Ex Parte Kim et alDownload PDFPatent Trial and Appeal BoardNov 14, 201610562615 (P.T.A.B. Nov. 14, 2016) Copy Citation United States Patent and Trademark Office UNITED STATES DEPARTMENT OF COMMERCE United States Patent and Trademark Office Address: COMMISSIONER FOR PATENTS P.O.Box 1450 Alexandria, Virginia 22313-1450 www.uspto.gov APPLICATION NO. FILING DATE FIRST NAMED INVENTOR ATTORNEY DOCKET NO. CONFIRMATION NO. 10/562,615 07/27/2006 Myung-Hwa Kim 428.1145 6138 7590 11/16/2016 LUCAS & MERCANTI, LLP 30 BROAD STREET 21st FLOOR NEW YORK, NY 10004 EXAMINER SZNAIDMAN, MARCOS L ART UNIT PAPER NUMBER 1628 NOTIFICATION DATE DELIVERY MODE 11/16/2016 ELECTRONIC Please find below and/or attached an Office communication concerning this application or proceeding. The time period for reply, if any, is set in the attached communication. Notice of the Office communication was sent electronically on above-indicated "Notification Date" to the following e-mail address(es): info@lmiplaw.com PTOL-90A (Rev. 04/07) UNITED STATES PATENT AND TRADEMARK OFFICE BEFORE THE PATENT TRIAL AND APPEAL BOARD Ex parte MYUNG-HWA KIM, KWNAGWOO CHUN, JAE-WON CHOL, BO-YOUNG JOE, SANG-WOO PARK, KWANG HEE KIM, BYUNG-KYU OH, and JONG-HEE CHOL1 Appeal 2014-007893 Application 10/562,615 Technology Center 1600 Before DEMETRA J. MILLS, MELANIE L. McCOLLUM, and TAWEN CHANG, Administrative Patent Judges. McCOLLUM, Administrative Patent Judge. DECISION ON APPEAL This is an appeal under 35U.S.C. § 134 involving claims to a tricyclic derivative and to a composition containing it. The Examiner has rejected the claims for obviousness and for obviousness-type double patenting. We have jurisdiction under 35 U.S.C. § 6(b). We affirm. 1 Appellants identify the real party in interest as JE IL PHARMA CEUTICAL CO., LTD. (Br. 2). Appeal 2014-007893 Application 10/562,615 STATEMENT OF THE CASE Claims 12, 13, and 16—21 are on appeal (Br. 2). The claims have not been argued separately and therefore stand or fall together. 37 C.F.R. § 41.37(c)(l)(iv). Claim 12 is representative and is set forth in Appellants’ Claims Appendix (Br. 10—11). Claims 12, 13, and 16—21 stand rejected under 35 U.S.C. § 103(a) as obvious over Kim '8242 in view of Patani3 and Park4 (Ans. 2). Claims 12, 13, and 16—21 also stand rejected on the ground of nonstatutory obviousness-type double patenting as being unpatentable over claims 1—5 of U.S. Patent No. 7,119,229 B2 to Kim et al. (hereinafter “Kim '229”) in view of Patani and Park (Ans. 21).5 OBVIOUSNESS The Examiner relies on Kim '824 for teaching, in Example 12, a compound, which the Examiner refers to as compound A, that “differs from the instant compounds 10, 12 and 17, in the presence of a Hydrogen atom instead of Fluorine atom in the aromatic ring” (Ans. 4). The Examiner relies on Patani for teaching “that the substitution of Hydrogen by Fluorine is one of the most commonly employed monovalent isosteric replacements” (id.). In particular, the Examiner finds that Patani “in Figure 2 . . . give[s] an example wherein replacing Hydrogen with 2 Kim et al., WO 02/100824 Al, published Dec. 19, 2002. 3 George A. Patani & Edmond J. LaVoie, Bioisosterism: A Rational Approach in Drug Design, 96 Chem. Rev. 3147—76 (1996). 4 B. Kevin Park et al., Metabolism of Fluorine-Containing Drugs, 41 Annu. Rev. Pharmacol. Toxicol. 443—70 (2001). 5 A second obviousness-type double patenting rejection was withdrawn by the Examiner (Ans. 22). 2 Appeal 2014-007893 Application 10/562,615 Fluorine in an aromatic ring maintains or improves the pharmacological properties of the compounds” {id. at 4—5). The Examiner relies on Park for teaching: Fluorine substitution can alter the chemical properties, disposition, and biological activity of drugs. Many fluorinated compounds are currently widely used in the treatment of a disease. These include antidepressants, anti-inflammatory drugs, antimalarial drugs, etc. The chemistry and medicinal chemistry of fluoro-organic compounds have been extensively reviewed. The development of new fluorinating agents has vastly increased the potential for synthesis of novel fluorinated drugs .... The replacement of a hydrogen atom or hydroxyl group by a fluorine atom is a strategy widely used in drug development to alter biological function .... In terms of drug design, fluorine substitution can be used to alter the rate of drug metabolism and thereby produce a drug with a longer duration of action. Such an approach has already been used successfully for several classes of drugs. In addition, fluorine substitution can be used to reduce toxicity by blocking the formation of toxic metabolites and, in particular, chemically reactive metabolites. This can be achieved by fluorine substitution, at the appropriate site of the molecule, with an alteration in the balance between direct detoxication and metabolic bioactivation, provided the chemical modification does not impair drug efficacy. {Id. at 5.) The Examiner concludes that it would have been obvious “to replace any Hydrogen of the aromatic ring of compound A with a Fluorine in order to obtain any of the instant compound[s]: 10, 12, or 17, and expect these compounds to have . . . similar biological/pharmaceutical properties” {id. at 7). 3 Appeal 2014-007893 Application 10/562,615 Analysis We incorporate the Examiner’s findings of fact and conclusions of law as set forth in the Final Rejection at pages 4—8 and in the Examiner’s Answer at pages 2—7, which are summarized above. Appellants argue, however, that none of the cited legal authority on structural obviousness supports a prima facie case for fluorination (Br. 4). We are not persuaded. We agree with Appellants that the Examiner has not provided a specific legal authority for the proposition that it is prima facie obvious to replace a hydrogen with a fluorine. However, Appellants have not adequately explained why it would not have been obvious in view of the teachings in Patani and Park. Appellants also argue that the “Examiner’s narrow focus on the phenyl substituent clearly indicates impermissible hindsight because the combination of Kim ['824], Patani and Park does not teach or suggest one skilled in the art to focus on just the phenyl substituent for possible fluorination” {id. at 6). We are not persuaded. According to Appellants, ‘“compound A’ has at least 24 possible sites for fluorination” {id.). In response, the Examiner finds that this “is still a small number of hydrogens, so the skilled in the art will envision each and every fluorine isomer” (Ans. 12). In addition, the Examiner provides reasoning as to why one of skill in the art may focus on phenyl substitutions {id. at 12—14). We conclude that Appellants have not adequately explained why the Examiner’s reasoning is incorrect. In addition, Appellants argue that “the Examiner provides no definitive rationale as to why Appellants’ data on toxicity is not sufficient to 4 Appeal 2014-007893 Application 10/562,615 demonstrate unexpected results indicative of non-obviousness under the Graham factors” (Br. 7). We are not persuaded. As noted by the Examiner (Ans. 17), Appellants’ Declaration6 compares the compounds in Examples 8 and 12 of the present Specification to compound 6 of Kim '824 (Decl. 3—4, | 8), which differ not only in fluorination but also in the presence of a 10-methylsulfanyl group rather than a 10-methoxy group (compare Spec. 82—83 & 86—87 to Kim '824, p. 24).7 In contrast, Example 12 of Kim '824, which is specifically relied on by the Examiner (Ans. 4), discloses a compound that, like the compounds in present Examples 8 and 12, has a 10-methylsulfonyl group (Kim '824, p. 28). Thus, Appellants have not compared the present invention to the closest prior art. As a result, it is not clear whether the “improved toxicology profile” indicated in the Declaration (Decl. 19) is actually due to the fluorination. Moreover, even if it is, we agree with the Examiner that Appellants have not provided sufficient evidence indicating that improved toxicity would have been unexpected in view of Park (Ans. 20), which specifically teaches that “fluorine substitution can be used to reduce toxicity by blocking the formation of toxic metabolites and, in particular, chemically reactive metabolites” (Park 464). 6 Declaration Under 37 C.F.R. § 1.132 of Myung-Hwa Kim dated September 20, 2011 (filed September 21, 2011). 7 The compound in present Example 8 also differs in having a 3-ethoxy group rather than a 3-methoxy group. 5 Appeal 2014-007893 Application 10/562,615 Conclusion The evidence supports the Examiner’s conclusion that Kim '824, Patani, and Park suggest the derivative of representative claim 12. We therefore affirm the obviousness rejection. DOUBLE PATENTING The Examiner finds that “Claims 1-5 of [Kim '229] teach similar compounds and pharmaceutical compositions as claimed in the instant application” (Ans. 21). In particular, the Examiner finds that these “compounds only differ in the absence of a[] halogen (i.e. F, Cl, Br or I) in the aromatic ring” (id.). For the reasons discussed in the obviousness rejection, the Examiner concludes that it would have been obvious, “based on the teachings of Patani and Park[,] ... to replace a[] hydrogen atom of the aromatic ring of any of the compounds disclosed in [Kim '229] and arrive at the compounds of the instant application” (id.). Analysis We incorporate the Examiner’s findings of fact and conclusions of law as set forth in the Final Rejection at pages 10—11 and in the Examiner’s Answer at page 21, which are summarized above. Appellants argue that the “double patenting rejection should be reversed because the current claims are not an obvious variation of the claims of [Kim '229] for the reasons discussed above” (Br. 8). We are not persuaded by these arguments for the reasons discussed above. Conclusion The evidence supports the Examiner’s conclusion that claims 1—5 of Kim '229 in view of Patani and Park suggest the derivative of representative 6 Appeal 2014-007893 Application 10/562,615 claim 12. We therefore affirm the obviousness-type double patenting rejection. TIME PERIOD FOR RESPONSE No time period for taking any subsequent action in connection with this appeal may be extended under 37 C.F.R. § 1.136(a). AFFIRMED 7 Copy with citationCopy as parenthetical citation