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 .
Information Disclosure Statement
The Information Disclosure Statement (IDS) filed on 10/26/2023 has been considered by the Examiner inasmuch as foreign documents have been submitted into the file wrapper in English.
Claim Status
The preliminary amendment filed October 26, 2023 has been entered. Claims 1-16 are canceled. Claims 17-31 are new. Thus, claims 17-31 are examined on the merits herein.
Specification
The disclosure is objected to because of the following informalities:
The Examiner respectfully notes the specification discloses a sulfate moiety can be represented by formula (X-VI) depicted as ----SO3- M+, see specification pg. 7, lines 10-15.
However, the Examiner respectfully notes the structure as represented by formula (X-VI) is a sulfonate moiety and not a sulfate as recited within the specification.
Additionally, the Examiner respectfully notes the exemplification stated above is contrary to the normal definition of “sulfate” which is -SO42-.
Thus, the specification is objected to base on the exemplification as stated above.
Appropriate correction is required.
Claim Objections
Claims 22 and 31 are objected to because of the following informalities:
(I) Claim 22, line 2 recites the phrase “a a perfluorinated (C5-C7)cycloalkyl”, which recites a redundant “a” immediately before the word “perfluorinated”.
Thus, to promote clarity the Examiner respectfully suggests deleting one of the two article “a” recited immediately before the word “perfluorinated” as discussed above.
(II) Claim 31, line 2, recites “FhuA” which is an uncommon abbreviation. The Examiner respectfully notes within Applicant’s specification “FhuA” is the abbreviation for the membrane protein known as Ferrichrome outer membrane transporter/phase receptor, see specification, pg. 2, lines 20-25.
Thus, to promote clarity the Examiner respectfully suggests replacing the phrase “FhuA” with the phrase “Ferrichrome outer membrane transporter/phase receptor (FhuA)”.
Appropriate correction is required.
Claim Rejections - 35 USC § 102
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.
Claims 17 and 22-23 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Holland et al. (Published 02 October 1973, US-3763207-A, IDS filed 10/26/2023).
Holland teaches perfluorocyclic carbinol sulfate salts, see Col. 1, lines 1-5.
Holland teaches compounds having the general structure,
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, wherein X is fluorine and Y is an alkali metal, see lines 30-40.
The Examiner respectfully notes when X is fluorine it results in a perfluorinated hexyl with the chemical formula C6F11 as shown above.
The Examiner also respectfully notes the general structure of Holland as discussed above reads on the compound of formula (I) of claim 17, wherein X is a sulfate, required in claim 17, line 5; Y is a C1 aliphatic linker, required in claim 17, line 6; and Z is a perfluorinated C6-cycloalkyl, required in claim 17, line 9; and claims 22-23.
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.
(I) Claims 17-21, 24 and 27-28 are rejected under 35 U.S.C. 103 as being unpatentable over Polidori et al. (Published 07 April 2016, New Journal of Chemistry, Vol. 40, pp. 5364-5378, IDS filed 10/26/2023) in view of Baba et al. (Published 07 January 2020, Chemistry and Physics of Lipids, Vol. 227, Article Number: 104870, pp. 1-6, PTO-892).
Regarding claims 17-21, 24 and 27-28, Polidori teaches sparingly fluorinated maltoside-based surfactants, see pg. 5364, title.
Polidori teaches a synthesized maltose-based fluorosurfactant bearing a perfluoroethyl (F2H9) or a perfluorobutyl (F4H5) tip at the end of the chain, see pg. 5364, abstract.
Polidori illustrates the structure of the maltose-based fluorosurfactants bearing either a perfluoroethyl (F2H9) or a perfluorobutyl (F4H5) tip within scheme 1 as,
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375
659
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, see pg. 5365, scheme 1.
The Examiner respectfully notes the maltose-based fluorosurfactants taught by Polidori as shown above comprise a maltoside as a polar moiety (e.g. X is maltoside, required in claims 17-19 and 25-28); and where the maltoside is connected to a pentylene when m=1 as exemplified within F4H5βM as shown above (e.g. Y is a C5 aliphatic linker, required in claims 17-19; a C5-alkylene, required in claim 20 and claim 25; a pentylene, required in claim 21; and wherein n is 3, required in claims 26-28).
The Examiner also respectfully notes scheme 1 depicts either a perfluoroethyl (F2H9) or a perfluorobutyl (F4H5) tip at the end of the chain of the maltose-based fluorosurfactants of Polidori as discussed above.
Polidori teaches the chemical synthesis of both F2H9βM and F4H5βM in scheme 2, see pg. 5370, scheme 2.
Although, Polidori does not teach the maltose-based fluorosurfactant has a perfluorinated isopentyl, as required in claims 17, 19, 24, and 27-28.
However, in the same field of endeavor of fluorosurfactants, the Examiner respectfully reiterates within scheme 1 of Polidori the scheme explicitly teaches the -CF2- of the perfluorinated alkyl is n=1 in F2H9βM or n=3 in F4H5βM. Therefore, based on these combined teachings the Examiner respectfully notes a range of n=1-3 is suggested by the teachings of Polidori as discussed above.
The Examiner further respectfully notes when n=2 as discussed above it would result in and correspond to m=1 of formula (III) within instant claim 27. Thus, it would have been within the scope of the artisan to have modified the -CF2- of the perfluorinated alkyl of the maltose-based fluorosurfactants taught by Polidori above to be where n=2, as the Examiner reasonably interprets n=2 as a homologous structure in view of the teachings of Polidori which explicitly teach n=1 or n=3 as discussed above.
Additionally, MPEP 2144.09(II) states “homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties”. Thus, it would have been within the scope of the artisan to include the limitation n=2 into the maltose-based fluorosurfactants taught by Polidori above, as one of ordinary skill in the art would have reasonably interpreted the structure that resulted from the limitation n=2 to be a homolog based on the structures taught by Polidori above; and would had reasonably expected said structure possesses similar properties to the structures where n=1 or n=3 as taught by Polidori above.
Moreover, Baba teaches partially fluorinated octyl-phosphocholine surfactants, see pg. 1, title.
Baba teaches the chemical structure of F7+2H1PC depicted as,
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, see pg. 2, Figure 1, F7+2H1PC.
Baba teaches the chemical synthesis of F7+2H1PC, see pg. 2, right column, 2.2.4. F7+2H1PC (3,7-bis(trifluoromethyl)-2,2,3,4,4,5,5,6,6,7,8,8,8 tridecafluorooctyl-PC).
In view of the teachings of Baba as discussed above, the Examiner respectfully notes the terminal carbon at the end of the perfluorinated chain of F7+2H1PC as depicted and taught by Baba above is further substituted with two trifluoromethyls as required in formula (III) of instant claim 27.
Accordingly, the Examiner respectfully notes Baba teaches branched perfluorinated alkyls as a known consideration in the art as required in instant claims 17, 19, 24 and 27-28; and for this reason it would have been well within the scope of the artisan to have modified the terminal CF3 of the maltose-based fluorosurfactants taught by Polidori above with two trifluoromethyl as taught by Baba above and thus arrive at the terminal -CF- substituted with two trifluoromethyls as recited within formula (III) of instant claim 27 in view of the combined teachings of Polidori and Baba above.
The Examiner also respectfully notes the terminal -CF- substituted with two trifluoromethyls is comprised within the compound of 5-(perfluoroisopentyl)-pentoxy-4-O-(α-D-glucopyranosyl)-β-D-glucopyranoside as recited within instant claim 28.
Consequently, based on the teachings of Polidori and Baba as discussed above, the Examiner respectfully notes that using the teachings of scheme 1 of Polidori, where m=1, wherein this limitation corresponds to a pentylene structure as required of the compound as recited within the instant claims; the modification within the scope of the artisan where n=2 as discussed above, corresponding to the limitation of m=1 in formula (III) of instant claim 27; and the known substitution in the art of replacing the terminal -CF3 of the perfluorinated structure as exemplified within the maltose-based fluorosurfactants taught by Polidori for a terminal -CF- substituted with two trifluoromethyls as taught by the fluorosurfactants of Baba above, which correspond to the terminating end of the perfluorinated alkyl as recited within formula (III) of instant claim 27; the Examiner respectfully notes the combined teachings of Polidori and Baba as discussed above suggest a compound which meets all structural limitations as recited and required within instant claims 17-21, 24 and 27; and when all of these teachings and considerations are taken together would suggest and result in the compound recited as 5-(perfluoroisopentyl)-pentoxy-4-O-(α-D-glucopyranosyl)-β-D-glucopyranoside within instant claim 28, as evidenced by the specification which discloses 5-(perfluoroisopentyl)-pentoxy-4-O-(α-D-glucopyranosyl)-β-D-glucopyranoside as compound 8c (see pg. 33, lines 20-25) and visually depicts the structure of compound 8c (see pg. 29, scheme 2, compound 8c).
Therefore, in view of the foregoing reasons above, it would have been prima facie obvious to one of ordinary skill in the art before the invention was filed to have incorporated the teachings of Baba into the compounds as taught by Polidori above and thus would have arrived at the maltose-based fluorosurfactant having a perfluorinated isopentyl as recited and required by the instant claims as discussed above as within the scope of the artisan as combining prior art elements according to known compounds to yield predictable results.
One of ordinary skill in the art would have been motivated to create sparingly fluorinated maltoside-based surfactants as taught by Polidori above. One of ordinary skill in the art would have had a reasonable expectation of success as both Polidori and Baba teach chemical synthesis of surfactants comprising polar moieties, alkylene linkers and perfluorinated alkyls as discussed above.
Thus, the claimed invention as a whole would have been prima facie obvious over the combined teachings of the prior art.
(II) Claims 29-31 are rejected under 35 U.S.C. 103 as being unpatentable over Polidori et al. (Published 07 April 2016, New Journal of Chemistry, Vol. 40, pp. 5364-5378, IDS filed 10/26/2023) in view of Baba et al. (Published 07 January 2020, Chemistry and Physics of Lipids, Vol. 227, Article Number: 104870, pp. 1-6, PTO-892) as applied to claims 17-21, 24 and 27-28 above, and further in view of Barnidge et al. (Published 10 April 1999, Analytical Biochemistry, Vol. 269, Issue 1, pp. 1-9, PTO-892).
Polidori and Baba address claims 17-21, 24 and 27-28 as written above.
Polidori further teaches their sparingly fluorinated maltoside-based surfactants for membrane-protein stabilization, see pg. 5364, title.
Polidori teaches F2H9βM and F4H5βM were tested for their ability to keep membrane-proteins (MP) soluble and in their native form using bacteriorhodopsin (bR) as a model protein, see pg. 5375, right column, biochemical evaluation.
Polidori shows in Fig. 6 the results of sucrose density gradient experiments where small globular micelles formed by both surfactants; and where a sharp color band indicated homogenous protein-surfactant complexes, pg. 5375, right column, biochemical evaluation.
Polidori teaches when the bacteriorhodopsin (bR) protein is solubilized in detergent, the protein appears purple, pg. 5375, right column, biochemical evaluation.
Polidori teaches when the solubilized monomeric bR protein is transferred into a fluorinated surfactant it gives a blue color to the protein-surfactant, see pg. 5375, right column, biochemical evaluation. Polidori teaches that bR in F2H9βM migrated as a blue band nearly at the same position as that in H12βM, e.g. the commercial detergent dodecyl maltoside, see pg. 5375, right column, biochemical evaluation.
Polidori teaches this observation is in agreement with the fact that F2H9βM being less fluorinated has a density closer to that of H12βM; and that when transferred into F4H5βM, bR still gave rise to the blue band but migrated a bit deeper into the gradient, which is expected for a protein-surfactant complex of higher density, see pg. 5376, left column, paragraph 1. Polidori depicts the purple band of H12βM and the blue bands of F2H9βM and F4H5βM visually within Figure 6, see pg. see pg. 5376, left column, Figure 6.
Polidori teaches high-resolution mass spectrometry by electro spray ionization (HRMS-ESI) was carried out on a QStar Elite mass spectrometer, see pg. 5366, left column, paragraph 1; in the characterization of F4H5βM, see pg. 5366, right column, 6’,6’,7’,7’,8’,8’,9’,9’,9’-Nonafluorononanyl-4-O-(α-D-glucopyranosyl)-β-D-glucopyranoside (F4H5βM), paragraph 2; as well as F2H9βM, see pg. 5367, right column, 10’,10’,11’,11’,11’-Pentafluoroundecyl 4-O-(α-D-glucopyranosyl)-β-D-glucopyranoside, paragraph 2.
Although, Polidori does not teach the extraction method as required in claim 30.
However, in the same field of endeavor of membrane-protein applications, Barnidge teaches an extraction method for analysis of detergent-solubilized bacteriorhodopsin by electrospray ionization mass spectrometry (e.g. an in-vitro method for extracting a membrane-protein, required in claim 30, line 1), see pg. 1, title.
Barnidge teaches sample preparation where bacteriorhodopsin (e.g. the membrane-protein, required in claim 31, line 2) was obtained from purple membranes isolated from H. salinarium (e.g. a biological sample, required in claim 30, lines 1-2) and purified by sucrose gradient centrifugation (e.g. recovering a membrane-protein, required in claim 30, line 5), see pg. 2, right column, materials and methods, sample preparation, paragraph 1.
Barnidge teaches a 100-µL volume of the membrane suspension, containing 370 pmol of bacteriorhodopsin was mixed with 100-µL of a 1% detergent solution, where the membranes were totally dissolved by either of three detergents chosen from and including octyl-β-glucoside, see pg. 2, right column, materials and methods, sample preparation, paragraph 1.
Therefore, in view of the foregoing teachings above, it would have been prima facie obvious to one of ordinary skill in the art at the invention’s effective filing date to have incorporated the teachings of Barnidge as discussed above into the sucrose density gradient experiments of Polidori as discussed above as within the scope of the artisan as combining prior art elements according to known methods to yield predictable results. One of ordinary skill in the art would have had a particular motivation to combine these references as Polidori teaches their synthesized maltose-based fluorosurfactants for membrane-protein stabilization, specifically for stabilizing the membrane protein bacteriorhodopsin as taught by both Polidori and Barnidge as discussed above.
One of ordinary skill in the art would have had a reasonable expectation of success of incorporating the teachings of Barnidge into the sucrose density gradient experiments of Polidori; as both Polidori and Barnidge are drawn to using sucrose density gradient experiments in recovering bacteriorhodopsin as discussed above.
Furthermore, with particular respect to the limitation “contacting a compound as defined in claim 17 of a detergent composition comprising said compound with a biological sample comprising a membrane-protein”, required in claim 20, lines 3-4; the Examiner reasonably interprets this limitation to be a physical limitation of mixing said biological sample with the detergent composition as required in claim 30. Since the combination of Polidori and Barnidge teach extracting and purifying bacteriorhodopsin from a biological sample using a detergent composition, which comprises the compound as defined within claim 17 for the express purpose of membrane-protein stabilization of bacteriorhodopsin within said sucrose density gradient experiments as taught by the combination of Polidori and Barnidge, the Examiner respectfully notes the physical limitation of “contacting” as required within the limitation as discussed above will be met by the combined teachings of Polidori and Barnidge as discussed above.
Therefore, it would have been prima facie obvious to one of ordinary skill in the art before the invention was filed to have incorporated the teachings of Barnidge into the sucrose density gradient experiments of Polidori as discussed above as within the scope of the artisan as combining prior art elements according to known methods to yield predictable results. One of ordinary skill in the art would have been motivated to combine these references in order to use the teachings of Barnidge in order to first extract bacteriorhodopsin from a biological sample; solubilize said bacteriorhodopsin with the detergent composition of Barnidge; and then to have purified said bacteriorhodopsin with sucrose density gradient centrifugation as taught by Barnidge; by specifically adding into the detergent composition of Barnidge the sparingly fluorinated surfactant as taught by Polidori and Baba above in order to stabilize the membrane protein bacteriorhodopsin as discussed above.
One of ordinary skill in the art would have had a reasonable expectation of success of incorporating the teachings of Barnidge into the sucrose density gradient experiments of Polidori, because both Barnidge and Polidori are drawn to implementing sucrose density gradient experiments in purifying and stabilizing, respectively, the model membrane-protein bacteriorhodopsin as discussed above.
Thus, the claimed invention as a whole would have been prima facie obvious over the combined teachings of the prior art.
(III) Claims 22-23 and 25-26 are rejected under 35 U.S.C. 103 as being unpatentable over Polidori et al. (Published 07 April 2016, New Journal of Chemistry, Vol. 40, pp. 5364-5378, IDS filed 10/26/2023) and Baba et al. (Published 07 January 2020, Chemistry and Physics of Lipids, Vol. 227, Article Number: 104870, pp. 1-6, PTO-892) as applied to claims 17-21, 24 and 27-28 above, and further in view of Holland et al. (Published 02 October 1973, US-376320-7A, IDS filed 10/26/2023).
Polidori and Baba address claims 17-21, 24 and 27-28 as written above.
Although, Polidori and Baba do not teach the perfluorinated hexyl, required in claims 22-23 and 25-26.
However, in the same field of endeavor of compounds used as surfactants, Holland teaches as discussed above and further teaches said compounds having highly desirable physical properties when employed for a variety of uses, e.g. reducing surface tension, see Col. 1, lines 15-20.
Holland teaches the compounds may be prepared by reacting α,α-dihydro-perfluorocyclohexane carbinol compositions with sulfonating agents and reacting the resulting compositions with alkali metal containing compositions, see Col. 1, lines 10-20.
Therefore, it would have been prima facie obvious to one of ordinary skill in the art before the invention was filed to have substituted the perfluorinated branched alkyl within the maltose-based fluorosurfactants as taught by the combination of Polidori and Baba as discussed above for the perfluorinated cyclohexane as taught by Holland above as within the scope of the artisan as a simple substitution of one known element for another to yield predictable results. One of ordinary skill in the art would have been motivated to modify the maltose-based fluorosurfactants of Polidori with the substitution as discussed above in order to create sparingly fluorinated maltoside-based surfactants as taught by Polidori above.
One of ordinary skill in the art would have had a reasonable expectation of success of making the substitution as discussed above, as Polidori, Baba and Holland are all drawn to the synthesis of compounds comprising a polar moiety, an aliphatic linker, and a perfluorinated alkyl, including linear alkyls, branched alkyls and/or cycloalkyls, respectively; and wherein Polidori, Baba, and Holland all teach the use of their compounds as surfactants as discussed above.
Thus, the claimed invention as a whole would have been prima facie obvious over the combined teachings of the prior art.
Conclusion
No claims are allowed in this action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JARET J CREWS whose telephone number is (571)270-0962. The examiner can normally be reached Monday-Friday: 9:00am-5:30pm EST.
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/JARET J CREWS/Examiner, Art Unit 1691
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691