`
`1111111111111111111111111111111111111111111111111111111111111
`US009066980B2
`
`(12) United States Patent
`Calderari et al.
`
`(JO) Patent No.:
`(45) Date of Patent:
`
`US 9,066,980 B2
`*Jun.30,2015
`
`(54) LIQUID PHAUMACEUTICAL
`FORMULATIONS OF PALONOSETRON
`(71) Applicants:Helsinn Hcalthcarc SA, Lugano (CH);
`Roche Palo Alto LLC, Palo Alto, CA
`(US); Simone Macciocchi, Melide (CH);
`Giulio Macciocchi, Breganzona (CH)
`
`(72)
`
`Inventors: Giorgio Calderari, Rancate (CH);
`Daniele Bonadeo, Casalzuigno (IT);
`Roberta Cannella, Varese (lT); Alberto
`Macciocchi, Melide (CH); Andrew
`Miksztal, Palo Alto, CA (US); Thomas
`Malefyt, Carmel Valley, CA (US);
`Kathleen M Lee, Palo Alto, CA (US)
`
`(73) Assignees: Belsinn Bealthcare SA,
`Lugano/Pazzallo (CH); Roche Palo Alto
`LLC, Palo Alto, CA (US)
`
`( *) Notice:
`
`Subject to any disclaimer, the term of this
`patent is extended or adjusted under 35
`U.S.C. 154(b) by 0 days.
`This patent is subject to a terminal dis-
`claimer.
`
`(21)
`(22)
`(65)
`
`Appl. No.: 13/902,299
`Filed:
`May 24, 2013
`Prior Publication Data
`US 2013/0289065 AI
`Oct. 31, 2013
`
`Related U.S. Application Data
`(63) Continuation of application No. 13/901,437, filed on
`May 23, 2013, now Pat. No. 8,598,219, which is a
`continuation-in-part of application No. 13/087,012,
`filed on Apr. 14, 2011 , now Pat. No. 8, 518,981 , which
`is a continuation of application No. 11/1 86,31 1, filed
`on Jul. 21, 2005, now Pat. No. 7,947,724, which is a
`continuation of application No. PCT/EP2004/000888,
`filed on Jan. 30, 2004.
`(60) Provisional application No. 60/444,351 , filed on Jan.
`30,2003.
`
`(51)
`
`(2006.01)
`(2006.01 )
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01 )
`(2006.01 )
`(2006.01)
`
`Int. Ct.
`A6IK 31147
`A6IK 47126
`A6JK 311473
`A61K 47118
`A61K 47112
`A61K 47100
`A61K 47102
`A6IK9100
`(52) U.S. CI.
`CPC ............... A61K 47126 (2013.01); A61K 471183
`(2013.01); A61K47112 (2013.01); A61K 47100
`(2013.01); A61K 311473 (2013.01); A6JK
`47102 (2013.01); A61K 910019 (2013.01);
`A61K 910095 (2013.01)
`(58) Field of Classification Search
`USPC .................................................. 514/296, 397
`See application file for complete search history.
`
`(56)
`
`References Cited
`
`U.S. PATENT DOCUMENTS
`
`4,695,578 A
`4,753,789 A
`4,886,808 A
`4,906,755 A
`4,929,632 A
`4,937,247 A
`5,011,846 A
`5,034,398 A
`5,202,333 A
`5,240,954 A
`5,272,137 A
`5,344,658 A
`5,578,628 A
`5,578,632 A
`5,622,720 A
`5,854,270 A
`5922,749 A
`5,955,488 A
`6,063,802 A
`6,132,758 A
`6,284,749 Bl
`6,287,592 Bl
`6,294,548 Bl
`6,699,852 B2
`7,109,339 B2
`7,947,724 B2
`7,947,725 B2
`7,960,424 B2
`8,5 18,981 B2
`8,598,218 82
`
`9/!987 Coates et a!.
`611988 Tyers eta!.
`1211989 Kino
`311990 Gitt~s
`511990 Tyers eta!.
`6/.1990 King
`4/1991 Gittos eta!.
`711991 King
`411 993 Berger et a!.
`81!993 Tyers eta!.
`1211993 Blase et a!.
`911 994 Collin
`1111996 Tyers eta!.
`1111996 Tyers eta!.
`4/1997 Collin
`1211998 Gambhir
`7/1999 Tyers eta!.
`911999 Winterborn
`5/2000 Winterborn
`10/2000 Munayyer et al.
`9/200 I Castillo eta!.
`9/2001 Dickinson
`9/200 I James
`3/2004 Robichaud
`9/2006 Lee et a!.
`5!20 I I Calderari et a!.
`5/20 II Calderari et a!.
`6/20 II Calderari et a!.
`8120 13 Calderari et a!.
`12120 13 Calderari et al.
`(Continued)
`
`FOREIGN PATENT DOCUMENTS
`
`EP
`WO
`
`411992
`0 512 400 A I
`12/2003
`W0-03100091
`(Continued)
`OTHER PUBLICATIONS
`Perez et al. (cancerJ. Sci AJn. (1998) 4_ 1):52*
`R. M. Eg.len et al., "Pharmacological characterization of RS 25259-
`197, a novel and selective 5-HT3 receptor antagonist, in vivo:' Br. J
`Pharmacology 114:860-866 (1995).
`Chelly, Jacques elal., Oral RS-25259 Prevents Postoperative Nause;l
`and Vomiting Following Laparoscopic Surgery, Anesthesiology,
`1996, vol. 85, No. 3A, p. A2 1.
`Sorbe, Bengt, 5-HT-3 Receptor Antagonists as Antiemetic Agents in
`Cancer Chemotherapy, extracted from Expe1t Opinion on l.nvestiga-
`tional Dmgs, 1996, vol. 5 No. 4, pp. 389-407.
`Gaster, Laramie M. and King, Frank D., Serotonin 5-HT3 and 5-HT4
`Receptor Antagonists, extracted from Medicinal Research Reviews,
`1997 vol. 17, No. 2, pp. 163-2 14.
`Tang, Jun et al., "Efficacy of RS-25259, a Novel 5-HT3 Antagonist,
`In the Prevention of Postoperative Nausea and Vomi ring after Major
`Gynecologic Surgery," Anesthesiology, 1997, vol. 85, No. 3 suppl. p.
`A329.
`
`(Continued)
`Primary Examiner - Shirley V Gembeh
`(74) Attorney, Agenl, or Firm - Clark G. Sullivan;
`Troutman Sanders LLP
`AUSTRACT
`(57)
`The present invention relates to shelf-stable liquid formula-
`tions of palonosetron for reducing chemotherapy and radio-
`· . Dr. Reddy's Laboratori~s Ltd. et al.
`therapy _induced emes·
`are parttcularly useful
`'
`'
`oral liquid medicamet
`v.
`Helsinn Healthcare SA, et al.
`16 C
`U.S. Patent No. 8,729,094
`Reddy Exhibit 1037
`
`
`
`IIIII
`
`lllllllllllllllllllllllllllllllllllllllllllllllllllllllllllll
`
`US009066980B2
`
`( 12) United States Patent
`Calderari et al.
`
`(JO) Patent No.:
`(45) Date of Patent:
`
`US 9,066,980 B2
`*Jun. 30,2015
`
`(54) LIQUID PHARMACEUTICAL
`FORMULATIONS O F PALONOSETRO N
`(71) A pplicants:Hclsinn Hcalthcarc SA, Lugano (CH);
`Roche Palo Alto LLC, Palo Alto, CA
`(US); Simone Macciocchi, M elide (CH);
`G iulio Macciocchi, Breganzona (CH)
`
`(72)
`
`Inventors: G iorgio Caldcrari, Rancate (CH);
`Daniele Bonadeo, Casalzuigno (JT);
`Robl'rta Cannella, Varese (IT); Albl'rto
`~accioccbi, Mel ide (CH); Andrew
`~iksztal, Palo Alto, CA (US); Thomas
`Malcfyt, Carmel Valley, CA (US);
`Kathleen l\1 Lee, Palo Alto, CA (US)
`
`(73) Assignees: Helsinn Healthcare SA,
`LuganofPazzallo (CH); Roche Palo Alto
`LLC, Palo Alto, CA (US)
`
`( * ) Notice:
`
`Subject to any disclaimer, t·he term of this
`patent is extended or adjusted under 35
`U .S.C . 154(b) by 0 days.
`This patent is subject to a terminal dis-
`claimer.
`
`(21) Appl. No.: 13/902,299
`(22) Filed:
`-"lay 24,2013
`(65)
`Prior Publication Dat a
`US 2013/0289065 AI
`Oct. 31,2013
`
`(63)
`
`(60)
`
`(5 1)
`
`(52)
`
`(58)
`
`Related U.S. Application Data
`Continuation of appllcation No. 13/901,437, filed on
`May 23, 2013, now Pat. No. 8,598,219, wllicb is a
`continuation-in-part of application No. 13/087,012,
`filed on Apr. 14, 201 1, now Pat. No. g,s Jg,981, which
`is a continuation of application No. J 11186,311, filed
`on Jul. 2 1, 2005, now Pat. No. 7,947,724, which is a
`continuation of application No. PCT/EP2004/000888,
`filed on Jan. 30, 2004.
`Provisional application No. 60/444,351, filed on Jan.
`30, 2003.
`
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`(2006.01)
`
`Int. C l.
`A6IK 31147
`A61K 47126
`A6IK 311473
`A61K 47118
`A6IK 47112
`A6IK 47100
`A61K47102
`A6IK 9/00
`U.S. <.:I.
`CPC ............... A61K 47126 (2013.01); A61K 471183
`(2013.01); A6JK 47112 (2013.01); A61K 47100
`(2013.01); A6/K 3/1473 (2013 .01 ); A61K
`47102' (2013.01);A6IK 9/0019 (2013.01);
`A6JK910095 (2013.01)
`Field of C lassification Search
`USPC ................................................ 5141296, 397
`See application tile tor complete search history.
`
`(56)
`
`References Cited
`
`U.S. PATENT DOCUMENTS
`
`4,695,578 A
`4.753,789 A
`4,886,808 A
`4,906,755 A
`4,929,632 A
`4,937,247 A
`5,01 t,R46 A
`5,034,398 A
`5,202,333 A
`5,240,954 A
`5,272,137 A
`5,344,658 A
`5,sn,6n A
`5,578,632 A
`5,622,720 A
`5,854,270 A
`5,922,749 A
`5,955,488 A
`6,063,802 A
`6,132,758 A
`6,284.749 Bl
`6,287,592 131
`6,294,548 Bl
`6,699,852 B2
`7,109,33\J H2
`7,947,724 B2
`7,947,725 B2
`7,960,424 02
`8,518,981 B2
`8,598,218 B2
`
`911987 Coates et al.
`6!1988 Tyers c l al.
`1211989 King
`3/1990 Gittos
`511990 Tyers et al.
`6Ji990 King
`41t99 1 Girtos et al.
`711991 King
`41!993 Berger et al.
`811993 T ycrs ct al.
`1211993 Blase et al.
`911994 Collin
`1111\J96 'fyers el al.
`I I 11996 Tyers et al.
`411997 Collin
`1211998 Gambhir
`711999 Tyers et al.
`911999 Winterborn
`512000 Winterborn
`1012000 Munayyeretal.
`91200 I Castillo el aJ.
`91200 I Dickinson
`91200 1 James
`312004 Robichaud
`912006 Lee et al.
`5120 I I Calderati et a!.
`5120 I I Calderari et a!.
`6t20 11 Calderari et a!.
`812013 Calderari ct al.
`1212013 Calderari et a!.
`(Continued)
`
`FOREIGN PATENT DOCUMENTS
`
`EP
`WO
`
`411992
`05 t2400 AI
`1212003
`W0-031000\JJ
`(Continued)
`OrHER PU13LJCATIONS
`Perez eta]. (cancer J. Sci Am. (I 998) 4_ 1):52.•
`R. M. Eglen et al., "Pharmacological characterization of RS 25259-
`197, a novel and selective 5-HT3 receptor antagonist, in vivo," Br. J
`Pharmacology 114:860-866 (1995).
`Cbelly, Jacques et al., Oral RS-25259 Prevents Postoperative. ·au sea
`and Vomiting Following Lapamscopic Surgery, Anesthesiology,
`1996, vol. 85, No. 3A, p. A2 I.
`Sorbe, Bengt, 5-HT-3 Receptor Antagonists as Antiemetic Agents in
`Cancer Chemotherapy, extracted from Exper1 Opinio n o n Tnvestiga-
`tional Drugs, t996, vol. 5 No. 4, pp. 389-407.
`Gaster. Laramie M. and King. Frank D .. Serotonin 5-HTI and 5-HT4
`Receptor Antagooists, extracted f5om Medici.oal Research Reviews,
`1997 vol. 17, ~o. 2. pp. 163-214.
`Tang, Jun ct al.. "Efficacy of RS-25259, a ·ovcl S·HT3 Antagonist,
`In the Prevention of Postoperative Nausea and Vomiting after Major
`Gynecologic SUigery," Anesthesiology, .1997, vol. 85, No.3 suppl. p.
`A329.
`
`(Continued)
`
`Primary Examiner - Shirley V Gcmbcb
`(74) Artomey, Agent, or Firm - Clark G. Sullivan;
`Troutman Sanders LLP
`(57)
`ABST RACT
`The present invention relates to shelf-stable liquid fonnula-
`tions of palonosetron for reducing chemotherapy and radio-
`therapy induced emesis with palonosetron. The formulations
`arc particularly useful in the preparation of intravenous and
`oral liquid medicaments.
`16 Claims, No Drawings
`
`Exh. 1037
`
`
`
`US 9,066,980 B2
`Page 2
`
`(56)
`
`l~eferences Cited
`U.S. PATENT DOCUMENTS
`8,598,219 B2
`2001/0020029 AI
`200310095926 A I
`2004/0147510 AI*
`20131026 1149 AI
`2013/0261150 AI
`20 1310289065 A I
`2014/0039000 AI
`
`.l2.i20 13 Cahierari et al.
`9i 200 J James
`5i 2003 Dugger, Ill
`7i 2004 Landau et al.
`I Oi 20 13 Calderari et al.
`I Oi20 13 Calderari et al.
`10i 2013 Calderari et al.
`2.i20 14 Caldcrari et al.
`
`514/218
`
`wo wo
`wo
`
`FOREJGN PATENT DOCUMENTS
`W0-2004045615
`6/2004
`W0-2004067005
`8/2004
`W0-2004703714
`9/2004
`OTHER PUBLICATIONS
`Tang, Jlm et al .. The Efficacy of RS-25259, a Long-Acting Selective
`5-HT3 Receptor Antagonist, for Preventing Postoperative Nausea
`and Vomiting Alter Hysterectomy Procedures, Anesthesia and Anal-
`gesia. 199:', vol. R7, pp. 462-467.
`A dis R&D Profile. Palonosetmn RS 25259 197, Dmgs in R&D, Oct.
`1999. vol. 2, No. 4, pp. 251-252.
`Piraccini Gaia et al., An Interesting 5-HT3 Receptor Anragonisr
`Antiemetic for Patienrs Undergoing Chemorheraphy-based Condi-
`tioning Regimens, Blood, iNov. 16,2001, vol. 98, No. II. part 2, p.
`350b. abstmct No 5169.
`Stacl1er, Georg, l'alonoserron Helsinn, Current Opinion in Jnvestig.1-
`tional Drugs. Oct. 2002, vol. 3, No 10, pp. 1502-1 507.
`Navari, Rudolph M., Pathogenesis-Based Treatment of Cherno-
`thempy-lnduced Nausea and Vorniring-"1\vo New Agenrs, Journal
`of Supportive Oncology, 2003, vol. I (2), pp. Xl)- 103.
`Chaitow, 1990, 3 pages.
`Opposition Brief filed hy Or. Reddy's L~bomtories (lTK) Limited,
`opposition to European Parent No. 160 1359 B l dated Jul. 7, 2009
`Photolyric and oxidative degradation of an antiemetic agent, RG
`.129.15 (Won C. M. etal., lnternation~I.Jomnal ofPh~nnaceutics .12 1,
`95-105 (1995).
`Palonosetron: a phase II dose ranging shody to assess over a 7 d~y
`period the single dose phannacokinetic profile of palonosetron in
`palients receiving highly emetogenic chemotherapy. Piraccini eta!.,
`Proc. Am. Soc. Clin. Oncol 2002 21 Abs 449 (2002).
`Formulation and administration techniques to m inimize injection
`pain and tissue damage associated with parenleral products. La.rl)' A.
`Gatlin and Carol A. Brister Gatlin, from Injectable Dnog Develop-
`ment: · l"echniques to Reduce Pain and lrrilation (Edited by Pramod K.
`Gupta and Gayle A. Brazeau; published by lnfonna He>dlth Care)
`1999; ISB. 1574910957,978.1574910957, p.401-42! .
`Parenteml Dosage Forms. Joanne Broadhead, from Part 11-Ea.rly
`dnog development, pharmaceutical prefonnulation and formulation:
`a practice guide from candjdme drug selection 10 conunercial dosage
`form (Edited by Mark Gibson; Published by lnterphanna Press,
`200.1; ISBN 157491120 1, 9781574911206), p. 331-353.
`Opposition Brief tiled by l"ecnimede Sociedade Tecnico-Medicinal
`S.A. in opposition to Ew-opean Patent ·o. 1601359 Bl, Jul. 8, 2009.
`Response brieffiled by Helsinn Healthcare S.A. dated Jul. 13,2007,
`in response to the communication pursuant lo Art. 96(2) EPC of Jan.
`3, 2007 regardjng Serial No. 04 706 657.6-2123.
`European Patent Office official corrummication dated Jul. 19, 2006,
`regarding Serial o. 04 706 657 .6.
`Response ofHelsinn Healthcare S.A. dated o ov. 29, 2006, regarding
`EPO otlkial communicalion dare Jul. 19, 2006.
`Lachman et al., The Theol)' and Practice of Industrial Pharmacy,
`1986, third edition, pp. 652-784.
`Declaralion ofValenlino J. Stella, Ph.D. dated Sep. 19,2007.
`Opposition Brief filed by Martin Paul While, opposition to European
`Patentl\"o . . 1601359 B l. Jul. 8, 2009.
`Wong eta!. (.1995), in British Journal ofPharma.cology, vol. 114, pp.
`851-859.
`Cov-er page and pp. 642-644 and 783-784 ofThe Theory and Practice
`of lnduscrial Pharmacy, Third Edition, Lea and Febiger (1986).
`
`Cover page and pp. 514-5.15 of Modern Pharmaceurics, Second Edi-
`tion. Marcel Dekker (.1990).
`Cover page and pp. 142-143 of Pharmaceutical Dosage Forms:
`Parenteral Medications vol. I, Second Edition, Marcel Dekker
`(1992).
`Mitsuo Matsumoto et al., "Yaklo7..aigaku Manual", I st edition,
`Nanzando Co., Ltd. (1989) 2 pages.
`Michael J. Pika!, ··Freeze Drying", Encyclopedia of Pharmaceutical
`Technology, Third Edition, Jan. 2007, pp.l824-J825, vol. 3, Informa
`Phannaceuticals and Heahhcare.
`Daniele Bonadeo, <;Supplemental Declaration of Daniele Bonadeo
`Under 37 C.F.R. 1.132", filed in U.S. Appl. No. 11/388,270, Jun. 8,
`2009.
`Kranke et al., 2007 "Recent advances, trend~. ard economic consicl-
`erations in . . . "F.xpel1. Opinion Phannacotherp., 8( IS): 1217-1235.
`Morrow et at., 1995, '"Progress in reducing nausea and e mesis: Com-
`parisons of ondansetron, granisetron, and tropisetron." Cancer, vol.
`7fi, No. 3 pp. 343-357.
`lfSPTO Nolice of Allowance and Fees Due, lf.S. Appl. No.
`111388,270, foled Mar. 24,2006, Date Mailed Jan. 26.2010.
`lJSPTOOfficeAction, lf.S. Appl. No 11 '129,lG9, Date Mailed .Tan.
`15. 2010.
`lsraili, 7.aifarH .. "Clinic.•! Pharmacology of Serotonin Receptor Type
`(5-HD) Anlagonisrs," Com . :vied. Chem. Cenlral Nervous System
`Agents, 2001:1, 17 1-199.
`Ba11on (Citrale Buffer Calculalion) 2000, 2 pages.
`USI'TOUfficeAclion, U.S. Appl. No. 11/20 1,035. Dale Mailed Aug.
`19, 2009.
`Response of Helsinn Healthcllte ro opposition of F.P Serial No. 04
`706 657 .6 , dated Feb. 11, 2010.
`Annex I (Statemenl ofWalso Mossi, Ph.D.) ro Response ofHelsinn
`Healthcare to Opposition of EP Serial No. 04 706 657.6 dated Feb.
`II, 2010.
`Annex 2 to Response of Helsinn Healthc;~re r·n Opposit·ion of 1-:P
`Serial No. 04 706 657.6 dated Feb. 11, 2010.
`Annex 3 to Response of Helsinn HealthcMe to Opposition of F.P
`Serial No. 04 706 657 6 dated Feb .II, 20 10
`Smruna.ry of Product Characteristics for Aloxi 250 (2009) .
`Scientific Discussion from t.he European Public Assessment Repol1
`for Aloxi ( Palonoseteron Hydrochloride) 2006.
`6th Edition, Handbook of PhannaceuticaJ E.xcipients (2009), pp.
`247-250 ( RPS Publishing).
`Lewis, Gareth A (2006) 'Optimization Methods,' Encyclopedia of
`Pharmaceutical "J"ecbnology, I: I, 2452-2467.
`May 24, 20 I J Para. IV notice from Teva Pharmaceuticals re '724 and
`'725 patents.
`May 24, 2011 Para. IV notice from Sandoz re '724 and '725 patents.
`May 24, 2011 Para. IV notice from Dr. Reddy's re '724 and '725
`patents.
`Aug. 9. 2011 Para. IV notice fro.m l)r. Reddy's re '424 patent.
`Aug. 19, .201 1 Para. IV notice from Teva Pharmaceullicals re '424
`patent.
`Sep. 22, 2011 Para. IV notice from Sandoz re '724, '725 and '424
`patents.
`Jul. S, 2011 Complaint lor patent infringement (0. N.J. case o.
`11-03962).
`Sep. 23, 20 II Complaint for patent infringement (D. N.J. case o.
`11-5579).
`Aug. 31, 20 II Answer and counterclaim of Dr. Reddy's Laborato-
`ries, Ltd. and Dr. Reddy's Laboratories, Inc. (D. N.J. case No.
`11-03962).
`Sep. 13, 2011 Sandoz Inc.'s answer to complaint for patent infringe-
`ment and counterclaims (D. I.J. case 1\o. 11-03962).
`Sep. 13,2011 Teva Phannaceuticals USA, Inc. and Teva Pharmaceu-
`tical Industries Ltd.'s answer(D. N.J. case No. 11-03962).
`Oct. 5, 2011 Plaimill's reply to answer and cOlmterclaim of Dr.
`Reddy's Laboratories, Lid. and Dr. Reddy Laboratories, Inc. (D. N.J.
`case No. 11-03962).
`Oct. 2 1, 20 I 1 Plaintiffs reply to Sandoz Inc.'s answer to complaint
`for patent infringement and counterclaims (D. N.J. case . o.
`11-03962).
`Oct. 24, 201 J Answer and counterclaim of Dr. Reddy's !Laboralories,
`Ltd. and Dr. Reddy's Laboratories, Inc. (D. N.J. case No . .11 -5579).
`
`Exh. 1037
`
`
`
`US 9,066,980 B2
`Page 3
`
`(56)
`
`l~eferences C i ted
`OTHER PUBLICATIONS
`
`Oct. 24, 20.11 Sandoz Inc.'s answer to complaint for parent infringe-
`ment and counterclaims (D. N.J. case No. ll -5579).
`Ocr. 27, 201 I Order consolidating the two cases (0. N.J. case No.
`11-5579).
`Nov. 17, 20 11 Plaintiffs' reply t·o answer and counterclaim of Or.
`Reddy's Laboratories, Ltd. and Dr. Reddy's Laboratories, Inc. (D.
`N.J. case 1\'o. I I -03962).
`Nov. 17, 20 II Plaintiffs' reply to Sandoz Inc.'s answer to complaint
`for patent infringement aNi counterclaims (D. N .J. case No.
`11 -03962).
`Dec. 5. 20 I I Teva Phnrmaceuticals I JSA Inc. ancl Teva Phammceu-
`tic,11S Industries Lin. 's answer to complaint· for patent infringemenrof
`the "424 patent (D. 1'\.J. case ;\lo. 11 -03962).
`May 2 I, 2012 Defendants' opening claim constmction brief (includ-
`ing exhibits 1-3 1) .
`May 2.1, 20 12 Plaintiffs' opening claim constntction brief(including
`exhibits 1-1 5).
`Jul. 20, 20 12 Defendants' responsive claim <:onstmction brief
`(including exhibits 1-3).
`Jul. 20, 2012 Plaintiffs' responsive claim constmction brief (includ-
`ing Exhibits A and H).
`Sep. 7, 2012 Court transcript from Sep. 7, 20 12 :vlarlunan hea.ring and
`Plaintiffs' Power Point presentation (D. N.J. ca se No. 11-03962).
`Dec. I. 20.1.1 Sandoz Inc.'s. invalidity contentions pursuant to L. Pat.
`R. 3 .6(c) (D. N.J. case 1 o. I 1-03962).
`De.;. l, 20 U Tevfi Pll<l!Iml<;e\lti.;il!s VSA, 11!.;. MQ Tev;1 Pllill11l(l<;eu-
`tic,1l lnduslries, Ltd.'s invalidity contentions. pursuant to L. Pat. R.
`3.6(<:)(D. 1.J. case No. 11-03962).
`Dec. l, 20 II Dr. Reddy's Laboratories, Ltd.'s and Dr. Reddy's Labo-
`ratories, Inc.'s invalidity contentions pursuant to L. Pat. R. 3.6(c) (D .
`N.J. case No. 11-03962).
`Jan. Jl, LUll PlaiDttlfs responses to defendanls' IDvalrdJty conten-
`tions (D. ~.J. case o. I 1..()3962).
`Sep. 25. 2012 Sandoz Inc.'s first amended invalidity contentions
`ptiTSlllant to L. Pat. R. 3.6(c)(D. N.J. case No. 11-03962).
`Nov. 19, 2012 P1aintifts' responses to Sandoz Inc.'s first amended
`inval idity contentions (D. N.J. case No. 1 1-03962).
`L.G. Wade Jr., Organic Chemistry, Cb. 19: Amioes, pp. 867-936
`(Prentice Hall 3d ed. 1995).
`L. L achman et al., The Theory and Practice of Industrial Pharmacy,
`pp. 642~44, 783-784 (Lea & Febiger3d ed. 1986).
`P.P. DeLuca et al., Formulation of Small Volume Parenterals in Phar-
`maceutical Dosage Forms: Parenteral Medications, vol. I, Ch. 5, pp.
`173-248 (Avis, Lieberman, Lachmaneds., Marcel Dekker Inc. 2ded.
`1992).
`C.M. Won et al, Photolytic and Oxidative Degradation of an
`Antiemetic Agent, RGI2915, lnt'l J Phannaceutics 121:95-105
`(1995).
`R.D . Clark et al., 2-(Qu~ nuciidin-3 -yl)pyrido-(4,3-b]indol-l-ones
`and lsoquinoin-1-ones. Potent Conformationally Rest1icted 5-HT3
`Rece ptor Antagonists, J Med. Chern. 36:2645-57 (1993).
`L.A. Trisscl, Dmg Stability and Compatibility Issues, Handbook on
`Injectable Dmgs, pp. XI-XVI (ASHP 7th ed. 1 992).
`J. Broadhead, Parenteral Dosage Forms, Pharmaceutical Prefonnula-
`tion and Formulation: A Practical Guide from Candidate Drug Selec-
`tion to Commercial Dosage Fonn, Ch. 9, pp. 331-354 (Gibson cd.,
`CRC Press I s! ed. 2001).
`K.A. Connors et al., Chemical Stability ofPhannaceulicals: A Hand-
`book for Pharmacists (John Wiley & Sons 2d ed. 1986).
`Zofran®, in the Physician's Desk Reference, op. 1503-07 (5th ed.
`2001) .
`Anzemet®, in The Physician's Desk Reference, pp. 680-683 (5th ed.
`200:1).
`Kytril®, in The Physician's Desk Reference, pp. 3104-3106 (5th ed.
`2001).
`LA. Trissel, Ondansetron HCI, in Handbook on Injectable Dn1gs,
`pp. 683~88 (ASHP 7th ed. 1992).
`Navoban® (tropisetron HC l) Malaysian Prescribing Information
`(Sep. 2000).
`
`Kytril® (granisetron HCI) South African Prescribing Information
`(Dec . .1993).
`S. Motola and S. Agharkar, Preformulation Research of Parenteral
`Medications. Pharmaceutical Dosage Forms: Parenteral Medica-
`tions, vol. l, Ch. 4, pp. 115-172 (Avis, Lieberman, Lachman eds.,
`Marcel Dekker Inc. 2d ed. 1992) .
`J. Wells, Pharmaceutical Preformuatlion: The Physicochemical
`Properties of Dmg Substances, Ch. 5: Dmg Stability, pp . . 152-19 1
`(Ellis Horwod Lid. 1988).
`J. Swarbrick and Boylan, Encyclopedia of Pharmaceutical Technol-
`ogy, Excipienls Chapter: Their Role in Parenteral Dosage Forms, vol.
`19(2): 137-I 72 (Marcel Dekker, [nc. 2000).
`Handbook of Pharmaceutical F.xcipients, 3d F.d.,(Kibbe ed. Pharrna-
`ceutical Press 2000); pp. 140-143, 191-194, 324-23!\.
`G. Stacher, Palonosetron (Helsinn), Curro. ()pin. Investig. Drugs,
`3(10) 1502-7 (2002).
`Handbook of Modern Pharmaceutical An alysis, (S. Ahuja et al. ed.,
`Academic Press, 200 I).
`Jun. 8, 2009 Ronadeo Declaration.
`Jun. 8, 2009 Bonadeo Declaration, Exhibit 2.
`.Tun. R, 2009 BoMdeo DeclarRtion, Exhihit 3.
`HELSNO tt 17262-69 (2008).
`HELSNOU 17270-3 12 (2012).
`Feb. 13. 2007 Statutory Declara.tion of Daniele Ron;adeo, with
`Exhibit A.
`1\ov. 2 1. 2007 StMutory Declaration of Giorgio G1lderari, Daniele
`Bonadeo, Roberta Cannella, Enrico Braglia, and Riccardo Braglia
`Reddy's Paragraph IV notice regarding all three patents (D. N.J. Case
`No. 12-2S67), dated Mar. 30,20 12.
`May 1 1, 2012 Complaint for patent infringement filed by Helsinn a11d
`Roche (D. ),I.J_ Case No. 12-2867).
`Jun. 26, 20 12 Notice of Reddy' s motion to dismiss (D. N.J. Case. o.
`1 2-2~67).
`Jun. 26, 2012 t)r. Redrly's Laboratories, Ltd.'s ann t)r. !{eddy's
`L• boratories, Inc.'s memora.ndumoflaw in supportoftheir motion to
`clismiss or for Slunm,,ry judgment of non-infringement of U .S. patent
`No 7,947,724 (D. N.J. Case 'o. 12-2867) (including Exhibits 1-10).
`Aug. 16,2012 NoticeofPlainriffs' cross-motion for partial summary
`judgment of infringement (D. N.J. C1se No. 12-2867).
`Aug. 6, 2012 Plaintifis' opposition to Defendants' motion to dismiss
`or for suarnna.ry judgment of noninfringe.ment and cross-motion for
`partial sununary judgment of infringement (U. N.J . Case
`o .
`.12-1867) ( including exhibits 1-4).
`Schoneicb declaration (D. N.J. Case o. 12-2867) (Including Exhib·
`its A and 1-24), dated Aug. 6, 2012.
`Sep. 4, 2012 Reddy's brief in opposition to Plaintiffs' cross-motion
`for partia!l summary judgment and reply memorandum of Jaw in
`further support of Reddy's motion to dismiss or for summary judg-
`ment of non-infringement (D.
`.J. Case No. 12-2867)(1nduding
`Jixhibits l-4).
`DeLuca Declaration (D. N.J. Case o. I 2-2867)(lncluding exhibits
`A-J), dated Sep. 3, 2012.
`Sep. 10, 2012 Plaintiffs' letter to Judge Cooper in response to Red-
`dy's combined opposition to Plaintiffs' cross-motion for partial sum-
`mary judgment and reply in suppor1 of Reddy's motion to dismiss or
`for sununary judgment of noninfringement (D.
`.J. Case No.
`12-2867)(including exhibits A and B).
`Sep. 14, 2012 Dr. Reddy's letter in response to Plaintifis' Sep. 10,
`2012letter(D. N.J. Case 'o. 12·-2867).
`USPTO Office Action, U.S. Appl. No. 11/388,268, filed :vlar. 24,
`2006, Mail Date Mar. 29,2010.
`USPTO Kon-Final Office Action, U.S. Appl. No. I 1/186,3 11, mai led
`Aug. 30. 2006.
`USPTOJ'\on-Final OtiiceAction, U .S .Appl. No. I 1/186,3 11, mailed
`Oct. S, 2007.
`USPTOJ'\on-Fina.l Office Action, U.S .Appl. No. l l/l86,3 l l,mailed
`Oct. 6, 2008.
`USPTO Final Office Action, U .S. Appl. No. 11/186,311, 1nailed May
`20, 2009.
`USPTOAdvisory Action, U.S.Appl. !\o. 11/186,3 1.1, mailed Jul. 15,
`2009.
`USPTO Notice of Allowance and Fees Due, U.S. Appl. No.
`11/ 186,31 I , mailed Mar. 4, 2011.
`
`Exh. 1037
`
`
`
`US 9,066,980 B2
`Page4
`
`(56)
`
`l~eferences Cited
`OTHER PUBLICATIONS
`
`USPTO 1 otice of Allowability, U.S. Appl. No. 111186,3 11, dated
`May 24, 20 IJ.
`USPTOI\on-Final Office Action, U.S.Appl. o. I 1/388,268, mailed
`Jul. 17, 2006.
`USPTO !\on-Final Office Action, U.S.Appl. o. I l/388,26l!, mailed
`Nov. 17. 2006.
`USPTO Ken-Final Office Action, U.S.Appl. No. 11/388,268, mailed
`Oct. 3, 2007.
`USPTO 1\on-f iml Office Action, U.S.Appl. No. 11/388,268, mailed
`Mar. 26, 2008.
`USPTO Final OfficeAclioo, U.S. Appl. :-.lo. 11/388,268. mailed Nov.
`12. 2008.
`USPTOI\on-Final OfficeAclion, U.S.Appl. o. 11/388,268, mailed
`Jul. 15, 2009.
`USPTO ~otice of Allowance and Fees Due, U.S. Appl. No.
`111388,268, mailed Dec. 22, 2010.
`USPTO !\on-Final Office Action, U.S.Appl. 1 'o. 11/388,269, mailed
`Jul. 19, 2006.
`USPTO !\on-Final Offict:Action, U.S.Appl. No. 11/388,269, mailt:d
`Nov. 17, 2006.
`USPTO Ken-Final Office Action, U.S. Appl. o. 11/388,269, mailed
`Sep. 20, 2007.
`USPT0l':on-Fiml Office Action, U.S.Appl. o. 11/388,269, mailed
`Jul. 9, 2008.
`USPTO Interview SwJUnary, U.S. Appl. No. I I1J88,269, dated Apr.
`28, 2009.
`USPTO Final 01fice Aclion, U.S. Appl. No. 111388,269, mailed May
`20.2009.
`USPTO Advisory Action, U.S. Appl. No. I I 1388,269, mailed Jul. I 5,
`?OO'l
`USPTO 1\oticeof Abandonment, U.S.Appl. No. ] 1/3l!l!,269, mailed
`Dec. 18,2009.
`USPTO !\on-Final Office Action, U.S.Appl. o. 11/388,270, mailed
`Jul. 13, 2006.
`USPTO Interview Sununary, U.S. Appl. No. 11/388,270, dated Aug.
`3, 2006.
`USPTO !\on-Final Office Action, U.S.Appl. No. 11/388,270, mailed
`Nov. 16. 2006.
`USPTO Kon-Fin..1! Office Action, U.S.Appl. o. 11/388,270, mailed
`Sep. 20, 2007.
`USPTO Interview Summary, U.S. Appl 1o. 111388,270. dated Dec.
`14, 2007.
`USPTO . 'on-f inal Office Action, U.S.Appl. o. 11/388,270, mailed
`Mar. 25, 2008.
`USPTO Final Office Aclion, U .S. App!. No. 111388,270, mailed Oct.
`29.2008.
`TJSPTO Aovisory Action, l f.S. Appl.l\"o. II/3RR.270, moiled Jan. 23,
`2009.
`USPTO . ·on-Final Office Action, U.S.Appl. o. 11/388,270, mailed
`Jul. 9, 2009.
`USPTO lnlcrvicw Summary, U .S. Appl. No. I 1/388,270, dated Nov.
`12,2010.
`USPTO :--•oti<.:c of Allowanw and Fco:s Due, U.S. App!. No.
`111388,270, 1n..1iled Jan. 5, 2011.
`USPTO . ·on-Fi.na.l OtliceAction, U.S.Appl. o. 13/087,0 12, mailed
`M:u-. 12, 201 2.
`USPTO ·on-Final Office Action, U.S.Appl. o. 13/087,012, mailed
`Jul. 19, 2012.
`USPTO Interview SwlUnaory, U.S. Appl. No. I 31087,0 12, dated Feb.
`15, 2013.
`USPTO ~otice of Allowance and Fees Due, U.S. Appl. No.
`131087,012, mailed Feb. 27,2013.
`USPTO Response lo Amendment under Rule 3]2, U.S. Appl. No.
`131087,012, mailed Apr. 4, 2013.
`USPTO . "on-Final Office Action, U.S.Appl.. o. l l/129,839, mailed
`Jun. I 0, 2008.
`
`Eisenberg: e1 al. 2004, "Efficacy, safety and pharmacokinetics of
`palonosetron in patients receiving highly emetogenic cisplat:in-based
`chemotherapy: a dose-ranging c:tinical sn1dy." Annals of Oncology,
`vol. 15, pp. 330-337.
`i\>1ayron et al. 1996, "Stability and compatibility ofgranistron hydro-
`chloride in i.v. solutions and orall liquids and during simulated Y-site
`injection w ith selected dmgs." Am J Health-Sys Pharm, 53: 294-304.
`Trissel et al. 1997, "Compatibility of graoisetron hydrochloride w ith
`selected dmgs during simulaJedY -site admi nistration." Am J Health-
`Syst Pharm 54: 56-60.
`USPTO Final Office Action, U .S. Appl. >lo. I ll! 29,839. mailed Mar.
`I 7. 2009.
`USPTOAdvisory Action, U.S.App!. 1\o. I t/ 129,839, mailed Jul. 22,
`2009.
`liSPTO 1\"on-Final OfficeAction,lJ.S. Appl. No. I 1/ 129,839, mailed
`Jan. 15, 20 10.
`USPTO E.'<llminer Interview Summary, U.S. Appl. No. 11/ 129,839,
`moiled Nov. 9, 20 10.
`lfSPTO Nolice of Allowance and Fees Due, U.S. Appl. No.
`111129,839, mailed Jan. 3, 20 11.
`IJSPTOI\"'oticeof Abandonment, TI S Appl. No. 11/ 129,839, moiled
`Apr. 18, 20 I I.
`IJSPTOI\"'on-Finol Office Action, lf.S . Appl. No. 13/077,374, mailed
`Feb. 17,2012.
`Roila et al. 1998, "Prevention of chemotherapy- and radiotherapy-
`induced e mesis: Resulls of the Perugia consensus conference."
`Annals o f Oncology, vol. 9, pp. l!ll -1!19 .
`USPTO Final OfficeAclion, U.S. Appl. >lo. 13/077,374, mailed Nov.
`23, 201 2.
`Piraccini, Gaia et al.. A.mericru1 Society of Clinical Oncology May
`.12-1 5,200 1 San Francisco-USA (vol. 20, part I of 2, 2001) (Abstract
`No. 1595).
`USPTO !':on-Final Office Action, U.S.Appl. No . .l l /20.ll,035, mailed
`Moy 16, 200X.
`USPTO Final Office Action, U .S. Appl. l\"o. 11/201,035, mailed Feb
`4, 2009.
`USPTO Final Office Action, U.S. Appl. No. 11120.1,035, mailed Jun.
`8, 2010.
`FDA approvalletter of Aloxi (palonosetron hydrochloride injection),
`dated Jul. 25, 2003.
`Macciocchi A, Chernoff SB. Gallagher SC. A phase II dose-ranging
`study to assess intravenous doses of palonosetron for the prevention
`of highly emetogeo.ic cbemolherapy-induced nausea and vomiting.
`In: Program/Proceedings ofthe 38th Annual Meeting ofthe Am eri-
`can Society of Clinical Oncology; May 18-2 1, 2002; O rlando, Fla.
`Abstract 14MO.
`Gmnberg SM, Hajdenberg J, Cham V, et al. Palonosetron is aclive in
`preventing acute and delayed emesis
`following moderately
`emetogenic chemotherapy: results of a phase Ill !rial. Support Care
`Cancer 2002; IO:Abst:Jact P-113.
`Aapro MS, Selak E, Lichinitser M, el al. Palonosetron is more efl'ec-
`tive than ondansetron in preventing chemotherapy-induced nausea
`and vomiting in patients receiving moderately emetogenic chemo-
`therapy: results of a phase III trial. In: Progr.un/Proceedings of the
`39th Annual Meeting oftbe American Society of Clinical Oncology;
`May 3 1-Jun. 3, 2003; Chicago, III. Abstracl 2918.
`Aapro MS , Bertoli L, Lordick F, et al. Palonosetron is effective in
`preventing acute and delayed chemotherapy induced nausea and
`vom.iling in patients receiving highlyemetogenic chemotherapy. I S'h
`MASCC International Symposium, Berlin, Germany. S upport Care
`C mccr, vol. 11. No. 6, .Jun. 2003, A 17.
`Cat1Jnell AU, Ferguson S. Yanagibara R., et at. Proteo::tion against
`chemotherapy-induced nausea and vomiting is maintained over mul-
`tiple cycles of moderat.ely or highly emelogenic chemotherapy by
`palonosetron, a potent 5 HD rec:eptor antagonist. In: Program/Pro-
`ceedings of the 39th Annual Meeling of the American Sociely of
`Clinical Oncology; May 31-Jun. 3, 2003; Chicago, III. ~bst:Jact 3041.
`Sabra, Choice of a S-HT3 Receptor Antagonist for the Hospital
`Fonnulary, EHP, Oct. 1996, vol. 2, Supp I, S 19-S24.
`Gregory and Ettinger, SHTJ receptor antagonists for th e prevention
`of chemotherapy-induced nausea and vomili.ng. A comparison of
`their phannacology and clinical efficacy. Dn•gs, Feb. 1998; 55(2):
`173- 189.
`
`Exh. 1037
`
`
`
`US 9,066,980 B2
`Page 5
`
`(56)
`
`l~eferences Cited
`OTHER PUBLICATIONS
`
`Full Prescribing Information for Aloxi (palonosetron HCI) injection
`for Intravenous Use (2008) .
`Dnrg. Dose &Schedule Reconunendations for .t\ntiemet:ic Regimens
`(American Society for Clinical Oncology) (2006).
`Yamakuni, et t1l., The Journal of Phann:Lcology and F.xperimenta.l
`Therapeutics, Probable Involvement of the 5-Hydroxytryptamine4
`Rece ptor in Methotrexate-lnduced Delayed Emesis in Dogs, 2000,
`The American Society for Pharmacology and Experimental Thera-
`peutics, vol. 292, No ~. p. 1002- 1294.
`Geling, et al., Shnuld 5-1-lydroxyrrypt:unine-~ Receptor Antagonists
`Be Administered Beyond 24 Hours After Chemo-therapy to Prevent
`Delayed Emesis? Systematic Re-Evaluation of Clinical Evidence
`and Dnrg Cost Implications, Joumiil of Clinical Oncology, vol. 23,
`No. 6, Feb. 20, 2005 (American Society of Clinical Oncology), pp.
`12R9- 1294
`International Anesthesia Rese:trch Society,
`al.,
`Rojas, et
`Palonosetron Exhibits Unique Molecular Interactions with 5-HT3
`Rece pt'Or, vol. I 07, 1\o. 2, Aug. 2008, p. 469-478.
`Rojas, et at., Palonosetron triggers 5-HT3 receptor internalization
`and causes inhibition of receptor function, European Journal of Phar-
`macology 626 (201U), p. 193-199.
`Reg.,1.n-Shaw, e1 al., Dose translation from animal to human studies
`revisited, ·1be FASE13 Journal, Life Sciences fonun, p. 659-661.
`Saito. et