United States Patent
`(12)
`(10) Patent No.:
`US 8,835,382 B2
`O’Connor et al.
`(45) Date of Patent:
`Sep. 16, 2014
`
`
`US008835382B2
`
`(54) LIPOPEPTIDE COMPOSITIONS AND
`RELATED METHODS
`
`(75)
`
`Inventors: Sandra O’Comnor, Hudson, NH (US),
`Sophie Sun, Lexington, MA (US);
`Gaauri Naik, Cambridge, MA (US)
`
`(73) Assignee: Cubist Pharmaceuticals, Inc.,
`Loxinet MA (US
`cxington,
`MA
`(US)
`,
`,
`ee
`Subject to any disclaimer, the term of this
`patent is extended or adjusted under 35
`U.S.C. 154(b) by 0 days.
`
`,
`(*) Notice:
`
`(21) Appl. No.:
`.
`(22) PCT Filed:
`
`13/511,246
`
`Nov. 23, 2010
`
`PCT/US2010/057910
`
`Jul. 10, 2012
`
`(86) PCI No.:
`§ 371 (c)(),
`(2), (4) Date:
`.
`.
`(87) PCT Pub. No.:, WO2011/063419
`PCTPub. Date: May 26, 2011
`.
`,
`Prior Publication Data
`
`(65)
`
`5,955,509 A
`6,194,383 B
`6,468,967 B
`6,696,412 B
`6716-962 B2
`6,852,689 B2
`RE39,071 E
`7,138,487 B2
`7,279,597 B
`8,058,238 B2
`8,129,342 B2
`8,309,061 B2
`8,431,539 B2
`2002/OL11311 A
`2002/0132762 Al
`2003/0045484 A
`2003/0045678 A
`2004/0067878 Al
`2004/0077601 A
`2004/0242467 A
`2005/0009747 A
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`2005/0196418 A
`2006/0014674 Al
`2006/0018933 A
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`
`
`
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`(Continued)
`
`
`
`FOREIGN PATENT DOCUMENTS
`1592753 A
`3/2005
`1616083 A *
`5/2008
`(Continued)
`OTHER PUBLICATIONS
`
`US 2012/0270772 Al
`
`Oct. 25, 2012
`se
`Related U.S. Application Data
`(60) Provisional application No. 61/263,784, filed on Nov.
`23, 2009.
`
`CN
`CN
`
`......... AOLK 38/12
`
`a
`.
`.
`pH-water quality, from http://extension.usu.edu/waterquality/htm/
`whats-in-your-water/ph, pp. 1-2, accessed Jul. 23, 2013.*
`Smaleset al, Therapeutic proteins, methods and protocols, Humana
`press, 2005, pp. 287-292.*
`Wang, Lyophilization anddevelopmentofsolidprotein pharmaceu-
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`Machien translation ofCN 1616083 A,pp. 1-9, publication date May
`18. 2005.*
`Miaoetal., “Daptomycin biosynthesis in Streptomyces roseosporus:
`cloning and analysis of the gene cluster and revision of peptide
`stereochemistry,’ Microbiology 2005, vol. 151 (5), 1507-23.
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`iotics: Isolation, Chemistry, and Mass Spectral Structure Elucida-
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`ion,” The Journal of Antibiolics 1987, vol. XL (6), p. 761-77.
`(Continued)
`
`Primary Examiner — Julie Ha
`Assisiant Examiner — Li Ni Komatsu
`(74) Attorney, Agent, or Firm Lathrop & Gage LLP; Brian
`C. Trinque; Gang Wang,
`
`ABSTRACT
`(57)
`;
`;
`;
`The present disclosure provides novel powder daptomycin
`formulations which have improved chemical stability and
`faster reconstitution times when in the solid state. Some
`examples of the compositions comprise daptomycin and
`sucrose.
`
`18 Claims, 22 Drawing Sheets
`
`AMNEALEX. 1009
`
`(51)
`
`(2006.01)
`(2006.01)
`(2006.01)
`,
`(3008-013
`
`.
`
`Int. Cl.
`AGIK 38/12
`AGIK 38/10
`A61IP 30A
`onwe
`(52) U.S. Cl.
`CPC Loerie A6IK 38/12 (2013.01); AGIK 38/10
`(2013.01); A61K 9/00 (2013.01); CO7K 11/02
`(2013.01)
`USPC were 514/204; 514/2.9; 514/3.1, 514/211,
`514/21.5
`
`i
`i
`i
`(58) Field of Classification Search
`CPC... AG1K 38/10: AG1K 38/12: AG61K 9/00:
`an
`CO7K 11/02
`See applicationfile for complete search history.
`.
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`AMNEAL EX. 1009
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`* cited by examiner
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`U.S. Patent
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`Sep. 16, 2014
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`Sheet1 of 22
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`US 8,835,382 B2
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`Daptomycin
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`Sep. 16, 2014
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`Sheet 2 of 22
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`US 8,835,382 B2
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`“anhydro-daptomycin”
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`Sep. 16, 2014
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`Sheet3 of 22
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`US 8,835,382 B2
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`“B-isomer”or “B-isomer of daptomycin”
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`U.S. Patent
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`Sep. 16, 2014
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`Sheet4 of 22
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`US 8,835,382 B2
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`lactone hydrolysis product
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`U.S. Patent
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`Sep. 16, 2014
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`Sheet 5 of 22
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`US 8,835,382 B2
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`U.S. Patent
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`Sep. 16, 2014
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`Sheet 6 of 22
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`US 8,835,382 B2
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`ANEBION
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`U.S. Patent
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`Sep. 16, 2014
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`Sheet 7 of 22
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`US 8,835,382 B2
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`U.S. Patent
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`Sep. 16, 2014
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`Sheet 8 of 22
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`US 8,835,382 B2
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`Sep. 16, 2014
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`Sheet 9 of 22
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`US 8,835,382 B2
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`Sheet 11 of 22
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`US 8,835,382 B2
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`Sheet 12 of 22
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`US 8,835,382 B2
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`Sep. 16, 2014
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`Sheet 13 of 22
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`US 8,835,382 B2
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`U.S. Patent
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`Sep. 16, 2014
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`Sheet 14 of 22
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`US 8,835,382 B2
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`U.S. Patent
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`Sep. 16, 2014
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`Sheet 15 of 22
`
`US 8,835,382 B2
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`U.S. Patent
`
`Sep. 16, 2014
`
`Sheet 16 of 22
`
`US 8,835,382 B2
`
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