08128332 (B.P.A.I. Oct. 28, 1998)

Ex parte Rochat et al.

Board of Patent Appeals and InterferencesOct 28, 1998

08128332 (B.P.A.I. Oct. 28, 1998)

Application for patent filed September 29, 1993. 1 According to appellants, this application is a continuation of Application No. 08/047,886, filed April 15, 1993; which is a continuation of Application No. 07/381,212, filed July 17, 1989; both abandoned. -1- THIS OPINION WAS NOT WRITTEN FOR PUBLICATION The opinion in support of the decision being entered today (1) was not written for publication in a law journal and (2) is not binding precedent of the Board. Paper No. 40 UNITED STATES PATENT AND TRADEMARK OFFICE ________________ BEFORE THE BOARD OF PATENT APPEALS AND INTERFERENCES ________________ Ex parte ALAIN C. ROCHAT, OLOF WALLQUIST, ABUL IQBAL and JIN MIZUGUCHI ________________ Appeal No. 95-4721 Application No. 08/128,3321 ________________ ON BRIEF ________________ Before KIMLIN, JOHN D. SMITH and WEIFFENBACH, Administrative Patent Judges. KIMLIN, Administrative Patent Judge. DECISION ON APPEAL This is an appeal from the final rejection of claims 3-7 Appeal No. 95-4721 Application No. 08/128,332 -2- and 11, all the claims remaining in the present application. A copy of illustrative 11 is appended to this decision. The examiner relies upon the following reference as evidence of obviousness: Dix 3,484,487 Dec. 16, 1969 Appellants' claimed invention is directed to a process for preparing aminated diketobis(aryl or heteroaryl)pyrrolopyrroles of the recited formula. The process comprises reacting a pyrrolopyrrole of the claimed formula with a secondary amine in the presence of an anhydrous dipolar aprotic solvent, such as N-methylpyrrolidone. The reaction is conducted at a temperature in the range of 100E to 220EC at a pressure of from 1 to 3 bar. The present application is a grandchild of U.S. Application No. 07/381,212, filed July 17, 1989. Appellants took an appeal to this Board in the grandparent application, and the only difference between independent claim 11 now on appeal and independent claim 11 in the grandparent application is that in the present application the substituent X of the1 pyrrolopyrrole reactant is a brominated aryl group, whereas in Appeal No. 95-4721 Application No. 08/128,332 -3- the grandparent application X is either a chlorinated or1 brominated aryl group. The Board affirmed the examiner's rejection in the grandparent application under 35 U.S.C. Â§ 103 over the same Dix reference presently applied by the examiner. Also, appellants now rely upon the Wallquist Declaration, executed March 8, 1994, as evidence of unexpected results. The Declaration was not before the Board in the grandparent application. Appellants submit at page 5 of the principal Brief that "[c]laims 3-7 and 11 are argued together as to each issue." Accordingly, all the appealed claims stand or fall together with claim 11. In re Nielson, 816 F.2d 1567, 1572, 2 USPQ2d 1525, 1528 (Fed. Cir. 1987); Ex parte Schier, 21 USPQ2d 1016, 1018-19 (Bd. Pat. App. & Int. 1991). See also 37 CFR Â§ 1.192(c)(5) and (c)(6) (1994). Appealed claims 11 and 3-7 stand rejected under 35 U.S.C. Â§ 103 as being unpatentable over Dix. We have thoroughly reviewed each of appellants' arguments for patentability, as well as the declaration evidence relied upon in support thereof. However, we fully concur with the examiner's legal conclusion that the claimed subject matter Appeal No. 95-4721 Application No. 08/128,332 -4- would have been obvious to one of ordinary skill in the art within the meaning of Â§ 103 in view of the applied prior art. Accordingly, we will sustain the examiner's rejection. We have little doubt that one of ordinary skill in the art, armed with the disclosure of Dix, would have found appellants' claimed process prima facie obvious. As explained by the examiner, Dix evidences that it was known in the art to perform an amination process on aryl halides by reacting a secondary amine with an aryl halide in the presence of N- methylpyrrolidone as a solvent, which solvent is within the scope of appealed claim 11 and specifically recited in dependent claim 7. Dix teaches that N-methylpyrrolidone is a preferred solvent (column 1, line 62). Dix also teaches that bromine is a preferred halogen substituent on the aryl group (column 2, line 12). In addition, the reference teaches that a preferred temperature range for the reaction is 100 to about 280EC (column 2, line 27), which range totally embraces, and is almost congruent with, the claimed range of 100E to 220EC. Like appellants' process, the process disclosed by Dix provides an improved yield of aryl amine when the aryl halide is directly aminated Appeal No. 95-4721 Application No. 08/128,332 -5- in the presence of an organic solvent like N-methylpyrrolidone (column 1, lines 44-48). Appellants do not present any substantive argument that refutes the prima facie case of obviousness based on Dix. Rather, although appellants state a disagreement "with the underlying rejections based on obviousness" (page 5 of principal Brief), appellants rely upon a declaration by Dr. Olof Walquist, one of the present inventors, executed March 8, 1994, as evidence of unexpected and superior results (page 5 of principal Brief, last paragraph). According to appellants, the declaration demonstrates that the closest prior art process (Run No. 1 of Dix) gives only a 6.9% yield, while working Example 1 of the present specification gives a 51.3% yield. According to the declarant, "[t]his is indeed surprising and absolutely unexpected" (page 2 of declaration, last sentence). Our review of the declaration evidence leads us to the same conclusion as that reached by the examiner, i.e., the declaration is not sufficiently probative of nonobviousness to outweigh the evidence of obviousness represented by the Dix disclosure. First, we agree with the examiner that the Appeal No. 95-4721 Application No. 08/128,332 -6- probative value of the declaration is not commensurate in scope with the degree of protection sought by the appealed claims. In re Grasselli, 713 F.2d 731, 743, 218 USPQ 769, 778 (Fed. Cir. 1983); In re Clemens, 622 F.2d 1029, 1036, 206 USPQ 289, 296 (CCPA 1980). Example 1 of the specification that is reported in the declaration uses a temperature of 180EC which is considerably above the lower limit of the claimed range of 100EC. While appellants contend at page 7 of their principal Brief that 180EC is representative of the claimed range of 100E-220EC, no factual basis is offered for this conclusion. If, as appellants argue, it is unexpected that the claimed amination of an aryl halide gives high yields at a temperature as low as 180EC, it is reasonable to require appellants to demonstrate that a similar unexpected yield would result at a temperature that is considerably lower than 180EC, viz., at the claimed 100EC. In our view, the single temperature used in the declaration does not establish unexpected results for the claimed range which substantially coincides with the preferred temperature range disclosed by Dix. In re Greenfield, 571 F.2d 1185, 1188, Appeal No. 95-4721 Application No. 08/128,332 -7- 197 USPQ 227, 229 (CCPA 1978); In re Smith, 398 F.2d 849, 852, 158 USPQ 287, 289 (CCPA 1968). Secondly, although declarant Walquist characterizes the comparative results as surprising and unexpected, the declarant has not laid the requisite factual foundation upon which to conclude that the demonstrated results are truly unexpected in light of the Dix disclosure considered in its entirety. In re Longi, 759 F.2d 887, 896-97, 225 USPQ 645, 651 (Fed. Cir. 1985); In re Grunwell, 609 F.2d 486, 491, 203 USPQ 1055, 1059 (CCPA 1979); In re Lindell, 385 F.2d 453, 455, 155 USPQ 521, 523 (CCPA 1967). We find it significant that Example 1 of the declaration, in accordance with the present invention, uses a reaction time of 11 hours, whereas the reaction time of Comparative Run 1 of Dix is only 2 hours. We cannot ignore this discrepancy in reaction times because Dix expressly discloses that "[t]he reaction can be carried to any desired degree of completion and reaction times can vary from about 1 to about 25 hours" (column 2, lines 31-33). We note that Run 1 of Dix has an ultimate yield of 21% for a reaction time of 2 hours, and it seems reasonable to presume that if the Dix reaction was conducted for the disclosed 25 hours, a Appeal No. 95-4721 Application No. 08/128,332 -8- considerably higher yield would result. Also, the declarant fails to explain any expected affect on yield resulting from the amination of the claimed heterocyclic compounds vis-Ã -vis the phenol chloride of Dix. Consequently, for the reasons outlined above, we find that appellants have not carried their burden of demonstrating that the declaration and specification results are truly unexpected. In re Merck & Co., 800 F.2d 1091, 1099, 231 USPQ 375, 381 (Fed. Cir. 1986); In re Klosak, 455 F.2d 1077, 1080, 173 USPQ 14, 16 (CCPA 1972). In conclusion, based on the foregoing, it is our judgment that the evidence of obviousness presented by the examiner outweighs the evidence of nonobviousness submitted by appellants. Accordingly, the examiner's decision rejecting the appealed claims is affirmed. Appeal No. 95-4721 Application No. 08/128,332 -9- No time period for taking any subsequent action in connection with this appeal may be extended under 37 CFR Â§ 1.136(a). AFFIRMED EDWARD C. KIMLIN ) Administrative Patent Judge ) ) ) ) ) JOHN D. SMITH ) BOARD OF PATENT Administrative Patent Judge ) APPEALS AND ) INTERFERENCES ) ) ) CAMERON WEIFFENBACH ) Administrative Patent Judge ) clm Appeal No. 95-4721 Application No. 08/128,332 -10- Michael W. Glynn Ciba-Geicy Corp. Patent Dept. 520 White Plains Rod P.O. Box 2005 Tarrytown, NY 10591-9005 Appeal No. 95-4721 Application No. 08/128,332 -1- APPENDIX 11. A process for the preparation of a compound of formula wherein R is a group1 and R is a group2 Appeal No. 95-4721 Application No. 08/128,332 -2- or has the meaning of R , in which formulae above R and R are1 5 6 identical and are C -C alkyl, 2-hydroxyethyl, 2-mercaptoethyl,1 12 cyclohexyl, benzyl or phenylethyl, or -NR R is pyrrolidinyl,5 6 piperidyl, morpholinyl or thiomorpholinyl, and R and R are7 8 each independently of the other hydrogen, chloro, bromo, C -1 C alkyl or C -C alkoxy, which process comprises reacting a4 1 4 pyrrolopyrr ole of formula wherein X is a group1 Appeal No. 95-4721 Application No. 08/128,332 -3- and X is a group2 or has the same meaning as X , and R and R are defined1 7 8 hereinabove, with a secondary amine of formula R5 ' H ) N (VI), ( R6 wherein R and R are defined hereinabove in the molar ratio57 68 1:1 or, if X has the same meaning as X , in the molar ratio2 1 1:2, in the presence of an anhydrous dipolar aprotic solvent of an amount 0.1 to 15 times in excess of stoichiometric proportion, based on the amine of formula VI, of an annydrous Appeal No. 95-4721 Application No. 08/128,332 -4- organic base, in the temperature range from 100E to 220EC and under a pressure from 1 to 3 bar.