The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
DETAILED ACTION
Claims 4, 7-9 and 29-30 are presented for examination.
A request for continued examination under 37 C.F.R. §1.114, including the fee set forth in 37 C.F.R. §1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 C.F.R. §1.114, and the fee set forth in 37 C.F.R. §1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 C.F.R. §1.114. Applicant's submission filed on February 16, 2026 has been entered.
Claims 4, 7-9 and 29-30 remain pending. Claims 1-3, 5-6 and 20 are cancelled. Claims 4, 7-9 and 29-30 are amended.
Applicant’s arguments, filed February 16, 2026, have been fully considered. Rejections and/or objections not reiterated from previous Office Actions are hereby withdrawn. The following rejections and/or objections are either reiterated or newly applied. They constitute the complete set of rejections and/or objections presently being applied to the instant application.
Requirement for Restriction/Election
Applicant is reminded of his election without traverse of the invention of Group I (original claims 1-9), directed to a compound of general formula I, or a stereoisomer thereof, or a stereoisomer mixture thereof, or a pharmaceutically acceptable salt or solvate thereof, and the election of the species 2-[(1S)-1-[4-amino-3-(2,3-difluoro-4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-5-chloro-3-phenyl-4(3H)-quinazolinone as the single disclosed species of compound of formula I, which has the chemical structure
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, in which X is CR4, R4 is halogen (fluorine), R2 is C1-C6 alkyl (methyl), R3 is hydrogen, R1 is halogen (chlorine), m is 1, B is C5-C12 aryl (phenyl) and * has a S configuration, as stated in the reply filed February 24, 2025.
As previously indicated at p.3 of the March 20, 2025 Non-Final Office Action, Applicant’s claims 20 and 29 – newly added in the February 24, 2025 claim listing filed with the response to the restriction requirement – were included with the claims examined in the Non-Final Office Action of March 20, 2025, as they were directed to subject matter that would have been properly incorporated with the invention of Group I (original claims 1-9, which are directed to compounds of general formula I).
Applicant’s originally elected species of 2-[(1S)-1-[4-amino-3-(2,3-difluoro-4-methoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-5-chloro-3-phenyl-4(3H)-quinazolinone was determined to be free of prior art that would be applicable to the claims based upon the effective filing date of the claims under AIA 35 U.S.C. §102 and/or 35 U.S.C. §103, as indicated at p.6-7 of the Office Action dated March 20, 2025. For this reason, claims 29-30 were objected to as being dependent upon a rejected base claim, as set forth at p.6 of the Final Rejection dated September 4, 2025.
As such, the search was expanded to include another species within the genus of structural formula I encompassed by the claims – specifically, the compound of Applicant’s formula I, in which R1 is halogen (fluorine), m is 1, B is substituted or unsubstituted C5-C12 aryl (unsubstituted phenyl), * is in the S configuration, R2 is substituted or unsubstituted C1-C6 alkyl (isopropyl), R3 is hydrogen, X is CR4, and R4 is halogen (fluorine).
The amendments to the claims filed with the February 16, 2026 claim listing now cancel claims 1-3, 5-6 and 20, and amend claims 4 and 9 in a manner that obviates the rejection of such claims as reading upon the expanded species of Applicant’s formula I, in which R1 is halogen (fluorine), m is 1, B is substituted or unsubstituted C5-C12 aryl (unsubstituted phenyl), * is in the S configuration, R2 is substituted or unsubstituted C1-C6 alkyl (isopropyl), R3 is hydrogen, X is CR4, and R4 is halogen (fluorine).
Accordingly, the search has now been expanded to include another species within the scope of Applicant’s claims – specifically, the compound identified as II-A-14 (see instant claim 7), which has the chemical structure
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.
Accordingly, the claims that are drawn to the elected invention, elected species and expanded species are claims 4, 7-9 and 29-30 and such claims are herein acted on the merits infra.
Status of Objections/Rejections in the September 4, 2025 Final Action
In reply to the objection to claims 7-8 for depending from a rejected base claim, as set forth at p.5 of the previous Office Action dated September 4, 2025, Applicant now amends the claims to require expansion of the search of instant claim 7 beyond the elected species and first expanded species, and amends claim 8 to now be an independent claim. Accordingly, the objection is now hereby withdrawn.
In reply to the objection to claim 29 as set forth at p.6 of the previous Office Action dated September 4, 2025, Applicant now amends claim 29 to remove the extraneous comma. Accordingly, the objection is now hereby withdrawn.
In reply to the objection to claim 30 as set forth at p.6 of the previous Office Action dated September 4, 2025, Applicant now amends claim 30 to remove the extraneous comma. Accordingly, the objection is now hereby withdrawn.
In reply to the rejection of claims 1-6, 9 and 20 under 35 U.S.C. §103 as being unpatentable over Deng et al. (WO 2017/079558 A1; 2017) in view of Silverman (“The Organic Chemistry of Drug Design and Drug Action (Second Edition)”, Section 2, Elsevier Academic Press, 2004, p.29-32), as set forth at p.6-13 of the previous Office Action dated September 4, 2025, Applicant now cancels claims 1-3, 5-6 and 20, and amends claims 4 and 9 in a manner that no longer reads on the expanded species that was subject to rejection. Accordingly, the rejection is now hereby withdrawn.
Upon further reconsideration of the claimed subject matter, however, new grounds for rejection are necessitated and set forth infra.
Objection to the Claims
As previously set forth at p.6 of the Final Office Action dated September 4, 2025, claims 29-30 remain objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Claim Rejections - 35 USC § 103 (New Grounds of Rejection)
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.
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.
(1) Claim 7 is rejected under 35 U.S.C. 103 as being unpatentable over Lei et al. (“Discovery of the Potent Phosphoinositide 3-Kinase d (PI3K d) Inhibitors”, ChemistrySelect, 2020 January; 5:196-200) in view of Silverman (“The Organic Chemistry of Drug Design and Drug Action (Second Edition)”, Section 2, Elsevier Academic Press, 2004, p.29-32, cited on the 12/24/24 PTO-892).
Deng et al. teaches compound 4, which has the chemical structure
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, in which Het is
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, R1 is S2, which is
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, and R2 is hydrogen, as having potent PI3Kd inhibitory activity, as well as anti-cancer activity against jeko-1 cancer cells and low toxicity as measured in a peripheral blood mononuclear cell (PBMC) assay (abstract; col.2, para.1, p.197; Table 1, p.198; col.2, para.2, p.198-col.1, para.1, p.199; Fig.7, p.199).
This compound 4 of Lei et al. corresponds to Applicant’s instantly claimed compound II-A-14 of claim 7, which is
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, but for the fact that Applicant’s compound II-A-14 contains a fluorine substitution at position 2 of the pyridine ring, whereas compound 4 of Lei et al. contains a hydrogen substitution at this same position (claim 7).
Silverman teaches that fluorine and hydrogen are bioisosteric equivalents, which are defined as atoms, ions or molecules in which the peripheral layers of electrons are identical, with the expectation of producing broadly similar biological properties such that each may be substituted one for the other and preserve therapeutic functionality of the compound (para.1, p.29; Table 2.3, p.32).
A person of ordinary skill in the art before the effective filing date of the claimed invention would have had a reasonable expectation of success in modifying Lei’s PI3Kd inhibitor compound 4 by substituting the 2-hydrogen substitution of the 4-isopropoxypyridine ring with 2-fluoro because Silverman et al. teaches that fluorine and hydrogen were known bioisosteric equivalents and were, therefore, substantially interchangeable with one another with the expectation of similar biological properties. The skilled artisan would have found it prima facie obvious to make such a substitution because it was well-known in the art that fluorine and hydrogen were substituted one for the other in medicinal chemistry while still substantially preserving therapeutic functionality of the compound, as taught by Silverman. In addition, the ordinarily skilled artisan would have been motivated by the reasonable expectation that compounds similar in structure (such as that of Lei et al. and the instant claims) have similar properties and that it was generally accepted in the art that compounds of sufficiently close or homologous structure possess similar pharmacologic properties. MPEP §2144.09. It would, therefore, have been prima facie obvious to the ordinarily skilled artisan before the effective filing date of the claimed invention to modify the PI3Kd inhibitor compound 4 disclosed by Lei et al. to substitute the 2-hydrogen position of the 4-isopropoxypyridine ring with 2-fluoro to arrive at a compound of the structure of II-A-14 instantly claimed with a reasonable expectation of success in preserving substantially similar therapeutic activity.
Therefore, the invention as a whole would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention.
Response to Applicant’s Arguments
In reply, Applicant traverses the previously applied rejections in view of the submitted amendments and arguments (Remarks, p.9-11).
Applicant’s traversal and amendments have been fully and carefully considered, and the previously applied rejections have been withdrawn as indicated above.
Upon further reconsideration of the claimed subject matter as amended, however, new grounds for rejection are necessitated and are set forth infra.
For these reasons supra, rejection of claim 7 is proper.
Conclusion
Rejection of claim 7 is proper.
Claims 29-30 are objected to for depending from a rejected base claim.
Claims 4 and 8-9 of the present application are allowed.
Applicant is requested to specifically point out the support for any amendments made to the disclosure in response to this Office action, including the claims (M.P.E.P. §§ 714.02 and 2163.06). In doing so, applicant is requested to refer to pages and line (or paragraph) numbers (if available) in the as-filed specification, not the published application. Due to the procedure outlined in M.P.E.P. § 2163.06 for interpreting claims, other art may be applicable under 35 U.S.C. § 102 or 35 U.S.C. § 103(a) once the aforementioned issue(s) is/are addressed.
Applicant is reminded that MPEP §2001.06(b) clearly states that “[t]he individuals covered by 37 C.F.R. 1.56 have a duty to bring to the attention of the examiner, or other Office official involved with the examination of a particular application, information within their knowledge as to other copending United States applications which are "material to patentability" of the application in question." See Armour & Co. v. Swift & Co., 466 F.2d 767, 779, 175 USPQ 70, 79 (7th Cir. 1972). MPEP §2001.06(b) clearly indicates that “if a particular inventor has different applications pending in which similar subject matter but patentably indistinct claims are present that fact must be disclosed to the examiner of each of the involved applications.” See Dayco Prod. Inc. v. Total Containment, Inc., 329 F.3d 1358, 1365-69, 66 USPQ2d 1801, 1806-08 (Fed. Cir. 2003).
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Leslie A. Royds Draper whose telephone number is (571)272-6096. The examiner can normally be reached Tuesday to Thursday (08:30 AM to 05:00 PM).
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jeffrey S. Lundgren can be reached at (571)-272-5541. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/Leslie A. Royds Draper/Primary Examiner, Art Unit 1629
March 1, 2026