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 .
DETAILED ACTION
Priority
This application claims benefit for foreign priority under 35 U.S.C. § 119(a)-(d) to
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, however the certified copy of priority document (with English language translation) has not been received or made part of the file. Therefore, any priority claim to this document has not been perfected.
Status of Claims
Claims 1-15 are currently pending in the application.
Receipt is acknowledged of amendment / response filed on November 21, 2025 and that has been entered.
Information Disclosure Statement
Receipt is acknowledged of Information Disclosure Statement (IDS), filed on 01/24/2025, which has been entered in the file.
Response to Election/Restriction
In response to the restriction requirement, Applicants have elected Group I, which includes claims 1-10, drawn to a method for preparing chiral nitro derivatives thereof, and the elected species as set forth and found to a Compound of formula 3-2, such as,
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, without traverse, is acknowledged
Claims 11-15 are withdrawn from further consideration pursuant to 37 C.F.R. 1.142 (b) as being drawn to a non-elected subject matters and therefore, the requirement for restriction is still deemed proper made it final.
Applicants preserve their right to file a divisional on the non-elected subject matter.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1 and 2 are rejected under 35 U.S.C. § 102(a)(1) as being anticipated by Shim et al (Catalyst, 2021, IDS). Applicant claims a method for preparing chiral nitro derivatives thereof. Shim et al (2021) teach a similar process having asymmetric organocatalyzed Michael Addition reaction for the preparation of unsaturated nitroalkenes utilizing analogous reagents and reaction conditions [such as,
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, see Scheme 1, page 2 and also,
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, see Table 1, page 3], which anticipates the instantly claimed inventions.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. § 103(a), which forms the basis for all obviousness rejections, set forth in this Office action:
(a) A patent may not be obtained though the invention is not identically disclosed or described as set forth in section 102 of this title, if the differences between the subject matter sought to be patented and the prior art are such that the subject matter as a whole would have been obvious at the time the invention was made to a person having ordinary skill in the art to which said subject matter pertains. Patentability shall not be negative by the manner in which the invention was made.
Claims 1-10 are rejected under 35 U.S.C. § 103(a) as being unpatentable over Shim et al (Catalyst, 2021, IDS) and further in view of Shim et al (Molecules, 2022, IDS). Applicant claims a method for preparing chiral nitro derivatives thereof.
Determination of the scope and content of the prior art (MPEP §2141.01)
Shim et al (2021) teach a similar process for the preparation of unsaturated nitroalkenes utilizing analogous reagents and reaction conditions [such as,
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, see Table 1, page 3]. Shim et al (2022) also teach a similar process having organocatalyzed Michael Addition reaction of Isobutyraldehyde to Maleimides in aqueous media (see abstract and whole reference).
Ascertainment of the difference between the prior art and the claims (MPEP §2141.02)
The difference between the process taught in the references and the claimed process herein lies merely in the variation of reagents and reaction conditions such as, the use of water instead of organic solvent [e.g., chloroform or dichloromethane, Shim et al (2022) page 2, line 6] under specific set of reaction conditions in order to obtain the chiral nitro derivatives for instantly claimed inventions. Further, the disclosure of Shim et al (2021) that teach the asymmetric Michael addition of various ketones and unsaturated nitroalkenes (see Table 2, page 3) reaction for the synthesis of nitroalkenes derivatives that would easily place Applicants invention in possession of the public at the time of Applicants invention was filed. The differences between the instant claims and the prior art references are so negligible, that one of ordinary skill in the chemical arts would expect slight variations to be within the expected purview of 35 U.S.C. 103(a).
Finding of prima facie obviousness--rational and motivation (MPEP §2142-2413)
It is obvious to prepare compounds by an old method using analogous starting materials and determining the optimum reaction conditions in the absence of any unobvious or unexpected results. The motivation to make the claimed process / method derives from the expectation that the use of analogous reactants / reagents (e.g., use of thiourea based catalyst,
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, Shim et al page 3, line 1) and reaction conditions would have made similar yield of product. The selection of reaction conditions are more optimization by more modification of routine experimentation and within one skilled in the art (In re Aller, et al., 105 USPQ 233). Since there is an exemplary teaching in the prior art to obtain the instantly claimed method, it is obvious for those ordinary skilled in the chemical art with a reasonable expectation of success that such modification and optimization of reaction conditions would give process with similar rate of recovery. Therefore, in looking at the instantly claimed method as a whole, the claimed method would have been suggested to one skilled in the art and therefore, is obvious, absent evidence to the contrary.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the examiner should be directed to Golam Shameem, Ph.D. whose telephone number is (571) 272-0706. The examiner can normally be reached on Monday-Thursday from 7:30 AM - 6:00 PM. If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Clinton Brooks, Ph.D. can be reached at (571) 270-7682.
Information regarding the status of an application may be obtained from the Patent Application Information Retrieval (PAIR) system. Status information for published applications may be obtained from either Private PAIR or Public PAIR. Status information for unpublished applications is available through Private PAIR only. For more information about the PAIR system, see http://portal.uspto.gov/external/portal. Should you have questions about access to the Private PAIR system, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free).
Any inquiry of a general nature or relating to the status of this application should be directed to the Group receptionist, whose telephone number is (571) 272-1600.
/GOLAM M SHAMEEM/Primary Examiner, Art Unit 1621