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
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 08/21/2025 has been entered. A suspension of action was not requested.
Claim Status
Claims 70-72, 74-76 and 79-92 are pending. Claims 85-89 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim.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 with traverse in the reply filed on 09/18/2024. Accordingly, claims 70-72, 74-76, 79-84 and 90-92 are under examination.
Claims 70-71, 74 and 79 are rejected. Claims 72, 75-76, 80-84 and 90-92 are objected to. No claims allowed.
Specie Election
Applicant's election without traverse of the immediately below specie in the reply
filed on 09/18/2024 is acknowledged. The elected specie reads on claims 70-72, 74-76, 79-84 and 90-92. The elected specie was found to be free of the art.
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The specie election has been withdrawn.
Filing Receipt
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72
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Note: An approved power of attorney is not of record per the above filing receipt.
Response to Amendments/Arguments
Applicant's amendments and arguments filed 07/21/2025 are acknowledged and have been fully considered. The Examiner has re-weighed all the evidence of record. Any rejection and/or objection not specifically addressed below in original or modified form is herein withdrawn.
The 102 rejection of claims 70-72, 74 and 79 as anticipated by STN (STN 16 Nov 1984, 1 page, Published 11-1984) in the final mailed 04/22/2025 is withdrawn. The claim amendments have overcome the rejection.
The 102 rejection of claims 70-72, 74, 79 and 84 as anticipated by Lianquan et al. (CN1201789, Published 12-1998) in the final mailed 04/22/2025 is withdrawn. The claim amendments have overcome the rejection.
The 102 rejection of claims 70-72, 74 and 79 as anticipated by Schoellkopf et al. (CAPLUS Abstract of Angewandte Chemie (1979), 91(4), 329-30) in the final mailed 04/22/2025 is withdrawn. The claim amendments have overcome the rejection.
The 103 rejection of claims 70-72, 74, 79, 84 and 90-92 over Lianquan et al. (CN1201789, Published 12-1998. Translation attached) and Kahn et al. (Novel Carbopol-based transfersomal gel of 5-fluoroutacil for skin cancer treatment: in vitro characterization and in vivo study, Drug Delivery, 22(6), pp. 795-802, Published 2015) in the final mailed 04/22/2025 is withdrawn.
The 103 rejection of claims 70-72, 74-76, 79-84 and 90-92 over Huang et al. (US2017/0128395, Published 05-2017) in view of Larsen, I. K., Design and Application of Prodrugs, Drug Design and Development (Krogsgaard-Larsen et al., eds., Harwood Academic Publishers, 1991, pages 114-191) and Andersson (US20120065179) in the final mailed 04/22/2025 was withdrawn per the advisory action mailed 08/14/2025.
The following newly applied 102 rejections constitutes the complete set of rejections and/or objections presently being applied to the instant application.
Response to Arguments
Applicant's arguments filed 07/21/2025 have been fully considered. Applicant’s arguments with respect to claim(s) 70-72, 74-76, 79-84 and 90-92 have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
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) 70-71 and 74 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Wen et al. (Synthesis of Aminocyclopentitols from Chromium Carbene Complex Derived Aminocyclobutanones, J. Org. Chem., 65, pp. 2096-2103, Published 2000).
Wen et al. disclose the immediately below compound 13 (p. 2097, right column).
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Variables R1 and R2 form a polycyclic 6-membered heterocycle containing 1 O and the polycyclic 6-membered heterocycle is substituted with a monocyclic heterocycle (Heterocycles are defined on page 57 of the current specification and include substitutions). Variable R3 is methyl (current claim 74) (unsubstituted alkyl), R4 is a C3 alkyl. This anticipates the claims.
Claim(s) 70-71, 74 and 79 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Hegedus et al. (Synthesis and Exchange Reactions of 1,4,8,11 -Tetraazacyclotetradeca-7(E), 14(E)-diene-5,12-diones, J. Org. Chem. 59, pp. 7779-7784, Published 1994).
Hegedus et al. disclose the below compound 1a-g wherein variables R1 and R2
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form a polycyclic 7-membered heterocycle containing 2 N and the polycyclic 7-membered heterocycle is substituted with two methyl groups (alkyl). Variable R3 is ethyl (current claim 74) (unsubstituted alkyl), R4 is a linear/branched unsubstituted alkyl.
This anticipates the claims.
Allowable Subject Matter
Claims 72, 75-76, 80-84 and 90-92 are 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.
The following is a statement of reasons for the indication of allowable subject matter: The closest prior art to claims 72, 75-76, 80-84 and 90-92 is Xavier Creary (Reaction of Organometallic Reagents with Ethyl Trifluoroacetate and Diethyl Oxalate. Formation of Trifluoromethyl Ketones and alpha-Keto Esters via Stable Tetrahedral Adducts, J. Org. Chem., Vol. 52, No. 22, pp. 5026-5030, Published 1987).
Xavier Creary disclose compound 15 as seen immediately below.
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R1 is -O(C=O)methyl, R2 is an ethoxy/alkoxy, R4 is H, and R3 is ethyl.
Concerning R4, it would not have been obvious to have modified compound 15 of the prior art to arrive at the current invention. There being no motivation to do so.
Compound 15 is not disclosed to have a utility and is only prepared for proof of concept for stabilization of a tetrahedral adduct (p. 5028, right column).
MPEP 2144.09 VI. If the prior art does not teach any specific or significant utility
for the disclosed compounds, then the prior art is unlikely to render structurally similar claims prima facie obvious in the absence of any reason for one of ordinary skill in the art to make the reference compounds or any structurally related compounds. In re Stemniski, 444 F.2d 581, 170 USPQ 343 (CCPA 1971).
Similarly, if the prior art merely discloses compounds as intermediates in the production of a final product, one of ordinary skill in the art would not ordinarily stop the reference synthesis and investigate the intermediate compounds with an expectation of arriving at claimed compounds which have different uses. In re Lalu, 747 F.2d 703, 223 USPQ 1257 (Fed. Cir. 1984).
Moreover, selecting compound 15 as a lead compound having no utility would
not have been obvious nor the modification needed to obtain the inventive compound without a specific teaching.
Yes, substituting a hydrogen for a methyl group may be simple. However, simplicity alone does not render the current compound obvious over the prior art. This simplistic alteration/substitution is considered hindsight reconstruction without a specific teaching. The question becomes, why select the compound taught by Xavier Creary and why remove the hydrogen and replace it with a methyl to achieve the claimed R4
variable and the invention. The reason, the current application says so.
The following art is made of record. Aronovich et al. (Conjugated halogenation of
unsaturated compounds. XI. Direction of addition to α-substituted acrylates, Zhurnal
Organicheskoi Khimii, 11(4), pp. 695-702, Published 1975).
Aronovich et al. disclose the immediately below compound as an intermediate
without a utility (p.696 middle left as compound III).
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R1 is -O(C=O)methyl, R2 is an methoxy/alkoxy, R4 is Cl, and R3 is methyl.
Concerning R4, it would not have been obvious to have modified compound III of the prior art to arrive at the current invention. There being no motivation to do so.
Concerning the pharmaceutical compositions and claims 84 and 90-92, the art presently
being applied does not disclose or fairly suggest pharmaceutical compositions of the claimed compounds.
Conclusion
Any inquiry concerning this communication or earlier communications from the
examiner should be directed to BLAINE G DOLETSKI whose telephone number is (571)272-2766. The examiner can normally be reached M-F 7-4 EST.
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/B.G.D/Examiner, Art Unit 1692
/MEDHANIT W BAHTA/Primary Examiner, Art Unit 1692