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 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.
Claim(s) 1-21 is/are rejected under 35 U.S.C. 103 as being unpatentable over CN111072966A abstract, page 2 lines 21-37, page 3 lines 3-134 lines 21-31and claim 1; in view of CN101215379A abstract, page 2 lines 3-4, and 17-25, page 3 lines 8-17, page 4 lines 3-29.and Examples 1-5 on pages 5-6.
Claim 1 is directed to a polythioamide, characterized in that its structure comprises comprising thioamide repeating units positioned at least partly in the side chains of the polymer, and wherein in that it the polythioamide has an average molecular weight of 2.5kDa-1000kDa.
CN111072966A discloses a polythioamide resin prepared by polymerizing piperazine with biphenol derivatives to obtain a polymer comprising thioamide containing repeating units. The reference also teaches polymerization degrees of approximately n+10-1000 which would result in polymers having molecular weights within or overlapping the claimed range.
CN101215379A discloses sulfur containing amide polymers and recognizes that the polymer structure and molecular weight may be selected to obtain the physical and chemical properties desired. See abstract, page 2 lines 3-4, and 17-25 and page 4 lines 3-12 and 23-29.
Thus, it would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to modify the polymer structure of the polythioamide disclosed by CN111072966B in view of CN101215379A to include the thioamide moiety within the polymer backbone. Moreover, the selection of an average molecular weight as routine optimization of known reaction conditions or process parameters to obtain the desired properties.
Claim 2 is directed to the polythioamide according to claim 1, wherein the
polythioamide is selected from a thionated product of a poly(2-oxazoline), poly(2-oxazine), polyacrylamide, polymethacrylamide, or polyvinylcaprolactam.
CN101215379A discloses sulfur containing amide polymers and recognizes that the polymer structure and molecular weight may be selected to obtain the physical and chemical properties desired. It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to select the claimed polymer backbone from known amide polymers since CN101215379A recognizes that thionation of different amide polymers is a routine variation for obtaining polymers containing thioamide functional groups while keeping the desired polymer properties.
Claim 3 is directed to the polythioamide according to claim 1, having a structure containing thioamide repeating units positioned entirely in the polymer side chains.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to place the thioamide repeating units within the polymer side chains since the location of the functional groups in the polymer backbone or side chains is recognized as a routine choice used to adjust polymer properties such as solubility, reactivity and mechanical performance.
Claim 4 is directed to the polythioamide according to claim 1,
which-wherein the polythioamide is selected from a thionated product of a polyacrylamide, polymethacrylamide, or polyvinylcaprolactam. It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to employ a sulfur containing amide polymer as taught by CN101215379A (abstract) in combination with the polythioamide of CN111072966A (abstract) since both references are directed to sulfur containing amide polymers which may be inclusive of polyacrylamides and related polymers since the selection of a particular amide containing polymer for incorporating sulfur would have been an obvious choice depending on the desired polymer properties.
Claim 5 is directed to the polythioamide according to claim 1,
wherein the polythioamide which an average molecular weight of 25kDa-500kDa.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention since, in addition to the discussion for claim 1 above, molecular weight is routinely optimized to obtain desired viscosity, mechanical strength and processing characteristics.
Claim 6 is directed to the polythioamide according to claim 1,
wherein the polythioamide which has a degree of substitution (DS) of at least 1%.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention since the extent of thionation is controlled through routine adjustment of reaction conditions such as reagent concentrations, reaction time and temperature to obtain the desired level of functionalization and the degree of substitution would represent routine optimization.
Claim 7 is directed to a method for preparing a polythioamide having a structure
comprising thioamide repeating units positioned at least partly in the side chains of the polymer, and having an average molecular weight of 2.5kDa-1000kDa, the method comprising: reacting a polyamide having its-amide repeating unit-units at least partly in a side chain of the polymer with 2,4-bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane (C14H₁₄O₂P₂S₄),1,3,5,7-tetrakis(sulfanylidene)-2,4,6,8,9,10-hexathia-1,3)5,7 tetraphosphatricyclo[3.3.1.1²']decane (phosphorus pentasulphide, P4S10), 2,4-Bis(p-tolylthio)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (C14H₁₄P₂S₆), or pentathiodiphosphorus(V) acid-P,P'-bis(pyridinium betaine) (C10H₁₀N₂P₂S₅), as a thiolation reagent.
CN111072966A teaches a method of preparing a thioamide polymer by converting amide functionalities into thioamide functionalities to produce a polythioamide having thioamide repeating units positioned at least particle with the polymer side chains. CN101215379A further teaches the use of sulfurizing or thionation reagents for converting amide groups into thioamide groups during the preparation of the polymers including the use of known thionation reagents suitable for the process. See abstract, page 3 lines 8-17, page 4 lines 3-22.and Examples 1-5 on pages 5-6.
It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to employ one of the recited thionation reagents as claimed since these reagents were well known equivalents for converting amide groups to thioamide groups. Generally, it is prima facie obvious to select a known material for incorporation into a composition, based on its recognized suitability for its intended purpose. See Sinclair & Carroll Co. v. Interchemical Corp., 325 US 327, 65 USPQ 297 (1945). (Selection of solvent having boiling point and vapor pressure properties recognized as being ideal for printing inks into printing ink compositions found obvious on its face). See also In re Leshin, 227 F.2d 197, 125 USPQ 416 (CCPA 1960). (Selection of a known plastic to make a plastic container found obvious on its face).
Claim 8 is directed to the method according to claim 7, wherein the polyamide is reacted with the thiolation reagent, 2,4-bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane (C₁₄H₁₄O₂P₂S₄).It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention since theses reagents were well-known reagents for converting amides to thioamides and are recognized equivalents for accomplishing the claimed reaction.
Claim 9 is directed to the method according to claim 7, wherein the polyamide is reacted with the thiolation reagent at a temperature of 50-200 °C. It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention since the reaction temperatures are routinely optimized to obtain efficient conversion while maintaining the desired reaction rates and products yields and it is well-established that merely selecting proportions and ranges is not patentable absent a showing of criticality. In re Becket, 33 U.S.P.Q. 33 (C.C.P.A. 1937). In re Russell, 439 F.2d 1228, 169 U.S.P.Q. 426 (C.C.P.A. 1971).
Claim 10 is directed to the method according to claim 7, wherein 5 to 500,000 mols of the thiolation reagent, is added for each mol of polyamide. It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to select the claimed molar ration of thionation reagent to polyamide since reagent concentration is routinely optimized to obtain the desired degree of thionation while minimizing the side reactions and it is well-established that merely selecting proportions and ranges is not patentable absent a showing of criticality. In re Becket, 33 U.S.P.Q. 33 (C.C.P.A. 1937). In re Russell, 439 F.2d 1228, 169 U.S.P.Q. 426 (C.C.P.A. 1971).
Claim 11 is directed to the method according to claim 7, wherein at least 1%, of the amide repeating units are thionated. It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention since the extent of thionation is controlled by routine adjustments of reaction conditions and it is well-established that merely selecting proportions and ranges is not patentable absent a showing of criticality. In re Becket, 33 U.S.P.Q. 33 (C.C.P.A. 1937). In re Russell, 439 F.2d 1228, 169 U.S.P.Q. 426 (C.C.P.A. 1971).
Claim 12 is directed to the method according to claims 7, wherein the polyamide is obtained by cationic or anionic ring opening polymerization, by free radical polymerization, or by controlled radical polymerization. It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention since each step is well known for preparing amide polymers suitable for thionation.
Claim 14 is directed to the polythioamide according to claim 1, wherein the polythioamide is selected from a thionated product of a poly(2-oxazoline), poly(2-oxazine), polyacrylamides, polymethacrylamides, polyvinylpyrrolidone, or poly(n-acryloyl glycinamide).It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention since CN111072966A discloses the preparation of a polythioamide resin and CN101215379A discloses the preparation of sulfur containing amide polymers. The selection of a particular amide polymer as the starting material would have been an obvious routine choice based on the desired properties sought in the resulting polymer.
Claim 15 is directed to the polythioamide according to claim 1, wherein the polythioamide has a degree of substitution (DS) of at least 20%.It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention since the degree of substitution is routinely controlled though reaction conditions and represents a routine optimization.
Claim 16 is directed to the method according to claim 1, wherein the polythioamide is a homopolymer consisting of thioamide repeating units. It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention since homopolymers and copolymers were both well-known polymer structures and selecting a homopolymer would have been obvious to the skilled artisan based on the material properties sought.
Claim 17 is directed to the method according to claim 1, wherein a therapeutic compound is conjugated to the polythiomide. It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention to conjugate a therapeutic compound to the polythioamide since functional polymers were commonly used as carriers for biologically active agents.
Claim 18 is directed to the method according to claim 7, wherein 5 to 50,000 mols of the thiolation reagent is added for each mol of polyamide. It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention since a reagents concentration is routinely optimized to achieve the desired degree of thionation.
Claim 19 is directed to the method according to claim 7, wherein at least 10% of the amide repeating units are thionated. It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention since the degree of thionation is a result effective variable which is controlled by reaction conditions.
Claim 20 is directed to the method according to claim 7, wherein the polyamide is obtained by cationic or anionic ring opening polymerization, by free radical polymerization, or by controlled radical polymerization with 25 to 10,000 monomer repeating units. It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention since each CN111072966B and CN101215379A disclose known methods of synthesizing amide polymers which re suitable for thionation.
Claim 21 is directed to the method according to claim 7, the polyamide is reacted with the thiolation reagent in a solvent comprising a member selected from the group consisting of dichloromethane, chlorobenzene, chloroform, tetrachloromethane, dimethylsulfide, dimethylsulfoxide, tetrahydrofuran, dioxane, tetrahydropyrane, trifluorotoluene, and hexafluoroisopropanol. It would have been obvious to one having ordinary skill in the art before the effective filing date of the claimed invention since the selection of a suitable organic solvent for carrying out thionation reactions was well known in the art and constitutes routine optimization based on solubility, reaction rates and processing conditions.
In conclusion, in view of the above, there appears to be no significant difference between the reference(s) and that which is claimed by applicant(s). Any differences not specifically mentioned appear to be conventional. Consequently, the claimed invention cannot be deemed as unobvious and accordingly is unpatentable.
Information Disclosure Statement
Note that any future and/or present information disclosure statements must comply with 37 CFR § 1.98(b), which requires a list of the publications to include: the author (if any), title, relevant pages of the publication, date and place of publication to be submitted for consideration by the Office.
Improper Claim Dependency
Prior to allowance, any dependent claims should be rechecked for proper dependency if independent claims are cancelled.
Correspondence
Any inquiry concerning this communication or earlier communications from the examiner should be directed to TERRESSA M BOYKIN whose telephone number is (571)272-1069. The examiner can normally be reached M-F 7-5:30.
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/Terressa Boykin/ Primary Examiner, Art Unit 1765
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