DETAILED ACTION
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 .
Change of Examiner
This application has been reassigned to Examiner Valenrod whose contact information is provided in the conclusion portion of this document.
Election/Restrictions
Upon further review, the restriction requirement set forth on 2/9/2026 is withdrawn. Claims 47-73 are considered on the merits.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 51, 53, 59, 61, 62, 64, 67 and 68 rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance:
Claim 51 recites the broad recitation “0.5% - 5%” and the claim also recites “1% - 3%” and “1.5% - 3%” with regards to Pd catalyst, which are the narrower statement of the range/limitation.
Claim 51 recites the broad recitation “0.5% - 5%” and the claim also recites “1% - 3%” and “1.5% - 3%” with regards to ligand, which are the narrower statement of the range/limitation.
Claim 53 recites the broad recitation “45OC to 100OC”, and the claim also recites 55OC to 100OC and 55OC to 83OC which are the narrower statement of the range/limitation.
Claim 59 recites the broad recitation “1:1 to 3:4”, and the claim also recites 3:4 ratio which is the narrower statement of the range/limitation.
Claim 61 recites the broad recitation “benzyl bromide is 1.0 time or more than 1.0 time”, and the claim also recites 1.0 to 4.0, 1.0 to 1.5 and 1.1 to 1.7 which are the narrower statement of the range/limitation.
Claim 62 recites the broad recitation “sodium tert-pentoxide is 1.0 time or more than 1.0 time”, and the claim also recites 1.0 to 4.0, 1.0 to 1.5 and 1.1 to 1.7 which are the narrower statement of the range/limitation.
Claim 64 recites the broad recitation “room temperature to 900C”, and the claim also recites 30OC to 90OC and 30OC to 60OC which are the narrower statement of the range/limitation.
Claim 67 recites the broad recitation of reagents for acidic conditions, and the claim also recites 2 narrower scopes of the same reagents as preferred embodiments which are the narrower statement of the limitation.
Claim 68 recites the broad recitation 50O to 75OC, and the claim also recites 50OC to 70OC which is the narrower statement of the range/limitation.
The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims.
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.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 65-66, 68 and 73 is/are rejected under 35 U.S.C. 103 as being obvious over Wang et al (US 12,527,763).
The applied reference has a common applicant with the instant application. Based upon the earlier effectively filed date of the reference, it constitutes prior art under 35 U.S.C. 102(a)(2).
This rejection under 35 U.S.C. 103 might be overcome by: (1) a showing under 37 CFR 1.130(a) that the subject matter disclosed in the reference was obtained directly or indirectly from the inventor or a joint inventor of this application and is thus not prior art in accordance with 35 U.S.C.102(b)(2)(A); (2) a showing under 37 CFR 1.130(b) of a prior public disclosure under 35 U.S.C. 102(b)(2)(B); or (3) a statement pursuant to 35 U.S.C. 102(b)(2)(C) establishing that, not later than the effective filing date of the claimed invention, the subject matter disclosed and the claimed invention were either owned by the same person or subject to an obligation of assignment to the same person or subject to a joint research agreement. See generally MPEP § 717.02.
Scope of prior art
Wang teaches preparation of:
PNG
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310
306
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Greyscale
The synthesis comprises the step of removal of benzyl protecting group from a racemic compound followed by chiral resolution to obtain the (S) isomer. Deprotection is carried out in the presence of palladium and hydrogen gas in methanol solvent.
Ascertaining the difference
Claim 65 is directed to a deprotection reaction of the (S) isomer, while art teaches deprotection of a racemate followed by resolution to obtain the (S) isomer.
Obviousness
At issue is whether it would have been obvious for a skilled artisan to change the order of the steps in Wang. Meaning, would it have been obvious to carry out the resolution first and then remove the benzyl group by a reduction with Pd/H2. There are two possible solutions for arriving to the deprotected (S) isomer from a benzyl protected racemate.
Solution 1 is to first deprotect and then to resolve the isomers.
Solution 2 is to first resolve the isomers then deprotect.
Wang teaches how to carry out both a resolution step and a deprotection step and provides motivation to prepare the final product.
The KSR Court recognized that “[w]hen there is a design need or market pressure to solve a problem and there are a finite number of identified, predictable solutions, a person of ordinary skill has good reason to pursue the known options within his or her technical grasp.” KSR, 550 U.S. at 421, 82 USPQ2d at 1397. In such circumstances, “the fact that a combination was obvious to try might show that it was obvious under § 103.”
In the current case, the method of claims 65-66, 68 and the compound of claim 73 represent one of two possible solutions to preparation of the deprotected (S) product. A person of ordinary skill can readily recognize that reversing the order of steps is another solution to the same problem. A skilled artisan, prior to the earliest effective filing date of the current application would have found it obvious to arrive at the deprotected (S) isomer by reversing the sequence of steps taught by Wang. It would have been obvious to first resolve the isomers and then to deprotect the (S) isomer to arrive at the same product.
Allowed claims
Claims 47-50, 52, 54-58, 60, 63 and 72 are allowed. Closest art is Wang et al, who teaches preparation of the same product but uses acyl chloride and substituted aniline to arrive at the core structure (see scheme 1, column 37). This is materially different from the Pd catalyzed coupling reaction between in current claim 47. Additionally Wang does not resolve the isomers until the end of the synthesis, while current claims are directed to a process that begins with a chiral starting material and the stereocenter is preserved through the synthetic steps.
Conclusion
Claims 47-73 are pending
Claims 47-50, 52, 54-58, 60, 63 and 72 are allowed
Claims 69-71 are objected to
Claims 51, 53, 59, 61, 62, 64-68 and 73 are rejected
Any inquiry concerning this communication or earlier communications from the examiner should be directed to YEVGENY VALENROD whose telephone number is (571)272-9049. The examiner can normally be reached Mon-Fri 9am-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.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Amy L Clark can be reached at 571-272-1310. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/YEVGENY VALENROD/Primary Examiner, Art Unit 1628
