Ex Parte Pagoria et al

Patent Trial and Appeal BoardApr 29, 2016

12426774 (P.T.A.B. Apr. 29, 2016)

UNITED STA TES p A TENT AND TRADEMARK OFFICE APPLICATION NO. FILING DATE 12/426,774 78980 7590 LLNL/Zilka-Kotab 0412012009 05/03/2016 Lawrence Livermore National Laboratory L-703, P.O. Box 808 Livermore, CA 94551 FIRST NAMED INVENTOR Philip F. Pagoria 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 ATTORNEY DOCKET NO. CONFIRMATION NO. IL-11975/LLNLP037 5629 EXAMINER WILLIS, DOUGLAS M ART UNIT PAPER NUMBER 1624 NOTIFICATION DATE DELIVERY MODE 05/03/2016 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): llnl-docket@llnl.gov zk-uspto@zilkakotab.com PTOL-90A (Rev. 04/07) UNITED STATES PATENT AND TRADEMARK OFFICE BEFORE THE PATENT TRIAL AND APPEAL BOARD Ex parte PHILIP F. PAGORIA and MAO XI ZHANG 1 Appeal2014-004800 Application 12/426,774 Technology Center 1600 Before MELANIE L. MCCOLLUM, ULRIKE W. JENKS, and JOHN E. SCHNEIDER, Administrative Patent Judges. SCHNEIDER, Administrative Patent Judge. DECISION ON APPEAL This is an appeal under 35 U.S.C. Â§ 134(a) involving claims to methods for manufacturing pyrazines, which have been rejected as failing to comply with the written description, enablement, and indefiniteness requirements. We have jurisdiction under 35 U.S.C. Â§ 6(b). We affirm-in-part. 1 Appellants identify the Real Party in Interest as Lawrence Livermore National Security, LLC. Appeal Br. 2. Appeal2014-004800 Application 12/426,774 STATEMENT OF THE CASE The present invention relates to synthesis of organic compounds, and more particularly to synthesis of compounds such as 2,6-diaminopyrazine-1- oxide and 2,6-diamino-3,5-dinitropyrazine-l-oxide. Spec. 1. Claims 1--4, 37, 38, 42, and 43 are on appeal. Claim 1 is illustrative and reads as follows: 1. A method for synthesizing a pyrazine-containing material, compnsmg: contacting an iminodiacetonitrile derivative with a base and a reagent selected from a group consisting of a hydroxylamine, a hydroxylamine salt, an aliphatic amine, a primary amine, a secondary amine, an aryl-substituted alkylamine, an alcohol, an alkanolamine and an aryl alcoholamine, wherein the base is selected from a group consisting of a metal hydroxide, pyridine, a tertiary amine, and a secondary amme. The claims stand rejected2 as follows: Claims 37 and 38 have been reject under 35 U.S.C. Â§ 112, first paragraph, as lacking written description. Claims 1--4 and 43 have been rejected under 35 U.S.C. Â§ 112, first paragraph, as not enabled. 2 Appellants have also asked the Board to consider the objections to the claims raised by the Examiner. The Board normally only considers matters affecting the merits of the invention, i.e., rejections of claims. See 37 C.F.R. Â§ 41.31 ( c) (2011 ). Matters not affecting the merits of the invention, such as objections to the claims or Specification or allegations of procedural errors by the Examiner (e.g., failure to designate a new ground of rejection as such), are to be raised by petition to the Director. See 37 C.F.R. Â§Â§ 1.181- 183; see also MPEP Â§Â§ 1002, 1207.03 (IV) (9th Ed., Rev. 7, Nov. 2015). 2 Appeal2014-004800 Application 12/426,774 Claim 42 has been rejected under 35 U.S.C. Â§ 112, second paragraph, as indefinite. I Issue The Examiner has rejected claims 37 and 38 under 35 U.S.C. Â§ 112, first paragraph, for lacking written description. The Examiner finds that the Specification only teaches a yield of 2,6 diamino-3,5-dinitropyrazine -1- oxide (LLM-105") ranging from 0% to 95% and that there is nothing in the disclosure to explicitly or inherently teach a yield of 65% to 95%. Ans. 15- 19. The Examiner also notes that the disclosure only teaches a yield on LLM-105 of 64 %, outside the range recited in the claims. Ans. 17. Appellants contend that the recited range need not be literally disclosed in the Specification. Appellants further contend that the range 65- 95% falls within the range of 0-95% and is therefore inherently disclosed. Appeal Br. 6-10. Appellants further argue that the Examiner has introduced no evidence to show why a person of ordinary skill in the art would not appreciate that Appellants had in their possession a yield range of from 65% to 95% given the disclosure of a yield from 0% to 95%. Appeal Br. 7. Appellants also asserts that it would be against public policy to allow the rejection to stand. Appeal Br. 10-12. The issue with respect to this rejection is whether the Examiner has established by a preponderance of the evidence that claims 37 and 38 fail to satisfy the written description requirement as defined by 35 U.S.C. Â§ 112, first paragraph. 3 Appeal2014-004800 Application 12/426,774 Findings of Fact FF 1. According to the Specification, most prior art "syntheses of LLM-105 [2,6-diamino-3,5-dinitropyrazine-l-oxide] ... proceed through the intermediate compound, 2,6-diamino-3,5-dinitropyrazine (ANPZ), which upon oxidation with trifluoroacetic peracid yields LLM-105 .... This gives LLM-105 in high yield that is contaminated with 3-10% ANPZ." Spec. 1- 2: i-f 3, see also 9-10 i-f 34: "[T]he syntheses that proceed through ANPZ energetic compounds are produced in each of the last three steps. There are added costs associated with the synthesis of energetic compounds, mostly due to additional safety requirements and fewer commercial companies authorized to produce energetic compounds." FF2. The Specification explains that "synthesis ofLLM-105 based on the nitration ofDAPO [2,6-diaminopyrazine-1-oxide] has several advantages over the procedure described ... , including reduced cost, improved safety and purer final product." Spec. 9: i-f 34. "Nitration of D APO in various conditions produces LLM-10 5 in the yield of about 0- 95 %. "Spec. 10: i-f 35. "Nitration ofDAPO in various conditions produces LLM-105 in the yield of 30-80%." Spec. 7: i-f 21. The Specification, however, only exemplifies the production ofLLM-105 using DAPO resulting in a yield of LLM-105 of 64 %. Spec. 17-18. Principles of Law "[T]he question is whether, on the facts, the PTO has presented sufficient reason to doubt that the broader described range also describes the 4 Appeal2014-004800 Application 12/426,774 somewhat narrower claimed range." In re Wertheim, 541F.2d257, 264 (CCPA 1976) (emphasis added). The "written description" requirement ... serves both to satisfy the inventor's obligation to disclose the technologic knowledge upon which the patent is based, and to demonstrate that the patentee was in possession of the invention that is claimed .... The descriptive text needed to meet these requirements varies with the nature and scope of the invention at issue, and with the scientific and technologic knowledge already in existence. Capon v. Eshhar, 418 F.3d 1349, 1357 (Fed. Cir. 2005). Analysis We agree with the Examiner that the present disclosure does not adequately support the claimed yield range of 65% to 95%. While the Specification need not expressly support the claim limitation, we find that there is insufficient disclosure in the Specification to support the limitation either implicitly or inherently. The Specification states that nitration of DAPO in various conditions produces LLM-105 in the yield of about 0-95% and also recites a yield 30-80% ofLLM-105 (see FF2) .. According to the Examiner, this range from 0-95% embraces almost every conceivable product yield including ones where the reaction does not work. Ans. 17. "[I]n a yield as low as 0% (i.e. the reaction will fail!!!)" Id. The only exemplified yield recited in the disclosure is 64%, a level just below the range recited in the claims. Ans. 17-18. We agree with the Examiner's position that the disclosure in the Specification is insufficient to support the claimed range from 65% to 95%. Appellants point to no additional evidence to support the limitation but instead rely on Wertheim to support their positon that a narrow range is 5 Appeal2014-004800 Application 12/426,774 inherently disclosed within a broad range. Appeal Br. 9--10. Appellants' reliance on Wertheim is misplaced. In Wertheim, the Court of Customs and Patent Appeals found while a narrow range was not specifically recited in the Specification, it was supported by both the broader range and several examples disclosing values within the narrow range. Wertheim, 541 F .2d at 256. Unlike the disclosure in Wertheim, the present disclosure contains no examples within the claimed range. Appellants' suggestion that the Examiner has acquiesced to the Appellants' Wertheim argument is unpersuasive. Reply Br. 8 & 9. While the Examiner did not specifically reference the Wertheim decision, the Examiner did discuss why the Examiner found that the narrower range in the claims was not supported by the broad range in the claims. The Examiner's maintenance of the written description rejection is an implicit response to Appellants' Wertheim arguments as well as Appellants' policy arguments. Finally, we have considered Appellants' policy arguments and find them unpersuasive. Part of the quid pro quo of granting a patent is the requirement that the inventor provide a written description of his invention so as to convey to those skilled in the art that the inventor was in possession of the invention when the application was filed. Capon, 418 F.3d at 1357. Appellants' public arguments would have us ignore the explicit requirements of Section 112. We decline to do so. Conclusion of Law We conclude that the Examiner has shown by a preponderance of the evidence that claims 37 and 38 are not supported by the present disclosure 6 Appeal2014-004800 Application 12/426,774 and do not satisfy the written description requirement as defined by 3 5 U.S.C. Â§ 112, first paragraph. II Issue The Examiner has rejected claims 1--4 and 43 under 35 U.S.C. Â§ 112, first paragraph, as non-enabled. The Examiner finds that while the Specification is enabling for the four specific species recited in the Specification, it is not enabling for the entire scope of the claims. Ans. 19. The Examiner finds that it would require undue experimentation for one skilled in the art to practice the claimed method to produce all the possible compounds embraced by the claims. Id. Appellants contend that the Specification provides sufficient guidance to one skilled in the art to synthesize pyrazine containing compounds without undue experimentation. Appeal Br. 16. While some experimentation may be required, given the chemistry involved, it does not involve "undue" experimentation. Appeal Br. 15-16. The issue with respect to this rejection is whether the Examiner has established by a preponderance of the evidence that claims 1--4 and 43 are not enabled as defined by 35 U.S.C. Â§ 112, first paragraph. Findings of Fact FF3. The Specification discloses the general reaction conditions for making pyrazine containing materials. See Spec. 7: i-f 24 FF4. The Specification discloses a method for preparing the required precursors. See Spec. 8: i-fi-125-27. 7 Appeal2014-004800 Application 12/426,774 FF5. The Specification discloses the synthesis of 2,6- diaminopyrazine-1-oxide ("DAPO"). See Spec 8-9: i-fi-128-32. FF6. The Specification discloses the synthesis of 2,6-diamino-3,5- dinitropyrazine-1-oxide, a.k.a. LLM-105. See Spec. 9-10: i-fi-132-37 FF7. The Specification discloses the preparation of 4 species of pyrazine containing compounds. Spec. 14--18. The Examiner identifies the 4 species disclosed in the Specification to have the following structure: (Ans. 6.) Principles of Law The first paragraph of 35 U.S.C. Â§ 112 requires, inter alia, that the specification of a patent enable any person skilled in the art to which it pertains to make and use the claimed invention. Although the statute does not say so, enablement requires that the specification teach those in the art to make and use the invention without "undue experimentation." In re Wands, 858 F.2d 731, 737 ... (Fed. Cir. 1988). That some experimentation may be required is not fatal; the issue is whether the amount of experimentation required is "undue." In re Vaeck, 947 F.2d 488, 495 (Fed. Cir. 1991). Some experimentation, even a considerable amount, is not "undue" if, e.g., it is merely routine, or if 8 Appeal2014-004800 Application 12/426,774 the specification provides a reasonable amount of guidance as to the direction in which the experimentation should proceed. In re Wands, 858 F.2d 731, 737 (Fed. Cir. 1988). Analysis We agree with the Appellants that that the Examiner has not set forth a prima facie case that claims 1--4 and 43 are not enabled as required by 35 U.S.C. Â§ 112, first paragraph. The Specification gives guidance as to how to make pyrazine containing compounds in general and contains several working examples. This is sufficient guidance for one skilled in the art to practice the claimed method over the full scope of the claims. While some experimentation may be required, given the nature of the chemistry involved and the state of the art, we agree with Appellants that it does not rise to the level of undue experimentation. Appeal Br. 15-16. The Examiner's arguments have been considered but are unpersuasive. The teachings of the instant Specification are not limited to the four species identified by the Examiner but embrace the entire genus of pyrazine containing compounds. The broad disclosure teaches the preparation of a broad class of precursors as well as intermediates. FF3-7. The Specification discloses the different substituents that can be used as well as the different reactants contemplated by the inventors. FF4. Reaction conditions are described as well. FF3. The Specification provides a reasonable amount of guidance to one skilled in the art to make pyrazine containing materials satisfying the enablement requirement. 9 Appeal2014-004800 Application 12/426,774 Conclusion of Law We conclude that the Examiner has failed to establish by a preponderance of the evidence that claims 1--4 are not enabled as defined by 35 U.S.C. Â§ 112, first paragraph. III Issue The Examiner has rejected claim 42 as indefinite as defined by 35 U.S.C. Â§ 112, second paragraph. The Examiner finds that the presence of an undefined R group in the pyrazine containing compound renders the claim indefinite. The Examiner finds that "[ c ]laims are unduly speculative where they define only a portion of the molecule." Ans. 12. Appellants contend that under existing case law the claims are not indefinite even though they present a partial structure. Appeal Br. 33-35. Appellants go on to argue that when read in light of the Specification, the claim is not ambiguous as the Specification defines what is included in the R group. Id. The issue with respect to this rejection is whether the Examiner has established by a preponderance of the evidence that claim 42 is indefinite as defined by 35 U.S.C. Â§ 112, second paragraph. Findings of Fact FF8. Claim 42 refers to a method for synthesizing 2-amino-6-R- substituted pyrazines. Appeal Br. 46. 10 Appeal2014-004800 Application 12/426,774 Principles of Law Recitation of only part of a chemical structure broadens the claim but does not render it indefinite. In re Fisher, 427 F.2d 833, 838 (CCPA 1970). Analysis We agree with Appellants that the use of the symbol R does not render the claims indefinite. The absence of a definition of R broadens the claim but does not render the claim indefinite. In response, the Examiner only states that the Examiner disagrees since the second paragraph of section 112 requires the claims to particularly point out what the Appellants regard as his invention. Ans. 24. The Examiner then goes on to recite several cases regarding the definiteness requirement but offers no explanation as to how they apply to the instant claim. Ans. 24--25. For example, the Examiner recites In re Wiggins, 488 F .2d 358 (CCP A 1973) for the proposition that when the scope of the claims cannot be determined when considered in light of the Specification, the claim is indefinite. The Examiner fails to show why one reading the specification would not know what R comprises. Similarly, the Examiner cites to Ex parte Miyazaki, 89 USPQ2d 1207 (BPAI 2008) for the proposition that if a claim can be construed in two or more ways, the Examiner is justified in requiring the applicant to more precisely define the claim terms. Again, the Examiner fails to explain how the instant claims are amenable to two or more interpretations. We find that the Examiner has failed to articulate a sufficient reason why the use of a generic "R" group renders the present claim indefinite. 11 Appeal2014-004800 Application 12/426,774 Conclusion of Law We find that the Examiner has failed to establish that claim 42 is indefinite as defined by 35 U.S.C. Â§ 112, second paragraph. IV Issue The Examiner has rejected claim 42 under 35 U.S.C. Â§ 112, second paragraph, as indefinite. The Examiner finds that the inclusion of specific esters as well as the general term ester in a Markush group renders the claim indefinite. Ans. 25. The Examiner also finds that since the claim can have more than on interpretation, the Examiner can require the Appellants to more precisely define the claim terms. Ans. 25. Appellants argue that the double inclusion of an element by members of a Markush group does not render the claim indefinite. Appeal Br. 37. Legal Principles "It is well known that 'members of the Markush group are ... alternatively usable for purposes of the invention."' Abbott Labs. v. Baxter Pharm. Prod., Inc., 334 F.3d 1274, 1281 (Fed. Cir. 2003) (citing In re Driscoll, 562 F.2d 1245, 1249 (CCPA 1977)). [T]he double inclusion of an element by members of a Markush group is not, in itself, sufficient basis for objection to or rejection of claims. Rather, the facts in each case must be evaluated to determine whether or not the multiple inclusion of one or more elements in a claim renders that claim indefinite. The mere fact that a compound may be embraced by more than one member of a Markush group recited in the claim does not necessarily render the scope of the claim unclear. For example, the Markush group, 12 Appeal2014-004800 Application 12/426,774 "selected from the group consisting of amino, halogen, nitro, chloro and alkyl" should be acceptable even though "halogen" is generic to "chloro." MPEP Â§ 2173.0S(h). Analysis We agree with Appellants that the inclusion of the term "ester" in the present claim does not render the claim indefinite. The Markush group lists alternative compounds that can be used as the leaving group in the practice of claim 42. The use of the term "ester" in addition to the recitation of specific esters may broaden the claim, but it does not render the claim indefinite. The double inclusion of compounds in a Markush group does not render the claims indefinite. MPEP Â§ 2173.0S(h). The Examiner argues that one skilled in the art cannot determine the scope of the claim because it includes both the broad term ester and specific ester. Ans. 26. This argument is unpersuasive. First, the Examiner has offered no explanation as to why one skilled in the art would not be able determine the scope of the claims. The term ester is one that is well understood by chemists. That the claim also recites specific esters does not change or confuse that meaning. Moreover, the Specification gives one skilled in the art guidance as to what is meant by the term ester. Spec. 8. The inclusion of esters in conjunction with the recitation of several specific esters does make the scope of claim indeterminable. The Examiner's reliance on Ex parte Wu, 10 USPQ2d 2031 (BP AI 1989), is misplaced. Ex parte Wu did not address the issue of the use of 13 Appeal2014-004800 Application 12/426,774 broad and narrow terms but was concerned with the use of the term "optionally" which is not at issue here. Finally, the Examiner argues that since the claim is amenable to two possible interpretations, the Examiner can require the Appellants to more precisely define the limits of his claim. Ans. 26. However, the Examiner offers no explanation as to why the claim is amenable to two different interpretations. The use of the term ester is consistent with the recitation of specific esters and does not yield two different interpretations. Conclusion of Law We find that the Examiner has failed to establish by a preponderance of the evidence that claim 42 is indefinite as defined by 35 U.S.C. Â§ 112, second paragraph. SUMMARY We affirm the rejection of claims 37 and 38 as failing to meet the written description requirement of 35 U.S.C. Â§ 112, first paragraph. We reverse the rejection of claims 1--4 for failing to meet the enablement requirement of 35 U.S.C. Â§ 112, first paragraph, and we reverse the rejection of claim 42 as indefinite under 35 U.S.C. Â§ 112, second paragraph. 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. Â§ 1.136(a). AFFIRMED-IN-PART 14