US007157456B2
`US007157456B2
`
`Illlllllll
`
`(12) United States Patent
`(12) United States Patent
`Straub et al.
`Straub et a1.
`
`(io) Patent No.:
`(10) Patent N0.:
`(45) Date of Patent:
`(45) Date of Patent:
`
`US 7,157,456 B2
`US 7,157,456 B2
`Jan. 2, 2007
`Jan. 2, 2007
`
`AND
`(54) SUBSTITUTED OXAZOLIDINONES
`(54) SUBSTITUTED OXAZOLIDINONES AND
`THEIR USE IN THE FIELD OF BLOOD
`THEIR USE IN THE FIELD OF BLOOD
`COAGULATION
`COAGULATION
`
`(75)
`Inventors: Alexander Straub, Wuppertal (DE);
`(75) Inventors: Alexander Straub, Wuppertal (DE);
`Thomas Lampe, Wuppertal (DE); Jens
`Thomas Lampe, Wuppertal (DE); Jens
`Pohlmann, Wuppertal (DE); Susanne
`Pohlmann, Wuppertal (DE); Susanne
`Rohrig, Essen (DE); Elisabeth
`Rohrig, Essen (DE); Elisabeth
`Perzborn, Wuppertal (DE); Karl-Heinz
`Perzborn, Wuppertal (DE); Karl-Heinz
`Schlemmer, Wuppertal (DE); Joseph
`Schlemmer, Wuppertal (DE); Joseph
`Pernerstorfer, Wuppertal (DE)
`Pernerstorfer, Wuppertal (DE)
`
`(73) Assignee: Bayer HealthCare AG, Leverkusen
`73
`Assi nee: Ba er HealthCare AG, Leverkusen
`g
`y
`(DE)
`(DE)
`the
`Subject to any disclaimer,
`Sub'ect to an disclaimer, the term of this
`J
`y
`patent is extended or adjusted under 35
`patent is extended or adjusted under 35
`U.S.C. 154(b) by 59 days.
`U.S.C. 154(b) by 59 days.
`
`( * ) Notice:
`*
`Notice:
`
`(21) Appl. No.:
`(21) App1.No.:
`
`10/181,051
`10/1s1,051
`
`(22) PCT Filed:
`(22) PCT Filed:
`
`Dec. 11, 2000
`Dec. 11, 2000
`
`(86) PCT No.:
`(86) PCT N0.:
`
`PCT/EP00/12492
`PCT/EP00/12492
`
`§ 371 (c)(1),
`§ 371 (0X1)’
`(2), (4) Date:
`(2), (4) Date:
`
`Jun. 24, 2002
`Jun. 24, 2002
`
`(87) PCT Pub. No.: WOOl/47919
`(87) PCT Pub. No.: WO01/47919
`
`PCT Pub. Date: Jul. 5, 2001
`PCT Pub. Date: Jul. 5, 2001
`
`(65)
`(65)
`
`Prior Publication Data
`Prior Publication Data
`US 2003/0153610 Al Aug. 14, 2003
`US 2003/0153610 A1
`Aug. 14, 2003
`
`Foreign Application Priority Data
`(30)
`Foreign Application Priority Data
`(30)
`Dec. 24, 1999
`(DE)
`199 62 924
`Dec. 24, 1999 (DE) .............................. .. 199 62 924
`
`(51) Int. CI.
`(51) Int. Cl.
`(2006.01)
`A6IK 31/5377
`(2006.01)
`A61K 31/53 77
`(2006.01)
`C07D 409/14
`(2006.01)
`0070 409/14
`514/236.8; 544/139
`(52) U.S. CI
`(52) US. Cl. .................................. .. 514/236.8;544/139
`(58) Field of Classification Search
`544/139;
`(58) Field of Classi?cation Search .............. .. 544/139;
`514/236.8
`514/236.8
`See application
`file for complete search history.
`See application ?le for complete search history.
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`
`FOREIGN PATENT DOCUMENTS
`FOREIGN PATENT DOCUMENTS
`
`AU
`AU
`CA
`CA
`CA
`CA
`CA
`CA
`DE
`DE
`EP
`EP
`EP
`EP
`EP
`EP
`term
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`EP
`WO wo
`WO
`WO
`WO wo
`WO
`WO
`WO
`WO
`wo
`WO
`WO
`WO
`WO
`WO
`
`of
`
`744002
`744002
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`196 04 223
`0 127 902
`0 127 902
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`0 316 594
`0 352 781
`0 352 781
`this
`0 623 615
`0 623 615
`0645376
`0645376
`0 738 726
`0 738 726
`0 785 200
`0 785 200
`WO-93/09103
`WO-93/09103
`WO-93/23384
`WO-93/23384
`WO-97/03072
`WO-97/03072
`WO-97/09328
`WO-97/09328
`WO-97/10223
`WO-97/10223
`WO-98/01446
`WO-98/01446
`WO-98/54161
`WO-98/54161
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`WO-99/02525
`
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`12/1998
`12/1998
`1/1999
`1/1999
`
`(Continued)
`(Continued)
`OTHER PUBLICATIONS
`OTHER PUBLICATIONS
`
`""This reference is not being famished since it was cited in the
`*This reference is not being furnished since it Was cited in the
`International Search Report for PCT/EP 00/12492.*
`International Search Report for PCT/EP 00/ 12492.*
`
`(Continued)
`(Continued)
`Primary Examiner—Kamal A. Saeed
`Primary ExamineriKamal A. Saeed
`Assistant Examiner—Rebecca Anderson
`Assistant ExamineriRebecca Anderson
`(74) Attorney, Agent, or Firm—Connolly Bove Lodge &
`(74) Attorney, Agent, or FirmiConnolly Bove Lodge &
`Hutz LLP
`HutZ LLP
`
`(57)
`(57)
`
`ABSTRACT
`ABSTRACT
`
`Novel
`The invention relates to the field of blood coagulation.
`The invention relates to the ?eld of blood coagulation. Novel
`oxazolidinone derivatives of the general formula (I)
`oxaZolidinone derivatives of the general formula (I)
`
`(I)
`
`o
`
`X
`
`R2 JR
`Ri
`\N
`0
`R5
`R5
`R6
`R6
`
`R3'
`
`R4
`
`R8—
`
`R7
`R7
`
`R1, Y O
`
`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.
`
`30 Claims, No Drawings
`30 Claims, No Drawings
`
`MYLAN - EXHIBIT 1008
`
`

`

`US 7,157,456 B2
`US 7,157,456 B2
`Page 2
`Page 2
`
`FOREIGN PATENT DOCUMENTS
`FOREIGN PATENT DOCUMENTS
`
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
`WO
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`WO
`WO
`WO
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`WO
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`WO-99/03846
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`WO-01/42242
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`
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