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 .
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 1-3, 5-11, and 13-20 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 C34-C60
bidenate diphosphine ligand having a natural bite-angle between 93° and 130° (page 3, lines 8-10). 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, N° 1). The example has a low conversion, but a higher selectivity of the desired product compared to the other trials in the table. 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 Rh4(CO)12 and Rh6(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 R1, R2 represent
each a hydrogen atom, R3, R4, R5 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 R1, R2, R3, R4 and
R5 is not a hydrogen atom; R3 and R4, when taken together, represent a C4 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 5, the Rh precursor disclosed in Aviron-Violet et al. is Rh4(CO)12 and Rh6(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 C34-C60 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 C5-14 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 Rh4(CO)12 and Rh6(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 Rb represents a C6-10 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 13, the Rh precursor disclosed in Aviron-Violet et al. is Rh4(CO)12 and Rh6(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 C34-C60 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 C5-14 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 Rh4(CO)12 and Rh6(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 Rb represents a C6-10 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 R11 represents a C1-4 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).
Response to Arguments
Applicant's arguments filed 06/24/2026 have been fully considered but they are not persuasive. Applicant argues that Aviron-Violet et al. discloses a different reaction context and selectivity because the reactant, neral/geranial, is not a conjugated dienal and the hydrogenation is an asymmetric hydrogenation. As a result, Aviron-Violet et al. does not establish sufficient basis to modify the catalyst in Saudan with a Rh(I) complex derived from a CO-containing precursor.
Applicant’s reply fails to address similarities of regioselectivity in the hydrogenation reaction of Aviron-Violet et al. and the present invention. Additionality, the asymmetric hydrogenation of Aviron-Violet et al. is not relevant because it is not precluded from the claims and conjugated dienals/dienones of the present application can also be asymmetrically hydrogenated.
There are similarities of regioselectivity between Aviron-Violet et al. and the present application because of the reactants and products in the hydrogenation reaction. Aviron-Violet et al. discloses the reactants geranial and neral and the product citronellal (paragraph 0005). The hydrogenation of geranial/neral to produce citronellal happens across the alpha and beta carbons; the same carbons as
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the present invention (see figures below).
The reactants neral and geranial also require selective α,β-alkene reduction because of additional carbon double bonds that can be hydrogenated (see the arrows above). One having ordinary skill in the art would have had a reasonable expectation of success for the same catalyst to hydrogenate the same alpha beta carbons in a conjugated dienal/dienone because of the structural similarity in reactant and product. This rationale is further supported because the carbon double bond closest to the carbonyl (α,β-alkene) in Formula (I), neral, and geranial is most reducible since the carbonyl pulls electron density away from the alpha beta carbons.
Based off these similarities, the reaction context of Aviron-Violet et al. is very close to the present invention and provides sufficient basis to modify the catalyst in Saudan.
Applicant’s arguments with respect to claims 1-20 have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument. Regarding the CO ligand, Aviron-Violet et al. does provide sufficient basis to modify the catalyst in Saudan with a CO ligand. Regarding the absence of a base, Saudan provides an example that hydrogenates (2E,4E)-4-methyl-5-(p-tolyl)penta-2,4-dienal with no base and actually has a higher selectivity than the other experimental trials (page 16, example 2, table 3, N° 1).
Conclusion
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 A CALDERON whose telephone number is (571)272-9866. The examiner can normally be reached Monday-Friday 8-5PM.
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/DAVID ANDREW CALDERON/Examiner, Art Unit 1742
/BENJAMIN A SCHIFFMAN/Primary Examiner, Art Unit 1742
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