`Calderari et a].
`
`(10) Patent N0.:
`(45) Date of Patent:
`
`US 8,598,219 B2
`*Dec. 3, 2013
`
`US008598219B2
`
`(54) LIQUID PHARMACEUTICAL
`FORMULATIONS OF PALONOSETRON
`
`.
`.
`(71) Appl1cants:Helsmn Healthcare S.A., Lugano (CH);
`Roche Palo Alto LLC, Palo Alto, CA
`(US); Simone Macciocchi, Melide (CH);
`Giulio Macciocchi, BreganZona (CH)
`
`.
`
`.
`
`.
`
`(72) Inventors: Giorgio Calderarl, Rancate (CH);
`Dalllele 13011211160, casallulgno (1T);
`Roberta Cannella, Varese (IT); Alberto
`Macciocchi, Melide (CH); Andrew
`?llisital’cpalo ‘Al‘lglo’ncAgiskgllomas
`“6 YL anne a 6%
`(
`)’
`Kathleen M Lee, P2110 Alto, CA (Us);
`Carmine Panuccio, Casnate con Bernat
`(IT)
`
`-
`
`.
`
`-
`_
`.
`(73) Asslgnees. Helsmn Healthcare SA,
`LuganO/PaZZaHO (CH); Roche P910 Alto
`LLC, P2110 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)
`
`(56)
`
`Appl. No.2 13/901,437
`
`Filed:
`
`May 23, 2013
`
`Prior Publication Data
`
`US 2013/0261592 A1
`
`Oct. 3, 2013
`
`Related US. Application Data
`Continuation-in-part of application No. 13/087,012,
`?led onApr. 14, 2011, noW Pat. No. 8,518,981, Which
`is a continuation of application No. 11/186,311, ?led
`on Jul. 21, 2005, noW Pat. No. 7,947,724, Which is a
`continuation of application No. PCT/ EP2004/ 000888,
`?led on Jan. 30, 2004.
`
`Provisional application No. 60/444,351, ?led on Jan.
`30, 2003.
`
`(2006.01)
`
`Int. Cl.
`A01N 43/52
`US. Cl.
`USPC ........................................................ .. 514/397
`Field of Classi?cation Search
`USPC ........................................................ .. 514/397
`See application ?le for complete search history.
`
`References Cited
`
`U.S. PATENT DOCUMENTS
`
`9/1987 Coates et al.
`4,695,578 A
`6/1988 Tyers et al.
`4,753,789 A
`4,886,808 A 12/1989 King
`4,906,755 A
`3/1990 Gittos
`4,929,632 A
`5/1990 Tyers et al.
`4,937,247 A
`6/1990 King
`
`4/1991 Gittos et a1.
`5,011,846 A
`7/ 1991 K1118
`5,034,398 A
`4/1993 Berger et a1.
`5,202,333 A
`8/1993 T ers et a1.
`5,240,954 A
`5,272,137 A 12/1993 Bilge et a1‘
`5,344,653 A
`9/1994 Collin
`5,578,628 A 11/1996 Tyers et a1.
`5,578,632 A 11/1996 TyerF et a1~
`5,622,720 A
`4/1997 Collln
`5,854,270 A 12/1998 G bh'
`5,922,749 A
`7/l999 T3318 eéral‘
`5,955,488 A
`9/1999 Winterborn
`6,063,802 A
`5/2000 Winterborn
`2,
`Q1
`gunfiyyer 9; a1~
`6,287,592 B1
`9/2001 Dickinson
`6294548 B1
`90001 Jmn?
`6,699,852 B2
`3/2004 Robichaud
`7,109,339 B2
`9/2006 Lee et al.
`7,947,724 B2
`5/2011 Calderari et al.
`7,947,725 B2
`5/2011 Calderari et al.
`7,960,424 B2
`6/2011 Calderari et al.
`8,518,981 B2
`8/2013 Caldemriet a1‘
`2001/0020029 A1
`9/2001 James
`2003/0095926 A1
`5/2003 Dugger, III
`
`,
`
`,
`
`ast1 0 eta .
`
`FOREIGN PATENT DOCUMENTS
`
`4/1992
`0 512 400 A1
`EP
`12/2003
`WO-03100091
`WO
`6/2004
`WO WO-2004045615
`8/2004
`WO WO-2004067005
`9/2004
`WO WO-2004703714
`OTHER PUBLICATIONS
`
`Center for Drug Evaluation and Research (Sep. 2002).*
`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).
`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 Expert 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. 163-214.
`Tang, Jun et al., “Ef?cacy of RS-25259, a Novel 5-HT3 Antagonist,
`In the Prevention of Postoperative Nausea and Vomiting after Maj or
`Gynecologic Surgery,”Anesthesiology, 1997, vol. 85, No. 3 suppl. p.
`A329.
`Tang, Jun et al., The Ef?cacy ofRS-25259, a Long-Acting Selective
`5-HT3 Receptor Antagonist, for Preventing Postoperative Nausea
`and Vomiting After Hysterectomy Procedures, Anesthesia and Anal
`gesia, 1998, vol. 87, pp. 462-467.
`Adis R&D Pro?le, Palonosetron RS 25259 197, Drugs in R&D, Oct.
`1999, vol. 2, No. 4, pp. 251-252.
`(Continued)
`Primary Examiner * Shirley 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.
`8 Claims, No Drawings
`U.S. Patent No. 9,(cid:20)(cid:26)(cid:22),(cid:28)(cid:23)(cid:21)
`Reddy Exhibit 1014
`
`
`
`(12) Ulllted States Patent
`Calderari et a].
`
`(10) Patent N0.:
`(45) Date of Patent:
`
`US 8,598,219 B2
`*Dec. 3, 2013
`
`US008598219B2
`
`(54) LIQUID PHARMACEUTICAL
`FORMULATIONS OF PALONOSETRON
`
`.
`.
`(71) Appl1cants:Helsmn Healthcare S.A., Lugano (CH);
`Roche Palo Alto LLC, Palo Alto, CA
`(US); Simone Macciocchi, Melide (CH);
`Giulio Macciocchi, BreganZona (CH)
`
`.
`
`.
`
`.
`
`(72) Inventors: Giorgio Calderarl, Rancate (CH);
`Dalllele 13011211160, casallulgno (1T);
`Roberta Cannella, Varese (IT); Alberto
`Macciocchi, Melide (CH); Andrew
`?llisital’cpalo ‘Al‘lglo’ncAgiskgllomas
`“6 YL anne a 6%
`(
`)’
`Kathleen M Lee, P2110 Alto, CA (Us);
`Carmine Panuccio, Casnate con Bernat
`(IT)
`
`-
`
`.
`
`-
`_
`.
`(73) Asslgnees. Helsmn Healthcare SA,
`LuganO/PaZZaHO (CH); Roche P910 Alto
`LLC, P2110 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)
`
`(56)
`
`Appl. No.2 13/901,437
`
`Filed:
`
`May 23, 2013
`
`Prior Publication Data
`
`US 2013/0261592 A1
`
`Oct. 3, 2013
`
`Related US. Application Data
`Continuation-in-part of application No. 13/087,012,
`?led onApr. 14, 2011, noW Pat. No. 8,518,981, Which
`is a continuation of application No. 11/186,311, ?led
`on Jul. 21, 2005, noW Pat. No. 7,947,724, Which is a
`continuation of application No. PCT/ EP2004/ 000888,
`?led on Jan. 30, 2004.
`
`Provisional application No. 60/444,351, ?led on Jan.
`30, 2003.
`
`(2006.01)
`
`Int. Cl.
`A01N 43/52
`US. Cl.
`USPC ........................................................ .. 514/397
`Field of Classi?cation Search
`USPC ........................................................ .. 514/397
`See application ?le for complete search history.
`
`References Cited
`
`U.S. PATENT DOCUMENTS
`
`9/1987 Coates et al.
`4,695,578 A
`6/1988 Tyers et al.
`4,753,789 A
`4,886,808 A 12/1989 King
`4,906,755 A
`3/1990 Gittos
`4,929,632 A
`5/1990 Tyers et al.
`4,937,247 A
`6/1990 King
`
`4/1991 Gittos et a1.
`5,011,846 A
`7/ 1991 K1118
`5,034,398 A
`4/1993 Berger et a1.
`5,202,333 A
`8/1993 T ers et a1.
`5,240,954 A
`5,272,137 A 12/1993 Bilge et a1‘
`5,344,653 A
`9/1994 Collin
`5,578,628 A 11/1996 Tyers et a1.
`5,578,632 A 11/1996 TyerF et a1~
`5,622,720 A
`4/1997 Collln
`5,854,270 A 12/1998 G bh'
`5,922,749 A
`7/l999 T3318 eéral‘
`5,955,488 A
`9/1999 Winterborn
`6,063,802 A
`5/2000 Winterborn
`2,
`Q1
`gunfiyyer 9; a1~
`6,287,592 B1
`9/2001 Dickinson
`6294548 B1
`90001 Jmn?
`6,699,852 B2
`3/2004 Robichaud
`7,109,339 B2
`9/2006 Lee et al.
`7,947,724 B2
`5/2011 Calderari et al.
`7,947,725 B2
`5/2011 Calderari et al.
`7,960,424 B2
`6/2011 Calderari et al.
`8,518,981 B2
`8/2013 Caldemriet a1‘
`2001/0020029 A1
`9/2001 James
`2003/0095926 A1
`5/2003 Dugger, III
`
`,
`
`,
`
`ast1 0 eta .
`
`FOREIGN PATENT DOCUMENTS
`
`4/1992
`0 512 400 A1
`EP
`12/2003
`WO-03100091
`WO
`6/2004
`WO WO-2004045615
`8/2004
`WO WO-2004067005
`9/2004
`WO WO-2004703714
`OTHER PUBLICATIONS
`
`Center for Drug Evaluation and Research (Sep. 2002).*
`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).
`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 Expert 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. 163-214.
`Tang, Jun et al., “Ef?cacy of RS-25259, a Novel 5-HT3 Antagonist,
`In the Prevention of Postoperative Nausea and Vomiting after Maj or
`Gynecologic Surgery,”Anesthesiology, 1997, vol. 85, No. 3 suppl. p.
`A329.
`Tang, Jun et al., The Ef?cacy ofRS-25259, a Long-Acting Selective
`5-HT3 Receptor Antagonist, for Preventing Postoperative Nausea
`and Vomiting After Hysterectomy Procedures, Anesthesia and Anal
`gesia, 1998, vol. 87, pp. 462-467.
`Adis R&D Pro?le, Palonosetron RS 25259 197, Drugs in R&D, Oct.
`1999, vol. 2, No. 4, pp. 251-252.
`(Continued)
`Primary Examiner * Shirley 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.
`8 Claims, No Drawings
`
`Exh. 1014
`
`
`
`US 8,598,219 B2
`Page 2
`
`(56)
`
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`Aug. 9, 2011 Para. IV notice from Dr. Reddy’s re ’424 patent.
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`Jul. 8, 2011 Complaint for patent infringement (D. N.J. case No.
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`
`Exh. 1014
`
`
`
`US 8,598,219 B2
`Page 3
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`(56)
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