DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Status of the Claims
Claims 1-23 are pending. Claims 13-23 are withdrawn. Thus, claims 1-12 are examined herein.
Withdrawn Rejections
The rejection of claims 2-4 and 12 under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, is withdrawn in view of the claim amendments.
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 1-4, 6-7 and 9 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Freudenberg 1965 (Science, 1965).
Regarding instant claims 1-4, 6-7 and 9, Freudenberg discloses the following dilignols, trilignols and tetralignols (pg. 597-598):
PNG
media_image1.png
294
404
media_image1.png
Greyscale
PNG
media_image2.png
324
338
media_image2.png
Greyscale
PNG
media_image3.png
364
812
media_image3.png
Greyscale
PNG
media_image4.png
296
146
media_image4.png
Greyscale
.
Freudenberg further discloses the presence of pentalignols and olignols (pg. 598-599). Freudenberg discloses a method of dehydrogenation of p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol in extremely dilute aqueous solution at pH 5.5 and 20 °C (paragraph bridging pg. 596-597).
Regarding instant claim 9, it is noted that less than 0.1% includes 0%. Freudenberg does not include acetic acid, methanol or ethanol in their compositions.
Response to Arguments
Applicant's arguments filed 24 October 2025 have been fully considered but they are not persuasive. Applicant argues that Freudenberg does not disclose that the at least one lignin oligomer does not repolymerize in absence of a stabilizer, and thus fails to anticipate the subject matter of claim 1.
The examiner respectfully argues that Freudenberg discloses compounds that are within the scope of the lignin oligomers of instant claims 1-4, 6-7 and 9. For example, Freudenberg discloses compound dehydrodiconiferyl alcohol (XVII) (redrawn below, rotated 180 degrees, and in the same orientation as the instant claims), which is the same as instant claims 3-4, formula (i) when R1 and R3 are H and O-CH3; R2 is H; R4 is O-CH3; and R5 is -CH=CHCH2OH.
PNG
media_image5.png
370
172
media_image5.png
Greyscale
=
PNG
media_image6.png
533
525
media_image6.png
Greyscale
In the absence of evidence to the contrary, since the compounds of Freudenberg fall within the scope of claims 3-4, they must inherently also possess the properties claimed in instant claims 1-2.
Claims 1, 3-7 and 9 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Freudenberg et al. (Chemische Berichte, 1965).
Regarding instant claims 1 and 3-7, Freudenberg et al. disclose compositions comprising the dilignol and oligolignol compounds (pg. 1881):
PNG
media_image7.png
224
772
media_image7.png
Greyscale
PNG
media_image8.png
256
242
media_image8.png
Greyscale
.
Regarding instant claim 9, it is noted that less than 0.1% includes 0%. Freudenberg et al. do not include acetic acid, methanol or ethanol in their compositions.
Response to Arguments
Applicant's arguments filed 24 October 2025 have been fully considered but they are not persuasive. Applicant argues that Freudenberg does not disclose that the at least one lignin oligomer does not repolymerize in absence of a stabilizer, and thus fails to anticipate the subject matter of claim 1.
The examiner respectfully argues that Freudenberg et al. disclose compounds that are within the scope of the lignin oligomers of instant claims 1, 3-7 and 9. For example, Freudenberg et al. discloses compound IV: R=H (redrawn below, rotated 180 degrees, and in the same orientation as the instant claims), which is the same as instant claims 3-4, formula (ix), wherein R21 is a 4-O-5 linkage or carbon-oxygen linkage to an aromatic monomer, and R22 and R23 are H and O-CH3; and the same as instant claim 5, formula (i).
PNG
media_image8.png
256
242
media_image8.png
Greyscale
=
PNG
media_image9.png
414
666
media_image9.png
Greyscale
In the absence of evidence to the contrary, since the compounds of Freudenberg et al. fall within the scope of claims 3-5, they must inherently also possess the properties claimed in instant claims 1-2.
Also, Applicant asserts that the only biphenyl and -O- diaryl compounds recited in claim 4 are the compounds (xix) and (xx). The examiner respectfully argues that the instant claims and specification do not recite compounds (xix) or (xx).
Claims 1, 3-7 and 9 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Ferreira et al. (European Journal of Medicinal Chemistry, 2019).
Regarding instant claims 1 and 3-7, Ferreira et al. disclose neolignan compound 19 (pg. 168):
PNG
media_image10.png
146
278
media_image10.png
Greyscale
Regarding instant claim 9, it is noted that less than 0.1% includes 0%. Ferreira et al. do not include acetic acid, methanol or ethanol in their composition comprising compound 19 (pg. 166).
Response to Arguments
Applicant's arguments filed 24 October 2025 have been fully considered but they are not persuasive. Applicant argues that Ferreira does not disclose that the compound 19 does not repolymerize in absence of a stabilizer, and thus fails to anticipate the subject matter of claim 1.
The examiner respectfully argues that Ferreira et al. disclose a compound that is within the scope of the lignin oligomers of instant claims 1, 3-7 and 9. Ferreira et al. disclose compound 19, which is the same as instant claims 3-4, formula (ix), wherein R21 is a 4-O-5 linkage or carbon-oxygen linkage to an aromatic monomer, and R22 and R23 are H and O-CH3; and instant claim 5, formula (i).
In the absence of evidence to the contrary, since the compound of Ferreira et al. falls within the scope of claims 3-4, it must inherently also possess the properties claimed in instant claim 1.
Claims 1, 3-4, 6-7 and 11-12 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Zhou et al. (Drug Development and Industrial Pharmacy, 2018).
Regarding instant claims 1, 3-4, 6-7 and 11-12, Zhou et al. disclose a liposomal honokiol (HNK) prepared with a new type of excipient, Kolliphor HS15 (Abstract; pg. 2005-2006). Kolliphor HS15 is a nonionic surfactant (pg. 2005). Zhou et al. further disclose compositions comprising honokiol, lipoid E80 and Kolliphor HS15 dissolved in ethanol (pg. 2006). Also, it is noted that honokiol is a dimeric lignin with the formula:
PNG
media_image11.png
426
308
media_image11.png
Greyscale
.
Response to Arguments
Applicant's arguments filed 24 October 2025 have been fully considered but they are not persuasive. Applicant argues that Zhou does not disclose that honokiol, in an aqueous solution, exhibits a pH in the range of 5.0 to 8.0 and does not repolymerize in absence of a stabilizer, and thus fails to anticipate the subject matter of claim 1.
The examiner respectfully argues that Zhou et al. disclose honokiol that is within the scope of the lignin oligomers of instant claims 1, 3-4, 6-7 and 11-12. Zhou et al. disclose honokiol, which is the same as instant claims 3-4, formula (xviii), wherein R21 is H, R22 and R23 are H and a carbon linkage to an aromatic monomer.
In the absence of evidence to the contrary, since the compound of Zhou et al. falls within the scope of claims 3-4, it must inherently also possess the properties claimed in instant claim 1.
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.
Claims 1-4 and 6-12 are rejected under 35 U.S.C. 103 as being unpatentable over Boland et al. (US 10,285,932).
Regarding instant claims 1, 3-4 and 6-7, Boland et al. teach a topical skin care formulation comprising a Magnolia officinalis bark extract in an amount of 0.001-5% (col. 5, ln. 65 to col. 6, ln. 14 and 51-55). Boland et al. teach that the magnolia extract is extracted from the bark of the plant. In several embodiments, the extract comprises one or more anti-inflammatory substances. For example, the extract comprises, in some embodiments magnolol and/or honokiol. These substances act synergistically to inhibit activation of inflammatory mediators and mediators of skin aging (col. 44, ln. 43-53).
It is noted that magnolol and honokiol are lignin dimers with the structure:
PNG
media_image12.png
448
954
media_image12.png
Greyscale
.
Therefore, it would have been prima facie obvious for a person of ordinary skill in the art prior to the effective filing date of the instant claims to prepare topical formulations according to Boland et al. comprising magnolol and honokiol, since they act synergistically to inhibit activation of inflammatory mediators and mediators of skin aging.
It is noted that the recitation of the intended use “plant defense elicitor” has not been given patentable weight to distinguish over Boland et al. because the intended use of the claimed invention must result in a structural difference between the claimed invention and the prior art in order to patentably distinguish the claimed invention from the prior art. If the prior art structure is capable of performing the intended use, then it meets the claim. See In re Casey, 152 USPQ 235 (CCPA 1967) and In re Otto, 136 USPQ 458, 459 (CCPA 1963).
Regarding instant claim 2, Boland et al. teach in some embodiments, the pH of the formulations is slightly basic, slightly acidic or neutral. In some embodiments, a pH of 3-5, 4-6, 5-7, 6-8, or ranges in between, are provided (col. 8, ln. 51-52).
Therefore, it would have been prima facie obvious for a person of ordinary skill in the art to prepare formulations according to Boland et al. wherein the formulations have a pH in the range of 5-8, as reasonably suggested by Boland et al.
Regarding instant claim 8, Boland et al. teach that magnolol and honokiol act synergistically to inhibit activation of inflammatory mediators and mediators of skin aging (col. 44, ln. 43-53).
It would have been prima facie obvious for a person of ordinary skill in the art to prepare formulations according to Boland et al. comprising a combination of magnolol and honokiol, wherein one of the compounds is present in an amount of 50-90% by weight of the total weight of the two compounds combined.
Such would have been obvious because a person of ordinary skill in the art would have been motivated to determine the effective ratio of magnolol and honokiol for use in the formulations according to Boland et al.
Regarding instant claim 9, the formulations according to Boland et al. do not comprise ethanol, methanol or acetic acid.
Regarding instant claim 10, Boland et al. teach a topical skin care formulation comprising a Magnolia officinalis bark extract in an amount of 0.001-5% (col. 5, ln. 65 to col. 6, ln. 14 and 51-55).
Therefore, it would have been prima facie obvious for a person of ordinary skill in the art to prepare formulations according to Boland et al. comprising up to 5% magnolol and/or honokiol.
Regarding instant claims 11-12, Boland et al. teach the formulations further comprising one or more additional ingredients selected from the group consisting of: sunscreen agents, viscosity agents, surfactants, emulsifiers, fragrances, colorants, and solvents (col. 2, ln. 56-59; Table 1; Claim 4).
Therefore, it would have been prima facie obvious for a person of ordinary skill in the art to prepare formulations according to Boland et al. comprising a surfactant (e.g., anionic, cationic, nonionic and/or amphoteric surfactant) and a solvent.
Response to Arguments
Applicant's arguments filed 24 October 2025 have been fully considered but they are not persuasive. Applicant argues that Boland pertains to treatment of skin in mammalian subjects, not to plant defense, and is thus not in the same field of endeavor.
The examiner respectfully argues that the instant claims and the prior art are both drawn to compositions comprising lignin oligomers. The recitation of “plant defense elicitor” is an intended use for the claimed composition. The compositions of claims 1-7 only recite the lignin oligomer as a component of the composition, claim 9 recites less than 0.1% each of acetic acid, methanol, and ethanol, claim 11 recites a surfactant, and claim 12 recites a polar aprotic solvent. Boland et al. teach formulations comprising magnolol and honokiol, as well as additional ingredients such as surfactants and solvents. Therefore, the instantly claimed formulations according to the instant claims are obvious in view of the compositions according to Boland et al.
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.
Contact Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Nathan W Schlientz whose telephone number is (571)272-9924. The examiner can normally be reached 10:00 AM to 6:00 PM, Monday through Friday.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Sue Liu can be reached at (571) 272-5539. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/N.W.S/Examiner, Art Unit 1616
/Mina Haghighatian/Primary Examiner, Art Unit 1616