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/EP2022/050708 (01/14/2022)
and claims foreign priority to EP 21154605.6 (02/01/2021).
Status
Claims 1-2, 5-12 are pending.
Claim rejections not reiterated in this action are withdrawn.
New Claim Rejections - 35 USC § 103
Claims 1-2, 5-11 are rejected under 35 U.S.C. 103 as being unpatentable over Kienzel et al. (Machine Translation of: Helv. Chimica Acta., v. 58, 1 (1975), No. 4, p. 27-39) in view of Kotha et al. (Heterocycles, v. 90, no. 1, 2015, p. 226-237), Subramanian et al. (Synth. Comm., 27:23, p. 4067-4072), Subramanian et al (Tetrahedron Letters, Vol. 38, No. 14, pp.2585-2586, 1997) (Subramanian-2) and Turk et al. (“Formation of Five-membered Cyclic Sulfones”, chapter 2 in 1,4-Cycloaddition Reactions, Ed. Hamer, Academic Press, 1967, p. 13-45).
Kienzle teaches forming polyene products such as Vitamin A using a scheme such as taught on page 34:
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287
787
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130
781
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118
187
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274
987
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Kienzle’s product, compound 23, corresponds to claim 1’s formula (I) where R is CH3, R1 is
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163
201
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, and Kienzle’s reaction, compound 6, similarly has the same R/R1 meaning as claim 1’s formula (II).
Kienzle does not specify an alcohol solvent.
Kotha teaches in Scheme 3, page 228, the following reaction:
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101
250
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which corresponds to claim 1’s formula (I) when R is CH3, R1 is H, and reacted with SO2 in methanol at rt (20-25C), and has hydroquinone as stabilizer. Kotha teaches the yield was 83%.
Subramanian teaches versatile building blocks for the synthesis of natural products with conjugated diene systems via 3-sulfolenes (p. 4067). Subramanian teaches compound 8 (p. 4069):
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290
334
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which is used in the synthesis of chamigrene.
Subramanian-2 teaches the use of sulfolene in the synthesis of retinoids/Vitamin A as shown in Scheme I.
Turk teaches the well-known synthetic technique of forming cyclic sulfones with dienes exemplified by the following (p. 13):
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93
432
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including a variety of different dienes as shown in Table 1 where an inhibitor/stabilizer is used, including TBP also known as 4-tert-butylcatechol (p. 18-19).
One of ordinary skill in the art following the teaching of Kienzle would have considered the known synthetic techniques such as taught by Kotha which is an analogous reaction, in formulating a synthesis of natural products such as chamigrene and vitamin A as taught by Subramanian and Subramanian-2. One of ordinary skill in the art would have considered utilizing the solvent methanol in the Kienzle process because of Kotha and Turks teaching of success in the related process. One of ordinary skill in the art would be motivated to combine the references because of Kotha’s teaching of high yield of 83%. One of ordinary skill in the art would have had a reasonable expectation of success in the combination to arrive at the claimed invention because of the structural similarities in the products and the well-known technique for using sulfones/sulfolenes as taught by Turk.
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.
Conclusion
Claim 12 as amended is allowable over the prior art of record. No other claims allowable.
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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ROBERT H HAVLIN whose telephone number is (571)272-9066. The examiner can normally be reached 9am - 6pm.
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/ROBERT H HAVLIN/Primary Patent Examiner, Art Unit 1626