DETAILED ACTION
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on November 3 2025 has been entered.
Receipt of Arguments/Remarks filed on November 3 2025 is acknowledged. Claims 9-21, 25-26, 28, 34-35, 37-40, 44-48, 51-52 and 55 were/stand cancelled. Claims 1 and 56-58 were amended. Claims 1-8, 22-24, 27, 29-33, 36, 41-43, 49-50, 53-54 and 56-58 are pending. Claims 3, 5, 7, 30-33, 36, 41-43, 49-50 and 53-54 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on February 20 2025. Claims 1-2, 4, 6, 8, 22-24, 27, 29 and 56-58 are directed to the elected invention.
As previously indicated, the elected species of formula A is free of prior art. The examiner additionally notes that species falling within the scope of Formula K, L, M, N, O, P, Q and R as recited in claim 8 encompassing the elected species is also free of prior art. Specifically, the prior art does not suggest the instantly claimed compound where L1 is -CH2CH2OCH2CH2OCH2CH2- and R1 is H.
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 .
Withdrawn Objections/Rejections
Acknowledgement is made of amendments to the specification capitalizing the trademark. Therefore, the objection is withdrawn.
Claim Rejections - 35 USC § 112
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 1-2, 4, 6, 8, 23-24, 27, 29 and 56-58 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.
In light of the amendments to the claims, the scope of the claim terms is unclear.
In claim 1: R is a chemical moiety selected from hydrogen, halogens, hydroxyls, alkoxyl which are not indefinite. But the claim also recites species for R of “straight aliphatics, branched aliphatics, cyclic aliphatics, unsubstituted aliphatics, saturated aliphatics, unsaturated aliphatics” which are indefinite. The instant specification provides no limiting definition of the term aliphatic. Therefore, the broadest reasonable interpretation of these terms is their normal terminology in the art.
Britannica defines aliphatic compound as “any chemical compound belonging to the organic class in which the atoms are connected by single, double, or triple bonds to form nonaromatic structures. One of the major structural groups of organic molecules, the aliphatic compounds include the alkanes, alkenes, and alkynes and substances derived from them—actually or in principle—by replacing one or more hydrogen atoms by atoms of other elements or groups of atoms.”
Fiveable defines aliphatic compounds to be organic molecules consisting of carbon and hydrogen arranged in straight chains, branched chains, or non-aromatic rings. They can be saturated (alkanes) or unsaturated (alkenes and alkynes).
In light of the definition of the terms in the art, and the use of modifiers before the recitation aliphatics, the scope of the claims are not clear. If aliphatics is intended to “consist of” carbon and hydrogen as recited in the definition in fiveable, then why would the recitation “unsubstituted” be necessary. Since the claims include the modifier “unsubstituted” before aliphatic this seems to indicate that the recitation “straight aliphatics, branched aliphatics, cyclic aliphatics, saturated aliphatics and unsaturated aliphatics” would allow for substitutions as encompassed by the definition in Britannica of aliphatic. If these terms were not intended to encompass substitution, then how is the scope of “unsubstituted aliphatics” of a different scope than the other terms in the claim.
Since the specification provides no explanation of the scope of these terms, the resulting scope is indefinite. The examiner will interpret these aliphatic recitations as allowing for substitution except for the recitation unsubstituted aliphatics as that recitation makes it clear that substitution is not allowed.
The examiner notes claim 22 is not included in the rejection as this claim is interpreted as limited to those species recited and not including substitutions.
Claims 23-24, 27, 29 and 56-58 are included in the rejection as they depend on a rejected base claim and they do not clarify the issues.
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.
Claim(s) 1-2, 4, 6, 8, 24, 27, 29 and 56-58 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Noguchi et al. (Bioorganic & Medicinal Chemistry, 2008, cited in the Office Action mailed on 12/12/2024).
The instant application claims a photocleavable heterobifunctional linker comprising a structure of formula A. The recitation chemical moiety is interpreted to mean any chemical group of any length. With regards to leaving group, this is interpreted as reading on any group which has a cleavable bond. Capture agent includes a ligand. As recited in paragraph 0086 of the instant specification, the capture entity is configured or selected for the desired target, where the capture entity has affinity of selectively for the desired target.
Noguchi et al. is directed to the development of novel water-soluble photocleavable protective group and its application for design of photoresponsive paclitaxel prodrugs. A specifically taught compound is compound 11:
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. This reads on the instantly claimed compound wherein R9 and R10 are hydrogen, L2 is a sub-linker (NH-CH(phenyl)-CH(OBz)-) and R2 is a leaving group/capture entity (i.e. isotaxel) (i.e. a C(O)O bond), R is a substituted aliphatic, L1 is a sublinker (CH2-C(O)), R1 is a leaving group/protecting group.
Compound 11 reads on formula B, D, F and H.
Regarding R of claim 1, claim 1 recites R can be straight chain or branched aliphatics. The recitation aliphatic is indefinite for the reasons set forth above. Since the term is indefinite, the scope of aliphatics, unless expressly stated as unsubstituted, is interpreted as including substitution. Therefore the CH2-C(O)-NH-CH2-CH2-N(CH3)2 reads on substituted straight or branched aliphatic.
Regarding claim 24, the recitation carboxyl protecting group, aryl ester, is interpreted as reading on any aryl ester (i.e. it includes any substitutions and is not limited to benzyl). Since compound 11 above include C(O)-O-Aryl containing compound, it reads on the instantly claimed aryl ester protecting group.
Regarding claim 27, the claim recites the L1 and L2 sub-linkers each independently include…This is interpreted as requiring, for example, alkyl, but additional chemical moieties can be present. This interpretation is based on the “includes” recitation which the examiner equates to comprising. Compound 11 as recited would include L2 sub-linker (NH-CH(phenyl)-CH(OBz)-) (i.e. includes alkyl) and L1 is a sublinker (CH2-C(O)) (i.e. ester).
Regarding claim 29, the isotaxel reads on ligand as it would bind to a receptor.
Regarding claims 56-58, R9 and R10 are hydrogen.
Response to Arguments
Applicants’ arguments filed November 3 2025 have been fully considered but they are not persuasive.
Applicants argue that claim 1 has been amended to recite subject matter that is not taught or suggested by Noguchi et al.
Regarding Applicants’ arguments, the examiner cannot agree. In light of the indefiniteness of the recitation aliphatic, the claim is interpreted as allowing for substitution unless expressly stated as “unsubstituted”. Claim 1 recites R can be straight or branched aliphatics. Thus the CH2-C(O)-NH-CH2-CH2-N(CH3)2 reads on substituted straight or branched aliphatic. Therefore, the claims have not been amended to distinguish the instant claims from Noguchi et al.
Claim(s) 1-2, 4, 6, 8, 27, 29 and 56-58 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Chen et al. (Nanomaterials, 2019, cited in the Office action mailed on April 14 2025).
The instant application claims a photocleavable heterobifunctional linker comprising a structure of formula A. The recitation chemical moiety is interpreted to mean any chemical group of any length. With regards to leaving group, this is interpreted as reading on any group which has a cleavable bond. Capture agent includes a ligand. As recited in paragraph 0086 of the instant specification, the capture entity is configured or selected for the desired target, where the capture entity has affinity of selectively for the desired target.
Chen et al. is directed to a photocleavable amphiphilic prodrug self-assembled nanoparticles with effective anticancer activity in vitro. Scheme 1 shows the synthesis of MTX-AMC-PEG conjugate:
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. Compound 4 reads on the instantly claimed compound. Specifically it reads on formula B, D, F and H. R9 and R10 are H. L1 is sublinker CH2C(O) (i.e. ester). L2 is sublinker (CH2)2CH(COOH)NH (i.e. contains alkyl). R1 is a capture entity as it reads on ligand and R2 is a leaving group.
Regarding R of claim 1, claim 1 recites R can be straight chain or branched aliphatics. The recitation aliphatic is indefinite for the reasons set forth above. Since the term is indefinite, the scope of aliphatics, unless expressly stated as unsubstituted, is interpreted as including substitution. Therefore the CH2-C(O)-NH-CH2-CH2-O-(CH2)2-OCH3 reads on substituted aliphatic.
Regarding claims 56-58, R9 and R10 are hydrogen.
Response to Arguments
Applicants’ arguments filed November 3 2025 have been fully considered but they are not persuasive.
Applicants argue that (1) claim 1 has been amended to recite subject matter that is not taught or suggested by Chen et al.
Regarding Applicants’ arguments, the examiner cannot agree. In light of the indefiniteness of the recitation aliphatic, the claim is interpreted as allowing for substitution unless expressly stated as “unsubstituted”. Claim 1 recites R can be straight or branched aliphatics. The CH2-C(O)-NH-CH2-CH2-O-(CH2)2-OCH3 reads on substituted branched or straight aliphatic. Therefore, the claims have not been amended to distinguish the instant claims from Noguchi et al.
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 of this title, 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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-2, 4, 6, 8, 22, 27, 29 and 56-58 are rejected under 35 U.S.C. 103 as being unpatentable over Lv et al. (Chem. Sci. 2015, cited in the Office action mailed on April 14 2025) in view Kulkarni et al. (Cancer Research, 1981, cited in the Office Action mailed on April 14 2025) and Chen et al. (Nanomaterials, 2019, cited in the Office Action mailed on April 14 2025) as evidenced by Asiaei (Biomicrofluidics, 2015).
Applicant Claims
The instant application claims a photocleavable heterobifunctional linker comprising a structure of formula A. The recitation chemical moiety is interpreted to mean any chemical group of any length. With regards to leaving group, this is interpreted as reading on any group which has a cleavable bond. Capture agent includes a ligand. As recited in paragraph 0086 of the instant specification, the capture entity is configured or selected for the desired target, where the capture entity has affinity of selectively for the desired target.
Determination of the Scope and Content of the Prior Art
(MPEP §2141.01)
Lv et al. is directed to photoresponsive immunomagnetic nanocarrier for capture and release of rare circulating tumor cells. Taught is a compound (7):
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which is formed by coupling biotin to a photoresponsive molecule via EDC/DMAP. This compound is then coupled with EDC/NHS to IgG (see Scheme 1) which would result in C(O)NH-IgG as evidenced by Asiaei et al. IgG is a capture agent as shown in scheme 1 (see also supporting information). The coumarin moieties produce cleavage of a C-O bond under illumination, leading to separation of the two ends (page 6434, left column).
Ascertainment of the Difference Between Scope the Prior Art and the Claims
(MPEP §2141.02)
While Lv et al. suggests the use of coumarin to bridge a capture antibody and streptavidin, Lv et al. does not teach bridging with outer molecules which would lead to the instantly claimed L2-C(O)-R2. However, this deficiency is cured by Chen et al. and Kulkarni et al.
Kulkarni et al. is directed to covalent binding of methotrexate to immunoglobulin and the effect of antibody-linked drug on tumor growth in vivo. A number of factors may contribute to the increase in tumor-inhibitory capacity that arises on conjugation to an antitumor IgG. The binding of methotrexate to anti-ELF4 globulin conjugates on EL4 cells shows that specific antibody-mediated targeting of the drug on free-floating tumor cells (page 2705).
Chen et al. is directed to a photocleavable amphiphilic prodrug self-assembled nanoparticles with effective anticancer activity in vitro. Scheme 1 shows the synthesis of MTX-AMC-PEG conjugate:
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. Conjugation of methotrexate to the coumarin is done via EDC (scheme 1).
Finding of Prima Facie Obviousness Rationale and Motivation
(MPEP §2142-2143)
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to combine the teachings of Lv et al., Kulkarni et al. and Chen et al. and replace biotin of Lv et al. with methotrexate. One skilled in the art would have been motivated to utilize methotrexate with IgG in order to provide improved specificity of the chemotherapeutic agent as taught by Kulkarni et al. Specifically, Lv et al. recognizes the use of IgG to capture circulating tumor cells. Since Chen et al. teaches the use of coumarin derivatives with methotrexate and Kulkarni et al. teaches that methotrexate/IgG conjugates can target the drug to free-floating tumor cells, there is a reasonable expectation of success in combining the coumarin photocleavable moiety with both IgG and methotrexate.
Regarding the claimed structure of the instantly claimed linker, coupling of IgG and methotrexate to the photoresponsive molecule of Lv et al. results in R1-NH of a capture entity/antibody (i.e. IgG); L1 being a sublinker CH2-C(O) (i.e. contains alkyl); R is CH2-CH3 (i.e. ethyl); R9 and R10 being H; L2 is sublinker (CH2)2CH(COOH)NH (i.e. contains alkyl); and R2 is a leaving group.
As evidenced by Asiaei et al. (Fig. 1) an antibody is coupled to a carboxylic acid via EDC/NHS via the NH2 on the antibody which results in R-C(O)-N(H)-R’. This structure is also supported in the supplemental (page 16).
Claims 1-2, 4, 6, 8, 22-24, 27, 29 and 56-58 are rejected under 35 U.S.C. 103 as being unpatentable over Noguchi et al. as applied to claims 1-2, 4, 6, 8, 24, 27, 29 and 56-58 above in view of Patani et al. (Chemical Reviews, 1996, cited in the Office Action mailed on April 14 2025).
Applicant Claims
The instant application claims wherein R, R9, and R10 are each independently selected from hydrogen, methyl, ethyl, propyl, butyl, cyclopropyl, cyclobutyl, cyclohexyl, or combinations thereof.
The instant application claims R1 is selected from hydrogen, tert-butyloxycarbonyl (Boc), 9-a fluorenylmethyloxycarbonyl (Fmoc), trifluoroacetyl, benzyl, 2-nitrophenylethyl carbamate or 6-nitroveratryl carbamate, fluoride, trimethylsilylethyloxycarbonyl (Teoc), or 1,3-dithian-2-ylmethoxycarbonyl (Dmoc).
Determination of the Scope and Content of the Prior Art
(MPEP §2141.01)
Noguchi et al. is directed to the development of novel water-soluble photocleavable protective group and its application for design of photoresponsive paclitaxel prodrugs. A specifically taught compound is compound 11:
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. This reads on the instantly claimed compound wherein R9 and R10 are hydrogen, L2 is a sub-linker (NH-CH(phenyl)-CH(OBz)-) and R2 is a leaving group/capture entity (i.e. isotaxel) (i.e. a C(O)O bond). In one reading R is a chemical moiety, L1 is a sublinker (CH2-C(O)), R1 is a leaving group/protecting group.
Ascertainment of the Difference Between Scope the Prior Art and the Claims
(MPEP §2141.02)
The instant claims encompass a coumarin derivative. Therefore, one reading of the compound of Noguchi et al. is where the coumarin is a coumarin derivative with (CH3)2-(CH2)2-NH. Specifically the following structure is the “coumarin” portion of phototaxel 11 in Noguchi et al.
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which would then leave this portion:
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corresponding to (Left to Right) R1-NH-L1-N(R).
The difference between the instant claims and the prior art is the methyl groups on the terminal nitrogen, corresponding to R1 instead of the instantly claimed hydrogens. However, this deficiency is cured by Patani et al.
Patani et al. is directed to bioisosterism: a rational approach in drug design. Bioisosterism is the idea of similarities of various physiochemical properties of atoms, groups., radical and molecules (page 3148, left column). It is taught that fluorine and hydroxyl, amino or methyl groups are replacements for hydrogen which is Grimm’s hydride displacement law (page 3152, section 4.).
Finding of Prima Facie Obviousness Rationale and Motivation
(MPEP §2142-2143)
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to combine the teachings of Noguchi et al. and Patani et al. and replace the methyl with hydrogens. One skilled in the art would have expected that replacement of the methyl with hydrogen would afford similar properties as hydrogen and methyl are bioisosteres as taught by Patani et al.
It is well established that the substitution of methyl for hydrogen on a known compound is not a patentable modification absent unexpected or unobvious results. In re Lincoln, 126 U.S.P.Q. 477, 53 U.S.P.Q. 40 (C.C.P.A. 1942); In re Druey, 319 F.2d 237, 138 U.S.P.Q. 39 (C.C.P.A. 1963); In re Lohr, 317 F.2d 388, 137 U.S.P.Q. 548 (C.C.P.A. 1963): In re Hoehsema, 399 F.2d 269, 158 U.S.P.Q. 598 (C.C.P.A. 1968); In re Wood, 582 F.2d 638, 199 U.S.P.Q. 137 (C.C.P.A. 1978); In re Hoke, 560 F.2d 436, 195 U.S.P.Q. 148 (C.C.P.A. 1977); Ex parte Fauque, 121 U.S.P.Q. 425 (P.O.B.A. 1954); Ex parte Henkel, 130 U.S.P.Q. 474, (P.O. B.A. 1960) MPEP 2144.08.
Response to Arguments
Applicants’ arguments filed November 3 2025 have been fully considered but they are not persuasive.
Applicants argue that (1) the second 103 is over Noguchi and the examiner states that the substituent on the N still reads on the instant claims because the instant claims encompass R as being substituted aliphatics. Since claim 1 no longer species that R may be substituted, the rejection is no moot.
Regarding Applicants’ first argument, firstly, as indicated in the 102 the instantly claimed aliphatics is indefinite and encompasses substitution. Nonetheless, the rejection under 103 is not based on this interpretation. As clarified above, the “coumarin” in the instant claims encompasses “coumarin derivative” and nothing in the specification or the claims places a structural limitation on the recitation derivative. Therefore, in Noguchi et al.
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portion of the molecule reads on “coumarin derivative” and
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corresponding to (Left to Right) R1-NH-L1-N(R). Therefore, R is H in this portion of the molecules and R1 is methyl. However, this portion of the molecule includes a methyl instead of the claimed H. The rejection is based the obviousness of replacing methyl with hydrogen. The amendments have not distinguished the instant claims from this interpretation nor established an unexpected effect with the instant claimed NH-CH3 compared to N-(CH3)2 taught in Noguchi et al.
Applicants argue that (2) LV does not teach the presence of L1-NH-R1. The office action asserts that compound 7 is coupled with EDC/NHC to IgG which would result in C(O)-NH-IgG. It is argued that LV fails to teach instances where L1-NH-R1. It is argued that while one hand the Office action appears to be asserting that LV teaches NH is not part of the IgG while on the other hand asserting that NH is part of the IgG. LV provides the following structure for the combination of compound 7 with IgG which suggest that no NH of the IgG would be coupled to compound 7. It is argued that the Office Action has not provide any indication as to where the NH in the asserted C(O)NH-IgG is derived.
Regarding Applicants’ second argument, LV teaches “Here, a 7-aminocoumarin compound with a hydroxyl group and a carboxyl group was reacted with biotin via the hydroxyl group to construct a biotin-7-aminocoumarin compound (biotin-photoresponsive molecule, BPM) as the photoresponsive linker, and the carboxyl group was subsequently used for conjugation with antibodies” (synthesis of photoresponsive linker and references figure Fig. S2). The supplemental material (previously provided with the LV reference) expressly teaches the mechanism of photoinduced release:
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Which as pointed to (see arrow) shows bonding of the antibody (IgG) to the carboxyl group of the BPM. This clearly shows an C(O)-NH-R1. As evidenced by Asiaei et al. conjugation of an antibody to a carboxylic acid with EDC/NHS is via an amine on the antibody. This results in the instantly claimed L1-NH-R1
Regarding Applicants of the NH being part/not part of IgG. The instant claims are directed to a product. The question for obviousness is does the prior art suggest the same structure. Here, when coupling IgG to the photoresponsive BPM (as suggested by LV et al.) would result in L1-NH-R1. While the NH might come from IgG, this NH is not the sole structure of IgG. Since attachment would have to occur at some position on IgG. While Applicants may not specifically teach such reaction, this does not distinguish the instant claims from the prior art. Nothing in the claims exclude the NH-R1 portion of Formula A from originating from IgG. Therefore, contrary to Applicants assertion, there are not a nearly infinite number of different chemical modification patterns that could be at R and L1-NH-R1 as LV et al. expressly teaches coupling IgG to the BPM which the supplemental material clearly shows results in L1-NH-R1 and R falling within the scope claimed.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ABIGAIL VANHORN whose telephone number is (571)270-3502. The examiner can normally be reached M-Th 6 am-4 pm EST.
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/ABIGAIL VANHORN/Primary Examiner, Art Unit 1636