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
The preliminary amendment dated 3 January 2024, in which claims 4, 6, 9, 12, 15, 17-19, 24, 30, 32-33, 37, 42, 47, 55, 57-58, 70 have been amended, and claims 5, 7-8, 10-11, 13-14, 16, 20-23, 25-29, 31, 34-36, 38-41, 43-46, 48-52, 56, 59-69, 71-94, and 96-109 have been cancelled, is acknowledged.
Claims 1-4, 6, 9, 12, 15, 17-19, 24, 30, 32-33, 37, 42, 47, 53-55, 57-58, 70, 95 are pending in the instant application.
Claims 47, 70, 95 are withdrawn, as being drawn to a non-elected invention or to a non-elected species.
Claims 1-4, 6, 9, 12, 15, 17-19, 24, 30, 32-33, 37, 42, 53-55, 57-58 are being examined on their merits herein.
Priority
The instant application is a National Stage entry of International Application No. PCT/US2022/037208, filed on 14 July 2022, which claims priority from U.S. Provisional Patent Application No. 63/224,202, filed on 21 July 2021, and from U.S. Provisional Patent Application No. 63/222,673, filed on 16 July 2021.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 3 January 2024 is acknowledged and considered.
Election/Restrictions
Applicant’s election without traverse of Group (I), claims 1-4, 6, 9, 12, 15, 17-19, 24, 30, 32-33, 37, 42, 47, 53-55, 57-58, drawn to a compound of formula (I), or a pharmaceutically acceptable salt thereof, in the reply filed on 14 April 2026, is acknowledged. Claims 70, 95 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to nonelected inventions, there being no allowable generic or linking claim.
Applicants’ election without traverse of the compound below (compound 68, page 41 Specification):
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as the species of a compound of formula (I)
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, for initial examination, in the Reply of 14 April 2026, is acknowledged.
The elected species is a compound of formula (I) of instant claim 1, for which the following definitions apply:
X = Y = O;
R1 = R3 = -OH; R2 = R4 = H;
R5 = R9 = H; R6 = R7 = R8 = -OH;
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wherein R10 is F; R14 = H; R11 = R12 = -OH;
R13 = OMe (C1 alkoxy).
Claims 1, 2, 4, 6, 9, 12, 15, 17-19, 24, 30, 32-33, 37, 42, 53-55, 57-58 read on the elected species. Claim 47 is withdrawn, as being drawn to a non-elected species.
Since Applicant has set forth no arguments (pages 2-3, Remarks of 14 April 2026) against the requirement for restriction/election of species, Applicant’s election is treated as an election without traverse, and the requirement for restriction is herein maintained and is made FINAL.
Claims 1-4, 6, 9, 12, 15, 17-19, 24, 30, 32-33, 37, 42, 53-55, 57-58 have been examined to the extent they read on the elected species and the following objections and rejections are made below.
Claims Objections
Claims 47, 70, 95, while currently withdrawn, are objected to because of the following informality: The withdrawn claims are objected to for being presented in a non-compliant form. Specifically, the status identifier states the claims is “(Currently amended)”, or “(Original)”, but the claims are withdrawn because of the election made by the Applicant on 14 April 2026. As such, claims 47, 70, 95 should be identified as "(Withdrawn)" until such time as examiner rejoins the claims for examination. Appropriate correction is required. See MPEP 714(C).
Objection to the Specification
The Specification is objected to because in the Table, [0058], page 46, the structure drawn does not correspond to the chemical name listed near the structure. Further, importantly, this chemical name appears in claims 53, 54 and 55 as the last compound listed in each of these claims.
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Appropriate clarification is required.
The Specification is objected to because the Scheme Scaffold 3 on page 94 contains
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. Clarification of the structure Scaffold 3 is required.
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 1-4, 6, 9, 12, 15, 17-19, 24, 30, 32-33, 37, 42, 57-58 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.
Claim 1 is drawn to a compound of formula (I)
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or a pharmaceutically acceptable salt thereof. It is unclear what the dotted lines in the structure stand for. It is unclear whether formula (I) refers to racemic mixtures, cis diastereomers, enantiomers. There is no indication that claim 1 includes enantiomers of a compound of formula (I) or diastereoisomers of a compound of formula (I).
In organic chemistry, dashed lines are used to show atoms and bonds that go into the page, behind the plane, away from the reader. As such, the dashed lines in formula (I) seem to be consistent with cis 2, 3-disubstituted chromans (X = O) or tetralins (X = C); racemic mixtures. This is however in disagreement with the proviso in claim 1 which excludes from the claim a number of enantiomers, including (2S, 3R) substituted chromans.
Claim 2 depends on claim 1 and recites
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, which shows a trans 2, 3-disubstituted chroman (X = O) or tetralin (X = C); yet, claim 1 does not recite cis or trans stereoisomers of a compound of formula (I). As such, there is insufficient antecedent basis for the compound of formula (IA) above (of claim 2), in claim 1.
Claim 3 depends on claim 1 and recites
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It is unclear how formula (IB) is distinct from formula (I) in claim 1.
Appropriate clarification is required.
In the interest of compact prosecution, the examiner interprets claim 1 as being drawn to a compound of formula (I) (structure with solid lines covalent bonds, not dotted lines), or a stereoisomer, or an enantiomer, or a pharmaceutically acceptable salt thereof. If claims 2 and 3 are meant to include enantiomers, the claims should clearly state that.
Claims 24, 30, 32-33, 37, 42 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.
It is unclear what the difference is between structures (II) and (II-B) in claim 24.
Further, 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 24 recites the broad recitation
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, and the claim also recites
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,which is the narrower statement of the range/limitation. Claim 24 recites the broad recitation
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, and the claim also recites
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,which is the narrower statement of the range/limitation. Claim 24 recites the broad recitation formula (II-B), and the claim also recites formula (III-B), which is the narrower statement of the range/limitation. 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.
Appropriate correction is required.
Claim 53 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 53 depends on claim 1 and recites (the third compound listed in claim 53)
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;
yet this compound has been excluded by proviso (third compound under “where the compound is not […] in claim 1) from claim 1. As such, there is insufficient antecedent basis for this compound of claim 53, in claim 1.
Appropriate correction is required.
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.
(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.
Claims 1, 2, 4, 6, 9, 15, 19, 24, 30, 37 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by PubChem SID 341461851 (available 13 September 2017, cited in IDS).
PubChem SID 341461851 discloses the compound below
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,
which is a compound of instant formula I of claim 1, and is a compound of formula (I-A)
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of claim 2, for which the following definitions apply:
X is O; Y is O;
R1 = R2 = R3 = R4 = R5 = R6 = R7 = R8 = R9 = H;
Z is
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, wherein R10 = R11 = R12 = R13 = R14 = H.
As such, a compound of instant claims 1, 2, 4, 6, 9, 15, 19, 24, 30, 37 is anticipated by PubChem SID 341461851.
Claims 1, 2, 4, 6, 9, 12, 15, 17-19, 24, 30, 37 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by PubChem SID 247320529 (available 17 March 2015, cited in IDS).
PubChem SID 247320529 discloses the compound below
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(+/-),
which is a compound of instant formula I of claim 1, and is a compound of formula (I-A)
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of claim 2, for which the following definitions apply:
X is O; Y is O;
R1 = R3 = OH; R2 = R4 = R5 = R6 = R9 = H; R7 = R8 = OH;
Z is
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, wherein R10 = R13 = R14 = H; R11 = R12 = OH.
As such, a compound of instant claims 1, 2, 4, 6, 9, 12, 15, 17-19, 24, 30, 37 is anticipated by PubChem SID 247320529.
Claims 1-4, 6, 9, 12, 15, 17-19, 24, 30, 37, 42, 57 are rejected under 35 U.S.C. 102(a)(1) and 102(a)(2) as being anticipated by Anderson et al. (US 7,700,646 of 20 April 2010, cited in IDS).
Anderson discloses (column 4, lines 50-65 (also column 31, lines 45-60), column 5, lines 1-25) the compounds below:
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,
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which are compounds of instant formula I of claim 1, and are compounds of formula (I-B)
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of claim 3, for which the following definitions apply:
X is O; Y is O;
R1 = R3 = OH; R2 = R4 = H;
R5 = R9 = H; R6 or R7 or R8 is OH; or both R6 and R8 are OH;
Z is
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, wherein R10 = R14 = H; R11 = R12 = R13 = OH.
Anderson also discloses (column 23, 24) the following compounds:
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,
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which are compounds of instant formula I of claim 1; compound 21 above is a compound of formula (I-B)
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of claim 3, for which the following definitions apply:
X is O; Y is NH;
R1 = R3 = OH; R2 = R4 = H;
R5 = R6 = R9 = H; R7 =R8 = OH;
Z is
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, wherein R10 = R14 = H; R11 = R12 = R13 = OH.
Anderson teaches pharmaceutical compositions comprising the compounds of the invention, as in instant claim 57.
As such, a compound of instant claims 1-4, 6, 9, 12, 15, 17-19, 24, 30, 37, 42, or a composition comprising said compound, is anticipated by Anderson.
Claims 1-2, 4, 6, 9, 12, 15, 17-19, 24, 30, 37, 42, 57 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Dell’Agli et al. (Cell Mol Life Sci 2005, 62, 2896-2903, cited in IDS).
Dell’Agli discloses (Figure 1, page 2897) the compounds below as trans racemates
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which are compounds of instant formula I of claim 1, and are compounds of formula (I-A)
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of instant claim 2, for which the following definitions apply:
X is O; Y is O;
R1 = R3 = OH; R2 = R4 = H;
R5 = R9 = H; R6, R7, R8 are H or OH;
Z is
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, wherein R10 = R14 = H; R11, R12, R13 are H or OH.
Dell’Agli teaches pharmaceutical compositions comprising the compounds, as in instant claim 57.
As such, a compound of instant claims 1-2, 4, 6, 9, 12, 15, 17-19, 24, 30, 37, 42, 57, or a composition comprising said compound, is anticipated by Dell’Agli.
Claims 1-4, 6, 9, 12, 15, 17-19, 24, 30, 37, 42, 57 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Abe et al. (Biochemical and Biophysical Research Communications 2000, 268, 767-771, cited in PTO-892).
Abe discloses (Figure 2, page769) the following compounds
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, which are compounds of instant formula I of claim 1. Compound 4 taught by Abe is a compound of formula (I-B)
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of instant claim 3, for which the following definitions apply:
X is O; Y is O;
R1 = R3 = OH; R2 = R4 = H;
R5 = R8 = R9 = H; R7= R6 = OH;
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, wherein R10 = R14 = H; R11= R12 = OH; R13 = OMe (C1 alkoxy).
Compound 6 taught by Abe is a compound of formula (I-A)
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of instant claim 2, for which the following definitions apply:
X is O; Y is O;
R1 = R3 = OH; R2 = R4 = H;
R5 = R9 = H; R7= R6 = R8 = OH;
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, wherein R10 = R14 = H; R11= R12 = OH; R13 = OMe (C1 alkoxy).
Abe teaches pharmaceutical compositions comprising the compounds, as in instant claim 57.
As such, a compound of instant claims 1-4, 6, 9, 12, 15, 17-19, 24, 30, 37, 42, 57, or a composition comprising said compound, is anticipated by Abe.
Claims 1-2, 4, 6, 9, 12, 15, 17-19, 24, 30, 37, 42, 57 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Saeki et al. (Phytochemistry 2000, 53, 391-394, cited in PTO-892).
Saeki discloses (Figure 1, page 392) the following compound
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, which is a compound of instant formula I of claim 1, and is a compound of formula (I-A)
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of instant claim 2, for which the following definitions apply:
X is O; Y is O;
R1 = R3 = OH; R2 = R4 = H;
R5 = R9 = H; R7= R6 = R8 = OH;
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, wherein R10 = R14 = H; R11= R12 = OH; R13 = OMe (C1 alkoxy).
Saeki teaches pharmaceutical compositions (Fig. 2, in vitro testing) comprising the compound, as in instant claim 57.
As such, a compound of instant claims 1-2, 4, 6, 9, 12, 15, 17-19, 24, 30, 37, 42, 57, or a composition comprising said compound, is anticipated by Saeki.
Claims 1-4, 6, 9, 12, 15, 17-19, 24, 30, 37, 42, 57 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Sano et al. (J Agric Food Chem 2003, 51, 2912-2916, cited in PTO-892).
Sano discloses (Figure 1, page 2914) the following compounds
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, which are compounds of instant formula I of claim 1, and are compounds of formula of formula (I-A)
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of instant claim 2, for which the following definitions apply:
X is O; Y is O;
R1 = R3 = OH; R2 = R4 = H;
R5 = R9 = H; R7= R6 = R8 = OH;
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, wherein R10 = R14 = H; and
R11= R12 = OH; R13 = OMe (C1 alkoxy) (GCG3”Me), or
R11= R13 = OH; R12 = OMe (C1 alkoxy) (GCG4”Me).
Sano also discloses (Figure 1, page 2914) the following compounds
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, which are compounds of instant formula I of claim 1, and are compounds of formula of formula (I-B)
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of instant claim 3, for which the following definitions apply:
X is O; Y is O;
R1 = R3 = OH; R2 = R4 = H;
R5 = R9 = H; R7, R6 are OH or OMe; R8 is H, OH or OMe;
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, wherein R10 = R14 = H; R11= R12 = OH; R13 = OMe (C1 alkoxy) or OH.
Sano teaches pharmaceutical compositions (Fig. 5, in vitro testing) comprising the compounds, as in instant claim 57.
As such, a compound of instant claims 1-4, 6, 9, 12, 15, 17-19, 24, 30, 37, 42, 57, or a composition comprising said compound, is anticipated by Sano.
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.
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.
Claims 1-2, 4, 6, 9, 12, 15, 17-19, 24, 30, 32-33, 37, 42, 53-55, 57-58 are rejected under 35 U.S.C. 103 as being unpatentable over Sano et al. (J Agric Food Chem 2003, 51, 2912-2916, cited in PTO-892), in view of Patani et al. (Chemical Reviews 1996, 96, 3147-3176, cited in PTO-892), in further view of Araldi (WO 2019/235521, published 12 December 2019, cited in PTO-892).
Sano discloses (Figure 1, page 2914) compound GCG3”Me below
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, ,
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which is a structural analog H vs. F of the instant elected species compound 68
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of instant claims 53-55,
and is a structural analog H vs. F of compound 50
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of instant claims 53, 54,
and is a structural analog H vs. F of compound 59
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of instant claim 53,
and is a structural analog R10, R14 = H vs. R10, R14 = F of compounds of instant formula (I-A)
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of instant claim 2, for which the following definitions apply:
X is O; Y is O;
R1 = R3 = OH; R2 = R4 = H;
R5 = R9 = H; R7= R6 = R8 = OH;
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, wherein
R11= R12 = OH; R13 = OMe (C1 alkoxy).
Sano teaches a pharmaceutical composition (Figure 5, in vitro assay) comprising compound GCG3”Me, having antioxidant activity (IC50 = 20 mM).
Sano does not specifically teach the instant fluorinated compounds 68, 50, 59.
Patani et al. (Chemical Reviews 1996, 96, 3147-3176, cited in PTO-892) teach that fluorine vs. hydrogen replacement is a classical bioisosteric replacement based on monovalent atoms, frequently used in drug design (see page 3149, Chapter II.A.1., lines 1-5 below):
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Araldi (WO 2019/235521) teaches pharmaceutical formulations for intranasl administration comprising a catechin, present in the formulation at between about 1% to about 40% w/w, and one or more of
(a) 0 1 -20% w/w% of a permeation enhancer;
(b) 0.1-20% w/w% of a chelator/anti-oxidant;
(c) 1 -30% w/w% of a humectant; and/or
(d) 0.03%-2% preservative;
wherein the formulation has a pH of between 4.0 and 6.5, as in instant claim 58.
It would have been obvious to a person of ordinary skill in the art to combine the teachings of Sano and Patani in a compound of the instant application. The person of ordinary skill in the art would have been motivated to replace a H atom on the phenyl ring of compound GCG3”Me taught by Sano with a F substituent, based on the teachings of Patani, because such fluorine vs. hydrogen replacements often result in better biological activity (here anti-oxidant activity) and better overall physicochemical and pharmacological properties of the molecules. Thus, absent some demonstration of unexpected results with the instantly claimed compounds versus the prior art by Sano, the instant compounds would have been obvious at the time of applicant's invention.
Regarding claim 58, it would have been obvious to formulate the fluoro-substituted analogs of compound GCG3”Me as an intranasal formulation, because Araldi teaches pharmaceutical formulations for intranasal administration comprising structurally similar catechins, a permeation enhancer; a chelator/anti-oxidant; a humectant; and/or preservative; with a pH of between 4.0 and 6.5. The person of ordinary skill in the art would have been motivated to formulate the F-substituted analogs of compound GCG3”Me taught by Sano as an intranasal formulation, using the ingredients and concentrations taught by Araldi, with a reasonable expectation of success.
As such, claims 1-2, 4, 6, 9, 12, 15, 17-19, 24, 30, 32-33, 37, 42, 53-55, 57-58 are rejected as prima facie obvious.
Conclusion
Claims 1-4, 6, 9, 12, 15, 17-19, 24, 30, 32-33, 37, 42, 53-55, 57-58 are rejected.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to IRINA NEAGU whose telephone number is (571)270-5908. The examiner can normally be reached Mon-Fri 8-5.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
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/IRINA NEAGU/Primary Examiner, Art Unit 1629
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