CTNF 18/556,343 CTNF 101758 Notice of Pre-AIA or AIA Status 07-03-aia AIA 15-10-aia The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA. Claim Objections 07-29-01 AIA Claim 1 is objected to because of the following informalities: Line 7 “at least one of said R 1 , R 2 , R 3 , R 4 and R 5 ” should be “at least one of said R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 ” . Appropriate correction is required. 07-29-01 AIA Claim 2 is objected to because of the following informalities: Line 5 “at least one of said R 1 , R 2 , R 3 , R 4 and R 5 ” should be “at least one of said R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 ”. Line 5 “R 3 and R 4 ” should be “or R 3 and R 4 ”. Line 6 “R 4 and R 5 ” should be “or R 4 and R 5 ” . Appropriate correction is required. 07-29-01 AIA Claim 3 is objected to because of the following informalities: Line 8 “R 3 and R 4 ” should be “or R 3 and R 4 ” . Appropriate correction is required. Claim Rejections - 35 USC § 103 07-06 AIA 15-10-15 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. 07-20-aia AIA 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. 07-23-aia AIA 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. 07-21-aia AIA Claim s 1-20 are rejected under 35 U.S.C. 103 as being unpatentable over Saudan (WO2012150053), and further in view of Aviron-Violet et al. (EP0000315) Regarding claim 1, Saudan discloses the hydrogenation of a conjugated dienal to a deconjugated enal with the same possible structures as the present application (page 2, lines 14-16) (page 2, lines 20-29) (page 3, lines 1-5). Saudan discloses a Rh(I) complex by reacting a Rh(I) precursor and C 34 -C 60 bidenate diphosphine ligand having a natural bite-angle between 93° and 130° (page 3, lines 8-10). Saudan does not disclose the Rh precursor has at least one CO ligand. Aviron-Violet et al. discloses the hydrogenation of neral or geranial to citronellal with a catalyst consisting of a rhodium derivative and chiral phosphine (paragraph 0004) (paragraph 0005). The rhodium complexes include Rh 4 (CO) 12 and Rh 6 (CO) 16 (paragraph 0018). While neral or geranial are not conjugated dienals, the hydrogenation is done across the same bond as the present invention which is the carbon-carbon double bond (alpha and beta carbons). Therefore, it would have been obvious to one having ordinary skill in the art, before the effective filing date of the claimed invention to improve the catalyst used in Saudan with the Rh CO ligand precursor taught in Aviron-Violet et al. because these ligands are well suited to asymmetric hydrogenation as they provide a high hydrogenation rate and good selectivity (paragraph 0018). Regarding claim 2, Saudan discloses an embodiment of the invention where the structures of formula (I) and (II) are the same as those claimed in the present invention (page 4, lines 7-14). Regarding claim 3, Saudan discloses the substrate of formula (I) is one wherein R 1 , R 2 represent each a hydrogen atom, R 3 , R 4 , R 5 represent each a hydrogen atom or a methyl or ethyl group or a cyclohexyl or phenyl group optionally substituted, provided that at least one of said R 1 , R 2 , R 3 , R 4 and R 5 is not a hydrogen atom; R 3 and R 4 , when taken together, represent a C 4 alkadienyl group optionally substituted (page 5, lines 1-5). Saudan does not mention anything about formula (II), but it is necessary for the R groups to be the same as formula (I) when hydrogenation is done on the alpha and beta carbons. Regarding claim 4, Saudan discloses an example that hydrogenates (2E,4E)-4-methyl-5-(p-tolyl)penta-2,4-dienal and uses no base (page 16, example 2, table 3). Regarding claim 5, the Rh precursor disclosed in Aviron-Violet et al. is Rh 4 (CO) 12 and Rh 6 (CO) 16 (paragraph 0018). Regarding claim 6, Saudan discloses the Rh(I) complex having the formula [Rh(L2)(L)](Y) (page 9, lines 6-10). L2 is a C 34 -C 60 bidenate diphosphine ligand with a natural bite-angle comprised between 93° and 130° (page 7, lines 28-29). Y is a mono-anion which has the capability of being a coordinated anion (page 8, line 4). Saudan discloses L which is a C 5-14 hydrocarbon diene (page 8, line 2) but does not disclose CO in the Rh(I) complex. Aviron-Violet et al. discloses the hydrogenation of neral or geranial to citronellal with a catalyst consisting of a rhodium derivative and chiral phosphine (paragraph 0004) (paragraph 0005). The rhodium complexes include Rh 4 (CO) 12 and Rh 6 (CO) 16 (paragraph 0018). While neral or geranial are not conjugated dienals, the hydrogenation is done across the same bond as the present invention which is the carbon-carbon double bond (alpha and beta carbons). Therefore, it would have been obvious to one having ordinary skill in the art, before the effective filing date of the claimed invention to substitute the hydrocarbon diene in Saudan with the CO ligand taught in Aviron-Violet et al. because these ligands are well suited to asymmetric hydrogenation as they provide a high hydrogenation rate and good selectivity (paragraph 0018). Regarding claim 7, Saudan discloses the structure of compound (A) in the same way as the claimed invention (page 10, lines 15-27) (page 11, lines 1-7) (page 12, lines 17-19) (page 12, lines 23-26). Regarding claim 8, Saudan discloses each R b represents a C 6-10 aromatic group optionally substituted or a cyclohexyl group optionally substituted (page 12, lines 4-5). Regarding claim 9, Saudan discloses the structure of Q in the same way as the claimed invention (page 11, lines 8-21). Regarding claim 10, Saudan discloses L2 has a natural-bite angle comprised between 97° and 120° (page 12, lines 15-16). Regarding claim 11, we see in table 1 of the present invention that the structure of L1 and L2 is (9,9-dimethyl-9H-xanathene-4,5-diyl)bis(diphenylphosphane) and 4,6-bis(diphenylphosphaneyl)-10H-phenoxazine) respectively. Saudan discloses the same structures Lc and Ld (page 15, table 1). These diphosphine ligands are used in the examples below the table (page 15, table 2) (page 16, example 2). Regarding claim 12, Saudan discloses the hydrogenation of (2E,4E)-4-methyl-5-(p-tolyl)penta-2,4-dienal which satisfies the structure limitations of claim 3 and uses no base (page 16, example 2, table 3). Regarding claim 13, the Rh precursor disclosed in Aviron-Violet et al. is Rh 4 (CO) 12 and Rh 6 (CO) 16 (paragraph 0018). Regarding claim 14, Saudan discloses the Rh(I) complex having the formula [Rh(L2)(L)](Y) (page 9, lines 6-10). L2 is a C 34 -C 60 bidenate diphosphine ligand with a natural bite-angle comprised between 93° and 130° (page 7, lines 28-29). Y is a mono-anion which has the capability of being a coordinated anion (page 8, line 4). Saudan discloses L which is a C 5-14 hydrocarbon diene (page 8, line 2) but does not disclose CO in the Rh(I) complex. Aviron-Violet et al. discloses the hydrogenation of neral or geranial to citronellal with a catalyst consisting of a rhodium derivative and chiral phosphine (paragraph 0004) (paragraph 0005). The rhodium complexes include Rh 4 (CO) 12 and Rh 6 (CO) 16 (paragraph 0018). While neral or geranial are not conjugated dienals, the hydrogenation is done across the same bond as the present invention which is the carbon-carbon double bond (alpha and beta carbons). Therefore, it would have been obvious to one having ordinary skill in the art, before the effective filing date of the claimed invention to substitute the hydrocarbon diene in Saudan with the CO ligand taught in Aviron-Violet et al. because these ligands are well suited to asymmetric hydrogenation as they provide a high hydrogenation rate and good selectivity (paragraph 0018). Regarding claim 15, Saudan discloses the structure of compound (A) in the same way as the claimed invention (page 10, lines 15-27) (page 11, lines 1-7) (page 12, lines 17-19) (page 12, lines 23-26). Regarding claim 16, Saudan discloses each R b represents a C 6-10 aromatic group optionally substituted or a cyclohexyl group optionally substituted (page 12, lines 4-5). Regarding claim 17, Saudan discloses the structure of Q in the same way as the claimed invention (page 11, lines 8-21). Regarding claim 18, Saudan discloses that R 11 represents a C 1-4 linear or branched alkyl group, preferably a methyl (page 11, line 15). Regarding claim 19, Saudan discloses L2 has a natural-bite angle comprised between 97° and 120° (page 12, lines 15-16). Regarding claim 20, Saudan discloses L2 has a natural-bite angle comprised between 97° and 120° (page 12, lines 15-16). Conclusion Any inquiry concerning this communication or earlier communications from the examiner should be directed to DAVID A CALDERON whose telephone number is (571)272-9866. The examiner can normally be reached Monday-Friday 8-5PM. Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice. 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If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000. /DAVID ANDREW CALDERON/Examiner, Art Unit 1742 /CHRISTINA A JOHNSON/Supervisory Patent Examiner, Art Unit 1742 Application/Control Number: 18/556,343 Page 2 Art Unit: 1742 Application/Control Number: 18/556,343 Page 3 Art Unit: 1742 Application/Control Number: 18/556,343 Page 4 Art Unit: 1742 Application/Control Number: 18/556,343 Page 5 Art Unit: 1742 Application/Control Number: 18/556,343 Page 6 Art Unit: 1742 Application/Control Number: 18/556,343 Page 7 Art Unit: 1742