DETAILED ACTION
Status of Claims
The amendment submitted June 17, 2026 has been entered. Claims 1-15 are pending and under consideration. Claims 11-15 are withdrawn in the instant office action as explained below in the Election/Restriction section. Claims 1-10 are under consideration in the instant office action as explained below in the Election/Restriction section
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 .
Election/Restrictions
Applicant’s election without traverse of Group I, claims 1-10, drawn to a compound of Formula (I) in the reply filed on June 17, 2026 is acknowledged.
Applicant’s election without traverse of Example 10 (page 5) as a species of compound of Formula (I) in the reply filed on June 17, 2026 likewise acknowledged.
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The elected species reads upon claims 1-10 when RN is hydrogen, R¹, R², R⁴, and R⁵ are hydrogen, R³ is alkyl, specifically methyl, and ring A is A-1, specifically a phenyl ring with RA¹ is -O(C1-5 alkyl), specifically wherein the alkyl is methyl, and RA2 is -(C0-5 alkylene)-O-(C1-5 alkylene)-O(C1-12 alkyl), wherein the group is specifically -OCH₂CH₂OCH₃.
Claims 11-15 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on June 17, 2026.
Claims 1-10 are under consideration and the subject of this Office Action.
Priority
This application is a 371 National Phase Application of PCT/EP2022/079833 filed October 25, 2022, which claims the benefit of priority to European Patent Application No. EP21315226.7, filed on October 25, 2021.
Acknowledgment is made of applicant’s claim for foreign priority under 35 U.S.C. 119
(a)-(d), and the certified copy has been filed.
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Information Disclosure Statement
One information disclosure statements (IDS) submitted on April 22, 2024 is acknowledged. The submission is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statements are being considered by the examiner.
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.
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 Passeron No. 1 (US PG-PUB 2020/0181089 A1) in view of Passeron No. 2 (USPN 12,048,693 B2) in view of Schönherr (Schönherr, H. and Cernak, T., 2013. Profound Methyl Effects in Drug Discovery and a Call for New C-H Methylation Reactions. Angewandte Chemie International Edition, 52(47), pp.12256-12267).
Regarding claims 1-10, Passeron No. 1 teaches similar 4-anilino-quinoline compounds relative to the instantly claimed invention as anticancer agents of general formula (I) (abstract and page 1, paragraphs [0007] to [0014]) (see below).
[AltContent: textbox (R1 = R4 = R5 =H,RN = H,X = C,R3 = H,RA2= O(CH2)n1O(CH2)n2CH3,where n1 is 2, n2 is 0. )][AltContent: rect][AltContent: rect][AltContent: rect]
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Specifically, Passeron’s genus of compounds only differ based on the R3 substituent being hydrogen compared to the instantly claimed invention with respect to the elected species where R3 is methyl.
Passeron’s genus teaches various aryl substitutions as per A-1 of the instant invention such as at page 1, paragraph [0009] that “R1 is selected from H, alkyl, Halo, OH, O-alkyl, NH2, NH-alkyl, N-(alkyl)2, S-alkyl, CF3, OCF3, OCF2H and O(CH2)n1O(CH2)n2CH3, n1 being 1 to 4 and n2 being 0 to 3, Halo being selected from Cl, F, Br and I.” Consequently, Passeron teaches it is possible to modify the phenyl ring without loss in activity and at a site to explore structure-activity relationships via varying substitution patterns, electronics and sterics.
Passeron No. 2 teaches additional haloquinoline derivatives as anticancer compounds which are similar to instant invention. Particularly, compound 42 (column 10, lines 16-43) only differs from instant invention based on the ortho methoxy substituent and the chloro substituent.
As aforementioned, Passeron No. 1 teaches that the R3 position can be substituted with other groups such as hydrogen with no loss in activity.
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As per MPE 2144.09.I: “A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. "An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties." In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979).”
Furthermore, “Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977),” and “Prior art structures do not have to be true homologs or isomers to render structurally similar compounds prima facie obvious. In re Payne, 606 F.2d 303, 203 USPQ 245 (CCPA 1979).”
Consequently, it is reasonable that a person of ordinarily skill in the art would have been motivated to apply the teachings of Passeron to access compound with anticancer properties as per instant invention based on structural similarities as a predictable result with a reasonable expectation of success.
Schönherr teaches that “The methyl group is one of the most commonly occurring carbon fragments in small-molecule drugs. This simplest alkyl fragment appears in more than 67 % of the top-selling drugs of 2011 and can modulate both the biological and physical properties of a molecule. This Review focuses on so-called magic methyl effects on binding potency, where the seemingly mundane change of C-H to C-Me improves the IC50 value of a drug candidate more than 100-fold …One reason the methyl group is so popular in drug discovery is the magic methyl effect: a rare but welcome phenomenon where installation of a methyl group induces a conformational change that can induce up to 590-fold boosts in potency. ”
Therefore, it would have been prima facie obvious before the effective filing date of the claimed invention to have combined the teachings of Passeron No.1 and No.2 to arrive at the instant invention because Passeron No.1 teaches a similar genus of compounds with option for other substituents at the R3 position and various substitution patterns onto instant inventions’ A1 ring and because Passeron No. 2 teaches compounds such as 42 which only differ based on the R3 and ortho-methoxy substituent and because Schönherr teaches switching from a C-H to a C-Me bond can increase potency.
A person of ordinary skill in the art would have been motivated to combine the teachings of Passeron No. 1 and No. 2 as part of standard structure-activity relationship studies to probe the biological activity and optimize properties for the compounds as is standard in the art of medicinal chemistry in accessing compounds with anticancer properties. Neither teaching of Passeron suggests that such modification would lead to a loss in cancer activity. Consequently, an ordinarily skilled artisan would arrive at the instant invention as a predictable result with a reasonable expectation of success.
Therefore, claims 1-10 are rejected on grounds of obviousness.
Conclusion
Claims 1-10 are under consideration and are rejected. No claims are allowed.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to CAROLYN L. LADD whose telephone number is (703)756-5313. The examiner can normally be reached M-Th, 7:00 am to 5:30 pm EST.
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/C.L.L./Examiner, Art Unit 1622
/JAMES H ALSTRUM-ACEVEDO/Supervisory Patent Examiner, Art Unit 1622
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