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
Claims 21 – 40 are pending in this application. Applicant’s preliminary amendment, submitted March 27, 2024, is entered, wherein claims 21 – 40 are new and claims 1 – 20 are canceled.
Claims 21 – 40 are examined on the merits herein.
Priority
This application is a national stage application of PCT/EP2022/076634, filed September 26, 2022, which claims benefit of foreign priority document EP21199835.6, filed September 29, 2021.
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 04/06/2024 and 04/25/2024 were filed in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement has been considered by the examiner.
Specification
Applicant is reminded of the proper language and format for an abstract of the disclosure.
The abstract should be in narrative form and generally limited to a single paragraph on a separate sheet within the range of 50 to 150 words in length. The abstract should describe the disclosure sufficiently to assist readers in deciding whether there is a need for consulting the full patent text for details.
The language should be clear and concise and should not repeat information given in the title. It should avoid using phrases which can be implied, such as, “The disclosure concerns,” “The disclosure defined by this invention,” “The disclosure describes,” etc. In addition, the form and legal phraseology often used in patent claims, such as “means” and “said,” should be avoided.
The abstract is objected to because it exceeds 150 words. Applicant is required to amend the abstract so that it does not exceed 150 words.
Claim Objections
Claims 21 – 22, 28 – 30, 32, 36, and 38 are objected to because of the following informalities:
Claim 21, lines 6 – 7, “,” immediately after “selected from” and “methyl” should be removed.
Claim 21, line 6, “and” should be inserted immediately after “-CH2-(CO)-R,”.
Claim 22, line 1, “,” immediately after “-O-R” should be removed.
Claim 28, line 2, “accordingly” should read “according to”
Claim 28, line 2, “an aroma” should read “the aroma”,
Claim 28, line 2, “a composition” should read “the composition”.
Claim 29, line 2, “a composition” should read “ the composition”.
Claim 30, line 1, “,” immediately after “selected from” should be removed.
Claim 32, line 3, “or” immediately after “(I),” should be removed.
Claim 36, line 3, “or” immediately after “(II),” should be removed.
Claim 38, line 2, “a composition” should read “the composition”.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 34 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 34 recites “the weight ratio of total amount of compounds of formula (Ia) and total amount of compounds of formula (II)” in lines 1 – 2. Claim 34 depends from claim 32, which ultimately depends from claim 21, and claims 21 or 32 never recites “formula (Ia)” and “formula (II)”. Therefore, claim 34 lacks sufficient antecedence to an earlier claim.
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 21 – 22 are rejected under 35 U.S.C. 103 as being unpatentable over Weingarten et al. (EP3763352A1) in view of Brown (Wiley-Vch, Cop, 2012, PTO-892).
Weingarten et al. teach the compound 2,5,6-trimethylcyclohex-2-en-1-ol (para. [0078]).
However, Weingarten et al. differ from the structure of formula (I) in that Weingarten et al. teach a hydroxyl group at the position corresponding to X, and do not teach X as recited in claims 21 - 22.
Brown teaches that -CH3 is a classical bioisosteres of -H (page 17, 2.3.1 Monovalent Atoms and Groups).
It would have been prima facie obvious for a person of ordinary skill in the art before the effective filing date of the claimed invention to modify 2,5,6-trimethylcyclohex-2-en-1-ol as taught by Weingarten et al. by substituting the hydrogen of the hydroxyl group with a methyl group in view of Brown to provide the corresponding methyl ether because substitution of hydrogen with methyl is a classical bioisosteric substitution known in the art to provide predictable results. Brown establishes that substitution of H with CH3 is a known classical bioisosteric structural modification. Furthermore, MPEP § 2144.08(II) 4 states that structural similarities between the claimed and prior art compounds may support a prima facie case of obviousness where the compounds are sufficiently closely related and the prior art provides reason to expect similar properties. Accordingly, replacing the hydrogen of hydroxyl group in 2,5,6-trimethylcyclohex-2-en-1-ol of Weingarten et al. with methyl would provide 2,5,6-trimethylcyclohex-2-en-1-yl methyl ether, having X = -O-CH3 as encompassed by claim 21 and specifically recited in claim 22. A person of ordinary skill in the art would have had a reasonable expectation of success in making this modification because methyl-for-hydrogen substitution is known in the art as a classical bioisosteric substitution providing predictable results, and the proposed modification merely substitutes methyl for hydrogen attached to the oxygen of the disclosed hydroxyl group of Weingarten et al. while retaining the 2,5,6-trimethylcyclohexenyl scaffold.
Claims 21, 23, and 28 – 32 are rejected under 35 U.S.C. 103 as being unpatentable over Weingarten et al. (EP3763352A1) in view of Bruns et al. (US4080309).
Weingarten et al. teach the production process of aroma compounds (I):
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wherein the compounds (I) are produced from 2,5,6-trimethylcyclohex-2-en-1-ol (para. [0078]):
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2,5,6-trimethylcyclohex-2-en-1-ol provides a pleasant odor profile at concentrations of at most 100 ppm (para. [0079]). At concentration of 100 ppm in ethanol, 2,5,6-trimethylcyclohex-2-en-1-ol imparts a phenolic, green banana, nutty, milky and/or warm note (para. [0185]). Thus, Weingarten et al. teach that the 2,5,6-trimethylcyclohexenyl scaffold possesses aroma properties and is suitable for imparting an aroma impression to a composition. Weingarten et al. further exemplify the use of 2,5,6-trimethylcyclohex-2-en-1-ol as a starting material in preparing trimethylcyclohexenyl aroma compounds (para. [0308]), thereby demonstrating that this alcohol is a suitable and operative substrate within the disclosed synthetic scheme. Weingarten et al. teach a self-foaming bodywash, wherein the fragrance composition 1A is at 1.0 wt.% (page 47, Table 7). In a preferred embodiment, the composition comprises the synthesized compounds and at least one further component, such as aroma chemicals, non-aroma chemical carriers, anti-oxidants, and deodorant-active agents (para. [0203]). Weingarten et al. therefore further teach incorporating trimethylcyclohexenyl aroma compounds into fragrance compositions together with additional aroma chemicals and/or non-aroma chemical carriers, thereby teaching the general aroma-use and composition features recited in claims 28 – 29 and 32.
However, Weingarten et al. differ from the structure of formula (I) in that Weingarten et al. teach a hydroxyl group at the position corresponding to X, and do not teach X as recited in claims 21 and 23.
Bruns et al. teach carbonic acid esters of the formula:
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useful as perfumes and having very natural, pleasing, and persistent scents (Abstract; Col., 1, lines 10 – 13). Bruns et al. teach such carbonic acid esters by reacting a cycloaliphatic alcohol:
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with a chloroformic acid ester (Col. 1, lines 28 – 44):
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The cycloaliphatic alcohol may be an alkylcyclohexanol, including menthol, carvomenthol, trans-3,3,5-trimethylcyclohexanol, and cis-3,3,5-trimethylcyclohexanol (Col. 3, lines 45 – 50). Bruns et al. further teach methyl and ethyl chloroformates as suitable reaction partners and exemplify methyl and ethyl carbonate derivatives of cyclic alcohols, including methyl and ethyl trimethylcyclohexyl carbonates (Col. 4, lines 25 – 68). Bruns et al. further teach that methyl and ethyl chloroformates are of particular importance because products having intensive scents are obtained therefrom (Col. 2, lines 67 – 68; Col. 3, lines 1 – 2).
It would have been prima facie obvious for a person of ordinary skill in the art before the effective filing date of the claimed invention to modify the 2,5,6-trimethylcyclohex-2-en-1-ol as taught by Weingarten et al. by converting the hydroxyl group thereof to a corresponding methyl or ethyl carbonate in view of Bruns et al., thereby obtaining a compound of formula (I), wherein X is -O-(CO)-O-R and R is methyl or ethyl because Weingarten et al. teach that 2,5,6-trimethylcyclohex-2-en-1-ol may be used as a starting material for synthesizing an aroma compound and Bruns et al. establish that carbonate formation is a known modification of cycloaliphatic alcohols, including trimethyl-substituted cyclohexanols, and explicitly teach methyl and ethyl carbonate derivatives thereof. One of ordinary skill in the art would have been motivated to make such a modification because Weingarten et al. teach that 2,5,6-trimethylcyclohex-2-en-1-ol possesses useful odor properties and Bruns et al. teach that carbonate derivatives of cycloaliphatic alcohols are useful perfume materials having natural, pleasing, and persistent scents and particularly identify methyl and ethyl carbonate derivatives as providing intensive scents. Thus, one of ordinary skill in the art seeking additional aroma chemicals based on the odor active cyclic alcohol taught by Weingarten et al. would have had reason to prepare its methyl or ethyl carbonate derivative in view of the fragrance properties taught by Bruns et al. One of ordinary skill in the art would have had a reasonable expectation of success to prepare the modified compound because Bruns et al. explicitly teach formation of carbonate esters from cycloaliphatic alcohols and identify substituted cyclic alcohols, including trimethyl-substituted cyclohexanols, as suitable substrates, as well as methyl and ethyl chloroformates as suitable reagents for producing the corresponding methyl and ethyl carbonates. Accordingly, the teachings of Bruns et al. would have provided one of ordinary skill in the art with a known method and suitable reagents for converting the hydroxyl group of 2,5,6-trimethylcyclohex-2-en-1-ol of Weingarten et al. to the recited carbonate functionality with a reasonable expectation of success.
Regarding claim 30, the compound of formula (I) recited in claim 23 would have been prima facie obvious over Weingarten et al. in view of Bruns et al. Weingarten et al. teach that trimethylcyclohexenyl aroma compounds provide odor characteristics and are useful for imparting an aroma impression to a composition. The odor characteristics of a compound are properties resulting from its chemical structure. Accordingly, the compound of formula (I) resulting from the combination of Weingarten et al. and Bruns et al. would necessarily possess its inherent odor characteristics when prepared and used as an aroma chemical, thereby satisfying the odor characteristics recited in claim 30.
Regarding claim 31, the compound of formula (I) recited in claim 23 would have been prima facie obvious over Weingarten et al. in view of Bruns et al. Weingarten et al. further teach incorporating aroma compounds into fragrance compositions and exemplify a fragrance composition comprising an aroma compound in an amount of 1.0 wt.%, which falls within the recited range of ≥0.01 wt.% to ≤70 wt.%. It would have been obvious to one of ordinary skill in the art to employ the compound resulting from the combination of Weingarten et al. and Bruns et al. in a fragrance composition in an amount within the recited range and to determine the appropriate amount through routine experimentation based on the desired aroma intensity and the particular composition in which the aroma compound is employed.
Claims 21 and 24 are rejected under 35 U.S.C. 103 as being unpatentable over Weingarten et al. (EP3763352A1) in view of Ishihara et al. (US2005/0245407A1).
Weingarten et al. teach the production process of aroma compounds (I):
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wherein the compounds (I) are produced from 2,5,6-trimethylcyclohex-2-en-1-ol (para. [0078]):
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2,5,6-trimethylcyclohex-2-en-1-ol provides a pleasant odor profile at concentrations of at most 100 ppm (para. [0079]). At concentration of 100 ppm in ethanol, 2,5,6-trimethylcyclohex-2-en-1-ol imparts a phenolic, green banana, nutty, milky and/or warm note (para. [0185]). Thus, Weingarten et al. teach that the 2,5,6-trimethylcyclohexenyl scaffold possesses aroma properties and is suitable for imparting an aroma impression to a composition.
However, Weingarten et al. differ from the structure of formula (I) in that Weingarten et al. teach a hydroxyl group at the position corresponding to X, and do not teach X as recited in claims 21 and 24.
Ishihara et al. teach fragrance compositions comprising ester compounds as fragrance ingredients, wherein the ingredients may include compounds represented by formula (2) (para. [0012]):
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wherein R3 represents a methyl group and R4 represents a cyclic hydrocarbon group in which α-carbon or β-carbon to an ether linkage is an ester group in formula (2) has a branched chain (para. [0013]; para. [0037]). Ishihara et al. further teach that compounds of formula (2) include terpenyl esters of acetic acid, wherein the terpenyl esters of acetic acid may be carbyl acetate, dihydrocarbyl acetate, terpinyl acetate, menthyl acetate, dihydroterpinyl acetate, n-bornyl acetate, isobornyl acetate, and verbenyl acetate (para. [0039])
It would have been prima facie obvious for a person of ordinary skill in the art before the effective filing date of the claimed invention to modify the 2,5,6-trimethylcyclohex-2-en-1-ol as taught by Weingarten et al. by forming an acetate ester through its hydroxyl functionality in view of Ishihara et al., thereby obtaining a compound of formula (I), wherein X is -O-(CO)-R and R is methyl, as encompassed by claim 24 because Weingarten et al. teach that 2,5,6-trimethylcyclohex-2-en-1-ol may be used as a starting material for synthesizing an aroma compound and Ishihara et al. teach fragrance compounds of formula (2), wherein the acyl substituent may be methyl and the ester is attached to a branched cyclic hydrocarbon group, and explicitly identify acetate esters of terpene alcohol structures, including carvyl acetate, dihydrocarvyl acetate, terpinyl acetate, menthyl acetate, dihydroterpinyl acetate, n-bornyl acetate, isobornyl acetate, and verbenyl acetate, as fragrance ingredients. Thus, Ishihara et al. teach the known modification of alcohol functionality of cyclic terpene structures to provide the corresponding acetate fragrance compounds. One of ordinary skill in the art would have been motivated to modify the hydroxyl group of the 2,5,6-trimethylcyclohex-2-en-ol as taught by Weingarten et al. because Ishihara et al. specifically teach acetate esters corresponding to terpene alcohol structures as fragrance ingredients, including carvyl acetate, terpinyl acetate, menthyl acetate, bornyl acetate, and verbenyl acetate. Accordingly, starting from the odor active cyclic alcohol of Weingarten et al., one of ordinary skill in the art would have had reason to utilize the hydroxyl functionality of the alcohol to form the corresponding acetate ester in accordance with the cyclic terpene acetate of Ishihara et al. as fragrance materials, thereby providing another fragrance compound based on the odor active cyclic structure as taught by Weingarten et al. One of ordinary skill in the art would have had a reasonable expectation of success to obtain the proposed acetate derivative because Ishihara et al. teach numerous acetate esters corresponding to cyclic terpene alcohol structures, including acetate derivative of carvyl, terpinyl, menthyl, bornyl, and verbenyl structures, demonstrating that the hydroxyl functionality associated with structurally varied cyclic terpene alcohols is suitable for conversion to the corresponding acetate functionality. Accordingly, one of ordinary skill in the art would have reasonably expected the hydroxyl functionality of 2,5,6-trimethylcyclohex-2-en-ol of Weingarten et al. to be amenable to the corresponding acetate modification without requiring alteration of the underlying cyclic hydrocarbon structure .
Claims 21 and 25 are rejected under 35 U.S.C. 103 as being unpatentable over Weingarten et al. (EP3763352A1) in view of Hojo et al. (US8586009B2) and FAO (JECFA Monographs, 2008, PTO-892).
Weingarten et al. teach the production process of aroma compounds (I):
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wherein the compounds (I) are produced from 2,5,6-trimethylcyclohex-2-en-1-ol (para. [0078]):
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2,5,6-trimethylcyclohex-2-en-1-ol provides a pleasant odor profile at concentrations of at most 100 ppm (para. [0079]). At concentration of 100 ppm in ethanol, 2,5,6-trimethylcyclohex-2-en-1-ol imparts a phenolic, green banana, nutty, milky and/or warm note (para. [0185]). Thus, Weingarten et al. teach that the 2,5,6-trimethylcyclohexenyl scaffold possesses aroma properties and is suitable for imparting an aroma impression to a composition.
However, Weingarten et al. differ from the structure of formula (I) in that Weingarten et al. teach a hydroxyl group at the position corresponding to X, and do not teach X as recited in claims 21 and 25.
Hojo et al. teach l-menthyl acetoacetate and teach that several methods for synthesizing l-menthyl acetoacetate are known, including transesterification of l-menthol with methyl or ethyl acetoacetate (Col. 5 lines 24 – 67; Col. 6, lines 1 – 2). Hojo et al. further teach that l-menthyl acetoacetate can be obtained quantitatively by heating a mixture of l-menthol and methyl acetoacetate, without a solvent or in an aliphatic hydrocarbon having 5 to 8 carbon atoms, in the absence of a catalyst (Col. 6, lines 8 – 16). Particularly, example 1 teaches:
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reacting l-menthol with methyl acetoacetate in the presence of p-toluenesulfonic acid in heptane under reflux to obtain l-menthyl acetoacetate in 96.2% theoretical yield (Col. 15, lines 40 – 67). Thus, Hojo et al. teach conversion of the hydroxyl group of a substituted cyclic alcohol to an acetoacetate ester having an -O-(CO)-CH2-(CO)-CH3 group.
FAO teaches l-menthyl acetoacetate as a flavoring agent and identify the compound as 3-oxobutanoic acid (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester. FAO further characterizes l-menthyl acetoacetate as a clear colorless or pale yellow liquid having a minty aroma (page 101). FAO classifies l-menthyl acetoacetate among substances structurally related to menthol and conclude that its use as flavoring agent presents no safety concern at the evaluated intake (page 131, Table 3.1.4).
It would have been prima facie obvious for a person of ordinary skill in the art before the effective filing date of the claimed invention to modify the 2,5,6-trimethylcyclohex-2-en-1-ol as taught by Weingarten et al. by converting the hydroxyl group thereof to an acetoacetate ester in view of Hojo et al., thereby obtaining a compound of formula (I), wherein X is -O-(CO)-CH2-(CO)-R and R is methyl, as encompassed by claim 25 because Weingarten et al. explicitly teach that 2,5,6-trimethylcyclohex-2-en-1-ol possesses a pleasant odor profile at appropriate concentrations and imparts phenolic, green banana, nutty, milky, and/or warm notes and may be used as a starting material for synthesizing an aroma compound and Hojo et al. teach that the hydroxyl group of a substituted cyclic alcohol, l-menthol, is readily converted to the corresponding acetoacetate ester by transesterification with methyl acetoacetate. Thus, application of the acetoacetate derivatization taught by Hojo et al. to the hydroxyl functionality of the odor-active cyclic alcohol of Weingarten et al. would have provided the presently recited -O-(CO)-CH2-(CO)-CH3 substituent. One of ordinary skill in the art would have been motivated to make such modification because FAO teaches that l-menthyl acetoacetate, which is the same type of acetoacetate ester produced from a substituted cyclic alcohol according to Hojo et al., is a flavoring agent having a minty aroma. Accordingly, the prior art did not merely teach acetoacetylation as an arbitrary chemical transformation; instead, it specifically established that an acetoacetate derivative of a cyclic alcohol is useful for imparting sensory properties. In view of Weingarten et al. that 2,5,6-trimethylcyclohex-2-en-1-ol possesses aroma properties, one of ordinary skill in the art would therefore have had reason to derivatize its available hydroxyl group according to the known acetoacetate modification taught by Hojo et al. to obtain another cyclic alcohol-derived compound having potential utility as a flavor or aroma material. One of ordinary skill in the art would have had a reasonable expectation of success to obtain the proposed acetoacetate derivative because Hojo et al. teach transesterification of l-menthol with methyl acetoacetate and state that l-menthyl acetoacetate may be obtained quantitatively under the disclosed conditions. Moreover, Hojo et al. specifically demonstrate the reaction in example 1, wherein l-menthol is reacted with methyl acetoacetate to provide l-menthyl acetoacetate in 96.2% theoretical yield. Because 2,5,6-trimethylcyclohex-2-en-1-ol of Weingarten et al. also contains an alcohol hydroxyl functionality available for esterification, these teachings would have provided one of ordinary skill in the art with a reasonable expectation of success that the known transesterification would successfully furnish the corresponding acetoacetate ester recited in claim 25.
Claims 26 – 27, 33, and 35 – 40 are rejected under 35 U.S.C. 103 as being unpatentable over Weingarten et al. (EP3763352A1) in view of Hojo et al. (US8586009B2) and FAO (JECFA Monographs, 2008, PTO-892) as applied to claims 21 and 25 above, and further in view of Organic Syntheses (Organic Syntheses, 1990, Vol. 68, PTO-892) and Nowicki (Molecules, 2000, Vol. 5, Issue 8, page 1033 – 1050, PTO-892).
Weingarten et al., Hojo et al., and FAO teach the limitations discussed above.
Weingarten et al. further teach mixtures comprising two or more compounds selected from compounds of formulae (I), (II), (III), and/or (VI), or stereoisomers thereof, wherein the combination of compounds are used as fragrances (para. [0181]). Weingarten et al. further teach 2-(2,4,5-trimethylcyclohex-2-en-1-yl)acetaldehyde, corresponding to the compound of formula (II) recited in claim 33. Weingarten et al. teach that the compound has a prominent lily-of-the-valley odor note and may be used to impart a green, watery, chrysanthema, grassy, aldehydic, lily of the valley, leathery, terpene, and/or natural note (para. [0183]). The compositions is typically adapted to the particular intended use or the intended application. Thus, the total amount of the compounds vary over a wide range. As a rule, the customary standard commercial amounts for scents are used (para. [0271]. The compounds are in an overall amount of from 0.001 to 99.9% by weight based on the total weight of the composition (para. [0272]). In a preferred embodiment, the composition comprises the synthesized compounds and at least one further component, such as aroma chemicals, non-aroma chemical carriers, anti-oxidants, and deodorant-active agents (para. [0203]). Weingarten et al. therefore further teach incorporating trimethylcyclohexenyl aroma compounds into fragrance compositions together with additional aroma chemicals and/or non-aroma chemical carriers, thereby teaching the general aroma-use and composition features recited in claim 36.
However, Weingarten et al. differ from the structure of formula (I) in that Weingarten et al. teach a hydroxyl group at the position corresponding to X, and do not teach X as recited in claims 26 – 27. Weingarten et al. do not teach a mixture comprising the compound of formula (Ia) recited in claim 33 together with the compound of formula (II).
Organic Syntheses teaches the Carroll rearrangement for preparing an unsaturated methyl ketone from an allylic alcohol through the corresponding acetoacetate ester. Particularly, Organic Syntheses teach reacting the allylic alcohol 3-hydroxy-1-nonene with diketene in the presence of 4-dimethylaminopyridine to form (1-ethenyl)heptanyl 3-ketobutanoate, i.e., the corresponding acetoacetate ester. Organic Syntheses further teach subjecting the acetoacetate ester to Carroll rearrangement conditions to obtain (E)-5-dodecen-2-one, thereby demonstrating conversion of an allylic alcohol-derived acetoacetate ester to the corresponding unsaturated methyl ketone (page 2):
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Nowicki teaches that Claisen, Cope, and Carroll rearrangements have proven very useful in the synthesis of fragrance and flavor compounds both in laboratory and on an industrial scale (page 1035, para. 1). Nowicki further teaches that the Carroll rearrangement is developed for the synthesis of 2-methyl-2-hepten-6-one, which is identified as a basic intermediate for the production of numerous fragrance compounds in the terpenoid group, and further teaches that pseudoionone may be obtained by a similar Carroll reaction (page 1039, para. 2; page 1040, para. 1; Schemes 18 – 19).
It would have been prima facie obvious for a person of ordinary skill in the art before the effective filing date of the claimed invention to further modify the acetoacetate ester of 2,5,6-trimethylcyclohex-2-en-1-ol rendered obvious by the combined teachings of Weingarten et al. Hojo et al., and FAO by subjecting the acetoacetate ester to the Carroll rearrangement in view of Organic Syntheses and Nowicki because Organic Syntheses teaches that an allylic alcohol-derived acetoacetate ester may be converted by Carroll rearrangement to the corresponding unsaturated methyl ketone. Such modification would have resulted in an unsaturated methyl ketone having the -CH2-(CO)-CH3 group, as recited in claims 26 – 27, and represented by formula (Ia). One of ordinary skill in the art would have been motivated to make such a modification because Nowicki teaches that Carroll and related rearrangement are useful in synthesis of flavor and fragrance compounds and describes the use of Carroll chemistry in preparing ketones relevant to fragrance synthesis. Thus, one of ordinary skill in the art seeking additional fragrance-related derivatives would have had reason to employ the known Carroll rearrangement to obtain the corresponding methyl ketone derivative. One of ordinary skill in the art would have had a reasonable expectation of success to carry out the modification because Hojo et al. demonstrate preparation of an acetoacetate ester from a substituted cyclic alcohol, and Organic Syntheses demonstrates that an allylic alcohol-derived acetoacetate ester undergoes Carroll rearrangement to form an unsaturated methyl ketone. Nowicki further establishes that Carroll rearrangement are successfully employed in the synthesis of ketone compounds in the flavor and fragrance field. Thus, the prior art provide both a suitable acetoacetate precursor and an established reaction for converting such an acetoacetate functionality to an unsaturated methyl ketone.
Regarding claim 33, the combination of Weingarten et al., Hojo et al., FAO, Organic Syntheses, and Nowicki renders obvious the compound of formula (Ia), as set forth above. Weingarten et al. further teach the compound corresponding to formula (II) and teach mixtures comprising two or more of its disclosed aroma compounds for use as fragrances. It would therefore have been prima facie obvious to one of ordinary skill in the art to combine the formula (Ia) compound rendered obvious by the combined teachings with the formula (II) compound taught by Weingarten et al. to provide a mixture as recited in claim 33. One of ordinary skill in the art would have been motivated to make the combination because Weingarten et al. explicitly contemplate mixtures of aroma compounds for fragrance use, thereby providing reason to combine the aroma compounds rather than employ each compound individually. One of ordinary skill in the art would have had a reasonable expectation of success because Weingarten et al. teach the use of mixtures of aroma compounds in fragrance applications, and the combined teachings render formula (Ia) obvious and provide formula (II) as an aroma compound.
Regarding claim 35, Weingarten et al. teach that the compositions are adapted to the particular intended use and that the total amount of the compounds may vary over a wide range. It would have been obvious to one of ordinary skill in the art to optimize the relative amounts of the compounds in the mixture through routine experimentation depending on the desired aroma impression. Therefore, determining a weight ratio within the recited range would have required no more than routine experimentation.
Regarding claim 36, Weingarten et al. further teach fragrance compositions comprising the disclosed compounds or mixture thereof together with at least one further component selected from aroma chemicals and non-aroma chemical carriers. Thus, Weingarten et al. teach the additional limitations of claim 36.
Regarding claims 37 – 38, Weingarten et al. teach the use of the disclosed compounds and mixtures as fragrances and teach incorporating such compounds into compositions to impart or modify the scent character of the compositions. Thus, utilizing or adding the claimed mixture to composition to impart an aroma impression would have been obvious.
Regarding claim 40, Weingarten et al. teach that customary commercial amounts for scents may be used and disclose an overall amount of the compounds from 0.001 to 99.9% by weight based on the total weight of the composition. The range taught by Weingarten et al. overlaps the recited range. Therefore, the concentration limitation of claim 40 would have been obvious.
Conclusion
No claim is found to be allowable.
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/H.Y.L./Examiner, Art Unit 1693
/SCARLETT Y GOON/Supervisory Patent Examiner, Art Unit 1693
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