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 without traverse of Group (II) with the addition of compound of claim 58 as the elected species
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having the structure
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in the reply filed on 09/15/2025 is acknowledged and maintained.
Applicant argues that claim 60 properly belongs in the elected set of claims because claim 60 accounts for the fact that the compounds of claim 58 are typically obtained as a mixture according to the inventive procedure disclosed in Example I.3 )pages 47-49) of Applicant’s substitute specification, clean version.
This argument is not persuasive. The restriction requirement dated on 08/21/2025 required Applicant to a elect at least one compound species. The term “compound species” refers to a single, identifiable compound, not a mixture of multiple compounds. In the response to the election requirement dated on 09/15/2025, Applicant elected a specific compound species. A mixture, by definition, comprises more than one compound and therefore does not fall within the scope of a single elected species. Accordingly, claim 60, which is directed to a mixture, is not properly within the elected group and remains withdrawn.
Expansion of Species
The elected species has been found to be either anticipated or rendered obvious by prior art. During the course of examination, certain prior art that pertains to nonelected species
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was found, and in the interest of advancing prosecution of the application it has been applied to the appropriate claims below. The prior art search, however, has not be extended unnecessarily to cover all nonelected species, and the requirement for a species election has not been withdrawn because the claims include subject matter that has not been searched, such as the nonelected compounds of formula (IIIb). See MPEP § 803.02.
Priority
This application is a National Stage filing of International Application PCT/EP 2020/074890 filed September 7, 2020, claiming priority to PCT/EP 2020/069707 filed July 13, 2020.
Status of Claims
Acknowledgement is made of the receipt and entry of the amendment to the claims filed on March 03, 2026.
Claims 1-47 are canceled. Claims 48-69 are pending. Claims 48-55, 60, and 64-67 are withdrawn. Claims 56-59, 61-63, and 68-69 are examined in accordance to the elected species.
Action Summary
Claims 56, 57, 61-63, and 68-69 rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, are withdrawn in light of the fact the term “derived from” for R4 is clearly defined in the specification at page 33, lines 9-15.
Claims 56-59, 61-63, and 68-69 are rejected on the basis that it contains an improper Markush grouping of alternatives in light of Applicant’s argument filed 03/23/2026 indicating that Markush grouping is appropriate because both the Markush groups provide a very well define both a single structural similarity as well as a common use.
Claims 56-59, 61-63, and 68-69 rejected under 35 U.S.C. 103 as being unpatentable over Masayuki et al (JP2016193849A) in view of Ma et al (Biomaterials. 2018 September; 178: 383–400). A copy of the untranslated version is provided in the IDS dated 03/17/2023, are maintained.
Claims 56-59, 61-63, and 68-69 provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-9 of copending Application No. 19/328,682 (reference application), are maintained.
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.
Claims 56-59, 61-63, and 68-69 remain rejected under 35 U.S.C. 103 as being unpatentable over Masayuki et al (JP2016193849A) in view of Ma et al (Biomaterials. 2018 September; 178: 383–400). A copy of the untranslated version is provided in the IDS dated 03/17/2023. However, a copy of the English translation can be found in the 892-form.
Masayuki teaches a new dicarboxylic acid or its alkyl ester capable of forming a polymer of a high molecular weight even when much skeleton derived from hydroxyalkanoic acid (3-hydroxybutyric acid) having a secondary hydroxyl group is contained, and to provide a resin containing them as polymerization components, the dicarboxylic acid or its alkyl ester represented by the following formula (1)
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, wherein
The group A represents an aliphatic hydrocarbon group, an alicyclic hydrocarbon group or an aromatic hydrocarbon group,
the group R1 represents a halogen atom, an alkyl group, an aryl group, an alkoxy group, an acyl group, a carboxyl group, an alkoxycarbonyl group, a nitro group or a cyano group,
the group R2 is an alkyl group,
R3 and R4 are the same or different and each represents a hydrogen atom or an alkyl group,
s represents 0 or an integer of 1 or more, and n represents 0 to 10 (Indicates an integer of 10). (See claim 1 and Abstract.) Masayuki teaches the group A is an alkylene group, alkenylene group, mono or dicycloalkylene group, mono or dicycloalkenylene group, mono or biarylene group,
group R1 is a halogen atom, alkyl group, alkoxy group or nitro group, and
group R2 is C1-alkyl,
R3 and R4 are the same or different and are a hydrogen atom or a C 1-4 alkyl group, s is 0 to 6 and n is 1. (See claims 2-3.) Moreover, Masayuki teaches R3 and R4 each represent a hydrogen atom or an alkyl group. Examples of the alkyl group include linear or branched C1 1 -methyl group, ethyl group, propyl group, and more preferably a methyl group or an ethyl group. (See tenth paragraph of page 6.) Masayuki teaches examples of the carboxylic acids include, but not limited to aliphatic dicarboxylic acid include alkane dicarboxylic acids (e.g., C 2-16 alkane dicarboxylic acids such as malonic acid, succinic acid, glutaric acid, adipic acid, suberic acid, azelaic acid, sebacic acid, decanedicarboxylic acid, etc.) And unsaturated aliphatic dicarboxylic acids (for example, C 2-10 alkene-dicarboxylic acids such as maleic acid, fumaric acid, and itaconic acid). When a polycarboxylic acid (a carboxylic acid having three or more carboxyl groups) anhydride such as tricarboxylic acid anhydride or tetracarboxylic dianhydride is used, a polycarboxylic acid capable of forming a polymer having a branched structure in the polymerization reaction. Since the acid can be formed, the molecular weight of the polymer can be increased. (See second paragraph of page 7 bridging sixth and seventh paragraphs of page 9.) The dicarboxylic acid or its alkyl ester can be used in the medical field and in the food industries. (See last paragraph of page 14.) Furthermore, Masayuki teaches examples of the dicarboxylic acid or its alkyl ester includes
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having succinic acid moiety and
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, having maleic acid moiety. (See Examples 1-5.)
Masayuki does not teach the expanded species
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It would have been prima facie obvious to one of ordinary skill in the art at the time the invention was filed to select this compound
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and replace the hydrogen atom of the hydroxyl group with an ethyl group to give Applicant’s claimed compound. One would have been motivated to do so, because Masayuki teaches the hydrogen which is represented by R3 of the formula I can be hydrogen, ethyl and methyl and also because Masayuki teaches one of the preferred compounds, i.e.,
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contains a methyl group. One would reasonably expect the modification to give an effective polymer that can be used in the medical and food field with success.
Masayuki does not teach the elected species
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Differences between the elected species and the compound of Masayuki:
Elected compound Masayuki compound
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It
Ma teaches citric acid, containing three carboxyl groups and one hydroxyl group (Fig. 1A), is a biocompatible, reactive, and multifunctional monomer which contributes to the formation of hydrolysable ester bonds in combination with diol monomers to constitute pre-polymer chains. The tetra functional nature of the citrate monomer concurrently provides pendent carboxyl and hydroxyl groups that can be preserved during pre-polymer synthesis, not only contributing to further polymer network cross-linking post-polymerization, but also providing active sites for introducing functionalities. (See section 2.1.)
It would have been prima facie obvious to one of ordinary skill in the art at the time the invention was filed to have selected this compound
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taught by Masayuki and replace the hydrogen atom of the hydroxyl group with an ethyl group and the maleic acid moiety with a citric acid moiety to give Applicant’s claimed compound. One would have been motivated to do so, because Masayuki teaches the hydrogen which is represented by R3 of the formula I can be hydrogen, ethyl and methyl and because Masayuki teaches examples of the carboxylic acids include, but not limited to aliphatic dicarboxylic acid include alkane dicarboxylic acids (eg, C 2-16 alkane dicarboxylic acids such as malonic acid, succinic acid, glutaric acid, adipic acid, suberic acid, azelaic acid, sebacic acid, maleic acid, fumaric acid, and itaconic acid) and when a polycarboxylic acid (a carboxylic acid having three or more carboxyl groups) anhydride such as tricarboxylic acid anhydride or tetracarboxylic dianhydride is used, a polycarboxylic acid capable of forming a polymer having a branched structure in the polymerization reaction, and said acid can be formed, the molecular weight of the polymer can be increased, and also because Ma teaches citric acid, containing three carboxyl groups and one hydroxyl group (Fig. 1A), is a biocompatible, reactive, and multifunctional monomer which contributes to the formation of hydrolysable ester bonds in combination with diol monomers to constitute pre-polymer chains where the tetra functional nature of the citrate monomer concurrently provides pendent carboxyl and hydroxyl groups that can be preserved during pre-polymer synthesis, not only contributing to further polymer network cross-linking post-polymerization, but also providing active sites for introducing functionalities. One would reasonably expect the modification to give an effective compound/polymer that can be used in the medical and food field with success because citric acid is actually a tricarboxylic acid that contains three carboxylic acid groups, making the modified compound/polymer to be more reactive due to its multiple esterification sites, more efficient and more controlled ester, and more stable.
With respect to a pharmaceutical composition is a medicament or a drug and a food product is a food supplement or functional food recited in the preamble, Masayuki teaches the dicarboxylic acid or its alkyl ester used in the medical and food field. Therefore, the modified polymer/compound is capable of being a drug or a food product such as a dietary supplement or a function food. Where the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977).
Acknowledgement is made of the receipt and entry of Applicant’s remarks/arguments filed on March 03, 2026.
Applicant argues that Masayuki and Ma are directed to polymer and material science application, whereas the present invention is directed to Keto therapy and metabolic uses, and therefore the cited references are from non-analogous fields and/or teach away from the claimed invention. This argument is not persuasive because it improperly focuses on the end-use application rather than underlying chemical subject matter. Masayuki expressly teaches dicarboxylic acid and their esters derived from 3-hydroxybutanoic acid, which are the same class of compounds recited in the present claims. Similarly, Ma teaches citric acid and related polycarboxylic acids as multifunctional monomers capable of forming ester linkages. Thus, both references are directed to structurally related chemical compounds and their reactivity, which constitutes analogous art regardless of the ultimate intended use. In fact, there is guidance in the primary reference (Masayuki) to use polycarboxylic acids for forming ester linkage See MPEP 2141.01(a).
Applicant also argues that substituting citric acid into the system of Masayuki would render the prior art unsatisfactory for its intended purpose (i.e., formation of linear polymers), citing In re Gordon. This argument is not persuasive because the rejection does require that modified system retain the exact polymerization behavior or end-use properties emphasized by Masayuki. Rather, the rejection relies on the teachings of the references with respect to the chemical structures and reactivity of the disclosed compounds, including the formation of ester linkage from hydroxy acids and carboxylic acids. The proposed combination merely involves the use of a known alternative carboxylic acid (citric acid) in place of another known carboxylic acid within the same general class of compounds taught by Masayuki. Such substitution does not render the prior art inoperable for its disclosed purpose, but instead represents a predictable variation in the selection of monomeric components.
Similarly, Applicant’s reliance on In re Ratti is misplaced. The proposed modification does not change the principle of operation of the prior art, which is based on esterification reactions between hydroxy-containing compounds and carboxylic acids. Whether the resulting product is more linear or more branched does not alter this fundamental chemical principle, but merely affects the degree of crosslinking-an expected and well-understood consequence of using multifunctional acids such as citric acid.
In response to applicant's argument that the examiner's conclusion of obviousness is based upon improper hindsight reasoning and the lack of motivation, 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). In the present case, the rejection is based on the express teaching of Masayuki’s Formula (I), which provides a finite set of substituent options (including hydrogen and C1-C4 alkyl groups), and the known use of citric acid as multifunctional carboxylic acid in ester-forming systems as taught by Ma. The selection of these known alternatives constitutes a predictable variation within ordinary skill in the art and does not rely on impermissible hindsight reconstruction.
Finally, Applicant’s arguments regarding differences in pharmacokinetic behavior and biological activity are not commensurate in scope with the claims, which are drawn to chemical compounds and compositions and do not require any particular in vivo performance beyond what would be inherently expected of such esters. Applicant’s arguments improperly import limitations relating to polymer structure (e.g., linearity or crosslinking) that are not recited in the claims.
Accordingly, Applicant has not rebutted the prima facie case of obviousness.
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 56-59, 61-63, and 68-69 remain provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-9 of copending Application No. 19/328,682 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because the copending claims anticipate the instant claims.
The copending claims teach a method for producing carboxylic acid esters of 3-hydroxybutanoate, wherein at least one 3-hydroxybutanoate of general formula (I)
CH3- CH(OH)-CH2-C(O)OR1 (I) wherein, in general formula
(I), the radical R1 is selected among C1-C5-alkyl and hydroxy-C3-C5-alkyl, is reacted, in an esterification reaction, with at least one carboxylic acid
(II) selected from the group consisting of succinic acid, tartaric acid, lactic acid, citric acid, malic acid, adipic acid, fumaric acid and maleic acid and salts, anhydrides and esters thereof as well as combinations or mixtures thereof. (See claim 1.)
Moreover, the copending claims teach a method of treating a human or an animal suffering from a disease of the human or animal body, wherein the method comprises the step of administering to said human or animal a therapeutically efficient amount of at least one carboxylic acid ester of 3-hydroxybutanoate corresponding to general formula (IIIb)
CH3-CH(OR4)-CH2-C(0)OR1 (IIIb)
wherein, in the general formula (IIIb),
the radical R1 is selected among C1-C5-alkyl and hydroxy-C3-C5-alkyl, and
the radical R4 is selected among one or more of the following radicals:
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wherein, in said radicals, the radical Rs represents hydrogen or a radical -CH(CH3)-CH2- C(O)OR1 with R1 being selected among C1-C5-alkyl and hydroxy-C3-C5-alkyl. (See claim 9.)
With respect to a pharmaceutical composition is a medicament or a drug and a food product is a food supplement or functional food recited in the preamble, the compounds of the copending claims are capable of being a drug or a food product such as a dietary supplement or a function food because they are the same compounds as the instant claims. Where the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977).
This is a provisional nonstatutory double patenting rejection.
Applicant has not presented any arguments traversing the nonstatutory obviousness-type double patenting rejection set forth in the prior office action. In the absence of a showing of patentable distinction, the rejection stands.
Conclusion
Claims 56-59, 61-63, and 68-69 are not allowed.
THIS ACTION IS MADE FINAL. 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 JEAN P CORNET whose telephone number is (571)270-7669. The examiner can normally be reached Monday-Thursday from 7.00am-5.30pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Amy L Clark can be reached at 571-272-1310. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/JEAN P CORNET/Primary Examiner, Art Unit 1628
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