on Birkhahn or Rawat applied in the prior rejection of record for any teaching of a catalyst and stereoselectivity or matter associated with the catalyst or stereoselectivity specifically challenged in the argument.
Applicant’s arguments throughout the remarks submitted on 04 February 2026 with respect to Allan have been considered but are moot because the new ground of rejection does not rely on Allan applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
In response to applicant’s arguments C. on pages 12-14 of the remarks submitted on 04 February 2026 that the claimed method of Examples 3 and 4 “combination of catalyst, solvent, and hydrogen pressure provides the desired (R,R,R) product in high yield and high purity” illustrating superior results.
The fact that the inventor has recognized another advantage which would flow naturally from following the suggestion of the prior art cannot be the basis for patentability when the differences would otherwise be obvious, see Ex parte Obiaya, 227 USPQ 58, 60 (Bd. Pat. App. & Inter. 1985). In addition, “[t]o establish unexpected results over a claimed range, [appellants] should compare a sufficient number of tests both inside and outside the claimed range to show the criticality of the claimed range.” In re Hill, 284 F.2d 955, 128 USPQ 197 (CCPA 1960), see MPEP 716.02(d).
The instant specification Examples 3 and 4 are drawn to a hydrogenation process in ethanol using a Ru((R)-BINAP)Cl2 catalyst. Instant application claim 1 does not specify a solvent, including ethanol. Appellant’s argue superior results of synthesizing formula (Ia) are obtained through use of an ethanol solvent and a Ru((R)-BINAP)Cl2 catalyst as compared to a methanol solvent and differing acid/base catalysts. Throughout the remarks, applicant’s present a comparison applying the methanol solvent and acid/base catalysts of Lopez to synthesize compounds other than formula (Ia) and expert testimony from Professor Forzato regarding the effects associated with transesterification and stereoselectivity by the use of ethanol, methanol, acids, and bases in a hydrogenation reaction with no specific tests applying a differing solvent using a differing catalysts to synthesize formula (Ia); therefore, applicant’s have not provided a proper comparison to the closest prior art establishing test points inside and outside the use of the catalysts of Lopez with ethanol with or without an acid/base, the use of the Ru((R)-BINAP)Cl2 catalyst with methanol with or without an acid/base, and the use of differing hydrogen pressures to prepare instantly claimed formula (Ia) in order to support their argument of surprising and unexpected results, see MPEP 716.02(e).
The instant specification cannot be relied upon for any comparison tests/examples because the instant specification does not provide an example of the synthesis of formula (Ia) in a solvent other than ethanol, a catalysts other than Ru((R)-BINAP)Cl2, and a hydrogen pressure other than 35 bar; therefore, the instant specification does not provide a comparison to the closest prior art and tests inside and outside the ethanol solvent, Ru((R)-BINAP)Cl2 catalyst, and hydrogen pressure, i.e., tests in differing solvents using differing catalysts at differing hydrogen pressures to produce formula (Ia), in order to support the argument of surprising and unexpected results relating to the “combination of catalyst, solvent, and hydrogen pressure provid[ing] the desired (R,R,R) product in high yield and high purity”, see MPEP 716.02(e).
For the reasons indicated above, applicant’s above arguments are not persuasive.
In response to applicant’s argument on pages 16-17 of the remarks submitted on 04 February 2026 that the examiner’s conclusion of obviousness is based upon improper hindsight reasoning, it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant’s disclosure, such a reconstruction is proper, see In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971) and MPEP 2145 X.A. Only knowledge which was within the level of ordinary skill at the time the claimed invention was made has been applied to determine obviousness.
For the reasons indicated above, applicant’s above argument is not persuasive.
New Rejections Based on the RCE and Amendments to the Claims in the reply filed on 04 February 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.
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.
Claims 1-3, 5, 11, and 13-18 are newly rejected under 35 U.S.C. 103 as being unpatentable over Kitamura et al. (“Homogeneous Asymmetric Hydrogenation of Functionalized Ketones”, published 1988, Journal of the American Chemical Society, Vol. 110, Pgs. 629-631 and S1-S14, hereinafter Kitamura) in view of Birkhahn et al. (US5693850, published 02 December 1997, hereinafter Birkhahn).
Kitamura is in the known prior art of the hydrogenation of functionalized ketones, such as β-keto carboxylic esters, over BINAP-Ru catalysts, see Pg. 629, Col. 2, Last Para. – Pg. 630, Col. 2; Table 1.
Regarding the limitations of instant application claims 1-3, 11, 13, 14, 16, and 17, Kitamura teaches the hydrogenation of various ketones, such as 1 is methylolacetone
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and
2 is 2,4 pentanedione
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,
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over the catalysts RuCl2[(R)-binap] in “degassed anhydrous ethanol” at a hydrogen pressure of 40-100 atm or 40.5 to 101.3 bar to yield “(2R,4R)-pentanediol in 100% ee”, see Pg. 629, Col. 2, Last Para. – Pg. 630, Col. 2; Table 1; Pgs. S1, General-S3, Figure 1, where the “structures of the initially created hydroxy ketones including chirality of the stereogenic center (substrate control). Hydrogenation of acetylacetone (6) catalyzed by RuCl2[(R)-binap] produced first the (R)-hydroxy ketone 11 (98.5% ee at 10% conversion), as expected from eq 2, and then resulted in a 99:1 mixture of (R,R)-diol 8 in 100% ee and meso-diol 10.”, see Pg. 631, Col. 1, meeting:
The method of preparing a compound, having all stereogenic centers with a configuration (R) by the hydrogenation reaction of a compound in the presence of RuCl2[(R)-binap] and within the hydrogen pressure range in instant application claim 1 and instant application claim 11; and,
The solvent consists of ethanol in instant application claim 2, in instant application claim 3, in instant application claim 13, in instant application claim 14, in instant application claim 16, and in instant application claim 17.
Regarding the limitations of instant application claim 5, Kitamura teaches the reaction is carried out at a temperature of 20-32 °C, see Pg. 629, Col. 2, Last Para. – Pg. 630, Col. 2; Table 1; Pgs. S1, General-S3, Figure 1. See current specification, Pg. 8, Lns. 11-13 stating the temperature is about 25° C to the reflux temperature of the solvent, and Example 3 with an ethanol solvent and a reaction temperature of 40-45° C., meeting within the temperature range in instant application claim 5.
Regarding the limitations of instant application claims 15 and 18, Kitamura teaches the HPLC analysis of “asymmetrically synthesized (2R,4R)-pentanediol” with a purity of about 100%, see Pg. S3, Figure 1 right as compared to Figure 1 left; Pg. 629, Col. 2, Last Para. – Pg. 630, Col. 2; Table 1; Pgs. S1, General-S3, Figure 1, meeting within the HPLC purity in instant application claim 15 and in instant application claim 18.
Kitamura does not teach:
The instant application claims 1 and 11 limitations of formula (Ia) and formula (IV).
Birkhahn is in the known prior art field of “the reaction of glycerol or a protected glycerol and an acetoacetate ester or acetoacetate precursor, yielding an acetoacetyl glycerol which is thereafter reduced, providing a glycerol ester of 3-hydroxybutyric acid”, see Abstract, where 3-hydroxybutyrate and acetoacetate are “so-called ketone bodies”, see Col. 1, Lns. 53-60, and the reaction is the reduction of 1,2,3-propanetriyl acetoacetate under hydrogen pressure in the presence of a catalyst to produce tris(D-β-hydroxybutyryl) glycerol, see Col. 3, Ln. 54-Col. 4, Ln. 7; Col. 6, Ln. 55-Col. 7, Ln. 28, Scheme 2.
Regarding the limitations of instant application claims 1 and 11, Birkhahn teaches a method of preparing a compound of formula (I)
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as a single enantiomer, where 1,2,3-propanetriyl acetoacetate
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aka instantly claimed formula (IV) is reacted under hydrogen pressure in the presence of a catalyst to produce
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compound 2, see Col. 6, Ln. 55-Col. 7, Ln. 28, Scheme 2; Col. 13, Ln. 30-Col. 15, Ln. 33, Example 5 and Example 6, where compound 2, tris(β-hydroxybutyryl) glycerol, is preferably optically pure containing a majority of the composition in the form that is more readily metabolized by the body, such that the tris(β-hydroxybutyryl) glycerol is the isomer tris(D-β-hydroxybutyryl) glycerol in a concentration of at least 50%, i.e., instantly claimed formula (Ia) R, R, R configuration, see Col. 3, Ln. 65-Col. 4, Ln. 7; Col. 5, Lns. 5-7, meeting formula (Ia) and IV in instant application claim 1 and in instant application claim 11.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified the functionalized ketone substrate of Kitamura to choose the functionalized ketone body substrate as taught by Birkhahn with a reasonable predictability of success for the purpose of efficiently producing β-keto carboxylic esters that are optically pure “containing a majority of the composition in the form that is more readily metabolized by the body”, see Birkhahn, Col. 3, Ln. 65-Col. 4, Ln. 7; Col. 5, Lns. 5-7.
The rationale to support a conclusion that the claim would have been obvious is that a particular known technique was recognized as part of the ordinary capabilities of one skilled in the art. One of ordinary skill in the art would have been capable of modifying the functionalized ketone substrate of Kitamura by choosing the known functionalized ketone body substrate as taught by Birkhahn with a reasonable predictability of success for the purpose of efficiently producing β-keto carboxylic esters that are optically pure “containing a majority of the composition in the form that is more readily metabolized by the body”, see Birkhahn, Col. 3, Ln. 65-Col. 4, Ln. 7; Col. 5, Lns. 5-7; and, MPEP 2143 I. B-D.
“Where applicant claims a composition in terms of a function, property or characteristic and the composition of the prior art is the same as that of the claim but the function is not explicitly disclosed by the reference, the examiner may make a rejection under both 35 U.S.C. 102 and 103.”, see MPEP 2112 III. In this case, the chiral product of Kitamura is synthesized in a solvent consisting of ethanol in contact with a RuCl2[(R)-binap] catalyst. A person of ordinary skill in the art would naturally be lead to the reasonable expectation that the Kitamura synthesis procedures starting with the instantly claimed formula (IV) substrate would lead to the instantly claimed formula (Ia) with all three stereogenic centers in the R, R, R configuration.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Kitamura and Birkhahn both teach hydrogenation reactions involving β-keto carboxylic esters, a person of ordinary skill in the art has good reason to modify Kitamura by relying upon Birkhahn before the effective filing date of the claimed invention for knowledge generally available within the hydrogenation of β-keto carboxylic esters art, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing β-keto carboxylic esters that are optically pure “containing a majority of the composition in the form that is more readily metabolized by the body”, see Birkhahn, Col. 3, Ln. 65-Col. 4, Ln. 7; Col. 5, Lns. 5-7; and, MPEP 2141 and 2143 I. B-D.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §
103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its
actual application is beyond his or her skill”, see MPEP 2141.
Selection of a known material, such as a β-keto carboxylic ester to hydrogenate, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945), see MPEP 2144.07.
In addition, “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions, or degree,” such as all three stereogenic centers in the R, R, R configuration, “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. In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929)”, see MPEP 2144.05.
Claims 8 and 10 are newly rejected under 35 U.S.C. 103 as being unpatentable over Kitamura et al. (“Homogeneous Asymmetric Hydrogenation of Functionalized Ketones”, published 1988, Journal of the American Chemical Society, Vol. 110, Pgs. 629-631 and S1-S14, hereinafter Kitamura) in view of Birkhahn et al. (US5693850, published 02 December 1997, hereinafter Birkhahn), as applied to claims 1-3, 5, 11, and 13-18 in the 35 USC 103 rejection above, in further view of MIT (“8.4 – Extraction and Washing Guide”, published January 2012, 5.301 Chemistry Laboratory Techniques, Pgs. 61-63).
Regarding the limitations of instant application claim 10, Kitamura teaches “[t]he solvent of the bright yellowish orange solution was removed under reduced pressure. The residue was distilled to give (2R,4R)-pentanediol in 100% ee”, see Pg. S2, Lns. 3-6, meeting purification without chromatography in instant application claim 10.
Kitamura and Birkhahn do not teach the limitations of instant application claim 8.
Kitamura teaches a product purification by adding ether and water to a crude reaction mixture, then adding ether and washing with HCl, NaOH, water, and then brine followed by drying over anhydrous sodium sulfate, see Pg. S2.
MIT is in the known prior art field of product purification by “standard extraction and washing protocols that can be applied to virtually any crude reaction mixture”, see Pg. 61, Overview.
Regarding the limitations of instant application claim 8, MIT teaches in order to purify a product from an aqueous crude reaction mixture, the reaction mixture is first contacted with an appropriate organic solvent, such as ether or ethyl acetate, see Pgs. 61-62, Overview-4), meeting step a. one or more washings of the aqueous solution with organic solvent S1 ether or ethyl acetate and 0% NaCl in instant application claim 8;
After the washings, saturated NaCl is added to the solution to ““dry” the organic layer by extracting water that may have dissolved in the organic phase”, see Pg. 62, 6), meeting step b. increasing the concentration of NaCl within the range of higher than 5% w/w in instant application claim 8; and,
The solution is concentrated and dissolved in another higher boiling point solvent and dichloromethane repeatedly to isolate the product, see Pgs. 62-63, 10)-13), meeting steps c. and d. and the organic solvent S2 dichloromethane in instant application claim 8.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified the purification and washing techniques of Kitamura to choose the purification and washing with NaCl as taught by MIT with a reasonable predictability of success for the purpose of efficiently purifying the crude mixture through use of NaCl to “disrupt any emulsions” and to ““dry” the organic layer by extracting water that may have dissolved in the organic phase”, see MIT, Pg. 61, Overview; Pg. 62, 6).
The rationale to support a conclusion that the claim would have been obvious is that a particular known technique was recognized as part of the ordinary capabilities of one skilled in the art. One of ordinary skill in the art would have been capable of modifying the purification and washing techniques of Kitamura by choosing the known purification and washing techniques as taught by MIT with a reasonable predictability of success for the purpose of efficiently purifying the crude mixture through use of NaCl to “disrupt any emulsions” and to ““dry” the organic layer by extracting water that may have dissolved in the organic phase”, see MIT, Pg. 61, Overview; Pg. 62, 6); and, MPEP 2143 I. B-D.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Kitamura and MIT both teach purification and washing techniques of a crude mixture, a person of ordinary skill in the art has good reason to modify Kitamura by relying upon MIT before the effective filing date of the claimed invention for knowledge generally available within the purification and washing techniques art, see MPEP 2143 B & G and 2141, for the benefit of efficiently purifying the crude mixture through use of NaCl to “disrupt any emulsions” and to ““dry” the organic layer by extracting water that may have dissolved in the organic phase”, see MIT, Pg. 61, Overview; Pg. 62, 6); and, MPEP 2143 I. B-D.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §
103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its
actual application is beyond his or her skill”, see MPEP 2141.
In addition, “[t]he 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”, such as the concentration of the NaCl, “is the optimum combination of percentages.” In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969), see MPEP 2144.05.
Selection of a known material, such as a NaCl salting out, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945), see MPEP 2144.07.
Conclusion
No claims are allowed.
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/YO/Examiner, Art Unit 1692
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699
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