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 .
Response to Arguments
Applicants' arguments, filed January 27, 2026, have been fully considered. New grounds of rejection are set forth below to render obvious compounds in which the attachment point to the chelator ring is via the ring nitrogen heteroatom and not the ring carbon atom. Any arguments not addressed by the new ground of rejection are addressed below. The following rejections and/or objections constitute the complete set presently being applied to the instant application.
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.
The factual inquiries 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.
Claim(s) 11, 12, 17 and 25 are rejected under 35 U.S.C. 103 as being unpatentable over Eder et al. (WO 2015/055318) in view of Litau et al. (ChemMedChem, 2015), Morphy et al. (J Chem Soc Chem Commun, 1989) and Ruser et al. (Bioconjugate Chem, 1990).
Eder et al. discloses radiopharmaceuticals and their use in nuclear medicine as tracers, imaging agents and the treatment of various disease states of prostate cancer and the compounds are represented by either formulae (Ia) or (Ib) (whole document, e.g., abstract). As shown on page 8, with definitions of the variables continuing onto the next page, formula (Ia) comports with the formula set forth in instant claim 1:
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, X can be napthyl and Y can be cyclohexyl with the carbonyl next to the chelator being Y3 of the instant claims although the possible chelator moieties of Eder et al. do not fall within the scope of the instant claim chelator moiety portion of -Y2-A with u = 0. Pharmaceutical preparations with the active ingredient and organic or inorganic solid or liquid pharmaceutically acceptable carriers suited for the intended administration are also disclosed (p 20, ln 3 – 7). Radionuclides complexes of compounds according to formula (Ia) or (Ib) contain one or more radionuclides suitable for use as radioimaging agents or therapeutics for the treatment of rapidly proliferating cells and exemplified radionuclides include 61Cu, 62Cu, 64Cu and 67Cu (p 22, ln 8 – 12). As can be seen in scheme 2 on p 24, the chelator DOTA is conjugated to the PMSA inhibitors with an amide bond to a linker portion to the PMSA recognition element
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.
A chelator with a ring structure of
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or
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and Y2 being a phenylene as required by instant formula (1) is not disclosed.
Litau et al. discloses various chelators for the 64Cu radiolabeling of biomolecules to be used as in vivo positron emission tomography (PET) imaging agent (whole document, e.g., abstract). Commonly applied chelating agents with hard donor atoms such as oxygen and nitrogen are only of limited applicability in *Cu2+ complexation (p 1220, col 2, ¶ 3) even though it is of great utility in PET imaging with a favorable half-life of 12.7 h that enables successful target visualization even for slowly accumulating target ligands with a mean β+ energy that allows for high resolution PET images (p 1200, col 2, ¶ 2). Among the most potent chelating agents for radiocopper complexation are CB-TE2A and CB-TE1A-GA in figure 1 with structures of
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. The cavity size of these molecules is well suited for the relatively small Cu2+ ion and provides the preferred octahedral complex geometry (p 1201, col 1, ¶ 3). The additional carboxylic acid functionality in CB-TE1A-GA is application for conjugation with a targeting vector meaning that there is no decrease in complex stability from conjugation and the associated amide formation (p 1201, col 1, ¶ 4). Conjugation to a peptide is shown in figures 2 and 3 to obtain a radiolabeled materials that could be administered to animals to study the biodistribution of the conjugates (p 1205, col 2, ¶ 2 onward).
Morphy et al. discloses macrocyclic-conjugated antibodies are a key feature of radiolabeled tumor-localizing antibodies and macrocyclic ligands tend to undergo very slow acid-dependent decomplexation which makes the labeled antibody stable in vivo over a period of days (p 792). 64Cu and 67Cu can be used for positron emission tomography (PET) and immunotherapy and copper forms well-defined complexes with 13- and 14-membered tetra-aza-macrocyclic ligands insensitive to decomplexation even at low pH (sentence bridging p 792 and 793). Compounds 1 and 2
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with n = 0 or 1 includes a phenylene ring proximal to the chelator ring as shown in the upper left corner of p 793. These moieties were conjugated to an antibody using the scheme shown in column 1 on p 793. The conjugated antibodies were radiolabeled with either 64Cu and 67Cu (e.g., p 793, col 2, ¶ 3).
Ruser et al. discloses two new N- and C-functionalized tetraazamacrocyclic ligands intended to be covalently linked to biomolecules such as monoclonal antibodies and to bind to the γ-emitting isotope indium-111 (whole document, e.g., abstract). As shown in chart I,
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, compounds L1 and L2 have a phenylene substituent attached to the tetra-aza-macrocyclic ring while compounds L3 and L4 lack that phenylene substituent. Longer incubation times and higher ligand concentration were required for complete complex formation with L3 and L4 compared to L1 and L2 (p 347, col 1, ¶ 2). As shown in Figure 2, there was little if any dissociation from L1 and L2 over 180 minutes while both L3 and L4 showed significant dissociation and stated as too unstable for in vivo use (p 347, col 2, ¶ 2).
It would have been obvious to the person of ordinary skill in the art before the effective filing date of the claimed invention to use the CB-TE2A and CB-TE1A-GA bridged chelator moiety of Litau with an added phenylene moiety as the chelator portion in the compounds of formula (Ia) disclosed by Eder et al. or unbridged rings with the same phenylene linker as taught by Morphy et al. and Ruser et al. attached via the ring nitrogen atom. The person of ordinary skill in the art would have been motivated to make those modifications and reasonably would have expected success because Litau et al. discloses potent radioactive copper chelating motifs suitable for use in PET imaging with a cavity size well suited for Cu2+ that will allow for high resolution PET imaging even for slowly accumulating target ligands. Both the bridged and non-bridged rings are capable of chelating Cu as disclosed by Litau et al. and Morphy et al. respectively and compounds that differ only in the placement of substituents in a ring system are not patentably distinct absent unexpected results. The choice of radionuclide from those disclosed as suitable in the prior art is within the skill of one of ordinary skill in the art based on the type of imaging and/or therapy being carried out. Pharmaceutical compositions comprising such formulations can be prepared as disclosed by Eder et al. to enable administration to a subject for imaging and/or therapeutic purposes. Ruser et al. discloses that the presence of a phenylene ring proximal to the chelator rings results in shorter incubation times and lower amounts of ligand for complete metal ion-chelator complex formation. Given the highly similar nature of the chelator ring structures for use in biomolecule labeling, one of ordinary skill in the art would reasonably expect that the presence of a phenylene ring could improve the metal ion-chelator complex formation step even if the attachment point for the linker was moved from the ring C atom to the ring N atom and there is no evidence of record as to unexpected results.
Almost all of Applicants’ arguments regarding the previous rejections are addressed by the new grounds of rejection set forth above. Applicants argue that the compounds in Litau are very large and are linked via PEG3 linker rather than the small molecule linkers of Eder and teaches that conjugation of a chelator to a biomolecule can influence the ability of the chelator to form a complex with a metal and the stability of that complex. The compounds of Ruser are not attached to a larger linker-biomolecule system. Given the teachings of Litau, a person of ordinary skill in the art would have no reasonable expectation of that the chelators of Litau would lead to improved pharmacokinetic parameters and tumor targeting properties of PSMA targeting compounds when attached to a phenylene ring and conjugated to the compounds of Eder.
These arguments are unpersuasive. While one of ordinary skill in the art may not have an absolute expectation of success that phenylene ring insertion will improve the kinetics and reaction kinetics required for complete formation for the compounds of Eder et al. and Litau et al. in particular, only a reasonable and not an absolute expectation of success is required for a prima facie case of obviousness. In Litau, conjugation was either to the peptide PESIN (e.g., scheme 3 and Figure 2) which is not large and c(RGDfC) tetramers (e.g., scheme 2) which is larger than PESIN but smaller than proteins such as antibodies. Complex formation was carried out after conjugation (e.g., p 1207, col 2, ¶ 7). Ruser studied the kinetics of metal ion-complex formation with a short linker but there is discussion of the use of such compounds for application to radiolabel monoclonal antibodies (p 345, col 1, ¶ 1). The bifunctional derivatives maybe of additional benefit in antibody labeling (p 345, col 2, ¶ 2). These teachings and the knowledge of one of ordinary skill would indicate that complex formation could occur prior to or after conjugation of the chelator moiety to targeting ligands of various sizes while reasonably indicating that the presence of the phenylene ring can improve the complexation reaction even if the exact conditions when conjugated to a large biomolecule could have been absolutely predicted.
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 11, 12, 17 and 25 were rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 - 13 of U.S. Patent No. 10,980,901 in view of Eder et al. (WO 2015/055318), Litau et al. (ChemMedChem, 2015), Morphy et al. (J Chem Soc Chem Commun, 1989) and Ruser et al. (Bioconjugate Chem, 1990).
The claims of US’901 recite a method requiring the radionuclide Ac-225-containing compounds of formula (A) as in claim 1. Such compounds must be an administered to a patient which requires a pharmaceutical composition of the compounds be prepared as required by instant claim 17.
The presence of radioactive nuclide of copper with a compound of instant claim 1 is not claimed.
Eder et al., Litau et al., Morphy et al., and Ruser et al. are discussed above. Eder et al. lists not only radioactive isotopes of copper as mentioned above but also 225Ac as an illustrative radionuclide (p 22, ln 8 – 13).
It would have been obvious to the person of ordinary skill in the art before the effective filing date of the claimed invention to use the chelator moieties of Morphy et al. or Litau et al. with a phenylene ring connecting that chelator moiety to the compounds of US’901 and to bind a radioactive copper nuclide to that chelator portion as disclosed by Eder et al. The person of ordinary skill in the art would have been motivated to make those modifications and reasonably would have expected success because different chelator moieties exhibit different metal binding properties based on their different structures. Ruser et al. discloses that the presence of a phenylene ring next to the tetra-aza-macrocyclic ligand influences the rate of metal ion complex formation and dissociation with the presence of such a ring making it easier to form the metal complex and the resultant metal-chelator complex is also more stable. Litau et al. discloses potent radioactive copper chelating motifs suitable for use in PET imaging with a cavity size well suited for Cu2+ that will allow for high resolution PET imaging even for slowly accumulating target ligands. The different kinetics of metal ion binding observed for the addition of a phenylene ring next to the tetra-aza-macrocyclic ligands would motivate one of ordinary skill in the art to use a tetra-aza-macrocyclic ligands-phenylene chelating moiety capable of binding copper disclosed by Morphy et al. or Litau et al. as the chelator moiety in the complexes of US’901. Compounds that differ only in the placement of substituents in a ring system are not patentably distinct absent unexpected results. While the specific compounds of Morphy et al. contain a terminal amine, given the required structure of the carbonyl next to nitrogen containing repeating group in formula (Ia) of US’901, one of ordinary skill in the art would use their knowledge of conjugate formation chemistry to prepare suitable fragments that can be reacted form a compound of formula (Ia) of US’901 with the para-phenylene-tetra-aza-macrocyclic ligand and phenylene being attached to the carbonyl carbon of the amide and not via the nitrogen atom.
Applicants traverse the previous rejection based on US’901 on the grounds that the claimed compounds contain an Ac-225 radiopharmaceutical and correspond to the chemicals of Eder et al. The claimed compounds are not taught to suggested by Eder or the ‘901 patent.
Eder et al. and the teachings of the additional referenced in the modified rejection set forth above render obvious replacement of Ac-225 with a copper radionuclide and the other structural features as required by the instant claims.
Claims 11, 12, 17 and 25 were provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 15 – 29 of copending Application No. 18/440,783 in view of Eder et al. (WO 2015/055318), Litau et al. (ChemMedChem, 2015), Morphy et al. (J Chem Soc Chem Commun, 1989) and Ruser et al. (Bioconjugate Chem, 1990).
The claims of US’783 recite a 161Tb radiolabeled compound wherein R’ is chelator moiety shown. Pharmaceutical compositions of such metal complexes are recited in claim 11.
Compounds have the chelator moieties are required by formula (I) of instant claim 1 complexed with a copper radionuclide are not claimed.
Eder et al., Litau et al., Morphy et al., and Ruser et al. are discussed above. Note that 161Tb is also taught by Eder et al. along with various copper isotopes (p 22, ln 8 – 14).
It would have been obvious to the person of ordinary skill in the art before the effective filing date of the claimed invention to use the chelator moieties of Morphy et al. or Litau et al. with a phenylene ring connecting that chelator moiety to the compound of US’783 and to bind a radioactive copper nuclide to that chelator portion as disclosed by Eder et al. The person of ordinary skill in the art would have been motivated to make those modifications and reasonably would have expected success because different chelator moieties exhibit different metal binding properties based on their different structures. Ruser et al. discloses that the presence of a phenylene ring next to the tetra-aza-macrocyclic ligand influences the rate of metal ion complex formation and dissociation with the presence of such a ring making it easier to form the metal complex and the resultant metal-chelator complex is also more stable. Litau et al. discloses potent radioactive copper chelating motifs suitable for use in PET imaging with a cavity size well suited for Cu2+ that will allow for high resolution PET imaging even for slowly accumulating target ligands. The different kinetics of metal ion binding observed for the addition of a phenylene ring next to the tetra-aza-macrocyclic ligands would motivate one of ordinary skill in the art to use a tetra-aza-macrocyclic ligands-phenylene chelating moiety capable of binding copper disclosed by Morphy et al. or Litau et al. as the chelator moiety in the compound of US’783. Compounds that differ only in the placement of substituents in a ring system are not patentably distinct absent unexpected results. While the specific compounds of Morphy et al. contain a terminal amine, given the required structure of the carbonyl next to nitrogen in the claimed compound of US’783, one of ordinary skill in the art would use their knowledge of conjugate formation chemistry to prepare suitable fragments that can be reacted form a compound of US’783 with the para-phenylene-tetra-aza-macrocyclic ligand and phenylene being attached to the carbonyl carbon of the amide and not via the nitrogen atom.
This is a provisional nonstatutory double patenting rejection.
Applicants traverse the previous rejection based on US’783 on the grounds that the claimed compounds correspond to MB17 of Eder and the claimed compounds are not taught or suggested by Eder and US’783.
Eder et al. and the additional references in the modified rejection set forth above render obvious the compounds of the instant claims.
Claims 11, 12, 17 and 25 were provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 15 – 22 of copending Application No. 18/628,570 Eder et al. (WO 2015/055318), Litau et al. (ChemMedChem, 2015), Morphy et al. (J Chem Soc Chem Commun, 1989) and Ruser et al. (Bioconjugate Chem, 1990).
The claims of US’570 recite compositions comprising a means for treating prostate cancer or a metastasis thereof and a pharmaceutically acceptable carrier. No means are claimed but metal complexes such as those of original claim 5 that can be used in a method of treating prostate cancer and/or metastasis are disclosed means for carrying out the claimed function, such that compositions of radiolabeled compounds, such as with 64Cu of a compound of claim 1 (see claims 4 - 6) fall within the scope of claims 15 – 22 even though the specific structures are not recited in these claims.
Compounds that have the chelator moieties are required by formula (I) of instant claim 1 are not disclosed as means for treating prostate cancer or a metastasis thereof and a pharmaceutically acceptable carrier.
Eder et al., Litau et al., Morphy et al., and Ruser et al. are discussed above.
It would have been obvious to the person of ordinary skill in the art before the effective filing date of the claimed invention use the chelator moieties of Morphy et al. or Litau et al. with a phenylene ring connecting that chelator moiety to the compounds of US’570 and to bind a radioactive copper nuclide to that chelator portion as disclosed by Eder et al. The person of ordinary skill in the art would have been motivated to make those modifications and reasonably would have expected success because different chelator moieties exhibit different metal binding properties based on their different structures. Ruser et al. discloses that the presence of a phenylene ring next to the tetra-aza-macrocyclic ligand influences the rate of metal ion complex formation and dissociation with the presence of such a ring making it easier to form the metal complex and the resultant metal-chelator complex is also more stable. Litau et al. discloses potent radioactive copper chelating motifs suitable for use in PET imaging with a cavity size well suited for Cu2+ that will allow for high resolution PET imaging even for slowly accumulating target ligands. The different kinetics of metal ion binding observed for the addition of a phenylene ring next to the tetra-aza-macrocyclic ligands would motivate one of ordinary skill in the art to use a tetra-aza-macrocyclic ligands-phenylene chelating moiety capable of binding copper disclosed by Morphy et al. or Litau et al. as the chelator moiety in the complexes of US’570. Compounds that differ only in the placement of substituents in a ring system are not patentably distinct absent unexpected results. While the specific compounds of Morphy et al. contain a terminal amine, given the required structure of the carbonyl next to nitrogen containing repeating group in formula (Ia) of US’570, one of ordinary skill in the art would use their knowledge of conjugate formation chemistry to prepare suitable fragments that can be reacted form a compound of formula (Ia) of US’570 with the para-phenylene-tetra-aza-macrocyclic ligand and phenylene being attached to the carbonyl carbon of the amide and not via the nitrogen atom.
This is a provisional nonstatutory double patenting rejection.
Applicants traverse the previous rejection based on US’570 on the grounds that the claimed compounds correspond to MB17 of Eder and the claimed compounds are not taught or suggested by Eder and US’570.
Eder et al. and the additional references in the modified rejection set forth above render obvious the compounds of the instant claims.
Claims 11, 12, 17 and 25 were provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 15 - 44 of copending Application No. 19/326,445 in view of Eder et al. (WO 2015/055318), Litau et al. (ChemMedChem, 2015), Morphy et al. (J Chem Soc Chem Commun, 1989) and Ruser et al. (Bioconjugate Chem, 1990).
The claims of US’445 recite chelator containing compounds of formula Ia’ (claim 15) that can have a radionuclide such as 64Cu complexed to the chelator (e.g., claims 31 and 33). X can be napthyl (claims 38).
Eder et al., Litau et al., Morphy et al., and Ruser et al. are discussed above.
It would have been obvious to the person of ordinary skill in the art before the effective filing date of the claimed invention use the chelator moieties of Morphy et al. or Litau et al. with a phenylene ring connecting that chelator moiety to the compounds of formula (Ia’) in US’445 and to bind a radioactive copper nuclide to that chelator portion as disclosed by Eder et al. The person of ordinary skill in the art would have been motivated to make those modifications and reasonably would have expected success because different chelator moieties exhibit different metal binding properties based on their different structures. Ruser et al. discloses that the presence of a phenylene ring next to the tetra-aza-macrocyclic ligand influences the rate of metal ion complex formation and dissociation with the presence of such a ring making it easier to form the metal complex and the resultant metal-chelator complex is also more stable. Litau et al. discloses potent radioactive copper chelating motifs suitable for use in PET imaging with a cavity size well suited for Cu2+ that will allow for high resolution PET imaging even for slowly accumulating target ligands. The different kinetics of metal ion binding observed for the addition of a phenylene ring next to the tetra-aza-macrocyclic ligands would motivate one of ordinary skill in the art to use a tetra-aza-macrocyclic ligands-phenylene chelating moiety capable of binding copper disclosed by Morphy et al. or Litau et al. as the chelator moiety in the complexes of US’445. Compounds that differ only in the placement of substituents in a ring system are not patentably distinct absent unexpected results. While the specific compounds of Morphy et al. contain a terminal amine, given the required structure of the carbonyl next to nitrogen containing repeating group in formula (Ia’) of US’445, one of ordinary skill in the art would use their knowledge of conjugate formation chemistry to prepare suitable fragments that can be reacted form a compound of formula (Ia’) of US’445 with the para-phenylene-tetra-aza-macrocyclic ligand and phenylene being attached to the carbonyl carbon of the amide and not via the nitrogen atom.
This is a provisional nonstatutory double patenting rejection.
Applicants traverse the previous rejection based on US’445 on the grounds that the claimed compounds correspond to MB17 of Eder and the claimed compounds are not taught or suggested by Eder and US’445.
Eder et al. and the additional references in the modified rejection set forth above render obvious the compounds of the instant claims.
Conclusion
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/Nissa M Westerberg/Primary Examiner, Art Unit 1618
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