`
`1111111111111111111111111111111111111111111111111111111111111
`US009066980B2
`
`c12) United States Patent
`Calderari et al.
`
`(10) Patent No.:
`(45) Date of Patent:
`
`US 9,066,980 B2
`*Jun. 30, 2015
`
`(54) LIQUID PHARMACEUTICAL
`FORMULATIONS OF PALONOSETRON
`(71) Applicants:Helsinn Healthcare 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 (IT); 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: Helsinn Healthcare 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)
`
`(63)
`
`(60)
`
`(51)
`
`(52)
`
`(58)
`
`Appl. No.: 13/902,299
`Filed:
`May 24, 2013
`Prior Publication Data
`US 2013/0289065 Al
`Oct. 31, 2013
`
`Related U.S. Application Data
`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. 11/186,311, 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.
`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. Cl.
`A61K 31147
`A61K 47126
`A61K 311473
`A61K 47118
`A61K 47112
`A61K 47100
`A61K 47102
`A61K9/00
`U.S. Cl.
`CPC ............... A61K 47126 (2013.01); A61K 471183
`(2013.01); A61K 47112 (2013.01); A61K 47100
`(2013.01); A61K 311473 (2013.01); A61K
`47102 (2013.01); A61K 910019 (2013.01);
`A61K 910095 (2013.01)
`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
`5,922,749 A
`5,955,488 A
`6,063,802 A
`6,132,758 A
`6,284,749 B1
`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
`8,598,218 B2
`
`9/1987 Coates eta!.
`6/1988 Tyers et al.
`12/1989 King
`3/1990 Gittos
`5/1990 Tyers et al.
`6/1990 King
`4/1991 Gittos eta!.
`7/1991 King
`4/1993 Berger et al.
`8/1993 Tyers et al.
`12/1993 Blase eta!.
`9/1994 Collin
`1111996 Tyers et al.
`1111996 Tyers et al.
`4/1997 Collin
`12/1998 Gambhir
`7/1999 Tyers et al.
`9/1999 Winterborn
`5/2000 Winterborn
`10/2000 Munayyeretal.
`9/2001 Castillo et a!.
`9/2001 Dickinson
`9/2001 James
`3/2004 Robichaud
`9/2006 Lee eta!.
`5/2011 Calderari et a!.
`5/2011 Calderari et a!.
`6/2011 Calderari et a!.
`8/2013 Calderari et a!.
`12/2013 Calderari et a!.
`(Continued)
`
`FOREIGN PATENT DOCUMENTS
`
`EP
`wo
`
`4/1992
`0 512 400 A1
`12/2003
`W0-03100091
`(Continued)
`OTHER PUBLICATIONS
`
`Perez eta!. (cancer J. Sci Arn. (1998) 4_1):52.*
`R. M. Eglen eta!., "Pharmacological characterization ofRS 25259-
`197, a novel and selective 5-HT3 receptor antagonist, in vivo," Br. J
`Pharmacology 114:860-866 (1995).
`Chelly, Jacques eta!., 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 Expert Opinion on Investiga-
`tional Drugs, 1996, vol. 5 No.4, pp. 389-407.
`Gaster, Laramie M. and King, Frank D., Serotonin 5-HT3 and5-HT4
`Receptor Antagonists, extracted from Medicinal Research Reviews,
`1997 vol. 17, No.2, pp. 163-214.
`Tang, Jun eta!., "Efficacy ofRS-25259, a Novel 5-HT3 Antagonist,
`In the Prevention of Postoperative Nausea and Vomiting after Major
`Gynecologic Surgery," Anesthesiology, 1997, vol. 85, No.3 suppl. p.
`A329.
`
`(Continued)
`
`Primary Examiner- Shirley V Gembeh
`(74) Attorney, Agent, or Firm- Clark G. Sullivan;
`Troutman Sanders LLP
`(57)
`ABSTRACT
`The present invention relates to shelf-stable liquid formula-
`tions of palonosetron for reducing chemotherapy and radio-
`therapy induced emesis with palonosetron. The formulations
`Dr. Reddy’s Laboratories, Ltd., et al.
`are particularly useful in the preparation of intravenous and
`oral liquid medicaments.
`v.
`Helsinn Healthcare S.A., et al.
`16 Claims, No Drawings
`U.S. Patent No. 9,(cid:20)(cid:26)(cid:22),(cid:28)(cid:23)(cid:21)
`Reddy Exhibit 1027
`
`
`
`111111
`
`1111111111111111111111111111111111111111111111111111111111111
`US009066980B2
`
`c12) United States Patent
`Calderari et al.
`
`(10) Patent No.:
`(45) Date of Patent:
`
`US 9,066,980 B2
`*Jun. 30, 2015
`
`(54) LIQUID PHARMACEUTICAL
`FORMULATIONS OF PALONOSETRON
`(71) Applicants:Helsinn Healthcare 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 (IT); 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: Helsinn Healthcare 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)
`
`(63)
`
`(60)
`
`(51)
`
`(52)
`
`(58)
`
`Appl. No.: 13/902,299
`Filed:
`May 24, 2013
`Prior Publication Data
`US 2013/0289065 Al
`Oct. 31, 2013
`
`Related U.S. Application Data
`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. 11/186,311, 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.
`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. Cl.
`A61K 31147
`A61K 47126
`A61K 311473
`A61K 47118
`A61K 47112
`A61K 47100
`A61K 47102
`A61K9/00
`U.S. Cl.
`CPC ............... A61K 47126 (2013.01); A61K 471183
`(2013.01); A61K 47112 (2013.01); A61K 47100
`(2013.01); A61K 311473 (2013.01); A61K
`47102 (2013.01); A61K 910019 (2013.01);
`A61K 910095 (2013.01)
`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
`5,922,749 A
`5,955,488 A
`6,063,802 A
`6,132,758 A
`6,284,749 B1
`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
`8,598,218 B2
`
`9/1987 Coates eta!.
`6/1988 Tyers et al.
`12/1989 King
`3/1990 Gittos
`5/1990 Tyers et al.
`6/1990 King
`4/1991 Gittos eta!.
`7/1991 King
`4/1993 Berger et al.
`8/1993 Tyers et al.
`12/1993 Blase eta!.
`9/1994 Collin
`1111996 Tyers et al.
`1111996 Tyers et al.
`4/1997 Collin
`12/1998 Gambhir
`7/1999 Tyers et al.
`9/1999 Winterborn
`5/2000 Winterborn
`10/2000 Munayyeretal.
`9/2001 Castillo et a!.
`9/2001 Dickinson
`9/2001 James
`3/2004 Robichaud
`9/2006 Lee eta!.
`5/2011 Calderari et a!.
`5/2011 Calderari et a!.
`6/2011 Calderari et a!.
`8/2013 Calderari et a!.
`12/2013 Calderari et a!.
`(Continued)
`
`FOREIGN PATENT DOCUMENTS
`
`EP
`wo
`
`4/1992
`0 512 400 A1
`12/2003
`W0-03100091
`(Continued)
`OTHER PUBLICATIONS
`
`Perez eta!. (cancer J. Sci Arn. (1998) 4_1):52.*
`R. M. Eglen eta!., "Pharmacological characterization ofRS 25259-
`197, a novel and selective 5-HT3 receptor antagonist, in vivo," Br. J
`Pharmacology 114:860-866 (1995).
`Chelly, Jacques eta!., 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 Expert Opinion on Investiga-
`tional Drugs, 1996, vol. 5 No.4, pp. 389-407.
`Gaster, Laramie M. and King, Frank D., Serotonin 5-HT3 and5-HT4
`Receptor Antagonists, extracted from Medicinal Research Reviews,
`1997 vol. 17, No.2, pp. 163-214.
`Tang, Jun eta!., "Efficacy ofRS-25259, a Novel 5-HT3 Antagonist,
`In the Prevention of Postoperative Nausea and Vomiting after Major
`Gynecologic Surgery," Anesthesiology, 1997, vol. 85, No.3 suppl. p.
`A329.
`
`(Continued)
`
`Primary Examiner- Shirley V Gembeh
`(74) Attorney, Agent, or Firm- Clark G. Sullivan;
`Troutman Sanders LLP
`(57)
`ABSTRACT
`The present invention relates to shelf-stable liquid formula-
`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.
`16 Claims, No Drawings
`
`Exh. 1027
`
`
`
`US 9,066,980 B2
`Page 2
`
`(56)
`
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`U.S. PATENT DOCUMENTS
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`200110020029 AI
`2003/0095926 Al
`2004/0147510 Al *
`2013/0261149 Al
`2013/0261150 Al
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`2014/0039000 AI
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`12/2013 Calderari et al.
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`9/2004
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`Tang, Jun et al., The Efficacy ofRS-25259, a Long-Acting Selective
`5-HT3 Receptor Antagonist, for Preventing Postoperative Nausea
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`'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 from Dr. Reddy's re '424 patent.
`Aug. 19, 2011 Para. IV notice from Teva Pharmaceuticals re '424
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`Sep. 22, 2011 Para. IV notice from Sandoz re '724, '725 and '424
`patents.
`Jul. 8, 2011 Complaint for patent infringement (D. N.J. case No.
`11-03962).
`Sep. 23, 2011 Complaint for patent infringement (D. N.J. case No.
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`Aug. 31, 2011 Answer and counterclaim of Dr. Reddy's Laborato-
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`Sep. 13, 2011 Sandoz Inc.'s answer to complaint for patent infringe-
`ment and counterclaims (D. N.J. case No. 11-03962).
`Sep. 13, 2011 Teva Pharmaceuticals USA, Inc. and Teva Pharmaceu-
`tical Industries Ltd.'s answer (D. N.J. case No. 11-03962).
`Oct. 5, 2011 Plaintiffs reply to answer and counterclaim of Dr.
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`Oct. 21, 2011 Plaintiffs reply to Sandoz Inc.'s answer to complaint
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`11-03962).
`Oct. 24, 2011 Answer and counterclaim of Dr. Reddy's Laboratories,
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`
`Exh. 1027
`
`
`
`US 9,066,980 B2
`Page 3
`
`(56)
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`Nov. 17, 2011 Plaintiffs' reply to answer and counterclaim of Dr.
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`Nov. 17, 2011 Plaintiffs' reply to Sandoz Inc.'s answer to complaint
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`11-03962).
`Dec. 5, 2011 Teva Pharmaceuticals USA Inc. and Teva Pharmaceu-
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`May 21, 20 12 Plaintiffs' opening claim construction brief (including
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`Jul. 20, 2012 Defendants' responsive claim construction brief
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`Jul. 20, 2012 Plaintiffs' responsive claim construction brief (includ-
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