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Hydroxamic and carboxylic acid derivatives having MMP and TNF inhibitory activity

  • US 6,118,001 A
  • Filed: 08/07/1997
  • Issued: 09/12/2000
  • Est. Priority Date: 08/07/1996
  • Status: Expired due to Fees
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Petitions
24
Forward Citation
3
Assignments
First Claim
Patent Images

1. A compound of formula (I)



  • space="preserve" listing-type="equation">B--X--(CH.sub.2).sub.n --CHR.sup.1 --(CH.sub.2).sub.m --COY (I)
wherein m and n are each independently 0 or 1, but are not both 0;

X is S(O)0-2 ;

Y is selected from the group consisting of OR2 and NHOH;

R1 is H or is a group selected from the group consisting of H, C1-6 alkyl, C2-6 alkenyl, aryl, C1-6 alkyl-aryl, heteroaryl, C1-6 alkyl-heteroaryl, heterocycloalkyl, C1-6 alkyl-heterocycloalkyl, cycloalkyl, and C1-6 alkyl-cycloalkyl, and said group is optionally substituted with R9 ;

R2 is selected from the group consisting of h and C1-6 alkyl;

B is selected from the group consisting of heterocycloalkenyl and heterocycloalkyl optionally substituted by a substituent selected from the group consisting of R5, C1-6 alkyl-R5, C3-6 alkenyl-R7, aryl optionally substituted with R5, aryl-C1-6 alkyl-R5, C1-6 alkyl-aryl optionally substituted with R5, C1-6 alkyl-heteroaryl optionally substituted with R5, aryl-C2-6 alkenyl-R5, heteroaryl optionally substituted with R5, heteroaryl-C1-6 alkyl-R5, cycloalkyl optionally substituted with R5, benzofused cycloalkyl optionally substituted with R5, heterocycloalkyl optionally substituted with R5, benzofused heterocycloalkyl optionally substituted with R5, and the groups;

 ##STR6## R5 is selected from the group consisting of C1-6 alkyl, C2-6 alkenyl-R7, halogen, CN, NO2, N(R6)2, OR6, COR6, CO2 R2, CON(R6)2, NR6 R7, S(O)0-2 R8, and SO2 N(R6)2 ;

R6 is H or a group selected from the group consisting of C1-6 alkyl, aryl, C1-6 alkyl-aryl, heteraryl, C1-6 alkyl-heteroaryl, cycloalkyl, C1-6 alkyl-cycloalkyl, heterocycloalkyl, and C1-6 alkyl-heterocycloaklyl, wherein said group is optionally substituted with a substituent selected from the group consisting of R8, COR8, SO0-2 R8, CO2 R8, OR8, CONR2 R8, NR2 R8, halogen, CN, SO2 NR3 R8, and NO2, and for each case of N(R6)2 the R6 groups are the same or different or N(R6)2 is heterocycloalkyl optionally substituted with a substituent selected from the group consisting of R8, COR8, SO0-3 R8, OR8, CONR2 R8, NR2 R8, halogen, CN, SO2 NR2 R8, and NO2 ;

R7 is selected from the group consisting of COR6, CON(R6)2, CO2 R8, and SO2 R8 ;

R8 is selected from the group consisting of C1-6 alkyl, aryl, C1-6 alkyl-aryl, heteroaryl, and C1-6 alkyl-heteroaryl; and 

R9 is selected from the group consisting of OR6, COR6, CO2 R3, CON(R6)2, NR6 R7, S(O)0-2 R8, SO2 N(R6)2, phthalimido, succinimido, and the group ##STR7##  or a salt, solvate, hydrate, or protected amino or protected carboxy derivative thereof.
      

    

  

  
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