Prosecution Insights
Last updated: April 19, 2026
Application No. 18/453,549

COMPOUND, PREPARATION METHOD THEREFOR AND APPLICATION OF COMPOUND IN PREPARATION OF BICYCLOPYRONE INTERMEDIATE

Non-Final OA §101§102§103§112
Filed
Aug 22, 2023
Examiner
ROMERO, KRISTEN WANG
Art Unit
1624
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Shandong Weifang Rainbow Chemical Co. Ltd.
OA Round
1 (Non-Final)
88%
Grant Probability
Favorable
1-2
OA Rounds
3y 6m
To Grant
99%
With Interview

Examiner Intelligence

Grants 88% — above average
88%
Career Allow Rate
15 granted / 17 resolved
+28.2% vs TC avg
Moderate +12% lift
Without
With
+12.5%
Interview Lift
resolved cases with interview
Typical timeline
3y 6m
Avg Prosecution
42 currently pending
Career history
59
Total Applications
across all art units

Statute-Specific Performance

§101
6.0%
-34.0% vs TC avg
§103
18.2%
-21.8% vs TC avg
§102
20.4%
-19.6% vs TC avg
§112
38.9%
-1.1% vs TC avg
Black line = Tech Center average estimate • Based on career data from 17 resolved cases

Office Action

§101 §102 §103 §112
DETAILED ACTION The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA. Status of the Claims Claim s 21-47 are pending. Claims 1-20 are cancelled. Status of Priority The present application is a continuation of International patent application PCT/CN2023/098992 , filed on June 7, 2023 . This application also claims the benefits of foreign priority to CN202210637542.4 , filed on June 8, 2022 . Election/Restriction Examiner previously required a restriction of the claimed inventions. The requirement filed on December 10 , 2025 is now withdrawn and the prosecution will continue with a first non-final office action on the merits addressing pending claims 21-47 . Specification - Disclosure The specification has not been checked to the extent necessary to determine the presence of all possible minor errors. Applicant’s cooperation is requested in correcting any errors of which applicant may become aware in the specification . Claim Objections Claim s 23-25, 28-32, 36, 39, 40, 42 , 44, and 45 are objected to because of the following informalities: C laim 23: For clarity on what compound is actually being made, claim 23 should read: “… in the presence of a base, making a compound as shown in the formula III and/or enol tautomer thereof is subjected to a substitution reaction…” For consistency, claim 23 should also read: “… and i n the formulas Ia , Ib , Ic , II and III, X is the same.” Claim 24: For consistency, claim 24 should read: “ … the substitution reaction is performed in an organic solvent, wherein the organic solvent comprises…” Claim 25: For clarity on what compound is actually being made, claim 25 should read: “…1) in the presence of a base, making a compound as shown in the formula II I and/or enol tautomer thereof is subjected to a substitution reaction…” and should also read “ … 2) in the presence of an ammonium salt and/or ammonia, making a product of the substitution reaction in step 1) is subjected to a ring-closure reaction…” Claims 28-32: For clarity, “an compound” should read “ a compound” The “an compound” phrase appears multiple times throughout claims 28-32. Make sure all “an compound” phrases are replaced with “ a compound” Claim 36: For clarity on what compound is actually being made and which compound is actually used for subsequent reaction , claim 36 should read: “(1) making a material containing a salt of 2-methoxyethanol is reacted with…” and also “ ( 2) making the reaction material obtained in step (1) is subjected to a substitution reaction…” as well as “(3)… to the reaction material obtained in step (2)… Claims 39 and 40: For clarity on what compound is actually being used for subsequent reaction, claim 39 and 40 should read: “… wherein the reaction material obtained in step (2)…” Claim 42: For clarity, claim 42 should read: “ … S2: reacting the material containing a salt of 2-methoxyethanol reacted with ethyl 4-chloroacetoacetate…” Claim 44: For consistency, “…wherein in step (3), a reaction temperature for 2-methoxyethanol and a base is 40 o C – 180 o C …” should read “… wherein the reaction of 2-methoxyethanol under the action of a base occurs at a temperature of 40 o C – 180 o C …” Claim 45: For consistency, “wherein in step (3)” should read “wherein in step S1 ” Appropriate correction is required. Examiner has identified a number of claim objections . Applicant’s cooperation is requested in correcting any errors of which applicant may become aware in the claims. Claim 34 is objected to under 37 CFR 1.75 as being a substantial duplicate of claim 33 . Claim 34 is directed towards a method for the preparation of bicyclopyrone from the product prepared by the method according to claim 23 which is the same as the compound according to claim 21. Claim 33 is directed towards a method for the preparation of bicyclopyrone from the compound according to claim 21. Thus, claim 34 is a substantial duplicate of claim 33. When two claims in an application are duplicates or else are so close in content that they both cover the same thing, despite a slight difference in wording, it is proper after allowing one claim to object to the other as being a substantial duplicate of the allowed claim. See MPEP § 608.01(m). 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 appl icant regards as his invention. Claim s 22-29, 31-35, 37, 38, 41, 43, and 44 -47 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. Regarding claims 22, 24, 26 , 38, 41, 44, and 45 the phrase "optionally," renders the claim indefinite because it is unclear whether the narrower limitation(s) following the phrase are part of the claimed invention. Specifically, there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims . Claim 23 recites “…and [i]n the formulas … II and III…” Claim 23 is dependent on claim 21 which does not mention a formula II. Thus, there is insufficient antecedent basis for this limitation in the claim . Regarding claim 24: A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claim 24 recites the broad recitation “wherein the organic base comprises one or more of sodium alkoxide and potassium alkoxide”, and the claim also recites “the organic base comprises one or more of sodium methoxide, sodium ethoxide, potassium tert-butoxide, potassium methoxide, potassium ethoxide, sodium hexamethyldisilazane and lithium hexamethyldisilazane ” which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims. Claim 25 recites the limitation " wherein in the formula II and the formula III, X is the same.” Claim 25 does not depend on a claim that defines what X is. Claim 25 also does not itself define X. Thus, it is unclear what substituents X can represent and the claim is considered indefinite. For this office action, Examiner will assume that the “X” variable recited in claim 25 has the same definition as the “X” variable recited in claim 21. Claim 26 recites “…wherein the condition for the ring-closure reaction.” Claim 26 is dependent on claim 25 which does not mention a condition for the ring-closure reaction. Thus, t here is insufficient antecedent basis for this limitation in the claim. Claim 26 can be amended to recite “…wherein a condition for the ring-closure reaction…” Claim 27 recites “…wherein if X is Cl...” Claim 27 is dependent on claim 25 which does not mention that X can be Cl. As stated above, claim 25 does not define X at all. Thus, there is insufficient antecedent basis for this limitation in the claim. Claims 28 and 29 recites “…wherein if X is -O(CH 2 ) 2 OCH 3 ...” Claim s 28 and 29 are ultimately dependent on claim 25 which does not mention that X can be -O(CH 2 ) 2 OCH 3 . As stated above, claim 25 does not define X at all. Thus, there is insufficient antecedent basis for this limitation in the claim. Claim s 3 1 and 32 recite “[a] composition, comprising a reaction material prepared by the method according to” claim 23 or claim 25, respectively, and further recites a series of conditional limitations based on the identify of X (i.e., if X is H, Cl, or -O(CH 2 ) 2 OCH 3 , then the composition comprises…). However, the claim language is unclear as to whether the recited composition must include the “reaction material” in all embodiments, or whether the conditional limitations define separate compositions that may or may not include the reaction material. For example, the limitation “if X is H, the composition comprises a compound having the structural formula as shown in formula Ia , formula Ib , and/or formula Ic ” does not clearly indicate whether the recited compounds of formula Ia , Ib , and/or Ic is required to be present in addition to the “reaction material” (which Examiner interprets as encompassing a bicyclopyrone intermediate or side products), or whether it defines an alternative composition independent of the reaction material. Claims 33-35 are framed as a method for the preparation of bicyclopyrone , yet no operative steps are provided. According to MPEP § 2173.05(q): “ Attempts to claim a process without setting forth any steps involved in the process generally raises an issue of indefiniteness under 35 U.S.C. 112(b ) or pre-AIA 35 U.S.C. 112 second paragraph .” Hence, claim s 33-35 are rendered indefinite. Regarding claim 37: A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claim 37 recites the broad recitation “the substitution reaction is -15 o C to 30 o C ”, and the claim also recites “or 0 o C – 10 o C ” which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims . Claim 38 recites “… a molar ratio of a compound as shown in the formula Ib-3 to the ammonium salt…” Claim 38 is dependent on claim 36 which does not disclose a formula Ib-3. Thus, there is insufficient antecedent basis for this limitation in the claim. Regarding claim 41: A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claim 41 recites the broad recitation “the organic base comprises one or more of sodium alkoxide and potassium alkoxide”, and the claim also recites “the organic base comprises one or more of sodium methoxide, sodium ethoxide, potassium tert-butoxide, potassium methoxide and potassium ethoxide” which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claim s. Regarding claim 43: A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claim 43 recites the broad recitation “the organic base comprises one or more of sodium alkoxide and potassium alkoxide”, and the claim also recites “the organic base comprises one or more of sodium methoxide, sodium ethoxide, potassium tert-butoxide, potassium methoxide and potassium ethoxide” which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claim s. Claim 46 recites “step S2.” Claim 46 is dependent on claim 36 which does not disclose a “step S2.” Thus, there is insufficient antecedent basis for this limitation in the claim. Claim 47 recites “step (1).” Claim 47 is dependent on claim 42 which does not disclose a “step (1).” Thus, there is insufficient antecedent basis for this limitation in the claim. Claim Rejections - 35 USC § 101 35 U.S.C. 101 reads as follows: Whoever invents or discovers any new and useful process, machine, manufacture, or composition of matter, or any new and useful improvement thereof, may obtain a patent therefor, subject to the conditions and requirements of this title. Claim s 33-35 are rejected under 35 U.S.C. 101 because the claimed recitation of a use, without setting forth any steps involved in the process, results in an improper definition of a process, i.e., results in a claim which is not a proper process claim under 35 U.S.C. 101. See for example Ex parte Dunki , 153 USPQ 678 ( Bd.App . 1967) and Clinical Products, Ltd. v. Brenner, 255 F. Supp. 131, 149 USPQ 475 (D.D.C. 1966). Note on 35 USC § 102 and § 103 Rejections 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. Claim Rejections - 35 USC § 102 The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action: A person shall be entitled to a patent unless – (a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale , or otherwise available to the public before the effective filing date of the claimed invention. (a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention. Claims 21-26, 30-35, 42, 43 , and 47 are rejected under 35 U.S.C. 10 2(a)(1) as being anticipated by the following prior art as discussed below: Rejection Part 1: Claim s 21- 24 and 30-32 are rejected under 35 U.S.C. 102 (a)(1) as being anticipated by : Zanatta et al. ( Zanatta ) ( Zanatta , N. et al. Synthesis 1999 , 5, 765-768. ) Zanatta discloses how to synthesize a compound 3b . The reaction scheme to synthesize compound 3b and the structure of the compound are provided below: ( Zanatta , bottom of pg. 765). Compound 3b of Zanatta corresponds to a compound of instant formula Ib (i.e., wherein X = H ) which can tautomerize to form the compounds of instant formulas ( Ia ) and ( Ic ). Hence, claims 21-24 are anticipated by Zanatta . The reaction scheme disclosed in Zanatta (and partially printed above) show that the product yield of compound 3b is between 56-61%. In other words, the crude product is a composition comprising a compound 3b (i.e., a compound of instant formula Ib ). Hence, claims 30-32 are also anticipated by Zanatta . Rejection Part 2: Claims 25 and 26 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by : Fisher et al . (Fisher) (WO2006059103A2; published June 8, 2006) Fisher teaches the preparation of ethyl 2-(chloromethyl)-6-(trifluoromethyl)nicotinate: (see pg. 31 of Fisher) which anticipates instant claims 25 and 26. Rejection Part 3: Claims 33-35 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by : Edmunds et al. (Edmunds) ( WO01/94339A1 ; published December 13, 2001 ). Edmunds teaches how to prepare bicyclopyrone (i.e., 4-Hydroxy-3-[2-(2-methoxyethoxymethyl)-6-trifluoromethylpyridine-3-carbonyl]-bicyclo[3.2.1]oct-3-en-2-one ) as summarized below: (see Edmunds, examples H1 to H3; Examiner also thanks Applicant for providing the reaction scheme above in the instant specification. It is a very helpful visual of examples H1 to H3 disclosed by Edmunds.) Applicant asserts in the instant specification that the preparation of bicyclopyrone disclosed by Edmunds involves substantial side reactions that ultimately produces impurities and result s in reduced yields of bicyclopyrone intermediate(s) (see pg. 2, paragraph right below reaction scheme) and that the present invention aims to improve bicyclopyrone intermediate yield while minimizing such side reactions (abstract) . However, claims 33-35 do not include any limitations directed to reaction efficiency, bicyclopyrone yield, or suppression of side reactions. Rather, claims 33-35 merely recite: a method for the preparation of bicyclopyrone from the compound according to claim 21 or a method for the preparation of bicyclopyrone from the product prepared by the method according to claim 23 or 25. Since the preparation of bicyclopyrone disclosed by Edmunds also produces the same intermediates and ultimately yields bicyclopyrone , the prior art also satisfies the requirements of the claimed methods. Hence, Edmunds anticipates claims 33-35 Rejection Part 4 : Claims 42 , 43 , and 47 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by : Frank-Foltyn et al. (Frank-Foltyn) (EP3130589A1; published February 15, 2017). Frank-Foltyn teaches how to synthesize ethyl 4-(2-methoxyethoxy)-3-oxobutanoate (i.e., the compound of instant formula (III-a) which comprises the following steps (pg. 16, para. 0089) : React 2-methoxyethanol with sodium hydride (i.e., a base). To the reaction mixture recited in (1), add ethyl 4-chloro-3-oxobutanoate (i.e., same as ethyl 4-chloroacetoacetate) that is dissolved in THF The product obtained is the compound of instant formula (III-a) which can tautomerize to form the compound of instant formula (III-b) (reads on instant claim 47) Hence, claims 42 , 43 , and 47 are anticipated by Frank-Foltyn. 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. 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 21-26, 30-3 8 , and 40- 47 are rejected under 35 U.S.C. 103 as being unpatentable over the prior art discussed below: Rejection Part 1: The teachings of : Zanatta as they apply to claims 21-24 and 30-32 ; Fisher as they apply to claims 25 and 26 ; Edmunds as they apply to claims 33-35 ; Frank-Foltyn as they apply to claims 42 , 43 , and 47 are as discussed in “ Rejection Part 1 , ” “ Rejection Part 2 , ” “ Rejection Part 3 , ” and “ Rejection Part 4 , ” respectively, of section “ Claim Rejections - 35 USC § 102 ” discussed above and incorporated herein. Given that the claimed invention is anticipated by the prior art, a POSITA would have found it obvious to reproduce the subject matter disclosed. Rejection Part 2: Claims 36-38, 40, 41, 4 6, and 47 are rejected under 35 U.S.C. 103 as being unpatentable over : Jackson et al. (Jackson) (WO2004078729A1; published September 16, 2004) , Fisher et al. (Fisher) (WO2006059103A2; published June 8, 2006) Jackson teaches how to prepare the compound of instant formula IIC: (see Jackson, pg. 18, example P2) wherein the ring-closure step is conducted in the presence of trifluoroacetic acid (TFA). Note: reactant (1) of Jackson as shown in the reaction scheme above can be made according to the procedure disclosed on pg. 16, para. 0089 of Frank-Foltyn (EP3130589A1; published February 15, 2017). Jackson does not explicitly teach performing the ring-closure step in the presence of ammonium acetate (NH 4 OAc) and acetic acid ( AcOH ). Fisher is relied upon for this disclosure. Fisher teaches the preparation of ethyl 2-(chloromethyl)-6-(trifluoromethyl)nicotinate: (see pg. 31 of Fisher). Even though Fisher does not explicitly disclose the formation of an enamine intermediate (similar to the enamine intermediate disclosed in Jackson) before being further reacted with , a POSITA understands that in a solution comprising NH 4 OAc and AcOH , there still exists NH 3 . The NH 3 can then react with the β-keto ester to form an enamine intermediate (See scheme 1 of: Brandt, C. et al. Synthesis 2004 , 10, 1557-1559.) and t he enamine intermediate can subsequently react with to undergo a ring-closure reaction to form a substituted pyridine compound , all in the presence of NH 4 OAc and AcOH . Although the pyridine compound formed in Fisher differs from the pyridine compound disclosed in Jackson by one substituent, Fisher demonstrates that NH 4 OAc/ AcOH is capable of promoting pyridine ring formation across substrates bearing different functional groups (see examples on pg. 29-34). Thus, one of ordinary skill in the art would have found it prima facie obvious before the effective filing date of the claimed invention to substitute TFA used in Jackson with NH 4 OAc/ AcOH taught by Fisher as both reagents are known to provide acidic conditions suitable for promoting a ring-closure reaction to produce a pyridine compound. Although the instant specification states that the one-pot synthesis of the pyridine compound (reported in Fisher) in the presence of only acetic acid, ammonium acetate, and the two reactants results in a reaction mixture that is low in yield of the pyridine compound and is difficult to purify (see instant specification, pg. 3, 1 st paragraph), this would not have discouraged a person of ordinary skill in the art from using NH 4 OAc/ AcOH in the method of Jackson. Note: Jackson performs the reaction in a stepwise manner in which an enamine intermediate is first formed when reacts with NH 3 . Then, the enamine intermediate reacts with and subsequently, ring-closure step occurs in the presence of TFA. In contrast, Fisher discloses the synthesis of the pyridine compound under continuous conditions (i.e., in the presence of only NH 4 OAc/ AcOH and the reactants ) for the formation of the enamine intermediate and the pyridine product. A person of ordinary skill in the art would have recognized that the timing and sequence of reagent exposure can significantly affect reaction efficiency, yield, and selectivity. Accordingly, it would have been obvious to evaluate the NH 4 OAc/ AcOH system taught by Fisher under the stepwise conditions of Jackson, wherein enamine intermediate formation is formed prior to cyclization with a reasonable expectation that such modification could provide acceptable results. Furthermore, the modification required to arrive at the claimed invention involves a limited and straightforward variation of a short, two-step synthetic sequence, namely substituted one known cyclization medium (i.e., TFA) with another (i.e., NH 4 OAc/ AcOH ) while maintaining the overall reaction framework. A person of ordinary skill in the art would have routinely considered such variations in reagent selection, reaction sequencing, and reaction temperature determination as part of standard optimization of known synthetic methods. Where the number of variables is small and the alternatives are known, such optimization constitutes no more than the application of routine skill in the art, with a reasonable expectation of success. Thus, the preparation of the compound of instant formula IIC as disclosed in instant claims 36-38, 40, 41, 46, and 47 are rendered obvious. Rejection Part 3 : Claims 44 and 45 are rejected under 35 U.S.C. 103 as being unpatentable over : Frank-Foltyn et al. (Frank-Foltyn) (EP3130589A1; published February 15, 2017) and Ashenhurst , J. “How to use a pKa Table” Master Organic Chemistry . https://www.masterorganicchemistry.com/2010/09/29/how-to-use-a-pka-table/ (Accessed March 23, 2026). Frank-Foltyn teaches the deprotonation of 2-methoxyethanol with sodium hydride (i.e., a base) on pg. 16, para. 0089 . Frank-Foltyn does not teach how to deprotonate 2-methoxyethanol with a base that is one or more selected from the group consisting of sodium ethoxide, sodium methoxide, potassium methoxide and potassium ethoxide. Ashenhurst teaches how to use a pKa table to select a base that can be used to deprotonate an alcohol. Based off of the general organic chemistry topics taught in Ashenhurst , a POSITA would understand how to use a pKa table to select an alkoxide base that can deprotonate an alcohol such as 2-methoxyethanol (section 4-“Using pKa values and the Principle of Acid-Base Mediocrity to Predict Acid-Base Reactions” of Ashenhurst provides an example of sodium methoxide deprotonating ethanol). Therefore, one of ordinary skill in the art would have found it prima facie obvious before the effective filing date of the claimed invention to select an alkoxide base (such as sodium ethoxide, sodium methoxide, potassium methoxide, and potassium ethoxide) that is suitable for deprotonating alcohols including 2-methoxyethanol, based on established pKa relationships. Accordingly, it would have been obvious to substitute sodium hydride with one of these known alkoxide bases to achieve the same deprotonation, as such substitution represents the use of a known base for its established function with reasonable expectation of success. Furthermore, selection of reaction conditions, including temperature would have been within the routine skill of the art. Alkoxide bases are commonly employed in their corresponding alcohol solvents such that conducting the reaction at temperatures consistent with the boiling point of the corresponding alcohol solvent represents routine optimization of reaction conditions and does not render the claimed invention nonobvious. Hence, claims 44 and 45 are rendered obvious. Conclusion Claims 21- 38 and 40- 47 are rejected . Claim 39 is objected to . Any inquiry concerning this communication or earlier communications from the examiner should be directed to FILLIN "Examiner name" \* MERGEFORMAT KRISTEN ROMERO whose telephone number is FILLIN "Phone number" \* MERGEFORMAT (571)272-6478 . The examiner can normally be reached FILLIN "Work Schedule?" \* MERGEFORMAT M-F 9:30 AM - 6:00 PM ET . 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, FILLIN "SPE Name?" \* MERGEFORMAT JEFFREY H. MURRAY can be reached at FILLIN "SPE Phone?" \* MERGEFORMAT (571) 272-9023 . 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. /KRISTEN W ROMERO/ Examiner, Art Unit 1624 /JEFFREY H MURRAY/ Supervisory Patent Examiner, Art Unit 1624
Read full office action

Prosecution Timeline

Aug 22, 2023
Application Filed
Mar 23, 2026
Non-Final Rejection — §101, §102, §103 (current)

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Prosecution Projections

1-2
Expected OA Rounds
88%
Grant Probability
99%
With Interview (+12.5%)
3y 6m
Median Time to Grant
Low
PTA Risk
Based on 17 resolved cases by this examiner. Grant probability derived from career allow rate.

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