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
Acknowledgments are made that this application claims the priority to the following:
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Information Disclosure Statement
Filed information disclosure statements (IDS) comply with the provisions of 37 CFR 1.97, 1.98 and MPEP § 609. Accordingly, they have been placed in the application file and the information therein has been considered as to the merits.
Response to Restriction
Applicant's response to restriction requirement and election of group I corresponding to claims 1, 3, 9, 11, 17, 23, 33, 36-37, 42, 45-47, 52, 60-61, 79, 82, 84 and 92, without traverse, in the reply filed on 2nd March 2026 is acknowledged.
The examiner also acknowledges applicants response to election of species and providing a single following species for the claimed compound of formula (I):
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which is Phe-Arg-Phe-Lys, wherein Arg side chain is protected with ethoxy carbonyl group.
The above elected species reads claims 1,3,9,11,17,23,33,36-37,42,45-47,52,60-61,79,82,84 and 92 and these are examined on merits in this office action.
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. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. 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 1,3,9,11,17,23,33,36-37,42,45-47,52,60-61,79,82,84 and 92 are rejected under 35 U.S.C. 103 as being unpatentable over Wilson (US 2018/0362579 A1) in view of Altenburger (WO98/42700) and Isidro-Llobet (Chem.Rev., 2009, 109, 2455-2504).
For claim 1:
Wilson teaches the following tetrapeptides:
H-Phe-Arg-Phe-Lys-NH2,
H-Phe-D-Arg-D-Phe-Lys-NH2 and
H-Phe-D-Arg-Phe-D-Lys-NH2 [see page 2]
Difference is that in the above peptide(s), side chain of Arg is not protected with applicants elected ethoxy carbonyl group.
However, ethoxy carbonyl and its structurally similar protecting groups are known in the art. For example, Altenburger teaches the following the compound, wherein side chain of Arg is protected with ethoxy carbonyl or its structurally similar protecting groups:
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, wherein R is H, R1 is H, and R’1 is -COOCH2CH3, -COOCH3 and Ph-CH2-COO- [see Table, pages 43 and 46].
In addition, Isidro-Llobet teaches butyloxycarbonyl (Boc) and benzyloxycarbonyl protecting groups [see Table 18 and 19] for side chain of Arg.
Protecting groups, viz., Boc and benzyloxycarbonyl are very common in peptide synthesis or organic chemistry. The Boc is differed with applicants ethoxy carbonyl group in the size of alkyl group or replacing methylene group with di-alkyl substituted methylene group. Applicants ethyoxy carbonyl is obvious over Boc based on the following case laws:
"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 homologs 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." In re Deuel 34 USPQ2d 1210 at 1214. Furthermore MPEP 2144.09 (II) states: "Compounds which are … 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)."
The issue of patentability over the replacement of alkyl groups for hydrogen has arisen many times. For instance, the replacement of a methylene group with a dialkyl-substituted methylene group was determined to be prima facie obvious on the ground that "one skilled in the art would have been, prima facie, motivated to make the claimed compounds in the expectation that they, too, would possess antimicrobial activity." (In re Wood 199 USPQ 137) See also In re Doebel 174 USPQ 158 (where replacement of methyl for hydrogen on an amino nitrogen was considered prima facie obvious - at page 159); In re Druey 138 USPQ 39 (where replacement of methyl for hydrogen on a known compound was considered prima face obvious based on the homologous and close structural relationship to the known compound - at page 41); In re Lohr 137 USPQ 548 (where the replacement of a methyl group for a hydrogen on two positions of a tetrahydropyran ring on a known compound was not considered a patentable modification given the close structural relationship to the known compounds - at page 550); Ex parte Bluestone 135 USPQ 199 (where fungicidal compounds differing by hydrogen versus methyl on the nitrogen of a thiazolidine-2-thione ring were considered homologs and were not found to be patentable over each other without a showing of unexpected results - at page 200); Ex parte Weston 121 USPQ 429 (where the replacement of methyl for hydrogen on the nitrogen of a piperazine ring was not found to be a patentable modification).
The motivation to make a substitution of an alkyl group for hydrogen stems from the fact that a person having ordinary skill in the art would expect that the compounds could be prepared by the same method as taught by the prior art and have the same utility as the compounds taught by the prior art.
MPEP 2144.09 (VII) states "A prima facie case of obviousness based on structural similarity is rebuttable by proof that the claimed compounds possess unexpectedly advantageous or superior properties. In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963)."
For claim 3:
In the compound of Wilson, side chain of Lys reads applicants X, when R1 and R15 are H atoms.
For claim 9:
In the compound of Wilson, side chain of Arg reads applicants Y. However, Wilson is silent on applicants R2 group, for example, elected ethoxy carbonyl group as a protecting group on (H2N)(HN)CN(H) on the side chain of Arg. As explained above, this protecting group is known in the art and is obvious, see the reasoning above under For claim 1.
For claim 11:
In the compound of Wilson, side chain of Lys reads applicants X, when R1 is H atom.
For claim 17:
In the compound of Wilson, side chain of Arg reads applicants Y. However, Wilson is silent on applicants R2 group, for example, elected ethoxy carbonyl group as a protecting group on (H2N)(HN)CN(H) on the side chain of Arg. As explained above, this protecting group is known in the art and is obvious, see the reasoning above under For claim 1.
For claim 23:
In the compound of Wilson, N-terminus H reads applicants R3.
For claims 33, 36-37, 42 and 45-46:
In the compound of Wilson, side chain of Phe reads applicants R4 and R5, wherein R14 is H atoms.
For claim 47:
In the compound of Wilson, H atoms on C-terminus -NH2 read applicants R6 and R7.
For claim 52:
In the compound of Wilson, N-terminus H reads applicants R8.
For claims 60-61:
Wilson silent on applicants ethoxy carbonyl protecting group, viz., R10OC(O)- on the side chain of Arg, wherein R10 is alkyl group. As explained above, this protecting group is known in the art and is obvious, see the reasoning above under For claim 1.
For claim 79:
In the compound of Wilson, side chain of Lys reads applicants X, when R15 is H atom.
For claim 82:
In the compound of Wilson, side chain of Lys reads applicants X, wherein n is 4.
For claim 84:
In the compound of Wilson, side chain of Arg reads applicants Y, wherein n is 3.
For claim 92:
First compound in the list is applicants elected species. See the reasoning For claim 1 above.
Based on the above established facts from the cited prior art, it appears that all the claimed elements, i.e, applicants individual components in the compound of formula (I), were known in the prior art, and one skilled person in the art could have combined the elements as claimed by known relationships, with no change in their respective functions, and the combination would have yielded predictable results to one of ordinary skill in the art.
The motivation to combine the art can arise from the expectation that the prior art elements will perform their expected functions to achieve their expected results when combined for their common known purpose. See MPEP 2144.07. Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention by taking the advantage of the teaching of the above cited reference and to make the instantly claimed compound with a reasonable expectation of success.
The strongest rationale for combining references is a recognition, expressly or impliedly in the prior art or drawn from a convincing line of reasoning based on established scientific principles or legal precedent, that some advantage or expected beneficial result would have been produced by their combination. In re Sernaker, 702 F.2d 989, 994-95, 217 USPQ 1, 5-6 (Fed. Cir. 1983).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SUDHAKAR KATAKAM whose telephone number is (571)272-9929. The examiner can normally be reached 8:30 am to 5 pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Melissa Fisher can be reached at 571-270-7430. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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SUDHAKAR KATAKAM
Primary Examiner
Art Unit 1658
/SUDHAKAR KATAKAM/Primary Examiner, Art Unit 1658