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 preliminary amendment filed on 05/21/2024 has been entered. Claims 9-10 have been amended, thus claims 1-10 are currently pending and are under examination.
Claim Objections
Claim 8 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.
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 1 and 3 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.
The parenthetical limitations where the R groups are defined render the claims vague and indefinite because it is unclear whether the limitations are part of the claimed invention.
Claims 4-7 and 9 are also rendered indefinite for their dependency on claims 1 and 3 and for not obviating the indefinite languages of claims 1 and 3.
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.
Claims 1 and 10 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Dong (Dong, H. et al. “Effects of emodin on treating murine nonalcoholic fatty liver induced by high caloric laboratory chaw” World J Gastroenterol 2005; 11(9):1339-1344; cited in IDS 05/21/2024) as evidenced by Middleton (Middleton, S. A. et al. “BET Inhibition Improves NASH and Liver Fibrosis” Scientific Reports (2018) 8:17257 DOI:10.1038/s41598-018-35653-4).
Regarding claim 1, Dong teaches emodin having the structure as below, which is a specie of the claimed formula 2:
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Regarding claim 10, the reference further teaches a composition comprising emodin for treating murine nonalcoholic fatty liver induced by high caloric laboratory chaw.
Regarding claim 9, Dong fails to teach that the compound is a bromodomain extra-terminal (BET) protein inhibitor as instantly set forth in the preamble of the claim. However, MPEP § 2111.02 indicates that statements in the preamble reciting the purpose or intended use of the claimed product must be evaluated to determine whether the recited purpose or intended use results in a structural difference (or, in the case of process claims, manipulative difference) between the claimed invention and the prior art. In this instance, the intended use of the claimed quinizarin derivative is of no significance to the structure of the compound, is not considered to be a limitation of the claim and thus is not given patentable weight.
Even if the preamble of claim 9 is given patentable weight, Dong meets the limitation as evidenced by Middleton. As discussed earlier, Dong teaches that emodin is used for treating murine nonalcoholic fatty liver. Middleton discusses the association of non-alcoholic fatty liver disease (NAFLD) and bromodomain and extra-terminal motif (BET), where the inhibition of BET improves NASH (non-alcoholic steatohepatitis) and Liver Fibrosis. NAFLD encompasses a spectrum of fatty liver diseases observed in individuals that do not consume excessive alcohol, ranging from simple steatosis to steatosis accompanied by hepatocyte ballooning and inflammation (referred to as nonalcoholic steatohepatitis, NASH) and fibrosis 2. As such, Dong’s emodin for treating murine nonalcoholic fatty liver would necessarily inhibit bromodomain and extra-terminal motif (BET).
Claims 1, 3 and 9 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Paquette (Paquette, J. A. et al. “Anthra- and pentacenequinone derivatives: influence of structure on the formation of columnar liquid crystal phases” New J. Chem., 2016, 40, 5985--5988; cited in IDS 05/21/2024).
Regarding claim 1, Paquette teaches compound 1, a specie of the claimed formula 1:
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Regarding claim 3, the reference further teaches a method for preparing compound 1 by reacting anthracene 6 with compound 9, a specie of claimed formula 3:
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Regarding claim 9, as discussed earlier, the intended use as bromodomain extra-terminal (BET) protein inhibitor set forth in the preamble is of no significance to the structure of the compound and thus is not considered to be a limitation of the claim and is not given patentable weight.
Claims 1, 3, 5-6, 7 and 9 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Grover (Grover, J. et al. “Synthesis, biological evaluation, molecular docking and theoretical evaluation of ADMET properties of nepodin and chrysophanol derivatives as potential cyclooxygenase (COX-1, COX-2) inhibitors” European Journal of Medicinal Chemistry 80 (2014) 47-56; cited in IDS 05/21/2024).
Regarding claim 1, Grover teaches in Scheme 2 compounds 2 and 2a-i, species of the claimed formula 1:
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Regarding claim 3, the reference further teaches in the scheme a method for preparing compounds 2a-i by reacting 2 with bromo compounds RX, species of the claimed formula 5.
Regarding claims 5-6, while the claims further limit the compounds of formula 3 and 4, the recited species are not given patentable weight because formula 3 and 4 are recited in claim 3 as alternatives to formula 5. As discussed earlier, Kun’s RX are species of formula 5.
Regarding claim 7, Grover teaches benzyl bromide BrCH2C6H5 that obtains 2f.
Regarding claim 9, as discussed earlier, the intended use as bromodomain extra-terminal (BET) protein inhibitor set forth in the preamble is of no significance to the structure of the compound and thus is not considered to be a limitation of the claim and is not given patentable weight.
Claims 1, 3-6 and 9 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Liu (Liu, Y-J. et al. “Cyclic and open tetra-benzimidazolium sensors for dihydrogen phosphate sensing” Tetrahedron 86 (2021) 132080).
Regarding claim 1, Liu teaches in Scheme 1 the following compounds, species of the claimed formula 1:
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Regarding claims 3-4, Liu teaches a method of reacting 1,4-dihydroxy-anthracene-9,10-dione with 1,2-dibromoethane, specie of formula 5:
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Regarding claims 5-6, while the claims further limit the compounds of formula 3 and 4, the recited species are not given patentable weight because formula 3 and 4 are recited in claim 3 as alternatives to formula 5. As discussed earlier, Liu’s 1,2-dibromoehtane is a specie formula 5.
Regarding claim 9, as discussed earlier, the intended use as bromodomain extra-terminal (BET) protein inhibitor set forth in the preamble is of no significance to the structure of the compound and thus is not considered to be a limitation of the claim and is not given patentable weight.
Claim Rejections - 35 USC § 103
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 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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-2 and 9 are rejected under 35 U.S.C. 103 as being unpatentable over Kun (Kun, E. et al. Patent number US6,316,495).
Regarding claim 1, Kun teaches guinizarines of the formula in which most of the R group definitions are encompassed by the R groups as instantly claimed
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Regarding claim 2, R1 or R5 of Kun can be substituted phenyl with hydroxy groups, which would obtain the claimed compounds:
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Regarding claim 9, Dong fails to teach that the compound is a bromodomain extra-terminal (BET) protein inhibitor as instantly set forth in the preamble of the claim. However, MPEP § 2111.02 indicates that statements in the preamble reciting the purpose or intended use of the claimed product must be evaluated to determine whether the recited purpose or intended use results in a structural difference (or, in the case of process claims, manipulative difference) between the claimed invention and the prior art. In this instance, the intended use of the claimed quinizarin derivative is of no significance to the structure of the compound, is not considered to be a limitation of the claim and thus is not given patentable weight.
The difference between Kun and the instant claim is that the instant claim is drawn to a compound of formula 1 with specific substituents as R groups whereas Kun teaches a compound with R groups as instantly claimed (see the underlined below) and additional groups.
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Therefore, a skilled artisan would have had reason to try Kun's limited number of R groups, including the claimed ones and would have a reasonable expectation of success in arriving at the instantly claimed compound.
MPEP § 2143 states that the Supreme Court in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) identified a number of rationales to support a conclusion of obviousness which are consistent with the proper “functional approach” to the determination of obviousness as laid down in Graham and discussed circumstances in which a patent might be determined to be obvious. Importantly, the Supreme Court reaffirmed principles based on its precedent that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp and that a combination was obvious to try might show that it was obvious under § 103.”KSR, 550 U.S. at 421, 82 USPQ2d at 1397.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to arrive at the instantly claimed compound of formula 1 in view of the teachings of Kun.
Allowable Subject Matter
The subject matter of claim 8 is free of prior art. The closest prior art references have been set forth above but fail to teach a method for preparing the quinizarin derivatives as instantly claimed.
Citation of Relevant Prior Art
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Patent application DE102011079970A1 teaches in [0008] compounds that can read on the claimed formula 2.
Conclusion
Claims 1-7 and 9-10 are rejected and no claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MEDHANIT W BAHTA whose telephone number is (571)270-7658. The examiner can normally be reached Monday-Friday 8am-5pm.
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/MEDHANIT W BAHTA/ Primary Examiner, Art Unit 1692
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