DETAILED ACTION
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 the Claims
The amendment filed on 03/06/2026 has been entered. Claims 1-20 have been amended and are thus currently pending and are under examination.
Withdrawn Objections and Rejections
The objection to the specification and claim 10 have been withdrawn in view of the amendment.
Claim 1 has been amended by canceling F and Cl for R1 and reciting “a halogen” and by adding the new limitation “optionally, wherein R3 and R4 and/or R5 and R6 in each case together form a heterocyclic 5-membered ring or 6-membered ring having at least one heteroatom selected from O, S or N”. As such, the insufficient antecedent basis of limitations in clams 3 and 11 have been obviated. Furthermore, claim 13 has been amended to now be drawn to a method claim by reciting the method step. Accordingly, the 112(b) rejection of claims 3, 11 and 13 and the 101 rejection of claim 13 have been withdrawn.
Claim 19 has been amended to be in a proper dependent form and the 112(d) rejection of the claim has been withdrawn.
Claim Objections
Claim 5 is objected to because of the following informalities: the following moieties on page 3 (page 5 of 33) have not been canceled by strikethrough and as such have been recited twice in view of the same added moieties on page 6 (page 8 of 33).
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Claim 6 is objected to because of the following informalities: the following moieties on page 7 (page 9 of 33) have not been canceled by strikethrough and as such have been recited twice in view of the same added moieties on page 10 (page 12 of 33).
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Claim 7 is objected to because of the following informalities: “The chemical compound of any of the preceding claim 1” is deemed with idiomatic error. Applicant is advised to cancel “any of the preceding” from the limitation.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 6-7 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claim 6 recites the broad recitation before the term preferably, and the claim also recites the narrower statement of the range/limitation after the term preferably. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
Regarding claim 7, the limitation "R1 is a monocyclic 5-membered ring or 6-membered ring" renders the claim indefinite. Firstly, it is unclear if the intention is to further limit claim 1’s (a) the homocyclic 6-membered ring or (b) the heterocyclic 5-membered or 6-membered ring recited. If (a), there is insufficient antecedent basis for " R1 is a monocyclic 5-membered ring” in the claim since claim 1 requires that R1 can only be substituted homocyclic 6-membered ring.
Response to Arguments
With respect to claim 7, Applicant argues:
Claim 1 includes the features "R1 is a substituted homocyclic 6-membered ring . . . or is a substituted or unsubstituted heterocyclic 5-membered ring or 6-membered ring[.]" The feature of claim 7 "R1 is a monocyclic 5-membered ring or 6-membered ring" is a further limitation of the features of claim 1.
The arguments are not persuasive. There are two features in claim 1 for R1, (a) the homocyclic 6-membered ring or (b) the heterocyclic 5-membered or 6-membered ring recited. Claim 7 does not specify if the “monocyclic 5-membered ring or 6-membered ring” is further limiting (a) or (b). Note, if the “monocyclic 5-membered ring or 6-membered ring” is further limiting (a), there is a lack of antecedent basis for the “monocyclic 5-membered ring” since (a) is only a 6-membered homocyclic ring with NO 5-membered homocyclic ring. Thus, claim 7 remains unclear and indefinite.
Allowable Subject Matter
Claims 1-4 and 8-20 are allowed and the subject matter of claims 5-7 is free of prior art references.
The closest prior art references are Shimogawa (Shimogawa, H. et al. “Impacts of Dibenzo- and Dithieno-fused Structures at the b, g Bonds in the BODIPY Skeleton” Chem. Lett. 2013, 42, 986-988; cited in IDS 07/05/2023) and Yang (Yang, Y. et al. “Thienopyrrole-expanded BODIPY as a potential NIR photosensitizer for photodynamic therapy” Chem. Commun., 2013, 49, 3940; cited in PTO-892 01/28/2026).
Shimogawa teaches BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) skeleton has unique electrochemical and optical properties, such as intense absorption profiles, high photostability, and high electron-accepting ability. Various structural modifications on this skeleton have been extensively studied to demonstrate their significant utilities in a variety of applications, such as dye sensitized solar cells (DSSCs),2 organic photovoltaics (OPVs), organic light-emitting diodes (OLEDs), photodynamic therapy, etc. and the reference modified the structure simple structural modification by the introduction of a ring-fused structure to the BODIPY skeleton.
The fused compounds, dibenzo- (2) and dithieno-fused (3) structures and their syntheses have been taught by the reference (reproduced below):
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Compound 3 is similar in structure to the claimed compound of formula I, in which X1 and X2 are S, R1 is a homocyclic 6-membered ring with 2 Hs substituted by CF3, R2 and R7 are H, R4 and R5 are H, and R3 and R6 are H.
Shimogawa also teaches the synthetic route of BODIPY-3:
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The electronic effects of the introducing dibenzo- and dithieno-fused structures at both of the b and g bonds in the BODIPY skeleton were investigated and it was demonstrated that such introduction perturbs the electronic structure to enhance the quinoid and azafulvene character in the indole or thienopyrrole subunits, which effectively increases the electron-accepting ability.
The difference between the instant compound and BODIPY-3 of Shimogawa is that R3 and R6 in the claimed compound independently of one another are a substituted or unsubstituted homocyclic 6-membered ring or a substituted or unsubstituted heterocyclic 5-membered ring or 6-membered ring whereas R3 and R6 in BODIPY-3 of Shimogawa are H.
Yang teaches compound I with BODIPY skeleton as a potential NIR photosensitizer for photodynamic therapy.
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In the above compound, X1 and X2 are S, R1 is a homocyclic 6-membered ring with 1 H substituted by -CO2Me, R2 is H, R7 is Br, R4 and R5 are H, and R3 and R6 are substituted heteroaryl 5-membered ring.
The reference further provides a synthetic route to compound I in Scheme 1:
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However, Yang fails to teach or suggest R1 as instantly claimed.
The synthetic routes in obtaining BODIPY compounds in both Shimogawa and Yang are similar, in which thienopyrrole is reacted with aryl aldehydes and BF3.Et2O. While using the thienopyrrole of Yang in place of that of Shimogawa would yield the compound as instantly claimed, a skilled artisan would not have been motivated to modify the compound of Shimogowa with that of Yang as there is no teaching, suggestion or motivation in modifying Shimogowa. “Obviousness can be established by combining or modifying the teachings of the prior art to produce the claimed invention where there is some teaching, suggestion, or motivation to do so.” See MPEP § 2143.01.
Furthermore, the compounds of Shimogowa’s and Yang’s do not appear to have the same utility and one of ordinary skilled in the art would not have been motivated to modify Shimogowa with the teachings of Yang. “If a proposed modification would render the prior art invention being modified unsatisfactory for its intended purpose, there may be no suggestion or motivation to make the proposed modification.” MPEP § 2143.01.
In view of the foregoing, the instantly claimed compound is deemed novel and unobvious over the closest prior art reference.
Conclusion
Claims 1-4 and 8-20 are allowed and claims 6-7 are rejected.
THIS ACTION IS MADE FINAL. 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.
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/MEDHANIT W BAHTA/ Primary Examiner, Art Unit 1692