Prosecution Insights
Last updated: April 19, 2026
Application No. 17/491,676

3,3-DIFLUOROPIPERIDINE CARBAMATE HETEROCYCLIC COMPOUNDS AS NR2B NMDA RECEPTOR ANTAGONISTS

Final Rejection §DP
Filed
Oct 01, 2021
Examiner
FERGUSON, JALISA HOLMES
Art Unit
1626
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Rugen Holdings (Cayman) Limited
OA Round
2 (Final)
70%
Grant Probability
Favorable
3-4
OA Rounds
3y 2m
To Grant
99%
With Interview

Examiner Intelligence

Grants 70% — above average
70%
Career Allow Rate
16 granted / 23 resolved
+9.6% vs TC avg
Strong +64% interview lift
Without
With
+63.6%
Interview Lift
resolved cases with interview
Typical timeline
3y 2m
Avg Prosecution
21 currently pending
Career history
44
Total Applications
across all art units

Statute-Specific Performance

§101
1.6%
-38.4% vs TC avg
§103
17.9%
-22.1% vs TC avg
§102
19.5%
-20.5% vs TC avg
§112
38.4%
-1.6% vs TC avg
Black line = Tech Center average estimate • Based on career data from 23 resolved cases

Office Action

§DP
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 . Status of the Claims Claims 26-53 are pending. Claims 27-33 and 35-53 are withdrawn. Claims 26 and 34 are rejected. Response to Amendments and Arguments The amendment filed 08/22/2025 is compliant with the requirements of 37 CFR 1.121(c), accordingly the amendment has been entered. Applicant’s arguments have been fully considered and are addressed below: 35 USC § 103 Rejection The rejection of claim 26 under 35 USC 103 for being obvious over Liverton et al. in US 2007/0149568 in view of Patani and LaVoie “Bioisosterism: A Rational Approach in Drug Design” Chemical Reviews, (1996) Vol. 96, no. 8, pages 3147-3176 and in further view of King et al. in US 2015/0191452 has been overcome by Applicant’s arguments and the Declaration of Dr. Gideon Shapiro Under 37 CFR 1.132 filed 08/22/2025. Applicant argues that prior art compound MK-0657 was not identified as a lead compound (see page 14 of the Remarks dated 08/22/2025) and that MK-0657 actually had undesirable properties that would not motivate a person having ordinary skill in the art to pursue selecting the prior art compound for further modification. Applicant’s arguments of unexpected results, see pages 23-26 of the Remarks filed 08/22/2025, are considered persuasive. Applicant notes that the presently claimed compounds E1-22.2-22.6 all have significantly improved binding affinity to NR2B when compared with prior art compound MK-0657. In light of Applicant’s persuasive arguments, the rejection has been withdrawn. Double Patenting Rejection The rejection of claims 26 and 34 for nonstatutory obvious double patenting over U.S. Patent 10,584,127 and U.S. Patent 11,136,328 has been overcome by Applicant’s terminal disclaimer filed 08/22/2025. The rejections have been withdrawn. Regarding the rejection of claims 26 and 34 for nonstatutory obvious double patenting over U.S. Patent No. 11,752,155, Applicant states that the instant claims are patentably distinct from the claims of the ‘155 patent as “the ‘155 patent claims a method of treating a subject in need thereof comprising administering to the subject a composition comprising the chemical entity above and a pharmaceutically acceptable carrier” whereas the instant claims are directed to “a method of inhibiting NR2B in a biological sample, comprising administering to the biological sample a chemical entity of the formula above.” Applicant appears to argue that the patentable distinction is due to the difference in 1) administering to a subject in the ‘155 patent vs. a biological sample in the instant claims and 2) administration of a composition in the ‘155 patent vs. administration of a chemical entity in the instant claims. As it relates to the administration of the species, claim 1 of the patent is drawn to the chemical entity PNG media_image1.png 176 424 media_image1.png Greyscale . With respect to the instant claims, the claims in US ‘155 do not explicitly claim the method of administering the chemical entity to a biological sample. With respect to conflicting claims 1 and 2 in US ‘155 being directed to a different statutory class of invention (instantly claimed methods rather than the patented chemical entity and pharmaceutical composition used in the method), the Federal Circuit, in Sun v. Lilly, recounts its own decisions in Geneva and Pfizer, In both cases, we found claims of a later patent invalid for obviousness-type double patenting where an earlier patent claimed a compound, disclosing its utility in the specification, and a later patent claimed a method of using the compound for a use described in the specification of the earlier patent. ` Sun Pharmaceutical Industries Ltd. v. Eli Lilly and Co., 95 USPQ2d 1797 at 1800 (Fed. Cir. 2010). In reaffirming its holding in Geneva and Pfizer, the Court finds that a "claim to a method of using a composition is not patentably distinct from an earlier claim to the identical composition in a patent disclosing the identical use.” (Id. at 1801, quoting Pfizer, 518 F.3d at 1363; Geneva, 349 F.3d at 1385-86. The Court reasserts this notion by stating, [i]t would shock one's sense of justice if an inventor could receive a patent upon a composition of matter, setting out at length in the specification the useful purposes of such composition, . . .and then prevent the public from making any beneficial use of such product by securing patents upon each of the uses to which it may be adapted. Pfizer, 518 F.3d at 1363 n.8 (emphases added); Geneva, 349 F.3d at 1386 (quoting In re Byck, 48 F.2d 665, 666 [9 USPQ 205] (CCPA 1931)). Sun Pharmaceutical Industries Ltd. v. Eli Lilly and Co., 95 USPQ2d 1797 at 1802 (Fed. Cir. 2010). See also section 804 IIb of the M.P.E.P. In the instant case, the specification in US ‘155 identifies the utility of the compound as an NR2B subunit-selective N-methyl-D-aspartate (NMDA) receptor antagonist effective for the treatment of ASDs, OCD and/or anxiety disorders. See, e.g., column 4, lines 11-19. The specification also demonstrates the use of the compound in an NR2B Radioligand Binding Assay: PNG media_image2.png 597 907 media_image2.png Greyscale (see column 167, line 10 through column 168, line 3) wherein the compound is administered to the brain tissue of male Wistar rats. Table 1.2 (see col. 177) depicts the results of the patented compound in the assay: PNG media_image3.png 372 685 media_image3.png Greyscale . Since the utility of the compound as claimed in US ‘155 is identical to the utility of the compound claimed in the instant claims, the claims in US ‘155 render the instant claims 26 and 34 unpatentable for anticipatory-type double patenting. Regarding the rejection of claims 26 and 34 for nonstatutory obvious double patenting over U.S. Patent No. 11,000,526, Applicant states that the instant claims are patentably distinct from the claims of the ‘526 patent as “the ‘526 patent claims a method of treating a subject in need thereof comprising administering to the subject E1-22.2B’, E1-22.4 B’, E122.5 B’, or E1-22.6 B’” whereas the instant claims are directed to “a method of inhibiting NR2B in a biological sample, comprising administering to the biological sample a chemical entity of the formula above.” Applicant appears to argue that the patentable distinction is due to the difference in administering to a subject in the ‘526 patent vs. a biological sample in the instant claims. The Examiner finds this argument unpersuasive. It is expected that a person having ordinary skill in the art would pursue a preliminary in vitro test given the method provided in claim 1 of US ‘526 before immediately treating a subject. Fischer et al. (as cited in the updated double patenting rejection in the next section) provide a method for testing the comparable NR2B antagonist Ro 25-6981 in vitro. A skilled artisan would have been motivated to pursue a preliminary in vitro method and identified the Fischer reference as a source with a reasonable expectation of success. Updated Double Patenting Rejections (1 of 2) Claims 26 and 34 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-23 of U.S. Patent No. 11,752,155. Although the claims at issue are not identical, they are not patentably distinct from each other because the claimed compounds of patent ‘155 are identical to the presently claimed compounds. Patent ‘155 claim 3 recites methods of treating NMDA receptor-mediated disorders using a salt form of the elected species, which anticipates the present claims drawn to a method of inhibiting NR2B in a biological sample or patient using a compound of the same chemical entity formula. As noted in the discussion in the previous section, claim 1 of patent ‘155 is drawn to the chemical entity PNG media_image4.png 172 418 media_image4.png Greyscale . With respect to the fact that the claims of the patent are drawn to compounds and compositions while the instant claims are drawn to methods of inhibiting NR2B in a biological sample, Applicant is directed to Sun Pharmaceutical Industries Ltd. v. Eli Lilly and Co. 95 USPQ2d 1797, Geneva Pharmaceuticals, Inc. v. GlaxoSmithKline PLC, 349 F.3d 1373 [68 USPQ2d 1865] (Fed. Cir. 2003), and Pfizer, Inc. v. Teva Pharmaceuticals USA, Inc., 518 F.3d 1353 [86 USPQ2d 1001] (Fed. Cir. 2008) for analogous situations. The patent discloses the instantly claimed utilities in, for instance as an NR2B subunit-selective N-methyl-D-aspartate (NMDA) receptor antagonist effective for the treatment of ASDs, OCD and/or anxiety disorders. See, e.g., column 4, lines 11-19. See also column 167, line 10 through column 168, line 3 and Table 1.2 in column 177 wherein patent specification demonstrates the use of the compound in an NR2B Radioligand Binding Assay when the compound is administered to the brain tissue of male Wistar rats. Thus, claims 26 and 34 are obvious over the patented claims. (2 of 2) Claims 26 and 34 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-25 of U.S. Patent No. 11,000,526 in view of Fischer, G. et al., Ro 25-6981, a highly potent and selective blocker of N-methyl-D-aspartate receptors containing the NR2B subunit, Characterization in vitro, J. Pharmacol. Exp. Ther., 283(3): 1285-1292 (1997), as cited in IDS dated 03/15/2022. Although the claims at issue are not identical, they are not patentably distinct from each other because the claimed compounds of patent ‘526 are identical to the presently claimed compounds. Patent ‘526 claim 1 recites a method of treating an NMDA receptor-mediated disorder by administering to subject in need a compound such as E1-22.2B’ or E1-22.6B’ which read on the instant species wherein R5 is -CH3 or -CF2H, respectively, while the instant claims are directed to administering to a biological sample which is not taught in US ‘526. However, it would have been obvious to a person having ordinary skill in the art to first test the patented compounds in an in vitro assay before administering to a subject or patient. As such, the skilled artisan would seek methods of similar NR2B antagonists, such as that taught be Fischer et al. Fischer et al. does not teach a method of treating using either E1-22.2B’ or E1-22.6B’ compounds. Fischer et al. does teach a method wherein comparable NR2B antagonist Ro 25-6981 is administered in vitro to young cultured rat cortical neurons expressing NR2B. See page 1288, second column, second paragraph: PNG media_image5.png 498 428 media_image5.png Greyscale . Thus, claims 26 and 34 are obvious over the patented claims. Conclusion Claims 26 and 34 are rejected. Applicant's amendment necessitated the new ground(s) of rejection 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. Contact Information Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jalisa H. Ferguson whose telephone number is (703)756-1489. The examiner can normally be reached Monday - Friday 9:00am - 5:00pm. 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, Joseph McKane can be reached on (571) 272-0699. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /J.H.F./Examiner, Art Unit 1626 /JOSEPH K MCKANE/Supervisory Patent Examiner, Art Unit 1626
Read full office action

Prosecution Timeline

Oct 01, 2021
Application Filed
Mar 15, 2022
Response after Non-Final Action
Mar 20, 2025
Non-Final Rejection — §DP
Aug 22, 2025
Response after Non-Final Action
Aug 22, 2025
Response Filed
Sep 24, 2025
Final Rejection — §DP (current)

Precedent Cases

Applications granted by this same examiner with similar technology

Patent 12599674
CONJUGATES, THEIR COMPOSITIONS, AND THEIR RELATED METHODS
2y 5m to grant Granted Apr 14, 2026
Patent 12582653
METHOD FOR TREATING IDIOPATHIC PULMONARY FIBROSIS
2y 5m to grant Granted Mar 24, 2026
Patent 12577197
METHODS OF PREPARING N6-((2-AZIDOETHOXY)CARBONYL)LYSINE
2y 5m to grant Granted Mar 17, 2026
Patent 12540129
KIF18A INHIBITORS
2y 5m to grant Granted Feb 03, 2026
Patent 12533343
NOVEL METHOD FOR PREPARING (-)-CIBENZOLINE SUCCINATE
2y 5m to grant Granted Jan 27, 2026
Study what changed to get past this examiner. Based on 5 most recent grants.

AI Strategy Recommendation

Get an AI-powered prosecution strategy using examiner precedents, rejection analysis, and claim mapping.
Powered by AI — typically takes 5-10 seconds

Prosecution Projections

3-4
Expected OA Rounds
70%
Grant Probability
99%
With Interview (+63.6%)
3y 2m
Median Time to Grant
Moderate
PTA Risk
Based on 23 resolved cases by this examiner. Grant probability derived from career allow rate.

Sign in with your work email

Enter your email to receive a magic link. No password needed.

Personal email addresses (Gmail, Yahoo, etc.) are not accepted.

Free tier: 3 strategy analyses per month