Ex Parte Donde et alDownload PDFBoard of Patent Appeals and InterferencesMay 17, 201010916243 (B.P.A.I. May. 17, 2010) Copy Citation UNITED STATES PATENT AND TRADEMARK OFFICE __________ BEFORE THE BOARD OF PATENT APPEALS AND INTERFERENCES __________ Ex parte YARIV DONDE, ROBERT M. BURK and MICHAEL E. GARST __________ Appeal 2009-012378 Application 10/916,243 Technology Center 1600 __________ Decided: May 18, 2010 __________ Before LORA M. GREEN, MELANIE L. McCOLLUM, and STEPHEN WALSH, Administrative Patent Judges. GREEN, Administrative Patent Judge. DECISION ON APPEAL This is a decision on appeal under 35 U.S.C. § 134 from the Examiner’s rejection of claims 1-23, 25, 26, 28, and 29. We have jurisdiction under 35 U.S.C. § 6(b). Appeal 2009-012378 Application 10/916,243 2 STATEMENT OF THE CASE The claims are directed to a compound of specified formula, a method of administering the compound for the prevention or treatment of glaucoma or ocular hypertension, and a liquid comprising the compound. Claim 1 is representative of the claims on appeal, and reads as follows: 1. A compound having a formula or a pharmaceutically acceptable salt or a prodrug thereof, wherein a dashed line represents the presence or absence of a bond; A is -(CH2)6-, or cis -CH2-CH=CH-(CH2)3-, wherein 1 or 2 carbons may be substituted with S or O; B is hydrogen, -CH3, or =CH2; J is -OH or =O; D is -(CH2)n-, -X(CH2)n, or -(CH2)nX-, wherein n is from 0 to 3 and X is S or O; and E is thienyl or benzothienyl, or substituted thienyl or benzothienyl having substituents comprising from 1 to 6 non-hydrogen atoms each. We reverse. Appeal 2009-012378 Application 10/916,243 3 ISSUE Has the Examiner established by a preponderance of the evidence of record that the combination of Burk and Patani suggests modifying the compounds taught by Burk to arrive at the claimed compound? FINDINGS OF FACT FF1 The Examiner rejects claims 1-23, 25, 26, 28, and 29 under 35 U.S.C. § 103(a) as being rendered obvious by the combination of Burk1 and Patani.2 (Ans. 4.) FF2 Burk teaches compounds of the formula: (Burk, col. 3, ll. 25-35.) FF3 The Examiner finds that Burk teaches the compound: 1 Burk, US Patent No. 6,124,344, issued Sep. 26, 2000. 2 Patani, et. al, Bioisosterism: A Rational Approach in Drug Design, Chem Rev, pp. 3147-3176 (1996). Appeal 2009-012378 Application 10/916,243 4 and its use in the treatment of hypertension. (Ans. 4.) FF4 The Examiner notes that “while Burk show[s] the effects of varying the X substituent, the hydroxyl group on the omega chain, and the carboxylic acid group on the alpha chain, Burk does not preclude the person of ordinary skill in the art to try reasonable bioisosteric replacements on the other functional groups of the molecule, namely the[ ] hydroxyl groups on the cyclopentane ring.” (Id. at 6.) FF5 The Examiner notes that “Burk does not teach a carbon in place of the oxygen in the cyclopentane ring substituent ortho to the chain containing the thienyl group.” (Id. at 4.) FF6 The Examiner relies on Patani for its teaching “that methyl and hydroxyl are bioisosteres of each other.” (Id. at 5.) FF7 Specifically, the Examiner relies on Figure 14 and Table 12 at page 3153 of Patani that show thymidylate synthase enzyme inhibition activity for benzo(f)quinazalin-4(2H)-ones. (Ans. 7.) The compounds having a methyl group had an IC50 of 0.178, and the compound that had a hydroxyl group had an IC50 of 0.48. (Id.) FF8 According to the Examiner, the data presented “shows that inserting a methyl or a hydroxyl group in the X position gives compounds that possess the same utility, namely inhibiting thymidylate synthase enzyme.” (Id.) The Examiner acknowledges that the data does not deal with prostaglandins, but concludes that “one of ordinary skill in the art would infer that hydroxyl and methyl are bioisosteres of each other and that the groups could be swapped in other molecules with a reasonable expectation that another molecule with the same utility would be generated.” (Id.) Appeal 2009-012378 Application 10/916,243 5 PRINCIPLES OF LAW While the analysis under 35 U.S.C. § 103 allows flexibility in determining whether a claimed invention would have been obvious, KSR Int’l Co. v. Teleflex Inc., 550 U.S. 398, 418 (2007), it still requires showing that “there was an apparent reason to combine the known elements in the fashion claimed by the patent at issue.” Id. “We must still be careful not to allow hindsight reconstruction of references to reach the claimed invention without any explanation as to how or why the references would be combined to produce the claimed invention.” Innogenetics, N.V. v. Abbott Labs., 512 F.3d 1363, 1374 n.3 (Fed. Cir. 2008). In order to make a prima facie case of obviousness based on the structural similarity between the claimed compound and the compound disclosed by the prior art, not only must the structural similarity exist, but the prior art must also provide reason or motivation to make the claimed compound. See In re Dillon, 919 F. 2d 688, 692 (Fed. Cir. 1990) (en banc), In re Mayne, 104 F. 3d 1339, 1341 (Fed. Cir. 1997); In re Payne, 606 F.2d 303, 313 (CCPA 1979); see also In re Grabiak, 769 F.2d 729, 731-32 (Fed. Cir. 1985 (noting that in addition similarity in structures between the prior art compound and the claimed compound, a prima facie case of obviousness also requires a showing of “adequate support in the prior art” for the change in structure). Therefore, in order to establish a prima facie case of obviousness, there need be “a showing that the ‘prior art would have suggested making the specific molecular modifications necessary to achieve the claimed invention.’” Takeda Chemical Industries, Ltd. v. Alphapharm Appeal 2009-012378 Application 10/916,243 6 Pty., Ltd., 492 F.3d 1350, 1356 (Fed. Cir. 2007), quoting In re Deuel, 51 F.3d 1552, 1558 (Fed. Cir. 1995). The court in Takeda noted that the “test for prima facie obviousness for chemical compounds is consistent with the legal principles enunciated in KSR,” Takeda, 492 F.3d at 1356, and thus, “in cases involving new chemical compounds, it remains necessary to identify some reason that would have led a chemist to modify a known compound in a particular manner to establish prima facie obviousness of a new claimed compound.” Id. at 1357. ANALYSIS Appellants argue that there are a nearly infinite number of substitutions that could be made to the structure of Burk. (App. Br. 20.) Appellants assert that there must be something in the prior art that suggests the modification, and that nothing in the combination of references as set forth by the Examiner suggests the modification of replacing the oxygen in the cyclopentane ring substituent ortho to the chain containing the thienyl group with a carbon. (Id. at 20-21.) We agree with Appellants. As acknowledged by the Examiner, while Burk shows the effects of varying the X substituent, the hydroxyl group on the omega chain, and the carboxylic acid group on the alpha chain (FF4), Burk does not suggest replacing the oxygen in the cyclopentane ring substituent ortho to the chain containing the thienyl group with any group, much less than the claimed carbon group. If we were to adopt the Examiner’s reasoning, any substitution of any group for a known bioisostere would be prima facie obvious, whether there is any suggestion in the art to Appeal 2009-012378 Application 10/916,243 7 make the modification or not. But that is not the state of the law, because as noted by the Court of Appeals for the Federal Court, in order to establish a prima facie case of obviousness, there must be a reason in the prior art that would have suggested making the specific molecular modifications necessary to achieve the claimed invention. Takeda 492 F.3d at 1356. CONCLUSION OF LAW We conclude that the Examiner has not established by a preponderance of the evidence of record that the combination of Burk and Patani suggests modifying the compounds taught by Burk to arrive at the claimed compounds. We are therefore compelled to reverse the rejection of claims 1-23, 25, 26, 28, and 29 under 35 U.S.C. § 103(a) as being rendered obvious by the combination of Burk and Patani. REVERSED alw ALLERGAN, INC. 2525 DUPONT DRIVE, T2-7H IRVINE, CA 92612-1599 Copy with citationCopy as parenthetical citation