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
Claims 1-7 of H. Y. Jung, et al., US 18/712,003 (05/21/2024) are pending and are under examination on merits.
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
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.
Claim 7 is rejected under 35 U.S.C. 102 (a)(1)as being anticipated by J. Kim, et al,
62 J. Med. Chem. 1837-1858 (2019)(“Kim”).
Kim teaches a process for preparing of (E)-4-(5-Hydroxy-1-(4-(4-isopropylpiperazin-1-yl)phenyl)-2-phenylpent-1-en-1-yl)phenol Dihydrochloride Salt (12) through the following two steps of reaction:
(b). Treating of the compound (E)-Methyl 5-(4-(4-Isopropylpiperazin-1-yl)phenyl)-4-phenyl-5-(4-(pivaloyloxy)phenyl)pent-4-enoate (3e) with LiAlH4 in THF; and
(c). Reacting of the intermediate with HCl to produce the hydrochloride salt.
Kim at page 1839, Scheme 1, 3e to 12; page 1852, left col. preparation of compound 12.
It needs to be noted that the experimental section for the preparation of compound 12 only describes the procedure for step b.
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Kim at page 1839, Scheme 1, 3e to 12.
The Kim compound 3e has a same chemical structure as that of the compound 10 of the specification. Specification at page 6, Reaction scheme 1, compound 10. The specification Example 6 teaches that the compound 10 is transformed into the compound 1 by treating of the compound 10 with LiAlH4 in THF. See Specification at page 12, Example 6. Therefore, the product in the Kim step b has a same chemical structure as that of the compound 1 of the specification [the compound of formula (1) in claim 1]. Therefore, the Kim step c is a method of reacting of the compound of formula (1) in claim 1 with hydrogen chloride to produce the dihydrochloride salt 12.
The language of “the compound of formula (1) prepared by the process according to claim 1” in claim 7 is interpreted as a product-by-process language. 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. MPEP 2113.
Although the cited product-by-process language is nested within a method claim, this does not change the proper construction of the product-by-process limitation itself. MPEP § 2113(I); Biogen MA Inc. v. EMD Serono, Inc., 976 F.3d 1326, 1334 (Fed. Cir. 2020) (“[t]he nesting of the product-by-process limitation within a method . . . claim does not change the proper construction of the product-by-process limitation itself”); see also non-binding, non-precedential opinion in Ex parte Wohaibi, Appeal No. 2024-004112, 17/750,212 (PTAB 2025) discussing this Federal Circuit decision.
Herein, the source of the compound formula (1) does not change the structure of claim 7. Therefore, the Kim method meets each and every limitation of claim 7 and claim 7 is anticipated.
Allowable Subject Matter
Claims 1-6 are allowed.
The closet prior art is S. Y. Hwang, et al, US20190167820A1 (2019)(“Hwang”).
S. Y. Hwang, et al, US 20190167820A1 (2019)(“Hwang”)
Hwang teaches that biological effects of ERRγ has been extensively studied in various disease models and ligand inhibiting activity of ERRγ can improve the function of NIS ( sodium iodide symporter ) to increase an ATC (anaplastic thyroid cancer) intracellular radioiodine uptake and exhibit an effect of increasing radioiodine treatment. Hwang at page 2, [0012].
Hwang teaches an arylethene derivative represented by the following Chemical Formula 1, which may effectively inhibit an activity of ERRγ. Hwang at page 9, [0019].
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Hwang teaches examples of the compound Formula 1, such as compound 18a that has a same chemical structure as that of the compound 1 in the instant claim 1. Hwang at page 97, Table 3, Example 20. Compound 18a.
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Hwang teaches that compound 18a is prepared using the process of Example 19. Hwang at page 97, right col.[0157], line 1-2. Hwang teaches the Example 19 is conducted as the following reactions. Hwang at page 96, [0153].
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Thus, Hwang fairly teaches one of ordinary skill in the art that the Hwang compound 18a was prepared through the following method.
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Hwang tested the binding activities of example compounds including 18a with ERRγ, ERRα, ERRβ, Erα (Huang at page 139, Table 12); ERRγ inhibiting activities of example compounds including 18a (Huang at page 140, Table 13); membrane permeability of example compounds including 18a (Huang at page 142, Table 16) and in vivo PK of example compounds including 18a (Huang at page 143, Table 18).
Difference Hwang and Claims 1-6
The Hwang synthetic method comprises a step of reduction of the instant claim 1 compound 10 to form the compound 18a (the compound 1 in the instant claim 1).
The Hwang method differs from the instant claim 1 in that Hwang does not teach to prepare the instant claim 1 compound 10 with the claimed method.
Claims 1-6 are Not Obvious
Claims 1-6 are not obvious because one ordinary skill in the art is not motivated to modify the Hwang compound 18a synthetic method. Motivation lacks as one ordinary skill in the art has no motivation to elect the Hwang compound 18a as a lead candidate for further investigation because it has poor membrane permeability (see Huang at page 142, Table 16) and lower in vivo AUC compared to other compounds tested ( see Huang at page 143, Table 18).
Conclusion
Claim 7 is rejected and claims 1-6 are allowed.
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/FRANK S. HOU/Examiner, Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
