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 .
FINAL ACTION
Priority
Instant application 17/759782 filed on 07/29/2022 claims benefit as follow:
CONTINUING DATA:
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Status of the Application
Claims 32, 36-41, 45-48 and 52 are pending.
Response to Arguments/Amendments
The amendment filled on 11/19/2025 has been entered.
Applicant amended claims 32, 36, 40, 41 and 45.
Applicant canceled claims 33-35, 42-44, 49-51 and 53-65.
It should be noted that Applicant deleted ester and limited the instant claims to acceptable salts of formula (II) and (III).
In addition, Applicant limited the instant claims into (see amended claim 32):
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Applicant’s amendment and Applicants arguments have overcome the 101 rejection and all 102 rejections of record; therefore the 101 and 102 rejections of record are withdrawn.
In the previous office action Examiner requested details about the purchase of sodium salt of the elected species (C17:1 n-9).
Regarding the sodium salt of the elected species, Applicant submitted a declaration under 37 CFR 1.132 filed 11/29/2025. Applicant submitted (see declaration):
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Further, Applicant submitted (see Applicant’s arguments):
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The declaration under 37 CFR 1.132 filed 11/19/2025 is insufficient to overcome the 103 rejections as set forth in the last Office action because it would have been obvious to prepare sodium salt of a known acid.
Regarding the 103 rejections, Applicant's arguments filed 11/19/2025 have been fully considered but they are not persuasive.
Regarding the 103 rejections, Applicant submitted:
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Applicant's arguments that the salt of civetic acid unexpectedly provides higher antiproliferative effect in glicoma cell lines have been fully considered but they are not persuasive because the instant claims are products claims not a method claims. In addition, the claims are not commensurate in scope with the result.
MPEP 2112.02 states that the discovery of a new use for an old structure based on unknown properties of the structure might be patentable to the discoverer as a process of using.
In the instant case, it is examiner position that it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to prepare and test sodium salt of civetic acid (aka 8-heptadecenoic acid 17:1) as anti-inflammatory agent because Grimmer teaches that sodium salt of cis-9-heptadecenoic acid (isomer of cis-8-heptadecenoic acid) have anti-inflammatory properties (see claim 1). Further, it should be noted that civetic acid is a well know acid.
For example, Alves (Alves, S.P., Marcelino, C., Portugal, P.V., et al. Short communication: The nature of heptadecenoic acid in ruminant fats. J. Dairy Sci. 89(1), 170-173 (2006)) teaches 8-heptadecenoic acids (aka civetic acid) is present in ruminant milk intramuscular fat of bovine, ovine and caprine origin (see abstract and Figure 1):
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A person of ordinary skill would have been capable of preparing a sodium salt of a known acid. Further, the skilled artisan would have been motivated to use the sodium salt of cis-8-heptadecenoic acid as anti-inflammatory because Grimmer teaches that sodium salt of cis-9-heptadecenoic (isomer of cis-8-heptadecenoic) have anti-inflammatory properties.
The skilled artisan would have been motivated to pick sodium salt because Grimmer teaches sodium salts are readily soluble in water (machine translation, page 3, paragraph 4):
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Applicant's arguments that:
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has been fully considered but is not persuasive because it is examiner position that a skilled artisan would have been motivated to use sodium salt of cis-8-heptadecenoic acid as anti-inflammatory agent. Grimmer teaches that sodium salt of cis-9-heptadecenoic (isomer of cis-8-heptadecenoic) have anti-inflammatory properties. MPEP 2144.09 states: Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or 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.
Therefore, the 103 rejections are maintained below.
Election/Restrictions
Applicant’s election, without traverse, of Group I, directed to products, in the reply filed on 07/07/2025 is acknowledged.
Claims 37, 38, 39, 46-48 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 07/07/2025.
Regarding species election, Applicant’s elected, without traverse, “salt or ester” of compound of Formula (II) wherein a=6, b=1 and c=6:
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However, it should be noted that Applicant delated “ester”, and the instant amended claims are limited to “salt” (amendment filled on 11/19/2025 has been entered).
Please note that in the previous office action, examiner requested election of a single, disclosed compound or a single, disclosed pharmaceutical composition.
In addition, examiner requested:
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Applicant elected a salt or ester of compound of Formula (II): civetic acid (C17:1 n-9, 8-heptadecenoic acid). Applicant did not elect pharmaceutical composition, any excipient species nor second compound species.
Examination will begin with the elected species. In accordance with the MPEP 803.02, if upon examination of the elected species, no prior art is found that would anticipate or render obvious the instant invention based on the elected species, the search of the Markush-type claim will be extended. If prior art is then found that anticipates or renders obvious the non-elected species, the Markush-type claim will be rejected. It should be noted that the prior art search will not be extended unnecessarily to cover all non-elected species. Should Applicant overcome the rejection by amending the claim, the amended claim will be reexamined. The prior art search will be extended to the extent necessary to determine patentability of the Markush-type claim. In the event prior art is found during reexamination that renders obvious or anticipates the amended Markush-type claim, the claim will be rejected and the action made final.
Species Election
Applicant stated on page 50 of the instant specification that Applicant purchased sodium salt of C17:1 n-9 8-heptadecenoic acid from Medalchemy, SL:
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The data for the sodium salt of 8-heptadecenoic acid is not available in STN and the website of Medalchemy does not provide a list of compounds.
In the response to the previous office action, Applicant submitted (see Applicant arguments):
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As discussed in the previous office action, Esters of C17:1 n-9, 8-heptadecenoic acid (the elected species) have been identified in prior art.
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However, Applicant delated “ester” and limited the instant claims to “salt”.
Therefore, sodium salt of C17:1 n-9, 8-heptadecenoic acid (sodium salt of civetic acid) is under current consideration.
Claim Objections
Claims 32, 36, 40, 41 and 45 are objected to because of the following informalities:
The COOH group in formula (II), (III) and (I) should be connected through carbon not through hydrogen. The person of ordinary skill would understand that the connection is through carbon, however, for clarity examiner suggest to draw e.g. structure (II) as HOOC-(CH2)a-(CH=CH-CH2)b-(CH2)c-CH3.
Appropriate correction is suggested.
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 (i.e., changing from AIA to pre-AIA ) 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, 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.
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 32, 36, 40 and 45 are rejected under 35 U.S.C. 103 as being unpatentable over Grimmer (DE114721B) evidenced by Alves (Alves, S.P., Marcelino, C., Portugal, P.V., et al. Short communication: The nature of heptadecenoic acid in ruminant fats. J. Dairy Sci. 89(1), 170-173 (2006)).
Grimmer teaches and claims sodium salts of cis-9-pentadecenoic acid and cis-9-hexadecenoic acid (see claim 1):
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(It should be noted that for cis-9-Pentadecenoic acid a=7, b=1, c=5 and a+3b+c+3 = 18 and cis-9-pentadecenoic n a = 7, b = 1, c = 3 and a+3b+c+3 = 16).
Grimmer teaches and claims:
PATENT CLAIM: “Process for the production of anti-inflammatory and anti-edema Salts of pentadecanoic and heptadecenoic acids, characterized in that the cis-9-pentadecenoic acid or cis-9-heptadecenoic acid in a manner known per se with a physiologically compatible base in the salt, preferably in the sodium or Potassium salt transferred” (machine translation, page 1, claim 1).
Regarding claims 40 and 45, Grimmer teaches a composition comprising pharmaceutically acceptable excipient, e.g., water and ethanol (machine transition see page 4, last two lines, page 5, line 2).
Grimmer teaches: The properties of the sodium salt of 9-heptadecinic acid were determined at 19.5 ° C. Solubility in ethanol: 0.02 g per cubic centimeter of ethanol (machine transition see page 4, last two lines). Solubility in water: 0.042 g per cubic centimeter of water (machine transition see page 5, line 2)
Grimmer teaches “The new salts are preferably in the form of aqueous solutions, such as physiological saline, injected intravenously or intramuscularly” (see machine translation, page 3, paragraph 5).
Grimmer teaches (machine translation, page 3, paragraph 4):
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Grimmer does not teach a sodium salt of the elected species (instant formula (II) wherein a=6, b=1, c=6):
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As evidenced by Alves, civetic acid (the compound of formula (II) wherein a=6, b=1, c=6) is a known compound that can be separated from milk or butterfat as methyl ester (see abstract).
Alves teaches 8-heptadecenoic acid (aka civetic acid) are present in ruminant milk intramuscular fat of bovine, ovine and caprine origin (see abstract and Figure 1):
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Please note that cis-8 isomer (the elected species) falls under instant formula (II) wherein a = 6, b = 1, c = 6.
Further, Alves teaches (page 171, last paragraph):
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Regarding claims 40, Alves teaches excipients (water, proteins, vitamins, and minerals) present in milk.
In addition, MPEP 2144.09 states:
Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or 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.
Applying KSR prong (B) - it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to substitute sodium salt of cis-9-heptadecenoic acid with a sodium salt of cis-8-heptadecenoic acid and use it for the same purpose with a reasonable expectation of success.
One of ordinary skill would have been motivated to test additional isomers of heptadecenoic acid for the same purpose because Grimmer teaches the disclosed salts of heptadecenoic acids have anti-inflammatory properties (see claim 1). The skilled artisan would have been motivated to pick sodium salt because Grimmer teaches sodium salts are readily soluble in water (machine translation, page 3, paragraph 4):
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Claim 41 is rejected under 35 U.S.C. 103 as being unpatentable over Grimmer (DE114722) in view of Ruiz (US-20120108550-A1) evidenced by Alves (Alves, S.P., Marcelino, C., Portugal, P.V., et al., J. Dairy Sci. 89(1), 170-173 (2006)).
The teachings of Grimmer are discussed above and are incorporated herein by reference.
Grimmer teaches salts of pentadecanoic and heptadecenoic acids have anti-inflammatory properties (see claim 1).
Regarding claim 41, Grimmer does not teach combinations of compounds of formula (I) and (II).
The deficiency is resolved by Ruiz.
Ruiz discloses compounds of instant formula (I) (e.g., compound 182A1 and 205A1) (see Table 2):
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Ruiz also discloses acids from natural sources (Table 2) and teaches:
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Ruiz teaches:
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Ruiz teaches:
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Ruiz teaches pharmaceutical compositions comprising excipients and/or other active ingredients:
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Applying KSR prong (A) - it would have been prima facie obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to prepare compositions of salts of pentadecanoic or heptadecanoic acids in combination with a compound of formula (I), for example compound 205A1, for the same purpose.
Ruiz teaches the hydroxylated compounds have slower metabolism, which results in an increased presence in the cell membrane compared to the PUFAs used before (see paragraph [0014]). The skilled artisan would understand that the compounds disclosed by Grimmer may be quickly metabolized and would have been motivated to test the compounds in combination with compounds disclosed by Ruiz for the same purpose.
Art Made of Record but not Applied
U.S. Patent No. US-10201515-B2
The claims of US-10201515-B2 recite compounds of instant formula (I):
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The claims of US-10201515-B2 recite a pharmaceutical composition comprising excipients:
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The claims of US-10201515-B2 recite a pharmaceutical composition for treatment of inflammatory disease comprising sodium salt of compound 182-A1:
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However, the claims of US-10201515-B2 are silent about compounds of instant formula (II) and combinations of compounds of formula (I) and (II).
U.S. Patent No. US-9359281-B2
The claims of U.S. Patent No. US-9359281-B2 recite:
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However, the claims of U.S. Patent No. US-9359281-B2 are silent about compounds of instant formula (II) and combinations of compounds of formula (I) and (II).
U.S. Patent No. US-9161928-B2
The claims of US-9161928-B2 recite:
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However, the claims of U.S. Patent No. US-9161928-B2 are silent about compounds of formula (II) and combinations of compounds of formula (I) and (II).
Conclusion
No claim is allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to IZABELA SCHMIDT whose telephone number is (703)756-4787. The examiner can normally be reached Monday - Friday from 9 am to 5 pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Clinton A Brooks can be reached at (571)270-7682. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/I.S./Examiner, Art Unit 1621
/CLINTON A BROOKS/Supervisory Patent Examiner, Art Unit 1621