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 .
Response to Amendment
The Amendment filed 08/08/2025 has been entered. Applicant’s amendments are in response to in the Non-Final Office Action mailed 05/12/2025. Applicant’s claims have been amended in the following manner: Applicant amends the claims generally according to the objections and rejections of the previous Non-Final Office Action (i.e., by narrowing the species claimed in light of the Art). Further note, Applicant filed an IDS on 10/15/2025 (with Art FR3003860A1 that reads on the amended claim set), after the Non-Final Office Action filed 05/12/2025, prompting a new claim rejection, which is considered proper. Claims 244-245 have been cancelled, and new claims 260-263 have been added to draw new grounds of rejection, by Applicant. The following objections/rejections are withdrawn: claims 250 and 258 objections, 112b rejection of claim 251, and the 101 rejection of claims 255-257 (see response to arguments below for full explanation).
Claims 240-243 and 246-263 are pending.
Claims 240-243 and 248-263 are presented for examination and rejected as set forth below.
Claims 246-247 are objected to.
New 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.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 255-259 are rejected as being unpatentable over 35 U.S.C. 102(a1) as anticipated by Herve (FR3003860A1; reference provided in the IDS filed 10/15/2025, after the non-final rejection filed 05/12/2025; machine translation provided).
Applicant’s claims are directed to (for claims 240-243 and 246-254, and 263) a composition comprising: a semi-permanent colorant, wherein the semi-permanent colorant comprises a genipin derivative; a solvent; and further comprising a semi-volatile semi-permanent colorant solubilizer or a film-forming agent or a thickening agent; and wherein the genipin derivative is a compound of Formula I. Note that the term “semi-permanent colorant” is a property of the instant compounds and does not impact the structure of the composition. When the prior art teaches the same compound, the property is expected. Also, the term “genipin derivative” is limited to the scope of the compounds claimed by instant claim set.
Further note that claims 255-259 specify only certain compound species (i.e., that are not mixed with other ingredients as a part of a larger composition). Claims 260-261 are directed to a method, and claim 262 is directed to an article
Herve discloses iridoid compounds (reads on the genipin derivatives of claim 240, as defined by species presented by Herve, as shown below, which overlap with the instantly claimed genipin derivatives) as direct hair dyes and a process for dying keratinous fibers such as hair (abstract of English translation, [0001]). Generally, Herve discusses iridoid compounds of structure (I) below (pg 1-2 of the French publication), compared to Applicant’s instant formula (I) of claim 240:
Herve,
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compared to instant claim 240,
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Regarding claims 255-259: Herve claims a coloring composition comprising a genipin derivative that can function as a dye for keratin fibers (abstract, [0019, 0054]). Herve names exact compound species for this purpose (pg 18 Figures in Foreign publication, reproduced below, where structures did not transfer to the English translation):
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The aldehyde above (4 rows down, on the left) reads on the aldehyde species of claim 258 (13th compound listed; and claim 258 depends from claim 255), and claim 259 (1st compound listed).
The aldehyde also reads on claims 255-257. Focusing on the general structure IIa of claim 255 to address the R groups in question: the aldehyde represents R3 = -CH(=O), and R9 = H (note this also translates to structure I of claim 240 (where a double bond is present and R1 = -C(=O)OMe) and structure IIb of claim 257.
From instant claims 258-259, the aforementioned compound,
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, which is essentially the same compound (slightly different drawing notation) as the aldehyde from Herve shown above.
Therefore, the reference is deemed to anticipate the instant claims above.
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 240-243, 248-259, and 263 are rejected under 35 U.S.C. 103 as being unpatentable over Herve (FR3003860A1; reference provided in the IDS filed 10/15/2025, after the non-final rejection filed 05/12/2025; machine translation provided).
As discussed above, Herve teaches specific a genipin derivative compound that reads on instant claims 255-259. Furthermore, as shown below, Herve teaches the obviousness of the instant composition (instant claims 240-243, 248-254, 260-263) and additional compounds of the claim set (instant claims 240-243 and 248-263).
Regarding claims 240-243, 248-259, and 263: Herve claims a coloring composition comprising an iridoid-type compound [0001] (which also fits the broad classification of a genipin derivative, since genipin is an iridoid, and general formula as shown below encompasses genipin) ([0019, 0054]; pg 15-18 Tables and Figures, wherein pg 15, line 2 describes the R groups for genipin) that can include a solvent [0021] and thickeners (reads on thickening agent of claim 240) [0022]. Herve teaches incorporation of one or more of these genipin derivatives into a coloring composition (Herve – claim 12; pg 6-7 of machine translation), and lawsone is also recognized as a direct dye of incorporation [0019]. Herve teaches a pH of 6-11 [0023], which overlaps with the instant range of 4-7 (in claim 263).
Herve also discusses the following allowable variations of the disclosed compound series on the pg 15-16 Tables (reproduced below), as obvious. Note the preferred analog of Herve below (pg 18), and how it applies to substitution of the table below it:
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:
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685
690
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Notably (from the table above and pg 1-2 of the French publication), Herve teaches variations for genipin derivatives in terms of Formula I (pg 1-2 of the French publication), where it would be obvious to make one or more substitutions from the parent (preferred) compound described above:
R1 (Herve) can be a primary alcohol, aldehyde, carboxylic acid, carboxylic ester, amide (primary, secondary, tertiary), primary amine, imine, etc (pg 1-2 of french publication). – This maps to instant R3 (when the double bond is present) in instant formula I of claim 240, such that R3 = -CH2OH, -CH(=O), -C(=O)OR10, -C(=O)NR10R10, -CH2NR7R8.
R2 (Herve) can be H, Me, alcohol, acids, esters, amides, etc. – This maps to instant R1 (when the double bond is present) in instant formula I of claim 240, such that R1 = -C(=O)OR6, C1-alkyl.
R3 (Herve) is not necessarily present (i.e., n = 0, etc.) (found below structure on pg 15). – This is not present in instant formula I of claim 240.
R4 (Herve) is H, alkyl, etc. – This maps to instant R2 (when the double bond is present) in instant formula I of claim 240, such that R2 = -OH.
Structures are provided below for reference to the discussion above:
Herve:
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; from instant claim 240:
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Thus, the Examiner suggests removing the specific groups from the instant R3 listings from the general instant formulas I, IIa, and IIb (at least when a double bond is present), that are taught by Herve (where Herve teaches this substituent as R1 on pg 1-2 of the French publication). The instant species of the claim set will also have to be considered with these changes (see below for more information). Note that while the Examiner discusses mapping and suggestions in this Office Action, due to the complexity of the chemical structures, Applicant is encouraged to make their own assessments in comparison to this Office Action, based on the Art.
In summary, Herve teaches the elements and desirability for the limitations of the instant claims, and thus, their obviousness. It must be remembered that “[w]hen a patent simply arranges old elements with each performing the same function it had been known to perform and yields no more than one would expect from such an arrangement, the combination is obvious.” KSR v. Teleflex, 127 S.Ct. 1727, 1740 (2007) (quoting Sakraida v. A.G. Pro, 425 U.S. 273, 282 (1976)). “[W]hen the question is whether a patent claiming the combination of elements of prior art is obvious,” the relevant question is “whether the improvement is more than the predictable use of prior art elements according to their established functions.”
In addition to the discussion of formula mappings above, several instantly claimed species are at issue (i.e., as being obvious from Herve) in the current claim set (numbering of compounds for reference below, numbers from left to right, including structures marked for deletion, as presented in the claim set filed 08/08/2025):
Claim 250: the aldehyde structure (compound 1), the primary alcohol (compound 10), the primary alcohol (compound 15); note there is no issue with the epoxide (compound 13).
Claim 258: the acid structure (compound 1), the acid structure (compound 5), the amide structure (compound 6), the phenol ether (compound 12, already marked for deletion), the aldehyde (compound 13), the amide (compound 16).
Claim 259: the aldehyde (compound 1), the aldehyde (compound 2), the unsaturated diester (compound 3), the acid (compound 4), the amide (compound 5), the unsaturated phenyl (compound 6), the unsaturated phenyl (compound 8).
This list may not be complete, and it is up to Applicant to distinguish the Art from the instant claims. Applicant could amend the claim set according to these species and R-group (i.e., pertaining to formulas I, IIa, and IIb) conflicts, or argue the instantly claimed compounds against the Art. Any scope-changing amendments to the current claim set would require further search and/or consideration.
Claims 240-243 and 248-263 are rejected under 35 U.S.C. 103 as being unpatentable over Herve (FR3003860A1; reference provided in the IDS filed 10/15/2025, after the non-final rejection filed 05/12/2025; machine translation provided), as applied to claims 240-243, 248-259, and 263, and in further view of Handley (US 2016/0367460 A1).
As discussed above, Herve teaches specific genipin derivative compound species and the obviousness of the instant composition (instant claims 240-243 and 248-254) and additional compounds of the claim set (instant claims 240-243 and 248-259). However, Herve does not teach a method of applying the genipin derivative composition to the skin (instant claim 260-261), nor an applicator article comprising the genipin derivative (instant claim 262).
Handley teaches body ink compositions and applicators based on genipin and genipin derivatives (abstract, [0070-0072]).
Regarding claims 260-262: Handley teaches that PHOSITA are interested in determining the coloring capability of genipin derivatives in the tattooing arts [0070-0072]. Handley further discloses that different colors and/or improved stability can arise from different genipin derivatives such as genipa red [0070] in contrast to the blue of genipin [0058].
Handley also teaches a method of applying a multi-layered pad with a first adhesive layer, second adhesive layer, tattoo ink (where genipin is embedded into a non-woven material) (Handley – claims 1 and 16-20), where the backing is found in Figure 6 as the non-sticky side [0055].
It would have been prima facie obvious for one of ordinary skill in the art before the effective filing date of the claimed invention to apply Handley’s method of body ink application for use on genipin and genipin derivatives to Herve’s compounds and compositions because Herve teaches genipin derivatives that are able to dye keratin fibers (abstract), and Handley has interest in the dying properties of genipin derivatives on skin (i.e., skin also comprises keratin) [0070-0072]. Handley further discloses that different colors and/or improved stability can arise from different genipin derivatives such as genipa red [0070] in contrast to the blue of genipin [0058]. Thus, a PHOSITA at the time of filing would be motivated to use Herve’s compounds in tattooing in order to find advantageous dyeing properties such as different coloration or improved stability.
Allowable Subject Matter
Claims 246-247 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims. The Art does not teach the specified configuration, where the double bond is absent, such that the R4 and R5 form a 3- or 4-membered ring (also, because the absence of a double bond as stated by claim 246 would trigger the “wherein” clause of claim 240, regarding the 3-4 membered heterocyclic rings).
Response to Arguments
Applicants arguments, see pg 15-16, filed 08/08/2025, with respect to the claims 250 and 258 objections, 112b rejection of claim 251, and the 101 rejection of claims 255-257 have been fully considered and are persuasive due to the amendments made by Applicant.. Therefore, these objections/rejections have been withdrawn. As for the specific reasons for withdrawing the rejections/objections above, we acknowledge: (1) the 112b antecedent basis claim numbering issue has been fixed in claim 251, (2) the 101 issue for claims 255-257 has been fixed by removing CH2OR as an option that amends away from the natural product genipin, and (3) claims 250 and 258 objections have been fixed by importing structure lists into the claim set.
Applicants arguments, see pg 16-26, filed 08/08/2025, with respect to the 102 and 103 rejections of claims 240-245 and 248-259 have been fully considered and are considered persuasive. However, in view of the IDS, new rejections have been applied due to submitting a reference with relevant Art. This is because Applicant filed an IDS on 10/15/2025 with Art (FR3003860A1) that reads on the claim set after the Non-Final Office Action filed 05/12/2025. Furthermore, Applicant has added new claims 260-263. Thus, the 102 and 103 rejections have been modified with respect to the reference from the new IDS and newly added claims.
On page 16-26, Applicant has argued the references of the previous 102 and 103 rejections. The Examiner has found that the amendments made to the claim set in order to avoid the species of the previously-used references, render the arguments moot. Note that the references of the previous Office Action are no longer currently applied in the claim rejections above. However, the Examiner directs Applicants attention to the references of Herve and Handley, which is Art that reads on the current claim set in the 102 and 103 rejections above.
Correspondence
Applicant's submission of an information disclosure statement under 37 CFR 1.97(c) with the timing fee set forth in 37 CFR 1.17(p) on 10/15/2025 prompted the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 609.04(b). 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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/R.P./Examiner, Art Unit 1614 10/21/2025
/SEAN M BASQUILL/Primary Examiner, Art Unit 1614
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