Illllllllllllllllllllllllllllllllll
`
`US007592339B2
`US007592339B2
`
`II
`
`(12) United States Patent
`(12) Ulllted States Patent
`Straub et al.
`Straub et a].
`
`US 7,592,339 B2
`(io) Patent No.:
`(10) Patent N0.:
`US 7,592,339 B2
`(45) Date of Patent:
`*Sep. 22, 2009
`*Sep. 22, 2009
`(45) Date of Patent:
`
`(54) SUBSTITUTED OXAZOLIDINONES
`(54) SUBSTITUTED OXAZOLIDINONES AND
`THEIR USE IN THE
`FIELD
`OF
`THEIR USE IN THE FIELD OF BLOOD
`COAGULATION
`COAGULATION
`
`AND
`
`(75)
`(75) Inventors: Alexander Straub, Wuppertal (DE);
`Inventors: Alexander Straub, Wuppertal
`(DE);
`Thomas Lampe, Wuppertal
`
`(DE); Jens
`Thomas Lampe, Wuppertal (DE); Jens
`_
`Pohlmann, Wuppertal
`Susanne
`(DE);
`Pohhflanns WuPPenal (PE), Susanne
`Rohrig, Essen
`(DE); Elisabeth
`Rohrlg, 13556110313); Ellsabeth
`_
`Perzborn, Wuppertal
`(DE); Karl-Heinz
`Perzborn, wuppertal (DE); Karl-Helm
`Schlemmer, Wuppertal
`Joseph
`(DE);
`Schlemmer, Wuppertal (DE); Joseph
`Pernerstorfer, Wuppertal
`(DE)
`Pernerstorfer, Wuppertal (DE)
`
`5,910,504 A
`6/1999 Hutchinson et al.
`5,910,504 A
`6/1999 Hutchinson et al.
`BLOOD
`5,922,708 A
`7/1999 Riedl et al.
`5,922,708 A
`7/1999 Riedl et al.
`5,929,248 A
`al.
`7/1999 Barbachyn et
`5,929,248 A
`7/ 1999 Barbachyn et al.
`5,972,947 A
`10/1999 Tsaklakidis et al.
`5,972,947 A 10/1999 Tsaklakidis et al.
`6,069,160 A
`5/2000 Stolle et al.
`23??’
`$1
`12211151122131‘
`6,251,869 B1
`6/2001 Bohanon
`80001 W .
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`6,273,913 B1
`8/2001 Wright et al.
`r1ght et al.
`,
`,
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`6,294,201 B1
`6,294,201 B1
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`6,413,981 B1
`6,413,981 B1
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`6,610,682 B2
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`6,805,881 B1
`6,805,881 B1
`10/2004 Kanikanti et al.
`6,818,243 B2
`11/2004 Nagashima et
`al.
`6,818,243 B2 11/2004 Nagashima et a1.
`7,034,017 B2
`4/2006 Straub et al.
`4/2006 Straub et al.
`7,034,017 B2
`7,045,631 B2
`5/2006 Rosentreter et al.
`5/2006 Rosentreter et al.
`7,045,631 B2
`7,078,417 B2
`7/2006 Rosentreter et al.
`7/2006 Rosentreter et al.
`7,078,417 B2
`7,109,218 B2
`9/2006 Rosentreter et al.
`9/2006 Rosentreter et al.
`7,109,218 B2
`7,129,255 B2
`10/2006 Rosentreter et al.
`this
`of
`7’l29’255 B2 10/2006 Rosentreter et a1‘
`7,157,456 B2
`1/2007 Straub et al.
`1/2007 Straub et al.
`7,157,456 B2
`400% B
`7 351 823 B2
`7,351,823 B2
`4/2008 Berwe et al.
`erWe et al.
`,
`,
`2001/0029351 A1 10/2001 FalOtlCO 61 al.
`2001/0029351 Al
`10/2001 Falotico et al.
`2003/0153610 Al
`8/2003 Straub et al.
`8/2003 Straub 61 al.
`2003/0153610 A1
`55/2003 Waterman
`2003/0161882 A1
`2003/0161882 Al
`8/2003 Waterman
`2004/0162427 Al
`8/2004 Rosentreter et al.
`8/2004 Rosentreter 61 al.
`2004/0162427 A1
`2004/0242660 Al *
`514/376
`12/2004 Straub etal
`2004/0242660 A1* 12/2004 Straub et al. .............. .. 514/376
`2005/0064006 Al
`3/2005 Perzborn et al.
`3/2005 PerZborn 61 a1.
`2005/0064006 A1
`2005/0182055 Al
`8/2005 Berwe et al.
`8/2005 BerWe et al.
`2005/0182055 A1
`_
`(Continued)
`(C0nt1nued)
`FOREIGN PATENT DOCUMENTS
`744002
`7/l999
`7/1999
`744002
`
`term
`
`AU
`AU
`
`( * ) Notice:
`( * ) Notice:
`
`(73) Assignee: Bayer Schering Pharma
`(73) Assignee; Bayer Schering Pharma
`Aktiengesellschaft, Berlin
`Aktiengesellschaft Berlin (DE)
`3
`Subject to any disclaimer,
`the
`Subject to any disclaimer, the term of this
`.
`.
`patent is extended or adjusted under 35
`patent 1s extended or adjusted under 35
`U.S.C. 154(b) by 0
`days.
`U-S-C- 154(1)) by 0 days-
`_
`_
`_
`_
`_
`This patent is subject to a terminal dis­
`Th1s patent 1s subject to a term1nal d1s-
`claimer.
`claimer.
`
`(DE)
`
`(21) Appl.No.: 11/460,529
`(21) Appl. No.: 11/460,529
`
`(22) Filed:
`(22) Filed:
`
`Jul. 27, 2006
`Jul. 27, 2006
`
`(65)
`
`Prior Publication Data
`US 2006/0258724 Al Nov. 16, 2006
`US 2006/0258724 A1
`Nov. 16, 2006
`
`Related U.S. Application Data
`Related US. Application Data
`(62) Division of application No. 10/181,051,
`filedas appli­
`(62) Division of application No. 10/1 81,05 1, ?led as appli-
`cation No. PCT/EP00/12492 on Dec. 11, 2002, now
`cation No. PCT/EPOO/ 12492 on Dec. 11, 2002, noW
`Pat NO_ 7 157 4 56_
`Pat. No. 7,157,456.
`’
`’
`
`(51) Int. CI.
`(51) Int. Cl.
`(2006.01)
`A6IK 31/5377
`(2006.01)
`A61K 31/5377
`(2006.01)
`C07D 409/14
`(2006,01)
`C0 7D 409/14
`(52) U.S. CI
`514/236.8; 544/139
`(52) us. Cl. .................................. .. 514/236.8; 544/139
`(58) Field of Classification
`Search
`514/236.8
`(58) Field of Classi?cation Search ............. .. 514/2368
`search
`See application
`file for
`complete
`See application ?le for complete search history.
`References Cited
`References Cited
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`(Continued)
`(Continued)
`OTHER PUBLICATIONS
`OTHER PUBLICATIONS
`
`and
`
`Thera­
`Pharmacology
`of
`Journal
`Wong et al., The
`Wong et al., The Journal of Pharmacology and Experimental Thera
`peutics, vol. 295, No.
`1,
`
`(2000), 212-218.*
`pp.
`peutics, VOl. 295, N0. 1, (2000), pp. 212-218.*
`(Continued)
`(Continued)
`Primary Examiner—Rebecca
`Anderson
`L
`Primary ExamineriRebecca L Anderson
`(J A) Attorney, Agent, or Firm—Connolly Bove Lodge & Hutz
`(70411001948911, 0rFirm%OnnO11y Bove LO<18e&H11IZ
`LLP
`LLP
`history.
`(57)
`(57)
`
`ABSTRACT
`ABSTRACT
`
`Experimental
`
`coagulation.
`blood
`field of
`The invention relates to the
`The invention relates to the ?eld of blood coagulation. Novel
`oxazolidinone derivatives
`of
`the
`general
`formula
`oxaZolidinone derivatives of the general formula (I)
`
`Novel
`
`(I)
`
`o
`
`(I)
`(I)
`
`R4
`4
`R
`R,
`R7
`R8 —
`R8 — N\H/ R1,
`0
`
`use as medicinally
`
`their
`their preparation and
`processes for
`processes for their preparation and their use as medicinally
`active compounds for the prophylaxis and/or treatment of
`active compounds for the prophylaxis and/or treatment of
`disorders are described.
`disorders are described.
`
`21 Claims, No Drawings
`21 Claims, N0 Drawings
`
`R2 A N
`
`R2,
`
`R3'
`3
`R
`
`0
`R5
`R5
`R6
`R6
`
`X
`R1, Y O
`
`MYLAN - EXHIBIT 1009
`
`

`

`US 7,592,339 B2
`US 7,592,339 B2
`Page 2
`Page 2
`
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`
`AU
`AU
`CA
`CA
`CA
`CA
`CA
`CA
`DE
`DE
`DE
`DE
`DE
`DE
`DE
`DE
`DE
`DE
`DE
`DE
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`GB
`GB
`WO
`W0
`WO
`W0
`WO
`W0
`WO
`W0
`WO
`W0
`WO
`W0
`WO
`W0
`WO
`W0
`WO
`W0
`WO
`W0
`WO
`W0
`WO
`W0
`WO
`WO
`WO
`WO
`WO
`W0
`WO
`W0
`WO
`WO
`WO
`W0
`WO
`W0
`WO
`W0
`WO
`W0
`WO
`W0
`WO
`W0
`WO
`W0
`WO
`W0
`WO
`WO
`WO
`W0
`WO
`W0
`WO
`W0
`WO
`W0
`WO
`WO
`WO
`W0
`WO
`W0
`WO
`WO
`WO
`W0
`WO
`WO
`WO
`WO
`WO
`WO
`
`WO
`WO-03/053441 A1
`WO
`WO-03/053441 A1
`WO-2004/060887 A1
`WO
`WO WO-2004/060887 A1
`W0 WO_2005/060940 A1
`WO-2005/060940 A1
`WO
`W0 WO_2005/06g456 A1
`WO-2005/068456 A1
`WO
`WO-2006/072367 A1
`WO
`W0 WO_2006/072367 A1
`W0 WO_2006/079474 A1
`WO-2006/079474 A1
`WO
`WO-2007-036306 A1
`WO
`W0 WO_2007_036306 A1
`W0 WO_2007/039122 A2
`WO-2007/039122 A2
`WO
`WO-2007/039132 A1
`WO
`W0 WO_2007/039132 A1
`WO-2007/039134 A1
`WO
`W0 WO_2007/039134 A1
`W0 WO_2007/042146 A1
`WO-2007/042146 A1
`WO
`WO-2008/012002 A1
`WO
`WO WO-2008/012002 A1
`WO WO-2008/052671 A1
`WO-2008/052671 A1
`WO
`
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`5/2008
`
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