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 Claims
Claims 1-40 are pending in the instant application.
Priority
This application claims priority to provisional applications 63/433,339, filed 12/16/2022 and 63/350,545, filed 06/09/2022.
Information Disclosure Statement
The Information Disclosure Statements (IDS) filed 08/10/2023, 11/16/2023 and 11/17/2023 were considered by the Examiner.
Restriction/Election
Applicant’s election with traverse of “compound 9, N-[(2S)-3-cyclopropyl-1-({(2)-4-hroxy-3-oxo-1-[(3)-2-oxopiperidin-3-yl]butan-2-yl)amino)-1- oxopropan-2-yl]-7-fluoro-1H-indole-2-carboxamide” to prosecute the invention of Group I, drawn to a compound of Formula (I) in the reply filed on April 16th, 2026 is acknowledged.
Applicant has traversed the restriction requirement as Applicant believes that it would not be unduly burdensome to perform a search on all of the claims together in the present application. However, this is not persuasive. As provided in the restriction requirement, the groups fall into distant classes, requiring separate search and consideration.
Applicant states claims 1-3, 5, 9-10, 12, 14-16 and 18 read on the elected species; claims 19-40 are withdrawn as being drawn to the nonelected invention of Group II, drawn to a method of inhibiting a Baltimore Group IV RNA virus with a compound of Formula (I) and claims 4, 6-8, 11, 13 and 17 are withdrawn as being drawn to a nonelected species.
As per MPEP 803.02, the examiner will determine whether the entire scope of the claims is patentable. Applicants' elected species of the compound 9, N-[(2S)-3-cyclopropyl-1-({(2)-4-hroxy-3-oxo-1-[(3)-2-oxopiperidin-3-yl]butan-2-yl)amino)-1- oxopropan-2-yl]-7-fluoro-1H-indole-2-carboxamide appears allowable. Therefore, according to MPEP 803.02: should the elected species be found allowable, the examination of the Markush-type claim will be extended. If the examination is extended and a non-elected species found not allowable, the Markush-type claim shall be rejected and claims to the nonelected invention held withdrawn from further consideration. The examination of the Markush-type claims has been extended to include the scope of claims 9, 14 and 18, as well as structural species:
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Since a non-elected species has been found not allowable, examination has been limited to claims directed to the elected species, which are presently claims 1-3, 5, 9-10, 12, 14-16 and 18. Claims 1-3, 5, 9-10, 12, 14-16 and 18 have been examined to the extent that they are readable on the elected embodiment and the above identified nonelected species. Since the nonelected species has been found not allowable, subject matter not embraced by the elected embodiment or the above identified nonelected species is therefore withdrawn from further consideration.
Claims 4, 6-8, 11, 13, 17 and 19-40 are withdrawn from further consideration by the examiner, 37 CFR 1.142(b), as being drawn to a non-elected invention or species. Election was made with traverse in reply filed April 16th, 2025.
Claim Objections
Claims 9, 14 and 18 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.
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.
Claim(s) 1-3, 5, 10, 12 and 15-16 is/are rejected under 35 U.S.C. 103 as being unpatentable over Hoffman et al (WO 2005/113580, published December 1st, 2005, as cited on the IDS dated 08/10/2023) in view of Wermuth et al (The Practice of Medicinal Chemistry. London ; Academic Press, 1996) and Patani et al (Chem. Rev. 1996,96, 3147−3176).
Determining the scope and contents of the prior art. (See MPEP § 2141.01)
Hoffman teaches the following compound (page 80, Example 5):
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This compound is nearly embraced by instant formula (I), wherein R1 is each -H, R3 is -CH(CH3)2-, R4 is -H, X is -CH2- and Y is absent.
Ascertainment of the differences between the prior art and the claims. (See MPEP § 2141.02)
The closest structure instantly claimed to the compound taught by Hoffman is:
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The only difference between the instantly claimed compound and compound as taught by Hoffman is that the instantly claimed compound has a fluorine in the R2 position, where the compound taught by Hoffman has a hydrogen.
Finding of prima facie obviousness --- rationale and motivation (See MPEP § 2142-2143)
Replacing the hydrogen in the compound as taught by Hoffman with fluorine would have been obvious to a person having ordinary skill in the art in view of Wermuth. Wermuth teaches that there is fluorine and hydrogen isosterism. Wermuth teaches that fluorine often mimics an atom of hydrogen (page 226). Wermuth teaches that both hydrogen and fluorine are chemically inert and of small size. Wermuth teaches that from the steric point of view, fluorine resembles hydrogen. Further, Wermuth teaches that the hydrogen to fluorine isosterism often serves to five analogues that are more resistant to metabolic degradation, for example CF3 is biostable, whereas CH3 is easily oxidized (Page 227).
Further, Patani teaches that the substitution of hydrogen by fluorine is one of the more commonly employed monovalent isosteric replacements (page 3149, left column, paragraph 4). Patani also teaches that the steric parameters for hydrogen and fluorine are similar (page 3149, left column, paragraph 4). Further, Patani teaches that the ability of fluorine to replace hydrogen is an effective method of exploring the affinity of an agent to the target site by virtue of its greater electronegativity while other parameters such as steric size and lipophilicity are maintained (page 3150, left column, paragraph 2).
Further, Hoffman teaches that the compound nearly embraced by instantly claimed general formula (I) has the same utility as the instantly claimed compounds. Hoffman teaches that the above compound is useful in the treatment of coronavirus and SARS related infections (claims 14-18).
Regarding claim 1, as Wermuth and Patani teach that hydrogen and fluorine are similar and commonly replaced in the art and Hoffman teaches isosteric compounds for the same utility as instantly claimed, one of ordinary skill in the art, absent a showing of unexcepted results, would have been motivated to replace the hydrogen as taught in the compound by Hoffman with fluorine to arrive at the compound as instantly claimed. Applicant can obviate the rejection with a showing of unexpected results, see MPEP 716.02. The burden is on the Applicant to establish that the results are in fact unexpected, unobvious, and of statistical and practical significance.
Regarding claim 2, as seen above, R1 is -H.
Regarding claim 3, as seen above, R2 being -F has been rendered obvious.
Regarding claim 5, R3 is -CH(CH3)2.
Regarding claims 10 and 12, R4 is H.
Regarding claims 15-16, X is -CH2-.
Conclusion
No claim is allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Anna Grace Kuckla whose telephone number is (703)756-5610. The examiner can normally be reached Monday-Friday 7:30-5.
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/A.G.K./Examiner, Art Unit 1626
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699
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