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
This Office action is responsive to Applicant's Response to Election/Restriction, filed Nov. 07, 2025. As filed, claims 1-13 are pending in the instant application.
Priority
This application filed 03/03/2023 Claims Priority from provisional application 63,318/047, filed 03/09/2022.
Information Disclosure Statement
No information disclosure statement has been filed in the instant application. Applicants are reminded of the duty to disclose anything believed to be material to the patentability of the instant application in accordance with 37 CPR 1.56.
Election/Restrictions
Applicant's election of Group I, claims 1-10, drawn to compound of Structure 1 in the reply filed on 11/07/2025 is acknowledged.
Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)).
Claims 11-13 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Claims 1-10 will be examined on the merits herein.
Claim Objections
Claim 1 is objected to because of the following informalities: the capitalized recitation “1-Chloro-4-(4'-hydroxy-3'-methoxyphenyl)-but-3-en-2-one” should be replaces with lower case.
Appropriate correction is required.
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 1-10 are rejected under 35 U.S.C. 103 as being unpatentable over US 9365486, Jun.14,2016 by Majeed et al. (cited in PTO-892 attached herewith) in view of Thornber, Chem. Soc. Rev.,1979, 563-580 (cited in PTO-892 attached herewith).
Instant claim 1 is drawn to a compound of formula STR1:
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Claims 2-10 are product-by-process claims.
Determining the scope and contents of the prior art: The ‘486 patent discloses a compound 8 (col. 3 line 16). Shown below are compounds disclosed by the ‘486 as displayed in Registry database:
RN 1108610-67-8 CAPLUS
CN 3-Buten-2-one, 4-(4-hydroxy-3-methoxyphenyl)-1-iodo-, (3E)- (CA INDEX
NAME)
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The compounds of the prior art by ‘486 patent share the same core structure with instantly claimed compound and can be used as an intermediate for synthesis of Calebin-A, same utility as instant application.
Ascertaining the differences between the prior art and the claims at issue:
The difference in compound 8 of the prior art and the claimed compound, is the iodide instead of chloride group as same structural loci.
Conclusion:
A prima facie case of obviousness based on structure exists if the prior art suggests to one of ordinary skill in the art to make the substitution or modification. In re Tabor, 502 F.2d 775 (CCPA 1974). It has been held several times that structurally similar compounds are obvious over one another. In re Jones, 162 F.2d 638 (CCPA 1947) (Absent unexpected results, one of skill in the art would expect compounds that differ in only the position of a substituent to possess similar chemical and physical properties.); In re Norris, 179 F.2d 970 (CCPA 1950) (A novel and useful chemical compound, which is isomeric with compounds of prior art, is not patentable where new compound is not shown to possess new and unexpected utilities.); In re Payne, 606 F.2d 303, (CCPA 1979) (An obviousness rejection based on similarity in chemical structure and function entails motivation of one skilled in the art to make the claimed compound with an expectation that compounds similar in structure will have similar properties.
In the instant application, the difference between the closest prior art, the '486 patent, is the substitution of one halogen for another - the compound disclosed by the prior art has an iodide atom whereas the instantly claimed compound has a chloride atom. The prior art teach the compound 8 as intermediate in the synthesis of Calebin-A. Before the effective filing date the skilled artisan would have been motivated to make the structural modification and substitute a halogen for another from a known substrate which is routine in the chemical art, and have reasonable expectation of success in arriving at instant invention.
The motivation to make a substitution of iodine group for chlorine stems from the fact that a person having ordinary skill in the art would expect that the compounds could be prepared by the same method as taught by the prior art and have the same utility as the compounds taught by the prior art- as intermediates in the synthesis of Calebin-A.
Moreover, the article by Thornber, specifically teach that Cl is functional equivalent to I, Br, F (Table 1 page 564, where I, Br, Cl, F are listed as univalent groups). Thornber shows that halogen atoms are functional equivalent and structural modification such as replacing one halogen for another in the same location of core structure in known practice in the chemical art.
As a whole, the prior art suggests that halogen atoms other than iodide, such as a chloride or bromide, may be used in the same location of core structure. For example, Thornber illustrates the use of a halogen as equivalents groups I, Cl, Br may be used at the same location of the core structure and that such replacing one halogen for another in the same loci of core structure is routine in the chemical art.
Exemplary rationales that may support a conclusion of obviousness include:
(B) Simple substitution of one known element for another to obtain predictable results.
(E) "Obvious to try" - choosing from a finite number of identified, predictable
solutions, with a reasonable expectation of success.”
Based on structural similarity and obvious structural modification of replacing halogen for another, the instant compound is found to be prima facie obvious over the compound of the prior art.
Regarding instant claims 2-10, these are product-by-process claims. During patent prosecution, product-by-process claims are examined based upon a claim interpretation of the structure of the product only; i.e., without any limitations based on recited steps. See MPEP § 2113; In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985) (“Even though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process.”).
In the instant case, the prior art by the ‘486 patent discloses a compound 8
which is structurally similar to the compound of Structure 1 as required by instant claims[AltContent: textbox ()] and as discussed supra, found to be to be prima facie obvious over the compound of the prior art.
Consequently, the instant claims are prima facie obvious over the teachings of the prior art.
Conclusion
Claims 1-10 are rejected. Claims 11-13 are withdrawn from further consideration.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ANA MURESAN whose telephone number is (571)-270-7587. The examiner can normally be reached on Monday through Friday, 8:30 am to 5:30 pm EST.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/ANA Z MURESAN/Primary Examiner, Art Unit 1692