111111
`
`1111111111111111111111111111111111111111111111111111111111111
`US008598219B2
`
`c12) United States Patent
`Calderari et al.
`
`(JO) Patent No.:
`(45) Date of Patent:
`
`US 8,598,219 B2
`*Dec. 3, 2013
`
`(54) LIQUID PHARMACEUTICAL
`FORMULATIONS OF PALONOSETRON
`
`(7 1) Applicauts:Helsinn Healthcare S.A., Lugano (CH);
`Roche Palo Alto LLC, Palo Alto, CA
`(US); Simone Macciocch i, Mel ide (CH);
`G iulio M acciocchi, Breganzona (C H)
`
`(72)
`
`Jnventors: G iorgio C alde ra ri, Rancate (C H);
`Daniele Bonadeo, Casalzuigno (IT);
`R oberta Can neiJa, Varese (IT); Alberto
`Macciocchi, Melide (CH); Andrew
`Miksztal, Palo .t\lto, CA (US); Th omas
`Malefyt, Carmel VaJiey, C A (US);
`Kathleen M Lee, Palo Alto, CA (US);
`Carmine Panuccio, Casnate con Bernat
`(JT)
`
`(73) Assignees: Helsinn 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) Appl. No.: 13/901.437
`
`(22) Filed:
`
`May23, 2013
`
`(65)
`
`Prior P ublication Data
`US 2013/0261592 AI
`Oct. 3, 2013
`
`Related U.S. Application Dat:a
`(63) 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. 11/186,311, filed
`on Jul. 21 , 2005, now Pat. No. 7,947,724, which is a
`continuation of app Iicat:ion No. PCT/EP2004/000888,
`filed on Jan. 30, 2004.
`(60) Provisional application No. 60/444,351 , filed on Jan.
`30,2003.
`
`(51)
`
`(2006.01 )
`
`Int. C l.
`AOIN 43152
`(52) U.S. C l.
`USPC .......................................................... 514/397
`(58) F ield of C lassification Search
`USPC .......................................................... 514/397
`See application fi le for complete search history.
`
`(56)
`
`Referen ces 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
`
`911987 Coates et al.
`6/1988 Tyers et al.
`12/1989 King
`311990 Gittos
`511990 Tyers et aJ.
`6/1990 King
`
`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
`5,922,749 A
`5,955,488 A
`6,063,802 A
`6,132,758 A
`6,284,749 Bl
`6,287,592 B1
`6,294,548 B1
`6,699,852 B2
`7,109,339 B2
`7,947,724 B2
`7,947,725 B2
`7,960,424 B2
`8,518,981 B2
`200110020029 AI
`2003/0095926 A I
`
`4/1991 Gittos et al.
`7/1991 King
`411993 Berger et al.
`811993 Tyers et a!.
`12/1993 Blase et al.
`9/1994 Collin
`11/1996 Tyers eta!.
`11/1996 Tyers et a!.
`411 997 Collin
`12/1998 Gambhir
`7/1999 Tyers eta!.
`911 999 Winterborn
`5/2000 Winterborn
`10/2000 Munayyer eta!.
`9/200 I Castillo el: al.
`9/2001 Dickinson
`9/200 I James
`3/2004 Robichaud
`9/2006 Lee et al.
`5/20 I I Calderari el: al.
`5/2011 Calderari et al.
`6120 I I Calderari el: al.
`81201 3 Calderari el: al.
`9/200 I James
`5/2003 Dugger, III
`
`FORE IGN PATENT DOCUMENTS
`
`EP wo wo wo wo
`
`4/1992
`0 512 400 A1
`12/2003
`W0-03100091
`6/2004
`W0-2004045615
`8/2004
`W0-2004067005
`9/2004
`W0-2004703714
`OTHER PUBLICATIONS
`
`Center for Dmg Evaluation and Research (Sep. 2002).*
`R. M. Eglen et al., "Pharmacological characterization ofRS 25259-
`197, a novel and selective 5-HT3 receptor antagonist, in vivo," Br. 1
`Phannacology 114:860-866 (1995).
`Chelly, Jacques et al., Oral RS-25259 Prevents Postoperative Nausea
`and Vomiting Following Laparoscopic Surgery, Anesthesiology,
`1996, vol. 85, No. 3A, p. A21.
`Sorbe, Bengt, 5-HT-3 Receptor Antagonists as Antiemetic Agents in
`Cancer Chemotherapy, extracted from Expe1t Opinion on Investiga-
`tional Drugs, 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 Smgery," Anesthesiology, 1997, vol. 85, No.3 suppl. p.
`A329.
`Tang, Jun eta!., The Efficacy ofRS-25259, a Long-Acting Selective
`5-HT3 Receptor Antagonist, for Preventing Postoperative Nausea
`and Vomiting After Hysterectomy Procedures, Anesthesia and AmLI·
`gesia, 1998, vol. 87, pp. 462-467.
`Ad.is R&D Profile, Palonosetron RS 25259 197, Drugs in R&D, Oct.
`1999, vol. 2, No.4, pp. 251-252.
`
`(Continued)
`Primary Examiner - Sl1irley Gembeh
`(74) Attorney, Agent, or Finn - Clark G . Sullivan;
`Troutman Sanders LLP
`(57)
`ABSTRACT
`The present invention relates to shelf-stable liquid fonnula-
`tious of palonosetron for reducing chemotherapy and radio-
`therapy induced •mPOt O Ultth n~l
`T h P fnmmbttl'\110
`are particularly l
`Dr. Reddy's Laboratories, Ltd., et al.
`oral liquid medi<
`v.
`Helsinn Healthcare S.A., et al.
`U.S. Patent No. 8,729,094
`Reddy Exhibit 1005
`
`

`
`111111
`
`1111111111111111111111111111111111111111111111111111111111111
`US008598219B2
`
`(.12) United States Patent
`Calderari et al.
`
`(J O) Patent No.:
`(45) Date of Patent:
`
`US 8,598,219 B2
`*Dec. 3, 2013
`
`(54) LIQUID PIIARMACEUTICAL
`FORMULATIONS OF PALONOSF.TRON
`
`(71) Applicants:l:lclsinn l:lcalthcare S.A., Lugano (CH);
`Roche Palo Alto LLC, Palo Alto, CA
`(US); Simone Maccioccbi, Mel ide (CH);
`G iulio Macciocchi, Bregaozooa (CH)
`
`(72)
`
`Inventors: Giorgio Calderari, Rancate (CH);
`Daniele Bonadco, Casalzuigno (lT);
`Roberta Cannella, Yarese (JT); Alberto
`Macciocchi, Melide (CH); Andrew
`Miksztal, Palo Alto, CA (US); Thomas
`Malefyt, Canuel Valley, CA (US);
`Kathleen M Lee, Palo Alto, CA (US);
`Carmine Panuceio, Casnate con l:lemat
`
`on
`
`(73) Assigne~;:s: Bclsinn Bcaltlu:arc 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.
`
`(2 J) Appl. No.: 13/901,437
`
`(22) Filed:
`
`May 23, 2013
`
`(65)
`
`Prior Publication Data
`US 201 3/0261592 AI
`Oct. 3, 2013
`
`Related U.S. Application Data
`(63) Continuation-in-part of application No. 131087,012,
`filed on Apr. 14, 201 1, now Pat. No. &,518,981, which
`is a continuation of application No. 111186,311, ft.led
`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) Pmvisional applicarion No. 60/444,35 I, fi led on Jan.
`30, 2003.
`
`(51)
`
`(2006.01)
`
`Int. Cl.
`AOJN 43152
`(52) U.S. Cl.
`USPC ........................................................... 514/397
`(58) Field of Classification s~arch
`USPC .......................................................... 51 4/397
`See application file for complete search hjstory.
`
`(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
`
`911987 Coates et at.
`6/1988 T yers ct al.
`12/t989 King
`3/ 1990 G ittos
`5/ 1990 Tyers et at.
`6ft990 King
`
`5,0 1 1,846 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
`5,922,749 A
`5,955,488 A
`6,063,802 A
`6.132,758 A
`6,284,749 B l
`6,287,592 13 1
`6,294,548 B I
`6,699,852 62
`7,109,339 B2
`7,947, 724 l:l2
`7.947,725 B2
`7.960,424 B2
`8,518,981 62
`200 1100 20029 A 1
`2003/0095926 A I
`
`4/1991 Gittos ct at.
`7/1991 King
`4/1993 Berger et al.
`811993 Tyers et at.
`12/ I 993 Blase et a!.
`9/ 1994 Collin
`11/ 1996 Tyers et al.
`11/ 1996 Tyers et a!.
`4/ 1997 Collin
`12/1998 Grunbhir
`7/ 1999 Tyers et al.
`9/ 1999 Winterborn
`512000 Winterborn
`t 0/2000 M unayyer et at.
`91200 I Cal;tillo et at.
`91200 t Dickinson
`91200 t James
`3/2004 Robichaud
`912006 Lee et at.
`5/20 ll Calderari eta!.
`5120 t I Calderari et a I.
`6120 I I Calderari er at.
`8/20 t 3 Caldenui el at.
`91200 I James
`5/2003 Dugger, Ill
`
`FOREIGN PATENT DOCUMENTS
`
`EP wo wo
`wo
`WO
`
`411992
`0 512 400 AI
`1212003
`\V0-03100091
`612004
`W0 -2004045615
`8t2004
`W0-2004067005
`912004
`W0 -20047037 14
`OTHER PUBLICATIONS
`Center for Dntg Evaluation and Research (Sep. 2002).+
`R. M. Eglen et at., "Pharmacological characterization of RS 25259·
`197, a novel and selective 5-HT3 receptor antagonist, in vivo," Br. 1
`Phaimacology 114:860-866 (1995).
`Chclly, Ja.:qucs ct at., Oral RS-25259 Prevents Postoperative Nausea
`and Vomiting Following Laparoscopic Surgery, .'\ncst:hesiolo!,'Y,
`1996, vol. 85, l\o. 3A, p. A21.
`Sorbc, I3engt, 5-IIT-3 Receptor Antagonists as Antiemetic Agents in
`Cancer Cbemotherapy, extracted from Expe11 Opinion on Jnvestiga·
`tiona! Dmgs, 1996, vol. 5 No.4, pp. 389-407.
`Gaster, l :uamie M. <llld King, Frank D., Serotonin 5-HT3 and 5-HT4
`Receptor An tagonists, extracted from Medicinal Research Reviews,
`.1997 vol. t 7, No. 2, pp . .163-2 14.
`Tang. Jnn et at.. ''Efficacy ofRS-25259. a ·ovel 5·HT3 Antagonist,
`In the Prevention of Postoperative Nausea and Vomiting after Major
`Gynecologic Surgery," Anesthesiology, 1997, vol. 85, l'.' o.1 suppl. p.
`A329.
`Tang, Jun et at., The Efficacy of RS-25259, a Long-Acting Seleclive
`5-HT3 Receptor Antagonist, for Preventing Postoperative Nausea
`and Vomiting After Hysterectomy Procedures, Anesthesia and Anal·
`gesia, 19<J8, vol. 87. pp. 462-467.
`Adis R&D Profile, Patonoscrron RS 25259 197, Drugs in R&D, Oct.
`1999, vol. 2, No. 4, pp. 25 I -252.
`(Continued)
`Primary Examiner - Shirley Gembeh
`(74) Attorney, Af{ent, or Firm - Clark G. Sullivan;
`Troutman Samlcrs LLP
`(57)
`ABSTRACT
`Tht: preseul iuvt:Jlliuu rt:latcs tu sht:lf-stablc lil.juid furmulc•-
`tions of palonosetron for reducing chemotherapy and radio-
`therapy induced emesis with palonosetron. The formulations
`are particularly useful in the preparation of intravenous and
`oral liquid medicaments.
`8 Claims, No Drawings
`
`Exh. 1005
`
`

`
`US 8,598,219 B2
`Page2
`
`(56)
`
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`Serial No. 04 706 657.6 dated Feb. 11, 2010.
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`May 24, 20 I I Para. rv notice from Teva Pb.'lrmaceuticals re '724 and
`'725 patents.
`May 24, 20 II Para. rv notice from Sandoz re '724 and '725 patenls.
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`Aug. 9, 201 I Pam. IV nolicc froJn Dr. Reddy's rc '424 patent.
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`Scp. 22, 2011 Para. IV notice from Sandoz re '724, '725 and '424
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`Jul. 8, 20 II Complaint for patent infringement (D. N.J. case No.
`11-03962).
`Sep. 23, 2011 Complaint for patent infring.emenl (D. N.J. case . o.
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`Aug. 3 1, 20 II Answer and counterclaim of Dr. Reddy's Laborato-
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`N.J. case N o. l J -03962).
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`the '424 parent (D. N.J. case No. 11-03962).
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`ing exhibits 1-3 1 ).
`May2 1, 20 12 Plaintiffs' opening claim constn1ction brief(includi ng
`e.'<hibits I -15).
`Jul. 20, 2012 J)efendants' responsive claim construction brief
`(including exhibits 1-3).
`
`Exh. 1005
`
`

`
`US 8,598,219 B2
`Page3
`
`(56)
`
`l~eferences Cited
`
`OTHER PUBLICATIONS
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`3.6(cXD. "<.J. case :-.•o. 11-03%2).
`Dec. I, 2011 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.
`. .J. case No. 11-03962).
`Jan. 31,2012 Plaintiff's responses to defendants· invalidity conten-
`tions (D. • . .1. case No. 11-()3962).
`Sep. 25, 20 t2 Santloz Inc.'s first amentletl invalitlity contentions
`pu.rsua.nt to L . Pat. R. 3.6(c) (D. ' .J. case No. t l-03962).
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`invalidity contentions (D.
`.J. case No. 11-03\162).
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