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 .
Amended claims 1, 6-8, 10, 12, 15-22, new claims 25-27 are pending.
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.
New claims 25 and 27 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.
Claims 25 and 27 depend on claim 1. These claims lack antecedent basis for starting materials and product.
The starting materials as recited do not correspond to the starting materials (and products) of claims 25 and 27. Claim 27 as recited does even have the alcohol (OH) and lactone functionalities present in 2 and 1 of claim 1.
Claim 25 needs starting material 2 isopulegol, which does not fall under the scope of 2 of claim 1 because as per claim 1, n in formula 2 is 1
(
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= an unsubstituted methylene)
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, 6-8, 10, 12, 15-22, 25-27 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claim 2 of copending Application No. 18145383 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other because:
Claim 2 of 18145383, reads
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In the conflicting claims, the oxidizing agent, acid and solvent relate to each other as genus (18145383) and species (instant). Single vessel without isolation of intermediates is equivalent to instant one step.
NOTE: The above (2) in claim 2 of 18145383 corresponds to isopulegol 2 of instant dependent claim 25
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Thus rejection (claim 1) is based on disclosure in the specifications in the conflicting cases.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Previously presented rejection of 1, 6-8, 10, 12, 15-22, new claims 25-27 rejected under 35 U.S.C. 112, first paragraph, because the specification, while being enabling for making two compounds of formula 1, each of which with specific combination of reactants, reagents and very specific process parameters, does not reasonably provide enablement for the large number of reactants, products, reagents and process parameters, is maintained for reasons of record.
Amendments to claims address the issues raised with respect to scope of starting materials and products.
Applicants arguments focus on the amendments to claim 1 which includes limitations with respect to reagent (oxidizing agents), acids and solvents. Applicant at bottom of page 8, points out disclosure in the specification as to oxidizing agents and solvents as being exemplified in working examples 4, 6-8 and 10.
Applicant at page 9 points out that
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More specifically, at page 9 according to Applicant, given the high level of skill in the art, the unpredictability in the art could be overcome with the ‘numerous scientific references’ for the guidance, for the claimed chemical reaction mechanism and procedures disclosed in the specification. Further at top of page 10, Applicant states that the need for experiments should not preclude embodiment(s as claimed). At page 10 second paragraph, Applicant states that the technology is not new and further specification could include inoperative elements. Starting from bottom of page 10, Applicant argues that the rejection is untenable in the context of many case laws. Specifically, Applicant provides Exhibits A-C, relate to three Board decision (more on this later). Further at top of page 11, Applicant notes that Board reversed a rejection that based lack of parameters (such as temperature and reaction times as required by the instant rejection). Again at page 11, Applicant asserts that the rejection does not provide a reasonable explanation of why the scope is not enabled:
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Exhibit A: Board disagreed because
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Exhibit B: Board disagreed because
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Exhibit C: Board disagreed because
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Response:
Above reiteration of some and not all of Applicant;s Remarks with page numbers and also some and not all of ‘whys’ for the Board’s decisions) is to make clear that Appplicants argumentts are fully understood and considered by this Examiner and the Borad decisions do not pertain to the core issue here.
Applicant pointed out limitations (Examples 4, 6-8 and 10 ) teaches selective combination of known reactants, solvents and reagent. However Applicants Remakrs are specieious arguments at best. In addition to specific combination, the actual process parameters of temperature and concentration in the working examples is inconsistent with the breadth of the oxidizing agents and solvents in the claims. None of the working examples point to the use of meta-chloroperoxybenzoic acid, tert-butyl hydroperoxide, or to the use of hydrochloric acid, perchloric acid, phosphoric acidtrifluoromethanesulfonic acid, methanesulfonic acid, trifluoroacetic acid, or nitric acid. Likewise, the use of acetic anhydride or any and all polar protoic solvents (other than water/acetic acid) as solvent does not find support. Similarly, the argument that esters and ketones are usable is questionable since the working example 10 (where these solvents are shown) has no acid as reactant and further the procedure of Example 10 is under non-aqueous condtion. The claim 1 requires the presence of acid.
Applicant submits (Reamrks page 10) that the claimed invention is not directed to nascent technology and therefore the ‘numerous scientific references in the specification” (page 9), provide guidance of how to carry out the process (with varied parameters). First of all, none of the references (see specification page 1 onto page 2, pages 25-27), teach a one step conversion of an ally alcohol to gamma-butyrolactone. Consider for example, the teaching of venerable Gilbert Stork (cited at top of page 27 of specification). Stork teaches the oxidation of an allyl alcohol with mcpba (one of agents included in the claim) to make epoxy alcohol (see Stork’s supplementary material). The formation of epoxy alcohol by the most anticipated product of allyl alcohol by (the recited reagents) was expliticitly acknowldeged by this Examiner at previous action (page 5 onto page 6). Just as Stork, none of the references (drawn to variations of oxidizing agents, solvents and varied process parameters) teach direct convertion of an allyl alcohol to gamma butyro lactone in a single step (as limited by the claim). Citations such as these further substantiate Examiner’s assertion that the claimed process is unique and unprecedented. The relevant working examples (Examples 1 and 5) have the claimed limitiations: suluric acid (for acid) peracetic acid (for oxidising agent) and acetic acid and water.
Applicant is not responsive to the references cited by the Examiner in the previous action (at page 7 onto page 8) with respect to unpredictability in the art, espceially for Hayahsi reference as to the caveats associated with one-pot, single step procedures. The references overlooked by the Applicant includes Applicants own work that shows the need for multi-step procedures for the transformation of isopulegol to 3,6-dimethylhexahydrobenzofuran-2(3H)-one in support of the extradinary natue of the claimed process.
Exhibit A relates to multistep process, the instantly claimed process is drawn to single step process. In Exhibit B, the Board points to 38 working examples. Similarly, with respect to Exhibit C, Board notes that the generic term ester is well understood and the interpretation of the claims (by the Examiner in that case) is questionable.
As note above, the scope of starting materials, or even for some of the reagents and solvents in the claimd single step is/are not the issue. The problem is the manner in which the step is performed, how these are mixed. In addition the rejection is under 112-1 for scope of enablement not for enablement. Two compounds (working examples) were made under ‘specific combination of reactants, reagents and very specific process parameters’, not any and all reagents and solvents using any process condition. Examiner is not looking for ‘operating manual’ (as Applicant alleges see Remarks top of page 11)
Again, the results obtained here for processes for two compounds each reflecting very specific combination of reactants, reagents, how the reactants are mixed under specific process parameters such as concertation, rate of mixing of various solvents temperature etc. This position taken by the Examiner is that these exemplifications do not represent a process that can be extended to any allyl alcohol. As noted in previous action at page 4
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Chemistry mechanistic reasoning for the above statement was presented in extensive detail in previous action for
why the two working examples reflect optimized versions of a hitherto unknown transformation extraordinary transformation
and while
reasonable amount of routine experimentation is permissible,
undue experimentation
would be needed for predictable use (for the full scope of the claims with regards to starting materials, reagents, solvents and implied any and process parameters of solvent and temperature and rate of addition etc.)
THIS ACTION IS MADE FINAL. Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to NIZAL S CHANDRAKUMAR whose telephone number is (571)272-6202. The examiner can normally be reached M-F 8-5 EST.
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, Andrew Kosar can be reached at (571) 272-0913. 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.
/NIZAL S CHANDRAKUMAR/Primary Examiner, Art Unit 1625
Followinfg is from office action 10/16/2025:
All of the factors have been considered with regard to the claims, with the most relevant factors discussed below:
The claimed one-pot chemical process to make previously known products using previously known starting materials and reagents.
The two working examples disclosed at page 27 Example 1 and at page 29 Example 5 (Applicant needs to correct the title of Example 5)
Both the starting materials and products are very similar with respect to chemical structures:
Homoallylic alcohols transformed to gamma-butyrolactone, using
same oxidizing agent, solvent and acid in both cases. As surmised these are H2O2, acetic acid and sulfuric and in same relative stoichiometry.
In spite of the major structural similarity and the same stoichiometry of the (same) reactants substantially different yields are obtained. Conformationally constrained homoallyl alcohol (Example 1) provides lactone in 5 fold higher yield compared to the flexible homoallylic alcohol (Example 5), due to the intramolecular nature of the participating functionalities.
There is no example of starting materials (2) wherein n is other than 1.
There is no example of starting material (2) wherein the R is other than H.
There is no example wherein any of the R group is optionally substituted, for example, as defined in [00025] of specification of the ‘substituents’.
There is no example for oxidizing agent other than hydrogen peroxide (Note that peracetic acid is anticipated to form from H2O2 and acetic acid). As such claims such as 15 just does not find support in the specification.
There is no example where in the solvent is other than acetic acid. As such claims such as 18 just does not find support in the specification.
There is no example wherein the acid (sulfuric acid) could be replaced by a base!. That acid and base could be used interchangeably for the same purpose, just does not make sense, given the opposite functions of acids and base.
The claimed process is unprecedented, unique and challenges conventional chemical wisdom. The is explained below in the context of the (only) two working examples:
It is clear that the working examples are optimized versions of the claimed process, optimized with respect to oxidizing agent, stoichiometry, solvent and temperature AND most importantly the method of mixing (order of addition) the different reactants.
One of skill in the art would at once anticipate that reaction of H2O2 in acetic acid and terminal olefin is known to make epoxide. The reaction of a terminal epoxides even in the presence of excess H2O2 to make necessary carboxylic acid function is unknown in the art and defies commonsense.
Initial step in known reactions of epoxide with an acid (H-A) is anticipated to start with protonation of oxygen of the epoxide:
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The opening of the epoxide at the tertiary C with H2O or sulfate or acetate anions present is just not expected to make the necessary intermediate to make a lactone. For instance, in the presence of water, a 1.2-vicinal diol is anticipated. The terminal C in the protonated epoxide in the presence of acid, as per claimed process need to undergo two level oxidation to make the carboxylic acid (for lactonization).
In the disclosed working examples, there is/are enough oxidant (3 eq of H2O2). As such the observed lactone formation, while acknowledged, is a result of substrate specific major process research effort (more on this below with citations).
One of skill in the art of (paper) organic chemistry, by pushing arrows, could imagine rearrangement of the protonated epoxide to make primary alcohol which in turn could get oxidized to carboxaldehyde (which in turn could further oxidized to carboxylic acid for cyclization to lactone). The initial said formation of primary alcohol by !,2 migration of the H on the terminal epoxide C, to the positively charged C can happen only on paper. Such an imagination parallels the speculated scheme (guidance? and direction?), without being bound by theory [00040] at page 25) for the ‘invention’ claimed. Many of the indicated indicated/theorized transformation not only do not find support in the chemical literature, but also contradict commonly known fundamental established principles. For example, the transformation of (3) to (7) in the scheme at page 18 onto page 19 would be a 5-endo-tet cyclization (contradicting fundamental organic chemistry principles such as Baldwin rules). See for example the teachings of Bats in Tetrahedron VoL 38, No. 14, pp. 2139 to 2146, 1982 and Tetrahedron Letters Vol. 21, pp 3051 – 3054, Fig.2 at page 2140 and Fig. 3051.
As noted above, except for H2O2, the limitations of claim 15 (for oxidizing agents) do not find support and contradicts reactions widely known to be mediated by the recited reagents. For example many of the agents are well-known to oxidize alcohol to ketone. Another example is Applicant provided reference Schomaker (IDS 11/19/2024 cite no. 5) teaches in Table 1 at page 3090 that osmium tetroxide (of claim 15) would cleave the double bond.
Similarly, the list of solvents included in claim 18 defies commonsense. Thus alcohol solvents included in claim 18 are at once anticipated to be oxidized by the oxidants and thus would be incompatible with the claimed process.
The position taken is that the two working examples are optimized versions of a one pot, hitherto unknown transformation. A multi-step version of this extradentary transformation of isopulegol to the lactone (working example 1) is the subject matter of US 10399954 (to instant Applicant). 10399954 teaches at column 3 and at column 9, at least six steps are needed for the instantly claimed one-pot process.
The position taken by this Examiner is that extending the chemistry of Examples 1, 4 and 5 to the full scope of the instant claims, in predictable manner would require undue amount of effort.
Note that a patent application's disclosure must enable a person skilled in the art to make and use the invention without "undue experimentation,"
though a reasonable amount of routine experimentation is permissible.
The law does not require every single embodiment of a broad claim to be enabled by a specific example, but it does prevent an applicant from claiming a scope that requires the public to engage in a research program to figure it out.
This serves a fundamental purpose: in exchange for a limited monopoly, the public receives a meaningful disclosure that allows others to practice the invention once the patent expires.
According to Susannah, ACS Catalysis 2022 12 (6), 3644-3650, titled “To Err is Human; To Reproduce Takes Time”, at page 3644, column B
A lack of reproducibility in scientific research has important practical consequences: future investigators cannot build on prior results; large quantities of researchers’ time and taxpayers’ money are wasted.
(emphasis added by the examiner).
Unpredictable nature of organic chemical reactions is art acknowledged, for example see Dorwald, Side Reactions in Organic Synthesis, 2005, Wiley: VCH, Weinheim pg. IX of Preface pg. 1-15. Similarly, as exemplified by Hayashi, Pot economy and one-pot synthesis, | Chem. Sci., 2016, 7, 866–880, multiple process parameters dictate the outcome of one pot chemistry. For example, Hayashi teaches several restrictions in carrying out a one-pot synthesis and especially at page 868-870 teaches issues when same reagent is used in multiple transformations in a one-pot synthesis. Also see Taylor, A Brief Introduction to Chemical Reaction Optimization. Chem. Rev. 2023, 123, 3089−3126.
There is a substantial gap between what is taught in the specification and what is being claimed. For these reasons, one skilled in the art would be faced with undue amount of research. The specification lacks disclosure sufficient to make and use the invention.
MPEP 2164.01(a) states, “A conclusion of Iack of enablement means that, based on the evidence regarding each of the above factors, the specification, at the time the application was filed, would not have taught one skilled in the art how to make and/or use the full scope of the claimed invention without undue experimentation. ln re Wright, 999 F.2d 1557,1562, 27 USPQ 2d 1510, 1513 (Fed. Cir. 1993).'' That conclusion is clearly justified here.
Undue experimentation would be required to make and use Applicants' invention.
Genentech Inc. v. Novo Nordisk A/S (CA FC) 42 USPQ2d 1001, states “a patent is not a hunting license. It is not a reward for search, but compensation for its successful conclusion” and “[p]atent protection is granted in return for an enabling disclosure of an invention, not for vague intimations of general ideas that may or may not be workable”.
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Prosecution Insights