Ex Parte Shi et alDownload PDFPatent Trial and Appeal BoardMay 29, 201813396805 (P.T.A.B. May. 29, 2018) Copy Citation UNITED STA TES p A TENT AND TRADEMARK OFFICE APPLICATION NO. FILING DATE 13/396,805 02/15/2012 21364 7590 05/29/2018 US ARMY RESEARCH LABORATORY ATTN: RDRL-LOC-1 2800 POWDER MILL RD ADELPHI, MD 20783-1138 FIRST NAMED INVENTOR Jianmin Shi 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. ARL 11-69 8753 EXAMINER OTTON, ALICIA L ART UNIT PAPER NUMBER 1626 MAILDATE DELIVERY MODE 05/29/2018 PAPER 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. PTOL-90A (Rev. 04/07) UNITED STATES PATENT AND TRADEMARK OFFICE BEFORE THE PATENT TRIAL AND APPEAL BOARD Ex parte JIANMIN SHI, ERIC W. FORSYTHE, and DAVID C. MORTON Appeal2017-004954 Application 13/396,805 1 Technology Center 1600 Before FRANCISCO C. PRATS, KRISTI L. R. SA WERT, and DAVID COTTA, Administrative Patent Judges. COTT A, Administrative Patent Judge. DECISION ON APPEAL This is an appeal under 35 U.S.C. § 134 involving claims to a method of making benzazole compounds. The Examiner rejected the claims on appeal under 35 U.S.C. § 103(a) as obvious. We affirm. 1 According to Appellants, the real party in interest is the United States Government as represented by the Secretary of the Army. App. Br. 3. Appeal2017-004954 Application 13/396,805 STATEMENT OF THE CASE The Specification discloses that "[b ]enzazole derivatives ... have been widely used for many applications," including as "surface coatings for absorbers of UV light," and "in organic electroluminescent (EL) devices." Spec. i-f 4. The Specification discloses "Shi's original U.S. Pat. Nos. 5,645,948 and 5,766,779 use a two step synthesis ofbenzazole[] derivatives from aryl acid chlorides by high temperature condensation." Id. i-f 6. The Specification further states "Guidry ... disclosed another two step synthesis of this class of material from acid chlorides by condensing the amide with a proximate anilino group present in the adduct in the presence of the condensing agent." Id. i-f 7. The Specification asserts that it is "an object of this invention to provide a one step process of making aryl or alkyl benzazoles from the corresponding aryl acid chlorides or alkyl acid chlorides without applying hazardous condensing agents." Id. i-f 8. Claims 1, 3-8 and 10 are on appeal. Claims 1 and 10 are illustrative and read as follows: 1. A method of making benzazole compounds of formula I: R' B ~NyA z~ n [w]herein: n is an integer equal to 1 or an integer of from 3 to 8· ' Z is O,NR or S; and Rand R' are individually hydrogen; alkyl of from 1 to 24 carbon atoms; aryl or hetero-atom substituted aryl of 5 to 20 carbon atoms and other heterocyclic systems; 2 Appeal2017-004954 Application 13/396,805 or a chloro, fluoro or bromo group; or Rand R' are individually cyano; or Rand R' are atoms necessary to complete a fused aromatic ring; wherein B is a linkage unit comprising alkyl, aryl, substituted alkyl, or substituted aryl which conjugately or unconjugately connects the multiple benzazoles together by a one step process of AC AB; and further wherein the benzazoles are prepared by a one step process from corresponding aryl acid chlorides or alkyl acid chlorides (AC) and 2-aminobenzaoles (AB) in a polar solvent. 10. The method according to claim 1, wherein benzazole is 1,3,5-tris(l-phenyl- lH-benzo[ d]imidazole-2-yl)benzene ~-o N b 1,3,5-tris(1-phenyl-1 H-benzo[ d]imidazol-2- yl)benzene App. Br. 17, 19 (Claim App.). 3 Appeal2017-004954 Application 13/396,805 The claims stand rejected as follows. Claims 1 and 3-8 were rejected under 35 U.S.C. § 112 for failure to comply with the written description requirement. Final Act. 9. 2 In the Examiner's Answer, the Examiner withdrew this rejection. Ans. 7. Accordingly, this rejection is no longer a part of this appeal. Claims 1 and 3-8 were rejected as containing an improper Markush grouping. Final Act. 10. In the Examiner's Answer, the Examiner withdrew this rejection. Ans. 7. Accordingly, this rejection is no longer a part of this appeal. Claims 1, 3-8 and 10 were rejected under 35 U.S.C. § 103(a) as obvious over Shi. 3 Final Act. 12. FINDINGS OF FACT 1. Shi discloses: The following molecular structures constitute specific examples of preferred benzazoles satisfying the requirement of the invention: y N 0 Shi, col. 12, 11. 37---65. The Examiner finds, and Appellants do not dispute, that the above compound corresponds to the compound recited in claim 10. Ans. 4. 2 Office Action mailed Oct. 7, 2015 ("Final Act."). 3 US Patent No. 5,645,948, issued July 8, 1997 ("Shi"). 4 Appeal2017-004954 Application 13/396,805 2. Shi discloses that 1,3,5,-tris(N-phenyl-N-phenylamino) benzamide may be synthesized using the following method, which it labels as "Example 1." To a solution ofN-phenyl-1,2-phenylenediamine (16.6 g, 0.09 mol) in 100 mL ofN-methyl pyrrolidinone was added 1,3,5,- benzenetricarbonyl chloride (8.0 g, 0.03 mol) in portion at room temperature under nitrogen. The reaction mixture was stirred at room temperature for two hours then raise the reaction temperature to 50Q C. for another half hour. After cooling the reaction mixture was poured into 300 ml of cool water with stirring. The resulting precipitates were filtered and washed with water. After drying, the tribenzamide was collected to give 19.5 g (yield 92%). Id. at col. 26, 1. 66- col. 27, 1. 8. The Examiner finds, and Appellants do not dispute, that the 1,3,5-benzenetricarbonyl chloride used in the above process corresponds to compound AC in the reaction recited in claim 1. Final Act. 14. The Examiner also finds, and Appellants do not dispute, that the N- phenyl-1,2-phenylenediamine used in the above process corresponds to compound AB in the reaction recited in claim 1. Id, 3. Shi discloses that 2-2', 2"-(1,3,5-phenylene)tris[l-phenyl-lH- benzimidazole] (TPBI) may be synthesized using the following method, which it labels as "Example 2." TPBI was prepared by heating 1,3,5-tris(N-phenyl-N- phenylamino )benzamide in 0.3 atm. nitrogen pressure at 280Q- 295Q C. for about one hour. The pure TPBI (which can be used directly for cell fabrication) was obtained by sublimation twice at 315Q C. at 2 Torr pressure. Id. at col. 27, 11. 11-16. 4. The Specification discloses: In a typical example, 2-aminobenzoles (AB), aryl or alkyl acid chloride (AC) was slowly added to a polar solvent under 5 Appeal2017-004954 Application 13/396,805 moisture protection. Preferably, the polar solvent, such as N- methyl-2-pyrrolidinone (NMP), has a high boiling temperature. The reaction mixture was stirred at ambient temperature from one to several hours under moisture protection. Then, with vigorous stirring, the reaction mixture was raised to a higher temperature (up to 205 QC) for a few hours until the reaction was completed. The reaction mixture was then cooled to room temperature and poured into water with vigorous stirring. The resultant precipitates were filtered and washed with a carefully chosen solvent, such as water, methanol, ethanol, acetone or mixture of them. In most cases, the product can be directly sublimed for organic EL device fabrication without going through future purification process. Spec. ,-r 11. ANALYSIS Appellants argue claims 1, 3-8, and 10 together. We designate claim 1 as representative. In rejecting claims 1, 3-8, and 10 as obvious, the Examiner found that "each and every element of the claimed process is explicitly taught [by Shi], with the exception of the fact that the compound of Example 1 [described in FF2] is isolated prior to its use in the preparation of Example 2 [described in FF3]." Ans. 9. The Examiner concluded that it would have been obvious to eliminate the step by which the intermediate product - i.e. the compound produced by the process set forth in FF2 -was isolated and purified, thus performing the process in the manner claimed. Id. The Examiner explained: "[i]t would have been readily apparent to the skilled artisan that cutting out a step where the intermediate compound is isolated would also eliminate the possibility of losing any of the yield of that compound in the process of isolation/ purification." Id. The Examiner further reasoned that "making a batch process continuous ... is prima facie obvious where there is no 6 Appeal2017-004954 Application 13/396,805 evidence of unexpected results." Id. (citing In re Dilnot, 319 F .2d 188, 13 8 (CCPA 1963)). We adopt the Examiner's findings of fact and reasoning regarding the scope and content of the prior art (Ans. 3-10; Final Act. 6-8, 12-16) and agree that the claims would have been obvious over Shi. We address Appellants' arguments below. Appellants argue that Example 1 (FF2) "only teaches the precursor compound ... [i]t does not teach the final product as in the instant application." App. Br. 10-11. According to Appellants, "[i]n order to obtain the [claimed] compound ... one of ordinary skill would have to proceed to the second step of [Shi], which is shown in Example 2 [FF3]." Id. Appellants thus summarize, "Shi et al. teaches a two-step process to obtain the compound shown in Appellant's claim 10. The instant application teaches a one step process." Id. We are not persuaded that Appellants' arguments show reversible error in the Examiner's conclusion of obviousness. As noted by the Examiner, the Specification teaches a process including the same steps as described in Shi' s process. Ans. 7; compare FF2 and FF3 with FF4. The Examiner acknowledges that Shi includes "the additional step ... [of] isolation of the intermediate (Example 1) prior to the formation of the final product (Example 2)," (Ans. 7-8) but finds that it would have been obvious to eliminate the step of isolating the intermediate, which would result in the claimed method. Appellants' argument that Shi teaches a two-step process does not account for the Examiner's proposed elimination of the step of isolating the intermediate. 7 Appeal2017-004954 Application 13/396,805 Appellants argue that the Examiner erred by "using a hindsight analysis to piece together components of the Applicant's one-step process for synthesizing benzazoles (BZZ) while failing to provide any rationale for why or how it would have been obvious for one of ordinary skill to combine these references." App. Br. 13. We are not persuaded because the Examiner did, in fact, provide a rationale for eliminating the step of isolating Shi' s intermediate, reasoning that the skilled artisan would have understood that doing so would "minimize loss of product between steps and ultimately produce a higher yield of the end product." Ans. 8; see also, id. at 6, 9. With respect to Appellants' hindsight argument, Appellants point to no evidence that any of the Examiner's findings were beyond the level of ordinary skill at the time of the invention or could have been taken only from Appellants' Specification. See In re McLaughlin, 443 F.2d 1392, 1395 (CCPA 1971). Accordingly, we affirm the Examiner's rejection of claim 1 as obvious over Shi. Because they were not argued separately, claims 3-8 and 10 fall with claim 1. SUMMARY For the reasons provided herein and those set forth in the Examiner's Answer and Final Action, we affirm the Examiner's rejection of claims 1, 3- 8, and 10 under 35 U.S.C. § 103(a) as obvious over Shi. No time period for taking any subsequent action in connection with this appeal may be extended under 37 C.F.R. § 1.136(a)(l )(iv). AFFIRMED 8 Copy with citationCopy as parenthetical citation