Claims
- 1. A compound having the formula (I): ##STR75## or a pharmaceutically acceptable salt thereof, wherein:
- R.sup.1 is ##STR76## Y is O or S; Z is O, S(O).sub.p or NR.sup.11 ;
- R.sup.2a and R.sup.2b are each independently:
- (a) hydrogen,
- (b) halogen (Cl, Br, I, F),
- (c) --NO.sub.2,
- (d) NH.sub.2,
- (e) C.sub.1 -C.sub.4 -alkylamino,
- (f) --SO.sub.2 NHR.sup.9,
- (g) CF.sub.3,
- (h) C.sub.1 -C.sub.6 -alkyl substituted with:
- (1) H,
- (2) F,
- (3) aryl,
- (4) thiophenyl,
- (5) furyl,
- (6) pyridyl,
- (7) imidazoyl,
- (8) pyrimidinyl,
- (9) C.sub.1 -C.sub.6 -alkoxy,
- (10) --O(CH.sub.2).sub.m --O--C.sub.1 -C.sub.4 -alkyl, wherein m is 2 to 4, or
- (11) C.sub.3 -C.sub.7 -cycloalkyl, or
- when R.sup.2a and R.sup.2b are on adjacent carbons, they can be bonded together to form a phenyl ring;
- R.sup.3a is
- (a) H,
- (b) halo (Cl, Br, I, F)
- (c) C.sub.1 -C.sub.6 -alkyl,
- (d) C.sub.1 -C.sub.6 -alkoxy,
- (e) C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.4 -alkyl;
- R.sup.3b is
- (a) H,
- (b) halo (Cl, Br, I, F),
- (c) NO.sub.2,
- (d) C.sub.1 -C.sub.6 -alkyl,
- (e) C.sub.1 -C.sub.5 -alkylcarbonyloxy,
- (f) C.sub.3 -C.sub.6 -cycloalkyl;
- (g) C.sub.1 -C.sub.6 -alkoxy,
- (h) --NHSO.sub.2 R.sup.4,
- (i) hydroxy-C.sub.1 -C.sub.4 -alkyl,
- (j) aryl-C.sub.1 -C.sub.4 -alkyl,
- (k) C.sub.1 -C.sub.4 -alkylthio,
- (l) C.sub.1 -C.sub.4 -alkylsulfinyl,
- (m) C.sub.1 -C.sub.4 -alkylsulfonyl,
- (n) NH.sub.2,
- (o) C.sub.1 -C.sub.4 -alkylamino,
- (p) di(C.sub.1 -C.sub.4 -alkyl)amino,
- (q) CF.sub.3,
- (r) --SO.sub.2 --NHR.sup.9,
- (s) aryl,
- (t) furyl, or
- when R.sup.3a and R.sup.3b are on adjacent carbons, they can be bonded together to form a phenyl ring;
- wherein aryl is phenyl, biphenyl or naphthyl unsubstituted or substituted with one, two or three substituents selected from the group consisting of halo (Cl, Br, I, F), C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, NO.sub.2, CF.sub.3, C.sub.1 -C.sub.4 -alkyl-S(O).sub.p --, CF.sub.3 SO.sub.2 --, --OH, --NR.sup.9 R.sup.10, --SO.sub.2 NR.sup.9 R.sup.10, C.sub.3 -C.sub.7 -cycloalkyl, --CO.sub.2 H, --CO.sub.2 --C.sub.1 -C.sub.4 -alkyl, --CONR.sup.21 R.sup.22, --CN, C.sub.3 -C.sub.10 -alkenyl, --NHCOR.sup.9, --OCF.sub.3, phenyl-C.sub.1 -C.sub.2 -alkyl, phenyl-S(O).sub.p and phenyl-C.sub.1 -C.sub.2 -alkyl-S(O).sub.p ;
- R.sup.4 is H, straight chain or branched C.sub.1 -C.sub.6 alkyl, --CH.sub.2 -aryl or aryl;
- R.sup.5 is H or --CH(R.sup.4)--O--CO--R.sup.4a ; wherein R.sup.4a is C.sub.1 -C.sub.6 -alkyl, aryl or --CH.sub.2 -aryl;
- E is a single bond, --NR.sup.13 (CH.sub.2).sub.s --, --S(O).sub.x (CH.sub.2).sub.s -- where x is 0 to 2 and s is 0 to 5, --CH(OH)--, --O(CH.sub.2).sub.s --, or --CO--;
- R.sup.6 is
- (a) phenyl unsubstituted or substituted with 1 or 2 substituents selected from the group consisting of Cl, Br, I or F, --O--C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkyl, --NO.sub.2, --CF.sub.3, --SO.sub.2 NR.sup.9 R.sup.10, --S--C.sub.1 -C.sub.4 -alkyl, --OH, --NH.sub.2, C.sub.3 -C.sub.7 -cycloalkyl and C.sub.3 -C.sub.10 -alkenyl;
- (b) straight chain or branched C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl or C.sub.2 -C.sub.6 -alkynyl each of which is unsubstituted or substituted with one or more substituents selected from the group consisting of aryl as defined above, C.sub.3 -C.sub.7 -cycloalkyl, halo (Cl, Br, I, F), --OH, --O--C.sub.1 -C.sub.4 -alkyl, --NH.sub.2, --NH(C.sub.1 -C.sub.4 -alkyl), --N(C.sub.1 -C.sub.4 -alkyl).sub.2, --NH--SO.sub.2 R.sup.4, --COOR.sup.4, --SO.sub.2 NHR.sup.9, --S--C.sub.1 -C.sub.4 -alkyl;
- (c) heteroaryl, wherein heteroaryl is an unsubstituted, monosubstituted or disubstituted five- or six-membered aromatic ring which contains 1 to 2 heteroatoms selected from the group consisting of O, N and S and wherein the substituents are members selected from the group consisting of --OH, --SH, --C.sub.1 -C.sub.4 -alkyl, --C.sub.1 -C.sub.4 -alkoxy, --CF.sub.3, Cl, Br, F, I, --NO.sub.2, --CO.sub.2 H, --CO.sub.2 --C.sub.1 -C.sub.4 -alkyl, --NH.sub.2, --NH(C.sub.1 -C.sub.4 -alkyl) and --N(C.sub.1 -C.sub.4 -alkyl).sub.2 ;
- (d) mono-, di-, tri- or polyfluoro-C.sub.1 -C.sub.5 -alkyl;
- (e) C.sub.3 -C.sub.7 -cycloalkyl optionally substituted with one or more substituents selected from the group consisting of C.sub.1 -C.sub.4 -alkyl, O--C.sub.1 -C.sub.4 -alkyl, S--C.sub.1 -C.sub.4 -alkyl, OH, perfluoro-C.sub.1 -C.sub.4 -alkyl, or halo (Cl, Br, F, I); or
- (f) C.sub.3 -C.sub.7 -cycloalkyl-C.sub.1 -C.sub.3 -alkyl wherein the cycloalkyl is substituted as in (e) above;
- A is O, S or NR.sup.21 ;
- B is
- (a) H provided A is not NR.sup.21,
- (b) C.sub.1 -C.sub.10 -alkyl,
- (c) substituted C.sub.1 -C.sub.10 -alkyl in which one or more substituent(s) is selected from
- (1) halogen (I, Br, Cl, F),
- (2) hydroxy,
- (3) C.sub.1 -C.sub.10 -alkoxy,
- (4) C.sub.1 -C.sub.5 -alkoxycarbonyl,
- (5) C.sub.1 -C.sub.4 -alkylcarbonyloxy,
- (6) C.sub.3 -C.sub.8 -cycloalkyl,
- (7) phenyl, biphenyl or naphthyl,
- (8) substituted phenyl, biphenyl or naphthyl in which the substituents are V.sub.1, V.sub.2, V.sub.3, V.sub.4 and V.sub.5,
- (9) C.sub.1 -C.sub.10 -alkyl-S(O).sub.p,
- (10) C.sub.3 -C.sub.8 -cycloalkyl-S(O).sub.p,
- (11) phenyl-S(O).sub.p,
- (12) substituted phenyl-S(O).sub.p in which the substituents are V.sub.1 -V.sub.5,
- (13) oxo,
- (14) carboxy,
- (15) NR.sup.9 R.sup.9,
- (16) C.sub.1 -C.sub.5 -alkylaminocarbonyl,
- (17) di(C.sub.1 -C.sub.5 -alkyl)aminocarbonyl,
- (18) cyano,
- (19) --OCONR.sup.21 R.sup.22,
- (20) --NR.sup.21 COR.sup.22,
- (21) --NR.sup.21 CO.sub.2 R.sup.22,
- (22) --NR.sup.21 CONR.sup.21 R.sup.22,
- (23) --NR.sup.21 CON(CH.sub.2 CH.sub.2).sub.2 L,
- (24) --OCON(CH.sub.2 CH.sub.2).sub.2 L, wherein L is a single bond, CH.sub.2, O, S(O).sub.p or NR.sup.9,
- (d) C.sub.2 -C.sub.10 -alkenyl,
- (e) C.sub.2 -C.sub.10 -alkynyl,
- (f) C.sub.3 -C.sub.8 -cycloalkyl,
- (g) substituted C.sub.3 -C.sub.8 -cycloalkyl or substituted C.sub.3 -C.sub.8 -cycloalkyl-C.sub.1 -C.sub.4 -alkyl having one or more substituents selected from the group:
- (1) halo (Cl, Br, F, I),
- (2) hydroxy,
- (3) C.sub.1 -C.sub.6 -alkyl,
- (4) C.sub.1 -C.sub.6 -alkoxy,
- (5) C.sub.1 -C.sub.4 -alkylcarbonyloxy,
- (6) C.sub.1 -C.sub.5 -alkoxycarbonyl,
- (7) carboxy,
- (8) oxo,
- (9) C.sub.1 -C.sub.5 -alkylaminocarbonyl,
- (10) di(C.sub.1 -C.sub.5 -alkyl)aminocarbonyl,
- (11) C.sub.1 -C.sub.4 -alkylcarbonyl,
- (12) aryl,
- (13) substituted phenyl or naphthyl in which the substituents are V.sub.1, V.sub.2, V.sub.3, V.sub.4 and V.sub.5,
- (14) --NR.sup.21 COR.sup.22,
- (15) --NR.sup.21 CO.sub.2 R.sup.22,
- (16) --OCONR.sup.21 R.sup.22, and
- (17) --CN,
- (h) phenyl, biphenyl or naphthyl,
- (i) substituted phenyl, biphenyl or naphthyl in which the substituents are V.sub.1, V.sub.2, V.sub.3, V.sub.4 and V.sub.5,
- (j) phenyl-(CH.sub.2).sub.r --(Q).sub.c --(CH.sub.2).sub.t --,
- (k) substituted phenyl-(CH.sub.2).sub.r --(Q).sub.c --(CH.sub.2).sub.t -- in which the phenyl group is substituted with V.sub.1, V.sub.2, V.sub.3, V.sub.4 and V.sub.5,
- (l) heterocycle-(CH.sub.2).sub.r --(Q).sub.c --(CH.sub.2).sub.t --, wherein the heterocycle is 5- or 6-membered containing one or two heteroatoms such as pyridine, furan, pyrrole, imidazole or thiazole and unsubstituted or substituted with V.sub.1 and V.sub.2 ;
- R.sup.9 is H, C.sub.1 -C.sub.5 -alkyl, aryl or --CH.sub.2 -aryl;
- R.sup.10 is H, C.sub.1 -C.sub.4 -alkyl, or
- R.sup.9 and R.sup.10 together can be --(CH.sub.2).sub.m -- where m is 3-6;
- R.sup.11 is H, C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, or --CH.sub.2 --C.sub.6 H.sub.4 R.sup.20 ;
- R.sup.12 is --CN, --NO.sub.2 or --CO.sub.2 R.sup.4 ;
- R.sup.13 is H, C.sub.2 -C.sub.4 -alkanoyl, C.sub.1 -C.sub.6 -alkyl, allyl, C.sub.3 -C.sub.6 -cycloalkyl, phenyl or benzyl;
- R.sup.14 is H, C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -perfluoroalkyl, C.sub.3 -C.sub.6 -cycloalkyl, phenyl or benzyl;
- R.sup.15 is H, C.sub.1 -C.sub.6 -alkyl, or hydroxy;
- R.sup.16 is H, C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.6 -cycloalkyl, phenyl or benzyl;
- R.sup.17 is --NR.sup.9 R.sup.10, --OR.sup.10, --NHCONH.sub.2, --NHCSNH.sub.2, --NHSO.sub.2 CF.sub.3, ##STR77## R.sup.18 and R.sup.19 are independently C.sub.1 -C.sub.4 -alkyl or taken together are --(CH.sub.2).sub.q -- where q is 2 or 3;
- R.sup.20 is H, --NO.sub.2, --NH.sub.2, --OH or --OCH.sub.3 ;
- R.sup.21 is
- (a) H,
- (b) phenyl unsubstituted or substituted with 1 or 2 substituents selected from the group consisting of Cl, Br, I or F, --O--C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkyl, --NO.sub.2, --CF.sub.3, --SO.sub.2 NR.sup.9 R.sup.10, --S--C.sub.1 -C.sub.4 -alkyl, --OH, --NH.sub.2, --COOR.sup.4, C.sub.3 -C.sub.7 -cycloalkyl and C.sub.3 -C.sub.10 -alkenyl,
- (c) straight chain or branched C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl or C.sub.2 -C.sub.6 -alkynyl each of which is unsubstituted or substituted with one or more substituents selected from the group consisting of aryl as defined above, C.sub.3 -C.sub.7 -cycloalkyl, halo (Cl, Br, I, F), --OH, --O--C.sub.1 -C.sub.4 -alkyl, --NH.sub.2, --NH(C.sub.1 -C.sub.4 -alkyl), --N(C.sub.1 -C.sub.4 -alkyl).sub.2, --NH--SO.sub.2 R.sup.4, --COOR.sup.4, --SO.sub.2 NHR.sup.9, and --S--C.sub.1 -C.sub.4 -alkyl,
- (d) heteroaryl as defined hereinabove, or
- (e) C.sub.3 -C.sub.7 -cycloalkyl unsubstituted or substituted with one or more substituents selected from the group consisting of C.sub.1 -C.sub.4 -alkyl, --O--C.sub.1 -C.sub.4 -alkyl, --S--C.sub.1 -C.sub.4 -alkyl, --OH, --COOR.sup.4, perfluoro-C.sub.1 -C.sub.4 -alkyl or halo (Cl, Br, F, I);
- R.sup.22 is R.sup.21, excluding H;
- R.sup.23 is
- (a) H,
- (b) aryl as defined above, or
- (c) C.sub.1 -C.sub.6 -alkyl unsubstituted or substituted with aryl, F, Cl, Br, --OH, --NH.sub.2, --NH(C.sub.1 -C.sub.4 -alkyl), --N(C.sub.1 -C.sub.4 -alkyl).sub.2, or CF.sub.3 ;
- R.sup.24 is
- (a) aryl as defined above,
- (b) C.sub.1 -C.sub.6 -alkyl unsubstituted or substituted with aryl, F, Cl, Br, --OH, --NH.sub.2, --NH(C.sub.1 -C.sub.4 -alkyl), --N(C.sub.1 -C.sub.4 -alkyl).sub.2, CF.sub.3, --COOR.sup.4, or CN,
- (c) --OCH(R.sup.4)--O--CO--R.sup.4a, or
- (d) --OH, --O--C.sub.1 -C.sub.6 -alkyl wherein alkyl is as defined in (b);
- R.sup.25 is
- (a) H,
- (b) C.sub.1 -C.sub.6 -alkyl unsubstituted or substituted with aryl, F, Cl, Br, --OH, --NH.sub.2, --NH(C.sub.1 -C.sub.4 -alkyl), --N(C.sub.1 -C.sub.4 -alkyl).sub.2, CF.sub.3, --COOR.sup.4, or CN, or
- (c) F, Cl, Br;
- X is
- (a) a single bond,
- (b) --CO--,
- (c) --O--,
- (d) --S--, ##STR78## (h) --OCH.sub.2 --, (i) --CH.sub.2 O--,
- (j) --SCH.sub.2 --,
- (k) --CH.sub.2 S--,
- (l) --NHC(R.sup.9)(R.sup.10)--,
- (m) --NR.sup.9 SO.sub.2 --,
- (n) --SO.sub.2 NR.sup.9 --,
- (o) --C(R.sup.9)(R.sup.10)NH--,
- (p) --CH.dbd.CH--,
- (q) --CF.dbd.CF--,
- (r) --CH.dbd.CF--,
- (s) --CF.dbd.CH--,
- (t) --CH.sub.2 CH.sub.2 --,
- (u) --CF.sub.2 CF.sub.2 --, ##STR79## Q is --C(O)--, --S--, --O-- or --NR.sup.4 ; c is 0 or 1;
- p, r and t are 0 to 2;
- V.sub.1, V.sub.2, V.sub.3, V.sub.4 and V.sub.5 are each independently selected from:
- (a) H,
- (b) C.sub.1 -C.sub.5 -alkoxy,
- (c) C.sub.1 -C.sub.5 -alkyl,
- (d) hydroxy,
- (e) C.sub.1 -C.sub.5 -alkyl-S(O).sub.p,
- (f) --CN,
- (g) --NO.sub.2,
- (h) --NR.sup.9 R.sup.10,
- (i) C.sub.1 -C.sub.5 -alkyl-CONR.sup.21 R.sup.22,
- (j) --CONR.sup.21 R.sup.22,
- (k) --CO.sub.2 R.sup.9,
- (l) --(CH.sub.2).sub.t COR.sup.22,
- (m) CF.sub.3,
- (n) halogen (I, Br, Cl, F),
- (o) hydroxy-C.sub.1 -C.sub.4 -alkyl-,
- (p) carboxy-C.sub.1 -C.sub.4 -alkyl-,
- (q) -1H-tetrazol-5-yl,
- (r) --NH--SO.sub.2 CF.sub.3,
- (s) aryl,
- (t) C.sub.1 -C.sub.5 -alkyl-CO.sub.2 R.sup.9,
- (u) aryloxy,
- (v) aryl-C.sub.1 -C.sub.3 -alkoxy,
- (w) aryl-C.sub.1 -C.sub.3 -alkyl,
- (x) carboxyphenyl,
- (y) heteroaryl,
- (z) 2-oxazolin-2-yl optionally bearing one or more C.sub.1 -C.sub.4 -alkyl substituents,
- (aa) --(CH.sub.2).sub.t OCOR.sup.22,
- (bb) --(CH.sub.2).sub.t OCONR.sup.21 R.sup.22,
- (cc) --(CH.sub.2).sub.t NR.sup.21 COR.sup.22,
- (dd) --(CH.sub.2).sub.t NR.sup.21 CO.sub.2 R.sup.22,
- (ee) --(CH.sub.2).sub.t NR.sup.21 CONR.sup.21 R.sup.22,
- (ff) --(CH.sub.2).sub.t NR.sup.21 CON(CH.sub.2 CH.sub.2).sub.2 L,
- (gg) --(CH.sub.2).sub.t OCON(CH.sub.2 CH.sub.2).sub.2 L,
- (hh) --N(CH.sub.2 CH.sub.2).sub.2 L,
- (ii) --C.sub.1 -C.sub.5 -alkyl-CON(CH.sub.2 CH.sub.2).sub.2 L, or
- (jj) --CON(CH.sub.2 CH.sub.2).sub.2 L,
- wherein L is a single bond, O, CH.sub.2, S(O).sub.p or NR.sup.9 ;
- u is 1 or 2; and
- Z is O, NR.sup.13 or S.
- 2. The compound according to claim 1, wherein:
- R.sup.1 is: ##STR80## R.sup.2a and R.sup.2b are independently: H, F, Cl, CF.sub.3 or C.sub.1 -C.sub.4 -alkyl;
- R.sup.3a is H or F;
- R.sup.3b is H, F, Cl, CF.sub.3, C.sub.1 -C.sub.4 -alkyl, C.sub.5 -C.sub.6 -cycloalkyl, --COOCH.sub.3, --COOC.sub.2 H.sub.5, --SO.sub.2 --CH.sub.3, NH.sub.2, --N(C.sub.1 -C.sub.4 - alkyl).sub.2 or --NH--SO.sub.2 CH.sub.3 ;
- E is a single bond, --O-- or --S--;
- R.sup.6 is
- (a) C.sub.1 -C.sub.6 -alkyl optionally substituted with a substituent selected from the group consisting of Cl, F, CF.sub.3, --OH, --O--CH.sub.3, --OC.sub.2 H.sub.5, --S--CH.sub.3, --S--C.sub.2 H.sub.5, phenyl, C.sub.1 -C.sub.2 -alkylcyclopropyl or cyclopropyl,
- (b) C.sub.2 -C.sub.6 -alkenyl or C.sub.2 -C.sub.6 -alkynyl,
- (c) aryl as defined above,
- (d) a heteroaryl selected from the group consisting of 2-pyridyl, 4-pyridyl, 2-pyrimidyl, 4-pyrimidyl, imidazoyl, thiazolyl, thienyl, or furyl,
- (e) perfluoro-C.sub.1 -C.sub.4 -alkyl which is a member selected from the group consisting of CF.sub.3 --, CF.sub.3 CF.sub.2 --, CF.sub.3 CF.sub.2 CF.sub.2 --, or CF.sub.3 CF.sub.2 CF.sub.2 CF.sub.2 --, or
- (f) C.sub.3 -C.sub.7 -cycloalkyl optionally substituted with a substituent selected from the group consisting of methyl, ethyl, CF.sub.3 or CF.sub.3 CF.sub.2 ;
- A is O, S or NR.sup.21 ;
- B is
- (a) H provided A is not NR.sup.21,
- (b) C.sub.1 -C.sub.10 -alkyl,
- (c) substituted C.sub.1 -C.sub.10 -alkyl in which one or two substituents are selected from:
- (1) hydroxy,
- (2) C.sub.1 -C.sub.5 -alkoxy,
- (3) C.sub.1 -C.sub.5 -alkoxycarbonyl,
- (4) C.sub.1 -C.sub.4 -alkylcarbonyloxy,
- (5) C.sub.3 -C.sub.8 -cycloalkyl,
- (6) phenyl,
- (7) substituted phenyl in which the substituents are V.sub.1, V.sub.2, V.sub.3, V.sub.4 and V.sub.5,
- (8) C.sub.1 -C.sub.5 -alkyl-S(O).sub.p,
- (9) phenyl-S(O).sub.p,
- (10) substituted phenyl-S(O).sub.p in which the substituent is V,
- (11) oxo,
- (12) carboxy,
- (13) C.sub.1 -C.sub.5 -alkylaminocarbonyl,
- (d) C.sub.2 -C.sub.10 -alkenyl,
- (e) C.sub.2 -C.sub.10 -alkynyl,
- (f) C.sub.3 -C.sub.8 -cycloalkyl,
- (g) substituted C.sub.3 -C.sub.8 -cycloalkyl or substituted C.sub.3 -C.sub.8 -cycloalkyl-C.sub.1 -C.sub.4 -alkyl in which one or more substituent(s) is selected from:
- (1) hydroxy,
- (2) C.sub.1 -C.sub.5 -alkoxy,
- (3) C.sub.1 -C.sub.5 -alkoxycarbonyl,
- (4) C.sub.1 -C.sub.4 -alkylcarbonyloxy,
- (5) C.sub.1 -C.sub.6 -alkyl,
- (6) phenyl,
- (7) substituted phenyl in which the substituents are V.sub.1, V.sub.2, V.sub.3, V.sub.4, and V.sub.5,
- (8) oxo,
- (9) carboxy,
- (10) C.sub.1 -C.sub.5 -alkylaminocarbonyl;
- (h) mono-, di-, tri-, or polyfluoro-C.sub.1 -C.sub.10 -alkyl,
- (i) phenyl, biphenyl or naphthyl,
- (j) substituted phenyl, biphenyl or naphthyl in which the substituents are V.sub.1, V.sub.2, V.sub.3, V.sub.4 and V.sub.5,
- (k) phenyl--(CH.sub.2).sub.r --(Q).sub.c --(CH.sub.2).sub.t --,
- (l) substituted phenyl--(CH.sub.2).sub.r --(Q).sub.c --(CH.sub.2).sub.t --,
- (m) heterocycle--(CH.sub.2).sub.r --(Q).sub.c --(CH.sub.2).sub.t --, wherein the heterocycle is 5- or 6-membered containing one or two heteroatoms such as pyridine, furan, pyrrole, imidazole or thiazole and unsubstituted or substituted with V.sub.1 and V.sub.2 ;
- V.sub.1, V.sub.2, V.sub.3, V.sub.4 and V.sub.5 are independently selected from:
- (a) hydrogen,
- (b) C.sub.1 -C.sub.5 -alkoxy,
- (c) C.sub.1 -C.sub.5 -alkyl,
- (d) hydroxy,
- (e) NR.sup.9 R.sup.10,
- (f) CO.sub.2 R.sup.9,
- (g) trifluoromethyl,
- (h) halogen,
- (i) hydroxy-C.sub.1 -C.sub.4 -alkyl,
- (j) -1H-tetrazol-5-yl,
- (k) --NH--SO.sub.2 CF.sub.3,
- (l) CN,
- (m) NO.sub.2,
- (n) C.sub.1 -C.sub.5 -alkyl-CO.sub.2 R.sup.9,
- (o) aryl,
- (p) aryl-C.sub.1 -C.sub.3 -alkyl,
- (q) heteroaryl,
- (r) C.sub.1 -C.sub.5 -alkyl-CONR.sup.21 R.sup.22,
- (s) --CONR.sup.21 R.sup.22,
- (t) 2-oxazolin-2-yl optionally bearing one or more C.sub.1 -C.sub.4 -alkyl substituents,
- (u) C.sub.1 -C.sub.5 -alkyl-S(O).sub.p,
- (v) (CH.sub.2).sub.t OCOR.sup.22,
- (w) (CH.sub.2).sub.t NR.sup.21 COR.sup.22,
- (x) (CH.sub.2).sub.t NR.sup.21 CONR.sup.21 R.sup.22,
- (y) --(CH.sub.2).sub.t OCONR.sup.21 R.sup.22,
- (z) --(CH.sub.2).sub.t NR.sup.21 CO.sub.2 R.sup.22,
- (aa) --(CH.sub.2).sub.t NR.sup.21 CON(CH.sub.2 CH.sub.2).sub.2 L,
- (bb) --(CH.sub.2).sub.t OCON(CH.sub.2 CH.sub.2).sub.2 L,
- (cc) --N(CH.sub.2 CH.sub.2).sub.2 L,
- (dd) --C.sub.1 -C.sub.5 -alkyl-CON(CH.sub.2 CH.sub.2).sub.2 L,
- (ee) --CON(CH.sub.2 CH.sub.2).sub.2 L,
- (ff) aryl-C.sub.1 -C.sub.3 -alkoxy, or
- (gg) --(CH.sub.2).sub.t COR.sup.22 ;
- u is 1; and
- X is:
- (a) a single bond,
- (b) --C(O)--, or
- (c) --NR.sup.15 C(O)--.
- 3. The compound according to claim 2 wherein:
- R.sup.1 is ##STR81## E is a single bond or --S--; R.sup.6 is
- (a) C.sub.1 -C.sub.6 alkyl unsubstituted or substituted with --F, --CF.sub.3, cyclopropyl, or C.sub.1 -C.sub.2 -alkyl-cyclopropyl or
- (b) cyclopropyl, unsubstituted or substituted with --CH.sub.3, --C.sub.2 H.sub.5, --CF.sub.3 or --CF.sub.2 CF.sub.3 ;
- A is O, S or NR.sup.21 ;
- B is
- (a) H provided A is not NR.sup.21,
- (b) C.sub.1 -C.sub.10 -alkyl,
- (c) substituted C.sub.1 -C.sub.10 -alkyl in which one or two substituents are selected from:
- (1) hydroxy,
- (2) C.sub.1 -C.sub.5 -alkoxy,
- (3) C.sub.1 -C.sub.5 -alkoxycarbonyl,
- (4) C.sub.1 -C.sub.4 -alkylcarbonyloxy,
- (5) C.sub.3 -C.sub.8 -cycloalkyl,
- (6) phenyl,
- (7) substituted phenyl in which the substituents are V.sub.1, V.sub.2, V.sub.3, V.sub.4 and V.sub.5,
- (8) C.sub.1 -C.sub.5 -alkyl-S(O).sub.p
- (9) phenyl-S(O).sub.p
- (10) substituted phenyl-S(O).sub.p in which the substituent is V,
- (11) oxo,
- (12) carboxy,
- (13) C.sub.1 -C.sub.5 -alkylaminocarbonyl;
- (d) C.sub.2 -C.sub.10 -alkenyl,
- (e) C.sub.2 -C.sub.10 -alkynyl,
- (f) C.sub.3 -C.sub.8 -cycloalkyl,
- (g) substituted C.sub.3 -C.sub.8 -cycloalkyl or substituted C.sub.3 -C.sub.8 -cycloalkyl-C.sub.1 -C.sub.4 -alkyl in which one or more substituent(s) is selected from:
- (1) hydroxy,
- (2) C.sub.1 -C.sub.5 -alkoxy,
- (3) C.sub.1 -C.sub.5 -alkoxycarbonyl,
- (4) C.sub.1 -C.sub.4 -alkylcarbonyloxy,
- (5) C.sub.1 -C.sub.6 -alkyl,
- (6) phenyl,
- (7) substituted phenyl in which the substituents are V.sub.1, V.sub.2, V.sub.3, V.sub.4, and V.sub.5,
- (8) oxo,
- (9) carboxy,
- (10) C.sub.1 -C.sub.5 -alkylaminocarbonyl;
- (h) mono-, di-, tri-, or polyfluoro-C.sub.1 -C.sub.10 -alkyl,
- (i) phenyl, biphenyl or naphthyl,
- (j) substituted phenyl, biphenyl or naphthyl in which the substituents are V.sub.1, V.sub.2, V.sub.3, V.sub.4 and V.sub.5,
- (k) phenyl--(CH.sub.2).sub.r --(Q).sub.c --(CH.sub.2).sub.t --,
- (l) substituted phenyl--(CH.sub.2).sub.r --(Q).sub.c --(CH.sub.2).sub.t --,
- (m) heterocycle--(CH.sub.2).sub.r --(Q).sub.c --(CH.sub.2).sub.t --, wherein the heterocycle is 5- or 6-membered containing one or two heteroatoms such as pyridine, furan, pyrrole, imidazole or thiazole and unsubstituted or substituted with V.sub.1 and V.sub.2 ;
- V.sub.1, V.sub.2, V.sub.3, V.sub.4 and V.sub.5 are independently selected from:
- (a) hydrogen,
- (b) C.sub.1 -C.sub.5 -alkoxy,
- (c) C.sub.1 -C.sub.5 -alkyl,
- (d) hydroxy,
- (e) NR.sup.9 R.sup.10,
- (f) CO.sub.2 R.sup.9,
- (g) trifluoromethyl,
- (h) halogen,
- (i) hydroxy-C.sub.1 -C.sub.4 -alkyl,
- (j) -1H-tetrazol-5-yl,
- (k) --NH--SO.sub.2 CF.sub.3,
- (l) CN,
- (m) NO.sub.2,
- (n) C.sub.1 -C.sub.5 -alkyl-CO.sub.2 R.sup.9,
- (o) aryl,
- (p) aryl-C.sub.1 -C.sub.3 -alkyl,
- (q) heteroaryl,
- (r) C.sub.1 -C.sub.5 -alkyl-CONR.sup.21 R.sup.22,
- (s) --CONR.sup.21 R.sup.22,
- (t) 2-oxazolin-2-yl optionally bearing one or more C.sub.1 -C.sub.4 -alkyl substituents,
- (u) C.sub.1 -C.sub.5 -alkyl-S(O).sub.p,
- (v) (CH.sub.2).sub.t OCOR.sup.22,
- (w) (CH.sub.2).sub.t NR.sup.21 COR.sup.22,
- (x) (CH.sub.2).sub.t NR.sup.21 CONR.sup.21 R.sup.22,
- (y) --(CH.sub.2).sub.t OCONR.sup.21 R.sup.22,
- (z) --(CH.sub.2).sub.t NR.sup.21 CO.sub.2 R.sup.22,
- (aa) --(CH.sub.2).sub.t NR.sup.21 CON(CH.sub.2 CH.sub.2).sub.2 L,
- (bb) --(CH.sub.2).sub.t OCON(CH.sub.2 CH.sub.2).sub.2 L,
- (cc) --N(CH.sub.2 CH.sub.2).sub.2 L,
- (dd) --C.sub.1 -C.sub.5 -alkyl-CON(CH.sub.2 CH.sub.2).sub.2 L,
- (ee) --CON(CH.sub.2 CH.sub.2).sub.2 L,
- (ff) aryl-C.sub.1 -C.sub.3 -alkoxy, or
- (gg) --(CH.sub.2).sub.t COR.sup.22,
- u is 1; and
- X is:
- (a) a single bond,
- (b) --C(O)--, or
- (c) --NR.sup.15 C(O)--.
- 4. The compound according to claim 3 wherein:
- A is O, S or NR.sup.21 ;
- B is
- (a) H provided A is not NR.sup.21,
- (b) C.sub.1-C.sub.10 -alkyl,
- (c) C.sub.3 -C.sub.8 -cycloalkyl,
- (d) C.sub.3 -C.sub.8 -cycloalkyl-C.sub.1 -C.sub.4 -alkyl,
- (e) substituted C.sub.1 -C.sub.10 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, or C.sub.3 -C.sub.8 -cycloalkyl-C.sub.1 -C.sub.4 -alkyl each of which can have one or two substituents selected from the group;
- (1) hydroxy,
- (2) C.sub.1 -C.sub.5 -alkoxy,
- (3) C.sub.1 -C.sub.5 -alkoxycarbonyl,
- (4) phenyl, naphthyl or biphenyl,
- (5) substituted phenyl, naphthyl or biphenyl wherein the substitutents are V.sub.1, V.sub.2, V.sub.3, V.sub.4 and V.sub.5,
- (6) carboxy,
- (7) C.sub.1 -C.sub.5 -alkylaminocarbonyl,
- (8) oxo,
- (9) --NR.sup.21 COR.sup.22,
- (10) --NR.sup.21 CO.sub.2 R.sup.22,
- (11) --OCONR.sup.21 R.sup.22, or
- (12) --CN,
- (f) mono-, di-, tri-, or polyfluoro-C.sub.1 -C.sub.10 -alkyl,
- (g) phenyl, biphenyl or naphthyl,
- (h) substituted phenyl in which the substituents are V.sub.1, V.sub.2, V.sub.3, V.sub.4 and V.sub.5,
- (i) phenyl-(CH.sub.2).sub.r --(Q).sub.c --(CH.sub.2).sub.t --,
- (j) substituted phenyl-(CH.sub.2).sub.r --(Q).sub.c --(CH.sub.2).sub.t -- in which the substituents are V.sub.1, V.sub.2, V.sub.3, V.sub.4 and V.sub.5, or
- (k) a heterocyclic moiety selected from: ##STR82## V.sub.1, V.sub.2, V.sub.3, V.sub.4 and V.sub.5 are selected from: (a) hydrogen,
- (b) C.sub.1 -C.sub.5 -alkyl,
- (c) C.sub.1 -C.sub.5 -alkoxy,
- (d) CO.sub.2 R.sup.9,
- (e) halogen,
- (f) hydroxy-C.sub.1 -C.sub.4 -alkyl-,
- (g) C.sub.1 -C.sub.5 -alkyl-CO.sub.2 R.sup.9,
- (h) C.sub.1 -C.sub.5 -alkyl-CONR.sup.21 R.sup.22,
- (i) CONR.sup.21 R.sup.22,
- (j) CN,
- (k) NO.sub.2,
- (l) CF.sub.3,
- (m) aryl,
- (n) heteroaryl,
- (o) 2-oxazolin-2-yl optionally bearing one or more C.sub.1 -C.sub.4 -alkyl substituents,
- (p) C.sub.1 -C.sub.5 -alkyl-S(O).sub.p,
- (q) (CH.sub.2).sub.t OCOR.sup.22,
- (r) (CH.sub.2).sub.t NR.sup.21 COR.sup.22,
- (s) (CH.sub.2).sub.t NR.sup.21 CO.sub.2 R.sup.22,
- (t) (CH.sub.2).sub.t NR.sup.21 CONR.sup.21 R.sup.22,
- (u) --(CH.sub.2).sub.t OCONR.sup.21 R.sup.22,
- (v) --(CH.sub.2).sub.t NR.sup.21 CON(CH.sub.2 CH.sub.2).sub.2 L,
- (w) --(CH.sub.2).sub.t OCON(CH.sub.2 CH.sub.2).sub.2 L,
- (x) --N(CH.sub.2 CH.sub.2).sub.2 L,
- (y) --C.sub.1 -C.sub.5 -alkyl-CON(CH.sub.2 CH.sub.2).sub.2 L,
- (z) --CON(CH.sub.2 CH.sub.2).sub.2 L,
- (aa) hydroxy,
- (bb) NR.sup.9 R.sup.10,
- (cc) aryl-C.sub.1 -C.sub.3 -alkyl,
- (dd) aryl-C.sub.1 -C.sub.3 -alkoxy, or
- (ee) --(CH.sub.2).sub.t COR.sup.22,
- X is --NR.sup.15 C(O)-- or a carbon--carbon single bond.
- 5. The compound according to claim 4 wherein:
- R.sup.1 is --SO.sub.2 NHCO.sub.2 R.sup.22 ;
- R.sup.6 is C.sub.1 -C.sub.6 -alkyl;
- R.sup.21 is H, substituted or unsubstituted aryl, substituted or unsubstituted C.sub.1 -C.sub.6 -alkyl, or heteroaryl;
- R.sup.22 is
- (a) substituted or unsubstituted aryl,
- (b) substituted or unsubstituted C.sub.1 -C.sub.6 -alkyl, or
- (c) heteroaryl;
- A is O;
- B is substituted phenyl in which the substituents are V.sub.1, V.sub.2, V.sub.3, V.sub.4 and V.sub.5 ;
- V.sub.1, V.sub.2, V.sub.3, V.sub.4 and V.sub.5 are selected from:
- (a) hydrogen,
- (b) C.sub.1 -C.sub.5 -alkyl,
- (c) C.sub.1 -C.sub.5 -alkoxy,
- (d) C.sub.1 -C.sub.5 -alkyl-S(O).sub.p --,
- (e) halogen,
- (f) CONR.sup.21 R.sup.22,
- (g) CN,
- (h) NO.sub.2,
- (i) CF.sub.3,
- (j) aryl,
- (k) heteroaryl,
- (l) --NR.sup.21 COR.sup.22,
- (m) --NR.sup.21 CO.sub.2 R.sup.22,
- (n) --NR.sup.21 CONR.sup.21 R.sup.22,
- (o) --NR.sup.21 CON(CH.sub.2 CH.sub.2).sub.2 L,
- (p) --CON(CH.sub.2 CH.sub.2).sub.2 L,
- (q) NR.sup.9 R.sup.10, or
- (r) --(CH.sub.2).sub.t COR.sup.22 ;
- X is a carbon--carbon single bond;
- E is a single bond; and
- u is 1.
- 6. The compound according to claim 5 having the formula III: ##STR83## wherein:
- __________________________________________________________________________R.sup.1 R.sup.2 R.sup.3 R.sup.x R.sup.y R.sup.z__________________________________________________________________________--SO.sub.2 NHCO.sub.2 Et H H CF.sub.3 H H--SO.sub.2 NHCO.sub.2 i-Pr H H CF.sub.3 H H--SO.sub.2 NHCO.sub.2 n-Pr H H CF.sub.3 H H--SO.sub.2 NHCO.sub.2 i-Bu H H CF.sub.3 H H--SO.sub.2 NHCO.sub.2 n-Bu H H CF.sub.3 H H--SO.sub.2 NHCO.sub.2 t-Bu H H CF.sub.3 H H--SO.sub.2 NHCO.sub.2 t-Bu H H Cl H H--SO.sub.2 NHCO.sub.2 t-Bu H H Br H H--SO.sub.2 NHCO.sub.2 t-Bu 5'-n-Pr H CF.sub.3 H H--SO.sub.2 NHCO.sub.2 t-Bu 5'-n-Pr 3-F CF.sub.3 H H--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H H--SO.sub.2 NHCO.sub.2 t-Bu H H CF.sub.3 NO.sub.2 H--SO.sub.2 NHCO.sub.2 t-Bu H H CF.sub.3 NH.sub.2 H--SO.sub.2 NHCO.sub.2 t-Bu H H CF.sub.3 NHCOCH.sub.2 CH.sub.3 H--SO.sub.2 NHCO.sub.2 t-Bu H H Cl H NO.sub.2--SO.sub.2 NHCO.sub.2 t-Bu H H Cl H NH.sub.2--SO.sub.2 NHCO.sub.2 t-Bu H H Cl H NH(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H Cl H NHCH.sub.2 -phenyl--SO.sub.2 NHCO.sub.2 t-Bu H H Cl H NHCOCH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H Cl H NHCOCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H Cl H NHCO(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H Cl H NHCO(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H Cl H NHCOCH(CH.sub.3).sub.2--SO.sub.2 NHCO.sub.2 t-Bu H H Cl H NHCOCH.sub.2 CH(CH.sub.3).sub.2--SO.sub.2 NHCO.sub.2 t-Bu H H Cl H NHCO-cyclopropyl--SO.sub.2 NHCO.sub.2 t-Bu H H Cl H NHCO-phenyl--SO.sub.2 NHCO.sub.2 t-Bu H H Cl H NHCOCH.sub.2 -phenyl--SO.sub.2 NHCO.sub.2 t-Bu H H Cl H NHCO(CH.sub.2).sub.2 -phenyl--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H NHCO-(4-pyridyl)--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H NHCO-(3-pyridyl)--SO.sub.2 NHCO.sub.2 t-Bu H H Cl H NHCOO(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H Cl H NHCONH(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H NHCO-(4-morpholinyl)--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H NHCOCH.sub.2 OCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H NHCOCH.sub.2 SCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H CONHCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H Cl H CONH(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H Cl H CONH(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H Cl H CON(CH.sub.3)(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H COCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H Cl H CO(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H Cl H CO(CH.sub.2).sub.3 CH.sub.3--SO.sub. 2 NHCO.sub.2 t-Bu H 3-F Cl H CO(CH.sub.2).sub.4 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H SO(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H NHCOCH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu 5'-n-Pr 3-F Cl H NHCOCH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H NHCOCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H NHCO(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H NHCO(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H NHCO-phenyl--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H CONH(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H CONH(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H CO(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H CO(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu 5'-Et 3-F Cl H NHCOCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu 5'-F 3-F Cl H NHCOCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu 3',6'-diF H Cl H NHCOCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 2-F Cl H NHCOCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H CF.sub.3 H NHCOCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H CF.sub.3 H NHCO(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H CF.sub.3 H NHCO(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H CF.sub.3 H NHCO-phenyl--SO.sub.2 NHCO.sub.2 t-Bu H H CF.sub.3 H CONH(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H CF.sub.3 H CONH(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H CF.sub.3 H CO(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H CF.sub.3 H CO(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H NHCOCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H NHCO(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H NHCO(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H NHCO-phenyl--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H CONH(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H CONH(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H CO(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H CO(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H Br H NHCOCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H Br H NHCO(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H Br H NHCO(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H Br H NHCO-phenyl--SO.sub.2 NHCO.sub.2 t-Bu H H Br H CONH(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H Br H CONH(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H Br H CO(CH.sub.2).sub.2 CH.sub.3-- SO.sub.2 NHCO.sub.2 t-Bu H H Br H CO(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H NHCOCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H NHCO(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H NHCO(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H NHCO-phenyl--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H CONH(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H CONH(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H CO(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H CO(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H H H NHCO(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H H H H CONH(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F H H NHCO(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F H H CONH(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu 5'-n-Pr 3-F H H NHCOCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu 5'-n-Pr 3-F H H CONHCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 n-Bu H 3-F Cl H NHCOCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 i-Bu H 3-F Cl H NHCOCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 n-Pr H 3-F Cl H NHCOCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H NHCOCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et 5'-n-Pr 3-F Cl H NHCOCH.sub.3--SO.sub.2 NHCO.sub.2 Et 5'-n-Pr 3-F Cl H NHCOCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H COCH.sub.2 -phenyl--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H Co-phenyl--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H NHCO(CH.sub.2).sub.4 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H NHCO(CH.sub.2).sub.5 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H CONH-phenyl--SO.sub.2 NHCO.sub.2 t-Bu 5'-Et 3-F Cl H NHCO(CH.sub.2).sub.3 CH.sub.3--SO.sub. 2 NHCO.sub.2 t-Bu 5'-F 3-F CF.sub.3 H NHCOCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu 3',6'-diF H CF.sub.3 H NHCOCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 2-F CF.sub.3 H NHCOCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H NHCO(CH.sub.2).sub.4 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H NHCOCH.sub.2 OCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H NHCOCH.sub.2 SCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H NHCOCH.sub.2 SCH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H NHCOCH.sub.2 OCH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H NHCO(CH.sub.2).sub.2 OCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H NHCO(CH.sub.2).sub.2 SCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H NHCO(CH.sub.2).sub.2 OCH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H NHCO(CH.sub.2).sub.2 SCH.sub.3-- SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H NHCOCH.sub.2 OCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H NHCOCH.sub.2 SCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H NHCOCH.sub.2 SCH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H NHCOCH.sub.2 OCH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H NHCO(CH.sub.2).sub.2 OCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H NHCO(CH.sub.2).sub.2 SCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H NHCO(CH.sub.2).sub.2 OCH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H NHCO(CH.sub.2).sub.2 SCH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H NHCOCH.sub.2 SCH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H NHCOCH.sub.2 OCH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H NHCO(CH.sub.2).sub.2 OCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H NHCO(CH.sub.2).sub.2 SCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H NHCO(CH.sub.2).sub.2 OCH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H NHCO(CH.sub.2).sub.2 SCH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H CONH(CH.sub.2).sub.4 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H CONH(CH.sub.2).sub.5 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H CONHCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H CONH-phenyl--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H CO(CH.sub.2).sub.4 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H CO-phenyl--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H COCH.sub.2 -phenyl--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H CONH(CH.sub.2).sub.4 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H CONHCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H NHCO(CH.sub.2).sub.4 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H CO(CH.sub.2).sub.4 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H CO-phenyl--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H COCH.sub.2 -phenyl--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H CONH(CH.sub.2).sub.2 OCH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H CONH(CH.sub.2).sub.2 SCH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H CONH(CH.sub.2).sub.2 OCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Cl H CONH(CH.sub.2).sub.2 SCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H CONH(CH.sub.2).sub.2 OCH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H CONH(CH.sub.2).sub.2 SCH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H CONH(CH.sub.2).sub.2 OCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H CONH(CH.sub.2).sub.2 SCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H CONH(CH.sub.2).sub.2 OCH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H CONH(CH.sub.2).sub.2 SCH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H CONH(CH.sub.2).sub.2 OCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H CONH(CH.sub.2).sub.2 SCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H NHCO-(4-pyridyl)--SO.sub.2 NHCO.sub.2 t-Bu H 3-F CF.sub.3 H NHCO-(3-pyridyl)--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H NHCO-(4-pyridyl)--SO.sub.2 NHCO.sub.2 t-Bu H 3-F Br H NHCO-(3-pyridyl)--SO.sub.2 NHCO.sub.2 n-Pr H 3-F CF.sub.3 H NHCOCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 t-Bu 5'-n-Pr 3-F Cl H NHCO-cyclopropyl--SO.sub.2 NHCO.sub.2 Et 5'-n-Pr 3-F Cl H NHCO-cyclopropyl--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H NHCOCH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H NHCO-cyclopropyl--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H NHCO(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H NHCO(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H NHCO(CH.sub.2).sub.4 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H NHCO-phenyl--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H CONHCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H CONH(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H CONH(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H CONH(CH.sub.2).sub.2 OCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H CONH(CH.sub.2).sub.2 SCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H CONH(CH.sub.2).sub.2 OCH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H CONH(CH.sub.2).sub.2 SCH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H CO(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H CO(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H CO-phenyl--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H COCH.sub.2 -phenyl--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H NHCOCH.sub.2 OCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H NHCOCH.sub.2 SCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H NHCOCH.sub.2 SCH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H NHCOCH.sub.2 OCH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H NHCO(CH.sub.2).sub.2 OCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H NHCO(CH.sub.2).sub.2 SCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H NHCO(CH.sub.2).sub.2 OCH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H NHCO(CH.sub.2).sub.2 SCH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H NHCO-(4-pyridyl)--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H NHCO-(3-pyridyl)--SO.sub.2 NHCO.sub.2 Et H 3-F Cl H SO(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H NHCOCH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H NHCO-cyclopropyl--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H NHCOCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H NHCO(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H NHCO(CH.sub.2).sub.3 CH.sub.3--SO.sub. 2 NHCO.sub.2 Et H 3-F CF.sub.3 H NHCO(CH.sub.2).sub.4 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H NHCO-phenyl--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H CONHCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H CONH(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H CONH(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H CONH(CH.sub.2).sub.2 OCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H CONH(CH.sub.2).sub.2 SCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H CONH(CH.sub.2).sub.2 OCH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H CONH(CH.sub.2).sub.2 SCH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H CO(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H CO(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H CO-phenyl--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H COCH.sub.2 -phenyl--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H NHCOCH.sub.2 OCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H NHCOCH.sub.2 SCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H NHCOCH.sub.2 SCH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H NHCOCH.sub.2 OCH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H NHCO(CH.sub.2).sub.2 OCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H NHCO(CH.sub.2).sub.2 SCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H NHCO(CH.sub.2).sub.2 OCH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H NHCO(CH.sub.2).sub.2 SCH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H NHCO-(4-pyridyl)--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H NHCO-(3-pyridyl)--SO.sub.2 NHCO.sub.2 Et H 3-F CF.sub.3 H SO(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H NHCOCH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H NHCO-cyclopropyl--SO.sub.2 NHCO.sub.2 Et H 3-F Br H NHCOCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H NHCO(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H NHCO(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H NHCO(CH.sub.2).sub.4 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H NHCO-phenyl--SO.sub.2 NHCO.sub.2 Et H 3-F Br H CONHCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H CONH(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H CONH(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H CONH(CH.sub.2).sub.2 OCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H CONH(CH.sub.2).sub.2 SCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H CONH(CH.sub.2).sub.2 OCH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H CONH(CH.sub.2).sub.2 SCH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H CO(CH.sub.2).sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H CO(CH.sub.2).sub.3 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H CO-phenyl--SO.sub.2 NHCO.sub.2 Et H 3-F Br H COCH.sub.2 -phenyl--SO.sub.2 NHCO.sub.2 Et H 3-F Br H NHCOCH.sub.2 OCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H NHCOCH.sub.2 SCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H NHCOCH.sub.2 SCH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H NHCOCH.sub.2 OCH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H NHCO(CH.sub.2).sub.2 OCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H NHCO(CH.sub.2).sub.2 SCH.sub.2 CH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H NHCO(CH.sub.2).sub.2 OCH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H NHCO(CH.sub.2).sub.2 SCH.sub.3--SO.sub.2 NHCO.sub.2 Et H 3-F Br H NHCO-(4-pyridyl)--SO.sub.2 NHCO.sub.2 Et H 3-F Br H NHCO-(4-pyridyl)--SO.sub.2 NHCO.sub.2 Et H 3-F Br H SO(CH.sub.2).sub.3 CH.sub.3__________________________________________________________________________
- 7. The compound according to claim 5 which is:
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]biphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]biphenyl-4-yl]methyl]-5-n-butyl-2-[2-chloro-5-(valerylamino)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2-[5-(N-n-butylcarbamoyl)-2-chlorophenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2-[2-(trifluoromethyl)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]biphenyl-4-yl]methyl]-5-n-butyl-2-[2-(trifluoromethyl)-5-(propionylamino)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one,
- 2-[2-Bromo-5-(propionylamino)phenyl]-4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one
- 2-[5-(Benzoylamino)-2-bromophenyl]-4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-2-[5-(propionylamino)-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-2-[2-(trifluoromethyl)-5-(valerylamino)phenyl]-3H-1,2,4-triazol-3-one,
- 2-[5-(Benzoylamino)-2-(trifluoromethyl)phenyl]-4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2-[2-chloro-5-(propionylamino)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]biphenyl-4-yl]methyl]-5-n-butyl-2-[2-chloro-5-(propionylamino)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one,
- 2-[5-(Acetylamino)-2-chlorophenyl]-4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]-3-fluoro-5'-n-propylbiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2-[2-chloro-5-(2-ethoxyacetylamino)phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2-[2-chloro-5-[(ethylthioacetyl)amino]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2-[5-(N-n-butylcarbamoyl)-2-(trifluoromethyl)phenyl-2,4-dihydro-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-2-[5-(N-n-propylcarbamoyl)-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-2-[5-(N-ethylcarbamoyl)-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-2-[5-(N-phenylcarbamoyl)-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one,
- 2-[2-Bromo-5-(N-n-butylcarbamoyl)phenyl]-4-[[2'-N-(t-butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]-methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one,
- 2-[2-Bromo-5-(N-n-propylcarbamoyl)phenyl]-4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one,
- 2-[2-Bromo-5-(N-ethylcarbamoyl)phenyl]-4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one
- 2-[2-Bromo-5-(N-phenylcarbamoyl)phenyl]-4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-2-[5-[(ethylthioacetyl)amino]-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-2-[5-[(methylthioacetyl)amino]-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-2-[5-[[3-(methylthio)propionyl]amino]-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl-5-n-butyl-2,4-dihydro-2-[5-[(ethoxyacetyl)amino]-2-(trifluoromethyl)phenyl]3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-2-[5-[(methoxyacetyl)amino]-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-2-[5-[(3-methoxypropionyl)amino]-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-2-[5-[(3-ethoxypropionyl)amino]-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one,
- 2-[2-Bromo-5-[(ethylthioacetyl)amino]phenyl]-4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one,
- 2-[2-Bromo-5-[(methylthioacetyl)amino]phenyl]-4-[[2'-[N-t-butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one,
- 2-[2-Bromo-5-[[3-(methylthio)propionyl]amino]phenyl]-4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one,
- 2-[2-Bromo-5-[(ethoxyacetyl)amino]phenyl]-4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one,
- 2-[2-Bromo-5-[(methoxyacetyl)amino]phenyl]-4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one,
- 2-[2-Bromo-5-[(3-methoxypropionyl)amino]phenyl]-4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]methyl]5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one,
- 2-[2-Bromo-5-[(3-ethoxypropionyl)amino]phenyl-4-[[2'-[N-t-butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-]methyl-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one,
- 2-[5-(Acetylamino)-2-chlorophenyl]-5-n-butyl-2,4-dihydro-4-[[2'-[N-(ethoxycarbonyl)sulfamoyl]-3-fluoro-5'-n-propylbiphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one,
- 2-[5-(Acetylamino)-2-chlorophenyl]-5-n-butyl-2,4-dihydro-4-[[2'-[N-(ethoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one,
- 5-n-Butyl-2-[2-chloro-5-[(cyclopropanecarbonyl)amino]phenyl]-2,4-dihydro-4-[[2'-[N-(ethoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one,
- 5-n-Butyl-2-[2-chloro-5-(propionylamino)phenyl]-2,4-dihydro-4-[[2'-[N-(ethoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one,
- 5-n-Butyl-2-[5-(N-n-butylcarbamoyl)-2-chlorophenyl]-2,4-dihydro-4-[[2'-[N-(ethoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one,
- 2-[5-(Acetylamino)-2-(trifluoromethyl)phenyl]-5-n-butyl-2,4-dihydro-4-[[2'-[N-(ethoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one,
- 5-n-Butyl-2-[5-[(cyclopropanecarbonyl)amino]-2-(trifluoromethyl)phenyl]-2,4-dihydro-4-[[2'-[N-(ethoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one,
- 5-n-Butyl-2,4-dihydro-4-[[2'-[N-(ethoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-2-[5-(propionylamino)-2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one,
- 5-n-Butyl-2-[5-(N-n-butylcarbamoyl)-2-(trifluoromethyl)phenyl]-2,4-dihydro-4-[[2'-[N-(ethoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one,
- 2-[2-Bromo-5-(propionylamino)phenyl]-5-n-butyl-2,4-dihydro-4-[[2'-[N-(ethoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one,
- 2-[2-Bromo-5-(N-n-butylcarbamoyl)phenyl]-5-n-butyl-2,4-dihydro-4-[[2'-[N-(ethoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-3H-1,2,4-triazol-3-one,
- 2-[5-(Acetylamino)-2-chlorophenyl]-4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-2,4-dihydro-5-n-propyl-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-2-[2-chloro-5-[(cyclopropanecarbonyl)amino]phenyl]-2,4-dihydro-5-n-propyl-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-2-[2-chloro-5-(propionylamino)phenyl]-2,4-dihydro-5-n-propyl-3H-1,2,4-triazol-3-one,
- 2-[5-(N-n-Butylcarbamoyl)-2-chlorophenyl]-4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-2,4-dihydro-5-n-propyl-3H-1,2,4-triazol-3-one,
- 2-[5-(Acetylamino)-2-(trifluoromethyl)phenyl]-4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-2,4-dihydro-5-n-propyl-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-2,4-dihydro-2-[5-[(cyclopropanecarbonyl)amino]-2-(trifluoromethyl)phenyl]-5-n-propyl-3-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-2,4-dihydro-2-[5-(propionylamino)-2-(trifluoromethyl)phenyl]-5-n-propyl-3H-1,2,4-triazol-3-one,
- 4-[[2'-[N-(t-Butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-2-[5-(N-n-butylcarbamoyl)-2-(trifluoromethyl)phenyl]-2,4-dihydro-5-n-propyl-3H-1,2,4-triazol-3-one,
- 2-[5-(Acetylamino)-2-chlorophenyl]-2,4-dihydro-4-[[2'-[N-(ethoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-propyl-3H-1,2,4-triazol-3-one,
- 2-[2-Chloro-5-[(cyclopropanecarbonyl)amino]phenyl]-2,4-dihydro-4-[[2'-[N-(ethoxycarbonyl)-sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-propyl-3H-1,2,4-triazol-3-one,
- 2-[2-Chloro-5-(propionylamino)phenyl]-2,4-dihydro-4-[[2'-[N-(ethoxycarbonyl)-sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-propyl-3H-1,2,4-triazol-3-one,
- 2-[5-(N-n-Butylcarbamoyl)-2-chlorophenyl]-2,4-dihydro-4-[[2'-[N-(ethoxycarbonyl)-sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-propyl-3H-1,2,4-triazol-3-one,
- 2-[5-(Acetylamino)-2-(trifluoromethyl)phenyl]-2,4-dihydro-4-[[2'-[N-(ethoxycarbonyl)-sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-propyl-3H-1,2,4-triazol-3-one,
- 2-[5-[(Cyclopropanecarbonyl)amino]-2-(trifluoromethyl)phenyl]-2,4-dihydro-4-[[2'-[N-(ethoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-propyl-3H-1,2,4-triazol-3-one,
- 2,4-Dihydro-4-[[2'-[N-(ethoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-2-[5-(propionylamino)-2-(trifluoromethyl)phenyl]-5-n-propyl-3H-1,2,4-triazol-3-one, or
- 2-[5-(N-n-Butylcarbamoyl)-2-(trifluoromethyl)phenyl]2,4-dihydro-4-[[2'-[N-(ethoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-propyl-3H-1,2,4-triazol-3-one.
- 8. A pharmaceutical composition useful in the treatment of hypertension which comprises a pharmaceutically acceptable carrier and a pharmaceutically effective amount of a compound of claim 1.
- 9. A method of treating hypertension which comprises administering to a patient in need of such treatment a pharmaceutically effective amount of a compound of claim 1.
- 10. An ophthalmological formulation for the treatment of ocular hypertension comprising an ophthalmologically acceptable carrier and an effective ocular antihypertensive amount of a compound of claim 1.
- 11. A method of treating ocular hypertension comprising administering to a patient in need of such treatment an effective ocular antihypertensive amount of a compound of claim 1.
RELATED APPLICATION
The present patent application is a continuation-in-part of copending application Ser. No. 07/875,038 filed May 1, 1992 now abandoned, which is a continuation-in-part application of application Ser. No. 07/698,505, filed May 10, 1991, now abandoned.
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323841 |
Jul 1989 |
EPX |
400974 |
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EPX |
409332 |
Jan 1991 |
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412594 |
Feb 1991 |
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475898 |
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WOX |
Continuation in Parts (2)
|
Number |
Date |
Country |
Parent |
875038 |
May 1992 |
|
Parent |
698505 |
May 1991 |
|