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 .
Amended claims 1, 6-15 are pending.
Claim Rejections - 35 USC § 103
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.
Previously presented rejection of claims 1, 6-15 rejected under 35 U.S.C. 103 as being unpatentable over Zaidlewicz, 2011 Science of Synthesis, 2: Stereoselective Synthesis 2, page 59-131, further in view of Cheung, Org.Lett.,Vol.9,No.22,2007, Parekh, Catal. Sci. Technol., 2012, 2, 406–414, Okano, Tetrahedron Letters 41 (2000) 9277-9280 is maintained for reasons of record.
Cheung, Parekh and Okano are new references added to augment previously stated rationale.
Amendment to base claim 1 to limit the catalysts is noted.
Applicants arguments focus on the structural aspect of the ketones and catalysts
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This specious argument contradicts the multiple possibilities for II, multiple possibilities for Ru catalyst, and the wide possibilities of process parameters recited in the claims. There is but one, o n e example for II and few Ru IIIa, IIIb, IVa, IVb, and narrow possibilities of other process parameters such as solvent and H donor in the disclosure. Such wide breadth in claims is inconsistent with the ‘proven results’ pointed out by Applicant at the bottom of Remarks page 10 onto first full paragraph of page 11.
That structurally diverse ketones can be reduced is known in the prior art as taught by Cheung, Parekh and Okano. That said, these references do make clear that obtaining predictable useful ee depends on the structure of (the ketones and) catalyst: see Cheung page 4661, column B last paragraph onto column A last paragraph; Parekh at column A page 410 conclusion; and Okano bottom of page 9279 onto page 9280. Further catalysis is generally considered unpredictable merely from the chemical nature of the catalyst as acknowledged in Corona Co. v. Dover; (USSC 1928) 276 US 358, 369. Catalytic effects are not ordinarily predictable with certainty. In re Doumani et al. (CCPA 1960) 281 F2d 215, 126 USPQ 408. The effect of a modification of one prior art catalytic process in a manner employed in another prior art process which employs a different catalyst was held unpredictable in Ex parte Berger et al. (POBA 1952) 108 USPQ 236. As such the argued upon ‘proven results’ can be acknowledged only for the narrow combination of possibilities with respect to the ketone and catalyst(s) and process parameters as per the disclosure in Table 1.
Suggestion:
Amend limiting ketone as per claim 7; limit catalysts and solvent and H donor as per Table 1.
From previous action:
Zaidlewicz teaches asymmetric transfer hydrogenation (ATH) reduction of ketones using chiral Ru catalyst to make chiral alcohols, in organic solvents (bottom of page 65) and in water.(at page 78).
The catalysts include instantly exemplified catalyst, see Scheme 12 at page 67.
Zaidlewicz teaches at page 68 that a variety of ketones, including aryl and heteroaryl pyridyl ketones.
Zaidlewicz teaches mechanistic details of ATH at page 66, Scheme 11. The intermediate 15, shown in the Scheme 11, in the reduction of acetophenone (and the above-pointed out variety of ketones at once suggests that any ketone could be reduced by the catalyst.
Zaidlewicz teaching, line 1 of first full paragraph at page 67, the ‘donor’ see Scheme 11, is the same as exemplified in the instant case (page 21, Table 1 column 5, formic acid and salt (indicated as Reductant).
Zaidlewicz teaching, line 5 of first full paragraph at page 67, also includes the same DMF solvent exemplified in the instant case Table 1 column 4.
Dependent claims:
As such the catalyst(s) (of claims 2-5, 17, ), hydrogen source (of claims 8-11), temperature at pages 70, 75 (of claim 11), solvent (of claim 12) are taught by Zaidlewicz in anticipatory manner. Further instantly recited starting material and product CAS Registry Numbers 247185-54-2 and 247185-52-0 are commercially available and also disclosed by Naik, Chemical Communications (Cambridge, United Kingdom) (2010), 46(25), 4475-4477 (page 4476 column 2 Table 2 entry 2). Thus the starting material and product are also known in anticipatory manner.
Claims 14 is drawn to commonly method for enhancing ee of desired products which entails Camphor sulfonic acid (CSA) to resolve enantiomers of chiral pyridine compounds through the formation of diastereomeric salts. The process relies on the different physical properties of the diastereomers, which allows for their separation by crystallization. For an example of this within the purview of laboratory technicians see Yasuda US 5457201). Claim 15 is drawn to recycling ultimately aimed at increasing ee of desired product, entailing tempo oxidation. For an example of this within the purview of laboratory technicians see Liardo, Eur. J. Org. Chem. 2018, 3031–3035. Yasuda and Liardo procedures are so common that these are not included in the rejection statement.
As such difference if any is in the plethora of possibilities with respect to recited (in the claims) starting materials, products, catalysts, donor (of H) and solvents. The pointed out disclosure, working examples, in the specification is/are limited with respect to these process parameters.
Since all the claimed elements were known in the prior art, one of skilled in the art could have combined the elements as claimed by known methods with no change in their respective functions to arrive at the instantly claimed method. Obviousness can be established by combining or modifying the teachings of the prior art to produce the claimed invention where there is some teaching, suggestion, or motivation to do so found either in the references themselves or in the knowledge generally available to one of ordinary skill in the art.
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 NIZAL S CHANDRAKUMAR whose telephone number is (571)272-6202. The examiner can normally be reached M-F 8-5 EST.
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/NIZAL S CHANDRAKUMAR/Primary Examiner, Art Unit 1625