Substituted imidazo-fused 6-membered heterocycles as angiotensin II antagonists

Abstract

Substituted Imidazo-fused 6-membered heterocycles of structural formula: ##STR1## wherein A, B, C, and D are independently carbon atoms or nitrogen atoms are angiotensin II antagonists useful in the treatment of hypertension and congestive heart failure.

Description

Claims

1. A compound of structural formula: ##STR33## or a pharmaceutically acceptable salt thereof, wherein: R.sup.1 is

(a) --CO.sub.2 R.sup.4,

(b) --SO.sub.3 R.sup.5,

(c) --NHSO.sub.2 CF.sub.3,

(d) --PO(OR.sup.5).sub.2,

(e) --SO.sub.2 NHR.sup.9,

(f) --CONHOR.sup.5, ##STR34## (h) --SO.sub.2 NH-heteroaryl, (i) --CH.sub.2 SO.sub.2 NH-heteroaryl,

(j) --SO.sub.2 NHCOR.sup.23,

(k) --CH.sub.2 SO.sub.2 NHCOR.sup.23,

(l) --CONHSO.sub.2 R.sup.23,

(m) --CH.sub.2 CONHSO.sub.2 R.sup.23,

(n) --NHSO.sub.2 NHCOR.sup.23,

(o) --NHCONHSO.sub.2 R.sup.23,

(p) --SO.sub.2 NHCONR.sup.23, ##STR35## wherein heteroaryl is an unsustituted, monosubstituted or disubstituted five- or six-membered aromatic ring which contains 1 to 3 heteroatoms selected from the group consisting of O, N or S and wherein the sustituents are members selected from the group consisting of --OH, --SH, --C.sub.1 -C.sub.4 alkoxy, halo, --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 ;

R.sup.2a and R.sup.2b are independently H, halo, --NO.sub.2, --NH.sub.2, C.sub.1 -C.sub.4 alkylamino, di(C.sub.1 -C.sub.4 alkyl)amino --SO.sub.2 NHR.sup.9, CF.sub.3, C.sub.1 -C.sub.4 alkyl, or C.sub.1 -C.sub.4 alkoxy;

R.sup.3a is

(a) H,

(b) halo,

(c) C.sub.1 -C.sub.6 alkyl,

(d) C.sub.1 -C.sub.6 alkoxy, or

(e) C.sub.1 -C.sub.6 alkoxyalkyl;

R.sup.3b is

(a) H,

(b) halo,

(c) NO.sub.2,

(d) C.sub.1 -C.sub.6 alkyl,

(e) C.sub.1 -C.sub.6 acyloxy,

(f) C.sub.1 -C.sub.6 cycloalkyl,

(g) C.sub.1 -C.sub.6 alkyoxy,

(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) C.sub.1 -C.sub.4 dialkylamino,

(q) fluoro C.sub.1 -C.sub.4 alkyl,

(r) --SO.sub.2 NHR.sup.9,

(s) aryl, or

(t) furyl;

wherein aryl is phenyl or naphthyl either unsubstituted or substituted with one or two substituents selected form the group consisting of halo, 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 alkylthio, OH, NH.sub.2, NH(C.sub.1 -C.sub.4 alkyl), N(C.sub.1 -C.sub.4 alkyl).sub.2, CO.sub.2 H, and CO.sub.2 --C.sub.1 -C.sub.4 alkyl;

R.sup.4 is H, straight chain or branched C.sub.1 -C.sub.6 alkyl, aryl or --CH.sub.2 aryl where aryl is as defined above;

R.sup.4a is C.sub.1 -C.sub.6 alkyl, aryl or --CH.sub.2 aryl where aryl is as defined above;

R.sup.5 is H, ##STR36## E is a single bond, --NR.sup.13 CCH.sub.2).sub.s 13 , --S(O).sub.x --(CH.sub.2).sub.s --, where x is 0 to 2 and s is 0 to 5, --CH(OH)--, --O--, --CO--;

R.sup.6 is

(a) aryl as defined above which is unsubstituted or substituted with 1 or 2 substituents selected from the group consisting of halo, --OC.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, --SC.sub.1 -C.sub.4 alkyl, --OH, --NH.sub.2, C.sub.3 -C.sub.7 cycloalkyl, C.sub.3 -C.sub.10 alkenyl;

(b) straight chain or branched C.sub.1 1.varies.C.sub.9 alkyl, C.sub.2 -C.sub.6 alkenyl or C.sub.2 -C.sub.6 alkynyl each of which is unsubstituted or substituted with a substituent selected from the group consisiting of aryl as defined above, C.sub.3 -C.sub.7 cycloalkyl, halo, --OH, --NH.sub.2, --NH(C.sub.1 -C.sub.4 alkyl), --CF.sub.2 CF.sub.3, --N(C.sub.1 -C.sub.4 alkyl).sub.2, --NH--SO.sub.2 R.sup.4, --COOR.sup.4, --CF.sub.3, --CF.sub.2 CH.sub.3, --SO.sub.2 NHR.sup.9 ; or

(c) an unsubstituted, monosubstituted or disubstituted aromatic 5 or 6 membered ring which contains one or two members selected from the group consisting of N, O, 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 alkyloxy --CF.sub.3, halo, or NO.sub.2,

(d) perfluoro C.sub.1 -C.sub.4 alkyl,

(e) C.sub.3 -C.sub.7 cycloalkyl which is unsubstituted mono- or disubstituted with C.sub.1 -C.sub.4 alkyl or --CF.sub.3 ;

R.sup.9 is H, C.sub.1 -C.sub.5 alkyl, aryl or --CH.sub.2 aryl, where aryl is as defined above;

R.sup.10 is H, or C.sub.1 -C.sub.4 alkyl;

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, ##STR37## R.sup.12 is --CN, --NO.sub.2 or --CO.sub.2 R.sup.4 ; R.sup.13 is H, --CO(C.sub.1 -C.sub.4 alkyl), 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 cycloalky, phenyl or benzyl;

R.sup.15 is H, C.sub.1 -C.sub.6 alkyl;

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, ##STR38## 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, --OH or --OCH.sub.3 ;

R.sup.23 is

(a) aryl as defined above,

(b) neteroaryl as defined above,

(c) C.sub.3 -C.sub.4 cycloalkyl,

(d) C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted wiht a substituent that is a member selected from the group consisting of aryl as defined above, heteroaryl as defined above, --OH, --Sh, --C.sub.1 -C.sub.4 alkyl, --O(C.sub.1 -C.sub.4 alkyl), --S(C.sub.1 -C.sub.4 alkyl), --CF.sub.3 halo --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), --NHCOR.sup.4a, --N(C.sub.1 -C.sub.4 alkyl).sub.2, --PO.sub.3 H, --PO(OH)(C.sub.1 -C.sub.4 alkyl), --PO(OH)(aryl) or --PO(OH)(O--C.sub.1 -C.sub.4 alkyl),

(e) perfluoroC.sub.1 -C.sub.4 alkyl;

X is

(a) a carbon-carbon single bond,

(b) --CO--,

(c) --O--,

(d) --S--, ##STR39## (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 --, ##STR40## --A--B--C--D-- represents the constituent atoms of a 6-member saturated or unsaturated heterocyclic ring with the imidazole to which they are attached containing 1 to 3 nitrogen atoms and is selected from the following: ##STR41## R.sup.7 groups can be the same or different and represent: a) hydrogen,

b) C.sub.1 -C.sub.6 straight or branched chain alkyl, or C.sub.2 -C.sub.6 alkenyl, or alkynyl each of which is unsubstituted or substituted with:

i) --OH

ii) C.sub.1 -C.sub.4 alkoxy,

iii) --CO.sub.2 R.sup.4,

iv) --OCOR.sup.4, ##STR42## vii) --N--CR.sup.4 viii) --N(R.sup.4).sub.2,

ix) aryl as defined above,

x) heterocyclic as defined in (o) below,

xi) --S(O).sub.x R.sup.23,

xii) tetrazol--5--yl,

xiii) --CONHSO.sub.2 R.sup.23,

xiv) --SO.sub.2 NH--heteroaryl,

xv) --SO.sub.2 NHCOR.sup.23, ##STR43## xix) --PO(OR.sup.4).sub.2, xx) --PO(OR.sup.4)R.sup.9,

c) chloro, bromo or iodo,

d) perfluoro--C.sub.1 -C.sub.4 alkyl,

e) --OH,

f) --NH.sub.2, ##STR44## i) --OR.sup.23, j) --CO.sub.2 R.sup.4,

k) --CON(R.sup.4).sub.2,

l) --NHC.sub.3 -C.sub.7 cycloalkyl,

m) C.sub.3 -C.sub.7 cycloalkyl,

n) aryl as defined above, or

o) heterocyclic which is a five- or six- membered saturated or unsaturated ring containing up to three heteroatoms selected from the group consisting of O, N or S wherein S may in the form of sulfoxide or sulfone and which is unsubstituted or substituted with one or two substituents which are members selected from the group consisting of halo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C=hd 4 alkoxy, C.sub.1 -C.sub.4 alkyl--S(O).sub.x -- where x is as defined above, CF.sub.3, NO.sub.2, OH, 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) or N(R.sup.4).sub.2 ;

p) --CN,

q) (CH.sub.2).sub.n N-- where n is 4 to 6,

r) --SO.sub.2 N(R.sup.4).sub.2 ;

s) tetrazol-5-yl,

t) --CONHSO.sub.2 R.sup.23,

u) --PO(OR.sup.4).sub.2,

v) --NHSO.sub.2 CF.sub.3,

w) --SO.sub.2 NH--heteroaryl,

x) --SO.sub.2 NHCOR.sup.23,

y) --S(O).sub.x R.sup.23, ##STR45## aa) --PO(OR.sup.4)R.sup.9, bb) --NHSO.sub.2 R.sup.23,

cc) --NHSO.sub.2 NHR.sup.23,

dd) --NHSO.sub.2 NHCOR.sup.23,

ee) NHCONHSO.sub.2 R.sup.23,

ff) --N(R.sup.4)CO.sub.2 R.sup.23, ##STR46## hh) --CO--aryl, ##STR47## jj) --COC.sub.1.sup.-C.sub.4 alkyl, kk) --SO.sub.2 NH--CN, ##STR48## R.sup.8 groups can be the same or different and represent: a) hydrogen,

b) C.sub.1 -C.sub.6 alkyl or alkenyl either unsubstituted or substituted with hydroxy, C.sub.1 -C.sub.4 alkoxy, --N(R.sup.4).sub.2, --CO.sub.2 R.sup.4, or C.sub.3 -C.sub.5 cycloalkyl,

c) C.sub.3 -C.sub.5 cycloalkyl,

R.sup.8a is R.sup.8 or C.sub.1 -C.sub.4 acyl; and

R.sup.9a groups can be the same or different and represent:

a) hydrogen,

b) C.sub.1 -C.sub.6 alkyl either unsubstituted or substituted with

i) hydroxy,

ii) --CO.sub.2 R.sup.4,

iii) --CONHR.sup.4, or

iv) --CON(R.sup.4).sub.2.

2. A compound of structural formula: ##STR49## or a pharmaceutically acceptable salt thereof, wherein: R.sup.1 is

a) --CO.sub.2 R.sup.4, ##STR50## c) --NHS0.sub.2 CF.sub.3, d) --SO.sub.2 NH--heteroaryl,

e) --CH.sub.2 SO.sub.2 NH--heteroaryl,

f) --SO.sub.2 NHCOR.sup.23,

g) --CH.sub.2 SO.sub.2 NHCOR.sup.23,

h) --CONHSO.sub.2 R.sup.23, or

i) --CH.sub.2 CONHSO.sub.2 R.sup.23 ;

heteroaryl is an unsubstituted, monsubstituted or disubstituted five- or six-membered aromatic ring which contains 1 to 3 heteroatoms selected from the group consisting of O, N or S and wherein the substituent are members selected from the group consisting of --OH, --SH, --C.sub.1 -C.sub.4 alkyl, --C.sub.1 -C.sub.4 alkoxy, halo, --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 ;

R.sup.2a and R.sup.2b are independently

a) C.sub.1 -C.sub.4 alkyl,

b) chloro, or

c) hydrogen;

R.sup.3a and R.sup.3b are independently

a) C.sub.1 -C.sub.4 alkyl,

b) chloro,

c) C.sub.1 -C.sub.4 alkoxy, or

d) hydrogen;

R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl;

E is a single bond;

R.sup.6 is

a) branched or straight chain C.sub.1 -C.sub.c alkyl, alkenyl or C.sub.2 -C.sub.6 alkynyl each of which is either unsubstituted or substituted with CF.sub.3, CF.sub.2 CH.sub.3 or CF.sub.2 CH.sub.3,

b) C.sub.3 -C.sub.7 cycloalkyl, or

c) perfluoro--C.sub.1; -C.sub.4 alkyl;

--A--B--C--D-- represents the constituent atoms of a 6-member heterocyclic ring with imidazole to which they are attached of the following formula: ##STR51## R.sup.7 groups are the same or different and represent: a) hydrogen,

b) --C.sub.1 -C.sub.4 alkyl, either unsubstituted or substituted with --OH or --CO.sub.2 R.sup.4,

c) halo,

d) --OH,

e) --N(R.sup.4).sub.2,

f) --C.sub.1 -C.sub.4 alkoxy,

g) --C).sub.2 R.sup.4,

h) aryl,

i) heterocyclic,

j) --CF.sub.3, or

k) tetrazol-5-yl;

aryl is phenyl or naphthyl either unsubstituted or substituted with one or two substituents selected from the group consisting of halo, 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 alkylthio, OH, NH(C.sub.1 -C.sub.4 alkyl), N(C.sub.1 -C.sub.4 alkyl).sub.2, C).sub.2 H, and CO.sub.2 --C.sub.1 -C.sub.4 alkyl;

hetero cyclic which is a five- or six-membered saturated or unsaturated ring containing up to three heteroatoms selected from the group consisting of O, N or S wherein S may in the form of sulfoxide or sulfone and which is unsubstituted or substituted with one or two substituents which are members selected from the group consisting of halo, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 --S(O).sub.x -- where x is 0 to 2, CF.sub.3, N).sub.2, OH, CO.sub.2 --C.sub.1 -C.sub.4 alkyl, NH.sub.2, NH(C.sub.1 -C.sub.4 alkyl) or N(R.sup.4).sub.2 ;

R.sup.8 is

a) hydrogen, or

b) C.sub.1 -C.sub.4 alkyleither unsubstituted or substituted with --OH or --CO.sub.2 R.sup.4 ;

X is a single bond;

R.sup.23 is

a) aryl,

b) heteroaryl,

c) C.sub.1 -C.sub.4 cycloalkyl,

d) C.sub.1 -C.sub.4 alkyl which is unsubstituted or substituted with a substituent that is a member selected from the group consisting of aryl, heteroaryl, --OH, --SH, --C.sub.1 -C.sub.4 alkyl, --O(C.sub.1 -C.sub.4 alkyl), --S(C.sub.1 -C.sub.4 alkyl, --CF.sub.3, halo, --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). --NHCOR.sup.4a, --N(C.sub.1 -C.sub.4 alkyl).sub.2, --PO.sub.3 H, --PO(OH)(C.sub.1 -C.sub.4 alkyl), --PO(OH)(aryl) or --PO(OH)(O--C.sub.1 -C.sub.4 alkyl),

e) perfluoro--C.sub.1 -C.sub.4 alkyl; and

R.sup.4a is C.sub.1 -C.sub.6 alkyl, aryl or --CH.sub.2 aryl.

3. The compound of claim 2 wherein:

--A--B--C--D-- is ##STR52##

4. The compound of claim 3 wherein:

R.sup.1 is --CO.sub.2 R.sup.4.

5. The compound of claim 4 which is:

(1) 3-(2'-carboxybiphen-4-yl)methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine;

(2) 3-(2'-carboxybiphen-4-yl)methyl-2ethyl-7-methyl-3H-imidazo[4,5-b]pyridine;

(3) 3(2'-carboxybiphen-4-yl)methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine; or

(4) 3-(2'-carboxybiphen-4-yl)methyl-2-cyclopropyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine.

6. The compound of claim 3 wherein:

R.sup.1 is ##STR53##

7. The compound of claim 6 which is:

(1) 2-butyl-3-(2'-tetrazol-5-yl)biphen-4yl)methyl-3H-imidazo[4,5-b]pyridine;

(2) 2-propyl-3-(2'-(tetrazol-5-yl)biphen-4-yl)mehtyl-3H-imidazo[4,5-b]pyridine

(3) 5,7-dimethyl-2ethyl-3-(2'-tetrazol-5-yl)biphen-4-yl)mehtyl-3H-imidazo[4,5-b]pyridine;

(4) 2-ethyl-7-methyl-3-(2'-(tetrazol-5-yl)biphen-4-yl)methyl-3H-imidazo[4,5-b]pyridine;

(5) 5,7-dimethyl-2-propyl-3-(2'-(tetrazol-5-yl)biphen-4-yl)methyl-3H-imidazo[4,5-b]pyridine;

(6) 2-cyclopropyl-5,7-dimethyl-3-(2'-(tetrazol-5-yl)biphen-4-yl)methyl-3H-imidaza[4,5-b]pyridine;

(7) 5-ehtyl-7-methyl-2-propyl-3-(2'-(tetrazol-5-yl)biphen-4-yl)mehtyl-3H-imidazo[4,5-b]pyridine;

(8) 5-amino-2-ethyl-3-(2-(tetrazol-5-yl)biphen-4-y)methyl-7-trifluoromethyl-3H-imidazo[4,5-b]pyridine;

(9) 2-ethyl-5-hydroxymethyl-7-methyl-3-(2'-(tetrazol-5-yl)biphen-4-yl)mehtyl-3H-imidazo[4,5-b]pyridine;

(10) 5-carbomethoxy-2-ethyl-7methyl-3-(2'-(tetrazol-5-yl)biphen-4-yl)methyl-3H-imidazo-[4,5-b]pyridine;

(11) 5,7-dimethyl-3-(2'-(tetrazol-5-yl)biphen-4-yl)methyl-2-(3,3,3,-trifluoro)propyl-3H-imidazo[4,5-b]pyridine;

(12) 5,7-dimethyl-3-(2'-(tetrazol-5-yl)biphen-4-yl)mehtyl-2-(trans-1-propenyl)-3H-imidazo[4,5-b]pyridine;

(13) 7-methyl-2-propyl-3-(2'-(tetrazol-5-yl)biphen-4-yl)methyl-3H-imidazo[4,5-b]pyridine sodium salt; or

(14) 7-methyl-2-propyl-3-(2'-(tetrazol-5-yl)biphen-4-yl)methyl-3H-imidazo[4,5-b]pyridine potassium salt.

8. The compound of claim 3 wherein:

R.sup.1 is SO.sub.2 NHCOR.sup.23.

9. The compound of claim 8 which is:

(1) 3-(2'-(N-acetyl)sulfonamidobiphen-4-yl)methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine;

(2) 3-(2'-(N-benzoyl)sulfonamidobiphen-4-yl)methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine;

(3) 5,7-dimethyl-2-ethyl-3-(2'-(N-(4-nitro)-benzoyl)sulfonamidobiphen-4-yl)methyl-3H-imidazo[4,5-b]pyridine; or

(4) 3-(2'-(N-(4-chloro)benzoyl)sulfonamidodiphen-4-yl)methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine.

10. The compound of claim 3 wherein:

R.sup.1 is

a) --NHSO.sub.2 CH.sub.3,

b) --SO.sub.2 NH-heteroaryl,

c) --CH.sub.2 SO.sub.2 NH-heteroaryl,

d) --CH.sub.2 SO.sub.2 NHCOR.sup.23,

e) --CONHSO.sub.2 R.sup.23, or

f) --CH.sub.2 CONHSO.sub.2 R.sup.23.

11. The compound of claim 10 which is:

(1) 7-methyl-3-(2'-(N-phenylsulfonyl)carboxamidobiphen-4-yl)methyl-2-propyl-3H-imidazo[4,5-b]pyridine;

(2) 3-(2'-((N-acetylsulfonamido)methyl)biphen-4-yl)methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine; or

(3) 7-methyl-2-propyl-3-(2'-trifluoromethanesulfonylamino)-biphen-4-yl)methyl-3H-imidazo[4,5-b]pyridine.

12. The compound of claim 2 wherein:

--A--B--C--D-- is ##STR54##

13. The compound of claim 7 which is:

(1) 9-(2'-carboxybiphen-4-yl)methyl-2,6-dimethyl-8-ethylpurine;

(2) 6-methyl-8-propyl-9-(2'-(tetrazol-5-yl)biphen-4-yl)-methylpurine;

(3) 2,6-dimethyl-8-propyl-9-(2'-(tetrazol-5-yl)biphen-4yl)-methylpurine;

(4) 2,6-dimethyl-8-ethyl-9-(2'-(tetrazol-5-yl)biphen-4-yl)-methylpurine;

(5) 8-ethyl-6-methyl-2-methylamino-9-(2'-(tetrazol-5-yl)biphen-4-yl)methylpurine;

(6) 8-ethyl-6-methyl-2-(morpholin-4-yl)-9-(2'-(tetrazol-5-yl)-biphen-4-yl)methylpurine;

(7) 2-carboxy-8-ethyl-6-methyl-9-(2'-(tetrazol-5-yl)biphen-4-yl)methylpurine; or

(8) 6-methyl-2-methylamino-8-propyl-9-(2'-(tetrazol-5-yl-biphen-4-yl)methylpurine.

14. The compound of claim 6 which is:

7-methyl-2-propyl-3-(2'-tetrazol-5-yl)biphen-4-yl0methyl-3H-imidazo[4,5-b]pyridine.

15. The compound of claim 7 which is:

5,7-dimethyl-2-ethyl-3-(2'-(tetrazol-5-yl)methyl-3H-imidazo[4,5-b]pyridine.

16. The compound of claim 6 which is:

5-carboxy-2-ethyl-7-methyl-3-(2'-(tetrazol-5-yl)biphen-4-yl)methyl-3H-imidazo-[4,5-b]pyridine.

17. The compound of claim 6 which is:

5,7-dimethyl-2-ethyl-3-(2'-trifluoromethanesulfonylamino)biphen-4-yl)methyl-3H-imidazopyridine.

18. The compound of claim 9 which is:

3-(2'-(N-acetyl)sulfonamidobiphen-4-yl)methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine.

19. The compound of claim 9 which is:

3-(2'-(N-benzoyl)sulfonamidobiphen-4-yl)methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine.

20. A pharmaceutical formulation for the treatment of hypertension and congestive heart failure comprising a pharmaceutically acceptable carrier and an effective antihypertensive amount of the compound of claim 2.

21. A method of treating hypertension and congestive heart failure comprising the administration of an effective antihypertensive amount of the compound of claim 2 to a patient in need of such treatment.