Ex Parte Manners et al

Patent Trial and Appeal Board

Jul 8, 2016

11289240 (P.T.A.B. Jul. 8, 2016)

UNITED STA TES p A TENT AND TRADEMARK OFFICE
APPLICATION NO. FILING DATE FIRST NAMED INVENTOR
111289,240 11129/2005 Gary D. Manners
25278 7590 07112/2016
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EXAMINER
GOON, SCARLETT Y
ART UNIT PAPER NUMBER
1673
NOTIFICATION DATE DELIVERY MODE
07/12/2016 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):
Claudia.Reynolds@ars.usda.gov
Robin.McCormick@ars.usda.gov
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte GARY D. MANNERS and ANDREW P. BREKSA III
Appeal2013-000987
Application 11/289,240
Technology Center 1600
Before DONALD E. ADAMS, LORA M. GREEN, and
RICHARD M. LEBOVITZ, Administrative Patent Judges.
LEBOVITZ, Administrative Patent Judge.
DECISION ON APPEAL 1
This appeal involves claims directed to an analytically certified single
component amorphous solid consisting essentially of a purified alkali metal
salt of an individual species of isolated limonoid glycoside mono-carboxylic
acid. Appellants appeal from the Examiner's final rejection of claims 17,
20, 39, and 40 as obvious under 35 U.S.C. § 103. We have jurisdiction
under 35 U.S.C. § 134. The obviousness rejections are affirmed.
1 Appellants identify the real party in interest as "The United States of
America, as represented by the Secretary of Agriculture" (Br. 3).
Appeal2013-000987
Application 11/289,240
STATEMENT OF CASE
Claims 17, 20, 39, and 40 are pending. The claims stand finally
rejected by the Examiner as follows:
1. Claims 17 and 392 under 35 U.S.C. § 103(a) (pre-AIA) as obvious
in view of Guthrie et al. (U.S. Patent 6,251,400, issued June 26, 2001)
("Guthrie"), Berge (Pharmaceutical Salts, 66 J. Pharmaceutical Sciences 1-
19 (1977)), and Lipinski ("Aqueous Solubility in Discovery, Chemistry, and
Assay Changes" in Drug Bioavailability, Estimation of Solubility,
Permeability, Absorption and Bioavailability, Han van de Waterbeemd et al.
eds., pp. 215-231 (2003)). Final Rej. 4.
2. Claims 17, 20, 39, and 40 under 35 U.S.C. § 103(a) (pre-AIA) as
obvious in view of Tian (Differential Inhibition of Human Cancer Cell
Proliferation by Citrus Limonoids, 40 Nutrition and Cancer 180-184
(2001)), Guthrie, Berge, and Lipinski. Final Rej. 12.
Claim 17 is representative and reads as follows:
17. An analytically certified single component amorphous solid
consisting essentially of a purified alkali metal salt of an
individual species of isolated limonoid glycoside mono-
carboxylic acid made according to a production scale method
compnsmg:
(i) separating limonoid glycoside mono-carboxylic acids
from limonoid glycoside di-carboxylic acids in an aqueous
solution, wherein the separating comprises:
(a) acidifying the aqueous solution to achieve a pH of
less than 6.5;
2 We note that Appellants' Brief refers to claim 20 as rejected. However,
both the Final Rejection and Answer states claims 17 and 39 are rejected.
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Application 11/289,240
(b) applying the acidified aqueous solution from step (a)
to a strong anion ion exchange resin;
( c) eluting the strong anion ion exchange resin with a
linear gradient of an ionic solvent; and
( d) collecting eluate fractions that comprise separated
limonoid glycoside mono-carboxylic acids and separated
limonoid glycoside di-carboxylic acids;
(ii) separating an individual species of limonoid
glycoside mono-carboxylic acid from other species of limonoid
glycoside mono-carboxylic acid in an aqueous solution,
wherein the separating comprises:
( e) applying the collected eluate fractions comprising
limonoid glycoside mono-carboxylic acids from step
(i)( d) to an aromatic-selective chromatographic medium;
(f) eluting the aromatic-selective chromatographic
medium with a polar solvent; and
(g) collecting eluate fractions comprising the separated
individual species of limonoid glycoside mono-
carboxylic acid, thereby separating the individual species
of limonoid glycoside mono-carboxylic acid from the
other species of limonoid glycoside mono-carboxylic
acid in an aqueous solution;
(iii) combining eluate fractions from step (ii)(g) which
comprise the same individual species of limonoid glycoside
mono-carboxylic acid to provide combined fractions;
(iv) adding an aqueous alkali metal base to the combined
fractions to make the combined fractions alkaline;
(v) applying the alkaline combined fractions from step
(iv) to a styrene divinylbenzene resin;
(vi) washing the styrene divinylbenzene resin with water
to remove excess alkali;
(vii) eluting the styrene divinylbenzene resin with a polar
solvent;
(viii) collecting eluate fractions comprising the individual
species of limonoid glycoside mono-carboxylic acid; and
(ix) evaporating the polar solvent present in the collected
fractions,
thereby yielding an analytically certified single
component amorphous solid consisting essentially of a purified
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Application 11/289,240
alkali metal salt of the individual species of isolated limonoid
glycoside mono-carboxylic acid.
Product-by-process claims
Independent claim 17 is directed to an "analytically certified single
component amorphous solid consisting essentially of a purified alkali metal
salt of an individual species of isolated limonoid glycoside mono-carboxylic
acid." The claim is a "product-by-process" because it claims the salt product
by the process by which it is made. With respect to product-by-process
claims, it is "'well settled that the presence of process limitations in product
claims, which product does not otherwise patentably distinguish over the
prior art, cannot impart patentability to that product.'" SmithKline Beecham
Corp. v. Apotex Corp., 439 F.3d 1312, 1318 (Fed. Cir. 2006) (quoting In re
Stephens, 345 F.2d 1020, 1023 (CCPA 1965). "[E]ven thoughproduct-by-
process claims are limited by and defined by the process, determination of
patentability is based on the product itself." Jn re Thorpe, 777 F.2d 695, 697
(Fed. Cir. 1985). Process steps are relevant to the extent they change a
structure or characteristic of the product which distinguishes it from
products made by other processes. See In re Garnero, 412 F.2d 276, 279
(CCPA 1979). Independent claims 20, 39, and 40 are also product-by-
process claims.
Obviousness Rejections
Rejections
The Examiner found that Guthrie describes the claimed "limonoid
glycoside mono-carboxylic acid" as a therapeutic agent to treat cancer and
other diseases. Final Rej. 4--5. However, the Examiner found that Guthrie
does not describe the limonoid in the form of an alkali metal salt or as an
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Appeal2013-000987
Application 11/289,240
amorphous solid as required by the claim. Id. The Examiner found that
Berge describes the advantages of an alkali metal salt for pharmaceutical
compositions. Id. at 5-6. Furthermore, the Examiner found that Lipinski
teaches that compounds frequently exist in the amorphous form and such
form is advantageous because it is more soluble in all solvents. Id. at 6.
Based on these teachings, the Examiner determined it would have been
obvious to one of ordinary skill in the art to convert Guthrie's limonoid to an
alkali metal salt in amorphous form for the advantages described by Berge
and Lipinski. Id. at 6-7.
The rejection based on Tian uses the same rationale as the one for
Guthrie, Berge, and Lipinski, but relies on Tian for the claimed "limonoid
glycoside mono-carboxylic acid." Id. at 12-13.
Citing the Bennett3 and Moodley4 publications, Appellants contend
that it was known in the art that the addition of an alkali metal base will
convert the structure of the liminoid compound to another form and produce
a mixture of liminoid compounds. Br. 16-18. For this reason, Appellants
contend that the claimed "amorphous solid consisting essentially of a
purified alkali metal salt of an individual species of isolated limonoid
glycoside mono-carboxylic acid" is not possible and there would have been
no reasonable expectation of success. Id. at 18, 22. Appellants also argue
the cited publications do not teach the process steps recited in the claims nor
how to overcome the problem of making the alkali metal salt. Id. at 22.
3 Bennett et al., Limonoid Glucosides in Citrus Aurantium, 30
Phytochemistry 3803-3805 (1991) ("Bennett").
4 Moodley et al., Micellar electrokinetic capillary chromatography of
limonoid glucosides from citrus seeds, 718 J. Chromatogr. A 187-193
(1995) ("Moodley").
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Application 11/289,240
Appellants make the same arguments for the rejection based on Tian. Id. at
23-31.
Discussion
Appellants' principal argument is that the alkali conditions required to
make the claimed limonoid alkali metal salt would convert the structure of
the limonoid to another form, producing a mixture of limonoids in contrast
to the claim which requires a "single component" that "consists essentially"
of the limonoid alkali metal salt. The evidence to support this argument is
based on the Bennett and Moodley publications. Bennett teaches the
alkaline conversion of ichangin 17-Beta-D-glucopyranoside to 19-
hydroxydeacetylnomilinic acid 17-beta-D-glucopyranoside. Bennett 3805.
Moodley teaches the alkaline conversion of nomilin glycoside to obacunone
glucoside at a pH greater than 7.5. Moodley 189. Based on these two
teachings for alkaline conversion of two specific limonoid compounds into
other structures, Appellants state that alkaline conditions are undesirable for
limonoids and must be avoided. Br. 17.
Appellants' argument is not supported by a preponderance of the
evidence. First, as found by the Examiner, neither of the two starting
compounds described in Bennett and Moodley correspond to those
compounds in the Guthrie and Tian publications relied upon by the
Examiner. Answer 15. Appellants have not provided evidence that one of
ordinary skill in the art would have generalized the teachings for these
specific compounds to other limonoid compounds. Id. at 16-17. As
indicated by the Examiner, there are structural differences between the
compounds claimed and described in Guthrie and Tian and those said by
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Application 11/289,240
Bennett and Moodley to be unstable under alkaline conditions. Id. Thus,
the Examiner had scientific basis to find Appellants' alkaline instability
argument unpersuasive. Appellants acknowledged the Examiner's argument
(Br. 27, 30), but did not identify an error in it.
Furthermore, the Examiner found that the skilled worker would have
inferred that obacunone glucoside, a monocarboxylic acid limonoid
disclosed by Tian and encompassed by the claims, is stable under alkaline
conditions. Answer 20. Specifically, Moodley teaches that, at a pH greater
than 7.5, nomilin glucoside is converted to obacunone glucoside, indicating
that the obacunone glucoside is a stable product of the alkaline reaction.
Answer 20; Moodley 189. Appellants did not rebut the Examiner's
scientific reasoning, which we find to be fact-based and credible.
Appellants also argue that the cited publications do not teach the
process steps recited in the claims. Br. 22. As discussed above, all the
independent claims are "product-by-process" claims and are not limited by
the process by which the purified alkali metal salt of the isolated limonoid
glycoside mono-carboxylic acid made, unless the process limitations change
the structure of the recited product. Thorpe, 777 F.2d at 697; Garnero, 412
F.2d at 279. Appellants have not provided evidence that the process by
which the claimed limonoid is made makes it different from the same
limonoids described in Guthrie and Tian. Consequently, Appellants'
argument are unavailing.
Appellants also argue that the prior art teaches that there were known
problems with obtaining the claimed "analytically certified single
component amorphous solid consisting essentially of a purified alkali metal
salt of the individual species of isolated limonoid glycoside mono-carboxylic
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Application 11/289,240
acid," such as the structural conversion associated with alkaline conditions.
Br. 22, 29. However, Appellants do not explain how they solved the
problem nor how their solution is any different from conventional methods
for preparing alkali salts.
For the foregoing reasons, we affirm the obviousness rejections of
claim 17. Claims 20, 39, and 40 were not argued separately and fall with
claim 17. 37 C.F.R. § 41.37(c)(iv).
TIME PERIOD
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
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