www.uspto.gov
`
`UNITED STATES DEPARTMENT OF COMMERCE
`United States Patent and TrademarkOffice
`Address; COMMISSIONER FOR PATENTS
`P.O. Box 1450
`Alexandria, Virginia 22313-1450
`
`16/493,675
`
`HAY
`
`09/12/2019
`
`Teppei HOSOKAWA
`
`14434.0714USWO
`
`7156
`
`M
`
`ULERS
`
`HAMRE, SCHUMANN, MUELLER & LARSON P.C.
`45 South Seventh Street
`Suite 2700
`MINNEAPOLIS, MN 55402-1683
`
`PAGANO, ALEXANDER R
`
`1622
`
`PAPER NUMBER
`
`NOTIFICATION DATE
`
`DELIVERY MODE
`
`01/05/2022
`
`ELECTRONIC
`
`Please find below and/or attached an Office communication concerning this application or proceeding.
`
`The time period for reply, if any, is set in the attached communication.
`
`Notice of the Office communication was sent electronically on above-indicated "Notification Date" to the
`following e-mail address(es):
`PTOMail @hsml.com
`
`PTOL-90A (Rev. 04/07)
`
`

`

`
`
`Disposition of Claims*
`1-10 is/are pending in the application.
`)
`Claim(s)
`5a) Of the above claim(s) 5-9 is/are withdrawn from consideration.
`() Claim(s)__ is/are allowed.
`Claim(s) 1-4 and 10 is/are rejected.
`1 Claim(s)__ is/are objected to.
`C] Claim(s)
`are subjectto restriction and/or election requirement
`* If any claims have been determined allowable, you maybeeligible to benefit from the Patent Prosecution Highway program at a
`participating intellectual property office for the corresponding application. For more information, please see
`http:/Awww.uspto.gov/patents/init_events/pph/index.jsp or send an inquiry to PPHfeedback@uspto.gov.
`
`) ) ) )
`
`Application Papers
`10) The specification is objected to by the Examiner.
`11)() The drawing(s) filedon__ is/are: a)C) accepted or b)C) objected to by the Examiner.
`Applicant may not request that any objection to the drawing(s) be held in abeyance. See 37 CFR 1.85(a).
`Replacement drawing sheet(s) including the correction is required if the drawing(s) is objected to. See 37 CFR 1.121 (d).
`
`Priority under 35 U.S.C. § 119
`12) Acknowledgment is made of a claim for foreign priority under 35 U.S.C. § 119(a)-(d)or (f).
`Certified copies:
`cc) None ofthe:
`b)L) Some**
`a)¥) All
`1.4) Certified copies of the priority documents have been received.
`2.1) Certified copies of the priority documents have beenreceived in Application No.
`3.2.) Copies of the certified copies of the priority documents have been receivedin this National Stage
`application from the International Bureau (PCT Rule 17.2(a)).
`* See the attached detailed Office action for a list of the certified copies not received.
`
`Attachment(s)
`
`1)
`
`Notice of References Cited (PTO-892)
`
`2) (J Information Disclosure Statement(s) (PTO/SB/08a and/or PTO/SB/08b)
`Paper No(s)/Mail Date
`U.S. Patent and Trademark Office
`
`3) (J Interview Summary (PTO-413)
`Paper No(s)/Mail Date
`(Qj Other:
`
`4)
`
`PTOL-326 (Rev. 11-13)
`
`Office Action Summary
`
`Part of Paper No./Mail Date 20211222
`
`Application No.
`Applicant(s)
`16/493,675
`HOSOKAWAetal.
`
`Office Action Summary Art Unit|AIA (FITF) StatusExaminer
`ALEXANDER R PAGANO
`1622
`Yes
`
`
`
`-- The MAILING DATEofthis communication appears on the cover sheet with the correspondence address --
`Period for Reply
`
`A SHORTENED STATUTORY PERIOD FOR REPLYIS SET TO EXPIRE 3 MONTHS FROM THE MAILING
`DATE OF THIS COMMUNICATION.
`Extensions of time may be available underthe provisions of 37 CFR 1.136(a). In no event, however, may a reply betimely filed after SIX (6) MONTHSfrom the mailing
`date of this communication.
`If NO period for reply is specified above, the maximum statutory period will apply and will expire SIX (6) MONTHSfrom the mailing date of this communication.
`-
`- Failure to reply within the set or extended period for reply will, by statute, cause the application to become ABANDONED (35 U.S.C. § 133}.
`Any reply received by the Office later than three months after the mailing date of this communication, evenif timely filed, may reduce any earned patent term
`adjustment. See 37 CFR 1.704(b).
`
`Status
`
`1) Responsive to communication(s) filed on 29 October 2021.
`C) A declaration(s)/affidavit(s) under 37 CFR 1.130(b) was/werefiled on
`2a)¥) This action is FINAL.
`2b) (J This action is non-final.
`3)02 An election was madeby the applicant in responseto a restriction requirement set forth during the interview
`on
`; the restriction requirement and election have been incorporated into this action.
`4\0) Since this application is in condition for allowance except for formal matters, prosecution as to the merits is
`closed in accordance with the practice under Exparte Quayle, 1935 C.D. 11, 453 O.G. 213.
`
`

`

`Application/Control Number: 16/493,675
`Art Unit: 1622
`
`Page 2
`
`Notice of Pre-AlA 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.
`
`DETAILED ACTION
`
`Claims 1-10 of T. Hosokawaet al., US 16/493,675 (Mar. 15, 2018) are pending. Claims
`
`5-9 the non-elected species/invention stand withdrawn from consideration. Claims 1-4
`
`and 10 have been examined on the merits and stand rejected.
`
`Election/Restrictions
`
`Applicant previously elected of Group (I), claims 1-4, without traverse, in the Reply to
`
`Restriction Requirement filed on June 10, 2021. New claim 10 is addedto the invention
`
`of Group (I). Claims 5-9 to the non-elected invention of Groups(II) and (III) are maintained
`
`as withdrawn from consideration pursuant to 37 CFR 1.142(b).
`
`In view of the foregoing,
`
`the Examiner’s restriction/election requirement is maintained as FINAL.
`
`Pursuantto the Election of Species Requirement, Applicant elected without traverse, E)-
`
`2-cyano-3-(4-((4-methoxyphenyl)(phenyl)amino)phenyljacrylicacid as a cyanoacrylic
`
`acid derivative and triphenylmethylamine as a species oftrisubstituted methylamine.
`
`N
`
`.
`
`N
`\I
`
`Le
`
`CC
`
`(E)-2-cyano-3-(4-((4-
`methoxyphenyl)(phenyl)amino)phenyl)acrylic acid.
`
`triphenylmethylamine
`
`Of the elected invention of Group (1), claims 1-4 read on the elected species. The elected
`
`species were searched and determined to befree of the art of record. Pursuant to MPEP
`
`§ 803.02,
`
`the search was extended to the orange-fluorescing species disclosed by
`
`

`

`Application/Control Number: 16/493,675
`Art Unit: 1622
`
`Page 3
`
`Yamamoto discussed in detail below, which was found to anticipate instant claims 1-4.
`
`As such, the provisional election of species is given effect pursuant to 37 CFR 1.142(b)
`
`and no claims are provisionally withdrawn as not reading on the elected species. See,
`
`MPEP § 803.02.
`
`In view of the foregoing, the Examiner’s restriction/election requirement
`
`is made FINAL.
`
`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 dependentform shall be construed to incorporate by
`referenceall the limitations of the claim to which it refers.
`
`Failure to Limit a Base Claim
`
`Rejection of claim 2, dependent upon claim 1 under 35 U.S.C. 112(d) as being of improper
`
`dependent form for failing to further limit the subject matter of claim 1 upon whichit
`
`dependsis maintained for the reasons given in the previous Office action. See MPEP
`
`2173.05(e); 608.01 (n)(Il).
`
`Applicant's Argument
`
`Applicant argues that while claim 1 requires the presence of molecular cavities that are
`
`free from a guest molecule, claim 1 does not preclude the presence of some molecular
`
`cavities that include a guest molecule. Applicant points to the specification at page 9,
`
`[0039], which contemplates that in certain embodiments, some molecular cavities may
`
`contain a guest molecule.
`
`However, Applicant's argument requires that claim 1 be interpreted as encompassing a
`
`complex crystal comprising two types of “molecular cavities’. One molecular cavity set
`
`empty and one set comprising a guest molecule. Note that with respect to the term “guest
`
`

`

`Application/Control Number: 16/493,675
`Art Unit: 1622
`
`Page 4
`
`molecule’, the specification fairly teaches that when a “guest molecule’ is present, it can
`
`only be present in a “molecular cavity”. See Specification at pages 8-9, [0031]-[0039]
`
`(discussing Fig. 2). Applicant thus argues that the claim 2 limitation “where the complex
`
`crystal does not substantially contain the guest molecule” limits claim 1
`
`in the sense that
`
`the number of unrecited filled “molecular cavities” falls to less than 1 mol%. Specification
`
`at page 8, [0035] (defining "not substantially containing").
`
`This argument is not considered persuasive because claim 1 recites only one instanceof
`
`
`
`“molecular cavities” which according to claim 1 in “each of which a guest molecule.. . is
`
`not disposed’.
`
`It is agreed that the specification, in particular embodiments, contemplates
`
`complex crystals where some molecular cavities comprise a guest molecule and other
`
`molecular cavities are empty. But under a broadest reasonable interpretation, words of
`
`the claim must be given their plain meaning, unless such meaning is inconsistent with the
`
`specification. MPEP § 2111.01(I). And specific embodiments of the specification cannot
`
`be imported into the claims, particularly where the subject claim limitation is broader than
`
`the embodiment. MPEP § 2111.01(II). The plain language of claim 1 “in each of which”
`
`as underlined below:
`
`Claim 1... the complex crystal has, between the supramolecular units, molecular
`cavities in each of which a quest molecule for which the supramolecularunit is a
`host is not disposed.
`
`can only be interpreted as meaning all of the molecular cavities do not contain a guest
`
`molecule. MPEP § 2111.01. Suchinterpretation is consistent with the specification. E.g.,
`
`Specification at page 7, [0024]. An interpretation that the claimed complex crystal may
`
`comprise other, non-recited unfilled “molecular cavities” is not reasonable because they
`
`are not positively recited in claim 1. Such aninterpretation is further unreasonable in view
`
`of the claim 1
`
`transitional phrases “having”, “composed of’, and “has”. MPEP §
`
`2111.03(IV).
`
`

`

`Application/Control Number: 16/493,675
`Art Unit: 1622
`
`Page 5
`
`Claim Rejections 35 U.S.C. 112(a) -- New Matter
`
`The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
`
`the
`IN GENERAL.—The specification shall contain a written description of
`(a)
`invention, and of the manner and process of making and usingit, in such full, clear, concise,
`and exact terms as to enable any person skilled in the art to whichit pertains, or with whichit 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.
`
`Amendments narrowing the claims by introducing elements or limitations which are not
`
`supported by the as-filed disclosure is a violation of the written description requirement of
`
`35 U.S.C. 112(a). MPEP § 2163.05(II)
`
`Claim 10 is rejected under 35 U.S.C. 112(a) as failing to comply with the written
`
`description requirement on the grounds that the claim 10 recitation of:
`
`wherein the cavity rate is a ratio of a number of the molecular cavities in which the
`guest molecules are not disposed to a sum of a number of the guest molecules
`and the number of the cavities in which the guest molecules are not disposed
`
`is not described in the specification asfiled in such a way as to reasonably conveyto one
`
`skilled in the relevant art that the inventor, at the time the application was filed, had
`
`possession of the claimed subject matter. This claim 10 recitation can be represented by
`
`the formula:
`
`cavity rate —
`
`numberof the molecular cavities in which the guest molecules are not disposed
`
`number of the guest molecules + numberof the cavities in which the guest molecules are not disposed
`
`In the instant case, no particular supporting disclosure for
`
`the subject claim 10
`
`amendmentis readily apparent in the application. See MPEP § 2163(II)(A).
`
`

`

`Application/Control Number: 16/493,675
`Art Unit: 1622
`
`Page 6
`
`Applicant cites the specification at page 9, [0039], which in the relevant portion recites:
`
`the ratio of the number of the molecular cavities 3 to the sum of the number of the
`guest molecules 2 and the number of the molecular cavities 3
`
`This specification recitation can be represented by the formula:
`
`cavity rate =
`
`number of molecular cavities
`
`numberof guest molecules + numberof molecularcavities
`
`The portion of the specification cited by Applicant clearly does not support the claim 10
`
`subjectlimitation.
`
`Claim Rejections - 35 USC § 102 (AIA)
`
`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 madein this Office action:
`
`A personshall 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 waseffectivelyfiled before the
`effective filing date of the claimed invention.
`
`§ 102(a)(1) A. Yamamoto et al., “Hierarchical Construction of Fluorescent Organic Porous
`
`Structures and Guest Responsive Fluorescent Modulation by Ammonium Carboxylates”
`
`Division of Organic Crystals Newsletter, No. 29 (2011) (“Yamamoto”)
`
`Rejection of claims 1-4 under 35 U.S.C. § 102(a)1 over A. Yamamotoetal., “Hierarchical
`
`Construction of Fluorescent Organic Porous Structures and Guest Responsive
`
`Fluorescent Modulation by Ammonium Carboxylates” Division of Organic Crystals
`
`

`

`Application/Control Number: 16/493,675
`Art Unit: 1622
`
`Page 7
`
`Newsletter, No. 29 (2011) (“Yamamoto”) is maintained for the reasons given in the
`
`previous Office action.
`
`Applicant Argument That Yamamoto’s Orange Fluorescence Crystals Are Composedof
`
`Only
`
`(4-Diphenylamino)Phenylcyanoacrylic Acid
`
`Applicant argues that Yamamoto’s crystalline material exhibiting orange fluorescenceis
`
`composedof only (4-diphenylamino)phenylcyanoacrylic acid and therefore does not meet
`
`the instant claim 1
`
`limitation of “composed of two or more types of molecules”(i.e., that
`
`Yamamoto is not a complex crystal). Applicant relies on the Rule 132 Declaration by Dr.
`
`Tohnai (the “Tohnai Declaration’).
`
`It is first noted that the Tohnai Declaration contradicts the teachings of Yamamoto. The
`
`relevant portion of the Yamamoto English-langue translation is reproduced below.
`
`Compounds 1 and 2 were mixed in methanol, and the solvent was removedto give
`an organic salt. This salt was recrystallized using various organic solvents. In this
`paper, we report the results of our experiments. As a result of recrystallization in
`various organic solvents, crystals with fluorescence ranging from blue to orange
`were obtained. As a result of calorimetric analysis and other measurements, all of
`the crystals except the orange fluorescence crystals were inclusion crystals with
`the recrystallization solvent as_a quest. As a result of powder X-ray diffraction
`measurement, the structures can be roughly classified into six types, and four of
`them were clarified by single crystal X-ray structure analysis. All of the crystal
`structures had supramolecular clusters of carboxylic acids and amines as the core
`structure, but the accumulation pattern varied greatly depending on the guest
`species.
`
`Yamamoto-Eng at page 5 of 6 [Experiment]. Yamamoto’s statement that “[al]ll of the
`
`crystal structures had supramolecular clusters of carboxylic acids and amines as the core
`
`structure” indicates that the orange fluorescence crystals are composed of amine and
`
`carboxylic acid, which clearly meets the claim 1
`
`limitation of “two or more types of
`
`molecules”. On the other hand, Applicant argues that it reproduced the procedureof
`
`Yamamoto
`
`and
`
`the
`
`resulting
`
`crystals
`
`consisted
`
`only
`
`of
`
`((4-
`
`diphenylamino)phenylcyanoacrylic acid. Applicant's is thus arguing that Yamamoto is
`
`

`

`Application/Control Number: 16/493,675
`Art Unit: 1622
`
`Page 8
`
`inoperative with respect to the orange fluorescence crystal or alternatively that Yamamoto
`
`does not provide an enabling disclosure.
`
`When the reference relied on expressly anticipates or makes obvious all of the elements
`
`of the claimed invention, the reference is presumed to be operable. MPEP § 2121 Once
`
`such a reference is found,
`
`the burden is on applicant to rebut the presumption of
`
`operability. MPEP § 2121 (citing In re Sasse, 629 F.2d 675, 207 USPQ 107 (CCPA
`
`1980)). The test is whether the reference teachings cannot be produced without undue
`
`experimentation. MPEP § 2121.01 (citing Elan Pharm., Inc. v. Mayo Found. For Med.
`
`Educ. & Research, 346 F.3d 1051, 1054, 68 USPQ2d 1373, 1376 (Fed. Cir. 2003)).
`
`Applicant has failed to meet its burden that Yamamoto is inoperative with respectto its
`
`disclosure that the orange fluorescencecrystals are supramolecular clusters of carboxylic
`
`acids and amines as the core structure.
`
`The Tohnai Declaration states that the organic salt of Yamamoto was synthesized by
`
`mixing
`
`at
`
`room temperature
`
`((4-diphenylamino)phenylcyanoacrylic
`
`acid
`
`and
`
`triphenylmethylamine at a molar ratio of 1:1. Then, the methanol removed under reduced
`
`pressure to form the organic salt. The Tohnai Declaration provides only the following
`
`limited experimental details regarding forming compound 10 by recrystallization in
`
`pentafluorobenzonitrile and exhibited orange fluorescence.
`
`the formed organic salt of Yamamoto was dissolved in the solvent of
`Next,
`Compounds 3 to 10 shown in the Table below, and allowed to stand at room
`temperature for 48 hours to cause recrystallization, to obtain a single crystal. The
`crystals obtained by using the solvent of Compound 10 wasa crystal exhibiting
`orange fluorescence.
`
`Tohnai Declaration at page 3. The Tohnai Declaration goes on to state that a single crystal
`
`X-ray diffraction measurement of
`
`the crystal exhibiting orange fluorescence was
`
`performed. The Tohnai Declaration states that Reference Fig.
`
`1
`
`is the resulting crystal
`
`structure or the orange fluorescing material taught by Yamamoto. Reference Fig.
`
`1
`
`depicts only ((4-diphenylamino)phenylcyanoacrylic acid.
`
`

`

`Application/Control Number: 16/493,675
`Art Unit: 1622
`
`Page 9
`
`The Tohnai Declaration has not provided sufficient experimental data to meets is burden
`
`of showing that Yamamoto is inoperative because only a single experimental attemptis
`
`described with limited experimental detail. The Tohnai Declaration fails to disclose
`
`concentrations, temperatures (e.g. heating or cooling rates), reagent purities, and how
`
`the single crystal wasisolated.
`
`The ability of a single compound to crystallize in more than one crystallographic form
`
`(polymorphism) is encountered in a wide range of industries. See J. Mullin,
`
`in Ullmann’s
`
`Encyclopedia of Industrial Chemistry, 581-630, 591 (2012) (“Mullin”). Braga teachesthat
`
`variables that can influence or determine the outcome of the crystallization process with
`
`respect
`
`to crystal
`
`form include,
`
`temperature,
`
`crystallization conditions,
`
`rate of
`
`precipitation, and interconversion between solid forms.
`
`D Braga et al., Crystal
`
`Polymorphism and Multiple Crystal Forms, in 132 Molecular Networks: Structure Bonding,
`
`25-50 (2009) (“Braga”) (see pages 30-31).
`
`In view of the art teaching the complexity of arriving at specific crystal forms, the single
`
`experimental crystallization described in the Tohnai Declaration of limited detail is not
`
`dispositive that Yamamoto is not operative with selection of the appropriate crystallization
`
`conditions.
`
`Stated differently, Applicant has not met
`
`its burden of showing that
`
`Yamamoto’s orange fluorescence crystals are supramolecular clusters of carboxylic acids
`
`and amines as the core structure cannot be produced without undue experimentation.
`
`MPEP § 2121.01 (citing Elan Pharm., Inc. v. Mayo Found. For Med. Educ. & Research,
`
`346 F.3d 1051, 1054, 68 USPQ2d 1373, 1376 (Fed. Cir. 2003)).
`
`

`

`Application/Control Number: 16/493,675
`Art Unit: 1622
`
`Page 10
`
`Applicant Argument That Yamamoto Fails to Teach Molecular Cavities
`
`Applicant further argues that the complex crystal of claim 1 has molecular cavities, which
`
`are not spaces within the supramolecular unit, but are empty sites formed by the
`
`detachment of a guest molecule. Applicant argues that Yamamoto alsofails to teach that
`
`the crystal has molecular cavities in each of which a guest molecule for which the
`
`supramolecular unit is a host is not disposed, at least because Yamamoto does not teach
`
`any type of treatment of the crystal that would have resulted in the detaching of the guest
`
`molecules to form such molecular cavities.
`
`This argument is not considered persuasive because Yamamoto discloses the structure
`
`of a cluster of composed of
`
`((4-diphenylamino)phenylcyanoacrylic acid (1) and
`
`triphenylmethylamine (2) at Fig. 1(a). As clearly shownin Fig. 1(a), the dotted-line cube
`
`outlines a molecular cavity. As discussed above, Yamamoto discloses that “[alll of the
`
`crystal structures had supramolecular clusters of carboxylic acids and amines as the core
`
`structure”, which includes the orange fluorescence crystals that do not
`
`include the
`
`recrystallization solvent as a guest.
`
`Conclusion
`
`THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as
`
`set forth in 37 CFR 1.136(a).
`
`A shortenedstatutory period for reply to this final action is set to expire THREE MONTHS
`
`from the mailing date of this action.
`
`In the eventa 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 extension fee
`
`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.
`
`

`

`Application/Control Number: 16/493,675
`Art Unit: 1622
`
`Page 11
`
`Any inquiry concerning this communication or earlier communications from the examiner
`
`should be directed to ALEXANDER R PAGANO whosetelephone number is (571)270-
`
`3764. The examiner can normally be reached on 8:00 AM through 5:00 PM.
`
`Examiner interviewsare available via telephone, in-person, and video conferencing using
`
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`
`encouraged
`
`to
`
`use
`
`the USPTO Automated
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`Interview Request
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`(AIR)
`
`at
`
`
`
`If attempts to reach the examiner by telephone are unsuccessful,
`
`the examiner's
`
`supervisor, Brandon Fetterolf can be reached on (571) 272-2919. The fax phone number
`
`for the organization where this application or proceeding is assigned is 571-273-8300.
`
`Information regarding the status of an application may be obtained from the Patent
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`(PAIR) system.
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`Status information for published
`
`applications may be obtained from either Private PAIR or Public PAIR.
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`Status information for unpublished applications is available through Private PAIR only.
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`For
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`
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`

`

`Application/Control Number: 16/493,675
`Art Unit: 1622
`
`Page 12
`
`If you would like assistance from a USPTO Customer Service Representative or access
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`
`ALEXANDER R. PAGANO
`
`Examiner
`
`Art Unit 1622
`
`/ALEXANDER R PAGANO/
`Primary Examiner, Art Unit 1622
`
`