111111
`
`1111111111111111111111111111111111111111111111111111111111111
`US008729094B2
`
`c12) United States Patent
`Calderari et al.
`
`(JO) Patent No.:
`(45) Date of Patent:
`
`US 8,729,094 B2
`*May 20, 2014
`
`(54) LIQUID PHARMACEUTICAL
`FORMULATIONS O F PALONOSETRON
`
`(71) Applicauts:Helsinn Healthcare SA, Lugano (CH);
`Roche Palo Alto LLC, Palo Alto, CA
`(US); Simone Macciocchi, Mel ide (CH);
`G iulio M acciocchi, Breganzona (CH)
`
`(72) Jnventors: G iorgio Calderari, Rancate (CH);
`Daniele Bonadeo, Casalzuigno (IT);
`Roberta CanneiJa, Varese (IT); Alberto
`Macciocchi, Melide (CH); Andrew
`Miksztal, Palo .t\lto, CA (US); Thomas
`Malefyt, Carmel VaJiey, CA (US);
`Kathleen M Lee, Palo Alto, CA (US)
`
`(73) Assignees: Elelsinn Bealthcare SA,
`Pambio-Noranco (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.: 13/902,132
`
`(22) Filed:
`
`May24, 2013
`
`(65)
`
`Prior Publication Data
`Oct. 3, 2013
`US 2013/0261 150AJ
`
`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, 201 1, 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 Iication 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. CI.
`A61K 47100
`(52) U.S. CI.
`USPC .......................................................... 514/296
`(58) F ield of Classification Search
`USPC .......................................................... 514/296
`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
`
`91.1987 Coates et al.
`6/1988 Tyers et al.
`12/1989 King
`31.1990 Gittos
`51.1990 Tyers et al.
`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
`2004/0147510 AI ..
`
`4/1991 Gittos et a!.
`7/1991 King
`411993 Berger el al.
`811993 Tyers et a!.
`12/1993 Blase el al.
`9/1994 Collin
`11/1996 Tyers eta!.
`11/1996 Tyers et a!.
`411997 Collin
`12/1998 Gambhir
`7/1999 Tyers eta!.
`911999 Winterborn
`5/2000 Winterbom
`10/2000 Munayyer eta!.
`9/200 I Castillo el: al.
`9/2001 Dickinson
`9/200 I James
`3/2004 Robichaud
`9/2006 Lee el al.
`5/20 I I Calderari el: al.
`5/2011 Calderari et a!.
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`9/200 I James
`5/2003 Dugger, III
`7/2004 LancL1u etal. ........... .... 514/218
`
`FOREJGN PATENT DOCUMENTS
`
`EP wo
`wo
`wo
`wo
`
`0 512 400 A1
`W0-03!00091
`W0-2004045615
`W0-2004067005
`W0-2004703714
`
`4/1992
`12/2003
`6/2004
`8/2004
`9/2004
`
`OTHER PUBLICATIONS
`
`CDER (Clinical Pharmacology and Biopharmaceutics Review (Sep.
`2002).•
`Perez et al. (cancer J. Sci Am. (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
`Phannacoloh'Y 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, extract.ed from Expert Opinion on Investiga-
`tional Dmgs, !996, vol. 5 No. 4, pp. 389-407.
`Gaster, Laramie M. and King, Frank D., Serotonin 5-HD and 5-HT4
`Receptor Antagonists, extracted from Medicinal Research Reviews,
`!997 vol. 17, No.2, pp. !63-214.
`(Continued)
`
`Primary Examiner - Shirley V Gembeh
`(74) Attorney, Agent, or Finn - Clark G. Sullivan;
`Troutman Sanders LLP
`
`(57)
`
`AUSTRACT
`
`The present invention relates to shelf-stable liquid fommla-
`tions of palonosetron for reducing chemotherapy and radio-
`therapy indu
`·
`·
`·
`are particula
`oral liquid m
`
`v.
`Helsinn Healthcare S.A., et al.
`U.S. Patent No. 8,729,094
`Reddy Exhibit 1001
`
`

`
`111111
`
`1111111111111111111111111111111111111111111111111111111111111
`US008729094B2
`
`(.12) United States Patent
`Calderari et al.
`
`(JO) Patent No.:
`(45) Date of Patent:
`
`US 8,729,094 B2
`*May 20, 2014
`
`(54) LIQUID PIIARMACEUTICAL
`FORMULATIONS OF PALONOSF.TRON
`
`(71) Applicants: l:lclsinn l:lcalthcare SA, Lugano (CH);
`Roche Palo Alto LLC, Palo Alto, CA
`(US); S imone Maccioccbi, Mel ide (CH);
`Giulio Macciocchi, Bregaozooa (CH)
`
`(72)
`
`Inventors: G iorgio Calderari, Rancate (CI·I);
`Daniele Bonadco, Casalzuigno (IT);
`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)
`
`(73) Assignees: Helsinn Healthcarc SA,
`Pambio-Noraoco (CH); R oche Palo Alto
`LLC, Palo Alto, CA (US)
`
`( "') Notice:
`
`Subject to any disclaimer, the term oftl:tis
`patent is extended o r adjusted under 35
`U .S.C. 154(b) by 0 days.
`This patent is subject to a terminal dis-
`claimer.
`
`(21) Appl. No.: 13/902,132
`
`(22) Filed:
`
`May 24, 2013
`
`(65)
`
`Prior Publication Data
`
`US 2013/0261 150 AJ
`
`Oct. 3, 2013
`
`Related U.S. Application Da ta
`(63) Continuation of application No. 13/901 ,437, filed oo
`May 23, 2013, now Pat. No. 8,598, 219, wl:tich is a
`continuation-in-part of applicatio n No. 131087,012,
`filed on Apr. 14, 2011, now Pat. No. &,518,981, which
`is a continuation of application No. 111186,311, ft.led
`o n 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.
`(60) Pmvisional applicarion No. 60/444,351, filed on Jan.
`30, 2003.
`
`(51)
`
`(2006.01)
`
`Int. Ct.
`A6JK 47100
`(52) U.S. CI.
`USPC ........................................................... 514/296
`(58) Field of Classification s~arch
`.......................................................... 514/296
`VSPC
`See applicatio n 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 el at.
`6/1988 T yers cl al.
`12/1989 King
`3/ 1990 Gittos
`511990 Tyers et at.
`6/ t990 King
`
`5,01 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 Bl
`6,287,592 131
`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
`2004/01475 10 AI •
`
`4/199t Gittos ct at.
`7/t99t King
`4/t993 Berger et al.
`81l993 Tyers et al.
`12/ I 993 Blase et a!.
`9/ 1994 Collin
`11/ 1996 Tyers el al.
`11/ 1996 Tyers eta!.
`4/ 1997 Collin
`12/1998 Grunbhir
`7/ 1999 Tyers et al.
`9/ 1999 Winterborn
`512000 Winterborn
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`91200 I Cal;lillo et at.
`91200 t Dickinson
`91200 t James
`312004 Robichaud
`912006 Lee et al.
`5120 I l Calderari et al.
`5120 II Calderari et a 1.
`6120 t t Calderari er al.
`8120 13 Caldenui el al.
`91200 I James
`512003 Dugger, III
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`
`POREJGN PATENT DOCUMENTS
`
`EP
`wo
`wo
`WO
`wo
`
`0 512 400 AI
`W0-03100091
`W0.2004045615
`W0-2004067005
`W0-20047037 14
`
`4!1992
`1212003
`6t2004
`8t2004
`9/2004
`
`.... 514/218
`
`OrHER PUBLICATIONS
`
`COER (Clinical Phamlil,ology and Biopbanna~eutics Review (Sep.
`2002).•
`Pef'C'l et at. (cancer J. Sci Am (I 998) 4(1):52•
`R. M. Eglcn cl at., "Pharmacological characterization of RS 25259·
`197, a novel and selective 5-IIT3 receptor antagonist, in vivo," Or. J
`Pharmacology I 14:860-866 (1995).
`Chelly, Ja<:ques et al., Oral RS-25259 J>revents Postopend:ive Nausea
`and Vomiting Following Laparoscopic Surgery, Anesthesiology,
`t996, vot. 85, l\o. 3A, p. A2 1.
`Sorbe, !3engt, 5-HT-3 Receptor Antagonists as Antiemetic Agents in
`Cancer Chemotherapy, extracted from Expert Opinion on lnvestiga·
`tiona! Dmgs, 1996, vol. 5 No. 4, pp. 389-407.
`Gaster, Larrunie M. and King, Frank D., Serotonin 5-HTI and 5 -I IT 4
`Receptor Antagonists, extracted from Medicinal Research Reviews,
`1997 vol. 17, No. 2, pp. 163·214.
`
`(Continued)
`
`Primary Examiner - Shirley V Gcmbeb
`(74) Attorney, Agent, or Firm - Clark G. Sullivan;
`Troutman Sanders LLP
`
`(57)
`
`ABSTRAC T
`
`The present invention rela tes to shelf-stable liquid fonnula-
`tion~ ofp::~lono~elmn for rerlncing chemother!lpy ::~nrl rnrlio-
`therapy induced emesis with palonosetron . The formulations
`arc particularly useful in the preparation of intravenous and
`oral liquid medicaments.
`
`30 C laims, No Drawings
`
`Exh. 1001
`
`

`
`US 8,729,094 B2
`Page2
`
`(56)
`
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`ment and cotmterclaims (D. N .J. case 1\o. 11-03962).
`Sep. 13, 20 I I Teva Pharmaceuticals USA, Inc. and Teva Pharmaceu-
`ticall.ndustries Ltd.'s answer (D. \I.J. case "io . .11 -03962).
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`Reddy's L~boratorics, Ltd. and Dr. Reddy Laboratories, Inc. (D. N.J.
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`Oct. 21, 20 II Plai.ntilfs reply to Sandoz Inc.'s answer to complaint
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`Oct. 27, 20 II O rder consolidaJing the two cases (D. N.J. case No.
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`N.J. case No. 11-03962).
`Nov. 17, 201 1 Plaintiffs' reply to Sandoz Inc.'s answer to complaint
`for patent infringement and counterclaims (D. N.J . case No.
`11-03962).
`
`Exh. 1001
`
`

`
`US 8,729,094 B2
`Page3
`
`(56)
`
`l~eferences Cited
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`OTHER PUBLICATIONS
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`. .J. case No. 11-03962).
`Jan. 31,2012 Plaintiff's responses to defendants' invalidity conten-
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