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
Amended Claims 41-43 and 102-105 (dated 08/30/2023) are pending are pending in this application is now under consideration for examination.
Priority
Applicants’ claim for the benefit of priority under 35 U.S.C. 119(e) or under 35 U.S.C. 120, 121, or 365(c) is acknowledged. This application is a DIV of 15/733,403 filed on 07/21/2020 now US 12,037,317, which is a 371 of PCT/US2019/014345 filed on 01/18/2019, which claims benefit of Provisional application: 62/622,052 filed on 01/25/2018.
Information disclosure statement
The information disclosure statement (IDS) submitted on 06/03/2024 is in compliance with the provisions of 37 CFR 1.97. Accordingly, the IDS statement is considered and initialed by the examiner.
Claim Rejection: 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.
Claim 41 and claims 42-43 and 102-105 depending therefrom are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112, second paragraph, as being incomplete for omitting essential steps, such omission amounting to a gap between the steps. See MPEP § 2172.01. Claim 41 recites “A method of preparing a compound of formula (XVII)…” and examiner interprets said compound of formula (XVII) is an S-form/enantiomer of the claimed compound and the steps recited in claims 41-43 and 102-105 comprising racemic intermediates/substrates of both R and S forms/enantiomers and catalyst/lipase will yield a racemate mixture of R and S forms/enantiomers of the claimed compound and thus requires a specific step that can resolve and purify the claimed compound from R form/ enantiomers. A claim is indefinite where a key step is missing from a method and how this method is actually practiced. Examiner suggests amending claims 41-43 and 102-105 to disclose “an event for step” that results or contributes to “A method of preparing a compound of formula (XVII)…” and examiner interprets said compound of formula (XVII) is a S-form/enantiomer of the claimed compound. Clarification and correction is required.
Double Patenting rejection
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 obviousness-type 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); and 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 a nonstatutory double patenting ground provided the conflicting application or patent either is shown to be commonly owned with this application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement.
Effective January 1, 1994, a registered attorney or agent of record may sign a terminal disclaimer. A terminal disclaimer signed by the assignee must fully comply with 37 CFR 3.73(b).
Claims 41-43 and 102-105 are rejected under the judicially created doctrine of obviousness-type double patenting as being unpatentable over claims 1-6 of US 12,037,317 B2 and in view of Lorenz et al., (Angew. Chem. Int. Ed., 2014, Vol. 53: 1218-1250). An obviousness-type double patenting rejection is appropriate where the conflicting claims are not identical, but an examined application claims are not patentably distinct from the reference claims, because the examined claims are either anticipated by, or would have been obvious over reference claims. 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). Although the conflicting claims are not identical, they are not patentably distinct from each other.
Although the conflicting claims are not identical, they are not patentably distinct from each other. Claims 41-43 and 102-105 of the instant application are directed to “a method of making formula XVII (S-form/enantiomer) contacting racemic β-butyrolactone (formula II) with a lipase (as in claims 41-43 and 102) …contacted with a solvent and separated by adding bicarbonate salt and reduced in the presence of sodium borohydride…” (as in claims 103-105; also see 35 U.S.C. 112(b) rejection above for claims interpretation) and reproduce below:
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Claims 1-6 of US 12,037,317 B2 and in view of Lorenz et al., (Angew. Chem. Int. Ed., 2014, Vol. 53: 1218-1250) are directed to and method of making said compound of formula XIII; examiner takes the position that the method claims of the instant application is directed to “a method of preparing a compound of formula (XVII)…” and examiner interprets said compound of formula (XVII) is an S-form/enantiomer of the claimed compound XIII of the allowed patent and as the method claims of the instant invention and the method claims of allowed patent is identical (reproduced below):
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and thus requires a specific step that can resolve and purify the claimed compound S-form/enantiomer of the instant application from R form/enantiomers of the allowed patent claims and therefore both the allowed patent claims and the instant application is racemate mixture of R and S-forms/enantiomers, as the methods are identical and comprises overlapping subject-matter. Additionally the following reference of prior art Lorenz et al., (Angew. Chem. Int. Ed., 2014, Vol. 53: 1218-1250), clearly teaches processes to separate enantiomers, i.e., compound of formula XVII of the instant application.
Therefore, claims 41-43 and 102-105 of the of the instant application cannot be considered patentably distinct over 1-6 of US 12,037,317 B2 and in view of Lorenz et al., (Angew. Chem. Int. Ed., 2014, Vol. 53: 1218-1250 that supports claims 1-6 of that patent and falls within the scope of the claims 41-43 and 102-105 herein i.e., “a method of making formula XVII (S-form/enantiomer) contacting racemic β-butyrolactone (formula II) with a lipase (as in claims 41-43 and 102) …contacted with a solvent and separated by adding bicarbonate salt and reduced in the presence of sodium borohydride…” (as in claims 103-105; also see 35 U.S.C. 112(b) rejection above for claims interpretation), because it would have been obvious to one having ordinary skill in the art to modify claims 1-6 of US 12,037,317 B2 and in view of Lorenz et al., (Angew. Chem. Int. Ed., 2014, Vol. 53: 1218-1250) by selecting a specifically disclosed embodiment that supports those claims of the reference patent. One of ordinary skill in the art would have been motivated to do this because that embodiment is disclosed as being preferred embodiment within claims 1-6 of US 12,037,317 B2 and in view of Lorenz et al., (Angew. Chem. Int. Ed., 2014, Vol. 53: 1218-1250).
Therefore, examiner takes the position that claims 41-43 and 102-105 of the instant application are rejected under the judicially created doctrine of obviousness-type double patenting as being unpatentable over claims 1-6 of US 12,037,317 B2 and in view of Lorenz et al., (Angew. Chem. Int. Ed., 2014, Vol. 53: 1218-1250) renders claims 41-43 and 102-105 of the instant application obvious. This is a obviousness-type double patenting rejection.
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.
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.
Claims 41-43 and 102-105 are rejected under 35 U.S.C. 103(a) as being unpatentable over Verdin et al., (WO 2017/21399 A1) and in view of Huang et al., (Appl. Microbiol. Biotechnol., 2014, Vol. 98: 621-628), Watanabe et al., (US 2006/0046286 A1, in IDS), Ohlinger et al., (Chem. Eng. Sci., 2003, Vol. 58: 1453-1461, in IDS), Dzulkefly et al., (The Malay. J. Anal. Sci., 2007, Vol. 11(2): 395-399, in IDS) and Ikemoto et al., (US 7,468,448 B2).
Claims 41-43 and 102-105 of the instant application as interpreted are directed to “a method of making formula XVII (S-form/enantiomer) contacting racemic β-butyrolactone (formula II) with a lipase (as in claims 41-43 and 102) …contacted with a solvent and separated by adding bicarbonate salt and reduced in the presence of sodium borohydride…” (as in claims 103-105; also see 35 U.S.C. 112(b) rejection above for claims interpretation).
Regarding claims 41-42, analogous art Verdin et al., (WO 2017/21399 A1) teach therapeutic compositions comprising ketone esters having the chemical formula XVII of the instant invention (Abstract; ¶ [0083-0085], reproduced below; and entire document), said ketone esters are (R)-1,3, butanediol ester of (R)-3-hydroxybutyrate derivatives (col. 2, lines 29-49); said (R)-3-hydroxybutyrate derivatives and oligomers (¶ [0003], [0036-0050], [0056], [0063-0066], [0086]).
Verdin et al., (WO 2017/21399 A1)
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However, Verdin et al., (WO 2017/21399 A1) does not teach or silent regarding wherein said method comprising a method of making formula XVII contacting racemic β-butyrolactone (formula II) with a lipase (as in claims 41-43) …contacted with a solvent and separated by adding bicarbonate salt and reduced in the presence of sodium borohydride… (as in claims 102-105).
Regarding claims 41-43 and 102-105, the following references teach the structural and functional elements of the instant invention i.e., a method of making formula XXVII contacting racemic β-butyrolactone (formula II) with a lipase;…contacted with a solvent and separated by adding bicarbonate salt and reduced in the presence of sodium borohydride…; Applicants’ are directed to the following references:
Regarding claims 41-43 and 102, Huang et al., (Appl. Microbiol. Biotechnol., 2014, Vol. 98: 621-628) teach the synthesis (R)-β-butyrolactone, (S)-methyl-3-hydroxybutyrate (Scheme 1, col. 1, page 622; and entire document) in the presence of benzene, methyl tert-butyl ether (MTBE), toluene and Candida antartica lipase (see Materials and Methods, col. 2, page 622- col. 1, page 624).
Regarding claims 41-43, Watanabe et al., (US 2006/0046286 A1, in IDS) teach a method of preparing the optically pure butyrolactone precursor of formula IIb (¶ [0018]) to make the non-acylated analog of the compound of formula XVlI (¶ [0134], [0135]), the method comprising step a) contacting a racemic b-butyrolactone of formula II with a Candida antartica lipase, wherein the compound of formula lla is hydrolyzed to prepare a mixture of the compound of formula IIb and a compound of formula II (¶ [0013]; [0016]; [0024]; [0028]).
Regarding claims 41-43, Ohlinger et al., discloses a method of step b, comprising preparing a diol from the reduction of a gamma-butyrolactone (page 1454, Figure 1 'GBL to BDO’).
Regarding claims 41-43, Dzulkefly et al., (The Malay. J. Anal. Sci., 2007, Vol. 11(2): 395-399, in IDS) discloses a method of acylating an alcohol by contacting the alcohol similar to formula IV, with a compound of formula XII wherein R1 is C5-alkyl, to prepare the acylated product similar to that of formula XVII (page 396, Scheme 1, Compound DS1 to DS2).
Regarding claims 103-105, Ikemoto et al., (US 7,468,448 B2) separation, purification and reduction methods of lactones, said separation, purification and reduction methods comprising sodium bicarbonate and reduction method comprising sodium borohydride (see, Abstract; Example 1, col. 49, lines 1-50; and entire document).
Therefore, it would have been obvious to a person of ordinary skill in the art to combine and modify the teachings of Verdin et al., and employ structural and functional elements of the instant invention i.e., a method of making formula XVII contacting racemic β-butyrolactone (formula II) with a lipase (as in claims 41-43 and 102-105) as advantageously suggested by Huang et al., Watanabe et al., Ohlinger et al., Dzulkefly et al., depending on the experimental need and utilize the separation, purification and reduction methods comprising sodium bicarbonate and reduction method comprising sodium borohydride as suggested by Ikemoto et al., because said modifications will lead to a wide repertoire of therapeutic compositions comprising ketone esters, said ketone esters are (R)-1,3, butanediol ester of (R)-3-hydroxybutyrate derivatives and oligomers including applications in pharmaceutical industry. The expectation of success is high, because the combined teachings of Verdin et al., Huang et al., Watanabe et al., Ohlinger et al., Dzulkefly et al., and Ikemoto et al., teach the construction of fusion proteins and said references also provide the structural and functional elements of the instant invention (Teaching, Suggestion and Motivation).
Hence, claims 36-37 and 102-106 are rejected under 35 U.S.C. 103(a) as being unpatentable over 41-43 and 102-105 are rejected under 35 U.S.C. 103(a) as being unpatentable over Verdin et al., (WO 2017/21399 A1) and in view of Huang et al., (Appl. Microbiol. Biotechnol., 2014, Vol. 98: 621-628), Watanabe et al., (US 2006/0046286 A1, in IDS), Ohlinger et al., (Chem. Eng. Sci., 2003, Vol. 58: 1453-1461, in IDS), Dzulkefly et al., (The Malay. J. Anal. Sci., 2007, Vol. 11(2): 395-399, in IDS) and Ikemoto et al., (US 7,468,448 B2).
Allowable Subject Matter/Conclusion
None of the claims are allowable.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to GANAPATHIRAMA RAGHU whose telephone number is (571)272-4533. The examiner can normally be reached on M-F 8:30am-5pm EST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Robert Mondesi can be reached on 408-918-7584. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/GANAPATHIRAMA RAGHU/ Primary Examiner, Art Unit 1652
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