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 .
DETAILED ACTION
Claims 1-7 and 11-14 are pending in the application. Claims 1-7 and 11-14 are rejected.
Response to Amendment / Argument
The amendment to the claims filed on December 10th, 2025 does not comply with the requirements of 37 CFR 1.121(c) because claims 8-10 are labelled as cancelled but contain marked claim text. Amendments to the claims filed on or after July 30, 2003 must comply with 37 CFR 1.121(c) which states:
(c) Claims. Amendments to a claim must be made by rewriting the entire claim with all changes (e.g., additions and deletions) as indicated in this subsection, except when the claim is being canceled. Each amendment document that includes a change to an existing claim, cancellation of an existing claim or addition of a new claim, must include a complete listing of all claims ever presented, including the text of all pending and withdrawn claims, in the application. The claim listing, including the text of the claims, in the amendment document will serve to replace all prior versions of the claims, in the application. In the claim listing, the status of every claim must be indicated after its claim number by using one of the following identifiers in a parenthetical expression: (Original), (Currently amended), (Canceled), (Withdrawn), (Previously presented), (New), and (Not entered).
(1) Claim listing. All of the claims presented in a claim listing shall be presented in ascending numerical order. Consecutive claims having the same status of “canceled” or “not entered” may be aggregated into one statement (e.g., Claims 1–5 (canceled)). The claim listing shall commence on a separate sheet of the amendment document and the sheet(s) that contain the text of any part of the claims shall not contain any other part of the amendment.
(2) When claim text with markings is required. All claims being currently amended in an amendment paper shall be presented in the claim listing, indicate a status of “currently amended,” and be submitted with markings to indicate the changes that have been made relative to the immediate prior version of the claims. The text of any added subject matter must be shown by underlining the added text. The text of any deleted matter must be shown by strike-through except that double brackets placed before and after the deleted characters may be used to show deletion of five or fewer consecutive characters. The text of any deleted subject matter must be shown by being placed within double brackets if strike-through cannot be easily perceived. Only claims having the status of “currently amended,” or “withdrawn” if also being amended, shall include markings. If a withdrawn claim is currently amended, its status in the claim listing may be identified as “withdrawn—currently amended.”
(3) When claim text in clean version is required. The text of all pending claims not being currently amended shall be presented in the claim listing in clean version, i.e., without any markings in the presentation of text. The presentation of a clean version of any claim having the status of “original,” “withdrawn” or “previously presented” will constitute an assertion that it has not been changed relative to the immediate prior version, except to omit markings that may have been present in the immediate prior version of the claims of the status of “withdrawn” or “previously presented.” Any claim added by amendment must be indicated with the status of “new” and presented in clean version, i.e., without any underlining.
(4) When claim text shall not be presented; canceling a claim.
(i) No claim text shall be presented for any claim in the claim listing with the status of “canceled” or “not entered.”
(ii) Cancellation of a claim shall be effected by an instruction to cancel a particular claim number. Identifying the status of a claim in the claim listing as “canceled” will constitute an instruction to cancel the claim.
(5) Reinstatement of previously canceled claim. A claim which was previously canceled may be reinstated only by adding the claim as a “new” claim with a new claim number.
Nevertheless, the amendment has been treated on the merits.
Objections and rejections made in the previous Office Action that do not appear below have been overcome by Applicant's amendments to the claims. Therefore, arguments pertaining to these objections and rejections will not be addressed.
On pages 8 and 9 of the response, Applicant traverses the rejection of claims under 112(b) in view of amendment; however, claim 1 still recites a confusing combination of singular and plural language, which rejection is maintained in modified form based on the amended language.
Beginning on page 9 of the response filed December 10th, 2025, Applicant traverses the rejection of claims under 35 USC 103. Applicant first refers to the disclosure of Crede and that it “represents deficient prior art from a technical and logistical perspective” due to generation of methyl chloride. It is unclear how Applicant considers this relative to the rejection. If Applicant is suggesting this is a known problem, it would appear to motivate a person of ordinary skill in the art to avoid using methanol. Applicant states on page 9 “the prior art provides no motivation to specifically select n-propanol over other candidates like ethanol.” The prior art teaches that various alcohols can be used and there is no requirement that the prior art must suggest the instantly claimed option would necessarily be superior.
On pages 9-11 of the response, Applicant further refers to alleged “superior and advantageous results” when using n-propanol including data found in the specification. This issue is addressed in the rejection in that the comparisons do not compare directly with the closest procedure of the prior art.
For these reasons, the rejection of claims under 35 USC 103 is maintained.
On page 11 of the response, Applicant states that they are “prepared to execute a terminal disclaimer to address this rejection once otherwise allowable subject matter has been agreed upon.” Until such time, the rejection below is maintained.
Claim Rejections - 35 USC § 112(b)
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1-7 and 11-14 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 1-6 are rejected as indefinite based on the reference to plural and singular compounds and mixtures. Claim 1 contains various references to “compounds,” “hydrochloride compounds” and “mixtures” in the plural as well as references to “a base,” “a strong base” and “a protic acid” in the singular. It is unclear what effect these different references have on the scope of the claim. There would appear to be several possible interpretations including:
Applicant is using the reference to plural instances to mean that within a single embodiment embraced by the claim, multiple different compounds, hydrochlorides, and mixtures are obtained and/or used;
Applicant is using the reference to plurals to only mean that more than one molecule must be present; and
Applicant is using the reference to plurals to indicate that the claims are generic to multiple embodiments, i.e. methods of making different compounds.
No one interpretation is reasonably consistent with the claim language as drafted. For instance regarding interpretation (1), the reference to multiple non-identical entities would appear to be inconsistent with the reference to “mixtures” since a mixture is still a singular mixture no matter how many components are present, i.e. a mixture of six different compounds of formulae (IV’), (V’) and (VI’) is still a singular mixture. Regarding interpretation (2), the same issue regarding “mixtures” exists. Regarding interpretation (3), if Applicant were attempting to indicate generic coverage, it is unclear why the formula (XV) refers to plural compounds when the compound can only be n-propanol based on the definition of R7. It is unclear how the difference in number affects the scope of the claims under interpretation (3). For these reasons, the instant claims are considered indefinite due to an inconsistent and unclear convention regarding singular and plural entities.
Claim 7 is rejected in view of the discussion above and based on the amendment to claim 7 to limit the scope of R7 to only one option. It is unclear if Applicant is attempting to embrace situations where only multiple molecules are present or, for instance, provide coverage over isotopically labeled versions that could be considered a different compound. It is suggested that Applicant amend claim 7 to recite “A compound of formula (V’)”.
Claim 11 is rejected as indefinite since it defines variables R1 to R6 and n that are not otherwise required in the claim.
Claim 12 is rejected as indefinite since it defines variable n that is not otherwise required in the claim.
Claim 13 is rejected as indefinite since it defines variable n that is not otherwise required in the claim.
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 14 recites the broad recitation “optionally branched”, and the claim also recites “n-propyl” 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. If Applicant intended for the claim to encompass both n- and iso-propyl, it is unclear why the claim refers to n-propyl as a specific term instead of simply “optionally branched propyl”.
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.
Claim(s) 1-7 and 11-14 is/are rejected under 35 U.S.C. 103 as being unpatentable over WO 2018/024659 A1 by Crede et al. (published February 8th, 2018 and where an English language version was published as U.S. Patent PGPub No. 2019/0202837 A1 and will be referred to herein) in view of U.S. Patent PGPub No. 2011/0086762 A1 by Fischer et al. and in further view of U.S. Patent PGPub No. 2008/0305955 A1 by Breschneider et al.
Determining the scope and contents of the prior art. (See MPEP § 2141.01)
Crede et al. discuss a synthesis on pages 1 and 2 where the procedure includes the following step:
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The prior art describes the step above as follows on page 1: “These amino acids are then esterified by known methods of organic chemistry (for example by reaction with an alcohol R7—OH and thionyl chloride) to give the spiroketal-substituted amino acid esters of the general formula (IV; R7 equals C1-C6-alkyl).” The prior art step above corresponds to the instant first step of claim 1 except where the prior art does not explicitly state that hydrochlorides are obtained. Bridging pages 1 and 2, the prior art teaches the next step as follows:
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The prior art describes the step above as follows on page 1: “These amino acid esters are then acylated at the nitrogen with phenylacetyl chlorides of the general formula (VII) to give the compounds of the general formula (VIII).” The step above corresponds to the instant step involving compound of formula (VII) except where the prior art does not explicitly teach the use of a base as recited in the instant scheme. As a final step, the prior art teaches reaction with a strong base on page 1 as follows: “The compounds of the general formula (VIII) are subsequently cyclized in a Dieckmann reaction by action of a strong base such as potassium tert-butoxide or sodium methoxide, affording the spiroketal-substituted cyclic ketoenols of the general formula (XI).” This prior art step corresponds to the instant step of claim 1 involving a Dieckmann reaction using a strong base. As a final step, the prior art depicts the following on page 2:
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The prior art describes the step involving formula (XIV) as follows on page 1: “Accordingly, in order to obtain a clean product of the general formula (XI) under industrial conditions (where, for example, purification of the target compound by chromatography is not an option), it is essential to convert, in an additional step, this mixture of the compounds of the general formulae (XI), (XII) and (XIII) with a diol of the general formula (XIV) in the presence of an acidic catalyst into the uniform compound of the general formula (XI).” This step taught by the prior art corresponds to the same step involving formula (XIV) of instant claim 1.
Ascertainment of the differences between the prior art and the claims. (See MPEP § 2141.02)
The prior art teaches the general steps instantly claimed but does not teach an explicit example having the variable definitions instant claimed including where R7 is n-propyl and the prior art does not explicitly teach the generation of an HCl salt. Limitations of dependent claims and compound claims are addressed below.
Finding of prima facie obviousness --- rationale and motivation (See MPEP § 2141.02)
Regarding the identity of the variables, specifically the instant variables n, R1-R6 and R8-R12, a person of ordinary skill in the art in viewing the general structures of Crede et al. would have been familiar with permutations that have been prepared in the art. For instance, Crede et al. themselves teach the following structure on page 14 in demonstrating a comparison:
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Similarly, Fischer et al. teach the generation of salts of analogous compounds and teach the following cyclization on page 18 that results in a compound having the same n, R1-R6 and R8-R12 variable definitions:
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The variable definitions of n, R1-R6 and R8-R12 correspond to definitions embraced by the instant claims where n is 0, R1-R6 are hydrogen, R9 and R11 are hydrogen, R8 and R12 are methyl and R10 is halogen (chlorine) and meet the narrowing limitations of each claim 1-6.
Regarding the definition of the variable R7, Crede et al. generally teach that the corresponding group can be C1-C6 alkyl. A person having ordinary skill in the art would have been familiar with analogous disclosures that teach esterifications. For instance, Bretschneider et al. teach generation of compounds of the following general formula on page 4:
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The disclosure above teaches an analogous structure where the ester would be a C1-C6 alkyl group. Furthermore, Bretschneider et al. teach an example on page 22 using an ethyl ester:
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The structure above contains the same variable definitions discussed above except where n is 1 instead of 0. Furthermore, Bretschneider et al. teach conditions for generating the ester on page 54 as follows:
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The prior art teaches the use of thionyl chloride and further teaches the generation of an HCl salt as required by instant claim 1 and where the general scheme of Crede et al. teaches a second step of treatment with a base. A person having ordinary skill in the art in seeking to optimize the known prior art procedures would have been motivated to test the use of the possible C1-C6 alkyl groups especially where the prior art teaches methyl and ethyl examples that would at least suggested higher homolog of n-propyl as embraced by each of claims 1-6.
Regarding the use of a base in the instant step of reaction with a compound of formula (VII), Breschneider et al. teach an example on page 51 (Example II-1, paragraph [0639]) of an analogous reaction of an amine with an acid chloride using potassium carbonate. Accordingly, a person having ordinary skill in the art in practicing the overall scheme of Crede et al. would have been motivated to use known reaction conditions such as those disclosed by Breschneider et al.
Regarding a potential argument that Crede et al. teach away from the claimed invention, Crede et al. teach the following on page 1 regarding the final step of the known procedure: “This additional step is time-consuming, cost-intensive and uneconomical.” The teaching of Crede et al. only suggests that known procedures were imperfect and that their invention attempted to improve on known procedures. As noted in MPEP 2123: “A reference may be relied upon for all that it would have reasonably suggested to one having ordinary skill in the art, including nonpreferred embodiments. Merck & Co. v. Biocraft Labs., Inc. 874 F.2d 804, 10 USPQ2d 1843 (Fed. Cir. 1989), cert. denied, 493 U.S. 975 (1989).” At least for the purposes of optimizing the synthesis of any singular final product, a person having ordinary skill in the art would have been motivated to test the general known conditions (including variations of ester groups as discussed above) for the purposes of comparison and determining which known conditions would provide the best results in terms of yield, purity, etc.
The Examiner has reviewed the specification and Applicant presents examples beginning on page 25 where different length esters are prepared. The specification discloses that example 1 on page 26 results in a lower yield (61%) than ethyl (83.6%) and propyl (69%). MPEP 716.02(e) discusses comparisons with prior art as follows:
An affidavit or declaration under 37 CFR 1.132 must compare the claimed subject matter with the closest prior art to be effective to rebut a prima facie case of obviousness. In re Burckel, 592 F.2d 1175, 201 USPQ 67 (CCPA 1979). "A comparison of the claimed invention with the disclosure of each cited reference to determine the number of claim limitations in common with each reference, bearing in mind the relative importance of particular limitations, will usually yield the closest single prior art reference." In re Merchant, 575 F.2d 865, 868, 197 USPQ 785, 787 (CCPA 1978) (emphasis in original).
In this situation, the conditions of the specification are significantly different from the closest prior art example of Bretschneider et al. If Applicant intends to rely on unexpected results, the conditions of Bretschneider et al. should be repeated while minimizing changes including the ratio of reactants, temperature, reaction times, etc.
Regarding instant claims 7 and 11-14, these claims recite compounds depicted on pages 1 and 2 of Crede et al. Optimization of the procedure as discussed above including optimization of the identity of the instant variable R7 would have resulted in compounds of the instant formula. Accordingly, the instantly claimed intermediates are deemed obvious for the same reasons as discussed above. The instantly claimed formulae correspond to the same prior art numbering except where the instant formulae are labeled with as prime.
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 7 and 11-14 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-7 of U.S. Patent No. 12,006,327. Although the claims at issue are not identical, they are not patentably distinct from each other because the claims of the patent recite methods of using compounds instantly claimed. Claim 1 of the patent recites a method involving a compound of formula (V’) recited in instant claim 7, a compound of instant formula (IX’) as recited in instant claim 11, a compound of instant formula (X’) as recited in instant claim 12, a compound of instant formula (XII’) as recited in instant claim 13, and a compound of instant formula (VI’) as recited in instant claim 14. Furthermore, the dependent claims of the patent recite variable definitions embraced by the instant claims. Claim 7 of the patent recite definitions embraced by instant claims 7 and 11-14.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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 MATTHEW P COUGHLIN whose telephone number is (571)270-1311. The examiner can normally be reached Monday - Friday, 10 am - 6 pm 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, Renee Claytor can be reached at 571-272-8394. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/MATTHEW P COUGHLIN/Primary Examiner, Art Unit 1626