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) 1-5 is/are rejected under 35 U.S.C. 103 as being unpatentable over Watanabe et al. (us Pub. 2019/0322605, hereafter USPub’605).
Claim 3 is directed to a process for preparing a (4Z,6E)-1-halo-4,6-undecadiene by (i) converting (4Z,6E)-4,6-undecadienyl trimethylacetate to the corresponding (4Z,6E)-4,6-undecadien-1-ol and (ii) halogenating that alcohol.
USPUB’605 discloses a process for preparing a closely related compound, namely (4E,6Z)-1-chloro-4,6-undecadiene. In USPUB’605, 1-bromopentane is reacted with triphenylphosphine and dimethylformamide to give a pentyltriphenylphosphonium intermediate, which is then reacted with potassium t-butoxide and (2E)-6-chloro-2-hexenal (see paragraph [0074], Synthesis Example 1). The product is used as an intermediate in the preparation of pheromonal compounds (paragraphs [0001], [0003]).
The claimed process differs from USPUB’605 in that the product has the (4Z,6E) configuration and the process employs different starting materials. The resulting product is simply the corresponding stereochemical isomer of the compound prepared in USPUB’605.
The record does not show that the stereochemical modification produces any unexpected result. The steps recited in claim 3—hydrolyzing an ester to form the corresponding alcohol and halogenating that alcohol—are basic and well-known synthetic transformations.
A person of ordinary skill seeking to prepare the (4Z,6E) isomer of the known halo-undecadiene would have found it obvious to begin with a starting material already possessing the desired stereochemistry and convert it to the halo compound using conventional reactions. No new carbon–carbon bonds are formed, and the sequence of steps represents routine synthetic practice.
Accordingly, the process of claim 3 would have been obvious in view of USPUB’605, and claims 4 and 5 are also obvious with claim 3.
Regarding claims 1-2
Claim 1 is directed to (4Z,6E)-4,6-undecadienyl trimethylacetate, which is used as the starting material in the process of claim 3. As explained for claim 3, USPUB’605 teaches the preparation of 1-halo-4,6-undecadiene compounds having the same carbon skeleton but a different stereochemical configuration. The only difference between the compound of claim 1 and the intermediates used in USPUB’605 is the geometric configuration of the double bonds and the specific protecting/derivatizing group at the terminal alcohol position.
It is well established in the chemical arts that where the desired final product has a specific stereochemical configuration, the skilled artisan would select a precursor already possessing that same configuration whenever such precursor is commercially available, easily synthesized, or otherwise routine to prepare. Because the applicant’s end product is merely the (4Z,6E) isomer of a compound well known in USPUB’605, a person of ordinary skill would reasonably expect to begin the synthesis from a correspondingly configured starting material.
Esterification of an allylic alcohol with a sterically hindered acyl protecting group such as trimethylacetate (pivalate) is a well-known protecting-group strategy in the organic synthesis arts, and pivalate esters have been widely taught and utilized in the patent literature. For example, patents and published applications recognize acyl protecting groups, including pivaloyl esters, for masking alcohol functionalities to prevent undesired reactions and to simplify downstream chemistry (see US 8,338,620, col. 10-11, discussing alkanoyl protecting groups such as pivaloyl in the context of general protecting group strategies).
Pivalate esters are similarly disclosed as protecting groups in numerous organic synthesis contexts, with explicit mention of their ease of removal by hydrolysis under conventional conditions (see US Pub. 2009/0318434, ¶ [0002] (“a suitable protecting group for a hydroxy group is … pivaloyl”), and methods of deprotection by base-mediated hydrolysis).
Thus, selecting the pivalate ester of a known (4Z,6E) allylic alcohol would have been a predictable and conventional choice that one skilled in the art would utilize to mask an alcohol, control volatility, and provide a stable functional handle for later transformations, particularly where the subsequent step in the process is simple deprotection (e.g., acyl cleavage by hydrolysis).
Accordingly, a person of ordinary skill in the art, having knowledge of USPUB’605 and seeking to prepare the stereochemically inverted halo-undecadiene, would have found it obvious to employ the corresponding precursor bearing the desired double-bond configuration and a routine alcohol-protecting group.
Claim 2 is directed to a process for preparing the compound of claim 1. As noted above, the starting material of claim 1 is itself an obvious intermediate for use in an obvious process (claim 3). The process of claim 2 merely recites obtaining that intermediate via conventional synthetic steps.
Typical methods for preparing pivalate esters from alcohols are well established in the prior art and include reaction of the corresponding alcohol with pivaloyl chloride or related acylating agents in the presence of a base or catalyst. Pivaloyl chloride itself is a known synthetic intermediate produced on industrial scales for use as an acylating agent (see US 6,605,743 B1, teaching continuous preparation of pivaloyl chloride for use in subsequent acylation reactions).
Although that patent does not depict a specific alcohol esterification, the widespread industrial preparation and availability of pivaloyl chloride confirms its conventional use in ester synthesis. Likewise, US Pub. 2001/0011141 disclose methods of reacting pivaloyl chloride with oxygen-containing substrates in the presence of base to form pivaloyl esters as routine transformations, reflecting the common practice of employing pivaloyl chloride for esterification.
In the context of protecting an allylic or homoallylic alcohol, the patent literature is replete with references to acylation protocols that do not indicate unusual challenges with unsaturated alcohol substrates. For example, the conventional teachings of pivalate protecting group introduction and removal (e.g., as noted in US 8,338,620 and US Pub. 2009/0318434) apply to a broad range of alcohols, with no indication in the prior art that a (4Z,6E)-4,6-undecadien-1-ol precursor would exhibit atypical reactivity, instability, or stereochemical sensitivity that would render pivaloylation unpredictable or non-routine. Therefore, formation of the pivalate ester from the corresponding allylic alcohol would have been well within the ordinary skill of the art.
Where a claimed method simply applies well-known acylation chemistry to a known alcohol precursor, without producing any unexpected result or solving any recognized problem in the art, such a method is considered obvious. The applicant has not provided evidence that the claimed process for producing the pivalate ester is conducted under unconventional conditions, provides unexpected advantages, or involves any non-routine steps. The process therefore amounts to no more than the routine application of standard esterification techniques.
It is well-established case law (e.g., In re Durden and later chemical-process cases) that a process of making an obvious compound is itself obvious unless (i) the process employs an unexpected or non-routine technique, or (ii) the process demonstrates unexpected results. Neither is present here.
Therefore, as the method of claim 2 is simply an ordinary method for preparing an intermediate that is itself obvious in view of the process of claim 3,
Allowable Subject Matter
Claim 6 is considered to be allowable over the prior of record.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DEBORAH D CARR whose telephone number is (571)272-0637. The examiner can normally be reached Monday-Friday (10:30 am -7:00 pm).
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/DEBORAH D CARR/ Primary Examiner, Art Unit 1691