CTNF 18/719,447 CTNF 100136 DETAILED ACTION Notice of Pre-AIA or AIA Status 07-03-aia AIA 15-10-aia The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA. Claim Status Claims 1-10 were previously pending. The preliminary amendment filed 13 June 2024 amended claims 1-10. Therefore, claims 1-10 are pending and examined on the merits herein. Priority This application claims the following priority: PNG media_image1.png 105 659 media_image1.png Greyscale Claim Objections Claim 1 recites the following chemical compounds: methyl(2R* ,4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbo - nyl]amino]tetrahydrofuran-2-carboxylate (I); methyl(2R,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl] - amino]tetra - hydrofuran-2-carboxylate (Ia); and (2S,4S)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate (Ib). There are several inconsistencies between (I) and (Ia) including, but not limited to, a dash between carbo-nyl and tetra-hydrofuran. Examiner attempted to highlight each inconsistency above. These are assumed to be typographical errors and appropriate correction is required. Claim Rejections - 35 USC § 112(b) 07-30-02 AIA 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. The following is a quotation of 35 U.S.C. 112 (pre-AIA), second paragraph: The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention. 07-34-01 Claims 1-10 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention. Independent claim 1 recites: “use of a stereoisomeric mixture of methyl(2R*,4R*)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4Hisoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate (I) , wherein the stereoisomeric mixture comprises: Methyl(2R,4R)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]-amino]tetrahydrofuran-2-carboxylate of formula (Ia) and methyl (2S,4S)-4-[[(5S)-3-(3,5-difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate of formula (Ib) . Additionally, dependent claims 6, 7, and 8 recite the limitation “the stereoisomeric mixture of formula (I) .” Conventionally, reference to a formula denotes a generic chemical structure or class of compounds. In the instant case, the compounds represented by formula (Ia) and formula (Ib) in claim 1 are single compounds, not formulas. Therefore, it is unclear what limitation the recitation of formula (Ia) and formula (Ib) is attempting to impose. Additionally, claims 6-8, which are dependent upon claim 1, recite “…the stereoisomeric mixture of formula (I)…” However, claim 1 does not recite a formula (I), only formulas (Ia) and (Ib). Therefore, claims 6-8 are rejected for lack of antecedent basis. Because claims 2-5 and 9-10 depend directly or indirectly from a rejected base claim, the indefiniteness of claims 1 and 6-8 renders the scope of these claims also unclear and therefore, claims 2-5 and 9-10 are included in this rejection. Claim Rejections - 35 USC § 103 07-20-aia AIA 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. 07-23-aia AIA 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. 07-20-02-aia AIA 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. 07-21-aia AIA Claim s 1, 5-10 are rejected under 35 U.S.C. 103 as being unpatentable over Peters (WO 2018/228985 A1*; published 20 December 2018) . *Of note: the English equivalent of WO 2018/228985 A1 – US PGPub No. 2021/0292312 A1 – was relied upon for this rejection. See MPEP 901.05(d). In addition, the patent family which includes WO 2018/228985 A1 and US 2021/0292312 A1 names the same Applicant and Inventors as the current application. However, WO 2018/228985 A1 was published more than one year before the date in which the current application claims priority (10 December 2021). Peters discloses herbicidally active 3-phenylisoxazoline-5-carboximides of tetrahydro and dihydrofuran carboxylic acids and esters. Specifically: Regarding claim 1 , Peters discloses preparation of methyl-cis-4[[(5s)-3-(3,5 difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate ([0556]), which may be present as a stereoisomer ([0055]). The prior art compound “methyl-cis-4[[(5s)-3- (3,5 difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate” appears to correspond to the same relative stereochemical form as applicant’s “methyl(2R*,4R*)-4[[(5s)-3-(3,5 difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate (hereinafter ‘claimed compound I’),” since both compounds describe the cis relationship of the substituents at the 2- and 4- positions of the tetrahydrofuran ring. In addition, Peters discloses examples I-11 and I-12 as individual enantiomers of the 2,4-cis configuration of example I-10, which was methyl-cis-4[[(5s)-3-(3,5 difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate ([0152] - Table 1 on p. 11 and [0055]). This corresponds to the claimed stereoisomers methyl(2R,4R)-4[[(5s)-3-(3,5 difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate (hereinafter ‘claimed compound Ia’) and methyl(2S,4S)-4[[(5s)-3-(3,5 difluorophenyl)-5-vinyl-4H-isoxazole-5-carbonyl]amino]tetrahydrofuran-2-carboxylate (hereinafter ‘claimed compound Ib’). Therefore, Peters discloses claimed compounds I, Ia, and Ib. With respect to the claimed method of sprout inhibition, Peters’ disclosed invention provides a method for controlling unwanted plants or for regulating the growth of plants, preferably in plant crops, in which one or more compound(s) of the invention is/are applied to the plants ([0161]). The compounds in Peters may be applied to vegetative propagules such as tubers or shoot parts with buds ([0161]). In addition, depending on the plant species, the inventive treatment disclosed by Peters results in synergistic effects including better storage stability ([0420]). Sprouting in harvest crops represents a form of plant growth arising from meristematic tissue, involving cell division and metabolic activation. Peters teaches the regulation of plant growth affecting such processes. Therefore, one of ordinary skill in the art would have been motivated to use the compounds disclosed in Peters to inhibit sprouting with a reasonable expectation of success. The claimed method represents a predictable use of a prior art compound according to their established function as plant growth modulating agents. Inhibition of sprouting is a specific instance of plant growth inhibition. Regarding claim 5 , Peters discloses the composition further comprises a formulation auxiliary such as a safener (Peters’ claims 14, 16, and 17 on p. 73) or other active compounds such as insecticides, herbicides, and fungicides ([0196]). Combining plant-active compounds with additional agricultural active ingredients represents a routine formulation strategy in the art. Regarding claim 6 , Peters discloses applying the compounds of the invention prior to sowing, prior to emergence, or after emergence ([0161]). Application of plant growth modulating compounds to plant material, including harvested crops, represents a predictable use of such compounds. Regarding claim 7 , though Peters does not teach a range of 0.01 to 2000 g of the stereoisomeric mixture of claimed compound I, Peters teaches that “the following text will, for the sake of simplicity, always mention compounds of formula (I), even though this is understood as meaning not only the pure compounds, but also, if appropriate, mixtures with various amounts of isomeric compounds” ([0056]). Furthermore, “[w]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation” (see MPEP 2144.05(II)). The amount of compound applied constitutes a result-effective variable, as it is well-known that the efficacy of plant-active compounds depends on the dosage and optimization of such ranges would have been routine to one of ordinary skill. As such, an artisan having ordinary skill in the art would have been motivated to modify the amount of stereoisomeric mixture of formula (I) encompassed by the range of instant claim 7, to predictably arrive at a range that provides the most stable, safe, and effective sprout inhibition product. The optimization of known amounts for known active agents is considered well within the competence level of an artisan of ordinary skill in the pharmaceutical sciences; it has been held that the selection of optimal parameters, such as amounts of active agents, to achieve a beneficial effect, is within the skill in the art of an ordinary artisan. See In re Boesch, 205 USPT 215 (CCPA 1980) and MPEP 2144.05. Regarding claim 8 , Peters discloses a method of controlling one or more unwanted plants comprises applying an effective amount of at least one compound of formula (I) or a herbicidal composition thereof to the plants (Peters’ claims 1 and 18 on p. 73). The motivation to do so is discussed above in claim 1. Regarding claims 9 and 10 , Peters discloses plants which can be treated in accordance with the invention include potatoes and onions ( Alliaceae spp.) ([0417]). The difference between the applied reference and the claimed invention is that the applied references may not teach the instantly claimed method with particularity so as to amount to anticipation. See MPEP 2131 “[t]he identical invention must be shown in as complete detail as is contained in the ... claim.” Richardson v. Suzuki Motor Co. , 868 F.2d 1226, 1236, 9 USPQ2d 1913, 1920 (Fed. Cir. 1989). The elements must be arranged as required by the claim, but this is not an ipsissimis verbis test, i.e., identity of terminology is not required. In re Bond, 910 F.2d 831, 15 USPQ2d 1566 (Fed. Cir. 1990). Peters discloses various embodiments of compounds used in the regulation of plant growth, particularly in potato and onion crops, which would require the skilled artisan pick and choose which compound to use in the application. However, the applied reference discloses the elements of the claimed method with sufficient guidance, particularity, and with a reasonable expectation of success for the skilled artisan, that the invention would be prima facie obvious to one of ordinary skill in the art. As discussed above, Peters discloses all the claim limitations of instant claims 1 and 5-10 with a reasonable expectation of success. It would have been obvious to use the compounds of Peters in a sprout inhibition treatment because Peters finds success in a method for controlling unwanted plants or for regulating the growth of plants using such compounds. Therefore, Peters renders claims 1 and 5-10 obvious . 07-22-aia AIA Claim s 2 and 3 are rejected under 35 U.S.C. 103 as being unpatentable over Peters as applied to claim s 1, 5-10 above, and further in view of Riggle (US Pat. No. 5,811,372; date of patent: 22 September 1998) . The disclosures of Peters are discussed above. Peters teaches a method for controlling unwanted plants or for regulating the growth of plants, preferably in plant crops, in which currently claimed compounds Ia, Ib, or a combination thereof are applied to the plants. In addition, Peters teaches specific plant growth regulators as possible mixing partners of which maleic hydrazide is disclosed as a growth regulating mixing partner ([0194-0195]). Peters differs from instant claims 2 and 3 in that Peters does not explicitly teach maleic hydrazide as a sprout inhibitor or availability of chlorpropham as a mixing partner. However, as discussed below, Riggle cures this deficiency. Riggle discloses a method of controlling sprout formation in tubers comprising application of chlorpropham (CIPC) and carvone (abstract). Regarding claim 2 , Riggle discloses maleic hydrazide and CIPC are typical synthetically-derived sprout inhibitors used in the art to inhibit sprout formation in potatoes (col. 1, lines 35-39). Regarding claim 3 , Riggle discloses sprout inhibition of benzothiazole and carvone, alone, is marginal (col. 3, lines 23-25). However, a combination of benzothiazole and CIPC or carvone and CIPC result in enhanced sprout inhibiting capabilities (col. 3, lines 17-23). It would have been obvious to one of ordinary skill before the effective filing date of the claimed invention to substitute what was disclosed by Peters as plant growth regulators that are possible mixing partners with an additional sprout inhibitor, such as CIPC taught by Riggle. One would be motivated to do so for the following reasons: Peters discloses maleic hydrazide as a possible plant growth regulator mixing partner. Riggle discloses maleic hydrazide is known in the art as a sprout growth inhibitor and further teaches CIPC as another compound used to control sprout formation in potatoes. Therefore, substituting the maleic hydrazide in Peters with CIPC taught by Riggle would be well within the grasp of one of ordinary skill. The claimed subject matter therefore represents a simple substitution of one known element (maleic hydrazide) with another (CIPC). Both are disclosed by Riggle as suitable sprout inhibitors, so results of the substitution would have been predictable. Therefore, Peters, in view of Riggle, renders claims 2 and 3 obvious . 07-22-aia AIA Claim 4 is rejected under 35 U.S.C. 103 as being unpatentable over Peters as applied to claim s 1, 5-10 above, and further in view of Riggle (US Pat. No. 5,811,372; date of patent: 22 September 1998) and Frazier (“Organic and Alternative Methods for Potato Sprout Control in Storage,” published: September 2004) . The disclosures of Peters and Riggle are discussed above. Peters teaches a method for controlling unwanted plants or for regulating the growth of plants, preferably in plant crops, in which currently claimed compounds Ia, Ib, or a combination thereof are applied to the plants. In addition, Peters teaches plant growth regulators as possible mixing partners which include maleic hydrazide. Riggle discloses that maleic hydrazide is a known sprout inhibitor in the art. In addition, Riggle discloses use of essential oils, such as carvone, as potential sprout inhibitors. Riggle and Peters differ from claim 4 in that neither reference explicitly discloses use of peppermint oil extract as a sprout inhibitor. However, as discussed below, Frazier cures this deficiency. Frazier teaches peppermint oils and spearmint oils applied in storage can be used as effective sprout suppressants (p. 2). Regarding claim 4, Frazier teaches both peppermint and spearmint oils are equally effective sprout suppressants, but peppermint oil caused fewer problems with culinary and palatability concerns (p. 2). Therefore, Peters teaches plant growth modulating compounds and combination formulations, in particular with a known sprout inhibitor maleic hydrazide. Riggle teaches known sprout inhibitors in the art include maleic hydrazine, CIPC, and other natural compounds such as carvone. Riggle further discloses carvone is an essential oil of caraway seeds and has been promoted as a natural sprout suppressant for potatoes, but is less effective alone compared to a combination of carvone and CIPC. Additionally, it is known in the art that carvone is present in high concentrations in spearmint oil. Finally, Frazier teaches both peppermint and spearmint oil as equally effective natural sprout suppressants for potatoes, but peppermint oil is preferred. It would be obvious to one of ordinary skill before the effective filing date of the claimed invention to substitute the sprout inhibitor maleic hydrazide in Peters with a combination of carvone and CIPC taught by Riggle as an optimal combination for sprout inhibition. Further, one of ordinary skill would be motivated to substitute the carvone in Riggle with peppermint oil because Frazier teaches that while both spearmint oil and peppermint oil are equally effective sprout inhibitors, peppermint oil is preferable for culinary and palatability reasons. The claimed subject matter in claim 4 therefore represents the substitution of known elements performing their known functions, yielding nothing more than predictable results, and is therefore unpatentable under 35 U.S.C. 103 over Peters and in further view of Riggle and Frazier . Conclusion 12-151-07 AIA 07-97 12-51-07 Claim s 1-10 are rejected. No claim is allowed. Communication Any inquiry concerning this communication or earlier communications from the examiner should be directed to Julia A. Rossi whose telephone number is (571)272-0138. The examiner can normally be reached M-Th 7:30-5:30 (MST). Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Robert A. Wax can be reached at (571)272-0623. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300. Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /JULIA A ROSSI/Examiner, Art Unit 1615 /Robert A Wax/Supervisory Patent Examiner, Art Unit 1615 Application/Control Number: 18/719,447 Page 2 Art Unit: 1615 Application/Control Number: 18/719,447 Page 3 Art Unit: 1615 Application/Control Number: 18/719,447 Page 4 Art Unit: 1615 Application/Control Number: 18/719,447 Page 5 Art Unit: 1615 Application/Control Number: 18/719,447 Page 6 Art Unit: 1615 Application/Control Number: 18/719,447 Page 7 Art Unit: 1615 Application/Control Number: 18/719,447 Page 8 Art Unit: 1615 Application/Control Number: 18/719,447 Page 9 Art Unit: 1615 Application/Control Number: 18/719,447 Page 10 Art Unit: 1615 Application/Control Number: 18/719,447 Page 11 Art Unit: 1615 Application/Control Number: 18/719,447 Page 12 Art Unit: 1615 Application/Control Number: 18/719,447 Page 13 Art Unit: 1615
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