--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 .
Applicant’s response dated December 15, 2025 is acknowledged.
Priority
This application is a 371 of PCT/EP2019/066095 filed on 06/18/2019, and claims foreign
priority in EP18179137.7 filed on 06/21/2018.
Claim status
Claims 1, 2, and 4-20 are pending. Claims 6-14 and 17-20 remain withdrawn. Claim 1 was amended. Claim 3 was canceled. Claims 1, 2, 4, 5, 15, and 16 are examined.
Election/Restrictions
Applicants elected Group I and Compound 9 in the reply filed October 2, 2023. The
election has been treated as an election without traverse (MPEP § 818.01 (a)). The elected
species of Compound 9 appears to be free of the prior art, so examination was expanded to other
species falling within the scope of the present claims.
Withdrawn Claim Rejections -35 USC§ 112
Rejections of claims 1-5, 15, and 16 are withdrawn because claim 1 was amended by deleting "long-lasting", and claims 2-5, 15, and 16 no longer depend from an indefinite base claim.
Withdrawn Claim Rejections - 35 USC§ 103
Rejections of claims 1-4 and 16 over Aschwanden (Reduction of 2,3-Dihydroisoxazoles to B-Amino Ketones and B-Amino Alcohols, Organic Letters, Vol. 7, No 25, pp. 5741-5742, 2005) are withdrawn because claim 1 was amended to further limit the compound of formula I to the list of compounds recited in the newly added wherein clause, and Aschwanden’s compound 1 in Table 1 of formula
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is not a homologue of the claimed compounds and it would not have been obvious to modify Aschwanden’s compound 1 by addition of repeating units to arrive at the instantly claimed compounds.
Withdrawn Double Patenting Rejections
Double patenting rejections of claims 1, 2, 4, and 15 over claims 1-3 and 5 of US Patent 12,291,689 B2 are withdrawn because instant claim 1 was amended by limiting the scope of the compound of Formula I to compounds listed in the newly added wherein clause, which are not obvious over the compounds in the patented claims.
Maintained Claim Rejections - 35 USC§ 103
Modified as Necessitated by Amendment
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:
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 CPR 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, 2, 4, 5, 15, and 16 are rejected under 35 U.S.C. 103 as being unpatentable over
Herrmann (U.S. 2016/0222327 Published August 4, 2016).
The claims are drawn to a compound of formula I.
Herrmann teaches thioether derivatives as controlled precursors for a controlled release
of active perfumery molecules. Herman teaches a thioether derivative of formula I
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wherein P represents a group susceptible of generating a perfuming alpha,beta- unsaturated
ketone or aldehyde and is represented by formula II
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in which the wavey lines represents the location of the bond between
said P and the sulfur atom; R1 represents a hydrogen atom, a C1-C 15 linear, cyclic, or branched
alkyl, alkenyl, or alkadienyl radical; and R2, R3, and R4 represent a hydrogen atom, an aromatic
ring, or a Cl-C15 linear, cyclic, or branched alkyl, alkenyl, or alkandienyl radical, and X
represents a functional group selected from i, ii, and iii, having the structure
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, in which formula the wavey lines are as defined
previously and the bold lines indicate the location of the bond between said X and R; and R
represents a C3-C5 alkyl group optionally comprising 1 or 2 functional groups selected from NO2, ether, alcohol, and thioether (paragraphs 0008-0013).
It would have been prima facie obvious to a person of ordinary skill in the art before the
effective filing dated of the claimed invention to have formed a compound of formula I in which
Rl is a C4 linear alkyl, R2 is hydrogen, R3 is methyl, R4 is hydrogen, X is formula i) and R is a
C3-C5 alkyl comprising an alcohol group, with a reasonable expectation of success because Herrmann teaches compounds of formula I as described above having said substituents.
Thus, a prima facie case of obviousness is established. MPEP 2143.
Prior art compounds of formula I having the variables as described above are
encompassed by the claimed genus of formula I when the claimed compound is a 2-((hydroxyalkyl)thio)octan-4-one derivative with the size of the alkyl group varying between C2 and C18 in claims 1, 2, 4, 15, and 16. It would have been reasonable to expect the prior art compounds to have a vapor pressure below 2.0 at room conditions, and it would have been reasonable to expect the prior art compounds to generate oct-2-ene-4-one by reaction with room humidity to emit a strawberry odor because a compound and its properties are inseparable. The Office does not have the means to test prior art compounds to determine if the compounds have the same properties as claimed compounds. Claim 1 describes compound properties, and the prior art is not required to disclose said properties in order to render the claimed compound obvious. It is the examiner's position that if the vapor pressure of prior art compounds was measured under the same conditions as claimed, the vapor pressure would have been below to 2.0 Pa; and if prior art compounds were placed under the same room humidity conditions as claimed they would have generated oct-2-ene-4-one and emitted a strawberry odor because prior art compounds are species of compound of formula I and a compound and its properties are inseparable.
Regarding claim 5, it would have been prima facie obvious to a person of ordinary skill in the art before the effective filing dated of the claimed invention to have formed a compound of formula I in which Rl is a C4 linear alkyl, R2 is hydrogen, R3 is methyl, R4 is hydrogen, X is formula i) and R is a C3-C5 alkyl, with a reasonable expectation of success because Herrmann teaches compounds of formula I as described above having said substituents. Thus, a prima facie case of obviousness is established. MPEP 2143.
The claimed compound of formula I, 2-(alkylthio)octan-4-one derivative with the size of the alkyl group varying between C6 and C18, would have been obvious over the prior art compounds as described above because it is a homolog of the prior art compounds where the difference between the two genera compounds is in the number of methylene groups in the alkyl group bonded to the sulfur atom. The claimed alkyl having between 6 and 18 carbon atoms would have been obvious over an alkyl group having from 3 to 5 carbon atoms because it has been held that compounds which are 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. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious); Aventis Pharma Deutschland v. Lupin Ltd., 499 F.3d 1293, 84 USPQ2d 1197 (Fed. Cir. 2007) (5(S) stereoisomer of ramipril obvious over prior art mixture of stereoisomers of ramipril.).
It would have been reasonable to expect the prior art compounds to have a vapor pressure below 2.0 at room conditions, and it would have been reasonable to expect the prior art compounds to generate oct-2-ene-4-one by reaction with room humidity to emit a strawberry odor because a compound and its properties are inseparable. The Office does not have the means to test prior art compounds to determine if the compounds have the same properties as claimed compounds. Claim 1 describes compound properties, and the prior art is not required to disclose said properties in order to render the claimed compound obvious. It is the examiner's position that if the vapor pressure of prior art compounds was measured under the same conditions as claimed, the vapor pressure would have been below to 2.0 Pa; and if prior art compounds were placed under the same room humidity conditions as claimed they would have generated oct-2-ene-4-one and emitted a strawberry odor because prior art compounds are species of compound of formula I and a compound and its properties are inseparable.
Response to Arguments
In the remarks dated December 15, 2025, the applicant traversed the rejections.
Applicant’s argument that claims are patentable over Hermann in view claim amendments is not persuasive because at least two claimed genera of compounds are obvious over Hermann as explained in the rejection. Arguments against withdrawn rejections are moot because rejections are withdrawn.
Conclusion
No claims are allowed.
THIS ACTION IS MADE FINAL. 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
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supervisor, Michael Hartley can be reached on 571-272-0616. The fax phone number for the
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/ALMA PIPIC/Primary Examiner, Art Unit 1617