DETAILED ACTION
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 .
Priority
This application is a 371 of PCT/US2022/071870 which claims the benefit of US Provisional 63/201,313 with an effective filing date of 23 April 2021 as reflected in the filing receipt mailed on 13 March 2024.
Information Disclosure Statement
The information disclosure statements (IDSs) submitted are in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements have been considered by the examiner. Lined through reference(s) appear to not be attached.
Election/Restrictions
Applicant's election with traverse of Group 1, claims 1-9, and Applicant’s species election of Formula A, Formula H, Formula L, and Formula J reading on the single species of the claim 5 Compound 2 of Group 1, claims 1-5, in the reply filed on 13 July 2026 are acknowledged.
The traversal is on the ground(s) that “without providing any particular rationale or relevant teaching that would sufficiently guide a person of ordinary skill in the art to select a certain combination of components represented by the claimed components, even less with any expectation of success in doing so, the Examiner has not articulated a rationale disclosed in Jian that would provide a proper basis for achieving the claims of the present application”. Pages 5-6 of the restriction requirement dated 14 April 2026 clearly state “[s]ince “compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups” and analogs, homologs, and/or compounds having very close structural similarities and similar utilities “are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties”, see MPEP 2144.09, the Jian general compound and compound 16 are homologs and/or of sufficiently close structural similarity to the instantly claimed Compound 1. Therefore, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to have modified the Jian compound to add an addition C1 hydrocarbon in the R1 position of the general compound, i.e., a branched hydrocarbon, or to add two C1 hydrocarbons in the R1 position and remove the phenols in the R1 and R2/R3 positions of compound 16 with a reasonable predictability of success for the purpose of efficiently producing an environmentally friendly small organic molecule with the desired chiral activity in order to synthesize chiral amine structural units, see Translation, Abstract; Paras. [0004];[0027]-[0028]” (emphasis added).
In response to Applicant’s with traverse argument that rejoinder of claims 10-20 “should not result in a “serious burden” on the Examiner”. The instant application is a national stage application filed under 35 U.S.C. 371. The search burden criteria only applies to restriction under national applications filed under 35 U.S.C 111(a).
Applicant’s above arguments are not found persuasive; therefore, the restriction requirement is still deemed proper and is therefore made FINAL.
Claims 6-9 are withdrawn from further consideration pursuant to PCT Rule 13.1, as being drawn to a nonelected species of Group I. Claims 10-20 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to the nonelected Group II, there being no allowable generic or linking claim. Claims 1-5 are herein examined on the merits.
Elected Species - Free of Prior Art
As elected by applicants in the response to the species restriction requirement dated 13 July 2026, the single species of the claim 5 Compound 2 of Group 1, appears to be free of prior art. As a result, the species of Compound 2 within the list of variables in claims 1-5 appears to be free of prior art.
Species Search Extension
As per MPEP 803.02C.2., the herein search and examination is extended to the non-elected species or group of species that falls within the scope of a proper Markush grouping that includes the elected species. The herein search is extended to the instant application claim 1 Formula A and B variables of:
Formula A where R6 and R8 are -(CH2)p1- and -(CH2)p3- with p1 and p3 are 0, R4 and R5 are H, R7 and R9 are -(CH2)p2- and -(CH2)p4- with p2 and p4 are 0, R10 is –(CH2)m- with m is 0, j is 0 and k is 0; and,
Formula B where R6 and R8 are -(CH2)p1- and -(CH2)p3- with p1 and p3 are 0, R7 is -(CH2)p2- with p2 is 0, R10 is –(CH2)m- with m is 0, j is 1 and k is 0.
Accordingly, claims 1-5 have been examined on the merits herein. The withdrawals of Group I, claims 6-9, and Group II, claims 10-20, are maintained.
In the Spirit of Compact Prosecution
While the examiner has attempted to identify all objections and clarity issues amongst the claims, applicant is advised that some objections and clarity issues may still remain. Going forward, the examiner respectfully requests applicant to perform a detailed review of the claims regarding clarity, grammar, antecedent basis, word spacing, and spelling issues.
Claim Objections
Claims 1, 3, and 4 are objected to because of the following informalities: Regarding claims 1, 3, and 4, some of the R variables include the limitation “Net”, which appears to include a typographical mistake. The limitation is interpreted as “NEt”.
Claim 1, line 1 states “GAP”. The definition of the acronym GAP should be presented in the claim. For example, “Group-Assisted Purification (GAP)”.
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.
Claim 5 is rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention.
Claim 5 depends from claim 4. The claim 4 compound comprises a general Formula A GAP, a general Formula H linker, a general Formula L first amino acid, and a general Formula J stopper. Claim 5 is drawn to a specific compound. It is unclear as to whether claim 5 is drawn to the compound of claim 4 further comprising the compound of claim 5 or if the compound of claim 5 is limiting the general Formula A GAP, the general Formula H linker, the general Formula L first amino acid, and the general Formula J stopper of claim 4 to one or more of the particular species defined in claim 4.
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.
Claim 1 is rejected under 35 U.S.C. 102(a)(1) as being anticipated by Itaya et al. (“Synthesis and Absolute Configuration of Wybutine, the Fluorescent Minor Base from Phenylalanine Transfer Ribonucleic Acids”, published June 1991, Chemical and Pharmaceutical Bulletin, Vol. 39, Iss. 6, Pgs. 1407-1414, hereinafter Itaya).
Itaya is in the known prior art field of phosphine oxides produced in organic synthesis chemical reactions that are easily removed by washing with ether, see Pg. 1408 and Chart 2; Pg. 1412, Col. 1, (S)-2-[(Methoxycarbonyl)amino] -4-phenylbutanoic Acid (12).
Regarding the limitations of instant application claim 1, Itaya discloses a chemical synthesis composition containing a product “mixture of 12 and 15 (molar ratio, 4:1). This was dissolved in ether (23 ml) and insoluble 15 was filtered off. Recrystallization of crude 15 from ethyl acetate afforded colorless needles, mp 115-125 ◦C, see Pg. 1412, Col. 1, (S)-2-[(Methoxycarbonyl)amino] -4-phenylbutanoic Acid (12), where compound 15 is represented by the following formula:
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110
214
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aka
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310
386
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, see Pg. 1408 and Chart 2. Compound 15 of Itaya corresponds to instant application:
Formula A where R6 and R8 are -(CH2)p1- and -(CH2)p3- with p1 and p3 are 0, R4 and R5 are H, R7 and R9 are -(CH2)p2- and -(CH2)p4- with p2 and p4 are 0, R10 is –(CH2)m- with m is 0, j is 0 and k is 0; and,
Formula B where R6 and R8 are -(CH2)p1- and -(CH2)p3- with p1 and p3 are 0, R7 is -(CH2)p2- with p2 is 0, R10 is –(CH2)m- with m is 0, j is 1 and k is 0, meeting:
A composition with a constituent selected from Formula A or Formula B in instant application claim 1.
In regard to the instant application claim 1 limitation of a/the “GAP constituent”, “[w]here applicant claims a composition in terms of a function, property or characteristic and the composition of the prior art is the same as that of the claim but the function is not explicitly disclosed by the reference, the examiner may make a rejection under both 35 U.S.C. 102 and 103”, see MPEP 2112 III. In this case, Itaya teaches compound 15 is an easily removeable compound that is removed by washing in ether, see Pg. 1412, Col. 1, (S)-2-[(Methoxycarbonyl)amino] -4-phenylbutanoic Acid (12). As stated in Paras. [0004];[0059] of the instant specification, “Group-Assisted Purification (GAP) chemistry/technology as a chemistry for organic synthesis that avoids traditional purification methods such as chromatography and/or recrystallization” and the GAP compound is removed/deprotected by ethers, such as tetrahydrofuran or methyltetrahydrofuran. As a result, compound 15 of Itaya is inherently a GAP constituent in the composition of Itaya.
Claims 2-5 are objected to as being dependent upon the rejected base claim 1, but may be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Conclusion
No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Y. Lynnette Kelly-O'Neill whose telephone number is (571) 270-3456. The examiner can normally be reached Tuesday-Friday, 8:30 a.m. - 6:30 p.m., EST, with Flex Time.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Yen-Ye Goon can be reached at (571) 270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/YO/Examiner, Art Unit 1692
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699
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