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 .
Claim Objections
Claim 10 is objected to because of the following informalities: the claim appears to be missing a period at the end. Appropriate correction is required.
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.
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) 1-9, 11-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over US20020035169 (‘169), Cadenaro et al. (WO2021/094960 (with priority to 11/12/2019)), and Patani et al. (Chem. Rev., 1996, 96, 3147-3176), as evidenced by CN106659639 (machine English translation provided).
Determination of the scope and content of the prior art
(MPEP 2141.01)
Regarding claims 1-9, ‘169 teaches very structurally similar antimicrobial monomer compounds which are bioisosteres to the instantly claimed compounds, specifically they teach compounds of the following formulae:
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, which corresponds to wherein applicant’s m is 1, A1 is C(=O), and A2 is O, one of L1 is a single bond and L2 corresponds to the (CH2)n in ‘169, and L3 is a single bond as in the top compound and applicant’s B1 is/are the alkyl group(s) on the positively charged N atom in the pyridine ring and applicant’s R1-R3 correspond to H or applicant’s R2 and R3 are H and R1 is methyl, and as such these compounds only differ from the instantly claimed compounds in that applicant’s NH is an O atom in the antimicrobial monomers of ‘169 ([0050]; [0113]; structure IV and [0095-0109]; [0115 (defines the claimed variables in this paragraph)]; abstract; claims), and ‘169 discloses that A can be NH ([0198]; structure IV and [0095-0109]; [0050]; abstract; claims) and it would be obvious to switch the O atom for NH since ‘169 clearly teaches that their A can be NH and still lead to antimicrobial compounds ([0100]; [0198]; structure IV and [0095-0109]; [0050]; abstract; claims), which would then make this compound read on the instantly claimed compounds wherein applicants R1 is Me, R2 and R3 are H, A1 is C(=O); m is 1; B1 corresponds to the alkyl group coming off the positively charged N atom of the pyridine ring, and L3 corresponds is a direct bond.
Regarding claims 11-13, ‘169 teaches an antimicrobial polymer composition which comprises the very structurally similar monomer to that of applicant’s formula I as discussed above and wherein the composition can further comprise a multifunctional monomer and a monofunctional monomer with a hydrophilic group, e.g. hydroxyethyl methacrylate, that is different from the antibacterial monomer, and wherein the multifunctional monomer is an (meth)acrylate multifunctional monomer and the monofunctional monomer is an (meth)acrylate monofunctional monomer, and wherein an amount of the antibacterial monomer is about 0.1 wt% based on the total amount of monomers in the antibacterial composition ([0150-0158]; [0116, 0.000001 to 50% by weight of antibacterial polymerizable monomer in the antibacterial primer]; [0113]; structure IV and [0095-0109]; [0115]; abstract; claims; [0198]).
Regarding claims 17, ‘169 teaches forming a film with their dental adhesive composition which comprises at least one of the above structurally similar monomers which are antimicrobial due to the presence of the positively charged nitrogen in the pyridine ring and which polymerize with the polymerization initiator in the dental adhesive composition thereby leading to compounds structurally similar to applicant’s formula 3 which are structurally similar for the same reasons as discussed above ([0202]; [0223];[0113 (defines the claimed variables in this paragraph)]; structure IV and [0095-0109]; [0115]; abstract; claims).
Regarding claim 18, ‘169 teaches wherein the film is metal-free as ‘169 does not mention or disclose that their compositions or films comprise metals (See entire document; claims; [0113]; structure IV and [0095-0109]; [0115]; abstract; claims; [0202]; [0223]; [0197]).
Regarding claim 20, ‘169 teaches articles comprising the antibacterial film of claim 17, specifically wherein it is applied to teeth/dental applications ([0197]; [0202]; [0223]).
Ascertainment of the difference between prior art and the claims
(MPEP 2141.02)
Regarding claims 1-9, 11-20, as discussed above ‘169 does not specifically teach examples of the claimed compounds, and does not teach for instance examples wherein the NH is directly bound to the pyridinium ring as instantly claimed:
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, though as discussed above they teach very structurally similar examples wherein there is the bioisosteric O directly linked to the pyridinium ring. It would have been obvious to substitute this O atom for the claimed NH and have the L3 be a single bond as claimed because O and NH were known classical bioisoisteres of one another as is taught by Patani (Table 2, Grimms hydride displacement: O, NH, and CH2 are known classical bioisosteres; see also tables 19-20).
Regarding claim 14, ‘169 does not specifically teach wherein an amount of the multifunctional monomer is greater than an amount of the monofunctional monomer.
Regarding claim 15, ‘169 does not teach wherein a content ratio of the multifunctional monomer to the monofunctional monomer is in a range of about 1:1 to about 1.5:1.
Regarding claim 16, 169 does not teach wherein an amount of the monofunctional monomer with a hydrophilic group is in a range of about 29 wt% to about 45 wt% based on the total amount of the composition.
However, these deficiencies in ‘169 are addressed by Cadenaro.
Cadenaro teaches antimicrobial/antibacterial monomers comprising pyridinium groups and the claimed (meth)acrylate monofunctional and multifunctional monomers which are useful for forming dental compositions, Cadenaro teaches wherein the compositions comprise from 0.1-10% by weight based on total weight of the composition of the antimicrobial monomers, 10-50% by weight based on total weight of the monomers/photopolymerizable compounds of the composition of the monofunctional (meth)acrylate monomers which have/can have the claimed hydrophilic groups, e.g. hydroxyethyl methacrylate which reads on/overlaps the claimed range in claim 16, and 30-90% by weight based on total weight of the monomers/photopolymerizable compounds of the composition of the multifunctional (meth)acrylate monomers, which on the low end of the ranges requires more of the multifunctional monomer than the monofunctional monomer as instantly claimed (abstract; pg. 9, ln. 20-pg. 10, ln. 2; pg. 10, ln. 23-pg. 12, ln. 33, inclusive).
Finding of prima facie obviousness
Rationale and Motivation (MPEP 2142-2143)
It would have been obvious to form the claimed antimicrobial monomers because it would be obvious to substitute the O in the specific example/formula cited above for the claimed NH to form the NH version of the exemplified compound shown in the rejection above because as discussed above O and NH are known classical bioisosteres of one another and as such it would be obvious to form additional antimicrobial/antibacterial monomers of ‘169 to have the claimed NH for the O that is directly bonded to the pyridine ring in the example shown above because Patani teaches that these were known classical bioisosteres of one another and one of ordinary skill in the art would be motivated to make this substitution, e.g. and form the compounds of the instant claims, e.g. claim 5, in order to probe the activity of the antimicrobial compounds of ‘169 and form additional antimicrobial/antibacterial compounds for use in dental compositions.
It also would have been obvious to use the percentages of the monofunctional and multifunctional monomers that are instantly claimed in the composition of ‘169 because ‘169 and Cadenaro both teach using the same monofunctional methacrylate monomers which are hydrophilic, e.g. hydroxyethyl methacrylate, with the claimed multifunctional methacrylate monomers claimed and Cadenaro teaches using an excess of the multifunctional monomer over the monofunctional monomer to form the same types of dental compositions as taught by ‘169. Thus, it would have been obvious to one of ordinary skill in the art to optimize the amounts/ratios of the multifunctional and monofunctional monomers to fall within the claimed about 1:1 to about 1.5:1 as it was known from the teachings of ‘169 and Cardenaro to optimize the amounts of the photopolymerizable monomers in the dental compositions in order to formulate the most effective antimicrobial dental compositions for use in the mouth and which have the necessary strength/adhesion for use on teeth.
Regarding claim 19, it would have been obvious to one of ordinary skill in the art to optimize the hardness of the film of ‘169 and Cadenero to provide a hard film that will not easily scratch/be removed, e.g. a pencil hardness of at least 6H, because teeth are regularly cleaned with sharp/forceful dental tools, e.g. dental pick, and as such films placed on the teeth with dental work are subject to strong forces of chewing etc. and as such it was known to optimize the strength of the dental compositions, e.g. dental adhesives/cements of ‘169 and Cadenero to provide the most effective/strong dental adhesives/cements while also providing good antimicrobial effect. It also would have been obvious for the compositions of ‘169 and Cadenero to have the claimed water contact angle and/or optimize the film to have the claimed water contact angle because as is evidenced by CN106659639 it was known to form dental compositions, e.g. dental adhesives/dental coating agents which are antimicrobial, having water contact angles less than 40 degrees (See section Namely, the invention relates to the following [1] to [9], specifically [1]-[3]; The purpose of the invention is to provide excellent hydrophilicity, antifouling property and excellent dental material, especially a dental prosthesis; Here, the dental composition of the invention as a tooth, dental coating agent for repairing body is lower, in order to enhance the adhesion to a surface, can implement various pre-treatment prosthesis for the tooth, dental. For example, for coated on the natural tooth in the oral cavity of the case, the phosphoric acid aqueous solution, oxalic acid aqueous solution, citric acid solution, tartaric acid aqueous solution, ferric chloride solution to implement etching processing, or can be coated with the dentine adhesion of functional monomer with adhesion primer and adhesive). Thus, one of ordinary skill in the art would optimize the amount of hydrophilic groups in the polymer to afford the desired water contact angle that is useful for dental applications and which is known in the art to be below 40°.
In light of the forgoing 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 USC 103(a).
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. Therefore, the invention as a whole would have been prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
Allowable Subject Matter
Claim 10 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Response to Arguments/Remarks
Applicant’s amendments to the claims have overcome/rendered moot the previous grounds of rejection under 102 and have prompted the new grounds of rejection under 102 and revised/new grounds of rejection under 103 presented herein.
Applicants arguments with respect to the 102 rejection are thereby rendered moot and not further addressed herein. Applicant’s arguments with respect to claim 10 under the 103 rejection are also persuasive as applicants are correct in that the compound previously cited by the examiner has the pyridinium ring at the end of the chain and it is not similar to compound 3. This rejection has been withdrawn and further search of the 3 compounds claimed in claim 10 has prompted the examiner to acknowledge this claim as containing allowable subject matter as these compounds and obvious variants of these compounds were not found in an updated search. The claim is objected to for the reasons discussed above.
Applicant’s arguments with respect to the 103 rejection have been fully considered but are not persuasive with respect to the new/revised grounds of rejection prompted by applicant’s amendments. These arguments, insofar as they pertain to the revised/new grounds of rejection are addressed herein. Applicant’s argue that formula IV cannot be correlated to applicant’s amended formula I as now currently claimed. The examiner respectfully disagrees and respectfully points out that the examiner does not assert that formula IV corresponds to the claimed compounds of the currently amended compound scope. However, formula IV, specifically the exemplified example below which falls within the scope of formula IV shown here and above,
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corresponds to a structurally similar compound to those instantly claimed. Specifically, this compound is close bioisosteric compound, to the instantly claimed compounds and only differs from the claimed compounds in that it has an O-direct bond to the pyridine ring whereas the instant compounds have the NH-direct bond to the pyridine ring. Specifically, with respect to the above shown compound, this compound corresponds to applicant’s compounds wherein A1 is C(=O), m is 1, A2 is O, L1 and L2 are both alkyl groups which correspond to wherein n is 2-25 in the above formula and wherein the NH-L3 direct bond group now instantly claimed is instead the O-direct bond group in the above formula which is the only difference between the exemplified compound of ‘169 and the instantly claimed compounds. However, as discussed above it would be obvious to replace the O for the claimed NH group and form the claimed antimicrobial monomers/compounds when looking to ‘129 and the combined references because O and NH are well-known classical bioisoisteres of one another as is taught by Patani (Table 2, Grimms hydride displacement: O, NH, and CH2 are known classical bioisosteres; see also tables 19-20) and it is known, from In re Merck & Co., Inc., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986) (claimed and prior art compounds used in a method of treating depression would have been expected to have similar activity because the structural difference between the compounds involved a known bioisosteric replacement), because contrary to applicant’s arguments the compound(s) wherein m is 0, A1 is C(=O) and L3 being a single bond are not required by the instant claim scope.
Applicants then argue that the office has not established a reason to modify ‘129 based on the teachings of Patani. The examiner respectfully disagrees because the above rejection and previous arguments have clearly explained it would be obvious to modify ‘129 by replacing the O which is directly bonded to the pyridinium ring for the claimed NH group and form the claimed antimicrobial monomers/compounds when looking to ‘129 and the combined references because O and NH are well-known classical bioisoisteres of one another as is taught by Patani (Table 2, Grimms hydride displacement: O, NH, and CH2 are known classical bioisosteres; see also tables 19-20) and it is known, from In re Merck & Co., Inc., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986) (claimed and prior art compounds used in a method of treating depression would have been expected to have similar activity because the structural difference between the compounds involved a known bioisosteric replacement), because contrary to applicant’s arguments the compound(s) wherein m is 0, A1 is C(=O) and L3 being a single bond are not required by the instant claim scope, and it would be obvious to make the argued substation of the claimed NH as taught by Patani for the O atom in ‘129 in order to form additional antimicrobial monomers which retain the antimicrobial activity afforded by the positively charged pyridinium group.
In light of the forgoing 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 USC 103(a).
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. Therefore, the invention as a whole would have been prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
Conclusion
No claims are allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Erin E Hirt whose telephone number is (571)270-1077. The examiner can normally be reached 10:30-7:30 ET M-F.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Sue X Liu can be reached at 571-272-5539. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/ERIN E HIRT/Primary Examiner, Art Unit 1616