DETAILED ACTION
Background
The amendment dated July 01, 2026 (amendment) amending claims 7-13 adding new claims 16-19 and canceling claims 1-6 and 14-15 has been entered. Claims 7-13 and 16-19 as filed with the amendment have been examined. In view of the amendment, all outstanding claim objections have been withdrawn. In view of the cancelation of claims 1-6 and 14-15, all outstanding rejections of those claims have been withdrawn.
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 .
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 7-13 and 16-19 are rejected under 35 U.S.C. 103 as being unpatentable over US2014/0147529 A1 to Duval et al. (Duval) in view of US 7,763,273 B2 to Losa (Losa) and WO2021/163148 A1 to Farmer et al. (Farmer), all of record.
Regarding instant claims 7-8, 10, 17 and 19, Duval at [0014] discloses a method for reducing the production of methane emanating from the digestive activities of ruminants (“reducing the formation of methane emanating from the digestive activities of ruminants” - claim 7) comprising orally administering to a ruminant (claim 7) a compound of formula (I) comprising at least one nitrooxy group including (at [0031]) 3-nitrooxypropanol, which is the same compound as the claimed propanediol mononitrate. At [0039]-[0040], Duval discloses the use of compounds of formula (I) together with essential oils that also reduce methane formation in the rumen, wherein the amount of propanediol mononitrate disclosed (at [0071]) ranges from about 1 mg to about 10 g per kg of feed. At Example 18 and [0157]-[0159] and accompanying Table 8, Duval discloses administering 500 mg/day and 2500 mg/day of the propanediol mononitrate (PMDN) to dairy cows (“domestic cattle” - claim 19), or about 0.5 to 2.5 g PMDN/ animal/day (claims 7-8 and 17). Duval in Example 3 at [0106] discloses that PDMN has a MW 121.04, and thereby Duval discloses in Example 18 administering 0.5 to 2.5 g PDMN/ animal/ day or about 0.5/121 moles to about 2.5/121 moles PDMN/ animal/ day or about 0.0041 to about 0.021 moles PDMN/ animal/ day or 0.496 to about 2.5 g PDMN/ animal/ day as in claim 7. Further, Table 9 of Duval discloses in its Example 18 administering 18.9 Kg feed/ animal/ day or about 500 to 2500 mg/18.9 Kg feed/day or about 26.5 to about 132 mg propanediol mononitrate (PMDN) per kg dry feed as in claim 10. And Duval at [0051] discloses animal feeds comprising from 50 to 500 mg of the PMDN per kg of feed, which the claimed 20 to 250 mg PMDN per kg of dry matter feed as in claim 10 overlaps. In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art", the Office considers that a prima facie case of obviousness exists. See MPEP 2144.05.I. The ordinary skilled artisan in Duval would have found it obvious to use the claimed amount of propanediol mononitrate or PDMN in its feed because Duval discloses that the claimed amount of PDMN provides a desirable animal feed for reducing methane production in ruminants.
Further, and regarding instant claims 9-11 and 17-18, Duval does not disclose limonene as its essential oil as in claim 7 or any specific amount of limonene; however, Duval at [0040] generally discloses including essential oils and at [0051] discloses compositions containing the PMDN and essential oils contained in feed as a premix in a dosage amount of about 10 mg to 1g per kg or food, which the claimed 20 to 250 mg of PMDN per kg of dry matter feed in claim 10 lies within. See MPEP 2144.05.I. Further, Duval does not disclose administering the limonene to the ruminant in an amount selected in the range from 0.05 to 100 g limonene/ animal/ day as in claim as in claim 7; and Duval does not disclose a method comprising orally administering the propanediol mononitrate as a powderous formulation comprising propanediol mononitrate in an amount of 1% to 20%, by weight, based on the total weight of the powderous formulation as in claims 7 and 10. In addition, Duval does not disclose a method of administering from 0.1 to 50 g limonene/ animal/ day as in claims 9 and 17, and, further Duval does not disclose from 0.2 to 25 g limonene/ animal/ day as in claims 9 and 17. In further claims, Duval does not disclose a feed composition or feed additive comprising limonene and propanediol mononitrate, wherein the feed composition is a ruminant feed comprising limonene in an amount selected in the range from 5 mg to about 5 g limonene per kg dry matter feed as in claim 10; and, Duval does not disclose a method wherein the molar ratio of limonene to propanediol mononitrate is, respectively, between and from 100:1 and 1:1 as in claims 11 and 18.
In addition, regarding instant claims 12 and 16 Duval does not disclose administering as its essential oil a D-limonene as in claims 12 and 16.
Losa at Abstract discloses methods for reducing the production of methane emanating from the digestion of animals by administering to the animal feed a formulation comprising one or more essential oil compounds selected from the group consisting of limonene. At col. 2, lines 15-17, Losa discloses capsules as a feed premix. The Office considers the claimed propanediol mononitrate that is orally administered as a powderous formulation to include the powder in the capsules of Losa. At col. 2, line 60 to col. 3, lines 27, Losa discloses its formulations as feed premixes (“feed additives”) wherein the powderous formulation comprises from 0.1 to 20 wt% essential oils, based on the total weight of the powderous formulation. The Office considers the claimed powderous formulation comprising the active ingredients in an amount of 1% to 20%, by weight, based on the total weight of the feed additive formulation to include the feed premix of Losa. At col. 3, lines 24-31, Losa discloses compositions as feed additive comprising its active essential oil compounds including 100% limonene suitably administered per day in an amount from 0.01-50 mg/Kg bodyweight of the animal per day. And, in Example 1 at col. 4, lines 35-40 and Table 1, Losa discloses methane reduction in the digestion of ruminants.
Calculating the amount of limonene used in Losa, and using a molecular weight (MW) for limonene of about 136 g/mol (page 2 of the instant specification) gives an amount of 0.0055 to 40 g limonene/ animal/ day disclosed in Losa at col. 2, lines 24-31, and equals from 0.0055 g/136 g/mol to 40g/136 g/mol or 4.04 x 10-5 to about 0.29 mol or about 0.00004 to about 0.29 mol limonene/ animal/ day. The cows in disclosed in Example 18 of Duval at [0157] weigh from 550 to 800 Kg. Accordingly, Losa at col. 2, lines 24-31 a discloses using or administering to cows from a minimum of 550 Kg x 0.01 mg/Kg or 5.5 mg to a maximum of 800 Kg x 50 mg/Kg or 40,000 mg or 40 g limonene per animal per day or 0.0055 to 40 g limonene/ animal/ day which the claimed 0.1 to 50 g limonene/ animal/ day in claim 9 overlaps and the claimed 0.2 to 2g limonene/animal/ day in claim 17 lies within. See MPEP 2144.05.I. The ordinary skilled artisan in Losa would have found it obvious in view of Losa to administer or use the claimed amount of limonene/ animal/ day because Losa discloses that the claimed amount of limonene provides desirable reduction in methane production in ruminants.
Farmer at page 4, lines 12-20 discloses methods for reducing greenhouse gas emissions comprising methane from livestock including (at page 2, lines 32-36) cattle by administering to the ruminant animals a composition of (at page 6, lines 14-22) 3-nitrooxy propanol or propanediol mononitrate and D-limonene as a terpene, including combinations thereof. Further, Farmer discloses powderous formulations of its compositions at p. 5, lines 1-2. While Farmer does not disclose an example of administering propanediol mononitrate and D-limonene together, Farmer discloses at page 4, lines 12-20 that administering such a combination of those compounds to a ruminant desirably reduces methane formation in digestion.
Before the effective filing date of the present invention, the ordinary skilled artisan would have found it obvious in view of Losa for Duval to use or administer the claimed amount of 0.05 to 100 g limonene/ animal/ day as in claim 7, to administer the claimed amount of from 0.1 to 50 g limonene/ animal/ day as its essential oil as in claim 9 and to administer the claimed 0.2 to 2g limonene/animal/ day as in claim 17. In addition, it would have been obvious in view of Losa for Duval to administer its composition in a feed premix comprising propanediol mononitrate in an amount of 1% to 20%, by weight, based on the total weight of the formulation; and, it would have been obvious in view of Losa for Duval to administer a feed additive formulation to an animal wherein the molar ratio of limonene to propanediol mononitrate is, respectively, between and from 100:1 and 1:1. Both references disclose administering essential oils to ruminants as feed additives or in feeds to reduce methane production in ruminant digestion containing the active ingredient in an amount sufficient to provide a dosage as claimed of active methane reducing feed additive ingredients including 0.05 to 100 g/day of essential oil as limonene and 0.5 to 2.5 g/day of PMDN per animal. The ordinary skilled artisan would have desired to use the limonene of Losa and the amounts of the claimed limonene as in Losa and PMDN as in Duval in its feed additive formulation to formulate the essential oil of Duval to help reduce methane production in ruminants as disclosed in Losa at col. 2, lines 24-31. Further, the ordinary skilled artisan in Duval would found it obvious to use the claimed molar ratio of limonene to propanediol mononitrate of between 100:1 and 1:1 as in claims 11 and 18 to reduce methane emissions because Losa at col. 2, line 60 to col. 3, line 27 discloses using the claimed amount of limonene to reduce methane production while Example 18 of Duval discloses 0.0041 to about 0.021 moles propanediol mononitrate to reduce methane production, or a molar ratio of limonene to propanediol mononitrate of from a maximum of 0.29 moles limonene: 0.021 minimum moles propanediol mononitrate or about 14:1 to a minimum of 0.00004 moles limonene: 0.0041 maximum moles of propanediol mononitrate or about 1:100, which the claimed molar ratio of between 100:1 and 1:1 overlaps. See MPEP 2144.05.I. Further, in Duval as modified by Losa the 0.0055 to 40 g limonene/ animal disclosed in Losa at col. 2, lines 24-31 when used as the essential oil in 18.9 kg of the dry feed in Example 18 of Duval equates to about 0.3 mg to about 2.1 g limonene per kg fry feed, which the claimed 5 mg to 5 g limonene per kg dry matter feed overlaps. See MPEP 2144.05.I.
Before the effective filing date of the present invention, the ordinary skilled artisan in Duval would have found it obvious in view of Losa to administer or use the claimed molar ratio of limonene to propanediol mononitrate and the claimed mass of limonene and of propanediol mononitrate per kg dry matter feed and amount limonene per kg dry matter of feed because Duval discloses that the claimed amount of propanediol mononitrate in moles and per kg of dry matter feed provides desirable reduction in methane production in ruminants and includes an essential oil, while Losa discloses that the claimed amount of the essential oil of Duval as limonene in the claimed amount per animal/ day, the claimed amount of PMDN by weight, based on the total weight of the feed additive formulation, and the claimed amount of PMDN and limonene per kg of dry matter feed provides a desired reduction in methane production from animal feed.
Further regarding claims 12 and 16, before the effective filing date of the present invention, the ordinary skilled artisan in Duval as modified by Losa would have found it obvious in view of Farmer to formulate its feed premix as a powderous formulation and administer it as a powderous formulation and for Duval to use D-limonene as its essential oil. All references disclose methods of reducing the production of methane emanating from the digestive activities of ruminants using essential oils in feed additives. The ordinary skilled artisan in Duval as modified by Losa would have desired to formulate a powderous formulation of its feed additive for shelf stability or use as a concentrate feed additive. Further, the ordinary skilled artisan in Duval would have desired to use the D-limonene of Farmer as its active essential oil because Farmer discloses that D-limonene provides a desirable methane reduction when fed with propanediol mononitrate to ruminants. Further, the use of Duval as modified by Farmer is substantially the same as the claimed use. Accordingly, absent a clear showing as to how the effect of the method of Duval at [0014], [0031] and [0039]-[0040] as modified by Losa at col. 2, lines 14-35 and col. 2, line 60 to col. 3, line 27 and Farmer at p. 5, lines 1-2 differs from that as claimed, the Office considers the use of propanediol mononitrate and D-limonene as in Duval as modified by Farmer at page 6, lines 14-21 to synergistically reduce methane reducing properties of the propanediol mononitrate in Duval as modified by Losa. See MPEP 2112.01.I.
Regarding instant claim 13, Duval at [0050] discloses the composition as a feed or feed additive that is a mineral premix, a vitamin premix or a bolus.
Response to Arguments
In view of the amendment dated July 01, 2026, the following rejections have been withdrawn as moot:
The rejections of claims 1-15 under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite because the claims 1-6 and 14-16 do not recite any affirmative method steps; and because claims 3, 4, 5, 6, 8, 9, 11 and 14-15 recite a broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation using “preferably”;
The rejections of claims 1 and 3-6 under 35 U.S.C. 103 as being unpatentable over US2014/0147529 A1 to Duval et al. in view of US 7,763,273 B2 to Losa;
The rejection of claim 2 under 35 U.S.C. 103 as being unpatentable over US2014/0147529 A1 to Duval et al. in view of US 7,763,273 B2 to Losa and WO2021/163148 A1 to Farmer et al.; and,
The rejections of claims 14-15 under 35 U.S.C. 103 as being unpatentable over US2014/0147529 A1 to Duval et al. in view of US 7,763,273 B2 to Losa and WO2021/163148 A1 to Farmer et al.
Regarding the positions taken in the remarks accompanying amendment dated July 01, 2026 (Reply), the Office has fully considered the positions taken and does not find the positions persuasive for the following reasons:
The position taken that the art of Duval and Losa do not disclose a method comprising orally administering the propanediol mononitrate as a powderous formulation, respectfully the Office does not rely on Duval or Losa for disclosing orally administering the propanediol mononitrate as a powderous formulation. The rejection relies on Farmer for this. However, Losa at col. 2, lines 15-17 discloses powder formulations that are placed in capsules.
Conclusion
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 ANDREW E MERRIAM whose telephone number is (571)272-0082. The examiner can normally be reached M-H 8:00A-5:30P and alternate Fridays 8:30A-5P.
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/ANDREW E MERRIAM/Examiner, Art Unit 1791
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