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
Claim Status
Claims 1-20 are pending. Claims 1-20 are under examination. Claims 1-20 are rejected. No claims allowed.
Filing Receipt
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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.
Claim(s) 1, 3-5, 8-10, 14-15 and 18-19 is/are rejected under 35 U.S.C. 103 as being unpatentable over Pickenhagen et al. (US Patent 5,892,062), Dash et al. (Oxidation by Permanganate: Synthetic and Mechanistic Aspects, Tetrahedron, 65, pp. 707-739, Published 2009) and Semmler et al. (Zur Kenntnis der Bestandteile atherischer ole (Untersuchungen fiber das Sesquiterpen Cedren), BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, DE, Vol. 40, No. 3, pages 3521-3528, Published 1907, IDS filed 10/20/2023, D1 in written opinion for PCT/EP2021/060525, Translation attached).
Scope of the Prior Art
The cis and trans-cedrene diols of alpha-cedrene are taught by Pickenhagen et al. to have odors and that derivatives of cedrene are sensorially desirable fragrances (column 2, lines 20-30, and column 1, lines 30-55).
Alternatively, Pickenhagen et al. teach the diols of cedrene in mixed or pure form are utilized to prepare compounds that have quite unique odoriferous properties (column 1, lines 45-67).
Pickenhagen et al. teach methods to prepare the diol and the compounds that have quite unique odoriferous properties (See Examples).
Pickenhagen et al. teach alpha cedrene (column 2). The purity is interpreted to be 100%. (current claim 3).
Ascertain the Differences
Pickenhagen et al. does not teach the process to prepare cis-cedrene diols from alpha-cedrene via oxidation by potassium permanganate (KMnO4) in the presence of water and one further protic solvent.
Secondary References
Dash et al. teach in general the oxidation of carbon-carbon double bonds by permanganate ion is an important and well-known reaction in organic chemistry, in a mechanistic as well as a synthetic prospective. Under alkaline conditions, olefins are converted into the corresponding diols in good yield (p. 708 right column). Dash teach alkaline conditions leading to the cis-diols (p. 712, left column).
Dash et al. teach permanganate oxidations of organic substances are performed in aqueous media with organic co-solvents, in which KMnO4 shows an appreciable solubility and inertness. The co-solvents mostly used are tert-butanol (current claim 14), acetone, pyridine and acetic acid (p. 712, right column).
Dash et al. teach permanganate has been widely used as a strong, easily handled, readily available and versatile oxidant that reacts with alcohols, alkenes… The reaction pathway is influenced by solvent, pH, substrate and other variables, thus complicating the mechanistic understanding. The use of organic solvents allows the substrate and solvent to be in the same phase and avoids some of the complications of aqueous permanganate reactions…(p.724, left column).
Semmler et al. teach the oxidation of cedrene in aqueous acetone to prepare the glycol C15H26O2 (p. 3523). Concerning the current solution without the further protic solvent, Semmler et al. teach the cedrene is dissolved in aqueous acetone (p. 3523). Concerning addition rate of the KMnO4, Semmler et al. teach the KMnO4 is gradually added (p. 3523).
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have prepared the current cis-cedrene diol to determine if the compound has any odors useful as fragrances. The ordinary artisan would have done so with a reasonable expectation of success because the cis and trans-cedrene diols of alpha-cedrene are taught by Pickenhagen et al. to have been prepared and which have odors. Additional motivation to prepare the diols being derivatives of cedrene are sensorially desirable fragrances (column 2, lines 20-30, and column 1, lines 30-55).
Alternatively, It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have prepared the current cis-cedrene diol and to have utilized the cis-cedrene diol as an intermediate for the production of compounds that have quite unique odoriferous properties. The ordinary artisan would have had a reasonable expectation of success because Pickenhagen et al. teach methods to prepare the diol and the compounds that have quite unique odoriferous properties.
Next, it would have been prima facie obvious for an ordinary artisan before the
effective filing date of the claimed invention to have tried to prepare the current cis-
cedrene diol from the known alpha-cedrene using an alternative oxidative method via KMnO4, water and t-butanol. MPEP 2143 I (B) and/or (E).
The ordinary artisan would have had a reasonable expectation of success because Semmler et al. teach the oxidation of cedrene in aqueous acetone to prepare the glycol C15H26O2 and because Dash et al. teach in general the oxidation of carbon-carbon double bonds by permanganate ion is an important and well-known reaction in organic chemistry, in a mechanistic as well as a synthetic prospective. Under alkaline conditions, olefins are converted into the corresponding diols in good yield (p. 708 right column). Dash teach alkaline conditions leading to the cis-diols (p. 712, left column).
Concerning the protic solvent, Dash teach permanganate oxidations of organic substances are performed in aqueous media with organic co-solvents, in which KMnO4 shows an appreciable solubility and inertness. The co-solvents mostly used are listed by Dash and the list includes tert-butanol. It would have been obvious to test the solvents taught by Dash and Semmler et al. to find the optimal solvent with a reasonable expectation of success via routine experimentation because Dash teach the solvent being a variable that effects the mechanism of the reaction. Moreover, choosing and/or trying a solvent from a list of known solvents is obvious. MPEP 2143 I (B) and/or (E).
Alternatively, the ordinary artisan would have investigated the known solvents with a reasonable expectation of success to establish the best solvent for solubility and inertness and to ensure the substrate and solvent are in the same phase.
In doing so the ordinary artisan would have arrived at the current invention.
A solution of the t-butanol, water and starting material would have been obvious to prepare with a reasonable expectation of success because Semmler et al. teach the cedrene is dissolved.
Concerning providing a solution of alpha-cedrene in a solvent and adding a base and KMnO4, adding reagents in any order is obvious. Selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results In re Burhans, 154 F.2d 690, 69 USPQ 330 (CCPA 1946) and Selection of any order of mixing ingredients is prima facie obvious. In re Gibson, 39 F.2d 975, 5 USPQ 230 (CCPA 1930). See MPEP 2144.04 IV C.
Concerning claim 4, it would have been obvious to arrive at the current ratios via routine experimentation. The ordinary artisan knowing the solvent being an art recognized variable, would have adjusted the amounts of the water and t-butanol to ensure the substrate and solvent to be in the same phase.
Concerning claim 5 and 8, adding reagents in any order is obvious. Thus, adding the KMnO4 in the base with water first and secondly adding the base mixture to the claimed solution is obvious. Selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results In re Burhans, 154 F.2d 690, 69 USPQ 330 (CCPA 1946) and Selection of any order of mixing ingredients is prima facie obvious. In re Gibson, 39 F.2d 975, 5 USPQ 230 (CCPA 1930). See MPEP 2144.04 IV C.
Concerning the current time interval of adding the base/KMnO4 solution, Semmler et al. teach the KMnO4 is gradually added. The ordinary artisan knowing the reaction (Dash et al. p. 708 right column) and being instructed by Semmler et al. to gradually add the KMnO4, would have optimized the gradual addition to the claimed
timeframe.
Concerning claim 9 and 18, the ordinary artisan knowing both water and KMnO4 were needed would have found the workable ranges and arrived at the ratios of claim 18. MPEP 2144.05 II. A. and B. “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).
Concerning claim 10 and 19 and the current temperature of the mixture, the prior art is silent to a temperature of the water/protic solvent and alpha-cedrene solution. As argued above the ordinary artisan was taught to dissolve the starting material in solvents. Without a specific teaching of a temperature, the ordinary artisan would have tried room temperature when dissolving the starting material to prepare the current solution. Room temperature overlaps the current temperature range of 5 to 40C. MPEP 2144.05 I.: “In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).”
Concerning claim 15 and the current ratios of the alpha-cedrene to the further protic solvent and to water, the ordinary artisan in view of Dash et al. would have been aware of the solubility of the MnO4 and the substrate and solvent being in the same phase. To ensure the solubility of MnO4 and substrate, the ordinary artisan would have arrived at the current ratios via routine experimentation. Too little, no dissolution. Too much, diminishing returns.
Claim(s) 2, 6-7, 12-13, 16-17 and 20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Pickenhagen et al. (US Patent 5,892,062), Dash et al. (Oxidation by Permanganate: Synthetic and Mechanistic Aspects, Tetrahedron, 65, pp. 707-739, Published 2009) and Semmler et al. (Zur Kenntnis der Bestandteile atherischer ole (Untersuchungen fiber das Sesquiterpen Cedren), BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, DE, Vol. 40, No. 3, pages 3521-3528, Published 1907, IDS filed 10/20/2023, D1 in written opinion for PCT/EP2021/060525,Translation attached) as applied to claims 1, 3-5, 8, 9-10, 14-15, 18-19 and in further view of Dalmizrak et al. (Supporting Materials, A Facial Synthesis of Vicinal cis-diols from olefins Catalyzed by in Situ Generated MNxOy nanoaggregates, pp. 1-19, Published 2015) and Aota et al. (Bronsted Acid-Catalyzed Intramolecular alfa-Arylation of Ketones with Phenolic Nucleophiles via Oxy-Allyl Cation Intermediates, Eur. J. Org. Chem., pp. 1907-1911, Published 2020, Supporting Information, pp. 1-151, Published 2020).
Scope of the Prior Art
The teachings of Pickenhagen et al., Dash et al., and Semmler et al. are in the above 103 rejections and are incorporated by reference.
Ascertain the Differences
The teachings of Pickenhagen et al., Dash et al., and Semmler et al. do not teach extraction of the cis-cedrene and the removal of the extractant to obtain the cis-cedrene.
Secondary References
Dalmizrak et al. teach the extraction of alkyl and cyclical vicinal diols with ethyl
acetate (current claim 12) from oxidizing aqueous/organic mixtures and removal of the solvent (pages 2-3 of 19). Dalmizrak et al. teach preparing the diols from the respective olefins (pages 2-3 of 19).
Aota et al. teach a cyclic vicinal diol extracted from a t-butanol/water reaction mixture via ethyl acetate with removal of the solvent/extractant via evaporation and column chromatography (p. S3-4, Supporting Information). Aota et al. teach the preparation of the cyclic vicinal diol via the respective olefin in t-butanol and water in the presence of NaOH and KMnO4 (p. S3-4, Supporting Information).
Concerning claim 7 and 17, Aota et al. teach 1.1 and 1.0 equivalences of KMnO4
and NaOH respectively (p. S3-4, Supporting Information). These ranges overlap the
claimed ranges.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention with a reasonable expectation of success to have extracted the current diol with the ethyl acetate taught by Dalmizrak et al. and Aota et al. The ordinary artisan would have done so to satisfy a need for obtaining the product. Upon removal of the extractant/solvent taught by both Dalmizrak et al. and Aota et al., the current diol would have been obtained. The reasonable expectation of success being from the fact that a variety of vicinal diol compounds prepared from the respective olefins in oxidizing, organic, and aqueous mixtures are extracted using ethyl
acetate.
Concerning claim 6 and 16, to satisfy a source of alkali, the ordinary artisan
would have utilized the NaOH taught by Aota et al. with a reasonable expectation of
success.
Concerning claim 7 and 17, MPEP 2144.05 I.: “In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).”
Concerning claim 13 and the ratio of extractant to the starting material alpha cedrene, the ordinary artisan would have arrived at the current ratios via routine experimentation. Not enough extractant would have led to the product not being extracted. Too much extractant diminishing returns.
Claim(s) 11 is/are rejected under 35 U.S.C. 103 as being unpatentable over
Pickenhagen et al. (US Patent 5,892,062), Dash et al. (Oxidation by Permanganate: Synthetic and Mechanistic Aspects, Tetrahedron, 65, pp. 707-739, Published 2009) and Semmler et al. (Zur Kenntnis der Bestandteile atherischer ole (Untersuchungen fiber das Sesquiterpen Cedren), BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, DE, Vol. 40, No. 3, pages 3521-3528, Published 1907, IDS filed 10/20/2023, D1 in written opinion for PCT/EP2021/060525, Translation attached), Dalmizrak et al. (Supporting Materials, A Facial Synthesis of Vicinal cis-diols from olefins Catalyzed by in Situ Generated MNxOy nanoaggregates, pp. 1-19, Published 2015), Aota et al. (Bronsted Acid-Catalyzed Intramolecular alfa-Arylation of Ketones with Phenolic Nucleophiles via Oxy-Allyl Cation Intermediates, Eur. J. Org. Chem., pp. 1907-1911, Published 2020, Supporting Information, pp. 1-151, Published 2020) as applied to claims 1-10, 12-20 and in further view of Rochester (Remove Sticky Reagents, pages 1-2, Published 12-2020) and Boulder (Solvent Removal, pp. 1-10, Published 03-2017).
Scope of the Prior Art
The teachings of Pickenhagen et al., Dash et al., Semmler et al., Dalmizrak et al., and Aota et al. are in the above 103 rejections and are incorporated by reference.
Ascertain the Differences
The teachings of Pickenhagen et al., Dash et al., Semmler et al., Dalmizrak et al.,
and Aota et al. do not teach removing the at least one further protic solvent from the
reaction mixture, wherein the removal is carried out by distillation.
Secondary References
Rochester teach complications can occur to mixed solvents in an aqueous workup (p. 1). Rochester goes on to teach alcohols do not cooperate during typical aqueous workup (p. 1). Rochester teach removing the solvent by rotoevaporation first (p. 1). Rochester teach removal of solvents via binary distillates as azeotropes (p. 2).
Boulder teach simple distillation can be used to remove solvent (p. 1). Advantages of distillation are that the solvent can be collected and recycled and that no vapors are released into the atmosphere (p. 1). Boulder teach rotary evaporators can also be used to remove solvent.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have removed the t-butanol prior to the extraction to avoid complications as taught by Rochester. Additionally, the ordinary artisan knowing that t-butanol being an alcohol does not cooperate during typical aqueous workup, would have removed the t-butanol before any workup of the reaction mixture. A reasonable expectation of success in removal of the alcohol being from the fact that Rochester teach removal via rotoevaporation or as a distillate.
Next it would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have tried to remove the t-butanol via an alternative method of distillation with a reasonable expectation of success. MPEP 2141
III (B) and/or (E).
The ordinary artisan would have tried distillation as taught by Boulder because
simple distillation can be used to remove solvents that can be collected and recycled and that no vapors are released into the atmosphere. The ordinary artisan would have looked to Rochester due to both Dash et al. and Rochester teach aqueous mixtures and alcohol solvents. The ordinary artisan would have looked to Boulder because of the distillates and rotoevaporation taught by Rochester.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to BLAINE G DOLETSKI whose telephone number is (571)272-2766. The examiner can normally be reached M-F 7-4 EST.
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/B.G.D/Examiner, Art Unit 1692 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625
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