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 .
This is a Non-Final Office Action.
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on January 6, 2026 has been entered.
Election/Restrictions
Applicant's election with traverse of Group I in the reply filed on May 22, 2025 is acknowledged. Group I, drawn to a method of making and/or isolating isoidide of formula (I), embraced by claims 1-9, 14, 15 and 19-22 was elected by Applicant.
Claims 1-13, 16 and 20-22 are pending and claims 1-9 and 20-22 are under examination. Claims 10-13 and 16 are withdrawn based on the restriction requirement.
Claim Objections
The objection of claims 1, 5, 8 and 9 because of the term “received” is withdrawn based on the amendments.
Claim 1 is objected to because of the following informalities: the phrase, “selected from the group consisting of” should be removed from step M4), prior to carboxylic acid anhydrides and carboxylic acids. There is only one group. Appropriate correction is required.
Claim Rejections - 35 USC § 112
The rejection of claim 19 under 35 U.S.C. 112, 4th paragraph, as being of improper dependent form is withdrawn based on the amendments.
The rejection of claims 14 and 15 under 35 U.S.C. 112, 4th paragraph, as being of improper dependent form is withdrawn based on the amendments.
Claim Rejections - 35 USC § 112
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.
Claims 4 and 9 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 pre-AIA the applicant regards as the invention.
Regarding claim 4, the phrase, “the mixture of compounds of formula II provided or prepared in step M3) comprises a mixture comprising or consisting of…” is vague. The term “comprises” followed by “a mixture comprising or consisting of” is confusing. The term comprising embraces the phrase consisting of, and only one comprising is needed.
The rejection may be overcome by stating, ““the mixture of compounds of formula II provided or prepared in step M3) comprise…”
With regards to claim 9, the phrase, “the mixture…obtained after separation in step M5) and/or one or more reaction products thereof” is vague. What are the other reaction products intended?
The rejection may be overcome by removing the phrase “and/or one or more reaction products thereof” from claim 9.
The following is a quotation of the fourth paragraph of 35 U.S.C. 112:
Subject to the [fifth paragraph of 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 8 is rejected under 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Said claims does not further limit claim 1 because the phase separation is required for the liquid-liquid extraction, and is therefore, broader than the liquid-liquid extraction. Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Claims 14 and 15 are rejected under 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Said claims do not further limit claim 1. Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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 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 § 103
The following is a quotation of 35 U.S.C. 103(a) which forms the basis for all obviousness rejections set forth in this Office action:
(a) A patent may not be obtained though the invention is not identically disclosed or described as set forth in section 102 of this title, if the differences between the subject matter sought to be patented and the prior art are such that the subject matter as a whole would have been obvious at the time the invention was made to a person having ordinary skill in the art to which said subject matter pertains. Patentability shall not be negatived by the manner in which the invention was made.
The factual inquiries set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied for establishing a background for determining obviousness under 35 U.S.C. 103(a) 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 under 35 U.S.C. 103(a), the examiner presumes that the subject matter of the various claims was commonly owned at the time any inventions covered therein were made absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and invention dates of each claim that was not commonly owned at the time a later invention was made in order for the examiner to consider the applicability of 35 U.S.C. 103(c) and potential 35 U.S.C. 102(e), (f) or (g) prior art under 35 U.S.C. 103(a).
Claims 1-5, 8, 9 and 20-22 are rejected under AIA 35 U.S.C. 103(a) as being unpatentable over Stoss et al. (Synthesis, 1987, 174-176) in view of Matt et al. (ACS Sustainable Chemistry & Engineering, 2018, 6(12), 17382-17390).
The present application claims a process of making and/or isolating isoidide of formula (I) comprising providing or preparing a mixture of compounds of formula (II) comprising isoidide and one or both of compounds selected from isosorbide and isomannide in the presence of a metal catalyst by reacting the mixture with a carboxylic anhydride that consists of a total number of carbon atoms in the range from 2 to 8.
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The Stoss reference teaches the regioselective acylation or esterification of a mixture of 1,4:3,6-dianhydro-D-glucitol, shown in the formula scheme below using barium, mercury, lead or bismuth salts, see left-hand column under the scheme.
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The selectivity of the acylation occurs with the OH groups on the opposite face of the bridgehead hydrogens. For example, in the top part of the scheme below, compound 1 is acylated at the OH at the 5-position, which is opposite to the bridgehead hydrogen at the 4-position, in 70 to 85% yield for compounds 2a-f.
The 90 mole % of the isolated non-esterfied isoided is dependent on the starting composition of formula (II).
Claims 4 and 20-22 are drawn to concentrations of the different components of the M3 mixture, which is the esterified mixture or differences in temperatures for the selective esterification reaction. The reference goes on to state the yield of the acylation is affected by the R group of the anhydride, the shorter alkyl R group, shorter reaction times and decreased temperatures, favor compound 2 over compound 4, see Table 1, In other words, longer alkyl R groups, higher temperatures and longer reaction times favor the formation of compound 4. The concentration ranges are broad, e.g. 10 to 95 mole % or molar ratios, which are also broad. The molar ratio of the nonesterified isosorbide, isomannide and isoidide to esterified, isosorbide, isomannide and isoidide, respectifully, in claim 1 will vary based on these result-effective variables.
Generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. "Where 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." In re Aller, 220 F.2d 454, 105 USPQ 233, 235 (CCPA 1955). Accordingly, this type of modification would have been well within the purview of the skilled artisan and no more than an effort to optimize results.
The Stoss reference further teaches the saponification of the mixture of acylated products to obtain compounds previously difficult to make, see page 175, left-hand column.
The Stoss reference does not teach a method of making and/or the isolating isoidide. However, the reference does teach that the esterified isosorbide and isomannide may be recovered by crystallization and/or distillation.
Moreover, a person of ordinary skill in the art would realize the difference in properties between the esters and hydroxyl groups. Based on the changed properties ofbtained from the esterification or acylation versus unreacted di-ol compounds, the esterified compounds may be removed by organic solvents and the di-ols removed by water through a separating or partitioning between the two solvents. The esters would be soluble in e.g. ethyl acetate, and the di-ols in water.
The Matt reference provides this rationale with a isosorbide and a single ester of isosorbide. Matt et al. teach the separation of an unreacted isosorbide and a single ester of isosorbide by way of liquid-liquid extraction, see page 17384, right-hand column, lines 1-3, that shows the separation with ethyl acetate and water.
Thus, the Stoss reference provides guidance on the separation of unreacted isoidide from the selective esterification of isomannide from isoidide.
Applicant traverses by stating, “Initially, claim 1 is amended for precision. The Office did not reject all the elements of the present claims. Applicant therefore respectfully submits that the rejections are deficient at least for this reason.”
This is not persuasive. The Examiner is uncertain if Applicant intends the amended elements or the previous claim 1. Regardless, all the elements were addressed previously and the currently amended claim 1 will be addressed further below.
Applicant further states, “Stoss does not teach or suggest to esterify a mixture of dianhydrohexitols (comprising isoidide and one or both compounds selected from the group consisting of isosorbide and isomannide) but only report of ways to selectively esterify iso-sorbide, while their respective reaction time is between 20 and 40 hours at room temperature. In contrast, the method of amended claim 1 only requires a reaction time of between 15 minutes and 10 hours to subsequently obtain and/or isolate non-esterified isoidide. Stoff is deficient at least for this reason.”
This is also unpersuasive. Applicant is correct that the Stoss does not teach or suggest to esterify a mixture of dianhydrohexitols (comprising isoidide and one or both compounds selected from the group consisting of isosorbide and isomannide) but only report of ways to selectively esterify iso-sorbide. It is this teaching that a skilled artisan would be able to apply the teaching to isolate isoidide as noted in the rejection. Applicant is not correct to state the respective reaction time is between 20 and 40 hours at room temperature. Based on the scheme from the Stoss reference above, the second route is only 1 hour, see also the experimental section on page 175, right-hand column.
Applicant notes, “Nor would Stoss disclose how the reaction rates for the single or double esterifications of isoidide, isosorbide, and isomannide would relate to each other, which would be critical if one would plan to separate the non-esterified and partially or completely esterified different dianhydrohexitols by a method as convenient as liquid-liquid extraction (as is now specified in amended claim 1).”
This is also not persuasive. The Matt reference addresses the liquid-liquid extraction method of claim 1 with a different single ester of isosorbide and unreacted isosorbide. This teaching can be applied to the present claimed method.
Claims 1-6, 8, 9 and 20-22 are rejected under AIA 35 U.S.C. 103(a) as being unpatentable over Stoss et al. (Synthesis, 1987, 174-176) in view of Matt et al. (ACS Sustainable Chemistry & Engineering, 2018, 6(12), 17382-17390) and Le Notre et al. (ChemSusChem., 2013, 6, 693-700).
The 103 rejection above is incorporated here.
Claim 6 is drawn to a transfer hydrogenation in the presence of a transition metal catalyst to react one or more compounds selected from isosorbide, isomannide, esters of isosorbide, esters of isomannide and mixtures thereof to obtain the mixtures provided in claim 4.
Le Notre teaches the epimerization of isosorbide using ruthenium on carbon, see page 694, Scheme 1 and 2. The reference also teaches the use nickel-on-Kieselguhr, Raney nickel and ruthenium on silica as catalyst, see page 694, third full paragraph in the left-hand column.
Thus, the isomerization step in claim 6 using a transition metal is found in the Le Notre reference.
Applicant traverses by stating, “Le Notre does not the cure the deficiencies of Stoss at least because Le Notre does not teach or suggest all the elements of the present claims and has not been cited for such. Rather, the Office merely cited Le Notre for allegedly teaching the elements of claim 6. Thus, Le Notre is deficient at least for this reason.”
This is not persuasive for the same reasons noted above in the first art rejection.
Claims 1-9 and 20-22 are rejected under AIA 35 U.S.C. 103(a) as being unpatentable over Stoss et al. (Synthesis, 1987, 174-176) in view of Matt et al. (ACS Sustainable Chemistry & Engineering, 2018, 6(12), 17382-17390), Le Notre et al. (ChemSusChem., 2013, 6, 693-700) and Dussenne et al. (Green Chemistry, 2017, 19, 5332-5344).
The 103 rejection over claims 1-6, 8 and 9 above is incorporated here.
Claim 7 is drawn to a method comprising reacting one or both compounds selected from the group consisting of sorbitol, mannitol and mixtures thereof, under acidic conditions, to receive one or more compounds selected from the group consisting of isosorbide, isomannide and mixtures thereof.
Dussenne et al. teach the double dehydration reaction of sorbitol to isosorbide with a variety of acids, see page 5335, Scheme 4 and page 5336, Scheme 5.
Therefore, Dussenne et al. teach the double dehydration step in claim 7 under acidic conditions.
Applicant traverses by stating, “Dussenne does not the cure the deficiencies of Stoss at least because Dussenne does not teach or suggest all the elements of the present claims and has not been cited for such. Rather, the Office merely cited Dussenne for allegedly teaching the elements of claim 7. Thus, Dussenne is deficient at least for this reason.”
This is not persuasive for the same reasons noted above in the first art rejection.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SUSANNA MOORE whose telephone number is (571)272-9046. The examiner can normally be reached Monday - Friday, 10:00 am to 7:00 pm.
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/SUSANNA MOORE/Primary Examiner, Art Unit 1624
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