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
1. This application is a 371 of PCT/PT2022/050003 01/25/2022; FOREIGN APPLICATIONS: SWITZERLAND 00068/21 01/25/2021, SWITZERLAND 00066/21 01/25/2021.
Claims 1, 3-18 are pending.
Restriction Election Maintained.
2. Applicant’s election of group II and the species, compound 52 of formula (4) claim 16,
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in the reply filed on February 4, 2026 was previously acknowledged. Claims 16-17 read on the elected species. As detailed in the following rejections, the generic claim encompassing the elected species was not found patentable. The search and examination was continued until prior art was found that anticipated or rendered obvious a non-elected species that falls within the scope of the generic Markush claim reading on the elected species. As per MPEP 803.02 II. C. “[T]he examiner must continue to search the species of the claim unless the claim has been found to be unpatentable over prior art.” The examiner “need not continue to search the claim if the claim is rejected over prior art”. [ibid. D.] Therefore, the search and examination is restricted to the claims reading on the elected species, and claims not reading on the elected species are held withdrawn. Accordingly, claim 18, which does not read on the elected species is withdrawn.
Claim Rejections/Objections Withdrawn
3. The objection to claim 16 for the grammatical informality is withdrawn in view of the amendments. The rejection of claims 16-17 under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, is withdrawn based upon the amendments. The rejection of claim(s) 16 under 35 U.S.C. 102(a)(1) as being anticipated by Wadsworth “The Chemical Basis of Serine Palmitoyltransferase Inhibition by Myriocin.” Journal of the American Chemical Society, 2013, 135(38), 14276-14285 is withdrawn based upon the amendments.
Claim Rejections/Objections Maintained/ New Grounds of Rejection
4. The rejection of claim(s) 16-17 under 35 U.S.C. 103 as being unpatentable over Enders AND Greene and Wuts is maintained. Applicant's arguments filed July 31, 2026 have been fully considered but they are not persuasive. According to the argument “one of ordinary skill in the art would not have viewed the benzylidene acetal as a simple substitution for or an equivalent of the aldehyde” (arguments page 16), however Greene and Wuts is evidence in the record that shows both groups to be used for the same purpose. Since the alternative group was shown to perform the same, little more can be expected from changing the ligand than the same or similar result.
Applicants representative argues that “the Office Action does not give a reason why one of ordinary skill would have selected a benzylidene acetal from among the numerous other protecting groups disclosed by Greene.” (arguments page 16). This lacks the necessary factual predicate since as discussed in the rejection, “There may be an improvement since “The benzylidene acetal has the advantage that it can be removed under neutral conditions by hydrogenolysis or by acid hydrolysis.”” The claimed invention is no more than the simple substitution of one known element for another or the mere application of a known technique to a piece of prior art ready for improvement.
A new objection for an informality is raised in the amendment.
Objections
5. Claim 16 is objected to for the following informality: The amended claims introduce the misspellings “naphtyl” for naphthyl and “phenantryl” for phenanthryl. Appropriate correction is required.
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.
6. Claim(s) 16-17 is/are rejected under 35 U.S.C. 103 as being unpatentable over Enders Chemical Communications 2006, pages 655-657(cited on the IDS) AND Greene and Wuts “PROTECTION FOR THE HYDROXYLGROUP, INCLUDING 1,2- AND 1,3=DIOLS” chapter 2 in Protective Groups in Organic Synthesis, Third Edition. 1999 John Wiley & Sons, Inc. page 17-245. The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
Determining the scope and contents of the prior art
Enders page 665 Scheme 3 teaches compounds 12 as shown below:
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This is a compound of Formula (5) where R1 is a C14 alkyl, and one of R2a/R3a is methyl.
The intermediate 5 in Enders was made by condensation of the aldehyde with the intermediate 3 as shown below.
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Greene and Wuts on page 201, PROTECTION FOR 1,2- AND 1,3-DIOLS “The prevalence of diols in synthetic planning and in natural sources (e.g., in carbohydrates, macrolides, and nucleosides) has led to the development of a number of protective groups of varying stability to a substantial array of reagents. Dioxolanes and dioxanes are the most common protective groups for diols.” The prior art group Acetonide (Isopropylidene Ketal) is discussed on page 207:
Acetonide (Isopropylidene Ketal) (Chart 3)
Acetonide formation is the most commonly used protection for 1,2- and 1,3-diols. The acetonide has been used extensively in carbohydrate chemistry to mask selectively the hydroxyls of the many different sugars.’ In preparing acetonides of triols, the 1,2-derivative is generally favored over the 1,3-derivative which in turn is favored over the 1,4-derivative,* but the extent to which the 1,2- acetonide is favored is dependent upon the structure of the trio1.3-6
The claimed group in compounds of formula (5) where one of R2b/R3b is H and the other is an aryl or substituted aryl is a known alternative to an acetonide offering certain advantages and is discussed on page 217:
Benzylidene Acetal (Chart 3)
A benzylidene acetal is a commonly used protective group for 1,2- and 1,3-diols. In the case of a 1,2,3-triol, the 1,3-acetal is the preferred product, in contrast to the acetonide, which gives the 1,2-derivative. The benzylidene acetal has the advantage that it can be removed under neutral conditions by hydrogenolysis or by acid hydrolysis.
Another derivative is p-Methoxybenzylidene, discussed on page 224:
p-Methoxybenzylidene Acetal (Chart 3)
The p-methoxybenzylidene acetal is a versatile protective group for diols that undergoes acid hydrolysis 10 times faster than the benzylidene group.’ As with the benzylidene derivative, the 1,3-derivative is thermodynamically favored over the 1,2-derivative.2
Various other substituted benzaldehydes are discussed in Greene and Wuts including 2,4-Dimethoxybenzylidene, page 227; 3,4-Dimethoxybenzylidene, page 227; 2-Nitrobenzylidene, page 228 and 4-Nitrobenzylidene, page 228.
Ascertaining the differences between the prior art and the claims at issue
The prior art uses an acetonide protecting group while the instant claims are drawn to various benzylidene compounds.
Resolving the level of ordinary skill in the pertinent art and considering objective evidence present in the application indicating obviousness or nonobviousness.
When a chemical reaction is to be carried out selectively at one reactive site in a multifunctional compound, other reactive sites must be temporarily blocked. A protective group must react selectively in good yield to give a protected substrate. Since the alternative group was shown to perform the same, little more can be expected from changing the ligand than the same or similar result. There may be an improvement since “The benzylidene acetal has the advantage that it can be removed under neutral conditions by hydrogenolysis or by acid hydrolysis.” The claimed invention is no more than the simple substitution of one known element for another or the mere application of a known technique to a piece of prior art ready for improvement. In light of the forgoing discussion, the Examiner concludes that the subject matter defined by the instant claims would have been obvious within the meaning of 35 USC 103. From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
Conclusion
6. THIS ACTION IS MADE FINAL. 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 DAVID K O'DELL whose telephone number is (571)272-9071. The examiner can normally be reached on Monday - Friday 9:30 - 7:00 PM.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Clinton Brooks can be reached on 571-270-7682. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/DAVID K O'DELL/Primary Examiner, Art Unit 1621
