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
Claims 1-3, 6, 8-10, 12-13, 19-20, 31, 34-35, 37-42 pending in the present application.
AMENDMENTS
The amendment filed January 15, 2026 has been acknowledged and
entered in the present application file.
Previous Claim Objections
Claim 8 was previously objected to because of the following informalities:
Claim 8, line 1, “-C(O)-“ should read “-C(=O)-“, for consistency of representing the carbonyl moiety throughout the claims.
Applicant has amended claim 8 to correct the informalities.
The objection of October 17, 2025 has been withdrawn.
Previous Claim Rejections - 35 USC § 102
Claims 1-3, 8-10, 12, 20 were previously rejected under 35 U.S.C. 102(a)(1) as being anticipated by Papireddy, Kancharla, et al. "Antimalarial activity of natural and synthetic prodiginines." Journal of medicinal chemistry 54.15 (2011): 5296-5306.
Claims 1-3, 8-10, 12, 20 were previously rejected under 35 U.S.C. 102(a)(1) as being anticipated by CAS Registry No. 1094749-76-4 (which entered STN on January 21, 2009).
Claims 1-3, 8-10, 12, 20 were previously rejected under 35 U.S.C. 102(a)(1) as being anticipated by CAS Registry No. 1094648-97-1 (which entered STN on January 21, 2009).
Applicant has amended the previous claims to exclude the compounds of Papireddy, CAS Registry No. 1094749-76-4 and CAS Registry No. 1094648-97-1 from the present claims, namely removing 2,6-difluorophenyl and -OH as options at the R2 position for compounds of formula I. Applicant has submitted the present claims are not anticipated.
Applicant’s amendments and arguments, see page 16, filed January 15, 2026, with respect to the previous rejection of claims 1-3, 8-10, 12 and 20 have been fully considered and are persuasive. The rejection of October 17, 2025 has been withdrawn.
However, upon further consideration, a new ground(s) of rejection under 35 U.S.C. 102(a)(1) is made over claims 1-3, 8-10, 12, 20 in view of WO 2016/042341 (Reuillon et al.), CAS Registry No 936832-06-3, Halder (Halder, Nyancy, et al. "meso-Aryl substituted stable unorthodox 5, 10-porphodimethenes with α, β and β, β-N-methyl pyrrole connectivities: synthesis and spectroscopic, solid state and theoretical characterization." Organic & Biomolecular Chemistry 17.25 (2019): 6131-6135.), and Kumar (Kumar, Togiti Uday, et al. "Application of Polyphosphoric Acid‐Mediated Acyl Migration for Regiospecific Synthesis of Diverse 2‐Acylpyrroles from Chalcones." Journal of Heterocyclic Chemistry 56.4 (2019): 1283-1290.).
Previously Allowable Subject Matter
Claim 35 was previously 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.
The previous objection of claim 35 is maintained.
Election/Restrictions
Applicant’s affirmation of the election of Group I (directed to a compound, or a pharmaceutically acceptable salt thereof, having a structure represented by Formula I (first formula (I)) of present claim 1), claims 1-3, 6, 8-10, 12-13, 19-20, 31, 34-35, 37-38, as well as a species of Compound 78 in the reply filed January 15, 2026 is acknowledged.
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As per MPEP 803.02, the examiner will determine whether the entire scope of the claims is patentable. Applicants' elected species of present formula (I) appears free of the prior art. Therefore, according to MPEP 803.02: should the elected species be found allowable, the examination of the Markush-type claim will be extended. If the examination is extended and a non-elected species found not allowable, the Markush-type claim shall be rejected and claims to the nonelected invention held withdrawn from further consideration. The examination of the Markush-type claims has been extended to include the species cited below under 35 U.S.C. 102, which are not allowable, as well as the species of claim 35, which is 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.
As a non-elected species has been found not allowable, the Markush-type claims have been rejected and claims to the nonelected invention held withdrawn from further consideration.
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Compound 78 has been construed as a compound of present formula (I), wherein:
V, W, Y and Z are C,
X is NR6,
R1 is absent,
R2 is
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R3 is -C(=O)-,
R4 is 2-fluorophenyl.
Compound 78 has also been construed as a compound of present formula (Id).
Claims 1-3, 8-10, 12, 20 and 35 have been examined to the extent that they embrace and are readable on the elected embodiment and the above identified nonelected species.
Claims 6, 13, 19, 31, 34 and 37-42 do not read on the presently searched and examined subject matter. Therefore, claims 6, 13, 19, 31, 34 and 37-42 are withdrawn from consideration by the Examiner under 37 CFR 1.142(b) as being drawn to a non-elected invention.
Claim Rejections - 35 USC § 102
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 1-3, 8-10, 12 and 20 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by WO 2016/042341 (Reuillon et al.; Publication Date: March 24, 2016).
Reuillon discloses compounds of formula (I) or a tautomer, stereoisomer, N-oxide, pharmaceutically acceptable salt or solvate thereof as well as methods for the prophylaxis or treatment of a disease state or condition mediated by ERK5, in particular cancers, comprising administration of a compound of formula (I), or pharmaceutical composition thereof. See pages 3-5.
Reuillon discloses several compound of formula (I) which are encompassed by the present claims, compound examples 121, 122 and 124 in Table 12 on pages 141-142.
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Compound 121 of Reuillon corresponds to a compound of present formula (I) where,
V, W, Y and Z are C
X is NR6
R1 is NH (see present claim 3),
R2 is
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R3 is -C(=O)- (see present claims 8-10),
R4 is 2,6-difluorophenyl (see present claims 12 and 20)
R6 is -H
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Compound 122 of Reuillon corresponds to a compound of present formula (I) where,
V, W, Y and Z are C
X is NR6
R1 is NH (see present claim 3),
R2 is
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R3 is -C(=O)- (see present claims 8-10),
R4 is 2,6-difluorophenyl (see present claims 12 and 20)
R6 is -H
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Compound 124 of Reuillon corresponds to a compound of present formula (I) where,
V, W, Y and Z are C
X is NR6
R1 is NH (see present claim 3),
R2 is
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R3 is -C(=O)- (see present claims 8-10),
R4 is 2,6-difluorophenyl (see present claims 12 and 20)
R6 is -H
Compounds 121, 122 and 124 are also encompassed by present formula (Id). See present claim 2.
Claims 1-3, 8-10 and 20 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by CAS Registry No. 936832-06-3 (which entered STN on June 08, 2007).
CAS Registry No. 936832-06-3 is drawn to (5-Benzoyl-1H-pyrrol-3-yl)-2-pyridinylmethanone, which has the following structure:
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CAS Registry No. 936832-06-3 corresponds to a compound of formula (I) where,
X is NR6,
V, W, Y and Z are C,
R1 is absent (see present claim 3),
R2 is phenyl,
R3 is –C(=O)- (see present claims 8-10),
R4 is
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(see present claim 20),
R6 is -H.
CAS Registry No. 936832-06-3 also corresponds to compound of formula (Id). See present claim 2.
Claims 1-3, 8-10 and 20 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Halder (Halder, Nyancy, et al. "meso-Aryl substituted stable unorthodox 5, 10-porphodimethenes with α, β and β, β-N-methyl pyrrole connectivities: synthesis and spectroscopic, solid state and theoretical characterization." Organic & Biomolecular Chemistry 17.25 (2019): 6131-6135.).
Halder discloses synthetic route towards the exclusive formation of two different highly stable doubly mutant porphodimethenes via the α,β and β,β-connectivities of N-methyl pyrrole rings within the macrocyclic core. See page 6134, left column, last paragraph.
Halder discloses the synthesis of precursor materials comprising the formation of compound 6 in the synthetic route. See Supplemental Information page S4, Scheme S1.
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Compound 6 of Halder corresponds to a compound having the structure of formula (I) where,
X is NR6,
V, W, Y and Z are C,
R1 is absent (see present claim 3),
R2 is phenyl,
R3 is –C(=O)- (see present claims 8-10),
R4 is phenyl (see present claim 20),
R6 is -H.
Compound 6 also corresponds to compound of formula (Id). See present claim 2.
Claims 1-3 and 20 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Kumar (Kumar, Togiti Uday, et al. "Application of Polyphosphoric Acid‐Mediated Acyl Migration for Regiospecific Synthesis of Diverse 2‐Acylpyrroles from Chalcones." Journal of Heterocyclic Chemistry 56.4 (2019): 1283-1290.).
Kumar discloses a metal-free approach for the synthesis of 2-acylpyrroles started from chalcones which was carried out in two steps. See abstract.
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Kumar discloses a screening of reaction conditions for the acyl migration to produce 2-acylpyrrole compound 3a from 3-acylpyrrole compound 2a. See page 1285 for Table 1.
Compound 3a of Kumar corresponds to a compound having the structure of formula (I) where,
X is NR6,
V, W, Y and Z are C,
R1 is absent (see present claim 3),
R2 is phenyl,
R3 is not present,
R4 is phenyl (see present claim 20),
R6 is -H.
Compound 3a also corresponds to compound of formula (Id). See present claim 2.
Allowable Subject Matter
Claim 35 is 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.
Conclusion
Claims 6, 13, 19, 31, 34 and 37-42 are withdrawn.
Claims 1-3, 8-10, 12, 20 are rejected.
Claim 35 is objected to.
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 QUINCY A MCKOY whose telephone number is (703)756-4598. The examiner can normally be reached Monday - Thursday 8:00 - 6:00.
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/QUINCY A. MCKOY/
Patent Examiner
Art Unit 1626
/KAMAL A SAEED/Primary Examiner, Art Unit 1626