Ex Parte Rozman et al

Board of Patent Appeals and Interferences

Apr 27, 2010

10875864 (B.P.A.I. Apr. 27, 2010)

UNITED STATES PATENT AND TRADEMARK OFFICE
____________

BEFORE THE BOARD OF PATENT APPEALS
AND INTERFERENCES
____________

Ex parte KARL K. ROZMAN KRISTIAN FRIED,
PAUL F. TERRANOVA, GUNDA I. GEORG, and APURBA DUTTA
____________

Appeal 2009-007193
Application 10/874,864
Technology Center 1600
____________

Decided: April 27, 2010
____________

Before TONI R. SCHEINER, DONALD E. ADAMS, and JEFFREY N.
FREDMAN, Administrative Patent Judges.

ADAMS, Administrative Patent Judge.

DECISION ON APPEAL
This appeal under 35 U.S.C. § 134 involves claims 10, 27, 28, 31, 32,
and 50. We have jurisdiction under 35 U.S.C. § 6(b). Of the remaining
claims, the Examiner has indicated that claims 1-4, 6-9, 12-16, and 18-21,
and 27-51 are allowable and claims 29, 30, 33-49, and 51 stand objected to
as being dependent upon a rejected base claim (App. Br. 2; Ans. 2).
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STATEMENT OF THE CASE
The claims are directed to phenothiazine compounds. Claim 10 is
illustrative:
10. Phenothiazine compounds having the following formula:

wherein X1 and X4 are both Cl; and
wherein at least one of X2 and X3, is independently, hydrogen,
halogen or trifluoromethyl; and not more than one of X2 and X3 is hydrogen;
and
wherein R is H or lower alkyl; and
wherein the sulfur is optionally oxidized.

The Examiner relies on the following evidence:
Du-xin Li, et al. (Li I), Synthesis of N-Ethyl-Phenothiazine and its
Derivatives, 3 J. Shanxi Univ., China 66-71 (1988), as translated in
PTO2007-0744.

Du-xin Li, et al. (Li II), Synthesis of N-Ethyl-Phenothiazine and its
Derivatives, 3 J. Shanxi Univ., China 66-71 (1988), original Chinese
Document.

Shouping Huang, et al., Fluorescence spectra study of 2,3,7,8-tetrachloro-N-
ethylphenothiazine, 17(3) Guangpuxue Yu Guangpu Fenxi 112-114 (1997),
CAPLUS Accession No. 1997:466205.

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Appellants rely upon the following evidence:

Kristian Fried’s Third Supplemental Declaration, executed August 20, 2007.

Dieter Lenoir’s Declaration, executed September 7, 2007.

The rejection presented by the Examiner follows:
Claims 10, 27, 28, 31, 32, and 50 stand rejected under 35 U.S.C.
§ 102(b) as being anticipated by Li I.
We affirm.

ISSUE

Does the evidence of record support a conclusion that Li I’s teaching
of the use of Cl2 that has passed through an ice bath at 0 °C infers that the
entire reaction is to be carried out at or near the melting temperature of the
solvent?

FINDINGS OF FACT
FF 1. Li teaches “2,3,7,8-tetrachloro-10-ethyl-10H-Phenothiazine that is
the same as appellants when appellant’s [sic] formula has the following
substiuents:X1 =X2 = X3 = X4 = Cl; and R = ethyl” (Ans.3).
FF 2. The Examiner finds that Li teaches the “synthetic route” for 2,3,7,8-
tetrachloro-10-ethyl-10H-Phenothiazine “at page 67” of the “Chinese
language” document

(Ans. 5-6).
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FF 3. Li I teaches the synthesis of 2,3,7,8-tetrachloro-10-ethyl-10H-
Phenothiazine, wherein “5 g phenthiazine and 1 g anhydrous FeCl3 are
placed in a 250 ml three-necked flask; to them is added 50 ml of glacial
acetic acid, Cl2 is passed through an ice bath at 0°C, and the reaction goes
for 1.5 hours” (Li I 21: 7-9; see also Ans. 5).
FF 4. Fried declares that Li I and II do not teach the synthesis of 2,3,7,8-
tetrachloro-10-ethyl-10H-Phenothiazine, but instead “teaches the production
of 1,3,7,9-tetrachlorophenothiazine” (Fried Dec. 2: ¶ 5).
FF 5. Fried declares that:
[M]y laboratory reproduced the reaction precisely following the
instructions given in the Li Article, as well as other variations
of the original reaction conditions. More specifically, I
attempted to make 2,3,7,8-TCPT by chlorination of the
unsubstituted phenothiazine. . . . [T]he work-up was likely
identical to that described in Example 2 of the Li article. In
particular, the Li Article states that “Cl2 passed through an ice
bath at 0 ºC, and the reaction goes for 1.5 hours.” The Li
Article did not specify the temperature of the reaction mixture
itself, but only notes that the ice bath is at 0 ºC. I kept my
reaction cooled with an ice bath (like the Li Article). I found
that when temperatures below the melting point of the solvent
(glacial acetic acid), which is 16 ºC, were used, the mixture
solidified, and no reaction could take place. Thus, I removed
the ice bath periodically to maintain the reaction temperature at
about 14 ºC so the reaction could proceed.
. . .
I also conducted additional experiments with variations in the
scheme outlined by the authors of the Li Article. I varied the
reaction time and temperature. More specifically, in addition to
keeping the reaction mixture at or near its melting point, I tried

1 This reference is not paginated. Accordingly, page numbers refer to the
page of the reference as if it were numbered consecutively starting with the
first page (page 1).
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keeping the mixture cooled but liquid. I also tried
experimenting with brief chlorination times, and those that
lasted for hours. None of those modifications resulted in the
production of 2,3,5,8-TCPT . . . [but] [i]nstead, 1,3,7,9-TCPT
was produced.

(Fried Dec. 2: ¶ 8; 3: ¶ 11; and 3: ¶ 15.)
FF 6. Lenoir declares that the “Li Article teaches only the production of
1,3,7,9-tetrachlorophenothiazine” (Lenoir Dec. 2: ¶ 6).
FF 7. The Examiner finds that the reaction conditions set forth in the Fried
Declaration are different from those set forth in Li I, because Fried
performed the reaction at 0 or 14 °C, whereas Li I does not teach that the
reaction be performed in an ice bath at 0 °C, but instead teaches only that Cl2
is passed through an ice bath at 0 °C (Ans. 10).

PRINCIPLES OF LAW
“A claim is anticipated only if each and every element as set forth in
the claim is found, either expressly or inherently described, in a single prior
art reference.” Verdegaal Bros. v. Union Oil Co. of California, 814 F.2d
628, 631 (Fed. Cir. 1987).
[T]he proper test of a description in a publication as a bar
to a patent as the clause is used in section 102(b) requires a
determination of whether one skilled in the art to which the
invention pertains could take the description of the invention in
the printed publication and combine it with his own knowledge
of the particular art and from this combination be put in
possession of the invention on which a patent is sought.

In re Sasse, 629 F.2d 675, 681 (CCPA 1980), citing In re LeGrice, 301 F.2d
929, 933 (CCPA 1962) and In re Samour, 571 F.2d 559, (CCPA 1978).
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The Examiner bears the burden of presenting at least a prima facie
case of anticipation. In re King, 801 F.2d 1324, 1327 (Fed. Cir. 1986); In re
Wilder, 429 F.2d 447, 450, (CCPA 1970). Once a prima facie case is
established, the burden shifts to Appellants to rebut the Examiner’s prima
facie case. In re Sasse, 629 F.2d at 681; In re Oetiker, 977 F.2d 1443, 1445
(Fed.Cir.1992). The question then becomes whether, based on the totality of
the record, the preponderance of the evidence establishes that the Examiner
carried his burden of proof. See Id.

ANALYSIS
The claims have not been argued separately and therefore stand or fall
together. 37 C.F.R. § 41.37(c)(1)(vii). Claim 10 is representative.
The Examiner finds that Li I teaches “2,3,7,8-tetrachloro-10-ethyl-
10H-Phenothiazine that is the same as appellants when appellant’s [sic]
formula has the following substiuents:X1 =X2 = X3 = X4 = Cl; and R = ethyl”
(FF 1).
Appellants contend that “the Li Article is not enabled and therefore
does not anticipate the claimed invention” (App. Br. 6). Appellants
recognize that “the Li Article states that th[e] ‘Cl2 [is] passed through an ice
bath at 0 °C, and the reaction goes for 1.5 hours’” (App. Br. 9; FF 3; and FF
6). Nevertheless, Appellants contend that since “[t]he Li Article did not
specify the temperature of the reaction mixture itself, but only notes that the
ice bath is at 0 °C[,] Dr. Fried kept his reaction cooled with an ice bath (like
the Li Article)” and found that because this temperature is below the melting
temperature of the solvent in the system “the mixture solidified, and no
reaction could take place” (App. Br. 9; FF 6). Appellants’ also contend that
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in a variation of their interpretation of Li I’s methodology the reaction
mixture was removed from “the ice bath periodically to raise the temperature
near the melting point of the solvent” or “cooled but liquid” and again failed
to produce the claimed compound (App. Br. 9-10; FF 4-6; see also Reply Br.
6). We are not persuaded by this argument or evidence.
Notwithstanding Appellants’ contention to the contrary, Li I does not
teach that the reaction is carried out below or near the melting point of the
solvent, or cooled but liquid (Cf. FF 5). Instead, Li I teaches that it is the Cl2
that is passed through an ice bath at 0 °C (FF 8). While, Appellants contend
that they “follow[ed] the procedures of the Li Article precisely” (App. Br.
10); we find that Appellants have extrapolated Li I’s teaching of passing Cl2
through an ice bath at 0 °C to performing the entire reaction at or near the
melting temperature of the solvent or cooled but liquid. The evidence on
this record fails to support Appellants’ interpretation of Li I.
Li I teaches the synthesis of 2,3,7,8-tetrachloro-10-ethyl-10H-
Phenothiazine, wherein “5 g phenthiazine and 1 g anhydrous FeCl3 are
placed in a 250 ml three-necked flask; to them is added 50 ml of glacial
acetic acid, Cl2 is passed through an ice bath at 0°C, and the reaction goes
for 1.5 hours” (FF 3). Li I teaches measurement of an IR spectra for 2,3,7,8-
tetrachloro-10-ethyl-10-Phenothiazine and states “[f]rom the above
measurements it is clear that the compounds we have synthesized have the
correct structure” (Li I 4:16-17; 5:11-12). While Appellants are correct in
that Li I fails to identify the specific temperature at which the reaction is
performed, Appellants have failed to establish a factual basis on this record
to support the conclusion that a person of ordinary skill in this art would
have reasonably performed Li I’s reaction at or near the melting temperature
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of the solvent or cooled in any manner other than through the addition of Cl2
that is passed through an ice bath at 0 °C. We find that a person of ordinary
skill in this art would have interpreted Li I as teaching a reaction above the
melting temperature of the solvent, that is “cooled” only by the addition of
the Cl2 used in the reaction that has passed through an ice bath at 0°C.
In view of the foregoing, and the lack of evidence to the contrary, we
are compelled to rule in favor of the Examiner’s finding that Appellants’
rebuttal evidence fails to utilize the same reaction conditions set forth in the
reference (FF 8). Accordingly, Appellants have failed to establish that Li I
fails to provide an enabling description of Appellants’ claimed invention.

CONCLUSION OF LAW
The evidence of record fails to support a conclusion that Li I’s
teaching of the use of Cl2 that has passed through an ice bath at 0 °C infers
that Li’s entire reaction is to be carried out at or near the melting
temperature of the solvent.
The rejection of claim 10 under 35 U.S.C. § 102(b) as being
anticipated by Li I is affirmed. Claims 27, 28, 31, 32, and 50 fall together
with claim 10.

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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

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