DETAILED ACTION
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 .
Response to Amendments and Arguments
Claims 1, 2, 9, 12, 13, 15, 16, 18 and 19 have been amended and are pending in the amendment submitted 10/3/25. Claims 3-8, 10, 11, 14, and 17 have been canceled.
Any rejection and/or objection not specifically addressed below in original or modified form is herein withdrawn.
Applicants have amended independent claims 1 and 19, overcoming the indefiniteness rejection of claims 1, 2, 9, 12, 13, 15, 16, 18 and 19 and the anticipatory rejections of claims 1, 2, 9, 12, 13, 15, 16, and 18.
Applicant’s cancelation of claims 5-7 have rendered the statutory double patenting rejection moot.
With regards to the non-statutory double patenting rejections over 17/932,334 Applicant argues the claims have been amended and requests the rejection be held in abeyance until the claims are otherwise in condition for allowance. While there is no provision in the MPEP for holding a rejection in abeyance, the claims have been amended in both the instant and reference application, and is maintained as modified below to reflect the current claim set and amendments in the reference applications.
With regards to 17/997,675, the reference application is without a response to the outstanding office action with the statutory response period beginning 7/2/25, and thus the rejection is withdrawn as moot. Should the application status change (e.g. revival of the application) the relevance to the instant claims will be revisited.
New Grounds of Rejection- Necessitated by Amendment
As indicated above, the claims have been amended overcoming the anticipatory rejection.
Claim Rejections - 35 USC § 103
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 (i.e., changing from AIA to pre-AIA ) 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.
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, 2, 9, 12, 13, 15, 16, and 18 is/are rejected under 35 U.S.C. 103 as being unpatentable over US 2017/0334878 A1 (’878) in view of US 6,784,137 B2 (’137), US 2012/0190548 A1 (’548), and SUZUKI (Miyaura & Suzuki, Chem. Rev. 1995, 95, 2457–2483).
The claims are generally drawn to a process of synthesizing 6-aryl-4-aminopicolinates of formula I via Suzuki coupling.
’878 teaches the same direct Suzuki coupling on unprotected 4-amino-6-halo picolinates to afford 6-aryl-4-aminopicolinates, using Pd(OAc)2 or PdCl2 with PPh3, carbonate/bicarbonate bases (including K2CO3 and KHCO3), mixed organic/water solvents (e.g., MIBK/MeCN/MeOH/H2O; it also identifies toluene and benzyl alcohol as acceptable organic media), nitrogen sparging prior to catalyst addition, and reaction temperatures about 50–65 °C (’878 [0052], [0069]–[0075], [0078]–[0084]; bases/pH at [0071]; catalysts/ligands at [0072]; solvents/sparge at [0073]–[0074]). ’878’s examples include benzyl and methyl ester substrates and use 4-chloro-2-fluoro-3-methoxyphenylboronic acid as the arylboronic acid (meeting claim 9), with isolation of products after phase separation (meeting claim 2).
While ’878’s examples use 6-chloro substrates, ’137 states that, for these palladium-catalyzed couplings on the 4-aminopicolinate core, the leaving group L can be chlorine, bromine, iodine, or triflate, and that organoboron partners are suitable (’137, col. 5–7). SUZUKI (Miyaura & Suzuki, Chem. Rev. 1995, 95, 2457–2483) provides an overview of Suzuki cross-coupling conditions and specifically states the aryl halide reactivity order (I > OTf > Br » Cl) that underlies the substitution of bromide for chloride in oxidative addition and provides the mechanistic context that oxidative addition is often the rate-determining step in the catalytic cycle and states the relative reactivity order I > OTf > Br » Cl (SUZUKI, Chem. Rev. 1995, at 2461–2462). In view of ’137 and SUZUKI, a person of ordinary skill in the art would have understood that substituting a 6-bromo substrate for the 6-chloro substrate in ’878’s otherwise identical coupling is a routine selection expected to provide the same coupled product under the same Pd(OAc)2/PPh3, base, and temperature conditions.
’878 teaches mixed aqueous/organic solvent systems for the same direct Suzuki process (e.g., MIBK/MeCN/MeOH/H2O, and toluene and benzyl alcohol) but does not explicitly identify THF/water. ’137 shows THF as a Pd-coupling solvent on the same picolinate core (e.g., Ex. 26) and also teaches ACN/H2O as a coupling medium (e.g., Ex. 25), indicating that THF (alone or with water) is a routine cross-coupling solvent. Selecting THF/water from among the known solvent systems for Suzuki couplings would have been a standard choice in view of ’137. The remaining process conditions in claim 1 (bases, catalyst, ligands, deoxygenation, and temperature range) are taught in ’878, providing the use of KHCO3 (claim 18) and K2CO3 ([0071]), PPh3 (claim 15; [0072]), Pd(OAc)2 (claim 16; [0072]), and nitrogen sparging prior to catalyst addition (claim 13; [0075]–[0084]), and its examples are conducted at temperatures within the claimed range ([0073]). ’548 presents additional examples of palladium-catalyzed couplings on closely related 4-amino-6-halo picolinates (and 3-vinyl analogs) under nitrogen sparge with Pd(PPh3)2Cl2 and related Pd catalysts in polar organic solvents at typical cross-coupling temperatures (e.g., 70–120 °C).
Substituting a bromide for a chloride leaving group in a Pd-catalyzed Suzuki coupling is a predictable variation that would have been made with an expectation of success in light of ’137’s teaching that L may be Br or Cl and SUZUKI’s statement that oxidative addition rates decrease in the order I > OTf > Br » Cl. See KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398, 417 (2007) (predictable variation); In re Fout, 675 F.2d 297, 301 (CCPA 1982) (substitution of known equivalent reactants is prima facie obvious absent unexpected results). Selecting THF/water as the solvent is a routine choice among known solvent systems for Suzuki couplings, consistent with ’878’s disclosure of mixed aqueous/organic media and ’137’s use of THF and ACN/H2O on the same core. See KSR, 550 U.S. at 421 (obvious to try among finite predictable options), and In re Aller, 220 F.2d 454, 456 (CCPA 1955) (routine optimization). Combining the direct coupling taught in ’878 with the leaving-group guidance and solvent practices in ’137, supported by the reactivity order set out in SUZUKI, yields the claimed process with each element performing its known function to achieve the anticipated result. See In re Kerkhoven, 626 F.2d 846, 850 (CCPA 1980).
Instant claim 2 is described in ’878’s examples ([0075]–[0084]); claim 9 (4-chloro-2-fluoro-3-methoxyphenylboronic acid) is used as the coupling partner in ’878’s examples; claim 12 (THF/water) is supported by ’137’s THF and ACN/H2O usage on the same core; claim 13 (deoxygenation) is met by ’878’s nitrogen sparging prior to catalyst addition; claim 15 (PPh3) and claim 16 (Pd(OAc)2) are taught in ’878 ( [0072]); and claim 18 (KHCO3) is taught in ’878 ( [0071] and examples).
A reference is good not only for what it teaches by direct anticipation but also for what one of ordinary skill in the art might reasonably infer from the teachings. (In re Opprecht 12 USPQ 2d 1235, 1236 (Fed Cir. 1989); In re Bode 193 USPQ 12 (CCPA) 1976). In light of the foregoing discussion, the Examiner concludes that the subject matter defined by the instant claims would have been obvious within the meaning of 35 USC 103(a). From the teachings of the references, it is apparent that one of ordinary skill in the art would have had a reasonable expectation of success in producing the claimed invention. Therefore, the invention as a whole was prima facie obvious to one of ordinary skill in the art at the time the invention was made, as evidenced by the references, especially in the absence of evidence to the contrary.
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, 2, 9, 12, 13, 15, 16, and 18 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-18 of copending Application No. 17/932,334 (reference application). Although the claims at issue are not identical, they are not patentably distinct from each other.
The instant claims are described above.
’334 claims and teaches a direct Suzuki coupling on unprotected 4-amino-6-halo picolinates (Formula A) to prepare 6-aryl-4-aminopicolinates (Formula I) using the 6-bromopicolinate instantly claimed. The coupling partner is an arylboron reagent (boronic acid or boronate ester) (’334 claim 1).
’334 claims the same process used for that direct coupling including palladium catalysts: palladium(II) acetate (Pd(OAc)2) and palladium(II) chloride (PdCl2) (’334 claims 1 and 16); optional ligands: phosphines including triphenylphosphine (PPh3) (’334 claims 14 and 15); bases: carbonates, bicarbonates, acetates, hydroxides, phosphates, amines, and related salts, including potassium bicarbonate (KHCO3) and potassium carbonate (K2CO3) (’334 claims 17 and 18); solvents: mixed aqueous/organic systems drawn from MIBK, acetonitrile (MeCN), THF, MeOH, benzyl alcohol, toluene, water, and combinations (’334 claims 11 and 12; deoxygenation (e.g., nitrogen sparge) of the reaction mixture before adding the palladium catalyst/ligand (’334 claim 13); temperature: about 25–100 °C (’334 claim 1); and isolation of the coupled 6-aryl-4-aminopicolinate from the reaction mixture (’334 claim 2). ’334 also claims and exemplifies the specific arylboronic acid 4-chloro-2-fluoro-3-methoxyphenylboronic acid as the coupling partner in this process (’334 claim 10).
The instantly claimed process would have been an obvious implementation of the direct Suzuki process of ’334. Selecting particular members (e.g., a named base, solvent pair, ligand, or catalyst) from expressly claimed families in ’334 is routine optimization that does not confer patentable distinctness.
The additional dependent limitations in the instant claims are claimed as alternatives in ’334 and would have been obvious, as they are the same recited steps, conditions, or reaction modifications-isolating the coupled product after reaction, using 4‑chloro‑2‑fluoro‑3‑methoxyphenylboronic acid, using in THF/water, deoxygenating the mixture before adding Pd, using triphenylphosphine as ligand and palladium acetate as catalyst, and potassium bicarbonate as base. See KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398, 417 (2007) (predictable variation); In re Fout, 675 F.2d 297, 301 (CCPA 1982) (substitution of known equivalent reactants is prima facie obvious absent unexpected results); KSR, 550 U.S. at 421 (obvious to try among finite predictable options), and In re Aller, 220 F.2d 454, 456 (CCPA 1955) (routine optimization).
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Claims 1, 2, 9, 12, 13, 15, 16, and 18 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-45 of U.S. Patent No. 10087164 (‘164) in view of US 2017/0334878 A1 (’878) in view of US 6,784,137 B2 (’137), US 2012/0190548 A1 (’548), and SUZUKI (Miyaura & Suzuki, Chem. Rev. 1995, 95, 2457–2483), discussed above.
The instant claims and teachings of ‘878, ‘137, ‘548, and Suzuki are above.
‘164 is drawn to the Suzuki coupling process utilizing a 6-chloropicolinate, where the instant claims are drawn to using the 6-bromo, under the same conditions, using the same catalysts, reactants, and reagents. Substituting a bromide for a chloride leaving group in a Pd-catalyzed Suzuki coupling is a predictable variation that would have been made with an expectation of success in light of ’137’s teaching that L may be Br or Cl and SUZUKI’s statement that oxidative addition rates decrease in the order I > OTf > Br » Cl. See KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398, 417 (2007) (predictable variation); In re Fout, 675 F.2d 297, 301 (CCPA 1982) (substitution of known equivalent reactants is prima facie obvious absent unexpected results).
Allowable Subject Matter
Claim 19 is allowed. While Formula E2 is referenced in US Patents 12017993 and 1401242, the patents do not constitute prior art and neither is applicable under double patenting, as the claims are not drawn to a synthetic method, nor does it suggest isolation of compounds of Formula E2 during the synthesis.
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 Andrew D Kosar whose telephone number is (571)272-0913. The examiner can normally be reached Monday-Friday, 7am-3:30pm.
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/Andrew D Kosar/ Supervisory Patent Examiner, Art Unit 1625