DETAILED ACTION
Claims 1-17 are pending, of which claims 8-11 are withdrawn.
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 .
Response to Arguments
On page 8 of the response, Applicant argues that the amendments to claims 1 and 5-7 overcome the pending objections and rejections under 35 USC §112. Examiner agrees, and as such, these objections and rejections have been withdrawn.
Applicant's arguments concerning the pending rejections under 35 USC §103 have been fully considered but they are not persuasive.
On pages 9-10 of the response, Applicant argues that Ramaseshan fails to teach the recited linker Y in the claimed structure and the use of a bridging agent selected from the recited options. Examiner agrees with this assessment as stated in the prior office action. However, as shown in the prior office action, these limitations are obvious in view of the other cited prior art.
On pages 10-11 of the response, Applicant argues that the synthetic route for the cyclodextrin derivative describe in Ramaseshan appears unlikely, the characterization is incomplete, and the experimental data has not been supported by subsequent literature. Applicant points to a declaration by Prof. Francois Estour in support of these statements. Applicant concludes that Ramaseshan should not be considered a reliable teaching of the prior art.
On page 2 of the affidavit, Prof. Estour states that Ramaseshan fails to provide precision for the mechanism of the reaction of b-cyclodextrin and 2-iodosobenzoic acid. The affidavit states that Ramaseshan fails to prove the location for the introduction of the phenyl group on the b-cyclodextrin. However, Ramaseshan provides evidence showing that the substitution occurs at the “2” position in the cyclodextrin rather than the 3 or the 6 position (see e.g. page 2951, first column, first paragraph, starting “Functionalization of b-CD…”). Ramaseshan describes that the first step in the process is deprotonation with sodium hydride, and that as the 2-position is the most acidic and least hindered, it is likely that this is the location for substitution (Id.). Although the affidavit states that this is not proven, the affidavit does not provide any factual evidence to support a conclusion that a different position is substituted.
The affidavit also states on page 2 that it is “not clear how the nucleophilicity of the iodoso function could influence the regioselectivity of the reaction.” However, the mechanism for the substitution is not claimed, and therefore immaterial. Further, the affidavit provides no factual evidence to support a conclusion that substitution occurs at a different location than that described in Ramaseshan.
Further on page 2, the affidavit states that it is unclear how the authors could claim compound (c) in 80% yield while also stating that the selectivity for compound (c) compared to compound (b) is 66% to 34%. However, it seems likely that Ramaseshan is stating that the total yield of substituted b-cyclodextrin by this method is 80%, 66% of which is compound (c). Further, as the yield of the compound is not claimed in the instant application, the yield is not material to patentability.
On pages 2-3, the affidavit states that the data used to confirm the structure in Ramaseshan lacks precision. Notably, the authors of Ramaseshan did not use mass spectroscopy or explain the procedures to analyze the NMR spectra provided. However, the affidavit does not provide any factual evidence to suggest that the structure shown in Ramaseshan is incorrect. The affidavit states that more precision should have been used in the analysis of the data, but provides no evidence that the structure is wrong and no showing that the correct structure would have different properties or NMR characteristics.
On page 3, the affidavit states that the reaction scheme provided in Masurier only allows for a single position for substitution on the aromatic ring. However, the mere fact that the compound could have been made by the process of Masurier, or that Masurier provided more data to support the various structures, does not show that the method of Ramaseshan would fail.
On pages 3-4, the affidavit states that, when using different conditions than Ramaseshan, different effectiveness for specific compounds are obtained. However, as the affidavit notes, specific conditions used during the hydrolysis tests affect the results. As such, this is not persuasive evidence that the structure or results of Ramaseshan is incorrect when one would expect different results when using different conditions.
On page 4, the affidavit concludes that one of ordinary skill in the art would not be motivated to combine the teachings of Masurier and/or Vraz to arrive of the claimed invention. However, no reasoning is provided for this conclusion.
Accordingly, the affidavit is not persuasive in overcoming the pending rejections under 35 USC §103.
Claim Objections
Claim 13 is objected to because of the following informalities: the claim does not end in a period. Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 13 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Regarding claim 13, the claim recites that the linker is both O-(CH2)3- and the triazole linker. As such, it is unclear whether the linker needs to include both types of functional groups, or whether the linker can include either one of the listed options. Based on the disclosure, which does not include any compounds having both the ether and triazole linker, claim 13 is interpreted as if the word “or” was provided between the two groups.
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.
Claims 1-7, 12, and 15 are rejected under 35 U.S.C. 103 as being unpatentable over Ramaseshan, et al. "Functionalized polymer nanofibre membranes for protection from chemical warfare stimulants." Nanotechnology 17.12 (2006): 2947 (“Ramaseshan”) in view of Masurier, et al. "Synthesis of 2-substituted β-cyclodextrin derivatives with a hydrolytic activity against the organophosphorylester paraoxon." European journal of medicinal chemistry 40.7 (2005): 615-623 (“Masurier”) and Vraz, et al. "Wool fabric treated with eco-friendly insect repellent." Fibres & Textiles in Eastern Europe 4 (124 (2017): 102-105 (“Vraz”).
Regarding claim 1, Ramaseshan teaches functionalization of a fiber using b-cyclodextrin, which meets the general structure recited where n is 2 (see e.g. page 2949, first column, last paragraph starting “In this paper…”). Ramaseshan further teaches that the cyclodextrin is modified by bonding with IBA, which meets the limitation for Nu, where R is COOH and X is C-I=O (see e.g. scheme 1 on page 2951). Ramaseshan teaches that the method includes contacting the fiber with the cyclodextrin derivative to obtain a fiber with the immobilized cyclodextrin derivative (see e.g. page 2949, second column, fifth paragraph, starting “Five different membranes…”).
Ramaseshan does not teach using one of the bridging agents. However, Vraz teaches a method for immobilizing cyclodextrin derivatives on fibers (see e.g. page 102, second column, first full paragraph, starting “Cyclodextrins have…”). Vraz teaches that using a substance like 1, 2, 3, 4 butanetetracarboxilic acid allows for permanent links between the cyclodextrins and the fiber (see e.g. page 103, first column, first full paragraph, starting “This phenomenon is…”). Accordingly, prior to the effective filing date of the invention, it would have been obvious to modify the method of Ramaseshan to include a bridging agent of 1, 2, 3, 4 butanetetracarboxilic acid to more permanently attach the cyclodextrins to the fibers, as taught by Vraz.
The Nu portion of Ramaseshan is directly attached to the hydroxyl of the cyclodextrin, which is a different linkage than the recited linker Y. However, Masurier teaches a very similar cyclodextrin derivative that functionalized at the same position by IBA (see Scheme 1 on page 616). Masurier teaches that the IBA is linked to the cyclodextrin by a linker -O-CH2-, which meets the limitation recited for Y when m is 1 (Id.). Masurier further teaches that IBA and derivatives connected to the cyclodextrin via a linker meeting the limitation of Y effectively hydrolyzes the organophosphorus agent paraoxon (see e.g. page 620, second column, last paragraph, starting “Different b-CD derivatives…”). Accordingly, prior to the effective filing date of the invention, it would have been obvious to modify the textile of Ramaseshan to use the linker of Masurier because Masurier teaches that IBA connected via this linker can effectively hydrolyze paraoxon.
Regarding claim 2, Vraz teaches that using a catalyst, and in particular cyanamide, can reduce the temperature necessary for linking the cyclodextrins to the fiber, which allows modification of fibers that cannot tolerate high temperatures (see e.g. paragraph bridging pages 102-103, starting “Polycarboxylic acids…”). Accordingly, prior to the effective filing date, it would have been obvious to use a cyanamide catalyst as taught by Vraz in the method of Ramaseshan in order to allow immobilization of the cyclodextrin at a lower temperature, as taught by Vraz.
Regarding claim 3, the bridging agent taught by Vraz is 1, 2, 3, 4 butanetetracarboxilic acid, and the catalyst is cyanamide (see e.g. paragraph bridging pages 102-103, starting “Polycarboxylic acids…”).
Regarding claim 4, as noted above the Nu portion recited in claim 4 is not one of the Nu portions recited in claim 1. However, Masurier teaches that the iodosobenzoic acid used as the Nu portion is in equilibrium with the Nu recited in claim 4 (see e.g. FIG. 3 on page 618). As such, at least some of the cyclodextrin derivatives in the product would be expected to have the recited configuration. Further, both Ramaseshan and Masurier teach that the method uses b-cyclodextrin, which is the type of cyclodextrin recited in claim 4 (see e.g. Ramaseshan at page 2949, first column, second full paragraph, starting “In this paper…”; as well as Masurier at page 616, first column, third full paragraph, starting “Ortho-iodosobenzoic acid…”).
Regarding claim 5, Ramaseshan teaches that the fiber is made from a PVC fiber, which is a synthetic fiber (see e.g. page 2949, first column, second full paragraph, starting “In this paper…”).
Regarding claim 6, Vraz teaches that, when using the cyanamide catalyst, the temperature during the contacting can be 115 °C, which is within the claimed range (see e.g. paragraph bridging pages 102-103, starting “Polycarboxylic acids…”).
Regarding claim 7, Vraz teaches rinsing the textile after immobilization of the cyclodextrin (see e.g. page 103, paragraph bridging second and third columns, starting “Wool fabric samples…”).
Regarding claim 12, Masurier teaches that the IBA is linked to the cyclodextrin by a linker -O-CH2-, which meets the limitation recited for Y when m is 1 (see Scheme 1 on page 616).
Regarding claim 15, Vraz teaches that step (a) is carried out for 3 minutes, which is within the claimed range (see e.g. page 103, paragraph bridging second and third columns, starting “Wool fabric samples…”).
Claims 16-17 are rejected under 35 U.S.C. 103 as being unpatentable over Ramaseshan in view of Masurier and Vraz as applied to claim 7 above, as evidenced by International Standard ISO 105-C10 (“ISO”).
Regarding claim 16, Vraz teaches that the rinsing of step (b) is carried out at 40°C, which is within the claimed range, by standard test method ISO 105-C10 (see e.g. page 103, paragraph bridging second and third columns, starting “Wool fabric samples…”). As shown in ISO, the rinsing referred to that is performed at 40°C is done for 30 minutes, which is within the claimed range (see e.g. ISO at Table 2).
Regarding claim 17, Vraz teaches that the rinsing of step (b) is carried out by standard test method ISO 105-C10 (see e.g. page 103, paragraph bridging second and third columns, starting “Wool fabric samples…”). As shown in ISO, the rinsing portion of the test includes rinsing with grade 3 water and tap water, which are within the claimed pH range (see e.g. ISO at page 4, section 7.3).
Claim 13 is rejected under 35 U.S.C. 103 as being unpatentable over Ramaseshan in view of Masurier and Vraz as applied to claim 1 above, and further in view of Letort, et al. "Structure–efficiency relationships of cyclodextrin scavengers in the hydrolytic degradation of organophosphorus compounds." Beilstein Journal of Organic Chemistry 13.1 (2017): 417-427 (“Letort”).
Regarding claim 13, Ramaseshan in view of Masurier and Vraz teaches the limitations of claim 1 as described above, but do not teach that the linker is O-(CH2)3-. Rather, Masurier teaches that the linker is O-CH2- (see Scheme 1 on page 616). However, Letort teaches the same Nu portion connected to cyclodextrin for degradation of organophosphorus compounds, which is the same purpose as Ramaseshan (see e.g. structure 4 in FIG. 3 of Letort). Letort teaches that compounds that use a 3-carbon linker are more effective at hydrolysis of the target organophosphorus compound than those that use a 1 carbon linker (compare compounds 2 vs. 3 in FIG.’s 5-6). Letort further teaches that this more effective linker has the same effectiveness when used with the cyclodextrin compound that is otherwise not further functionalized (compare compounds 2 vs. 4 in FIG. 7). That is, the same increase in effectiveness occurs when looking only at the linker to the IBA portion. Accordingly, prior to the effective filing date of the invention, it would have been obvious to a person of ordinary skill in the art to use a 3-carbon linker as taught by Letort in place of the 1-carbon linker of Masurier in order to increase the effectiveness of the IBA in hydrolyzing organophosphorus agents.
Claim 14 is rejected under 35 U.S.C. 103 as being unpatentable over Ramaseshan in view of Masurier and Vraz as applied to claim 1 above, and further in view of WO 2006077604 (“Ranaldo”).
Regarding claim 14, Ramaseshan in view of Masurier and Vraz teaches the limitations of claim 1 as described above. Ramaseshan teaches that the fiber is made from a PVC fiber rather than one of the recited materials. However, Ranaldo teaches a similar method for fixing a cyclodextrin compound to fabric (see e.g. page 5, 3rd full paragraph, starting “Still another object…”). Ranaldo teaches that the cyclodextrin can be stably fixed to materials such as cotton (see e.g. page 11, second paragraph, starting “Preferably, the composition…”). Accordingly, prior to the effective filing date of the invention, it would have been obvious to a person of ordinary skill in the art to use a cotton fabric as taught by Ranaldo in place of the PVC fiber of Ramaseshan in order to expand the types of fabrics that can be protected by the method of Ramaseshan.
Conclusion
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.
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/E.S.S./Examiner, Art Unit 1736
/ANTHONY J ZIMMER/Supervisory Patent Examiner, Art Unit 1736