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 .
Priority
Applicant’s claim for the benefit of a prior-filed application under 35 U.S.C. 119(e) or under 35 U.S.C. 120, 121, 365(c), or 386(c) is acknowledged. Applicant has not complied with one or more conditions for receiving the benefit of an earlier filing date under 35 U.S.C. 120 as follows:
The later-filed application must be an application for a patent for an invention which is also disclosed in the prior application (the parent or original nonprovisional application or provisional application). The disclosure of the invention in the parent application and in the later-filed application must be sufficient to comply with the requirements of 35 U.S.C. 112(a) or the first paragraph of pre-AIA 35 U.S.C. 112, except for the best mode requirement. See Transco Products, Inc. v. Performance Contracting, Inc., 38 F.3d 551, 32 USPQ2d 1077 (Fed. Cir. 1994).
The disclosure of the prior-filed application, Application No. 63/538,942, fails to provide adequate support or enablement in the manner provided by 35 U.S.C. 112(a) or pre-AIA 35 U.S.C. 112, first paragraph for one or more claims of this application. A claim by claim analysis indicated a lack of support for the formula in claim 1, for example the priority document does not provide support for X being other than O, R8 and R7 being other than OCH3, R6 being other than CH3, or R1 being other than methyl , H or acetyl. It also provides no support for a pharmaceutically acceptable carrier. For these reasons a date of 09/18/2024 was used for priority for all claims.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 08/15/2025 is being considered by the examiner.
Specification
The disclosure is objected to because of the following informalities: the chemical compounds on page.
Appropriate correction is required.
Applicant is reminded of the proper content of an abstract of the disclosure.
In chemical patent abstracts for compounds or compositions, the general nature of the compound or composition should be given as well as its use, e.g., “The compounds are of the class of alkyl benzene sulfonyl ureas, useful as oral anti-diabetics.” Exemplification of a species could be illustrative of members of the class. For processes, the type of reaction, reagents and process conditions should be stated, generally illustrated by a single example unless variations are necessary.
The applicant is reminded to provide details including use of the compound in the abstract.
Claim Objections
Claims 11-12 are objected to because of the following informalities: poor figure resolution. Appropriate correction is required.
Claims 2 and 9 are objected to because of the following informalities: the stereocenters have been improperly labeled because it is impossible for the center to change but the “R” and “S” labels to remain the same. Appropriate correction is required.
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Applicant is advised that should claim 2 be found allowable, claim 5 will be objected to under 37 CFR 1.75 as being a substantial duplicate thereof. When two claims in an application are duplicates or else are so close in content that they both cover the same thing, despite a slight difference in wording, it is proper after allowing one claim to object to the other as being a substantial duplicate of the allowed claim. See MPEP § 608.01(m).
Applicant is advised that should claim 3 be found allowable, claim 4 will be objected to under 37 CFR 1.75 as being a substantial duplicate thereof. When two claims in an application are duplicates or else are so close in content that they both cover the same thing, despite a slight difference in wording, it is proper after allowing one claim to object to the other as being a substantial duplicate of the allowed claim. See MPEP § 608.01(m).
Applicant is advised that should claim 9 be found allowable, claim 11 will be objected to under 37 CFR 1.75 as being a substantial duplicate thereof. When two claims in an application are duplicates or else are so close in content that they both cover the same thing, despite a slight difference in wording, it is proper after allowing one claim to object to the other as being a substantial duplicate of the allowed claim. See MPEP § 608.01(m).
Applicant is advised that should claim 10 be found allowable, claim 12 will be objected to under 37 CFR 1.75 as being a substantial duplicate thereof. When two claims in an application are duplicates or else are so close in content that they both cover the same thing, despite a slight difference in wording, it is proper after allowing one claim to object to the other as being a substantial duplicate of the allowed claim. See MPEP § 608.01(m).
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.
Claim 19-20 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 19 is rejected as indefinite because it depends on a claim that does not exist. There is no claim 25. If the base claim has been canceled, a claim which is directly or indirectly dependent thereon should be rejected as incomplete. MPEP 608.01(n) (V).
Claim 20 is rejected for the term analog because one of ordinary skill in the art would not know what could be considered an analog. For example one would not know if any isomer could be considered an analog or if non-isomers would be considered analogs thus the scope of the claim is unclear.
Claim Rejections - 35 USC § 101
35 U.S.C. 101 reads as follows:
Whoever invents or discovers any new and useful process, machine, manufacture, or composition of matter, or any new and useful improvement thereof, may obtain a patent therefor, subject to the conditions and requirements of this title.
Claims 1-6 and 9-14 are rejected under 35 U.S.C. 101 because the claimed invention is directed to a natural phenomenon without significantly more. Claim 1 recites a compound of the formula:
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, which includes the natural compounds from nutmeg, seeds of Crataegus pinnatifida, Oenanthe javanica (Blume) and the aril of Myristica fragrans, (see Oanh et al., Insights into the inhibitory activities of neolignans and diarylnonanoid derivatives from nutmeg (Myristica fragrans Houtt.) seeds on soluble epoxide hydrolase usingin vitro and in silico approaches. JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY2023, VOL. 38, NO. 1, 2251099, Huang et al., The cytotoxicity of 8-O-40 neolignans from the seeds of Crataegus pinnatifida, Bioorganic & Medicinal Chemistry Letters 23 (2013) 5599–5604 and Ma et al., ANTI-INFLAMMATORY PHENYLPROPANOID DERIVATIVES FROM THE AERIAL PARTS OF Oenanthe javanica, Chemistry of Natural Compounds, Vol. 57, No. 4, July, 2021 and HADA et al., NEW NEOLIGNANS AND LIGNANS FROM THE ARIL OF MYRISTICA FRAGRANS, Phytochemistry, Vol. 27, No. 2, pp. 563-568, 1988).
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In accordance with the 2019 Revised Patent Subject Mater Eligibility Guidance (aka 2019 PEG), the following revised flowchart found in MPEP §2106(III), is used when considering whether or not a claimed invention recites eligible subject matter:
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The invention recited in claims 1-6 and 9-14 are drawn to a composition of matter. Step 1 is satisfied.
Step 2 has now been broken out into a two-prong analysis:
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Step 2A first asks whether or not the claimed invention is directed to a judicial exception such as a natural phenomenon (e.g., product of nature). Here, the answer is yes, since the only compositional requirement set forth in the claims is a compound of the formula of claim 1 which includes natural compounds found in plants.
The second leg of the analysis evaluates whether the claim recites additional elements that integrate the established judicial exception into a practical application of the exception. Based on the recitations provided in claims 1-6 and 9-14 the answer is no. There is not a practical application of the law of nature. These claims recite further ingredients (a pharmaceutically-acceptable carrier) that may be naturally occurring (e.g., water). Lastly, step 2B asks if the claim recites additional elements that amount to “significantly more” than the judicial exception. Asked another way, do the claims recite anything additional demonstrating that the recited composition provides an inventive concept? Here, again, the answer is no because the claims simply do not recite anything else, compositionally or structurally, which provides an inventive concept that departs from a natural product. The composition as claimed is composed of all naturally occurring ingredients. As such, the claims fail to recite subject matter that is patent eligible, and thus the claims do not amount to significantly more than the judicial exception.
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.
Claim(s) 1-6, 9-14 and 20 is/are rejected under 35 U.S.C. 102(a)(1) as being clearly anticipated by Kuo (Kuo et al., Photosensitized oxidation of isoeugenol in protic and aprotic solvents, Chemical & pharmaceutical bulletin. , 1991, Vol.39(9), p.2196-2200).
The reference KUO teaches the following compounds 12a-12d (page 2197), wherein R1= H, R2=methyl, X=O, R3= methoxy, R4=H, R5=methyl, R6=methyl, R7=H, R8=methoxy.
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This anticipates claims 1-6, 9-13.
The reference KUO teaches “The oxidation of isoeugenol (1) has been studied previously as a model of the formation of lignan-related dimers during ferric chloride oxidation and enzymatic
oxidation. Photolysis and free radical oxidation of isoeugenol also give similar products”(page 2196) and the following synthesis method(page 2198):
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This anticipates claims 14 and 20.
Claim(s) 1, 3, 4, 6, 14 and 15-18 is/are rejected under 35 U.S.C. 102(a)(1) as being clearly anticipated by Huang et al., The cytotoxicity of 8-O-40 neolignans from the seeds of Crataegus pinnatifida, Bioorganic & Medicinal Chemistry Letters 23 (2013) 5599–5604.
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The reference Huang teaches “Repeated column chromatography of the 70% ethanol extract of the seeds of C. pinnatifida resulted in the isolation of nine new 8-O-40 neolignans together with 9 known analogs8 (Fig. 1). The chemical structures of the known compounds were identified to be threo-(7R,8R)-guaiacylglycerol-b-coniferyl aldehyde ether (10),9 erythro-(7S,8R)-guaiacylglycerol-b-coniferyl aldehyde ether (11),9 threo-(7R,8R)-guaiacyl-glycerol-b-O-40-dihydroconiferyl ether (12),10 erythro-(7S,8R)-guaiacyl-glycerol-b-O-40-dihydroconiferyl ether (13),10 threo-(7R,8R)-3-methoxy-8,40-oxyneoligna-30,4,7,9,90 pentol (14),11 threo-(7R,8R)-1-(4-hydroxy-3-methoxyphenyl)-2 {4-[(E)-3-hydroxy-1-propenyl]-2-methoxyphe-noxy}-1,3-propanediol (15),12 erythro-(7S,8R)-1-(4-hydroxy-3-methoxyphenyl)-2-{4-[(E) 3-hydroxy-1-propenyl]-2-methoxyphe-noxy}-1,3-propanediol (16),12 threo-(7R,8R)-guaiacylglycerol 8-vanillin ether (17)13 and erythro (7S,8R)-guaiacylglycerol 8-vanillin ether (18)” (page 5599), , wherein R1= H, R2=methyl, X=O, R3= methoxy, R4=H, R5=methoxymethyl, R6=hydroxymethyl, R7=H, R8=methoxy.
This anticipates claims 1, 3, 4, 6, 14.
The reference Huang teaches (pages 5602-5603):
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This anticipates claims 15-18.
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.
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.
Claim(s) 1 and 7-8 is/are rejected under 35 U.S.C. 103 as being unpatentable over Zhen (Zhen et al., Machilin D, a Lignin Derived from Saururus chinensis, Suppresses Breast Cancer Stem Cells and Inhibits NF-κB Signaling, Biomolecules 2020, 10, 245, IDS) further in view of Barillari (Barillari et al., Classical Bioisosteres, Bioisosteres in Medicinal Chemistry, First Edition. Edited by Nathan Brown 2012 Wiley-VCH Verlag GmbH & Co. KGaA. Published 2012 by Wiley-VCH Verlag GmbH & Co. KGaA pages 15-29).
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The reference Zhen teaches Machilin D derived from the plant Saururus chinensis (figure 2, page 4), wherein R1=H, R2=H, X=O, R3=H, R4=H, R5=methyl, R6=methyl, R7=methoxy, R8=methoxy.
The reference Zhen teaches “Machilin D, a Lignin Derived from Saururus chinensis, Suppresses Breast Cancer Stem Cells and Inhibits NF-κB Signaling” (title). The reference Zhen teaches “To determine whether machilin D has a potent inhibitory effect on human cancer cells, we first tested the antiproliferative effect on machilin D at various concentrations in MCF-7 and MDA-MB-231 cells. We observed an antiproliferative effect of ≥ 25 µM machilin D after one day of stimulation (Figure 3A,B)” (page 7) and “We also tested the killing effects of machilin D on ALDH-positive cancer cells. Machilin D reduced the ALDH-positive cell fraction from 7.8% to 4.2% (Figure 5B). Our results showed that machilin D specifically inhibits mammosphere formation”(page 9). The reference Zhen teaches “Cancer cells (3.5 × 104 or 0.5 × 104 cells) were cultured in an ultralow attachment 6-well plate with a MammoCultTM culture medium (StemCell Technologies, Vancouver, BC, Canada)”(page 4).
This helps to teach claims 7-8.
The reference Zhen does not teach X=NH (claim 7) or X=S (claim 8).
The reference Barillari teaches “The discovery and development of a candidate for clinical valuation is a long process that involves small modifications to a lead compound to improve some of its properties, such as pharmacological activity, selectivity, and pharmacokinetics. This is often achieved by the medicinal chemists by replacing a functional group with groups sharing similar physical or chemical properties and maintaining similar activity, which are defined as bioisosteres. We will hereby provide a historical overview of the development and evolution of the concepts of isosterism and bioisosterism, followed by a selection of successful examples of bioisosteric modifications reported in the literature”(page 15).
The reference Barillari teaches (page 17):
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This helps to teach claims 7-8.
It would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the instant invention to have modified the compound from Zhen with the bioisosteres from Barillari because it is common practice as taught by Barillari to replace a functional group with groups sharing similar physical or chemical properties and maintaining similar activity, which are defined as bioisosteres such as -OH to -NH2 or -SH. One would have a reasonable expectation of success because these are acknowledged monovalent bioisospheres. One would be motivated to do so because small modifications to a lead compound may improve some of its properties, such as pharmacological activity, selectivity, and pharmacokinetics for the treatment of cancer.
Conclusion
Claims 1-20 are rejected.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ALISON AZAR HASTINGS whose telephone number is (703)756-4584. The examiner can normally be reached Mon-Thurs 7:30am-5pm EST Friday 7:30-4pm EST (every other Friday off).
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Kortney Klinkel can be reached at (571) 270-5239. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/A.A.H./ Examiner, Art Unit 1627
/Kortney L. Klinkel/ Supervisory Patent Examiner, Art Unit 1627
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