Prosecution Insights
Last updated: April 19, 2026
Application No. 18/043,163

HYDROXYNORKETAMINE COMPOUNDS AND METHODS OF USE THEREOF

Non-Final OA §102§112
Filed
Feb 27, 2023
Examiner
RAO, PADMAJA S
Art Unit
1627
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
The United States Department of Veterans Affairs
OA Round
1 (Non-Final)
71%
Grant Probability
Favorable
1-2
OA Rounds
2y 8m
To Grant
99%
With Interview

Examiner Intelligence

Grants 71% — above average
71%
Career Allow Rate
84 granted / 118 resolved
+11.2% vs TC avg
Strong +40% interview lift
Without
With
+40.4%
Interview Lift
resolved cases with interview
Typical timeline
2y 8m
Avg Prosecution
61 currently pending
Career history
179
Total Applications
across all art units

Statute-Specific Performance

§101
2.3%
-37.7% vs TC avg
§103
32.8%
-7.2% vs TC avg
§102
17.2%
-22.8% vs TC avg
§112
25.2%
-14.8% vs TC avg
Black line = Tech Center average estimate • Based on career data from 118 resolved cases

Office Action

§102 §112
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 and Response to Restriction Requirement Claims 1-9 and 14-21 are pending as of the response filed 10/21/2025. Claims 10-13 are cancelled. Applicant’s election of a group I claims 1-9 and 14, without traverse is acknowledged, in this transfer case. Claims 15-21 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim. Applicant’s election of a species of disease or condition as depressive disorders is acknowledged. Because Applicant did not distinctly and specifically point out the supposed errors in the election of species requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)). Claims 1-9 and 14 are examined herein. Priority This application is a 371 of PCT/US2021/048095 filed 08/27/2021, which claims priority to PRO 63/071,334 filed 08/27/2020. Information Disclosure Statement The information disclosure statement submitted on 02/27/2023 has been considered. The submission is in compliance with the provisions of 37 CFR 1.97. Additionally, the listing of references in the specification is not a proper information disclosure statement. 37 CFR 1.98(b) requires a list of all patents, publications, applications, or other information submitted for consideration by the Office, and MPEP § 609.04(a), subsection I. states, "the list may not be incorporated into the specification but must be submitted in a separate paper." Therefore, unless the references have been cited by the examiner on form PTO-892, they have not been considered. Specification The disclosure is objected to because it contains an embedded hyperlink and/or other form of browser-executable code on Pg. 130, reference # 20; Pg. 131, reference # 22 of the instant specification. Applicant is required to delete the embedded hyperlink and/or other form of browser-executable code; references to websites should be limited to the top-level domain name without any prefix such as http:// or other browser-executable code. See MPEP § 608.01. Additionally, Applicants are required to amend the specification in response to the 35 U.S.C. 112(b) rejection of claim 7, as noted below. Claim Rejections - 35 USC § 112 The following is a quotation of 35 U.S.C. 112(b): (b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention. The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph: The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention. Claims 1-9 and 14 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention. Regarding claims 1-4 and 7-9, the claims recite the limitation “or prodrug thereof”. Paras. [0040]-[0041] of the instant specification defines the term "prodrug" to refer to a compound that results in vivo to the active compound as a result of chemical or metabolic processes. The instant specification further defines a prodrug as “any compound that can be converted in vivo to provide the bioactive agent” to be included within the scope of the invention. Although the specification lists free carboxyl groups derivatized as amides or alkyl esters, acetates, pivalates, methylcarbonates, benzoates and the like as examples of prodrugs, the specification does not provide a limiting definition of the term “prodrug”. The full scope of the compounds – possible prodrugs encompassed by the claims has not been defined. Therefore, the metes and bounds of the claim is indefinite. Claims 5-6 and 14 depend from these rejected claims, and are similarly rejected. For the purpose of applying prior art, the claims have been interpreted without the limitation “or prodrug thereof” appearing in the claim. Additionally, regarding claim 5, the claim depends from claim 1 and recites the limitation “wherein R1 is independently selected at each occurrence from C1-C4alkyl”. The compounds of formula (I), formula (II), or formula (III) only have one R1 group in the compound. The recitation of “independently selected at each occurrence” render the scope of the claim indefinite. For the purpose of applying prior art, claim 5 has been interpreted to read “wherein R1 is selected from C1-C4alkyl”. Additionally, regarding claim 7, the claim recites the following compounds, compound 1007, 1014, 1021, 1028, 1035, 1042, 1049, 1056, 1063, 1070, 1077, and 1084, wherein R1 is -(CH3)3. The attachment of “-(CH3)3” to the cyclohexane ring is not permitted by the valency of carbon at the point of attachment. This renders the metes and bounds of the claim indefinite. For the purpose of applying prior art, the cited compounds of claim 7 have been interpreted as wherein, R1 is “-C(CH3)3” in line with the definition of R1 which allows for R1 to be C4 alkyl. Claim Rejections - 35 USC § 102 In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status. The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action: A person shall be entitled to a patent unless – (a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention. Claims 1-9 and 14 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Myerson et al. (WO 2018/104729 A1, 14 June 2018, hereinafter Myerson). Regarding instant claims 1, 3, 5-7, Myerson teaches conformationally stabilized analogues of the ketamine metabolites 6-hydroxyketamine and 6-hydroxynorketamine with applications in the treatment of depression disorders and anxiety disorders (Abstract). Myerson teaches compounds of Formula I, or a pharmaceutically acceptable salt thereof; wherein R1 is H or C1-C4 alkyl; R2 is H or C1-C4 alkyl; R3 is H or C1-C4 alkyl; R4 is H or C1-C4 alkyl; R5 is H or C1-C4 alkyl; and R6 represents 0, 1, 2, 3, 4 or 5 haloatoms each independently selected from F, CI, Br, I, wherein when R2 is H, preferably at least one of R3, R4and R5 is not H (Abstract; Pg. 1, Lns. 4-13). PNG media_image1.png 144 147 media_image1.png Greyscale Myerson teaches the exemplary compound, compound 11 (Pg. 12, Lns. 1-4). PNG media_image2.png 138 172 media_image2.png Greyscale Compound 11 of Myerson falls within the scope of instant formula (II), specifically formula (IIa) (as in instant claims 3 and 6), wherein R1 is methyl. Regarding instant claims 2, 4 and 8, wherein the instant R1 group is ortho or para to the hydroxyl group of the cyclohexane ring, Myerson teaches embodiments in which R3 is H or Me; R4 is H or Me and when R2 is H and at least one of R3, R4, and R is not H (Pg. 8, Lns. 13-17). Moreover, Myerson teaches the variables R3, R4 and R5 to be H or C1-C4 alkyl (Pg. 8, Lns. 9-10) (this anticipates R1 groups as in instant claim 7). According to MPEP 2131.02(III), “A GENERIC DISCLOSURE WILL ANTICIPATE A CLAIMED SPECIES COVERED BY THAT DISCLOSURE WHEN THE SPECIES CAN BE "AT ONCE ENVISAGED" FROM THE DISCLOSURE”. A reference disclosure can anticipate a claim when the reference describes the limitations but "'d[oes] not expressly spell out' the limitations as arranged or combined as in the claim, if a person of skill in the art, reading the reference, would ‘at once envisage’ the claimed arrangement or combination." Kennametal, Inc. v. Ingersoll Cutting Tool Co., 780 F.3d 1376, 1381, 114 USPQ2d 1250, 1254 (Fed. Cir. 2015) (quoting In re Petering, 301 F.2d 676, 681(CCPA 1962)). In the instant case, compounds of formula (I) and formula (III) (as in instant claims 1-2, 4 and 7-8) can be clearly envisaged from the disclosure of Myerson. Therefore, the compounds of instant claims 1-8 are anticipated by Myerson. Regarding instant claims 9 and 14, Myerson teaches compositions are prepared by uniformly and intimately admixing the active ingredient with liquid carriers or finely divided solid carriers or both and may be prepared by mixing the principle active agent(s) with a pharmaceutical carrier (Pg. 3, Lns. 3-9). Myerson teaches oral dosage forms for oral administration (Pg. 2, Ln. 37 – Pg. 3, Ln. 13; Pg. 13, Lns. 19-24). Therefore, Myerson anticipates the pharmaceutical composition as in instant claims 9 and 14. Miscellaneous The examiner would like to bring Applicant’s attention to the following: A power of attorney document is not present in the application file. Conclusion Claims 1-9 and 14 are rejected. No claims are allowed. Any inquiry concerning this communication or earlier communications from the examiner should be directed to PADMAJA S RAO whose telephone number is (571)272-9918. The examiner can normally be reached 9:00-5:30 pm EDT. 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, Kortney L Klinkel can be reached on (571) 270-5239. 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. /P.S.R./ Examiner, Art Unit 1627 /SARAH PIHONAK/Primary Examiner, Art Unit 1627
Read full office action

Prosecution Timeline

Feb 27, 2023
Application Filed
Nov 19, 2025
Non-Final Rejection — §102, §112
Mar 26, 2026
Response Filed

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Study what changed to get past this examiner. Based on 5 most recent grants.

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Prosecution Projections

1-2
Expected OA Rounds
71%
Grant Probability
99%
With Interview (+40.4%)
2y 8m
Median Time to Grant
Low
PTA Risk
Based on 118 resolved cases by this examiner. Grant probability derived from career allow rate.

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