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 and Claim Status
Applicant’s election without traverse of Group 1 in the reply filed on 12/10/25 is acknowledged.
The restriction requirement incorrectly listed claim 4 as part of group 2. Claim 4 is part of Group 1. The grouping of claims is as follows: Group 1 – claims 1-2 and 4; Group 2 – claim 3; Group 3 – claims 5-7 and Group 4 – claims 8-10.
Claims 3 and 5-10 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.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 without traverse in the reply filed on 12/10/25.
Applicant’s election without traverse of the species of YC55 in the reply filed on 12/10/25 is acknowledged.
The elected species was found to be free of the prior art. The search was extended in accord with MPEP 803.02.
Claims 1-2 and 4 are being examined.
Priority
The priority information is found in the filing receipt of 8/16/23.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 4/6/23 has been considered by the examiner.
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 1-2 and 4 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.
For the R4 variable of claim 1 the variable ‘n’ is described as ‘n = 2 a 8’. The scope of n is unclear. It is unclear if n can be 2-8 or if ‘2 or 8’ is intended. Dependent claim 4 does not clarify the claim scope.
In claim 1 the R1 variable recites CH3 (L-Ala), CH(CH3)2 (L-Val), CH(CH3)CH2CH3 (L-Ile). First, such description is confusing because the R1 corresponds to a side chain not a complete amino acid. Second the claim refers to both broad and narrow limitations. For example, the stereochemistry of CH3 is not specified so it can be attached in various orientations while L-Ala is suggesting a specific orientation. 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 1 recites the broad recitation CH3, CH(CH3)2 and CH(CH3)CH2CH3, and the claim also recites (L-Ala), (L-Val) and (L-Ile) 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. Dependent claim 4 does not clarify the claim scope.
In claim 1 the R4 variable recites isobutyle, neopentyle, cyclohexylmethyle and n-butyle. The meaning of these terms is unclear as no art-recognized definition for such terms could be found. It is unclear if these are alternate spellings of known terms. It is unclear if such terms are to be identical with the corresponding structure shown. Dependent claim 4 does not clarify the claim scope.
Within claim 1 (R1, R2 and R3, R4, R5, Y, Z and X) and claim 2, various groupings are recited. The last options within the groupings are not separated by the word ‘and’ or the word ‘or’ making the scope of the claims unclear. It is unclear if additional options are possible. It is also unclear if all options are required. For example, claim 2 recites 23 different formulas and it is not clear if each of those formulas is required. In similar fashion, formula I of claim 1 recites ‘1,2’ within the formula. It is unclear if such is to represent ‘1 or 2’ (requiring only a single compound) or represent ‘1 and 2’ (requiring 2 compounds).
Although unclear, the claims have been given the broadest reasonable interpretation consistent with the specification.
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 4 is/are rejected under 35 U.S.C. 103 as being unpatentable over Chu et al. (EP 0360258 03-1990; ‘Chu’) in view of Deber (WO 2018/132920 07-2018; ‘Deber’).
Chu teach antibacterial compounds and teach a goal of improved solubility and improved cell permeability (page 2 lines 15-30). Chu teach the use of ‘A’ as a solubilizing group where ‘A’ can be Gly-Gly-Gly-Ala (page 2 lines 36-55 and claims 3-4). Chu teach that the peptide solubilizing groups can be prepared by any of a variety of recognized methods (page 14 lines 52-54). Chu recognizes the reaction of a carboxyl group of an amino acid with a free amino group (page 10 lines 38-40 and page 15 lines 15-17). In claims 11-12, Chu expressly teach modifying a base compound by attaching the ‘A’ group. Chu also recognizes that the compounds can act as prodrugs (pages 46-47).
Chu does not teach examples using N-substituted amino acids.
Deber teach solubility-increasing tags and membrane insertion tags specifically those that contain 2-6 peptoid residues specifically N-isobutylglycine (NLeu) where the tag can be at the N-terminus (page 3 lines 1-9). Deber specifically teach that to achieve a burrowing property that the peptide includes an acetylated N-terminal residue followed by 3 additional residues (page 18 lines 16-22). Deber teach that methods of peptide synthesis were known (pages 18-19 connecting paragraph).
It would have been obvious to one of ordinary skill in the art before the effective filing date to modify the teachings of Chu because Chu teach antibacterial compounds and teach a goal of improved solubility and improved cell permeability (page 2 lines 15-30). Chu teach the use of ‘A’ as a solubilizing group where ‘A’ can be Gly-Gly-Gly-Ala (page 2 lines 36-55 and claims 3-4). Since Deber teach solubility-increasing tags and membrane insertion tags specifically those that contain 2-6 peptoid residues specifically N-isobutylglycine (NLeu) where the tag can be at the N-terminus (page 3 lines 1-9) and specifically teach that to achieve a burrowing property that the peptide includes an acetylated N-terminal residue followed by 3 additional residues (page 18 lines 16-22) one would have been motivated to modify the Gly-Gly-Gly-Ala peptide of Chu to obtain Ac- N-isobutylglycine - N-isobutylglycine - N-isobutylglycine – Ala. Stated another way, since Chu expressly refers to improved cell permeability one would have been motivated to modify the peptide of Chu (Gly-Gly-Gly-Ala) based on the known modifications that allow for membrane insertion as taught by Deber (N-acetylation and use of N-modified glycine). Such peptide is an intermediate that would then be conjugated to obtain an antibacterial compound (see page 2 lines 36-55 of Chu) for example by creating an amide bond between the C-terminal group of the peptide and the NH2 group (claim 11 of Chu and page 10 lines 38-40 and page 15 lines 15-17 of Chu). One would have had a reasonable expectation of success since methods of synthesizing peptides was known. Chu teach that the peptide solubilizing groups can be prepared by any of a variety of recognized methods (page 14 lines 52-54). Deber teach that methods of peptide synthesis were known (pages 18-19 connecting paragraph).
In relation to claim 1, Ac- N-isobutylglycine - N-isobutylglycine - N-isobutylglycine – Ala as discussed above is such that R5 is CH3, R4, R3 and R2 are CH2CH(CH3)2 and R1 is CH3 and the third residue is an N-substituted alpha amino acid (n is 1).
In relation to claim 4, in claims 11-12, Chu expressly teach modifying a base compound by attaching the ‘A’ group. Chu teach that the peptide solubilizing groups can be prepared by any of a variety of recognized methods (page 14 lines 52-54) which would include preparing the peptide in a composition with a carrier.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RONALD T NIEBAUER whose telephone number is (571)270-3059. The examiner can normally be reached M - F 6:30 - 2:30 EST.
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RONALD T. NIEBAUER
Primary Examiner
Art Unit 1658
/RONALD T NIEBAUER/Examiner, Art Unit 1658