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, 3-19, 21 and 22 are pending in the application. Claims 1 and 3-13 are rejected. Claims 14-19, 21 and 22 are withdrawn from further consideration.
Election/Restrictions
Applicant’s election without traverse of the species of the third structure in claim 11, the third structure in claim 12 and the sixth structure in claim 13 to prosecute the invention of Group I, claims 1 and 3-13, Chemical formula 5 in the reply filed on December 8th, 2025 is acknowledged.
As per MPEP 803.02, the examiner will determine whether the entire scope of the claims is patentable. Applicants' elected species are not allowable. MPEP 803.02 states:
Following election, the Markush claim will be examined fully with respect to the elected species and further to the extent necessary to determine patentability. […]
If the Markush claim is not allowable, the provisional election will be given effect and examination will be limited to the Markush claim and claims to the elected species, with claims drawn to species patentably distinct from the elected species held withdrawn from further consideration. […]
If on examination the elected species is found to be anticipated or rendered obvious by prior art, the Markush claim and claims to the elected species will be rejected, and claims to the nonelected species will be held withdrawn from further consideration.
As the elected species have been found not allowable, the Markush-type claims have been rejected and claims to the nonelected invention held withdrawn from further consideration. Claims 1 and 3-13 have been examined to the extent that they are readable on the elected embodiment. Since the elected species are not allowable, subject matter not embraced by the elected embodiment is therefore withdrawn from further consideration. Additional rejections were discovered incidental to the search of the elected species and are presented below in the interest of compact prosecution.
Claims 14-19, 21 and 22 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on December 8th, 2025.
Priority
This application is a 35 U.S.C. 371 National Stage Filing of International Application No. PCT/KR2022/001563, filed January 28th, 2022, which claims priority under 35 U.S.C. 119(a-d) to KR10-2021-0016149, filed February 4th, 2021.
Receipt is acknowledged of papers submitted under 35 U.S.C. 119(a)-(d), which papers have been placed of record in the file.
Information Disclosure Statement
The Examiner has considered the Information Disclosure Statement(s) filed on April 15th, 2025, July 2nd, 2024, December 11th, 2023, and June 7th, 2023.
Claim Objections
In claim 10, “the compound of Chemical Formula 7 or 8,” should be replaced with “a compound of Chemical Formula 7 or 8,” since the noted limitation is the first mention of these Chemical Formulae in claim 10 or any parent claim.
Claim Rejections - 35 USC § 112(b)
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.
Claim 7 is 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.
Claim 7 recites the limitation "a third halogen supplying agent" in lines 2 and 3. There is insufficient antecedent basis for this limitation in the claim. Neither claim 7 nor claim 1 previously recite first or second halogen supplying agents.
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.
Claim(s) 1, 4, 8 and 9 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Fleming et al. J. Chem. Soc. Perkin Trans 1 1975, 964.
Fleming et al. teach the following reaction on page 964:
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The prior art further teaches “That the pathway followed is the sequence (5) + (4) [Wingdings font/0xE0] (8)…” where the prior art depicts the following scheme on page 964:
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Accordingly, the prior art teaches generation of an enolate (of prior art formula (4)) and reaction with a halogenated benzene (either formula (13) or (14) in the prior art) and generation of an anthracene compound (formula (16) or (17) in the prior art). Furthermore, the preparation of compound (16) is embraced by instant claim 4 where b is from 1 to 8. Regarding instant claims 8 and 9, these claims recite passive language where “the enolate of Chemical 1 is formed from” a particular structure, which appears to be a product-by-process nested in method. If Applicant intends for these steps to be limiting, they should be recited in positive direction, for instance “where the method further comprises forming the enolate of Chemical Formula 1 from the following Chemical Formula 7 or 8…”.
Regarding the limitation of claim 1 of “a deuterated anthracene compound” and “a halogenated benzene having at least one deuterium,” the instant claims do not require any level of deuterium and the prior art’s presence of deuterium at natural abundance is deemed to be embraced by the instant limitation.
Claim Rejections - 35 USC § 103
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.
Claim(s) 1 and 3-13 is/are rejected under 35 U.S.C. 103 as being unpatentable over WO 2010/071362 A2 by Hong et al. (where a machine translation is appended to the reference) in view of Fleming et al. J. Chem. Soc. Perkin Trans 1 1975, 964-965 and in further view of Borthakur et al. Org. Lett. 2019, 21, 2768-2771.
Determining the scope and contents of the prior art. (See MPEP § 2141.01)
Hong et al. teach the following general approach on page 17 of the original document:
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The prior art teaches that the steps were (machine translation, Synthesis Example 18) “carried out in the same manner as in Synthesis Example 1 ~ 7”.
Ascertainment of the differences between the prior art and the claims. (See MPEP § 2141.02)
The prior art teaches conversion of d6-benzene to d8-anthracene; however, the steps do not involve a halogenated benzene intermediate or an enolate of Chemical Formula 1. Additional limitations of dependent claims are addressed below.
Finding of prima facie obviousness --- rationale and motivation (See MPEP § 2141.02)
At least in the interesting of determining which methods of synthesizing anthracene would provide an optimum overall synthesis in terms of yield, cost, safety, etc., a person having ordinary skill in the art would have been motivated to test additional known methods that would result in the production of d8-anthracene starting with d6-benzene. As one possibility, Fleming et al. teach the following reaction on page 964:
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The prior art further teaches “That the pathway followed is the sequence (5) + (4) [Wingdings font/0xE0] (8)…” where the prior art depicts the following scheme on page 964:
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Accordingly, Fleming et al. teach generation of an enolate (of prior art formula (4)) and reaction with a halogenated benzene (formula (13) in the prior art) and generation of anthracene (formula (16) in the prior art). The prior art scheme further teaches that the hydrogen atoms from the enolate are found on the central anthracene ring such that starting with only deuterated halogenated benzene would result in the same material (d8-anthracene) of Hong et al. Furthermore, a person having ordinary skill in the art would have been familiar with methods that could be used to generate the required d5-bromobenzene. Borthakur et al. teach the following transformation in Scheme SI-6:
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The compound d5-bromobenzene is embraced by instant claim 3. Applying the generation of d5-bromobenzene is embraced by instant claim 7 where the third halogen supplying agent is NaBrO3. Regarding instant claim 4, d8-anthracene (where only the outer rings contain deuterium) is embraced by Chemical Formula where b is 8.
Regarding instant claim 5, as noted above Hong et al. teach analogous steps to Synthesis Examples 1-7 where Hong et al. teach introduction of bromine in Synthesis Example 5 as follows:
Was dissolved anthracene (D4) 10g (1eq, 0.06mol) and 11.9g NBS (1.1eq, 0.07mol) obtained in Preparation Example 4 to put the flask 150ml DMF, was stirred for 2 hours. After the reaction the reaction solution was placed in 200ml of distilled water. […]
The prior art teaches a solution of the corresponding compound of instant Chemical Formula 2 and a first halogen supplying agent of NBS. Hong et al. further teach the following transformation in Synthesis Example 6:
Synthesis Example 5 9-bromoanthracene (D4) obtained from putting 15g (1eq, 0.06mol) and 2-naphthalenboronic acid 13.76g (1.2eq, 0.08mol) in a flask and dissolved into the toluene 150ml. Then Pd (PPh 3) 4 0.3g (0.02eq, 0.4mmol), K 2 CO 3 and 60ml 2M solution was stirred with heating for 12 hours after each addition. […]
The prior art teaches the use of a boronic acid corresponding to instant formula L1-Ar1 where Ar1 is an aryl group and L1 is a leaving group.
Regarding instant claim 6, Hong et al. teach an analogous iteration of introducing bromine using NBS in Synthesis Example 7. Hong et al. further teach preparation of a compound represented by Formula 3-2 in Synthesis Example 19 via “the same procedure as in synthesis example 11” where compound Formula 3-2 is disclosed on page 7 of the original document as follows:
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Synthesis Example 11 using an analogous boronic acid that would correspond to instant formula L2-Ar2.
Regarding instant claims 8 and 9, these claims recite passive language where “the enolate of Chemical 1 is formed from” a particular structure, which appears to be a product-by-process nested in method. If Applicant intends for these steps to be limiting, they should be recited in positive direction, for instance “where the method further comprises forming the enolate of Chemical Formula 1 from the following Chemical Formula 7 or 8…”.
Regarding instant claim 11, the non-brominated precursor to the following structure corresponds to the third structure of instant claim 11:
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Regarding instant claim 12, the structure above is recited as the third option in the claim. Regarding instant claim 13, the prior art compound 3-2 corresponds to the sixth structure recited in the claim.
Regarding instant claim 10, Fleming et al. teach the following reaction on page 965:
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The authors teach the presence of halogenated benzene (where adapting the synthesis to use halogenated d5-benzene is addressed above), a base (2,2,6,6-tetramethylpiperide), an alkyllithium (n-butyl-lithium) and a solvent (THF). Regarding the presence of the Chemical Formula 7 or 8, Fleming et al. teach that the reaction generates an enolate that would correspond to the deprotonated form of Chemical Formula 8 where L4 is hydrogen or a Chemical Formula 7 where L3 is considered lithium. Furthermore, the identity of the system being a solution is considered inherent at least since the prior art teaches addition of organic components or components already in solution.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MATTHEW P COUGHLIN whose telephone number is (571)270-1311. The examiner can normally be reached Monday - Friday, 10 am - 6 pm EST.
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/MATTHEW P COUGHLIN/Primary Examiner, Art Unit 1626