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 .
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.
Withdrawn Objections/Rejections
The objections to the specification are withdrawn in response to the amendments.
The objections to the claims are withdrawn in response to the amendments. However, new objections are set forth below.
The rejections of the claims under 112a are withdrawn in response to the amendments. However, new grounds of rejection are set forth below.
The rejections of the claims under 112b are withdrawn in response to the amendments. However, new grounds of rejection are set forth below.
The rejections under 112d are withdrawn in response to the amendments.
The rejections of claims 1, 9-11 and 17-18 under 102 are withdrawn in response to the amendments.
The rejections of claims 1-3, 5, 9-11, 17-18, 30, 32 and 77-78 under non-statutory double patenting are withdrawn in response to the amendments. However, new grounds of rejection are set forth below.
Priority
Acknowledgment is made of the present application as a proper National Stage (371) entry of PCT Application No. PCT/US2020/036285, filed 06/05/2020, which claims benefit under 35 U.S.C. 119(e) to provisional application No. 62/982,576, filed 02/27/2020 and to provisional application No. 62/858,539, filed 06/07/2019.
However, a claim-by-claim analysis results in only claims 77, 79, 89-90 and 92-94 receiving priority benefit. Claims 1-3, 5-6, 14-19, 30, 32, 78, 80-88 and 91 fail to receive priority benefit since these contain subject matter not disclosed in the provisional applications. Specifically, it appears that the limitation of single electron energy transfer from a transition metal photocatalyst (as recited in claims 1 and 30) or from a flavin (as recited in claim 77) to a protein labeling agent comprising a diazirine or an azide (as recited in claims 1 and 30) or comprising a phenol moiety (as recited in claim 77) in not disclosed. Regarding claim 91, it appears that only the limitation of the “BCN, DBCO, TCO, tetrazine ” is not supported by priority benefit because this limitation is missing in the provisional applications.
Thus, for purposes of applying prior art, claims 1-3, 5-6, 14-19, 30, 32, 78, 80-88 and 91 are subject to a priority date of 06/05/2020.
Should applicant disagree with the examiner’s factual determination above, applicant should provide evidence that either or both of the provisional applications provide support for the invention now claimed in the manner required by 35 U.S.C. 112 (a) or 35 U.S.C. 112 (pre-AIA ), first paragraph. This could be accomplished, for example, by pointing to the specific page and line numbers within the provisional applications which disclose each limitation of the claimed invention.
Status of the Claims
Claims 1-3, 5-6, 14-19, 30, 32 and 77-94 are pending; claims 1, 14-19, 30, 32 and 77 are amended, claims 4, 7-13, 20-29, 31, 33-76 are canceled; claims 79-94 are newly recited; no claims are withdrawn. Claims 1-3, 5-6, 14-19, 30, 32 and 77-94 are examined below.
New Objections
Claim Objections
Claims 16 and 91 are objected to because of the following informalities:
In claims 16 and 91 line 2, Applicant uses the abbreviations “BCN, DBCO, TCO”. It is suggested that abbreviations be accompanied by their full meaning at least at the first instance that the abbreviation is used in order to improve clarity of the record and avoid confusion.
Appropriate correction is required.
New Rejections
Claim Rejections - 35 USC § 101
35 U.S.C. 101 reads as follows:
Whoever invents or discovers any new and useful process, machine, manufacture, or composition of matter, or any new and useful improvement thereof, may obtain a patent therefor, subject to the conditions and requirements of this title.
Claims 77-78 are rejected under 35 U.S.C. 101 because the claimed invention is directed to a natural phenomenon (specifically to a nature-based product), without significantly more.
Claim 77 recites “[a] composition for proximity-based labeling comprising: a flavin photocatalyst; and a protein labeling agent comprising a phenol moiety wherein the flavin photocatalyst has an electronic structure to activate the protein labeling agent to a reactive intermediate via energy transfer, wherein the reactive intermediate has a diffusion radius prior to quenching”.
Claim 78 recites “wherein the energy transfer is single electron transfer”.
The claim therefore encompasses nature-based products, namely flavins, i.e. vitamin B2, and phenolic compounds. Flavins and phenolic compounds are present in food, e.g. tea.
See for example, Yashin et al. Journal of Food Research; Vol. 4, No. 3; 2015 doi:10.5539/jfr.v4n3p56 (“Yashin”) teaches “chemical compounds present in tea…Catechins…riboflavin” (page 57 Table 1). Note that catechins are phenols (“content of polyphenols…Catechins” page 73 Table 12). Therefore, Yashin teaches that the composition claimed, a flavin and a phenol, is found in nature, namely in tea.
The additional elements of the claims fail to add significantly more than the judicial exception. The limitation “for proximity-based labeling”, is mere intended purpose of the nature-based product and therefore is not imparting any structural limitation to the nature-based product. Similarly, the specification fails to clearly define a “protein labeling agent” therefore, the reactive intermediate of the phenol is inherently interpreted to provide the “protein labeling agent” limitation claimed. Note that the specification page 13 lines 11-15 discloses that “For example, an organocatalyst can be a flavin photocatalyst. The excited flavin photocatalyst can undergo single electron transfer with phenol moieties to generate a reactive phenoxy radical. FIG. 3 illustrates a reaction mechanism for flavin-based protein labeling according to some embodiments. As illustrated in FIG. 3, the phenol protein labeling agent is functionalized with a tag or marker for assisting in identification of proteins labeled by the protein labeling agent”. The language “the phenol protein labeling agent” used by the specification suggests that the “protein labeling agent” encompasses the phenol by itself, e.g. a natural protein. Furthermore, vitamin B2, are photocatalysts that inherently activate phenols to a reactive intermediate via single electron transfer, i.e. oxidation reactions and the reactive intermediate has a diffusion radius prior to quenching.
For all of these reasons, the claimed subject matter is ineligible under 35 U.S.C. 101 because the claimed article is a nature-based product not markedly different than from what exists in nature
New Rejections
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 1-3, 5-6, 14-19, 30, 32 and 80-88 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the enablement requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to enable one skilled in the art to which it pertains, or with which it is most nearly connected, to make and/or use the invention.
The specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to use the invention commensurate in scope with these claims. The specification does not reasonably provide enablement for a transition metal photocatalyst absorbing light in the visible region of the electromagnetic spectrum and comprising a triplet excited state having energy greater than 60 kcal/mol; and a protein labeling agent comprising a diazirine or an azide, wherein the transition metal activates the protein labeling agent to a reactive intermediate comprising a carbene or nitrene via single electron transfer from the triplet excited state.
The specification does not provide sufficient evidence that the claimed transition metal photocatalyst is effective at activating the protein labeling agent comprising a diazirine or an azide to a reactive intermediate comprising a carbene or nitrene via single electron transfer. The evidence provided merely shows evidence of “a flavin photocatalyst. The excited flavin photocatalyst can undergo single electron transfer with phenol moieties to generate a reactive phenoxy radical. FIG. 3 illustrates” (page 13 lines 11-13). Notably, a flavin photocatalyst is not the transition metal photocatalyst claimed. Indeed, the specification suggests that “single electron transfer…generate[s] a reactive…radical” (page 13 lines 11-13). Given that the claim recites a carbene or nitrene, and not a carbene or nitrene radical, the claim suggests that the energy transfer is not via single electron. Therefore, the specification does not enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the invention.
MPEP § 2164.01 states:
The standard for determining whether the specification meets the enablement
requirement was cast in the Supreme Court decision of Minerals Separation Ltd. v. Hyde, 242 U.S.261, 270 (1916) which postured the question: is the experimentation needed to practice the invention undue or unreasonable? That standard is still the one to be applied.
In re Wands, 858F.2d 731, 737, 8 USPQ2d 1400, 1404 (Fed. Cir. 1988). Accordingly, even though the statute does not use the term "undue experimentation," it has been interpreted to require that the claimed invention be enabled so that any person skilled in the art can make and use the invention without undue experimentation.
In re Wands, 858 F.2d at 737, 8 USPQ2d at 1404 (Fed. Cir. 1988).
There are many factors to be considered when determining whether there is sufficient evidence to support a determination that a disclosure does not satisfy the enablement requirement and whether any necessary experimentation is "undue." These factors include, but are not limited to:
(A) The breadth of the claims;
(B) The nature of the invention;
(C) The state of the prior art;
(D) The level of one of ordinary skill;
(E) The level of predictability in the art;
(F) The amount of direction provided by the inventor;
(G) The existence of working examples; and
(H) The quantity of experimentation needed to make or use the invention based on the content of the disclosure.
In re Wands, 858 F.2d 731, 737, 8 USPQ2d 1400, 1404 (Fed. Cir. 1988).
In regard to Wands factors (A) and (B), the breadth of the claims needed to enable the invention is determined by whether the scope of enablement provided to one skilled in the art by the disclosure is commensurate with the scope of protection sought in the claims. AK Steel Corp. v. Sollac, 344 F.3d 1234, 1244, 68 USPQ2d 1280, 1287 (Fed. Cir. 2003); In re Moore, 439 F.2d 1232, 1236, 169 USPQ 236, 239 (CCPA 1971). The propriety of a rejection based upon the scope of a claim relative to the scope of the enablement concerns (1) how broad the claim is with respect to the disclosure and (2) whether one skilled in the art could make and use the entire scope of the claimed invention without undue experimentation.
The nature of the invention is a biological/chemical case, where there is natural unpredictability in performance of certain species other than those specifically enumerated; see MPEP § 2163. Accordingly, it is the Office’s position that undue experimentation would be required to practice the claimed method(s), with a reasonable expectation of success, because it would not have been predictable from the disclosure that the claimed transition metal photocatalyst would function as claimed with respect to activating the diazirine or azide to a carbene or nitrene using single electron transfer (see MPEP § 2164.03). For example, the Appendix of provisional application 62858539 discloses the “IRidium-mediated Diazirine Activation… The mechanism of the proposed transformation is… Dexter energy transfer” (page 2 col. 3 para. 2). Furthermore, it would not have been predictable from the disclosure that any transition metal photocatalyst absorbing light in the visible region of the electromagnetic spectrum would comprise a triplet state having energy greater than 60 kcal/mol (see Fig 2B of the Appendix of provisional application 62858539 showing different species of iridium or ruthenium with a triplet state having energy less than 60 kcal/mol, page 2).
In regard to Wands factors (C), (D) and (E), the state of the prior art is what one skilled in the art would have known, at the time the application was filed, about the subject matter to which the claimed invention pertains and provides evidence for the degree of predictability in the art; see MPEP § 2164.05(a).
Accordingly, Farney and Yoon Angew Chem Int Ed Engl. 2014 January 13; 53(3): 793–797. doi:10.1002/anie.201308820 (“Farney”) teaches a “recently reported visible light induced photoreduction of aryl azides using Ru(bpy)32+ as a photocatalyst (Scheme 1, eq 1). The key intermediate in this reaction, however, was proposed to be a nitrene radical anion generated by one-electron reduction of the azide, and these intermediates do not exhibit the characteristic reactivity of neutral nitrenes” (page 1 para. 2). Farney further suggests that the energy transfer of the Ru(bpy)32+ as a photocatalyst to the azide is not through single electron transfer (“We also observed little dependence on solvent polarity; reactions in chloroform (ε = 4.81) and acetonitrile (ε = 36.6) gave similar results (entries 5–9). These data, too, support an energy transfer mechanism, as charged radical ion intermediates would be strongly destabilized in nonpolar media” page 2 para. 3).
Also, Eric R. Welin MacMillan Group Meeting February 12th, 2015 (retrieved online https://macmillan.princeton.edu/wp-content/uploads/ERW_Behind_the_Scenes.pdf on 3/13/2026) teaches that “moving from ruthenium to iridium has a profound effect on photophysical properties… Electronegativity (EN)… Ligand Field Stabilization Energy (LFSE)… Spin-Orbit Coupling (SO)” (page 7). Welin further teaches that “Common Transition Metal Photocatalysts: the "Big 4"” have light absorption in the UV range “λabs = 375 nm… λabs = 380 nm” (page 4) and also . Welin further teaches that “Single Electron Transfer” involves “*PC + sub → PC– + sub+” or “*PC + sub PC+ + sub– ”(page 22), i.e. the generation of a radical. Welin further suggests that Dexter energy transfer generates a neutral substrate (“unlike electron transfer, relaxation of T1 (excited state) to S0 (ground state) occurs in a single step…energy transfer can occur via 2 potential mechanisms (Förster transfer or Dexter transfer)” page 23).
Prier et al. Chem Rev. 2013 Mar 19;113(7):5322–5363. doi: 10.1021/cr300503r (“Prier”) teaches that “[t]he products of this single electron-transfer event are the radical anion of A and the oxidized form of the photocatalyst, Ru(bpy)33+” (page 4 para. 1).
Brachet et al. Chem. Sci., 2015,6, 987-992 DOI https://doi.org/10.1039/C4SC02365J
(“Brachet”) teaches that “Ru(bpy)3Cl2 acts upon blue light irradiation as a triplet sensitizer for benzoyl azides. The interaction of the excited ruthenium complex and the azide was confirmed by a Stern Volmer experiment (see ESI† for data). An electron transfer pathway is excluded, as benzoyl azides are insufficiently electron deficient to be easily reduced by ruthenium photocatalysis: the reduction potentials of [Ru(bpy)3Cl2]* and benzoyl azide 1b, respectively, are 0.89 and 1.49 V versus the saturated calomel electrode (SCE)” (page 990 col. 2 para. 1).
Given the cited teachings of the prior art that single electron transfer generates a radical, the cited references demonstrate that the use of the transition metal photocatalyst to activate the diazirine or azide into a carbene or nitrene using single electron transfer is unpredictable. Additionally, the cited teachings of the prior art demonstrate that the photophysical properties of the transition metal photocatalysts claimed are highly unpredictable.
While the level of skill in the art is high, the amount of guidance provided regarding how to use the claimed transition metal photocatalyst to activate the diazirine or azide into carbene or nitrene via single electron transfer is scant. Accordingly, the amount of experimentation required to determine how to use the recited composition is quite extensive.
Due to the large quantity of experimentation necessary to determine how to use the recited composition/system, the lack of direction/guidance presented in the specification regarding the same, the absence of working examples directed to the same, the complex nature of the invention, the limited state of the prior art, the unpredictability of the effects of complex biological molecules on physiological systems, and the breadth of the claims, undue experimentation would be required of the skilled artisan to make and/or use the claimed invention.
In view of all of the above, one of skill in the art would be forced into undue experimentation to practice the claimed invention, and thus, the claimed invention does not satisfy the requirements of 35 U.S.C. §112 first paragraph.
New Rejections
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 5, 18, 80-88 and 93 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claims 5, 18, 82, 87 and 93 recite the term “aqueous-based”. The limitation “aqueous-based” is a relative term which renders the claims indefinite. The term “aqueous-based” is not defined by the claim, the specification does not provide a standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the scope of the invention. Aqueous-based involves an arbitrary level of water, therefore, a person having ordinary skill in the art would not be able to recognize the metes and bounds of the claim. It is not clear how much water, i.e. how aqueous, an aqueous-based solution is.
Claims 80-88 recite the limitation "the composition of claim 30" in line 1. There is insufficient antecedent basis for this limitation in the claim. It is not clear to what composition the claims are referring to in claim 30 because claim 30 fails to recite any composition. A person having ordinary skill in the art would not be able to recognize the metes and bounds of the claim. For this reason the claims are indefinite.
Maintained Rejections
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 77-78 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Cardoso et al. Food Funct., 2012, 3, 487 DOI: 10.1039/c2fo10246c- Cite No. V of PTO 892 9/24/2025 ("Cardoso").
Regarding claims 77-78, Cardoso teaches a composition for proximity-based labeling comprising: a flavin (“Riboflavin, vitamin B2, and flavins (as riboflavin building blocks or degradation products) are efficient photosensitizers inducing oxidative damage to light-exposed tissue and food by substrate-dependent mechanisms” Abstract); and a protein labeling agent (“Phenolic and N-heterocyclic amino acids and their peptides and proteins” Abstract), wherein the flavin photocatalyst has an electronic structure to activate the protein labeling agent comprising a phenol moiety to a reactive intermediate via energy transfer, wherein the reactive intermediate has a diffusion radius prior to quenching, wherein the energy transfer is single electron transfer (“Phenolic and N-heterocyclic amino acids and their peptides and proteins deactivate triplet-excited state riboflavin in diffusion controlled processes, … resulting in direct (so called Type I) protein degradation through electron transfer or proton-coupled electron transfer” Abstract, “Quenching by tyrosine, a phenolic amino acid, is diffusion controlled and shows neither pH effect nor kinetic deuterium/hydrogen isotope effect suggesting at first a electron transfer mechanism. Tyrosine has an accessible one-electron oxidation potential for 3 Rib* and forms a very strong acid cation radical, pKa of -2, thus the mechanism has been classified as a step-wise proton-coupled electron transfer (PCET)” page 491 col. 2 para. 2). Note that although Cardoso fails to use the language “a composition for proximity-based labeling”, the teaching of phenol accepting an electron from flavin under diffusion control processes and while being part of a protein, inherently provides a composition for proximity-based labeling of a protein, i.e. through an oxidation reaction of the phenol in the protein by the flavin. Furthermore, although Cardoso fails to use the language “reactive intermediate”, the teaching of a “cation radical” inherently provides a reactive intermediate of the phenol (protein labeling agent).
New Rejections
Claims 77-78 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Yashin et al. Journal of Food Research; Vol. 4, No. 3; 2015 doi:10.5539/jfr.v4n3p56 (“Yashin”).
Yashin teaches “Determination of the Chemical Composition of Tea by Chromatographic Methods: A Review” (Title). Yashin furth teaches the “chemical compounds present in tea…Catechins…riboflavin” (page 57 Table 1). Note that catechins are phenols (“content of polyphenols…Catechins” page 73 Table 12). Therefore, Yashin teaches the composition claimed, a flavin and a phenol. The limitation “for proximity-based labeling”, is mere intended purpose and therefore is not imparting any structural limitation. Similarly, the specification fails to clearly define a “protein labeling agent” therefore, the reactive intermediate of the phenol is inherently interpreted to provide the “protein labeling agent” limitation claimed. Note that the specification page 13 lines 11-15 discloses that “For example, an organocatalyst can be a flavin photocatalyst. The excited flavin photocatalyst can undergo single electron transfer with phenol moieties to generate a reactive phenoxy radical. FIG. 3 illustrates a reaction mechanism for flavin-based protein labeling according to some embodiments. As illustrated in FIG. 3, the phenol protein labeling agent is functionalized with a tag or marker for assisting in identification of proteins labeled by the protein labeling agent”. The language “the phenol protein labeling agent” used by the specification suggests that the “protein labeling agent” encompasses the phenol by itself. Furthermore, vitamin B2, are photocatalysts that inherently activate phenols to a reactive intermediate via single electron transfer, i.e. oxidation reactions and the reactive intermediate has a diffusion radius prior to quenching. Therefore, the teaching of Yashin regarding tea containing a flavin and a catechins, which comprise a phenol moiety, anticipates the composition for proximity-based labeling of claims 77-78.
Claims 89-90 and 92-94 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Lowry et al. Chem. Mater. 2005, 17, 5712-5719 (“Lowry”) as evidenced by Jespersen et al. Org Process Res Dev. 2019 May 17; 23(5): 1087–1095. doi:10.1021/acs.oprd.9b00041 (“Jespersen”).
Regarding claims 89-90 and 94, Lowry teaches a composition comprising a transition metal photocatalyst of the formula
PNG
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427
435
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Greyscale
wherein M is a transition metal of the platinum group;
wherein A, D, E, G, Y and Z are independently selected from C and N; wherein R1 -R6 each represent one to four ring substituents, each of the one to four ring substituents independently selected from the group consisting of alkyl, haloalkyl, halo, -C(O)O-, and -R8OH, wherein R7 is selected from the group consisting of hydrogen and alkyl, and R8 is alkyl; and wherein X- is a counterion (“a highly luminescent ionic transition metal complex [Ir(dF(CF3)ppy)2(dtbbpy)](PF6)” Abstract). See Figure 1 of Lowry showing the claimed transition metal photocatalyst. Note that the specification page 11 line 4 discloses “[Ir(dF(CF3)ppy)2(dtbbpy)](PF6)” as an example of the transition metal photocatalyst claimed. The recitation “for proximity-based labeling”, does not impart any structural limitation to the composition comprising the transition metal photocatalyst because “for proximity-based labeling” recites the mere intended use of the composition. Therefore, although Lowry fails to use the language “for proximity-based labeling”, the [Ir(dF(CF3)ppy)2(dtbbpy)](PF6) composition would still be capable of proximity-based labeling and anticipates the claim.
Regarding claim 92, Lowry further teaches wherein the transition metal photocatalyst has a visible light extinction coefficient greater than 1000 M-1cm- 1 (“[Ir(dF(CF3)ppy)2(dtbbpy)](PF6)” Abstract). Note that the Appendix of provisional application 62858539 discloses that “[t]he extinction coefficient of the photocatalyst (3) [[Ir(dF(CF3)ppy)2(dtbbpy)](PF6) ] is five orders of magnitude larger than that of the diazirine (1) at the wavelength emitted by blue LEDs used for sensitization (450 nm)” (page 3 col. 2 para. 1). Therefore, the teaching of [Ir(dF(CF3)ppy)2(dtbbpy)](PF6) inherently provides has a visible light extinction coefficient greater than 1000 M-1cm- 1.
Regarding claim 93, although the claim is indefinite (see 112b rejection above), in the interest of compact prosecution, an aqueous-based solution is interpreted as a solution with at least 50% water. Lowery further teaches wherein the transition metal photocatalyst is soluble in an aqueous-based environment (Abstract). Note that as evidenced by Jespersen, Ir[dF(CF3)ppy]2(dtbbpy)PF6 has a solubility of “3.6×10-3” “Molar Concentration” in “1:1…Acetonitrile:Water” solvent (page 24 Table 13). Therefore, Ir[dF(CF3)ppy]2(dtbbpy)PF6 inherently provides being soluble in an aqueous-based environment.
New Rejections
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.
Claim 79 is rejected under 35 U.S.C. 103 as being unpatentable over Cardoso as applied to claim 77 above, and further in view of G-BIOSCIENCES The Protein Man's Blog Posted by The Protein Man on Aug 7, 2018 2:30:00 PM (retrieved online https://info.gbiosciences.com/blog/the-advantages-of-biotinylation-tagging-in-protein-purification on 3/15/2026) (“The Protein Man”).
Regarding claim 79, Cardoso teaches the composition of claim 77 as discussed above.
Cardoso teaches “Riboflavin as a photosensitizer. Effects on human health and food quality” (Title).
Cardoso fails to teach wherein the protein labeling agent is functionalized with a tag.
The Protein Man teaches “the advantages of biotinylation tagging in protein purification” (Title). The Protein Man further teaches that adding a biotin tag to a macromolecule “is perfectly suited for isolating and purifying proteins and protein complexes, as well as identifying protein-protein interactions and post-translational events” (page 1 para. 1). The Protein Man further teaches that a biotin tag “can be fused to a single protein molecule without interfering with its natural functions. Biotin also possesses an easily derivatized valeric side chain that can bind to reactive moieties without causing any adverse effects to its avidin-binding function” (page 1 para. 2).
It would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have modified the teachings of Cardoso to rely on the biotin-tag taught by The Protein Man because The Protein Man teaches that is perfectly suited for isolating and purifying proteins and protein complexes, as well as identifying protein-protein interactions and post-translational events and Cardoso is interested in protein-protein interactions. A person having ordinary skill in the art would have had a reasonable expectation of success because The Protein Man further teaches that a biotin tag “can be fused to a single protein molecule without interfering with its natural functions” (page 1 para. 2) and both Cardoso and The Protein Man are drawn to proteins.
Claim 91 is rejected under 35 U.S.C. 103 as being unpatentable over Lowry as applied to claim 89 above, and further in view of Wang et al. Journal of Inorganic Biochemistry 180 (2018) 179–185 https://doi.org/10.1016/j.jinorgbio.2017.12.019 (“Wang”).
Regarding claim 91, Lowry teaches the composition of claim 89 as discussed above.
Lowry fails to teach Lowry fails to teach wherein one of R1- R6 comprises a click chemistry moiety selected from the group consisting of BCN, DBCO, TCO, tetrazine, alkyne, and azide.
Wang teaches “Imaging of a clickable anticancer iridium catalyst” (Title). Wang further suggests a transition metal photocatalyst (“iridium complexes” Abstract, “Next, we selected [IrH2(Me2CO)2(PPh3)2]SbF6 as the precursor organo‑iridium complex, an effective catalyst in many catalytic reactions, including C-H activation” page 180 col. 1 para. 1). Wang further suggests the transition metal photocatalyst wherein one of R1- R6 comprises one of R1- R6 comprises a click chemistry moiety selected from the group consisting of BCN, DBCO, TCO, tetrazine, alkyne, and azide (“Complex 1-AMP exhibited the best antiproliferation activity towards human ovarian cancer A2780 cells. The azide group in complex 1-AMP” Abstract). Wang further teaches that the azide enables the imaging of cells (“After the reaction of DBCO with the azide in 1-AMP, we obtained an increasingly obvious fluorescent change in cells with time (Fig. 3a and b), while the control cells exhibited very weak fluorescence (Fig. 4a). We repeated this process and found significant fluorescence discrepancy of 1-AMP treated cells with no treated HeLa cells by both whole cells fluorescence detection and flow cytometry detection methods (Fig. 3)” page 181 col. 2 para. 1).
It would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have modified the teachings of Lowry to rely on the azide taught by Wang as one of R1- R6 because Wang suggests this enables the imaging of cells and Lowry teaches a composition for proximity-based labeling. A person having ordinary skill in the art would have had a reasonable expectation of success because both Lowry and Wang teach iridium-based photocatalysts.
New Rejections
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 89-91 and 94 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-24 and 26 of copending Application No. 19124667 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because copending Application No. 19124667 recites the transition metal photocatalyst of claims 89-90 (see claim 4 of copending Application No. 19124667), the BCN, DBCO, TCO, tetrazine, alkyne and azide click chemistry moiety of claim 91 (claim 5 of copending Application No. 19124667), wherein the transition metal is of the platinum group of claim 94 (claims 6-7 of copending Application No. 19124667).
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 92-93 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-24 and 26 of copending Application No. 19124667 in view of Lowry as evidenced by Jespersen.
Copending Application No. 19124667 recites the composition of claim 89 as discussed above.
Copending Application No. 19124667 fails to recite wherein the transition metal photocatalyst has a visible light extinction coefficient greater than 1000 M-1cm- 1 wherein the transition metal photocatalyst is soluble in an aqueous or aqueous-based environment.
Lowry teaches “[Ir(dF(CF3)ppy)2(dtbbpy)](PF6)” (Abstract). Lowry suggests that the transition metal photocatalyst has the potential for “a multitude of optoelectronic and photocatalytic applications, including organic light emitting diodes (OLEDs), photovoltaic cells, and hydrogen production via the photoreduction of water” (page 5712 col. 1 para. 1). Note that the Appendix of provisional application 62858539 discloses that “[t]he extinction coefficient of the photocatalyst (3) [[Ir(dF(CF3)ppy)2(dtbbpy)](PF6) ] is five orders of magnitude larger than that of the diazirine (1) at the wavelength emitted by blue LEDs used for sensitization (450 nm)” (page 3 col. 2 para. 1). Therefore, the teaching of [Ir(dF(CF3)ppy)2(dtbbpy)](PF6) inherently provides has a visible light extinction coefficient greater than 1000 M-1cm- 1. Note also that as evidenced by Jespersen, Ir[dF(CF3)ppy]2(dtbbpy)PF6 has a solubility of “3.6×10-3” “Molar Concentration” in “1:1…Acetonitrile:Water” solvent (page 24 Table 13). Therefore, Ir[dF(CF3)ppy]2(dtbbpy)PF6 inherently provides being soluble in an aqueous-based environment.
It would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have modified the teachings of copending Application No. 19124667 to rely on the transition metal photocatalyst having visible light extinction coefficient greater than 1000 M-1cm- 1 taught by Lowry because Lowry suggests this enables the potential for a multitude of optoelectric and photocatalytic applications, including organic light emitting diodes (OLEDs), photovoltaic cells, and hydrogen production via the photoreduction of water. A person having ordinary skill in the art would have had a reasonable expectation of success because both references are drawn to transition metal photocatalysts.
Claims 89-91 and 94 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-22, 24, 27, 30 and 33 of copending Application No. 19128844 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because copending Application No. 19128844 recites the transition metal photocatalyst of claims 89-91 (see claims 3, 6 and 12 of copending Application No. 19128844), wherein the transition metal is of the platinum group of claim 94 (claims 5 and 14 of copending Application No. 19128844).
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claim 92-93 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-22, 24, 27, 30 and 33 of copending Application No. 19128844 in view of Lowry as evidenced by Jespersen.
Copending Application No. 19128844 recites the composition of claim 89 as discussed above.
Copending Application No. 19128844 fails to recite wherein the transition metal photocatalyst has a visible light extinction coefficient greater than 1000 M-1cm- 1 wherein the transition metal photocatalyst is soluble in an aqueous or aqueous-based environment.
Lowry teaches “[Ir(dF(CF3)ppy)2(dtbbpy)](PF6)” (Abstract). Lowry suggests that the transition metal photocatalyst has the potential for “a multitude of optoelectronic and photocatalytic applications, including organic light emitting diodes (OLEDs), photovoltaic cells, and hydrogen production via the photoreduction of water” (page 5712 col. 1 para. 1). Note that the Appendix of provisional application 62858539 discloses that “[t]he extinction coefficient of the photocatalyst (3) [[Ir(dF(CF3)ppy)2(dtbbpy)](PF6) ] is five orders of magnitude larger than that of the diazirine (1) at the wavelength emitted by blue LEDs used for sensitization (450 nm)” (page 3 col. 2 para. 1). Therefore, the teaching of [Ir(dF(CF3)ppy)2(dtbbpy)](PF6) inherently provides has a visible light extinction coefficient greater than 1000 M-1cm- 1. Note also that as evidenced by Jespersen, Ir[dF(CF3)ppy]2(dtbbpy)PF6 has a solubility of “3.6×10-3” “Molar Concentration” in “1:1…Acetonitrile:Water” solvent (page 24 Table 13). Therefore, Ir[dF(CF3)ppy]2(dtbbpy)PF6 inherently provides being soluble in an aqueous-based environment.
It would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have modified the teachings of copending Application No. 19128844 to rely on the transition metal photocatalyst having visible light extinction coefficient greater than 1000 M-1cm- 1 taught by Lowry because Lowry suggests this enables the potential for a multitude of optoelectric and photocatalytic applications, including organic light emitting diodes (OLEDs), photovoltaic cells, and hydrogen production via the photoreduction of water. A person having ordinary skill in the art would have had a reasonable expectation of success because both references are drawn to transition metal photocatalysts.
This is a provisional nonstatutory double patenting rejection.
Claims 89-91 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-33 of copending Application No. 19134520 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because copending Application No. 19134520 recites the transition metal photocatalyst of claims 89-91 (see claims 10 and 14 of copending Application No. 19134520).
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claim 92-94 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-33 of copending Application No. 19134520 in view of Lowry as evidenced by Jespersen.
Copending Application No. 19134520 recites the composition of claim 89 as discussed above.
Copending Application No. 19134520 fails to recite wherein the transition metal photocatalyst has a visible light extinction coefficient greater than 1000 M-1cm- 1 wherein the transition metal photocatalyst is soluble in an aqueous or aqueous-based environment, wherein M is selected from transition metals of the platinum group.
Lowry teaches “[Ir(dF(CF3)ppy)2(dtbbpy)](PF6)” (Abstract). Lowry suggests that the transition metal photocatalyst has the potential for “a multitude of optoelectronic and photocatalytic applications, including organic light emitting diodes (OLEDs), photovoltaic cells, and hydrogen production via the photoreduction of water” (page 5712 col. 1 para. 1). Note that the Appendix of provisional application 62858539 discloses that “[t]he extinction coefficient of the photocatalyst (3) [[Ir(dF(CF3)ppy)2(dtbbpy)](PF6) ] is five orders of magnitude larger than that of the diazirine (1) at the wavelength emitted by blue LEDs used for sensitization (450 nm)” (page 3 col. 2 para. 1). Therefore, the teaching of [Ir(dF(CF3)ppy)2(dtbbpy)](PF6) inherently provides has a visible light extinction coefficient greater than 1000 M-1cm- 1. Note also that as evidenced by Jespersen, Ir[dF(CF3)ppy]2(dtbbpy)PF6 has a solubility of “3.6×10-3” “Molar Concentration” in “1:1…Acetonitrile:Water” solvent (page 24 Table 13). Therefore, Ir[dF(CF3)ppy]2(dtbbpy)PF6 inherently provides being soluble in an aqueous-based environment.
It would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to have modified the teachings of copending Application No. 19134520 to rely on the platinum group transition metal photocatalyst having visible light extinction coefficient greater than 1000 M-1cm- 1 taught by Lowry because Lowry suggests this enables the potential for a multitude of optoelectric and photocatalytic applications, including organic light emitting diodes (OLEDs), photovoltaic cells, and hydrogen production via the photoreduction of water. A person having ordinary skill in the art would have had a reasonable expectation of success because both references are drawn to transition metal photocatalysts.
This is a provisional nonstatutory double patenting rejection.
Response to Arguments
Applicant's arguments filed 2/24/2026 have been fully considered but they are not persuasive.
Regarding the Priority Benefit,
Applicant argues that “the single electron transfer is discussed in the Appendix of provisional application serial number 62/858,539 and illustrated in FIG. 2 above” (page 11 para. 4).
However, FIG. 2 of the Appendix of provisional application serial number 62/858,539 clearly shows “Dexter energy transfer”. Furthermore, the discussion regarding single-electron transfer in the Appendix of provisional application serial number 62/858,539 is with regards to “phenoxy
radicals…through peroxidase activation” (page 2 col. 1 para. 1). Therefore, this is clearly not the same as the transition metal photocatalyst activation reaction claimed.
Regarding the 102 rejections of claims 77-78,
Applicant argues that “Cardoso fails to disclose or teach the limitations of claims 77 and 78” (page 14 para. 5).
However, Cardoso does anticipate the claims (see rejection above).
Regarding the double patenting rejections,
Applicant “requests that the non-statutory double patent rejections be held in abeyance until allowed claims are identified in the present application” (page 14 para. 6).
However, there is no allowable subject matter.
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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to FERNANDO IVICH whose telephone number is (703)756-5386. The examiner can normally be reached M-F 9:30-6:00 (E.T.).
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/Fernando Ivich/Examiner, Art Unit 1678
/CHRISTOPHER L CHIN/Primary Examiner, Art Unit 1677