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
Claim Status
Claims 1-9 are pending. Claims 1-9 are under examination. Claims 1-9 are rejected. No claims allowed.
Filing Receipt
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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.
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.
Claim(s) 1-9 is/are rejected under 35 U.S.C. 103 as being unpatentable over Karame et al (Highly Enantioselective Hydrogenation of β-Alky and β-(ω-Chloroalkyl) Substituted β-Keto Esters, Synthetic Communications, 37, pp. 1067-1076, Published 2007), Noyori et al. (Asymmetric Hydrogenation of β-Keto Carboxylic Esters. A Practical, Purely Chemical Access to β-Hydroxy Esters in High enantiomeric Purity, J. Am. Chem. Soc., 109, p. 5856-5858, published 1987) and Sotoguchi et al. (USPGPub 2003/0105341, Published 06-2003). The above NPL’s can be found in the IDS filed 06/25/2024.
The instant claims are generally drawn to…
Scope of the Prior Art
Karame et al. teach preparation of ethyl ester homologs of current compound (B) via the reduction of the respective β-keto ethyl esters. The reductions can be catalyzed with ruthenium BINAP catalysts. See Karame et al. pages 1068-1070, Table 1, Schemes 1-3.
Karame et al. broadly teach the β-hydroxy esters are available by reaction of the dianion of ethyl acetoacetate with alkyl iodides (p. 1068).
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The ethyl ester of current compounds (A) and (B) are represented in the above Scheme 1 when n is 2 and x is Cl.
Karame et al. teach the β-hydroxy esters are important building blocks for the synthesis of biologically active compounds and natural products (p. 1068, top of page.).
Karame et al. teach Ru[(R)-BINAP]Cl2 catalyst being active in the above hydrogenation (p. 1070). This catalyst reads on variable current variable X1 being Cl.
Ascertain the Differences
Karame et al. does not teach the t-butyl protecting group nor the specific catalysts of claims 1 and 7.
Secondary References
Noyori et al. teach a methyl, ethyl and t-butyl β-keto esters being reduced to the equivalent β-hydroxy esters utilizing ruthenium Br2/Cl2[(S/R)-BINAP] catalysts (Table I., p. 5857). Although the catalysts taught by Noyori et al. are not the current catalyst, this teaching establishes t-butyl as a protecting group utilized in the current chemistries.
Noyori et al. goes on to teach broad success with the use of asymmetric catalytic hydrogenation for production of optically active β-hydroxy esters:
“Thus, synthetic organic chemists no longer must envy bakers' yeast to effect stereoselective reduction of β-keto esters. The hydrogenation method is clean, operationally simple, economical, and hence is capable of conducting large-scale production of optically active β-hydroxy esters. A wide range of hydroxy esters of either chirality sense is available in high enantiomeric purity” (p. 5857).
Additionally, the teachings of Noyori et al. overlap with Karame et al. in that BINAP Ru catalysts are utilized to reduce β-keto esters to the corresponding alcohols. These teachings render Noyori et al. analogous art to the invention.
Sotoguchi et al. was brought in to teach the use of the current catalysts in reductions of β-keto esters to the respective β-hydroxy esters (par. 31 and pages 3 and 4 and Example 3 and page 5). For example, Sotoguchi et al. teach BINAP and H8-BINAP (partially hydrogenated BINAP) and SegPhos (claim 1) can be used in a reaction to reduce a β-keto ethyl ester to a β-hydroxy ester.
Alternatively, Sotoguchi et al. teaches [RuCl{(S)-segphos}]2(µ-Cl3[Me2NH2] catalyst utilized in a reaction to reduce a β-keto ethyl ester to a β-hydroxy ester with a chemical purity, optical purity and yield being 95.5, 99.1 and 87.6% respectively (Example 3) (current claims 7-9).
Concerning the S or R configuration of the catalyst, choosing the R or S
configuration of the catalyst is dependent on the desired product chirality. For example, Sotoguchi et al. teach the configuration (R or S) is chosen to obtain the absolute configuration of the reduced product (par. 79).
The teachings of Sotoguchi et al. overlap the teachings of Noyori et al. and Karame et al. in that Ru BINAP catalysts are utilized to reduce β-keto esters. The above teachings render Karame et al., Noyori et al. and Sotoguchi et al. analogous art.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have prepared the compound of formula 2 taught by Karame et al. with a reasonable expectation of success. The ordinary artisan would have done so because Karame et al. teach the β-hydroxy esters are important building blocks for the synthesis of biologically active compounds and natural products (p. 1068, top of page). There would have been a reasonable expectation of success because Karame et al. teach the β-hydroxy esters are available by reaction of the dianion of ethyl acetoacetate with alkyl iodides (p. 1068).
The ordinary artisan would have generated the ethyl ester of the current compound (B) from (A) because Karame et al. teach a Markush group that encompasses the ethyl ester of the current compound (p. 1068). See immediately below. Note: when variable n is two and variable x is Cl, the ethyl ester of the current compound (B) is present, or at least a racemic mixture thereof.
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Next, the ordinary artisan would have known that other protecting groups for esters existed and would have tried the t-butyl protecting group with a reasonable expectation of success because Noyori et al. teach a t-butyl β-keto ester being reduced to the equivalent β-hydroxy ester utilizing a ruthenium catalyst. The ordinary artisan would have looked to Noyori et al. due to the overlapping subject matter as argued above.
Next, the ordinary artisan, needing a catalyst would have utilized the
[RuCl{(S)-segphos}]2(µ-Cl3[Me2NH2] catalyst taught by Sotoguchi et al. with a reasonable expectation of success. The ordinary artisan would have done so because of the chemical purity, optical purity and yield of the product being 95.5, 99.1 and 87.6% respectively when reducing a β-keto ethyl ester to a β-hydroxy ester. The ordinary artisan would have looked to Sotoguchi et al. due to the overlapping subject matter as argued above.
Alternatively, due to Sotoguchi et al. teaching overlapping phosphine ligands as taught by Karame et al., Noyori et al., mainly BINAP ligands, and further teaching ligands SegPhos and H8-BINAP, it would have been obvious to place the ligands in the Ru catalysts to make Cl2/Br2[(R/S)-ligand] versions of the Cl2[(R)-BINAP] catalyst and arrive at the invention.
Regarding the S and R chirality if the current catalysts, this is chosen depending on the desired product.
Concerning claims 5-6 and 8-9, the combined processes of the prior art are substantially identical to those of the prior art. Thus, the products would be substantially identical, especially with Sotoguchi et al. teaching optical purity of 99.1%.
Substantially identical methods yield substantially identical products. See MPEP 2112.01 I. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). "When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990).
After combining the teachings of Karame et al., Noyori et al., and Sotoguchi et al. the ordinary artisan would have arrived at the current invention.
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 1-9 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 5 and 12 of U.S. Patent No. 11,999,757.
Although the conflicting claims are not identical, they are not patentably distinct from each other because the instantly claimed subject matter embraces or is embraced by the patented subject matter. For example, 11,999,757 claims the following.
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11,999,757 does not claim the catalysts of claim 7. However, the ordinary artisan in need of the full scope of the claimed reduction, would have consulted the patented specification and would have found on columns 28-32 the preferred catalysts and parameters of the currently claimed reduction.
The specification can be utilized as a dictionary to interpret the reference’s claims and to confirm the scope of the reference’s claims. See MPEP 804(II)(B)(1).
The specification can be used as a dictionary to learn the meaning of a term in the claim. Toro Co. v. White Consol. Indus., Inc., 199 F.3d 1295, 1299, 53 USPQ2d 1065, 1067 (Fed. Cir. 1999) ("[W]ords in patent claims are given their ordinary meaning in the usage of the field of the invention, unless the text of the patent makes clear that a word was used with a special meaning."); Renishaw PLC v. Marposs Societa' per Azioni, 158 F.3d 1243, 1250, 48 USPQ2d 1117, 1122 (Fed. Cir. 1998) ("Where there are several common meanings for a claim term, the patent disclosure serves to point away from the improper meanings and toward the proper meanings."). "The Patent and Trademark Office (‘PTO’) determines the scope of the claims in patent applications not solely on the basis of the claim language, but upon giving claims their broadest reasonable construction ‘in light of the specification as it would be interpreted by one of ordinary skill in the art.’ " Phillips v. AWH Corp., 415 F.3d 1303, 1316, 75 USPQ2d 1321, 1329 (Fed. Cir. 2005) (en banc) (quoting In re Am. Acad. of Sci. Tech. Ctr., 367 F.3d 1359, 1364, 70 USPQ2d 1827, 1830 (Fed. Cir. 2004); see also MPEP § 2111.01.
Consequently, the ordinary artisan would have recognized the obvious variation of the instantly claimed subject matter over the patented subject matter.
Conclusion
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/B.G.D/Examiner, Art Unit 1692 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625