DETAILED ACTION
Notice of 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 .
Response to Arguments
Applicant’s elected species, Compound I-28 having the following structure:
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,
reads upon claims 1-6 and 8-13.
As discussed in the Action mailed on, 10/17/2025, the elected species is determined to be free of the art and non-obvious. In particular, the closest prior art is considered to be Qabar et al (US 2005/0250780; of record) which teach “[r]everse-turn mimetics” (Abstract) including the following compound:
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(Page 35, Table 2)
which, as indicated by arrows, differs from Applicant’s elected compound species Compound I-28 in the following three ways:
(i) comprising -CH2- as opposed to the instantly claimed -O- in the structure core;
(ii) comprising a C4 alkyl group as opposed to a C5 alkyl group at variable Q; and
(iii) comprising a substituted arylalkyl group as opposed to the instantly claimed unsubstituted cycloalkylalkyl at variable R33.
It would not have been obvious to modify the prior art compound of Qabar et al in these three ways to arrive at Applicant’s instantly elected compound species.
Accordingly, in the Action mailed on 10/17/2025, the search was expanded as called for under current Office Markush practice – a compound-by-compound search – to the following compound species, all of which were rejected under 35 U.S.C. 103(a):
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(b)
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(c)
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and (d)
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In Applicant’s response, filed 1/15/2026, Applicant traverses the rejections of the above compounds. In particular, Applicant notes that “the above prior art molecules differ from the elected species by possessing a -CH2- linker in place of the -O- linker in the elected species” (Applicant Arguments, Page 5). And, as argued by Applicant, “one skilled in the art would have no expectation that the [prior art] mimicking or mimetic compounds described in any of the... references could remain as mimicking or mimetic compounds... once the compounds therein are modified by replacing a -CH2- linker with an -O- linker” (Applicant Arguments, Page 6).
The argument is not found persuasive. As discussed in the basis of the rejection, Williams et al teach that the “[r]eplacement or modification of functional groups with other groups having similar properties is known as isosteric or bioisosteric replacement” (Page 59) and one well-known bioisosteric replacement is -CH2- for -O- (Page 60, Table 2.8, Page 61, Table 2.9, Page 63, Table 2.10, Reference 45). Similarly, Hevey et al – also noting that “[b]ioisosteric replacement of functional groups is commonly used in medicinal chemistry to improve the desired properties of a molecule” (Page 6, Section 4) – teach that one common bioisosteric replacement is -CH-2- for -O- (Page 6, Table 2). Moreover, Ueda et al (see Page 4705, Figure 1) specifically teach replacing -CH-2- with -O- in the mimetic compound C699 to provide the structurally and functionally related mimetic compound mS-11:
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In view of all the foregoing, it is MAINTAINED that it would have been prima facie obvious to replace the -CH2- linker in the prior art compounds with an -O- linker to arrive at structurally and functionally related compounds with a reasonable expectation of success.
Applicant, however, further argues that “[e]ven if, pro arguendo, -CH2- and -O- linkers may be considered in some circumstances to be bioisosteres, this does not detract from the common knowledge in the chemical arts that -CH2- and -O- linkers have substantially different properties (e.g., substantially hydrophobic and incapable of hydrogen bonding in the case of -CH2- and substantially hydrophilic and highly capable of hydrogen bonding in the case of -O-). Such significant differences in the properties of these two groups would be expected to impart very different properties in the molecule as a whole, which thus renders their desired mimicking or mimetic ability... unpredictable when such a significant change to the molecule is made” (Applicant Arguments, Page 6).
The argument is not found persuasive. At the outset, Applicant is advised that the arguments of counsel cannot take the place of evidence in the record. In re Shulze, 346 F.2d 600 (CCPA 1965). Additionally, obviousness does not require absolute predictability, only a reasonable expectation of success of obtaining similar properties. In re O'Farrell, 853 F.2d 894 (Fed. Cir. 1988). And finally, Ueda et al (see Page 4705, Figure 1) specifically teach replacing -CH-2- with -O- in the mimetic compound C699 to provide the structurally and functionally related mimetic compound mS-11:
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Applicant, however, argues that the “proposed modifications of compounds of [the prior art are] even less predictable considering that the modifications are being made to the very core (i.e., backbone or scaffold) of the molecule as opposed to side chains of the molecule” (Applicant Arguments, Page 6) and “while bioisosteric modifications are widely used at the functional-group level, it is quite another matter when it comes to modifying the scaffold” which “would effectively nullify the structure-activity relationship (SAR)” (Applicant Arguments, Page 7).
The argument is not found persuasive. There is nothing in Williams et al, Hevey et al or Ueda et al to suggest that the bioisosteric replacement taught therein cannot be applied to a compound’s core. In fact, Ueda et al specifically teach modification of the compound’s core.
Applicant, however, argues that “Ueda et al., in particular, exemplifies modifications of the backbone along with additional multiple changes” (Applicant Arguments, Page 7).
The argument is not found persuasive. Rather, the teaching of Ueda et al suggests that mimetic compounds, in particular, are flexible, and further indicates that there would have been a reasonable expectation of success in obtaining a functionally related compound when carrying out the single modification proposed by the prior art to a mimetic compound.
Lastly, Applicant notes that “Hevey et al. explains that the effect of such replacements is context-dependent and does not necessarily yield appropriate results in all cases” (Applicant Arguments, Page 8).
This is not disputed. However, as discussed above, obviousness does not require absolute predictability, only a reasonable expectation of success of obtaining similar properties. In re O'Farrell, 853 F.2d 894 (Fed. Cir. 1988). In the instant case, it is MAINTAINED that the combination of Williams et al, Hevey et al and Ueda et al provide a reasonable expectation of success in replacing -CH-2- with -O- in the prior art mimetic/mimicking compounds in an effort to synthesize similar compounds that retain biological activity, but have improved physiochemical properties and better pharmacokinetic behavior, with a reasonable expectation of success. One cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413 (CCPA 1981); In re Merck & Co., 800 F.2d 1091 (Fed. Cir. 1986).
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.
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 1-6 and 8-13 are rejected under 35 U.S.C. 103(a) as being unpatentable over Qabar et al (US 2005/0250780; of record) in view of Williams et al (Foye’s Principles of Medicinal Chemistry, 5th Ed., Pages 59-63, 2002; of record), Hevey et al (Biomimetics 4:53 (23 pages), 2019; of record) and Ueda et al (Bioorg Med Chem Lett 27:4705-4709, 2017; of record).
Claim 1 is drawn to a compound of formula (I) which embraces the following compound species
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wherein Q is formula I-1wherein R1a is alkyl and R1b is hydrogen; U is -(C(O))-; R2 is substituted alkyl; R4a is substituted alkyl or arylalkyl; R4b is hydrogen; R3 is -W31-W32-R33- wherein W31 is -C(O)-, W32 is -O- and R33 is substituted alkyl or substituted arylalkyl; and R5 is hydrogen - which reads on claims 1-6 and 8-13.
Qabar et al teach “[r]everse-turn mimetics” (Abstract) including the following compound species
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(Page 35, Table 2) which differs from the instantly claimed compound in comprising a -CH2- in place of the instantly claimed -O- as indicated by arrow.
Yet, as taught by Williams et al “[w]hen a lead compound is first discovered for a particular disease state, it often lacks the required potency and pharmacokinetic properties suitable for making it a viable clinical candidate… The medicinal chemist therefore must modify the compound to reduce or eliminate these undesirable features without losing the desired biological activity. Replacement or modification of functional groups with other groups having similar properties is known as isosteric or bioisosteric replacement” (Page 59). Although it is clear that "the use of bioisosteric replacement (classical or nonclassical) in drug development is highly dependent upon the biological system being investigated” and that “[n]o hard and fast rules exist to determine what bioisosteric replacement is going to work with a given molecule” it is also clear that “some generalizations have been possible” (Page 60). Notably, one such generalization is that -CH2- and -O- can replace each other (Page 60, Table 2.8, Page 61, Table 2.9, Page 63, Table 2.10, Reference 45).
As similarly taught by Hevey et al – also noting that “[b]ioisosteric replacement of functional groups is commonly used in medicinal chemistry to improve the desired properties of a molecule” (Page 6, Section 4) – one common bioisosteric replacement is -CH-2- for -O- (Page 6, Table 2).
And, significantly, Ueda et al (see Page 4705, Figure 1) specifically teach replacing -CH-2- with -O- in the mimetic compound C699 (comprising the same core as Qabar et al) to provide the structurally and functionally related compound mS-11 (having the instantly claimed core):
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In view of all the foregoing, it would have been obvious to a person of ordinary skill in the art at the time the invention was made to replace -CH-2- with -O- in the compound taught by Qabar et al with to arrive at the instantly claimed compound. The person of ordinary skill in the art at the time the invention was made would have been motivated to make the bioisosteric modifications in an effort to synthesize similar compounds that retain biological activity, but have improved physiochemical properties and better pharmacokinetic behavior, with a reasonable expectation of success.
As such, claims 1-6 and 8-13 are rejected as prima facie obvious.
Claims 1-6 and 8-13 are ADDITIONALLY rejected under 35 U.S.C. 103(a) as being unpatentable over Kahn et al (US 6,013,458; of record) in view of Williams et al (Foye’s Principles of Medicinal Chemistry, 5th Ed., Pages 59-63, 2002; of record), Hevey et al (Biomimetics 4:53 (23 pages), 2019; of record) and Ueda et al (Bioorg Med Chem Lett 27:4705-4709, 2017; of record).
Claim 1 is drawn to a compound of formula (I) which embraces the following compound species
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wherein Q is I-1 wherein R1a is alkyl and R1b is hydrogen; U is -(C(O))-; R2 is substituted alkyl or arylalkyl; R4a is substituted alkyl or arylalkyl; R4b is hydrogen; R3 is -W31-W32-R33- wherein W31 is -C(O)-, W32 is -O- and R33 is substituted alkyl or arylalkyl; and R5 is hydrogen - which reads on claims 1-6 and 8-13.
Kahn et al teach “compounds which mimic the secondary structure of reverse-turn regions of biologically active peptides and proteins” (Abstract) including the following compound species
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(Column 27, Table I, Compound 8) which differs from the instantly claimed compound in comprising a -CH2- in place of the instantly claimed -O- as indicated by arrow.
Yet, as taught by Williams et al “[w]hen a lead compound is first discovered for a particular disease state, it often lacks the required potency and pharmacokinetic properties suitable for making it a viable clinical candidate… The medicinal chemist therefore must modify the compound to reduce or eliminate these undesirable features without losing the desired biological activity. Replacement or modification of functional groups with other groups having similar properties is known as isosteric or bioisosteric replacement” (Page 59). Although it is clear that "the use of bioisosteric replacement (classical or nonclassical) in drug development is highly dependent upon the biological system being investigated” and that “[n]o hard and fast rules exist to determine what bioisosteric replacement is going to work with a given molecule” it is also clear that “some generalizations have been possible” (Page 60). Notably, one such generalization is that -CH2- and -O- can replace each other (Page 60, Table 2.8, Page 61, Table 2.9, Page 63, Table 2.10, Reference 45).
As similarly taught by Hevey et al – also noting that “[b]ioisosteric replacement of functional groups is commonly used in medicinal chemistry to improve the desired properties of a molecule” (Page 6, Section 4) – one common bioisosteric replacement is -CH-2- for -O- (Page 6, Table 2).
And, significantly, Ueda et al (see Page 4705, Figure 1) specifically teach replacing -CH-2- with -O- in the mimetic compound C699 (comprising the same core as Kahn et al) to provide the structurally and functionally related compound mS-11 (having the instantly claimed core):
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In view of all the foregoing, it would have been obvious to a person of ordinary skill in the art at the time the invention was made to replace -CH-2- with -O- in the compound taught by Kahn et al with to arrive at the instantly claimed compound. The person of ordinary skill in the art at the time the invention was made would have been motivated to make the bioisosteric modifications in an effort to synthesize similar compounds that retain biological activity, but have improved physiochemical properties and better pharmacokinetic behavior, with a reasonable expectation of success.
As such, claims 1-6 and 8-13 are rejected as prima facie obvious.
Claims 1-6 and 8-13 are ADDITIONALLY rejected under 35 U.S.C. 103(a) as being unpatentable over Kahn et al (US 6,184,223; of record), Kahn et al (US 6,413,963), Kahn et al (US 6,548,500; of record), and/or Kahn et al (US 7,598,253; of record) in view of Williams et al (Foye’s Principles of Medicinal Chemistry, 5th Ed., Pages 59-63, 2002; of record), Hevey et al (Biomimetics 4:53 (23 pages), 2019; of record) and Ueda et al (Bioorg Med Chem Lett 27:4705-4709, 2017; of record).
Claim 1 is drawn to a compound of formula (I) which embraces the following compound species
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wherein Q is I-1 wherein R1a is substituted alkyl or substituted arylalkyl and R1b is hydrogen; U is -(C(O))-; R2 is substituted alkyl or substituted arylalkyl; R4a is substituted alkyl; R4b is hydrogen; R3 is -W31-W32-R33- wherein W31 is -C(O)-, W32 is -O- and R33 is substituted alkyl or arylalkyl; and R5 is hydrogen - which reads on claims 1-6 and 8-13.
Kahn et al teach “compounds which mimic the secondary structure of reverse-turn regions of biologically active peptides and proteins” (Abstract) including the following compound species
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(Table 6) which differs from the instantly claimed compound in comprising a -CH2- in place of the instantly claimed -O- as indicated by arrow.
Yet, as taught by Williams et al “[w]hen a lead compound is first discovered for a particular disease state, it often lacks the required potency and pharmacokinetic properties suitable for making it a viable clinical candidate… The medicinal chemist therefore must modify the compound to reduce or eliminate these undesirable features without losing the desired biological activity. Replacement or modification of functional groups with other groups having similar properties is known as isosteric or bioisosteric replacement” (Page 59). Although it is clear that "the use of bioisosteric replacement (classical or nonclassical) in drug development is highly dependent upon the biological system being investigated” and that “[n]o hard and fast rules exist to determine what bioisosteric replacement is going to work with a given molecule” it is also clear that “some generalizations have been possible” (Page 60). Notably, one such generalization is that -CH2- and -O- can replace each other (Page 60, Table 2.8, Page 61, Table 2.9, Page 63, Table 2.10, Reference 45).
As similarly taught by Hevey et al – also noting that “[b]ioisosteric replacement of functional groups is commonly used in medicinal chemistry to improve the desired properties of a molecule” (Page 6, Section 4) – one common bioisosteric replacement is -CH-2- for -O- (Page 6, Table 2).
And, significantly, Ueda et al (see Page 4705, Figure 1) specifically teach replacing -CH-2- with -O- in the mimetic compound C699 (comprising the same core as Kahn et al) to provide the structurally and functionally related compound mS-11 (having the instantly claimed core):
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In view of all the foregoing, it would have been obvious to a person of ordinary skill in the art at the time the invention was made to replace -CH-2- with -O- in the compound taught by Kahn et al with to arrive at the instantly claimed compound. The person of ordinary skill in the art at the time the invention was made would have been motivated to make the bioisosteric modifications in an effort to synthesize similar compounds that retain biological activity, but have improved physiochemical properties and better pharmacokinetic behavior, with a reasonable expectation of success.
As such, claims 1-6 and 8-13 are rejected as prima facie obvious.
Claims 1-6 and 8-13 are ADDITIONALLY rejected under 35 U.S.C. 103(a) as being unpatentable over Kouji et al (US 8,691,819; of record), Kouji et al (US 9,126,981; of record) and/or Kouji et al (US 9,682,996; of record) in view of Williams et al (Foye’s Principles of Medicinal Chemistry, 5th Ed., Pages 59-63, 2002; of record), Hevey et al (Biomimetics 4:53 (23 pages), 2019; of record) and Ueda et al (Bioorg Med Chem Lett 27:4705-4709, 2017; of record).
Claim 1 is drawn to a compound of formula (I) which embraces the following compound species
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wherein Q is I-1 wherein R1a is substituted alkyl or substituted heteroarylalkyl and R1b is hydrogen; U is -(C(O))-; R2 is substituted alkyl or substituted arylalkyl; R4a is alkyl; R4b is alkyl; R3 is -W31-W32-R33- wherein W31 is -C(O)-, W32 is -NH- and R33 is substituted alkyl or arylalkyl; and R5 is hydrogen - which reads on claims 1-6 and 8-13.
Kouji et al teach “[a]lpha-helix mimetic structures and compounds represented by the formula (I)” (Abstract) including the following compound species
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(see ACCESSION NUMBER 2010:504003, CAS RN 1222062-38-5) which differs from the instantly claimed compound in comprising a -CH2- in place of the instantly claimed -O- as indicated by arrow.
Yet, as taught by Williams et al “[w]hen a lead compound is first discovered for a particular disease state, it often lacks the required potency and pharmacokinetic properties suitable for making it a viable clinical candidate… The medicinal chemist therefore must modify the compound to reduce or eliminate these undesirable features without losing the desired biological activity. Replacement or modification of functional groups with other groups having similar properties is known as isosteric or bioisosteric replacement” (Page 59). Although it is clear that "the use of bioisosteric replacement (classical or nonclassical) in drug development is highly dependent upon the biological system being investigated” and that “[n]o hard and fast rules exist to determine what bioisosteric replacement is going to work with a given molecule” it is also clear that “some generalizations have been possible” (Page 60). Notably, one such generalization is that -CH2- and -O- can replace each other (Page 60, Table 2.8, Page 61, Table 2.9, Page 63, Table 2.10, Reference 45).
As similarly taught by Hevey et al – also noting that “[b]ioisosteric replacement of functional groups is commonly used in medicinal chemistry to improve the desired properties of a molecule” (Page 6, Section 4) – one common bioisosteric replacement is -CH-2- for -O- (Page 6, Table 2).
And, significantly, Ueda et al (see Page 4705, Figure 1) specifically teach replacing -CH-2- with -O- in the mimetic compound C699 (comprising the same core as Kouji et al) to provide the structurally and functionally related compound mS-11 (having the instantly claimed core):
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Indeed, Kouji et al generically teach that the -CH2- group in the compounds disclosed therein can alternatively be -O- (see Column 3, Line 40, variable G in Formula (I) and Column 4, Line 1).
In view of all the foregoing, it would have been obvious to a person of ordinary skill in the art at the time the invention was made to replace -CH-2- with -O- in the compound taught by Kahn et al with to arrive at the instantly claimed compound. The person of ordinary skill in the art at the time the invention was made would have been motivated to make the bioisosteric modifications in an effort to synthesize similar compounds that retain biological activity, but have improved physiochemical properties and better pharmacokinetic behavior, with a reasonable expectation of success.
As such, claims 1-6 and 8-13 are rejected as prima facie obvious.
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 §§ 706.02(l)(1) - 706.02(l)(3) 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 USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The 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/process/file/efs/guidance/eTD-info-I.jsp.
Claims 1-6 and 8-13 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-18 of copending Application No. 18/014,556.
Although the claims at issue are not identical, they are not patentably distinct from each other. The ‘556 claims are similarly drawn to compounds of formula (I) which embrace the instantly claimed compounds.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Conclusion
No new ground(s) of rejection are 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 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 date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to CRAIG D RICCI whose telephone number is (571) 270-5864. The examiner can normally be reached on Monday through Thursday, and every other Friday, 7:30 am - 5:00 pm ET.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Bethany Barham can be reached on (571) 272-6175. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/CRAIG D RICCI/Primary Examiner, Art Unit 1611