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 (i.e., claims 1-8 and 10-12), and Species 1: conjugate formula (I), wherein L is
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, R is H and A is Ac-K(Aib)SHLRKLRKRLL-NH2; in the reply filed on 06/23/2026 is acknowledged.
Claims 13-21 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention there being no allowable generic or linking claim. Likewise claims 5 and 7 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species; there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 06/23/2026.
Applicant’s elected species of conjugate of formula (I) (i.e., SEQ ID NO: 50) was searched and found to be free of the art. Please also note that the search was expanded to include conjugates of formula (I) represented by SEQ ID NOs: 52-56.
The species search was extended to include additional species within the genus of claim 1, comprising the elected species for variable L (i.e.,
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), wherein R is H. Art was found and the rejections were made accordingly.
However, the search was not extended to include additional species of conjugates as recited in claim 11, because there were several species of conjugates which are not encompassed within the elected species of conjugate of formula (I). For instance, SEQ ID NOs: 19-21, 28-29, 35-37 and 54. Because the scope of claim 11 is unclear, the species search was not extended to all of those listed in claim 11. Clarification is required before a novelty determination can be made.
Claims 1-8 and 10-21 are pending, and claims 1-4, 6, 8 and 10-12 are under examination.
Claim Status
Claims 1-21 were originally filed on 01/05/2024.
The amendment filed on 09/30/2024, cancelled claim 9 and amended claims 1, 8, 10, 12-13, and 16-21.
Priority
The present application claims status as a 371 (National Stage) of PCT/US2022/073561 filed 07/08/2022 and claims the benefit under 35 U.S.C 119 (e) to U.S. Provisional Application No. 63/243,629 filed 09/13/2021, and to U.S. Provisional Application No. 63/219,488 filed 07/08/2021. Applicant’s claim for the benefit of a prior-filed application under 35 U.S.C 119 (e) or under 35 U.S.C 120, 121, or 365 (c) is acknowledged.
Information Disclosure Statement
The IDS filed on 04/05/2024 has been considered.
Claim Interpretation
For claim 1, regarding the scope of variable A in conjugate formula (I), “a peptide or a derivative thereof” it is noted that the instant specification does not define what constitutes a derivative thereof. Instead, the specification teaches examples of the peptides and the derivatives thereof (see instant spec, pg. 15, para[0082], Table 1).
Pursuant to MPEP 2111.01, under a broadest reasonable interpretation, words of the claim must be given their plain meaning, unless such meaning is inconsistent with the specification. The plain meaning of a term means the ordinary and customary meaning given to the term by those of ordinary skill in the art at the time of the invention. Merriam-Webster Dictionary defines “derivative” as a substance that can be made from another substance (see Merriam-Webster Dictionary, definition 4b, at https://www.merriam-webster.com/dictionary/derivative, retrieved on 08/18/2026). As such, the scope of variable A (i.e., a peptide or a derivative thereof) is interpreted as any peptide (i.e., any structure) that can be made from another peptide and exhibits the function of being retained in the lungs.
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.
1. Claim 11 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 11 recites the limitation "selected from any one of SEQ NOs: 14-55" in line 1. There is insufficient antecedent basis for this limitation in the claim. Claim 11 depends upon claim 1, which is drawn to a conjugate formula (I):
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,
Wherein
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and R is H or phenyl, and A is a peptide designed to be retained in the lungs or a derivative thereof.
However, variable A, in SEQ ID NOs: 19-21, 28-29, 35-37 and 57, is conjugated to 3,5-diamino-N-(N'-benzylcarbamimidoyl)-6-chloropyrazine-2-carboxamide which corresponds to
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.
Therefore, the structure shown within the dotted square
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is not encompassed by any of the options for variable L as recited in independent claim 1. Therefore claim 11 is indefinite because a conjugate of formula (I) is not represented by any one of SEQ ID NOs: 14-55, since SEQ ID NOs: 19-21, 28-29, 35-37 and 54 lack antecedent basis.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
2. Claim 2 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 2 recites “…wherein the peptide comprises ASHLRKLRKRL (SEQ ID NO: 1) or a derivative thereof.” The scope of the term “derivative thereof” encompasses any peptide that can be derived from SEQ ID NO: 1. Therefore the term is extensively broad and as a result it fails to further limit parent claim 1. Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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.
103 - KSR Examples of 'Rationales' Supporting a Conclusion of Obviousness
(Consistent with the "Functional Approach" of Graham)
Further regarding 35 USC 103(a) rejections, the Supreme Court in KSR International Co. v. Teleflex Inc., 550 U.S. 398, 127 S. Ct. 1727, 82 USPQ2d 1385, 1395-97 (2007) (KSR) identified a number of rationales to support a conclusion of obviousness which are consistent with the proper "functional approach" to the determination of obviousness as laid down in Graham. The key to supporting any rejection under 35 U.S.C. 103 is the clear articulation of the reason(s) why the claimed invention would have been obvious. The Supreme Court in KSR noted that the analysis supporting a rejection under 35 U.S.C. 103 should be made explicit.
Exemplary rationales that may support a conclusion of obviousness include:
(A) Combining prior art elements according to known methods to yield predictable results;
(B) Simple substitution of one known element for another to obtain predictable results;
(C) Use of known technique to improve similar devices (methods, or products) in the same way;
(D) Applying a known technique to a known device (method, or product) ready for improvement to yield predictable results;
(E) "Obvious to try" - choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success;
(F) Known work in one field of endeavor may prompt variations of it for use in either the same field or a different one based on design incentives or other market forces if the variations are predictable to one of ordinary skill in the art;
(G) Some teaching, suggestion, or motivation in the prior art that would have led one of ordinary skill to modify the prior art reference or to combine prior art reference teachings to arrive at the claimed invention.
Note that the list of rationales provided is not intended to be an all-inclusive list. Other rationales to support a conclusion of obviousness may be relied upon by Office personnel.
Also, a reference is good not only for what it teaches by direct anticipation but also for what one of ordinary skill in the art might reasonably infer from the teachings. (In re Opprecht 12 USPQ 2d 1235, 1236 (Fed Cir. 1989); In re Bode 193 USPQ 12 (CCPA) 1976).
3. Claims 1-4, 6, 8, 10, and 12 are rejected under 35 U.S.C. 103 as being unpatentable over US 8,034,762 B2 Date of Patent: Oct. 11, 2011 (herein after “Vitek”), in view of Yao et al. Am J Respir Cell Mol Biol. 2016. Vol 55, Issue 2, pp. 159-169 (herein after “Yao”); Schoenberger et al., Expert Opin. Ther. Patents (2013) 23(10), pp. 1383-1389 (herein after “Schoenberger”); Li et al., J. Membrane Biol. 1987. 95:171-185 (herein after “Li”); and Harmuth et al., 2003., DDT Vol. 8, No. 24, pp. 1128-1137 (herein after “Harmuth”).
Regarding claim 1, Vitek is in the field of novel ApoE peptide derivatives and ApoE-protein transduction domain conjugates useful for treating disorders (see front pg. abstract). More specifically, Vitek teaches analogs and derivatives of COG 133, a truncated peptide comprised of residues 133-149 of ApoE (see column 9, lines 33-35). Vitek adds that the ApoE analogs include, without limitation, naturally occurring or synthetic ApoE polypeptides or biologically active fragments, additionally the ApoE peptides may exhibit different properties relative to human ApoE, including stability, phospholipid binding, altered specific activity and the like (see column 9, lines 59-60 and 65-67). As discussed in the “Claim Interpretation” section above, the peptide or derivative thereof encompasses any peptide (i.e., any structure) that can be made from another peptide. Thereby Vitek’s teachings read on a conjugate comprising a peptide or a derivative thereof.
With respect to the function (i.e., designed to be retained in the lungs) of the claimed peptide or derivative thereof:
Yao teaches the emerging roles of Apolipoprotein E and Apolipoprotein A-1 in the pathogenesis and treatment of lung disease (see pg. 159, Title). Yao discusses that these emerging roles are based on the ApoE and ApoA-I ability to suppress inflammation, oxidative stress, and tissue remodeling, and to promote adaptive immunity and host defense (see pg. 159, abstract). Yao also teaches that ApoE containing lipoprotein particles are internalized into cells by low density lipoprotein receptors (LDLRs); ApoA-I and ApoE facilitate the transport of cholesterol, triglycerides, and phospholipids between plasma and cells (see pg. 159, abstract). Both apoE and apoA-I are expressed by lung cells, which allows apoE/LDLR- and apoA-I/ABCA1- dependent pathways to modulate normal lung health and the pathogenesis of respiratory diseases, including asthma, acute lung injury, cancer, emphysema, pulmonary fibrosis, and pulmonary hypertension (see pg. 159, abstract). The literature reviewed by Yao reports that that apolipoprotein mimetic peptides corresponding to the LDLR-binding domain of apoE or the class A amphiphatic α-helical structure of apoA-I have anti-inflammatory and antioxidant effects that attenuate the severity of lung disease in murine models (see pg. 159, abstract).
The combined teachings of Vitek and Yao are pertinent, because an ordinary skilled artisan would have been motivated with reasonable expectation of success to modify ApoE truncated peptides corresponding to the LDLR binding domain of ApoE, to arrive at a peptide or derivative thereof, that binds and interacts with the LDLR lung receptor. An ordinary skilled artisan would have had a reasonable expectation of success given that it was known that ApoE is expressed in the lungs. Thus, the combined teachings of Vitek and Yao read on variable A of conjugate formula (I).
However, Vitek does not expressly teach a conjugate of formula (I):
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or a pharmaceutical acceptable salt thereof, wherein: variable L in formula (I) is
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and R is H (i.e., Applicant’s elected species).
Schoenberger teachings pertain to the epithelial sodium channel (ENaC) inhibitor known as amiloride (i.e.,
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) and its inclusion in six different patents (i.e., WO2012035158(A1); WO2009074575(A2); WO2011028740(A1); WO2009150137(A2); WO2011079087(A1); WO2008135557(A1)); wherein the inhibitor has been modified to increase structural diversity in a sterically tolerant region (see pg. 1383, abstract). The patented ENaC inhibitors resemble the classical ENaC blocker amiloride; but include modifications to i) enhance potency of ENaC inhibition, ii) reduce epithelial permeability, and iii) broaden applicability in order to be used as potential drugs for cystic fibrosis (see pg. 1383, abstract) and graphical depiction at pg. 1385, reproduced herewith for convenience.
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Li’s teachings pertain to the structure-activity relationship of amiloride analogs as blockers of epithelial sodium channels, in particular side chain modifications (see pg. 171, Title). Li adds that the 2-position side chain structure of amiloride was varied in order to obtain structure/rate constant relationships (see pg. 172, abstract); wherein hydrophobic chain elongations increase the stability of the blocking complex (lowered off-rate) (see pg. 172, abstract). Li’s Table 1 depicts the structure, method of preparation and blocking rate constants of amiloride and some of its analogs with modifications at the side chain terminal (see pg. 174, Table 1). It is noted that the R group in analog number 15 includes a modification wherein one of the NH2 side chains has been modified to include N(C2H5)2, an enlarged amidino moiety which includes four alkyl substituents on the terminal nitrogen atom (i.e.,
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) (see pg. 173, right column, last paragraph; and pg. 174, Table 1, Analog Number 15). Li indicates that although the basicity of Analog 15 is somewhat reduced, it does not have a pKa below 7.5; therefore, the degree of protonation during measurements at pH 5.5 is nearly the same as with amiloride (see pg. 173, right column, last paragraph). Hence, a decrease in Kon would be due to changes in structure-related interactions with the receptor site on the Na channel; however, the Koff constant is nearly the same as amiloride (see pg. 175, left column, last paragraph). Li adds that the encounter complex is modeled distinct from the blocking complex, since analog 15 has a decrease on rate compared to amiloride, but no appreciable change in the off rate (see pg. 181, left column, third paragraph, and Fig. 3 at pg. 180). Therefore, a change in the encounter complex stability does not imply a change in the blocking complex stability and vice versa (see pg. 180, left column, third paragraph). Thus, the combined teachings of Schoenberg and Li are pertinent because before the effective filing date of the claimed invention, molecular platforms for epithelial sodium channel (ENaC) modulators were known, wherein amiloride, the classical ENaC blocker, comprised modifications that included substitutions at the side chain of position 2 in the six-member ring. As indicated by the arrow and dotted squares in the adjacent image
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. Also, before the effective filing date of the claimed invention, it was known that amiloride analogs comprising four alkyl substituents on the terminal nitrogen atom of the side chain at position 2 of the 6 membered ring, does not interfere with amiloride’s function of blocking Na channels.
Furthermore, pursuant to MPEP 2144.09 (I), A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. Additionally, per MPEP 2144.09 (II) compounds which are homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977).
In the instant case, Li’s amiloride analog number 15, has a close structural similarity and utility to a conjugate of formula (I), wherein the pentyl chain (i.e.,
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) of the L variable (i.e.,
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) is conjugated to amiloride thereby resulting in a modified amiloride with five alkyl substituents at one of the terminal nitrogens in the side chain of position 2 of the 6 membered ring. Thereby resulting in an amiloride with a structure as depicted in the adjacent image
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.
With respect to the five-membered ring made of two carbon atoms and three nitrogen atoms (C₂H₃N₃) (i.e., triazole
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) which is present in variable L:
Hartmuth writes about the growing impact of click chemistry on drug discovery (see pg. 1128, Title). Hartmuth teaches that click chemistry uses carbon–heteroatom bond-forming connection chemistry (see pg. 1127, left column, second paragraph); and elaborates that cycloaddition reactions, especially from the 1,3-dipolar family, but also hetero-Diels-Alder reactions are relevant for drug discovery (see pg. 1129, left column, last paragraph). Hartmuth emphasizes that Huisgen’s 1,3-dipolar cycloaddition of alkynes and azides yielding triazoles is, undoubtedly, the premier example of a click reaction; since azides and alkynes are easy to install, and, despite being among the most energetic species known, they are also among the least reactive functional groups in organic chemistry (see pg. 1129, right column, second paragraph). Hartmuth also teaches that given the dramatic rate acceleration of the azide–alkyne coupling event under copper-(I) catalysis, the beneficial effects of water, this unique connection process seems to be redefining the concept of a prefect reaction as depicted in figure 1b, reproduced below for convenience (see pg. 1130).
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Thus, the ready availability of the staring materials; the absence of protecting groups and a complete conversion and selectivity for the 1,4-disubstituted 1,2,3-triazole; structural uncertainties do not exist, rendering purification unnecessary (see pg. 1129, right column, third and fourth paragraphs). Moreover, triazoles cannot be cleaved hydrolytically or otherwise, and are almost impossible to oxidize or reduce (see pg. 1130, left column, first paragraph). The teachings of Hartmuth are pertinent because before the effective filing date of the claimed invention, it was known to employ click chemistry more specifically cycloaddition reactions in drug discovery processes thereby forming a connection between two or more compounds of interest. As such, the combined teachings of Vitek, Li and Hartmuth are suggestive of a conjugate of formula (I) wherein variable A (i.e., a peptide designed to be retained in the lungs or a derivative thereof) is conjugated to a modified amiloride via cycloaddition reaction involving azide and alkyne groups.
From the teachings of the references, the Examiner recognizes that it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to combine the teachings of Vitek, Yao, Schoenberger, and Li to arrive at the claimed conjugate of formula (I). One of ordinary skill in the art would have been motivated to do so because it was known that:
-ApoE, analogs and derivatives thereof may exhibit different properties including stability, phospholipid binding and altered specific activity, relative to unmodified ApoE, as taught by Vitek;
-apolipoprotein mimetic peptides, corresponding to the LDLR-binding domain of ApoE or the class A amphiphatic α-helical structure of ApoA-I, have anti-inflammatory and antioxidant effects that attenuate the severity of lung disease, as taught by Yao; and
-click chemistry involving cycloaddition of alkynes and azides is a technique widely employed in drug discovery because it allows the connection of two compounds via triazole linkage which is not susceptible to cleavable, oxidation or reduction, as taught by Hartmuth.
One of ordinary skill in the art would have had a reasonable expectation of success in achieving the claimed conjugate of formula (I) given that -amiloride, the epithelial sodium channel inhibitor, has been previously modified to enhance potency of inhibition, reduce epithelial permeability and/or broaden its applicability as a potential drug for cystic fibrosis, as taught by Schoenberger. Given that an amiloride analog with four alkyl substituents on the terminal nitrogen atom, had a markedly reduced on-rate constant (i.e., Kon or delay attachment to the receptor due to structural interaction), but nearly the same Koff as unmodified amiloride (i.e., blocking complex or performed function not affected by structural change), as taught by Li, and given that the roles of ApoE in the pathogenesis and treatment of lung disease had already been documented and tested by studies in murine models as taught by Yao.
As such, the combined teachings of the Vitek, Yao, Schoenberger, and Li would support the instantly claimed invention by constituting some teaching, suggestion, or motivation in the prior art that would have led one of ordinary skill to modify the prior art reference or to combine prior art reference teachings to arrive at the claimed invention; and/or combining prior art elements according to known methods to yield predictable results; and/or the use of known technique to improve similar devices (methods, or products) in the same way, pursuant to KSR.
Regarding claims 2-3, Vitek teaches examples of ApoE peptide mimetics, which include without limitation Ac-ASHLRKLRKRLL-NH2 (apoe138-149) represented by SEQ ID NO: 44 (see column 11, lines 44-45). Thereby Vitek’s SEQ ID NO: 44 constitutes wherein the instantly claimed peptide comprises ASHLRKLRKRL (SEQ ID NO: 1) or a derivative thereof, and wherein the peptide derivative is acetylated.
Regarding claim 4, Vitek’s SEQ ID NO: 44 comprises SHLRKLRKRLL from position 2-11; thereby constituting wherein the peptide comprises SEQ ID NO: 58 (i.e., SHLRKLRKRLL) as recited in instant claim 4.
Regarding claim 6, Vitek’s SEQ ID NO: 44 represents the sequence Ac-ASHLRKLRKRLL-NH2, Vitek’s peptide also comprises an additional leucine on the C-terminus. Thereby Vitek’s SEQ ID NO: 44 reads on a peptide comprising instant SEQ ID NO: 1 (i.e., ASHLRKLRKRL) with an additional L at the C-terminus.
Regarding claims 8 and 10, Schoenberg teaches that NOVARTIS Series VI represents bivalent ligands, wherein two amiloride or amiloride like molecular fragments are presented on either side of a linker, which can be varied in lengths and flexibility (see pg. 1385, right column, first paragraph). Schoenberg teachings are being interpreted as the attachment of a peptide via an amino acid side chain at either the C or to the N-terminus of a modified amiloride. Additionally, as previously discussed, Harmuth teaches that click chemistry uses carbon-heteroatom bond-forming connection chemistry (see pg. 1129, left column, third paragraph), and also depicts the schematic reaction that forms a triazole and chemically joins two groups R1 and R2 (see pg. 1130, Fig. 1b). Therefore, an ordinary skilled artisan would have been motivated with reasonable expectation of success to bind a peptide to a modified amiloride via the side chain of an amino acid residue at either the N or the C terminus of the peptide.
Regarding claim 12, Vitek’s invention includes a pharmaceutical composition comprising at least one of the ApoE analogs described (see column 4, lines 49-51) in combination with a pharmaceutically acceptable carrier (see column 16, lines 24-25).
In light of the foregoing discussion, the Examiner concludes that the subject matter defined by the above claims would have been obvious to one of ordinary skill in the art within the meaning of 35 U.S.C. 103. Therefore, the invention as a whole would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention, as evidenced by the references discussed above.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to CLAUDIA E ESPINOSA whose telephone number is (703)756-4550. The examiner can normally be reached Monday-Friday 9:30-5:30 EST.
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/CLAUDIA ESPINOSA/Patent Examiner, Art Unit 1654
/JEANETTE M LIEB/Primary Examiner, Art Unit 1654
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