Prosecution Insights
Last updated: July 17, 2026
Application No. 18/555,027

PRODUCTION METHOD FOR PRODUCING DIMETHANOL COMPOUND HAVING NORBORNANE SKELETON

Non-Final OA §103§DP
Filed
Oct 12, 2023
Priority
Apr 12, 2021 — JP 2021-067275 +1 more
Examiner
BAHTA, MEDHANIT W
Art Unit
1692
Tech Center
1600 — Biotechnology & Organic Chemistry
Assignee
Mitsubishi Gas Chemical Company, Inc.
OA Round
1 (Non-Final)
80%
Grant Probability
Favorable
1-2
OA Rounds
0m
Est. Remaining
99%
With Interview

Examiner Intelligence

Grants 80% — above average
80%
Career Allowance Rate
629 granted / 782 resolved
+20.4% vs TC avg
Strong +29% interview lift
Without
With
+28.8%
Interview Lift
resolved cases with interview
Fast prosecutor
2y 0m
Avg Prosecution
37 currently pending
Career history
826
Total Applications
across all art units

Statute-Specific Performance

§101
0.7%
-39.3% vs TC avg
§103
57.5%
+17.5% vs TC avg
§102
10.9%
-29.1% vs TC avg
§112
11.3%
-28.7% vs TC avg
Black line = Tech Center average estimate • Based on career data from 782 resolved cases

Office Action

§103 §DP
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 . Status of the Claims The preliminary amendment filed on 10/12/2023 has been entered. Claims 3-7 and 9 have been amended. Thus claims 1-11 are currently pending and are under examination. Claim Objections Claim 11 is objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening 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. Claims 1 and 4-5 are rejected under 35 U.S.C. 103 as being unpatentable over Patent application publication number US2017/0088504A1 (US’504; cited in IDS 10/12/2023). Regarding claim 1, US’504 exemplifies a method for producing compound (3b) (specie of claimed formula (1)) by subjecting a mixed liquid comprising compound (1b) (specie of claimed formula (2)) and toluene as a solvent to a hydrogenation reduction in the presence of Cu-Zn-Al catalyst having hydrogenation ability ([103]-[109] and [116]). PNG media_image1.png 90 262 media_image1.png Greyscale PNG media_image2.png 95 286 media_image2.png Greyscale (1b) (3b) The reference fails to exemplify the claimed solvent that is a linear or branched secondary alcohol or tertiary alcohol. However, in a non-exemplified embodiment, the reference teaches the reduction reaction can use a solvent such as aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, alcohols, etc. and among them, preferred are alicyclic hydrocarbons, aromatic hydrocarbons and alcohols, with specific examples including cyclohexane, toluene, xylene, methanol, ethanol, 1-propanol and cyclohexanol ([61], the underlined solvents read on the claimed solvent). Regarding claims 4-5, US’504 teaches that the reaction produces (3b) as the main product at a yield of 96% ([103] and [116]). Thus, any by-products formed would be present at a yield of 4%. Furthermore, because US’504 teaches that compound (3b) is prepared by the same method as claimed, i.e. where the starting material, the catalyst, the solvent and the reaction process meet the claimed limitations, there is a prima facie case of anticipation or obviousness in the reference for the content of the claimed by-products to be 0.5% by mass or less. It would thus have been prima facie obvious to the skilled artisan before the effective filing date of the instant invention to conduct a method for producing a target compound represented by the formula (1), the production method comprising: a step (A) of subjecting a mixed liquid comprising a starting compound represented by the formula (2) and a solvent to a hydrogenation reduction in a presence of a catalyst having hydrogenation ability, wherein the solvent is a linear or branched secondary alcohol or tertiary alcohol in view of the teachings of US’504. Claim 2 is rejected under 35 U.S.C. 103 as being unpatentable over Patent application publication number US2017/0088504A1 (US’504; cited in IDS 10/12/2023) as applied to claims 1 and 4-5 above, and further in view of Patent application publication number US2013/0225875A1 (US’875). The teachings of US’504 have been set forth above. Regarding claim 2, as set forth earlier, US’504 teaches the hydrogenation reaction can be conducted using alcohol as a solvent, and further lists methanol, ethanol and 1-propanol, wherein these solvents have a boiling point less than 100 °C. The reference however fails to specifically provide listing of alcohols with a boiling point of 100 to 230 °C as in claim 2. In the same field of endeavor, US’875 teaches a liquid phase hydrogenation reaction of carbonyl groups in the presence of at least one catalyst comprising Cu, Mn, Al, Cr, Zn, Ba and/or Zr, wherein the combination of Cu, Al and Zn would result to the same catalyst as disclosed in US’504. US’875 further teaches that a solvent is used in the reaction, and is selected from the group consisting of a C1-C6 branched or unbranched alcohol such as methanol, ethanol, isopropanol, n-propanol, iso-butanol, 1,6-hexanediol, ethyleneglycol or propyleneglycol. Propyleneglycol is a branched secondary alcohol with a boiling point of 188.2 °C. Furthermore, some solvents that are encompassed by the generic C1-C6 branched or unbranched alcohol of US’875 would also have boiling points that fall under the claimed range of 100 to 230 °C. In accordance to MPEP § 2143, the Supreme Court in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) identified a number of rationales to support a conclusion of obviousness which are consistent with the proper “functional approach” to the determination of obviousness as laid down in Graham and discussed circumstances in which a patent might be determined to be obvious. In this case, at least prong (B) simple substitution of one known element for another to obtain predictable results applies. US’504 suggests the use of generic alcohol as the solvent that can be used in the catalytic hydrogenation reaction of carbonyl groups of compound (1b) and further lists linear alcohols with boiling point of less than 100 °C. US’875 teaches alcohol solvents in the catalytic hydrogenation process of carbonyl groups, and wherein some of the solvents possess a boiling point falling within the claimed range of 100 to 230 °C. Thus, a simple substitution of the solvent of US’504 with that of US’875 would yield nothing more than the predictable hydrogenated product compound (3b). It would thus have been prima facie obvious to the skilled artisan before the effective filing date of the instant invention to conduct a method for producing a target compound represented by the formula (1), the production method comprising: a step (A) of subjecting a mixed liquid comprising a starting compound represented by the formula (2) and a solvent to a hydrogenation reduction in a presence of a catalyst having hydrogenation ability, wherein the solvent is a linear or branched secondary alcohol or tertiary alcohol and wherein a boiling point of the solvent is 100 to 230° C in view of the teachings of US’504 and US’875. Claims 2-3 and 6 are rejected under 35 U.S.C. 103 as being unpatentable over Patent application publication number US2017/0088504A1 (US’504; cited in IDS 10/12/2023) as applied to claims 1 and 4-5 above, and further in view of International publication WO2020213389A1 (WO’389; cited in IDS 02/05/2025 and machine translation attached herewith). The teachings of US’504 have been set forth above. Regarding claims 2-3 and 6, it has been discussed above that US’504 teaches the hydrogenation reaction can be conducted using alcohol as a solvent, and further lists methanol, ethanol and 1-propanol, wherein these solvents have a boiling point less than 100 °C. The reference however fails to specifically provide listing of alcohols with a boiling point of 100 to 230 °C as in claim 2. US’504 also fails to teach alcohols encompassed by the formula (a) as in claim 3 and the solvent of claim 6. However, the deficiencies are cured by WO’389. Regarding claims 2 and 6, in the same field of endeavor, WO’389 teaches a liquid phase hydrogenation reaction of a compound (1-2) with carbonyl groups in the presence of a catalyst to obtain a hydrogenated product (1) ([0049]) of the translation). PNG media_image3.png 134 499 media_image3.png Greyscale WO’389 further teaches that a solvent is used in the reaction, and includes aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and alcohols, with alicyclic hydrocarbons, aromatic hydrocarbons, or alcohols being preferred among these, specifically, cyclohexane, toluene, xylene, methanol, ethanol, 1-propanol, 2-octanol, and the like are preferred ([0053] of the translation). WO’389 exemplifies production of (1)-1 by the hydrogenation reaction of (1-2)-1 in the presence of Cu-Zn-Al catalyst (same catalyst as disclosed in US’504) and in the presence of 2-octanol ([0109] of the translation), with a boiling point of 178.5 °C. PNG media_image4.png 114 480 media_image4.png Greyscale Regarding claim 3, 2-octanol is a specie of the solvent of formula (a), in which R1 is H, R2 is CH3 and R3 is C6H13. In accordance to MPEP § 2143, the Supreme Court in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) identified a number of rationales to support a conclusion of obviousness which are consistent with the proper “functional approach” to the determination of obviousness as laid down in Graham and discussed circumstances in which a patent might be determined to be obvious. In this case, at least prong (B) simple substitution of one known element for another to obtain predictable results applies. US’504 suggests the use of generic alcohol as the solvent that can be used in the catalytic hydrogenation reaction of carbonyl groups of compound (1b) and further lists linear alcohols with boiling point of less than 100 °C. WO’389 teaches alcohol solvents in the catalytic hydrogenation process of carbonyl groups, and wherein 2-octanol reads on the solvent of claims 2-3 and 6. Thus, a simple substitution of the solvent of US’504 with that of WO’389 would yield nothing more than the predictable hydrogenated product compound (3b). It would thus have been prima facie obvious to the skilled artisan before the effective filing date of the instant invention to conduct a method for producing a target compound represented by the formula (1), the production method comprising: a step (A) of subjecting a mixed liquid comprising a starting compound represented by the formula (2) and a solvent to a hydrogenation reduction in a presence of a catalyst having hydrogenation ability, wherein the solvent is a linear or branched secondary alcohol or tertiary alcohol; wherein a boiling point of the solvent is 100 to 230° C, wherein the solvent is formula (a) and wherein the solvent is 2-octanol and/or tetrahydrolinalool in view of the teachings of US’504 and WO’389. Claims 7-10 are rejected under 35 U.S.C. 103 as being unpatentable over Patent application publication number US2017/0088504A1 (US’504; cited in IDS 10/12/2023) as applied to claims 1 and 4-5 above, and further in view of Patent number US7,084,312B1 (US’312). The teachings of US’504 have been set forth above. Regarding claim 7, the reference fails to teach that the catalyst is activated prior to conducting the hydrogenation reaction. The deficiency is cured by US’312. US’312 teaches hydrogenation of an organic compound with carbonyl groups comprising contacting the compound in the presence of hydrogen with a catalyst that comprises Cu, Zn and Al (same catalyst as disclosed in US’504) (col. 2, lines 3-27). The reference further teaches that the catalyst is activated prior to the hydrogenation reaction by a reduction oven or after installation in the hydrogenation reactor under hydrogenation pressure (col. 5, lines 60-67). Catalyst activation is a known process that increases and maximizes the performance of a catalyst and as such, a skilled artisan would have been motivated to use the methods of US’312 in the process of US’504 with a reasonable expectation of success in activating Cu-Zn-Al prior to conducting the hydrogenation process and in optimizing the hydrogenation process. Regarding claims 8-9, US’504 that teaches the hydrogenation reaction of the compound that is encompassed by the claimed compound of formula (2), also further discloses that the reaction is conducted at pressure of 1 to 20 MPa ([0060]). Regarding claim 10, the linear alcohol solvent has already been addressed earlier, in which US’504 teaches solvents such as methanol, ethanol and 1-propanol. It would thus have been prima facie obvious to the skilled artisan before the effective filing date of the instant invention to conduct a method for producing a target compound represented by the formula (1), the production method comprising: a step (A) of subjecting a mixed liquid comprising a starting compound represented by the formula (2) and a solvent to a hydrogenation reduction in a presence of a catalyst having hydrogenation ability, wherein the solvent is a linear or branched secondary alcohol or tertiary alcohol and wherein, in the step (A), the catalyst is activated at a first temperature and a first pressure, and after the activation, the starting compound is hydrogenated at a second temperature and a second pressure in view of the teachings of US’504 and US’312. Allowable Subject Matter The subject matter of claim 11 is free of prior art. The closest prior art reference, Patent application publication number US2017/0088504A1 (US’504; cited in IDS 10/12/2023), and its teachings have been set forth above. As set forth earlier, it has been discussed that US’504 teaches that the hydrogenation reaction can be conducted using alcohol as a solvent, and further lists methanol, ethanol and 1-propanol. However, the reference fails to teach tetrahydrolinalool as the solvent of the hydrogenation reaction. Furthermore, while the reference teaches a generic use of alcohol solvent, there is no guidance or motivation to specifically use tetrahydrolinalool out of all known alcohol solvents that encompass a vast number of species. In view of the foregoing, claim 11 is deemed novel and unobvious. Double Patenting The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969). A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b). The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13. The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer. Claims 1, 4-5 and 7-9 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-6 of copending Application No. 18,555,052 (reference application). Claims 1, 4-5 and 7-9 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-6 of copending Application No. 18,555,052 in view of Patent application publication number US2017/0088504A1 (US’504; cited in IDS 10/12/2023). The claims at issue are drawn to a method for producing a target compound represented by the formula (1), the production method comprising: a step (A) of subjecting a mixed liquid comprising a starting compound represented by the formula (2) and a solvent to a hydrogenation reduction in a presence of a catalyst having hydrogenation ability. While the copending recite that the hydrogenation reaction is conducted in the presence of a solvent, the claims fail to recite that the solvent is a linear or branched secondary alcohol or tertiary alcohol. The deficiency is cured by US’504. US’504 exemplifies a method for producing compound (3b) (specie of claimed formula (1)) by subjecting a mixed liquid comprising compound (1b) (specie of claimed formula (2)) and toluene as a solvent to a hydrogenation reduction in the presence of Cu-Zn-Al catalyst having hydrogenation ability ([103]-[109] and [116]). PNG media_image1.png 90 262 media_image1.png Greyscale PNG media_image2.png 95 286 media_image2.png Greyscale (1b) (3b) The reference further teaches in a non-exemplified embodiment that the hydrogenation reaction can also be conducted in a solvent such as aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, alcohols, etc. and among them, preferred are alicyclic hydrocarbons, aromatic hydrocarbons and alcohols, with specific examples including cyclohexane, toluene, xylene, methanol, ethanol, 1-propanol and cyclohexanol ([61], the underlined solvents read on the claimed solvent). Thus, a skilled artisan would have been motivated in using the solvent of US’504, including the linear alcohols in the process of copending method and would have a reasonable expectation of success in arriving at the instantly claimed method. It would thus have been prima facie obvious to the skilled artisan before the effective filing date of the instant invention to conduct a method for producing a target compound represented by the formula (1), the production method comprising: a step (A) of subjecting a mixed liquid comprising a starting compound represented by the formula (2) and a solvent to a hydrogenation reduction in a presence of a catalyst having hydrogenation ability, wherein the solvent is a linear or branched secondary alcohol or tertiary alcohol in view of the copending claims and the teachings of US’504. This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented. Claim 2 is provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-6 of copending Application No. 18,555,052 in view of Patent application publication number US2017/0088504A1 (US’504; cited in IDS 10/12/2023) and further in view of Patent application publication number US2013/0225875A1 (US’875). The teachings of copending claims in combination of US’504 have been set forth above. Regarding claim 2, it has already been discussed that US’504 teaches the hydrogenation reaction can be conducted using alcohol as a solvent, and further lists methanol, ethanol and 1-propanol, wherein these solvents have a boiling point less than 100 °C. However, the combination of the copending claims and US’504 fails to specifically provide listing of alcohols with a boiling point of 100 to 230 °C as in claim 2. In the same field of endeavor, US’875 teaches a liquid phase hydrogenation reaction of carbonyl groups in the presence of at least one catalyst comprising Cu, Mn, Al, Cr, Zn, Ba and/or Zr, wherein the combination of Cu, Al and Zn would result to the same catalyst as disclosed in US’504. US’875 further teaches that a solvent is used in the reaction, and is selected from the group consisting of a C1-C6 branched or unbranched alcohol such as methanol, ethanol, isopropanol, n-propanol, iso-butanol, 1,6-hexanediol, ethyleneglycol or propyleneglycol. Propyleneglycol is a branched secondary alcohol with a boiling point of 188.2 °C. Furthermore, some solvents that are encompassed by the generic C1-C6 branched or unbranched alcohol of US’875 would also have boiling points that fall under the claimed range of 100 to 230 °C. In accordance to MPEP § 2143, the Supreme Court in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) identified a number of rationales to support a conclusion of obviousness which are consistent with the proper “functional approach” to the determination of obviousness as laid down in Graham and discussed circumstances in which a patent might be determined to be obvious. In this case, at least prong (B) simple substitution of one known element for another to obtain predictable results applies. US’504 suggests the use of generic alcohol as the solvent that can be used in the catalytic hydrogenation reaction of carbonyl groups of compound (1b) and further lists linear alcohols with boiling point of less than 100 °C. US’875 teaches alcohol solvents in the catalytic hydrogenation process of carbonyl groups, and wherein some of the solvents possess a boiling point falling within the claimed range of 100 to 230 °C. Thus, a simple substitution of the solvent of US’504 with that of US’875 and combining with the method of copending claim would yield nothing more than the predictable hydrogenated product. It would thus have been prima facie obvious to the skilled artisan before the effective filing date of the instant invention to conduct a method for producing a target compound represented by the formula (1), the production method comprising: a step (A) of subjecting a mixed liquid comprising a starting compound represented by the formula (2) and a solvent to a hydrogenation reduction in a presence of a catalyst having hydrogenation ability, wherein the solvent is a linear or branched secondary alcohol or tertiary alcohol and wherein a boiling point of the solvent is 100 to 230° C in view of the combination of copending claims, US’504 and US’875. This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented. Claim 2-3 and 6 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-6 of copending Application No. 18,555,052 in view of Patent application publication number US2017/0088504A1 (US’504; cited in IDS 10/12/2023) and further in view of International publication WO2020213389A1 (WO’389; cited in IDS 02/05/2025 and machine translation attached herewith). The teachings of copending claims in combination of US’504 have been set forth above. Regarding claims 2-3 and , it has already been discussed that US’504 teaches the hydrogenation reaction can be conducted using alcohol as a solvent, and further lists methanol, ethanol and 1-propanol, wherein these solvents have a boiling point less than 100 °C. However, the combination of the copending claims and US’504 fails to specifically provide listing of alcohols with a boiling point of 100 to 230 °C as in claim 2. The combination of the copending claims and US’504 also fails to teach alcohols encompassed by the formula (a) as in claim 3 and the solvent of claim 6. However, the deficiencies are cured by WO’389. Regarding claims 2 and 6, in the same field of endeavor, WO’389 teaches a liquid phase hydrogenation reaction of a compound (1-2) with carbonyl groups in the presence of a catalyst to obtain a hydrogenated product (1) ([0049]) of the translation). PNG media_image3.png 134 499 media_image3.png Greyscale WO’389 further teaches that a solvent is used in the reaction, and includes aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and alcohols, with alicyclic hydrocarbons, aromatic hydrocarbons, or alcohols being preferred among these, specifically, cyclohexane, toluene, xylene, methanol, ethanol, 1-propanol, 2-octanol, and the like are preferred ([0053] of the translation). WO’389 exemplifies production of (1)-1 by the hydrogenation reaction of (1-2)-1 in the presence of Cu-Zn-Al catalyst (same catalyst as disclosed in US’504) and in the presence of 2-octanol ([0109] of the translation), with a boiling point of 178.5 °C. PNG media_image4.png 114 480 media_image4.png Greyscale Regarding claim 3, 2-octanol is a specie of the solvent of formula (a), in which R1 is H, R2 is CH3 and R3 is C6H13. In accordance to MPEP § 2143, the Supreme Court in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) identified a number of rationales to support a conclusion of obviousness which are consistent with the proper “functional approach” to the determination of obviousness as laid down in Graham and discussed circumstances in which a patent might be determined to be obvious. In this case, at least prong (B) simple substitution of one known element for another to obtain predictable results applies. S’504 suggests the use of generic alcohol as the solvent that can be used in the catalytic hydrogenation reaction of carbonyl groups of compound (1b) and further lists linear alcohols with boiling point of less than 100 °C. WO’389 teaches alcohol solvents in the catalytic hydrogenation process of carbonyl groups, and wherein 2-octanol reads on the solvent of claims 2-3 and 6. Thus, a simple substitution of the solvent of US’504 with that of WO’389 and combining with the method of copending claims would yield nothing more than the predictable hydrogenated product. It would thus have been prima facie obvious to the skilled artisan before the effective filing date of the instant invention to conduct a method for producing a target compound represented by the formula (1), the production method comprising: a step (A) of subjecting a mixed liquid comprising a starting compound represented by the formula (2) and a solvent to a hydrogenation reduction in a presence of a catalyst having hydrogenation ability, wherein the solvent is a linear or branched secondary alcohol or tertiary alcohol and wherein a boiling point of the solvent is 100 to 230° C in view of the combination of copending claims, US’504 and WO’389. This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented. Conclusion Claims 1-10 are rejected and no claims are allowed. Any inquiry concerning this communication or earlier communications from the examiner should be directed to MEDHANIT W BAHTA whose telephone number is (571)270-7658. The examiner can normally be reached Monday-Friday 8am-5pm. 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, 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. 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. /MEDHANIT W BAHTA/ Primary Examiner, Art Unit 1692
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Prosecution Timeline

Oct 12, 2023
Application Filed
Jun 26, 2026
Non-Final Rejection mailed — §103, §DP (current)

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1-2
Expected OA Rounds
80%
Grant Probability
99%
With Interview (+28.8%)
2y 0m (~0m remaining)
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