DETAILED ACTION
This office action is in response to applicant’s filing dated May 11, 2026.
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 Claims
Claims 1-4, 7-21, 23-41, and 46 are pending in the instant application. Acknowledgement is made of Applicant's amendments and remarks filed May 11, 2026. Claims 5,6, 22, 42-45, 47, and 48 were previously canceled.
Election/Restrictions
Applicant’s election without traverse of Group I, drawn to a compound of Formula I below, or a solvate, stereoisomer or pharmaceutically acceptable salt thereof in the reply filed on May 11, 2026 is acknowledged.
Claim 46 is withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on May 11, 2026.
Applicant’s election without traverse of Example 46, (R)-N-(1-(3-amino-5-(trifluoromethyl)phenyl)ethyl)-1-(2-fluorophenyl)-6-oxo-1,6-dihydropyridazine-3-carboxamide:
PNG
media_image1.png
193
239
media_image1.png
Greyscale
in the reply filed on May 11, 2026 is acknowledged.
Example 46 is a compound of formula (I) wherein
PNG
media_image2.png
30
90
media_image2.png
Greyscale
is a double bond; Z1 is N; Z2 and Z3 are both CHR1, wherein each R1 is independently H; R’ and R” are independently H and C1-alkyl, methyl; A is Cy1, wherein Cy1 is C6 aryl, phenyl, substituted with 2 R2a, wherein each R2a is C1 haloalkyl, CF3, and NRbRc, wherein Rb and Rc are independently H; and B is –(CH2)0-Cy3, wherein o is 0, Cy3 is C6 aryl, phenyl, substituted with 1 R3a, wherein R3a is halogen, F.
Example 46 has been found free of the prior art. Thus, examination has been expanded to encompass Rapitalam:
PNG
media_image3.png
159
325
media_image3.png
Greyscale
,
Compound 258:
PNG
media_image4.png
183
385
media_image4.png
Greyscale
,
wherein R is H and R1 is Me (methyl),
PNG
media_image5.png
228
525
media_image5.png
Greyscale
,
PNG
media_image6.png
143
375
media_image6.png
Greyscale
,
PNG
media_image7.png
130
326
media_image7.png
Greyscale
, and
PNG
media_image8.png
125
297
media_image8.png
Greyscale
.
Claims 7, 16-21, 23, 25, and 31-39 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species, there being no allowable generic or linking claim.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 May 11, 2026.
Claims 1-4, 8-15, 24, 26-30, 40, and 41 are presently under examination as they relate to the elected species, Example 46:
PNG
media_image1.png
193
239
media_image1.png
Greyscale
and expanded species Rapitalam:
PNG
media_image3.png
159
325
media_image3.png
Greyscale
Compound 258:
PNG
media_image4.png
183
385
media_image4.png
Greyscale
,
wherein R is H and R1 is Me (methyl),
PNG
media_image5.png
228
525
media_image5.png
Greyscale
,
PNG
media_image6.png
143
375
media_image6.png
Greyscale
,
PNG
media_image7.png
130
326
media_image7.png
Greyscale
, and
PNG
media_image8.png
125
297
media_image8.png
Greyscale
Priority
The present application is a 371 of US Application No. PCT/KR2022/012254 filed on August 17, 2022, which claims benefit of foreign priority to KOREA 10-2021-0108316 filed on August 17, 2021.
Information Disclosure Statement
The information disclosure statements (IDS) submitted on March 1, 2024; April 24, 2025; March 24, 2026; and May 19, 2026 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner, except where marked with a strikethrough.
Specification
The lengthy specification has not been checked to the extent necessary to determine the presence of all possible minor errors. Applicant’s cooperation is requested in correcting any errors of which applicant may become aware in the specification.
Applicant is reminded of the proper language and format for an abstract of the disclosure.
The abstract should be in narrative form and generally limited to a single paragraph on a separate sheet within the range of 50 to 150 words in length. The abstract should describe the disclosure sufficiently to assist readers in deciding whether there is a need for consulting the full patent text for details.
The language should be clear and concise and should not repeat information given in the title. It should avoid using phrases which can be implied, such as, “The disclosure concerns,” “The disclosure defined by this invention,” “The disclosure describes,” etc. In addition, the form and legal phraseology often used in patent claims, such as “means” and “said,” should be avoided. In the instant case, the abstract contains language which can be implied.
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.
Claims 1-4, 8, 11-15, 24, 26-30, and 41 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Avdeeva (Research Results in Pharmacology, 2020; 6(2): 9-17).
Regarding claims 1-4, 8, 11-15, 24, 26-30, and 41, Avdeeva teaches Rapitalam 6 mg/kg and 20 mg/kg by gavage (Abstract, Materials and methods). Rapitalam has the structure:
PNG
media_image3.png
159
325
media_image3.png
Greyscale
as evidenced by STN (CAS registry number: 1004384-08-0, STN entry date: February 19, 2008). Rapitalam is a compound of formula (I) wherein
PNG
media_image2.png
30
90
media_image2.png
Greyscale
is a double bond; Z1 is N; Z2 and Z3 are both CHR1, wherein each R1 is independently H and C1 alkoxy, methoxy; R’ and R” are independently H; A is Cy1, wherein Cy1 is C6 aryl, phenyl, substituted with 1 R2a, wherein R2a is halogen, Cl; and B is –(CH2)o-Cy3, wherein o is 0, Cy3 is C6 aryl, phenyl, substituted with 1 R3a, wherein R3a is C1 alkyl, methyl.
Thus, the teachings of Avdeeva anticipate the compounds of claims 1-4, 8, 11-15, 24, 26-30, and 41.
Claims 1-4, 8, 11-15, 24, and 26-30 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Severin et al (Research Results in Pharmacology, 2020; 6(1): 69-82).
Regarding claims 1-4, 8, 11-15, 24, and 26-30, Severin teaches Compound 258 (Table 1). Compound 258 has the structure:
PNG
media_image4.png
183
385
media_image4.png
Greyscale
wherein R is H and R1 is Me (methyl). Compound 258 is a compound of formula (I) wherein
PNG
media_image2.png
30
90
media_image2.png
Greyscale
is a double bond; Z1 is N; Z2 and Z3 are both CHR1, wherein each R1 is independently H and C1 alkoxy, methoxy; R’ and R” are independently H and methyl; A is Cy1, wherein Cy1 is C6 aryl, phenyl; and B is –(CH2)o-Cy3, wherein o is 0, Cy3 is C6 aryl, phenyl, substituted with 1 R3a, wherein R3a is C1 alkyl, methyl.
Thus, the teachings of Avdeeva anticipate the compounds of claims 1-4, 8, 11-15, 24, and 26-30.
Claims 1-4, 8, 9, 11-15, and 26-30 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Chemical Library (Registry Chemcats, April 23, 2021, XP093232546, cited in the IDS filed April 24, 2025).
Regarding claims 1-4, 8, 9, 11-15, and 26-30, Chemical Library teaches the compound:
PNG
media_image5.png
228
525
media_image5.png
Greyscale
The compound taught by Chemical Library is a compound of formula (I) wherein
PNG
media_image2.png
30
90
media_image2.png
Greyscale
is a double bond; Z1 is N; Z2 and Z3 are both CHR1, wherein each R1 is independently H; R’ and R” are independently H and C1 alkyl, methyl; A is Cy1, wherein Cy1 is C6 aryl, phenyl, substituted with 2 R2a, wherein each R2a is C1 alkyl, methyl; and B is –(CH2)o-Cy3, wherein o is 0, Cy3 is C6 aryl, phenyl.
Thus, the teachings of Chemical Library anticipate the compounds of claims 1-4, 8, 9, 11-15, and 26-30.
Claims 1-4, 8, 9, 11-15, and 26-30 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Registry (STN, April 21, 2021, CAS Registry Nos. 2636017-10-0, 263016-90-3, cited in the IDS filed May 19, 2026).
Regarding claims 1-4, 8, 9, 11-15, 24, and 26-30, Chemical Library teaches the compound:
PNG
media_image6.png
143
375
media_image6.png
Greyscale
The compound taught by Registry is a compound of formula (I) wherein
PNG
media_image2.png
30
90
media_image2.png
Greyscale
is a double bond; Z1 is N; Z2 and Z3 are both CHR1, wherein each R1 is independently H; R’ and R” are independently H and C1 alkyl, methyl; A is Cy1, wherein Cy1 is C6 aryl, phenyl, substituted with 2 R2a, wherein each R2a is C1 alkyl, methyl; and B is –(CH2)o-Cy3, wherein o is 0, Cy3 is C6 aryl, phenyl.
Thus, the teachings of Chemical Library anticipate the compounds of claims 1-4, 8, 9, 11-15, 24, and 26-30.
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.
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.
Claims 9, 10, 40, and 41 are rejected under 35 U.S.C. 103 as being unpatentable over Severin et al (Research Results in Pharmacology, 2020; 6(1): 69-82) as applied to claims 1-4, 8, 11-15, 24, and 26-30 above.
Severin teaches N-substituted 4-methoxy-6-oxo-1-aryl-pyridazine-3-carboxamide derivatives as potential modulators of glutamate receptors. As set forth above, Severin teaches a Compound 258 (Table 1). Compound 258 has the structure:
PNG
media_image4.png
183
385
media_image4.png
Greyscale
wherein R is H and R1 is Me (methyl) (Table 1).
Severin does not explicitly teach the methyl of R’ or R” is in the stereochemistry of claims 9 or 10. The compound of Severin is a construed as a racemate of a compound of formula (I). However, MPEP 2144.09 states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. "An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties." In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious); Aventis Pharma Deutschland v. Lupin Ltd., 499 F.3d 1293, 84 USPQ2d 1197 (Fed. Cir. 2007) (5(S) stereoisomer of ramipril obvious over prior art mixture of stereoisomers of ramipril.) In the instant case, a stereoisomer of compound 258 having the stereochemical structure of claims 9 or 10 is obvious. Moreover, the skilled artisan would have been motivated to formulate the stereoisomer of compound 258 to determine if the individual isomers would dock and modulate glutamate receptors.
Taken together, all this would result in a compound of claims 9 and 10 with a reasonable expectation of success.
Regarding claim 40, Compound 258 is a positional isomer of compounds:
PNG
media_image7.png
130
326
media_image7.png
Greyscale
and
PNG
media_image8.png
125
297
media_image8.png
Greyscale
MPEP 2144.09 states: A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious); Aventis Pharma Deutschland v. Lupin Ltd., 499 F.3d 1293, 84 USPQ2d 1197 (Fed. Cir. 2007) (5(S) stereoisomer of ramipril obvious over prior art mixture of stereoisomers of ramipril.) In the instant case, compound 258 is a racemic compound of a positional isomeric compound of the instant claims wherein the methyl is in different positions of the Cy1 ring and is of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. Moreover, the skilled artisan would have been motivated to formulate the stereoisomer and positional isomer of compound 258 to produce additional compounds with similar activity (e.g. glutamate receptor modulator).
Taken together, all this would result in a compound of claim 40 with a reasonable expectation of success.
Conclusion
Claims 1-4, 8-15, 24, 26-30, 40, and 41 are rejected.
No claim is allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RAYNA B RODRIGUEZ whose telephone number is (571)272-7088. The examiner can normally be reached 8am-5:00pm, Monday - Thursday.
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, Amy L Clark can be reached at 571-272-1310. 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.
/Rayna Rodriguez/ Primary Examiner, Art Unit 1628
Prosecution Insights