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 .
Priority
This application is a 371 of PCT/CN2020/119345 (09/30/2020) and claims foreign priority to CHINA 201911411861.8 (12/31/2019).
Status
Any rejection not reiterated in this action are withdrawn.
Claims 1, 5, 9, and 10 are pending.
New 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.
Claims 1, 5, 9 and 10 are rejected under 35 U.S.C. 103 as being unpatentable over Li et al. (Angew. Chem. Int. Ed. 2018, 57, p. 3995 –3998, S1-S16) in view of CN104559069 (‘069, machine translation), Bazan et al. (US20150075622), CN103224486 (‘486, machine translation), and Gaudiana et al. (US 20070014939).
Li teaches photothermal therapy with nanoparticles comprising the semiconducting polymer amphiphiles PCB1 and PCB2 which were shown to have to have good conversion efficiency (Abstract; p. 3995; p. 3996: “The photothermal conversion efficiency of PCB1 and PCB1-Bro at 808 nm was measured to be 42.8%”). Li teaches the structure of the semiconducting polymers PCB1 and PCB2 as in Fig. 2:
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Regarding claim 1, Li teaches the polymeric monomer starting material as follows (p. S2):
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which differs from claim 1’s formula (I) by a lack of sulfone modification of the sulfur and the R group terminating with the reactive Br group instead of one of the structures “X” as recited in the claims, such as N(CH2CH3)2).
Regarding claim 1’s difference of “X”, ‘069 teaches techniques for improving water solubility and biological application of the polymers through attachment of water-soluble ionic groups via sidechains (page 2/8 translation, emphasis added):
Water-soluble conductive conjugated polyelectrolytes are conjugated polymers with side chains of ionic functional groups. These compounds combine the good photoelectric properties of traditional conjugated polymers with the water solubility of polyelectrolytes. On the one hand, as conjugated polymers, they have strong light absorbing properties in the ultraviolet-visible region, and electrons or energy can transfer rapidly on the conjugated backbone. On the other hand, they achieve water solubility by attaching water-soluble ionic groups to the side chains of the conjugated system, which makes it possible to process materials in environmentally friendly solvents such as water and ethanol, and they can be used In a solvent environment compatible with biological systems, its application in the field of biomedicine has received more and more attention.
‘069 provided several examples, including the following scheme in Figure 6 showing the point of attachment of the sidechain “R” in the preparation of the monomer:
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‘069 describes the sidechain R group as including “unsaturated hydrocarbon compounds with side chains containing long-chain quaternary ammonium salt structures” and “long-chain sulfonate structures” (page 3/8).
Bazan teaches conjugated polymers with improved water solubility by altering the sidechains including to a sulfonate as shown in Fig 1(b) (-SO3(-)N(n-Bu)4(+) is the TBA salt):
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.
Similarly, ‘486 teaches chemically related thiophene polymers such as P1 shown below:
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‘486 teaches that the modifications are for the purpose of improving solubility through the use of the S,S-dioxy polar group and a substituent (p. 2/10):
The present invention develops a series of water/alcohol-soluble polymers based on S,S-dioxy-dibenzothiophene derivatives by introducing polar groups into the side chains of S,S-dioxy-dibenzothiophene units . This type of polymer not only has excellent solubility and electron injection properties in environmentally friendly solvents
…
Another object of the present invention is to use said water/alcohol soluble linear polymers and hyperbranched polymers based on polar group S, S-dioxy-dibenzothiophene units
…
A kind of polar substituent group replaces S, S-dioxy-dibenzothiophene monomer, and its structural formula is:
In the formula, R is hydrogen; or -(CH2)nX, n=1 to 30, X is a diethylamine group, a zwitterionic group, a diethanolamine group, a trimethylamine group, a phosphate ester group and Its derivative etc., specific structural formula such as:”
Thus, ‘486 suggests the use of an alkyl sidechain with a polar group to improve solubility in water and a S,S-dioxy (sulfone) thiophene modification.
In addition regarding the sulfone modification, Gaudiana teaches chemically related thiophene polymers which are “Polymers with low band gaps and high charge mobility” (Abstract), including comonomers of Table 1 and 2:
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Gaudiana also teaches that the use of the cyclopentadithiophene in the polymer allows tuning of the absorption wavelength ([0040]: “An advantage of a co-polymer containing a cyclopentadithiophene moiety is that its absorption wave length can shift toward the red and near IR portion (e.g., 650-800 nm) of the electromagnetic spectrum, which is not accessible by most other polymers.”).
One of ordinary skill in the art viewing Li’s success with photothermal therapy would have had a reasonable expectation that Li’s polymer could be optimized using the well-known techniques of polar group additions including a similar alkyl sidechain as used by Li as also suggested by ‘069 and ‘486, and Bazan including the polar group of a sulfonate. Furthermore, one of ordinary skill in the art would have known that the wavelength of absorption is optimizable by use of the cyclopentadithiophene monomer. Therefore, the comparable polymers of Li, ‘486, ‘069, Bazan and Gaudiana in the same field of endeavor would have given one of ordinary skill in the art an expectation that the modifications suggested by the secondary references when applied to Li would have predictably resulted in the same improvement of water solubility and wavelength tuning. Thus, one of ordinary skill in the art would have modified Li’s compound 1 to a bis sulfone and convert the Br to sulfonate and arrive at the claimed invention.
Regarding claim 5, one of ordinary skill in the art would have prepared the monomer of claim 1 for the purpose of synthesizing a polymer, such as was suggested by Gaudiana, including in combination with a fluorenyl group to optimize the wavelength of absorption in a predictable manner. Thereby meeting the limitation of claim 5 Ar=fluorenyl and the chemical structure of the resulting polymer would be “characterized in that” (i.e. comprising – MPEP 2111.03) it would have at least n=1. Thus, the claim is obvious.
Regarding claims 9 and 10 to a photothermal treatment method comprising administering and irradiating, Li teaches use of the polymers for photothermic cancer therapy including administering the compound to a tumor and irradiating with NIR light such that one of ordinary skill in the art would have used the modified polymer for the same purpose and arrive at the claimed invention with a reasonable expectation of success.
With each of the claims, the level of skill in the art is very high such that one of ordinary skill in the art would consider routine the combination of elements from the teaching of the art. One of ordinary skill in the art would have recognized that the results of the combination would be predictable due to the well-known nature and optimizations routinely performed in the art. Thus, one of ordinary skill in the art would have arrived at the invention as claimed before the effective filing date with a reasonable expectation of success.
Conclusion
No claim 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.
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/ROBERT H HAVLIN/Primary Patent Examiner, Art Unit 1626