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
Status of the Claims
Claims 1-13 are pending and are examined on their merits.
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Information Disclosure Statement
The Information Disclosure Statement filed on April 18th 2024 is in compliance with the provisions of 37 CFR 1.97 and has been considered in full. A signed copy of references cited from the IDS is included with this Office Action.
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, 13, and their dependent claims 2-12 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.
The phrases "optionally" and “particularly” render the claims indefinite because it is unclear whether the limitations following the phrases are part of the claimed invention. See MPEP § 2173.05(d).
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.
Claims 1-9 and 11-13 are rejected under 35 U.S.C. 103 as being unpatentable over McLaughlin (McLaughlin et al., Organic Letters 2006 8 (15), 3311-3314) in view of Zhaoguang (Zhaoguang et al., Organic Letters 2008 10 (15), 3263-3266) and Williams (US 2007/0293508A1 published on December 20th 2007).
The claims are directed towards a method for producing a compound of Formula (I):
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167
215
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from a compound of Formula (II):
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167
182
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comprising:
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161
625
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.
This reaction involves the cyclization of a terminal urea moiety wherein the nitrogen forms a bond with the pyridine core structure, kicking off the leaving group, L.
Such reactions are found in the art in McLaughlin:
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329
341
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(McLaughlin, pg. 3313, Table 3).
McLaughlin’s cyclization reaction differs from applicant’s reaction in the use of a palladium catalyst in place of applicant’s copper catalyst, and the lack of the diamine additive as described by applicant. However, one of ordinary skill in the art would have a reasonable expectation of success in using both a copper catalyst and a diamine additive in this cyclization reaction, because both are known to be used in urea cyclization reactions.
For example, Zhaoguang teaches the following copper-catalyzed urea cyclization:
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374
334
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(Zhaoguang, pg. 3264, Table 1).
As urea cyclization reactions are known in the art to be catalyzed by catalysts such as CuI, one of ordinary skill in the art would have a reasonable expectation of success in using such a catalyst in the terminal urea cyclization described by McLaughlin.
Regarding the diamine additive, they are similarly known in the art to be used in urea cyclizations. See Williams, who teaches the following urea cyclization in the presence of a CuI catalyst, potassium carbonate, and diamine additives:
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467
318
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(Williams, pg. 10).
As such diamine additives are known to be used in in urea cyclizations, and copper catalysts are known to catalyze urea cyclization reactions, one of ordinary skill in the art would have a reasonable expectation of success in using such an additive and catalyst in the terminal urea cyclization described by McLaughlin, and claim 1 is prima facie obvious.
Claim 2 requires that, in the method of claim 1, the leaving group L is a halogen. McLaughlin teaches a chlorine leaving group (McLaughlin, pg. 3313, Table 3, above), and claim 2 is thereby prima facie obvious.
Claim 3 requires that, in the method of claim 1, the leaving group L is chloride. McLaughlin teaches a chlorine leaving group (McLaughlin, pg. 3313, Table 3, above), and claim 3 is thereby prima facie obvious.
Claim 4 requires that, in the method of claim 1, the copper catalyst is a Cu(I) or Cu(II) salt. As the catalyzation of the reaction with CuI is prima facie obvious (see the above 103 rejection for claim 1), claim 4 is prima facie obvious.
Claim 5 requires that, in the method of claim 1, the copper catalyst is CuI. As the catalyzation of the reaction with CuI is prima facie obvious (see the above 103 rejection for claim 1), claim 5 is prima facie obvious.
Claim 6 requires that, in the method of claim 1, the amount of copper catalyst is between 0.1 and 0.6 equivalents of the compound of Formula (II). Zhaoguang teaches reaction conditions wherein the reactant (i.e. the analogous compound of Formula (II)) is present at 0.5 mmol and the CuI catalyst is present at 0.1 mmol (Zhaoguang, pg. 3264, Table 1). This is equivalent to a 0.2:1 catalyst:reactant ratio, and claim 6 is thereby prima facie obvious.
Claim 7 requires that the solvent in the method of claim 1 is an organic solvent or mixture of organic solvents, with a water content of 0-50%. McLuaghlin teaches organic solvents including toluene and i-PrOH, with a maximum water content of 1250 ppm (0.125%). Claim 7 is thereby prima facie obvious.
Claim 8 requires that the diamine additive of claim 1 is a bidentate ligand. Williams teaches trans-1,2-diaminocyclohexane (DACH) and as the diamine additive (Williams, pg. 10, above), and claim 8 is thereby prima facie obvious.
Claim 9 requires that the diamine additive of claim 8 is DACH. Williams teaches DACH as the diamine additive (Williams, pg. 10, above), and claim 8 is thereby prima facie obvious.
Claim 11 requires that the inorganic base of claim 1 is a carbonate or bicarbonate salt. McLaughlin teaches sodium bicarbonate as the inorganic base (McLaughlin, pg. 3313, Table 3, above), and claim 11 is prima facie obvious.
Claim 12 requires that the inorganic base of claim 1 is present in an amount less than 5.0 equivalents in relation to the compound of Formula (II). McLaughlin teaches sodium carbonate present at 300 mol% in relation to the compound of Formula (II) (McLaughlin, pg. 3313, Table 3, above), and claim 12 is prima facie obvious.
Claim 13 is directed towards a method of producing an acid adduct of a compound of Formula (I) via
Producing the compound of Formula (I) via the method described in claim 1.
Reacting the compound of Formula (I) with an acid.
Regarding the production method described in claim 1, it is prima facie obvious for the reasons stated in the above 103 rejection of claim 1. Regarding the production of an acid adduct, by definition, an acid adduct is formed by the reaction of a Lewis base with an acid. Therefore, one of ordinary skill in the art would have a reasonable expectation of success in reacting an acid with a compound of Formula (I) to form an acid adduct of the compound, and claim 13 is prima facie obvious.
Claims 10 is rejected under 35 U.S.C. 103 as being unpatentable over McLaughlin in view of Zhaoguang and Williams and in further view of Surry (Surry et al., Diamine Ligands in Copper-Catalyzed Reactions. Chem Sci. 2010;1(1):13-31).
Claim 10 requires that, in the method of claim 9, the diamine additive is ethylenediamine (EDA). For the teachings of McLaughlin, Zhaoguang, and Williams as they are relevant to claim 9, see the above 103 rejection of claim 9.
Regarding the use of EDA as the diamine additive in place of DACH, while both are known in the art to be useful ligands in copper catalyzed reactions (Surry, pg. 1, Abstract), one of ordinary skill in the art would have a reasonable expectation of success in choosing EDA over DACH, because ethylenediamine-based ligands (such as EDA) are known to be a lower cost choice in comparison to cyclohexanediamine-based ligands (such as DACH) (Surry, pg. 2, paragraph 3). One of ordinary skill in the art would therefore have a reasonable expectation of success in using EDA as the diamine additive in the method of claim 9 and claim 10 is prima facie obvious.
Conclusion
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/A.J.S./Examiner, Art Unit 1629
/JEFFREY S LUNDGREN/Supervisory Patent Examiner, Art Unit 1629