111111
`
`1111111111111111111111111111111111111111111111111111111111111
`US009173942B2
`
`c12) United States Patent
`Calderari et al.
`
`(10) Patent No.:
`(45) Date of Patent:
`
`US 9,173,942 B2
`*Nov. 3, 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,
`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.: 13/901,830
`
`(22) Filed:
`
`May24, 2013
`
`(65)
`
`Prior Publication Data
`US 2013/0261149 Al
`Oct. 3, 2013
`
`(63)
`
`(60)
`
`(51)
`
`(52)
`
`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)
`(2006.01)
`(2006.01)
`
`Int. Cl.
`A01N 43152
`A61K 47126
`A61K 47118
`A61K 47112
`A61K 47100
`A61K 311473
`A61K 47102
`A61K9/00
`B65B 7116
`B65B 55102
`U.S. Cl.
`CPC ............... A61K 47126 (2013.01); A61K 910019
`(2013.01); A61K 910095 (2013.01); A61K
`311473 (2013.01); A61K 47100 (2013.01);
`
`A61K 47102 (2013.01); A61K 47112 (2013.01);
`A61K 471183 (2013.01); B65B 7116 (2013.01);
`B65B 55102 (2013.01)
`Field of Classification Search
`USPC .......................................................... 514/397
`See application file for complete search history.
`References Cited
`
`(58)
`
`(56)
`
`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
`
`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!.
`(Continued)
`
`FOREIGN PATENT DOCUMENTS
`
`EP
`wo
`
`4/1992
`0 512 400 A1
`12/2003
`W0-031 00091
`(Continued)
`OTHER PUBLICATIONS
`Tang eta!., (Anesth Analg 1998; 87 462-467; Ref. 105. *
`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.
`(Continued)
`
`Primary Examiner- Shirley V Gembeh
`(74) Attorney, Agent, or Firm- Troutman Sanders LLP
`ABSTRACT
`(57)
`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
`v.
`oral liquid medicaments.
`Helsinn Healthcare S.A., et al.
`19 Claims, No Drawings
`U.S. Patent No. 9,(cid:20)(cid:26)(cid:22),(cid:28)(cid:23)(cid:21)
`Reddy Exhibit 1001
`
`

`
`111111
`
`1111111111111111111111111111111111111111111111111111111111111
`US009173942B2
`
`c12) United States Patent
`Calderari et al.
`
`(10) Patent No.:
`(45) Date of Patent:
`
`US 9,173,942 B2
`*Nov. 3, 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,
`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.: 13/901,830
`
`(22) Filed:
`
`May24, 2013
`
`(65)
`
`Prior Publication Data
`US 2013/0261149 Al
`Oct. 3, 2013
`
`(63)
`
`(60)
`
`(51)
`
`(52)
`
`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)
`(2006.01)
`(2006.01)
`
`Int. Cl.
`A01N 43152
`A61K 47126
`A61K 47118
`A61K 47112
`A61K 47100
`A61K 311473
`A61K 47102
`A61K9/00
`B65B 7116
`B65B 55102
`U.S. Cl.
`CPC ............... A61K 47126 (2013.01); A61K 910019
`(2013.01); A61K 910095 (2013.01); A61K
`311473 (2013.01); A61K 47100 (2013.01);
`
`A61K 47102 (2013.01); A61K 47112 (2013.01);
`A61K 471183 (2013.01); B65B 7116 (2013.01);
`B65B 55102 (2013.01)
`Field of Classification Search
`USPC .......................................................... 514/397
`See application file for complete search history.
`References Cited
`
`(58)
`
`(56)
`
`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
`
`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!.
`(Continued)
`
`FOREIGN PATENT DOCUMENTS
`
`EP
`wo
`
`4/1992
`0 512 400 A1
`12/2003
`W0-031 00091
`(Continued)
`OTHER PUBLICATIONS
`Tang eta!., (Anesth Analg 1998; 87 462-467; Ref. 105. *
`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.
`(Continued)
`
`Primary Examiner- Shirley V Gembeh
`(74) Attorney, Agent, or Firm- Troutman Sanders LLP
`ABSTRACT
`(57)
`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.
`19 Claims, No Drawings
`
`Exh. 1001
`
`

`
`US 9,173,942 B2
`Page 2
`
`(56)
`
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`Sep. 23, 2011 Complaint for patent infringement (D. N.J. case No.
`11-5579).
`
`Exh. 1001
`
`

`
`US 9,173,942 B2
`Page 3
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`(56)
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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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