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 .
Election/Restrictions
Applicant’s election without traverse of Group I and the following prepared compound in the reply filed on 1/21/2026 is acknowledged.
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Claims 4, 5, 8, 9, 16, 19-22, 24, 27-30, 39, 40, 42, 44-52, and 59 withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected prepared compound (4, 5, 8, 9, and 16) and Group II-VII (19-22, 24, 27-30, 39, 40, 42, 44-52, and 59) and there being no allowable generic or linking claim.
Status of Claims
Cancelled: 7, 10-15, 17, 18, 23, 25, 26, 31-38, 41, 43, 53-58
Withdrawn: 4, 5, 8, 9, 16, 19-22, 24, 27-30, 39, 40, 42, 44-52, and 59
Examined Herein: 1, 2, 3, 6
Priority
Acknowledgment is made of applicant's claim for priority under based upon an application filed in PRO 63/059,041 on 7/30/2020 and PCT/CA2021/051069 on 7/29/2021.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 7/20/2023 and 9/5/2025 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Drawings
The drawings received on 1/30/2023 are accepted.
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 1-3 and 6 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.
Claims 1, 2, and 3 recite the limitation “(C ≤ 12).” It is unclear why this notation is in parenthesis. Specifically, it is unclear whether this notation limits the claim to include chemical groups having less than or equal to 12 carbon atoms or whether it merely represents a preferred embodiment of the chemical groups. The specification does not provide clarification as the definitions for the chemical groups recited therein do not include parenthetical notations and do not clearly resolve the scope of the claim language. Accordingly, the scope of the claims cannot be reasonably ascertained. Further clarification is required. Dependent claims fall therewith.
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.
The factual inquiries 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.
Claim 1 is rejected under 35 U.S.C. 103 as being unpatentable over Wang (Studies towards asymmetric synthesis of 4(S)-11-dihydroxydocosahexaenoic acid (diHDHA) featuring cross-coupling of chiral stannane under mild conditions, 2015, Organic and Biomolecular Chemistry, 13;1624-1628), in view of Mohamed (Z-Stereoselective semi-reduction of alkynes: modification of the Boland protocol, 2013, Tetrahedron, 59:3872-3877).
With respect to claim 1, Wang discloses a method of preparing a protectin, protectin analog, structural isomer, or a pharmaceutically acceptable salt thereof, the method comprising reacting a compound of formula (I):
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[Page 1626, Scheme 5, 21]
wherein,
R1 is alkenyl (decatriene),
X1 is hydroxy,
X3 is hydroxy, and
X2 is CH3COONa;
with a reducing agent, Red-Al or Zn(Cu/Ag), under conditions sufficient to produce a compound of Formula (II):
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671
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[Page 1625, Scheme 1, 1(b); see also Page 1624, Figure 2]
wherein,
R1 is alkenyl (decatriene)
X1 is hydroxy,
X3 is hydroxy, and
X2 is COOH.
Wang does not disclose X2 is hydroxy or OP.
However, Mohamed stereoselective reductions of internal alkynes are commonly employed in the synthesis of conjugated polyunsaturated fatty acids, esters, or alcohols. [Mohamed, Page 3872, Col. 1, Paragraph 1 & Figure 1]
In a specific embodiment, Mohamed discloses a method for preparing a polyunsaturated fatty methyl ester comprising reacting a E,Z,E-substituted triene:
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[Mohamed, Page 3873, Table 1, Alkyne 6]
wherein,
R1 is C4-alkyl, and
X2 is methyl ester;
with a reducing agent, Zn(Cu/Ag), under conditions sufficient to produce a compound:
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[Mohamed, Page 3873, Table 1, Product 7]
In another embodiment, Mohamed discloses a method for preparing a polyunsaturated fatty alcohol comprising reacting a E,Z,E-substituted triene:
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[Mohamed, Page 3873, Table 1, Alkyne 8]
wherein,
R1 is C4-alkyl, and
X2 is hydroxy;
with a reducing agent, Zn(Cu/Ag), under conditions sufficient to produce a compound:
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[Mohamed, Page 3873, Table 1, Product 9]
Modifying the method disclosed by Wang such that Formula (I) comprises a terminal -OH group in place of the terminal COONa group results in the method of claim 1;
In which case, Formula (I) has the following structure:
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[Structure drawn by Examiner using CAS Draw based on the modification described above]
wherein,
X2 is hydroxy; and
Formula (II) has the following structure:
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[Structure drawn by Examiner using CAS Draw based on the modification described above]
wherein,
X2 is hydroxy.
It would be obvious to one of ordinary skill in the art to modify the method disclosed by Wang such that Formula (I) comprises a terminal -OH group in place of the terminal -COONa group and have a reasonable expectation of success. Wang discloses the synthesis of a polyunsaturated fatty acid comprising reacting a 4(S)-11-diHDHA intermediate with a reagent to obtain 4(S)-11-diHDHA, wherein the intermediate is an internal alkyne with a terminal -COONa. Mohamed discloses internal alkynes are commonly employed in the synthesis of conjugated polyunsaturated fatty acids esters, or alcohols. Mohamed demonstrates the synthesis of a polyunsaturated fatty acid comprising reacting an internal alkyne intermediate with a reagent to obtain a stereoisomeric alkene, wherein the intermediate comprises a terminal -COOMe or -OH. Thus, Wang and Mohamed establish that an internal alkyne intermediate may comprise a terminal -COONa, -COOMe, or -OH and be employed in the synthesis of polyunsaturated fatty acids, methyl esters, or alcohols. Accordingly, the combined teachings of Wang and Mohamed suggest the internal alkyne intermediate employed in the synthesis of 4(S)-11-diHDHA disclosed by Wang may comprise a terminal -OH group. One would have been motivated to do so because it is prima face obvious to combine references when some advantage or expected beneficial result would have been produced by their combination. In the instant case, Mohamed discloses and demonstrates that internal alkynes bearing variable terminal groups (including -COOH, -COOMe, or -OH) with a terminal -COONa may be employed in the synthesis of many conjugated polyunsaturated natural products (including fatty acids, methyl esters, and alcohols). [Mohamed, Page 3872, Col. 1, Paragraph 1 & Figure 1, Page 3873, Table 1] Therefore, one would have been motivated by the expectation that the aforementioned modification could enable the synthesis of a polyunsaturated natural products other than a fatty acid, like fatty alcohol.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to KAILA A CRAIG whose telephone number is (703)756-4540. The examiner can normally be reached Monday-Friday 0800-1600.
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/K.A.C./Examiner, Art Unit 1618
/Michael G. Hartley/Supervisory Patent Examiner, Art Unit 1618
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