DETAILED ACTION
Claims 71-78 are currently pending and are examined on the merits herein.
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 .
Application Priority
This application filed 06/26/2024 is a DIV of PAT 12054507( 17/178,156) filed on 02/17/2021 which has PRO 62/977,969 filed on 02/18/2020.
Information Disclosure Statement
The information disclosure statement(s) (IDS) filed on 10/7/2024 are in compliance with the provisions of 37 CFR 1.97. Accordingly, the IDS is being considered by the Examiner.
The following rejections are made:
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.
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.
Claims 71-78 are rejected under 35 U.S.C. 103 as being unpatentable over Butler et al. (WO2011035250 -- IDS).
Butler et al. teaches a method of preparation of
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466
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R1 is H, (C1-C8)alkyl, (C4-C8)carbocyclylalkyl, (C1-C8)substituted alkyl, (C2-C8)alkenyl, (C2-C8) substituted alkenyl, (C2-C8)alkynyl, (C2-C8)substituted alkynyl, or aryl(C! -C8)alkyl;
each R2a or R2b is independently H, F or OR4;
each R3 is independently (Cj-C8) alkyl, (C1-Cs) substituted alkyl, C6— C20 aryl,
C6-C20 substituted aryl, C2-C20 heterocyclyl, C2-C20 substituted heterocyclyl, C7-C20 arylalkyl, C7-C20 substituted arylalkyl, (Cj-C8) alkoxy, or (Cj-Cs) substituted alkoxy; each R* or R7 is independently H, optionally substituted allyl,
Si(R3)3, C(O)R5, C(O)OR5, -(C(R5)2)ra-R15 or
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223
394
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or any two of R4 or R7 when taken together are -C(R19)2-, -C(O)- or
Si(R3)2(X2)mSi(R3)2-; each R15 is independently -0-C(R5)2R6, -Si(R3)3, C(O)OR5, -OC(O)R5 or
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279
487
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each R5, R58 or R19 is independently H, (C1-C8) alkyl, (C1-C8) substituted alkyl, (C2-C8)alkenyl, (C2-Q) substituted alkenyl, (C2-C8) alkynyl, (C2-C8) substituted alkynyl, C6— C20 aryl, C6-C20 substituted aryl, C2-C20 heterocyclyl, C2-C20 substituted heterocyclyl, C7-C20 arylalkyl, or C7-C20 substituted arylalkyl;
each R6 is independently C6— C20 aryl, C6— C20 substituted aryl, or optionally substituted heteroaryl;
each Ra is independently H, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, aryl(C1-C8)alkyl, (C4-C8)carbocyclylalkyl, -C(=O)R' -C(=O)0R' -C(=O)NR' 'R12, -C(=O)SR1 1, -S(O)R1 1, -S(O)2R1 1, -S(O)(OR1 1), -S(O)2(OR1 1), or -SO2NRMR12;
X! is C-R10 or N;
each X2 is O or CH2;
each m is 1 or 2;
each n is independently 0, 1 or 2;
each R8 is halogen, NR1 1R12, N(R1 1)OR1 1, NR1 1NR11R12, N3, NO, NO2, CHO, CH(=NR1 1), -CH=NHNR1 1, -CH=N(OR1 1), -CH(OR1 1)2, -C(=O)NR1 1R12, -C(=S)NR1 LR12, -C(=O)OR1 1, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl,
(C4-C8)carbocyclyIalkyl, optionally substituted aryl, optionally substituted heteroaryl, -C(=O)(C1-C8)alkyl, -S(O)n(C1-C8) alkyl, aryl(C1-C8)alkyl, CN, OR1 1 or SR1 1 ;
each R9or R10 is independently H, halogen, NR1 'R12, NCR1 1)OR1 1,
N(R' ')N(R1 1)(R12), N3, NO, NO2, CHO, CN, -CH(=NR1 1), -CH=NNH(R1 1), - CH=N(OR1 1), -CH(0R' % -C(=O)NR1 1R12, -C(=S)NR "R12, -C(=O)OR, ], R1 1, OR1l or SR 1 1;
each R1 1 or R12 is independently H, (C1-C8)alkyl, (C2-C8)alkenyl, (C2- C8)alkynyl, (C3-C8)carbocyclyl, (C4-C3)carbocyclylalkyl, optionally substituted aryl, optionally substituted heteroaryl, -C(=O)(C1-C8)alkyl, -S(O)n (C1-C8)alkyl, aryl(Ci- C8)alkyl or Si(R3)3; or R1 1 and R12 taken together with a nitrogen to which they are both attached form a 3 to 7 membered heterocyclic ring wherein any one carbon atom of said heterocyclic ring can optionally be replaced with -0-, -S(O)„- or— N a-; or R11 and R12 taken together are -Si(R3)2(X2)niSi(R3)2-;
R17 is OH, OR18, -OC(O)OR18 or -OC(O)R18;
wherein each (C1-Cs)alkyl, (C2-C8)alkenyl, (C -C8)alkynyl or aryl(C1-C8)alkyl of each R1, R3, R4, R5, R6, R18, R19, R1 1 or R12 is, independently, optionally substituted with one or more halo, hydroxy, CN, N , N(Ra)2 or OR"; and wherein one or more of the non-terminal carbon atoms of each said (C1-C8)alkyl is optionally replaced with - 0-, -S(O)n- or -NRa~;
provided that when R17 is OH or OCH3, R1 is H or CH3 and each R2a and R2b is OR4, then each R7 and each R4 is not H. Non-limiting examples of Lewis acids comprising trialkylsilyl groups that are suitable for promoting this conversion are tri-(C1-Ci2 alkyl)silyl -poIyfluoro(C1-C12)alkylsulfonates, trimethylsilyl polyfiuoro(C1- C^alkylsulfonates, trimethylsilyl trifiuoromethanesulfonate, tert-butyldimethylsilyl trifluoromethanesulfonate and triethylsilyl trifiuoromethanesulfonate.
While Butler teaches the components of the reaction, the example of formula I-11 is not specified.
It would have been obvious to one of ordinary skill in the art at the time of filing to modify the Formula IV of Butler. The motivation to modify the Formula IV is because Butler teaches the variables that are compatible for making the formula, and that tert-butyldimethylsilyl are suitable for promoting conversion for the Lewis acids. A skilled artisan would have reasonable expectation of successfully achieving stability.
Conclusion
No claims allowed.
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/LAYLA SOROUSH/ Primary Examiner, Art Unit 1622
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