DETAILED ACTION
Status of the Claims
Claims 1-10 are pending in the instant application and are being examined on the merits in the instant application.
Advisory Notice
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Priority
The U.S. effective filing date for claims 1-5 has been determined to be 12/14/2022, the filing date of the U.S. Provisional Application No. 63/432,491.
The U.S. effective filing date for claims 6-10 has been determined to be 12/14/2023, the filing date of the instant Application.
Information Disclosure Statement
No Information Disclosure Statements have been filed in the instant application. Applicants are reminded of their duty to disclose patents and publications relevant to the patentability of the instant claims. Applicant is reminded of the requirements of 37 CFR 1.56 and Li Second Family Limited Partnership v. Toshiba Corp., 56 USPQ2d 1681 (Fed. Cir. 2000); accord McKesson Information Solutions, Inc. v. Bridge Medical, Inc. 487 F.3d 897, 913. (Fed.Cir.2007).
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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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 1-5 are rejected under 35 U.S.C. 103 as being unpatentable over Jain et al. (“Anion recognition through novel C-thiophenecalix[4]resorcinarene: PVC based sensor for chromate ions,” 2005, ELSEVIER; Talanta, Vol. 65, pp. 716-721) in view of Nemat et al. (“Thioderivatives of Resorcin[4]arene and Pyrogallol[4]arene: Are Thiols Tolerated in the Self-Assembly Process?”, 2021, ACS; Organic Letters, Vol. 23, pp. 6861-6865) and On-Too (US 2007/0295398; published December, 2007).
Applicants Claims
Applicant claims a compound having the formula [see claim 1] wherein R is H or an OH group (instant claim 1). Applicant further claims a thiophene functionalized calixarene selected from the group consisting of C-thiopheneresorcin[4]arene and C-thiopheneprogallol[4]arene (claims 3-5). Applicant further claims a tetrameric reaction product of heterocyclic 3-thiophenecarboxaldehyde and an aromatic compound, the reaction product being a calix[4]arene (instant claim 2)
Determination of the scope
and content of the prior art (MPEP 2141.01)
Jain et al. teaches the synthesis of a novel ionophore C-thiophenecalix[4]resorcinarene having the following structure and synthesis route:
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(abstract, see whole document, p. 717, Figure 1).
Jain et al. teaches that: “To a solution of resorcinol (18.06 g, 0.164 mol) dissolved in 70 ml of ethanol, was added 20 ml concentrated HCl, maintaining the reaction mixture below 50 ◦C. Thiophene-2-aldehyde (19.04 g, 0.17 mol) was added drop wise over a period of 30 min to obtain a heterogeneous reaction mixture. The mixture was slowly heated to give a homogenous solution. It was refluxed for 8 h to obtain dark brown coloured precipitates, filtered and washed with water to remove excess HCl [18]. The precipitates of C-thiophenecalix[4]resorcinarene thus obtained were crystallized from hot acetone (Fig. 1).” (p. 717, col. 1, §2.2).
Ascertainment of the difference between
the prior art and the claims (MPEP 2141.02)
The difference between the rejected claims and the teachings of Jain et al. is that Jain et al. teaches reacting 2-thiophenecarboxaldehyde rather than 3-thiophenecarboxaldehyde, and Jain et al. does not teach the pyrogallol[4]arene species of the calix[4]arene.
Nemat et al. teaches thioderivatives of resorcin[4]arene and pyrogallol[4]arene and self assembly of the same (title, see whole document).
Nemat et al. teaches that: “Macrocycles constitute a large proportion of molecules investigated in supramolecular chemistry. Phenolic macrocycles of the calix[4]arene family, in particular, have proven to be highly functional and versatile bowl-shaped building blocks. Calix[4]arene and its sister molecules resorcin[4]arene (RS) and pyrogallol[4]arene (PG) (Figure 1a) are obtained via simple one-step procedures and are even commercially available. They feature a conformationally restricted and easily derivatizable framework. Both RS and PG are capable of self-assembly in apolar solvents, forming hexameric capsules I and II through hydrogen bonds. These supramolecular assemblies are capable of guest uptake, and in the case of RS, the structure’s interior serves as an enzyme-like catalytic pocket for numerous reactions.” (p. 6861, 1st paragraph).
On-Too teaches conducting polymers with porphyrin cross-linkers (see whole document), and teaches that: “3-Thiophenecarboxaldehyde (98%) was sourced from Aldrich.” ([0085]).
Finding of prima facie obviousness
Rationale and Motivation (MPEP 2142-2143)
A prima face case of obviousness based upon a substitution rationale requires (1) a finding of fact that the prior art contained a product which differed from the claimed product by the substitution of some components with other components; (2) a finding of fact that the substituted components and their functions were known in the art; (3) a finding that one of ordinary skill in the art could have substituted one known element for another, and the results of the substitution would have been predictable; and (4) whatever additional findings based upon the Graham factual inquiries may be necessary, in view of the case under consideration, to explain a conclusion of obviousness (MPEP § 2143-B).
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 substitute 3-thiophenecarboxylate for the 2-thiophenecarboxylate in synthesis of C-thiophenecalix[4]resorcinarene, as suggested by Jain et al., and produce the instantly claimed invention because the both 2- and 3- thiophenecarboxylate species were know in the prior art, as disclosed by Jain et al. and On-Too, the reaction being the same, the result would have predictably resulted in the compound of instant claim 1 wherein R=H; and further to substitute the resorcinol with pyrogallol as resorcin[4]arenes and pyrogallol[4]arenes are considered obvious variants in the art, as taught by Nemat et al., and substitution of resorcinol with pyrogallol would have predictably resulted in C-thiophenecalix[4]pyrogallolarene.
From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention because it would have required no more than an ordinary level of skill in the art to substitute 3-thiophenecarboxylate for the 2-thiophenecarboxylate in synthesis of C-thiophenecalix[4]resorcinarene. 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, especially in the absence of evidence to the contrary.
In light of the forgoing discussion, the Examiner concludes that the subject matter defined by the instant claims would have been obvious within the meaning of 35 USC 103.
Claims 6-7, 9 and 10 are rejected under 35 U.S.C. 103 as being unpatentable over Jain et al. in view of Nemat et al. and On-Too as applied to claims 1-5 above, and further in view of Shumatbaeva et al. (“Synthesis of Ag-AgCl nanoparticles capped by calix[4]resorcinarene-mPEG conjugate and their antimicrobial activity,” 2020, ELSEVIER; Colloids and Surfaces A, Vol. 602, Article 125124, pp. 1-13) and BARLOW (WO 2013/104916 A2; published July, 2013).
Applicants Claims
Applicant claims a compound having the formula [see claim 1] wherein R is H or an OH group (instant claim 1). Applicant further claims a thiophene functionalized calixarene selected from the group consisting of C-thiopheneresorcin[4]arene and C-thiopheneprogallol[4]arene (claims 3-5). Applicant further claims the composition of claim 3 further comprises silver nanoparticles, and an imaging agent comprising the composition of claim 1 (claim 9) and an antibiotic coating containing a composition comprising thiophene-based pyrogallol[4]arene-capped silver nanoparticles having the formula Pg4THP4-AgNP (claims 7 and 10).
Claim interpretation: The examiner is interpreting the “the formula Pg4THP4-AgNP” as requiring four compounds of claim 1 wherein R is -OH (or C-thiophenepyrogallol[4]arene as in claim 5) complexed with a silver nanoparticle.
Determination of the scope
and content of the prior art (MPEP 2141.01)
Jain et al. teaches the synthesis of a novel ionophore C-thiophenecalix[4]resorcinarene, as discussed above and incorporated herein by reference.
Nemat et al. teaches thioderivatives of resorcin[4]arene and pyrogallol[4]arene and self assembly of the same, as discussed above and incorporated herein by reference.
On-Too teaches conducting polymers with porphyrin cross-linkers including 3-Thiophenecarboxaldehyde, as discussed above and incorporated herein by reference.
Ascertainment of the difference between
the prior art and the claims (MPEP 2141.02)
The difference between the rejected claims and the teachings of Jain et al. is that Jain et al. does not expressly teach combining silver nanoparticles with the suggested thiophene functionalized calixarenes.
Shumatbaeva et al. teaches that: “The growing resistance of bacteria to traditional antibiotics makes it necessary to develop new antimicrobial agents with the dissimilar mode of action such as Ag and AgCl nanoparticles. Here the synthesis of silver NPs in the colloidal solutions of calix[4] resorcinarene-mPEG conjugate C11-mPEG was reported. NPs were synthesized under varied conditions: different Ag+/C11-mPEG molar ratio, presence/absence of reducing agent (NaBH4), in dark or LED light exposure. It was found that in all cases Ag-AgCl NPs, stabilized by C11-mPEG, were obtained with the difference in the Ag NPs content and sizes. Physicochemical characteristics of the Ag-AgCl@C11-mPEG NPs were evaluated by UV–vis, FT-IR, XRPD, XRF, DLS, and TEM methods. The antimicrobial activity of NPs against Gram-positive and Gram-negative bacteria and fungi was studied and the preferred antimicrobial activity against Gram-positive bacteria was found. The proposed scheme of Ag-AgCl@C11-mPEG NPs and the influence of NPs content on the antimicrobial activity were discussed.” (abstract, see whole document).
Shumatbaeva et al. teaches that: “One of the materials with unique antimicrobial action is silver materials: silver ions, silver nanoparticles (Ag NPs), silver chloride nanoparticles (AgCl NPs), silver–silver chloride nanoparticles (Ag–AgCl NPs) and others. Usually, the antimicrobial properties of silver materials are associated with silver ions action. The mechanism of antibacterial activity of silver ions includes their interaction with the bacterial cell envelope which leads to the destabilization of the cells membrane and loss of K+ ions as well as the decrease of ATP level, bonded with phospholipids. Also, silver ions interact with nucleic acids and enzymes inside the cell and produce reactive oxygen species. Herewith, due to the oligodynamic effect, silver ions show high antibacterial efficacy even in low concentrations. Unfortunately, the endogenous and exogenous mechanisms of bacteria resistance against silver ions are known, which is connected with the changes in the permeability of bacteria cell envelope and extracellular and intracellular sequestration of metal ions and others, although in the case of Gram-positive bacteria (especially staphylococci), the silver ions resistance does not widely occur.” (p. 2, col. 1, 2nd paragraph).
Shumatbaeva et al. teaches that: “ Silver nanoparticles are one of the most attractive inorganic materials, which are characterized by a wide spectrum of action against bacteria, fungi and viruses. It is considered that they have a lower ability to cause resistance due to more complex mechanisms of biological exposure. The antimicrobial properties of AgNPs are related to two factors: the release of Ag+ and their toxic action, which is described above, and the specific effects of nanosilver. It is reported that nanosilver inhibits the transcription by ribonucleic acid (RNA) polymerase and prevents correct replication of DNA [5,6]. Also, AgNPs can serve as nanocarriers of drug agents like antibiotics that can lead to the synergistic enhancement of antimicrobial effects of the hybrid nanomaterial. (p. 2, col. 1, 3rd paragraph).
Shumatbaeva et al. teaches that: “Here we describe the synthesis of silver NPs in the colloid solution of calixresorcinarene bearing methoxy-PEG fragments, attached via acylhydrazone bonds (C11-mPEG, Fig. 1). Calixresorcinarenes are the convenient macrocyclic platform for the different groups’ attachment and obtaining derivatives with various topology and developed receptor properties, produced by the aromatic cavity of the macrocycle, the functionality of the substituents, as well as the cooperative effect, created by the macrocycle molecules in the solution and on the surface [25–29]. Recently the use of amphiphilic calixresorcinarenes as capping agents for silver, gold and platinum NPs were described [30–34]. They stabilize the NPs surface and give them receptor properties including antitumor drugs binding.” (paragraph bridging pp. 2-3).
Shumatbaeva et al. does not teach an antibiotic coating, however, BARLOW teaches medical coatings including calixarenes.
BARLOW teaches: “Implantable medical devices, such as catheters, which comprise a calixarene-derived coating that resists adhesion and/or colonisation of bacteria and/or fungi are described. Also described are calixarene-derived coating materials, intermediates useful in their manufacture, processes for their preparation, and methods for coating of implantable medical devices with the calixarene compounds.” (abstract, see whole document). BARLOW teaches that: “When the medical device is implanted into a patient, the coating will preferably resist adhesion and/or colonisation of bacteria onto the surface of the device. Preferred embodiments of the device may provide a coating that, either as an alternative to, or in addition to resisting adhesion and/or colonisation of bacteria, has an antimicrobial effect. Said antimicrobial effect will ideally be exhibited at a surface concentration that also provides a safe pharmacological profile.” (p. 5, lines 22-27).
Regarding claim 9, the silver nanoparticles, suggested by Shumatbaeva et al., in combination with the medical device coating of BARLOW would have inherently acted as an imaging contrast agent providing contrast in, e.g. an X-ray image.
Regarding claim 7, it would have been prima facie obvious to optimize the synthesis parameters, as suggested by Shumatbaeva et al., to produce the best antibacterial silver nanoparticle coating thereby resulting in thiophene-based pyrogallol[4]arene-capped silver nanoparticles having the formula Pg4THP4-AgNP.
Finding of prima facie obviousness
Rationale and Motivation (MPEP 2142-2143)
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 react 3-thiophenecarboxylate with resorcinol or pyrogallol and produce a C-thiopheneresorcin[4]arene or a C-thiophenepyrogallol[4]arene, as discussed above, and further to combine/synthesize silver nanoparticles for their antimicrobial (antibiotic) properties, as suggested by, Shumatbaeva et al. and to incorporated the same into a coating on a medical device to provide an antimicrobial surface thereon, as suggested by BARLOW, to overcome antibiotic resistant bacteria.
From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention because it would have required no more than an ordinary level of skill in the art to produce silver nanoparticles complexed with 4 thiophenepyrogallol[4]arene species (Pg4THP4-AgNP), and incorporate the same in a medical device coating. 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, especially in the absence of evidence to the contrary.
In light of the forgoing discussion, the Examiner concludes that the subject matter defined by the instant claims would have been obvious within the meaning of 35 USC 103.
Claims 8 is rejected under 35 U.S.C. 103 as being unpatentable over Jain et al. in view of Nemat et al. and On-Too as applied to claims 1-5 above, and further in view of Hoskins et al. (“Simple Cali[n]arenes and Calix[4]resorcinarenes as Drug Solubilizing Agents,” Journal of Nanomedicine Research, Vol. 2, No. 3, Article 00028, pp. 1-8).
Applicants Claims
Applicant claims a compound having the formula [see claim 1] wherein R is H or an OH group (instant claim 1). Applicant further claims a thiophene functionalized calixarene selected from the group consisting of C-thiopheneresorcin[4]arene and C-thiopheneprogallol[4]arene (claims 3-5). Applicant further claims a pharmaceutical drug comprising the composition of claim 1 (instant claim 8).
Determination of the scope
and content of the prior art (MPEP 2141.01)
Jain et al. teaches the synthesis of a novel ionophore C-thiophenecalix[4]resorcinarene, as discussed above and incorporated herein by reference.
Nemat et al. teaches thioderivatives of resorcin[4]arene and pyrogallol[4]arene and self assembly of the same, as discussed above and incorporated herein by reference.
On-Too teaches conducting polymers with porphyrin cross-linkers including 3-Thiophenecarboxaldehyde, as discussed above and incorporated herein by reference.
Ascertainment of the difference between
the prior art and the claims (MPEP 2141.02)
The difference between the rejected claims and the teachings of Jain et al. is that Jain et al. does not expressly teach pharmaceutical drug comprising the composition of claim 1.
Hoskins et al. teaches that: “Many drug molecules have low solubility in aqueous media and, hence, poor bioavailability. The formation of a host-guest complex with some other compound which has a good solubility profile can facilitate solubilization of hydrophobic drugs. Complex formation relies upon the formation of non-covalent interactions between the host molecule and the drug guest. The use of calix[n]arenes, a well-characterized class of cyclic oligomers, has been investigated for their ability to form complexes with a variety of ionic and molecular species. This review highlights those studies which have demonstrated the potential of calix[n]arenes as host molecules in novel drug delivery systems.” (abstract, see whole document).
Hoskins et al. teaches that: “Calix[n]arenes and the closely related calix[4]resorcinarenes area group of cyclic oligomers with characteristic structures prepared easily from the reaction of a phenolic substrate with an aldehyde, typically under acidic conditions. The synthesis, properties and potential of calix[n]arenes and calix[4]resorcinarenes has been described. Calix[n]arenes and calix[4]resorcinarenes have found use in supramolecular chemistry, catalysis and separation science but they have attracted much interest for their potential use in drug design and delivery. The compounds consist of substituted aromatic rings joined together by a bridging atom, normally the carbon within a methylene group, to form a cyclic structure typically represented as a truncated cone with an upper and lower rim (Figure 1). Substituents on these peripheral rims confer specific chemical, structural and physical properties on the molecules. Closely related series of compounds, heterocalix[n]arenes in which the phenolic residues are bridged by sulfur atoms and calix[4]pyrroles, for example, have also been studied but not to the same extent as the parent compounds. This review will focus on the use of calix[n]arenes and calix[4]resorcinarenes bearing functionalities on the upper and lower rims in facilitating the solubilization of drug molecules in aqueous media.” (p. 1, paragraph bridging cols. 1-2).
Hoskins et al. teaches that: “The interior cavity of calix[n]arenes and calix[4]resorcinarenes in the cone conformation is typically hydrophobic and this can be exploited to form reversible host-guest complexes with small organic molecules via non-covalent interactions. In studies such as these the calix[n]arenes are often referred to colloquially as ‘nano-baskets’, indicating their proposed use. Many early studies into complex formation with calix[n]arenes have been undertaken in non-aqueous environments. Once in an aqueous environment water-soluble calix[n]arenes can, in some cases, enhance the solubility of hydrophobic drugs via a non-covalent hydrophobic interaction within the core of the calix[n]arene. Studies in aqueous environments in which there is an abundance of water molecules capable of forming hydrogen bond networks with polar functional groups present on the calix[n]arene have shown that the solubilization of specific drugs with particular structural features depends not only upon this hydrophobic interaction but also the functional groups on the upper and lower rims and the size of the calix[n]arene, whether it is a calix[4]arene or calix[6]arene for example.” (p. 3, col. 1, lines, 8-26).
Finding of prima facie obviousness
Rationale and Motivation (MPEP 2142-2143)
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 react 3-thiophenecarboxylate with resorcinol or pyrogallol and produce a C-thiopheneresorcin[4]arene or a C-thiophenepyrogallol[4]arene, as discussed above, and to produce a drug delivery pharmaceutical composition by forming host-guest complex with a hydrophobic drug for increased solubility and delivery of the same.
From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention because it would have required no more than an ordinary level of skill in the art to produce a C-thiopheneresorcin[4]arene and/or C-thiopheneprogallol[4]arene pharmaceutical hydrophobic drug, as taught by Hoskins et al., with increased solubility of the hydrophobic drug. 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, especially in the absence of evidence to the contrary.
In light of the forgoing discussion, the Examiner concludes that the subject matter defined by the instant claims would have been obvious within the meaning of 35 USC 103.
Double Patenting
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 §§ 706.02(l)(1) - 706.02(l)(3) 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 USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The 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/process/file/efs/guidance/eTD-info-I.jsp.
Claim 2 is rejected on the ground of nonstatutory double patenting as being unpatentable over claims 2-16 of U.S. Patent No. 11,629,113 (hereafter ‘113) in view of Jain et al. in view of Nemat et al. and On-Too.
Applicant claims a tetrameric reaction product of heterocyclic 3-thiophenecarboxaldehyde and an aromatic compound, the reaction product being a calix[4]arene (instant claim 2).
‘113 claim 2 recites a method of making a mixed macrocycle of resorcinol and pyrogallol comprising: (a.) mixing pyrogallol and resorcinol with an aldehyde in a solvent selected from the group consisting of acetonitrile, ethanol, acetone, water and combinations thereof; (b.) irradiating the mixture using microwaves to produce a product; and (c.) crystallizing the product; wherein the product comprises the mixed macrocycle. ‘113 claim 12 recites a
A method of making a mixed macrocycle of resorcinol and pyrogallol comprising: (a.) mixing pyrogallol and resorcinol with an aldehyde in a solvent selected from the group consisting of acetonitrile, ethanol, acetone, water and combinations thereof; (b.) heating the mixture in the presence of at least one catalyst selected from the group consisting of concentrated HCl, a macroreticular polystyrene-based sulfonic acid ion exchange resin and sulfonated graphitic carbon nitride, to produce a product; and (c.) crystallizing the product; wherein the product comprises the mixed macrocycle.
The difference between the instantly rejected claims and the claims of ‘113 is that the claim of ‘113 do not expressly claim the aldehyde is 3-thiophenecarboxaldehyde.
Jain et al. teaches the synthesis of a novel ionophore C-thiophenecalix[4]resorcinarene, as discussed above and incorporated herein by reference.
Nemat et al. teaches thioderivatives of resorcin[4]arene and pyrogallol[4]arene and self assembly of the same, as discussed above and incorporated herein by reference.
On-Too teaches conducting polymers with porphyrin cross-linkers including 3-Thiophenecarboxaldehyde, as discussed above and incorporated herein by reference.
It would have been prima facie obvious before the effective filing date of the claimed invention that the instantly rejected claims are an obvious variant of the claims of ‘113 because they are directed to the same process of making macrocycles
of resorcinol and pyrogallol. The skilled artisan would have been motivated to modify the claims of ‘113 and produce the instantly rejected claim because the aldehyde species 3-Thiophenecarboxaldehyde is an obvious species to select for producing the macrocycles. Furthermore, the skilled artisan would have had a reasonable expectation of success in producing the invention of the instantly rejected claims because it would have required no more than an ordinary level of skill in utilizing 3-Thiophenecarboxaldehyde in as the aldehyde in the claims of ‘113.
This is a provisional obviousness-type double patenting rejection.
Duplicate Claim Warning
Applicant is advised that should claim 1 be found allowable, claim 3 will be objected to under 37 CFR 1.75 as being a substantial duplicate thereof. When two claims in an application are duplicates or else are so close in content that they both cover the same thing, despite a slight difference in wording, it is proper after allowing one claim to object to the other as being a substantial duplicate of the allowed claim. See MPEP § 608.01(m).
Citation of Pertinent Prior Art
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. PIPINO (US 2002/0122179; published September, 2002) is cited as teaching resorcin[4]arenes bonded to gold nanoparticles ([0057], Figure 2) and teaches silver nanoparticles as well ([0011], [0019] and claim 8). The examiner further cites US 4,010,165 teaching manufacture (chemical synthesis) of thiophene-3-aldehyde (see whole document, particularly col. 1, lines 1-30). Christy et al. (“Conductometric studies on complexation of Ag+ cation by C-thiophene calix[4]resorcinarene in pure and mixed non-aqueous solvent systems,’ 2015; Journal of Inclusion Phenomena and Macrocyclic Chemistry, Vol. 83, No. 3, pp. 343-353) is cited as teaching silver complexes with the C-thiophene calix[4]resorcinarene disclosed by Jain et al. (see whole document).
Conclusion
Claims 1-10 are pending and have been examined on the merits. Claims 1-10 are rejected under 35 U.S.C. 103, and claim 2 is rejected on the ground of nonstatutory double patenting as being unpatentable over claims of U.S. Patent No. 11,629,113. No claims allowed at this time.
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/IVAN A GREENE/Examiner, Art Unit 1619
/TIGABU KASSA/Primary Examiner, Art Unit 1619