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 .
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.
Claim(s) 1-7 is/are rejected under 35 U.S.C. 103 as being unpatentable over Shen et al. (Organic Letters, 2007) and Begue et al. (Synthetic Communications, 1992) in combination.
The claims are drawn to a method for producing a cyclohexenone compound by isomerization of a raw material including a compound represented by formula (4) and an isomerization catalyst, to form the compound represented by formula (3).
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Further limitations include the isomerization catalyst being a ruthenium-containing catalyst; forming the compound of formula (3) by cyclization of a compound of formula (2) in the presence of a solvent and a strong acid;
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and reacting a compound of formula (1) with methyl vinyl ketone in a solvent, and in the presence of a base, to obtain the compound of formula (2).
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Begue et al. teach a process, wherein a compound represented by instant formula (1) is reacted with methyl vinyl ketone, in the presence of benzene as solvent, and sodium hydride base, to produce a compound represented by formula (2). The compound of formula (2) undergoes cyclization in the presence of acetic acid/piperidine in benzene as solvent, thereby producing a cyclohexene compound (page 574).
The differences between Begue et al. and the present invention are that the former uses acetic acid/piperidine for the cyclization step, not a “strong acid”, such as sulfuric acid (as used in the present examples), and therefore produces a trifluoromethylated cyclohexenone compound that still has a -COOEt group attached to the ring; and, Begue et al. do not teach isomerization of the cyclohexenone ring, resulting in double bond migration.
A person having ordinary skill in the art would know how to substitute the acetic acid/piperidine reagents used in the cyclization step taught by Begue et al. in order to remove the ethyl carboxylate group from the compound of formula (1) taught by Begue et al., if so desired.
Shen et al. teach the isomerization (double bond migration) of a substituted cyclohexenone compound using a ruthenium-containing catalyst, in a dichloromethane solvent, at a temperature of 23°C (page 1058).
In view of the combined reference teachings, it would have been obvious to a person having ordinary skill in the art, looking for a means of isomerizing (migrating the double bond) a substituted cyclohexenone compound, such as compound (1) taught by Begue et al., to employ the process taught by Shen et al., using a ruthenium-containing catalyst, since Shen et al. teach a successful double bond migration for substituted cyclohexenone compounds.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SIKARL A WITHERSPOON whose telephone number is (571)272-0649. The examiner can normally be reached M-F 9am-9pm IFP.
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/SIKARL A WITHERSPOON/Primary Examiner, Art Unit 1692