(12) Unlted States Patent
`(10) Patent No.:
`US 8,633,309 B2
`
`Ross et al.
`(45) Date of Patent:
`*Jan. 21, 2014
`
`USOO8633309B2
`
`(54) NUCLEOSIDE PHOSPHORAMIDATES
`
`~
`.
`-
`~
`(71) Appl1cant. SileadSPharmasset LLC, Foster C1ty,
`(U )
`
`(72)
`
`Inventors: Bruce Ross, El Granada, CA (US);
`Michael Joseph Sofia, Doylestown, PA
`(US); Ganapati Reddy Pamulapati,
`San Ramon CA (US) 511 una
`’
`.
`’
`g
`Rachakondas TWlnsburgs OH (US);
`Hai-Ren Zhang, San Jose, CA (US);
`Byoung—Kwon Chun, Robbinsville, NJ
`.
`-
`(US)’ Pelyuan Wang, Tomwa’ NJ (Us)
`.
`.
`(73) Ass1gnee: Gilead Pharmasset LLC, Foster C1ty,
`CA (US)
`
`( * ) Notice:
`
`Subject to any disclaimer, the term ofthis
`'
`'
`patent 1s extended or adjusted under 35
`U~S~C~ 15403) by 0 days
`~
`~
`~
`~
`~
`This patent 1s subject to a term1nal d1s-
`0131111131
`
`(21) Appl. No.: 13/738,425
`
`(22)
`
`(65)
`
`Filed:
`
`Jan. 10 2013
`3
`Prior Publication Data
`US 2013/0137654 A1
`May 30, 2013
`
`Related US. Application Data
`
`(62) Division of application No. 12/783,680, filed on May
`20, 2010
`(60) Provisional application No. 61/319,513, filed on Mar.
`31, 2010, provisional application No. 61/179,923,
`filed on May 20, 2009.
`
`(51)
`
`(200601)
`(2006.01)
`(2006.01)
`
`Int Cl
`'
`'
`A61K 31/7072
`A61K 31/664
`C0 7H 19/10
`(52) US. Cl.
`CPC
`
`............
`
`C07H 19/10 (2013 01). A6IK 31/7072
`~
`.
`,
`(201301)a A61K 31/664 (201301)
`USPC .......................................... 53 6/28.53; 514/51
`(58) Field of Classification Search
`None
`.
`.
`.
`See appl1cat1on file for complete search h1story.
`,
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`OTHER PUBLICATIONS
`
`U.S.App1. No. 13/925,078, filed Jun. 2013, Ross et al.*
`Mitchell et a1., “B10revers1b1e Protection for the Phospho Group:
`Bioactivation
`0f
`the Di(4-acy10xybenzyl)
`and M0n0(4-
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`-
`C t
`d
`( on 1nue )
`Primary Examiner 7 Eric S Olson
`(74) Allorney,Agenl, orFirm 7 Fitzpatrick, Cella, Harper&
`Scinto
`
`ABSTRACT
`(57)
`Disclosed herein are nucleoside phosphoramidates and their
`use as agents for treating viral diseases. These compounds are
`inhibitors of RNA-dependent 5 RNA viral replication and are
`useful as inhibitors of HCV NSSB polymerase, as inhibitors
`of HCV replication and for treatment ofhepatitis C infection
`in mamma15~
`
`12 Claims, 21 Drawing Sheets
`
`1PR201 8-00125
`
`Page 1 of 69
`
`l-MAK 100 l
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`IPR2018-00125
`
`Page 1 of 69
`
`I-MAK 1001
`
`

`

`US 8,633,309 B2
`
`Page 2
`
`(56)
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`IPR2018-00125
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`Page 2 of 69
`
`I-MAK 1001
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`Page 2 of 69
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`I-MAK 1001
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`

`

`US 8,633,309 B2
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