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 .
Election/Restrictions
Applicant’s election without traverse of
PNG
media_image1.png
177
287
media_image1.png
Greyscale
in the reply filed on 4/6/2026 is acknowledged.
This compound is free of the prior art. The Markush search was extended to
PNG
media_image2.png
390
540
media_image2.png
Greyscale
This compound reads on claims 1-3, 8, 13, and 14.
Claims 4-7, 9-12, 15-18 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 4/6/2026.
Priority
This application is a national stage entry of PCT/US2022/073244, which claims priority to US provisional application 63/218,555.
The instant claims find support from the provisional application. Therefore, the effective filing date is 07/06/2021.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 3/5/2024, is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Claim Objections
Claim 1 is objected to because of the following informalities: R2b in claim 1 needs a comma between morpholinyl and the next option (which is depicted visually). The last option in R2a in claim 1 has a phrase which is cut off (the word “alkyl” in C1--C4 alkyl). Appropriate correction is required.
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.
Claim(s) 1-3, 8, 13, and 14 are rejected under 35 U.S.C. 103 as being unpatentable over Chupak (WO2015/160641) in view of KHALIMON (Khalimon et al., “Base Metal Catalysts for deoxygenative Reduction of Amides to Amines”, MDPI, May 28, 2019) and KUMARI (Kumari et al., “Amide Bond Bioisosteres: Strategies, Synthesis, and successes”, Journal of Medicinal Chemistry, July 20, 2020) and WAGER (Wager et al., “Defining Desirable Central Nervous System Drug Space through the Alignment of Molecular Properties, in Vitro ADME, and Safety Attributes”, ACS Chemical Neuroscience, March 25, 2010).
Chupak teaches this compound
PNG
media_image2.png
390
540
media_image2.png
Greyscale
. This compound maps for formula I, wherein R1 is
PNG
media_image3.png
111
93
media_image3.png
Greyscale
, R2 is -CH2R2a, where R2a is
PNG
media_image4.png
128
136
media_image4.png
Greyscale
that is substituted with an oxo group (the substitution is not within the scope of the claims), t is 0, R4 is H, R3 is methyl, and s is 0 (Chupak page 365 fourth compound on the page).
This helps teach claims 1, 2, and 3.
Chupak teaches this compound as part of a pharmaceutical composition with a pharmaceutically acceptable carrier (reference claim 15 on page 378). This helps teach claims 8, 13, and 14.
Chupak does not teach removing the oxo in the instant R2a group.
KHALIMON teaches deoxygenative reduction of amides to amines is well known in the art (title and abstract).
Kumari teaches that bioisosterism is widely employed in the rational modification of lead compounds, being used to increase potency, enhance selectivity, improve pharmacokinetic properties, eliminate toxicity, and acquire novel chemical space to secure intellectual property (abstract).
Wager teaches that amides impart substation polarity and are less common for drugs targeting the central nervous system because they hamper permeation (page 422).
The artisan would be motivated to remove the oxo from the CONH2 in R2a group because medicinal chemists commonly modify compounds in order to modify the activity of a lead compound (Kumari abstract). Deoxygenative reduction of amides to amines is well known in the art (KHALIMON title and abstract). Specifically, an artisan would be motivated to increase permeation into the central nervous system by modifying polarity of a compound. Therefore, the artisan would expect that removing the oxo group (arriving at the instant compound) of Chupak would result in a compound (the instant compound ) that has increased permeation and/or modified pharmaceutical activity. This teaches claims 1, 2, and 3.
Chupak teaches this compound as part of a pharmaceutical composition with a pharmaceutically acceptable carrier (reference claim 15 on page 378). This teaches claims 8, 13, and 14.
Conclusion
No claims are allowable as written.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to GILLIAN A HUTTER whose telephone number is (571)272-6323. The examiner can normally be reached M-F 7:30-5.
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, Andrew Kosar can be reached at 571-272-0913. 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.
/G.A.H./ Examiner, Art Unit 1625 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625
Prosecution Insights