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 response to the Applicant’s Arguments/Remarks filed 08 June 2026 for application 18/293,766 filed 30 January 2024, 371 of PCT/EP2022/071261 filed 28 July 2022, claiming priority from EP21188879.7 filed 30 July 2021. Claim 1 is 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REJECTIONS WITHDRAWN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 1, further limiting the claim to a heterogenous acidic catalyst in a concentration from 0.5 wt.% to 20 wt.% relative to the total amount of the 1,4- or 1,5-diol, is sufficient to overcome this rejection.
REJECTIONS – MAINTAINED & NEW
Applicant’s amendments to claim 1 have resulted in the below new rejection.
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.
(New) Claims 1-3, 5-9 and 12-16 are rejected under 35 U.S.C. 103 as being unpatentable over Steenkamp et al. (Process for the production of ambrafuran, US 2010/0248316 A1, 2010) in view of Knuebel et al. (Process for the production of 8α,12-oxido-13,14,15,16-tetranorlabdane, US 5,670,670, 1997; entered into the IDS on 08 June 2026).
(New) Steenkamp discloses the synthesis of (-)-Ambrox from Amdradiol catalyzed by zeolites. Here (-)-Ambrox reads upon formula (II) where m = 1, R¹ = C1 alkyl, R² and R³ are a C₃-alkanediyl group, R³ and R⁴ are a C₅-alkanediyl group, and R⁵ is a C₁-alkyl. Amdradiol reads upon formula (I) where m = 1, R¹ = C1 alkyl, R² and R³ are a C₃-alkanediyl group, R³ and R⁴ are a C₅-alkanediyl group, and R⁵ is a C₁-alkyl. Zeolites are aluminosilicates that are categorically different from clays with a few commercial examples exemplified including NaY-type and CaY-type zeolites (Example 3). Zeolyst, the specified vendor, characterizes Zeolite Y-type products by SiO₂/Al₂O₃ mole ratios ranging between 5.1-80. Cyclodehydration was conducted in a variety of solvents including toluene, ethyl acetate, diethyl ether, ethanol, or hexane, warmed to a temperature between room temperature and 110°C for 1 to 24 hours.
They do not, however, teach where the heterogenous acidic catalyst is used in a concentration of 0.5 wt.% to 20 wt.% relative to the total amount of the 1,4- or 1,5-diol.
Knubel addresses this paucity by teaching the production of Ambrox through the use of 5 to 80% by weight, based on the diol, using at least one alumino layer silicate (abstract). 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)As both Steenkamp and Knubel are purposed for the production of Ambrox through the diol precursor using aluminosilcate acidic heterogenous catalysts, the teachings of catalyst loading by Knubel overlay upon the disclosure of Steenkamp.
As such, it would be prima facie obvious, to a person of ordinary skill in the art, before the effective filing date, to consider the use the range of catalyst loading as taught by Knubel to use in the production of Ambrox.
(New) Regarding the limitations of claim 2, wherein the heterogenous acidic catalyst is crystalline, are met as zeolites are generally crystalline.
(New) Concerning the limitations of claim 3, wherein the heterogenous catalyst comprises silicon and a second metal selected from the group consisting of aluminum, boron, iron, tin, titanium, zirconium, hafnium and a mixture thereof, are met as zeolites are broadly characterized as aluminosilicates and therefore contain both silicon and aluminum.
(New) With respect to the limitation of claim 5, that the heterogenous acidic catalyst is an aluminosilicate catalyst, is met as zeolites are characterized as aluminosilicates.
(New) With regards to the limitation of claim 6, that the aluminosilicate catalyst is a zeolite, is met as Steenkamp and Knubel utilize catalytic zeolite in the synthesis of (-)-Ambrox.
(New) With concern to the limitation of claim 7, that the zeolite is a large pore zeolite, is 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).
(New) Regarding the limitation of claim 8, that the zeolite has a FAU, BEA or MOR topology, is met as the NaY-type zeolite are faujasite, or FAU, zeolites.
(New) Concerning the limitation of claim 9, wherein the silicon:aluminum ratio is comprised in the range between 3:1 and 300:1, are met as the exemplified commercially available Y-type zeolites as sold by vendor Zeolyst are characterized as having SiO2/Al2O3 mole ratios ranging between 5.1-80.
(New) With respect to the limitation of claim 12, where the variable m = 1, is met by both Amdradiol and (-)-Ambrox.
(New) With regards to the limitations of claim 13, where the 1,4-diol is a compound of formula (III), are met as Amdradiol reads on formula (III) where n = 1, R⁶ = C₁-alkyl, R⁷ = R⁸ = H, R⁹ and R¹⁰ are an alkanediyl group, and R¹¹ = C₁-alkyl.
(New) With concern to the limitations of claim 14, where the oxacylopentane derivative is a compound of formula (IV), are met as (-)- Ambrox reads on formula (IV) where n = 1, R⁶ = C₁-alkyl, R⁷ = R⁸ = H, R9 and R¹⁰ are an alkanediyl group, and R¹¹ = C₁-alkyl.
(New) Regarding the limitations of claim 15, where the 1,4-diol is a compound of formula (V), is met as Amdradiol reads on formula (V) where R⁶ = R¹¹ = R¹² = R¹³ = C₁-alkyl.
(New) Concerning the limitations of claim 16, where the silicon:aluminum ratio of claim 9 is comprised in the range between 5:1 and 300:1, is inherently met as are inherently met as the exemplified commercially available Y-type zeolites as sold by vendor Zeolyst are characterized as having SiO₂/Al₂O₃ mole ratios ranging between 5.1-80.
(New) Claim 4 is rejected under 35 U.S.C. 103 as being unpatentable over Steenkamp and Knubel as applied to claims 1-3, 5-9 and 12-16 above, and further in view of Yang et al. (One-pot synthesis of (-)-Ambrox, Sci. Rep. 2016, 6, 32650)
Steenkamp and Knubel disclose the synthesis of (-)-Ambrox by zeolite catalyzed cyclization of Amdradiol within a taught catalyst loading range.
They do not, however, disclose the use of a heterogenous acidic catalyst free of calcium, potassium, sodium, and/or lanthanum.
Yang rectifies this by teaching the synthesis of (-)-Ambrox from (-)-Sclareol catalyzed by a polyoxometalate, the acidic heterogenous catalyst phosphotungstate with chemical composition {[CH₃CH₂CH₂CH₂)4N][H₂PW₁₂O₄₀]}. In this synthesis, Yang utilizes this catalyst with hydrogen peroxide to transform (-)-Sclareol to (-)-Ambrox by peroxide substitution followed by radical fragmentation and cyclization.
As such, it would have been prima facie obvious, to a person of ordinary skill in the art, before the effective filing date, to consider the use of polyoxometalates to synthesize (-)-Ambrox from a diol such as (-)-Sclareol to avoid the use of elements calcium, sodium, potassium, and lanthanum as is feasibly demonstrated by Yang.
(New) Claims 10-11 are rejected under 35 U.S.C. 103 as being unpatentable over Steenkamp and Knubel as applied to claims 1-3, 5-9 and 12-16 above, and further in view of Y-type Zeolites (Y- type Zeolites, ACS Materials LLC, 19 August 2019) and Sani-Souna-Sido et al. (Behavior of arylvinylketones in zeolites: a systematic study, Applied Catalysis A: General 2008, 338, 101-108).
Steenkamp and Knubel disclose the synthesis of (-)-Ambrox by zeolite catalyzed cyclization of Amdradiol within a taught catalyst loading range.
They do not, however teach the use of dealuminated ultrastable Y-type (USY) zeolites.
The ACS Materials page on Y-type Zeolites addresses this in an informational blog on dealuminated ultrastable Y zeolites as good adsorbents and stable acid catalysts, exhibiting high thermal and hydrothermal stability as well as higher catalytic activity than that of aluminum-rich synthesized Y zeolites. They are noted to be common in fluid cracking catalysis and further additionally stabilized by ion-exchange with rare earth cations, also known as REUSY. REUSYs are prepared from an ammonium Y zeolite, described by Steenkamp, by steaming at high temperatures above 773 K, dislodging aluminum cations from the zeolite framework, with the structure of the Y zeolite self-stabilizing in the process.
Sani-Souna-Sido surmounts this by teaching the use of acidic form ultra-stable Y-type zeolites (H-USY) to catalyze the cyclization of arylvinylketones to indanones through the formation of a stabilized primary or secondary cationic intermediate, not a traditionally predictable mechanism, which is illustrated in Scheme 5. The capacity to protonate and stabilize cationic intermediates appears to be directly applicable to the cyclodehydration of Amdradiol where the mechanism possibly involves the formation of a cationic intermediate after protonation of a hydroxy leaving group, followed by substitution.
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 dealuminated ultra-stable Y-zeolites for their reported higher catalytic activity to improve the conversion efficiency in the cyclodehydration of Amdradiol to (-)-Ambrox.
(New) Regarding the limitations of claim 11, the use of the protonic form of zeolites, are met as Sani-Souna-Sido teaches the use of acidic-form ultrastable zeolites to perform the cationic stabilized intramolecular cyclization of Amdradiol to (-)-Ambrox.
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. 6 – Rejections Under 35 U.S.C. § 102(a)(1), filed 08 June 2026, with respect to the rejection(s) of claim(s) 1-3, 5-9, and 12-16 under 35 U.S.C. § 102(a)(1) 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 Knuebel et al. (Process for the production of 8α,12-oxido-13,14,15,16-tetranorlabdane, US 5,670,670, 1997; entered into the IDS on 08 June 2026) who teaches the use of catalytic amounts aluminosilicates by wt. % for the production of (-)-Ambrox.
On pg. 7 – Rejections Under 35 U.S.C. § 103, filed 08 June 2026, the Applicant argues:
… Steenkamp does not disclose or suggest using the catalyst in such a catalytic amount…Yang does not cure the deficiencies of Steenkamp as Yang is silent to the claimed cyclodehydration process….Steenkamp teaches use of zeolites in excess….neither Y-type zeolites nor Sani-Souna-Sido remedies this deficiency…
Applicant's arguments filed 08 June 2026 have been fully considered but they are not persuasive. The response to Steenkamp is addressed 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). While Yang nor Sani-Souna-Sido did not address the argument in paragraph 36, they were not purposed to do so in the prior office action. As such, the arguments are unpersuasive.
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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