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 with traverse of the species set forth in the reply filed on 8/3/26 is acknowledged. The traversal is on the ground(s) that there are only 3 solvent options available. This is not found persuasive because claim 1 recites ‘wherein the acylation solvent, and the displacement solvent are polar aprotic solvents that are non-reactive to secondary amines’ and such wherein clause is followed by ‘or’. Claim 1 broadly recites ‘acylation wash solvent’ and ‘displacement wash solvent’. Such language does not limit to only 3 solvent options.
The requirement is still deemed proper and is therefore made FINAL.
As noted below, the claim scope is unclear. Applicants state that claims 1-2, 9, 12, 16, 20, 21, 28, 38 and 41 read on the elected species. It appears that claims 31, 33-34 and 36-37 also read on the elected species. Any relevant art that was uncovered during the search for the elected species is cited herein in order to advance prosecution.
Claims 5, 13, 17, 19, 39, 42 and 44 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected species, there being no allowable generic or linking claim. Applicant timely traversed the restriction (election) requirement in the reply filed on 8/3/26.
Claims 3-4, 6-8, 10-11, 14-15, 18, 22-27, 29-30, 32, 35, 40, 43 and 45-47 have been canceled.
Claims 1-2, 9, 12, 16, 20-21, 28, 31, 33-34, 36-38 and 41 are being examined.
Priority
The priority information is provided in the filing receipt of 7/30/24.
Acknowledgment is made of applicant's claim for foreign priority as set forth in the filing receipt. It is noted, however, that applicant has not filed a certified copy (or any copy) of the foreign application as required by 37 CFR 1.55. As such, the priority date for the instant claims is 3/28/24.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 7/23/24 has been being considered by the examiner.
Specification
The disclosure is objected to because of the following informalities:
The disclosure is objected to because it contains an embedded hyperlink and/or other form of browser-executable code specifically page 39 lines 28-32. Applicant is required to delete the embedded hyperlink and/or other form of browser-executable code; references to websites should be limited to the top-level domain name without any prefix such as http:// or other browser-executable code. See MPEP § 608.01.
Appropriate correction is required.
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, 9, 12, 16, 20-21, 28, 31, 33-34, 36-38 and 41 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.
Claim 1 step e recites ‘where the amine group is the terminal amine group in step a)’. Claim 1 step a refers to a terminal amine group. Claim 1 step d refers to an amine group. A terminal amine group is not necessarily the same as an amine group. It is unclear if the claim language is putting a further limitation on the type of product in step d or if the claim language is setting forth starting material for a further repeated step. As such, it is unclear what product is acceptable for step 1d and what components are acceptable for the repeated steps. One would not necessarily equate an elongating step as the same as a reacting a solid support step. None of the dependent claims clarify the claim scope.
Claim 1 recites for example ‘when the acylation solvent is EtOAc’. The first paragraph of page 19 of the specification states that reference to a solvent being a particular solvent means for example that that solvent is about 100% (page 19 section 01039). The specification recognizes that about may mean plus or minus 10% (page 12 section 00101).
Claim 1 recites for example ‘the acylation solvent is not EtOAc’. The first paragraph of page 19 of the specification states that reference to a solvent not being a particular solvent means for example that that solvent is not about 100% (page 19 section 01039). The specification recognizes that about may mean plus or minus 10% (page 12 section 00101).
The specification including claim 13 refers to a ratio of 10:1 where the second component is EtOAc. At a ratio of 10:1 the EtOAc is approximately present at 10%. However, based on the paragraph above ‘not being present’ allows for being present at 10%. The language used and the specification definitions makes it unclear how to determine what solvents are acceptable and in what amounts they are acceptable. Further, references to percentages are unclear because it is not clear if they are on a per weight or per volume basis (page 18 section 00138 merely states ‘In general’ which is not a definition). None of the dependent claims clarifies the claim scope (optional limitations are not further limiting).
Claim 28 recites ‘similar structure’. The term “similar” in claim 28 is a relative term which renders the claim indefinite. The term “similar” is not defined by the claim, the specification does not provide a standard for ascertaining the requisite degree, and one of ordinary skill in the art would not be reasonably apprised of the scope of the invention. The basis for the determination of similar structures (size, charge, hydrophobicity, etc.) is unclear.
Claim 1 recites “wherein the acylation solvent, and the displacement solvent are polar aprotic solvents that are non-reactive to secondary amines” and further refers to “provides for a resin swelling of at least…” and “the acylation wash solvent is able to solubilize 1,2-diisopropylurea”. Claim language that merely states a result to be obtained without providing boundaries on the claim scope (e.g., by not specifying any way to achieve those results) is unclear. The recited functional characteristics do not necessarily occur in all solvents. Thus, one of ordinary skill in the art would not be able to draw a clear boundary between what is and is not covered by the claims. See MPEP 2173.05(g) for more information. The last sentence of MPEP 2173.05(g) recognizes that applicant can amend the claims to recite the particular structure that accomplishes the function. In the instant case, claims 20-21 recites specific solvents.
Claim 38 depends on claim 1 and recites the limitation "the deprotection solvent". There is insufficient antecedent basis for this limitation in the claim since claim 38 and claim 1 do not recite a deprotection solvent.
Although unclear, the claims have been given the broadest reasonable interpretation consistent with the specification.
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, 9, 12, 16, 28, 31, 33-34, 36-38 and 41 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains 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, or for pre-AIA the inventor(s), at the time the application was filed, had possession of the claimed invention.
The MPEP states that the purpose of the written description requirement is to ensure that the inventor had possession, as of the filing date of the application, of the specific subject matter later claimed by him. The courts have stated:
“To fulfill the written description requirement, a patent specification must describe an invention and do so in sufficient detail that one skilled in the art can clearly conclude that “the inventor invented the claimed invention.” Lockwood v. American Airlines, Inc., 107 F.3d 1565, 1572, 41 USPQ2d 1961, 1966 (Fed. Cir. 1997); In re Gostelli, 872 F.2d 1008, 1012, 10 USPQ2d 1614, 1618 (Fed. Cir. 1989) (“[T]he description must clearly allow persons of ordinary skill in the art to recognize that [the inventor] invented what is claimed.”). Thus, an applicant complies with the written description requirement “by describing the invention, with all its claimed limitations, not that which makes it obvious,” and by using “such descriptive means as words, structures, figures, diagrams, formulas, etc., that set forth the claimed invention.” Lockwood, 107 F.3d at 1572, 41 USPQ2d at 1966.” Regents of the University of California v. Eli Lilly & Co., 43 USPQ2d 1398.
The MPEP lists factors that can be used to determine if sufficient evidence of possession has been furnished in the disclosure of the Application. These include “level of skill and knowledge in the art, partial structure, physical and/or chemical properties, functional characteristics alone or coupled with a known or disclosed correlation between structure and function, and the method of making the claimed invention. Disclosure of any combination of such identifying characteristics that distinguish the claimed invention from other materials and would lead one of skill in the art to the conclusion that the applicant was in possession of the claimed species is sufficient.” MPEP § 2163. While all of the factors have been considered, a sufficient amount for a prima facie case are discussed below.
Further, to provide evidence of possession of a claimed genus, the specification must provide sufficient distinguishing identifying characteristics of the genus. The factors to be considered include: a) the scope of the invention; b) actual reduction to practice; c) disclosure of drawings or structural chemical formulas; d) relevant identifying characteristics including complete structure, partial structure, physical and/or chemical properties, and structure/function correlation; e) method of making the claimed compounds; f) level of skill and knowledge in the art; and g) predictability in the art.
(1) Scope of the invention/Partial structure/disclosure of drawings:
Claim 1 recites “wherein the acylation solvent, and the displacement solvent are polar aprotic solvents that are non-reactive to secondary amines” and further refers to “provides for a resin swelling of at least…” and “the acylation wash solvent is able to solubilize 1,2-diisopropylurea”. None of dependent claims 2, 9, 12, 16, 28, 31, 33-34, 36-38 and 41 specifically define both the acylation and displacement solvent.
(2) Level of skill and knowledge in the art/predictability in the art:
The level of skill in the art is high.
(3) Physical and/or chemical properties and (4) Functional characteristics:
Claim 1 and dependent claims 2, 9, 12, 16, 28, 31, 33-34, 36-38 and 41 encompass functional language specifically “wherein the acylation solvent, and the displacement solvent are polar aprotic solvents that are non-reactive to secondary amines” and further refers to “provides for a resin swelling of at least…” and “the acylation wash solvent is able to solubilize 1,2-diisopropylurea”.
When functional claim language is found indefinite as set forth above, it typically lacks an adequate written description under § 112(a), because an indefinite, unbounded functional limitation would cover all ways of performing a function and indicate that the inventor has not provided sufficient disclosure to show possession of the invention.
There is no specific disclosed correlation between structure and function particularly related to what structures are adequate to result in the functions as recited in the claims. It is unclear what structural elements are required for the recited function. One of skill in the art would reasonably conclude that the disclosure fails to provide a representative number of species to describe the genus and that there is a lack of the predictability in the art thus that the applicant was not in possession of the claimed genus.
(5) Method of making the claimed invention/actual reduction to practice:
The specification (beginning in page 24) describes peptoid synthesis. However, mere synthesis of a peptoid does not show solvents with functions as claimed.
The description requirement of the patent statue requires a description of an invention, not an indication of a result that one might achieve if one made that invention. See In re Wilder, 736, F.2d 1516, 1521, 222 USPQ 369, 372-73 (Fed. Cir. 1984) (affirming rejection because the specification does “little more than outlin[e] goals appellants hope the claimed invention achieves and the problems the invention will hopefully ameliorate.”) Accordingly, it is deemed that the specification fails to provide adequate written description for the genus of the claims and does not reasonably convey to one skilled in the relevant art that the inventor(s), at the time the application was filed, had possession of the entire scope of the claimed invention.
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.
Claim(s) 1, 2, 28, 31, 33, 34, 36 and 37 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Connolly et al. (NPL cite 6 of IDS of 7/23/24; ‘Connolly’).
Connolly teach submonomer synthesis of peptoids (title). Connolly teach manual submonomer peptoids synthesis (section 3.1 beginning on page 249) and automated peptoid synthesis (section 3.2 beginning on page 250). Connolly teach a specific submonomer synthesis method (Table 1 on page 251). Connolly teach cleavage of the peptoid (section 5 on page 263).
In relation to the peptoid of claims 1 and 28, Connolly specifically teach peptoids (title and figure 4 on page 248).
In relation to the solid support and synthesis of claims 1, 31 and 34, Connolly teach the use of a Rink amide resin (section 2.1 item 10 on page 246) and teach automated peptoid synthesis (section 3.2 beginning on page 250)
In relation to the reacting, washing , reacting, washing and repeating steps of claim 1-2, page 251 of Connolly teach such steps and specifically teach the use of bromoacetylation.
In relation to the solvent of claim 1, Connolly teach the use of DMF (page 251). Although unclear, DMF is interpreted as meeting the limitation. Specifically, DMF is a polar aprotic solvent non-reactive to secondary amines (see first wherein clause after step e of claim 1).
In relation to the cleavage of claim 33, Connolly teach cleavage of the peptoid (section 5 on page 263).
In relation to claims 36-37, Connolly teach swelling and deprotection (page 251).
Claim(s) 1-2, 9, 12, 16, 20-21, 28, 31, 33-34, 36-38 and 41 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Clapperton et al. (‘Green and sustainable solvents for solid-phase peptoid synthesis’ ACS Sustainable Chem Eng v11 2023 pages 13024-13032; ‘Clapperton’).
The first page (bottom right) states that Clapperton was published August 21 2023. As set forth in the priority section above, the priority date for the instant claims is 3/28/24. Further, as set forth in MPEP 2153.01(a) “If, however, the application names fewer joint inventors than a publication (e.g., the application names as joint inventors A and B, and the publication names as authors A, B and C), it would not be readily apparent from the publication that it is an inventor-originated disclosure and the publication would be treated as prior art”. In the instant case, the application names joint inventors and the publication names 4 authors.
Clapperton teach various peptoid synthesis methods (Table 1 page 13028 and Table 2 page 13029). Clapperton teach the use of Rink amide resin (page 13025 first paragraph of column 2). Clapperton teach that particular peptides were synthesized (figure 3 on page 13027). Table 1 of Clapperton teach specific methods including method 4 and 6 (page 13028).
In relation to the peptoid of claims 1 and 28, figure 3 of Clapperton teach a specific peptoid that was synthesized (Npe6).
In relation to the solid support and synthesis of claims 1, 31 and 34, Clapperton teach the use of Rink amide resin (page 13025 first paragraph of column 2) and teach manual solid phase peptoid synthesis (table 1 title).
In relation to the reacting, washing , reacting, washing and repeating steps of claim 1-2, Figure 1 of Clapperton specifically shows such steps. Table 2 and figure 1 show the use of BrAc.
In relation to the solvents of claims 1, 9 , 12, 16 and 20, Clapperton teach specific solvents for specific steps (for examples methods 4 and 6 of Table 1). As shown in Table 1, the acylation and acylation wash solvent are not identical for methods 4 and 6.
In relation to claim 21, the first option reads on method 4 of Clapperton and the 5th option reads on method 6 of Clapperton (see Table 1).
In relation to the solvents and steps of claims 1 and 31, Clapperton teach manual solid phase peptoid synthesis (Table 1 page 13028, specifically methods 4 and 6 and Table 2 page 13029).
In relation to the cleavage of claim 33, Clapperton teach cleavage (Table 1).
In relation to claims 36-38 and 41, Clapperton teach swelling and deprotection and use of the solvent EtOAc (Table 2).
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.
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) 1-2, 9, 12, 16, 20-21, 28, 31, 33-34, 36-38 and 41 is/are rejected under 35 U.S.C. 103 as being unpatentable over Connolly et al. (NPL cite 6 of IDS of 7/23/24; ‘Connolly’) in view of Pawlas et al. (‘Regreen SPPS: enabling circular chemistry in environmentally sensible solid phase peptide synthesis’ Green Chem v21 2019 pages 5990-5998; ‘Pawlas’) in view of Zuckermann et al. (US 5,877,278; cited with IDS 7/23/24; ‘Zuckermann’).
Connolly teach submonomer synthesis of peptoids (title). Connolly teach manual submonomer peptoids synthesis (section 3.1 beginning on page 249) and automated peptoid synthesis (section 3.2 beginning on page 250). Connolly teach a specific submonomer synthesis method (Table 1 on page 251). Connolly teach cleavage of the peptoid (section 5 on page 263). Connolly teach that peptoids have shown good solubility in common solvents (section 1 on page 242). On page 251 Connolly teach the use of DMF as the solvent.
Connolly does not teach the use of DMSO or EtOAc as solvents.
Pawlas teach that DMF has been deemed undesirable from the green chemistry standpoint as it is a hazardous solvent (page 5991 first complete paragraph). Pawlas teach a goal of greener methods of peptide synthesis in which inexpensive ethyl acetate (EtOAc) and dimethylsulfoxide (DMSA) are used as solvents (abstract). Pawlas teach the use of DMSO/EtOAc at 1:9 for synthesis and at a ratio of 1:49 for wash steps teaching that the amount of DMSO was adjusted based on the solubility needs at various steps (page 5992 first paragraph of column 2 and scheme 1). Pawlus teach cost-efficiency of inexpensive starting materials and solvents with synthetic efficiency along with recycling (page 5994 last paragraph).
Zuckermann teach solid phase methods for the synthesis of peptoids (abstract). Zuckermann specifically teach the use of dimethylsulfoxide as a solvent (column 11 lines 51-53). Zuckermann teach solubility of compounds in DMSO (column 27 lines 24-25 and 59-60). Zuckermann also recognizes the use of ethyl acetate as a solvent (column 67 lines 1-4).
It would have been obvious to one of ordinary skull in the art before the effective filing date to modify the teachings of Connolly because Connolly teach that peptoids have shown good solubility in common solvents (section 1 on page 242) and teach the use of DMF as the solvent (page 251). Since Pawlas teach that DMF has been deemed undesirable from the green chemistry standpoint as it is a hazardous solvent (page 5991 first complete paragraph) and teach methods of peptide synthesis in which inexpensive ethyl acetate (EtOAc) and dimethylsulfoxide (DMSA) are used as solvents (abstract) one would have been motivated to replace DMF in the method of Connolly (page 251). Since Pawlas teach the use of DMSO/EtOAc at 1:9 for synthesis and at a ratio of 1:49 for wash steps teaching that the amount of DMSO was adjusted based on the solubility needs at various steps (page 5992 first paragraph of column 2 and scheme 1) one would have been motivated to use such solvents at various ratios. Further, Zuckermann specifically teach the use of dimethylsulfoxide as a solvent (column 11 lines 51-53) in peptoid synthesis. One would have had a reasonable expectation of success since Connolly teach that peptoids have shown good solubility in common solvents (section 1 on page 242). Pawlus teach cost-efficiency of inexpensive starting materials and solvents with synthetic efficiency along with recycling (page 5994 last paragraph) when using DMSO/EtOAc.
In relation to the peptoid of claims 1 and 28, Connolly specifically teach peptoids (title and figure 4 on page 248). Further, Zuckermann teach synthesis of peptoids (example 11 (column 28).
In relation to the solid support and synthesis of claims 1, 31 and 34, Connolly teach the use of a Rink amide resin (section 2.1 item 10 on page 246) and teach automated peptoid synthesis (section 3.2 beginning on page 250)
In relation to the reacting, washing , reacting, washing and repeating steps of claim 1-2, page 251 of Connolly teach such steps and specifically teach the use of bromoacetylation.
In relation to the solvents of claims 1, 9 , 12, 16, 20, 21, 38 and 41, Pawlas teach the use of DMSO/EtOAc at 1:9 for synthesis and at a ratio of 1:49 for wash steps teaching that the amount of DMSO was adjusted based on the solubility needs at various steps (page 5992 first paragraph of column 2 and scheme 1). Although unclear, a 1:49 ratio clearly meets amounts as recited in section 00139 (page 19) of the specification (for example 95%).
In relation to the cleavage of claim 33, Connolly teach cleavage of the peptoid (section 5 on page 263).
In relation to claims 36-37, Connolly teach swelling and deprotection (page 251).
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
Prosecution Insights