DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after 16 March 2013, is being examined under the first inventor to file provisions of the AIA .
Response to Amendments
Status of Claims
The amendment, filed on 23 October 2025, is acknowledged.
Claims 57 has been amended.
Claims 58-59 have been cancelled.
New claims 83-84 have been added.
Claims 60-61 were previously withdrawn from consideration in the non-final Office Action, mailed on 22 July 2025, as being drawn to a nonelected species.
Claims 65-82 were previously withdrawn from consideration in the non-final Office Action, mailed on 22 July 2025, as being drawn to a nonelected invention.
Claims 57, 62-64, and 83-84 are pending and under consideration in the instant Office Action, to the extent of the following previously elected species:
the oxobutanol of the general formula (I) is ethyl-3-hydroxybutanoate (3-BHB-EE);
the polymeric carboxylic acid is polytartaric acid;
the reaction is performed in the absence of any catalyst; and
the reaction product is a mixture of metatartic acid mono(4-ethoxy-4-oxo-butan-2-ol) ester, metatartic acid di(4-ethoxy-4-oxo-butan-2-ol) ester, and metatartic acid poly(4-ethoxy-4-oxo-butan-2-ol) ester.
Rejections Withdrawn
Rejections pursuant to 35 U.S.C. § 112
The rejection of claim 59 under 35 U.S.C. § 112 is withdrawn in view of Applicant’s cancellation of the claim.
Rejections pursuant to 35 U.S.C. § 103
The rejection of claims 57 and 62-64 under 35 U.S.C. § 103 is withdrawn in view of Applicant’s amendment to claim 57 and in favor of the new grounds of rejection below. The rejections of claims 58-59 under 35 U.S.C. § 103 are withdrawn in view of Applicant’s cancellation of the claims.
New Grounds of Rejection
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 57, 62-64, and 83-84 are rejected under 35 U.S.C. 103 as being unpatentable over Clarke et al. (WIPO International Patent Publication No. WO 2010/021766 A1, published on 25 February 2010, hereafter referred to as Clarke) in view of Llosa et al. (U.S. Patent Application Publication No. US 2019/0177673 A1, published on 13 June 2019, hereafter referred to as Llosa), Krell et al. (Eur. J. Org. Chem. 2000, 2000 (7), 1207., hereafter referred to as Krell), Nan et al. (J. Cleaner Prod. 2019, 210, 687., hereafter referred to as Nan), and Afanasenko et al. (Chem. Commun. 2019, 2 (127), 1., hereafter referred to as Afanasenko).
Clarke teaches a method of synthesizing an oxobutanol ester that is a precursor to the biologically important ketone 3L-hydroxybutyrate (otherwise known as b-hydroxybutyrate or BHB) used for managing weight, promoting or improving cognitive function, or to treat, prevent, or reduce neuro degeneration (Abstract). Clarke teaches the importance of ketones to the human body and the ability of human metabolism to produce the biologically vital ketone BHB from its derivatives, including esters (pg. 2, lines 11-33). However, direct administration of BHB is taught to be not only impractical but potentially dangerous due to induced acidosis following rapid absorption in the gastrointestinal tract (pg. 2, lines 19-23).
To administer BHB sources that avoid the potential risks above, Clarke teaches the oxobutanol ester 3-hydroxybutyl 3-hydroxybutyrate, which has advantages including a palatable, lower bitterness flavor and decomposition products of BHB and 1,3-butanediol, which itself is converted into BHB in the liver (pg. 6, lines 11-22). The oxobutanol ester 3-hydroxybutyl 3-hydroxybutyrate is taught to be synthesized from 3-BHB-EE and 1,3-butanediol, present in a 2:1 ratio by mass and equivalent to a ~1.75:1 molar ratio, in the presence of solid-supported Candida antarctica lipase B, an enzyme that catalyzes the reaction (pg. 13, Example 1). The reaction takes place at a pressure of 8-10 torr, equivalent to ~0.011-0.013 bar, at a temperature of 40-45 °C (Example 1).
Clarke does not teach the oxobutanol ester to be synthesized from 3-BHB-EE and poly(tartaric acid), the reaction to be performed in the absence of solvent or catalyst, to be performed in the presence of an inert gas, nor the functionalization of carboxyl and hydroxyl side groups. These deficiencies are offset by the teachings of Llosa, Krell, Nan, and Afanasenko.
Llosa teaches a food product comprising 3-hydroxybutyrate (otherwise known as b-hydroxybutyrate or BHB) and/or derivatives of the oxobutanol, for the purpose of initiating or maintaining ketosis in a user (Abstract and para. [0001]). Ketosis is taught to be a fat-based metabolic state in which a human body consumes fats, rather than the normal source of carbohydrates, to produce glucose to support bodily functions (para. [0004]). During ketosis, the body is taught to produce ketones and fatty acids from fats, and the former is taught to be capable of passing the blood-brain barrier to provide energy to the brain, in addition to treating conditions such as epilepsy, Alzheimer’s disease, and concussions (para. [0005]). Further, ketones are taught to “improve muscle performance, such as in endurance athletes…[and] can improve endurance performance by as much as two percent” (para. [0006]).
Among the derivatives of the invention of Llosa which can be ingested by users are ethyl 3-hydroxybutyrate (3-BHB-EE) and the ester of BHB and 1,3-butanediol (para. [0007]). 3-BHB-EE and 1,3-butanediol are taught to be safe for human consumption and, following consumption, are taught to eventually be converted to a ketone that may be used in brain metabolism (para. [0021]). In addition, 3-BHB-EE is taught to be a hypoglycemic agent, which can reduce the levels of blood glucose in users (para. [0021]).
Krell teaches a method of preparing free and specifically protected polymers of the carboxylic acid malic acid, as well as their importance to biological processes in eukaryotes (Abstract and Introduction, pg. 1207, left column, para. 1). Polyhydroxyalkanoates (PHAs) are taught to be an important class of biopolymers to organisms, the most prominent member of which is poly(BHB) (PHB) (Introduction, pg. 1207, left column, para. 1). PHB and related PHAs are attractive research subjects due to their biocompatibility and biodegradability, but have relatively recently also been discovered to be present in many eukaryotic organisms transporting calcium ions across membranes, leading to the development of synthetic oligomers of BHB and higher alkanoic acids (Introduction, pg. 1207, left column, para. 1).
Poly(malic acid) (PMA), a naturally synthesized polymer that is structurally related to PHB, was found to have applications as a drug carrier and part of a prodrug compound due to its non-toxicity (Introduction, pg. 1207, left column, para. 2). However, in a buffered aqueous solution at pH 7.5 and room temperature, roughly equivalent to the in vitro environment, PMA is taught to spontaneously hydrolyze (Introduction, pg. 1207, left column, para. 2). Stability is added to PMA in biological environments by esterifying the carboxyl group side chains (Introduction, pg. 1207, left column, para. 2). One example of an esterified PMA compound is complex 22, a tetramer of malic acid that is protected on the C-terminal with an alkyl ester group and was found to be stable in aqueous solution and in the presence of the hydrolase enzyme P. polycephalum (Scheme 6, pg. 1210, right column, para. 2-3, and pg. 1211, right column, Enzymatic Degradation Studies).
Nan teaches a coating produced from tartaric acid that is clean to synthesize, biodegradable, and capable of functionalization (Abstract). Tartaric acids contain two carboxyl groups and two hydroxyl groups, leading to polycondensation products that contain “unchanged pendant carboxyl and hydroxyl groups providing hydrophilicity and reactivity for further functionalization” pg. 688, left column, para. 1). Another attractive characteristic of poly(tartaric acid) is that it can be synthesized “in a remarkably clean synthesis by simple heating without the necessity of using solvents or catalysts”, producing only water and trace CO2 as a byproduct (Conclusions, pg. 688, right column, para. 1, and pg. 689, 3.1.1. Synthesis of poly(tartaric acid)). To demonstrate the ability of poly(tartaric acid) to support side chain functionalization, Nan teaches linkage of glucosamine, a medically relevant derivative of glucose, to poly(tartaric acid) via a carboxyl group (pg. 693, right column, final para. and Scheme 6).
Afanasenko teaches methods of synthesizing b-amino acid esters via amination of b-hydroxyl acid esters (Abstract). b-amino acid esters are taught to be desirable synthetic products due to their presence in a wide variety of biologically active compounds and ability to be used as precursors to b-peptides and b-lactam antibiotics (pg. 2, para. 1). 3-hydroxypropionic acid, a C3 b-hydroxyl acid analogue of BHB, is taught to be one of the most desirable chemicals for its synthetic use, but previous reports on direct and selective amination of the chemical have not demonstrated success (pg. 2, right column, para. 2 - pg. 3, left column, para. 1). Recent focus has been on the ethyl ester of BHB, ethyl 3-hydroxybutanoate (3-BHB-EE, 1a in Table 1), and methods of production that are industrially relevant, scalable, and use feedstock that is renewable, readily available, and desirable to eliminate (pg. 3, left column, para. 1). Afanasenko teaches a one-step catalytic amination process of producing b-amino acid esters via amination of ethyl BHB that achieves the above aims, which requires the reaction to proceed at 100-120 °C and under an argon atmosphere (Fig. 4, Table 1, pg. 8, General procedure for the preparation of b-amino acid esters).
It would have been prima facie obvious to one of ordinary skill in the art to modify the method taught by Clarke with the teachings of Llosa, Krell, Nan, and Afanasenko because combining prior art elements according to known methods yields predictable results. An artisan would be motivated to use ethyl 3-hydroxybutyrate (3-BHB-EE) as the oxobutanol in the esterification reaction taught by Clarke because Llosa teaches 3-BHB-EE to be safe for human consumption, a precursor to a ketone that may be used in brain metabolism, and a hypoglycemic agent, which can reduce the levels of blood glucose in users. In view of the teachings of Krell, the person of ordinary skill would be motivated to use polymeric carboxylic acids conjugated to hydroxyalkanoates because the reference teaches their utility in transporting calcium ions across membranes, carrying drugs, and delivering drugs as part of a prodrug, in addition to being non-toxic, biodegradable, and biocompatible. As taught by Krell, polymeric carboxylic acids can be unstable in biological conditions, but stability can be achieved by esterifying the carboxyl group side chains, such as esterification with an alkyl ester group. Esterification with the oxobutanol 3-BHB-EE would be desirable to an artisan because the benefits of 3-BHB-EE would be combined with those of the polymeric carboxylic acid while advantageously adding stability via esterification of side groups.
Further, the ordinary artisan would be motivated to use poly(tartaric acid) as the polymeric carboxylic acid in view of the teachings of Nan because the reference teaches poly(tartaric acid) to be biodegradable, easily capable of functionalization, and to be synthesized in a remarkably clean synthesis by simple heating without solvents or catalysts, producing only water and trace CO2 as a byproduct. It would be desirable to an ordinary person in the art to perform the esterification reaction in the absence of solvent and catalyst because Nan teaches poly(tartaric acid) to be synthesized in this manner as well as the benefits of such a synthetic method, which would also be beneficial in the esterification reaction with 3-BHB-EE.
Finally, a person of ordinary skill would be motivated to perform the esterification reaction rendered obvious above under an argon atmosphere in view of the teachings of Afanasenko because the reference teaches that reactions of 3-BHB-EE under the inert gas proceed as desired and the aforementioned references do not state the atmospheric conditions of the reactions – information that a person of ordinary skill would require to perform an esterification reaction. As a result, there is a reasonable expectation of success in arriving at the method of instant claims 57, 62-64, and 83-84 in view of the teachings of Clarke, Llosa, Krell, Nan, and Afanasenko.
Response to Arguments
The Applicant’s arguments, filed on 23 October 2025, have been fully considered but are not persuasive.
In response to Applicant's arguments against the references individually from the final para. of pg. 15 to para. 1 of pg. 20 of the remarks, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).
In response to Applicant's argument in para. 2 of pg. 16 of the remarks that the Clarke reference is “fully unrelated” to the instant applicant and “cannot provide any support for the current rejections under 35 U.S.C. § 103”, it has been held that a prior art reference must either be in the field of the inventor’s endeavor or, if not, then be reasonably pertinent to the particular problem with which the inventor was concerned, in order to be relied upon as a basis for rejection of the claimed invention. See In re Oetiker, 977 F.2d 1443, 24 USPQ2d 1443 (Fed. Cir. 1992). In this case, the Examiner disagrees and directs the Applicant to the discussion of the Clarke reference above – in brief, the Clarke reference is related to the instant application because it teaches the use of oxobutanol esters, which contain the elected 3-BHB-EE, to deliver BHB to users via human metabolism as a method of treating medical conditions. As evidenced by the Brief Summary of the Invention in the instant specification (pg. 6), the instant application also has the goal of delivering BHB precursors to users, and therefore the Clarke reference is related to the instant application.
In para. 3 of pg. 17, Applicant states that “[b]ecause the preparation of the ethyl 3-hydroxybutyrate esterified with 3-hydroxybutiric acid is not described by Llosa, the specific measures of the method according to the invention…are also not disclosed either” and “all of the reaction parameters disclosed are fully different from Applicant’s claimed method and Llosa cannot fill in any of the deficiencies of Clarke”. This argument is not found to be persuasive because the teachings of all limitations in one embodiment are necessary for an anticipation rejection under 35 U.S.C. § 102, not for an obviousness rejection under 35 U.S.C. § 103 as was made in the non-final Office Action mailed on 22 July 2025, and as made above. The Llosa reference is considered relevant to both the Clarke reference and the instant application because Llosa teaches the benefit of users ingesting BHB precursors including 3-BHB-EE and the ester of BHB and 1,3-butanediol (vide supra).
In the para. that spans the end of pg. 17 and top of pg. 18, Applicant argues that the Krell reference does not “help fill in any of the noted deficiencies of Clarke and Krell” (bold added for emphasis), the latter being interpreted as the aforementioned Llosa reference which was erroneously labelled “Krell”. Applicant asserts this is because Krell teaches the use of solvents in reactions and different reaction parameters, and that, “[t]o the extent that so many of Krell’s required parameters are different, to some extent Krell teaches away from Applicant’s claimed method”. This argument is not found to be persuasive because the “mere disclosure of more than one alternative does not constitute a teaching away from any of these alternatives because such disclosure does not criticize, discredit, or otherwise discourage the solution claimed…." In re Fulton, 391 F.3d 1195, 1201, 73 USPQ2d 1141, 1146 (Fed. Cir. 2004). See MPEP § 2123 and 2141.02.VI. The Krell reference teaches methods of synthesizing esterified polymeric carboxylic acids, the utility of polymeric BHB, and medical applications including drug delivery or use in a prodrug (vide supra). As a result, the Krell reference is relevant to the Clarke and Llosa references, as well as the instant application, and is suitable for use in an obviousness rejection under 35 U.S.C. § 103.
In the final para. of pg. 19 and para. 1 of pg. 20, Applicant argues that “[n]o aspect of Nan’s teaching is related to Applicant’s claimed method”. This is not found to be persuasive because, as the Applicant also wrote in para. 1 of pg. 20, Nan teaches a “reaction without a catalyst and a solvent involves the preparation of a potential starting material for Applicant’s method” and “[t]he noted parameters are related to the preparation of a starting material that could be used in Applicant’s claimed method…and no more”. Because the teachings of Nan are related to the instant application, they are suitable for use in an obviousness rejection under 35 U.S.C. § 103.
Finally, in the section spanning the final para. of pg. 20 to para. 1 of pg. 22, Applicant argues that the combination of the Clarke, Llosa, Krell, and Nan references “fails to show every element of the claimed invention and a prima facie case for obviousness has not been made”. However, no specific argument has been presented against the rationale for combining the references, but instead an argument specifically against the teachings of Nan are presented (see final para. of pg. 20). Further, the experimental parameters that the Applicant claims are not taught, namely the absence of a solvent and catalyst and the presence of an inert gas, either were taught (e.g., Nan teaches the benefit of the absence of catalysts) or were rejected in further view of the Afanasenko reference, which has been included in the new grounds of rejection above. As a result, these arguments are not found to be persuasive.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 57, 62-64, and 83-84 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 48, 51, and 54-55 of copending Application No. 18/004,748 in view of Clarke (WIPO International Patent Publication No. WO 2010/021766 A1, published on 25 February 2010), Nan (J. Cleaner Prod. 2019, 210, 687.), and Afanasenko (Chem. Commun. 2019, 2 (127), 1.).
This is a provisional nonstatutory double patenting rejection.
Copending Application No. 18/004,748 recites in claim 48 a method for producing carboxylic acid esters of an oxobutanol, wherein the carboxylic acid may be tartaric acid and the oxobutanol is of the general formula (I), CH3-CH(OH)-CH2-C(O)OR1, wherein R1 may be a C1-5 alkyl group and therefore includes ethyl-3-hydroxybutanoate (3-BHB-EE). The esterification reaction that produces the carboxylic acid ester of an oxobutanol is recited to proceed in the absence of any solvent or catalyst and with a ratio of oxobutanol: carboxylic acid of 1:1 to 10:1 (claims 48 and 51). Copending Application ‘748 further recites that the hydroxyl and carboxyl groups present in the reaction product are at least partially functionalized, said functionalization including esterification (claims 54-55).
Copending Application No. 18/004,748 does not recite the method to include poly(tartaric acid), the temperature or pressure of the reaction method, nor the reaction to proceed in an inert gas environment. These deficiencies are offset by the teachings of Clarke, Nan, and Afanasenko.
Clarke, Nan, and Afanasenko have been described above.
It would have been prima facie obvious to a person of ordinary skill in the art to modify the method recited in copending Application ‘748 in view of the teachings of Clarke, Nan, and Afanasenko because applying known techniques to a known method ready for improvement yields predictable results. An artisan would be motivated to use the temperature and pressure conditions taught by Clarke in the reaction method recited in ‘748 because the copending application does not recite these conditions, which are necessary to know to perform reactions. The reaction conditions taught by Clarke are used in an esterification reaction with the oxobutanol 3-BHB-EE, which the ordinary artisan would recognize as being applicable to the reaction recited in claim 48 of Application ‘748.
An artisan would further be motivated to use poly(tartaric acid) in the esterification reaction recited by Application ‘748 because Nan teaches the polymeric carboxylic acid to be synthesized by simple heating in the absence of solvent or catalyst, which are the conditions recited in claims 48 and 51 of ‘748, and poly(tartaric acid) to have pendant carboxyl and hydroxyl groups that enable further functionalization, beyond what is available with a single tartaric acid molecule. Finally, an artisan would be motivated to perform the esterification reaction of ‘748 under an argon inert gas atmosphere in view of the teachings of Afanasenko because the reference teaches that reactions of 3-BHB-EE under the inert gas proceed as desired and the above references do not state the atmospheric conditions of the reactions – information that a person of ordinary skill would require to perform an esterification reaction. As a result, there is reasonable expectation of success in arriving at the method of instant claims 57, 62-64, and 83-84 in view of claims 48, 51, and 54-55 of copending Application No. 18/004,748 and further in view of the teachings of Clarke, Nan, and Afanasenko.
Claims 57, 62-64, and 83-84 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 82, 84, and 90-91 of copending Application No. 18/004,753 in view of Nan (J. Cleaner Prod. 2019, 210, 687.), Afanasenko (Chem. Commun. 2019, 2 (127), 1.), and Clarke (WIPO International Patent Publication No. WO 2010/021766 A1, published on 25 February 2010).
This is a provisional nonstatutory double patenting rejection.
Copending Application No. 18/004,753 recites a method for producing esters of one or more oxobutanols, polycarboxylic acids, and polyglycerols, wherein the oxobutanols are of the general formula (I), CH3-CH(OH)-CH2-C(O)OR1, wherein R1 may be a C1-5 alkyl group and therefore includes ethyl-3-hydroxybutanoate (3-BHB-EE), and the polycarboxylic acids may be tartaric acid (claims 82 and 84). Additionally, the method is “carried out in the absence of any solvent” (claim 82). Application ‘753 further recites the produced ester to have side hydroxyl and carboxyl groups that are at least partially functionalized, optionally being esterified (claims 90-91).
Copending Application No. 18/004,753 does not recite the reaction conditions to be without any catalyst, under an inert atmosphere, or at a certain temperature or pressure nor the ratio of the oxobutanols to polycarboxylic acids. These deficiencies are offset by the teachings of Nan, Afanasenko, and Clarke.
Nan, Afanasenko, and Clarke have been described above.
It would have been prima facie obvious to a person of ordinary skill in the art to modify the method recited in copending Application ‘753 in view of the teachings of Nan, Afanasenko, and Clarke because applying known techniques to a known method ready for improvement yields predictable results. An artisan would be motivated to perform the reaction recited in ‘753 in the absence of a catalyst because Nan teaches that poly(tartaric acid), one of the polycarboxylic acids recited in claim 84 of Application ‘753, may be synthesized without a catalyst and the benefits of doing so, such as improved environmental cleanliness, which would be desirable to also have in the esterification reaction.
An artisan would further be motivated to perform the esterification reaction of ‘753 under an argon inert gas atmosphere in view of the teachings of Afanasenko because the reference teaches that reactions of 3-BHB-EE under the inert gas proceed as desired and the above references do not state the atmospheric conditions of the reactions – information that a person of ordinary skill would require to perform an esterification reaction. Finally, a person of ordinary skill would be motivated to use the molar ratios and the temperature and pressure conditions taught by Clarke in the reaction method recited in ‘753 because the copending application does not recite these reaction conditions, which are necessary to successfully perform the esterification reactions. The reaction conditions taught by Clarke are used in an esterification reaction with the oxobutanol 3-BHB-EE, which the ordinary artisan would recognize as being applicable to the reaction recited in claim 82 of Application ‘753. While the reaction of claim 82 of copending Application ‘753 also includes one or more polyglycerols in the reaction mixture, removal of the component would result in the same reaction mixture as instant claim 57 and would be obvious to an artisan, particularly in view of the esterification reaction taught by Clarke. As a result, there is reasonable expectation of success in arriving at the method of instant claims 57, 62-64, and 83-84 in view of claims 82, 84, and 90-91 of copending Application No. 18/004,753 and further in view of the teachings of Nan, Afanasenko, and Clarke.
Claims 57, 62-64, and 83-84 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 78, 82, and 84-85 of copending Application No. 18/004,754 in view of Nan (J. Cleaner Prod. 2019, 210, 687.), Afanasenko (Chem. Commun. 2019, 2 (127), 1.), and Clarke (WIPO International Patent Publication No. WO 2010/021766 A1, published on 25 February 2010).
This is a provisional nonstatutory double patenting rejection.
Copending Application No. 18/004,754 recites a method of producing esters of one or more oxobutanols, polycarboxylic acids, and polyglycerols, wherein the oxobutanols are of the general formula (I), CH3-CH(OH)-CH2-C(O)OR1, wherein R1 may be a C1-5 alkyl group and therefore includes ethyl-3-hydroxybutanoate (3-BHB-EE), and the polycarboxylic acids may be tartaric acid (claims 78 and 82). Additionally, the method is “carried out in the absence of any solvent” (claim 78). Application ‘754 further recites the produced ester to have side hydroxyl and carboxyl groups that are at least partially functionalized, optionally being esterified (claims 84-85).
Copending Application No. 18/004,754 does not recite the reaction conditions to be without any catalyst, under an inert atmosphere, or at a certain temperature or pressure nor the ratio of the oxobutanols to polycarboxylic acids. These deficiencies are offset by the teachings of Nan, Afanasenko, and Clarke.
Nan, Afanasenko, and Clarke have been described above.
It would have been prima facie obvious to a person of ordinary skill in the art to modify the method recited in copending Application ‘754 in view of the teachings of Nan, Afanasenko, and Clarke because applying known techniques to a known method ready for improvement yields predictable results. An artisan would be motivated to perform the reaction recited in ‘754 in the absence of a catalyst because Nan teaches that poly(tartaric acid), one of the polycarboxylic acids recited in claim 82 of Application ‘754, may be synthesized without a catalyst and the benefits of doing so, such as improved environmental cleanliness, which would be desirable to also have in the esterification reaction.
An artisan would further be motivated to perform the esterification reaction of ‘754 under an argon inert gas atmosphere in view of the teachings of Afanasenko because the reference teaches that reactions of 3-BHB-EE under the inert gas proceed as desired and the above references do not state the atmospheric conditions of the reactions – information that a person of ordinary skill would require to perform an esterification reaction. Finally, a person of ordinary skill would be motivated to use the molar ratios and the temperature and pressure conditions taught by Clarke in the reaction method recited in ‘754 because the copending application does not recite these reaction conditions, which are necessary to successfully perform the esterification reactions. The reaction conditions taught by Clarke are used in an esterification reaction with the oxobutanol 3-BHB-EE, which the ordinary artisan would recognize as being applicable to the reaction recited in claim 78 of Application ‘754. While the reaction of claim 78 of copending Application ‘754 also includes one or more polyglycerols in the reaction mixture, removal of the component would result in the same reaction mixture as instant claim 57 and would be obvious to an artisan, particularly in view of the esterification reaction taught by Clarke. As a result, there is reasonable expectation of success in arriving at the method of instant claims 57, 62-64, and 83-84 in view of claims 78, 82, and 84-85 of copending Application No. 18/004,754 and further in view of the teachings of Nan, Afanasenko, and Clarke.
Response to Amendments
A complete response to a nonstatutory double patenting (NSDP) rejection is either a reply by the Applicant showing that the claims subject to the restriction are patentably distinct from the reference claims, or the filing of a terminal disclaimer in accordance with 37 CFR 1.321 in the pending application(s) with a reply to the Office action (see MPEP § 1490 for a discussion of terminal disclaimers). Such a response is required even when the nonstatutory double patenting rejection is provisional.
Conclusion
No claims are allowed.
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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Sean J. Steinke, whose telephone number is (571) 272-3396. The examiner can normally be reached Monday - Friday, 09:00 - 17:00 ET.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, David Blanchard, can be reached at (571) 272-0827. The fax phone number for the organization where this application or proceeding is assigned is (571) 273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at (866) 217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call (800) 786-9199 (IN USA OR CANADA) or (571) 272-1000.
/S.J.S./
Examiner, Art Unit 1619
/DAVID J BLANCHARD/Supervisory Patent Examiner, Art Unit 1619