Ex Parte Coggan et al

Board of Patent Appeals and Interferences

Jul 1, 2010

11263671 (B.P.A.I. Jul. 1, 2010)

UNITED STATES PATENT AND TRADEMARK OFFICE
__________

BEFORE THE BOARD OF PATENT APPEALS
AND INTERFERENCES
__________

Ex parte JENNIFER A. COGGAN and TIMOTHY P. BENDER
__________

Appeal 2010-001733
Application 11/263,671
Technology Center 1600
__________

Before DEMETRA J. MILLS, FRANCISCO C. PRATS, and
JEFFREY N. FREDMAN, Administrative Patent Judges.

FREDMAN, Administrative Patent Judge.

DECISION ON APPEAL
This is an appeal under 35 U.S.C. § 134 involving claims to methods
of preparing tertiary arylamine compounds. We have jurisdiction under 35
U.S.C. § 6(b). We affirm.

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Statement of the Case
Claims 1-4, 6-8, and 10-26 are on appeal. In response to an Election
of Species, Appellants “elected, with traverse, the species where the aryl
halide is 4-bromobiphenyl, the arylamine is diphenylamine, the ionic liquid
is (tetradecyl) trihexyl phosphonium chloride, and the resulting tertiary
arylamine compound is N,N-diphenyl-4-aminobiphenyl” (App. Br. 9). We
limit our consideration of the merits of the appealed rejections to the elected
species. See Ex parte Ohsaka, 2 USPQ2d 1460, 1461 (Bd. Pat. App. Int.
1987). Claim 1 is representative and reads as follows:
1. A process for the preparation of a tertiary arylamine
compound, comprising:
reacting an arylhalide and an arylamine in an ionic
liquid in the presence of a catalyst,
adding water and an organic solvent to a product
formed by the reaction, wherein the organic solvent is
selected from the group consisting of toluene, decane,
saturated hydrocarbons, dimethoxyethane, and mixtures
thereof;
wherein the addition forms a triphasic system that
comprises a first phase comprising the tertiary arylamine
and the organic solvent, a second phase comprising the
catalyst and the ionic liquid; and a third phase comprising
water and inorganic salts, and
separating the first phase from the second phase.

The prior art
The Examiner relies on the following prior art references to show
unpatentability:
Hartwig et al. US 6,100,398 Aug. 8, 2000

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Gerritsma et al., Heck reactions of aryl halides in phosphonium salt
ionic liquids: library screening and applications, 45 TETRAHEDRON LETTERS
7629-7631 (2004).
The issue
The Examiner rejected claims 1-4, 6-8, and 10-26 under 35 U.S.C. §
103(a) as being obvious over Hartwig and Gerritsma (Ans. 4-5).
The Examiner finds that “Hartwig et al. teach the process for
preparing tertiary aryl amine compounds by reacting an aryl bromide with a
secondary aryl amine in an organic solvent with a palladium catalyst such as
palladium acetate with tri-t-butylphosphine and sodium t-butoxide” (Ans. 4).
The Examiner finds that “Hartwig et al. does not teach the use of
(tetradecyl)trihexyl phosphonium chloride, making a triphasic mixture,
recycling the catalyst by recovering the (tetradecyl)trihexyl phosphonium
chloride layer, or performing the reaction in a continuous mode” (Ans. 4).
The Examiner finds that
Gerritsma et al. teach the use of (tetradecyl)trihexyl
phosphonium chloride for palladium acetate catalyzed
processes, with addition of hexane and brine to create a
triphasic mixture in which the product is in the organic
layer, the catalyst is in the (tetradecyl)trihexyl phosphonium
chloride layer, and salts are in the aqueous layer, the
(tetradecyl)trihexyl phosphonium chloride is isolated and
reused for a total of four reaction cycles.

(Ans. 4-5.)
Appellants argue that “Hartwig nowhere provides any reason or
rationale for specifically selecting these reactants, and specifically
conducting the reaction of these materials in any ionic liquid, and especially
not in the specific elected ionic liquid THP-Cl” (App. Br. 10-11).
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Appellants argue that “Hartwig would not have motivated one of ordinary
skill in the art to have modified the disclosed process to add water and an
organic solvent to form the claimed triphasic system, and then to separate
the first phase from the second phase” (App. Br. 11). Appellants argue that
Gerritsma “fails to teach or suggest preparing a tertiary arylamine compound
by reacting an arylhalide and an arylamine in an ionic liquid in the presence
of a catalyst” (App. Br. 12).
Appellants also argue that the “mere similar use of a palladium
catalyst does not provide sufficient motivation to have combined the
references” (App. Br. 13). Appellants argue that “there was no reason or
rationale, other than based on Applicants’ own disclosure, to have combined
the references by inserting the ionic liquid of Gerritsma into the reaction of
the Hartwig reference in order to recycle the catalyst” (App. Br. 14).
In view of these conflicting positions, we frame the obviousness issue
before us as follows:
Does the evidence of record support the Examiner’s conclusion that
Hartwig and Gerritsma render obvious the process of Claim 1?
Findings of Fact (FF)
1. Hartwig teaches the synthesis “of N-aryl amine compounds.
The process of the invention comprises reacting an amine-containing
compound, such as an aryl amine, heterocyclic amine, secondary
alkylamine, or carbamate, with an arylating compound in the presence of a
base and transition metal catalyst under reaction conditions effective to form
an N-aryl amine compound” (Hartwig, col. 3, ll. 8-15).
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2. Hartwig teaches that “[p]referred arylating compounds used in
the process of the invention include aryl bromides and aryl chlorides.
Examples of suitable aryl bromides include . . . p-phenyl phenyl bromide”
(Hartwig, col. 4, ll. 5-10).
3. Hartwig teaches a procedure
for the Reaction of Amines with Aryl Halides: In a dry box,
aryl halide (1.00-1.10 mmol), amine (1.00 mmol), Pd(dba) 2
or Pd(OAc)2 (0.01-0.02 mmol), tri-t-butylphosphine (1.6-
3.2 mg, 0.008-0.016 mmol, 0.8 eq/Pd), and sodium tert-
butoxide (144 mg, 1.50 mmol) were weighed directly into a
screw cap vial. A stir bar was added followed by 1.0-2.0 mL
of toluene to give a purple mixture. The vial was removed
from the dry box and the mixture was stirred at room
temperature. The reaction was monitored by thin layer
chromatography or GC. After complete consumption of
starting materials, the resulting thick brown suspension was
adsorbed onto silica gel and purified by flash
chromatography.

(Hartwig, col. 7, ll. 24-37).
4. Hartwig teaches that “P(t-Bu)3 -complexes of palladium have
allowed from Suzuki and Heck chemistry to be conducted with aryl
chlorides” (Hartwig, col. 16, ll. 60-62).
5. Hartwig teaches that the “catalyst system involving P(t-Bu)3 as
ligand allowed for much milder arylation of azoles than the combination of
Pd(OAc)2 and DPPF reported previously” (Hartwig, col. 21, ll. 34-36).
6. The Examiner finds that Hartwig “does not teach the use of
(tetradecyl)trihexyl phosphonium chloride, making a triphasic mixture,
recycling the catalyst by recovering the (tetradecyl)trihexyl phosphonium
chloride layer, or performing the reaction in a continuous mode” (Ans. 4).
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7. Gerritsma teaches that the “Heck cross-coupling reaction has
now become a common procedure for carbon-carbon bond formation
between alkenes and organic halides or triflates lacking sp3-hybridized β-
hydrogens” (Gerritsma 7629, col. 1).
8. Gerritsma teaches that “[u]sing ionic liquids, it is often possible
to recycle the active (and often expensive) catalyst subsequent to extraction
of the organic product and inorganic salt by-products. A number of Heck
reactions have been performed in ionic liquids” (Gerritsma 7629, col. 1).
9. Gerritsma teaches that “[a]nother class of readily available,
often overlooked ionic liquid are those based on quaternary phosphonium
salts” (Gerritsma 7629, col. 1).
10. Gerritsma teaches that “initial efforts focused on the Heck
couplings of aryl iodides” (Gerritsma 7629, col. 2).
11. Gerritsma teaches that “the counter anion to the
trihexyl(tetradecyl)- phosphonium (THP) cation plays a significant role in
the outcome of the reaction. The best ionic liquids were shown to be THP-Cl
. . . and THP-decanoate” (Gerritsma 7629, col. 2).
12. Gerritsma teaches that “THP-Cl demonstrated itself to be much
easier to work with in the purification stage. Addition of hexane and brine to
the reaction mixture containing THP-Cl allowed for the separation of three
distinct phases with the palladium remaining in the middle ionic liquid layer,
the coupled product in the organic layer and any salts in the aqueous layer”
(Gerritsma 7629, col. 2).
13. Gerritsma teaches that “[p]urification simply required
separation of the phases” (Gerritsma 7629, col. 2 to 7630, col. 1).
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14. Gerritsma teaches that “the IL layer containing the Pd catalyst
was shown to be active and reuseable” (Gerritsma 7630, col. 1).
15. Gerritsma teaches that “judious [sic, judicious] choice of
phosphonium salt ionic liquid provides an economical, recyclable media for
the Heck cross-coupling reaction” (Gerritsma 7631, col. 1).
16. The Examiner finds, and Appellants do not dispute, that brine
“is salt water” (Ans. 8).
Principles of Law
The question of obviousness is resolved on the basis of underlying
factual determinations including: (1) the scope and content of the prior art;
(2) the level of ordinary skill in the art; (3) the differences between the
claimed invention and the prior art; and (4) secondary considerations of
nonobviousness, if any. Graham v. John Deere Co., 383 U.S. 1, 17 (1966).
The Supreme Court has recently emphasized that “the [obviousness] analysis
need not seek out precise teachings directed to the specific subject matter of
the challenged claim, for a court can take account of the inferences and
creative steps that a person of ordinary skill in the art would employ.” KSR
Int'l v. Teleflex Inc., 550 U.S. 398, 418 (2007).
“The combination of familiar elements according to known methods
is likely to be obvious when it does no more than yield predictable results.”
Id. at 416. “If a person of ordinary skill can implement a predictable
variation, § 103 likely bars its patentability.” Id. at 417.
Analysis
Hartwig teaches preparation of N-aryl amine compounds involving
the reaction of an arylhalide and an arylamine (FF 1-3). Hartwig teaches the
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use of the aryl bromide, p-phenyl phenyl bromide as well as diphenylamine
and palladium catalysts such as palladium acetate with tri-t-butylphosphine
and sodium t-butoxide (FF 2, 3, 5; App. Br. 10). Hartwig teaches toluene as
the reaction solvent (FF 3).
Hartwig also teaches that “P(t-Bu)3 -complexes of palladium have
allowed from Suzuki and Heck chemistry to be conducted with aryl
chlorides” (Hartwig, col. 16, ll. 60-62; FF 4). Hartwig teaches that the
“catalyst system involving P(t-Bu)3 as ligand allowed for much milder
arylation of azoles than the combination of Pd(OAc)2 and DPPF reported
previously” (Hartwig, col. 21, ll. 34-36; FF 5).
The Examiner acknowledges that Hartwig “does not teach the use of
(tetradecyl)trihexyl phosphonium chloride, making a triphasic mixture,
recycling the catalyst by recovering the (tetradecyl)trihexyl phosphonium
chloride layer, or performing the reaction in a continuous mode” (Ans. 4).
However, Gerritsma teaches that in a Heck reaction, “[u]sing ionic
liquids, it is often possible to recycle the active (and often expensive)
catalyst subsequent to extraction of the organic product and inorganic salt
by-products. A number of Heck reactions have been performed in ionic
liquids” (Gerritsma 7629, col. 1; FF 8). Gerritsma teaches that “[a]ddition of
hexane and brine to the reaction mixture containing THP-Cl allowed for the
separation of three distinct phases with the palladium remaining in the
middle ionic liquid layer, the coupled product in the organic layer and any
salts in the aqueous layer” (Gerritsma 7629, col. 2; FF 12). Gerritsma
teaches that “[p]urification simply required separation of the phases”
(Gerritsma 7629, col. 2 to 7630, col. 1; FF 13).
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As noted by the Court in KSR, “[a] person of ordinary skill is also a
person of ordinary creativity, not an automaton.” 550 U.S. at 421. Here, as
the Examiner finds, the ordinary artisan would reasonably understand that
modifying the palladium catalyst reaction of an aryl halide (aryl bromide) of
Hartwig with the use of an ionic liquid as taught by Gerritsma in the
palladium catalyst Heck reaction of aryl halides would reasonably allow
recycling of the expensive palladium catalyst (FF 7-13).
Appellants argue that “Hartwig nowhere provides any reason or
rationale for specifically selecting these reactants, and specifically
conducting the reaction of these materials in any ionic liquid, and especially
not in the specific elected ionic liquid THP-Cl” (App. Br. 10-11). Appellants
argue that “Hartwig would not have motivated one of ordinary skill in the art
to have modified the disclosed process to add water and an organic solvent
to form the claimed triphasic system, and then to separate the first phase
from the second phase” (App. Br. 11). Appellants argue that Gerritsma “fails
to teach or suggest preparing a tertiary arylamine compound by reacting an
arylhalide and an arylamine in an ionic liquid in the presence of a catalyst”
(App. Br. 12).
Appellants also argue that the “mere similar use of a palladium
catalyst does not provide sufficient motivation to have combined the
references” (App. Br. 13). Appellants argue that “there was no reason or
rationale, other than based on Applicants’ own disclosure, to have combined
the references by inserting the ionic liquid of Gerritsma into the reaction of
the Hartwig reference in order to recycle the catalyst” (App. Br. 14).

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We are not persuaded. Neither reference alone renders the claims
obvious, rather the obviousness case is predicated on the combination of
Gerritsma’s teaching of recycling palladium catalysts in triphasic systems
which suggests and motivates the use of such triphasic systems in the
reaction of Hartwig (FF 1-13). That is, the ordinary artisan, apprised by
Gerritsma that the use of a triphasic system and ionic liquid permits the
recycling of the expensive palladium catalyst, would have reasonably
modified the very similar reaction of Hartwig to incorporate this
improvement. The Federal Circuit has recognized that
an implicit motivation to combine exists not only when a
suggestion may be gleaned from the prior art as a whole, but
when the “improvement” is technology-independent and the
combination of references results in a product or process that
is more desirable, for example because it is stronger,
cheaper, cleaner, faster, lighter, smaller, more durable, or
more efficient.

DyStar Textilfarben GmbH & Co. Deutschland KG v. C.H. Patrick Co., 464
F.3d 1356, 1368 (Fed. Cir. 2006). Here, the improvement is cheaper
production by reuse of the expensive catalyst (FF 7-13).
Appellants argue that “Gerritsma nowhere teaches the use of water
itself (rather than brine) in the separation step. Nor does Gerritsma teach, or
even imply, that water and brine have the same effect when washing a
completed chemical reaction” (Supp. Reply Br. 1).
We are not persuaded. Appellants do not dispute that brine is salt
water, i.e., water which comprises dissolved salts (FF 16). Appellants’
Claim 1 uses the open transitional phrase “comprising” and contains no
language which excludes the use of water with additional components such
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as dissolved salts. See Genentech, Inc. v. Chiron Corp., 112 F.3d 495, 501
(Fed. Cir. 1997) (‘“Comprising’ is a term of art used in claim language
which means that the named elements are essential, but other elements may
be added and still form a construct within the scope of the claim.”)
We therefore agree with the Examiner’s claim interpretation, which
the Examiner explicated in the Final Rejection mailed August 12, 2008. The
Court recognizes the fairness of reading claims broadly “before a patent is
granted [since] the claims are readily amended as part of the examination
process.” Burlington Indus., Inc. v. Quigg, 822 F.2d 1581, 1583 (Fed. Cir.
1987). “Thus, a patent applicant has the opportunity and responsibility to
remove any ambiguity in claim term meaning by amending the application.”
In re Bigio, 381 F.3d 1320, 1324 (Fed. Cir. 2004). Applying the broadest
reasonable interpretation to claims also “‘serves the public interest by
reducing the possibility that claims, finally allowed, will be given broader
scope than is justified.”’ In re Am. Acad. Of Sci. Tech. Ctr., 367 F.3d 1359,
1364 (Fed. Cir. 2004).

Conclusion of Law
The evidence of record support the Examiner’s conclusion that
Hartwig and Gerritsma render obvious the process of Claim 1.

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SUMMARY
In summary, we affirm the rejection of claim 1 under 35 U.S.C. §
103(a) as being obvious over Hartwig and Gerritsma. Pursuant to 37 C.F.R.
§ 41.37(c) (1)(vii)(2006), we also affirm the rejection of claims 2-4, 6-8, and
10-26, as these claims were not argued separately.

No time period for taking any subsequent action in connection with
this appeal may be extended under 37 C.F.R. § 1.136(a)(1)(iv)(2006).

AFFIRMED

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