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 .
Status of the Claims
The amendment filed on 08/18/2026 has been entered. Claim 1 has been amended; claims 2 and 10-12 have been canceled; and claim 16 has been newly added. Thus, claims 1, 3-9 and 13-16 are currently pending and are under examination.
Withdrawn Objections and Rejections
The objections to the specification and drawing have been withdrawn in view of the amendment.
Claim 1 has been amended by narrowing the terminal alkene and internal alkene to specific species. Sharma I (Sharma, S. K. et al. "Ruthenium containing hydrotalcite as a solid base catalyst for >C=C< double bond isomerization in perfumery chemicals" Journal of Molecular Catalysis A: Chemical 317 (2010) 27-33), Sharma II (Sharma, S. K. et al. " Solvent-free isomerization of methyl chavicol to trans-anethole using transition metal complexes as catalysts" Catalysis Communications 6 (2005) 205–209), and Patent application publication number US2013/0288947A1 (US’947), all cited in PTO-892 3/18/2026, fail to teach or suggest every limitation of amended claim 1. Thus, the 102(a)(1) rejections of the record have been withdrawn.
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:
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, 3-9 and 13-16 are rejected under 35 U.S.C. 103 as being unpatentable over Sharma II (Sharma, S. K. et al. " Solvent-free isomerization of methyl chavicol to trans-anethole using transition metal complexes as catalysts" Catalysis Communications 6 (2005) 205–209; cited in PTO-892 3/18/2026) in view of Narula (Narula, A. P. S. et al. Patent application publication number US2013/0165532A1; cited in PTO-892 3/18/2026).
Regarding claims 1, 3 and 15, Sharma II teaches a process for making perfumery chemicals by isomerizing starting materials comprising a terminal alkene to form a product comprising an internal alkene in the presence of ruthenium catalyst at a temperature of 491 K (217.85 °C) (Schemes 1-2 and Tables 1-2).
Regarding claims 4, 6 and 8-9, Sharma II teaches that the ruthenium catalyst is either ruthenium salt, RuCl3.3H2O, or ruthenium complex, RuCl2(PPh3)3, RuCl3(AsPh3)2.CH3OH and RuCl2(SbPh3)3 (Tables 1-2).
Regarding claims 5 and 7, the isomerization process uses 1.0 g of methyl chavicol ( 148.2 g/mol) and 0.01 of each catalysts (Table 1), thus the amount of the catalyst based on the total molar amount of methyl chavicol is:
RuCl3.3H2O (260.47 g/mol) 0.57 mol% (claim 5),
RuCl2(PPh3)3 (958.83 g/mol) 0.156 mol% (claim 7),
RuCl3(AsPh3)2.CH3OH (958.83 g/mol) 0.175 mol% (claim 7), and
RuCl2(SbPh3)3 (1231.19 g/mol) 0.12 mol% (claim 7).
Regarding claim 13, Sharma II teaches that the isomerization process is solvent free.
Regarding claim 14, Sharma II teaches that the reaction mixture was cooled down to room temperature and then filtered (1st col., pg. 206).
Regarding claim 16, the claimed mol% is merely close to the above mole % of the ruthenium catalyst taught by Sharma II. MPEP §2144.04 states a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close.
Regarding claim 1, the reference fails to teach that the terminal alkene is a mixture of 2-propoxy-5-vinylcyclohexan-1-ol and 2-propoxy-4-vinylcyclohexan-1-ol, and the internal alkene is a mixture of 2-propoxy-5-ethylidenecyclohexan-1-ol and 2-propoxy-4-ethylidenecyclohexan-1-ol or the terminal alkene is 9-decen-1-ol and the internal alkene comprises a mixture of 6-decen-1-ol, 7-decen-1-ol and 8-decen-1-ol. The deficiency is however cured by Narula.
Narula teaches a process of isomerizing 9-decen-1-ol to 6,7,8-decene-1-ol ([0037]-[0038]) in the presence of RhCl3 at 65-80° C. The reference further teaches that 6,7,8-Decene-1ol have aldehydic, green, floral, rosy, and waxy notes ([0039]. Thus, replacing the catalyst and reaction temperature of Narula with the ruthenium catalyst and temperature of Sharma II, a skilled artisan would still have a reasonable expectation of success in conducting nothing more than the isomerization reaction of 9-decen-1-ol to 6,7,8-decene-1-ol.
It would thus have been prima facie obvious to a skilled artisan before the effective filing date of the instant invention to conduct a process for making fragrance ingredient or fragrance intermediate, comprising isomerizing a starting material comprising a terminal alkene to form a product comprising an internal alkene in the presence of a ruthenium catalyst at a temperature of at least about 120° C, wherein the terminal alkene is a mixture of 2-propoxy-5-vinylcyclohexan-1-ol and 2-propoxy-4-vinylcyclohexan-1-ol, and the internal alkene is a mixture of 2-propoxy-5-ethylidenecyclohexan-1-ol and 2-propoxy-4-ethylidenecyclohexan-1-ol or the terminal alkene is 9-decen-1-ol and the internal alkene comprises a mixture of 6-decen-1-ol, 7-decen-1-ol and 8-decen-1-ol in view of the teachings of Sharma II and Narula.
Response to Arguments
Applicant argues
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The arguments have been considered but are not persuasive. The specific ratio described in Narula refers only to internal decenal isomer mixture but not to the internal dicenol mixture. As described in Example 1, the isomerization of 9-dicenol affords 6,7,8-decene-1-ol (463 g), with no specific ratios of each. Thus, there is no criticality mentioned in Narula in using the specific catalyst, solvent and temperature of Narula to obtain a specific ratio of 6,7,8-decene-1-ol. Thus, changing the catalyst and reaction temperature of Narula with that of Sharma II, the latter also applicable in isomerizing terminal alkenes to internal alkenes, a skilled artisan would still have a reasonable expectation of success in arriving at the instantly claimed invention, i.e. in obtaining 6,7,8-decene-1-ol from 9-dicenol.
In view of the foregoing, amended claim 1 remains obvious for reasons set forth above.
Conclusion
Claims 1, 3-9 and 13-16 are rejected and no claims are 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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to MEDHANIT W BAHTA whose telephone number is (571)270-7658. The examiner can normally be reached Monday-Friday 8am-5pm.
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/MEDHANIT W BAHTA/Primary Examiner, Art Unit 1692
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