111111
`
`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
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`6,294,548 Bl
`6,699,852 B2
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`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!.
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`3/2004 Robichaud
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`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
`
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`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
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`6,294,548 Bl
`6,699,852 B2
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`811993 T ycrs ct al.
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`1111\J96 'fyers el al.
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`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
`
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`
`Exh. 1037
`
`

`
`US 9,066,980 B2
`Page 3
`
`(56)
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