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
1. This application is a 371 of PCT/US21/39653 06/29/2021, PCT/US21/39653 has PRO 63/045,627 06/29/2020.
Claims 1, 3, 5, 7, 9-14, 31, 37-38, 41, 44-47, 53-57 are pending.
Response to Arguments
2. The rejection of claim(s) 1, 5, 7, 9-14, 31, 54-56 under 35 U.S.C. 103 as being unpatentable over Qiu CN 107915738 A (machine translation) and Nishino US 20080045712 A1 is maintained. Applicants’ representative’s arguments submitted on April 8, 2026 have been fully considered but are not persuasive. Applicant asserts that the International Searching Authority found the claims novel and inventive over QIU. All written opinions of PCT applications are nonbinding and a patent does not issue; and the international preliminary examination report (IPER) is nonbinding on the Elected States. See M.P.E.P. § 1878.01, Item V. Findings of foreign patent offices do not obviate applicant’s burden to comply with the relevant patent statutes of the United States. Also this analysis does not consider Nishino, one cannot show nonobviousness by attacking references individually where the rejections are based on combinations of references. See In re Keller, 642 F.2d 413, 208 USPQ 871 (CCPA 1981); In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986). In response to applicant’s argument that there is no teaching, suggestion, or motivation to combine the references, the examiner recognizes that obviousness may be established by combining or modifying the teachings of the prior art to produce the claimed invention where there is some teaching, suggestion, or motivation to do so found either in the references themselves or in the knowledge generally available to one of ordinary skill in the art. See In re Fine, 837 F.2d 1071, 5 USPQ2d 1596 (Fed. Cir. 1988), In re Jones, 958 F.2d 347, 21 USPQ2d 1941 (Fed. Cir. 1992), and KSR International Co. v. Teleflex, Inc., 550 U.S. 398, 82 USPQ2d 1385 (2007). In this case, Nishino teaches that vinyl amino nitriles are also used in these reactions they would be expected to provide the same or similar results as the vinyl alcohols. This was not a prophetic or generic suggestion since, In the Example 5 on page 4, 3-aminocrotonnitrile was used to make 6-methyl-4-aminopyrimidine with “methyl orthoformate and 1.42 g (17.5 mmol) of 21% by weight ammonia-methanol solution” (the second set of conditions in claim 1). Simply using an alternative known condition is prima facie obvious. Amino groups and hydroxy groups are isosteres, and behave in similar ways in condensation reactions. Finally, while the mechanism is not known for certain the use of ammonia in Qiu suggests that imine formation on carbonyl/enol carbon the -keto-nitriles is involved. This suggests that the claimed process could also be viewed as a reversal of the steps, with the formation of the imine/amine conducted first in the instant case with an isolated intermediate, while it is generated in situ in Qiu after the first reaction. Regardless, based upon the prior art substituting the cyanovinylamines for the cyanovinylalcohols is prima facie obvious.
With respect to claim 31 applicant’s representative argues that the dimethyl acetal is too different than the diethyl acetal suggesting differences in steric bulk electronic effects and solubility will influence the chemical reactivity. There is no evidence in the record to suggest that this is the case. The homologous is very close differing only in single methylene groups. As previously noted applicant elected the entire genus of C1-C10 alkyl, which could have been taken as an admission that any C1-C10 alkyl is an obvious variant each over the other since applicant has identified these as the same species. As explained in the requirement, “[I]f the examiner finds one of the species unpatentable over the prior art, the evidence or admission may be used in a rejection under 35 U.S.C. 103 or pre-AIA 35 U.S.C. 103(a) of the other species.” This is not necessary. As explained in the rejection the dimethyl acetal is slightly more atom economical, easier to form and may offer some improvement in purification since methanol is slightly more volatile having a lower boiling point facilitating removal with less energy.
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.
3. Claim(s) 1, 5, 7, 9-14, 31, 54-56 is/are rejected under 35 U.S.C. 103 as being unpatentable over Qiu CN 107915738 A (machine translation) and Nishino US 20080045712 A1. The factual inquiries set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
Determination of the scope and content of the prior art
(MPEP 2141.01)
Qiu on pages 4- 5 teaches the condensation of the intermediate B to give the compound D by the steps of the instant claims with formamidine salts.1
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These are the claimed compounds B, C and E, where R1 is H, and R3 is alkyl. According to page 10 ammonia is also present in the reaction:
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Ethanol is a preferred solvent as per page 10. This reaction is a condensation with loss of water.
Nishino US 20080045712 A1 teaches the same type of heterocyclization to make the pyrimidine with both cyanovinylalcohols and cyanovinylamines on page 1 [0004] to [0007]. Nishino explains that both E/Z isomers of the acrylonitrile may be used:
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In the first definition of Y, Y is defined as OR and R may be H, a cyanovinylalcohol. In the second set of definitions at paragraph [0010] Y is amino group, a cyanovinylamine. In the Example 5 on page 4, 3-aminocrotonnitrile was used to make 6-methyl-4-aminopyrimidine with “methyl orthoformate and 1.42 g (17.5 mmol) of 21% by weight ammonia-methanol solution” (the second set of conditions in claim 1). According to page 3 “As the solvent to be used, it is not particularly limited so long as it does not inhibit the reaction, and there may be mentioned, for example, an alcohol Such as methanol, ethanol, isopropyl alcohol, n-butyl alcohol…hydrocarbon Such as benzene, toluene, Xylene, mesitylene, etc.;” which meets limitations of claims 10 and 12.
Ascertainment of the difference between the prior art and the claims
The prior art differs only in the use of the cyanovinylamines instead of the cyanovinylalcohols2 in the prior art reaction.
Finding of prima facie obviousness
Rationale and Motivation
(MPEP 2142-2143)
It would have been obvious to one of ordinary skill in the art at the time the claimed invention was made to substitute cyanovinylamines in the reaction of Qiu using cyanovinylalcohols to produce the instant invention. Since Nishino teaches that amino groups are also used in these reactions they would be expected to provide the same or similar results. Finally, while the mechanism is not known for certain the use of ammonia in Qiu suggests that imine formation on carbonyl/enol carbon the b-keto-nitriles is involved. This suggests that the claimed process could also be viewed as a reversal of the steps, with the formation of the imine/amine conducted first in the instant case with an isolated intermediate, while it is generated in situ in Qiu after the first reaction. Regardless, based upon the prior art substituting the cyanovinylamines for the cyanovinylalcohols is prima facie obvious. Claim 31 is drawn to using the dimethyl acetal, while Qiu used the diethyl acetal. Both acetals are expected to work the same, with the former being slightly more atom economical.
Objections
4. Claims 3, 53, 57 are objected to for depending from a rejected base claim, but would be allowable in independent format with the requisite limitations of the base claim and any intervening claim.
Conclusion
5. 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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DAVID K O'DELL whose telephone number is (571)272-9071. The examiner can normally be reached on Monday - Friday 9:30 - 7:00 PM.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Clinton Brooks can be reached on 571-270-7682. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/DAVID K O'DELL/Primary Examiner, Art Unit 1621
1 The machine translation above has mistranslated 甲脒盐 formamidine salt in the first portion to formazan, perhaps by conflating 臜 with 脒.
2 “Turning now to the b-keto-nitriles it is obvious that these (IVa) are in tautomeric equilibrium with the enolic forms (IVb)…”
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[ Chase, B. H.; Walker, James “Preparation of enol ethers from certain β-keto nitriles” Journal of the Chemical Society (1953), 3518-3525, page 3519 ¶ 2, structures IVa and IVb on page 3518].
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