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 .
Priority
This application is a 371 of PCT/IB2022/051869 (03/03/2022)
and claims foreign priority to ITALY 102021000005321 (03/08/2021).
Status
Rejections not reiterated in the action are withdrawn.
New Claim Rejections - 35 USC § 103
Claims 1-13 and 16 are rejected under 35 U.S.C. 103 as being unpatentable over Bi et al. (CN101279973, citations to English translation) in view of Zhen et al. (CN1546492A (2004-11-17, machine translation)), Formenti et al. (Chem. Eur. J. 2020, 26, p. 15589 – 15595, p. S1-S46), and Johnson-Matthey (Chemical Catalyst – Product List, 2013, 6 pages).
Bi teaches the synthesis of 1.8-diaminebicyclo(5,4,0)-7-undecene (DBU) (corresponding to instant claim 1’s formula (V)) in three steps: addition - caprolactam (corresponding to instant claim 1’s formula (I)) and acrylonitrile (corresponding to instant claim 1’s formula (II)) in t-butanol with catalytic NaOH to form cyanoethyl caprolactam (corresponding to instant claim 1’s formula (III)) at 10-50C; hydrogenation of the formed cyanoethyl caprolactam directly in the same solvent using a Raney-Ni catalyst under 5 MPa hydrogen at 115C to form the amine (corresponding to instant claim 1’s formula (IV)); and cyclization/dehydration with a p-toluenesulfonic acid at 150-180C (Abstract, pages 1-4).
Bi differs from claim 1 by the catalysts used – i.e., Raney-Ni vs. the claim’s “not of the Raney type or of the sponge type”.
Zhen teaches the synthesis of 1.8-diaminebicyclo(5,4,0)-7-undecene (DBU) (corresponding to instant claim 1’s formula (V)) in three steps: A) caprolactam (corresponding to instant claim 1’s formula (I)) and acrylonitrile (corresponding to instant claim 1’s formula (II)) in toluene with catalytic NaOH or KOH to form cyanoethyl caprolactam (corresponding to instant claim 1’s formula (III)) at 50-60C; B) hydrogenation of cyanoethyl caprolactam using an “catalyst of Al, Ni, Fe, and Cr” “prepared in a mass percentage ratio of 50:40:7:3” under hydrogen at 90-120C to form the amine (corresponding to instant claim 1’s formula (IV)); and C) cyclization with a “0.5-2 wt% of catalyst antimony trioxide” at 150-160C (Abstract, claims 1-2).
Formenti teaches Co catalysts for “efficient and general nitrile hydrogenation” that “outperformed all other tested commercial catalysts, for example, Raney Nickel” (title, abstract).
Johnson-Matthey teaches commercially available catalysts including “HTC CO 2000 RP 1.2” for “hydrogenation of nitriles” (p. 4).
One of ordinary skill in the art following the teaching of Bi and Zhen would have considered utilizing different catalysts known in the art for hydrogenation of nitriles such as those taught by Formenti and Johnson-Matthey. One of ordinary skill in the art would have been motivated to substitute a catalysts because such modifications are routinely done to employ improved efficiency catalysts and commercially available catalysts. Furthermore, such a modification is a substitution of a known equivalent which is prima facie obvious. MPEP 2144.06.
Thus, claims 1-3, 6-10 are obvious.
Regarding claim 4, Bi teaches in Example 1, 50.2g acrylonitrile to 100g caprolactam is (0.95:0.88 = 1.08).
Regarding claim 5, Bi teaches in Example 1 step A at 40C and at atmospheric pressure. Regarding the time of reaction, Bi teaches 1 hour.
Regarding claim 11, Zhen teaches the reaction is performed in a reactor with stirring such the one of skill in the art would at once envisage a stirred reactor CSTR. MPEP 2131.02.III.
Regarding claim 12, Bi teaches the use of p-toluenesulfonic acid in the condensation reaction but does not teach the claimed solvent. Formenti teaches the hydrogenation reaction is general across a variety of solvents including xylene which one of ordinary skill in the art would have considered given the success of the prior art. Regarding claim 13, Bi teaches a heterogenous catalyst based on resins.
Regarding claim 16, the combined teaching of the prior art teaches hydrogenation in the absence of ammonia and in the presence of water and one of ordinary skill in the art would have routinely optimized the solvent, ratios, temperature, and pressure as these are all well-known results effective variable in the optimization of products in a synthetic scheme.
Claims 14-15 are rejected under 35 U.S.C. 103 as being unpatentable over Bi et al. (CN101279973, citations to English translation) in view of Zhen et al. (CN1546492A (2004-11-17, machine translation)), Formenti et al. (Chem. Eur. J. 2020, 26, p. 15589 – 15595, p. S1-S46), Johnson-Matthey (Chemical Catalyst – Product List, 2013, 6 pages) as applied to claims 1-13 and 16 above and further in view of Couper (Chemical Process Equipment, 3rd ed., 2012, 838 pages).
Regarding claim 14 to a continuous process in a solvent of xylene, one of ordinary skill in the art would have considered scaling up the obvious process for production of the commercially important pharmaceutical intermediate of DBU in a continuous process using xylene as a solvent with a reasonable expectation of success.
Regarding claim 15, the modified teaching of the prior art does not teach scaling up the reaction to industrial scale. However, Couper teaches reactor design including evaporators, distillation columns, heat exchangers, fixed bed and trickle bed reactors, and the significance of WHSV which were all well-known in the art and are part of the requisite in reaction optimization when scaling up. Thus, one of ordinary skill in the art following the teaching of the prior art utilizing their high level of skill in view of the well-known techniques of scaling up reactions would have arrived at the claimed invention with a reasonable expectation of success.
With each of the claims, the level of skill in the art is very high such that one of ordinary skill in the art would consider routine the combination of elements from the teaching of the art. One of ordinary skill in the art would have recognized that the results of the combination would be predictable due to the well-known nature and optimizations routinely performed in the art. Thus, one of ordinary skill in the art would have arrived at the invention as claimed before the effective filing date with a reasonable expectation of success.
New Double Patenting
Claims 1-16 are provisionally rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-11 of copending Application No. 18549412 (reference application) in view of Bi et al. (CN101279973, citations to English translation) in view of Zhen et al. (CN1546492A (2004-11-17, machine translation)), Formenti et al. (Chem. Eur. J. 2020, 26, p. 15589 – 15595, p. S1-S46), Johnson-Matthey (Chemical Catalyst – Product List, 2013, 6 pages). Although the claims at issue are not identical, they are not patentably distinct from each other because the reference application claims the synthesis of the same product as in the instant application such that one of ordinary skill in the art would find using the same intermediates in the same fashion in view of the prior art as detailed in the 35 USC 103 rejection supra and arrive at the claimed invention with a reasonable expectation of success.
This is a provisional nonstatutory double patenting rejection because the patentably indistinct claims have not in fact been patented.
Conclusion
No claims allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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.
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/ROBERT H HAVLIN/Primary Patent Examiner, Art Unit 1626
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