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.
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 May 14th, 2026 has been entered.
Response to Amendment / Argument
The rejection of claims 1-6 under 35 USC 103 has been withdrawn in view of Applicant’s amendment to require removal of n-propyl chloride; however, the newly added limitation is rejected as indefinite below. The 103 rejection below retains references to the general procedure of claim 1 for clarity in terms of how the products of instant claims 7 and 11-14 would be obtained. Regarding the rejection over claims 7 and 11-14, Applicant’s traversal “A” on page 9 of the remarks filed May 14th, 2026 refers to “a significant reduction in chemical impurities” for alleged unexpected results. This result appears to be dependent upon the method being practiced rather than the materials per se, i.e. since it would be possible to practice a method of making without concern or removal of n-propyl chloride. Applicant’s traversal “B” similarly refers to method steps, which is not found persuasive regarding claims to products. Applicant’s traversal “C” refers to an alleged functional incompatibility in view of Applicant’s data. Applicant’s data, however, is not prior art and cannot inform a reasonable expectation of success or a motivation to combine. See MPEP 2143.02(III). Applicant’s data is not found persuasive regarding unexpected results for the reasons above.
On page 11 of the response, Applicant refers to the ODP rejection and suggests a terminal disclaimer might be filed. Until such time, the double patenting rejection is maintained.
All other rejections made in the previous Office Action that do not appear below have been overcome by Applicant's amendments to the claims.
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 1-6 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.
Claim 1 recites the limitation "the offgas stream" in line 6 of the claim. There is insufficient antecedent basis for this limitation in the claim. Claim 1 does not previously recite or require an offgas stream. Dependent claims 2-6 are rejected as indefinite for the same reasons since they do not clarify the issue.
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) 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 instant claims are directed to products that would be obtained when applying the prior art process to use n-propyl at the prior art position R7.
Finding of prima facie obviousness --- rationale and motivation (See MPEP § 2141.02)
Regarding the identity of the variables, specifically the instant variables n 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 R8-R12 variable definitions:
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The variable definitions of R8-R12 correspond to definitions embraced by the instant claims where R9 and R11 are hydrogen, R8 and R12 are methyl and R10 is halogen (chlorine).
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. 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.
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.
Specifically 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 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
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.
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/MATTHEW P COUGHLIN/Primary Examiner, Art Unit 1626
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