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
Filing Receipt and Priority
The filing receipt mailed 06/11/2024 states that the instant application claims benefit of provisional application 63/469,178, filed 05/26/2023.
The provisional application supports the instant claims. Therefore, the effective filing date is 05/26/2023.
Information Disclosure Statement
The information disclosure statement submitted 06/17/2026 has been considered.
NPL entry 18, to a Braun et al. (J. Chem. Phys. 59, 3595-3599) has not been considered because the entry lacks a date.
Restriction/Species Election
Applicant’s election of the following in the remarks submitted 07/08/2026 have are acknowledged.
Applicant’s election of Group I, claims 1-9 is acknowledged.. Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)).
Applicant’s election with traverse of the compound V-178, shown below, is acknowledged.
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Applicant’s traversal argues that “it has not been shown that examining all of the claimed subject matter together would impose a serious burden.”
The instant specification discloses structures of compounds that embrace the general formula of claim 1 in Table A. Table A begins on p. 39 and extends to p.191. Included within the table are compounds similar to compound V-178 as well as compounds with drastically different connectivity and/or substituents. Additionally, where the claimed compound has a specific core substituted by substituent Va, the specification discloses compounds with a different core and different connectivity, as exampled below.
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These compounds are not obvious alternatives of the elected compound and would require a secondary search.
Therefore, the species election is maintained.
At examiner’s discretion search and examination has been broadened to the structure search below.
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wherein R1 is substituent -L-R1 as defined in claim 1.
Additionally, applicant has submitted several non-patent literature documents with compounds that embrace the general formula V of claim 1. In the interest of compact prosecution, examination has been broadened to include said structures. However, it should be noted that search has only been broadened to structure above.
Claims 11-12, 14, 16, and 18-20 are hereby withdrawn being drawn to non-elected invention. Claims 5, 6, 9 and 24 are hereby withdrawn being drawn to non-elected species. See claim interpretation discussion below.
Claim Interpretation
Claim 5 states “The compound of claim 1, wherein L is other than a bond and R1 is a selected from…”.
Claim 6 states “The compound of claim 1, wherein each R1 is independently selected from aryl and heteroaryl.”
Claim 9 states “The compound of claim 8, wherein each L is a bond and each R1 is independently CN or NH2.”
Claim 24 states “The compound of claim 1, wherein each R1 is independently selected from aryl and heteroaryl, wherein each R1 is substituted with one to four substituents independently selected from OH, NH, SH, halo, and C2-C4alkene.”
The claim language of claim 5 excludes embodiments wherein L is a bond. Therefore, the compounds of claim 5 are drawn to compounds wherein each carbon atom of the azulene core has a substituent Va wherein L is one of O, S, NH, etc. as claimed in claim 1. No carbons of the embodiments within claim 5 are left unsubstituted. Therefore, the claim is withdrawn being drawn to a non-elected species as compound V-178, below, is an embodiment wherein L can be either a bond or other than a bond.
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Similarly, claim 9 is drawn to an embodiment wherein each carbon would be substituted with a CN or NH2.
Claims 6 and 24 do not specify whether L is a bond or other than a bond. However, the claims specify that “each R1 is independently selected from aryl and heteroaryl” which is a limitation that is only possible when L is not a bond. Therefore, the examiner assumes that L is not a bond for each instance where there is a carbon atom on the azulene core.
Therefore, the claims are withdrawn being drawn to non-elected species as stated above. Additionally, the instant specification does not disclose a single compound wherein each carbon atom of the azulene core is substituted with a non-hydrogen substituent. The compounds of table A and table B each have instances where all possible substituents Va either include L as a bond or L as a non-bond.
Critically, there are no disclosed compounds within the specification where each L is a bond and each R1 is independently CN or NH2. Similarly, there are no compounds disclosed within the specification where each carbon atom is substituted with a substituent Va where L is other than a bond and R1 is as claimed.
Claim Objections
Claim 3 is objected to for containing an underscore, as shown below.
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Claim Rejections
Claim Rejections - 35 USC § 112(b)
Claims 1-4, 7, 8, and 21-23 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.
Indefiniteness
Claim 1 states “with one or two groups independently selected from =CHRa, C5-C0heteroaryl…”. This claim language is indefinite because the full range of heteroaryl is not claimed.
As claims 2-4, 8, and 21-23 are dependent on claim 1, they are also rejected.
Claim 7 is indefinite for referring to compounds shown in Table A or Table B of the specification. The MPEP section 2173.05(s) states:
“Where possible, claims are to be complete in themselves. Incorporation by reference to a specific figure or table “is permitted only in exceptional circumstances where there is no practical way to define the invention in words and where it is more concise to incorporate by reference than duplicating a drawing or table into the claim. Incorporation by reference is a necessity doctrine, not for applicant’s convenience.” Ex parte Fressola, 27 USPQ2d 1608, 1609 (Bd. Pat. App. & Inter. 1993) (citations omitted).”
Additionally, the contents of tables A and B may change which would change the scope of claim 7. One of ordinary skill would not know the full scope of claim 7 and, therefore, claim 7 is indefinite.
Claims 3, 8, and 22 are rejected for being indefinite. Claim 3 states “The compound of claim 1, wherein the compound comprises 2 or 3 substituents of Formula Va, or wherein the compound comprises 2 substituents of Formula Va.”
Claim 1 states “each of A23…and A30 that is a C is independently unsubstituted or substituted with a substituent of Formula Va” and defines the substituent “Va” as “-L-R1 wherein -L is any of a bond, O, S, NH, CRa=, -N=, C(O), C2-6alkenylene, C2-6alkenyleneO and C2-6alkenyleneS”. Claim 1 further states that “when L is a bond, R1 is selected from H, CN and halo; when L is other than a bond, R1 is selected from H,…” (see claim for full listing).
The claims are indefinite because the limitations of the dependent claims contradict the limitations of the parent claim. For example, Griesser (Journal of Photochemistry and Photobiology, A:Chemistry, 43 (1988) 247-261, of the record) discloses the following compound in Fig. 1.
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The above compound does not embrace the limitations of claim 1 because claim 1 excludes the methyl groups from its definition of substituent Va. However, the limitations of claim 3 only require that 2 or 3 substituents or simply 2 substituents match the substituent Va. In view of that reading, the above compound does embrace the limitations of claim 3 because the carbonyl and the 3 hydrogen atoms fulfill the requirements of claim 3 (“comprises 2 or 3 substituents of Formula Va”).
Similar issues are found in claims 8 and 22.
Improper Markush Rejection
Claims 1-4, 7-8 and 21-23 are rejected on the basis that it contains an improper Markush grouping of alternatives. See In re Harnisch, 631 F.2d 716, 721-22 (CCPA 1980) and Ex parte Hozumi, 3 USPQ2d 1059, 1060 (Bd. Pat. App. & Int. 1984). A Markush grouping is proper if the alternatives defined by the Markush group (i.e., alternatives from which a selection is to be made in the context of a combination or process, or alternative chemical compounds as a whole) share a “single structural similarity” and a common use. A Markush grouping meets these requirements in two situations. First, a Markush grouping is proper if the alternatives are all members of the same recognized physical or chemical class or the same art-recognized class, and are disclosed in the specification or known in the art to be functionally equivalent and have a common use. Second, where a Markush grouping describes alternative chemical compounds, whether by words or chemical formulas, and the alternatives do not belong to a recognized class as set forth above, the members of the Markush grouping may be considered to share a “single structural similarity” and common use where the alternatives share both a substantial structural feature and a common use that flows from the substantial structural feature. See MPEP § 2117.
The Markush grouping of the compounds of formula V is improper because the alternatives defined by the Markush grouping do not share both a single structural similarity.
Claim 1 is drawn to the following.
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As stated above, the instant specification discloses compounds which include the following structures. See Tables A and B for full listing of compounds.
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Compounds V-1405 and V-1406 differ from the elected compounds. Where the elected compound has a core moiety shown below, compounds V-1405 and V-1406 have a core structure that is contains the same number of N atoms but in different connectivity.
Core Structure of elected compound
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Additionally, the V-1405 and V-1406 compounds have different connectivity and substituents from the elected compound. The structure of the V-1405 and V14-6 compounds are drastically different from the structure of the claimed compound. The only similarity is that both groups of compounds contain a [3.5]-bicyclic heterocyclic ring structure, which is not even shared.
Further, as discussed in the 102 rejection below, the instant claims embrace compounds which do not contain any nitrogen atoms, which is even further removed from the elected compound.
To overcome this rejection, Applicant may set forth each alternative (or grouping of patentably indistinct alternatives) within an improper Markush grouping in a series of independent or dependent claims and/or present convincing arguments that the group members recited in the alternative within a single claim in fact share a single structural similarity as well as a common use.
Examiner suggests amending the claim to compounds similar to the elected compound.
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.
(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.
Claim(s) 1, 3-4, 8, 22 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Zeng (Chem. Asian J. 2020, 15, 1904-1915, of the record).
Zeng on p. 1905, Fig. 2 discloses the following compounds 2a – 2h.
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Claim(s) 1-4, 8, 21-22 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Burke (Chemical Physics Letters, 1973, Vol. 19, No. 4, of the record)
Burke o p. 574 discloses the following compound.
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Claim(s) 1-4, 8, 21-23 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Xie (Bioorganic & Medicinal Chemistry, 24, 2016, 2595-2602).
Xie on p. 2597 discloses compound 23a.
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Claim(s) 1, 3-4, 8, and 22 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by STN (STN RN entry 2484909-71-7, entered 2020).
STN discloses the following compound.
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Note: Claim 1 claims the limitation “the compound has a negative singlet-triplet gap and an oscillator strength greater than or equal to about 0.01”. This limitation is an inherent property of the compound and it is assumed the any compound that embraces the general formula of claim would have this property.
Conclusion
No claims allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to LUISALBERTO GONZALEZ whose telephone number is (571)272-1154. The examiner can normally be reached M-F 8:30-5:30.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Jeffrey Murray can be reached at (571) 272-9023. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/LUISALBERTO GONZALEZ/Examiner, Art Unit 1624
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