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.
This office action is a response to applicant’s communication submitted June 27, 2024, wherein claims 1, 18, and 20 were preliminarily amended, and claims 21-33 were added.
Claims 1-33 are pending in this application.
Priority
This application is a continuation of U.S. Application Serial No. 17/943,824, filed September 13, 2022, which claimed priority to U.S. Provisional Application Serial No. 63/243,539 filed September 13, 2021.
Specification
The disclosure is objected to because it contains an embedded hyperlink and/or other form of browser-executable code (pg. 13, para. 0042, pg. 17, top of page). Applicant is required to delete the embedded hyperlink and/or other form of browser-executable code; references to websites should be limited to the top-level domain name without any prefix such as http:// or other browser-executable code. See MPEP § 608.01.
Appropriate correction is required.
Claim Objections
Claims 20-21, 24-25, 28-29, and 31-33 are objected to because of the following informalities:
Claims 20-21, 24-25, 28-29, and 32-33 are objected to because the term “luekemia” should read “leukemia”.
Claims 31-33 are objected to under 37 CFR 1.75 as being a substantial duplicate of claims 27-29. When two claims in an application are duplicates or else are so close in content that they both cover the same thing, despite a slight difference in wording, it is proper after allowing one claim to object to the other as being a substantial duplicate of the allowed claim. See MPEP § 608.01(m).
Appropriate correction is required.
Claim Rejections - 35 USC § 112 (d)
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 21, 23-25 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Claim 21 recites a method comprising administering the pharmaceutical composition of claim 1. However, claim 1 is directed towards a compound, not a pharmaceutical composition. Thus claim 21 expands, rather than limits claim 1.
Claim 23 recites a pharmaceutical composition comprising the compound of claim 21. However, claim 21 is directed towards a method of administering a pharmaceutical composition, not a compound. Thus claim 23 expands, rather than limits claim 21.
Claim 24 recites a method comprising administering the compound of claim 21. However, claim 21 is directed towards a method, not a compound . Thus claim 24 fails to further limit claim 21.
Claim 25 recites a method comprising administering the pharmaceutical composition of claim 23. However, claim 23 already depends from a method comprising administering a composition. Thus claim 25 fails to further limit claim 23.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1 and 18 rejected under 35 U.S.C. 102(a)(1) as being anticipated by PubChem (CID 146297652, IDS filed on May 6, 2024).
Regarding claims 1 and 18: PubChem teaches a compound with structure:
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(pg. 2). The structure falls under the scope of formula (IV) as recited by instant claims 1 and 18: wherein R1 is R18C(O)NH-; R18 is the residue of a hydroxamic acid histone deacetylase inhibitor (Panobinostat, pg. 23 of the instant specification).
Claims 1 and 17-18 rejected under 35 U.S.C. 102(a)(1) as being anticipated by PubChem (CID 146297597, cited on PTO-892).
Regarding claims 1 and 17-18: PubChem teaches a compound with structure:
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(pg. 2). The structure falls under the scope of formula (IV) as recited by instant claims 1 and 17-18: wherein R1 is R18C(O)NH-; R18 is the residue of a hydroxamic acid histone deacetylase inhibitor (Panobinostat, pg. 23 of the instant specification); and R9 is alkyl.
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.
Claims 1-21 and 23-33 are rejected under 35 U.S.C. 103 as being unpatentable over Gallop (US 2020/0016185, IDS filed August 7, 2024) in view of Hevey (Chem. Eur. J., 2021, IDS filed May 6, 2024).
Regarding claims 1-21 and 23-25: Gallop teaches compounds that are non-toxic prodrugs of senolytic agents which are activated by glycosidases that preferentially accumulate inside senescent cells:
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(pg. 1, para. 0006). The functionality of HDAC inhibitors (i.e., Panobinostat) is masked as a glycoside derivative (pg. 19, paras. 0108-109). This ensures that prodrugs are inactive as HDAC inhibitors, but will become activated upon hydrolysis within the lysosomes of senescent cells (pg. 19, paras. 0108-109). Gallop teaches prodrugs of histone deacetylase inhibitors capable of promoting apoptosis in senescent cells (pg. 1, paras. 0006-0008). These senolytic agents may be combined with at least one pharmaceutically acceptable excipient to form a pharmaceutical composition and administered to a subject for the purpose of killing senescent cells (pg. 57, para. 0269). Gallop further teaches HDAC inhibitors have been approved for the clinical treatment of cancers such as leukemia (pg. 47, paras. 0199-0201, pg. 48, para. 0207). Gallop teaches the methods are useful for inhibiting retarding or slowing progression of metastatic cancer including leukemia (pg. 48, para. 0208). Gallop teaches the following compound:
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(pg. 17, para. 0105). Gallop teaches acetyl as a protecting group for hydroxy groups to act as a mask or reduce reactivity of the functional group (pgs. 5-6, para. 0082).
Gallop does not teach wherein the R3 position is H or F. Gallop does not teach wherein R2, R3, R4, R6, R7, and R8 are fluorine (F).
However, Hevey teaches “the use of native glycan structures has met with limited success, which can be attributed to their characteristic high polarity (e.g., low binding affinities) and inherently poor pharmacokinetic properties (e.g., short drug–target residence times, rapid renal excretion), leading to the development of ’glycomimetics’. Fluorinated drugs have become increasingly common over recent decades, with fluorinated glycomimetics offering some unique advantages. Deoxyfluorination maintains certain electrostatic interactions, while concomitantly reducing net polarity through ’polar hydrophobicity’, improving residence times and binding affinities. Fluorination destabilizes the oxocarbenium transition state associated with metabolic degradation, and can restore exo and endo-anomeric effects in C-glycosides and carbasugars” (pg. 2241, abstract). There are two main fluorination strategies: OH to F substitution, and H to F substitution (pg. 2243, section 1.2). Fluorine substitution at the C-2 position is the most effective at slowing hydrolysis (pg. 2245, section 3.1). Additional changes such as replacing OH groups with hydrogen are also routinely studied in the art (pg. 2242, section 2.1). Hevey also teaches that in a pro-drug approach, esterification of glycans OH groups can be used to temporarily mask hydrophilicity to facilitate membrane permeability, in which, upon cell entry, endogenous esterases cleave the acetyl groups to produce the free glycan (pg. 2245, section 3.1). A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities (See MPEP 2144.09).
Taken together it would have been prima facie obvious to a person of ordinary skill in the art to modify the compounds of Gallop by replacing OH or OAc groups with fluorine as suggested by Hevey. A person of ordinary skill in the art would have had the motivation to do so with a reasonable expectation of success in order to impart greater enzymatic stability to the structure and replacement with fluorine groups in glycomimetic structures is a known technique in the art. A person of ordinary skill in the art would be capable of determining the optimal degree of substitution with fluorine.
Regarding claims 26-33: Gallop does not teach the specific compounds recited by instant claims 26 and 31. With respect to the specific compounds recited by instant claims 26 and 31, as discussed above, from the teachings of Gallop hydroxyl groups can be interchanged with acylated groups as shown in the following structures:
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(pg. 10, para. 0100, first compound)
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(pg. 12, para. 0102, first structure). A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities (See MPEP 2144.09). Hevey teaches OH to fluorine and H to fluorine substitutions in glycomimetic development are routine practices in the art (pg. 2243, section 1.2). Additional changes such as replacing OH groups with hydrogen are also routinely studied in the art (pg. 2242, section 2.1).
Taken together it would have been prima facie obvious to one of ordinary skill in the art to arrive at the compounds as claimed given that varying fluorine, hydrogen, hydroxyl, and acetyl groups in the glucuronide ring is a routine technique in the art of glycomimetic/senolytic drugs for the purpose of treating cancer.
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 1-21 and 23-33 are rejected on the ground of nonstatutory double patenting as being unpatentable over the claims of U.S. Patent No. 11,026,963 (IDS filed May 6, 2024, hereinafter “US-963) in view of Gallop (US 2020/0016185, IDS filed August 7, 2024) and Hevey (Chem. Eur. J., 2021, IDS filed May 6, 2024).
Patented claim 5 of US-963 recite a compound with the following structure:
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. Patented claim 7 of US-963 recite a compound with a structure of:
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. Claim 6 of US-963 recites a pharmaceutical composition comprising the compound of claim 5 and a pharmaceutically acceptable excipient. Patented claim 13 of US-963 recite a method for treating a senescence-associated disease or disorder comprising administering to a subject in need thereof a therapeutically-effective amount of the compound of claim 5.
The patented claims do not teach wherein the R3 position is H or F. The patented claims do not teach wherein R2, R3, R4, R6, R7, and R8 are fluorine (F). The patented claims do not teach the specific compounds recited by instant claims 26 and 31.
However, Gallop teaches compounds that are non-toxic prodrugs of senolytic agents which are activated by glycosidases that preferentially accumulate inside senescent cells:
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(pg. 1, para. 0006). The functionality of HDAC inhibitors (i.e., Panobinostat) is masked as a glycoside derivative (pg. 19, paras. 0108-109). This ensures that prodrugs are inactive as HDAC inhibitors, but will become activated upon hydrolysis within the lysosomes of senescent cells (pg. 19, paras. 0108-109). Gallop teaches prodrugs of histone deacetylase inhibitors capable of promoting apoptosis in senescent cells (pg. 1, paras. 0006-0008). These senolytic agents may be combined with at least one pharmaceutically acceptable excipient to form a pharmaceutical composition and administered to a subject for the purpose of killing senescent cells (pg. 57, para. 0269). Gallop further teaches HDAC inhibitors have been approved for the clinical treatment of cancers such as leukemia (pg. 47, paras. 0199-0201, pg. 48, para. 0207). Gallop teaches the methods are useful for inhibiting retarding or slowing progression of metastatic cancer including leukemia (pg. 48, para. 0208). Gallop teaches the following compound:
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(pg. 17, para. 0105). Gallop teaches acetyl as a protecting group for hydroxy groups to act as a mask or reduce reactivity of the functional group (pgs. 5-6, para. 0082). Hevey teaches “the use of native glycan structures has met with limited success, which can be attributed to their characteristic high polarity (e.g., low binding affinities) and inherently poor pharmacokinetic properties (e.g., short drug–target residence times, rapid renal excretion), leading to the development of ’glycomimetics’. Fluorinated drugs have become increasingly common over recent decades, with fluorinated glycomimetics offering some unique advantages. Deoxyfluorination maintains certain electrostatic interactions, while concomitantly reducing net polarity through ’polar hydrophobicity’, improving residence times and binding affinities. Fluorination destabilizes the oxocarbenium transition state associated with metabolic degradation, and can restore exo and endo-anomeric effects in C-glycosides and carbasugars” (pg. 2241, abstract). There are two main fluorination strategies: OH to F substitution, and H to F substitution (pg. 2243, section 1.2). Fluorine substitution at the C-2 position is the most effective at slowing hydrolysis (pg. 2245, section 3.1). Additional changes such as replacing OH groups with hydrogen are also routinely studied in the art (pg. 2242, section 2.1). Hevey also teaches that in a pro-drug approach, esterification of glycans OH groups can be used to temporarily mask hydrophilicity to facilitate membrane permeability, in which, upon cell entry, endogenous esterases cleave the acetyl groups to produce the free glycan (pg. 2245, section 3.1). A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities (See MPEP 2144.09).
Taken together it would have been prima facie obvious to a person of ordinary skill in the art to modify the compounds of the patented claims by replacing OH or OAc groups with fluorine or hydrogen as suggested by Hevey and arrive at the claimed compounds. A person of ordinary skill in the art would have had the motivation to do so with a reasonable expectation of success in order to impart greater enzymatic stability to the structure and replacement with fluorine or hydrogen groups in glycomimetic structures is a known technique in the art. A person of ordinary skill in the art would be capable of determining the optimal degree of substitution with fluorine.
The patented claims further differ from the instant application in that they do not teach a method of treating the specific cancers claimed.
However, Gallop further teaches HDAC inhibitors have been approved for the clinical treatment of cancers such as leukemia (pg. 47, paras. 0199-0201, pg. 48, para. 0207). Whereas the compounds of the instant claims were made obvious over the compound recited by claim 5 of US-963, it would have been prima facie obvious to administer a therapeutically effective amount of compounds recited by the instant claims for treating leukemia as taught by Gallop. One of ordinary skill in the art would have had the motivation to do so with a reasonable expectation of success as HADC inhibitor compounds have been used in the art to treat leukemia.
Claims 1-21 and 23-33 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over the claims of copending Application No. 19/049,614 (US 2025/0222115, cited on PTO-892) in view of Gallop (US 2020/0016185, IDS filed August 7, 2024) and Hevey (Chem. Eur. J., 2021, IDS filed May 6, 2024). Although the claims at issue are not identical, they are not patentably distinct from each other because:
Regarding claims 1-21 and 23-33: Copending claim 1 teaches the following structure:
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Copending claim 5 teaches the following structure:
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. The copending claims teach pharmaceutical compositions of the aforementioned compounds (copending claims 2 and 6). The copending claims teach methods of treating lung cancer, head and neck cancer, breast cancer, and leukemia comprising administering to a subject in need thereof a therapeutically effective amount of the aforementioned compounds/compositions (copending claims 3-4 and 7-8).
The copending claims do not teach wherein the R3 position is H or F. The copending claims do not teach wherein R2, R3, R4, R6, R7, and R8 are fluorine (F). The copending claims do not teach the specific compounds recited by instant claims 26 and 31.
However, Gallop teaches compounds that are non-toxic prodrugs of senolytic agents which are activated by glycosidases that preferentially accumulate inside senescent cells:
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(pg. 1, para. 0006). The functionality of HDAC inhibitors (i.e., Panobinostat) is masked as a glycoside derivative (pg. 19, paras. 0108-109). This ensures that prodrugs are inactive as HDAC inhibitors, but will become activated upon hydrolysis within the lysosomes of senescent cells (pg. 19, paras. 0108-109). Gallop teaches prodrugs of histone deacetylase inhibitors capable of promoting apoptosis in senescent cells (pg. 1, paras. 0006-0008). These senolytic agents may be combined with at least one pharmaceutically acceptable excipient to form a pharmaceutical composition and administered to a subject for the purpose of killing senescent cells (pg. 57, para. 0269). Gallop further teaches HDAC inhibitors have been approved for the clinical treatment of cancers such as leukemia (pg. 47, paras. 0199-0201, pg. 48, para. 0207). Gallop teaches the methods are useful for inhibiting retarding or slowing progression of metastatic cancer including leukemia (pg. 48, para. 0208). Gallop teaches the following compound:
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(pg. 17, para. 0105). Gallop teaches acetyl as a protecting group for hydroxy groups to act as a mask or reduce reactivity of the functional group (pgs. 5-6, para. 0082). Hevey teaches “the use of native glycan structures has met with limited success, which can be attributed to their characteristic high polarity (e.g., low binding affinities) and inherently poor pharmacokinetic properties (e.g., short drug–target residence times, rapid renal excretion), leading to the development of ’glycomimetics’. Fluorinated drugs have become increasingly common over recent decades, with fluorinated glycomimetics offering some unique advantages. Deoxyfluorination maintains certain electrostatic interactions, while concomitantly reducing net polarity through ’polar hydrophobicity’, improving residence times and binding affinities. Fluorination destabilizes the oxocarbenium transition state associated with metabolic degradation, and can restore exo and endo-anomeric effects in C-glycosides and carbasugars” (pg. 2241, abstract). There are two main fluorination strategies: OH to F substitution, and H to F substitution (pg. 2243, section 1.2). Fluorine substitution at the C-2 position is the most effective at slowing hydrolysis (pg. 2245, section 3.1). Additional changes such as replacing OH groups with hydrogen are also routinely studied in the art (pg. 2242, section 2.1). Hevey also teaches that in a pro-drug approach, esterification of glycans OH groups can be used to temporarily mask hydrophilicity to facilitate membrane permeability, in which, upon cell entry, endogenous esterases cleave the acetyl groups to produce the free glycan (pg. 2245, section 3.1). A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities (See MPEP 2144.09).
Taken together it would have been prima facie obvious to a person of ordinary skill in the art to modify the compounds of the copending claims by replacing OH or OAc groups with fluorine or hydrogen as suggested by Hevey and arrive at the claimed compounds. A person of ordinary skill in the art would have had the motivation to do so with a reasonable expectation of success in order to impart greater enzymatic stability to the structure and replacement with fluorine or hydrogen groups in glycomimetic structures is a known technique in the art. A person of ordinary skill in the art would be capable of determining the optimal degree of substitution with fluorine.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Allowable Subject Matter
Claim 22 allowed.
The following is a statement of reasons for the indication of allowable subject matter:
As discussed above Gallop and Hevey render obvious the compounds recited by instant claims 1-18, 26 and 30. Gallop and Hevey teach the sugar portion of the molecule can vary in H, OH, F, and OAc groups. However there is no teaching or suggestion to modify the compound by converting the hydroxyl groups into the cyclic acetal as demonstrated in the compound recited by instant claim 22. Thus, it would be improper hindsight to suggest a person of ordinary skill in the art would have the requisite motivation to make this structural change as there is no teaching or suggestion there is any benefit to do so. Therefore, the compound according to instant claim 22 is allowable over the prior art.
Conclusion
Claim 22 is allowed in this action.
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure:
Gallop (WO 2020/014409, cited on PTO-892) teaches agents for selectively killing senescent cells (abstract).
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SAMUEL L GALSTER whose telephone number is (571)270-0933. The examiner can normally be reached Monday - Friday 8:00 AM - 5:00 PM.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Y Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/S.L.G./Examiner, Art Unit 1693
/ERIC OLSON/Primary Examiner, Art Unit 1693