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 .
DETAILED ACTION
Status of 17/639,615
Claims 1-21 are currently pending.
Priority
Instant application 17/639,615, filed 3/2/2022, claims priority as follows:
PNG
media_image1.png
55
343
media_image1.png
Greyscale
Provisional application 62/896,081 provides support for the instant claims, and thus, claims 1-21 are granted the priority date of 9/5/2019.
Information Disclosure Statement
All references from the IDS submitted on 5/3/2022 have been considered unless marked with a strikethrough.
Response to Arguments/Amendments
The amendment filed 1/22/2026 has been entered. Applicant has amended claims 1 and 3. No claims have been cancelled or added.
The Examiner appreciates Exhibits A-C demonstrating Applicant’s interpretation of the limitation of “N-substituted” as recited in claims 1 and 5 with respect to R11, and recognizes that the limitation may be interpreted as a substituent attached to the nitrogen atom of the ring. However, the Examiner maintains that the limitation may also be interpreted as any N-containing substituent attached to a carbon, and one of ordinary skill in the art would readily use the terminology to describe an N-containing substituent attached to a carbon as evidenced Mateu (Mateu, N. et. al. Chem. Eur. J. 2018, 24, 13681-13687). Mateu discloses “N-substituted Quaternary Carbon-Containing Small Molecules” such as compounds 12 and 13 (Scheme 1):
PNG
media_image2.png
190
642
media_image2.png
Greyscale
which contain a -NH2 as a substituent. Thus, unless Applicant amends the claim to clarify the limitation, the interpretation of the limitation “N-substituted” can be interpreted as either a substituent on the nitrogen atom of the ring or as any N-containing substituent attached to a carbon atom.
Claims 1-2, 4-5, 9, 11-13, 16-17, and 20 were rejected under 35 U.S.C. 102(a)(1) and 102(a)(2) in the Non-Final dated 10/27/2025. In response, Applicant has argued that in light of their interpretation of the limitation “N-substituted” discussed above, the compounds of Gilead are properly characterized as C-substituted instead of N-substituted, and thus not anticipated by Gilead. Applicants arguments have been considered, but are not persuasive because the limitation can still be interpreted as any N-containing substituent attached to a carbon atom. Thus, the rejection is not overcome and the rejection is maintained.
In the Non-Final dated 10/27/2025, claims 1-4, 9, 11-13, and 16-17 were rejected under 35 U.S.C. 102(a)(1) and 102(a)(2). In response, Applicant has amended claim 1 to omit hydrogen from the variables of R11 and has specified that the alkoxy of R11 is unsubstituted, which overcomes the rejections of Gilead where anticipatory compounds contain a hydrogen at R11. However, the compound of Gilead where R11 is a Boc-group, (S)-tert-butyl-2-(8-iodo-4-oxo-3-phenyl-3,4-dihydroquinaolin-2-yl)pyrrolidine-1-carboxylate, is still anticipatory because an alternative interpretation of R11 includes alkyl, which further includes a substituted alkyl according to the instant disclosure (page 7, lines 23-26). The alkyl group can be substituted one or more times and include an oxo (page 7, line 7) and an alkoxy group (page 7, line 26). Consequently, (S)-tert-butyl-2-(8-iodo-4-oxo-3-phenyl-3,4-dihydroquinaolin-2-yl)pyrrolidine-1-carboxylate of Gilead still anticipates claims 1-4, 9, 11-13, and 16-17 under this alternative interpretation of the claims.
Election/Restriction
Applicants’ election of Group I, claims 1-20, drawn to compounds and compositions of Formulas (I) and (II), with traverse in the reply filed 3/6/2025 is acknowledged. Applicants’ election of compound 7a:
PNG
media_image3.png
344
540
media_image3.png
Greyscale
in the same reply of 3/6/2025, is also acknowledged.
Examination will begin with the elected species. In accordance with MPEP § 803.02, if
upon examination of the elected species, no prior art is found that would anticipate or render
obvious the instant invention based on the elected species, the search of the Markush-type
claim will be extended. If prior art is then found that anticipates or renders obvious the non-
elected species, the Markush-type claim will be rejected. It should be noted that the prior art
search will not be extended unnecessarily to cover all non-elected species. Should Applicant
overcome the rejection by amending the claim, the amended claim will be examined again. The
prior art search will be extended to the extent necessary to determine patentability of the
Markush-type claim. In the event prior art is found during further examination that renders
obvious or anticipates the amended Markush-type claim, the claim will be rejected and the
action made final.
The elected species was searched and no prior art was identified. In the Non-Final dated 3/24/2025, the Examiner expanded her search to a compound of instant Formula (I):
PNG
media_image4.png
306
454
media_image4.png
Greyscale
Where R10 is a pyrrolidine
PNG
media_image5.png
127
179
media_image5.png
Greyscale
, and R12 is H, and a 102 rejection was identified. The Examiner noted stereochemistry is not defined at the 2-position of the pyrrolidine, connected to the quinazolinone core. After Applicants amendment of claim 1, the rejection under 35 U.S.C. 102(a)(1) and 102(a)(2) was withdrawn. In the Final dated 7/17/2025, the scope of the search was expanded to compounds of Formula (I):
PNG
media_image4.png
306
454
media_image4.png
Greyscale
Where R10 is a pyrrolidine
PNG
media_image5.png
127
179
media_image5.png
Greyscale
, R12 is H, and R4 is H, and prior art was identified. In response, Applicant has amended claims 1 and 5 to omit the recitation of “C-substituted” from the definitions of nitrogen heterocyclyl groups encompassed by R11 , but did not overcome the rejection. Additionally, in the interest of compact prosecution, further rejections in the same document were identified, and were not fully overcome by Applicants amendments and arguments to the instant claims in the reply of 1/22/2026. The full scope of the claims has not yet been searched in accordance with Markush search practice. Claims 1-5, 9, 11-13, 16-17, and 20 read on the expanded species. Claims 6-8, 10, 14-15, 18-19, and 21 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to nonelected species and/or group, there being no allowable generic or linking claim.
Claim Interpretation
Claims 1 and 5 recite the limitation, “unsubstituted or N-substituted saturated or unsaturated nitrogen C4-C8 heterocyclyl” in reference to the variable R11. The specification is silent as to the definition of “N-substituted”, and thus the limitation is currently being interpreted as any N-containing substituent coming off of the heterocyclyl. This interpretation includes functional groups such as -NH2 and -CN. Further, the Examiner has taken Applicants arguments regarding the interpretation of this limitation into account, and recognizes that the limitation may also be interpretated as a substituent on the nitrogen atom of the ring.
Claim 20 recites an intended use of the pharmaceutical composition it is claiming. The intended use of the pharmaceutical composition is not given patentable weight, and therefore the claim is currently being interpreted as the respective pharmaceutical composition.
MAINTAINED REJECTIONS
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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1-2, 4-5, 9, 11-13, 16-17, and 20 are rejected under 35 U.S.C. 102(a)(1) and 102(a)(2) as being anticipated by Gilead Sciences, Inc. (WO 2015/200352 A1, herein after “Gilead”). This rejection applies to the expanded species.
With respect to claims 1-2, 4-5, 9, 11-13, and 16-17, the reference Gilead discloses compounds as phosphatidylinositol 3-kinase inhibitors, and specifically discloses compound 85 (page 142):
PNG
media_image6.png
193
189
media_image6.png
Greyscale
Which anticipates the expanded species of Formula (I):
PNG
media_image7.png
166
262
media_image7.png
Greyscale
when R1 is halogen, R2-R4 are H, R5, R7, and R9 are H, R6 and R8 are halogen, R10 is a pyrrolidine
PNG
media_image5.png
127
179
media_image5.png
Greyscale
, R12 is H, and R11 is an N-substituted unsaturated heterocyclyl. As stated above in the response to arguments/amendments and the claim interpretation sections, the substituents of -NH2 and -CN both satisfy the limitation of “N-substituted” in reference to the heterocyclyl of R11 of the instant claims.
With respect to instant claim 20, Gilead discloses compound 85 in DMSO for NMR characterization, which constitutes a pharmaceutical composition (page 142). Thus, Gilead anticipates claims 1-2, 4-5, 9, 11-13, 16-17, and 20.
With respect to claims 1-4, 9, 11-13, and 16-17, Gilead also discloses (S)-tert-butyl-2-(8-iodo-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)pyrrolidine-1-carboxylate (page 85, lines 23-24):
PNG
media_image8.png
223
269
media_image8.png
Greyscale
Which anticipates the expanded species of Formula (I):
PNG
media_image7.png
166
262
media_image7.png
Greyscale
when R1 is halogen, R2-R4 are H, R5-R9 are H, R10 is a pyrrolidine
PNG
media_image5.png
127
179
media_image5.png
Greyscale
, R11 is an alkyl, and R12 is H. The Examiner notes the broadest reasonable interpretation of alkyl includes the definitions of the instant specification, which further includes a substituted alkyl according to the instant disclosure (page 7, lines 23-26). The alkyl group can be substituted one or more times and include an oxo (page 7, line 7) and an alkoxy group (page 7, line 26). Consequently, (S)-tert-butyl-2-(8-iodo-4-oxo-3-phenyl-3,4-dihydroquinaolin-2-yl)pyrrolidine-1-carboxylate of Gilead still anticipates claims 1-4, 9, 11-13, and 16-17 under this alternative interpretation of the claims.
Conclusion
Claims 1-5, 9, 11-13, 16-17, and 20 are rejected. Claims 6-8, 10, 14-15, 18-19, and 21 are withdrawn.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Kendall Heitmeier whose telephone number is (703)756-1555. The examiner can normally be reached Monday-Friday 8:30AM-5:00PM ET.
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, Clinton Brooks can be reached on 571-270-7682. 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.
/K.N.H./Examiner, Art Unit 1621
/CLINTON A BROOKS/Supervisory Patent Examiner, Art Unit 1621
Prosecution Insights