Ex Parte Yamamoto et al

Patent Trial and Appeal Board

Jul 15, 2016

12751195 (P.T.A.B. Jul. 15, 2016)

UNITED STA TES p A TENT AND TRADEMARK OFFICE
APPLICATION NO. FILING DATE
121751,195 03/31/2010
65565 7590 07119/2016
SUGHRUE-265550
2100 PENNSYLVANIA AVE. NW
WASHINGTON, DC 20037-3213
FIRST NAMED INVENTOR
Yuji Yamamoto
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.
Ql 18336 1207
EXAMINER
KEYS,ROSALYNDANN
ART UNIT PAPER NUMBER
1671
NOTIFICATION DATE DELIVERY MODE
07/19/2016 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):
SUGHRUE265550@SUGHRUE.COM
PPROCESSING@SUGHRUE.COM
USPTO@sughrue.com
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte YUJI YAMAMOTO and HIROKI YOSHIOKA
Appeal2014-004735
Application 12/751,195
Technology Center 1600
Before DEMETRA J. MILLS, FRANCISCO C. PRATS, and
JACQUELINE T. HARLOW, Administrative Patent Judges.
MILLS, Administrative Patent Judge.
DECISION ON APPEAL
This is an appeal under 35 U.S.C. § 134. The Examiner has rejected
the claims for obviousness. We have jurisdiction under 35 U.S.C. § 6(b).
STATEMENT OF CASE
The present invention relates to a purification method of a
high-molecular-weight polyethylene glycol compound. More
specifically, the invention relates to a purification method of
obtaining a high-molecular-weight activated polyethylene glycol
compound to be used in pharmaceutical uses mainly including
chemical modification of physiologically active proteins such as
enzymes and the other drugs and chemical modification of
liposomes, polymer micelles, and the like in drug delivery systems
Appeal2009-005511
Application 10/739,849
or a highly pure high-molecular-weight polyethylene glycol raw
material useful as a starting material of the compound.
Spec. 1.
The following claim is representative.
1. A purification method of a high-molecular-weight polyethylene
glycol compound through removing, from a high-molecular-weight
polyethylene glycol compound whose total average number of moles of
ethylene oxide units added in the molecule is 220 to 4500, a polyethylene
glycol impurity different in molecular weight, which comprises:
(A) a mixing step of, in a state that the high-molecular-weight
polyethylene glycol compound is dissolved in at least one of water and
one or more organic solvents selected from the group consisting of
aromatic hydrocarbon solvents having 8 or less carbon atoms in total and
ester compound solvents having 5 or less carbon atoms in total, mixing
the water and the one or more organic solvents; and
(B) a separation step of separating the resulting mixture into an
organic layer and an aqueous layer and separating the organic layer from
the aqueous layer.
Cited References
Gurgiolo
Boehmke
Wolfe et al.
Reeve et al.
us 3,492,358
us 4,322,312
us 4,962,238
us 5,800,711
Grounds of Rejection
Jan.27, 1970
Mar. 30, 1982
Oct. 9, 1990
(Wolfe)
Sept. 1, 1998
(Reeve)
Claims 1-23 stand rejected under 35 U.S.C. § 103(a) as being
unpatentable over Boehmke, in view of Wolfe, Gurgiolo, and
Reeve.
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Application 12/751,195
FINDINGS OF FACT
The Examiner's findings of fact are set forth in the Answer at pages
3-10.
PRINCIPLES OF LAW
In making our determination, we apply the preponderance of the
evidence standard. See, e.g., Ethicon, Inc. v. Quigg, 849 F.2d 1422, 1427
(Fed. Cir. 1988) (explaining the general evidentiary standard for proceedings
before the Office).
"The combination of familiar elements according to known methods
is likely to be obvious when it does no more than yield predictable results."
KSR Int'! Co. v. Teleflex Inc., 550 U.S. 398, 416 (2007).
Under§ 103, "there must be some articulated reasoning with some
rational underpinning to support the legal conclusion of obviousness." KSR
Int'! Co. v. Teleflex, Inc., 550 U.S. 398, 418 (2007) (citation omitted). "If a
technique has been used to improve one device, and a person of ordinary
skill in the art would recognize that it would improve similar devices in the
same way, using the technique is obvious unless its actual application is
beyond his or her skill." Id. at 416. Obviousness is determined on the basis
of the evidence as a whole and the relative persuasiveness of the arguments.
See In re Oetiker, 977 F.2d 1443, 1445 (Fed.Cir.1992).
Obviousness
The Examiner finds that
Boehmke teaches a process for the purification of non-
ionic emulsifiers which are of the type comprising addition
products of alkylene oxides and compounds containing
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Application 12/751,195
hydroxyl groups, carboxyl groups or carboxamide groups from
impurities comprising polyglycols, polyols or polyol-
polyglycols originating from their preparation (see entire
disclosure). The non-ionic emulsifiers to be purified have a
chain of over 20 alkylene oxide units (see claim 7). Such
compounds are suggestive of the claimed high-molecular
weight polyethylene glycol compound. The process is
characterized in that an amount of water approximately
corresponding to that of the impurities is added to solutions of
the reaction mixtures in water-immiscible organic solvents, the
organic layer and aqueous layer separate and the aqueous layer
is separated off (see for example the paragraph bridging
columns 2 and 3 and claim 1 ).
Ans. 3.
The Examiner finds that Boehmke teaches that the
preferred water-immiscible organic solvents are aromatic
solvents such as benzene, toluene, and xylene (see col. 2, lines
27-35). The purification can be achieved at low or only
slightly elevated temperatures (see col. 2, lines 51-60). In an
advantageous embodiment of the emulsifier purification
consists in stirring in the 40-70% strength organic solvent with
2-25% water at 20-50°C (see the paragraph bridging col. 2 and
3 and claim 5).
Ans. 3.
Boehmke teaches the use of the claimed additive solvents, toluene and
benzene. See Ans. 3; Spec. 12 and Boehmke, col. 2, 11. 27-39. The
Examiner finds that Boehmke does not teach the use of an organic or
inorganic salt dissolved in the water, or carrying out the mixing and
separation at temperatures higher than 50°C. Ans. 3. The Examiner relies
on Wolfe, Gurgiolo, and Reeve to make up for these deficiencies. Ans. 3.
The Examiner concludes that
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Application 12/751,195
One having ordinary skill in the art at the time the
invention was made would have found it obvious that the
purification process of Boehmke could be modified to include
the use of the claimed additive solvents, the use of an organic or
inorganic salt dissolved in the water, or carrying out the mixing
and separation at temperatures higher than 50°C, since Wolfe et
al., Gurgiolo, and Reeve et al. teach that such solvents and salts
have been shown to be useful for extraction purification of
polyoxyalkylene glycol compounds and Wolfe et al. and Reeve
et al. have shown that temperatures higher than 50°C are also
suitable temperatures for carrying out purification of
polyoxyalkylene glycol compounds. Therefore, all the claimed
elements were known in the prior art and one skilled in the art
could have combined the elements as claimed by known
methods with no change in their respective functions, and the
combination would have yielded predictable results to one of
ordinary skill in the art at the time of the invention.
Ans. 4--5.
Appellants contend that,
Boehn:1ke teaches that his process provides the ability to purify
adducts with 20-100 mo ls of ethylene oxide units (see column
2, lines 51-54), which is outside the scope of the claimed high-
molecular weight polyethylene glycol compound whose total
average number of moles of ethylene oxide units added in the
molecule is 220 to 4500.
App. Br. 6. Appellants further argue that
Boehmke specifically teaches that previously known methods
are not adequate for purifying emulsifiers with a chain of over
20 alkylene oxide units since they display no turbidity point on
heating. Column 2, lines 23-26. Then Boehmke clearly states
"the purification process according to the invention extends the
known processes by providing them with the ability to also
purify adducts with 20-100 mo ls of ethylene oxide units ... "
Column 2, lines 51-54.
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Appeal2014-004735
Application 12/751,195
App. Br. 7. Appellants argue that, "under the conditions taught by
Boehmke, high-molecular-weight polyethylene glycols are all distributed in
an aqueous layer so that removal of polyethylene glycols as an impurity
having a molecular weight different from that of the high-molecular-weight
polyethylene glycols which is an object of the present invention, cannot be
achieved." App. Br. 9.
ANALYSIS
We agree with the Examiner's fact finding, statement of the rejection
and responses to Appellants' arguments as set forth in the Answer. We find
that the Examiner has provided evidence adequate to support a prima facie
case of obviousness. We provide the following additional comment to the
Examiner's argument set forth in the Final Rejection and Answer.
Appellants do not provide separate arguments for dependent claims,
therefore we select claim 1 as representative claim.
\Vith respect to 1A .. ppellants' argument that Boehmke teaches a process
outside the scope of the claimed high-molecular weight polyethylene glycol
compound whose total average number of moles of ethylene oxide units
added in the molecule is 220 to 4500, the Examiner responds, arguing that,
"Boehmke teaches in claim 7 that his process provides the ability to purify
adducts with over 20 alkylene oxide units. This is within the scope of the
claimed high-molecular weight polyethylene glycol compound whose total
average number of moles of ethylene oxide units added in the molecule is
220 to 4500, since 220 to 4500 is over 20." Ans. 5-6. The Examiner further
argues that "Boehmke discloses the use of low or slightly elevated
temperatures (see col. 2, lines 51-60) and expressly discloses the
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Application 12/751,195
temperature range of 20-50QC, which overlaps the claimed temperature range
at 50QC.
Appellants have not rebutted the Examiner's argument or evidence
with a sufficient showing. "If a technique has been used to improve one
process, and a person of ordinary skill in the art would recognize that it
would improve similar processes in the same way, using the technique is
obvious unless its actual application is beyond his or her skill." KSR, 550
U.S. at 416. In the present case, the prior art processes show an
improvement in removal of polyethylene glycol impurities from
polyethylene glycol-containing emulsifiers with chains over 20 alkylene
oxide units, using aromatic hydrocarbon solvents having 8 or less carbon
atoms, in the presence of water, as required by claim 1. See, e.g., Boehmke,
col. 2, 11. 27-39. This technique is known to be useful, as disclosed in
Reeve, for poloxamers ranging up to 16,000 daltons. Col. 4, 11. 53-64.
Thus, one of ordinary skill in the art \'l/ould have found it obvious ( \'l1ith a
reasonable expectation of success) to use this known purification technique
for removing lower molecular weight byproducts from polyethylene glycol-
containing emulsifiers compounds encompassed by claim 1, including those
having a molecular weight of about 20,000, as the technique was shown to
be successful for poloxamers ranging up to 16,000 daltons in Reeve.
Appellants argue that "neither of Wolfe nor Gurgiolo teach the
removal from a high-molecular weight polyethylene glycol compound
whose total average number of moles of ethylene oxide units added in the
molecule is 220 to 4500, a polyethylene glycol impurity different in
molecular weight." App. Br. 10. For the reasons given above, we are not
persuaded that Wolfe fails to suggest the impurity removal step of claim 1.
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Application 12/751,195
We agree with the Examiner, moreover, that Gurgiolo, and Reeve teach that
the solvents and salts taught in those references have been shown to be
useful for extraction purification of polyoxyalkylene glycol compounds, and
Wolfe and Reeve have shown that temperatures higher than 50QC are also
suitable temperatures for carrying out purification of polyoxyalkylene glycol
compounds. See Ans. 4--5 (citing Gurgiolo, cols. 2-3; Reeve, cols. 5---6).
Finally, we agree with the Examiner with respect to Appellants'
arguments regarding Boehmke' s disclosure about the prior art removal of
impurities. As the Examiner argued, the prior art methods mentioned in the
background section of Boehmke do
not include the use of an organic solvent in combination with
water, as taught by Boehmke. Further, the disclosure of
Boehmke being applicable to purifying adducts with 20-100
mols of ethylene oxide units, as disclosed in col. 2, lines 51-55,
should not be limiting, since Boehmke disclose that the
teaching is applicable to emulsifiers having 20 or more alkylene
oxide units (see claim 7).
Ans. 7.
Nor are we persuaded by Appellants' Declaration under 37 C.F.R. §
1.132. Br. 11. The Declaration states that the effective purification of high-
molecular-weight polyethylene glycol compounds cannot be achieved with
the system of Reeve et al using n-propanol as a solvent. Dec. 2; Br. 11. We
are not persuaded. Rather than n-propanol, as solvents, representative claim
1 recites the use of either aromatic hydrocarbon solvents having 8 or less
carbon atoms in total or ester compound solvents having 5 or less carbon
atoms in total. App. Br. 13. Reeve discloses that it is known to remove
lower molecular weight fractions from polymeric glycols by dissolving the
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Application 12/751,195
polymeric glycol in cyclohexane and/or toluene. Col. 2, 11. 45. Furthermore,
the Examiner also relies on Wolfe and Gurgiolo for the use of the claimed
solvents. Appellants are comparing and arguing the references individually
instead of in combination.
With respect to Appellants argument concerning the distribution of
high-molecular-weight polyethylene glycols in an aqueous layer in
Boehmke, we note that pending claim 20 also indicates that the high-
molecular-weight polyethylene glycol compound is collected from the
aqueous layer. Appellants have not shown how the disclosure of Boehmke
is distinguished from the method claimed. Furthermore, claim 1 step B)
does not appear to indicate whether the polyethylene glycols are present in
the organic layer or the aqueous layer.
The remaining arguments of Appellants have been addressed fully in
the Answer, and we adopt them as our own. We affirm the obviousness
rejection for the reasons of record.
CONCLUSION OF LAW
The cited references support the Examiner's obviousness rejection,
which is affirmed for the reasons of record. All pending, rejected claims
fall.
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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