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 .
Objections/Rejections Withdrawn
Rejections and/or objections not reiterated from previous Office Actions are hereby withdrawn. The following rejections and/or objections are either reiterated or newly applied, and constitute the complete set presently being applied to the instant application.
Response to Arguments
Applicant’s arguments filed 12/23/25, with respect to the claim rejections made under 35 U.S.C. 112(b), have been fully considered and are persuasive. The rejections have been withdrawn.
Applicant's arguments filed 12/23/25, with respect to the claim rejections made under 35 U.S.C. 102 and double patenting, have been fully considered but they are not persuasive.
Regarding the rejections made under 35 U.S.C. 102, and by extension 103, Applicant’s position is that the fluorous compounds described by Mizuno do not meet the limitations of claim 1 as they are not soluble in organic solvents. However, this contradicts the teachings of Mizuno, wherein the fluorous compound/anchor described is soluble in organic phase as the addition of a fluorous phase results in the partitioning of the fluorous anchor out of the organic phase and into the fluorous phase. In other words, to partition out of the organic phase, or move from the organic phase and into the fluorous phase, the fluorous compound/anchor should necessarily have been soluble in the organic phase. Moreover, simply because fluorous compounds/anchors may exhibit improved solubility in fluorous solvents does not negate their solubility in organic or apolar solvents. Thus, the rejection has been maintained/modified herein.
Regarding the double patenting rejections, the claims as currently recited are open to the presence or absence of protecting groups; therefore, the argument that ‘088 recites the lack of protecting groups, which makes it patentably distinct from the instant application, is not persuasive. The rejection has been maintained/modified herein.
Claim Status
Claims 1-4, 6-17, 19-20, and 22-23 are currently pending under examination. Claims 1-2, 4, 7, 9, 12, 14, and 16-17 are currently amended. Claims 3, 6, 8, 10-11, 13, 15, 16, and 17 were previously presented. Claims 5, 18, and 21 are cancelled. Claims 22 and 23 are new.
Priority
The application is 371 national stage entry of PCT/FR2019/000218, filed on 12/23/2019, which claims priority to FR1874091, filed 12/24/2018. Applicants have claimed the effective date of 12/24/2018 based on the FR1874091 although no translation has been made of record.
Maintained/Modified - Claim Objections
Claim 19 is are objected to because of the following informalities: The claim recites “1-ethyl-3-(3-dimethyl-aminopropyl carbodiimide” in lines 3 and 4, but should read as “1-ethyl-3-(3-dimethyl-aminopropyl) carbodiimide” with the closing parenthesis (emphasis added).
Appropriate correction is required.
Maintained/Modified - 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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1-2, 4, 6, 8-10, 14, 15, and 20 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Mizuno et al. (Mizuno et al., Peptide synthesis on fluorous support, Tetrahedron Letters, Volume 45, Issue 17, 2004, Pages 3425-3428.).
Mizuno teaches new fluorous supports used to synthesize peptides based on fluorous chemistry. In fluorous chemistry, a fluorous (highly fluorinated) solvent is immiscible in an organic solution, and a fluorous compound partitions out of the organic phase and into the fluorous phase. Therefore, a fluorous compound is readily separated from nonfluorinated compounds by a simple ‘fluorous/organic’ extraction. Similar to a solid-phase synthesis, fluorous synthesis does not resort to chromatography. Therefore, the strategy of ‘fluorous synthesis’ is designed to combine the advantages of solid-phase synthesis (facile purification) with those of traditional organic synthesis in the liquid-phase synthesis (purification of intermediate and reaction monitoring; large scale reaction).
Regarding claim 1, Mizuno use a hexakisfluorous (Hfa) chain-type support, as shown in Figure 1, which comprises 6 chains that collectively total more than 10 polymerized monomers of tetrafluorethylene, which are alkenes or olefins, thereby reading on polyolefins as claimed in the instant claim 1. A 4-hydroxy-methylphenoxyacetyl (HMPA)-type fluorous support was then prepared for the synthesis of a C-terminal COOH-type peptide. Table 1 shows Fmoc-Ala-OH coupled to the HMPA-Hfa support. Three other peptides were synthesized through elongation of the peptide chain, wherein the Nα amino group was protected/deprotected and the subsequent amino acid was added to the growing chain (Test Peptide 1 and 2 of Figure 3; Scheme 2; Pg 3426 right column, second paragraph – Pg 3427, left column, only paragraph).
Regarding claim 2, Mizuno discloses only Hfa/HMPA-Hfa has only one type of polyolefin chain composed of C8F17 found 6 times throughout the molecule (Figure 1).
Regarding claims 4 and 14, there are 6 total C8F17 chains in Hfa as shown in Figure 1. Chains of this length would result from the polymerization of 4 monomers per chain or a total of 24 monomers.
Regarding claims 6 and 15, the unsaturated carbon-carbon bonds of HMPA-Hfa do not exceed 3-5% of the total carbon-carbon bonds (Figure 1 and Table 1).
Regarding claim 8, HMPA-Hfa is functionalized with an -OH group (Table 1).
Regarding claims 9 and 10, Mizuno teaches the synthesis of test peptides 1 and 2, both of which are 7 amino acid residues (Figure 3).
Regarding claim 20, Mizuno teaches deprotection to remove a protecting group from an Nα as well as cleavage of the peptide chain from the HMPA-Hfa support (Figure 3; Pg 3425, right column, last paragraph – Pg 3426, left column, first paragraph; Pg 3426, right column, last paragraph – Pg 3427, left column, only paragraph).
Maintained/Modified - 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.
Claims 1-4, 6-12, 14-16, and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Mizuno et al. (Mizuno et al., Peptide synthesis on fluorous support, Tetrahedron Letters, Volume 45, Issue 17, 2004, Pages 3425-3428.) in view of Liang (Phase-selectively soluble polyisobutylene (PIB)-bound catalysts and their applications in green synthetic processes, PhD dissertation, August 2016).
The teachings of Mizuno have been set forth above. Briefly, Mizuno teaches new functionalized, fluorous polyolefin supports used in peptide synthesis (Abstract). Mizuno does not teach a method of peptide synthesis wherein the polyolefin chain is polyisobutene (polyisobutylene).
Liang teaches phase-selectively soluble polyisobutylene (PIB)-bound catalysts and their applications in green synthetic processes (Title). Liang teaches that green chemistry has driven innovation in the field of chemical catalysts, with a focus on improved methods to separate ligands and catalysts from the products after reactions such that the ligands and catalysts can be recovered and reused without loss of their catalytic activities. More efficient separations can simplify the workup procedures to minimize metal leaching to the product and reduce the amount of solvent waste (Pg 1-2). Soluble polymers can be used as supports to aid in catalyst recycling. In this case, catalysts are immobilized on phase selectively soluble polymer supports that can be recovered and reused after homogeneous reactions via facile separation strategies. A number of methods that facilitate the separation of soluble polymer-supported catalysts from products have been described including solid/liquid separations and biphasic liquid/liquid separations (Pg 11, first paragraph under “Recovery and Reuse of Soluble Polymer-supported Catalysts).
Liang further teaches that several types of polymer supports can be used in the above method, including polyethylene, polypropylene, and polyisobutylene (Pg 15, final line – Pg 16, line 1). Of these, polyisobutylene has certain advantageous, including that it is inexpensive and commercially available because of its wide use in sealants, lubricants, and fuel additives. Further, the terminal alkene group can be modified by chemical transformations to synthesize many useful functional groups that can be used to form a variety of polymer-supported ligands and catalysts. It is also phase-selectively soluble in nonpolar organic solvents like hexane, heptane, dichloromethane, toluene, and THF at ambient temperature but insoluble in polar solvents including methanol, acetonitrile, DMF, and water.
Regarding claim 3, Mizuno teaches functionalized, fluorous supports used in peptide synthesis. Liang teaches improved soluble polymer supports, such as polyisobutylene, that can be used in chemical synthesis and recycled without loss of activity, thereby minimizing environmental impacts. It would be prima facie obvious to use a soluble polyisobutylene polymer support, taught by Liang, in the method of peptide synthesis taught by Mizuno, in order to make the peptide synthesis process more environmentally-friendly. One skilled in the art would have a reasonable expectation of success because Liang had previously demonstrated that such an environmentally-friendly approach could be used without loss of activity of the catalysts due to its attachment to the polyisobutylene support.
Regarding claims 7 and 16, Liang teaches using vinyl terminated PIB (Glissopal) with a nominal molecular weight of 1000 Da or 2300 Da (Pg 125, first paragraph).
Regarding claim 11, Liang teaches that the phase-selective solubility of polyisobutylene makes it a useful polymer support for the recycling of homogeneous catalysts. In this approach, the catalyst-containing nonpolar phase and the product-containing polar phase are separated using a biphasic liquid/liquid separation strategy after the reaction, and then the catalyst-containing nonpolar phase is recovered through a facile gravity separation and reused in subsequent cycles (Pg 31, lines 15-20). Liang also teaches that the product can then be isolated by extraction with a solvent that dissolves the product but not the catalyst (Pg15, lines 2-6).
Regarding claim 12, Liang teaches that polyisobutylene is insoluble in polar solvents including methanol, acetonitrile, DMF, and water at ambient temperature (Pg 31, lines 12-15).
Claims 1-4, 6-12, 14-16, 20, and 22-23 are rejected under 35 U.S.C. 103 as being unpatentable over Mizuno et al. (Mizuno et al., Peptide synthesis on fluorous support, Tetrahedron Letters, Volume 45, Issue 17, 2004, Pages 3425-3428.) and Liang (Phase-selectively soluble polyisobutylene (PIB)-bound catalysts and their applications in green synthetic processes, PhD dissertation, August 2016), as applied to claims 1-4, 6-12, 14-16, and 20, and in further view of Albarran et al. (Albarran et al., Synthesis of functionalized polyisobutylene’s using the propylene epoxide/TiCl4 initiating system, Polym. Chem., 2014, 5, 4710.).
The teachings of Mizuno and Liang have been set forth above. Mizuno and Liang do not teach specific polyisobutylene species, such as those disclosed in claim 22.
Albarran teaches the synthesis of symmetric and asymmetric telechelic polyisobutylenes (PIBs), including the synthesis of HO-PIB-Allyl shown below (Scheme 2, Pg 4712), which reads on the 5th molecule of claim 22:
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Greyscale
Albarran states that primary hydroxyl functionalized telechelic polyisobutylenes (HO-PIB-OH) are of great interest for use in other applications, such as the synthesis of polyurethanes (Introduction, first sentence).
Regarding claim 22, Mizuno and Liang teach a method of peptide synthesis wherein the peptide chain is attached to a polyolefin anchor molecule, thereby making the peptide chain soluble in apolar solvents. Albarran teaches a method of producing polyisobutylene derivatives functionalized at one terminus with a hydroxyl group. It would be prima facie obvious to use a polyisobutylene derivative with a terminal functional hydroxyl group, taught by Albarran, in the method of peptide synthesis taught by Mizuno and Liang, in order to attach either the C-terminus, as claimed, or the N-terminus, as contemplated in the instant specification, of the elongating peptide chain to the polyisobutylene anchor molecule. One skilled in the art would have a reasonable expectation of success because -OH functionalized polyisobutylene derivatives had been previously shown to be useful in other downstream applications, such as the chemical synthesis of other polymers as described.
Regarding claim 23, Liang teaches that polyolefins, such as PIB, are phase-selectively soluble in nonpolar organic solvents like hexane or heptane; Liang also teaches that PIB is soluble in cyclohexane (Pg 133, first paragraph).
Claims 1-4, 6-17, and 20 are rejected under 35 U.S.C. 103 as being unpatentable over Mizuno et al. (Mizuno et al., Peptide synthesis on fluorous support, Tetrahedron Letters, Volume 45, Issue 17, 2004, Pages 3425-3428.) and Liang (Phase-selectively soluble polyisobutylene (PIB)-bound catalysts and their applications in green synthetic processes, PhD dissertation, August 2016), as applied to claims 1-4, 6-12, 14-16, 20, and 23 above, and further in view of Davidson et al. (US 20140051819 A1, published 2/20/2014).
The teachings of Mizuno and Liang have been set forth above. Mizuno and Liang do not teach that the anchoring molecule has a biobased content greater than 90%.
Davidson teaches a method for preparing isobutene from a renewable source and their use in the preparation of renewable polymers as well as purification and oligomerization (Abstract). Davidson teaches that traditional production of isobutene requires petrochemical sources and is energy-intensive because it requires many steps ([0003-0004]). There is increasing environmental concern that the use of petroleum-derived hydrocarbons as basic raw materials (e.g., butadiene or isoprene) contributes to environmental hazards such as global warming and pollution and fosters overdependence on unreliable petroleum sources. Thus, there is a need for a low carbon footprint solution to produce isobutene-based polymers using renewable energy (i.e., biologically derived) sources of monomers such as isobutene and low energy chemical processes ([0005]).
To achieve a desired biobased content in an isobutene-based polymer, the mixture ratio of biobased isobutene to petroleum-based isobutene in the polymer may be varied, ranging from greater than 0% to greater than 90% ([0052]). Alternatively or additionally, the multiolefin content of the final polymer can be modified by adjusting the multiolefin monomer feed for the polymerization reaction. For example, 4 mol% (petroleum-based isoprene, renewable isoprene or mixtures thereof) incorporation of isoprene into the final butyl polymer would result in a biobased content of between 5 to 95% (ASTM D6866). As another example, 0.9 mol % (petroleum-based isoprene, renewable isoprene or mixtures thereof) incorporation of isoprene into the final butyl polymer would result in a biobased content of between 1 to 99% (ASTM D6866). Polymerization of a butyl rubber polymer using biobased isoprene and bio-isobutene will yield a bio-butyl rubber with a bio-based content of 100% (ASTM D6866) ([0053]).
Regarding claims 13 and 17, Mizuno and Liang teach a method of peptide synthesis wherein the peptide chain is attached to a polyolefin anchor molecule, such as polyisobutylene, thereby making the peptide chain soluble in apolar solvents. Davidson teaches a method of obtaining polyisobutylene from renewable, environmentally-friendly sources. It would be prima facie obvious to use the environmentally-friendly sources of polyisobutylene, taught by Davidson, in the method of peptide synthesis taught by Mizuno and Liang, in order to reduce the energy and steps required to generate polyisobutylene, as described by Davidson. One skilled in the art would have a reasonable expectation of success as the polyisobutylene derived from renewable sources is structurally indistinguishable from those derived from petroleum sources.
Claims 1-2, 4, 6, 8-10, 14, 15, and 19-20 are rejected under 35 U.S.C. 103 as being unpatentable over Mizuno et al. (Mizuno et al., Peptide synthesis on fluorous support, Tetrahedron Letters, Volume 45, Issue 17, 2004, Pages 3425-3428.) in view of Ho et al. (Ho et al., Carbodiimide-mediated amide formation in a two-phase system. A high-yield and low-racemization procedure for peptide synthesis., J. Org. Chem., 1995, 60, 3569-3570.).
The teachings of Mizuno have been set forth above. Mizuno does not teach the method comprising a coupling reaction using EDC/HOBt (1-ethyl-3-(3-dimethyl-aminopropyl) carbodiimide and hydroxybenzotriazole orb)) or EDC/DMAP (1-ethyl-3-(3-dimethyl-aminopropyl) carbodiimide and 4-dimethylaminopyridine).
Ho teaches that the prevention of racemization is one of the major challenges in peptide synthesis. The addition of N-hydroxy compounds, such as 1-hydroxybenzotriazole (HOBt), suppresses side reactions and reduce racemization, although it still occurs to some degree. Ho teaches a two-phase coupling method which affords di- or tri-peptides in high yields with low degrees of racemization. In this method, the coupling reactions were carried out in dichloromethane using the water-soluble N-ethyl-N’-[3-(dimethylamino)propyl]carbodiimide hydrochloride (EDC) as the coupling reagent (Pg 1). Ho reported that the coupling reactions in the two-phase mixture generally afforded yields comparable to those in DMF and provides a more convenient workup, and in general higher recovery yields were generally obtained (Pg 2).
Regarding claim 19, Mizuno teaches a method of peptide synthesis wherein the peptide chain is attached to a polyolefin anchor molecule, thereby making the peptide chain soluble in apolar solvents. Ho teaches a carbodiimide-mediated amide formation in a two-phase system for peptide synthesis that produces relatively high yields and low racemization rates. It would be prima facie obvious to use EDC/HOBt in a coupling step of peptide synthesis, taught by Ho, in the method taught by Mizuno, in order to minimize racemization and produce high yields. One skilled in the art would have a reasonable expectation of success because this peptide synthesis step had been successfully performed in the art prior to the instant invention.
Maintained/Modified - Double Pateαting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-11, 14-17, and 20-21 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 2-5, 6-11, and 13-15 of copending Application No. 17/605,008 (‘008, reference application; claim set filed on 5/22/2025). Although the claims at issue are not identical, they are not patentably distinct from each other because they contain overlapping subject matter.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claim 1 of copending Application No. ‘008 recites a method for synthesizing peptides or proteins or peptidomimetics comprising a first end and a second end, wherein the method proceeds in a liquid phase by successive elongation of the second end, which has a primary or secondary amine functionality, a hydroxyl functionality or a thiol functionality, of a peptide or protein or peptidomimetic chain by units, characterized in that:
- said units are selected from the group made up of Qa - E – Qb type molecules, where Qa and Qb may be the same or different, and are selected from electrophilic groups or nucleophilic groups, and E represents a spacer;
- the first end of said peptide or protein or peptidomimetic is attached by a covalent bond to an anchoring molecule soluble in one or more organic solvents; wherein said one or more organic solvents comprise halogenated solvents selected from the group consisting of methylene chloride and chloroform, ethyl acetate, tetrahydrofuran, 2-methyletetrahydrofuran, isooctane, cyclohexane, hexane(s), methylcyclohexane, methyl tert-butyl ether, benzene or toluene;
- wherein said method does not involve protection groups for the primary amine or secondary amine functionality or for the hydroxyl or thiol functionality.
Dependent claims include further limitations regarding Qa – E – Qb type molecules (claims 2-5 and 11), the anchoring molecule (claims 6-10), and additional steps (claims 13 -15).
Conclusion
No claim is allowed.
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
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/SARA E KONOPELSKI SNAVELY/Examiner, Art Unit 1658
/FRED H REYNOLDS/Primary Examiner, Art Unit 1658