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 .
Claim Status
Claims 1-30 were filed on 11/16/2022 and are currently pending.
Priority
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See filing receipt dated 12/6/2022.
Information Disclosure Statement
The listing of references in the specification is not a proper information disclosure statement. 37 CFR 1.98(b) requires a list of all patents, publications, or other information submitted for consideration by the Office, and MPEP § 609.04(a) states, "the list may not be incorporated into the specification but must be submitted in a separate paper." Therefore, unless the references have been cited by the examiner on form PTO-892, they may have not been considered.
Claim Interpretation
Claim 16 recites “the method of claim 12, wherein the unsaturated fatty carboxyl derivative is derived from a natural oil”.
Claim 18 recites that a “plant-based impurity” is removed from the derivative of claim 16.
Both of these limitations are interpreted as product-by-process limitations. Therefore, they are only considered to the extent that they further limit the structure of the unsaturated fatty carboxyl derivative in claim 16 and the plant-based impurity of claim 18.
Claim Objections
Claims 1-30 are objected to because of the following informalities:
Claims 1-30 are objected to because the text is blurry and difficult to read, especially with respect to structures.
In line 2 of claim 18 the first instance of the word “prior” (after the word derivative) should be deleted.
Appropriate correction is required.
Claim Rejections - 35 USC § 112(b)
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.
Claim 22 is 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.
Claim 22, which depends from claim 21, which depends from claim 1, is rejected for being indefinite because the variable “z” is not defined in any of the claims.
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.
Claim(s) 1-18 and 21-30 is/are rejected under 35 U.S.C. 103 as being unpatentable over Mehdi (US 2017/0137365, published on 5/18/2017) in view of Johns (US 2018/0361371, published on 12/20/2018).
Mehdi teaches the production of fatty olefin derivatives via olefin metathesis. Mehdi teaches contacting an olefin of formula (I):
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with a metathesis reaction partner according to formula (II):
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in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product. Mehdi teaches that R1 is H, C1-18 alkyl or C2-18 alkenyl; that R2 is –(CH2)xOR2a or –(CH2)COOR2b, wherein R2a is an alcohol protecting group and R2b is C1-8 alkyl; x is 1 to 18; and y and z are independently 0 to 17. See [0006-0016]. Thus, when R1 is not hydrogen, compounds (I) and (II) can be understood to comprise internal olefins.
The metathesis catalyst comprises tungsten, molybdenum, or ruthenium, wherein ruthenium is a group 8 transition metal. See [0017]. Medhi also teaches that the catalysts include Z-selective catalysts, which would selectively produce the Z-olefin metathesis product. See [0031]. The scope of the catalysts is disclosed in [0209-0340]. Specific ruthenium catalysts are discussed in [0322-0340], including both Z-selective and E-selective catalysts.
Medhi teaches a preferred embodiment wherein the metathesis reaction partner (II) is a compound of formula (IIa):
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and wherein the metathesis product (III) is a compound of formula (IIIa):
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, wherein R1, R2a, x and z are the same as above. See [0018-0020]. Mehdi teaches that preferred protecting groups R2a include silyl, tert-butyl, benzyl, and acetyl, preferably acetyl. See [0101-0104]. When R2a is acetyl, the compounds of formula (IIa) and (IIIa) are both acylated alkenol, wherein compound (IIIa) corresponds to the instantly claimed fatty olefin metathesis product. Thus, the genus of compound (IIa) overlaps with the genus of instant formula (III) in claims 6 and 24-28 and compound (IIIa) overlaps with the genus of compounds of instant formula (I) in claims 6 and 24-28, wherein R1 is C1 alkyl. Further the compounds of formula (IV) in claims 6 and 24-28, said compounds correspond to the olefin of Formula (I) of Mehdi wherein instant R3 = R1 of Medhi and is not hydrogen. Also see MPEP 2144.08.
The embodiment is further depicted in Scheme 1 on p. 7:
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. If PG is acetyl and R is C8H17, then Scheme 1 would correspond to an embodiment of instant claim 1 wherein the olefin metathesis reaction partner is an alkylenyl alcohol (allyl alcohol or homologs thereof); the internal olefin is the acylated alkenol; and the fatty olefin metathesis product is the cross-metathesized acylated alkenol (middle product). When the internal olefin is cis/Z oriented then the acylated alkenol product will retain the cis/Z orientation. See Table 1 in [0100]. Medhi further teaches embodiments of selectively produced cis/Z oriented metathesis products (IV) and (IVc) in [0133-0142].
Medhi further teaches that the cis/Z oriented metathesis products are used to produce pheromones which can be used to control the behavior and/or growth of insects in various environments. See abstract and [0001-0005, 0031, and 0363-0385].
Johns teaches ruthenium-based olefin metathesis catalysts of the following Formula (I)
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See abstract and [0086-0110]. Exemplary embodiments are shown in claim 9 and [0111]. Johns teaches the following catalyst of formula C849z, which corresponds to the first catalyst in instant claim 9:
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. Thus, the catalyst also meets the limitations formula (V) of instant claims 7 and 8, wherein M is ruthenium; X and Y are S; Z is O; subscript m is 2; subscript n is 0 such that Rb is absent; each Ra is Cl (halogen); Rc, Rd, Re, Rf, and Rg are hydrogen; R14 is iso-propyl and the other R14 and R15 are taken together to form a bond; and R12 and R13 are both 2,6-di-iso-propyl phenyl. Additionally, the compounds of instant formula (V) of claim 7 also overlap in scope with the compounds of Formula (I) of Johns, when one R14 and R15 are taken together to form a bond. Also see MPEP 2144.08.
In examples 19-21 in [0210-0215], Johns teaches that the catalyst C849z is a Z selective catalyst (claim 2) in self-metathesis reactions. In example 20, when >99% cis/Z methyl-9-octadecenoate (MO) was subjected to self-metathesis conditions in the presence of C849z, the products (DE and 9C18) exhibited excellent stereo retention (>99%). However, when >97% trans/E MO was subjected to the same conditions no corresponding E products were detected. See Table 5. Therefore, the C849z catalyst is very selective toward the Z-isomer.
Catalyst C849z was further investigated in example 21 using mixtures of cis/trans (Z/E) MO according to the following equation:
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.
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and summarized in Table 6.
These results are consistent with those of example 20, which show that the metathesis products (DE and 9C18) have a higher Z/E ratio than the starting olefin (MO), including products which are >99% Z (claims 3 and 4). As example 20 of Johns is a self-metathesis reaction, the MO would qualify as both the instantly claimed olefin metathesis reaction partner and internal olefin. The fatty olefin metathesis product is an enoate (DE). Thus, entries 2-3 of Table 6 would appear to meet the limitations of claim 5. Also see MPEP 2144.05. The enoate (alkene-CO2Me) of Johns is analogous to the acylated alkenol (alkene-OC(O)-Me) of Medhi. Both are carboxylic ester groups, wherein the order is transposed. Further, their interchangeability is also suggested by Medhi in [0013] with respect to variable R2 of the metathesis reaction partner.
Medhi does not explicitly teach that the olefin metathesis partner and the olefin metathesis reaction partner comprise a mixture of Z olefins and E olefins in a starting Z:E ratio, wherein the product Z:E ratio is higher than the starting Z:E ratio.
It would have been prima facie obvious for a person of ordinary skill to combine the teachings of Medhi and Johns to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person of ordinary skill would have been motivated to use the Z-selective catalysts of Johns in the process of Medhi because Johns has shown that catalyst C849z is extremely selective to the formation of Z olefins and Medhi is directed toward the synthesis of Z olefins for use in synthesizing pheromones. Therefore, regardless of the Z/E purity level of the starting olefin metathesis reaction partner desired, the Z/E purity level of the product will predictably increase because the catalyst of Johns does not undergo metathesis with E/trans olefins. This also provides a more desirable and economical process because any E/trans contaminants contained within the reactants does not have to be removed prior to reaction to selectively obtain the desired Z/cis olefin, such as those encompassed with the E concentration in claim 5. Thus, lower quality reagents, which are also traditionally less expensive, can be efficiently utilized to produce high quality products. Also see MPEP 2143(I)(B) and MPEP 2144.05.
Regarding claims 10 and 11, Medhi teaches that alkenols of the following formula (Vc):
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can be reacted with an acylating agent, including acetic anhydride, to produce compounds of formula (VIc):
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. See [0114-0119]. Compound (VIc) is analogous to metathesis reaction partner (IIa)
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, wherein R2a is preferably methyl. See [0101-0104]. Therefore, though not explicitly taught by Medhi, it would be prima facie obvious to obtain metathesis reaction partner (IIa) using the well-known acylation procedure set forth in [0114-0119], wherein acetic anhydride will predictably produce a compound wherein R2a is methyl.
Regarding claims 12-15, Medhi teaches the reduction of ester compound (IIIb) to produce alkenol (Vb):
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, wherein R2b is a C1-8 alkyl See [0026-0027, 0013, and 0156-0160]. Therefore, though not explicitly taught by Medhi, it would be prima facie obvious to obtain the alkenol used to produce acylated metathesis reaction partner (IIa) from the corresponding ester using the well-known reduction procedure set forth in [0026-0027 and 0156-0160]. Medhi further teaches that the reduction can be carried out under any suitable homogeneous or heterogeneous conditions, including hydrogenolysis with heterogeneous catalysts or the use of bis(2-methoxyethyl) aluminum hydride. Medhi further teaches that solvents, including those that are basic, can also be included. See [0156-0160].
Regarding claims 16-18, Medhi teaches that the olefin metathesis reaction partner can be derived from a natural oil, including those of claim 17. See [0071-0072]. Medhi further teaches that the substrates may contain contaminants, which would also include plant-based impurities. See [0073]. Paragraph [0072] also indicates that the natural oil derivatives can be obtained through distillation, which would necessarily remove impurities from the desired oil derivative.
Regarding claims 21-23, Medhi teaches that the olefin is of formula (I): R1 can be a C1-18 alkyl and z is 0 to 17:
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and when R1 is a C1-18 alkyl and Z is 0 to 17, this corresponds to the claimed internal olefin of formula (VIa). Medhi explicitly teaches the metathesis reactions between two terminal alkenes to produce a Z selective internal alkene in the examples. See [0386-0404]. Medhi further generally teaches that the process can be extended to reactions between two internal alkenes. See [0075-0098] and discussion in claim 1 above.
Johns teaches that the Z selective Ru metathesis catalyst C849z can be used in reactions between terminal olefins, internal olefins, and mixtures thereof to produce self-metathesis and cross-metathesis products. See [0013-0032 and examples 16-31]. Johns teaches that the internal olefins can be Z-olefins of Formula (1):
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or E-olefins of Formula (2):
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and that the terminal olefin can be of Formula (3):
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. See [0114-0135]. When Z-selective catalysts, such as C849z, are employed, then the metathesis product is of the formula (4):
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. See [0144-0148]. Therefore, the genus of olefins (1), (2) and (3) of Johns encompass instant terminal olefins of formula (IVb) and the genus of olefin (4) of Johns encompasses the internal olefin of instant formula (VIa).
Johns and Medhi further teach examples wherein terminal olefins of instant formula (IVb) and (Via) are employed in metathesis reactions, including those between unfunctionalized alkenes to produce unfunctionalized Z selective olefins, analogous to those of instant formula (VIa). See examples of each reference. Also see MPEP 2144.08.
Therefore, though neither reference explicitly teaches using a preliminary metathesis reaction with a terminal alkene to form the internal olefin, it would be prima facie obvious to obtain an internal alkene by metathesis in accordance with the known procedures in Medhi and Johns for producing Z-selective catalysts. The person of ordinary skill would already be in possession of a Z-selective ruthenium metathesis catalyst to facilitate the reaction between the claimed internal olefin and olefin metathesis reaction partner, therefore using the same conditions to prepare the internal olefin would be efficient and predictable.
Further regarding claims 24-28, as discussed in the rejection of claims 1 and 6 above, all of these embodiments fall within the scope of the reactants of formula (III) and (IV) and products (I) of Mehdi. Additionally, Medhi teaches that products of claims 26-28 are pheromone products and/or intermediates which can be obtained using the disclosed method. See [0363], including Table 7. Instant (Z)-octadec-9-en-1-yl acetate is recited as (Z)-9-octadenyl acetate in the third col. on p. 84; regioisomers of (Z)-tetradecen-1-yl acetate in the second col of the Table on p. 82; and homologs of (Z)-icos-11-en-1-yl acetate in the third col. on p. 84. Therefore, the skilled artisan would be motivated to predictably prepare the claimed compounds using the combined method in order to obtain bioactive pheromones with a reasonable expectation of success.
Regarding claims 29 and 30, Medhi teaches that reaction materials containing contaminants can be treated with one or more conditioning agents to mitigate potentially adverse effects of one or more contaminants, including alumina and triethyl aluminum. See [0357].
Claim(s) 19-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Mehdi (US 2017/0137365, published on 5/18/2017) in view of Johns (US 2018/0361371, published on 12/20/2018) as applied to claims 1-18 and 21-30 above, and further in view of Abraham (US 2009/0264672, published on 10/22/2009) and Pederson (US 2002/0022741, published on 2/21/2002).
Medhi teaches that one of the intended uses of the acylated alkenol metathesis products obtained from the disclosed process is to convert said compounds to the corresponding alkenals of formulas (VIIa) and (VIIc). See [0114-0132]. Table 7 in [0363] further lists several pheromone products which include alkenals. For example, (E)-2-decenal in col. 1 (the third entry in the Table).
The combination of Mehdi and Johns does not explicitly teach that alkenals or alkenal acetals can be employed directly in the metathesis reaction to arrive at the instantly claimed process.
Abraham is directed toward methods of making organic compounds by metathesis. Abraham teaches that functionalized alkene intermediates can be self-metathesized or cross-metathesized with a second functionalized alkene to produce a desired organic compound or a precursor thereof. Abraham specifically mentions that the desired organic compounds can contain aldehyde functional groups. See abstract. Abraham teaches that the second functionalized alkene can comprise acetals, including 3-butenal diethyl acetal. See [0301]. Abraham teaches the following cross-metathesis reaction between methyl-9-dedecenoate (compound comprising an internal olefin which is analogous to instant compound (IV) in claim 19) with 3-butenal diethyl acetal (a compound analogous to instant compound (VII) in claim 19, wherein R1 is ethyl) in example 10 in [0345-0347]:
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. The product of Abraham is analogous to the compound of instant formula (VI) in claim 19. Abraham teaches tha the catalyst used in the transformation, C827, is a ruthenium-based metathesis catalyst. See final compound in col. 1 of p. 19.
Pederson is directed toward the metathesis synthesis of pheromones or their components. See abstract. In Figure 38, Pederson teaches the following metathesis reaction between 5-hexenal diethyl acetal and 11-docosene:
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. 5-Hexenal diethyl acetal is analogous to a compound of instant formula (VII), wherein R1 is ethyl; 11-docosene is a compound of instant formula (IV) wherein R3 is a C10 alkyl and z is 9; and the product is analogous to a compound of instant formula (VI).
Fig. 39 of Pederson is directed toward an alternative synthesis of the same product from different alkenes:
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; and Fig. 40 of Pederson teaches a metathesis reaction between an alkenyl acetal and a vinyl borate:
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. The product of the initial metathesis reaction is carried forward and the acetal group is converted with acid to produce the final alkenal (claim 20). Also see [0240-0245] regarding the experimental procedures for Fig. 38-40.
It would have been prima facie obvious to combine the teachings of Medhi, Johns, Abraham, and Pederson to arrive at the instantly claimed process with a reasonable expectation of success before the effective filing date of the claimed invention. A person or ordinary skill would have been motivated to substitute the alkenal acetal metathesis reaction partner of instant formula (VII) for the acylated alkenol metathesis reaction partner of instant formula (III) of claim 6 of the combined process of Medhi and Johns because Abraham and Pederson teach that alkenal acetals can be used in Ru-catalyzed metathesis reactions to predictably directly produce alkenal acetal products, which can be converted to alkenals. Medhi further teaches that one of the intended uses of the acylated alkenol metathesis products obtained from the disclosed process is to convert said compounds to the corresponding alkenals of formulas (VIIa) and (VIIc) and lists several pheromone products which include alkenals. Therefore, combining the teachings of Medhi, Johns, Abraham, and Pederson will predictably produce an alternative process for obtaining the alkenal pheromone derivatives in Medhi. Also see MPEP 2143(I)(B).
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AMY C BONAPARTE whose telephone number is (571)272-7307. The examiner can normally be reached 11-7.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/AMY C BONAPARTE/Primary Examiner, Art Unit 1692