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 applicant’s communication filed on 12/10/25.
Claims 16-30 are pending in this application.
Applicant's election of Group 1, claims 16-23, without traverse, in the reply filed on 12/25/25 is acknowledged. Thus claims 24-30 are withdrawn.
Applicant’s election of the following compound is acknowledged herewith:
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Claim 23 is withdrawn and being non-readable on the elected species. As a result, claims 16-22 are being examined in this Office Action.
Priority
The applicant claims benefit as follows:
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Claim Rejections – 35 USC 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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 of this title, 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.
The factual inquiries set forth in Graham v. John Deere Co., 383 U.S. 1, 148
USPQ 459 (1966), that are applied for establishing a background for determining obviousness under 35 U.S.C. 1 03(a) are summarized as follows:
Applicant Claims
Determining the scope and contents of the prior art.
Ascertaining the differences between the prior art and the claims at issue, and resolving the level of ordinary skill in the pertinent art.
Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 16-22 are rejected under 35 U.S.C. 103(a) as being unpatentable over Giroud et al. (J. Med. Chem., 2018, 61, 3370), in view of Greene’s Protective Groups in Organic Synthesis (4th Ed., Wuts and Greene, 2007, John Wiley).
Determination of the Scope and Content of the Prior Art
(MPEP §2141.01)
Giroud et al. exemplifies the following compound, which corresponds to applicant’s compound I as follows:
SG = t-butyl (Boc) protecting group
A = R1 – O – R2
R1 = ethylene
R2 = methyl
Halogen is Chlorine at the 3 position
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Ascertainment of the Difference Between Scope the Prior Art and the Claims
(MPEP §2141.012)
Giroud et al. is deficient in the sense that it does not teach applicant’s particular iodine substitution, 9-fluorenylmethyl (Fmoc) protecting group and methylene linker. Instead Giroud et al. teaches chlorine substitution, a t-butyl (Boc) protecting group and an ethylene linker.
Finding of Prima Facie Obviousness Rationale and Motivation
(MPEP §2142-2143)
However, it would be prima facie obvious to one of ordinary skill in the art at the time of the invention, to substitute a different halogen, an ethylene linker for a methylene linker and use the Boc protecting group instead of a FMOC protecting group on the tyrosine derivative. Both iodine and chlorine are halogens and are commonly employed as isosteric replacements for each other. Further, an ethylene linker (two CH2 groups) versus a methylene linker (one CH2 group) are homologous. Thus it would be obvious to substitute an methylene linker with an ethylene linker on the tyrosine derivative.
Additionally, both the t-butyl (Boc) and the 9-fluorenylmethyl (Fmoc) protecting groups are commonly used carbamate protecting groups for amino acids and amines. Greene’s Protective Groups in Organic Synthesis teaches the equivalency of the t-butyl (Boc) and the 9-fluorenylmethyl (Fmoc) protecting groups for the nitrogen amine in amino acids. (see page 707, second paragraph)
Note that an express suggestion to substitute one equivalent component or process for another is not necessary to render such substitution obvious. In re Fout, 675 F.2d 297, 213 USPQ 532 (CCPA 1982).
Thus the claims are obvious because it would have been obvious to try alternative isosteres, homologs and equivalent protecting groups, with a reasonable expectation of success. Thus the skilled artisan would have had reason to try these replacements, with the reasonable expectation that it would be successful. Synthesizing compounds with isosteres, homologs and equivalent protecting groups is not a method of innovation but of ordinary skill and common sense. Absent any showing of unusual and/or unexpected results over Applicant's particular tyrosine derivative, the art obtains the same effect on the compound' s efficacy and utility. The expected result would be the synthesis of tyrosine derivatives, for the chemical industry.
“Structural relationships may provide the requisite motivation or suggestion to modify known compounds to obtain new compounds. For example, a prior art compound may suggest its homolog because homologs often have similar properties and therefore chemists of ordinary skill would ordinarily contemplate making them to try to obtain compounds with improved properties.” (see MPEP § 2144.08c). In addition, homologs are generally so structurally similar that “without more” such structural similarity could give rise to prima facie obviousness (see In re Wilder, 563 F.2d 457, 195 USPQ 426).
The MPEP 2144.09 states “Compounds which are… homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977).
Conclusion
No claim is allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Jennifer Cho Sawyer whose telephone number is (571) 270 1690. The examiner can normally be reached on Monday-Friday 9 AM - 6 PM PST.
If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Renee Claytor can be reached on (571) 272-8394. The fax phone number for the organization where this application or proceeding is assigned is 571-274-1690.
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Jennifer Cho Sawyer
Patent Examiner
Art Unit: 1691
/RENEE CLAYTOR/Supervisory Patent Examiner, Art Unit 1691