EP0664803A1 - N-arylheteroarylalkyl 1-cycloalkyl-imidazol-2-one compounds for treatment of circulatory disorders - Google Patents

N-arylheteroarylalkyl 1-cycloalkyl-imidazol-2-one compounds for treatment of circulatory disorders

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EP0664803A1
EP0664803A1 EP93915307A EP93915307A EP0664803A1 EP 0664803 A1 EP0664803 A1 EP 0664803A1 EP 93915307 A EP93915307 A EP 93915307A EP 93915307 A EP93915307 A EP 93915307A EP 0664803 A1 EP0664803 A1 EP 0664803A1
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methyl
butyl
phenyl
pyridinyl
dihydro
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German (de)
French (fr)
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David B. Reitz
Robert E. Manning
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GD Searle LLC
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GD Searle LLC
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives

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  • Medicinal Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
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Abstract

A class of N-arylheteroarylalkyl 1-cycloalkyl-imidazol-2-one compounds is described for use in treatment of circulatory disorders such as hypertension and congestive heart failure. Compounds of particular interest are angiotension II antagonists of formula (A), wherein A is selected from (a), (b), (c), (d), (e) and (f); wherein each of R?1, R2 and R3¿ is independently selected from hydrido, alkyl, alkoxy, halo, hydroxy, carboxyl, alkoxycarbonyl, formyl and acetyl; wherein R7 is hydrido; R8 is alkyl; wherein R9 is an acidic group selected from COOH and (g); or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.

Description


  
 



      N-ARYLHETEROARYLALKYL 1 - CYCLOALKYL -IMIDAZOL- 2 - ONE   
 COMPOUNDS FOR TREATMENT OF CIRCULATORY DISORDERS
 Related   Application   
 This is a continuation-in-part of U.S.



  Application Ser. No. PCT/US92/02439 filed 1 April 1992 which is a continuation-in-part of U.S. Application Ser.



  No. 07/681,011 filed 5 April 1991.



   Field of the Invention
 Non-peptidic N-arylheteroarylalkyl imidazol-2one compounds are described for use in treatment of circulatory disorders such as hypertension and congestive heart failure. Of particular interest are angiotensin II antagonist compounds provided by a 1-cycloalkyl-imidazol2-one having an arylheteroarylmethyl moiety attached at the 3-nitrogen atom of the l-cycloalkyl-imidazol-2-one.



   Background of the Invention
 The renin-angiotensin system is one of the hormonal mechanisms involved in regulation of pressure/volume homeostasis and in expression of hypertension. Activation of the renin-angiotensin cascade begins with renin secretion from the juxtaglomerular apparatus of the kidney and culminates in the formation of angiotensin II, the primary active species of this system.



  This octapeptide, angiotensin   II,    is a potent vasoconstrictor agent and also produces other physiological effects such as promoting aldosterone secretion, promoting sodium and fluid retention, inhibiting renin secretion, increasing sympathetic nervous system activity, increasing vasopressin secretion, causing positive cardiac inotropic effect and modulating other hormonal systems.  



   Previous studies have shown that antagonizing angiotensin II at its receptors is a viable approach to inhibit the renin-angiotensin system, given the pivotal role of this octapeptide which mediates the actions of the renin-angiotensin system through interaction with various tissue receptors. There are several known angiotensin II antagonists, most of which are peptidic in nature. Such peptidic compounds are of limited use due to their lack of oral bioavailability or their short duration of action.



  Also, commercially-available peptidic angiotensin II antagonists (e.g., Saralasin) have a significant residual agonist activity which further limit their therapeutic application.



   Non-peptidic compounds with angiotensin II antagonist properties are known. For example, the sodium salt of   2-n-butyl-4-chloro-l- (2-chlorobenzyl) imidazole-5-    acetic acid has specific competitive angiotensin II antagonist activity as shown in a series of binding experiments, functional assays and in vivo tests [P. C.



  Wong et al, J. Pharmacol.   Exit.    Ther., 247(1), 1-7 (1988)].



  Also, the sodium salt of 2-butyl-4-chloro-l-(2nitrobenzyl)imidazole-5-acetic acid has specific competitive angiotensin II antagonist activity as shown in a series of binding experiments, functional assays and   ln    vivo tests [A. T. Chiu et al, European J. Pharmacol., 157, 13-21 (1988)]. A family of 1-benzylimidazole-5-acetate derivatives has been shown to have competitive angiotensin
II antagonist properties [A. T. Chiu et al, J. Pharmacol   Exc. Ther.,      250(3),    867-874 (1989)]. U.S. Patent No.



  4,816,463 to Blankey et al describes a family of 4,5,6,7   tetrahydro-1H-imidazo (4,5-c) -tetrahydro-pyridine    derivatives useful as antihypertensives, some of which are reported to antagonize the binding of labelled angiotensin
II to rat adrenal receptor preparation and thus cause a  significant decrease in mean arterial blood pressure in conscious hypertensive rats. EP No. 253,310, published 20 January 1988, describes a series of aralkyl imidazole compounds, including in particular a family of biphenylmethyl substituted imidazoles, as antagonists to the angiotensin II receptor.

  EP No. 323,841 published 12 July 1989 describes four classes of angiotensin II antagonists, namely, biphenylmethylpyrroles, biphenylmethylpyrazoles, biphenylmethyl-1,2,3-triazoles and biphenylmethyl   4-substituted-4H-1,2,4-triazoles,    including the compound   3,5-dibutyl-4-[(28-carboxybiphenyl-    4-yl)methyl]-4H-1,2,4-triazole. U.S. Patent No. 4,880,804 to Carini et al describes a family of biphenylmethylbenzimidazole compounds as angiotensin II receptor blockers for use in treatment of hypertension and congestive heart failure.



   There are several families of known compounds having one or two oxo substituents on a triazole ring.



  For example, East German Patent No. 160,447 published 3
August 1983 describes a family of 1,2,4-triazolin-5-one compounds, specifically 2,4-dihydro-4,5-bis(phenylmethyl)3H-1,2,4-triazol-3-one, for use as herbicides. Belgian
Patent No. 806,146 published 16 October 1972 describes a family of triazolinone compounds, including the compound   (3-(4-m-chlorophenyl-1-piperazinyl)-propyl)-3,4-diethyl-    1,2,4-triazolin-5-one, having tranquilizer, hypotensive and analgesic activities. Belgian Patent No. 631,842 published 28 February 1963 describes a family of 1,2,4-triazolones having hypnotic, tranquilizer, narcotic, sedative and analgetic activities, which includes a class of 4-Naralkyl-1,2,4-triazol-5-one compounds.

  EP #7,180 published 15 June 1978 describes a family of 1,2   disubstituted-4-alkyl-l, 2, 4-triazolidine-3 , 5-dione    compounds having a wide variety of activities, such as  antiulcer, bronchodilator, antifertility and cardiovascular-related activities which include antihypertensive,   antiarrhythmic,    platelet aggregation inhibition and smooth muscle activities. EP #283,310 published 18 March 1987 describes a family of N1   diarylmethyl-N2 -aminoalkyl-diaza-heterocyclic    derivatives for treating cerebral vascular and ischemic diseases and for protecting against anoxia.  



   DESCRIPTION OF THE INVENTION
 A class of N-substituted arylheteroarylalkyl 1cycloalkyl-imidazol-2-one compounds useful in treating circulatory disorders, particularly cardiovascular disorders, is defined by Formula I:
EMI5.1     
 wherein Q is a cycloalkyl group having three to about eight ring carbon atoms, and wherein said cycloalkyl group may be unsubstituted or substituted on one or more substitutable positions by one or more groups independently selected from hydrido, alkyl, alkoxy, cyano, halo, hydroxy, nitro, amino, alkylamino, carboxyl, alkoxycarbonyl,   form,    oxo, alkylcarbonyl and haloalkylcarbonyl; wherein R7 is selected from hydrido, alkyl, halo, haloalkyl, formyl, carboxyl and alkoxyalkyl; wherein R8 is selected from alkyl, phenyl, phenylalkyl, cycloalkyl and cycloalkylalkyl; 

   wherein A is an acidgroup-substituted pyridinyl-phenyl moiety selected from
EMI5.2     
 wherein m is a number selected from one to four, inclusive; wherein R9 is an acidic group selected from
COOH and  
EMI6.1     
 or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



     Regioisomers    of compounds of Formula I are also embraced as part of the invention, particularly those regioisomers formed by various substitutions on nitrogen atoms of the imidazole ring relative to substitutions on the carbon atoms of the imidazole ring. For purposes of nomenclature, a numbering system for the imidazole ring is   shown    below for a preferred set of compounds of the invention within Formula I:
EMI6.2     
 wherein each of Q, R7, R8, m and A is as defined above.



   Within Formula I, above, Q may be further defined as
EMI6.3     
 wherein each of R1, R2, R3, R4, R5 and R6 is independently selected from hydrido, alkyl, alkoxy, cyano, halo, hydroxy, nitro, amino, alkylamino, carboxyl,  alkoxycarbonyl, formyl, alkylcarbonyl and haloalkylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R3 and R4 may further be taken together to form oxo; wherein R5 and R6 may further be taken together to form oxo; wherein each of d, b and r is a number selected from zero through five, inclusive, and wherein the sum of d+b+r is a number from zero through five, inclusive;
 Examples of cycloalkyl groups embraced by the Q group are the following moieties:
EMI7.1     
 cyclopropyl cyclobutyl cyclopentyl
EMI7.2     

 cyclohexyl cycloheptyl cyclooctyl wherein each of R1, R2 and R3 is defined above.



   Compounds of Formula   I    would be useful in treating a variety of circulatory disorders and circulatory-related disorders, including cardiovascular disorders, such as hypertension, congestive heart failure and arteriosclerosis, and other disorders such as glaucoma. These compounds would also be useful as adjunctive therapies. For example, compounds of Formula I may be used in combination with other drugs, such as a diuretic, to treat hypertension. Also, compounds of
Formula I could be used in conjunction with certain surgical procedures. For example, these compounds could be used to prevent post-angioplasty re-stenosis.  



  Compounds of Formula I are therapeutically effective in treatment of cardiovascular disorders by acting as antagonists to, or blockers of, the angiotensin II   (AII)    receptor. Compounds of Formula I would be therapeutically effective in treatment of the above-mentioned circulatory and cardiovascular disorders or would be precursors to, or prodrugs of, therapeutically-effective compounds.



   Within Formula I there is a first group of compounds of more interest as represented by Formula II:
EMI8.1     
 wherein each of R1 through R6 is independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, cyano, fluoro, chloro, iodo, bromo, hydroxy, nitro, amino,
N-methylamino, N,N-dimethylamino, N-ethylamino, N,Ndiethylamino, carboxyl, methoxycarbonyl, ethoxycarbonyl, formyl, methylcarbonyl, ethylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R3 and R4 may further   b    taken together to form oxo; wherein R5 and R6 may further be taken together to form oxo; wherein each of d, b and r is a number selected from zero through five, inclusive, and wherein the sum of d+b+r is a number selected from zero through five, inclusive;

   wherein   7    is selected from hydrido, methyl, fluoro, chloro, monofluoromethyl, difluoromethyl, trifluoromethyl, formyl,  carboxyl and dimethoxymethyl; wherein R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, phenyl, benzyl, phenethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl and cyclohexylethyl; wherein A is an acidic-group-substituted pyridinyl-phenyl moiety selected from
EMI9.1     
 wherein R9 is an acidic group selected from COOH and
EMI9.2     
 or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   Within the compounds of Formula II there is a first group of compounds of more interest as represented by Formula III:  
EMI10.1     
 wherein each of R1, R2 and R3 is independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, cyano, fluoro, chloro, iodo, bromo, hydroxy, nitro, amino,
N-methylamino, N,N-dimethylamino, N-ethylamino, N,Ndiethylamino, carboxyl, methoxycarbonyl, ethoxycarbonyl, formyl, methylcarbonyl, ethylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is selected from hydrido, methyl, fluoro, chloro, monofluoromethyl, difluoromethyl, trifluoromethyl, formyl, carboxyl and dimethoxymethyl;

   wherein R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, phenyl, benzyl, phenethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl and cyclohexylethyl; wherein A is an acidic-group-substituted pyridinyl-phenyl moiety selected from
EMI10.2     
  wherein R9 is an acidic group selected from COOH and
EMI11.1     
 or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   Within this first group of compounds of Formula
III there is a first class of higher-interest compounds of
Formula III(a):
EMI11.2     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tert-butyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyi, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula   III (a)    consists of compounds and their stereoisomers and tautomers and the  pharmaceutically-acceptable salts thereof, said compounds consisting of    1-(2-methylcyclopropyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2 one;    1-(2-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-propylcyclopropyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-isopropylcyclopropyl)-4-butyl-1,3-dihydro-3-[[5-[2- (lH-tetrazol-5-yl)phenyl] -2-pyridinyl)methyl] -2H-imidazol-    2-one;

  ;    1-(2-tertbutylcyclopropyl)-4-butyl-1,3-dihydro-3-[[5-[2- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-methOxyCyclopropyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-hydroxyCyclopropyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-carboxyCyclopropyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-acetylcyclopropyl)-4-butyl-l,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyljmethyl]-2H-imidazol-2one;   l-(2-oxocyclopropyl)-4-butyl-l,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one; 

   1-(2,3-dimethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[5-[2 (1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one;  1-(2-ethyl-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3-[[5   [2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2 -one; 1-(2-isopropyl-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3    [[5-[2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2 -one; 1-(2-carboxy-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3    [[5-[2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2-one;

   1-(2-acetyl-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3    [[5-[2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2 -one;    1-(2-oXo-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3-[[5- [2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2-methyl-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[5- [2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2 -one;    1-(2,3-diethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[5-[2- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-isopropyl-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-    [[5-[2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;

  ;   1- (2-carboxy-3-ethylcyclopropyl)-4-butyl-l,3-dihydro-3-    [[5-[2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-acetyl-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[5   [2- (1H-tetrazol-5-yl)phenyl] -2-pyridinyl]methyl]-2H-    imidazol-2-one;

   1-(2-oxo-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[5-[2    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;   1-(2-methyl-3-isopropylcyclopropyl)-4-butyl-1,3-dihyaro-3-    [[5-[2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl)methyl]-2Himidazol-2 -one;     1- (2-ethyl-3-isopropylcyclopropyl)-4-butyl-1,3-dihydro-3- [[5-[2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2 -one;    1-(2,3-diisopropylcyclopropyl)-4-butyl-1,3-dihydro-3-[[5- [2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2 -one;

   1-(2-carboxy-3-isopropylcyclopropyl)-4-butyl-1,3-dihydro3-[[5-[2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;    1- (2-acetyl-3-isopropylcyclopropyl)-4-butyl-1,3-dihydro-3-    [[5-[2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;   1- (2-oxo-3-isopropylcyclopropyl) -4-butyl-1, 3-dihydro-3-    [[5-[2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one; 1-(2,2-dimethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[5-[2 (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one; and    1-(2,2-diethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[5-[2-    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one.



   Within this first group of compounds of Formula
III there is a second class of higher-interest compounds of Formula III(b):
EMI14.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tert-butyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo,  carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula III(b) consists of compounds and their stereoisomers and tautomers and the pharmaceutically-acceptable salts thereof, said compounds consisting of    1-(2-methylcyclopropyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-propylcyclopropyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-y1)phenyl] -3-pyridinyl]rnethyl]-2H-imidazol-2-    one;    1-(2-isopropylcyclopropyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;

  ;    1-(2-tertbutylcyclopropyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-methOxyCyclopropyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinylimethyl]-2H-imidazol-2-    one;    1-(2-hydroxyCyclopropyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyljmethyl]-2H-imidazol-2one;     1-(2-carboxyCyclopropyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-acetylcyclopropyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;   1- (2-oxocyclopropyl)-4-butyl-1,3-dihydro-3-[ [6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;

  ;    i-(2,3-dimethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-ethyl-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3-[[6- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one;

   1-(2-isopropyl-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3    [[6-[2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one;    1- (2-carboxy-3-methylcyclopropyl) -4-butyl-1, 3-dihydro-3-    [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl)methyl]-2Himidazol-2-one;   ¯h-(2-acetyl-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3-    [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    -(2-oXo-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3-[[6-
L2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one;

   1-(2-methyl-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[6   ,2-(lH-tetrazol-5-Yl)phenyl]-3-pyrizinyl]methyl]-2H-    imidazol-2-one;    ¯-(2,3-diethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[6-[2-
SlH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imiCazol-    -one; (2-isopropyl-3-ethylcyclopropyl)-4-butyl-l,3-dihydro-3 [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;  1-(2-carboxy-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3 [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    1-(2-acetyl-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[6- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one; 1-(2-oxo-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[6-[2    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;

   1-(2-methyl-3-isopropylcyclopropyl)-4-butyl-1,3-dihydro-3 [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    1- (2-ethyl-3-isopropylcyclopropyl)-4-butyl-l,3-dihydro-3-    [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; 1-(2,3-diisopropylcyclopropyl)-4-butyl-1,3-dihydro-3-[[6   [2- (1H-tetrazol-5-y1)phenyl] -3-pyridinyl]methyl) -2H-    imidazol-2-one; 

   1-(2-carboxy-3-isopropylcyclopropyl)-4-butyl-1,3-dihydro3-[[6-[2-(1H-tetrazol-5-yl]phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    1- (2-acetyl-3-isopropylcyclopropyl)-4-butyl-1,3-dihydro-3- [[6-[2- (1H-tetrazol-5-yl)phenyl] -3-pyridinyl]methyl]-2H-    imidazol-2-one;   1- (2-oxo-3-isopropylcyclopropyl) -4-butyl-1, 3-dihydro-3-    [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    1-(2,2-dimethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one; and 1-(2,2-diethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[6-[2    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one.  



   Within this first group of compounds of Formula
III there is a third class of higher-interest compounds of
Formula III(c):
EMI18.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tert-butyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula III(c) consists of compounds and their stereoisomers and tautomers and the pharmaceutically-acceptable salts thereof, said compounds consisting of    1-(2-methylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    l-(2-ethylcyclopropyl)-4-butyl-l,3-dihydro-3-[[4-[3-(l:

  :-t-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-propylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl] -2-pyridinyl]methyl]-2H-imidazol-2-    one;     1-(2-isopropylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-tertbutylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3-    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one;    1-(2-methOxyCyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-hydroxyCyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;

  ;    1-(2-carboxyCyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-y1)phenyl) -2-pyridinyl]methyl] -2H-imidazol-2-    one;    1-(2-acetylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;   l-(2-oxocyclopropyl)-4-butyl-1,3-dihydro-3-[ [4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one; 1-(2,3-dimethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3 (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one;

   1-(2-ethyl-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4   [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2-one;    1- (2-isopropyl-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;    1-(2-carboxy-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3- [[4- [3- (1H-tetrazol-5-yl)phenyl] -2-pyridinyl]methyl]-2H-    imidazol-2-one; 1-(2-acetyl-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3 [[4-[3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;     1- (2-oxo-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3-[ [4- [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2-one;

   1-(2-methyl-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4 [3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;    1-(2,3-diethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3- (1H-tetrazol-5-yl)phenyl) -2-pyridinyl]methyl) -2H-imidazol-    2-one;    1-(2-isopropyl-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl)methyl]-2Himidazol-2-one; i-(2-carboxy-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3 [[4-[3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-acetyl-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4   [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2-one;

   1-(2-oxo-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-methyl-3-isopropylcyclopropyl)-4-butyl-1,3-dihydro-3- [[4-[3- (1H-tetrazol-5-yl)phenyl] -2-pyridinyl]methyl]-2H-    imidazol-2-one;    1- (2-ethyl-3-isopropylcyclopropyl)-4-butyl-1,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;    1-(2,3-diisopropylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4- [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2-carboxy-3-lsopropylcyclopropyl)-4-butyl-1,3-dihydro-    3-[[4-[3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;

  ;    1- (2-acetyl-3-isopropylcyclopropyl)-4-butyl-1,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;     1- (2-oxo-3-isopropylcyclopropyl) -4-butyl-l,3-dihydro-3- [[4-[3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2,2-dimethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one; and    1-(2,2-diethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one.



   Within this first group of compounds of Formula
III there is a fourth class of higher-interest compounds of Formula III(d):
EMI21.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tert-butyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula III(d) consists of compounds and their stereoisomers and tautomers and the  pharmaceutically-acceptable salts thereof, said compounds consisting of    1-(2-methylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2 one;    1-(2-propylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-isopropylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[4-    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;

  ;    1-(2-tertbutylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[4-    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2-methoxycyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[4-(1Htetrazol-5-yl)phenyl]-3-pyridinylmethyl]-2H-imidazol-2one;   1-(2-hydroxycyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-carboxyCyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one; 1-(2-acetylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[4-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;   1-(2-oXocyclopropyl)-4-butyl-',3-dinyaro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one; 

   1-(2,3-dimethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[4    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;     1- (2-ethyl-3-methylcyclopropyl)-4-butyl-l,3-dihydro-3-[ [4- [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2-isopropyl-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3- [[4-[4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one; 1-(2-carboxy-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3    [[4-[4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2 -one; 1-(2-acetyl-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3    [[4-[4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one;

   1-(2-oxo-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4   [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2-methyl-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4- [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one; 1-(2,3-diethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[4 (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;    1- (2-isopropyl-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-    [[4-[4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]-methyl]-2Himidazol-2-one;   1- (2-carboxy-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-    [[4-[4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; l-(2-acetyl-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4   [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one;

   1-(2-oxo-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[4    (lH-tetrazol-5-yl)phenyl]-3-pyrizinyl]methyl]-2H-imidazol-    2-one;    1- (2-methyl-3-isopropylcyclopropyl) -4-butyl-l,3-dihydro-3-    [[4-[4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;  l-(2-ethyl-3-isopropylcyclopropyl)-4-butyl-l,3-dihydro-3    [[4-[4- (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one; 1-(2,3-diisopropylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4   [4- (1H-tetrazol-5-y1)phenyl] -3-pyridinyljmethyl] -2H-    imidazol-2-one;

   1-(2-carboxy-3-isopropylcyclopropyl)-4-butyl-1,3-dihydro3-[[4-[4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    1- (2-acetyl-3-isopropylcyclopropyl)-4-butyl-1,3-dihydro-3-    [[4-[4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;   1- (2-oxo-3-isopropylcyclopropyl) -4-butyl-1,3-dihydro-3-    [[4-[4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    1-(2,2-dimethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[4-    (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; and 1-(2,2-diethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[4    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one.



   Within this first group of compounds of Formula
III there is a fifth class of higher-interest compounds of
Formula III(e):
EMI24.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tert-butyl, hydroxy, methoxy, fluoro, chloro, iodo,   bromc,     carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula III(e) consists of compounds and their stereoisomers and tautomers and the pharmaceutically-acceptable salts thereof, said compounds consisting of    1-(2-methylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-4-pyridinylGmethyl]-2H-imidazol-2-    one;    1-(2-propylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-isopropylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one;

  ;    1-(2-tertbutylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-methOxyCyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3-(15:- tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-hydroxyCyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1H-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2one;     1-(2-carboxyCyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-acetylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2one;   l-(2-oxocyclopropyl)-4-butyl-1,3-dihydro-3-[ [4-[3-(1H-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2 one;

  ;    1-(2,3-dimethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-ethyl-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4- [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-    imidazol-2 -one; 1-(2-isopropyl-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3    [[4-[3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2-carboxy-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2Himidazol-2-one;   1-(2-acetyl-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2Himidazol-2-one;

   1-(2-oxo-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4   [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2-methyl-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4- [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-    imidazol-2-one; 1-(2,3-diethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyi]-2H-imidazol-    2-one;    1- (2-isopropyl-3-ethylcyclopropyl)-4-butyl-l,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2Himidazol-2-one;  1-(2-carboxy-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3    [[4-[3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-    imidazol-2-one;

   1-(2-acetyl-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4   [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-    imidazol-2-one; 1-(2-oxo-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2-methyl-3-isopropylcyclopropyl)-4-butyl-1,3-dihydro-3 [[4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2Himidazol-2-one;    1- (2-ethyl-3-isopropylcyclopropyl)-4-butyl-1,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2Himidazol-2-one;    1-(2,3-diisopropylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4- [3- (1H-tetrazol-5-yl)phenyl] -4-pyridinyl]methyl) -2H-    imidazol-2-one; 1-(2-carboxy-3-isopropylcyclopropyl)-4-butyl-1,3-dihydro3-[[4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2Himidazol-2-one; 

   1-(2-acetyl-3-isopropylcyclopropyl)-4-butyl-1,3-dihydro-3 [[4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2Himidazol-2-one;   1- (2-oxo-3-isopropylcyclopropyl) -4-butyl-1, 3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2Himidazol-2-one; 1-(2,2-dimethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[3 (1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol2-one; and    1-(2,2-diethylcyclopropyl)-4-butyl-1,3-dihyaro-3-[[4-[3-    (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol2-one.  



   Within this first group of compounds of Formula
III there is a sixth class of higher-interest compounds of
Formula III(f):
EMI28.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tert-butyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula III(f) consists of compounds and their stereoisomers and tautomers and the pharmaceutically-acceptable salts thereof, said compounds consisting of    i-(2-methylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH- tetrazol-5-y1)phenyl] -3-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[2-(1¯- tetrazol-5-yl)phenyl] -3-pyridinyl]methyl]-2H-imidazol-2-    one;    '-(2-propylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH- tetrazol-5-y1)phenyl] -3-pyridinyl]methyl]-2H-imidazol-2-    one;     1-(2-isopropylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;

  ;    1-(2-tertbutylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[2- (1H-tetrazol-5-y1)phenyl]-3-pyridinyl]methyl)-2H-imidazol-    2-one;    1-(2-methOxyCyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH- tetrazol-5-yl)phenyl] -3-pyridinyl]methyl) -2H-imidazol-2-    one;    1-(2-hydroxyCyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-carboxyCyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-acetylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one; 1-(2-oxocyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[2-(1Htetrazol-5-yl)pheny]-3-pyridinyl]methyl]-2H-imidazol-2one;

   1-(2,3-dimethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[2    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2-ethyl-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4   [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2-isopropyl-3-methylcyclopropyl)-4-butyl-1,3-dihydro-3-    [[4-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    i-(2-carboxy-3-methylcyclopropyl)-4-butyl-1,3-dihyaro-3- [[4- [2- (1H-tetrazol-5-y1)phenyl] -3-pyridinyl]methyl]-2H-    imidazol-2-one;   1-(2-acetyl-3-methylcyclopropyl)-4-butyl-1,3-dihyaro-3-    [[4-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;

  ;     1- (2-oxo-3-methylcyclopropyl)-4-butyl-l,3-dihydro-3-[ [4- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one; 1-(2-methyl-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4   [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one; 1-(2,3-diethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[2 (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2-isopropyl-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3 [[4-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;   1- (2-carboxy-3-ethylcyclopropyl) -4-butyl-1,3-dihydro-3-    [[4-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-acetyl-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4   [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one;

   1-(2-oxo-3-ethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[2    (1H-tetrazol-5-yl)phenyl] -3-pyridinylimethyl] -2H-imidazol-    2-one; 1-(2-methyl-3-isopropylcyclopropyl)-4-butyl-1,3-dihydro-3 [[4-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    1- (2-ethyl-3-isopropylcyclopropyl)-4-butyl-1,3-dihydro-3-    [[4-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    1-(2,3-diisopropylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2-carboxy-3-isopropylcyclopropyl)-4-butyl-1,3-dihydro-    3-[[4-[2-(1H-tetrazol-5-yl)pyhenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;

  ;    1- (2-acetyl-3-isopropylcyclopropyl)-4-butyl-1,3-dihydro-3- [[4-[2- (lH-tetrazol-5-yl)phenyl] -3-pyridinyl]methyl]-2H-    imidazol-2-one;     1- (2-oxo-3-isopropylcyclopropyl) -4-butyl-1, 3-dihydro-3- [[4-[2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2 -one;    1-(2,2-dimethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one; and    1-(2,2-diethylcyclopropyl)-4-butyl-1,3-dihydro-3-[[4-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one.



   Within the compounds of Formula II there is a second group of compounds of more interest as represented by Formula IV:
EMI31.1     
 wherein each of R1, R2 and R3 is independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, cyano, fluoro, chloro, iodo, bromo, hydroxy, nitro, amino,
N-methylamino, N,N-dimethylamino, N-ethylamino, N,Ndiethylamino, carboxyl, methoxycarbonyl, ethoxycarbonyl, formyl, methylcarbonyl, ethylcarbonyl and trifluoromethylcarbonyl; wherein   R1    and R2 may further be taken together to form oxo; wherein   7    is selected from hydrido, methyl, fluoro, chloro, monofluoromethyl, difluoromethyl, trifluoromethyl, formyl, carboxyl and dimethoxymethyl;

   wherein   R8    is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, phenyl, benzyl, phenethyl, cyclopropyl,   oyclobutyl,    cyclopentyl,  cyclohexyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl and cyclohexylethyl; wherein A is an acidic-group-substituted pyridinyl-phenyl moiety selected from
EMI32.1     
 wherein   R9    is an acidic group selected from COOH and
EMI32.2     
 or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.

 

   Within this second group of compounds of Formula
IV there is a first class of higher-interest compounds of
Formula IV(a):
EMI32.3     
 wherein each of R1,   R2    and   R3    may be independently selected from hydrido, methyl, ethyl, n-propyl,   isopropyl,     tert-butyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula IV(a) consists of compounds and their stereoisomers and tautomers and the pharmaceutically-acceptable salts thereof, said compounds consisting of    1-(2-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH- tetrazol-5-yl)phenyl) -2-pyridinyl]methyl] -2H-imidazol-2-    one;   1-(2-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-propylcyclobutyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;   1-(2-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3-[[5-[2-    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one;

  ;   1-(2-tertbutylcyclobutyl)-4-butyl-1,3-dihydro-3-[[5-[2-    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one;    1-(2-methOxycyclobutyl)-4-butyl-1,3-dihydro-3-[[5-[2-(1H- tetrazol-5-yl)phenyl] -2-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-hydroxycyclobutyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;     1-(2-carboxycyclobutyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2 one;    1-(2-acetylcyclobutyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2 one; 1-(2-oxocyclobutyl-4-butyl-1,3-dihydro-3-[[5-[2-(1Htetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2 one;

   1-(2,4-dimethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[5-[2 (1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one; 1-(2-ethyl-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[5 [2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;    1- (2-isopropyl-4-methylcyclobutyl)-4-butyl-l,3-dihydro-3-    [[5-[2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;

   1-(2-carboxy-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3 [[5-[2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H   imidazol-2 -one;    1-(2-acetyl-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[5 [2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H   imidazol -2-one;    1-(2-oxo-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[5-[2    (1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-methyl-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[5- [2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2-one;

   1-(2,4-diethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[5-[2    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;   1- (2-isopropyl-4-ethylcyclobutyl)-4-butyl-l,3-dihydro-3- [[5- [2- (1H-tetrazol-5-yl)phenyl] -2-pyridinyl]methyl] -2H- imidazol-2-one;     1-(2-carboxy-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[5   [2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2-one;    1- (2-acetyl-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[ [5- [2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2-oXo-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[5-[2- (lH-tetrazol-5-yl)phenyl] -2-pyridinyl)methyl] -2H-imidazol-    2-one;

   1-(2-methyl-4-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3 [[5-[2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;    1- (2-ethyl-4-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3-    [[5-[2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;    1-(2,4-diisopropylcyclobutyl)-4-butyl-1,3-dihydro-3-[[5- [2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2-one; 1-(2-carboxy-4-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3 [[5-[2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;    1- (2-acetyl-4-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3-    [[5-[2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-oxo-4-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3-[[5   [2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2 -one;

   1-(2,2-dimethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[5-[2 (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one; and 1-(2,2-diethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[5-[2    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one.  



   Within this second group of compounds of Formula
IV there is a second class of higher-interest compounds of
Formula IV(b):
EMI36.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tert-butyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula IV(b) consists of compounds and their stereoisomers and tautomers and the pharmaceutically-acceptable salts thereof, said compounds consisting of    1-(2-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lr.- tetrazol-5-yl)phenyl] -3-pyridinyl]methyl]-2H-imidazol-2-    one;    i-(2-propylcyclobutyl)-4-butyl-1,3-dihydro-3-[[6-[2-( lr-- tetrazol-5-yl)phenyl] -3-pyridinyl]methyl]-2H-imidazol-2-    one;     1-(2-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;

  ;    1-(2-tertbutylcyclobutyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-methOxycyclobutyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2 one;    1-(2-hydroxycyclobutyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-carboxycyclobutyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-acetylcyclobutyl)-4-butyl-1,3-dihydro-3-[[6-[2-tlH- tetrazol-5-yl)phenyl) -3-pyridinyl)methyl] -2H-imidazol-2-    one; 1-(2-oxocyclobutyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one; 

   2-(2,4-dimethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[6-[2    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imiGazol-    2-one; 1-(2-ethyl-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[6 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    i-(2-isopropyl-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3-    [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;   1- (2-carboxy-4-methylcyclobutyl) -4-butyl-l,3-dihydro-3-    [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    i-(2-acetyl-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[6- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one;  1-(2-oxo-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[6-[2    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;

   1-(2-methyl-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[6   [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2,4-diethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[6-[2- (1H-tetrazol-5-yl)phenyl] -3-pyridinyl)methyl] -2H-imidazol-    2-one; 1-(2-isopropyl-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3 [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-carboxy-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[6   [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one;

   1-(2-acetyl-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[6   [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2-oXo-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[6-[2-    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;    1- (2-methyl-3-isopropylcyclobutyl) -4-butyl-l,3-dihydro-3-    [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    1-(2-ethyl-3-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3-    [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H imidazol-2-one;    1-(2,4-diisopropylcyclobutyl)-4-butyl-1,3-dihydro-3-[[6-    [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;

  ;    1-(2-carboxy-4-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3- [[6-[2- (1H-tetrazol-5-yl)phenyl] -3-pyridinyl]methyl]-2H-    imidzol-2-one;    1- (2-acetyl-4-isopropylcyclobutyl)-4-butyl-l,3-dihydro-3-    [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;     1- (2-oxo-4-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3-[ [6- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2,2-dimethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[6-[2-    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; and    1-(2,2-diethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one.



   Within this second group of compounds of Formula
IV there is a third class of higher-interest compounds of
Formula IV(c):
EMI39.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tert-butyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula IV(c) consists of compounds and their stereoisomers and tautomers and the  pharmaceutically-acceptable salts thereof, said compounds consisting of    1-(2-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;   1-(2-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-propylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;

  ;    1-(2-tertbutylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-methOxycyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-hydroxycyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-carboxycyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-acetylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-oXocyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-2-pyridinylZmethyl]-2H-imidazol-,-    one;

  ;    1-(2,4-dimethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-l (lH-tetrazol-5-yl)phenyl]-2-pyrizinyl]methyl]-2H-imizazol-    2-one;     1-(2-ethyl-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4- [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2-one;    1- (2-isopropyl-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;    1- (2-carboxy-4-methylcyclobutyl)-4-butyl-l,3-dihydro-3- [[4- [3- (lH-tetrazol-5-yl)phenyl] -2-pyridinyl)methyl] -2H-    imidazol-2-one;    1-(2-acetyl-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4 [3- (1H-tetrazol-5-yl)phenyl] -2-pyridinyl]methyl) -2H-    imidazol-2-one;

   1-(2-oxo-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol    2-one;    1-(2-methyl-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4- [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2,4-diethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol    2-one;    1- (2-isopropyl-4-ethylcyclobutyl)-4-butyl-l,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;    1-(2-carboxy-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4    [3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one; 

  ;    1-(2-acetyl-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4- [3- (1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2-oXo-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol    2-one;    1-(2-methyl-4-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl2-2-pyridinyl]methyl]-2Himidazol-2-one;     1- (2-ethyl-4-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3- [[4-[3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2,4-diisopropylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4- [3- (1H-tetrazol-5-yl)phenyl] -2-pyridinyl)methyl] -2H-    imidazol-2-one;

  ;    1- (2-carboxy-4-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3-    [[$-[3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-acetyl-4-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3 [[$-[3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-oxo-4-isoporpylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4   [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2-one; 1-(2,2-dimethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-2-pyridinyljmethyl]-2H-imidazol-    2-one; and    1-(2,2-diethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one.



   Within this second group of compounds of Formula
IV there is a fourth class of higher-interest compounds of
Formula IV(d):
EMI42.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tert-butyl, hydroxy,   methoxy,    fluoro, chloro, iodo, bromo,  carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula IV(d) consists of Compounds and their stereoisomers and tautomers and the pharmaceutically-acceptable salts thereof, said compounds consisting of    1-(2-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-y1)phenyl] -3-pyridinyl]methyl) -2H-imidazol-2-    one;    1-(2-propylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;   1-(2-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[4-    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;

   1-(2-tertbutylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[4    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-methOxycyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazolo-2one;    1-(2-hydroxycyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;  1-(2-carboxycyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[4-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2 one; 1-(2-acetylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[4-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-oXocyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl] -3-pyridinyl]methyl) -2H-imidazol-2-    one;

   1-(2,4-dimethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[4    (1H-tetrazol-5-yl)phenyl] -3-pyridinyl]methyl) -2H-imidazol-    2-one;    1-(2-ethyl-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-    [4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2"Himidazol-2-one; 1-(2-isopropyl-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3 [[4-[4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;

   1-(2-carboxy-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3 [[4-[4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    1-(2-acetyl-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4- [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2-oXo-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[4- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-methyl-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4- [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2,4-diethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[4- (1H-tetrazol-5-yl)phenyl] -3-pyridinyljmethyl] -2H-imidazol-    2-one;    1-(2-isopropyl-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-    [[4-[4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;

  ;  1-(2-carboxy-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4   [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one; 1-(2-acetyl-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4   [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2-oXo-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[4- (1H-tetrazol-5-yl)phenyl] -3-pyridinyl)methyl] -2H-imidazol-    2-one;

   1-(2-methyl-4-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3 [[4-[4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    1-(2-ethyl-4-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3-    [[4-[4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    1-(2,4-diisopropylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4- [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one;    1- (2-carboxy-4-isopropylcyclobutyl) -4-butyl-1,3-dihydro-3-    [[4-[4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    1- (2-acetyl-4-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3-    [[4-[4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;

  ;    1-(2-oXo-4-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4- [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one; 1-(2,2-dimethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[4    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one; and   1-(2,2-diethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[4-    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one.  



   Within this second group of compounds of Formula
IV there is a fifth class of higher-interest compounds of
Formula IV(e):
EMI46.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tert-butyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.

 

   A family of specific compounds of particular interest within Formula IV(e) consists of compounds and their stereoisomers and tautomers and the pharmaceutically-acceptable salts thereof, said compounds consisting of    1-(2-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl] -4-pyridinyl]methyl]-2H-imidazol-2-    one;   1-(2-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2one;    l-(2-propylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1H-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2one;     1-(2-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one;

  ;    1-(2-tertbutylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-methOxycyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl) -4-pyridinyl)methyl] -2H-imidazol-2-    one;    1-(2-hydroxycyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-carboxycyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-acetylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2one;   1-(2-oXocyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2one;

   1-(2,4-dimethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-ethyl-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4- [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2-isopropyl-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3- [[4-[3-(lH-tetrazol-5-yl)phenyl] -4-pyridinyl]methyl]-2H-    imidazol-2-one;

   l-(2-carboxy-4-methylcyclobutyl)-4-butyl-l,3-dihydro-3 [[4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2Himidazol-2-one;    1-(2-acetyl-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4- [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinylimethyl]-2H-    imidazol-2-one;  1-(2-oxo-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol- 2-one;    1-(2-methyl-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4   [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-    imidazol-2-one;   1-(2,4-diethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3-    (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol2-one; 1-(2-isopropyl-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3 [[4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2Himidazol-2-one;

   1-(2-carboxy-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4   [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-    imidazol-2-one; 1-(2-acetyl-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4   [3- (lH-tetrazol-5-yl)phenyl] -4-pyridinyl]methyl) -2H-    imidazol-2-one;

   1-(2-oxo-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one;    1- (2-methyl-4-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2Himidazol-2-one;    1- (2-ethyl-4-isopropylcyclobutyl)-4-butyl-l,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2Himidazol-2-one;    1-(2,4-diisopropylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4- [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-    imidazol-2-one;    1- (2-carboxy-4-isopropylcyclobutyl)-4-butyl-l,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2Himidazol-2-one;

  ;    1- (2-acetyl-4-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2Himidazol-2-one;     1-(2-oXo-4-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4- [3- (1H-tetrazol-5-yl)phenyl] -4-pyridinylimethyl] -2H-    imidazol-2 -one;    1-(2,2-dimethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3-    (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol2-one; and    1-(2,2-diethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl) -4-pyridinyl]methyl) -2H-imidazol-    2-one.



   Within this second group of compounds of Formula
IV there is a sixth class of higher-interest compounds of
Formula IV(f):
EMI49.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tert-butyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula IV(f) consists of compounds and their stereoisomers and tautomers and the  pharmaceutically-acceptable salts thereof, said compounds consisting of    1-(2-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2 one;   1-(2-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2 one;    1-(2-propylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl2-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;

  ;    1-(2-tertbutylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[2- (lH-tetrazol-5-yl)phenyl) -3-pyridinyllmethyl] -2H-imidazol-    2-one;    1-(2-methOxycyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-hydroxycyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl2-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-carboxycyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-acetylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl2-3-pyridinyl]methyl]-2H-imidazol-2one; 1-(2-oxocyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one; 

   1-(2,4-dimethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[2    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;  1-(2-ethyl-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4   [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one; 1-(2-isopropyl-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3 [[4-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;   1- (2-carboxy-4-methylcyclobutyl) -4-butyl-1,3-dihydro-3-    [[4-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-acetyl-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    1-(2-oXo-4-methylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;

   1-(2-methyl-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4   [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one; 1-(2,4-diethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[2 (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;    1- (2-isopropyl-4-ethylcyclobutyl) -4-butyl-l,3-dihydro-3-    [[4-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H   imidazol -2-one;    1-(2-carboxy-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4   [2- (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidzol-2-one; 1-[2-acetyl-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4   [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one;

   1-(2-oxo-4-ethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[2 (1H-tetrazol-5-yl)phenyl2-3-pyridinyl]methyl]-2H-imidazol2-one;    1- (2-methyl-4-isopropylcyclobutyl)-4-butyl-l,3-dihydro-3- [[4- [2- (1H-tetrazol-5-yl)phenyl] -3-pyridinyl]methyl] -2H-    imidazoi-2-one;     1- (2-ethyl-4-isopropylcyclobutyl) -4-butyl-l,3-dihydro-3- [[4-[2- (1H-tetrazol-5-yl)phenyl] -3-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2,4-diisopropylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4- [2- (1H-tetrazol-5-yl)phenyl]-3-pyridinyl)methyl)-2H-    imidazol-2-one; 1-(2-carboxy-4-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3 [[4-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]-methyl]-2Himidazol-2-one;    1- (2-acetyl-4-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3-    [[4-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]-methyl]-2Himidazol-2-one;

   1-(2-oxo-4-isopropylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; 1-(2,2-dimethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[2    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one; and 1-(2,2-diethylcyclobutyl)-4-butyl-1,3-dihydro-3-[[4-[2 (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one.  



   Within the compounds of Formula II there is a third group of compounds of more interest as represented by
Formula V:
EMI53.1     
 wherein each of R1, R2 and R3 is independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy,   cyano,    fluoro, chloro, iodo, bromo, hydroxy, nitro, amino,
N-methylamino, N,N-dimethylamino, N-ethylamino, N,Ndiethylamino, carboxyl, methoxycarbonyl, ethoxycarbonyl, formyl, methylcarbonyl, ethylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is selected from hydrido, methyl, fluoro, chloro, monofluoromethyl, difluoromethyl, trifluoromethyl, formyl, carboxyl and dimethoxymethyl;

   wherein R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tertbutyl, n-pentyl, isopentyl, neopentyl, phenyl, benzyl, phenethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl and cyclohexylethyl; wherein A is an acidic-group-substituted pyridinyl-phenyl moiety selected from  
EMI54.1     
 wherein R9 is an acidic group selected from COOH and
EMI54.2     
 or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   Within this third group of compounds of Formula V there is a first class of higher-interest compounds of
Formula V(a):
EMI54.3     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl,  isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula V(a) consists of compounds and their stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of    1-(2-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-propylcyclopentyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-tertbutylcyclopentyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-methOxyCyclopentyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-hydroxyCyclopentyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one    1-(2-carboxyCyclopentyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-acetylcyclopentyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-oXocyclopentyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2,4-dimethylcycloentyl)-4-butyl-1,3-dihydro-3-[[(5-[2-(1H    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-ethyl-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[5-[2- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one; 1-(2-isopropyl-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3 [[5-[2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;  1-(2-carboxy-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[5    [2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-acetyl-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[5- [2- (lH-tetrazol-5-yl)phenyl] -2-pyridinyl)methyl] -2H-imidazol-    2-one;    l-(2-oxo-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[ [5-[2- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-methyl-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[5-[2-    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;

  ;    1-(2,5-diethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH- tetrazol-5-yl)phenyl] -2-pyridinyl)methyl] -2H-imidazol-2-one;    1-(2-isopropyl-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[5 [2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]-methyl]-2H-imidazol2-one;    1-(2-carboxy-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[5-    [2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]-methyl]-2H-imidazol2-one;    1-(2-acetyl-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[5-[2- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one; 1-(2-oxo-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[5-[2    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;   1-(2-methyl-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-    [[5-[2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one; 

   1-(2-ethyl-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[[5    [2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2,5-diisopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[[5-[2- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;  1-(2-carboxy-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3   [[5-[2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2-one;    1- (2-acetyl-5-isopropylcyclopentyl) -4-butyl-l,3-dihydro-3- [[5-[2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2-one; 1-(2-oxo-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[[5    [2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;

   1-(2,2-dimethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[5-[2-(1Htetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; and 1-(2,2-diethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[5-[2-(1H    tetrazol-5-yl)phenyl] -2-pyridinyl)methyl) -2H-imidazol-2-one.   



   Within this third group of compounds of Formula V there is a second class of higher-interest compounds of
Formula V(b):
EMI57.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and   trifluoromethylcarhonyl;    -wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.  



   A family of specific compounds of particular interest within Formula V(b) consists of compounds and their stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of   1-(2-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-propylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-tertbutylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-methOxyCyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-hydroxyCyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-carboxyCyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-acetylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-oxocyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2,4-dimethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-ethyl-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;   1-(2-isopropyl-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-    [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    1-(2-carboxy-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-    [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;     1-(2-acetyl-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;

   1-(2-oxo-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2 (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-methyl-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one; 1-(2,5-diethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-isopropyl-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6    [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2-carboxy-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6    [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-acetyl-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;

   1-(2-oxo-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2 (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;   1- (2-methyl-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-    [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    1-(2-ethyl-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-    [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;    1- (2,5-diisopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[ [6-[2-    (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1- (2-carboxy-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-    [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;

  ;     1- (2-acetyl-5-isopropylcyclopentyl) -4-butyl-1, 3-dihydro-3- [[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one;    1- (2-oxo-5-isopropylcyclopentyl) -4-butyl-1, 3-dihydro-3- [[6- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2,2-dimethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    and 1-(2,2-diethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one.   

 

   Within this third group of compounds of Formula V there is a third class of higher-interest compounds of
Formula V(c):
EMI60.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula V(c) consists of compounds and their  stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of    1-(2-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-2-pyridinylZmethyl]-2H-imidazol-2-one; 1-(2-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-propylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-tertbutylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-methOxyCyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-hydroxyCyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-carboxyCyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1H- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-acetylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-oXocyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2,4-dimethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-ethyl-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3- (1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one; 1-(2-isopropyl-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3   [[4-[3-(lH-tetrazol-5-yl)phenyl] -2-pyridinyl]methyl]-2H-    imidazol-2-one; 1-(2-carboxy-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4 [3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one;

   1-(2-acetyl-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4    [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;     1- (2-oxo-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[ [4-[3-    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-methyl-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    1-(2,5-diethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazdl-5-yl)phenyl] -2-pyridinyl]methyl] -2H-imidazol-2-one;    1-(2-isopropyl-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4    [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;

   1-(2-carboxy-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4 [3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one;    1-(2-acetyl-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3- (1H-tetrazol-5-yl)phenyl] -2-pyridinyl)methyl] -2H-imidazol-2-    one; 1-(2-oxo-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3 (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-methyl-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3- [[4-[3- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2-ethyl-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4- [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;

   1-(2,5-diisopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3 (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-carboxy-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;   1-(2-acetyl-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;     1- (2-oxo-5-isopropylcyclopentyl) -4-butyl-1,3-dihydro-3- [[4- [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2,2-dimethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;

   and 1-(2,2-diethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1Htetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;
 Within this third group of compounds of Formula V there is a fourth class of higher-interest compounds of
Formula V(d):
EMI63.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula V(d) consists of compounds and their stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of   1-(2-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[4-(15:- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;        1-(2-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-propylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-tertbutylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-methOxyCyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-hydroxyCyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-carboxyCyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-acetylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-oXocyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 

   1-(2,4-dimethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[4-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-onei 1-(2-ethyl-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[4 (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-isopropyl-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3- [[4- [4- (lH-tetrazol-5-yl)phenyl] -3-pyridinyl]methyl] -2H-    imidazol-2-one;    1-(2-carboxy-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-    [4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2-acetyl-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4 [4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;

   1-(2-oxo-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[4 (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;     1-(2-methyl-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[4-    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2,5-diethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[4-(1H-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-isopropyl-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4    [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;

   1-(2-carboxy-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4    [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-acetyl-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[4- (lH-tetrazol-5-yl)phenyl] -3-pyridinyl]methyl) -2H-imidazol-2-    one;   1-(2-oXo-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[4-    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;   1- (2-methyl-5-isopropylcyclopentyl) -4-butyl-1,3-dihydro-3-    [[4-[4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;

   1-(2-ethyl-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4    [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2,5-diisopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[4-    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one; 1-(2-carboxy-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3 [[4-[4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;

   1-(2-acetyl-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3   [[4-[4- (lH-tetrazol-5-yl)phenyl] -3-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2-oXo-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-    [4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;     1-(2,2-dimethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    and    1-(2,2-diethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one.   



   Within this third group of compounds of Formula V there is a fifth class of higher-interest compounds of
Formula V(e):
EMI66.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula V(e) consists of compounds and their stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of   1-(2-methylcyclopentyl)-4-butyl-ls3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl] -4-pyridinyl]methyl] -2H-imidazol-2-one; 1-(2-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl] -4-pyridinyl]methyl]-2H-imidazol-2-one;        1-(2-propylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1H    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-tertbutylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-methOxyCyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-hydroxyCyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-carboxyCyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-acetylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-4-pyridinyljmethyl]-2H-imidazol-2-one;    1-(2-oxocyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1H    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2,4-dimethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1H    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-ethyl-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-isopropyl-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3- [[4-[3- (lH-tetrazol-5-yl)phenyl] -4-pyridinyl]methyl]-2H-    imidazol-2-one; 1-(2-carboxy-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4    [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2-acetyl-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4 ([3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol2-one;

   1-(2-oxo-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3 (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-methyl-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-    (1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2one;     1-(2,5-diethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-isopropyl-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4    [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one;

   1-(2-carboxy-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4    [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-acetyl-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-    (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-oXo-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-    one;    1- (2-methyl-5-isopropylcyclopentyl) -4-butyl-1,3-dihydro-3- [[4-[3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-    imidazol-2-one;

   1-(2-ethyl-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4    [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl3-2H-imidazol-    2-one;    1-(2,5-diisopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3- (1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-carboxy-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3- [[4-[3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-    imidazol-2-one;    l-(2-acetyl-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3- [[4-[3- (1H-tetrazol-5-yl)phenyl] -4-pyridinyl]methyl]-2H-    imidazol-2 -one; 

   1-[2-oxo-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4 [3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol2-one;    1-(2,2-dimethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-4-pyridinylimethyl]-2H-imidazol-2-one;    and 1-(2,2-diethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1H   tetrazol-5-yl)phenyl]-4-pyridinylimethyl]-2H-imidazol-2-one.     



   Within this third group of compounds of Formula V there is a sixth class of higher-interest compounds of
Formula V(f):
EMI69.1     
 wherein each of   Rl,    R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula V(f) consists of compounds and their stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of    l-(2-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH- tetrazol-5-yl)phenyl) -3-pyridinyl}methyl] -2H-imidazol-2-one; 1-(2-propylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-tertbutylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[2-(1H    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;        1-(2-methOxyCyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-hydroxyCyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH- tetrazol-5-yl)phenyl) -3-pyridinyl]methyl] -2H-imidazol-2-one; 1-(2-carboxyCyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-acetylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-oXocyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2,4-dimethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-ethyl-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[2-    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;   1-(2-isopropyl-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-    [[4-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-carboxy-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4    [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2-acetyl-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4    [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;

   1-(2-oxo-5-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[2 (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-methyl-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[2-    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one; 1-(2,5-diethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-isopropyl-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;  1-(2-carboxy-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4    [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-acetyl-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[2-    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;

   1-(2-oxo-5-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[2    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;   1- (2-methyl-5-isopropylcyclopentyl) -4-butyl-1,3-dihydro-3-    [[4-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-ethyl-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4    [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1- (2,5-diisopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[ [4-[2- (lH-tetrazol-S-yl)phenyl] -3-pyridinyl)methyl] -2H-imidazol-2-    one;

   1-(2-carboxy-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3 [[4-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;   1- (2-acetyl-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-    [[4-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-oxo-5-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;    1-(2,2-dimethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[2-(1H- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    and 1-(2,2-diethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[4-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;
 Within the compounds of Formula II there is a fourth group of compounds of more interest as represented by
Formula VI:

  :  
EMI72.1     
 wherein each of R1, R2 and R3 is independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, cyano, fluoro, chloro, iodo, bromo, hydroxy, nitro, amino,
N-methylamino, N,N-dimethylamino, N-ethylamino,   N,N-    diethylamino, carboxyl, methoxycarbonyl, ethoxycarbonyl, formyl, methylcarbonyl, ethylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is selected from hydrido, methyl, fluoro, chloro, monofluoromethyl, difluoromethyl, trifluoromethyl, formyl, carboxyl and dimethoxymethyl;

   wherein R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tertbutyl, n-pentyl, isopentyl, neopentyl, phenyl, benzyl, phenethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl and cyclohexylethyl; wherein A is an acidic-group-substituted pyridinyl-phenyl moiety selected from
EMI72.2     
 wherein R9 is an acidic group selected from COOH and  
EMI73.1     
 or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   Within this fourth group of compounds of Formula
VI there is a first class of higher-interest compounds of
Formula VI(a):
EMI73.2     
 wherein each of   R1,    R2 and   R3    may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl methylcarbonyl and trifluoromethylcarbonyl; wherein   R1    and   R2    may further be taken together to form oxo; wherein   R7    is hydrido; wherein   R8    is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.

 

   A family of specific compounds of particular interest within Formula   VI (a)    consists of compounds and their stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of    1-(2-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;        1-(2-ethylcyclohexyl)-4-butyl-lw3-dihydro-3-[[5-[2-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-propylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5-[2-tlH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-tertbutylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-methOxycyclohexyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-hydroxycyclohexyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-carboxycyclohexyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH- tetrazol-5-yl)phenyl3-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-acetylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-oxocyclohexyl)-4-butyl-1,3-dihydro-3-[[5-[2-(1H    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2,6-dimethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5-[2-(1Htetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-ethyl-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5-[2- (lH-tecrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-isopropyl-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5-    [2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one;    1--(2-carboxy-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5-    [2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one;    1-(2-acetyl-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5-[2-    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;

  ;    1-(2-oXo-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5-[2- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imiCazol-2-    one;     1-(2-methyl-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5-[2-    (1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one; 1-(2,6-diethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5-[2-(1Htetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-isopropyl-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5    [2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-carboxy-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5-[2-    (1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-acetyl-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5-[2- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-oXo-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-methyl-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5- [2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;

  ;    1-(2-ethyl-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5- [2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2,6-diisopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5-[2    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;   1- (2-carboxy-6-isopropylcyclohexyl)-4-butyl-l,3-dihydro-3-    [[5-[2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;    1-(2-acetyl-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5- [2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;

   1-(2-oxo-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5-[2    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;    l-(2,2-dimethylcyclohexyl)-4-butyl-l,3-dihydro-3-[[5-[2-(lN-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; and     1-(2,2-diethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[5-[2-( 1H- tetrazol-5-yl)phenyl] -2-pyridinyl]methyl] -2N-imidazol-2-one.   



   Within this fourth group of compounds of Formula
VI there is a second class of higher-interest compounds of
Formula VI(b):
EMI76.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula VI(b) consists of compounds and their stereo isomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of   1-(2-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-propylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;  1-(2-tertbutylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-methOxycyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-hydroxycyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-carboxycyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-acetylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-oXocyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2,6-dimethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-ethyl-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one; 1-(2-isopropyl-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6    [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one; 

   1-(2-carboxy-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;    1-(2-acetyl-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-    (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-oXo-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-methyl-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;    l-(2,6-diethylcyciohexyl)-4-butyl-l,3-dihydro-3-[ [6-[2- (iN-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-isopropyl-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;     1-(2-carboxy-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-acetyl-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl3methyl]-2H-imidazol-2-    one;    1-(2-oXo-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-methyl-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;

   1-(2-ethyl-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6    [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2,6-diisopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;   1-(2-carboxy-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-    [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-acetyl-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6    [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;

   1-(2-oxo-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3[[6-[2    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2,2-dimethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    and 1-(2,2-diethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one.   



   Within this fourth group of compounds of Formula   there    is a third class of higher-interest compounds of
Formula VI(c):  
EMI79.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula VI(c) consists of compounds and their stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of    1-(2-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl] -2-pyridinyl]methyl]-2N-imidazol-2-one; 1-(2-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl] -2-pyridinyl]methyl]-2N-imidazol-2-one; 1-(2-propylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-tertbutylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-methoxycyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1Htetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-hydroxycyclohexyl)-4-butyl-1,3-dihydro-3-[[4-f3-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;        1-(2-carboxycyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-acetylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-oXocyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2,6-dimethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1H    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-ethyl-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3 (1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one; 1-(2-isopropyl-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4    [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-carboxy-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4- [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2-acetyl-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;

   1-(2-oxo-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3 (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-methyl-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3- tlH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2    one; 1-(2,6-diethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-isopropyl-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4 [3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one;    1-(2-carboxy-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;

   1-(2-acetyl-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2    one;  1-(2-oxo-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1H    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-methyl-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4- [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;    1-t2-ethyl-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4- [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2,6-diisopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one; 1-(2-carboxy-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3 [[4-[3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one; 

   1-(2-acetyl-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4    [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2-oxo-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3 (1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one; 1-(2,2-dimethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1H    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    and 1-(2,2-diethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1Htetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one.



   Within this fourth group of compounds of Formula
VI there is a fourth class of higher-interest compounds of
Formula VI(d):
EMI81.1     
  wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula VI(d) consists of compounds and their stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of    1-(2-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[4-(1H- tetrazol-5-yl)phenyl]-3-pyridinylimethyl3-2H-imidazol-2-one; 1-(2-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl]-3-pyridinylEmethyl3-2H-imidazol-2-one; 1-(2-propylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl] -3-pyridinyl]methyl] -2N-imidazol-2-one; 1-(2-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl] -3-pyridinyl]methyl] -2N-imidazol-2-one;

   1-(2-tertbutylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-methOxycyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl3-2H-imidazol-2-one; 1-(2-hydroxycyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-carboxycyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-acecylcyclohexyl)-4-butyl-1,3-dihydro-3-([[4-[4tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-oXocyclohexyl)-4-butyl-1,3-dihydro-3-[Ç4-[4-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

  ;   1-(2,6-dimethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[4-(1H- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;     1-(2-ethyl-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-([[4-[4    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one; 1-(2-isopropyl-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4    [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinylZmethylu-2H-imidazol-    2-one;    1-(2-carboxy-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4- [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyljmethyl]-2H-imidazol-    2-one;    1-(2-acetyl-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[4- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;

   1-(2-oxo-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-([[4-[4 (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-methyl-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[4- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;    1- (2,6-diethylcyclohexyl)-4-butyl-i,3-dihydro-3-[ [4-[4- (iN- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-isopropyl-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4    [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-carboxy-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[4- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;

   1-(2-acetyl-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-([[4-[4    tlH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-oXo-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;      1-    (2-methyl-6-isopropylcyclohexyl)-4-I::tyl-l,3-dihydro-3-[   [   4  [4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;

   1-(2-ethyl-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4    [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;  1-(2,6-diisoporpylcyclohexyl)-4-butyl-1,3-dihydro-3-([[4-[4 (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1- (2-carboxy-6-isopropylcyclohexyl) -4-butyi-l, 3-dihydro-3- [[4-[4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyllmethyl3-2H-    imidazol-2-one; 1-(2-acetyl-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4 [4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2-oxo-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-([[4-[4    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl3methyl]-2H-imidazol-2-    one;

   1-(2,2-dimethylcyclohexyl)-4-butyl-1,3-dihydro-3-([[4-[4    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    and 1-(2,2-diethylcyclohexyl)-4-butyl-1,3-dihydro-3-([[4-[4-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one.



   Within this fourth group of compounds of Formula
VI there is a fifth class of higher-interest compounds of
Formula VI(e):
EMI84.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl,   formal,    methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl,  isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula VI(e) consists of compounds and their stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of   1-(2-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-propylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-tertbutylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-methOxycyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-hydroxycyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-carboxycyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-acetylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-oXocyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one; 

   1-(2,6-dimethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-ethyl-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-    (1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-isopropyl-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4- [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one;  1-(2-carboxy-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4    [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2-acetyl-6-methyycyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3    tlH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-    one; 1-(2-oxo-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-    one;

   1-(2-methyl-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3    (iN-tetrazol-5-yl)phenyl] -4-pyridinyl]methyl) -2N-imidazoi-2-    one; 1-(2,6-diethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1Htetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-isopropyl-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4    [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2-carboxy-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3 (1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2one;

   1-(2-acetyl-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-oXo-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-methyl-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4- [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2-ethyl-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4    [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2,6-diisopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-    one;

   1-(2-carboxy-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3 [[4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2Himidazol-2-one;  1-(2-acetyl-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4    [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2-oxo-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3    (iN-tetrazol-5-yl)phenyi] -4-pyridinyl)methyi] -2N-imidazol-2-    one; 1-(2,2-dimethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1Htetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one; and    1-(2,2-diethylcyclohexyl)-4-butyl-i,3-dihydro-3-[ [4-[3- (iN- tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one.   



   Within this fourth group of compounds of Formula
VI there is a sixth class of higher-interest compounds of
Formula VI(f):
EMI87.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula VI(f) consists of compounds and their  stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of   1-t2-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-propylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one 1-(2-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

  ;    1-(2-tertbutylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-methOxycyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-hydroxycyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-carboxycyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-acetylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-oxocyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[2-(1H    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2,6-dimethylcyclohexyl)-4-butyl-1-[[4-(2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-ethyl-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one; 1-(2-isopropyl-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4    [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2-carboxy-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;

   1-(2-acetyl-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[2 (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazolo-2one;  1-(2-oxo-6-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[2 (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one; 1-(2-methyl-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[2    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one; 1-(2,6-diethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[2-(1H    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-isopropyl-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;

   1-(2-carboxy-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[2    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-acetyl-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[2- (iN-tetrazol-5-yl)phenyi] -3-pyridinyi)methyi) -2N-imidazoi-2-    one;    1-(2-oXo-6-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-methyl-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2-ethyl-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2,6-diisopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[2 (1H-tetrazol-5-yl)phenyl]-3-pyridintyl]methyl]-2H-imidazol-2one; 

   1-(2-carboxy-6-isoporpylcyclohexyl)-4-butyl-1,3-dihydro-3 [[4-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-acetyl-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;    1-(2-oXo-6-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;     1-(2t2-dimethylcyclohexyl)-4-butyl-lt3-dihydro-3-[[4-[2-(lH tetrazol-5-yl)phenyl] -3-pyridinyl]methyl] -2N-imidazol-2-one;    and    1-(2,2-diethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH- tetrazoi-5-yl)phenyl] -3-pyridinyl]methyl] -2N-imidazol-2-one.   



   Within the compounds of Formula II there is a fifth group of compounds of more interest as represented by
Formula VII:
EMI90.1     
 wherein each of R1, R2 and R3 is independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, cyano, fluoro, chloro, iodo, bromo, hydroxy, nitro, amino,
N-methylamino, N,N-dimethylamino, N-ethylamino,   N,N-    diethylamino, carboxyl, methoxycarbonyl, ethoxycarbonyl, formyl, methylcarbonyl, ethylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is selected from hydrido, methyl, fluoro, chloro, monofluoromethyl, difluoromethyl, trifluoromethyl, formyl, carboxyl and dimethoxymethyl;

   wherein R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tertbutyl, n-pentyl, isopentyl, neopentyl, phenyl, benzyl, phenethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl and cyclohexylethyl; wherein A is an acidic-group-substituted pyridinyl-phenyl moiety selected from  
EMI91.1     
 wherein R9 is an acidic group selected from COOH and
EMI91.2     
 or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   Within this fifth group of compounds of Formula
VII there is a first class of higher-interest compounds of
Formula VII(a):
EMI91.3     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl,  isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula VII(a) consists of compounds and their stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of   1-(2-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-propylcycloheptyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-tertbutylcycloheptyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-methOxyCycloheptyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-82-one; 1-(2-hydroxyCycloheptyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-carboxyCycloheptyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-acetylcycloheptyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-oxocycloheptyl)-4-butyl-1,3-dihydro-3-[[5-[2-(1Htetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2,7-dimethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[5-[2-(1Htetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-ethyl-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[5-[2- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-isopropyl-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3- [[5-[2- (iN-tetrazol-5-yl)phenyl] -2-pyridinyl]methyl]-2N-    imidazol-2-one;  1-(2-carboxy-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[5    [2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2-acetyl-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[5 [2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one; 1-(2-oxo-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[5-[2    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;

   1-(2-methyl-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[5-[2    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one; 1-(2,7-diethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[5-[2-(1H    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-isopropyl-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[5    [2- (lN-tetrazol-5-yl)phenyi) -2-pyridinyilmethyl] -2N-imidazol-    2-one; 1-(2-carboxy-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[5    [2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2-acetyl-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[5-[2 (1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-oXo-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[5-[2- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;

   1-(2-methyl-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3 [[5-[2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;    1-(2-ethyl-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-[[5-    [2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one; 1-(2,7-diisopropylcycloheptyl)-4-butyl-1,3-dihydro-3-[[5-[2    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;     1- (2-carboxy-7-isopropylcycloheptyl) -4-butyl-i, 3-dihydro-3- [[5-[2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2-one;    1-(2-acetyl-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3- [[5-[2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-    imidazol-2-one;

  ;    1- (2-oxo-7-isopropylcycloheptyl) -4-butyl-1,3-dihydro-3-[ [5- [2-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2,2-dimethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; and 1-(2,2-diethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[5-[2-(1H    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one.   

 

   Within this fifth group of compounds of Formula
VII there is a second class of higher-interest compounds of
Formula VII(b):
EMI94.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.  



   A family of specific compounds of particular interest within Formula VII(b) consists of compounds and their stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of    1-(2-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-propylcycloheptyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-tertbutylcycloheptyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-methOxyCycloheptyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-hydroxyCycloheptyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

  ;    1-(2-carboxyCycloheptyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-ylSphenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-acetylcycloheptyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;   l-(2-oxocycloheptyl)-4-butyl-1,3-dihydro-3-[[6-[2-(iN-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2,7-dimethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H tetrazol-5-yl0phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-ethyl-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[6-[2    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;

   1-(2-isopropyl-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3 [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    1-(2-carboxy-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[6- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol    2-one;     1-(2-acetyl-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[6-    [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;    1-(2-oXo-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lN-tetrazol-5-yl)phenyl] -3-pyridinyl)methyl) -2N-imidazol-2-    one;    1-(2-methyl-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;

   1-(2,7-diethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-isopropyl-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[6-    [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2-carboxy-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[6 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2-acetyl-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[6-[2    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;

   1-(2-oxo-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[6-[2    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-methyl-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3- [[6- [2- (iN-tetrazol-5-yl)phenyl] -3-pyridinyl]methyl] -2N-    imidazol-2-one;    1-(2-ethyl-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-[[6-    [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2,7-diisopropylcycloheptyl)-4-butyl-1,3-dihydro-3-[[6-[2 (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;

   1-(2-carboxy-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3 [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;     1-(2-acetyl-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3- [[6-[2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-    imidazol-2-one;    1- (2-oxo-7-isopropyicycloheptyl) -4-butyl-i,3-dihydro-3- [[6- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2,2-dimethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H    tetrazol-5-yl)phenyl]-3-pyridinyljmethyl]-2H-imidazol-2-one;    and 1-(2,2-diethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one.



   Within this fifth group of compounds of Formula
VII there is a third class of higher-interest compounds of
Formula VII(c):
EMI97.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula VII(c) consists of compounds and  their stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of   1-(2-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-3-one;   1-(2-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-3-one;   1-(2-propylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-3-one;    1-(2-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-3-one;

  ;    1-(2-tertbutylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-3-one;   1-(2-methOxyCycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-3-one;   1-(2-hydroxyCycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-3-one;   1-(2-carboxyCycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-3-one;   1-(2-acetylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-3-one; 1-(2-oxocycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1Htetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 

   1-(2,7-dimethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1Htetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-ethyl-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one; 1-(2-isopropyl-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3 [[4-[3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]melthyl]-2Himidazol-2-one;    1-(2-carboxy-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-    [3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one;    1-(2-acetyl-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4- [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;  1-(2-oxo-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3 (1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;

   1-(2-methyl-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3 (1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one; 1-(2,7-diethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1H    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-isopropyl-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4    [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2-carboxy-7-ethylcycloheptyl)-44-butyl-1,3-dihydro-3-[[4    [3- (iN-tetrazol-5-yl)phenyl] -2-pyridinyl)methyl) -2N-imidazol-    2-one; 1-(2-acetyl-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;

   1-(2-oxo-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidsszol-2-    one;   1-(2-methyl-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-ethyl-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4    [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;

   1-(2,7-diisopropylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-carboxy-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;   1- (2-acetyl-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-one;     1-(2-oXo-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4- [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;

   1-(2,2-dimethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1Htetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one and 1-(2,2-diethylcyclohepytl)-4-butyl-1,3-dihydro-3-[[4-[3-(1H    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one.   



   Within this fifth group of compounds of Formula
VII there is a fourth class of higher-interest compounds of
Formula VII(d):
EMI100.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula VII(d) consists of compounds and their stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of   1-(2-methylcyclOheptyl)-4-bUtyl-1,3-dihydro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;     1-(2-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-propylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-tertbutylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-methOxyCycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-hydroxyCycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-carboxyCycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-acetylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-oXocycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2,7-dimethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[4-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-ethyl-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[4- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;   1-(2-isopropyl-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-    [[4-[4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    1-(2-carboxy-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-    [4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2-acetyl-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4 [4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;

   1-(2-oxo-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[4    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imiGazol-2-    one;     1-(2-methyl-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[4-    (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2,7-diethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-isopropyl-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4    [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-carboxy-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4- [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-acetyl-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[4- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;

   1-(2-oxo-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[4    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;   1-(2-methyl-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-    [[4-[4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    1-(2-ethyl-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4- [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2,7-diisopropylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[4- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-carboxy-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-    [[4-[4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; 

   1-(2-acetyl-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3 [[4-[4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-oxo-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4    [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imiGazol-    2-one;     1-(2,2-dimethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl] -3-pyridinyl]methyl] -2N-imidazoi-2-one;    and    1-(2,2-diethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one.   



   Within this fifth group of compounds of Formula
VII there is a fifth class of higher-interest compounds of
Formula VII(e):
EMI103.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula VII(e) consists of compounds and their stereo isomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of   1-(2-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl] -4-pyridinyl]methyl] -2N-imidazol-2-one; 1-(2-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-4-pyridinylEmethyl]-2H-imidazol-2-one;     1-(2-propylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1H    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-isÏpropylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-tertbutylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl2-4-pyridinyl]methyl2-2H-imidazol-2-one;   1-(2-methOxyCycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl2-4-pyridinyl]methyl2-2H-imidazol-2-one;   1-(2-hydroxycycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3- (1H-    tetrazol-5-yl)phenyl2-4-pyridinyl]methyl2-2H-imidazol-2-one;   1-(2-carboxyCycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl2-4-pyridinyl]methyl2-2H-imidazol-2-one;    1-(2-acetylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-oxocycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1H    tetrazol-5-ylophenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2,7-dimethyicycloheptyl)-4-butyl-i,3-dihydro-3-[ [4-[3-(iN-    tetrazol-5-yl)phenyl2-4-pyridinyl]methyl2-2H-imidazol-2-one;    1-(2-ethyl-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-    one;   1-(2-isopropyl-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2Himidazol-2-one;    1-(2-carboxy-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-    [3-(1H-tetrazol-5-yl)phenyl2-4-pyridinyl]methyl]-2H-imidazol2-one;    1-(2-acetyl-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-    [3-(1H-tetrazol-5-yl)phenyl2-4-pyridinyl]methyl]-2H-imidazol2-one;

   1-(2-oxo-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-4-pyridinylZmethyl]-2H-imidazol-2-    one; 1-(2-methyl-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3 (1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl2-2H-imidazol-2one;  1-(2,7-diethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1Htetrazol-5-yl)phenyl2-4-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-isopropyl-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4- [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2-carboxy-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4    [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-acetyl-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-    (1H-tetrazol-5-yl)phenyl2-4-pyridinyl]methyl]-2H-imidazol-2one;

   1-(2-oxo-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-    one;   1-(2-methyl-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2Himidazol-2-one;    1-(2-ethyl-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-    [3-(1H-tetrazol-5-yl)phenyl2-4-pyridinyl]methyl]-2H-imidazol2-one; 1-(2,7-diisopropylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-    one;

   1-(2-carboxy-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3 [[4-[3-(1H-tetrazol-5-yl)phenyl2-4-pyridinyl]methyl]-2Himidazol-2-one;   1- (2-acetyl-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-oxo-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4    [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2,2-dimethylcycloheptyl)-4-butyl,3-dihydro-3-[[4-[3-(1Htetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one; and 1-(2,2-diethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1Htetrazol-5-yl)phenyl2-4-pyridinyl]methyl]-2H-imidazol-2-one.  



   Within this fifth group of compounds of Formula
VII there is a sixth class of higher-interest compounds of
Formula VII(f):
EMI106.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.

 

   A family of specific compounds of particular interest within Formula VII(f) consists of compounds and their stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of    1-(2-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH- tetrazol-5-yl)phenyl] -3-pyridinyl]methyl]-2N-imidazol-2-one;

   1-(2-propylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl3methyl]-2H-imidazol-2-onei 1-(2-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[2-(15:-    tetrazol-5-yl)phenyl2-4-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-tertbutylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[2-(1-- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-onei        1-(2-methOxyCycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-hydroxyCycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-carboxyCycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

  ;   1-(2-acetylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-oXocycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2,7-dimethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-ethyl-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[2 (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;   1- (2-isopropyl-7-methylcycloheptyl) -4-butyi-i, 3-dihydro-3-    [[4-([2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;

   1-(2-carboxy-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;    1-(2-acetyl-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2-oxo-7-methylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[2    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-methyl-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one; 1-(2,7-diethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-isopropyl-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;     1-(2-carboxy-7-ethylcycloheptyl)-4-butyl-lt3-dihydro-3-[[4- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-acetyl-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-oXo-7-ethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;   1-(2-methyl-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-    [[4-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;

   1-(2-ethyl-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4    [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinylZmethyl]-2H-imidazol-    2-one;    l-(2,7-diisopropylcycloheptyl)-4-butyl-i,3-dihydro-3-[ [4-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;

   1-(2-carboxy-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3 [[4-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;   1-(2-acetyl-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-    [[4-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    1-(2-oXo-7-isopropylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2,2-dimethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; and 1-(2,2-diethylcycloheptyl)-4-butyl-1,3-dihydro-3-[[4-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one.



   within the compounds Formula II there is an sixth group of compounds of more interest as represented by Formula
VIII:  
EMI109.1     
 wherein each of R1, R2 and R3 is independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, cyano, fluoro, chloro, iodo, bromo, hydroxy, nitro, amino,
N-methylamino, N,N-dimethylamino, N-ethylamino, N,Ndiethylamino, carboxyl, methoxycarbonyl, ethoxycarbonyl, formyl, methylcarbonyl, ethylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form   oç    ; wherein R7 is selected from hydrido, methyl, fluoro, chloro, monofluoromethyl, difluoromethyl, trifluoromethyl, formyl, carboxyl and dimethoxymethyl;

   wherein R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tertbutyl, n-pentyl, isopentyl, neopentyl, phenyl, benzyl, phenethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl and cyclohexylethyl; wherein A is an acidic-group-substituted pyridinyl-phenyl moiety selected from
EMI109.2     
 wherein F9 is an acidic   group    selected from   COO    an  
EMI110.1     
 or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   Within this sixth group of compounds of Formula
VIII there is a first class of higher-interest compounds of
Formula VIII(a):
EMI110.2     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and   R2    may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula   VIII (a)    consists of compounds and their stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of     1-(2-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-propylcyclooctyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;

  ;    1-(2-tertbutylcyclooctyl)-4-butyl-1,3-dihydro-3-[[5-[2-(1H    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-methOxycyclooctyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-hydroxycyclooctyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-carboxycyclooctyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-acetylcyclooctyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-oxocyclooctyl)-4-butyl-1,3-dihydro-3-[[5-[2-(1H    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2,8-dimethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[5-[2-(1Htetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-ethyl-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[5-[2-    (1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one; 1-(2-isopropyl-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[5 [2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one; 1-(2-carboxy-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[5 [2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one; 

   1-(2-carboxy-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[5-[2 (1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-oXo-8-methylcyclooctyl)-4-butyl-1,3-dihyaro-3-[[5-[2- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;  1-(2-methyl-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-([[5-[2    (lH-tetrazol-5-ylOphenyl]-2-pyridinyljmethyl]-2H-imidazol-2-    one;    l-(2,8-diethylcyclooctyl)-4-butyl-i,3-dihydro-3-[ [5-[2- (iN- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-isopropyl-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[5-    [2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one;    1-(2-carboxy-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[5-[2- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imiGazol-2-    one;    1-(2-acetyl-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[5-[2- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-oXo-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[5-[2-(lH-    tetrazol-5-yl)phyenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-methyl-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[5 [2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one;    1-(2-ethyl-8-isopropylcyciooctyl)-4-butyl-1,3-dihydro-3-[[5-    [2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one;

   1-(2,8-diisopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[5-[2    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;    1- (2-carboxy-8-isopropylcyclooctyl) -4-butyl-l,3-dihydro-3- [[5-[2- (lN-tetrazol-5-yl)phenyl] -2-pyridinyi]methyl]-2N-    imidazol-2-one;    1-(2-acetyl-8-isopropylcyclooctyl)-4-butyl-1,3-dihyd-o-3-[[5-    [2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one;    1-(2-oXo-8-isopropylcycloCctyl)-4-butyl-1,3-dihydro-3-[[5-[2- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one; 1-(2,2-dimethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[5-[2-(1Htetrazol-5-yl)phyenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;

   and     1-(2,2-diethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[5-[2-( 1H-    tetrazol-5-yl)phyenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;
 Within this sixth group of compounds of Formula
VIII there is a second class of higher-interest compounds of
Formula VIII(b)
EMI113.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula   VIII (b)    consists of compounds and their stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of 1-(2-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1Htetrazol-5-yl)phyenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1E:-    tetrazol-5-yl)phyenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-propylcyclooctyl)-4-butyl-',3-dihydro-3-[[6-[2-(1v-    tetrazol-5-yl)phyenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;  1-(2-isoprolpylcyclooctyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-tertbutylcyclooctyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-methOxycyclooctyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-hydroxycyclooctyl)-4-butyl-1,3-dihydro-3-[[6-[2-( 1H- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-carboxycyclooctyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-acetylcyclooctyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-oxocyclooctyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2,8-dimethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-ethyl-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[6-[2-    (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one; 1-(2-isopropyl-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[6 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2-carboxy-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[6 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;    1-(2-acetyl-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;

   1-(2-oxo-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[6-[2    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-methyl-8-ethylcyclooctyl)-4-butyl-l3-dihydro-3-[[6-[2 (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;    1- (2,8-diethylcyclooctyl)-4-butyi-1,3-dihydro-3-[ [6-[2- (iN-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;  1-(2-isopropyl-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[6    [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;

   1-(2-carboxy-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[6-[2    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-acetyl-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-oXo-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-methyl-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[6    [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;

   1-(2-ethyl-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[6    [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2,8-diisopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;   1- (2-carboxy-8-isopropylcyclooctyl)-4-butyl-i,3-dihydro-3-    [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]-methyl]-2Himidazol-2-one; 1-(2-acetyl-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[6 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2-oxo-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[6-[2    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one; 1-(2,2-dimethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 

   and 1-(2,2-diethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H   tetrazol-5-yl)phenyl]-3-pyridinylGmethyl]-2H-imidazo'-2-one.     



   Within this sixth group of compounds of Formula
VIII there is a third class of higher-interest compounds of
Formula VIII(c):
EMI116.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula VIII(c) consists of compounds and their stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of    1-(2-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl] -2-pyridinyl]methyl]-2N-imidazol-2-one; 1-(2-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-propylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl] -2-pyridinyl]methyl]-2N-imidazol-2-one;

   l-(2-isopropylcyclooctyl)-4-butyl-l,3-dihydro-3-[ [4-[3- (1.-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-tertbutylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1-.-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;     1-(2-methOxycyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-hydroxycyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-carboxycyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-acetylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-oXocyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2,8-dimethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1Htetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-ethyl-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one; 1-(2-isopropyl-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4 [3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one;

   1-(2-carboxy-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4 [3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one;    1-(2-acetyl-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-oXo-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;

   1-(2-methyl-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;    1- (2,8-diethylcyclooctyl)-4-butyl-l,3-dihydro-3-[[4-[3- (iN- tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-isopropyl-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4 [3-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol2-one;     1-(2-carboxy-8-ethylcyclooctyl)-4-butyl-1,3-dihyaro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-acetyl-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-oXo-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-methyl-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4    [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2-ethyl-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4    [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2,8-diisopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one; 1-(2-carboxy-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3 [[4-[3-(1H-tetrazol-5-yl)phenyl2-2-pyridinyl]methyl]-2Himidazol-2-one;    1-(2-acetyl-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4- [3-(lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-    2-one;

   1-(2-oxo-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2,2-dimethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one; and    1-(2,2-diethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-2-pyridinylimethyl]-2H-imidazol-2-one.   



   Within this sixth group of compounds of Formula
VIII there is a fourth class of higher-interest compounds   oS   
Formula VIII(d):  
EMI119.1     
 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula VIII(d) consists of compounds and their stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of    1-(2-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl] -3-pyridinyl]methyl]-2N-imidazol-2-one; 1-(2-propylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1H    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1H    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 

   1-(2-methoxycyclooctyl)-4-butyS 3-dihydro-3-[[4-[4-(l;:- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-hydroxyCyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[4-(1    tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2H-imidazol-2-one;     1-(2-carboxycyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-acetylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-oxocyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[4-(1H    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2,8-dimethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[4-(1H    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-ethyl-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[4 (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;

   1-(2-isopropyl-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4    [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-carboxy-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-    [4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;    1-(2-acetyl-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[4-    (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one; 1-(2-oxo-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[4    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;

   1-(2-methyl-8-ethylcyclooctyl)-44-butyl-1,3-dihydro-3-[[4-[4    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;    l-(2,8-diethylcyclooctyl)-4-butyl-l,3-dihydro-3-[ [4-[4- (iN- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-isopropyl-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4- [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-carboxy-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[4- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-acetyl-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[4- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imiCazoi-/-    one;  1-(2-oxo-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[4-(1Htetrazol-5-yl)phenyl]-3-pyrinyl]methyl]-2H-imidazol-2-one;

   1-(2-methyl-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4    [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2-ethyl-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4    [4-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2,8-diisopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[4- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;   1-(2-carboxy-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-    [[4-[4-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-acetyl-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4 [4-(1H-tetrazol-5-yl)phenyl]-3-pyrinyl]methyl]-2H-imidazol2-one;

   1-(2-oxo-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[4    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2,2-dimethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[4-(lH-    tetrazol-5-yl)phenyl]-3-pyrinyl]methyl]-2H-imidazol-2-one; and    1- (2,2-diethylcyclooctyl)-4-butyl-l,3-dihydro-3-[[4-[4- (iN- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one   
 Within this sixth group of compounds of Formula
VIII there is a fifth class of higher-interest compounds of
Formula   VIII(ei:   
EMI121.1     
  wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl;

   wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl,   n-pentyi,    isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula VIII(e) consists of compounds and their stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of   1-(2-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyrinyl]methyl]-2H-imidazol-2-one;    1-(2-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-propylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyrinyl]methyl]-2H-imidazol-2-one;    1-(2-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-tertbutylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyrinyl]methyl]-2H-imidazol-2-one;    1-(2-methOxycyclooctyl)-4-butyl-1,3-dihyaro-3-[[4-[3-(lH- tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-hydroxycyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyrinyl]methyl]-2H-imidazol-2-one;    1-(2-carboxycyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1H- tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-acetylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(lH-    tetrazol-5-yl)phenyl]-4-pyrinyl]methyl]-2H-imidazol-2-one;

   1-(2-oxocyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1H   tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;     1-(2,8-dimethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1Htetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-ethyl-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-    one; 1-(2-isopropyl-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4 [3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol 2-one; 1-(2-carboxy-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4    [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-acetyl-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-    one;

   1-(2-oxo-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3 (1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidzol-2one;    1-(2-methyl-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-    one;    1- (2,8-diethylcyclooctyl)-4-butyl-l,3-dihydro-3-[ [4-[3- (iN- tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one; 

   1-(2-isopropyl-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4- [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-carboxy-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-    (1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2one;    1-(2-acetyl-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3- (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-oXo-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(15- tetrazol-5-yl)phenyl]-4-pyridinyl)methyl]-2H-imidazol-2-one;    1-(2-methyl-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4 [3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidzol2-one;     1-(2-ethyl-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4- [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyljmethyl]-2H-imidazol-    2-one;

   1-(2,8-diisopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3    (lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-    one;   1- (2-carboxy-8-isopropylcyclooctyl) -4-butyl-l,3-dihydro-3-    [[4-[3-(1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-acetyl-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4    [3-(lH-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-    2-one; 1-(2-oxo-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3 (1H-tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2one;

   1-(2,2-dimethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1H    tetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;    and 1-(2,2-diethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[3-(1Htetrazol-5-yl)phenyl]-4-pyridinyl]methyl]-2H-imidazol-2-one;
 Within this sixth group of compounds of Formula
VIII there is a sixth class of higher-interest compounds of
Formula VIII(f):
EMI124.1     
 wherein each of   P-,      P.2    and   P.    may be independently   selected    from hydrido methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, broom, carboxyl, formyl, methylcarbonyl and  trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido;

   wherein
R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.



   A family of specific compounds of particular interest within Formula VIII(f) consists of compounds and their stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of    1-(2-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;   1-(2-propylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2-tertbutylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one 1-(2-methOxycyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl3methyl]-2H-imidazol-2-one; 1-(2-hydroxycyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-carboxycyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-acetylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-oxocyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

   1-(2,8-dimethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-ethyl-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[ - (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;     1-(2-isopropyl-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-carboxy-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-    [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;    1-(2-acetyl-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;

   1-(2-oxo-8-methylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[2    (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-methyl-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[2-    (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;    1-(2,8-diethylcyclooctyl)-4-butyl-1,3-dihydro-3-[ [4-[2-(iN- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;    1-(2-isopropyl-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4    [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-carboxy-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;

  ;    1-(2-acetyl-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one;    1-(2-oXo-8-ethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[2-(lH-    tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-methyl-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4    [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-ethyl-8-isopropylcyclooctyl)-4-butyl-1,3-dihyaro-3-[[4- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imiGazol-    2-one; 

   1-(2,8-diisopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[2 (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;     1- (2-carboxy-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-    [[4-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;    1-(2-acetyl-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-    2-one;    1-(2-oXo-8-isopropylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-    one; 1-(2,2-dimethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;

   and 1-(2,2-diethylcyclooctyl)-4-butyl-1,3-dihydro-3-[[4-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;  
 The term   hydrido    denotes a single hydrogen atom (H). This hydrido group may be attached, for example, to an oxygen atom to form a hydroxyl group; or, as another example, one hydrido group may be attached to a carbon atom to form a [ group; or, as another example, two hydrido groups may be attached to a carbon atom to form a -CH2- group. Where the term   asakyl.I    is used, either alone or within other terms such as "haloalkyl", the term "alkyl" embraces linear or branched radicals having one to about twenty carbon atoms or, preferably, one to about twelve carbon atoms. More preferred alkyl radicals are "lower alkyl" radicals having one to about ten carbon atoms.

  Most preferred are lower alkyl radicals having one to about five carbon atoms. The term "cycloalkyl" embraces cyclic radicals having three to about ten ring carbon atoms, preferably three to about six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term "haloalkyl" embraces radicals wherein any one or more of the alkyl carbon atoms is substituted with one or more halo groups, preferably selected from bromo, chloro and fluoro. Specifically embraced by the term   haloalkyl'    are monohaloalkyl, dihaloalkyl and polyhaloalkyl groups. A monohaloalkyl group, for example, may have either a bromo, a chloro, or a fluoro atom within the group. Dihaloalkyl and polyhaloalkyl groups may be substituted with two or more of the same halo groups, or may have a combination of different halo groups.

  A dihaloalkyl group, for example, may have two fluoro atoms, such as difluoromethyl and difluorobutyl groups, or two chloro atoms, such as a dichloromethyl group, or one fluoro atom and one chloro atom, such as a fluoro-chloromethyl group. Examples of a polyhaloalkyl are trifluoromethyl, l,l-difluoroethyl, 2,2,2-trifluoroethyl, perfluoroethyl and 2,2,3,3tetrafluoropropyl groups. The term   "difluoroalkyl"    embraces alkyl groups having two fluoro atoms substituted on any one or two of the alkyl group carbon atoms. The terms "alkoxy" and "alkoxyalkyl" embrace linear or branched  oxy-containing radicals each having alkyl portions of one to about ten carbon atoms, such as methoxy group. The term "alkoxyalkyl" also embraces alkyl radicals having two or more alkoxy groups attached to the alkyl radical, that is, to form monoalkoxyalkyl and dialkoxyalkyl groups.

  The "alkoxy" or "alkoxyalkyl" radicals may be further substituted with one or more halo atoms, such as fluoro, chloro or bromo, to provide haloalkoxy or haloalkoxyalkyl groups.



  The terms "benzyl" and "phenylmethyl" are interchangeable.



  For any of the foregoing defined radicals, preferred radicals are those containing from one to about ten carbon atoms.



   Specific examples of alkyl groups are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, methylbutyl, dimethylbutyl and neopentyl.



   Compounds of Formula I have been found to inhibit the action of angiotensin II in mammals. Angiotensin II is a potent vasoconstrictor and participates in the formation of aldosterone which regulates sodium and water balance in mammals. Thus, compounds of Formula I are therapeutically useful in methods for treating hypertension by administering to a hypertensive patient a therapeuticallyeffective amount of a compound of Formula I. The phrase "hypertensive patient" means, in this context, a mammalian subject suffering from or afflicted by the effects of hypertension or susceptible to a hypertensive condition if not treated to prevent or control such hypertension.



   Also included in the family of compounds of
Formula I are isomeric forms including diastereoisomers and the pharmaceutically-acceptable salts thereof. The term "pharmaceutically-acceptable salts" embraces salts commonly used to form alkali metal salts and to form addition salts of free acids or free bases. The nature of the salt is not  critical, provided that it is pharmaceutically-acceptable.



  Suitable pharmaceutically-acceptable acid addition salts of compounds of Formula I may be prepared from an inorganic acid or from an organic acid. Examples of such inorganic acids are hydrochloric, hydrobromic, hydroiodic, nitric, carbonic, sulfuric and phosphoric acid. Appropriate organic acids may be selected from aliphatic, cycloaliphatic, aromatic, araliphatic, heterocyclic, carboxylic and sulfonic classes of organic acids, example of which are formic, acetic, propionic, succinic, glycolic, gluconic, lactic, malic, tartaric, citric, ascorbic, glucuronic, maleic, fumaric, pyruvic, aspartic, glutamic, benzoic, anthranilic, p-hydroxybenzoic, salicyclic, phenylacetic, mandelic, embonic (pamoic), methansulfonic,   ethanesul fonic,    2-hydroxyethanesulfonic, pantothenic, benzenesulfonic, toluenesulfonic,   sulfanilic,    mesylic,

   cyclohexylaminosulfonic, stearic, algenic,   ss-hydroxybutyric,    malonic, galactaric and galacturonic acid. Suitable pharmaceutically-acceptable base addition salts of compounds of Formula I include metallic salts made from aluminium, calcium, lithium, magnesium, potassium, sodium and zinc or organic salts made from N,N'dibenzylethylenediamine, chloroprocaine, choline, diethanolamine, ethylenediamine, meglumine (N-methylglucamine) and procaine. All of these salts may be prepared by conventional means from thecorresponding compound of
Formula I by reacting, for example, the appropriate acid or base with the compound of Formula I.  

 

   General   Svnthetic    Procedures
 The compounds of the invention can be synthesized according to the following procedures of
Schemes I-XXXI, wherein the R substituents are as defined for Formula I, above, except where further noted.



   Scheme I
EMI131.1     
  
 Synthetic Scheme I shows the preparation of the boronic acid   1    where R9 equals N-tertbutyl-Nmethylcarboxamide. In step 1, benzoic acid is treated with thionyl chloride to give the corresponding acid chloride which is subsequently reacted with N-tertbutyl-Nmethylamine to give N-tertbutyl-N-methylbenzamide. In step 2, the amide is ortho-metalated and subsequently reacted with trimethyl borate. The free boronic acid   1    is produced on hydroylsis.  



  Scheme II
EMI133.1     
  
 Synthetic Scheme II shows the preparation of the boronic acid 1 where R9 equals N-triphenylmethyl-lHtetrazole. In step 1, 2-bromobenzonitrile (Aldrich) is reacted with tributyltin azide to give the corresponding tetrazole. In step 2, the tetrazole is reacted with triphenylmethyl chloride in the presence of triethylamine to give the protected bromophenyltetrazole. In step 3, halogen-metal interchange with n-butyllithium generates the corresponding ortho-lithiated species which is reacted with trimethyl borate. The free boronic acid   i    is produced on hydrolysis.  



  Scheme III
EMI135.1     
  
 Synthetic Scheme III shows the preparation of
N-Boc-amino ketones 2 (or aldehydes when R7 = H) from the corresponding N-Boc-amino acides   i.    In step 1, the amino acid   i    is reacted with isobutyl chloroformate in the presence of triethylamine and subsequently with N,Odimethylhydroxylamine to give the corresponding N-methoxy
N-methylamide   A.    In step 2, the amide A is reacted with an organolithium reagent   R7-Li    (or lithium aluminum hydride   (LAH)    when R7 = H) to give the desired ketone 2 (or aldehyde when R7 = H).  



   Scheme IV
METHOD A:
EMI137.1     
  
 Synthetic Scheme IV shows the preparation of imidazol-2-ones 5 from the corresponding amides   A    via
Method A. In step 1, the protected amide   @    (prepared in
Scheme III) is reacted with trifluoroacetic acid (TFA) to give the TFA salt 6 of the free amine. In step 2, the salt 6 is reacted with the appropriate isocyanate   1    in the presence of triethylamine to give the urea   B.    In step 3, the urea   a    is reacted with an organolithium reagent R7-Li (or lithium aluminum hydride   (LAH)    when R7 = H) and subsequently cyclized to the imidazole-2-one 5 on treatment with dilute acid during the work-up procedure.  



   Scheme V
METHOD B:
EMI139.1     
  
 Synthetic Scheme V shows the preparation of imidazol-2-ones   5    from the corresponding N-Boc-protected amino ketones 2 (or aldehydes when R7 = H) via Method B.



  In step 1, the carbonyl compound   Z    (prepared in Scheme III) is reacted with anhydrous hydrogen chloride in dioxane to give the HC1 salt   e.    In step 2, the salt   9    is reacted with the appropriate isocyanate 7 in chloroform to give the imidazol-2-one   L    directly.  



   Scheme VI
METHOD C:
EMI141.1     
  
 Synthetic Scheme VI shows the preparation of imidazol-2-ones 5 from the corresponding N-Boc-protected amino ketones   26    (or aldehydes when R7 = H) via Method C.



  In step 1, the carbonyl compound 2 (prepared in Scheme III} is reacted with 2,2-dimethyl-1,3-propandiol to give the cyclic ketal   1Q.    In step 2, the ketal 10 is reacted with
TFA to give the TFA salt 11 of the free amine. In step 3, the salt 11 is reacted with the appropriate isocyanate 7 in the presence of triethylamine to give the urea ketal   12.   



  In step   e,    the urea ketal   12    is reacted with 6N hydrochloric acid at 600C to give the desired imidazol-2one 5 directly.  



  Scheme VII
EMI143.1     
  
 Synthetic Scheme VII shows the preparation of 2-bromomethyl-5-bromopyridine (13) and 5-bromo-2pyridinecarboxaldehyde   (li)    from 2-picoline (Aldrich). In step 1, 2-picoline is reacted with bromine in the presence of a large excess of aluminum chloride at elevated temperatures to give 5-bromo-2-picoline (15). In step 2a,   12    is reacted with NBS to give the 2-pyridinylmethyl bromide 13. In step 2b, the intermediate 15 is treated with potassium permanganate to give the corresponding picolinic acid   1fi-    In step 3b, the acid   1E    is first converted to its N-methoxy-N-methylamide and subsequently reduced with LAH to provide 5-bromo-2pyridinecarboxaldehyde (14).  



  Scheme VIII
EMI145.1     
  
 Synthetic Scheme VIII shows the preparation of   2 -bromo-5 -bromomethylpyridine      (17)    and   2 -bromo-5-    pyridinecarboxaldehyde (18) from 2-amino-5-picoline (Aldrich). In step 1, 2-amino-5-picoline is reacted with bromine in the presence of hydrobromic acid and sodium nitrite at 0 C to give 2-bromo-5-picoline (19). In step 2a, 19 is reacted with NBS to give the 3-pyridinylmethyl bromide   17.    In step 2b, the intermediate 19 is treated with potassium permanganate to give the corresponding nicotinic acid 20. In step 3b, the acid   20    is first converted to its N-methoxy-N-methylamide and subsequently reduced with LAH to provide 2-bromo-5pyridinecarboxaldehyde (18).  



  Scheme IX
EMI147.1     
  
 Synthetic Scheme IX shows the preparation of (4-bromobenzyl)imidazol-2-ones   261    from the TFA salt of the amino amide   i    (prepared in Scheme III). In step 1, the TFA salt 6 is allowed to react with the 4-bromobenzaldehyde in the presence of triethylamine and anhydrous magnesium sulfate to give the imine 22. In step 2, the imine   261    is allowed to react with sodium borohydride to give the substituted benzylamine   261.    In step 3, the benzylamine   261    is allowed to react with the appropriate isocyanate 7 to give the substituted benzylurea 24.

  In step 4, the urea 24 is first allowed to react with an organolithium reagent   R'-   
Li (or lithium aluminum hydride   (LAH)    when R = H) and subsequently with dilute aqueous acid to give the desired 3-(4-bromobenzyl)imidazol-2-ones.  



  Scheme X
EMI149.1     
  
 Synthetic Scheme x shows the preparation of 3-(5-bromo-2-pyridinylmethyl)imidazol-2-ones   25    from the
TFA salt of the amino amide 6 (prepared in Scheme III). In step 1, the TFA salt 6 is allowed to react with the 5-bromo-2-pyridinylaldehyde 14 (prepared in Scheme VII) in the presence of triethylamine and anhydrous magnesium sulfate to give the imine 26 In step 2, the imine 26 is allowed to react with sodium borohydride to give the substituted benzylamine 22. In step 3, the benzylamine 27 is allowed to react with the appropriate isocyanate 7 to give the substituted   benzylurea    28. 

  In step 4, the urea   iS    is first allowed to react with an organolithium reagent R7
Li (or lithium aluminum hydride   (LAH)    when R7   = H)    and subsequently with dilute aqueous acid to give the desired 3-(5-bromo-2-pyridinylmethyl)imidazol-2-ones 25.  



  Scheme XI
EMI151.1     
  
 Synthetic Scheme XI shows the preparation of 3-(2-bromo-5-pyridinylmethyl)imidazol-2-ones   29    from the
TFA salt of the amino amide 6 (prepared in Scheme III). In step 1, the TFA salt 6 is allowed to react with 2-bromo-5pyridinylaldehyde   1i    (prepared in Scheme VIII) in the presence of triethylamine and anhydrous magnesium sulfate to give the imine   ssQ.    In step 2, the imine 30 is allowed to react with sodium borohydride to give the substituted benzylamine   i1-    In step 3, the benzylamine 31 is allowed to react with the appropriate isocyanate 7 to give the substituted   benzylurea    32.

  In step 4, the urea 32 is first allowed to react with an organolithium reagent R7-Li (or lithium aluminum hydride   (LAH)    when R7 = H) and subsequently with dilute aqueous acid to give the desired 3-(2-bromo-5pyridinylmethyl)imidazol-2-ones 29.  
EMI153.1     
  



   Synthetic Scheme XII shows the preparation of 3-(4-bromobenzyl)imidazol-2-ones   21,    3-(5-bromo-2   pyridinylmethyl) imidazol-2-ones    25, and 3-(2-bromo-5   pyridinylmethyl)imidazol-2-ones      ii    from the parent imidazol-2-ones 5 (prepared in Scheme IV, Scheme V, or
Scheme VI). The imidazol-2-one   5    is first treated with a base, such as potassium t-butoxide, and subsequently with the alkylating agent 4-bromobenzyl bromide, 13 (prepared in
Scheme VII), and   17    (prepared in Scheme VIII) to give 3-(4bromobenzyl) imidazol-2-ones 21, 3-(5-bromo-2pyridinylmethyl)imidazol-2-ones 25, and 3-(2-bromo-5pyridinylmethyl)imidazol-2-ones 29, respectively.  



  Scheme XIII
EMI155.1     
  
 Synthetic Scheme XIII shows the preparation of 3-[[5-[2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-ones   30    from the boronic acid   i    (prepared in
Scheme I and Scheme II) and the bromoimidazol-2-one coupling reagent 25 (prepared in Scheme X and Scheme XII).



  The boronic acid   j    is reacted with the bromoimidazol-2-one coupling reagent   2±    in the presence of a palladium zero catalyst via a Snieckus coupling [see M. J. Sharp and V.



  Snieckus, Tetrahedron Lett.,   5997(1985))    to give the angiotensin II antagonists 30 of this invention.  



  Scheme XIV
EMI157.1     
  
 Synthetic Scheme XIV shows the preparation of 3-[[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-ones   31    from the boronic acid   i    (prepared in
Scheme I and Scheme II) and the bromoimidazol-2-one coupling reagent   261    (prepared in Scheme XI and Scheme XII).



  The boronic acid   i    is reacted with the bromoimidazol-2-one coupling reagent   261    in the presence of a palladium zero catalyst via a Snieckus coupling [see M. J. Sharp and
V. Snieckus, Tetrahedron Lett., 5997(1985)] to give the angiotensin II antagonists 31 of this invention.  



  Scheme XV
EMI159.1     
  
 Synthetic Scheme XV shows the preparation of the imidazol-2-one boronic acid coupling reagents   261    from the corresponding 3-(4-bromobenzyl)imidazol-2-ones 21 (prepared in Scheme IX and Scheme XII). Halogen-metal interchange generates the corresponding lithiated species from   11    which is reacted with trimethyl borate. The free imidazol-2-one boronic acid coupling reagents 32 are produced on acid hydrolysis.  



  Scheme XVI
EMI161.1     
  
 Synthetic Scheme XVI shows the preparation of the 4-bromopyridine coupling reagent   iS    [R9 =   CON(CH3)C(CH3)3]    and the 2-bromopyridine coupling reagent   Ii    [R9 =   CONtCH3)C(CH3)3]    from nicotinic acid. In step 1, Ntertbuty-N-methylnicotinamide is prepared from nicotinoyl chloride and N-tertbutyl-N-methylamine. In step 2, orthometalalion with sec-butyllithium gives a mixture of regioanions which are reacted with trimethylsilyl chloride; subsequent conversion to the corresponding bromides on treatment with bromine in acetic acid and separation of the regioisomers by chromatography provides 33 and   34.     



  Scheme XVII
EMI163.1     
  
 Synthetic Scheme XVII shows the preparation of the 3-bromopyridine coupling reagent   iS    [R9 = CON(CH3)C(CH3)3] from isonicotinic acid. In step 1,
N-tertbutyl-N-methylisonicotinamide is prepared from isonicotinoyl chloride and N-tertbutyl-N-methylamine. In step 2, reaction with sec-butyllithium gives the ortho-lithiated species which is reacted with trimethylsilyl chloride and subsequently converted to the corresponding bromide   2±    on treatment with bromine in acetic acid.  



  Scheme XVIII
EMI165.1     
  
 Synthetic Scheme XVIII shows the preparation of the 3-bromopyridine coupling reagent 36 [R9 =   CON(CH3)C(CH3)3]    from picolinic acid. In step 1,
N-tertbutyl-N-methylpicolinamide is prepared from picolinoyl chloride and N-tertbutyl-N-methylamine. In step 2, reaction with sec-butyllithium gives the ortho-lithiated species which is reacted with trimethylsilyl chloride and subsequently converted to the corresponding bromide   36    on treatment with bromine in acetic acid.  



  Scheme XIX
EMI167.1     
  
 Synthetic Scheme XIX shows the preparation of 3-(pyridinylbenzyl)imidazol-2-ones 37, 38, 39 and   40    from the common imidazol-2-one boronic acids 32 (Scheme XV) and the corresponding bromo coupling reagents 36 (Scheme
XVIII), 33 (Scheme XVI, 35 (Scheme XVII), and 34 (Scheme
XVI), respectively. The boronic acids   261    are reacted with the bromo coupling reagents 36, 33, 35 and 34 in the presence of a palladium zero catalyst via a Snieckus coupling [see M. J. Sharp and V. Snieckus, Tetrahedron
Lett., 5997 (1985)] to give the angiotensin II antagonists 37,   38,    39 and   AQ,    respectively, of this invention.  



  Scheme XX
EMI169.1     
  
 Synthetic Scheme XX shows the preparation of carboxylic acid analogs   Aj    and   lH-tetrazole    analogs 42 from analogs which have R5 = CON(CH3)C(CH3)3. In step 1, the
N-tertbutyl-N-methylamide analog   ii    is reacted with trifluoroacetic acid at reflux to give the N-methylamide   li.    In step 2, the N-methylamide   44    is reacted with sodium nitrite in acetic anhydride/acetic acid at 0 C to give the corresponding N-methyl-N-nitrosoamide 45. In step 3, the
N-methyl-N-nitrosoamide 45 is hydrolyzed in base to give the corresponding carboxylic acid angiotensin II antagonists of this invention. 

  In step 4, the acid analog 41 is reacted with oxalyl chloride and subsequently with anhydrous ammonia to give the primary amide   Ai.    In step 5, the amide   46    is reacted with triphenylphosphine in carbon tetrachloride at 50 C to give the corresponding nitrile   47.   



  In step 6, the nitrile 47 is reacted with trimethyltin azide in xylene at reflux to provide the   lH-tetrazole    angiotensin II antagonists of this invention.  



  Scheme XXI
EMI171.1     
  
 Synthetic Scheme XXI shows the preparation of the organozinc reagent   AS    from the appropriate benzoic acid analog 49. In step 1, the analog 49 is brominated with bromine in the presence of a suitable catalyst, e.g., iron, to give the 2-bromo analog 50. In step 2, the 2-bromo analog 50 was converted to the organolithium reagent   L1    by reaction with n-butyllithium in THF at   -780C,    a process known as halogen-metal interchange.



  Alternatively, the organolithium reagent 51 can be generated directly by the reaction of   ji    with an   alkyllithium    reagent in the presence or absence of a suitable complexing agent in   ThF    at -780C, e.g., secbutyllithium/TMEDA (N,N,N',N'-tetramethylethylenediamine). In step 3, the organolithium reagent 51 was treated with anhydrous zinc chloride at -780C and subsequently allowed to warm to ambient   temperature.   



  The organozinc reagent 48 was generated and used in  
Scheme XXII
EMI173.1     
  
 Synthetic Scheme XXII shows the preparation of the 2-pyridinyl alkylating reagent and the 3pyridinyl alkylating 53 from 15 (Scheme VII) and   12    (Scheme VIII), respectively. In step 1,   15    and   12    were coupled with   1    using Snieckus conditions (Scheme XIII) or 48 using Negishi conditions [see E. Negishi, A. O.



  King, and N. Okukado, J.   Org.    Chem.,   AX,    1821 (1977)] to give 54 and 55, respectively. In step 2, the coupled biaryl compounds 54 and 55 were brominated using
NBS/AIBN to give the 2-pyridinyl alkylating reagent 52 and the 3-pyridinyl alkylating reagent   53,    respectively.  
Scheme XXIII
EMI175.1     
  
 Synthetic Scheme XXIII shows the preparation of   3-[[5-[2-(lH-tetrazol-5-yl)phenyl]-2-      pyridinyl]methyl]-2H-imidazol-2-ones      30    (R5=CN4H) and 3 [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-ones 31 (R5=CN4H) from the parent imidazol-2ones 5 (prepared in Scheme IV, Scheme V, or Scheme VI).



  The imidazol-2-one 5 was first treated with a base, such as potassium   t-butoxide,    and subsequently with the alkylating reagent   L2    or 53 (Scheme XXII) to give 3-[[5 [2-(1H-tetrazol-5-yl)phenyl]-2-pyridinyl]methyl]-2Himidazol-2-ones   5Q    (R5=CN4H) and 3-[[6-[2-(1H-tetrazol-    5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-ones i1    (R5=CN4H), respectively.  



  Scheme XXIV
EMI177.1     

 Synthetic Scheme XXIV shows the preparation of 4-methylphenylboronic acid   (56)    from 4-bromotoluene. In step 1, the Grignard reagent was generated by the reaction of 4-bromotoluene with metallic magnesium in ether at reflux. In step 2, a   ThF    solution of trimethoxyborane was cooled to   -78     C and slowly treated with the Grignard reagent. In step 3, the boronic ester was hydrolyzed with aqueous hydrochloric acid to give 4methylphenylboronic acid   (56).     



  Scheme XXV
EMI178.1     
  
 Synthetic Scheme XXV shows the 8-step preparation of the alkylating reagent 2-(4bromomethylphenyl)-3-cyanopyridine (57) from 2-amino-3picoline (58) (Aldrich). In step 1, the aminopicoline   58    was converted to the bromopicoline 59 by reaction with bromine, concentrated hydrobromic acid, and sodium nitrite at   OOC.    In step 2, the picoline 59 was oxidized with   KMNO4    to give the corresponding carboxylic acid 60.



  In step 3, the acid 60 was reduced to the alcohol 61 with borane/THF. In step 4, the alcohol   li    was oxidized to the   aldelyde      ±2    under Swern conditions or by using
MnO2. In step 5, the   aldehyde    62 was reacted with hydroxylamine to give the oxime   iL.    In step 6, the oxime 63 was converted to 2-bromo-3-cyanopyridine (64) with acetic anhydride at reflux. In step 7, the nitrile 64 was coupled with   4-methylphenylboronic    acid (56) (Scheme
XXIV) using Snieckus conditions (Scheme XIII) to give 3cyano-2-(4-methylphenyl)pyridine (65). In step 8, 65 was brominated with NBS/AIBN in carbon tetrachloride at reflux to give the desired alkylating reagent 57.  



  Scheme XXVI
EMI180.1     
  
 Synthetic Scheme XXVI shows the 6-step preparation of the alkylating reagent 3-(4bromomethylphenyl)-4-cyanopyridine (66) from 4-picoline (67) (Aldrich). In step 1, 4-picoline was brominated with bromine in fuming sulfuric acid at high temperatures to give 3-bromo-4-picoline   (68).    In step 2, the picoline 68 was oxidized to the corresponding carboxylic acid iS with KMnO4. In step 3, the acid 69 was first converted to its acid chloride with oxalyl chloride and subsequently treated with condensed ammonia to give the amide 1Q. In step 4, the amide   70    was converted to 3-bromo-4-cyanopyridine   (71)    by treatment with P2O5 at high temperatures.

  In step 5, the nitrile   71    was coupled with 4-methylphenylboronic acid   (56)    (Scheme XXIV) using Snieckus conditions (Scheme XIII) to give 4-cyano-3-(4-methylphenyl)pyridine   (1Z).    In step 6, 72 was brominated with NBS/AIBN in carbon tetrachloride at reflux to give the desired alkylating reagent 66.  



  Scheme XXVII
EMI182.1     
  
 Synthetic Scheme XXVII shows the 5-step preparation of the alkylating reagent 4-(4bromomethylphenyl)-3-cyanopyridine   (73)    from 4bromopyridine (74) (Aldrich). In step 1, the ortho-bromo carbanion was generated with LDA in   ThF    at -78  C and reacted with anhydrous DMF to give 4-bromo-3carboxaldehyde   75.    In step 2, the   aldehyde    75 was reacted with hydroxylamine to give the oxime 76. In step 3, the oxime 76 was dehydrated with 1,1 carbonyldiimidazole in methylene chloride at reflux to give 4-bromo-3-cyanopyridine (77). 

  In step 4, the nitrile 77 was coupled with   4-methylphenylboronic    acid   (Li)    (Scheme XXIV) using Snieckus conditions (Scheme
XIII) to give 3-cyano-4-(4-methylphenyl)pridine   (78).   



  In step 5, 78 was brominated with NBS/AIBN in carbon tetrachloride at reflux to give the desired alkylating reagent 73.  



  Scheme XXVIII
EMI184.1     
  
 Synthetic Scheme XXVIII shows the 4-step preparation of the alkylating reagent 2-cyano-3-(4bromomethylphenyl)pyridine (79) from 3-bromopyridine   (80)    (Aldrich). In step 1, the pyridine   80    was reacted with hydrogen peroxide in acetic acid at reflux to give the pyridine N-oxide 81. In step 2, the N-oxide   81    was converted to 3-bromo-2-cyanopyridine (82) by reaction with trimethysilylcyanide and triethyl anine in acetonitrile at reflux.

  In step 3, the nitrile 82 was coupled with   4-methylphenylboronic    acid (56) (Scheme
XXIV) using Snieckus conditions (Scheme XIII) to give 2cyano-3-(4-methylphenyl) pyridine   (83).    In step 4, 83 was brominated with NBS/AIBN in carbon tetrachloride at reflux to give the desired alkylating reagent   29.     



  Scheme XXIX
EMI186.1     
  
 Synthetic Scheme XXIX shows the preparation of 1,4,5-trisubstituted-1,3-dihydro-3-[[4-(2-cyano-3pyridinyl)phenyl]methyl]-2H-imidazol-2-ones 37 (R5=CN), 1,4,5-trisubstituted-1,3-dihydro-3-[[4-(3-cyano-4pyridinyl)phenyl]methyl]-2H-imidazol-2-ones 38 (R5=CN),   1,4, 5-trisubstituted-1, 3-dihydro-3- [[4- (4-cyano-3-    pyridinyl)phenyl]methyl]-2H-imidazol-2-ones 39 (R5=CN), and 1,4,5-trisubstituted-1,3-dihydro-3-[[4-(3-cyano-2prydinyl)phenyl]methyl]-2H-imidazol-2-ones 40 (R5=CN) from the parent   1,4,5-trisubstituted-1,3-dihydro-2H-    imidazol-2-ones 5 (prepared in Scheme IV, Scheme V, or
Scheme VI).

  The imidazol-2-one   2    was first treated with a base, such as potassium   t-butoxide,    and subsequently with the alkylating reagents 29 (Scheme XXVIII), 73 (Scheme XXVII), 66 (Scheme XXVI), and 57 (Scheme XXV) to give the   alkylated    products 37 (R5=CN), 38 (R5=CN, 39 (R5=CN), and   40    (R5=CN), respectively.  



  Scheme XXX
EMI188.1     
  
 Synthetic Scheme XXX shows the steriospecific synthesis of the parent 2H-imidazol-2-one   a      (Q=2a,6ss-      dimethyl-lss-cyclohexyl;      R7=H;    R8=butyl) from commercially available 1,3-dimethylcyclohexene (Wiley
Organics). In Step 1, the olefin was reacted with 9borabicyclo [3.3.1] nonane (9-BBN) in diglyme to give the   2a,6ss-dimethyl-lss-cyclohexylborane    adduct. In Step 2, the borane adduct was reacted with hydroxylamine-Osulfonic acid to give the corresponding amine with retention of steriochemistry. In Step 3, the amine was treated with l,l'-carbonyldiimidazole (CDI) to generate the acylimidazole in situ which was subsequently reacted with the aminoamide   i    (Scheme IV) to give the corresponding urea 8.

  In Step 4, the ureaamide 8 was reduced with the LAH to the corresponding ureaaldelyde, which partially cyclized to the 2H-imidazol-2-one 5   (Q=2α,6ss-dimethyl-1ss-cyclohexyl;      R7=H;    R8=butyl) on aqueous potassium bisulfate workup. The cyclization was completed by stirring the crude material in chloroform at reflux for 3h in the presence of a catalytic amount of trifluoroacetic acid (TFA).  



  Scheme XXXI
EMI190.1     
  
 Synthetic Scheme XXXI shows the synthesis of the parent 2H-imidazol-2-one   5      (Q=2,2-dimethylcyclohexyl;    R7=H;
R8=butyl) as a mixture of diastereomers from commercially available 2-methylcyclohexanone (Aldrich). In Step 1, the hydroxyeneone was prepared by the reaction of ethyl formate with the anion generated by sodium methoxide. In Step 2, the hydroxyeneone was converted to the corresponding butylthioeneone by reaction with n-butylmercaptan in the presence of acid. In
Step 3, the regiospecific anion at the 2-position was generated with potassium tert-butoxide and reacted with   methyliodide    to give the corresponding 2,2-dimethyl analog. In Step 4, the protecting group was removed with aqueos potassium hydroxide to give 2,2-dimethylcyclohexanone.

  In Step 5, reaction with hydroxyamine hydrochloride in the presence of sodium acetate gave the oxime. In Step 6, the oxime was reduced with LAH to give 2,2-dimethylcyclohexlamine as a mixture of diastereomers.



  In Step 7, the amine was treated with CDI to generate the acylimidazole in situ which was subsequently reacted with the aminoamide 6 (Scheme IV) to give the corresponding urea 8. In
Step 8, the ureaamide   a    was reduced with LAH to the corresponding ureaaldelyde which was cyclized by stirring in chloroform at reflux for 3h in the presence of a catalytic amount of TFA.  



   The following Examples contain detailed descriptions of the method of preparation of compounds of
Formula I. These detailed descriptions fall within the scope of, and serve to exemplify, the above described
General Synthetic Procedures which form part of the invention. These detailed descriptions are presented for illustrative purposes only and are not intended as a restriction on the scope of the invention. All parts are by weight and temperatures are in degrees Centigrade, unless otherwise indicated.



   Example 1
EMI192.1     
 1-cyclopentyl-4-butyl-1,3-dihydro-3-[[6-[2-(1H-tetrazol-5-yl)phenyl] 3-pyridinyl]methyl]-2H-imidzol-2-one   Stet:    PreDaratlon of 1-cyclopentyl-4-butyl-1,3-dihydro 2H-imidazol-2-one
 Following General Synthetic Schemes III and IV, l-cyclopentyl-4-butyl-1,3-dihydro-2H-imidazol-2-one was prepared: NMR (CDCl3)   3    0.91 (t, J=8 Hz, 3H), 1.29-1.42 (m, 2H), 1.48-1.85 (m,   10H),    1.98-2.12 (m, 2H), 2.47 (td,   J=8    and 1 Hz, 2H), 4.44-4.57 (m,   1H),    5.88 (t, J=1 Hz,   1H),    10.22 (br s,   lH);    MS (FAB) m/e (rel intensity) 209 (100), 141 (43); HRMS. Calc'd for M+H; 209.1654. Found:   200.1656.     



  Step 2: Preparation of 1-cyclopentyl-4-butyl-1,3-dihydro3-[[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one.

 

   Following General Synthetic Schemes XII and XIV or XXIII, the imidazol-2-one from Step 1 was converted to 1-cyclopentyl-4-butyl-1,3-dihydro-3-[[6-[2-(1H-tetrazol-5yl)phenyl]-3-pyridinyl]-methyl]-2H-imidazol-2-one as a colorless solid: NMR (CDCl3)   #    0.88 (t, J=7 Hz, 3H), 1.301.40 (m, 2H), 1.41-1.52 (m, 2H), 1.56-1.86 (m, 6H), 2.022.14 (m, 2H), 2.27 (t, J=7 Hz, 2H), 4.55 (m,   J=7    Hz,   1H),    4.97 (s, 2H), 5.98 (s, 1H), 7.27 (d, J=8 Hz,   1H),    7.44-7.54 (m, 3H), 7.62 (dd, J=8 and 2 Hz, 1H), 7.98-8.05 (m, 1H), 8.48 (d, J=2 Hz, 1H); MS (FAB) m/e (rel intensity) 444 (100), 416 (12), 401 (6), 387 (4), 233 (13), 209 (22), 194 (12), 180 (25); HRMS. Calc'd for M+H: 444.2512. Found: 444.2518.  



  Example 2
EMI194.1     
 1-cyclohexyl-4-butyl-1,3-dihydro-3-[[6-[2-(1H-tetrazol-5-yl)phenyl]3-pyridinyl]methyl2-2H-imidazol-2-one
Step 1:   Pretaratlon    of   1-cvclohexvl-4-butvl-1.3-dihvdro-    2H-imidazol-2-one.



   Following General Synthetic Schemes III and IV, 1-cyclohexyl-4-butyl-1,3-dihydro-2H-imidazol-2-one was prepared: NMR (CDCl3) 6 0.91 (t,   i=7    Hz, 3H), 1.05-1.24 (m, 2H), 1.26-1.46 (m, 4H), 1.47-1.58 (m, 2H), 1.63-1.76 (m, 2H), 1.78-1.96 (m, 4H), 2.36 (td, J=8 and 1 Hz, 2H), 3.874.00 (m,   1H),    5.89 (t, J=1 Hz,   1H),    9.82 (br s,   lH);    MS (FAB) m/e (rel intensity) 223 (100), 141 (53); HRMS. Calc'd for M+H: 223.1810. Found: 223.1738.



  Step 2: Preparation of 1-cyclohexyl-4-butyl-1,3-dihydro3-[[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one.



   Following General Synthetic Schemes XII and XIV or XXIII, the imidazol-2-one from Step 1 was converted to 1-cyclohexyl-4-butyl-1,3-dihydro-3-[[6-[2-(1H-tetrazol-5yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one as a colorless solid: mp   202-203     C (dec); NMR (CDCl3) 8 0.89   (t, =8 Hz, 3H), 1.08-1.24 (m, 2H), 1.26-1.54 (m, 7H), 1.66-1.76 (m,   1H),    1.77-2.00 (m, 4H), 2.28 (t, J=8 Hz, 2H), 3.95-4.07 (m,   lH),    4.97 (s, 2H), 6.00 (s, 1H), 7.32 (d,
J=8 Hz, 1H), 7.45-7.55 (m, 3H), 7.69 (dd, J=8 and 2 Hz, 1H), 7.96-8.04 (m, 1H), 8.47 (d, J=2 Hz,   lH);    MS (FAB) m/e (rel intensity) 458 (56), 430 (19), 237 (19), 208 (100), 194 (36), 180 (76); HRMS. Calc'd for M+H: 458.2668. Found: 458.2732.  



  Example 3
EMI196.1     
   1. (2α,6α-1ss-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H-tetrazol-5-    yl)phenyl]-3-pyridinyl]methyl]-2H-imidzol]-2-one
Step 1: preparation of   1-(2α,6α-dimethyl-1ss-cyclohexyl)-    4-butyl-1,3-dihydro-2H-imidazol-2-one.



  Following Synthetic Scheme XXX,   1-(2α,6α-dimethyl-1ss-    cyclohexyl)-4-butyl-1,3-dihydro-2H-imidazol-2-one was prepared: NMR (CDCl3) 8 0.78 (d, J=7 Hz, 6H), 0.90 (t, J=7
Hz, 3H), 1.08-1.26 (m, 2H), 1.26-1.40 (m, 3H), 1.46-1.59   (m,    4H), 1.66-1.85 (m, 3H), 2.37 (t, J=7 Hz, 2H), 3.35 (t,
J=11 Hz,   1H),    5.48 (s,   1H),    9.80 (br s,   1H);    MS (FAB) m/e (rel intensity) 251 (100), 141 (58).



     Stet2:      Preparatlon    of   1-(2α,6α-dimethyl-1ss-cyclohexyl)-    4-butyl-1,3-dihydro-3-[[6-[2-(1H-tetrazol-5-yl)phenyl]-3pyridinyl]methyl]-2H-imidazol-2-one.



  Following Synthetic Schemes XXII and XXIII, the imidazol-2one from Step 1 was converted to   1-(2α,6α-dimethyl-1ss-    cyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H-tetrazol-5yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one as a colorless solid: NMR   (CDCl3)    8 0.77 (d,   J=7    Hz,   6N),    0.88   (t, J=7 Hz, 3H), 1.06-1.39 (m, 5H), 1.41-1.63 (m, 4H), 1.65-1.86 (m, 3H), 2.27 (t, J=7 Hz, 2H), 3.41 (br t, J=11
Hz, 1H), 5.00 (s, 2H), 5.90 (s,   lH);    7.16(d, J=8 Hz, 1H), 7.42-7.48 (m, 3H), 7.52 (dd, J=8 and 2 Hz, 1H), 7.86-7.91 (m, 1H), 8.38 (d, J=2 Hz,   lH);    MS (FAB) m/e (rel intensity) 486 (100), 458 (21), 443 (6), 429 (6), 237 (15), 209 (47), 194 (20), 180 (51); HRMS.

  Calc'd for M+H:   486.2918.    Found:   486.2918.     



  Example 4
EMI198.1     
 1.(2,2-dimethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H-tetrazol 5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one
Step 1: Preparation of 1-(2,2-dimethylcyclohexyl)-4butyl-1,3-dihydro-2H-imidazol-2-one.



  Following Synthetic Scheme XXXI, 1-(2,2    dimethylcyclohexyl)-4-butyl-1,3-dihydro-2H-imidazol-2-one    was prepared: NMR (CDCl3)   8    0.91 (t, J=7 Hz, 3H), 0.93 (s, 6H), 1.21-1.87 (m, 12H), 2.35 (t, J=8 Hz, 2H), 3.59 (dd,
J=13 and 4 Hz,   1H),    5.80-5.85 (m,   1H),    10.2 (s,   1H).   



  Step 2: preparation of 1-(2,2-dimethylcyclohexyl)-4butyl-1,3-dihydro-3-[[6-[2-(1H-tetrazol-5-yl)phenyl]-3pyridinyl]methyl]-2H-imidazol-2-one.



  Following Synthetic Schemes XXII and XXIII, the imidazol-2one from Step 1 was converted to 1-(2,2dimethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H    tetrazol-5-yl)phenyl]-3-pyridinyl3methyl]-2H-imidazol-2-one    as a colorless solid: NMR (CDCl3) 8 0.79   (5,    3H), 0.82 (t,
J=7 Hz, 3H), 0.89   (s,    3H), 1.20-1.50 (m, 10H). 1.69-1.95   (m, 2H), 2.23 (t, J=7 Hz, 2H), 3.77 (dd, J=14 and 3 Hz, 1H), 7.78 (d, J=15 Hz, 1H), 7.83 (d, J=15 Hz, 1H), 6.23 (s, 1H), 7.40 (d, J=8 Hz, 1H), 7.53 (dd, J=8 and 2 Hz, 1H), 7.58-7.78 (m, 4H), 8.20 (d, J=2 Hz,   lH);    MS (FAB) m/e (rel intensity) 486 (47), 458 (32), 243 (26), 209 (100), 180 (78), 141 (40); HRMS.   Calc'd    for M+H: 486.2981. Found: 486.2979.  



   BIOLOGICAL EVALUATION
Assav A: Anaiotensin II Bindina Activitv
 Compounds of the invention were tested for ability to bind to the smooth muscle angiotensin II receptor using a rat uterine membrane preparation.



  Angiotensin II   (AII)    was purchased from Peninsula Labs.



     1251-angiotensin    II (specific activity of 2200 Ci/mmol) was purchased from Du Pont-New England Nuclear. Other chemicals were obtained from Sigma Chemical Co. This assay was carried out according to the method of Douglas et al   [Endocrlnologv,      106,    120-124 (1980)]. Rat uterine membranes were prepared from fresh tissue. All procedures were carried out at 40C. Uteri were stripped of fat and homogenized in phosphate-buffered saline at pH 7.4 containing 5 mM EDTA. The homogenate was centrifuged at 1500 x g for 20 min., and the supernatant was recentrifuged at 100,000 x g for 60 min. The pellet was resuspended in buffer consisting of 2 mM EDTA and 50 mM Tris-HCl   (pH    7.5) to a final protein concentration of 4 mg/ml.

  Assay tubes were charged with 0.25 ml of a solution containing 5 mM   MgCl2,    2 mM EDTA, 0.5% bovine serum albumin, 50 mM Tris   Howl,    pH 7.5 and 125I-AII (approximately 105 cpm) in the absence or in the presence of unlabelled ligand. The reaction was initiated by the addition of membrane protein and the mixture was incubated at 25 C for 60 min. The incubation was terminated with ice-cold 50 mM   Tris-KC1      (pH    7.5) and the mixture was filtered to separate membranebound labelled peptide from the free ligand. The incubation tube and filter were washed with ice-cold buffer. Filters were assayed for radioactivity in a Micromedic gamma counter. 

  Nonspecific binding was defined as binding in the presence of 10   gM    of unlabelled   AII.    Specific binding was calculated as total binding minus nonspecific binding. The  receptor binding affinity of an   All    antagonist compound was indicated by the concentration (IC50) of the tested   All    antagonist which gives 50% displacement of the total specifically bound 125I-AII from the high affinity   All    receptor. Binding data were analyzed by a nonlinear leastsquares curve fitting program. Results are reported in
Table I.



  Assav B: In Vitro Vascular Smooth   Muscle-ResDonse    for   All   
 The compounds of the invention were tested for antagonist activity in rabbit aortic rings. Male New
Zealand white rabbits (2-2.5 kg) were sacrificed using an overdose of pentobarbital and exsanguinated via the carotid arteries. The thoracic aorta was removed, cleaned of adherent fat and connective tissue and then cut into 3-mm ring segments. The endothelium was removed from the rings by gently sliding a rolled-up piece of filter paper into the vessel lumen.

  The rings were then mounted in a waterjacketed tissue bath, maintained at   37"C,    between moveable and fixed ends of a stainless steel wire with the moveable end attached to an   FT03    Grass transducer coupled to a Model 7D Grass Polygraph for recording isometric force responses.



  The bath was filled with 20 ml of oxygenated   (958    oxygen/5 carbon dioxide) Krebs solution of the following composition (mM): 130   Nail,    15   NaHC03,    15 KCl, 1.2   NaR2P04,    1.2   MgS04,    2.5   CaC12,    and 11.4 glucose. The preparations were equilibrated for one hour before approximately one gram   or    passive tension was placed on the rings. Angiotensin II concentration-response curves were then recorded (3   Y,    10-10 to 1 X 10-5 M).

  Each concentration of   All    was allowed to elicit its maximal contraction, and then   All    was washed out repeatedly for 30 minutes before rechallenging with a higher concentration of   All.    Aorta rings were exposed to  the test antagonist at 10-5 M for 5 minutes before challenging with   AII.    Adjacent segments of the same aorta ring were used for all concentration-response curves in the presence or absence of the test antagonist. The effectiveness of the test compound was expressed in terms of pA2 values and were calculated according to H.O. Schild   Lsr.    J. Pharmacol. Chemother.,   2,189-206    (1947)].

  The   pA2    value is the concentration of the antagonist which increases the EC50 value for   All    by a factor of two. Each test antagonist was evaluated in aorta rings from two rabbits. Results are reported in Table I.



  Assav C: In   Vivo    Intraaastric Pressor Assav ResDonse for
All   Antaaonists   
 Male Sprague-Dawley rats weighing 225-300 grams were anesthetized with methohexital (30 mg/kg, i.p.) and catheters were implanted into the femoral artery and vein.



  The catheters were tunneled subcutaneously to exit dorsally, posterior to the head and between the scapulae.



  The catheters were filled with heparin (1000 units/ml of saline). The rats were returned to their cage and allowed regular rat chow and water   adlibitum.    After full recovery from surgery (3-4 days), rats were placed in Lucite holders and the arterial line was connected to a pressure transducer. Arterial pressure was recorded on a Gould polygraph   (mmHg).    Angiotensin II was administered as a 30 ng/kg bolus via the venous catheter delivered in a 50   gl    volume with a 0.2 ml saline flush. The pressor response in mm Hg was measured by the difference from pre-injection arterial pressure to the maximum pressure achieved. The   All    injection was repeated every 10 minutes until three consecutive injections yielded responses within 4 mmHg   oe    each other.

  These three responses were then averaged and  represented the control response to   AII.    The test compound was suspended in 0.5% methylcellulose in water and was administered by gavage. The volume administered was 2 ml/kg body weight. The standard dose was 3 mg/kg.



  Angiotensin II bolus injections were given at 30, 45, 60, 75, 120, 150, and 180 minutes after gavage. The pressor response to   All    was measured at each time point. The rats were then returned to their cage for future testing. A minimum of 3 days was allowed between tests. Percent inhibition was calculated for each time point following gavage by the following formula: [(Control Response 
Response at time point)/Control Response] X 100. Results   ae    shown in Table I.  



   TABLE I
 In Vitro and In Vivo   Analotensln II   
 Activity of Compounds of the Invention
Test 1Assay A 2Assay B 3Assay C
Compound   ICso    (nM)   pA2    Dose: 3 mg/kg (i.g.)
Example # Inhibition (%) Duration (min.)
 1 50 9.04/8.60 50  > 180
 2 20 9.14/9.15 40  > 180
 3 4.9 NC 70  > 180
 4 3.6 NT NT -1Assay A: Angiotensin II Receptor Binding Activity 2Assay B: In Vitro Vascular Smooth Muscle Response 3Assay C: In Vivo Pressor Response (all test compounds
 administered intragastrically at 3 mg/kg).



   NT= Not Tested
 NC = Non-competitive antagonist  
 Also embraced within this invention is a class of pharmaceutical compositions comprising one or more compounds of Formula I in association with one or more nontoxic, pharmaceutically acceptable carriers and/or diluents and/or adjuvants (collectively referred to herein as "carrier" materials) and, if desired, other active ingredients. The compounds of the present invention may be administered by any suitable route, preferably in the form of a pharmaceutical composition adapted to such a route, and in a dose effective for the treatment intended.



  Therapeutically effective doses of the compounds of the present invention required to prevent or arrest the progress of the medical condition are readily ascertained by one of ordinary skill in the art. The compounds and composition may, for example, be administered intravascularly, intraperitoneally, subcutaneously, intramuscularly or topically.

 

   For oral administration, the pharmaceutical composition may be in the form of, for example, a tablet, capsule, suspension or liquid. The pharmaceutical composition is preferably made in the form of a dosage unit containing a particular amount of the active ingredient.



  Examples of such dosage units are tablets or capsules.



  These may with advantage contain an amount of active ingredient from about 1 to 250 mg, preferably from about 25 to 150 mg. A suitable daily dose for a mammal may vary widely depending on the condition of the patient and other factors. However, a dose of from about 0.1 to 3000 mg/kg body weight, particularly from about 1 to 100 mg/kg body weight, may be appropriate.



   The active ingredient may also be administered by injection as a composition wherein, for example, saline, dextrose or water may be used as a suitable carrier. A  suitable daily dose is from about 0.1 to 100 mg/kg body weight injected per day in multiple doses depending on the disease being treated. A preferred daily dose would be from about 1 to 30 mg/kg body weight. Compounds indicated for prophylactic therapy will preferably be administered in a daily dose generally in a range from about 0.1 mg to about 100 mg per kilogram of body weight per day. A more preferred dosage will be a range from about 1 mg to about 100 mg per kilogram of body weight. Most preferred is a dosage in a range from about 1 to about 50 mg per kilogram of body weight per day. A suitable dose can be administered, in multiple sub-doses per day. These subdoses may be administered in unit dosage forms.

  Typically, a dose or sub-dose may contain from about 1 mg to about 100 mg of active compound per unit dosage form. A more preferred dosage will contain from about 2 mg to about 50 mg of active compound per unit dosage form. Most preferred is a dosage form containing from about 3 mg to about 25 mg of active compound per unit dose.



   The dosage regimen for treating a disease condition with the compounds and/or compositions of this invention is selected in accordance with a variety of factors, including the type, age, weight, sex and medical condition of the patient, the severity of the disease, the route of administration, and the particular compound employed, and thus may vary widely.



   For therapeutic purposes, the compounds of this invention are ordinarily combined with one or more adjuvants appropriate to the indicated route of administration. If administered   re¯ os,    the compounds may be admixed with lactose, sucrose, starch powder, cellulose esters of alkanoic acids, cellulose alkyl esters, talc, stearic acid, magnesium stearate, magnesium oxide, sodium  and calcium salts of phosphoric and sulfuric acids, gelatin, acacia gum, sodium alginate, polyvinylpyrrolidone, and/or polyvinyl alcohol, and then tableted or encapsulated for convenient administration. Such capsules or tablets may contain a controlled-release formulation as may be provided in a dispersion of active compound in hydroxypropylmethyl cellulose. 

  Formulations for parenteral administration may be in the form of aqueous or non-aqueous isotonic sterile injection solutions or suspensions. These solutions and suspensions may be prepared from sterile powders or granules having one or more of the carriers or diluents mentioned for use in the formulations for oral   administration.    The compounds may be dissolved in water, polyethylene glycol, propylene glycol, ethanol, corn oil, cottonseed oil, peanut oil, sesame oil, benzyl alcohol, sodium chloride, and/or various buffers. Other adjuvants and modes of administration are well and widely known in the pharmaceutical art.



   Although this invention has been described with respect to specific embodiments, the details of these embodiments are not to be construed as limitations.

Claims

What Is Claimed Is:
1. A compound of Formula I: EMI208.1 wherein Q is a cycloalkyl group having three to about eight ring carbon atoms, and wherein said cycloalkyl group may be unsubstituted or substituted on one or more substitutable positions by one or more groups independently selected from hydrido, alkyl, alkoxy, cyano, halo, hydroxy, nitro, amino, alkylamino, carboxyl, alkoxycarbonyl, formyl, oxo, alkylcarbonyl and haloalkylcarbonyl; wherein R7 is selected from hydrido, alkyl, halo, haloalkyl, formyl, carboxyl and alkoxyalkyl; wherein R8 is selected from alkyl, phenyl, phenylalkyl, cycloalkyl and cycloalkylalkyl; wherein m is a number selected from one to four, inclusive;
wherein A is an acid-group-substituted pyridinyl-phenyl moiety selected from EMI208.2 wherein R9 is an acidic group selected from COOH and EMI208.3 or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof. 2. A compound of Claim 1 wherein Q is EMI209.1 wherein each of R1, R2, R3, R4, R5 and R6 is independently selected from hydrido, alkyl, alkoxy, cyano, halo, hydroxy, nitro, amino, alkylamino, carboxyl, alkoxycarbonyl, formyl, alkylcarbonyl and haloalkylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R3 and R4 may further be taken together to form oxo; wherein R5 and R6 may further be taken together to form oxo; wherein each of d, b and r is a number selected from zero through five, inclusive, and wherein the sum of d+b+r is a number from zero through five, inclusive.
3. Compound of Claim 2 wherein Q is selected from EMI209.2 wherein each of R1, R2 and R3 is independently selected from hydrido, alkyl, alkoxy, cyano, halo, hydroxy, nitro, amino, alkylamino, carboxyl, alkoxycarbonyl, formyl, alkylcarbonyl and haloalkylcarbonyl; and wherein R1 and R2 may further be taken together to form oxo.
4. Compound of Claim 1 of Formula II: EMI210.1 wherein each of R1 through R6 is independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, cyano, fluoro, chloro, iodo, bromo, hydroxy, nitro, amino, Nmethylamino, N,N-dimethylamino, N-ethylamino, N,Ndiethylamino, carboxyl, methoxycarbonyl, ethoxycarbonyl, formyl, methylcarbonyl, ethylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R3 and R4 may further be taken together to form oxo; wherein R5 and R6 may further be taken together to form oxo; wherein each of d, b and r is a number selected from zero through five, inclusive, and wherein the sum of d+b+r is a number selected from zero through five, inclusive;
wherein R7 is selected from hydrido, methyl, fluoro, chloro, monofluoromethyl, difluoromethyl, trifluoromethyl, formyl, carboxyl and dimethoxymethyl; wherein R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, phenyl, benzyl, phenethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl and cyclohexylethyl; wherein A is an acidicgroup-substituted pyridinyl-phenyl moiety selected from EMI211.1 wherein R9 is an acidic group selected from COOH and EMI211.2 or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.
5. Compound of Claim 4 of Formula V: EMI211.3 wherein each of R1, R2 and R3 is independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, cyano, fluoro, chloro, iodo, bromo, hydroxy, nitro, amino, N-methylamino, N,N-dimethylamino, N-ethylamino, N,Ndiethylamino, carboxyl, methoxycarbonyl, ethoxycarbonyl, formyl, methylcarbonyl, ethylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is selected from hydrido, methyl, fluoro, chloro, monofluoromethyl, difluoromethyl, trifluoromethyl, formyl, carboxyl and dimethoxymethyl;
wherein R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tertbutyl, n-pentyl, isopentyl, neopentyl, phenyl, benzyl, phenethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl and cyclohexylethyl; wherein A is an acidic-group-substituted pyridinyl-phenyl moiety selected from EMI212.1 wherein R9 is an acidic group selected from COOH and EMI212.2 or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.
6. Compound of Claim 5 of Formula V(b): EMI213.1 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.
7. Compound of Claim 6 selected from compounds and their stereoisomers and tautomers and the pharmaceutically-acceptable salts thereof, said compounds consisting of 1-(2-methylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one 1-(2-ethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-propylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-isopropylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-tertbutylcyclopentyl)-4-butyl-1,3-dihyuro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;
1-(2-methOxyCyclopentyl)-4-butyl-1,3-dihyaro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-hydroxyCyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; l-(2-carboxyCyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-acetylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-oxocyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-methyl-5-methyl-cyclopentyl)-4-butyl-1,3-dihydro-3-[[6- [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;
1-(2-ethyl-5-methyl-cyclopentyl)-4-butyl-1,3-dihydro-3-[[6 [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol- 2-one; 1-(2-isopropyl-5-methyl-cyclopentyl)-4-butyl-1,3-dihydro-3- [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;
1-(2-carboxy-5-methyl-cyclopentyl)-4-butyl-1,3-dihydro-3-[[6 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2-acetyl-5-methyl-cyclopentyl)-4-butyl-1,3-dihydro-3-[[6- [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2-oXo-5-methyl-cyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2- one; 1-(2-methyl-5-ethyl-cyclopentyl)-4-butyl-1,3-dihydro-3-[[6- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol- 2-one; 1-(2-ethyl-5-ethyl-cyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2- one;
; 1- (2-isopropyl-5-ethyl-cyclopentyl)-4-butyl-l,3-dihydro-3- [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;
1-(2-carboxy-5-ethyl-cyclopentyl)-4-butyl-1,3-dihydro-3-[[6 [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol- 2-one; 1-(2-acetyl-5-ethyl-cyclopentyl)-4-butyl-1,3-dihydro-3-[[6 [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol- 2-one; 1-(2-oXo-5-ethyl-cyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2- one;
1-(2-methyl-5-isopropyl-cyclopentyl)-4-butyl-1,3-dihydro-3 [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; l-(2-ethyl-5-isopropyl-cyclopentyl)-4-butyl-1,3-dihydro-3- [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-isopropyl-5-isopropyl-cyclopentyl)-4-butyl-1,3-dihydro3-[[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-carboxy-5-isopropyl-cyclopentyl)-4-butyl-1,3-dihydro-3 [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;
1-(2-acetyl-5-isopropyl-cyclopentyl)-4-butyl-1,3-dihydro-3 [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-oXo-5-isopropyl-cyclopentyl)-4-butyl-1,3-dihydro-3-[[6- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol- 2-one; 1-(2,2-dimethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)sphenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; and 1-(2,2-diethylcyclopentyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one.
8. Compound of Claim 7 which is 1-cyclopentyl-4 butyl-1,3-dihydro-3-[[6-[2-(lH-tetrazol-5-yl)phenyl]-3- pyridinyl3methyl]-2H-imidazol-2-one or a pharmaceuticallyacceptable salt thereof.
9. Compound of Claim 4 of Formula VI: EMI216.1 wherein each of R, R2 and R3 is independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, cyano, fluoro, chloro, iodo, bromo, hydroxy, nitro, amino, N-methylamino, N,N-dimethylamino, N-ethylamino, N,N- diethylamino, carboxyl, methoxycarbonyl, ethoxycarbonyl, formyl, methylcarbonyl, ethylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is selected from hydrido, methyl, fluoro, chloro, monofluoromethyl, difluoromethyl, trifluoromethyl, formyl, carboxyl and dimethoxymethyl;
wherein R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tertbutyl, n-pentyl, isopentyl, neopentyl, phenyl, benzyl, phenethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl and cyclohexylethyl; wherein A is an acidic-group-substituted pyridinyl-phenyl moiety selected from EMI217.1 wherein R9 is an acidic group selected from COOH and EMI217.2 or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.
10. Compound of Claim 9 of Formula VI(b): EMI217.3 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.
11. Compound of Claim 10 selected from compounds and their stereoisomers and tautomers and the pharmaceutically-acceptable salts thereof, said compounds consisting of 1-(2-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-propylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;
1-(2-tertbutylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-methOxycyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-hydroxycyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-carboxycyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-acetylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-oxocyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;
1-(2-methyl-6-methyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6- [2-(1H-tetrzol-5-yl)phenyl2-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2-ethyl-6-methyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2- (1H-tetrzol-5-yl)phenyl]-3-pyridinyl]-methyl]-2H-imidazol-2one; 1-(2-isopropyl-6-methyl-cyclohexyl)-4-butyl-1,3-dihydro-3 [[6-[2-(1H-tetrazol-5-yl)phenyl2-3-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-carboxy-6-methyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6- [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2-acetyl-6-methyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol- 2-one;
1-(2-oxo-6-methyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2 (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2- one; 1-(2-methyl-6-ethyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2- one; 1-(2-ethyl-6-ethyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2 (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2- one; 1-(2-isopropyl-6-ethyl-cyclohexyl)-4-butyl-1,3-dihyaro-3-[[6- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol- 2-one;
1-(2-carboxy-6-ethyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2-acetyl-6-ethyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2- one; 1-(2-oXo-6-ethyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2- one; 1-(2-methyl-6-isopropyl-cyclohexyl)-4-butyl-1,3-dihydro-3 [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;
1-(2-ethyl-6-isopropyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; l-(2-isopropyl-6-isopropyl-cyclohexyl) -4-butyl-1,3-dihydro-3- [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; l-(2-carboxy-6-isopropyl-cyclohexyl) -4-butyl-l,3-dihydro-- [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;
1-(2-acetyl-6-isopropyl-cyclohexyl)-4-butyl-1,3-dihydro-3 [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;
1-(2-oxo-6-isopropyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2,2-dimethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; and 1-(2,2-diethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one.
12. Compound of Claim 11 which is l-cyclohexyl-4- butyl-1,3-dihydro-3-[[6-[2-(lH-tetrazol-5-yl)phenyl]-3- pyridinyl]methyl]-2H-imidazol-2-one or a pharmaceuticallyacceptable salt thereof.
13. Compound of Claim 11 which is 1-(2a,6a-1P- cyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H-tetrazol-5 yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one or a pharmaceutically-acceptable salt thereof.
14. Compound of Claim 11 which is 1(2,2 dimethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl-3-pyridinyl]methyl]-2H-imidazol-2-one or a pharmaceutically-acceptable salt thereof.
15. A pharmaceutical composition comprising a therapeutically-effective amount of an angiotensin II antagonist compound and a pharmaceutically-acceptable carrier or diluent, said antagonist compound selected from a family of compounds of Formula VI: EMI221.1 wherein each of R1, R2 and R3 is independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, cyano, fluoro, chloro, iodo, bromo, hydroxy, nitro, amino, N-methylamino, N,N-dimethylamino, N-ethylamino, N,Ndiethylamino, carboxyl, methoxycarbonyl, ethoxycarbonyl, formyl, methylcarbonyl, ethylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is selected from hydrido, methyl, fluoro, chloro, monofluoromethyl, difluoromethyl, trifluoromethyl, formyl, carboxyl and dimethoxymethyl;
wherein R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tertbutyl, n-pentyl, isopentyl, neopentyl, phenyl, benzyl, phenethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl and cyclohexylethyl; wherein A is an acidic-group-substituted pyridinyl-phenyl moiety selected from EMI221.2 wherein R9 is an acidic group selected from COOH and EMI222.1 or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.
16. The composition of Claim 15 wherein said antagonist compound is of Formula VI(b): EMI222.2 wherein each of R1, R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.
17. The composition of Claim 16 wherein said antagonist compound is selected from compounds and their stereoisomers and tautomers and the pharmaceuticallyacceptable salts thereof, said compounds consisting of 1-(2-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl] -3-pyridinyl]methyi] -2N-imidazoi-2-one;
1-(2-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-propylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-( 1H- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-( 1H- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-tertbutylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one 1-(2-methoxycyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one 1-(2-hydroxycyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;
1-(2-carboxycyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-acetylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-oxocyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-methyl-6-methyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol 2-one; 1-(2-ethyl-6-methyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2 (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one; 1-(2-isopropyl-6-methyl-cyclohexyl)-4-butyl-1,3-dihydro-3- [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;
1-(2-carboxy-6-methyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol 2-one; 1-(2-acetyl-6-methyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol 2-one; 1-(2-oXo-6-methyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2- (1H-tetrazol-5-yl)phyenyl]-3-pyridinyl]methyl]-2H-imidazol-2one; 1-(2-methyl-6-ethyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2 (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2- one; 1-(2-ethyl-6-ethyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2- one; 1-(2-isopropyl-6-ethyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;
1-(2-carboxy-6-ethyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2-acetyl-6-ethyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2- one; 1-(2-oxo-6-ethyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2 (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2- one; 1-(2-methyl-6-isopropyl-cyclohexyl)-4-butyl-1,3-dihydro-3- [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-ethyl-6-isopropyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2-isopropyl-6-isopropyl-cyclohexyl)-4-butyl-1,3-dihydro-3 [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;
l-(2-carboxy-6-isopropyl-cyclohexyl)-4-butyl-i,3-dihydro-3 [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-acetyl-6-isopropyl-cyclohexyl)-4-butyl-1,3-dihydro-3 [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-oxo-6-isopropyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2,2-dimethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; and
1-(2,2-diethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one.
18. The composition of Claim 17 wherein said antagonist compound is l-cyclohexyl-4-butyl-1,3-dihydro-3 [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one or a pharmaceutically-acceptable salt thereof.
19. The composition of Claim 17 wherein said antagonist compound is 1-(2a,6a-lss-cyclohexyl)-4-butyl-lt3- dihydro-3-[[6-[2-(lH-tetrazol-5-yl)phenyl]-3- pyridinyl]methyl] -2H-imidazol-2-one or a pharmaceuticallyacceptable salt thereof.
20. The composition of Claim 17 wherein said antagonist compound is 1(2,2-dimethylcyclohexyl)-4-butyl-1,3 dihydro-3-[[6-[2-(lH-tetrazol-5-yl)phenyl-3- pyridinylimethyl] -2N-imidazoi-2-one or a pharmaceuticallyacceptable salt thereof.
21. A therapeutic method for treating a circulatory disorder or a circulatory-related disorder, said method comprising administering to a subject susceptible to or afflicted with such disorder a therapeutically-effective amount of an active compound of Formula VI: EMI225.1 wherein each of R1, R2 and R3 is independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, cyano, fluoro., chloro, iodo, bromo, hydroxy, nitro, amino, N-methylamino, N,N-dimethylamino, N-ethylamino, N,N- diethylamino, carboxyl, methoxycarbonyl, ethoxycarbonyl, formyl, methylcarbonyl, ethylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo;
wherein R7 is selected from hydrido, methyl, fluoro, chloro, monofluoromethyl, difluoromethyl, trifluoromethyl, formyl, carboxyl and dimethoxymethyl; wherein R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tertbutyl, n-pentyl, isopentyl, neopentyl, phenyl, benzyl, phenethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclobutylethyl, cyclopentylmethyl, cyclopentylethyl, cyclohexylmethyl and cyclohexylethyl; wherein A is an acidic-group-substituted pyridinyl-phenyl moiety selected from EMI226.1 wherein R9 is an acidic group selected from COOH and EMI226.2 or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.
22. The method of Claim 21 wherein said active compound is of Formula VI(b): EMI227.1 wherein each of R11 R2 and R3 may be independently selected from hydrido, methyl, ethyl, n-propyl, isopropyl, tertbutyl, hydroxy, methoxy, fluoro, chloro, iodo, bromo, carboxyl, formyl, methylcarbonyl and trifluoromethylcarbonyl; wherein R1 and R2 may further be taken together to form oxo; wherein R7 is hydrido; wherein R8 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl and neopentyl; or a stereoisomer or a tautomer thereof or a pharmaceutically-acceptable salt thereof.
23. The method of Claim 22 wherein said compound is selected from compounds and their stereoisomers and tautomers and the pharmaceutically-acceptable salts thereof, said compounds consisting of 1-(2-methylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-ethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-propylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidzol-2-one; 1-(2-isopropylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one;
1-(2-methOxycyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-hydroxycyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-carboxycyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-acetylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(lH- tetrazol-5-yl)phenyl)-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-oxocyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one; 1-(2-methyl-6-methyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6 [2-(1H-tetrazol-5-yl)phenyl)-3-pyridinyl]methyl]-2H-imidazol2-one;
1-(2-ethyl-6-methyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2 (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2- one; 1-(2-isopropyl-6-methyl-cyclohexyl)-4-butyl-1,3-dihydro-3- [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-carboxy-6-methyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6- [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2-acetyl-6-methyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol- 2-one; 1-(2-oxo-6-methyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2 (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one;
1-(2-methyl-6-ethyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2 (1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2one; 1-(2-ethyl-6-ethyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2- one; 1-(2-isopropyl-6-ethyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6- [2-(lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol- 2-one; 1-(2-carboxy-6-ethyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one;
1-(2-acetyl-6-ethyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2 (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2- one; 1-(2-oXo-6-ethyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2- (lH-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2- one; l-(2-methyl-6-isopropyl-cyclohexyi) -4-butyl-l,3-dihydro-3- [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one;
1-(2-ethyl-6-isopropyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6 [2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; i- (2-isopropyl-6-isopropyl-cyciohexyl) -4-butyl-i,3-dihydro-3- [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; l-(2-carboxy-6-isopropyl-cyciohexyl)-4-butyl-1,3-dihydro3 [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2Himidazol-2-one; 1-(2-acetyl-6-isopropyl-cyclohexyl)-4-butyl-1,3-dihydro-3- [[6-[2-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H imidazol-2-one; 1-(2-oXo-6-isopropyl-cyclohexyl)-4-butyl-1,3-dihydro-3-[[6- [3-(1H-tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol2-one; 1-(2,2-dimethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1Htetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-midazol-2-one;
and 1-(2,2-diethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2-(1H tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one.
24. The method of Claim 23 wherein said compound is 1-cyclohexyl-4-butyl-1,3-dihydro-3-[[6-[2-(1H-tetrazol-5 yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one or a
tautomer thereof or a pharmaceutically-acceptable salt thereof.
25. The method of Claim 23 wherein said compound is l-(2aZ6a-lss-cyclohexyl)-4-butyl-lw3-dihydro-3-[[6-[2-(lH tetrazol-5-yl)phenyl]-3-pyridinyl]methyl]-2H-imidazol-2-one or a pharmaceutically-acceptable salt thereof.
26. The method of Claim 23 wherein said compound is 1(2,2-dimethylcyclohexyl)-4-butyl-1,3-dihydro-3-[[6-[2 (1H-tetrazol-5-yl)phenyl-3-pyridinyl)methyl]-2H-imidazol-2one or a pharmaceutically-acceptable salt thereof.
27. The method of Claim 21 wherein said circulatory disorder is a cardiovascular disorder.
28. The method of Claim 27 wherein said cardiovascular disorder is hypertension.
29. The method of Claim 27 wherein said cardiovascular disorder is congestive heart failure.
30. The method of Claim 21 wherein said circulatory-related disorder is glaucoma.
EP93915307A 1992-10-13 1993-06-16 N-arylheteroarylalkyl 1-cycloalkyl-imidazol-2-one compounds for treatment of circulatory disorders Withdrawn EP0664803A1 (en)

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US5087634A (en) * 1990-10-31 1992-02-11 G. D. Searle & Co. N-substituted imidazol-2-one compounds for treatment of circulatory disorders
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