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
This office action is in reply to the Applicant’s Arguments/Remarks filed 08 June 2026 for application 18/293,768 filed 30 January 2024. Claims 1 and 16 are amended. Currently, claims 1-16 are pending.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 08 June 2026 was filed after the mailing date of the application on 30 January 2024. The submission is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
REJECTIONS WITHDRAWN
The status for each rejection and/or objection in the previous office action is set out below.
35 U.S.C. 102, 103, and Double Patenting
Applicant’s amendments to claim 16, further limiting the claim to a composition of matter comprising at least 98% of (3aR,5aS,9aS,9bR)-3a,6,69a-tetramethyldodecahydronaphtho[2,1-b]furan; and at most 2% of (3aS,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan, is sufficient to overcome this rejection.
REJECTIONS – MAINTAINED & NEW
Applicant’s amendments to claims 1 and 16 have resulted in the below new rejection.
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 1 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 1 is indefinite because the catalyst loading of heterogenous acidic catalyst is dependent on prophetic product yields that is simultaneously dependent on the catalyst loading. The initial product within the reaction mixture is by definition zero by any metric (moles or mass), therefore the calculated catalyst loading would necessarily be zero, falling outside of the range of the claim’s limitation of catalyst concentration range 0.5-20.0 wt.% relative to the cycloether. As the amount of product starts at zero and changes over time, it would be challenging to determine if the reaction remained within the scope of the claim. As such, the claim fails to properly establish the metes and bounds necessary for examination.
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claim 1 is rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
A review of the rejected claim language indicates that this claim is drawn to “a process for the preparation of a cycloether of formula (I) … wherein the heterogenous acidic catalyst concentration ranges from 0.5 wt. % to 20 wt. % relative to the total amount of the cycloether of formula (I)”. In Applicant’s originally filed specification, the limitation of the last three lines can be found on pgs. 8-9, starting on line 28. However, among the working examples provided, only Example 2 (pg. 32) provides means for calculating the amount of acidic heterogenous catalyst, utilizing the starting material, described as compound of formula (II), as the reference point for calculating weight equivalents. No working examples are available to demonstrate how this calculation would be performed as described by the limitations of claim 1.
As such, while the limitation is literally supported by the instant specification, it does not inherently support the amended limitations as they fail to adequately provide support in the form of working examples demonstrating how this limitation would be performed or carried out.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
As the limitations introduced by the amendment of claim 1 are unactionable as described above, they are not currently considered as part of the examination process.
(Maintained) Claim 1 is rejected under 35 U.S.C. 103 as being unpatentable over Ohloff et al. (Significance of the geminal dimethyl group in the odor principle of Ambrox, Helvetica Chimica Acta 1985, 68, 2022-2029) in view of Steenkamp et al. (Process for the production of ambrafuran, US 2010/0248316 A1, 2010).
Ohloff discloses the synthesis of (-)-ambrox, which reads on formula (I) from the pendant alcohol intermediate X, albicanol, which reads on formula (II), using nitromethane, tosyl- sulfonic acid, under reflexing conditions.
Ohloff does not, however, demonstrate cyclization of compound of formula (II) in the
presence of heterogenous acidic catalyst.
Steenkamp rectifies this deficiency by teaching the use of activated zeolites, aluminosilicates that are used as solid acid catalysts, to synthesize (-)-ambrox from sclareol. While (-)-sclareol does not read upon formula (II), the connective functional groups are evident, including a terminal olefin and available hydroxy groups. Zeolites are described as environmentally benign, show unique selectivity and reactivity, and have been used catalyze mono-alcohols to ethers and olefins.
As such, it would have been prima facie obvious, to a person of ordinary skill in the art, at the time of filing, to consider the use of heterogenous acidic catalysts as demonstrated by Steenkamp as a means to perform the intramolecular cyclization illustrated by Ohloff.
(Maintained) Claim 2 is rejected under 35 U.S.C. 103 as being unpatentable over Ohloff and Steenkamp as the limitations of claim 2, which further limits the claim by requiring the heterogenous acidic catalyst to be crystalline or polymorphic, are met as zeolites are generally crystalline.
(Maintained) Claim 3 is rejected under 35 U.S.C. 103 as being unpatentable over Ohloff and Steenkamp as the limitations of claim 3, where the heterogenous acidic catalyst comprises silicon, tin, zirconium, hafnium or titanium and a second metal selected from aluminum, boron, iron or a mixture, are met as zeolites are described as aluminosilicates, a composition of aluminum and silicon.
(Maintained) Claim 4 is rejected under 35 U.S.C. 103 as being unpatentable over Ohloff and Steenkamp as the limitations of claim 4, that the heterogenous acidic catalyst is an aluminosilicate catalyst, which are met as zeolites are described as aluminosilicate catalysts.
(Maintained) Claim 5 is rejected under 35 U.S.C. 103 as being unpatentable over Ohloff and Steenkamp as the limitations of claim 5, that the aluminosilicate catalyst is a zeolite or clay, are met as the catalyst taught by Steenkamp is a zeolite.
(Maintained) Claim 7 is rejected under 35 U.S.C. 103 as being unpatentable over Ohloff and Steenkamp as the limitations of claim 7, that the zeolite is a large-pore zeolite, are met as one example of zeolite taught by Steenkamp is the NaY-type zeolite, described by Yan et al. (Evolution of the pore and framework structure of NaY zeolite during alkali treatment and its effect on methanol oxidative carbonylation over a CuY catalyst, J. Chem. Res. 2020, 11-12, 710-720) as a large-pore diameter zeolite (pg. 711).
(Maintained) Claim 8 is rejected under 35 U.S.C. 103 as being unpatentable over Ohloff and Steenkamp as the limitations of claim 8, that the zeolite has a FAU, BEA or MOR topology, are met as the NaY-type zeolite are faujasite, or FAU, zeolites.
(Maintained) Claim 9 is rejected under 35 U.S.C. 103 as being unpatentable over Ohloff and Steenkamp as the limitations of claim 9, that the silicon:aluminum ratios in the range between 2.5:1 and 300:1, are met as Steenkamp teaches the use of zeolite CBV320 from Zeolyst International, which, according to the product website, has a SiO₂/Al₂O₃ mole ratio of 5.1:1 Zeolite Y (zeolyst.com/our-products/standard-zeolite-powders/zeolite-y.htm).
(Maintained) Claim 10 is rejected under 35 U.S.C. 103 as being unpatentable over Ohloff and Steenkamp as the limitations of claim 10, that in formula (I), R¹ = H and m = 1, are met as (-)- ambrox reads upon formula (I) and contains these substitutions.
(Maintained) Claim 11 is rejected under 35 U.S.C. 103 as being unpatentable over Ohloff and Steenkamp as the limitations of claim 11, that the cycloether is a compound of formula (III), are met as (-)-ambrox reads upon formula (III).
(Maintained) Claim 12 is rejected under 35 U.S.C. 103 as being unpatentable over Ohloff and Steenkamp as the limitations of claim 12, that the compound of formula (II) is a compound of formula (IV), are met as intermediate X, albicanol, as disclosed by Ohloff reads upon formula (IV).
(Maintained) Claim 13 is rejected under 35 U.S.C. 103 as being unpatentable over Ohloff and Steenkamp as the limitations of claim 13, that the cycloether is a compound of formula (V), are met as (-)-ambrox reads upon formula (V).
(Maintained) Claim 14 is rejected under 35 U.S.C. 103 as being unpatentable over Ohloff and Steenkamp as the limitations of claim 14, that the compound of formula (IV) is a compound of formula (VI), are met as intermediate X, albicanol, as disclosed by Ohloff reads upon formula (VI).
(Maintained) Claim 6 is rejected under 35 U.S.C. 103 as being unpatentable over Ohloff and Steenkamp as applied to claims 1-5 and 7-14 above, and further in view of Knuebel et al. (Process for the production of 8q,12-oxido-13,14,15,16-tetranorlabdane, US 5,670,670, 1997).
Ohloff disclose the synthesis of (-)-ambrox under acidic conditions whereas Steenkamp teaches that (-)-ambrox can be synthesized through zeolite catalysis.
They do not, however, teach the synthesis of (-)-ambrox where the catalyst is an acid-treated clay.
Knuebel addresses this by teaching the synthesis of ambroxan or (-)-ambrox in which cyclization-dehydration is conducted in the presence of aluminum-silicates such as talcum and clays such as kaolinite, montmorillonite, bentonites and hectorites and more specifically through the use of K-catalysts which are montmorillonite catalysts produced by a special acid treatment (col. 2, line 60).
Therefore, it would be prima facie obvious, to a person of ordinary skill in the art, at the time of filing, to consider the use of acid-treat clay to perform the synthesis of (-)-ambrox as had been previous demonstrated by Knuebel.
(Maintained) Claim 15 is rejected under 35 U.S.C. 103 as being unpatentable over Ohloff and Steenkamp
as applied to claims 1-5 and 7-14 above, and further in view of Belorgey et al. (Method for
producing albicanol compounds, WO 2019/229064, 2019).
Ohloff disclose the synthesis of (-)-ambrox under acidic conditions whereas Steenkamp
teaches that (-)-ambrox can be synthesized through zeolite catalysis.
They do not, however, teach the preparation of a compound of formula (II) comprising the
step of contacting farnesyl pyrophosphate with at least one enzyme.
33. Belorgey overcomes this by teaching biochemical methods of producing albicanol and related compounds such as phosphorylated albicanol compounds through the use of farnesyl pyrophosphate with albicanyl diphosphate synthase activity. Utilizing novel synthase DfHAD expressed from E. Coli, albicanol along with albicanyl monophosphate, farnesyl monophosphate, and farnesol were detected in an in vitro assay. After the addition of phosphatase BAP, albicanol and farnesol were the only compounds detected in the assay.
As such, it would have been prima facie obvious, to a person of ordinary skill in the art, at the
time of filing, to consider the use of enzymes such as novel enzyme DfHAD and phosphatase
BAP, disclosed by Belorgey, to synthesize albicanol from farnesyl pyrophosphate as a means
to obtain the penultimate intermediate to (-)-ambrox.
(New) Claim 16 is rejected under 35 U.S.C. 103 as being unpatentable over Knuebel et al. (Process for the production of 8a,12-oxido-13,14,15,16-tetranorlabdane, US 5,670,670, 1997).
Knuebel discloses the synthesis of Ambroxan® or (-)-ambrox from 8a,12-dihydroxy-13,14,15,16-tetranorlabdane using acid-treated clays. In several examples, including example E1 and E2, Ambroxan was obtained in 95.6% and 97.7% yield by weight, compared to isomers 8-epimer, 9-epimer and the dehydration product of >1.0% for both epimers and 3.0% for the dehydration product. As the undesired epimer (3aS,5aS,9aS,9bR)-3a,6,6,9a-tetramethyldodecahydronaphtho[2,1-b]furan is the 8-epimer, examples E1 and E2 report 0.14 and 0.15% of the isomer, respectively. 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); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990) (The prior art taught carbon monoxide concentrations of "about 1-5%" while the claim was limited to "more than 5%." The court held that "about 1-5%" allowed for concentrations slightly above 5% thus the ranges overlapped.); In re Geisler, 116 F.3d 1465, 1469-71, 43 USPQ2d 1362, 1365-66 (Fed. Cir. 1997) (Claim reciting thickness of a protective layer as falling within a range of "50 to 100 Angstroms" considered prima facie obvious in view of prior art reference teaching that "for suitable protection, the thickness of the protective layer should be not less than about 10 nm [i.e., 100 Angstroms]." The court stated that "by stating that ‘suitable protection’ is provided if the protective layer is ‘about’ 100 Angstroms thick, [the prior art reference] directly teaches the use of a thickness within [applicant’s] claimed range."). See also In re Bergen, 120 F.2d 329, 332, 49 USPQ 749, 751-52 (CCPA 1941) (The court found that the overlapping endpoint of the prior art and claimed range was sufficient to support an obviousness rejection, particularly when there was no showing of criticality of the claimed range). Similarly, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close. Titanium Metals Corp. of America v. Banner, 778 F.2d 775, 783, 227 USPQ 773, 779 (Fed. Cir. 1985) (Court held as proper a rejection of a claim directed to an alloy of "having 0.8% nickel, 0.3% molybdenum, up to 0.1% iron, balance titanium" as obvious over a reference disclosing alloys of 0.75% nickel, 0.25% molybdenum, balance titanium and 0.94% nickel, 0.31% molybdenum, balance titanium. "The proportions are so close that prima facie one skilled in the art would have expected them to have the same properties."). See also Warner-Jenkinson Co., Inc. v. Hilton Davis Chemical Co., 520 U.S. 17, 41 USPQ2d 1865 (1997) (under the doctrine of equivalents, a purification process using a pH of 5.0 could infringe a patented purification process requiring a pH of 6.0-9.0); In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955) (Claimed process which was performed at a temperature between 40°C and 80°C and an acid concentration between 25% and 70% was held to be prima facie obvious over a reference process which differed from the claims only in that the reference process was performed at a temperature of 100°C and an acid concentration of 10%); In re Scherl, 156 F.2d 72, 74-75, 70 USPQ 204, 205-206 (CCPA 1946) (prior art showed an angle in a groove of up to 90° and an applicant claimed an angle of no less than 120°); In re Becket, 88 F.2d 684 (CCPA 1937) ("Where the component elements of alloys are the same, and where they approach so closely the same range of quantities as is here the case, it seems that there ought to be some noticeable difference in the qualities of the respective alloys."); In re Dreyfus, 73 F.2d 931, 934, 24 USPQ 52, 55 (CCPA 1934)(the prior art, which taught about 0.7:1 of alkali to water, renders unpatentable a claim that increased the proportion to at least 1:1 because there was no showing that the claimed proportions were critical); In re Lilienfeld, 67 F.2d 920, 924, 20 USPQ 53, 57 (CCPA 1933)(the prior art teaching an alkali cellulose containing minimal amounts of water, found by the Examiner to be in the 5-8% range, the claims sought to be patented were to an alkali cellulose with varying higher ranges of water (e.g., "not substantially less than 13%," "not substantially below 17%," and "between about 13[%] and 20%"); K-Swiss Inc. v. Glide N Lock GmbH, 567 Fed. App'x 906 (Fed. Cir. 2014)(reversing the Board's decision, in an appeal of an inter partes reexamination proceeding, that certain claims were not prima facie obvious due to non-overlapping ranges); In re Brandt, 886 F.3d 1171, 1177, 126 USPQ2d 1079, 1082 (Fed. Cir. 2018)(the court found a prima facie case of obviousness had been made in a predictable art wherein the claimed range of "less than 6 pounds per cubic feet" and the prior art range of "between 6 lbs./ft3 and 25 lbs./ft3" were so mathematically close that the difference between the claimed ranges was virtually negligible absent any showing of unexpected results or criticality.)
As such, it would be prima facie obvious, to a person of ordinary skill in the art, before the effective filing date, to utilize the teachings of Knuebel when considering the ratio of isomers between Ambrox and possible isomers.
Response to Arguments
The office kindly thanks the Applicant for their consideration and arguments to the previous office action. Responses are detailed below.
Applicant’s arguments, see pg. 7 – Rejections under 35 U.S.C. § 102, filed 08 June 2026, with respect to the rejection of claim 16 under 35 U.S.C. § 102 have been fully considered and are persuasive. Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close. Titanium Metals Corp. of America v. Banner, 778 F.2d 775, 783, 227 USPQ 773, 779 (Fed. Cir. 1985).
On pgs. 7-8 – Rejections under 35 U.S.C. § 103, filed 08 June 2026, the Applicant argues:
… Ohloff is silent to the cyclization of albicanol in the presence of a heterogenous acidic catalyst… Steekamp does not in fact teach a catalyzed cyclization of sclareol to produce (-)-ambrox. As is well known in the art, a catalyst is a reagent that facilitates or accelerates a chemical reaction without being consumed in the overall transformation… used in a sub-stoichiometric amount and thus the ratio of the limiting reagent to catalyst is 1:<1.
In response to Applicant’s arguments, they are correct in stating that Ohloff is silent to cyclization in the presence of a heterogenous acidic catalyst. However, they are not correct in stating that a catalyst need be used in sub-stoichiometric quantities, as their purpose is to either increase the rate of a reaction or to facilitate the occurrence of a reaction by reducing the activation barrier to that reaction. Indeed Catalysis (en.wikipedia.org/wiki/Catalysis), cited here only for the purpose of response to this argument, notes that catalysts are not consumed by the reaction and remained unchanged and if the reaction is rapid, a very small quantity of catalyst suffices. However, there are many reactions where super-stoichiometric quantities of catalyst are used. One common example is hydrogenation where the equivalents of the hydrogenating metal, (i.e. palladium), can be used in excess of the substrate to achieve full hydrogenation.
On pgs. 8-9 - Rejections under 35 U.S.C. § 103, Obvious over Ohloff in view of Steenkamp in further view of Knuebel, filed 08 June 2026, the Applicant argues:
… as previously described, Steenkamp would not have provided one of skill in the art any motivation to employ a catalytic amount of heterogenous acidic catalyst in the reaction described by Ohloff. As instant claim 6 depends from instant claim 1, the rejection …. Is moot…
In response to Applicant's arguments against the references individually, one cannot show non-obviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986). While Ohloff does not teach heterogenous acidic catalysts, they do utilize a strongly acidic medium, concentrated H2SO4. It would also be obvious to a person of ordinary skill in the art to explore alternatives to achieve the same results utilizing less chemically harsh and dangerous mediums.
On pg. 9 - Rejections under 35 U.S.C. § 103, Obvious over Ohloff in view of Steenkamp in further view of Belorgey, filed 08 June 2026, the Applicant presents the same argument as above. In response to Applicant's arguments against the references individually, one cannot show non-obviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986).
Conclusion
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.
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/ALLEN CHAO/Examiner, Art Unit 1622
/JAMES H ALSTRUM-ACEVEDO/Supervisory Patent Examiner, Art Unit 1622
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