DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Status of the Claims
Claims 14-19 are pending. Claims 14-17 are withdrawn as being drawn to a non-elected invention.
Claim Rejections - 35 USC § 103
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.
Claims 18-19 are rejected under 35 U.S.C. 103 as being unpatentable over Langlois et al. (Eur. J. Med. Chem. Chimica Therapeutica, 1978).
Langlois et al. teach the following scheme for the preparation of compounds 5 by method C (pg. 163):
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Langlois et al. further teach compound 5h comprising 3-CF3 substituted phenyl, prepared by method C (Table IV).
Langlois et al. do not explicitly disclose compounds according to instant claims 18 and 19, but they would have prepared the following compounds during the preparation of compound 5h according to the following scheme:
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Therefore, it would have been prima facie obvious for a person of ordinary skill in the art to prepare compound 5h according to the method taught by Langlois et al., which would necessarily produce the compound according to instant claim 19.
Regarding the claimed enantiomer, it would have been obvious for a person of ordinary skill in the art to prepare the claimed enantiomer as opposed to the racemate taught by Langlois et al. See MPEP 2143(I)(B) Example 8.
Regarding the compound according to instant claim 18, it would have been obvious to substitute a methyl ester in the place of the ethyl ester in the compounds above. Such would have been obvious because a methyl is homologous to an ethyl. See MPEP 2144.09(II).
It is noted that the recitation of the intended use “for the preparation of (3S,4S)-N-(2-fluorophenyl)-1-methyl-2-oxo-4-]3-(trifluoromethyl)phenyl]-3-pyrrolidinecarboxamide” has not been given patentable weight to distinguish over Langlois et al. because the intended use of the claimed invention must result in a structural difference between the claimed invention and the prior art in order to patentably distinguish the claimed invention from the prior art. If the prior art structure is capable of performing the intended use, then it meets the claim. See In re Casey, 152 USPQ 235 (CCPA 1967) and In re Otto, 136 USPQ 458, 459 (CCPA 1963). Since Langlois et al. teaches compounds that are the same as those claimed, they would be capable of performing the intended use, as claimed.
Response to Arguments
Applicant's arguments filed 20 March 2026 have been fully considered but they are not persuasive. Applicant argues that the selection and isolation of a single stereospecific compound is a difficult undertaking in practice. The compound of Claim 18 requires not one, but two selections of stereospecific carbon atoms. This is in comparison to the reference compound technically disclosing a mixture of 4 possible combinations of enantiomers. There is no teaching in Langlois et al. to select the specific configuration of both carbon atoms to arrive at the compound of Claim18.
The examiner respectfully argues, as noted by Applicant, that Langlois et al. technically disclose a mixture of 4 possible combinations of enantiomers, including the instantly claimed selection. The presence of additional compounds in the mixture according to Langlois et al. does not exclude the presence of the instantly claimed enantiomer. Therefore, Langlois et al. disclose the claimed enantiomer, even though it is in a mixture with other enantiomers. The instant claims do not exclude other enantiomers from being present in a mixture with the claimed enantiomer. Also, it would have been obvious for a person of ordinary skill in the art to prepare the claimed enantiomer as opposed to the racemate taught by Langlois et al. See MPEP 2143(I)(B) Example 8.
MPEP 2143(I)(B) Example 8 states:
In Aventis Pharma Deutschland v. Lupin Ltd., 499 F.3d 1293, 84 USPQ2d 1197 (Fed. Cir. 2007), the claims were drawn to the 5(S) stereoisomer of the blood pressure drug ramipril in stereochemically pure form, and to compositions and methods requiring 5(S) ramipril. The 5(S) stereoisomer is one in which all five stereocenters in the ramipril molecule are in the S rather than the R configuration. A mixture of various stereoisomers including 5(S) ramipril had been taught by the prior art. The question before the court was whether the purified single stereoisomer would have been obvious over the known mixture of stereoisomers.
The Federal Circuit cautioned that requiring such a clearly stated motivation in the prior art to isolate 5(S) ramipril ran counter to the Supreme Court’s decision in KSR, and the court stated:
Requiring an explicit teaching to purify the 5(S) stereoisomer from a mixture in which it is the active ingredient is precisely the sort of rigid application of the TSM test that was criticized in KSR.
Id. at 1301, 84 USPQ2d at 1204. The Aventis court also relied on the settled principle that in chemical cases, structural similarity can provide the necessary reason to modify prior art teachings. The Federal Circuit also addressed the kind of teaching that would be sufficient in the absence of an explicitly stated prior art-based motivation, explaining that an expectation of similar properties in light of the prior art can be sufficient, even without an explicit teaching that the compound will have a particular utility.
Therefore, MPEP 2143(I)(B) Example 8 states that isolation of the 5(S) stereoisomer in stereochemically pure form was obvious when the mixture of various stereoisomers including 5(S) ramipril had been taught by the prior art. In the instant case, the compound according to claims 18 and 19 have two stereocenters, as opposed to the five stereocenters of ramipril. As stated in the MPEP, isolation of the purified specific stereoisomer claimed would have been prima facie obvious.
Applicant further argues that the second point of improvement lies in the selection of the methyl ester in view of the reference ethyl ester. Applicant asserts that when selected in combination with the stereochemistry described above, the combined selections should be viewed as a non-obvious improvement.
The examiner respectfully argues that structural relationships may provide the requisite motivation or suggestion to modify known compounds to obtain new compounds. For example, a prior art compound may suggest its homologs because homologs often have similar properties and therefore chemists of ordinary skill would ordinarily contemplate making them to try to obtain compounds with improved properties. MPEP 2144.08(II)(A)(4)(c). Thus, it would have been obvious to substitute a methyl ester in the place of the ethyl ester in the compounds above. Such would have been obvious because a methyl is homologous to an ethyl. Compounds which are homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. See MPEP 2144.09(II).
Similarly, as discussed above in MPEP 2143(I)(B) Example 8, that in chemical cases, structural similarity can provide the necessary reason to modify prior art teachings. The Federal Circuit also addressed the kind of teaching that would be sufficient in the absence of an explicitly stated prior art-based motivation, explaining that an expectation of similar properties in light of the prior art can be sufficient, even without an explicit teaching that the compound will have a particular utility.
Applicant argues that the third aspect of improvement lies in the positional selection of the 3-CF3 moiety on the phenyl ring. Applicant asserts that although the Office alleges that compound 5h (not shown) must pass through the intermediate there is no explicit compound disclosed in Langlois et. al. of a 3-CF3 moiety.
The examiner respectfully argues that Langlois et al. teach compound 5h having the 3-CF3 moiety on the phenyl ring (Table IV, No. 5h wherein R1, R2 and R3 are each H, and R4 is 3-CF3). Langlois et al. specifically teach that compound 5h (depicted above) was prepared by method C. As discussed above, the synthesis of compound 5h by method C will necessarily produce the following compounds:
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Applicant further argues that one skilled in the art of herbicide chemistry, when seeking structural activity, synthetic strategy or general chemistry advice are not prone to immediately seek out the teaching of a reference directed to the “Synthesis of Antidepressants...”
The examiner respectfully argues that it has been held that a prior art reference must either be in the field of the inventor’s endeavor or, if not, then be reasonably pertinent to the particular problem with which the inventor was concerned, in order to be relied upon as a basis for rejection of the claimed invention. See In re Oetiker, 977 F.2d 1443, 24 USPQ2d 1443 (Fed. Cir. 1992).
The examiner respectfully argues that the instant claims are drawn to compounds, and their use in organic synthesis. Langlois et al. also teach the synthesis of similar compounds. A person of ordinary skill in the art would have reasonably looked to the organic synthesis art for direction on the synthesis of the compounds according to the instant invention. A person of ordinary skill in the art that is conducting organic synthesis of an agrochemical compound would not limit their search and knowledge to organic synthesis of only agrochemical compounds, but would rather search for organic synthesis in general to determine how to effectively synthesize the desired compounds. Langlois et al. teach the synthesis of compounds or analogs of compounds according to the instant claims. Therefore, a person of ordinary skill in the art would have found the teachings of Langlois et al. as being relevant to the organic synthesis of the instantly claimed compounds.
Conclusion
THIS ACTION IS MADE FINAL. 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.
Contact Information
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Nathan W Schlientz whose telephone number is (571)272-9924. The examiner can normally be reached 10:00 AM to 6:00 PM, Monday through Friday.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Sue Liu can be reached at (571) 272-5539. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/N.W.S/Examiner, Art Unit 1616
/SUE X LIU/Supervisory Patent Examiner, Art Unit 1616
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