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 1-18 are pending.
Response to Restriction Election
2. Applicant’s election of group II and the species, compound 52 of formula (4) claim 16,
PNG
media_image1.png
148
130
media_image1.png
Greyscale
in the reply filed on February 4, 2026 is acknowledged.1 The election was made with traverse and the examiner finds the arguments unpersuasive. There is an argument that the newly amended claims overcome the questions of unity of invention by amending around the prior art the examiner used to break unity. Unity of invention is not perpetually reevaluated upon the submission of amendments. Applicants’ representative has failed to explain which claims read on the elected species. As best as can be understood, 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is restricted to the claims reading on the elected species, and claims not reading on the elected species are held withdrawn. Accordingly, claim 18, which does not read on the elected species is withdrawn.
Objections
3. Claim 16 is objected to for the following informality: In claim 16 near the end it is stated “one of R2a and R3a and one of R2b and R3b is hydrogen, and the other rest is a substituted or unsubstituted aryl,” The ”other rest is” is grammatically in error since other rest is non-specific and the verb are seems more appropriate. Something like “one of R2a and R3a and one of R2b and R3b is hydrogen, and the others are selected from the group consisting of a substituted or unsubstituted aryl.” 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.
4. Claims 16-17 are 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 16 and 17 recites the limitation "A protected derivative of a compound of Formula (2)". There is no formula (2) in the claim. There is insufficient antecedent basis for this limitation in the claim. The claim 16 is an independent claim and should be self-contained, and reference to the specification or other parts of the disclosure is forbidden except in design cases or situations where incorporation is not possible. The claim also casts doubt on the intended scope since the language “A protected derivative of a compound of Formula (2)” is superfluous if the claim is only meant to encompass the claimed formula (4), (5), (6), (7), (33), (9), (10) or (11), otherwise the claim could simply be a compound selected from the formula claimed.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
3. Claim(s) 16 is/are rejected 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. Wadsworth on page 14281 in Figure 6. E discloses compound 15, which is a compound of Formula (7) in claim 16 where R1 is C16 containing one double bond and functional group, a carbonyl, one of R2a is H, the other is substituted aryl (pyridine).2
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.
5. 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:
PNG
media_image2.png
152
177
media_image2.png
Greyscale
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.
PNG
media_image3.png
165
466
media_image3.png
Greyscale
PNG
media_image4.png
300
612
media_image4.png
Greyscale
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. 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.
Information regarding the status of an application may be obtained from Patent Center. Status information for published applications may be obtained from Patent Center. Status information for unpublished applications is available through Patent Center for authorized users only. Should you have questions about access to Patent Center, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free).
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) Form at https://www.uspto.gov/patents/uspto-automated- interview-request-air-form.
/DAVID K O'DELL/Primary Examiner, Art Unit 1621
1 Applicant has elected multiple species which appear in the non-elected group, Group I, and makes reference to claims 1-15 in the election, however the requirement was for the election of a single disclosed species for group I or II. At least of the many elections applicant presented, compound 52 reads on Group II, the compound claims and is a compound of Formula (4) in claim 17. There is no admission that the species are patentably indistinct.
2 As discussed in MPEP 2111.01 IV A. “An applicant is entitled to be their own lexicographer and may rebut the presumption that claim terms are to be given their ordinary and customary meaning by clearly setting forth a definition of the term that is different from its ordinary and customary meaning(s) in the specification at the time of filing. See In re Paulsen, 30 F.3d 1475, 1480, 31 USPQ2d 1671, 1674 (Fed. Cir. 1994) (holding that an inventor may define specific terms used to describe invention, but must do so "with reasonable clarity, deliberateness, and precision" and, if done, must "‘set out his uncommon definition in some manner within the patent disclosure’ so as to give one of ordinary skill in the art notice of the change" in meaning) (quoting Intellicall, Inc. v. Phonometrics, Inc., 952 F.2d 1384, 1387-88, 21 USPQ2d 1383, 1386 (Fed. Cir. 1992)). Toro Co. v. White Consolidated Industries Inc., 199 F.3d 1295, 1301, 53 USPQ2d 1065, 1069 (Fed. Cir. 1999) (meaning of words used in a claim is not construed in a "lexicographic vacuum, but in the context of the specification and drawings").” In the lexicographical paradigm of this application aryl includes pyridine, see specification page 9 lines 12-18 particularly lines 15-17, where pyridine is explicitly listed. In the section following on the same page, lines 19-24, substituents include any group(s).
Prosecution Insights