DETAILED ACTION
This is in response to communication received on 1/16/26.
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
The text of those sections of AIA 35 U.S.C. code not present in this action can be found in previous office actions dated 10/20/25.
Claim Rejections - 35 USC § 103
The claim rejection(s) under AIA 35 U.S.C. 103 as being obvious over Apffel Jr US PGPub 201410273080 hereinafter APFFEL in view of Bischoff et al. US PGPub 201910262745 hereinafter BISCHOFF on claims 1-11 are withdrawn because the independent claim 1 has been amended and claim 2 has been cancelled.
The claim rejection(s) under AIA 35 U.S.C. 103 as being obvious over Apffel Jr US PGPub 2014/0273080 hereinafter APFFEL in view of Bischoff et al. US PGPub 201910262745 hereinafter BISCHOFF as applied to claim 1 above, as evidenced by Sanchez Garcia et al. The Role of Tricarboxylic Acid Cycle Metabolites in Viral Infections hereinafter GARCIA on claim 3, 4, and 7 are withdrawn because the independent claim 1 has been amended.
The claim rejection(s) under AIA 35 U.S.C. 103 as being obvious over Apffel Jr US PGPub 2014/0273080 hereinafter APFFEL in view of Bischoff et al. US PGPub 2019/0262745 hereinafter BISCHOFF as applied to claim 1 above, as evidenced by Parith Wongkittichote et al. Tricarboxylic acid cycle enzyme activities in a mouse model of methylmalonic aciduria hereinafter WONGKITTICHOTE on claim 5 is withdrawn because the independent claim 1 has been amended.
The claim rejection(s) under AIA 35 U.S.C. 103 as being obvious over Apffel Jr US PGPub 201410273080 hereinafter APFFEL in view of Bischoff et al. US PGPub 201910262745 hereinafter BISCHOFF as applied to claim 1 above, as evidenced by Sanchez Garcia et al. The Role of Tricarboxylic Acid Cycle Metabolites in Viral Infections hereinafter GARCIA and losifina Foskolou et al. 2- hydroxyglutarate rides the cancer-immunity cycle hereinafter FOSKOLOU on claim 6 is withdrawn because the independent claim 1 has been amended.
The claim rejection(s) under AIA 35 U.S.C. 103 as being obvious over Apffel Jr US PGPub 201410273080 hereinafter APFFEL in view of Bischoff et al. US PGPub 2019/0262745 hereinafter BISCHOFF as applied to claim 1 above, and further in view of Lauber et al. US PGPub 2019/0086371 hereinafter LAUBER on claim 8 is withdrawn because the independent claim 1 has been amended.
The claim rejection(s) under AIA 35 U.S.C. 103 as being obvious over Apffel Jr US PGPub 2014/0273080 hereinafter APFFEL in view of Bischoff et al. US PGPub 2019/0262745 hereinafter BISCHOFF as applied to claim 1 above, and further in view of Xiao et al. US PGPub 2017/0198003 hereinafter XIAO on claim 9 is withdrawn because the independent claim 9 has been cancelled.
The claim rejection(s) under AIA 35 U.S.C. 103 as being obvious over Apffel Jr US PGPub 2014/0273080 hereinafter APFFEL, Bischoff et al. US PGPub 2019/0262745 hereinafter BISCHOFF and Xiao et al. US PGPub 2017/0198003 hereinafter XIAO as applied to claim 9 further in view of Grant et al. US2008/0128606 hereinafter GRANT on claim 9 is withdrawn because the independent claim 9 has been cancelled.
Claim(s) 1, 3-4, 7 and 11 are rejected under 35 U.S.C. 103 as being unpatentable over Apffel Jr US PGPub 2014/0273080 hereinafter APFFEL in view of Bischoff et al. US PGPub 2019/0262745 hereinafter BISCHOFF, and Xiao et al. US PGPub 2017/0198003 hereinafter XIAO as evidenced by Sanchez Garcia et al. The Role of Tricarboxylic Acid Cycle Metabolites in Viral Infections hereinafter GARCIA and Mirelmal et a. US PGPub 2018/0071369 hereinafter MIRELMAN.
As for claim 1, APFFEL teaches "metabolites may include substrates or products which are produced by metabolic processes including, but not limited to ... tricarboxylic acid cycle (i.e., TCA cycle, Krebs cycle)" (paragraph 52, lines 6-9), "Methods of the invention may further include separating the target compounds (e.g., metabolites) extracted from the biological sample cells from the ionic liquid, such as for example by microextraction ... For example, microextraction may include solid phase chromatography. In certain embodiments, solid phase chromatography includes, but is not limited to ion exchange chromatography, liquid chromatography employing a reverse phase stationary column (paragraph 80) and "some embodiments, separating the metabolites from the ionic liquid further includes analysis of the separated metabolites. By analyzed is meant characterizing the chemical com position of the separated metabolites, including but not limited to the am aunt and types of compounds in the extracted metabolites as well as any impurities present. Chemical analysis may be conducted using any convenient protocol, such as for example by mass spectrometry" (paragraph 81, lines 1-8), i.e. A method of separating and analyzing a sample comprising tricarboxylic acid cycle metabolites, the method comprising: injecting the sample into a chromatographic system ... flowing the injected sample through the chromatographic system along the sample flow path; separating the sample with the chromatographic system to produce a separated sample; analyzing the separated sample with a mass spectrometer.
APFFEL is silent on a chromatographic system having a fluid-contacting coating on a metallic surface defining a sample flow path, wherein the coating comprises an alkylsilyl coating, and wherein the coating covers at least 90% of the surfaces of the sample flow path.
BISCHOFF teaches "Liquid chromatography techniques are disclosed. Specifically, the liquid chromatography technique includes providing a liquid chromatography system having a coated metallic fluid-contacting element, and transporting a fluid to contact the coated metallic fluid-contacting element" (abstract, lines 1-5), i.e. A method of separating and analyzing a sample ... the method comprising: injecting the sample into a chromatographic system having a fluid contacting coating on a metallic surface defining a sample flow path ... flowing the injected sample through the chromatographic system along the sample flow path.
BISCHOFF teaches numerous advantages to systems with its coating ( paragraph 14).
BISCHOFF teaches "The coated metallic column 109 includes a substrate 201 and the coating 203" (paragraph 20) and "Any additional or alternative components are capable of being used, so long as the system 100 includes a coated metallic fluid contacting element, such as the coated meta Ilic column 109, or any other component of the system 100 that is contacted by a fluid, such as, a mobile phase, a solvent, an analyte, or a combination thereof. Additionally or alternatively, other components are capable of being similarly coated, such as, frits, fittings, pump heads, valves, tubing, vessels, or combinations thereof" (paragraph 16, lines 11-20) wherein the coating can be applied to all surface exposed to the fluid, i.e. a range that falls within wherein the coating covers at least 90% of the surfaces of the sample flow path. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990); In re Geisler, 116 F.3d 1465, 1469-71, 43 USPQ2d, 1362, 1365-66 (Fed. Cir. 1997). See MPEP 2144.05.
BISCHOFF further teaches "The coating 203 includes one or a plurality of depositions, decompositions, functionalizations, oxidations, or a com bi nation thereof. In one embodiment, the coating 203 includes carbon, silicon, oxygen, and hydrogen. In additional or alternative embodiments, other constituents in the coating 203 include, but are not limited to, fluorine, nitrogen, decompositional materials from precursor materials, functionalizations from precursor materials, or a combination thereof" (paragraph 39, lines 1-9; emphasis added), and "Suitable precursor materials include, but are not limited to ... dialkylsilyl dihydride, alkylsilyl trihydride, non-pyrophoric species (for example, dialkylsilyl dihydride and/or alkylsilyl trihydride ) ... species capable of a recombination of carbosilyl (disilyl or trisilyl fragments)" (paragraph 39, lines 9-18), i.e. wherein the coating comprises an alkylsilyl coating.
It would have been obvious to one of ordinary skill in the art before the effective filing date to include a chromatographic system having a fluid-contacting coating on a metallic surface defining a sample flow path, wherein the coating comprises an alkylsilyl coating, and wherein the coating covers a range that overlaps with at least 90% of the surfaces of the sample flow path in the process of APFFEL because BISCHOFF teaches teach such a coating improves the output of liquid chromatography.
APFFEL and BISCHOFF are silent on wherein separating the sample comprises using mixed mode anion exchange chromatographic method.
However APFFEL does teach "metabolites may include substrates or products which are produced by metabolic processes including, but not limited to ... tricarboxylic acid cycle (i.e., TCA cycle, Krebs cycle)" (paragraph 52, lines 6-9).
APFFEL also teaches "In certain embodiments, the sample analyzer may be liquid chromatography-mass spectrometry or gas chromatography- mass spectrometry systems. For example, the apparatus may include analytical separation device such as a liquid chromatograph (LC), including a high performance liquid chromatograph (HPLC)" (paragraph 114, lines 2-7).
XIAO teaches "A mixed-mode liquid chromatography separation protocol (anion exchange/norm al phase) was used to separate these glycolipids" (paragraph 153, lines 1-3).
GARCIA shows that oxaloacetate is a substance that is a metabolite of the TCA cycle (page 2). MIRELMAN teaches “A protein preparation comprising Glutamate Oxaloacetate Transaminase 1 (GOTl) polypeptide molecules is disclosed” (abstract, lines 1-2).
MIRELMAN teaches “the isolating is effected using a technique selected from the group consisting of heat precipitation, salt induced precipitation, mixed mode chromatography, cation exchange chromatography and anion exchange chromatography” (paragraph 38), i.e. wherein mixed mode chromatography is a known method of liquid chromatography for separating TCA cycle metabolites.
It would have been obvious to one of ordinary skill in the art to have wherein separating the sample comprises using a mixed mode anion exchange chromatographic method as the liquid chromatography of the combined APFFEL and BISCHOFF because XIAO teaches that such mixed mode anion exchange liquid chromatography can be used to separate out desired materials and MIRELMAN and GARCIA establish that it was known to use such a method to separate out the TCA cycle metabolites.
As for claim 3, APFFEL teaches "metabolites may include substrates or products which are produced by metabolic processes including, but not limited to ... tricarboxylic acid cycle (i.e., TCA cycle, Krebs cycle)" (paragraph 52, lines 6-9), but is silent on the specifical materials that constitute metabolites.
GARCIA on page 2 shows the various metabolites of the tricarboxylic acid cycle which includes citric acid.
As such it is inherent that APFFEL teaches wherein the one or more tricarboxylic acid cycle metabolites comprise at least one tricarboxylic acid metabolite selected from the group of citric acid.
As for claim 4, APFFEL teaches "metabolites may include substrates or products which are produced by metabolic processes including, but not limited to ... tricarboxylic acid cycle (i.e., TCA cycle, Krebs cycle)" (paragraph 52, lines 6-9), but is silent on the specifical materials that constitute metabolites.
GARCIA on page 2 shows the various metabolites of the tricarboxylic acid cycle which includes citric acid and isocitric acid.
As such it is inherent that APFFEL teaches wherein the sample comprises isocitric acid and citric acid.
As for claim 7, APFFEL teaches "metabolites may include substrates or products which are produced by metabolic processes including, but not limited to ... tricarboxylic acid cycle (i.e., TCA cycle, Krebs cycle)" (paragraph 52, lines 6-9), but is silent on the specifical materials that constitute metabolites.
GARCIA on page 2 shows the various metabolites of the tricarboxylic acid cycle which includes malic and fumaric acid.
As such it is inherent that APFFEL teaches wherein the sample comprises malic acid and fumaric acid.
As for claim 11, APFFEL is silent on wherein the metallic surface comprises column walls and frit surfaces; and wherein the coating on the metallic surface increases sample peak area relative to a non-coated metallic surface
BISCHOFF teaches "Embodiments of the present disclosure, for example, in comparison to concepts failing to include one or more of the features disclosed herein, expands the capabilities of liquid chromatography, perm its increased precision of liquid chromatography" (paragraph 14, lines 2-6) and "Additionally or alternatively, other components are capable of being similarly coated, such as, f rits, fittings, pump heads, valves, tubing, vessels, or combinations thereof" (paragraph 16, lines 15-18), i.e. wherein the metallic surface comprises column walls and frit surfaces; and wherein the coating on the metallic surface increases sample peak area relative to a non-coated metallic surface.
It would have been obvious to one of ordinary skill in the art before the effective filing date to include the wherein the metallic surface comprises column walls and frit surfaces; and wherein the coating on the metallic surface increases sample peak area relative to a non-coated metallic surface in the process of APFFEL because BISCHOFF teaches that such a coating provides benefits (paragraph 14).
Claim(s) 5 is rejected under 35 U.S.C. 103 as being unpatentable over Apffel Jr US PGPub 2014/0273080 hereinafter APFFEL in view of Bischoff et al. US PGPub 2019/0262745 hereinafter BISCHOFF, and Xiao et al. US PGPub 2017/0198003 hereinafter XIAO as evidenced by Sanchez Garcia et al. The Role of Tricarboxylic Acid Cycle Metabolites in Viral Infections hereinafter GARCIA and Mirelmal et a. US PGPub 2018/0071369 hereinafter MIRELMAN as applied to claim 1 above, as evidenced by Parith Wongkittichote et al. Tricarboxylic acid cycle enzyme activities in a mouse model of methylmalonic aciduria hereinafter WONGKITTICHOTE.
As for claim 5, APFFEL teaches "metabolites may include substrates or products which are produced by metabolic processes including, but not limited to ... tricarboxylic acid cycle (i.e., TCA cycle, Krebs cycle)" (paragraph 52, lines 6-9), but is silent on the specifical materials that constitute metabolites.
WONGKITTICHOTE specifically teaches that succinic and methylmalonic acid is a part of the TCA cycle's propionate pathway, as shown in Figure 1.
As such it is inherent that APFFEL teaches wherein the sample comprises methylmalonic acid and succinic acid.
Claim(s) 6 is rejected under 35 U.S.C. 103 as being unpatentable over Apffel Jr US PGPub 2014/0273080 hereinafter APFFEL in view of Bischoff et al. US PGPub 2019/0262745 hereinafter BISCHOFF, and Xiao et al. US PGPub 2017/0198003 hereinafter XIAO as evidenced by Sanchez Garcia et al. The Role of Tricarboxylic Acid Cycle Metabolites in Viral Infections hereinafter GARCIA and Mirelmal et a. US PGPub 2018/0071369 hereinafter MIRELMAN as applied to claim 1 above, and further in view of losifina Foskolou et al. 2- hydroxyglutarate rides the cancer-immunity cycle hereinafter FOSKOLOU.
As for claim 6, APFFEL teaches "metabolites may include substrates or products which are produced by metabolic processes including, but not limited to ... tricarboxylic acid cycle (i.e., TCA cycle, Krebs cycle)" (paragraph 52, lines 6-9), but is silent on the specifical materials that constitute metabolites.
GARCIA on page 2 shows the various metabolites of the tricarboxylic acid cycle which includes itaconic acid and cis-aconitic acid.
FOSKOLOU shows in the first line of its abstract that 2-hydroxygluratic acid is a biproduct of the Krebs cycle.
As such it is inherent that APFFEL teaches wherein the sample comprises itaconic acid and cis-aconitic acid.
Claim(s) 8 is rejected under 35 U.S.C. 103 as being unpatentable over Apffel Jr US PGPub 2014/0273080 hereinafter APFFEL in view of Bischoff et al. US PGPub 2019/0262745 hereinafter BISCHOFF, and Xiao et al. US PGPub 2017/0198003 hereinafter XIAO as evidenced by Sanchez Garcia et al. The Role of Tricarboxylic Acid Cycle Metabolites in Viral Infections hereinafter GARCIA and Mirelmal et a. US PGPub 2018/0071369 hereinafter MIRELMAN as applied to claim 1 above, and further in view of Lauber et al. US PGPub 2019/0086371 hereinafter LAUBER.
Examiner notes that the instant application does claim benefit of provisional applications 62/968639 and 63/071643. However these provisional applications never make mention of making a coating specifically made out of bis(trichlorosilyl)ethane or bis(trimethoxysilyl)ethane. As such the effective filing date for that subject matter is the filing date of the effective filing date of 1/15/2021 (from Application of 17/150802).
As for claim 8, APFFEL and BISCHOFF are silent on wherein the coating is made using vapors of bis(trichlorosilyl)ethane or bis( trimethoxysilyl)ethane.
LAUBER teaches "A device for separating analytes is disclosed. The device has a sample injector, sample injection needle, sample reservoir container in communication with the sample injector, chromatography column downstream of the sample injector, and fluid conduits connecting the sample injector and the column," (abstract, lines 1-6) and "The alkylsilyl coating of Formula I can be bis(trichlorosilyl)ethane or bis(trimethoxysilyl)ethane" (paragraph 19, lines 3-6).
LAUBER teaches "At least a portion of the wetted surfaces of the fluidic flow path are coated with a alkylsilyl coating, wherein the alkylsilyl coating is inert to at least one of the analytes in the sample" (paragraph 15, lines 9-12).
It would have been obvious to one of ordinary skill in the art before the effective filing date to include wherein the coating is made using vapors of bis(trichlorosilyl)ethane or bis( trimethoxysilyl)ethane in the process of APFFEL and BISCHOFF because LAUBER teaches that such a coating is inert to the analytes of a system.
Claim(s) 10 is rejected under 35 U.S.C. 103 as being unpatentable over Apffel Jr US PGPub 2014/0273080 hereinafter APFFEL in view of Bischoff et al. US PGPub 2019/0262745 hereinafter BISCHOFF, and Xiao et al. US PGPub 2017/0198003 hereinafter XIAO as evidenced by Sanchez Garcia et al. The Role of Tricarboxylic Acid Cycle Metabolites in Viral Infections hereinafter GARCIA and Mirelmal et a. US PGPub 2018/0071369 hereinafter MIRELMAN as applied to claim 1 above, and further in view of Grant et al. US2008/0128606 hereinafter GRANT.
As for claim 10, APFFEL and BISCHOFF when modified by XAIO as shown above in the rejection of claim 1, teach a mixed mode anion exchange chromatographic method.
XAIO is silent on the column used. GRANT teaches "Disclosed are methods and systems using liquid chromatography/ tandem mass spectrometry (LC-MS/MS ... MS) for the analysis of endogenous biomarkers" (abstract, lines 1-3).
GRANT further teaches "As used herein, "liquid chromatography" (LC) means a process of selective retardation of one or more components of a fluid solution as the fluid uniformly percolates through a column of a finely divided substance, or through capillary passageways" (paragraph 7 4, lines 1-5) and further "As used herein, the term "analytical column" refers to a chromatography column having sufficient chromatographic plates to effect a separation of the components of a test sample matrix. Preferably, the components eluted from the analytical column are separated in such a way to allow the presence or amount of an analyte(s) of interest to be determined. In some embodiments, the analytical column comprises particles having an average diameter of about 5 μm. In some embodiments, the analytical column is a functionalized silica or polymer-silica hybrid, or a polymeric particle or monolithic silica stationary phase, such as a phenyl-hexyl functionalized analytical column" (paragraph 76).
It would have been obvious to one of ordinary skill in the art before the effective filing date to include the column of GRANT into the process of APFFEL, BISCHOFF and XAIO such that wherein using a mixed mode anion exchange chromatographic method comprises using a phenyl-hexyl chromatographic column because GRANT teaches that such a column is known to be used in liquid chromatography when used in tandem with mass spectrometry, and useful for such a process.
Double Patenting
The provisional claim rejection(s) on the ground of nonstatutory double patenting over U.S. Patent No. 11,740,211 on claim 1, 3, 6, and 9-11 are maintained. The Applicant Arguments/Remarks dated 1/16/2026 state they have filed a terminal disclaimer, but no such terminal disclaimer was provided. As such, the rejection is maintained and updated below to meet the added claim limitations.
Claim 1, 2 and 4 of U.S. Patent No. 11,740,211 has the same subject matter as claim 1 and 8 of the instant specification save for the requirement for coverage. However, as claim 1 states that its coating covers the metal surface, it encompasses claim 1 and 8.
Claim 3 of U.S. Patent No. 11,740,211 is identical to claim 3 of the instant specification.
Claim 4 of U.S. Patent No. 11,740,211 is identical to claim 9 of the instant specification.
Claim 6 of U.S. Patent No. 11,740,211 is identical to claim 10 of the instant specification.
Claim 7 of U.S. Patent No. 11,740,211 is identical to claim 11 of the instant specification.
Claim 8 of U.S. Patent No. 11,740,211 has the same subject matter as claim 1, 8 and 11 of the instant specification save for the requirement for coverage. However, as claim 8 states that its coating covers the metal surface, it encompasses claim 1 and 8.
Claim 10 of U.S. Patent No. 11,740,211 is identical to claim 2 of the instant specification.
Claim 11 of U.S. Patent No. 11,740,211 is identical to claim 6 of the instant specification.
Claim 12 of U.S. Patent No. 11,740,211 is identical to claim 11 of the instant specification.
Claim 15 and 20 of U.S. Patent No.11,740,211 has the same subject matter as claim 1, 2 and 8 of the instant specification.
Claim 14 of U.S. Patent No. 11,740,211 is identical to claim 2 of the instant specification.
Claim 16 of U.S. Patent No. 11,740,211 is identical to claim 3 of the instant specification.
The provisional claim rejection(s) on the ground of nonstatutory double patenting over U.S. Patent No. 12,117,427 on claim 1, 4-11 are maintained. The Applicant Arguments/Remarks dated 1/16/2026 state they have filed a terminal disclaimer, but no such terminal disclaimer was provided. As such, the rejection is maintained and updated below to meet the added claim limitations, namely Sanchez Garcia et al. The Role of Tricarboxylic Acid Cycle Metabolites in Viral Infections hereinafter GARCIA is cited as evidence.
Claim 1, 2 and 6 of U.S. Patent No. 12,117,427 has the same subject matter as claim 1 and 8 and alternatively 4, 5, 6, 7 of the instant specification. Specifically, claim 1 of U.S. Patent No. 12,117,427 is silent on the amount of coverage, but does generally claim coating the metallic surface. This broad teaching encompasses the subject matter of claims 1 and 8 of the instant specification. Further, claim 1 and 8 are silent on critical pairs, but the dependent claims 4, 5, 6, and 7 name critical pairs of material, and as such claim 1 and 8 encompasses embodiments with critical pairs. Further claim 6 of U.S. Patent No. 12,117,427 teaches that mixed mode anion exchange chromatographic method and claim 2 teaches critic acid which GARCIA establishes is a part of the TCA cycle.
Claim 2 of U.S. Patent No. 12,117,427 overlaps with claim 4 of the instant specification.
Claim 3 of U.S. Patent No. 12,117,427 overlaps with claim 5 of the instant specification.
Claim 4 of U.S. Patent No. 12,117,427 overlaps with claim 6 of the instant specification.
Claim 5 of U.S. Patent No. 12,117,427 is identical to claim 7 of the instant specification.
Claim 6 of U.S. Patent No. 12,117,427 is identical to claim 9 of the instant specification.
Claim 7 of U.S. Patent No. 12,117,427 is identical to claim 10 of the instant specification.
Claim 8 and 9 of U.S. Patent No. 12,117,427 fall within claim 11 the instant specification.
Response to Arguments
Applicant’s arguments with respect to claim(s) 1, 3-8, 10-11 have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Conclusion
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.
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/KRISTEN A DAGENAIS/Examiner, Art Unit 1717
//Supervisory Patent Examiner, Art Unit 1717
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