*1 trial, further whether to ing requiring not de should state we My colleagues jury or to the bench. trial con clinical Sunovion’s cide whether Dey “did because “public use” stitutes enter court to the district us to direct
ask favor,” at 1360 n. 5. op. in its
judgment district to the argument
Dey’s primary law, matter of Suno that “as a court was PHARMACEUTICALS AVENTIS trial does 050 clinical vion’s confidential INC., Plaintiff-Appellant, Dey’s inven use of public not constitute Opp’n Mem. of Law Dey’s tion.” and Dey at 1. Summ. J. Mot. for Sunovion’s (now Technology, Inc., known AMR the dis argument fairly legal raised its Research, Albany as Molecular an court, given and Sunovion trict Inc.), Plaintiff-Appellant, court The district respond. opportunity summary judgment free to enter was thus v. v. Fin. Ins. Co. party. First for either LTD., Dipharma AMINO CHEMICALS Corp., 193 Demolition
Allstate Interior Francis, Sr.L., Dipharma Spa, and (2d Cir.1999) (“[I]f a motion F.3d Defendants-Appellees, made, a summary judgment has been summary judg may grant court district a nonmov- any party including ment to — Mylan Pharmaceuticals ant.”). Inc., Defendant. that this court Dey requested appeal, On Inc., Aventis Pharmaceuticals court’s the district or reverse” “vacate Plaintiff-Appellant,
judgment: in hold- court erred Whether district clinical Defendant-Appellee’s
ing (now Inc., Technology, known AMR trial, confidentiality re- conducted under Research, Albany Molecular con- alleged infringer, striction’s Inc.), Plaintiff-Appellant, Plaintiff-Ap- “public use” stituted v. family within the second pellants’ USA, 102(b), § and in meaning Pharmaceuticals of 35 U.S.C. Teva Defendants, that basis. invalidating patents Issue, Br. at Dey 3. We Statement of the than to answer no further go
need Ltd., Dipharma Amino Chemicals uncon- On the question presented: legal Francis, Sr.L., Dipharma facts, trial was clinical Sunovion’s tested Defendants-Appellees. Spa, “public not a use” within 2011-1335, 102(b). 2011-1336. § Nos. U.S.C. facts, legal ques- undisputed On the Appeals, States Court United readily The invention
tion is answered. Federal Circuit. in “public was not Dey’s patent claimed May trials. I re- clinical use” Sunovion’s refusal from the court’s spectfully dissent noth- for there is question, resolve the *2 Shaw, LLP, of
Anthony Arent Fox W. DC, argued for Washington, defendants- Ltd., Amino et al. Of appellees, Chemicals *3 Joerg-Uwe Szipl, the brief was on counsel PC, Arlington, Szipl & VA. Griffin BRYSON,* NEWMAN, Before REYNA, Judges. Circuit by Opinion for the court filed Circuit Judge REYNA. by
Dissenting opinion filed Circuit Judge BRYSON.
REYNA, Judge. Circuit Pharmaceuticals, Inc. and Alba- Aventis (AMRI) (col- Research, Inc. ny Molecular lectively “Appellants”) appeal stipulated by noninfringement entered judgment of for the District of District Court the U.S. Jersey. parties stipulated New following the district noninfringement 13, January opinion Markman court’s 2011, consolidated numerous which Boehnen Berghoff, H. McDonnell Paul terms of cases and infringement construed IL, LLP, Chicago, Berghoff Hulbert & (“the 5,750,703 Patent No. AMRI’s U.S. Aventis plaintiffs-appellants, argued for Because we among others.1 patent”), AMR Technolo- Inc. and Pharmaceuticals court’s Mark- the district conclude him the brief were Inc. With on gy, misinterpreted claim terms opinion man Gumina, Jeremy E. Noe and James C. reverse and remand. we counsel on the brief Paula Fritsch. Of S. LLP, Walsh, Foley Liza M. Connell were Background I. Roseland, NJ; Rich- Zappia, P. Andrew used to Harris, processes concerns McGuirk, Tate This case W. ard A. Wendell derivatives, which Jones, make various Shelley A. LeClair- T. Tischner and ingredients commonly used as active Rochester, Ryan, NY. * No.2011-1334, -1335, -1336, was heard on Judge Bryson senior status Circuit assumed 2012, 15, 7, panel by on January the same March claim construc- to the district court's relates court, originally before this 1. Two cases were Subsequent to the patent. tion of the '703 appealed though they from were both argument, Reddy’s Labs Dr. March 15 oral January Opinion and Order of same Markman engaged protracted settlement and AMRI case, 13, Albany Molecular 2011. The first finally culminating negotiations, settlement Labs., Ltd., Research, Reddy’s Inc. v. Dr. Reddy's involving Dr. pending matters of all No.2011-1232, panel the above was heard February settlement termi- 2013. The on to the dis- December and relates appeals. -1334 the 2011-1232 nated U.S. Patent trict court’s construction appeals case, -1336 re- 7,390,906. Only 2011-1335 and Aventis The second No. Labs, Pharmaceuticals, pending this court. Reddy's before main Inc. v. Dr. D’Ambra, 1, 6, appeal gravitate Dr. Thomas E. this around claims
antihistamines. patent. and 7 of the '703 pro- found the president, AMRI’s making piperidine derivatives cesses for Background A. Technical goal one of Dr. D’Am- inefficient. Because substantially pure was to obtain Independent bra’s work Claim of the '703 Patent compounds —ulti- mately required pharmaceutical-grade for Generally a. The Patented Process is, products; products suggests, As its title greater recognized than 98% —he processes synthesizing piper- describes *4 through that the reduced achieved supra idine derivatives. See note 2. teachings purifica- known meant additional '703, only independent Claim 1 of the steps required piperi- tion were after the suit, pre- describes a formed, fully leading dine derivative was paring piperidine using a CPK yields. prior processes, low The art piperidine intermediate and a intermedi- short, costly consuming. were and time piperidine ate. The structure of the deriv- ative to prepared be Dr. D’Ambra’s invention overcame the provided patent in claim 1 of the '703 as: by synthesiz- deficiencies in the ing piperidine using derivatives (“CPK”) cyclopropylketone
and intermedi- stage
ates at an earlier reaction. processes developed
The Dr. D’Ambra advantage readily
have the stated of more
separating substantially pure out a piperi- product,
dine derivative end if desired.
Dr. D’Ambra claimed these novel methods Fexofenadine, patent.2 his '703 a spe- derivative,
cific piperidine synthe can be using
sized pat these methods. See '703 (claim 7).
ent col. 26 ll.17-33
Dr. eventually assigned D’Ambra to AMRI.3 Sanofi-Aventis U.S., licensee, the exclusive uses '703 patent col. 23 ll. 47-61. In the abovedepiction, hydrogen hydroxyl is a or Rx - processes produce ented large quanti- group, hydrogen group,4 is a is a R2 R3 fexofenadine, ties of which is the active acid) (car- (carboxylic COOH or -COOR4 ingredient in its antihistamines marketed ester) boxylic acid group, hy is a R4 under the Allegra® brand name and Alle- drocarbon chain with one-to-six carbon at gra-D® 24 Hour. The issues relevant to oms. application patent, formerly
2.The for the '703 U.S. 3. AMRI was known as AMR Tech- 382,649, Application Patent No. on filed nology, Inc. 2, Feb. 1995. The '703 entitled “Pi- peridine Derivatives and Process for Their Alternatively, can form double R2 Rx Production,” May issued on 1998. The bearing bond between the atoms carbon Rx Ap- is a divisional of U.S. Patent and R2. 08/083,102 ("the plication applica- No. tion”), which was filed on June A, R2, defined as Rj,
where R3 described for See, patent col. 24 11. e.g., '703 10-17, 22-34. exists in one of
The CPK intermediate ei- predominant regioisomeric states:5 two para- or para-CPK ther meta-CPK.6 has the two regioisomer CPK intermediate on car- ring aromatic substituents located general intermediate of with a CPK directly opposite 1 and sides bons structure ring. meta-CPK inter- the aromatic the two aromatic regioisomer mediate has ring located on carbons substituents 3, in orientation. The different a nonlinear *5 depicted are below. regioisomeric forms synthesis yields impure regioi- stage of the these The difference between para-regioisomers. of meta- and mixture arrangements of constituents someric Dr. invented process But the new intermediate both CPK using a CPK intermediate D’Ambra is appears slight, but regioisom- para/meta that the means significant piperidine de- biologically —the readily separable eric mixture is more using para-CPK produced rivative resulting in a substan- para-CPK, obtain active, while the biologically is structure derivative end tially pure para-piperidine using the produced piperidine derivative biologically inac- meta-CPK structure is criti- extensively tive. The '703 “Substantially Pure” b. each processes because
cizes reads its 1 of the '703 Claim
entirety: preparing A compound of the formula: However, adjacent to each other. compounds with stituents Regioisomers chemical formula, little rarely produced but with differ- and of the same molecular is ortho-CPK bonding ignored ent orders. for the biological efficacy, it is so this discussion. remainder of in an can also exist 6. The CPK intermediate ortho-structure, ring sub- with the aromatic wherein
Rj hydrogen hydroxyl; or hydrogen;
isR2 Rj R2 together
or taken form a
second bond between the carbon atoms R2;
bearing andRx -COOR4; is -COOH or
R3 atoms; has 1 to 6 carbon *6 R4 patent '703 col. 23 1. 45 to col. 24 1. 35 (claim 1) added). (emphases There are A, B, and D are the substituents of 1 two notable features of claim of the '703 rings, their aromatic each of which First, patent. piperidine the same, may be different or the and are product synthesized through from group consisting selected process range claimed covers a broad hydrogen, halogens, alkyl, hydroxyl, potential piperidine compo- derivatives as alkoxy, substituents, or other A, B, nents and D—substituents of the rings aromatic can be selected from process said comprising; —that groups hydrogen, halogens, alkyl, such as providing substantially pure regioi- hydroxyl, alkoxy groups. or other '703 somer of following formula: Second, patent col. 23 11.45 to col. 24 1. 6. importantly, patent and more re- a “substantially pure regioisomer” fers to specific of a 24 patent formula. '703 col. 1. Notwithstanding, 8. the term “substan- tially pure” anywhere is not defined in the specification, as noted the district court. converting substantially pure re- c. “Providing” The gioisomer piperidine to the “Converting” Steps compound piperidine with a compound “providing” “converting” steps of the formula: patent of the method in claim 1 of the '703 3,2, by dependent are illuminated claims patent specification. as well as the dependent specification claims and the 1369 “pro- reducing methods for derivative under multiple teach examples intermediate, both para-CPK viding” hydroxy- to form a conditions effective product substantially pure para-CPK as a lated derivative of the formu- and meta- para-CPK mixture of or as a la: See, col. e.g., patent '703 products. CPK (specification); 19 1. col.
12 1. 65 to col. 35 (claims 2-5). 1. 62 For
24 1. 35 to col. 25 claims 2 and 3 de-
example, dependent acylation purification
scribe para- recovery
that results in the mixture intermediate from a “second col. 24 1. regioisomers”. patent 35 (claims 2-3). 2 of Example 1. 53
to col. 25 hand, on the other de- specification, teaching, “providing” pro-
scribes another a mixture ducing product” a “crude that is 1. to col. 1. col. 25 that could be para-CPK and meta-CPK (Claim 6). para- purified predominantly further col. 20 1. col. 19 65 to
CPK. 7 of the Patents-in-Suit 3.Claim 2, however, requires Example never Dependent specifies claim 7 further spe- to a regioisomeric purification further hydroxylated piperidine derivative type of fact, in the cific level. id. nowhere See claim 6—fexofenadine: any numeric value attached specification intermediate. to the of the CPK process according 7. A to claim coupling reaction of “Converting” is the hydroxylated piperedine de- wherein azacyclonol to create the para-CPK formula: rivative has the Again, end-product piperidine derivative. multiple pro- specification describes *7 step the claimed performing cesses for
“converting” the intermediate to a CPK compound. See '703
piperidine derivative As col. 16 1. 31 to 18
patent intermediate,
“providing” step not indicate that
“converting” does in a intermediate must be sub-
the CPK form, any
stantially pure provide or even required purity. level of (Claim 7). patent col. 26 11. 16-33 '703 Thus, patent produces 7 of the '703 Claim 6 of the Patents-in-Suit 2.Claim ingre- important pharmaceutical active process claim describes While against claim asserted dient and was the through derivatives producing piperidine anti- manufacturers’ accused generic generally, use of a CPK intermediate histamines. specify piperi- claims 6 and 7 further synthesized by product dine derivative end Art Processes 4.Prior Dependent claim 6 patented process. of the '703 Background The section describes: prior pro- art ent discusses in detail to claim 1 fur- process according 6. A making piperedine derivatives. cesses for comprising: ther '703 claimed patented process significant improve- patent represented processes,
ment over these taught in U.S. Pat-
particular the method (“the 4,254,129 patent”),
ent No. 3,1981.
which issued on March patent in the '129 disclosed to arrive
used a “Friedel-Crafts” reaction See '703 piperidine
at a derivative. reac-
col. 2 11.27-41. The Friedel-Crafts admixture, produced tion a statistical See, 2 1. 42 4 1. e.g., col. to col. the “second mixture of aromatic termed 25. The “second mixture of aromatic re- patent, regioisomers” contain- gioisomers” could then be converted to a of the de- ing 67% meta-isomer regioisomers” “third mixture of of the fol- para-isomer rivative end and 33% lowing formula: product:7 para-CPK col. 1. to col. 41. 25. novel 3 65 use intermediate. material, By using unique starting his Dr. D’Ambra discovered in the course of purer in- regioisomeric form of the CPK attempting teaching replicate *8 termediate, regioisomeric of the purity patent it practically impossi- that was product higher could be much than the separate ble to completely para-isomer para-CPK produced by the '129 of the product Dr. a process. ent’s D’Ambra discovered pharmaceutical purity using process synthesizing piperi- different a patent’s process. In improve order to higher regioi- dine derivative regioisomeric purity easily more at an ear- purity; by using recrystalli- someric then reaction, stage lier in the D’Ambra devel- purification techniques, zation and other he oped patented discussed pharmaceutical-grade could attain fexofe- above; in particular, expense. he discovered the nadine at a much lower extending 7. The illustrated bond into the low- and metaisomers. See '703 col. 3 ring para- er aromatic indicates a mixture of 15-30.
1371 purity.” than 95% at Background Procedural Id. 502-03. The B. only court extended this to describe not history is com- larger procedural The purity necessary products, level of end involving parties twenty plex, dozens but also the CPK compound. intermediate It suffices to limit the discussion to cases. declining preliminary Id. institute Defendant-Appellees, Amino Chemicals injunction patent, on the '703 based Francis, Sr.L., Ltd., Dipharma Dip- and district court did not reach the issue of (collectively Spa “Appellees”). Ap- harma whether describes drug manufacturers. pellees generic everything overall as to chemical Drug Master Amino Chemicals had filed compound or whether the term lim- in Abbreviated referenced, File that was i.e., regioisomeric purity, ited to (“ANDAs”) of two Drug Applications New only of the para-isomer relative to unwant- Inc. parties, Mylan former Pharmaceutical ed meta-isomer. Id. at 508. USA, Teva Pharmaceuticals sought Drug had Food and Adminis- which parties opening The thereafter filed (“FDA”) approval to market anti- tration briefs, responsive claim construction containing histamines fexofenadine. Simi- 10, 2010, on November a Markman hear- larly, Dipharma Dipharma Francis and ing Judge was held before Chief Brown. My- Spa suppliers are bulk-manufacture Opinion January Markman issued Upon lan and Teva. submission 13, 2010, construing two terms from the FDA, Appellants timely ANDAs 41; App’x relevant here. Joint brought against generic several suits Pharms., Impax see also Aventis Inc. v. Jersey in the New drug manufacturers Labs., Inc., 02-1322, 03-1179, Nos. 03- alia, court, alleging, infringe- inter district 1180, 03-5108, 04-1075, 04-1076, 03-5829, patent. ment of the '703 04-1077, 04-1078, 04-2305, 04-3194, 05- 07-5054, 09-0325, 4255, 06-5463, 07-5180, a tentative performed The district court 10-1471, 09-4638, 09-5179, 2011 WL with a claim construction connection (D.N.J. 2011) 31, 2175928, (pub- at *1 Jan. prelimi- for a September 2005 motion lically opinion). Markman available nary injunction began filed after Teva marketing generic drug. fexofenadine claim 1 of the '703 From Judge Greenaway’s January opin- court construed the terms “sub- district injunction preliminary ion denied the re- stantially pure regioisomer following an initial claim con- quest, and set forth formula disputed patent’s struction of the '703 “substantially pure.”
claim term See Pharms., Labs., Inc., Inc. v. Barr
Aventis (D.N.J.2006). F.Supp.2d patent’s
district court found that the '703 phrase “substantially used the
specification deriv- to describe both the products pure.” and the intermedi- The district ative end *9 the claims nor the Id. at 498-99. The district court also court held that neither ate. specific guid- sufficient prosecution specification give relied on statements from the of either claim history regarding purity piperi- meaning the of the ance as to the found, however, court that products dine derivative end to reach a term. The trial specification “indiscriminately” equates tentative claim construction that the the and final phrase “substantially pure” purity in the asserted the of the intermediates that there is no patent greater products of the means “of to such an extent claims patent scope of for his between “sub- clear disclaimer to differentiate justification Aventis, 54; intermediates para-CPK stantially pure” patent.” App’x Joint see also piperidine deriva- “substantially pure” and 2175928, Thus, by at virtue 2011 WL *8. According to the court: products. tive end nondiscrimination be- specification’s “[Bjecause the uses same specification end products, tween intermediates and consistently for both intermediates purity requirement was extended derivatives, that finds what the Court as well. para-CPK intermediate when it modifies ‘substantially pure’ means Finally, regard with applies equally to purity pure,” the court held that 98% re- ‘substantially in claims’ context its ” any kind impurities to chemical fers formula.’ Joint pure regioisomer of the just regioisom- present product, Aventis, 49; 2011 WL App’x see also (“The App’x plain impurity. eric Joint 2175928,at *5. language ‘substantially pure’ of the term “substantially pure” ac- Regarding what impurities relative to all solution of 25% —a to both the tually applied means when meta-CPK, dirt para-CPK, 0.2% and 74.8% deriva- CPK intermediate substantially pure.”); would not be see product, tive the district court Aventis, also 2011 WL at *8. history of rely prosecution forced to on the prosecution as well as the sum, In the district court construed the Patent No. history of the related U.S. relevant terms at issue from the '703 (“the (filed 1993) 5,578,610 June (1) “substantially pure” ent so that means another divisional de- patent”), which is all respect “at least 98% 08/083,102 parent appli- from the scended (2) impurities” “providing regioisomer cation. The district court determined following formula history that “the through prosecution inventor understood the ‘substantial- purity and that the
ly pure’ to mean 98% clearly unambiguously
inventor disa- any scope.” other claim Joint
vowed Aventis, 52;
App’x see also 2011 WL 2175928,at *7. regioisomer having means “the the struc- high at particularly To arrive this level ture formula is in at present shown court to a purity, the district cited state- impuri- least 98% to all during Dr. D’Ambra ment made 65; Aventis, App’x ties.” Joint see also There, interference light WL at *13. this allegedly Dr. stated several D’Ambra construction, Appellants stipulated that meant times they infringe- longer prove could no 98%, purity or pharmaceutical-grade, ment, final and the district court entered products consumption. From judgment Appellees in both favor despite acknowledging this — Appellants timely appealed cases. the dis- likely only describing statements were puted claim construction of the '703 end-products district court concluded —the jurisdiction pursu- to this court. We have by ‘substantially pure’ that “it is clear 1295(a)(1). § ant to 28 U.S.C. patentee pharmaceutical-grade meant an no purity, requires impurity which level II. Discussion greater than 2%. These statements both Claim construction is issue explain patentee assigned *10 ‘substantially Markman v. Instru- pure’ represent to law since Westview
1373 (Fed.Cir. ments, Inc., 967, 1317, at it provides 52 F.3d 981 415 F.3d still evidence 1995) (en 370, banc), aff'd, 517 U.S. 116 of the inventor how intended the term to (1996). 1384, 577 This 134 L.Ed.2d S.Ct. Mills, be construed. See Lemelson v. Gen. court court claim construc reviews district Inc., 1202, (Fed.Cir.1992). 968 F.2d 1206 Techs., Corp. v. Cybor tions de novo. FAS (Fed.Cir.1998) Inc., 1448, A. “Substantially 138 F.3d 1456 Pure” (en banc). 1, 6, Claims and 7 explicitly include' the term “substantially principle pat
“It is a bedrock pure regioisomer.” The district court con- ent of a define law that the claims language require strued this to patentee the invention to is enti “at least which Phillips tled the exclude.” v. right to all impurities.” 1303, (Fed.Cir, Corp., AWH 415 F.3d 1312 construction, however, This conflates the 2005) (en banc) (internal quotation marks purity required for omitted). a heavy presumption There is product with that of the CPK intermedi- claim are to given terms be their ate. ordinary customary meaning. Id. at
1312-13; Corp. v. Conceptronic, Vitronics Intermediate Versus 1576, (Fed.Cir.1996). 90 F.3d 1582 Piperidine End Product Courts “look to required therefore to agree parties We with both ... the words of claims themselves the claims themselves are insufficient to patented define the inven scope define the term pure.” Id.; tion.” see also Toro Co. v. White Therefore, we must turn to other sources Indus., Inc., Consol. 199 F.3d 1299 of intrinsic evidence to determine “what (Fed.Cir.1999). actually the inventors invented and intend
Claims, however,
con
must be
envelop with
ed to
the claim.” Renishaw
light
appropriate
context
strued
Azioni,
Marposs
per
PLC v.
Societa’
158
Toro,
in which
term
the claim
is used. See
(Fed.Cir.1998).
speci
F.3d
The
description
We have
crystallization
purifica-
construc
and
claim
can have different
various
ples,
term
of how
the context
depending upon
processes
purify
tions
are available to
the
tion
the
and
claims
the
is used within
term
piperidine
product
derivative end
to reach
En
Microprocessor
See
specification.
after
purity
synthe-
pharmaceutical-grade
.
Instruments,
Tex.
Corp v.
hancement
patent represents
The
an im-
sis.
(Fed.Cir.2008)
Inc.,.
1367, 1375
F.3d
processes.
the
art
provement
prior
over
that,
is a presumption
while there
(holding
the
improvement
was not that
patent-
construed consis
that a
be
will
guarantee a
technique
piperidine
ed
could
claims,
throughout
the
tently
used
when
purity
pharmaceutical
derivative of
absent
claim term
requirement
a
there is no
purification;
improvement
the
further
particularly if it
uniformly,
be construed
patented technique
provide
the
could
reading”).
to a
would lead
“nonsensical
piperidine
product
a
derivative end
Inc. v. Bauer Com
Epcon
Systems,
Gas
higher
purity requiring less
regioisomeric
(Fed.Cir.
F.3d
pressors,
than the end
purification
product
extensive
2002),
the term
example, we construed
process
patent.8
derived
interpre
“substantially” to
different
have
Reading “substantially
to
a
pure”
require
significant
on
tations
a
based
“subtle.but
the CPK inter-
consistent construction for
at
usage.
in
and
Id.
context
difference”
piperidine
end
mediate and
derivative
1030-31.
in
product
ignores
distinct contexts
“substantially pure” refers to both
While
which these terms
used.
and the piperidine
the CPK intermediate
a
Appellees argue that
common
reading
specification,
in the
product
derivative end
meanings
term to have different
in différ-
only
is used
pure”
not
here to the
apply
ent contexts does
in
to
intermediate
reference
the CPK
interpretation
pure.”
1, 6, and 7. And unlike
relevant claims
They distinguish Epcon
Microproces-
and
family,
there is no
patents
other
patents in
sor' because the
those cases
limitation
explicit “substantially pure”
clearly
which
contained intrinsic records
end
placed
piperidine
multiple
expressly supported
interpre-
in the
claims of the '703
relevant
single
Appellees
tations for a
claim term.
any “substantially
patent. The lack of
no
and express
maintain that
such clear
pure”
limitation on the
deriva-
support
patent specifi-
is found in
1, 6,
and 7
products
tive
in claims
end
at
But
apply
ignores
cation
this
that we
any explicit requirement
to
issue.
obviates
always
specification
construction
must
construe the
is consistent for both the CPK
knowledge
ordinary
.intermedi-
light
of one
prod-
ate
end
art.
Further, in the ordinary skill person of that, recognize purity artisan that the would recognize would an intermediate compound in a reaction is intermediate reaction would not claimed chemical of. not equivalent often be as the required have the same further, com- product, especially specifi- in the As mentioned cation, steps may .physical purification art mon be both reference in; tionally did tech- in the '129 difficult cost-ineffective described appear purity of to be able to reach a niques. supra Part See I.A.4. greater excep- resorting than without
1375 necessary. Interpreting specification piperidine this product, derivative end light knowledge person of of of in proper construe, to term “substantially art, ordinary in the hold that a skill we pure regioisomer,” still requires claim con requires in- proper construction different presumption struction. is The that claim pure” terpretations “substantially when given terms should “ordinary be their CPK applied pi- to the intermediate Vitronics, customary meaning,” 90 F.3d at peridine product. end derivative 1582, and not a restrictive construction The construction “one-size-fits-all” unless there clear to support is evidence it adopted by incorrectly the district court in evidence, the intrinsic aor broader “substantially separate construes pure” specifically during disclaimed very “regioisomer.” from next word — Grp., prosecution. See Saunders Inc. v. The district court’s artificial truncation of Comfortrac, 492 F.3d claim for the expediency of a (Fed.Cir.2007). A court can look to the single interpretation across different con prosecution history patents of related for descrip texts was error. Outside of the guidance in claim construction. See Orm tion of the from the '129 Tech., Inc., co Corp. Align v. 498 F.3d specification exclusively almost (Fed.Cir.2007). 1307, 1314 “regioisomer” uses the term refer to to Further, term, CPK full intermediate. The interpreted district court “substan- “substantially regioisomer,” is pure used tially pure” in isolation to mean “at least only in reference to the CPK intermediate. 98% purity respect impurities” to all See 11-12, 23, 40-41; col. 5 ll. part based in large prosecution on the 32-33, 43, 62-66; 55-56; 12 ll. col. col. 13 history of the related patent. 37-38, 53; 13 1. 14 ll. col. 67 to col. col. district court looked to statements made ll.13-14, 51-52, 54; 21-22, col. 16 11. 25- during patent’s the '610 pro- interference 26, 31-32, 34-35, 49; 4-5, ll. col. 18 7-8. ceedings before the U.S. Patent uniform use of pure Such (PTO), Trademark the paten- Office where whole, regioisomer,” exposes taken as a person tee ordinary stated that skill in by the error of the district court: decou the art would understand pling pure” the modifier 1-17 to pure” pharma- claims refer “regioisomer” from purposes claim ceutical-grade 1-17 purity. Claims include construction, imposed the district court claims, such as where “substan- single though interpretation even that con tially pure” only modifies the CPK inter- requires separate text definitions of “sub stantially basis, when applied the CPK mediate. On that the district court opposed intermediate as to the “substantially pure” concluded here that product. derivative end thusWe conclude applied required to the intermediate the district court in requiring erred “at least 98% to all have same impurities.” interpretation applied to the CPK In analyzing the claims of the '703 intermediate and the ent, we find made the '610 statements product.
patent’s proceedings interference little “Substantially Construction help. patentee and the PTO both Regioisomer” Pure explicitly noted the focus limited to patent’s interference was inter- it Although for the error dis preting pi- the claims reference trict court to limit the construed encompass peridine both the CPK intermediate and Even state- product, meta-piperidine 0.2% Dr. D’Ambra9 were made made
ments “subject com- regards to the “dirt.” The “dirt” and 74.8% specifically end-product, *13 interference, only which was of the pound” simple pu- through then be removed could most, the At construc- product. the end crystallization, processes, rification such “substantially pure” derived of from tion leaving para-piperidine 99.2% derivative applies to patent’s interference the '610 and de- meta-piperidine end 0.8% product not product, end the prod- end product. rivative end Such an in at this CPK intermediate issue the .case. at uct mixture arrive the standard would we found that Since have even pharmaceutical-grade for ap- when pure” has different constructions a substan- though representéd the “dirt” and the plied to the CPK intermediate early in of the impurity stages tial the in the '703 product end '129 Again, in the reaction. the weakness applying for the justification there is no an inability produce its to was “substantially pure” from the definition of ratio to product para- 125:1 of to patent’s '610 interference derivative, any- or even meta-piperidine regioisomer” patent. in pure the '703 It. thing such ratio. approaching determining the scope the of deficiency this inherent of the '129 the fur term district “pure,” cpurt in regioisomerie purity that ent’s “substantially pure” that ther assumed Further, upon. the patent improved impurities present in apply must to all in the the disclosed '129 and'703 processes solution, just regioisomerie purity. not patents puri- need for further consider the that plain The district court reasoned the steps fication after the claimed reactions. in of must language help purification steps these will While all “a of impurities, volve because solution improve para- meta-piperi- the ratio of meta-CPK, 0.2% para-CPK, 25% product, they will also remove other dine substantially 74.8% dirt would not be Therefore, gener- impurities. reaction 55; Aventis, pure.” App’x Joint see also al in components of other reaction 2175928, at *8. This flawed 2011 WL largely is irrelevant at CPK-mixture analysis again not the appro does consider stage. the intermediate district court for priate frame of reference claim con recognized point this a lesser actually ordinary skill in person struction. A extent, noting respect that “with to all recognize pat would does include ele- impurities” “intended improved regioisomerie purity ent solvents, solutions, cata- such as ments the end results from the lysts hold compounds.” and other We compared claimed reaction as to the Frie- “substantially -pure,” modifier acylation del-Crafts disclosed light person ordinary construed example, patent. For the district skill in the art in view of the claimed hypothetical “of 25% para- court’s mixture art, only ap- improvements over the CPK, dirt,” meta-CPK, 74.8% 0.2% im- all plies regioisomerie impurities, not very patented pro reaction could well purities. 25% derivative end para-piperidine duce prod- para-piperidine derivative end
9. The statements made Dr. D’Ambra dur- ing patent’s proceedings meta-piperidine interference uct to 0.2% point were focal court’s and district application puri- defendant’s of "at least 98% ty impurities” to all intermediate. Ecolab, 264 Appellants’ (noting Construction F.3d at 1366 that Web- ster’s New Collegiate Dictionary, Ninth construction explicit With no (9th 1983), ed. “substantially” defines claims, specifi “largely wholly mean but not that which cation, history, prosecution apply or we specified”). is “Largely wholly” but not is “ordinary customary” definition to the approach consistent with a contexts, court flexible to re- claim term. In other this “substantially” gioisomeric purity intermediate, non interpreted has as a specific approximation that avoids to the specification’s faithful silence re- *14 See, boundary. e.g., Playtex numerical and, garding precision numerical most im- Prods., Co., Inc. v. Procter & Gamble 400 is not portantly, arbitrarily tied to the 901, (Fed.Cir.2005); Dy 907 Liquid F.3d FDA for pharmaceutical-grade standard Co., Corp. Vaughan v. F.3d namics 355 products. ingests end No one the inter- (Fed.Cir.2004) (“The ‘sub 1368 compouhd, mediate so there is no reason meaningful implying is a modifier stantial’ end-product to impose purity on it. ”); ‘approximate,’ ‘perfect.’ than rather Therefore, adopt Appellants’ we pro- AVE, Corp. 339 Cordis v. Medtronic posed “substantially pure construction of (Fed.Cir.2003); Ecolab, F.3d regioisomer following formula” as Envirochem, Inc., Inc. v. 264 F.3d patent used in the '703 and construe the (Fed.Cir.2001). 1366-67 “largely term to mean not wholly but
In “substantially para regioisomer context of the intermediate of the intermediate, pure” applied shown, as to CPK structure as compared the meta “substantially” also not be amenable would isomer.” boundary. a numerical patent The '703
implies regioisomeric that purity III. Conclusion 67%, greater be than should the district in Because court erred con- 15-25, 4 11. patent specification col. but the struing “substantially pure” as used in the tellingly any does not- list mini necessary '703 patent, we reverse and remand. mum for the CPK in intermediate AND produce piperidine order to a desired de REVERSED REMANDED product pharmaceutical- rivative end purity.
grade As described Costs product end with a No costs. regioisomeric below pu 98% can be through crystallization rified other or BRYSON, Circuit Judge, dissenting. to reach physical techniques pharmaceuti majority that concludes the district cal-grade purity, showing that court erred its construction the term intermediate not itself at a does need to be “substantially pure” in claim 1 of U.S. regioisomeric purity higher. of 98% or 5,750,703 (“the patent”) Patent No. patent col. 1. 55 to 1. 14. col. 14 district therefore reverses the court’s Appellants propose I judgment. uphold would district regioisomer pure following formula” term, court’s construction of that and I “largely should be construed as but - respectfully therefore dissent.
wholly regioisomer the para of the inter- shown, mediate the structure as com- I pared to the meta isomer.” Appellants’ Br. 10. The district court construed the term This construction “substantial- ly” applied previously approval pure” “at least mean end and that the term “substan- impurities.” product, to all
purity with construction, the court arriving meaning has a tially pure” at different “substantially pure” first determined to intermediates than when used to refer it refers to whether has the same refer to As used products. used to or to the Aventis ar- regioisomer, reference The court intermediate. para-CPK gues that the term phrases uses noted that the “inventor wholly “largely [para-CPK], but not means ‘substantially pure ‘substantially pure’ and compared [meta-CPK].” indiscriminately to refer to regioisomers’ majority pro- Aventis’s embraces and intermediates. products final both construction, holding posed that the is no evidence that inventor There gives differ- term to mean different intended the referring ent to the terms meanings when histo- things.” prosecution Based on the “sub- “substantially pure regioisomer” and patent and related U.S. ries of the '703 *15 stantially derivative.” As pure piperidine (“the 5,578,610 patent”),1 Patent No. ruled, however, in- the court the district the term the court then held that “sub- distinguish evidence does not be- trinsic stantially pure” pharmaceutical refers to way “substantially pure” is used tween the i.e., Finally, 98% the purity, pure. grade terms, for respect to two those required that the purity court determined uphold that I the district reason would was be'measured with to level to court’s claim construction. just not unwanted impurities, all the meta- CPK, the except purity that level did seeking distinguish to the In between of not include “intended elements solutions meaning “substantially pure” of the term solvents, catalysts, or other com- such as re- applied when it is to the intermediate not pounds impuri- that are considered gioisomer opposed applied to as when it is ties.” product, to the derivative end is primary argument appeal
Averitis’s argument relies on that one of Aventis the “substantially pure” that the term should in that ordinary skill the would know meaning when it re- given be a different the purity may intermediates be differ- intermediate, para-CPK fers the which it purity products, ent the of end from the claim describes as a testimony in of that expert support offers CPK, regioisomer” of than when it pure person But if a of ordi- proposition. even refers the derivative end nary. necessarily in the skill art would essentially Aventis concedes that product. regard meaning thing the purity same ^substantially if the term at issue were product, as for an an intermediate end pure purity end with re- product,” 98% analysis the does not end there. an spect impurities to all would be accu- In at least two the intrinsic rec- places, the rate construction. But since “substantially pure” ord the term uses is “substantially pure” used claim 1 to way regard regioi- the to the same regioisom- “substantially pure refer the First, product. and the somer end i.e., para-CPK intermediate— er”— specification states: argues Aventis different construc- that regioi- Although second mixture of is that required. tion Aventis contends and the third [an intermediate] somers by the evidence relied the district upon only regioisomers piperi- mixture of final pertained [the court to the patent, and the two application 1. The as the '610 that as the '703 issued issued application specifications essentially the same. ent filed as division of fact, product] analyzed however, Carr process. dine derivative can be both the experiments, practical sepa- HPLC discussion of the art and the discus- gram of sub- quantities ration to obtain sion the claimed invention use pure stantially regioisomers has not referring to re- been achieved. gioisomers; of the one refer- “mixture[s]” (including Each mixture the first [also CPK, enced in the second is paragraph intermediate]), expected would be the piperidine prod- while another is para contain 33% the isomer and 67% Thus, uct. patentee distinguish fails to compo- isomer. these meta Since “substantially pure between regioisomer” inseparable, nents are it has not been “substantially pure product],” [end possible to obtain of the regioi- either in fact affirmatively suggests second, [first, somers in each and third] pure” does not substantially pure mixture in form. turn on it whether modifies “regioisomer” at col. 4 (emphasis 11. 16-24 or “piperidine derivative product].” [end added). Second, in an interference involv- Regarding reference, the second Aventis ing patentee the related argues that it clear in that the context wrote: passage concerns the light specification, When read argues Aventis also one the art have under skilled would “subject compound” that pas- described in e phras stood that *16 sage is the end product, making clear that pure”, used in 1-17 of as claims the pure” the discussion “substantially patent], Patent D’Ambra to [the passage only that applies prod- to the end subject compound mean the that has uct. The problem position with Aventis’s pharmaceutical grade and is in a quoted is that language expressly the re- than purer form that attained the “ ‘substantially fers to pure’ ... as used in (e.g., 4,254,- prior art U.S. Patent Nos. 1-17,” claims and claim 12 of the '610 129, 4,254,130, 4,285,957, 4,285,958 a pure refers to “substantially re- (collectively, to Carr “the Carr Pat Thus, “‘substantially gioisomer.” pure’ ents”). infra, demonstrated, As those ... used in claims unequivocally 1-17” as in the art that recognized phar skilled “substantially pure regioisomer.” includes grade purity requires maceutical im an That reference thus rebuts claim Aventis’s 2%, greater no level than and the patentee that the distin- careful to Carr to Patents were unable achieve guish regioi- between pure purity. such “substantially pure piperidine somer” Importantly, that response refers to patentee product].” [end claims patent; 1-17 one of “ ‘substantially pure pi- could have written recites, claims, those “a piperi- ... peridine derivative’ as used in claims dine produced by a compound 1-17,” to, referring only but it chose a comprising: providing substan- “ ‘substantially pure’ ... as in claims used tially pure regioisomer....” (emphasis that examples 1-17.” Those two show the added). patentee did not intend for the term “sub- pas- Aventis concedes that in the first stantially pure” have a mean- different sage distinguish the patentee failed to be- ing depending whether on it was describ- “substantially pure” tween the use of as ing product. or an intermediate applied to an intermediate and to an end product, Beyond passages, it two intrinsic passage but claims that the those the is provides irrelevant because it art record little in eon- help concerns else of Stamps.com Tech. Inc. v. “substantially pure.” case. See Kara struing the term claim, (Fed.Cir.2009) 1341, 1348. 582 F.3d However, con principles of general (“While helpful,, sources like ex- extrinsic pre “[W]e here. struction are instructive per- testimony cannot overcome more pert that the sume, compelled, otherwise unless evidence.”). intrinsic suasive or in the same same claim term construed patents carries same related testimony not indi- expert Aventis’s does Raytek Eng’g, Inc. v. meaning.” Omega “substantially pure regioisomer” that cate (Fed.Cir.2003); 1314, 1334 Corp., 334 F.3d specific that a a term connotes Solutions, v. Timex LLC Paragon also see purity relative to that of the level of (Fed.Cir.2009) 1075, 1087 Corp., 566 F.3d Thus, although product.
(“We that the same apply presumption mean- certainly could have different pure” portions contexts, in different appearing no evi- terms there is ings different mean given same the claims it some- indicating should that must mean dence be from the ing unless it is clear used describe thing different when specification history terms that prosecution regioisomer .opposed as an end meanings por majority have different at different its construction of the bases claims.”). Starting “substantially pure regioisomer” tions of the term “sub- general that definition presumption describing from an unrelat- thing stantially,” which is taken means the same dictio- describing general it ed case that in turn cites as does when “regioisomer” derivative,” appeal That to extrinsic nary definition. it is clear “piperidine evidence from outside art underscores put “compelling]” forth Aventis has not nothing the fact Aventis has offered Indeed, contrary.2 not evidence to the record, even the intrinsic or in the state above, supports intrinsic record ed art, focus to define the term that is the finding court’s district parties’ dispute. Instead of resort- throughout has the same *17 general as ing to extrinsic evidence to the to pointed and Aventis has patent, the meaning “substantially” term stand- the nothing sug the to compelling record own, the interpret its should ing on we on ex gest Aventis’s reliance otherwise.3' did “sub- claim term that Aventis define: ordinary one of skill in pert testimony that stantially pure.” w “substantially kno the would that can de pure” things mean different when ignoring There is for the intrin- no basis describ scribing intermediates than when that “sub- presumption sic record and the to over ing products enough stantially pure” end is is a discrete claim meaning throughout the persuasive come the intrinsic record this with consistent suggests presumption majority majority the 2. The cites two our cases for also patent proposition ap- same in a that the of consistent claim construction does not meanings Microprocessor can have different ply explicit in this case because "there is no — Inc., Corp. v. Tex. Enhancement Instruments placed 'substantially pure' limitation 1367, (Fed.Cir.2008), Ep 520 F.3d 1376 product end the rele- Inc., Sys., Compressors, Gas v. Bauer con Inc. However, patent.” claims vant 1022, (Fed.Cir.2002). 279 F.3d 1030-31 In “substantially pure” limits the the term cases, however, there was a both of those pat- product claimed end related applying clear the intrinsic record for basis in ent, applies presumption here. See so By meanings to the different contrast, same term. Inc., (applying OmegaEng’g, F.3d at 334 1334 compelling evidence that there is no consistency presumption “the same to pure” "substantially was intended to mean patents”). claim term in ... related things respect “regioisomer” different "piperidine derivative.”
1381 that apparently argues Aventis believes Aventis that this patent. evidence is ir- to be “substantially pure” pertains for construed relevant because it to the purity meaning it the same each time is product. have level of end But because the patent, patentee in the would patent used distinguish does not between the purity explicitly “link” pure” have meaning “substantially as applied to that of the end para-CPK intermediate to an as applied to an But has it If product. intermediate, Aventis backwards: it if a follows that “substan- pure” patentee wanted tially pure product]” means a product [end meanings different when applied to have pure that is at least 98% with respect to all elements, it explicitly different needed to impurities, then the same at- them. “unlink” to “substantially [para-CPK].” taches pure The cases that in support Aventis cites II position of its are to it. unhelpful Aventis arguments easily dis- Aventis’s other proposition cites several cases for the that (and essentially un- of. It is clear posed the term need “substantially” not have a “substantially pure” that disputed) means boundary. strict numerical E.g., Playtex pure” describing least 98% “at Prods., Co., Inc. v. Procter & Gamble 400 In prosecution history 901, (Fed.Cir.2005); 907 F.3d Anchor Wall equated substan- applicant Walls, Inc., Sys. Retaining v. Rockwood tially pure “a piperidine derivative with (Fed.Cir.2003); 340 F.3d 1310-11 pharmaceutical level suitable AVE, Inc., Corp. v. Cordis Medtronic 339 The district found that “[i]t use.” court (Fed.Cir.2003); Ecolab, F.3d essentially pharmaceuti- undisputed Envirochem, Inc. v. F.3d cally acceptable purity is 98%.” The (Fed.Cir.2001). cases Those have no made in the course of entee’s statements here, however, application because in this involving the proceeding an interference case the intrinsic evidence establishes that support also district court’s given the term the term conclusion strict numerical meaning, the district as used in the '906 and its pure,” court found. relatives, least In pure.” means “at 98% sum, I conclude that interference proceeding, patentee means “at least the term equated “substantially pure” with to all and that impurities” it has *18 purity” ex- “pharmaceutical grade respect regioi- with to both agreed “pharmaceutical grade pressly I somers the end would purity requires impurity great- level no affirm judg- therefore the district court’s prosecution than 2%.” er histories ment. support also the district court’s conclusion the required purity level referred to impurities, to all respect just single compo- other
nent, such as meta-CPK.