DETAILED ACTION
Claims 1-30 are currently pending in the instant application. Claims 1, 2, 4, 24, and 25 are rejected. Claim 25 is objected. Claims 3, 5-23, and 26-30 are withdrawn from consideration as being for non-elected subject matter.
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 Group I and the species of compound 36:
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in the reply filed on 4 June 2026 is acknowledged.
According to MPEP 803.02, the examiner has determined whether the elected species is allowable. Applicants’ elected species does not appear allowable. However, in order to expedite prosecution, the search and examination has been extended to the compounds:
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, and
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which are not allowable
Claims 1, 2, 4, 24, and 25 have been examined to the extent that they are readable on the elected embodiment, the elected species and the above mentioned compounds. In regards to withdrawn claims 6-10, 12, and 20, which applicant indicated reads on the elected species on page 2 of the remarks filed 4 June 2026, these claims do not read on the elected species. Claim 6 defines R1 to be:
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which requires R1 to be substituted with at least one fluoro which is not present on elected species compound 36. The same requirement that R1 be substituted with at least one fluoro is also found in claims 7-10, 12, and 20. Therefore, claims 6-10, 12, and 20 do not read on the elected species and are also considered withdrawn claims along with claims 3, 5, 11, 13-19, 21-23, and 26-30.
Drawings
The drawings are objected to because Figure 6 has table which is illegible due to the size of font which is too small. Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance.
Claim Objections
Claim 25 is objected to under 37 CFR 1.75(c) as being in improper form because a multiple dependent claim cannot depend from a multiple dependent claim. Claim 25 is dependent upon any one of claims 1-24 of which withdrawn claims 10-15 and 20-23 are also multiple dependent claims. Therefore, claim 25 is a multiple dependent claim which depends from additional multiple dependent claims. See MPEP § 608.01(n).
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 (i.e., changing from AIA to pre-AIA ) 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.
Claim(s) 1, 2, and 25 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by WO 2007/038372 (IDS filed 1/21/2025, Cite No. 1 Foreign Patent Documents).
WO 2007/038372 discloses the compound on page 6, scheme 2:
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which corresponds to the compound 35 of the instant claims:
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as step (f) of scheme 2 utilizes water, the compound
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is in water which corresponds to instant claim 25.
Claim(s) 24 and 25 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Blaazer et al. (IDS filed 7/31/2025, Cite No. 1 Non-Patent Literature Documents).
Blaazer et al. discloses the compound 21:
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on page 1301,which is the formula
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. The compound 21, after in vitro testing, was found to act as 5-HT2 receptor antagonist with the highest binding affinity, page 1303. In regards to claim 24 which claims the compounds:
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while the prior art compound stereochemistry is not provided, the prior art compound is either a mixture of stereoisomers which would necessarily include each formula 4ent1 and 4ent2 as found in instant claim 24, or the prior art compound is one specific stereoisomer of formula 4ent1 or 4ent2 whose stereochemistry is not provided. Both considerations anticipate instant claim 24. The in vitro testing with compound 21 anticipates instant claim 25.
Claim Rejections - 35 USC § 103
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 (i.e., changing from AIA to pre-AIA ) 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 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, 2, 4, 24 and 25 is/are rejected under 35 U.S.C. 103 as being unpatentable over Blaazer et al. (IDS filed 7/31/2025, Cite No. 1 Non-Patent Literature Documents).
Blaazer et al. discloses the compound 21:
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on page 1301,which is the formula
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. The compound 21, after in vitro testing, was found to act as 5-HT2 receptor antagonist with the highest binding affinity, page 1303:
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. Blaazer et al. also disclose the compounds 13 and 13 on page 1301:
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which correspond to
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(compound 13) and
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(compound 14). Applicant’s instant elected species 36 is
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which is a homolog of compounds 13 and 14 of the prior art at the chain X and is a homolog of the compound 21 at the amine containing substituent. Additionally see page 1302 which provides that homologation of the 4-alkyl group results in more potent agents such as compound 13 and 14:
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. Treatment of diseases by drugs that target 5-HT receptors are provided on page 1300. To those skilled in chemical art, one homologue is not such an advance over adjacent members of series as requires invention because chemists knowing properties of one member of series would in general know what to expect in adjacent members. In re Henze, 85 USPQ 261 (1950). The instant claimed compounds would have been obvious because one skilled in the art would have been motivated to prepare homologs of the compounds taught in the reference with the expectation of obtaining compounds which could be used to treat diseases related to 5HT receptors. Therefore, the instant claimed compounds would have been suggested to one skilled in the art. Additionally, please see MPEP 2144.09, Compounds which are homologs are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to REBECCA L ANDERSON whose telephone number is (571)272-0696. The examiner can normally be reached Monday-Friday from 6am-2pm.
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.
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/REBECCA L ANDERSON/Primary Examiner, Art Unit 1626 ____________________ 12 June 2026
Rebecca Anderson
Primary Examiner
Art Unit 1626, Group 1620
Technology Center 1600
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