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 .
DETAILED ACTION
2. This Office Action is responsive to Applicant’s Amendment and Remarks, filed March 9, 2026. The amendment, field March 9, 2026, is entered, wherein claims 1, 5 – 6, 9 – 10, 12, and 14 – 17 are amended, claims 2 – 4 and 7 – 8 are canceled, and claims 21 – 22 are withdrawn.
Claims 1, 5 – 6, and 9 – 25 are pending in this application and claims 1, 5 – 6, 9 – 20, and 23 – 25 are currently examined.
Priority
3. This application is a national stage application of PCT/JP2021/029573, filed August 10, 2021, which claims benefit of foreign priority document JP2020-137010, filed August 14, 2020.
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Should applicant desire to obtain the benefit of foreign priority under 35 U.S.C. 119(a)-(d) prior to declaration of an interference, a certified English translation of the foreign application must be submitted in reply to this action. 37 CFR 41.154(b) and 41.202(e).
Failure to provide a certified translation may result in no benefit being accorded for the non-English application is only pertinent when interference arises.
Withdrawn Objections
4. The objection of figures 5, 7, 9, 11, 23, 25, 27, 34, 36B, 69, and 72 in the previous Office Action, mailed December 9, 2025, is withdrawn in view of the amended figures.
The objection of claims 1 – 4, 6, 10, 12, and 17 in the previous Office Action, mailed December 9, 2025, is withdrawn in view of the amended claims 1, 6, 10, 12, and 17 and the canceled claims 2 – 4.
Withdrawn Rejections
5. The rejection of claims 9 and 15 in the previous Office Action, mailed December 9, 2025, 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for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention has been considered and is withdrawn in view of the amended claims 9 and 15.
The rejection of claims 1 – 5 in the previous Office Action, mailed December 9, 2025, under 35 U.S.C. 102(a)(1) as being anticipated by Liu et al. has been considered and is withdrawn in view of the amended claim 1.
The following are maintained / modified grounds of rejection necessitated by Applicant’s Amendment and Remarks, filed March 9, 2026, wherein claims 1, 5 – 6, 9 – 10, 12, and 14 – 17 are amended, claims 2 – 4 and 7 – 8 are canceled, and claims 21 – 22 are withdrawn. Previously cited references have been used to establish the maintained / modified grounds of rejection.
Maintained / Modified 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:
i. Determining the scope and contents of the prior art.
ii. Ascertaining the differences between the prior art and the claims at issue.
iii. Resolving the level of ordinary skill in the pertinent art.
iv. 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.
Claims 1, 5 – 6, and 9 are rejected under 35 U.S.C. 103 as being unpatentable over Yang et al. (Carbohydrate Polymers, 2011, Vol. 84, Issue 1, page 33 – 39, cited in the previous Office Action mailed December 9, 2025) in view of Liu et al. (Open Chemistry, 2010, Vol. 8, Issue 3, page 576 – 581, cited in the 03/15/2023 IDS).
a. Regarding claims 1, 5 – 6, and 9, Yang et al. teach a chemical modification of alginate. Alginate has an abundance of free hydroxyl and carboxyl groups distributed along the polymer chain backbone, and it, therefore, unlike neutral polysaccharides has two types of functional groups that can be modified to alter the characteristics in comparison to the parent compounds (Abstract). The microstructural features of alginate are biocompatible unbranched binary copolymers that have been widely used as a type of desired biomaterials in many fields, such as drug delivery and controlled-release (page 33, Right Col., para. 1; page 34, Left Col., para. 1). Yang et al. teach that alginate may be modified by amidation using the coupling agent of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC-HCl) to form amide linkages between amine-containing molecules and the carboxylate moieties on the alginate polymer backbone (page 37, Left Col., para. 3). The reaction scheme below shows the amidation of alginate using EDC as coupling agent (page 37, Right Col., Scheme 11):
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However, Yang et al. do not teach the formula (A-1) to amidate alginate using 4-aminobenzaldehyde and the modification rate.
Liu et al. teach to amidate the PEG-grafted chitosan copolymer (4)using 4-aminobenzaldehyde and EDC as the coupling agent to yield copolymer (5) (page 577, Scheme 1):
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. Liu et al. also teach that the copolymer (5) with both amino and formyl groups may conjugate drugs such as paclitaxel to form pH-sensitive chemical bonds for pH-controlled release of drugs, and the amino groups may be potential sites to bind genes, which achieves gene/drug co-delivery (page 580, Right Col., para. 2).
It would have been prima facie obvious for a person of ordinary skill in the art before the effective filing date of the claimed invention to modify the alginate as taught by Yang et al. with the 4-aminobenzaldehyde because Liu et al. teach that the formyl group may conjugate drugs to form pH-sensitive chemical bonds for pH-controlled release of drugs. One would have been motivated to make such modification because the combination will yield predictable and improved results. For the modification rate, it is defined in the specification as number of modifying group (A) contained in the polysaccharide derivative divided by number of monosaccharide units contained in the polysaccharide derivative (para. [0104]). Yang et al. disclosed the amidation of alginate using EDC that would produce a product that has one modifying group in one monosaccharide unit. The calculated modification rate would be 1. Therefore, one of the ordinary skill in the art would have had a reasonable expectation of success because it is known in the art that the formyl group will conjugate to drugs to form a drug with pH-controlled release property.
Claims 10 – 13, 16 – 20, and 23 – 25 are rejected under 35 U.S.C. 103 as being unpatentable over Yang et al. (Carbohydrate Polymers, 2011, Vol. 84, Issue 1, page 33 – 39, cited in the previous Office Action mailed December 9, 2025) in view of Liu et al. (Open Chemistry, 2010, Vol. 8, Issue 3, page 576 – 581, cited in the 03/15/2023 IDS) as applied to claims 1, 5 – 6, and 9 above, and further in view of Gao et al. (Nanoscale, 2017, Vol. 9, Issue 34, page 12533 – 12542, cited in the previous Office Action mailed December 9, 2025).
b. Regarding claims 10 – 13, 16 – 20, and 23 – 25, Yang et al. and Liu et al. teach the limitations discussed above. Yang et al. further teach that alginate is known to form a hydrogel in the presence of divalent cations, such as calcium, which act as crosslinkers between the functional group of alginate chains. These gels have been proposed to be stabilized by intermolecular hydrogen bonds (page 34, Left Col., para. 2).
However, these references do not teach a polysaccharide derivative-drug conjugate between a drug containing a primary amino group and the polysaccharide derivative, wherein the structure is represented by formula (D):
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wherein “Drug” represents the drug part excluding the primary amino group, R1, ring P and * are defined in claim 1. These references do not teach that the drug will be released from the conjugate under low pH conditions. These references do not teach that the drug is a low molecular weight compound. These references do not teach a crosslinked structure-drug conjugate between a drug containing a primary amino group and the crosslinked structure, wherein the primary amino group contained in the drug and formula (A-1) are covalently bonded via a Schiff base. These references do not teach the composition recited in claim 17.
Gao et al. teach that doxorubicin (Dox) can be covalently conjugated to the oxidized sodium alginate through a Schiff base reaction to produce an amphiphilic macromolecular prodrug (Abstract). Gao et al. disclose the synthetic process of Dox-OSA (page 12534, Figure 1):
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which is pH-sensitive (Abstract). Gao et al. further teach the Dox-OSA synthesis is based on the conjugation of amino groups of Dox to the aldehyde groups of OSA, via a Schiff base reaction. Briefly, OSA was dissolved in deionized water. Dox and HCl are mixed with trimethylamine in DMSO, which is subsequently added into an OSA solution and the mixture is stirred for 6 hours (page 12539, Right Col., para. 4).
It would have been prima facie obvious for a person of ordinary skill in the art before the effective filing date of the claimed invention to substitute paclitaxel as taught by Liu et al. with Dox in view of Gao et al. because it is known in the art to conjugate Dox to alginate. One would have been motivated to substitute paclitaxel with Dox because the substitution is well-known and would yield predictable results. Gao et al. also demonstrate that the primary amino group of Dox would react with the formyl group via Schiff base reaction. It is expected that the polysaccharide derivative as taught by Yang et al. and Liu et al. would react with Dox at the CHO site to achieve the claimed formula (D) and the drug conjugate will inherently possess the property of pH-controlled release. For the composition, calcium as a crosslinker will also be considered as a pharmaceutically acceptable additive. Moreover, it is known in the art to put a hydrogel into contact with a subject to be treated. Therefore, one of the ordinary skill in the art would have had a reasonable expectation of success to substitute paclitaxel as taught by Liu et al. with Dox in view of Gao et al. because Yang et al. and Liu et al. teach that paclitaxel may be conjugated with alginate copolymer and Gao et al. teach that Dox has been conjugated with alginate.
Claims 14 – 15 are rejected under 35 U.S.C. 103 as being unpatentable over Yang et al. (Carbohydrate Polymers, 2011, Vol. 84, Issue 1, page 33 – 39, cited in the previous Office Action mailed December 9, 2025) in view of Liu et al. (Open Chemistry, 2010, Vol. 8, Issue 3, page 576 – 581, cited in the 03/15/2023 IDS) and Gao et al. (Nanoscale, 2017, Vol. 9, Issue 34, page 12533 – 12542, cited in the previous Office Action mailed December 9, 2025) as applied to claims 1, 5 – 6, 9 – 13, 16 – 20, and 23 – 25 above, and further in view of Li et al. (Materials Science and Engineering C, 2014, Vol. 36, page 287 – 293, cited in the previous Office Action mailed December 9, 2025).
c. Regarding claims 14 – 15, the references teach limitations discussed above.
However, these references do not teach a crosslinked structure containing an amino group-containing polymer, wherein the polymer is an amino group-containing proteins.
Li et al. teach that there has been an increasing interest in using polysaccharide-based cross-linkers to prepare biocompatible polymeric hydrogels with wide biomedical applications for drug delivery, cell encapsulation, and tissue engineering. Some natural polysaccharides, containing vicinal hydroxyl groups, including sodium alginate, is modified with periodate to form aldehyde groups, and then is used to crosslink amino group-containing polymers in aqueous systems by the Schiff base reaction between amino and aldehyde groups. The resultant hydrogels could be formed in situ, and exhibit better biocompatibility when compared to those obtained from photo-crosslinking by a potentially toxic photosensitizer or chemical crosslinking by potentially toxic carbodiimide, glutaraldehyde, and adipic dihydrazide (page 287, Left Col., para .1). Li et al. teach that casein proteins can be used to crosslink a polysaccharide derivative as Li et al. disclose that casein proteins contain hydrophilic functional groups such as -COOH, -NH2, and -OH. They possess a number of favorable characteristics suitable for the development of hydrogel biomaterials, such as high hydrophilicity, good biodegradation, lack of toxicity, and availability of reactive sites for chemical modification. Moreover, they are less expensive and more readily available when compared to collagen, silk fibroin, bovine serum albumin and elastin-like polypeptides (page 287, Left Col., para. 2; Right Col., para. 1).
It would have been prima facie obvious for a person of ordinary skill in the art before the effective filing date of the claimed invention to combine the polysaccharide derivative as taught by Yang et al. and Liu et al. with casein proteins in view of Li et al. because casein proteins are known in the art to crosslink with polysaccharide. One would have been motivated to combine the polysaccharide derivative as taught by Yang et al. and Liu et al. with casein proteins in view of Li et al. because casein proteins bring in many benefits as disclosed by Li et al. and the combination would yield a product with improved properties. Therefore, one of ordinary skill in the art would have had a reasonable expectation of success to combine the polysaccharide derivative as taught by Yang et al. and Liu et al. with casein proteins in view of Li et al. because the combination of casein proteins with polysaccharide derivative is known in the art and the combination is expected to yield a product with improved properties.
Response to Applicant’s Remarks:
Applicant’s Remarks, filed March 9, 2026, have been fully considered and are found to be not persuasive.
Regarding Yang et al. and Liu et al., Applicant argues that Yang et al. fail to disclose or suggest any aspect of pH-controlled drug release and Applicant argues that the disclosure of Liu et al. is limited to a mere “theoretically possibility” without providing any experimental data or empirical evidence of actual drug release. In contrast, the claimed invention demonstrates that the combination of the claimed polysaccharides and benzaldehyde enables reliable release under low pH conditions, substantiated by concrete experimental data. One of ordinary skill in the art would not have had a reasonable expectation of success in achieving the remarkable pH-controlled release effects of the claimed invention by applying the benzaldehyde structure of Liu et al. to the system of Yang et al. The argument is not persuasive because the rejection is based on the combined teachings of the applied references, not on Yang et al. or Liu et al. individually. A proper obviousness analysis does not require that each reference individually disclose every claimed feature, but whether the combined teachings would have rendered the claimed invention obvious. Moreover, the rejection further relies on Gao et al., which teach conjugation of doxorubicin to aldehyde-functionalized alginate via Schiff base and teach that the resulting conjugate is pH-sensitive. Therefore, when the references are considered in combination, the cited art teach or suggest the claimed pH-responsive conjugation.
Applicant argues that the cited references fail to disclose all of the claim limitations of independent claim 1 and those claims dependent thereon. The argument is not persuasive because Applicant has not identified any specific claim limitation that is missing from the combined teachings of the cited references. Applicant merely asserts that the cited references fail to disclose all of the limitation of the claims. However, in an obviousness rejection, all claim limitations are considered, but the teachings of multiple references may properly be combined where there is an articulated reason to do so. The Office Action set forth where the cited references, in combination, teach or suggest the claimed invention, and Applicant has not specifically shown error in those findings.
Applicant further argues that the cited reference provide no proper reason or rationale that would allow one of ordinary skill in the art to arrive at the claimed invention. The argument is not persuasive because the Office Action sets forth a proper rationale for the combination of references and Applicant has not specifically addressed why that rationale is not proper. Applicant merely states that the cited references provide no proper reason or rationale that would have allowed one of ordinary skill in the art to arrive at the claimed invention, but does not explain why one of ordinary skill in the art would not have made the proposed combination or modification.
Maintained / Modified Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1, 5 – 6, 13 – 16, and 20 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1 – 6 and 9 – 12 of copending Application No. 18/835,632 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of ‘632 anticipate the claimed invention.
a. Independent claim 1 is directed to a polysaccharide derivative obtained by introducing a group represented by formula (A-1):
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into a polysaccharide, wherein R1 is a hydrogen atom; ring P is a phenyl; L1 is a single bond; and * is a linkage with the polysaccharide, wherein the polysaccharide is alginic acid. Dependent claim 5 is directed to the polysaccharide derivative, wherein the polysaccharide is a polysaccharide containing a carboxyl group and formula (A-1) is introduced into the polysaccharide by substitution of -OH in the carboxyl group and forming an amide bond. Dependent claim 6 is directed to the polysaccharide derivative, wherein the polysaccharide derivative contains at least one structural unit selected from formulae (c11) and (c12):
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wherein each of R11, R12, R13, and R14 is hydrogen atom. Independent claim 13 is directed to a crosslinked structure containing the polysaccharide derivative, wherein the polysaccharide derivative is crosslinked via a crosslinking group. Independent claim 14 is directed to a crosslinked structure containing the polysaccharide derivative together with one or both of an amino group-containing polymer and an amino group-containing low-molecular-weight compound containing two or more primary amino groups, wherein the crosslinked structure is crosslinked by covalent bonds formed via Schiff bases between the primary amino groups contained in the amino group-containing polymer and amino group-containing low-molecular-weight compound and the group represented by the formula (A-1) in the polysaccharide derivative. Dependent claim 15 is directed to the crosslinked structure, wherein the amino group-containing polymer is a linear polyamines. Independent claim 16 is directed to a crosslinked structure-drug conjugate between a drug containing a primary amino group and the crosslinked structure, wherein the primary amino group contained in the drug and the group presented by formula (A-1) in the crosslinked structure are covalently bonded via a Schiff Base. Independent claim 20 is directed to a drug delivery carrier or separation material containing the polysaccharide derivative containing the polysaccharide derivative, wherein the polysaccharide derivative is crosslinked via a crosslinking group.
‘632 teaches a tissue adhesive material comprising a polysaccharide derivative in which a group represented by Formula (A):
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wherein R1 is a hydrogen atom; ring P is a phenyl; Y is -NH-; and * is a linkage with the polysaccharide (claims 1 and 5). The polysaccharide is a alginic acid (claims 2 and 11), wherein the polysaccharide is a polysaccharide containing a carboxyl group and the group represented by Formula (A), wherein Formula (A) is further defined as Formula (A-1):
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wherein R1 is hydrogen; ring P is a phenyl; L1 is a single bond; and * is a linkage with the polysaccharide (claim 3). The polysaccharide contains a constituent unit represented by Formula (c11) and/or (c12):
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wherein each of R11, R12, R13, and R14 is hydrogen atom (claims 4 and 11). ‘632 teaches that the tissue adhesive material in which at least a part of polysaccharide derivative is crosslinked (claim 6). ‘632 also teaches a crosslinked structure, comprising the polysaccharide derivative, one or both of an amino group-containing polymer and an amino group-containing low-molecular-weight compound containing two or more primary amino groups, wherein the crosslinked structure is crosslinked by covalent bonds formed via Schiff bases (claims 9 and 12). The crosslinked structure, wherein the amino group-containing polymer is a linear polyamine (claim 10).
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not been patented.
Responses to Applicant’s Remarks:
Applicant’s Remarks, filed March 9, 2026, have been fully considered and are found to be not persuasive.
Regarding the rejection, Applicant argues that the present application has an earlier international filing date than the international filing date of the ‘632 application. However, the rejection is consistent with established practice for addressing nonstatutory double patenting. As explained in MPEP 804(II)(B)(5), a later-expiring patent or patent application may serve as a proper reference in a one-way obviousness-type double patenting rejection unless the applicant can show that the claims could not have been filed in a single application and that the Office was solely responsible for any delay that caused the reference patent to issue first. In the present case, Applicant does not provide evidence that the Office, rather than Applicant, is solely responsible for any prosecution delay, nor that the claims could not have been presented together. Courts have consistently held that applicant-driven prosecution choices, such as filing multiple applications or continuations, do not warrant application of the two-way test. Therefore, the one-way test applies, and the double patenting rejection over ‘632 remains proper.
Conclusion
No claim is found to be allowable.
Applicant's amendment necessitated the maintained / modified 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 HOI YAN LEE whose telephone number is 571-270-0265. The examiner can normally be reached Monday - Thursday 7:30 - 17:30.
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/H.Y.L./Examiner, Art Unit 1693
/SCARLETT Y GOON/Supervisory Patent Examiner, Art Unit 1693
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