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 .
Election/Restrictions
Applicant’s election without traverse of Group I, Claims 1-19 and 21, drawn to a compound of Formula I, and a compound having the structure of:
PNG
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192
348
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Greyscale
in the reply filed on April 17 2026 is acknowledged.
Claims 3, 10-12, 14-15 and 20 withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention and species, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on April 17 2026.
Status of the Claims
Claims 1-21 are pending. Claims 3, 10-12, 14-15 and 20 are withdrawn.
Claims 1-2, 4-9, 13, 16-19 and 21 are under examination in accordance with the elected compound species along with the expanded compound species.
Priority
The instant application 18/517,497 filed on November 3, 2023 claims priority to, and the benefits of U.S. Provisional Application No. 63/428,303 filed on November 28, 2022.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on March 24, 2024 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Claim Rejections - 35 USC § 112(a)
Written Description
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claims 1, 2, 4-9, 13, 16-18, and 21 are rejected under 35 U.S.C. 112(a) as failing to comply with the written description requirement. The claims contain subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, at the time the application was filed, had possession of the claimed invention. This is a written description rejection.
Independent claim 1 recites a large genus of briarane compounds encompassed by Formula I, wherein R1 is C1-C6 alkyl; R2 is C1-C6 alkyl, formyl, carboxyl, -CH=N-ORa, -CH=NRa, or -C(O)NH-O-Ra; R3 is H, hydroxy, or combined with R4, wherein R4 is H or C1-C6 alkyl, or R3 and R4 together form an epoxide ring; R5 is N3, methyl, or combined with X2 to form a heterocycloalkyl ring; R6 is H, halo, oxo, hydroxyl, -NRb, =N-NH-C(O)Rc, -OC(O)Rd, or -O-S(O)2Re; R7 is H or acetoxy; X1 is hydroxy or oxo; and X2 is O or N, wherein X2 may be combined with R5. The claim further recites that each indicated bond may be a single bond or double bond and that the alkyl, amino, aryl, heteroaryl, alkenyl, alkynyl, carboxylate, cycloalkyl, heterocycloalkyl, and related substituent groups may be unsubstituted or substituted with numerous further groups.
Adequate written description requires more than a mere statement that it is part of the invention and reference to a potential method for isolating it. See Fiers v. Revel, 25 USPQ2d 1601, 1606 (CAFC 1993) and Amgen Inc. v. Chugai Pharmaceutical Co. Ltd., 18 USPQ2d 1016.
According to MPEP 2163 I, “[t]o satisfy the written description requirement, a patent specification must describe the claimed invention in sufficient detail that one skilled in the art can reasonably conclude that the inventor had possession of the claimed invention. See, e.g., Moba, B.V. v. Diamond Automation, Inc., 325 F.3d 1306, 1319, 66 USPQ2d 1429, 1438 (Fed. Cir. 2003); Vas-Cath, Inc. v. Mahurkar, 935 F.2d at 1563, 19 USPQ2d at 1116… An applicant shows that the inventor was in possession of the claimed invention by describing the claimed invention with all of its limitations using such descriptive means as words, structures, figures, diagrams, and formulas that fully set forth the claimed invention. Lockwood v. Amer. Airlines, Inc., 107 F.3d 1565, 1572, 41 USPQ2d 1961, 1966 (Fed. Cir. 1997). Possession may be shown in a variety of ways including description of an actual reduction to practice, or by showing that the invention was “ready for patenting” such as by the disclosure of drawings or structural chemical formulas that show that the invention was complete, or by describing distinguishing identifying characteristics sufficient to show that the inventor was in possession of the claimed invention. See, e.g., Pfaff v. Wells Elecs., Inc., 525 U.S. 55, 68, 119 S.Ct. 304, 312, 48 USPQ2d 1641, 1647 (1998); Eli Lilly, 119 F.3d at 1568, 43 USPQ2d at 1406; Amgen, Inc. v. Chugai Pharm., 927 F.2d 1200, 1206, 18 USPQ2d 1016, 1021 (Fed. Cir. 1991)”.
Additionally, according to MPEP II-A-3-a-ii, “[t]he written description requirement for a claimed genus may be satisfied through sufficient description of a representative number of species by actual reduction to practice, reduction to drawings, or by disclosure of relevant, identifying characteristics, i.e., structure or other physical and/or chemical properties, by functional characteristics coupled with a known or disclosed correlation between function and structure, or by a combination of such identifying characteristics, sufficient to show the inventor was in possession of the claimed genus. See Eli Lilly, 119 F.3d at 1568, 43 USPQ2d at 1406”; “[a] ‘representative number of species’ means that the species which are adequately described are representative of the entire genus. Thus, when there is substantial variation within the genus, one must describe a sufficient variety of species to reflect the variation within the genus. See AbbVie Deutschland GmbH & Co., KG v. Janssen Biotech, Inc., 759 F.3d 1285, 1300, 111 USPQ2d 1780, 1790 (Fed. Cir. 2014).”; and “’[a] patentee will not be deemed to have invented species sufficient to constitute the genus by virtue of having disclosed a single species when … the evidence indicates ordinary artisans could not predict the operability in the invention of any species other than the one disclosed.’ In re Curtis, 354 F.3d 1347, 1358, 69 USPQ2d 1274, 1282 (Fed. Cir. 2004)”
Applicant has failed to show possession of the full scope of the diverse compounds encompassed by Formula I. The instant specification discloses a limited number of specific briarane compounds and synthetic examples, but the claims cover a much broader genus defined by multiple independently variable positions on a complex briarane scaffold. The claimed genus includes compounds having oxo, hydroxy, azido, imino, hydrazone, oxime, oxime ether, hydroxamate, acyloxy, sulfonyloxy, aminoalkyl, heterocycloalkyl, heteroaryl, piperidinyl, morpholinyl, piperazinyl, alkynyl, linker-containing, and thalidomide-type substituent embodiments. The specific compounds disclosed in the specification do not constitute a representative number of species across the full scope of the claimed genus. The working examples are directed to a narrow set of compounds having selected substituent patterns, while claim 1 permits numerous unexemplified combinations of R1, R2, R3, R4, R5, R6, R7, X1, X2, bond arrangements, and substituted group definitions. The specification does not identify structural features common to all members of the broad genus that would allow one of ordinary skill in the art to recognize that Applicant was in possession of the full scope of the claimed Formula I compounds. This issue is especially apparent for the broad alternatives recited for R2, R5, R6, Rc, Rd, and Re. The disclosure does not provide representative examples for each major class of these alternatives, including all oxime, hydrazone, hydroxamate, sulfonyloxy, azido, heterocycloalkyl, heteroaryl, aminoalkyl, alkynyl, linker-containing, and thalidomide-type embodiments. The specification therefore does not reasonably convey possession of the full claimed genus merely by disclosing selected species within the genus. Dependent claims 2, 4-9, 13, and 16-18 further recite selected subgenera and additional Markush alternatives, but these claims still encompass structurally diverse groups and unexemplified combinations that are not adequately represented by the disclosed examples. Claim 21 recites a pharmaceutical composition comprising the broad compound genus of claim 1 and a pharmaceutically acceptable carrier, and therefore also lacks adequate written description support for the full scope of compositions containing all compounds encompassed by claim 1. Accordingly, Applicant has not provided sufficient written description to show that the inventor or a joint inventor was in possession of the full scope of claims 1, 2, 4-9, 13, 16-18, and 21 at the time the application was filed.
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, 5-9, and 13 are rejected under 35 U.S.C. 102(a)(1) as being anticipatedby Sheu et al. (US 8,530,513 B1; hereinafter “Sheu”).
Sheu teaches a briarane-type diterpene, excavatolide B, also referred to as BrD1, and acyloxyl analogues thereof(see e.g. col. 3, line 45). Sheu teaches that excavatolide B has a briarane diterpene core and that analogues may be prepared by substituting the hydroxyl group at the C-12 position with an acyloxyl group(see e.g. col. 5, line 64). Sheu further teaches that the acyloxyl group may contain 2 to 12 carbon atoms and may be straight or branched (see e.g. col. 6, line 1).
The compound of Sheu, including excavatolide B and the disclosed acyloxyl analogues thereof, reads on the compound of instant claim 1 because it possesses the same briarane core structure recited in Formula I, including the bicyclic briarane skeleton, lactone/epoxy-containing fused ring system, ester substituents, and the substituent encompassed by Formula I.
Regarding claim 5, Sheu teaches the corresponding R1 ester substituent as an alkyl ester group, including propyl-containing acyl substitution(see e.g. col. 6, Formula 2-5).
Regarding claim 6, Sheu teaches the corresponding epoxide-containing briarane ring system(see e.g. col. 6, Formula 2-5).
Regarding claim 7, Sheu teaches the corresponding methyl/hydrogen/hydroxy substitution pattern on the briarane scaffold(see e.g. col. 6, Formula 2-5).
Regarding claim 8, Sheu teaches acetoxy substitution corresponding to the recited R7 acetoxy limitation(see e.g. col. 6, Formula 2-5).
Regarding claim 9, Sheu teaches a briarane compound corresponding to one of the receited Formula I-D subgenera(see e.g. col. 6, Formula 2-5).
Regarding claim 13, Sheu teaches the corresponding propyl and acetoxy substitution pattern(see e.g. col. 6, Formula 2-5).
Therefore, Sheu expressly teaches each and every limitation of claims 1, 5-9, and 13.
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, 4-9, 13, and 21 are rejected under 35 U.S.C. 103 as being unpatentable over Sheu et al. (US 8,530,513 B1; hereinafter “Sheu”) in view of Huynh et al. (Molecules, 2020, 25(6):1405).
Sheu teaches excavatolide B, also referred to as BrD1, a briarane-type diterpene, and acyloxyl analogues thereof(see e. g. col. 3 line 50). Sheu teaches that excavatolide B may be modified to provide 12-acyloxyl analogues of BrD1, including BrD1-5C, BrD1-6C, BrD1-7C, and BrD1-10C(see e. g. col. 10 line 6). Sheu therefore teaches the closest briarane/excavatolide scaffold and teaches that the hydroxyl-bearing briarane scaffold was known to be derivatized to provide acyloxy analogues.
Huynh et al. teaches additional 8,17-epoxybriarane diterpenoids from Briareum excavatum, including briarenols I-K and known analogues briaexcavatolide P and briaexcavatin P(see p. 1 introduction). Huynh et al. therefore confirms that structurally varied oxygenated, acetoxy-substituted, epoxide-containing, esterified, and lactone-containing briarane scaffolds from Briareum species were known in the art.
Regarding claim 1, Sheu teaches the briarane/excavatolide core structure of excavatolide B/BrD1 and acyloxyl analogues thereof. Huynh et al. further teaches structurally varied 8,17-epoxybriarane diterpenoids from Briareum excavatum. Therefore, the Formula I briarane compound genus would have been obvious as structurally related analogues of the known excavatolide/briarane scaffold.
Regarding claim 4, Sheu teaches acyloxyl analogues of excavatolide B. Thus, Sheu teaches or suggests the -OC(O)Rd alternative recited for R6.
Regarding claim 5, Sheu teaches acyloxyl analogues of excavatolide B, and Huynh et al. teaches esterified briarane diterpenoids. Selection of methyl, ethyl, n-propyl, or isopropyl for R1 would have been an obvious selection among closely related lower alkyl substituents on the known briarane scaffold.
Regarding claim 6, Sheu teaches the epoxide-containing excavatolide B/briarane scaffold. Huynh et al. further teaches 8,17-epoxybriarane diterpenoids. Therefore, the recited R3/R4 epoxide and hydroxy/hydrogen alternatives would have been obvious.
Regarding claim 7, Sheu and Huynh et al. teach briarane scaffolds having hydrogen, hydroxy, and methyl substitution patterns. Therefore, selection of H, OH, or methyl for R5 would have been an obvious substituent variation.
Regarding claim 8, Sheu and Huynh et al. teach acetoxy-substituted briarane diterpenoids. Therefore, R7 as acetyloxy would have been obvious.
Regarding claim 9, Sheu teaches the briarane/excavatolide scaffold and acyloxyl analogues thereof, and Huynh et al. teaches related 8,17-epoxybriarane substructures having different oxygenated, acetoxy, esterified, epoxide, and lactone substitution patterns. Therefore, selection of a compound of one of the recited Formula I subgenera would have been obvious as a selection among known briarane subgenera and routine structural variations thereof.
Regarding claim 13, Sheu teaches the excavatolide B/briarane scaffold and acyloxyl analogues, while Sheu and Huynh et al. teach acetoxy-substituted briarane structures. Therefore, the combination of R1 as propyl and R7 as acetyloxy would have been obvious.
Regarding claim 21, Sheu teaches pharmaceutical use and administration of excavatolide B and acyloxyl analogues thereof. Pharmaceutical compositions containing active small-molecule compounds and pharmaceutically acceptable carriers were routine and conventional in the art. Therefore, it would have been obvious to formulate a compound of claim 1 with a pharmaceutically acceptable carrier to obtain the pharmaceutical composition of claim 21.
Claims 2, 18, and 19 are rejected under 35 U.S.C. 103 as being unpatentable over Sheu in view of Ren et al. (Pest Manage. Sci. 2020, 76, 3560– 3567) and Hao et al. (J Agric Food Chem. 2022, 70(30):9337-9345),
Sheu teaches the closest briarane/excavatolide scaffold and acyloxyl analogues thereof, as discussed above.
Ren et al. teaches structural modification of the natural product osthole(see p. 3560 Abstract, results). Ren et al. teaches selective oxidation of one methyl group of the 3′-methyl-2′-butylenyl group of osthole, including selenium dioxide oxidation, followed by introduction of an oxime ester moiety (see p. 3562, 3.1 synthesis of osthole derivatives). Ren et al. therefore evidences that oxidation of a natural-product methyl/allylic substituent to an aldehyde-type intermediate and subsequent conversion to C=N-O-containing derivatives were known functional-group modifications.
Hao et al. teaches structural modification of the natural product osthole (see e. g. p. 9337 introduction). Hao et al. teaches that osthole was regioselectively oxidized by selenium dioxide to provide an aldehyde intermediate and that the aldehyde intermediate was further oxidized with sodium chlorite to provide the corresponding carboxylic acid(see e. g. p. 9339, figure 2). Hao et al. further teaches that the carboxylic acid was used to prepare ester and amide derivatives(see e. g. p. 9339, figure 2). Hao et al. therefore evidences that conversion of a natural-product methyl/allylic substituent to an aldehyde and then to a carboxylic acid using NaClO2 was a known functional-group modification of natural-product scaffolds.
Regarding claim 2, Sheu teaches the briarane/excavatolide scaffold. Ren et al. teaches aldehyde and C=N-O-containing derivative formation from a natural-product methyl/allylic substituent. Hao et al. teaches further oxidation of an aldehyde intermediate to the corresponding carboxylic acid. Therefore, selecting the recited R2 alternatives, including formyl, carboxyl, -CH=N-ORa, -CH=NRa, and -C(O)NH-O-Ra, with R6 as OH, would have been obvious as known aldehyde/carboxyl/C=N-derived functional-group modifications of a natural-product scaffold.
Regarding claim 18, to the extent Formula I-F includes carboxyl or carboxy-derived substituent embodiments, Hao et al. teaches oxidation of an aldehyde intermediate to the corresponding carboxylic acid and use of the carboxylic acid to prepare ester and amide derivatives. Therefore, the Formula I-F embodiments would have been obvious.
Regarding claim 19, at least Compounds 61, 62, and 63 would have been obvious over Sheu in view of Ren et al. and Hao et al. Sheu teaches the briarane/excavatolide core. Ren et al. teaches selenium dioxide oxidation of a natural-product methyl/allylic substituent to an aldehyde-type intermediate. Hao et al. teaches sodium chlorite oxidation of the aldehyde intermediate to the corresponding carboxylic acid and further ester/amide derivatization. Accordingly, Compounds 61-63 would have been obvious as structurally related Formula I-F derivatives of the known briarane scaffold using known aldehyde-to-carboxylic-acid functional-group modification.
Claims 16, 17, 18, and 19 are rejected under 35 U.S.C. 103 as being unpatentable over Sheu et al. in view of Wang et al.( Molecules, 2021, 26, 372), further in view of de Souza et al. (US 5,869,523)
Sheu teaches the closest briarane/excavatolide scaffold and acyloxyl analogues thereof, as discussed above.
Wang et al. teaches fluorinated 7-hydroxycoumarin oxime ether derivatives (see p. 3, Scheme 1 4h). Wang et al. teaches O-prop-2-yn-1-yl oxime compounds such as (E)-7-hydroxy-2-oxo-4-(trifluoromethyl)-2H-chromene-8-carbaldehyde O-prop-2-yn-1-yl oxime ( see p. 1 Abstract). and therefore teaches the C=N-O-CH2-C≡CH propargyl oxime ether motif present in elected Compound 66.
de Souza et al. teaches 6β-(3-substitutedamino)propionyloxy forskolin/labdane diterpenoid derivatives (see p.1 abstract). In particular, de Souza et al. teaches 7β-acetoxy-6β-[3-(piperidinopropionyl)oxy]-8,13-epoxy-labdane compounds, as well as corresponding 3-(N-methylpiperazinopropionyl)oxy and 3-(morpholinopropionyl)oxy diterpenoid analogues (see col. 3 line 35). de Souza et al. therefore evidences that piperidinopropionyl, piperazinopropionyl, and morpholinopropionyl acyloxy substituents were known substituent motifs on oxygenated diterpenoid natural-product scaffolds.
Regarding claim 16, Sheu teaches acyloxyl derivatization of the excavatolide B briarane scaffold. de Souza et al. teaches oxygenated diterpenoid compounds bearing 3-substitutedaminopropionyloxy groups, including piperidinopropionyloxy, piperazinopropionyloxy, and morpholinopropionyloxy groups. Therefore, the piperidinyl, piperazinyl, morpholinyl, aminoalkyl, and related acyloxy substituent alternatives recited in claim 16 would have been obvious as known substituent motifs used on oxygenated diterpenoid scaffolds.
Regarding claim 17, claim 17 depends from claim 16 and further requires R1 as propyl and R7 as acetyloxy. Sheu teaches the excavatolide B/briarane scaffold and acyloxyl analogues, and de Souza et al. teaches piperidinopropionyloxy, piperazinopropionyloxy, and morpholinopropionyloxy substituent motifs on oxygenated diterpenoid scaffolds. Therefore, claim 17 would have been obvious.
Regarding claim 18, Wang et al. teaches O-prop-2-yn-1-yl oxime compounds and therefore supports the prop-2-yn-1-yl Ra alternative recited in claim 18.
Regarding claim 19, at least elected Compound 66 would have been obvious over the cited references. Sheu teaches the closest excavatolide B/briarane core and acyloxyl analogue framework. Wang et al. teaches the right-side O-prop-2-yn-1-yl oxime motif, i.e., C=N-O-CH2-C≡CH. de Souza et al. teaches the left-side heterocyclic aminopropionyloxy motif, including piperidinopropionyloxy-type substituents, on an oxygenated diterpenoid scaffold. Accordingly, elected Compound 66 would have been obvious as a structurally related derivative of Sheu’s known excavatolide B scaffold in view of known right-side propargyl oxime ether and left-side piperidinopropionyloxy substituent motifs.
It would have been obvious to one of ordinary skill before the effective filing date to prepare structurally related briarane/excavatolide derivatives by modifying Sheu’s known excavatolide B scaffold using known peripheral functional-group modifications and known substituent motifs taught by Huynh et al., Ren et al., Wang et al., Hao et al., and de Souza et al. The motivation would have been to obtain additional structurally related natural-product analogues of a known briarane/excavatolide scaffold using known derivatization positions and known substituent motifs already applied to natural-product or diterpenoid scaffolds.
A person of ordinary skill would have had a reasonable expectation of success because Sheu teaches the closest briarane scaffold and acyloxyl analogues thereof; Huynh et al. confirms that structurally varied oxygenated and epoxidized briarane diterpenoids were known; Ren et al. teaches aldehyde/oxime-type functionalization of a natural-product methyl/allylic substituent; Hao et al. teaches the preparation of ester and amide derivative. Wang et al. teaches the exact O-prop-2-yn-1-yl oxime motif; de Souza teaches heterocyclic aminopropionyloxy substituent motifs on oxygenated diterpenoid scaffolds.
Therefore, the claimed invention is prima facie obvious to one of ordinary skill in the art at the time the application was filed, absent factual evidence to the contrary.
Conclusion
No Claims are allowed.
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/G.S./Examiner, Art Unit 1628
/AMY L CLARK/ Supervisory Patent Examiner, Art Unit 1628
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