TREA

6-membered aromatics as factor Xa inhibitors

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Information

  • Patent Grant
  • 6060491
  • Patent Number
    6,060,491
  • Date Filed
    Thursday, June 18, 1998
    26 years ago
  • Date Issued
    Tuesday, May 9, 2000
    24 years ago
Information
Abstract
The present application describes 6-membered aromatics of formula I: ##STR1## or pharmaceutically acceptable salt forms thereof, wherein D may be CH.sub.2 NH.sub.2 or C(.dbd.NH)NH.sub.2, which are useful as inhibitors of factor Xa.
Description

FIELD OF THE INVENTION
This invention relates generally to novel 6-membered aromatics which are inhibitors of trypsin-like serine protease enzymes, especially factor Xa, pharmaceutical compositions containing the same, and methods of using the same as anticoagulant agents for treatment and prevention of thromboembolic disorders.
BACKGROUND OF THE INVENTION
WO 96/28427 describes benzamidine anticoagulants of the formula: ##STR2## wherein Z.sup.1 and Z.sup.2 are O, N(R), S or OCH.sub.2 and the central ring may be phenyl or a variety of heterocycles. The presently claimed compounds do not contain the Z.sup.1 linker or the substitution pattern of the above compounds.
WO 95/18111 addresses fibrinogen receptor antagonists, containing basic and acidic termini, of the formula: ##STR3## wherein R.sup.1 represents the basic termini, U is an alkylene or heteroatom linker, V may be a heterocycle, and the right hand portion of the molecule represents the acidic termini. The presently claimed compounds do not contain the acidic termini of WO 95/18111.
Activated factor Xa, whose major practical role is the generation of thrombin by the limited proteolysis of prothrombina holds a central position that links the intrinsic and extrinsic activation mechanisms in the final common pathway of blood coagulation. The generation of thrombin, the final serine protease in the pathway to generate a fibrin clot, from its precursor is amplified by formation of prothrombinase complex (factor Xa, factor V, Ca.sup.2+ and phospholipid). Since it is calculated that one molecule of factor Xa can generate 138 molecules of thrombin (Elodi, S., Varadis K.: Optimization of conditions for the catalytic effect of the factor IXa-factor VIII Complex: Probable role of the complex in the amplification of blood coagulation. Thromb. Res. 1979, 15, 617-629), inhibition of factor Xa may be more efficient than inactivation of throibin in interrupting th e blood coagulation system.
Therefore, efficacious and specific inhibitors of factor Xa are needed as potentially valuable therapeutic agents for the treatment of thromboembolic disorders. It is thus desirable to discover new factor Xa inhibitors.
SUMMARY OF THE INVENTION
Accordingly, one object of the present invention is to provide novel 6-membered aromatics which are useful as factor Xa inhibitors or pharmaceutically acceptable salts or prodrugs thereof.
It is another object of the present invention to provide pharmaceutical compositions comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of at least one of the compounds of the present invention or a pharmaceutically acceptable salt or prodrug form thereof.
It is another object of the present invention to provide a method for treating thromboembolic disorders comprising administering to a host in need of such treatment a therapeutically effective amount of at least one of the compounds of the present invention or a pharmaceutically acceptable salt or prodrug form thereof.
These and other objects, which will become apparent during the following detailed description, have been achieved by the inventors' discovery that compounds of formula (I): ##STR4## or pharmaceutically acceptable salt or prodrug forms thereof, wherein A, B, D, E, M, R.sup.1a, R.sup.1b, and Z are defined below, are effective factor Xa inhibitors.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
[1] Thus, in a first embodiment, the present invention provides novel compounds of formula I: ##STR5## or a stereoisomer or pharmaceutically acceptable salt form thereof, wherein;
ring M contains from 0-4 N atoms;
D is selected from CN, C(.dbd.NR.sup.7)NR.sup.8 R.sup.9, NHC(.dbd.NR.sup.7)NR.sup.8 R.sup.9, NR.sup.8 CH(.dbd.NR.sup.7), C(O)NR.sup.8 R.sup.9, and (CR.sup.8 R.sup.9).sub.t NR.sup.8 R.sup.9 ;
E is selected from phenyl, 2-pyridyl, 4-pyridyl, pyrimidyl, and piperidinyl substituted with 1 R;
R is selected from H, F, Cl, Br, I, OR.sup.3, SR.sup.3, CO.sub.2 R.sup.3, NO.sub.2, and CH.sub.2 OR.sup.3, and (CR.sup.8 R.sup.9).sub.t NR.sup.8 R.sup.9 ;
alternatively, E and R combine to form methylenedioxy or ethylenedioxy;
Z is selected from a bond, C.sub.1-4 alkylene, (CH.sub.2).sub.r O(CH.sub.2).sub.r, (CH.sub.2).sub.r NR.sup.3 (CH.sub.2).sub.r, (CH.sub.2).sub.r C(O)(CH.sub.2).sub.r, (CH.sub.2).sub.r C(O)O(CH.sub.2).sub.r, (CH.sub.2).sub.r OC(O) (CH.sub.2).sub.r, (CH.sub.2).sub.r C(O)NR.sup.3 (CH.sub.2).sub.r, (CH.sub.2).sub.r NR.sup.3 C(O)(CH.sub.2).sub.r, (CH.sub.2).sub.r OC(O)O(CH.sub.2).sub.r, (CH.sub.2).sub.r OC(O)NR.sup.3 (CH.sub.2).sub.r, (CH.sub.2).sub.r NR.sup.3 C(O)O(CH.sub.2).sub.r, (CH.sub.2).sub.r NR.sup.3 C(O)NR.sup.3 (CH.sub.2).sub.r, (CH.sub.2).sub.r S(O)p(CH.sub.2).sub.r, (CH.sub.2).sub.r SO.sub.2 NR.sup.3 (CH.sub.2).sub.r, (CH.sub.2).sub.r NR.sup.3 SO.sub.2 (CH.sub.2).sub.r, and (CH.sub.2).sub.r NR.sup.3 SO.sub.2 NR.sup.3 (CH.sub.2).sub.r, provided that Z does not form a N--N, N--O, N--S, NCH.sub.2 N, NCH.sub.2 O, or NCH.sub.2 S bond with ring M or group A;
R.sup.1a and R.sup.1b are independently absent or selected from --(CH.sub.2).sub.r --R.sup.1', --CH.dbd.CH--R.sup.1', NCH.sub.2 R.sup.1", OCH.sub.2 R.sup.1", SCH.sub.2 R.sup.1", NH(CH.sub.2).sub.2 (CH.sub.2).sub.t R.sup.1', O(CH.sub.2).sub.2 (CH.sub.2).sub.R.sup.1', and S(CH.sub.2).sub.2 (CH.sub.2).sub.R.sup.1' ;
alternatively, R.sup.1a and R.sup.1b, when attached to adjacent carbon atoms, together with the atoms to which they are attached form a 5-8 membered saturated, partially saturated or unsaturated ring substituted with 0-2 R.sup.4 and which contains from 0-2 heteroatoms selected from the group consisting of N, O, and S;
alternatively, when Z is C(O)NH and R.sup.1a is attached to a ring carbon adjacent to Z, then R.sup.1a is a C(O) which replaces the amide hydrogen of Z to form a cyclic imide;
R.sup.1' is selected from H, C.sub.1-3 alkyl, F, Cl, Br, I, --CN, --CHO, (CF.sub.2).sub.r CF.sub.3, (CH.sub.2).sub.r OR.sup.2, NR.sup.2 R.sup.2a, C(O)R.sup.2c, OC(O)R.sup.2, (CF.sub.2).sub.r CO.sub.2 R.sup.2c, S(O).sub.p R.sup.2b, NR.sup.2 (CH.sub.2).sub.r OR.sup.2, CH(.dbd.NR.sup.2c)NR.sup.2 R.sup.2a, NR.sup.2 C(O)R.sup.2b, NR.sup.2 C(O)NHR.sup.2b, NR.sup.2 C(O).sub.2 R.sup.2a, OC(O)NR.sup.2a R.sup.2b, C(O)NR.sup.2 R.sup.2a, C(O)NR.sup.2 (CH.sub.2).sub.r OR.sup.2, SO.sub.2 NR.sup.2 R.sup.2a, NR.sup.2 SO.sub.2 R.sup.2b, C.sub.3-6 carbocyclic residue substituted with 0-2 R.sup.4, and 5-10 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4 ;
R.sup.1" is selected from H, CH(CH.sub.2 OR.sup.2).sub.2, C(O)R.sup.2c, C(O)NR.sup.2 R.sup.2a, S(O)R.sup.2b, S(O).sub.2 R.sup.2b, and SO.sub.2 NR.sup.2 R.sup.2a ;
R.sup.2, at each occurrence, is selected from H, CF.sub.3, C.sub.1-6 alkyl, benzyl, C.sub.3-6 carbocyclic residue substituted with 0-2 R.sup.4b, and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4b ;
R.sup.2a, at each occurrence, is selected from H, CF.sub.3, C.sub.1-6 alkyl, benzyl, phenethyl, C.sub.3-6 carbocyclic residue substituted with 0-2 R.sup.4b, and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4b ;
R.sup.2b, at each occurrence, is selected from CF.sub.3, C.sub.1-4 alkoxy, C.sub.1-6 alkyl, benzyl, C.sub.3-6 carbocyclic residue substituted with 0-2 R.sup.4b, and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4b ;
R.sup.2c, at each occurrence, is selected from CF.sub.3, OH, C.sub.1-4 alkoxy, C.sub.1-6 alkyl, benzyl, C.sub.3-6 carbocyclic residue substituted with 0-2 R.sup.4b, and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4b ;
alternatively, R.sup.2 and R.sup.2a, together with the atom to which they are attached, combine to form a 5 or 6 membered saturated, partially saturated or unsaturated ring substituted with 0-2 R.sup.4b and containing from 0-1 additional heteroatoms selected from the group consisting of N, O, and S;
R.sup.3, at each occurrence, is selected from H, C.sub.1-4 alkyl, and phenyl;
R.sup.3a, at each occurrence, is selected from H, C.sub.1-4 alkyl, and phenyl;
R.sup.3b, at each occurrence, is selected from H, C.sub.1-4 alkyl, and phenyl;
R.sup.3c, at each occurrence, is selected from C.sub.1-4 alkyl, and phenyl;
A is selected from:
C.sub.3-10 carbocyclic residue substituted with 0-2 R.sup.4, and
5-10 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4 ;
B is selected from: H, Y, and X--Y;
X is selected from C.sub.1-4 alkylene, --CR.sup.2 (CR.sup.2 R.sup.2b) (CH.sub.2).sub.t --, --C(O)--, --C(.dbd.NR.sup.1)--, --CR.sup.2 (NR.sup.1" R.sup.2)--, --CR.sup.2 (OR.sup.2)--, --CR.sup.2 (SR.sup.2)--, --C(O)CR.sup.2 R.sup.2a --, --CR.sup.2 R.sup.2a C(O), --S(O).sub.p --, --S(O).sub.p CR.sup.2 R.sup.2a --, --CR.sup.2 R.sup.2a S(O).sub.p --, S(O).sub.2 NR.sup.2 --, --NR.sup.2 S(O).sub.2 --, --NR.sup.2 S(O).sub.2 CR.sup.2 R.sup.2a --, CR.sup.2 R.sup.2a S(O).sub.2 NR.sup.2 --, --NR.sup.2 S(O).sub.2 NR.sup.2 --, --C(O)NR.sup.2 --, --NR.sup.2 C(O)--, --C(O)NR.sup.2c R.sup.2 R.sup.2a --, ,NR.sup.2 C(O)CR.sup.2 R.sup.2a --, --CR.sup.2 R.sup.2a C(O)NR.sup.2 --, --CR.sup.2 R.sup.2a NR.sup.2 C(O)--, --NR.sup.2 C(O)O--, --OC(O)NR.sup.2 --, --NR.sup.2 C(O)NR.sup.2 --, --NR.sup.2 --, --NR.sup.2 CR.sup.2 R.sup.2a --, --CR.sup.2 R.sup.2a NR.sup.2 --, O, --CR.sup.2 R.sup.2a O--, and --OCR.sup.2 R.sup.2a --;
Y is selected from:
(CH.sub.2).sub.r NR.sup.2 R.sup.2a, provided that X--Y do not form a N--N, O--N, or S--N bond,
C.sub.3-10 carbocyclic residue substituted with 0-2 R.sup.4a, and
5-10 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4a ;
R.sup.4, at each occurrence, is selected from H, .dbd.O, (CH.sub.2).sub.r OR.sup.2, F, Cl, Br, I, C.sub.1-4 alkyl, --CN, NO.sub.2, (CH.sub.2).sub.r NR.sup.2 R.sup.2a, (CH.sub.2).sub.r C(O)R.sup.2c, NR.sup.2 C(O)R.sup.2b, C(O)NR.sup.2 R.sup.2a, NR.sup.2 C(O)NR.sup.2 R.sup.2a, CH(.dbd.NR.sup.2)NR.sup.2 R.sup.2a, CH(.dbd.NS(O).sub.2 R.sup.5)NR.sup.2 R.sup.2a, NHC(.dbd.NR.sup.2)NR.sup.2 R.sup.2a, C(O)NHC(.dbd.NR.sup.2)NR.sup.2 R.sup.2a, SO.sub.2 NR.sup.2 R.sup.2a, NR.sup.2 SO.sub.2 NR.sup.2 R.sup.2a, NR.sup.2 SO.sub.2 -C.sub.1-4 alkyl, NR.sup.2 SO.sub.2 R.sup.5, S(O).sub.p R.sup.5, (CF.sub.2).sub.r CF.sub.3, NCH.sub.2 R.sup.1", OCH.sub.2 R.sup.1", SCH.sub.2 R.sup.1", N(CH.sub.2).sub.2 (CH.sub.2).sub.t R.sup.1', O(CH.sub.2).sub.2 (CH.sub.2).sub.t R.sup.1", and S(CH.sub.2).sub.2 (CH.sub.2).sub.t R.sup.1' ;
alternatively, one R.sup.4 is a 5-6 membered aromatic heterocycle containing from 1-4 heteroatoms selected from the group consisting of N, O, and S;
R.sup.4a, at each occurrence, is selected from H, .dbd.O, (CH.sub.2).sub.r OR.sup.2, (CH.sub.2).sub.r --F, (CH.sub.2).sub.r --Br, (CH.sub.2).sub.r --Cl, I, C.sub.1-4 alkyl, --CN, NO.sub.2, (CH.sub.2).sub.r NR.sup.2 R.sup.2a, (CH.sub.2).sub.r NR.sup.2 R.sup.2b, (CH.sub.2).sub.r C(O)R.sup.2c, NR.sup.2 C(O)R.sup.2b, C(O) NR.sup.2 R.sup.2a, C(O) NH(CH.sub.2).sub.2 NR.sup.2 R.sup.2a, NR.sup.2 C(O)NR.sup.2 R.sup.2a, CH(.dbd.NR.sup.2)NR.sup.2 R.sup.2a, NHC(.dbd.NR.sup.2)NR.sup.2 R.sup.2a, SO.sub.2 NR.sup.2 R.sup.2a, NR.sup.2 SO.sub.2 NR.sup.2 NR.sup.2a, NR.sup.2 SO.sub.2 -C.sub.1-4 alkyl, C(O)NHSO.sub.2 -C.sub.1-4 alkyl, NR.sup.2 SO.sub.2 R.sup.5, S(O).sub.p R.sup.5, and (CF.sub.2).sub.r CF.sub.3 ;
alternatively, one R.sup.4a is a 5-6 membered aromatic heterocycle containing from 1-4 heteroatoms selected from the group consisting of N, O, and S and substituted with 0-1 R.sup.5 ;
R.sup.4b, at each occurrence, is selected from H, .dbd.O, (CH.sub.2).sub.r OR.sup.3, F, Cl, Br, I, C.sub.1-4 alkyl, --CN, NO.sub.2, (CH.sub.2).sub.r NR.sup.3 R.sup.3a, (CH.sub.2).sub.r C(O)R.sup.3, (CH.sub.2).sub.r C(O)OR.sup.3c, NR.sup.3 C(O)R.sup.3a, C(O)NR.sup.3 R.sup.3a, NR.sup.3 C(O) NR.sup.3 R.sup.3a, CH(.dbd.NR.sup.3)NR.sup.3 R.sup.3a, NH.sub.3 C(.dbd.NR.sup.3)NR.sup.3 R.sup.3a, SO.sub.2 NR.sup.3 R.sup.3a, NR.sup.3 SO.sub.2 NR.sup.3 R.sup.3a, NR.sup.3 SO.sub.2 -C.sub.1-4 alkyl, NR.sup.3 SO.sub.2 CF.sub.3, NR.sup.3 SO.sub.2 -phenyl, S(O).sub.p CF.sub.3, S(O).sub.p -C.sub.1-4 alkyl, S(O).sub.p -phenyl, and (CF.sub.2).sub.r CF.sub.3 ;
R.sup.5, at each occurrence, is selected from CF.sub.3, C.sub.1-6 alkyl, phenyl substituted with 0-2 R.sup.6, and benzyl substituted with 0-2 R.sup.6 ;
R.sup.6, at each occurrence, is selected from H, OH, (CH.sub.2).sub.r OR.sup.2, F, Cl, Br, I, C.sub.1-4 alkyl, CN, NO.sub.2, (CH.sub.2).sub.r NR.sup.2 R.sup.2a, (CH.sub.2).sub.r C(O)R.sup.2b, NR.sup.2 C(O)R.sup.2b, NR.sup.2 C(O)NR.sup.2 R.sup.2a, CH(.dbd.NH)NH.sub.2, NHC(.dbd.NH)NH.sub.2, SO.sub.2 NR.sup.2 R.sup.2a, NR.sup.2 SO.sub.2 NR.sup.2 R.sup.2a, and NR.sup.2 SO.sub.2 C.sub.1-4 alkyl;
R.sup.7, at each occurrence, is selected from H, OH, C.sub.1-6 alkyl, C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkoxy, C.sub.1-4 alkoxycarbonyl, (CH.sub.2).sub.n -phenyl, C.sub.6-10 aryloxy, C.sub.6-10 aryloxycarbonyl, C.sub.6-10 arylmethylcarbonyl, C.sub.1-4 alkylcarbonyloxy C.sub.1-4 alkoxycarbonyl, C.sub.6-10 arylcarbonyloxy C.sub.1-4 alkoxycarbonyl, C.sub.1-6 alkylaminocarbonyl, phenylaminocarbonyl, and phenyl-C.sub.1-4 alkoxycarbonyl;
R.sup.8, at each occurrence, is selected from H, C.sub.1-6 alkyl and (CH.sub.2).sub.n -phenyl;
alternatively, R.sup.7 and R.sup.8 combine to form a 5 or 6 membered saturated, ring which contains from 0-1 additional heteroatoms selected from the group consisting of N, O, and S;
R.sup.9, at each occurrence, is selected from H, C.sub.1-6 alkyl and (CH.sub.2).sub.n -phenyl;
n is selected from 0, 1, 2, and 3;
m is selected from 0, 1, and 2;
p is selected from 0, 1, and 2;
r is selected from 0, 1, 2, and 3;
s is selected from 0, 1, and 2; and,
t is selected from 0 and 1.
[2] In a preferred embodiment, the present invention provides novel compounds of formulae Ia-Io: ##STR6## wherein: Z is selected from a bond, CH.sub.2 O, OCH.sub.2, CH.sub.2 NH, NHCH.sub.2, CH.sub.2 C(O), C(O)CH.sub.2, C(O)NH, C(O)NH, CH.sub.2 S(O).sub.2, S(O).sub.2 (CH.sub.2), SO.sub.2 NH, and SO.sub.2 NH;
B is selected from: Y, X--Y, and NR.sup.2 R.sup.2a ;
Y is selected from one of the following carbocyclic and heterocyclic systems which are substituted with 0-2 R.sup.4a ;
phenyl, piperidinyl, piperazinyl, pyridyl, pyrimidyl, furanyl, morpholinyl, thiophenyl, pyrrolyl, pyrrolidinyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, oxadiazole, thiadiazole, triazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,2,3-triazole, 1,2,4-triazole, 1,2,5-triazole, 1,3,4-triazole, benzofuran, benzothiofuran, indole, benzimidazole, benzoxazole, benzthiazole, indazole, benzisoxazole, benzisothiazole, and isoindazole;
Y may also be selected from the following bicyclic heteroaryl ring systems: ##STR7## K is selected from O, S, NH, and N.
[3] In a more preferred embodiment, the present invention provides novel compounds of formulae: ##STR8## wherein D is selected from C(.dbd.NR.sup.7)NR.sup.8 R.sup.9 and; (CR.sup.8 R.sup.9).sub.t NR.sup.8 R.sup.9 ;
R is selected from H, F, Cl, OR.sup.3, CH.sub.2 OR.sup.3, CH.sub.2 NH.sub.2 ;
A is selected from:
piperidinyl,
piperazinyl,
C.sub.5-6 carbocyclic residue substituted with 0-2 R.sup.4, and
5-6 membered heteroaryl containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4 ;
Y is selected from one of the following carbocyclic and heterocyclic systems which are substituted with 0-2 R.sup.4a ;
phenyl, piperidinyl, piperazinyl, pyridyl, pyrimidyl, furanyl, morpholinyl, thiophenyl, pyrrolyl, pyrrolidinyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, benzimidazolyl, oxadiazole, thiadiazole, triazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,2,3-triazole, 1,2,4-triazole, 1,2,5-triazole, and 1,3,4-triazole.
[4] In an even more preferred embodiment, the present invention provides novel compounds wherein:
E is phenyl;
D is selected from C(.dbd.NH)NH.sub.2 and CH.sub.2 NH.sub.2 ;
R is selected from H, F, Cl, and Br;
A is selected from:
C.sub.5-6 carbocyclic residue substituted with 0-2 R.sup.4, and
5-6 membered heteroaryl containing from 1-3 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4 ;
Y is selected from one of the following carbocyclic and heterocyclic systems which are substituted with 0-2 R.sup.4a ;
phenyl, piperidinyl, piperazinyl, pyridyl, pyrimidyl, furanyl, morpholinyl, thiophenyl, pyrrolyl, pyrrolidinyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, benzimidazolyl, oxadiazole, thiadiazole, triazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,2,3-triazole, 1,2,4-triazole, 1,2,5-triazole, and 1,3,4-triazole;
R.sup.2, at each occurrence, is selected from H, CF.sub.3, C.sub.1-6 alkyl, benzyl, C.sub.5-6 carbocyclic residue substituted with 0-2 R.sup.4b, and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4b ;
R.sup.2a, at each occurrence, is selected from H, CF.sub.3, C.sub.1-6 alkyl, benzyl, phenethyl, C.sub.5-6 carbocyclic residue substituted with 0-2 R.sup.4b, and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4b ;
R.sup.2b, at each occurrence, is selected from CF.sub.3, C.sub.1-4 alkoxy, C.sub.1-6 alkyl, benzyl, C.sub.5-6 carbocyclic residue substituted with 0-2 R.sup.4b, and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4b ;
R.sup.2c, at each occurrence, is selected from CF.sub.3, OH, C.sub.1-4 alkoxy, C.sub.1-6 alkyl, benzyl, C.sub.5-6 carbocyclic residue substituted with 0-2 R.sup.4b, and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4b ;
alternatively, R.sup.2 and R.sup.2a, together with the atom to which they are attached, combine to form a ring selected from imidazolyl, morpholino, piperazinyl, pyridyl, and pyrrolidinyl, substituted with 0-2 R.sup.4b ;
R.sup.4, at each occurrence, is selected from H, .dbd.O, OR.sup.2, CH.sub.2 OR.sup.2, F, Cl, C.sub.1-4 alkyl, NR.sup.2 R.sup.2a, CH.sub.2 NR.sup.2 R.sup.2a, C(O)R.sup.2c, CH.sub.2 C(O)R.sup.2c, C(O)NR.sup.2 R.sup.2a, CH(.dbd.NR.sup.2)NR.sup.2 R.sup.2a, CH(.dbd.NS(O).sub.2 R.sup.5)NR.sup.2 R.sup.2a, SO.sub.2 NR.sup.2 R.sup.2a, NR.sup.2 SO.sub.2 -C.sub.1-4 alkyl, S(O).sub.2 R.sup.5, and CF.sub.3 provided that if B is H, then R.sup.4 is other than tetrazole, C(O)-alkoxy, and C(O)NR.sup.2 R.sup.2a ;
R.sup.4a, at each occurrence, is selected from H, .dbd.O, (CH.sub.2).sub.r OR.sup.2, F, Cl, C.sub.1-4 alkyl, NR.sup.2 R.sup.2a, CH.sub.2 NR.sup.2 R.sup.2a, NR.sup.2 R.sup.2b, CH.sub.2 NR.sup.2 R.sup.2b, (CH.sub.2).sub.r C(O)R.sup.2c, NR.sup.2 C(O)R.sup.2b, C(O)NR.sup.2 R.sup.2a, C(O)NH(CH.sub.2).sub.2 NR.sup.2 R.sup.2a, NR.sup.2 C(O)NR.sup.2 R.sup.2a, SO.sub.2 NR.sup.2 R.sup.2a, S(O).sub.2 R.sup.5, and CF.sub.3 ; and,
R.sup.4b, at each occurrence, is selected from H, .dbd.O, (CH.sub.2).sub.r OR.sup.3, F, Cl, C.sub.1-4 alkyl, NR.sup.3 R.sup.3a, CH.sub.2 NR.sup.3 R.sup.3a, C(O)R.sup.3, CH.sub.2 C(O)R.sup.3, C(O)OR.sup.3c, C(O)NR.sup.3 R.sup.3a, CH(.dbd.NR.sup.3)NR.sup.3 R.sup.3a, SO.sub.2 NR.sup.3 R.sup.3a, NR.sup.3 SO.sub.2 -C.sub.1-4 alkyl, NR.sup.3 SO.sub.2 CF.sub.3, NR.sup.3 SO.sub.2 -phenyl, S(O).sub.2 CF.sub.3, S(O).sub.2 -C.sub.1-4 alkyl, S(O).sub.2 -phenyl, and CF.sub.3.
[5] In a further preferred embodiment, the present invention provides novel compounds selected from:
N-(2'-Aminosulfonyl-[1,1']biphen-4-yl)-2-(3'-amidinophenyl)nicotinamide;
N-[5-(2-aminosulfonyl)phenylpyrid-2-yl]-2-(3'-amidinophenyl)nicotinamide;
N-[5-(2-t-butylaminosulfonyl)phenylpyrid-2-yl]-2-(3'-amidinophenyl)nicotinamide; and,
N-[5-(2-aminosulfonyl)phenylpyrid-2-yl]-2-(3'-carboxamidophenyl)nicotinamide;
or a pharmaceutically acceptable salt thereof.
In a second embodiment, the present invention provides novel pharmaceutical compositions, comprising: a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt form thereof.
In a third embodiment, the present invention provides a novel method for treating or preventing a thromboembolic disorder, comprising: administering to a patient in need thereof a therapeutically effective amount of a compound of formula (I) or a pharmaceutically acceptable salt form thereof.
DEFINITIONS
The compounds herein described may have asymmetric centers. Compounds of the present invention containing an asymmetrically substituted atom may be isolated in optically active or racemic forms. It is well known in the art how to prepare optically active forms, such as by resolution of racemic forms or by synthesis from optically active starting materials. Many geometric isomers of olefins, C.dbd.N double bonds, and the like can also be present in the compounds described herein, and all such stable isomers are contemplated in the present invention. Cis and trans geometric isomers of the compounds of the present invention are described and may be isolated as a mixture of isomers or as separated isomeric forms. All chiral, diastereomeric, racemic forms and all geometric isomeric forms of a structure are intended, unless the specific stereochemistry or isomeric form is specifically indicated.
The term "substituted," as used herein, means that any one or more hydrogens on the designated atom is replaced with a selection from the indicated group, provided that the designated atom's normal valency is not exceeded, and that the substitution results in a stable compound. When a substitent is keto (i.e., .dbd.O), then 2 hydrogens on the atom are replaced. Keto substituents are not present on aromatic moieties.
The present invention is intended to include all isotopes of atoms occurring in the present compounds. Isotopes include those atoms having the same atomic number but different mass numbers. By way of general example and without limitation, isotopes of hydrogen include tritium and deuterium. Isotopes of carbon include C-13 and C-14.
When any variable (e.g., R.sup.6) occurs more than one time in any constituent or formula for a compound, its definition at each occurrence is independent of its definition at every other occurrence. Thus, for example, if a group is shown to be substituted with 0-2 R.sup.6, then said group may optionally be substituted with up to two R.sup.6 groups and R.sup.6 at each occurrence is selected independently from the definition of R.sup.6. Also, combinations of substituents and/or variables are permissible only if such combinations result in stable compounds.
When a bond to a substituent is shown to cross a bond connecting two atoms in a ring, then such substituent may be bonded to any atom on the ring. When a substituent is listed without indicating the atom via which such substituent is bonded to the rest of the compound of a given formula, then such substituent may be bonded via any atom in such substituent. Combinations of substituents and/or variables are permissible only if such combinations result in stable compounds.
As used herein, "alkyl" is intended to include both branched and straight-chain saturated aliphatic hydrocarbon groups having the specified number of carbon atoms. Examples of alkyl include, but are not limited to, methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, n-pentyl, and s-pentyl. "Haloalkyl" is intended to include both branched and straight-chain saturated aliphatic hydrocarbon groups having the specified number of carbon atoms, substituted with 1 or more halogen (for example --C.sub.v F.sub.w where v=1 to 3 and w=1 to (2v+1)). Examples of haloalkyl include, but are not limited to, trifluoromethyl, trichloromethyl, pentafluoroethyl, and pentachloroethyl. "Alkoxy" represents an alkyl group as defined above with the indicated number of carbon atoms attached through an oxygen bridge. Examples of alkoxy include, but are not limited to, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, t-butoxy, n-pentoxy, and s-pentoxy. "Cycloalkyl" is intended to include saturated ring groups, such as cyclopropyl, cyclobutyl, or cyclopentyl. Alkenyl" is intended to include hydrocarbon chains of either a straight or branched configuration and one or more unsaturated carbon-carbon bonds which may occur in any stable point along the chain, such as ethenyl, propenyl and the like. "Alkynyl" is intended to include hydrocarbon chains of either a straight or branched configuration and one or more triple carbon-carbon bonds which may occur in any stable point along the chain, such as ethynyl, propynyl and the like.
"Halo" or "halogen" as used herein refers to fluoro, chloro, bromo, and iodo; and "counterion" is used to represent a small, negatively charged species such as chloride, bromide, hydroxide, acetate, sulfate, and the like.
As used herein, "carbocycle" or "carbocyclic residue" is intended to mean any stable 3- to 7-membered monocyclic or bicyclic or 7- to 13-membered bicyclic or tricyclic, any of which may be saturated, partially unsaturated, or aromatic. Examples of such carbocycles include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, cyclooctyl, [3.3.0]bicyclooctane, [4.3.0]bicyclononane, [4.4.0]bicyclodecane, [2.2.2]bicyclooctane, fluorenyl, phenyl, naphthyl, indanyl, adamantyl, or tetrahydronaphthyl.
As used herein, the term "heterocycle" or "heterocyclic system" is intended to mean a stable 5- to 7-membered monocyclic or bicyclic or 7- to 10-membered bicyclic heterocyclic ring which is saturated partially unsaturated or unsaturated (aromatic), and which consists of carbon atoms and from 1 to 4 heteroatoms independently selected from the group consisting of N, O and S and including any bicyclic group in which any of the above-defined heterocyclic rings is fused to a benzene ring. The nitrogen and sulfur heteroatoms may optionally be oxidized. The heterocyclic ring may be attached to its pendant group at any heteroatom or carbon atom which results in a stable structure. The heterocyclic rings described herein may be substituted on carbon or on a nitrogen atom if the resulting compound is stable. If specifically noted, a nitrogen in the heterocycle may optionally be quaternized. It is preferred that when the total number of S and O atoms in the heterocycle exceeds 1, then these heteroatoms are not adjacent to one another. It is preferred that the total number of S and O atoms in the heterocycle is not more than 1. As used herein, the term "aromatic heterocyclic system" is intended to mean a stable 5- to 7-membered monocyclic or bicyclic or 7- to 10-membered bicyclic heterocyclic aromatic ring which consists of carbon atoms and from 1 to 4 heterotams independently selected from the group consisting of N, O and S. It is preferred that the total number of S and O atoms in the aromatic heterocycle is not more than 1.
Examples of heterocycles include, but are not limited to, acridinyl, azocinyl, benzimidazolyl, benzofuranyl, benzothiofuranyl, benzothiophenyl, benzoxazolyl, benzthiazolyl, benztriazolyl, benztetrazolyl, benzisoxazolyl, benzisothiazolyl, benzimidazolinyl, carbazolyl, 4aH-carbazolyl, carbolinyl, chromanyl, chromenyl, cinnolinyl, decahydroquinolinyl, 2H,6H-1,5,2-dithiazinyl, dihydrofuro[2,3-b]tetrahydrofuran, furanyl, furazanyl, imidazolidinyl, imidazolinyl, imidazolyl, 1H-indazolyl, indolenyl, indolinyl, indolizinyl, indolyl, 3H-indolyl, isobenzofuranyl, isochromanyl, isoindazolyl, isoindolinyl, isoindolyl, isoquinolinyl, isothiazolyl, isoxazolyl, morpholinyl, naphthyridinyl, octahydroisoquinolinyl, oxadiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl, oxazolidinyl, oxazolyl, oxazolidinyl, pyrimidinyl, phenanthridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxathiinyl, phenoxazinyl, phthalazinyl, piperazinyl, piperidinyl, pteridinyl, purinyl, pyranyl, pyrazinyl, pyrazolidinyl, pyrazolinyl, pyrazolyl, pyridazinyl, pyridooxazole, pyridoimidazole, pyridothiazole, pyridinyl, pyridyl, pyrimidinyl, pyrrolidinyl, pyrrolinyl, 2H-pyrrolyl, pyrrolyl, quinazolinyl, quinolinyl, 4H-quinolizinyl, quinoxalinyl, quinuclidinyl, tetrahydrofuranyl, tetrahydroisoquinolinyl, tetrahydroquinolinyl, 6H-1,2,5-thiadiazinyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, thianthrenyl, thiazolyl, thienyl, thienothiazolyl, thienooxazolyl, thienoimidazolyl, thiophenyl, triazinyl, 1,2,3-triazolyl, 1,2,4-triazolyl, 1,2,5-triazolyl, 1,3,4-triazolyl, and xanthenyl. Preferred heterocycles include, but are not limited to, pyridinyl, furanyl, thienyl, pyrrolyl, pyrazolyl, pyrrolidinyl, imidazolyl, indolyl, benzimidazolyl, 1H-indazolyl, oxazolidinyl, benzotriazolyl, benzisoxazolyl, oxindolyl, benzoxazolinyl, or isatinoyl. Also included are fused ring and Spiro compounds containing, for example, the above heterocycles.
The phrase "pharmaceutically acceptable" is employed herein to refer to those compounds, materials, compositions, and/or dosage forms which are, within the scope of sound medical judgment, suitable for use in contact with the tissues of human beings and animals without excessive toxicity, irritation, allergic response, or other problem or complication, commensurate with a reasonable benefit/risk ratio.
As used herein, "pharmaceutically acceptable salts" refer to derivatives of the disclosed compounds wherein the parent compound is modified by making acid or base salts thereof. Examples of pharmaceutically acceptable salts include, but are not limited to, mineral or organic acid salts of basic residues such as amines; alkali or organic salts of acidic residues such as carboxylic acids; and the like. The pharmaceutically acceptable salts include the conventional non-toxic salts or the quaternary ammonium salts of the parent compound formed, for example, from non-toxic inorganic or organic acids. For example, such conventional non-toxic salts include those derived from inorganic acids such as hydrochloric, hydrobromic, sulfuric, sulfamic, phosphoric, nitric and the like; and the salts prepared from organic acids such as acetic, propionic, succinic, glycolic, stearic, lactic, malic, tartaric, citric, ascorbic, pamoic, maleic, hydroxymaleic, phenylacetic, glutamic, benzoic, salicylic, sulfanilic, 2-acetoxybenzoic, fumaric, toluenesulfonic, methanesulfonic, ethane disulfonic, oxalic, isethionic, and the like.
The pharmaceutically acceptable salts of the present invention can be synthesized from the parent compound which contains a basic or acidic moiety by conventional chemical methods. Generally, such salts can be prepared by reacting the free acid or base forms of these compounds with a stoichiometric amount of the appropriate base or acid in water or in an organic solvent, or in a mixture of the two; generally, nonaqueous media like ether, ethyl acetate, ethanol, isopropanol, or acetonitrile are preferred. Lists of suitable salts are found in Remington's Pharmaceutical Sciences, 17th ed., Mack Publishing Company, Easton, Pa., 1985, p. 1418, the disclosure of which is hereby incorporated by reference.
"Prodrugs" are intended to include any covalently bonded carriers which release the active parent drug according to formula (I) in vivo when such prodrug is administered to a mammalian subject. Prodrugs of a compound of formula (I) are prepared by modifying functional groups present in the compound in such a way that the modifications are cleaved, either in routine manipulation or in vivo, to the parent compound. Prodrugs include compounds of formula (I) wherein a hydroxy, amino, or sulfhydryl group is bonded to any group that, when the prodrug or compound of formula (I) is administered to a mammalian subject, cleaves to form a free hydroxyl, free amino, or free sulfhydryl group, respectively. Examples of prodrugs include, but are not limited to, acetate, formate and benzoate derivatives of alcohol and amine functional groups in the compounds of formula (I), and the like. Preferred prodrugs are amidine prodrugs wherein D is C(.dbd.NR.sup.7)NH.sub.2, and R.sup.7 is selected from OH, C.sub.1-4 alkoxy, C.sub.6-10 aryloxy, C.sub.1-4 alkoxycarbonyl, C.sub.6-10 aryloxycarbonyl, C.sub.6-10 arylmethylcarbonyl, C.sub.1-4 alkylcarbonyloxy C.sub.1-4 alkoxycarbonyl, and C.sub.6-10 arylcarbonyloxy C.sub.1-4 alkoxycarbonyl. More preferred prodrugs are where R.sup.7 is OH, methoxy, ethoxy, benzyloxycarbonyl, methoxycarbonyl, and methylcarbonyloxymethoxycarbonyl.
"Stable compound" and "stable structure" are meant to indicate a compound that is sufficiently robust to survive isolation to a useful degree of purity from a reaction mixture, and formulation into an efficacious therapeutic agent.
"Substituted" is intended to indicate that one or more hydrogens on the atom indicated in the expression using "substituted" is replaced with a selection from the indicated group(s), provided that the indicated atom's normal valency is not exceeded, and that the substitution results in a stable compound. When a substituent is keto (i.e., .dbd.O) group, then 2 hydrogens on the atom are replaced.
"Therapeutically effective amount" is intended to include an amount of a compound of the present invention or an amount of the combination of compounds claimed effective to inhibit HIV infection or treat the symptoms of HIV infection in a host. The combination of compounds is preferably a synergistic combination. Synergy, as described for example by Chou and Talalay, Adv. Enzyme Regul. 22:27-55 (1984), occurs when the effect (in this case, inhibition of HIV replication) of the compounds when administered in combination is greater than the additive effect of the compounds when administered alone as a single agent. In general, a synergistic effect is most clearly demonstrated at suboptimal concentrations of the compounds. Synergy can be in terms of lower cytotoxicity, increased antiviral effect, or some other beneficial effect of the combination compared with the individual components.
SYNTHESIS
The compounds of the present invention can be prepared in a number of ways known to one skilled in the art of organic synthesis. The compounds of the present invention can be synthesized using the methods described below, together with synthetic methods known in the art of synthetic organic chemistry, or variations thereon as appreciated by those skilled in the art. Preferred methods include, but are not limited to, those described below. The reactions are performed in a solvent appropriate to the reagents and materials employed and suitable for the transformations being effected. It will sometimes require a judgment to modify the order of synthetic steps or to select one particular process scheme over another in order to obtain a desired compound of the invention. It will also be recognized that another major consideration in the planning of any synthetic route in this field is the judicious choice of the protecting group used for the protection of the reactive functional groups present in the compounds described in this invention. An authoritative account describing the many alternatives to the trained practitioner is Greene and Wuts (Protective Groups in Organic Chemistry, Wiley and Sons, 1991). All references cited herein are hereby incorporated in their entirety herein by reference. Compounds of this invention where B is either a carbocyclic or heterocyclic residue as defined in Formula 1 are coupled to A as shown generically and by specific example in Schemes 1 and 2, respectively. Either or both of A and B may be substituted with 0-2 R.sup.4. W is defined as a suitable protected nitrogen, such as NO.sub.2 or NHBOC; a protected sulfur, such as S-tBu or SMOM; or a methyl ester. Halogen-metal exchange of the bromine in bromo-B with n-butyl lithium, quenching with triisopropyl borate and acidic hydrolysis gives the required boronic acid, B--B(OH).sub.2. The W--A--Br subunit may be already linked to ring M before the Suzuki coupling reaction. Deprotection provides the complete subunit. ##STR9##
Scheme 2 describes a typical example of how the A-B subunit is prepared for attachment to ring M. 4-Bromoaniline is protected as Boc-derivative and the coupled to 2-(t-butylamino)sulfonylphenylboronic acid under Suzuki conditions. 2-(t-Butylamino)sulfonylphenylboronic acid is prepared by the method described by Rivero (Bioorg. Med. Chem. Lett. 1994, 189). Deprotection with TFA can provide the aminobiphenyl compound. The aminobiphenyl is then coupled to the core ring structures as described below. ##STR10##
When B is defined as X--Y, the following description applies. Groups A and B are available either through commercial sources, known in the literature or readily synthesized by the adaptation of standard procedures known to practitioners skilled in the art of organic synthesis. the required reactive functional groups appended to analogs of A and B are also available either through commercial sources, known in the literature or readily synthesized by the adaptation of standard procedures known to practitioners skilled in the art of synthesis. In the tables that follow the chemistry required to effect the coupling of A to B is outlined.
TABLE A______________________________________Preparation of Amide Ester, Urea, Sulfonamide and Sulfamide Linkages Between A and B. then the reactive to give the following If A contains: substituent of Y is: product A--X--Y:______________________________________A--NHR.sup.2 as a ClC(O)--Y A--NR.sup.2 --C(O)--Y substituent a secondary NH ClC(O)--Y A--C(O)--Y as part of a ring or chain A--OH as a ClC(O)--Y A--O--C(O)--Y substituent A--NHR.sup.2 as a ClC(O)--CR.sup.2 R.sup.2a -- A--NR.sup.2 --C(O)--CR.su p.2 R.sup.2a --Y substituent --Y a secondary NH ClC(O)--CR.sup.2 R.sup.2a -- A--C(O)--CR.sup.2 R.sup.2a --Y as part of a --Y ring or chain A--OH as a ClC(O)--CR.sup.2 R.sup.2a -- A--O--C(O)--CR.sup.2 R.sup.2a --Y substituent --Y A--NHR.sup.2 as a ClC(O)--CNR.sup.2 --Y A--NR.sup.2 --C(O)--CNR.sup.2 --Y substituent a secondary NH ClC(O)--CNR.sup.2 --Y A--C(O)--CNR.sup.2 --Y as part of a ring or chain A--OH as a ClC(O)--CNR.sup.2 --Y A--O--C(O)--CNR.sup.2 --Y substituent A--NHR.sup.2 as a ClSO.sub.2 --Y A--NR.sup.2 --SO.sub.2 --Y substituent a secondary NH ClSO.sub.2 --Y A--SO.sub.2 --Y as part of a ring or chain A--NHR.sup.2 as a ClSO.sub.2 --CR.sup.2 R.sup.2a -- A--NR.sup.2 --SO.sub.2 --CR.sup.2 R.sup.2a --Y substituent --Y a secondary NH ClSO.sub.2 --CR.sup.2 R.sup.2a -- A--SO.sub.2 --CR.sup.2 R.sup.2a --Y as part of a --Y ring or chain A--NHR.sup.2 as a ClSO.sub.2 --NR.sup.2 --Y A--NR.sup.2 --SO.sub.2 --NR.sup.2 --Y substituent a secondary NH ClSO.sub.2 --NR.sup.2 --Y A--SO.sub.2 --NR.sup.2 --Y as part of a ring or chain A--C(O)Cl HO--Y as a A--C(O)--O--Y substituent A--C(O)Cl NHR.sup.2 --Y as a A--C(O)--NR.sup.2 --Y substituent A--C(O)Cl a secondary NH as A--C(O)--Y part of a ring or chain A--CR.sup.2 R.sup.2a C(O)Cl HO--Y as a A--CR.sup.2 R.sup.2a C(O)--O--Y substituent A--CR.sup.2 R.sup.2a C(O)Cl NHR.sup.2 --Y as a A--CR.sup.2 R.sup.2a C(O)--NR.sup.2 --Y substituent A--CR.sup.2 R.sup.2a C(O)Cl a secondary NH as A--CR.sup.2 R.sup.2a C(O)--Y part of a ring or chain A--SO.sub.2 Cl NHR.sup.2 --Y as a A--SO.sub.2 --NR.sup.2 --Y substituent A--SO.sub.2 Cl a secondary NH as A--SO.sub.2 --Y part of a ring or chain A--CR.sup.2 R.sup.2a SO.sub.2 Cl NHR.sup.2 --Y as a A--CR.sup.2 R.sup.2a SO.sub.2 --NR.sup.2 --Y substituent A--CR.sup.2 R.sup.2a SO.sub.2 Cl a secondary NH as A--CR.sup.2 R.sup.2a SO.sub.2 --Y part of a ring or chain______________________________________
The chemistry of Table A can be carried out in aprotic solvents such as a chlorocarbon, pyridine, benzene or toluene, at temperatures ranging from -20.degree. C. to the reflux point of the solvent and with or without a trialkylamine base.
TABLE B______________________________________Preparation of Ketone Linkages between A and B. then the reactive to give the following If A contains: substituent of Y is: product A--X--Y:______________________________________A--C(O)Cl BrMg--Y A--C(O)--Y A--CR.sup.2 R.sup.2a C(O)Cl BrMg--Y A--CR.sup.2 R.sup.2a C(O)--Y A--C(O)Cl BrMgCR.sup.2 R.sup.2a --Y A--C(O)CR.sup .2 R.sup.2a --Y A--CR.sup.2 R.sup.2a C(O)Cl BrMgCR.sup.2 R.sup.2a --Y A--CR.sup.2 R.sup.2a C(O)CR.sup.2 R.sup.2a --Y______________________________________
The coupling chemistry of table B can be carried out by a variety of methods. The Grignard reagent required for Y is prepared from a halogen analog of Y in dry ether, dimethoxyethane or tetrahydrofuran at 0.degree. C. to the reflux point of the solvent. This Grignard reagent can reacted directly under very controlled conditions, that is low temperature (-20.degree. C. or lower) and with a large excess of acid chloride or with catalytic or stoichiometric copper bromide.cndot.dimethyl sulfide complex in dimethyl sulfide as a solvent or with a variant thereof. Other methods available include transforming the Grignard reagent to the cadmium reagent and coupling according to the procedure of Carson and Prout (Org. Syn. Col. Vol. 3 (1955) 601) or a coupling mediated by Fe(acac)3 according to Fiandanese et al. (Tetr. Lett. 1984, 4805), or a coupling mediated by manganese (II) catalysis (Cahiez and Laboue, Tetr. Lett. 1992, 33(31), 4437).
TABLE C______________________________________Preparation of Ether and Thioether linkages between A and B. then the reactive to give the following If A contains: substituent of Y is: product A--X--Y:______________________________________A--OH Br--Y A--O--Y A--CR.sup.2 R.sup.2a --OH Br--Y A--CR.sup.2 R.sup.2a O--Y A--OH Br--CR.sup.2 R.sup.2a --Y A--OCR.sup.2 R.sup.2a --Y A--SH Br--Y A--S--Y A--CR.sup.2 R.sup.2a --SH Br--Y A--CR.sup.2 R.sup.2a S--Y A--SH Br--CR.sup.2 R.sup.2a --Y A--SCR.sup.2 R.sup.2a --Y______________________________________
The ether and thioether linkages of Table C can be prepared by reacting the two components in a polar aprotic solvent such as acetone, dimethylformamide or dimethylsulfoxide in the presence of a base such as potassium carbonate, sodium hydride or potassium t-butoxide at a temperature ranging from ambient to the reflux point of the solvent used.
TABLE D______________________________________Preparation of --SO-- and --SO.sub.2 -- linkages from thioether of Table C. then it is oxidized then it is oxidized with wet with m- If the starting Alumina/Oxone to chloroperbenzoic acid material is: give: to give:______________________________________A--S--Y A--S(O)--Y A--SO.sub.2 --Y A--CR.sup.2 R.sup.2a S--Y A--CR.sup.2 R.sup.2a S(O)--Y A--CR.sup.2 R.sup.2a SO.sub.2 --Y A--SCR.sup.2 R.sup.2a --Y A--S(O)CR.sup.2 R.sup.2a --Y A--SO.sub.2 CR.sup.2 R.sup.2a --Y______________________________________
The thioethers of Table C serve as a convenient starting material for the preparation of the sulfoxide and sulfone analogs of Table D. A combination of wet alumina and Oxone can provide a reliable reagents for the oxidation of the thioether to the sulfoxide as shown by Greenhalgh (Syn. Lett. 1992, 235). The sulfone can be prepared according to the method of Satoh (Chem. Lett. 1992, 381) using m-chloroperbenzoic acid.
Scheme 3 describes the synthesis of compounds wherein M is a benzene ring and Q is a protected precursor of group D of Formula I and V is a nitro, protected sulfonamide or ester group and precursor of group Z of Formula I. The V group is placed on an appropriately substituted phenol either via nitration as shown by Poirier et al. (Tetrahedron 1989, 45(5), 1415), sulfonylation as shown by Kuznetsov (Akad. Nauk SSSR Ser. Khim 1990, 8, 1888) or carboxylation by Sartori et al. (Synthesis 1988, 10, 763). Bromination with triphenylphosphine and bromine (J. Am. Chem. Soc. 1964, 86, 964) gives the desired bromide. Suzuki coupling with the appropriate boronic acid provides the desired substituted pyridine. ##STR11##
Schemes 4, 5, 6, and 7 describe the synthesis of compounds wherein M is pyridine and Q is a protected precursor of group D of Formula I. Each scheme represents a different substitution pattern for the pyridine ring. In Scheme 4, a suitably protected aldehyde is subjected to base-catalyzed condensation with an activated ester to give after deprotection the desired aldehyde. Refluxing with ammonium chloride as shown by Dornow and Ische (Chem. Ber. 1956, 89, 876) provides the pyridinol which is brominated with POBr.sub.3 (Tjeenk et al. Rec. Trav. Chim. 1948, 67, 380) to give the desired 2-bromopyridine. Suzuki coupling with the appropriate boronic acid provides the desired substituted pyridine. ##STR12##
Treatment of an appropriately substituted 5-ethoxyoxazole with an alkene as shown by Kondrat'eva et al. Dokl. Akad. Nauk SSSR 1965, 164, 816) provides a pyridine with the V substituent at the para position. Bromination at the 3-position as shown by van der Does and Hertog (Rec. Trav. Khim. Pays-Bas 1965, 84, 951) followed by palladium-catalyzed boronic acid coupling provides the desired substituted pyridine. ##STR13##
Scheme 6 describes a synthesis of a third substitution pattern on a pyridine ring. The appropriate tricarbonyl compound which can be prepared by methods described in Scheme 4 is treated with ammonium chloride to form the pyridinol which is subsequently brominated. Palladium-catalyzed coupling provides the desired substituted pyridine. ##STR14##
Scheme 7 takes a suitably substituted dicarbonyl compound and by chemistry illustrated in Schemes 4 and 6, reacts it with ammonium chloride. Bromination gives the 3-bromopyridine which upon palladium-catalyzed coupling provides the desired substituted pyridine. ##STR15##
Schemes 8, 9, and 10 describe the synthesis of compounds wherein M is pyridazine and Q is a protected precursor of group D of Formula I. Each scheme represents a different substitution pattern for the pyridine ring. In Scheme 8 an activated ester is reacted with an appropriately substituted .alpha.-keto aldehyde and hydrazine as shown by Schmidt and Druey (Helv. Chim. Acta 1954, 37, 134 and 1467). Conversion of the pyridazinone to the bromide using POBr.sub.3 and palladium-catalized coupling provides the desired substituted pyridazine. ##STR16##
In Scheme 9, glyoxal can react under basic conditions with an activated ketone and subsequently brominated/dehydro-brominated to give the desired ketoaldehyde. Alternatively, a protected ketone can react with an activated aldehyde, undergo bromination/dehydrobromination, be deprotected and oxidized to give the regioisomeric ketoaldehyde. Cyclization as shown by Sprio and Madonia (Ann. Chim. 1958, 48, 1316) with hydrazine followed by palladium-catalyzed coupling provides the desired substituted pyridazine. ##STR17##
By analogy to Scheme 9, in Scheme 10 a aldehyde can be reacted with an activated ketone, brominated, dehydro-brominated and deprotected to give the desired diketone. Alternatively, a regioisomeric ketone can be placed through the same reaction sequence to produce an isomeric keto aldehyde. Reaction with hydrazine followed by palladium-catalized coupling provides the desired substituted pyridazine. ##STR18##
Schemes 11, and 12 describe the synthesis of compounds wherein M is pyrimidine and Q is a protected precursor of group D of Formula I. Each scheme represents a different substitution pattern for the pyrimidine ring. In Scheme 11, a condensation with an appropriately substituted acid chloride and an activated ester followed by conjugate reduction by tin hydride (Moriya et al. J. Org. Chem. 1986, 51, 4708) gives the desired 1,4 dicarbonyl compound. Cyclization with formamidine or a substituted amidine followed by bromination gives the desired regioisomeric pyrimidine. Palladium-catalyzed coupling provides the desired substituted pyrimidine. ##STR19##
Using similar chemistry, Scheme 12 shows how an amidine can be condensed with a 1,3-dicarbonyl compound and subsequently brominated in the 5-position (J. Het. Chem. 1973, 10, 153) to give a specific regioisomeric bromopyrimidine. Palladium-catalyzed coupling provides the desired substituted pyrimidine. ##STR20##
Using the same ketoaldehyde from Scheme 12, cyclization with an appropriately substituted 1,2-diamine (Chimia 1967, 21, 510) followed by aromatization (Helv. Chim. Acta 1967, 50, 1754) provides a regioisomeric mixture of pyrazines as illustrated in Scheme 13. Bromination of the hydrobromide salt (U.S. Pat. No. 2,403,710) yields the intermediate for the palladium-catalyzed coupling step which occurs as shown above. ##STR21##
Schemes 14 and 15 describe the synthesis of compounds wherein M is a 1,2,3-triazine and Q is a protected precursor of group D of Formula I. In Scheme 14, a vinyl bromide is palladium coupled to a molecule containing the substituent R.sup.1b. Allylic bromination followed by azide displacement provide the cyclization precursor. Triphenylphosphine-mediated cyclization (J. Org. Chem. 1990, 55, 4724) give the 1-aminopyrazole which is subsequently brominated with N-bromosuccimide. Lead tetraacetate mediated rearrangement as shown by Neunhoeffer et al. (Ann. 1985, 1732) provides the desired regioisomeric 1,2,3-triazine. Palladium-catalyzed coupling provides the substituted triazine. ##STR22##
In Scheme 15, an alkene is allylically brominated and the bromide is displaced to give a regioisomer of the azide in Scheme 14. Following the same reaction sequence as shown above, cyclization provides the 1-aminopyrazole. Bromination followed by lead tetraacetate mediated rearrangement give the 1,2,3-triazine. Palladium-catalyzed coupling provides the other desired triazine. ##STR23##
Schemes 16 and 17 describe the synthesis of compounds wherein M is a 1,2,4-triazine and Q is a protected precursor of group D of Formula I. In Scheme 16, a nitrile is converted using hydrazine to give the amidrazone which is condensed with a .alpha.-ketoester to give the triazinone as shown by Paudler and Lee (J. Org. Chem. 1971, 36, 3921). Bromination as shown by Rykowski and van der Plas (J. Org. Chem. 1987, 52, 71) followed by palladium-catalyzed coupling provides the desired 1,2,4-triazine. ##STR24##
In Scheme 16, to achieve the opposite regioisomer the reaction scheme shown above is modify by the substituting a protect .alpha.-ketoester. This allows the most nucleophilic nitrogen to attack the ester functionality setting up the opposite regiochemistry. Deprotection and thermal cyclization gives the triazinone which is brominated as shown above. Palladium-catalyzed coupling provides the other desired 1,2,4-triazine. ##STR25##
Scheme 18 describes the synthesis of compounds wherein M is a 1,2,3,4-tetrazine and Q is a protected precursor of group D of Formula I. Lithiation of a vinyl bromide, transmetallation with tin, palladium catalyzed carbonylation and hydrazone formation provides a diene for a subsequent Diels-Alder reaction as shown by Carboni and Lindsey (J. Am. Chem. Soc. 1959, 81, 4342). Reaction with dibenzyl azodicarboxylate followed by catalytic hydrogenation to debenzylate and decarboxylate should give after bromination the desired 1,2,3,4-tetrazine. Palladium-catalyzed coupling provides the desired substitution. ##STR26##
Other features of the invention will become apparent in the course of the following descriptions of exemplary embodiments which are given for illustration for the invention and are not intended to be limiting thereof.





EXAMPLES
Example 1
N-(2'-Aminosulfonyl-[1,1']biphen-4-yl)-2-(3'-amidinophenyl)nicotinamide, trifluoroacetic Acid Salt
Part A. Preparation of 2-bromonicotinic Acid.
Potassium permanganate (18.4 g, 116 mmol) was dissolved in water (400 mL) and added to 2-bromo-3-methylpyridine (10.0 g, 58 mmol) and refluxed for 16 hours. After cooling to room temperature, the slurry was filtered through a celite plug and rinsed with water and chloroform. The entire filtrate was transferred to a separatory funnel and the layers were separated. The aqueous layer was extracted again with CHCl.sub.3 and acidified with 6N HCl to pH 1. A white solid was obtained on standing (2.08 g of product). The pH of the remaining aqueous was adjusted to pH 4 with 2M NaOH and 2M HCl, then concentrated to <100 mL. A white precipitate was filtered. The pH was adjusted to 4 and the mixture filtered again, combining the isolated solids for a total of 3.88 g of product. The filtrate was concentrated again to <100 mL and adjusted to pH 1.5 and an additional quanitity of white solid was obtained (1.80 g), for a combined yield of 3 crops, (8.76 g, 66%). .sup.1 H NMR (DMSO-d6): .delta. 13.76 (bs, 1H), 8.46 (m, 1H), 8.09 (dd, 1H, J=7.7, J'=2.2), 7.51 (m, 1H).
Part B. Preparation of methyl 2-bromonicotinate.
2-Bromonicotinic acid (7.33 g, 36 mmol) was suspended in dry Et.sub.2 O (40 mL), and MeOH (2.3 mL) and diethyl azodicarboxylate (5.8 mL, 37 mmol) were added. Triphenylphosphine (9.61 g in 40 mL Et.sub.2 O, 37 mmol) was added dropwise over 2.5 hours. After stirring an additional two hours, the reaction was filtered and evaporated. The resulting clear liquid was chromatographed on silica gel (10-40% EtOAc/hexanes) to yield a clear oil (8.63 g, 100%). .sup.1 H NMR (CDCl.sub.3): .delta. 8.49 (dd, 1H, J=4.8, J'=2.2), 8.09 (dd, 1H, J=7.7, J'=1.8), 7.36 (m, 1H), 3.97 (s, 3H).
Part C. Preparation of 3-cyanophenylboronic Acid.
3-Bromobenzonitrile (10.0 g, 55 mmol) was dissolved in dry THF (100 mL) and cooled to -100.degree. C. (Et.sub.2 O/N.sub.2). n-Butyllithium (24.2 mL, 2.5 M in hexane) was added over 30 minutes, maintaining the internal temp under -90.degree.. After 20 minutes, triisopropylborate (18.0 mL) was added over 15 minutes, again maintaining the internal temperature. After the addition was complete, the reaction was allowed to warm slowly to room temperature over 1.5 hours. The reaction was stirred at room temp for 16 hours, then cooled to 15.degree. C., after which 6 M HCl (25 mL) was added. After stirring vigorously for 3.5 hours, the reaction was partitioned between water and EtOAc. After extracting a second time with EtOAc, the combined organics were washed with 2 M NaOH. The aqueous extract was neutralized with 6 M HCl. The white precipitate was filtered, yielding the desired product (4.80 g, 60%). .sup.1 H NMR (DMSO-d.sub.6): .delta. 8.37 (s, 2H), 8.10 (s, 1H), 8.03 (dt, 1H, J=7.3, J'=1.1), 7.83 (dt, 1H, J=7.6, J'=1.4), 7.53 (t, 1H, J=7.7).
Part D. Preparation of methyl 2-(3'-cyanophenyl)nicotinate.
Methyl 2-bromonicotinate (2.0 g, 9.3 mmol) and 3-cyanophenylboronic acid (2.7 g, 18.4 mmol) were combined in 190 mL benzene. Sodium carbonate (19 mL of a 2 M aqueous solution), tetrabutylammonium bromide (152 mg, 0.5 mmol), and bis(triphenylphosphine)palladium(II) chloride (325 mg, 0.5 mmol) were added. The entire mixture was evacuated to remove dissolved gasses, then placed under argon. The reaction was refluxed for 14 hours, diluted with water and EtOAc, separated, dried over Na.sub.2 SO.sub.4, filtered, and evaporated. The resulting yellow solid was chromatographed on silica gel (30% EtOAc/hexanes) to yield a light yellow solid (1.70 g, 77%). .sup.1 H NMR (CDCl.sub.3): .delta. 8.81 (dd, 1H, J=4.8, J'=1.8), 8.23 (dd, 1H, J=8.0, J'=1.9), 7.85 (s, 1H), 7.73 (m, 2H), 7.55 (t, 1H, J=7.7), 7.43 (m, 1H), 3.76 (s, 3H).
Part E. Preparation of 2-(t-butylaminosulfonyl)phenylboronic Acid.
To a solution of 206.5 g (0.968 mol) of benzene-(N-t-butyl)sulfonamide in 2500 mL of THF under N.sub.2 was added 790 mL (1.98 mol) of 2.5M n-butyllithium in hexane over 35 minutes, keeping the temperature between 0-5.degree. C. The reaction mixture was allowed to warm to 10.degree. C., at which time a thick precipitate formed. Triisopropylborate (305 mL, 1.32 mol) was added keeping the temperature below 35.degree. C. After 1 hour, the reaction mixture was cooled, 1N HCl (1570 mL) was added, and the mixture was stirred overnight. The mixture was extracted with 400 mL of ether three times, and the combined organic extracts were extracted with 500 mL of 1N NaOH three times. The aqueous extracts were acidified to pH 1 with 6N HCl, and then extracted with 500 mL ether three times. The combined ether extracts were dried over MgSO.sub.4, and the solvents evaporated in vacuo until the volume was 700 mL. Hexane (150 mL) was added and overnight, a white precipitate formed. The solid was collected and washed with 10% ether/hexane (250 mL), then dried in vacuo to give 216.3 g (87%) of the desired compound as white crystals. m.p. 118-119.degree. C.; .sup.1 H NMR (CDCl.sub.3): .delta. 8.00 (d, 1H); 7.82 (d, 1H); 7.53 (m, 2H); 6.29 (br s, 2H); 5.13 (s, 1H); 1.18 (s, 9H).
Part F. Preparation of 4-amino-21-t-butylaminosulfonyl-[1,1']biphenyl.
A mixture of 3.44 g (20 mmol) of 4-bromoaniline and 5.14 g (20 mmol) of 2-(t-butylaminosulfonyl)phenylboronic acid, 1.16 g of tetrakis(triphenylphosphine) palladium(O) (1 mmol), 0.32 g of tetrabutylammonium bromide (1 mmol) and 20 mL of 2M aqueous sodium carbonate were refluxed with 180 mL of benzene under N.sub.2 for 5.5 hours. After cooling, the mixture was diluted with methylene chloride and water. The two phases were separated and the organic phase was washed with water, dried with MgSO.sub.4 and concentrated in vacuo. The resulting thick oil was chromatographed on silica with 30% EtOAc/hexane to afford 2.52 g (41%) of the aniline. .sup.1 H NMR (CDCl.sub.3): .delta. 8.14 (d, 1H); 7.53 (t, 1H); 7.43 (t, 1H); 7.33 (d, 2H); 7.27 (d, 1H); 6.76 (d, 2H); 3.7 (br s, 1H); 0.99 (s, 9H).
Part G. Preparation of N-(2'-t-butylaminosulfonyl-[1,1']biphen-4-yl) -2-(3'-cyanophenyl)nicotinamide.
Methyl 2-(3'-cyanophenyl)nicotinate (300 mg, 1.3 mmol) was combined with of 4-amino-2'-t-butylaminosulfonyl-[1,1']biphenyl (383 mg, 1.3 mmol) in 12 mL dry CH.sub.2 Cl.sub.2. A solution of trimethylaluminum (3.8 mL, 2.0 M in heptane) was added, and an exothermic reaction immediately occurred and the mixture darkened. The resulting solution was stirred at room temperature under argon for 3 days and then quenched carefully with a few drops of 1 M HCl. An emulsion was obtained on dilution with EtOAc and water. The layers were separated, and the organic was extracted again with water and brine, dried over Na.sub.2 SO.sub.4, filtered, and evaporated. A small amount of additional material was obtained from the aqueous extract by adjusting the pH to 8 with sat. NaHCO.sub.3 and extracting with EtOAc. This material was dried over Na.sub.2 SO.sub.4, filtered, evaporated, and combined with the previous extract for chromatography on silica gel (50-60% EtOAc/hexanes) to yield the desired product (190 mg, 30%). .sup.1 H NMR (CDCl.sub.3): .delta. 8.86 (dd, 1H, J=4.7, J'=1.9), 8.14 (m, 3H), 8.00 (d, 1H, J=7.7), 7.73 (d, 1H, J=8.1), 7.50 (m, 9H), 7.29 (dd, 1H, J=7.4, J'=1.1), 3.60 (s, 1H), 1.02 (s, 9H).
Part H. Preparation of N-(2'-aminosulfonyl-[1,1']biphen-4-yl)-2-(3'-amidinophenyl)nicotinamide, trifluoroacetic acid Salt.
N-(2'-t-butylaminosulfonyl-[1,1']biphen-4-yl)-2-(3'-cyanophenyl)nicotinamide (190 mg, 0.37 mmol) was dissolved in dry MeOH (10 mL) and cooled to 0.degree. C. HCl(g) was generated by the addition of concentrated H.sub.2 SO.sub.4 (60 mL) to NaCl (240 g) over 40 minutes and was bubbled into the reaction mixture. The gas was permitted to continue bubbling through the reaction for 3 hours after the H.sub.2 SO.sub.4 addition was complete. At this point, the HCl generator and ice bath were removed, and the reaction stirred under argon for 19 hours. This solution was then evaporated, placed under high vacuum, and redissolved in dry MeOH (10 mL). Ammonium carbonate (200 mg) was added, stirred for 24 hours under argon, and evaporated. The product was purified by preparative HPLC on a C-18 reverse phase column (10-70% MeCN/H.sub.2 O/0.05% TFA), yielding a white powder (140 mg, 54%). .sup.1 H NMR (DMSO-d.sub.6): .delta. 10.65 (s, 1H), 9.38 (s, 2H), 8.92 (s, 2H), 8.81 (dd, 1H, J=4.4, J'=1.4), 8.10 (m, 2H), 7.97 (m, 2H), 7.76 (m, 1H), 7.67 (t, 1H, J=8.0), 7.57 (m, 5H), 7.29 (m, 5H). HRMS calc. for C.sub.25 H.sub.22 N.sub.5 O.sub.3 S: m/z 472.1443; found, 472.1457.
Examples 2, 3 and 4
N-[5-(2-aminosulfonyl)phenylpyrid-2-yl]-2-(3'-amidinophenyl)nicotinamide, trifluoroacetic acid salt (Example 2), N-[5-(2-t-butylaminosulfonyl)phenylpyrid-2-yl]-2-(3'-amidinophenyl)nicotinamide, trifluoroacetic acid salt (Example 3), and N-[5-(2-aminosulfonyl)phenylpyrid-2-yl]-2-(3'-carboxamidophenyl)nicotinanside, trifluoroacetic acid salt
Example 4
Part A. Preparation of 2-(3'-cyanophenyl)nicotinic acid.
Methyl 2-(3'-cyanophenyl)nicotinate (1.21 g, 5.1 mmol) was partially dissolved in MeOH (40 mL), and lithium hydroxide monohydrate (234 mg dissolved in 6 mL H.sub.2 O, 5.6 mmol) was added. After 20 hours, the resulting solution was diluted with water and extracted with CHCl.sub.3. The aqueous was acidified to pH 4 with 1 M HCl and extracted several times with CHCl.sub.3. Solid sodium chloride was added to the aqueous solution and the solution was extracted with 5-10% MeOH/CHCl.sub.3. The organic extracts were combined, dried over Na.sub.2 SO.sub.4, filtered, and evaporated to yield a white solid (1.06 g, 93%).
.sup.1 H NMR (CDCl.sub.3): .delta. 8.85 (dd, 1H, J=5.1, J'=1.5), 8.35 (dd, 1H, J=7.6, J'=1.4), 7.84 (s, 1H), 7.75 (m, 2H), 7.55 (t, 1H, J=7.7), 7.47 (m, 1H).
Part B. Preparation of 2-amino-5-(2-t-butylaminosulfonyl)phenylpyridine.
A mixture of 1.55 g (9.0 mmol) of 2-amino-5-bromopyridine and 2.3 g (9.0 mmol) of 2-(t-butylaminosulfonyl)phenylboronic acid, 0.52 g of tetrakis(triphenylphosphine) palladium(O) (0.45 mmol), 0.15 g of tetrabutylammonium bromide (0.45 mmol) and 9 mL of 2M aqueous sodium carbonate were refluxed with 80 mL of benzene under Ar for 5 hours. After cooling, the mixture was diluted with 25 mL of methylene chloride and 25 mL of water. The two phases were separated and the organic phase was washed with water, dried with MgSO.sub.4 and concentrated in vacuo. The resulting thick oil was chromatographed on silica with 50% EtOAc/hexane to afford 1.34 g (49%) of the aniline.
.sup.1 H NMR (CDCl.sub.3): .delta. 8.18 (d, 1H); 8.07 (m, 1H); 7.70 (dd, 1H); 7.58 (dt, 1H); 7.48 (dt, 1H); 7.28 (d, 1H); 6.56 (d, 1H); 4.62 (br s, 2H); 3.88 (br s, 1H); 1.06 (s, 9H).
Part C. Preparation of N-[5-(2-t-butylaminosulfonyl)phenylpyrid-2-yl]-2-(3'-cyanophenyl)nicotinamide.
2-(3'-cyanophenyl)nicotinic acid (300 mg, 1.3 mmol) was suspended in 5 mL dry CH.sub.2 Cl.sub.2, and oxalyl chloride (175 .mu.l, 2.0 mmol) was added, followed by 2 drops of dry DES. The reaction stirred at room temperature under argon for 2 hours and then evaporated. This solid was redissolved in 8 mL dry CH.sub.2 Cl.sub.2, and dimethylaminopyridine (490 mg, 4.0 mmol) was added, followed by 2-amino-5-(2-t-butylaminosulfonyl)phenylpyridine (410 mg, 1.3 mmol). The reaction was stirred 3 days at room temperature, diluted with CH.sub.2 Cl.sub.2, extracted with saturated NaHCO.sub.3, dried over Na.sub.2 SO.sub.4, filtered, and evaporated. The resulting material was chromatographed on silica gel (50-75% EtOAc/hexanes) to yield the desired product (423 mg, 62%).
.sup.1 H NMR (CDCl.sub.3): .delta. 8.83 (dd, 1H, J=4.8, J'=1.5), 8.40 (bs, 1H), 8.29 (bd, 1H, J=8.4), 8.17 (dd, 1H), J=8.0, J'=1.1), 8.09 (m, 3H), 7.97 (d, 1H, J=7.7), 7.79 (d, 1H, J=8.4), 7.69 (d, 1H, J=7.7), 7.54 (m, 4H), 7.25 (m, 1H), 4.19 (bs, 1H), 1.08 (s, 9H).
Part D. Preparation of N-[5-(2-aminosulfonyl)phenylpyrid-2-yl]-2-(3'-amidinophenyl)nicotinamide, trifluoroacetic acid salt (Example 2), N-[5-(2-t-butylaminosulfonyl)phenylpyrid-2-yl]-2-(3'-amidinophenyl)nicotinamide, trifluoroacetic acid salt (Example 3), and N-[5-(2-aminosulfonyl)phenylpyrid-2-yl]-2-(3'-carboxamidophenyl)nicotinamide, trifluoroacetic acid salt (Example 4).
N-[5-(2-t-butylaminosulfonyl)phenylpyrid-2-yl]-2-(3'-cyanophenyl)nicotinamide (410 mg, 1.03) was dissolved in a mixture of dry MeOH (5 mL) and dry CHCl.sub.3 (15 mL) and cooled to 0.degree. C. HCl(g) was generated by the addition of concentrated H.sub.2 SO.sub.4 (45 mL) to NaCl (220 g) over 55 min and was bubbled into the reaction mixture. The HCl generator and ice bath were removed, and the reaction was stirred under argon for 16 hours and evaporated. The resulting solid was redissolved in dry MeOH (15 mL), and ammonium carbonate (385 mg) was added. The reaction was stirred 19 hours at room temperature under argon and evaporated. The resulting solid was purified by preparative HPLC on a C-18 reverse phase column (5-70% MeCN/H.sub.2 O/0.05% TFA) to yield N-[5-(2-aminosulfonyl)phenylpyrid-2-yl]-2-(3'-amidinophenyl)nicotinamide, trifluoroacetic acid salt (Example 2), (250 mg, 45%). .sup.1 H NMR (DMSO-d.sub.6): .delta. 11.27 (s, 1H), 9.43 (s, 2H), 8.98 (s, 2H), 8.83 (dd, 1H, J=4.8, J'=1.9), 8.32 (s, 1H), 8.13 (m, 2H), 8.05 (m, 2H), 7.96 (d, 1H, J=7.3), 7.81 (d, 2H, J=8.4), 7.65 (m, 4H), 7.47 (s, 2H), 7.37 (m, 1H). HRMS calc. for C.sub.24 H.sub.21 N.sub.6 O.sub.3 S: m/z 473.1396; found, 473.1397. A second product, N-[5-(2-t-butylaminosulfonyl)-phenylpyrid-2-yl]-2-(3'-amidinophenyl)nicotinamide, trifluoroacetic acid salt (Example 3), was also obtained (58 mg, 10%). .sup.1 H NMR (DMSO-d.sub.6): .delta. 9.7 (s, 1H), 9.41 (s, 2H), 8.95 (s, 2H), 8.82 (m, 1H), 8.28 (s, 1H), 8.09 (m, 4H), 7.95 (d, 1H, J=7.7), 7.79 (m, 2H), 7.63 (m, 4H), 7.34 (d, 1H, J=7.7), 7.18 (s, 1H), 1.04 (s, 9H). HRMS calc. for C.sub.28 H.sub.29 N.sub.6 O.sub.3 S: 529.2022; found, 529.2050. A third product, N-[5-(2-aminosulfonyl)phenylpyrid-2-yl]-2-(3'-carboxamidophenyl)nicotinamide, trifluoroacetic acid salt (Example 4) was isolated and chromatographed on silica gel (10-20% MeOH/CHCl.sub.3) to yield a white solid (77 mg, 20%). .sup.1 H NMR (DMSO-d.sub.6): .delta. 11.13 (s, 1H), 8.75 (dd, 1H, J=4.8, J'=1.9), 8.26 (m, 2H), 8.02 (m, 4H), 7.84 (d, 1H, J=7.7), 7.74 (m, 2H), 7.59 (m, 2H), 7.47 (m, 2H), 7.36 (m, 4H).
TABLE 1______________________________________ #STR27## - MS Ex D R.sub.2 A' (M + H).sup.+______________________________________1 C(.dbd.NH)NH.sub.2 SO.sub.2 NH.sub.2 CH 472.1 2 C(.dbd.NH)NH.sub.2 SO.sub.2 NH.sub.2 N 473.1 3 C(.dbd.NH)NH.sub.2 SO.sub.2 NHtBu N 529.2 4 C(O)NH.sub.2 SO.sub.2 NH.sub.2 N 474.1______________________________________
The following table contains representative examples of the present invention. Each entry in the table is intended to be paired with each formulae at the start of the table. For example, example 1 in Table 2 is intended to be paired with each of formulae a.sub.1 -ss.sub.4.
TABLE 2__________________________________________________________________________ ##STR28##__________________________________________________________________________ #STR29## #STR30## ##STR31##__________________________________________________________________________a.sub.1 R = F, D = NH.sub.2 b.sub.1 R = F, D = NH.sub.2 c.sub.1 R = F, D = NH.sub.2 a.sub.2 R = H, D = NH.sub.2 b.sub.2 R = H, D = NH.sub.2 c.sub.2 R = H, D = NH.sub.2 a.sub.3 R = F, D = CH.sub.2 NH.sub.2 b.sub.3 R = F, D = CH.sub.2 NH.sub.2 c.sub.3 R = F, D = CH.sub.2 NH.sub.2 a.sub.4 R = H, D = CH.sub.2 NH.sub.2 b.sub.4 R = H, D = CH.sub.2 NH.sub.2 c.sub.4 R = H, D = CH.sub.2 NH.sub.2 a.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 b.sub.5 R = F, D = C(.dbd.NH)NH.su b.2 c.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 a.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 b.sub.6 R = H, D = C(.dbd.NH)NH.su b.2 c.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 a.sub.7 R = F, D = C(O)NH.sub.2 b.sub.7 R = F, D = C(O)NH.sub.2 c.sub.7 R = F, D = C(O)NH.sub.2 a.sub.8 R = H, D = C(O)NH.su b.2 b.sub.8 R = H, D = C(O)NH.sub.2 c.sub.8 R = H, D = C(O)NH.sub.2__________________________________________________________________________ #STR32## #STR33## ##STR34##__________________________________________________________________________d.sub.1 R = F, D = NH.sub.2 e.sub.1 R = F, D = NH.sub.2 f.sub.1 R = F, D = NH.sub.2 d.sub.2 R = H, D = NH.sub.2 e.sub.2 R = H, D = NH.sub.2 f.sub.2 R = H, D = NH.sub.2 d.sub.3 R = F, D = CH.sub.2 NH.sub.2 e.sub.3 R = F, D = CH.sub.2 NH.sub.2 f.sub.3 R = F, D = CH.sub.2 NH.sub.2 d.sub.4 R = H, D = CH.sub.2 NH.sub.2 e.sub.4 R = H, D = CH.sub.2 NH.sub.2 f.sub.4 R = H, D = CH.sub.2 NH.sub.2 d.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 e.sub.5 R = F, D = C(.dbd.NH)NH.su b.2 f.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 d.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 e.sub.6 R = H, D = C(.dbd.NH)NH.su b.2 f.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 d.sub.7 R = F, D = C(O)NH.sub.2 e.sub.7 R = F, D = C(O)NH.sub.2 f.sub.7 R = F, D = C(O)NH.sub.2 d.sub.8 R = H, D = C(O)NH.su b.2 e.sub.8 R = H, D = C(O)NH.sub.2 f.sub.8 R = H, D = C(O)NH.sub.2__________________________________________________________________________ #STR35## #STR36## ##STR37##__________________________________________________________________________g.sub.1 R = F, D = NH.sub.2 h.sub.1 R = F, D = NH.sub.2 i.sub.1 R = F, D = NH.sub.2 g.sub.2 R = H, D = NH.sub.2 h.sub.2 R = H, D = NH.sub.2 i.sub.2 R = H, D = NH.sub.2 g.sub.3 R = F, D = CH.sub.2 NH.sub.2 h.sub.3 R = F, D = CH.sub.2 NH.sub.2 i.sub.3 R = F, D = CH.sub.2 NH.sub.2 g.sub.4 R = H, D = CH.sub.2 NH.sub.2 h.sub.4 R = H, D = CH.sub.2 NH.sub.2 i.sub.4 R = H, D = CH.sub.2 NH.sub.2 g.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 h.sub.5 R = F, D = C(.dbd.NH)NH.su b.2 i.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 g.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 h.sub.6 R = H, D = C(.dbd.NH)NH.su b.2 i.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 g.sub.7 R = F, D = C(O)NH.sub.2 h.sub.7 R = F, D = C(O)NH.sub.2 i.sub.7 R = F, D = C(O)NH.sub.2 g.sub.8 R = H, D = C(O)NH.su b.2 h.sub.8 R = H, D = C(O)NH.sub.2 i.sub.8 R = H, D = C(O)NH.sub.2__________________________________________________________________________ #STR38## #STR39## ##STR40##__________________________________________________________________________j.sub.1 R = F, D = NH.sub.2 k.sub.1 R = F, D = NH.sub.2 l.sub.1 R = F, D = NH.sub.2 j.sub.2 R = H, D = NH.sub.2 k.sub.2 R = H, D = NH.sub.2 l.sub.2 R = H, D = NH.sub.2 j.sub.3 R = F, D = CH.sub.2 NH.sub.2 k.sub.3 R = F, D = CH.sub.2 NH.sub.2 l.sub.3 R = F, D = CH.sub.2 NH.sub.2 j.sub.4 R = H, D = CH.sub.2 NH.sub.2 k.sub.4 R = H, D = CH.sub.2 NH.sub.2 l.sub.4 R = H, D = CH.sub.2 NH.sub.2 j.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 k.sub.5 R = F, D = C(.dbd.NH)NH.su b.2 l.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 j.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 k.sub.6 R = H, D = C(.dbd.NH)NH.su b.2 l.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 j.sub.7 R = F, D = C(O)NH.sub.2 k.sub.7 R = F, D = C(O)NH.sub.2 l.sub.7 R = F, D = C(O)NH.sub.2 j.sub.8 R = H, D = C(O)NH.su b.2 k.sub.8 R = H, D = C(O)NH.sub.2 l.sub.8 R = H, D = C(O)NH.sub.2__________________________________________________________________________ #STR41## #STR42## ##STR43##__________________________________________________________________________m.sub.1 R = F, D = NH.sub.2 n.sub.1 R = F, D = NH.sub.2 o.sub.1 R = F, D = NH.sub.2 m.sub.2 R = H, D = NH.sub.2 n.sub.2 R = H, D = NH.sub.2 o.sub.2 R = H, D = NH.sub.2 m.sub.3 R = F, D = CH.sub.2 NH.sub.2 n.sub.3 R = F, D = CH.sub.2 NH.sub.2 o.sub.3 R = F, D = CH.sub.2 NH.sub.2 m.sub.4 R = H, D = CH.sub.2 NH.sub.2 n.sub.4 R = H, D = CH.sub.2 NH.sub.2 o.sub.4 R = H, D = CH.sub.2 NH.sub.2 m.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 n.sub.5 R = F, D = C(.dbd.NH)NH.su b.2 o.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 m.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 n.sub.6 R = H, D = C(.dbd.NH)NH.su b.2 o.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 m.sub.7 R = F, D = C(O)NH.sub.2 n.sub.7 R = F, D = C(O)NH.sub.2 o.sub.7 R = F, D = C(O)NH.sub.2 m.sub.8 R = H, D = C(O)NH.su b.2 n.sub.8 R = H, D = C(O)NH.sub.2 o.sub.8 R = H, D = C(O)NH.sub.2__________________________________________________________________________ #STR44## #STR45## ##STR46##__________________________________________________________________________p.sub.1 R = F, D = NH.sub.2 q.sub.1 R = F, D = NH.sub.2 r.sub.1 R = F, D = NH.sub.2 p.sub.2 R = Cl, D = NH.sub.2 q.sub.2 R = Cl, D = NH.sub.2 r.sub.2 R = Cl, D = NH.sub.2 p.sub.3 R = OMe, D = NH.sub.2 q.sub.3 R = OMe, D = NH.sub.2 r.sub.3 R = OMe, D = NH.sub.2 p.sub.4 R = F, D = CH.sub.2 NH.sub.2 q.sub.4 R = F, D = CH.sub.2 NH.sub.2 r.sub.4 R = F, D = CH.sub.2 NH.sub.2 p.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 q.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 r.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 p.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 q.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 r.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 p.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 q.sub.7 R = F, D = C(.dbd.NH)NH.su b.2 r.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 p.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 q.sub.8 R = Cl, D = C(.dbd.NH)NH. sub.2 r.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 p.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 q.sub.9 R = OMe, D = C(.dbd.NH)N H.sub.2 r.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 p.sub.10 R = F, D = C(O)NH.sub.2 q.sub.10 R = F, D = C(O)NH.sub.2 r.sub.10 R = F, D = C(O)NH.su b.2 p.sub.11 R = Cl, D = C(O)NH.sub.2 q.sub.11 R = Cl, D = C(O)NH.sub.2 r.sub.11 R = Cl, D = C(O)NH.sub.2 p.sub.12 R = OMe, D = C(O)NH.sub.2 q.sub.12 R = OMe, D = C(O)NH.sub.2 r.sub.12 R = OMe, D = C(O)NH.sub.2__________________________________________________________________________ #STR47## #STR48## ##STR49##__________________________________________________________________________s.sub.1 R = F, D = NH.sub.2 t.sub.1 R = F, D = NH.sub.2 u.sub.1 R = F, D = NH.sub.2 s.sub.2 R = Cl, D = NH.sub.2 t.sub.2 R = Cl, D = NH.sub.2 u.sub.2 R = Cl, D = NH.sub.2 s.sub.3 R = OMe, D = NH.sub.2 t.sub.3 R = OMe, D = NH.sub.2 u.sub.3 R = OMe, D = NH.sub.2 s.sub.4 R = F, D = CH.sub.2 NH.sub.2 t.sub.4 R = F, D = CH.sub.2 NH.sub.2 u.sub.4 R = F, D = CH.sub.2 NH.sub.2 s.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 t.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 u.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 s.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 t.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 u.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 s.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 t.sub.7 R = F, D = C(.dbd.NH)NH.su b.2 u.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 s.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 t.sub.8 R = Cl, D = C(.dbd.NH)NH. sub.2 u.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 s.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 t.sub.9 R = OMe, D = C(.dbd.NH)N H.sub.2 u.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 s.sub.10 R = F, D = C(O)NH.sub.2 t.sub.10 R = F, D = C(O)NH.sub.2 u.sub.10 R = F, D = C(O)NH.su b.2 s.sub.11 R = Cl, D = C(O)NH.sub.2 t.sub.11 R = Cl, D = C(O)NH.sub.2 u.sub.11 R = Cl, D = C(O)NH.sub.2 s.sub.12 R = OMe, D = C(O)NH.sub.2 t.sub.12 R = OMe, D = C(O)NH.sub.2 u.sub.12 R = OMe, D = C(O)NH.sub.2__________________________________________________________________________ #STR50## #STR51## ##STR52##__________________________________________________________________________v.sub.1 R = F, D = NH.sub.2 w.sub.1 R = F, D = NH.sub.2 x.sub.1 R = F, D = NH.sub.2 v.sub.2 R = Cl, D = NH.sub.2 w.sub.2 R = Cl, D = NH.sub.2 x.sub.2 R = Cl, D = NH.sub.2 v.sub.3 R = OMe, D = NH.sub.2 w.sub.3 R = OMe, D = NH.sub.2 x.sub.3 R = OMe, D = NH.sub.2 v.sub.4 R = F, D = CH.sub.2 NH.sub.2 w.sub.4 R = F, D = CH.sub.2 NH.sub.2 x.sub.4 R = F, D = CH.sub.2 NH.sub.2 v.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 w.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 x.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 v.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 w.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 x.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 v.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 w.sub.7 R = F, D = C(.dbd.NH)NH.su b.2 x.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 v.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 w.sub.8 R = Cl, D = C(.dbd.NH)NH. sub.2 x.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 v.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 w.sub.9 R = OMe, D = C(.dbd.NH)N H.sub.2 x.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 v.sub.10 R = F, D = C(O)NH.sub.2 w.sub.10 R = F, D = C(O)NH.sub.2 x.sub.10 R = F, D = C(O)NH.su b.2 v.sub.11 R = Cl, D = C(O)NH.sub.2 w.sub.11 R = Cl, D = C(O)NH.sub.2 x.sub.11 R = Cl, D = C(O)NH.sub.2 v.sub.12 R = OMe, D = C(O)NH.sub.2 w.sub.12 R = OMe, D = C(O)NH.sub.2 x.sub.12 R = OMe, D = C(O)NH.sub.2__________________________________________________________________________ #STR53## #STR54## ##STR55##__________________________________________________________________________y.sub.1 R = F, D = NH.sub.2 z.sub.1 R = F, D = NH.sub.2 aa.sub.1 R = F, D = NH.sub.2 y.sub.2 R = Cl, D = NH.sub.2 z.sub.2 R = Cl, D = NH.sub.2 aa.sub.2 R = Cl, D = NH.sub.2 y.sub.3 R = OMe, D = NH.sub.2 z.sub.3 R = OMe, D = NH.sub.2 aa.sub.3 R = OMe, D = NH.sub.2 y.sub.4 R = F, D = CH.sub.2 NH.sub.2 z.sub.4 R = F, D = CH.sub.2 NH.sub.2 aa.sub.4 R = F, D = CH.sub.2 NH.sub.2 y.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 z.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 aa.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 y.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 z.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 aa.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 y.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 z.sub.7 R = F, D = C(.dbd.NH)NH.su b.2 aa.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 y.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 z.sub.8 R = Cl, D = C(.dbd.NH)NH. sub.2 aa.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 y.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 z.sub.9 R = OMe, D = C(.dbd.NH)N H.sub.2 aa.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 y.sub.10 R = F, D = C(O)NH.sub.2 z.sub.10 R = F, D = C(O)NH.sub.2 aa.sub.10 R = F, D = C(O)NH.sub.2 y.sub.11 R = Cl, D = C(O)NH.sub.2 z.sub.11 R = Cl, D = C(O)NH.sub.2 aa.sub.11 R = Cl, D = C(O)NH.sub.2 y.sub.12 R = OMe, D = C(O)NH.sub.2 z.sub.12 R = OMe, D = C(O)NH.sub.2 aa.sub.12 R = OMe, D = C(O)NH.sub.2__________________________________________________________________________ #STR56## #STR57## ##STR58##__________________________________________________________________________bb.sub.1 R = F, D = NH.sub.2 cc.sub.1 R = F, D = NH.sub.2 dd.sub.1 R = F, D = NH.sub.2 bb.sub.2 R = Cl, D = NH.sub.2 cc.sub.2 R = Cl, D = NH.sub.2 dd.sub.2 R = Cl, D = NH.sub.2 bb.sub.3 R = OMe, D = NH.sub.2 cc.sub.3 R = OMe, D = NH.sub.2 dd.sub.3 R = OMe, D = NH.sub.2 bb.sub.4 R = F, D = CH.sub.2 NH.sub.2 cc.sub.4 R = F, D = CH.sub.2 NH.sub.2 dd.sub.4 R = F, D = CH.sub.2 NH.sub.2 bb.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 cc.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 dd.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 bb.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 cc.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 dd.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 bb.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 cc.sub.7 R = F, D = C(.dbd.NH)NH. sub.2 dd.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 bb.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 cc.sub.8 R = Cl, D = C(.dbd.NH)N H.sub.2 dd.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 bb.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 cc.sub.9 R = OMe, D = C(.dbd.NH )NH.sub.2 dd.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 bb.sub.10 R = F, D = C(O)NH.sub.2 cc.sub.10 R = F, D = C(O)NH.sub.2 dd.sub.10 R = F, D = C(O)NH.sub.2 bb.sub.11 R = Cl, D = C(O)NH.sub.2 cc.sub.11 R = Cl, D = C(O)NH.sub.2 dd.sub.11 R = Cl, D = C(O)NH.sub.2 bb.sub.12 R = OMe, D = C(O)NH.sub.2 cc.sub.12 R = OMe, D = C(O)NH.sub.2 dd.sub.12 R = OMe, D = C(O)NH.sub.2__________________________________________________________________________ #STR59## #STR60## ##STR61##__________________________________________________________________________ee.sub.1 R = F, D = CH.sub.2 NH.sub.2 ff.sub.1 R = F, D = CH.sub.2 NH.sub.2 gg.sub.1 R = F, D = CH.sub.2 NH.sub.2 ee.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 ff.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 gg.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 ee.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 ff.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 gg.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 ee.sub.4 R = CH.sub.2 NH.sub.2, ff.sub.4 R = CH.sub.2 NH.sub.2, gg.sub.4 R = CH.sub.2 NH.sub.2, D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2__________________________________________________________________________ #STR62## #STR63## ##STR64##__________________________________________________________________________hh.sub.1 R = F, D = CH.sub.2 NH.sub.2 ii.sub.1 R = F, D = CH.sub.2 NH.sub.2 jj.sub.1 R = F, D = CH.sub.2 NH.sub.2 hh.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 ii.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 jj.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 hh.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 ii.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 jj.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 hh.sub.4 R = CH.sub.2 NH.sub.2, ii.sub.4 R = CH.sub.2 NH.sub.2, jj.sub.4 R = CH.sub.2 NH.sub.2, D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2__________________________________________________________________________ #STR65## #STR66## ##STR67##__________________________________________________________________________kk.sub.1 R = F, D = CH.sub.2 NH.sub.2 ll.sub.1 R = F, D = CH.sub.2 NH.sub.2 mm.sub.1 R = F, D = CH.sub.2 NH.sub.2 kk.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 ll.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 mm.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 kk.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 ll.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 mm.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 kk.sub.4 R = CH.sub.2 NH.sub.2, ll.sub.4 R = CH.sub.2 NH.sub.2, mm.sub.4 R = CH.sub.2 NH.sub.2, D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2__________________________________________________________________________ #STR68## #STR69## ##STR70##__________________________________________________________________________nn.sub.1 R = F, D = CH.sub.2 NH.sub.2 oo.sub.1 R = F, D = CH.sub.2 NH.sub.2 pp.sub.1 R = F, D = CH.sub.2 NH.sub.2 nn.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 oo.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 pp.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 nn.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 oo.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 pp.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 nn.sub.4 R = CH.sub.2 NH.sub.2, oo.sub.4 R = CH.sub.2 NH.sub.2, pp.sub.4 R = CH.sub.2 NH.sub.2, D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2__________________________________________________________________________ #STR71## #STR72## ##STR73##__________________________________________________________________________qq.sub.1 R = F, D = CH.sub.2 NH.sub.2 rr.sub.1 R = F, D = CH.sub.2 NH.sub.2 ss.sub.1 R = F, D = CH.sub.2 NH.sub.2 qq.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 rr.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 ss.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 qq.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 rr.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 ss.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 qq.sub.4 R = CH.sub.2 NH.sub.2, rr.sub.4 R = CH.sub.2 NH.sub.2, ss.sub.4 R = CH.sub.2 NH.sub.2, D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2__________________________________________________________________________
______________________________________Ex # R.sup.1b A B______________________________________1 H phenyl 2-(aminosulfonyl)phenyl 2 H phenyl 2-(methylaminosulfonyl)phenyl 3 H phenyl 1-pyrrolidinocarbonyl 4 H phenyl 2-(methylsulfonyl)phenyl 5 H phenyl 4-morpholino 6 H phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 7 H phenyl 4-morpholinocarbonyl 8 H 2-pyridyl 2-(aminosulfonyl)phenyl 9 H 2-pyridyl 2-(methylaminosulfonyl)phenyl 10 H 2-pyridyl 1-pyrrolidinocarbonyl 11 H 2-pyridyl 2-(methylsulfonyl)phenyl 12 H 2-pyridyl 4-morpholino 13 H 2-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 14 H 2-pyridyl 4-morpholinocarbonyl 15 H 3-pyridyl 2-(aminosulfonyl)phenyl 16 H 3-pyridyl 2-(methylaminosulfonyl)phenyl 17 H 3-pyridyl 1-pyrrolidinocarbonyl 18 H 3-pyridyl 2-(methylsulfonyl)phenyl 19 H 3-pyridyl 4-morpholino 20 H 3-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 21 H 3-pyridyl 4-morpholinocarbonyl 22 H 2-pyrimidyl 2-(aminosulfonyl)phenyl 23 H 2-pyrimidyl 2-(methylaminosulfonyl)phenyl 24 H 2-pyrimidyl 1-pyrrolidinocarbonyl 25 H 2-pyrimidyl 2-(methylsulfonyl)phenyl 26 H 2-pyrimidyl 4-morpholino 27 H 2-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 28 H 2-pyrimidyl 4-morpholinocarbonyl 29 H 5-pyrimidyl 2-(aminosulfonyl)phenyl 30 H 5-pyrimidyl 2-(methylaminosulfonyl)phenyl 31 H 5-pyrimidyl 1-pyrrolidinocarbonyl 32 H 5-pyrimidyl 2-(methylsulfonyl)phenyl 33 H 5-pyrimidyl 4-morpholino 34 H 5-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 35 H 5-pyrimidyl 4-morpholinocarbonyl 36 H 2-Cl-phenyl 2-(aminosulfonyl)phenyl 37 H 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl 38 H 2-Cl-phenyl 1-pyrrolidinocarbonyl 39 H 2-Cl-phenyl 2-(methylsulfonyl)phenyl 40 H 2-Cl-phenyl 4-morpholino 41 H 2-Cl-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 42 H 2-Cl-phenyl 4-morpholinocarbonyl 43 H 2-F-phenyl 2-(aminosulfonyl)phenyl 44 H 2-F-phenyl 2-(methylaminosulfonyl)phenyl 45 H 2-F-phenyl 1-pyrrolidinocarbonyl 46 H 2-F-phenyl 2-(methylsulfonyl)phenyl 47 H 2-F-phenyl 4-morpholino 48 H 2-F-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 49 H 2-F-phenyl 4-morpholinocarbonyl 50 H 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 51 H 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl 52 H 2,5-diF-phenyl 1-pyrrolidinocarbonyl 53 H 2,5-diF-phenyl 2-(methylsulfonyl)phenyl 54 H 2,5-diF-phenyl 4-morpholino 55 H 2,5-diF-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 56 H 2,5-diF-phenyl 4-morpholinocarbonyl 57 H phenyl 2-(N-pyrrolidinyl-methyl)phenyl 58 H phenyl 2-(N-piperidinyl-methyl)phenyl 59 H phenyl 2-(N-morpholino-methyl)phenyl 60 H phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 61 H phenyl 2-(N-pyridinium-methyl)phenyl 62 H phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 63 H phenyl 2-(N-azatanyl-methyl)phenyl 64 H phenyl 2-(N-azetidinyl-methyl)phenyl 65 H phenyl 2-(N-piperazinyl-methyl)phenyl 66 H phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 67 H phenyl 2-(N-imidazolyl-methyl)phenyl 68 H phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 69 H phenyl 2-(N-pyridonyl-methyl)phenyl 70 H phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 71 H phenyl 2-(amidinyl)phenyl 72 H phenyl 2-(N-guanidinyl)phenyl 73 H phenyl 2-(imidazolyl)phenyl 74 H phenyl 2-(imidazolidinyl)phenyl 75 H phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 76 H phenyl 2-(2-pyrrolidinyl)phenyl 77 H phenyl 2-(2-piperidinyl)phenyl 78 H phenyl 2-(amidinyl-methyl)phenyl 79 H phenyl 2-(2-imidazolidinyl- methyl)phenyl 80 H phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 81 H phenyl 2-dimethylaminoimidazol-1-yl 82 H phenyl 2-(3-aminophenyl) 83 H phenyl 2-(3-pyrrolidinylcarbonyl) 84 H phenyl 2-glycinoyl 85 H phenyl 2-(imidazol-1-ylacetyl) 86 H 2-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl 87 H 2-pyridyl 2-(N-piperidinyl-methyl)phenyl 88 H 2-pyridyl 2-(N-morpholino-methyl)phenyl 89 H 2-pyridyl 2-(N,N'-methylmorpholinium- methyl)phenyl 90 H 2-pyridyl 2-(N-pyridinium-methyl)phenyl 91 H 2-pyridyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 92 H 2-pyridyl 2-(N-azatanyl-methyl)phenyl 93 H 2-pyridyl 2-(N-azetidinyl-methyl)phenyl 94 H 2-pyridyl 2-(N-piperazinyl-methyl)phenyl 95 H 2-pyridyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 96 H 2-pyridyl 2-(N-imidazolyl-methyl)phenyl 97 H 2-pyridyl 2-(N-methoxy-N-methylamino- methyl)phenyl 98 H 2-pyridyl 2-(N-pyridonyl-methyl)phenyl 99 H 2-pyridyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 100 H 2-pyridyl 2-(amidinyl)phenyl 101 H 2-pyridyl 2-(N-guanidinyl)phenyl 102 H 2-pyridyl 2-(imidazolyl)phenyl 103 H 2-pyridyl 2-(imidazolidinyl)phenyl 104 H 2-pyridyl 2-(2-imidazolidinyl- sulfonyl)phenyl 105 H 2-pyridyl 2-(2-pyrrolidinyl)phenyl 106 H 2-pyridyl 2-(2-piperidinyl)phenyl 107 H 2-pyridyl 2-(amidinyl-methyl)phenyl 108 H 2-pyridyl 2-(2-imidazolidinyl- methyl)phenyl 109 H 2-pyridyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 110 H 2-pyridyl 2-dimethylaminoimidazol-1-yl 111 H 2-pyridyl 2-(3-aminophenyl) 112 H 2-pyridyl 2-(3-pyrrolidinylcarbonyl) 113 H 2-pyridyl 2-glycinoyl 114 H 2-pyridyl 2-(imidazol-1-ylacetyl) 115 H 3-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl 116 H 3-pyridyl 2-(N-piperidinyl-methyl)phenyl 117 H 3-pyridyl 2-(N-morpholino-methyl)phenyl 118 H 3-pyridyl 2-(N,N'-methylmorpholinium- methyl)phenyl 119 H 3-pyridyl 2-(N-pyridiniuin-methyl)phenyl 120 H 3-pyridyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 121 H 3-pyridyl 2-(N-azatanyl-methyl)phenyl 122 H 3-pyridyl 2-(N-azetidinyl-methyl)phenyl 123 H 3-pyridyl 2-(N-piperazinyl-methyl)phenyl 124 H 3-pyridyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 125 H 3-pyridyl 2-(N-imidazolyl-methyl)phenyl 126 H 3-pyridyl 2-(N-methoxy-N-methylamino- methyl)phenyl 127 H 3-pyridyl 2-(N-pyridonyl-methyl)phenyl 128 H 3-pyridyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 129 H 3-pyridyl 2-(amidinyl)phenyl 130 H 3-pyridyl 2-(N-guanidinyl)phenyl 131 H 3-pyridyl 2-(imidazolyl)phenyl 132 H 3-pyridyl 2-(imidazolidinyl)phenyl 133 H 3-pyridyl 2-(2-imidazolidinyl- sulfonyl)phenyl 134 H 3-pyridyl 2-(2-pyrrolidinyl)phenyl 135 H 3-pyridyl 2-(2-piperidinyl)phenyl 136 H 3-pyridyl 2-(amidinyl-methyl)phenyl 137 H 3-pyridyl 2-(2-imidazolidinyl- methyl)phenyl 138 H 3-pyridyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 139 H 3-pyridyl 2-dimethylaminoimidazol-1-yl 140 H 3-pyridyl 2-(3-aminophenyl) 141 H 3-pyridyl 2-(3-pyrrolidinylcarbonyl) 142 H 3-pyridyl 2-glycinoyl 143 H 3-pyridyl 2-(imidazol-1-ylacetyl) 144 H 2-pyrimidyl 2-(N-pyrrolidinyl-methyl)phenyl 145 H 2-pyrimidyl 2-(N-piperidinyl-methyl)phenyl 146 H 2-pyrimidyl 2-(N-morpholino-methyl)phenyl 147 H 2-pyrimidyl 2-(N,N'-methylmorpholinium- methyl)phenyl 148 H 2-pyrimidyl 2-(N-pyridinium-methyl)phenyl 149 H 2-pyrimidyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 150 H 2-pyrimidyl 2-(N-azatanyl-methyl)phenyl 151 H 2-pyrimidyl 2-(N-azetidinyl-methyl)phenyl 152 H 2-pyrimidyl 2-(N-piperazinyl-methyl)phenyl 153 H 2-pyrimidyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 154 H 2-pyrimidyl 2-(N-imidazolyl-methyl)phenyl 155 H 2-pyrimidyl 2-(N-methoxy-N-methylamino- methyl)phenyl 156 H 2-pyrimidyl 2-(N-pyridonyl-methyl)phenyl 157 H 2-pyrimidyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 158 H 2-pyrimidyl 2-(amidinyl)phenyl 159 H 2-pyrimidyl 2-(N-guanidinyl)phenyl 160 H 2-pyrimidyl 2-(imidazolyl)phenyl 161 H 2-pyrimidyl 2-(imidazolidinyl)phenyl 162 H 2-pyrimidyl 2-(2-imidazolidinyl- sulfonyl)phenyl 163 H 2-pyrimidyl 2-(2-pyrrolidinyl)phenyl 164 H 2-pyrimidyl 2-(2-piperidinyl)phenyl 165 H 2-pyrimidyl 2-(amidinyl-methyl)phenyl 166 H 2-pyrimidyl 2-(2-imidazolidinyl- methyl)phenyl 167 H 2-pyrimidyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 168 H 2-pyrimidyl 2-dimethylaminoimidazol-1-yl 169 H 2-pyrimidyl 2-(3-aminophenyl) 170 H 2-pyrimidyl 2-(3-pyrrolidinylcarbonyl) 171 H 2-pyrimidyl 2-glycinoyl 172 H 2-pyrimidyl 2-(imidazol-1-ylacetyl) 173 H 2-Cl-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 174 H 2-Cl-phenyl 2-(N-piperidinyl-methyl)phenyl 175 H 2-Cl-phenyl 2-(N-morpholino-methyl)phenyl 176 H 2-Cl-phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 177 H 2-Cl-phenyl 2-(N-pyridinium-methyl)phenyl 178 H 2-Cl-phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 179 H 2-Cl-phenyl 2-(N-azatanyl-methyl)phenyl 180 H 2-Cl-phenyl 2-(N-azetidinyl-methyl)phenyl 181 H 2-Cl-phenyl 2-(N-piperazinyl-methyl)phenyl 182 H 2-Cl-phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 183 H 2-Cl-phenyl 2-(N-imidazolyl-methyl)phenyl 184 H 2-Cl-phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 185 H 2-Cl-phenyl 2-(N-pyridonyl-methyl)phenyl 186 H 2-Cl-phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 187 H 2-Cl-phenyl 2-(amidinyl)phenyl 188 H 2-Cl-phenyl 2-(N-guanidinyl)phenyl 189 H 2-Cl-phenyl 2-(imidazolyl)phenyl 190 H 2-Cl-phenyl 2-(imidazolidinyl)phenyl 191 H 2-Cl-phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 192 H 2-Cl-phenyl 2-(2-pyrrolidinyl)phenyl 193 H 2-Cl-phenyl 2-(2-piperidinyl)phenyl 194 H 2-Cl-phenyl 2-(amidinyl-methyl)phenyl 195 H 2-Cl-phenyl 2-(2-imidazolidinyl- methyl)phenyl 196 H 2-Cl-phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 197 H 2-Cl-phenyl 2-dimethylaminoimidazol-1-yl 198 H 2-Cl-phenyl 2-(3-aminophenyl) 199 H 2-Cl-phenyl 2-(3-pyrrolidinylcarbonyl) 200 H 2-Cl-phenyl 2-glycinoyl 201 H 2-Cl-phenyl 2-(imidazol-1-ylacetyl) 202 H 2-F-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 203 H 2-F-phenyl 2-(N-piperidinyl-methyl)phenyl 204 H 2-F-phenyl 2-(N-morpholino-methyl)phenyl 205 H 2-F-phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 206 H 2-F-phenyl 2-(N-pyridinium-methyl)phenyl 207 H 2-F-phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 208 H 2-F-phenyl 2-(N-azatanyl-methyl)phenyl 209 H 2-F-phenyl 2-(N-azetidinyl-methyl)phenyl 210 H 2-F-phenyl 2-(N-piperazinyl-methyl)phenyl 211 H 2-F-phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 212 H 2-F-phenyl 2-(N-imidazolyl-methyl)phenyl 213 H 2-F-phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 214 H 2-F-phenyl 2-(N-pyridonyl-methyl)phenyl 215 H 2-F-phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 216 H 2-F-phenyl 2-(amidinyl)phenyl 217 H 2-F-phenyl 2-(N-guanidinyl)phenyl 218 H 2-F-phenyl 2-(imidazolyl)phenyl 219 H 2-F-phenyl 2-(imidazolidinyl)phenyl 220 H 2-F-phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 221 H 2-F-phenyl 2-(2-pyrrolidinyl)phenyl 222 H 2-F-phenyl 2-(2-piperidinyl)phenyl 223 H 2-F-phenyl 2-(amidinyl-methyl)phenyl 224 H 2-F-phenyl 2-(2-imidazolidinyl- methyl)phenyl 225 H 2-F-phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 226 H 2-F-phenyl 2-dimethylaminoimidazol-1-yl 227 H 2-F-phenyl 2-(3-aminophenyl) 228 H 2-F-phenyl 2-(3-pyrrolidinylcarbonyl) 229 H 2-F-phenyl 2-glycinoyl 230 H 2-F-phenyl 2-(imidazol-1-ylacetyl) 231 H 2,5-diF-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 232 H 2,5-diF-phenyl 2-(N-piperidinyl-methyl)phenyl 233 H 2,5-diF-phenyl 2-(N-morpholino-methyl)phenyl 234 H 2,5-diF-phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 235 H 2,5-diF-phenyl 2-(N-pyridinium-methyl)phenyl 236 H 2,5-diF-phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 237 H 2,5-diF-phenyl 2-(N-azatanyl-methyl)phenyl 238 H 2,5-diF-phenyl 2-(N-azetidinyl-methyl)phenyl 239 H 2,5-diF-phenyl 2-(N-piperazinyl-methyl)phenyl 240 H 2,5-diF-phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 241 H 2,5-diF-phenyl 2-(N-imidazolyl-methyl)phenyl 242 H 2,5-diF-phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 243 H 2,5-diF-phenyl 2-(N-pyridonyl-methyl)phenyl 244 H 2,5-diF-phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 245 H 2,5-diF-phenyl 2-(amidinyl)phenyl 246 H 2,5-diF-phenyl 2-(N-guanidinyl)phenyl 247 H 2,5-diF-phenyl 2-(imidazolyl)phenyl 248 H 2,5-diF-phenyl 2-(imidazolidinyl)phenyl 249 H 2,5-diF-phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 250 H 2,5-diF-phenyl 2-(2-pyrrolidinyl)phenyl 251 H 2,5-diF-phenyl 2-(2-piperidinyl)phenyl 252 H 2,5-diF-phenyl 2-(amidinyl-methyl)phenyl 253 H 2,5-diF-phenyl 2-(2-imidazolidinyl- methyl)phenyl 254 H 2,5-diF-phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 255 H 2,5-diF-phenyl 2-dimethylaminoimidazol-1-yl 256 H 2,5-diF-phenyl 2-(3-aminophenyl) 257 H 2,5-diF-phenyl 2-(3-pyrrolidinylcarbonyl) 258 H 2,5-diF-phenyl 2-glycinoyl 259 H 2,5-diF-phenyl 2-(imidazol-1-ylacetyl) 260 --CN phenyl 2-(aminosulfonyl)phenyl 261 --CN phenyl 2-(methylaminosulfonyl)phenyl 262 --CN phenyl 1-pyrrolidinocarbonyl 263 --CN phenyl 2-(methylsulfonyl)phenyl 264 --CN phenyl 4-morpholino 265 --CN phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 266 --CN phenyl 4-morpholinocarbonyl 267 --CN 2-pyridyl 2-(aminosulfonyl)phenyl 268 --CN 2-pyridyl 2-(methylaminosulfonyl)phenyl 269 --CN 2-pyridyl 1-pyrrolidinocarbonyl 270 --CN 2-pyridyl 2-(methylsulfonyl)phenyl 271 --CN 2-pyridyl 4-morpholino 272 --CN 2-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 273 --CN 2-pyridyl 4-morpholinocarbonyl 274 --CN 3-pyridyl 2-(aminosulfonyl)phenyl 275 --CN 3-pyridyl 2-(methylaminosulfonyl)phenyl 276 --CN 3-pyridyl 1-pyrrolidinocarbonyl 277 --CN 3-pyridyl 2-(methylsulfonyl)phenyl 278 --CN 3-pyridyl 4-morpholino 279 --CN 3-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 280 --CN 3-pyridyl 4-morpholinocarbonyl 281 --CN 2-pyrimidyl 2-(aminosulfonyl)phenyl 282 --CN 2-pyrimidyl 2-(methylaminosulfonyl)phenyl 283 --CN 2-pyrimidyl 1-pyrrolidinocarbonyl 284 --CN 2-pyrimidyl 2-(methylsulfonyl)phenyl 285 --CN 2-pyrimidyl 4-morpholino 286 --CN 2-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 287 --CN 2-pyrimidyl 4-morpholinocarbonyl 288 --CN 5-pyrimidyl 2-(aminosulfonyl)phenyl 289 --CN 5-pyrimidyl 2-(methylaminosulfonyl)phenyl 290 --CN 5-pyrimidyl 1-pyrrolidinocarbonyl 291 --CN 5-pyrimidyl 2-(methylsulfonyl)phenyl 292 --CN 5-pyrimidyl 4-morpholino 293 --CN 5-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 294 --CN 5-pyrimidyl 4-morpholinocarbonyl 295 --CN 2-Cl-phenyl 2-(aminosulfonyl)phenyl 296 --CN 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl 297 --CN 2-Cl-phenyl 1-pyrrolidinocarbonyl 298 --CN 2-Cl-phenyl 2-(methylsulfonyl)phenyl 299 --CN 2-Cl-phenyl 4-morpholino 300 --CN 2-Cl-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 301 --CN 2-Cl-phenyl 4-morpholinocarbonyl 302 --CN 2-F-phenyl 2-(aminosulfonyl)phenyl 303 --CN 2-F-phenyl 2-(methylaminosulfonyl)phenyl 304 --CN 2-F-phenyl 1-pyrrolidinocarbonyl 305 --CN 2-F-phenyl 2-(methylsulfonyl)phenyl 306 --CN 2-F-phenyl 4-morpholino 307 --CN 2-F-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 308 --CN 2-F-phenyl 4-morpholinocarbonyl 309 --CN 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 310 --CN 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl 311 --CN 2,5-diF-phenyl 1-pyrrolidinocarbonyl 312 --CN 2,5-diF-phenyl 2-(methylsulfonyl)phenyl 313 --CN 2,5-diF-phenyl 4-morpholino 314 --CN 2,5-diF-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 315 --CN 2,5-diF-phenyl 4-morpholinocarbonyl 316 --CN phenyl 2-(N-pyrrolidinyl-methyl)phenyl 317 --CN phenyl 2-(N-piperidinyl-methyl)phenyl 318 --CN phenyl 2-(N-morpholino-methyl)phenyl 319 --CN phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 320 --CN phenyl 2-(N-pyridinium-methyl)phenyl 321 --CN phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 322 --CN phenyl 2-(N-azatanyl-methyl)phenyl 323 --CN phenyl 2-(N-azetidinyl-methyl)phenyl 324 --CN phenyl 2-(N-piperazinyl-methyl)phenyl 325 --CN phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 326 --CN phenyl 2-(N-imidazolyl-methyl)phenyl 327 --CN phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 328 --CN phenyl 2-(N-pyridonyl-methyl)phenyl 329 --CN phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 330 --CN phenyl 2-(amidinyl)phenyl 331 --CN phenyl 2-(N-guanidinyl)phenyl 332 --CN phenyl 2-(imidazolyl)phenyl 333 --CN phenyl 2-(imidazolidinyl)phenyl 334 --CN phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 335 --CN phenyl 2-(2-pyrrolidinyl)phenyl 336 --CN phenyl 2-(2-piperidinyl)phenyl 337 --CN phenyl 2-(amidinyl-methyl)phenyl 338 --CN phenyl 2-(2-imidazolidinyl- methyl)phenyl 339 --CN phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 340 --CN phenyl 2-dimethylaminoimidazol-1-yl 341 --CN phenyl 2-(3-aminophenyl) 342 --CN phenyl 2-(3-pyrrolidinylcarbonyl) 343 --CN phenyl 2-glycinoyl 344 --CN phenyl 2-(imidazol-1-ylacetyl) 345 --CN 2-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl 346 --CN 2-pyridyl 2-(N-piperidinyl-methyl)phenyl 347 --CN 2-pyridyl 2-(N-morpholino-methyl)phenyl 348 --CN 2-pyridyl 2-(N,N'-methylmorpholinium- methyl)phenyl 349 --CN 2-pyridyl 2-(N-pyridinium-methyl)phenyl 350 --CN 2-pyridyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 351 --CN 2-pyridyl 2-(N-azatanyl-methyl)phenyl 352 --CN 2-pyridyl 2-(N-azetidinyl-methyl)phenyl 353 --CN 2-pyridyl 2-(N-piperazinyl-methyl)phenyl 354 --CN 2-pyridyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 355 --CN 2-pyridyl 2-(N-imidazolyl-methyl)phenyl 356 --CN 2-pyridyl 2-(N-methoxy-N-methylamino- methyl)phenyl 357 --CN 2-pyridyl 2-(N-pyridonyl-methyl)phenyl 358 --CN 2-pyridyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 359 --CN 2-pyridyl 2-(amidinyl)phenyl 360 --CN 2-pyridyl 2-(N-guanidinyl)phenyl 361 --CN 2-pyridyl 2-(imidazolyl)phenyl 362 --CN 2-pyridyl 2-(imidazolidinyl)phenyl 363 --CN 2-pyridyl 2-(2-imidazolidinyl- sulfonyl)phenyl 364 --CN 2-pyridyl 2-(2-pyrrolidinyl)phenyl 365 --CN 2-pyridyl 2-(2-piperidinyl)phenyl 366 --CN 2-pyridyl 2-(amidinyl-methyl)phenyl 367 --CN 2-pyridyl 2-(2-imidazolidinyl- methyl)phenyl 368 --CN 2-pyridyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 369 --CN 2-pyridyl 2-dimethylaminoimidazol-1-yl 370 --CN 2-pyridyl 2-(3-aminophenyl) 371 --CN 2-pyridyl 2-(3-pyrrolidinylcarbonyl) 372 --CN 2-pyridyl 2-glycinoyl 373 --CN 2-pyridyl 2-(imidazol-1-ylacetyl) 374 --CN 3-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl 375 --CN 3-pyridyl 2-(N-piperidinyl-methyl)phenyl 376 --CN 3-pyridyl 2-(N-morpholino-methyl)phenyl 377 --CN 3-pyridyl 2-(N,N'-methylmorpholinium- methyl)phenyl 378 --CN 3-pyridyl 2-(N-pyridinium-methyl)phenyl 379 --CN 3-pyridyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 380 --CN 3-pyridyl 2-(N-azatanyl-methyl)phenyl 381 --CN 3-pyridyl 2-(N-azetidinyl-methyl)phenyl 382 --CN 3-pyridyl 2-(N-piperazinyl-methyl)phenyl 383 --CN 3-pyridyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 384 --CN 3-pyridyl 2-(N-imidazolyl-methyl)phenyl 385 --CN 3-pyridyl 2-(N-methoxy-N-methylamino- methyl)phenyl 386 --CN 3-pyridyl 2-(N-pyridonyl-methyl)phenyl 387 --CN 3-pyridyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 388 --CN 3-pyridyl 2-(amidinyl)phenyl 389 --CN 3-pyridyl 2-(N-guanidinyl)phenyl 390 --CN 3-pyridyl 2-(imidazolyl)phenyl 391 --CN 3-pyridyl 2-(imidazolidinyl)phenyl 392 --CN 3-pyridyl 2-(2-imidazolidinyl- sulfonyl)phenyl 393 --CN 3-pyridyl 2-(2-pyrrolidinyl)phenyl 394 --CN 3-pyridyl 2-(2-piperidinyl)phenyl 395 --CN 3-pyridyl 2-(amidinyl-methyl)phenyl 396 --CN 3-pyridyl 2-(2-imidazolidinyl- methyl)phenyl 397 --CN 3-pyridyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 398 --CN 3-pyridyl 2-dimethylaminoimidazol-1-yl 399 --CN 3-pyridyl 2-(3-aminophenyl) 400 --CN 3-pyridyl 2-(3-pyrrolidinylcarbonyl) 401 --CN 3-pyridyl 2-glycinoyl 402 --CN 3-pyridyl 2-(imidazol-1-ylacetyl) 403 --CN 2-pyrimidyl 2-(N-pyrrolidinyl-methyl)phenyl 404 --CN 2-pyrimidyl 2-(N-piperidinyl-methyl)phenyl 405 --CN 2-pyrimidyl 2-(N-morpholino-methyl)phenyl 406 --CN 2-pyrimidyl 2-(N,N'-methylmorpholinium- methyl)phenyl 407 --CN 2-pyrimidyl 2-(N-pyridinium-methyl)phenyl 408 --CN 2-pyrimidyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 409 --CN 2-pyrimidyl 2-(N-azatanyl-methyl)phenyl 410 --CN 2-pyrimidyl 2-(N-azetidinyl-methyl)phenyl 411 --CN 2-pyrimidyl 2-(N-piperazinyl-methyl)phenyl 412 --CN 2-pyrimidyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 413 --CN 2-pyrimidyl 2-(N-imidazolyl-methyl)phenyl 414 --CN 2-pyrimidyl 2-(N-methoxy-N-methylamino- methyl)phenyl 415 --CN 2-pyrimidyl 2-(N-pyridonyl-methyl)phenyl 416 --CN 2-pyrimidyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 417 --CN 2-pyrimidyl 2-(amidinyl)phenyl 418 --CN 2-pyrimidyl 2-(N-guanidinyl)phenyl 419 --CN 2-pyrimidyl 2-(imidazolyl)phenyl 420 --CN 2-pyrimidyl 2-(imidazolidinyl)phenyl 421 --CN 2-pyrimidyl 2-(2-imidazolidinyl- sulfonyl)phenyl 422 --CN 2-pyrimidyl 2-(2-pyrrolidinyl)phenyl 423 --CN 2-pyrimidyl 2-(2-piperidinyl)phenyl 424 --CN 2-pyrimidyl 2-(amidinyl-methyl)phenyl 425 --CN 2-pyrimidyl 2-(2-imidazolidinyl- methyl)phenyl 426 --CN 2-pyrimidyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 427 --CN 2-pyrimidyl 2-dimethylaminoimidazol-1-yl 428 --CN 2-pyrimidyl 2-(3-aminophenyl) 429 --CN 2-pyrimidyl 2-(3-pyrrolidinylcarbonyl) 430 --CN 2-pyrimidyl 2-glycinoyl 431 --CN 2-pyrimidyl 2-(imidazol-1-ylacetyl) 432 --CN 2-Cl-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 433 --CN 2-Cl-phenyl 2-(N-piperidinyl-methyl)phenyl 434 --CN 2-Cl-phenyl 2-(N-morpholino-methyl)phenyl 435 --CN 2-Cl-phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 436 --CN 2-Cl-phenyl 2-(N-pyridinium-methyl)phenyl 437 --CN 2-Cl-phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 438 --CN 2-Cl-phenyl 2-(N-azatanyl-methyl)phenyl 439 --CN 2-Cl-phenyl 2-(N-azetidinyl-methyl)phenyl 440 --CN 2-Cl-phenyl 2-(N-piperazinyl-methyl)phenyl 441 --CN 2-Cl-phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 442 --CN 2-Cl-phenyl 2-(N-imidazolyl-methyl)phenyl 443 --CN 2-Cl-phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 444 --CN 2-Cl-phenyl 2-(N-pyridonyl-methyl)phenyl 445 --CN 2-Cl-phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 446 --CN 2-Cl-phenyl 2-(amidinyl)phenyl 447 --CN 2-Cl-phenyl 2-(N-guanidinyl)phenyl 448 --CN 2-Cl-phenyl 2-(imidazolyl)phenyl 449 --CN 2-Cl-phenyl 2-(imidazolidinyl)phenyl 450 --CN 2-Cl-phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 451 --CN 2-Cl-phenyl 2-(2-pyrrolidinyl)phenyl 452 --CN 2-Cl-phenyl 2-(2-piperidinyl)phenyl 453 --CN 2-Cl-phenyl 2-(amidinyl-methyl)phenyl 454 --CN 2-Cl-phenyl 2-(2-imidazolidinyl- methyl)phenyl 455 --CN 2-Cl-phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 456 --CN 2-Cl-phenyl 2-dimethylaminoimidazol-1-yl 457 --CN 2-Cl-phenyl 2-(3-aminophenyl) 458 --CN 2-Cl-phenyl 2-(3-pyrrolidinylcarbonyl) 459 --CN 2-Cl-phenyl 2-glycinoyl 460 --CN 2-Cl-phenyl 2-(imidazol-1-ylacetyl) 461 --CN 2-F-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 462 --CN 2-F-phenyl 2-(N-piperidinyl-methyl)phenyl 463 --CN 2-F-phenyl 2-(N-morpholino-methyl)phenyl 464 --CN 2-F-phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 465 --CN 2-F-phenyl 2-(N-pyridinium-methyl)phenyl 466 --CN 2-F-phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 467 --CN 2-F-phenyl 2-(N-azatanyl-methyl)phenyl 468 --CN 2-F-phenyl 2-(N-azetidinyl-methyl)phenyl 469 --CN 2-F-phenyl 2-(N-piperazinyl-methyl)phenyl 470 --CN 2-F-phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 471 --CN 2-F-phenyl 2-(N-imidazolyl-methyl)phenyl 472 --CN 2-F-phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 473 --CN 2-F-phenyl 2-(N-pyridonyl-methyl)phenyl 474 --CN 2-F-phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 475 --CN 2-F-phenyl 2-(amidinyl)phenyl 476 --CN 2-F-phenyl 2-(N-guanidinyl)phenyl 477 --CN 2-F-phenyl 2-(imidazolyl)phenyl 478 --CN 2-F-phenyl 2-(imidazolidinyl)phenyl 479 --CN 2-F-phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 480 --CN 2-F-phenyl 2-(2-pyrrolidinyl)phenyl 481 --CN 2-F-phenyl 2-(2-piperidinyl)phenyl 482 --CN 2-F-phenyl 2-(amidinyl-methyl)phenyl 483 --CN 2-F-phenyl 2-(2-imidazolidinyl- methyl)phenyl 484 --CN 2-F-phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 485 --CN 2-F-phenyl 2-dimethylaminoimidazol-1-yl 486 --CN 2-F-phenyl 2-(3-aminophenyl) 487 --CN 2-F-phenyl 2-(3-pyrrolidinylcarbonyl) 488 --CN 2-F-phenyl 2-glycinoyl 489 --CN 2-F-phenyl 2-(imidazol-1-ylacetyl) 490 --CN 2,5-diF-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 491 --CN 2,5-diF-phenyl 2-(N-piperidinyl-methyl)phenyl 492 --CN 2,5-diF-phenyl 2-(N-morpholino-methyl)phenyl 493 --CN 2,5-diF-phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 494 --CN 2,5-diF-phenyl 2-(N-pyridinium-methyl)phenyl 495 --CN 2,5-diF-phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 496 --CN 2,5-diF-phenyl 2-(N-azatanyl-methyl)phenyl 497 --CN 2,5-diF-phenyl 2-(N-azetidinyl-methyl)phenyl 498 --CN 2,5-diF-phenyl 2-(N-piperazinyl-methyl)phenyl 499 --CN 2,5-diF-phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 500 --CN 2,5-diF-phenyl 2-(N-imidazolyl-methyl)phenyl 501 --CN 2,5-diF-phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 502 --CN 2,5-diF-phenyl 2-(N-pyridonyl-methyl)phenyl 503 --CN 2,5-diF-phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 504 --CN 2,5-diF-phenyl 2-(amidinyl)phenyl 505 --CN 2,5-diF-phenyl 2-(N-guanidinyl)phenyl 506 --CN 2,5-diF-phenyl 2-(imidazolyl)phenyl 507 --CN 2,5-diF-phenyl 2-(imidazolidinyl)phenyl 508 --CN 2,5-diF-phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 509 --CN 2,5-diF-phenyl 2-(2-pyrrolidinyl)phenyl 510 --CN 2,5-diF-phenyl 2-(2-piperidinyl)phenyl 511 --CN 2,5-diF-phenyl 2-(amidinyl-methyl)phenyl 512 --CN 2,5-diF-phenyl 2-(2-imidazolidinyl- methyl)phenyl 513 --CN 2,5-diF-phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 514 --CN 2,5-diF-phenyl 2-dimethylaminoimidazol-1-yl 515 --CN 2,5-diF-phenyl 2-(3-aminophenyl) 516 --CN 2,5-diF-phenyl 2-(3-pyrrolidinylcarbonyl) 517 --CN 2,5-diF-phenyl 2-glycinoyl 518 --CN 2,5-diF-phenyl 2-(imidazol-1-ylacetyl) 519 CF.sub.3 phenyl 2-(aminosulfonyl)phenyl 520 CF.sub.3 phenyl 2-(methylaminosulfonyl)phenyl 521 CF.sub.3 phenyl 1-pyrrolidinocarbonyl 522 CF.sub.3 phenyl 2-(methylsulfonyl)phenyl 523 CF.sub.3 phenyl 4-morpholino 524 CF.sub.3 phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 525 CF.sub.3 phenyl 4-morpholinocarbonyl 526 CF.sub.3 2-pyridyl 2-(aminosulfonyl)phenyl 527 CF.sub.3 2-pyridyl 2-(methylaminosulfonyl)phenyl 528 CF.sub.3 2-pyridyl 1-pyrrolidinocarbonyl 529 CF.sub.3 2-pyridyl 2-(methylsulfonyl)phenyl 530 CF.sub.3 2-pyridyl 4-morpholino 531 CF.sub.3 2-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 532 CF.sub.3 2-pyridyl 4-morpholinocarbonyl 533 CF.sub.3 3-pyridyl 2-(aminosulfonyl)phenyl 534 CF.sub.3 3-pyridyl 2-(methylaminosulfonyl)phenyl 535 CF.sub.3 3-pyridyl 1-pyrrolidinocarbonyl 536 CF.sub.3 3-pyridyl 2-(methylsulfonyl)phenyl 537 CF.sub.3 3-pyridyl 4-morpholino 538 CF.sub.3 3-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 539 CF.sub.3 3-pyridyl 4-morpholinocarbonyl 540 CF.sub.3 2-pyrimidyl 2-(aminosulfonyl)phenyl 541 CF.sub.3 2-pyrimidyl 2-(methylaminosulfonyl)phenyl 542 CF.sub.3 2-pyrimidyl 1-pyrrolidinocarbonyl 543 CF.sub.3 2-pyrimidyl 2-(methylsulfonyl)phenyl 544 CF.sub.3 2-pyrimidyl 4-morpholino 545 CF.sub.3 2-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 546 CF.sub.3 2-pyrimidyl 4-morpholinocarbonyl 547 CF.sub.3 5-pyrimidyl 2-(aminosulfonyl)phenyl 548 CF.sub.3 5-pyrimidyl 2-(methylaminosulfonyl)phenyl 549 CF.sub.3 5-pyrimidyl 1-pyrrolidinocarbonyl 550 CF.sub.3 5-pyrimidyl 2-(methylsulfonyl)phenyl 551 CF.sub.3 5-pyrimidyl 4-morpholino 552 CF.sub.3 5-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 553 CF.sub.3 5-pyrimidyl 4-morpholinocarbonyl 554 CF.sub.3 2-Cl-phenyl 2-(aminosulfonyl)phenyl 555 CF.sub.3 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl 556 CF.sub.3 2-Cl-phenyl 1-pyrrolidinocarbonyl 557 CF.sub.3 2-Cl-phenyl 2-(methylsulfonyl)phenyl 558 CF.sub.3 2-Cl-phenyl 4-morpholino 559 CF.sub.3 2-Cl-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 560 CF.sub.3 2-Cl-phenyl 4-morpholinocarbonyl 561 CF.sub.3 2-F-phenyl 2-(aminosulfonyl)phenyl 562 CF.sub.3 2-F-phenyl 2-(methylaminosulfonyl)phenyl 563 CF.sub.3 2-F-phenyl 1-pyrrolidinocarbonyl 564 CF.sub.3 2-F-phenyl 2-(methylsulfonyl)phenyl 565 CF.sub.3 2-F-phenyl 4-morpholino 566 CF.sub.3 2-F-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 567 CF.sub.3 2-F-phenyl 4-morpholinocarbonyl 568 CF.sub.3 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 569 CF.sub.3 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl 570 CF.sub.3 2,5-diF-phenyl 1-pyrrolidinocarbonyl 571 CF.sub.3 2,5-diF-phenyl 2-(methylsulfonyl)phenyl 572 CF.sub.3 2,5-diF-phenyl 4-morpholino 573 CF.sub.3 2,5-diF-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 574 CF.sub.3 2,5-diF-phenyl 4-morpholinocarbon yl 575 CF.sub.3 phenyl 2-(N-pyrrolidinyl-methyl)phenyl 576 CF.sub.3 phenyl 2-(N-piperidinyl-methyl)phenyl 577 CF.sub.3 phenyl 2-(N-morpholino-methyl)phenyl 578 CF.sub.3 phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 579 CF.sub.3 phenyl 2-(N-pyridinium-methyl)phenyl 580 CF.sub.3 phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 581 CF.sub.3 phenyl 2-(N-azatanyl-methyl)phenyl 582 CF.sub.3 phenyl 2-(N-azetidinyl-methyl)phenyl 583 CF.sub.3 phenyl 2-(N-piperazinyl-methyl)phenyl 584 CF.sub.3 phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 585 CF.sub.3 phenyl 2-(N-imidazolyl-methyl)phenyl 586 CF.sub.3 phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 587 CF.sub.3 phenyl 2-(N-pyridonyl-methyl)phenyl 588 CF.sub.3 phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 589 CF.sub.3 phenyl 2-(amidinyl)phenyl 590 CF.sub.3 phenyl 2-(N-guanidinyl)phenyl 591 CF.sub.3 phenyl 2-(imidazolyl)phenyl 592 CF.sub.3 phenyl 2-(imidazolidinyl)phenyl 593 CF.sub.3 phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 594 CF.sub.3 phenyl 2-(2-pyrrolidinyl)phenyl 595 CF.sub.3 phenyl 2-(2-piperidinyl)phenyl 596 CF.sub.3 phenyl 2-(amidinyl-methyl)phenyl 597 CF.sub.3 phenyl 2-(2-imidazolidinyl- methyl)phenyl 598 CF.sub.3 phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 599 CF.sub.3 phenyl 2-dimethylaminoimidazol-1-yl 600 CF.sub.3 phenyl 2-(3-aminophenyl) 601 CF.sub.3 phenyl 2-(3-pyrrolidinylcarbonyl) 602 CF.sub.3 phenyl 2-glycinoyl 603 CF.sub.3 phenyl 2-(imidazol-1-ylacetyl) 604 CF.sub.3 2-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl 605 CF.sub.3 2-pyridyl 2-(N-piperidinyl-methyl)phenyl 606 CF.sub.3 2-pyridyl 2-(N-morpholino-methyl)phenyl 607 CF.sub.3 2-pyridyl 2-(N,N'-methylmorpholinium- methyl)phenyl 608 CF.sub.3 2-pyridyl 2-(N-pyridinium-methyl)phenyl 609 CF.sub.3 2-pyridyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 610 CF.sub.3 2-pyridyl 2-(N-azatanyl-methyl)phenyl 611 CF.sub.3 2-pyridyl 2-(N-azetidinyl-methyl)phenyl 612 CF.sub.3 2-pyridyl 2-(N-piperazinyl-methyl)phenyl 613 CF.sub.3 2-pyridyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 614 CF.sub.3 2-pyridyl 2-(N-imidazolyl-methyl)phenyl 615 CF.sub.3 2-pyridyl 2-(N-methoxy-N-methylamino- methyl)phenyl 616 CF.sub.3 2-pyridyl 2-(N-pyridonyl-methyl)phenyl 617 CF.sub.3 2-pyridyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 618 CF.sub.3 2-pyridyl 2-(amidinyl)phenyl 619 CF.sub.3 2-pyridyl 2-(N-guanidinyl)phenyl 620 CF.sub.3 2-pyridyl 2-(imidazolyl)phenyl 621 CF.sub.3 2-pyridyl 2-(imidazolidinyl)phenyl 622 CF.sub.3 2-pyridyl 2-(2-imidazolidinyl- sulfonyl)phenyl 623 CF.sub.3 2-pyridyl 2-(2-pyrrolidinyl)phenyl 624 CF.sub.3 2-pyridyl 2-(2-piperidinyl)phenyl 625 CF.sub.3 2-pyridyl 2-(amidinyl-methyl)phenyl 626 CF.sub.3 2-pyridyl 2-(2-imidazolidinyl- methyl)phenyl 627 CF.sub.3 2-pyridyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 628 CF.sub.3 2-pyridyl 2-dimethylaminoimidazol-1-yl 629 CF.sub.3 2-pyridyl 2-(3-aminophenyl) 630 CF.sub.3 2-pyridyl 2-(3-pyrrolidinylcarbonyl) 631 CF.sub.3 2-pyridyl 2-glycinoyl 632 CF.sub.3 2-pyridyl 2-(imidazol-1-ylacetyl) 633 CF.sub.3 3-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl 634 CF.sub.3 3-pyridyl 2-(N-piperidinyl-methyl)phenyl 635 CF.sub.3 3-pyridyl 2-(N-morpholino-methyl)phenyl 636 CF.sub.3 3-pyridyl 2-(N,N'-methylmorpholinium- methyl)phenyl 637 CF.sub.3 3-pyridyl 2-(N-pyridinium-methyl)phenyl 638 CF.sub.3 3-pyridyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 639 CF.sub.3 3-pyridyl 2-(N-azatanyl-methyl)phenyl 640 CF.sub.3 3-pyridyl 2-(N-azetidinyl-methyl)phenyl 641 CF.sub.3 3-pyridyl 2-(N-piperazinyl-methyl)phenyl 642 CF.sub.3 3-pyridyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 643 CF.sub.3 3-pyridyl 2-(N-imidazolyl-methyl)phenyl 644 CF.sub.3 3-pyridyl 2-(N-methoxy-N-methylamino- methyl)phenyl 645 CF.sub.3 3-pyridyl 2-(N-pyridonyl-methyl)phenyl 646 CF.sub.3 3-pyridyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 647 CF.sub.3 3-pyridyl 2-(amidinyl)phenyl 648 CF.sub.3 3-pyridyl 2-(N-guanidinyl)phenyl 649 CF.sub.3 3-pyridyl 2-(imidazolyl)phenyl 650 CF.sub.3 3-pyridyl 2-(imidazolidinyl)phenyl 651 CF.sub.3 3-pyridyl 2-(2-imidazolidinyl- sulfonyl)phenyl 652 CF.sub.3 3-pyridyl 2-(2-pyrrolidinyl)phenyl 653 CF.sub.3 3-pyridyl 2-(2-piperidinyl)phenyl 654 CF.sub.3 3-pyridyl 2-(amidinyl-methyl)phenyl 655 CF.sub.3 3-pyridyl 2-(2-imidazolidinyl- methyl)phenyl 656 CF.sub.3 3-pyridyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 657 CF.sub.3 3-pyridyl 2-dimethylaminoimidazol-1-yl 658 CF.sub.3 3-pyridyl 2-(3-aminophenyl) 659 CF.sub.3 3-pyridyl 2-(3-pyrrolidinylcarbonyl) 660 CF.sub.3 3-pyridyl 2-glycinoyl 661 CF.sub.3 3-pyridyl 2-(imidazol-1-ylacetyl) 662 CF.sub.3 2-pyrimidyl 2-(N-pyrrolidinyl-methyl)phenyl 663 CF.sub.3 2-pyrimidyl 2-(N-piperidinyl-methyl)phenyl 664 CF.sub.3 2-pyrimidyl 2-(N-morpholino-methyl)phenyl 665 CF.sub.3 2-pyrimidyl 2-(N,N'-methylmorpholinium- methyl)phenyl 666 CF.sub.3 2-pyrimidyl 2-(N-pyridinium-methyl)phenyl 667 CF.sub.3 2-pyrimidyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 668 CF.sub.3 2-pyrimidyl 2-(N-azatanyl-methyl)phenyl 669 CF.sub.3 2-pyrimidyl 2-(N-azetidinyl-methyl)phenyl 670 CF.sub.3 2-pyrimidyl 2-(N-piperazinyl-methyl)phenyl 671 CF.sub.3 2-pyrimidyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 672 CF.sub.3 2-pyrimidyl 2-(N-imidazolyl-methyl)phenyl 673 CF.sub.3 2-pyrimidyl 2-(N-methoxy-N-methylamino- methyl)phenyl 674 CF.sub.3 2-pyrimidyl 2-(N-pyridonyl-methyl)phenyl 675 CF.sub.3 2-pyrimidyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 676 CF.sub.3 2-pyrimidyl 2-(amidinyl)phenyl 677 CF.sub.3 2-pyrimidyl 2-(N-guanidinyl)phenyl 678 CF.sub.3 2-pyrimidyl 2-(imidazolyl)phenyl 679 CF.sub.3 2-pyrimidyl 2-(imidazolidinyl)phenyl 680 CF.sub.3 2-pyrimidyl 2-(2-imidazolidinyl- sulfonyl)phenyl 681 CF.sub.3 2-pyrimidyl 2-(2-pyrrolidinyl)phenyl 682 CF.sub.3 2-pyrimidyl 2-(2-piperidinyl)phenyl 683 CF.sub.3 2-pyrimidyl 2-(amidinyl-methyl)phenyl 684 CF.sub.3 2-pyrimidyl 2-(2-imidazolidinyl- methyl)phenyl 685 CF.sub.3 2-pyrimidyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 686 CF.sub.3 2-pyrimidyl 2-dimethylaminoimidazol-1-yl 687 CF.sub.3 2-pyrimidyl 2-(3-aminophenyl) 688 CF.sub.3 2-pyrimidyl 2-(3-pyrrolidinylcarbonyl) 689 CF.sub.3 2-pyrimidyl 2-glycinoyl 690 CF.sub.3 2-pyrimidyl 2-(imidazol-1-ylacetyl) 691 CF.sub.3 2-Cl-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 692 CF.sub.3 2-Cl-phenyl 2-(N-piperidinyl-methyl)phenyl 693 CF.sub.3 2-Cl-phenyl 2-(N-morpholino-methyl)phenyl 694 CF.sub.3 2-Cl-phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 695 CF.sub.3 2-Cl-phenyl 2-(N-pyridinium-methyl)phenyl 696 CF.sub.3 2-Cl-phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 697 CF.sub.3 2-Cl-phenyl 2-(N-azatanyl-methyl)phenyl 698 CF.sub.3 2-Cl-phenyl 2-(N-azetidinyl-methyl)phenyl 699 CF.sub.3 2-Cl-phenyl 2-(N-piperazinyl-methyl)phenyl 700 CF.sub.3 2-Cl-phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 701 CF.sub.3 2-Cl-phenyl 2-(N-imidazolyl-methyl)phenyl 702 CF.sub.3 2-Cl-phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 703 CF.sub.3 2-Cl-phenyl 2-(N-pyridonyl-methyl)phenyl 704 CF.sub.3 2-Cl-phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 705 CF.sub.3 2-Cl-phenyl 2-(amidinyl)phenyl 706 CF.sub.3 2-Cl-phenyl 2-(N-guanidinyl)phenyl 707 CF.sub.3 2-Cl-phenyl 2-(imidazolyl)phenyl 708 CF.sub.3 2-Cl-phenyl 2-(imidazolidinyl)phenyl 709 CF.sub.3 2-Cl-phenyl 2-(2-imidazolidinyl- sultonyl)phenyl 710 CF.sub.3 2-Cl-phenyl 2-(2-pyrrolidinyl)phenyl 711 CF.sub.3 2-Cl-phenyl 2-(2-piperidinyl)phenyl 712 CF.sub.3 2-Cl-phenyl 2-(amidinyl-methyl)phenyl 713 CF.sub.3 2-Cl-phenyl 2-(2-imidazolidinyl- methyl)phenyl 714 CF.sub.3 2-Cl-phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 715 CF.sub.3 2-Cl-phenyl 2-dimethylaminoimidazol-1-yl 716 CF.sub.3 2-Cl-phenyl 2-(3-aminophenyl) 717 CF.sub.3 2-Cl-phenyl 2-(3-pyrrolidinylcarbonyl) 718 CF.sub.3 2-Cl-phenyl 2-glycinoyl 719 CF.sub.3 2-Cl-phenyl 2-(imidazol-1-ylacetyl) 720 CF.sub.3 2-F-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 721 CF.sub.3 2-F-phenyl 2-(N-piperidinyl-methyl)phenyl 722 CF.sub.3 2-F-phenyl 2-(N-morpholino-methyl)phenyl 723 CF.sub.3 2-F-phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 724 CF.sub.3 2-F-phenyl 2-(N-pyridinium-methyl)phenyl 725 CF.sub.3 2-F-phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 726 CF.sub.3 2-F-phenyl 2-(N-azatanyl-methyl)phenyl 727 CF.sub.3 2-F-phenyl 2-(N-azetidinyl-methyl)phenyl 728 CF.sub.3 2-F-phenyl 2-(N-piperazinyl-methyl)phenyl 729 CF.sub.3 2-F-phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 730 CF.sub.3 2-F-phenyl 2-(N-imidazolyl-methyl)phenyl 731 CF.sub.3 2-F-phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 732 CF.sub.3 2-F-phenyl 2-(N-pyridonyl-methyl)phenyl 733 CF.sub.3 2-F-phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 734 CF.sub.3 2-F-phenyl 2-(amidinyl)phenyl 735 CF.sub.3 2-F-phenyl 2-(N-guanidinyl)phenyl 736 CF.sub.3 2-F-phenyl 2-(imidazolyl)phenyl 737 CF.sub.3 2-F-phenyl 2-(imidazolidinyl)phenyl 738 CF.sub.3 2-F-phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 739 CF.sub.3 2-F-phenyl 2-(2-pyrrolidinyl)phenyl 740 CF.sub.3 2-F-phenyl 2-(2-piperidinyl)phenyl 741 CF.sub.3 2-F-phenyl 2-(amidinyl-methyl)phenyl 742 CF.sub.3 2-F-phenyl 2-(2-imidazolidinyl- methyl)phenyl 743 CF.sub.3 2-F-phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 744 CF.sub.3 2-F-phenyl 2-dimethylaminoimidazol-1-yl 745 CF.sub.3 2-F-phenyl 2-(3-aminophenyl) 746 CF.sub.3 2-F-phenyl 2-(3-pyrrolidinylcarbonyl) 747 CF.sub.3 2-F-phenyl 2-glycinoyl 748 CF.sub.3 2-F-phenyl 2-(imidazol-1-ylacetyl) 749 CF.sub.3 2,5-diF-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 750 CF.sub.3 2,5-diF-phenyl 2-(N-piperidinyl-methyl)phenyl 751 CF.sub.3 2,5-diF-phenyl 2-(N-morpholino-methyl)phenyl 752 CF.sub.3 2,5-diF-phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 753 CF.sub.3 2,5-diF-phenyl 2-(N-pyridinium-methyl)phenyl 754 CF.sub.3 2,5-diF-phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 755 CF.sub.3 2,5-diF-phenyl 2-(N-azatanyl-methyl)phenyl 756 CF.sub.3 2,5-diF-phenyl 2-(N-azetidinyl-methyl)phenyl 757 CF.sub.3 2,5-diF-phenyl 2-(N-piperazinyl-methyl)phenyl 758 CF.sub.3 2,5-diF-phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 759 CF.sub.3 2,5-diF-phenyl 2-(N-imidazolyl-methyl)phenyl 760 CF.sub.3 2,5-diF-phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 761 CF.sub.3 2,5-diF-phenyl 2-(N-pyridonyl-methyl)phenyl 762 CF.sub.3 2,5-diF-phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 763 CF.sub.3 2,5-diF-phenyl 2-(amidinyl)phenyl 764 CF.sub.3 2,5-diF-phenyl 2-(N-guanidinyl)phenyl 765 CF.sub.3 2,5-diF-phenyl 2-(imidazolyl)phenyl 766 CF.sub.3 2,5-diF-phenyl 2-(imidazolidinyl)phenyl 767 CF.sub.3 2,5-diF-phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 768 CF.sub.3 2,5-diF-phenyl 2-(2-pyrrolidinyl)phenyl 769 CF.sub.3 2,5-diF-phenyl 2-(2-piperidinyl)phenyl 770 CF.sub.3 2,5-diF-phenyl 2-(amidinyl-methyl)phenyl 771 CF.sub.3 2,5-diF-phenyl 2-(2-imidazolidinyl- methyl)phenyl 772 CF.sub.3 2,5-diF-phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 773 CF.sub.3 2,5-diF-phenyl 2-dimethylaminoimidazol-1-yl 774 CF.sub.3 2,5-diF-phenyl 2-(3-aminophenyl) 775 CF.sub.3 2,5-diF-phenyl 2-(3-pyrrolidinylcarbonyl) 776 CF.sub.3 2,5-diF-phenyl 2-glycinoyl 777 CF.sub.3 2,5-diF-phenyl 2-(imidazol-1-ylacetyl) 778 CONH.sub.2 phenyl 2-(aminosulfonyl)phenyl 779 CONH.sub.2 phenyl 2-(methylaminosulfonyl)phenyl 780 CONH.sub.2 phenyl 1-pyrrolidinocarbonyl 781 CONH.sub.2 phenyl 2-(methylsulfonyl)phenyl 782 CONH.sub.2 phenyl 4-morpholino 783 CONH.sub.2 phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 784 CONH.sub.2 phenyl 4-morpholinocarbonyl 785 CONH.sub.2 2-pyridyl 2-(aminosulfonyl)phenyl 786 CONH.sub.2 2-pyridyl 2-(methylaminosulfonyl)phenyl 787 CONH.sub.2 2-pyridyl 1-pyrrolidinocarbonyl 788 CONH.sub.2 2-pyridyl 2-(methylsulfonyl)phenyl 789 CONH.sub.2 2-pyridyl 4-morpholino 790 CONH.sub.2 2-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 791 CONH.sub.2 2-pyridyl 4-morpholinocarbonyl 792 CONH.sub.2 3-pyridyl 2-(aminosulfonyl)phenyl 793 CONH.sub.2 3-pyridyl 2-(methylaminosulfonyl)phenyl 794 CONH.sub.2 3-pyridyl 1-pyrrolidinocarbonyl 795 CONH.sub.2 3-pyridyl 2-(methylsulfonyl)phenyl 796 CONH.sub.2 3-pyridyl 4-morpholino 797 CONH.sub.2 3-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 798 CONH.sub.2 3-pyridyl 4-morpholinocarbonyl 799 CONH.sub.2 2-pyrimidyl 2-(aminosulfonyl)phenyl 800 CONH.sub.2 2-pyrimidyl 2-(methylaminosulfonyl)phenyl 801 CONH.sub.2 2-pyrimidyl 1-pyrrolidinocarbonyl 802 CONH.sub.2 2-pyrimidyl 2-(methylsulfonyl)phenyl 803 CONH.sub.2 2-pyrimidyl 4-morpholino 804 CONH.sub.2 2-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 805 CONH.sub.2 2-pyrimidyl 4-morpholinocarbonyl 806 CONH.sub.2 5-pyrimidyl 2-(aminosulfonyl)phenyl 807 CONH.sub.2 5-pyrimidyl 2-(methylaminosulfonyl)phenyl 808 CONH.sub.2 5-pyrimidyl 1-pyrrolidinocarbonyl 809 CONH.sub.2 5-pyrimidyl 2-(methylsulfonyl)phenyl 810 CONH.sub.2 5-pyrimidyl 4-morpholino 811 CONH.sub.2 5-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 812 CONH.sub.2 5-pyrimidyl 4-morpholinocarbonyl 813 CONH.sub.2 2-Cl-phenyl 2-(aminosulfonyl)phenyl 814 CONH.sub.2 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl 815 CONH.sub.2 2-Cl-phenyl 1-pyrrolidinocarbonyl 816 CONH.sub.2 2-Cl-phenyl 2-(methylsulfonyl)phenyl 817 CONH.sub.2 2-Cl-phenyl 4-morpholino 818 CONH.sub.2 2-Cl-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 819 CONH.sub.2 2-Cl-phenyl 4-morpholinocarbonyl 820 CONH.sub.2 2-F-phenyl 2-(aminosulfonyl)phenyl 821 CONH.sub.2 2-F-phenyl 2-(methylaminosulfonyl)phenyl 822 CONH.sub.2 2-F-phenyl 1-pyrrolidinocarbonyl 823 CONH.sub.2 2-F-phenyl 2-(methylsulfonyl)phenyl 824 CONH.sub.2 2-F-phenyl 4-morpholino 825 CONH.sub.2 2-F-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 826 CONH.sub.2 2-F-phenyl 4-morpholinocarbonyl 827 CONH.sub.2 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 828 CONH.sub.2 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl 829 CONH.sub.2 2,5-diF-phenyl 1-pyrrolidinocarbonyl 830 CONH.sub.2 2,5-diF-phenyl 2-(methylsulfonyl)phenyl831 CONH.sub.2 2,5-diF-phenyl 4-morpholino 832 CONH.sub.2 2,5-diF-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 833 CONH.sub.2 2,5-diF-phenyl 4-morpholinocarbo nyl 834 CONH.sub.2 phenyl 2-(N-pyrrolidinyl-methyl)phenyl 835 CONH.sub.2 phenyl 2-(N-piperidinyl-methyl)phenyl 836 CONH.sub.2 phenyl 2-(N-morpholino-methyl)phenyl 837 CONH.sub.2 phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 838 CONH.sub.2 phenyl 2-(N-pyridinium-methyl)phenyl 839 CONH.sub.2 phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 840 CONH.sub.2 phenyl 2-(N-azatanyl-methyl)phenyl 841 CONH.sub.2 phenyl 2-(N-azetidinyl-methyl)phenyl 842 CONH.sub.2 phenyl 2-(N-piperazinyl-methyl)phenyl 843 CONH.sub.2 phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 844 CONH.sub.2 phenyl 2-(N-imidazolyl-methyl)phenyl 845 CONH.sub.2 phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 846 CONH.sub.2 phenyl 2-(N-pyridonyl-methyl)phenyl 847 CONH.sub.2 phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 848 CONH.sub.2 phenyl 2-(amidinyl)phenyl 849 CONH.sub.2 phenyl 2-(N-guanidinyl)phenyl 850 CONH.sub.2 phenyl 2-(imidazolyl)phenyl 851 CONH.sub.2 phenyl 2-(imidazolidinyl)phenyl 852 CONH.sub.2 phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 853 CONH.sub.2 phenyl 2-(2-pyrrolidinyl)phenyl 854 CONH.sub.2 phenyl 2-(2-piperidinyl)phenyl 855 CONH.sub.2 phenyl 2-(amidinyl-methyl)phenyl 856 CONH.sub.2 phenyl 2-(2-imidazolidinyl- methyl)phenyl 857 CONH.sub.2 phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 858 CONH.sub.2 phenyl 2-dimethylaminoimidazol-1-yl 859 CONH.sub.2 phenyl 2-(3-aminophenyl) 860 CONH.sub.2 phenyl 2-(3-pyrrolidinylcarbonyl) 861 CONH.sub.2 phenyl 2-glycinoyl 862 CONH.sub.2 phenyl 2-(imidazol-1-ylacetyl) 863 CONH.sub.2 2-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl 864 CONH.sub.2 2-pyridyl 2-(N-piperidinyl-methyl)phenyl 865 CONH.sub.2 2-pyridyl 2-(N-morpholino-methyl)phenyl 866 CONH.sub.2 2-pyridyl 2-(N,N'-methylmorpholinium- methyl)phenyl 867 CONH.sub.2 2-pyridyl 2-(N-pyridinium-methyl)phenyl 868 CONH.sub.2 2-pyridyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 869 CONH.sub.2 2-pyridyl 2-(N-azatanyl-methyl)phenyl 870 CONH.sub.2 2-pyridyl 2-(N-azetidinyl-methyl)phenyl 871 CONH.sub.2 2-pyridyl 2-(N-piperazinyl-methyl)phenyl 872 CONH.sub.2 2-pyridyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 873 CONH.sub.2 2-pyridyl 2-(N-imidazolyl-methyl)phenyl 874 CONH.sub.2 2-pyridyl 2-(N-methoxy-N-methylamino- methyl)phenyl 875 CONH.sub.2 2-pyridyl 2-(N-pyridonyl-methyl)phenyl 876 CONH.sub.2 2-pyridyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 877 CONH.sub.2 2-pyridyl 2-(amidinyl)phenyl 878 CONH.sub.2 2-pyridyl 2-(N-guanidinyl)phenyl 879 CONH.sub.2 2-pyridyl 2-(imidazolyl)phenyl 880 CONH.sub.2 2-pyridyl 2-(imidazolidinyl)phenyl 881 CONH.sub.2 2-pyridyl 2-(2-imidazolidinyl- sulfonyl)phenyl 882 CONH.sub.2 2-pyridyl 2-(2-pyrrolidinyl)phenyl 883 CONH.sub.2 2-pyridyl 2-(2-piperidinyl)phenyl 884 CONH.sub.2 2-pyridyl 2-(amidinyl-methyl)phenyl 885 CONH.sub.2 2-pyridyl 2-(2-imidazolidinyl- methyl)phenyl 886 CONH.sub.2 2-pyridyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 887 CONH.sub.2 2-pyridyl 2-dimethylaminoimidazol-1-yl 888 CONH.sub.2 2-pyridyl 2-(3-aminophenyl) 889 CONH.sub.2 2-pyridyl 2-(3-pyrrolidinylcarbonyl) 890 CONH.sub.2 2-pyridyl 2-glycinoyl 891 CONH.sub.2 2-pyridyl 2-(imidazol-1-ylacetyl) 892 CONH.sub.2 3-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl 893 CONH.sub.2 3-pyridyl 2-(N-piperidinyl-methyl)phenyl 894 CONH.sub.2 3-pyridyl 2-(N-morpholino-methyl)phenyl 895 CONH.sub.2 3-pyridyl 2-(N,N'-methylmorpholinium- methyl)phenyl 896 CONH.sub.2 3-pyridyl 2-(N-pyridinium-methyl)phenyl 897 CONH.sub.2 3-pyridyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 898 CONH.sub.2 3-pyridyl 2-(N-azatanyl-methyl)phenyl 899 CONH.sub.2 3-pyridyl 2-(N-azetidinyl-methyl)phenyl 900 CONH.sub.2 3-pyridyl 2-(N-piperazinyl-methyl)phenyl 901 CONH.sub.2 3-pyridyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 902 CONH.sub.2 3-pyridyl 2-(N-imidazolyl-methyl)phenyl 903 CONH.sub.2 3-pyridyl 2-(N-methoxy-N-methylamino- methyl)phenyl 904 CONH.sub.2 3-pyridyl 2-(N-pyridonyl-methyl)phenyl 905 CONH.sub.2 3-pyridyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 906 CONH.sub.2 3-pyridyl 2-(amidinyl)phenyl 907 CONH.sub.2 3-pyridyl 2-(N-guanidinyl)phenyl 908 CONH.sub.2 3-pyridyl 2-(imidazolyl)phenyl 909 CONH.sub.2 3-pyridyl 2-(imidazolidinyl)phenyl 910 CONH.sub.2 3-pyridyl 2-(2-imidazolidinyl- sulfonyl)phenyl 911 CONH.sub.2 3-pyridyl 2-(2-pyrrolidinyl)phenyl 912 CONH.sub.2 3-pyridyl 2-(2-piperidinyl)phenyl 913 CONH.sub.2 3-pyridyl 2-(amidinyl-methyl)phenyl 914 CONH.sub.2 3-pyridyl 2-(2-imidazolidinyl- methyl)phenyl 915 CONH.sub.2 3-pyridyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 916 CONH.sub.2 3-pyridyl 2-dimethylaminoimidazol-1-yl 917 CONH.sub.2 3-pyridyl 2-(3-aminophenyl) 918 CONH.sub.2 3-pyridyl 2-(3-pyrrolidinylcarbonyl) 919 CONH.sub.2 3-pyridyl 2-glycinoyl 920 CONH.sub.2 3-pyridyl 2-(imidazol-1-ylacetyl) 921 CONH.sub.2 2-pyrimidyl 2-(N-pyrrolidinyl-methyl)phenyl 922 CONH.sub.2 2-pyrimidyl 2-(N-piperidinyl-methyl)phenyl 923 CONH.sub.2 2-pyrimidyl 2-(N-morpholino-methyl)phenyl 924 CONH.sub.2 2-pyrimidyl 2-(N,N'-methylmorpholinium- methyl)phenyl 925 CONH.sub.2 2-pyrimidyl 2-(N-pyridinium-methyl)phenyl 926 CONH.sub.2 2-pyrimidyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 927 CONH.sub.2 2-pyrimidyl 2-(N-azatanyl-methyl)phenyl 928 CONH.sub.2 2-pyrimidyl 2-(N-azetidinyl-methyl)phenyl 929 CONH.sub.2 2-pyrimidyl 2-(N-piperazinyl-methyl)phenyl 930 CONH.sub.2 2-pyrimidyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 931 CONH.sub.2 2-pyrimidyl 2-(N-imidazolyl-methyl)phenyl 932 CONH.sub.2 2-pyrimidyl 2-(N-methoxy-N-methylamino- methyl)phenyl 933 CONH.sub.2 2-pyrimidyl 2-(N-pyridonyl-methyl)phenyl 934 CONH.sub.2 2-pyrimidyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 935 CONH.sub.2 2-pyrimidyl 2-(amidinyl)phenyl 936 CONH.sub.2 2-pyrimidyl 2-(N-guanidinyl)phenyl 937 CONH.sub.2 2-pyrimidyl 2-(imidazolyl)phenyl 938 CONH.sub.2 2-pyrimidyl 2-(imidazolidinyl)phenyl 939 CONH.sub.2 2-pyrimidyl 2-(2-imidazolidinyl- sulfonyl)phenyl 940 CONH.sub.2 2-pyrimidyl 2-(2-pyrrolidinyl)phenyl 941 CONH.sub.2 2-pyrimidyl 2-(2-piperidinyl)phenyl 942 CONH.sub.2 2-pyrimidyl 2-(amidinyl-methyl)phenyl 943 CONH.sub.2 2-pyrimidyl 2-(2-imidazolidinyl- methyl)phenyl 944 CONH.sub.2 2-pyrimidyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 945 CONH.sub.2 2-pyrimidyl 2-dimethylaminoimidazol-1-yl 946 CONH.sub.2 2-pyrimidyl 2-(3-aminophenyl) 947 CONH.sub.2 2-pyrimidyl 2-(3-pyrrolidinylcarbonyl) 948 CONH.sub.2 2-pyrimidyl 2-glycinoyl 949 CONH.sub.2 2-pyrimidyl 2-(imidazol-1-ylacetyl) 950 CONH.sub.2 2-Cl-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 951 CONH.sub.2 2-Cl-phenyl 2-(N-piperidinyl-methyl)phenyl 952 CONH.sub.2 2-Cl-phenyl 2-(N-morpholino-methyl)phenyl 953 CONH.sub.2 2-Cl-phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 954 CONH.sub.2 2-Cl-phenyl 2-(N-pyridinium-methyl)phenyl 955 CONH.sub.2 2-Cl-phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 956 CONH.sub.2 2-Cl-phenyl 2-(N-azatanyl-methyl)phenyl 957 CONH.sub.2 2-Cl-phenyl 2-(N-azetidinyl-methyl)phenyl 958 CONH.sub.2 2-Cl-phenyl 2-(N-piperazinyl-methyl)phenyl 959 CONH.sub.2 2-Cl-phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 960 CONH.sub.2 2-Cl-phenyl 2-(N-imidazolyl-methyl)phenyl 961 CONH.sub.2 2-Cl-phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 962 CONH.sub.2 2-Cl-phenyl 2-(N-pyridonyl-methyl)phenyl 963 CONH.sub.2 2-Cl-phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 964 CONH.sub.2 2-Cl-phenyl 2-(amidinyl)phenyl 965 CONH.sub.2 2-Cl-phenyl 2-(N-guanidinyl)phenyl 966 CONH.sub.2 2-Cl-phenyl 2-(imidazolyl)phenyl 967 CONH.sub.2 2-Cl-phenyl 2-(imidazolidinyl)phenyl 968 CONH.sub.2 2-Cl-phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 969 CONH.sub.2 2-Cl-phenyl 2-(2-pyrrolidinyl)phenyl 970 CONH.sub.2 2-Cl-phenyl 2-(2-piperidinyl)phenyl 971 CONH.sub.2 2-Cl-phenyl 2-(amidinyl-methyl)phenyl 972 CONH.sub.2 2-Cl-phenyl 2-(2-imidazolidinyl- methyl)phenyl 973 CONH.sub.2 2-Cl-phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 974 CONH.sub.2 2-Cl-phenyl 2-dimethylaminoimidazol-1-yl 975 CONH.sub.2 2-Cl-phenyl 2-(3-aminophenyl) 976 CONH.sub.2 2-Cl-phenyl 2-(3-pyrrolidinylcarbonyl) 977 CONH.sub.2 2-Cl-phenyl 2-glycinoyl 978 CONH.sub.2 2-Cl-phenyl 2-(imidazol-1-ylacetyl) 979 CONH.sub.2 2-F-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 980 CONH.sub.2 2-F-phenyl 2-(N-piperidinyl-methyl)phenyl 981 CONH.sub.2 2-F-phenyl 2-(N-morpholino-methyl)phenyl 982 CONH.sub.2 2-F-phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 983 CONH.sub.2 2-F-phenyl 2-(N-pyridinium-methyl)phenyl 984 CONH.sub.2 2-F-phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 985 CONH.sub.2 2-F-phenyl 2-(N-azatanyl-methyl)phenyl 986 CONH.sub.2 2-F-phenyl 2-(N-azetidinyl-methyl)phenyl 987 CONH.sub.2 2-F-phenyl 2-(N-piperazinyl-methyl)phenyl 988 CONH.sub.2 2-F-phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 989 CONH.sub.2 2-F-phenyl 2-(N-imidazolyl-methyl)phenyl 990 CONH.sub.2 2-F-phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 991 CONH.sub.2 2-F-phenyl 2-(N-pyridonyl-methyl)phenyl 992 CONH.sub.2 2-F-phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 993 CONH.sub.2 2-F-phenyl 2-(amidinyl)phenyl 994 CONH.sub.2 2-F-phenyl 2-(N-guanidinyl)phenyl 995 CONH.sub.2 2-F-phenyl 2-(imidazolyl)phenyl 996 CONH.sub.2 2-F-phenyl 2-(imidazolidinyl)phenyl 997 CONH.sub.2 2-F-phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 998 CONH.sub.2 2-F-phenyl 2-(2-pyrrolidinyl)phenyl 999 CONH.sub.2 2-F-phenyl 2-(2-piperidinyl)phenyl 1000 CONH.sub.2 2-F-phenyl 2-(amidinyl-methyl)phenyl 1001 CONH.sub.2 2-F-phenyl 2-(2-imidazolidinyl- methyl)phenyl 1002 CONH.sub.2 2-F-phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1003 CONH.sub.2 2-F-phenyl 2-dimethylaminoimidazol-1-yl 1004 CONH.sub.2 2-F-phenyl 2-(3-aminophenyl) 1005 CONH.sub.2 2-F-phenyl 2-(3-pyrrolidinylcarbonyl) 1006 CONH.sub.2 2-F-phenyl 2-glycinoyl 1007 CONH.sub.2 2-F-phenyl 2-(imidazol-1-ylacetyl) 1008 CONH.sub.2 2,5-diF-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1009 CONH.sub.2 2,5-diF-phenyl 2-(N-piperidinyl-methyl)phenyl 1010 CONH.sub.2 2,5-diF-phenyl 2-(N-morpholino-methyl)phenyl 1011 CONH.sub.2 2,5-diF-phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 1012 CONH.sub.2 2,5-diF-phenyl 2-(N-pyridinium-methyl)phenyl 1013 CONH.sub.2 2,5-diF-phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 1014 CONH.sub.2 2,5-diF-phenyl 2-(N-azatanyl-methyl)phenyl 1015 CONH.sub.2 2,5-diF-phenyl 2-(N-azetidinyl-methyl)phenyl 1016 CONH.sub.2 2,5-diF-phenyl 2-(N-piperazinyl-methyl)phenyl 1017 CONH.sub.2 2,5-diF-phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 1018 CONH.sub.2 2,5-diF-phenyl 2-(N-imidazolyl-methyl)phenyl 1019 CONH.sub.2 2,5-diF-phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 1020 CONH.sub.2 2,5-diF-phenyl 2-(N-pyridonyl-methyl)phenyl 1021 CONH.sub.2 2,5-diF-phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 1022 CONH.sub.2 2,5-diF-phenyl 2-(amidinyl)phenyl 1023 CONH.sub.2 2,5-diF-phenyl 2-(N-guanidinyl)phenyl 1024 CONH.sub.2 2,5-diF-phenyl 2-(imidazolyl)phenyl 1025 CONH.sub.2 2,5-diF-phenyl 2-(imidazolidinyl)phenyl 1026 CONH.sub.2 2,5-diF-phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 1027 CONH.sub.2 2,5-diF-phenyl 2-(2-pyrrolidinyl)phenyl 1028 CONH.sub.2 2,5-diF-phenyl 2-(2-piperidinyl)phenyl 1029 CONH.sub.2 2,5-diF-phenyl 2-(amidinyl-methyl)phenyl 1030 CONH.sub.2 2,5-diF-phenyl 2-(2-imidazolidinyl- methyl)phenyl 1031 CONH.sub.2 2,5-diF-phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1032 CONH.sub.2 2,5-diF-phenyl 2-dimethylaminoimidazol-1-yl 1033 CONH.sub.2 2,5-diF-phenyl 2-(3-aminophenyl) 1034 CONH.sub.2 2,5-diF-phenyl 2-(3-pyrrolidinylcarbonyl) 1035 CONH.sub.2 2,5-diF-phenyl 2-glycinoyl 1036 CONH.sub.2 2,5-diF-phenyl 2-(imidazol-1-ylacetyl) 1037 SCH.sub.3 phenyl 2-(aminosulfonyl)phenyl 1038 SCH.sub.3 phenyl 2-(methylaminosulfonyl)phenyl 1039 SCH.sub.3 phenyl 1-pyrrolidinocarbonyl 1040 SCH.sub.3 phenyl 2-(methylsulfonyl)phenyl 1041 SCH.sub.3 phenyl 4-morpholino 1042 SCH.sub.3 phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 1043 SCH.sub.3 phenyl 4-morpholinocarbonyl 1044 SCH.sub.3 2-pyridyl 2-(aminosulfonyl)phenyl 1045 SCH.sub.3 2-pyridyl 2-(methylaminosulfonyl)phenyl 1046 SCH.sub.3 2-pyridyl 1-pyrrolidinocarbonyl 1047 SCH.sub.3 2-pyridyl 2-(methylsulfonyl)phenyl 1048 SCH.sub.3 2-pyridyl 4-morpholino 1049 SCH.sub.3 2-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 1050 SCH.sub.3 2-pyridyl 4-morpholinocarbonyl 1051 SCH.sub.3 3-pyridyl 2-(aminosulfonyl)phenyl 1052 SCH.sub.3 3-pyridyl 2-(methylaminosulfonyl)phenyl 1053 SCH.sub.3 3-pyridyl 1-pyrrolidinocarbonyl 1054 SCH.sub.3 3-pyridyl 2-(methylsulfonyl)phenyl 1055 SCH.sub.3 3-pyridyl 4-morpholino 1056 SCH.sub.3 3-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 1057 SCH.sub.3 3-pyridyl 4-morpholinocarbonyl 1058 SCH.sub.3 2-pyrimidyl 2-(aminosulfonyl)phenyl 1059 SCH.sub.3 2-pyrimidyl 2-(methylaminosulfonyl)phenyl 1060 SCH.sub.3 2-pyrimidyl 1-pyrrolidinocarbonyl 1061 SCH.sub.3 2-pyrimidyl 2-(methylsulfonyl)phenyl 1062 SCH.sub.3 2-pyrimidyl 4-morpholino 1063 SCH.sub.3 2-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 1064 SCH.sub.3 2-pyrimidyl 4-morpholinocarbonyl 1065 SCH.sub.3 5-pyrimidyl 2-(aminosulfonyl)phenyl 1066 SCH.sub.3 5-pyrimidyl 2-(methylaminosulfonyl)phenyl 1067 SCH.sub.3 5-pyrimidyl 1-pyrrolidinocarbonyl 1068 SCH.sub.3 5-pyrimidyl 2-(methylsulfonyl)phenyl 1069 SCH.sub.3 5-pyrimidyl 4-morpholino 1070 SCH.sub.3 5-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 1071 SCH.sub.3 5-pyrimidyl 4-morpholinocarbonyl 1072 SCH.sub.3 2-Cl-phenyl 2-(aminosulfonyl)phenyl 1073 SCH.sub.3 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl 1074 SCH.sub.3 2-Cl-phenyl 1-pyrrolidinocarbonyl 1075 SCH.sub.3 2-Cl-phenyl 2-(methylsulfonyl)phenyl 1076 SCH.sub.3 2-Cl-phenyl 4-morpholino 1077 SCH.sub.3 2-Cl-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 1078 SCH.sub.3 2-Cl-phenyl 4-morpholinocarbonyl 1079 SCH.sub.3 2-F-phenyl 2-(aminosulfonyl)phenyl 1080 SCH.sub.3 2-F-phenyl 2-(methylaminosulfonyl)phenyl 1081 SCH.sub.3 2-F-phenyl 1-pyrrolidinocarbonyl 1082 SCH.sub.3 2-F-phenyl 2-(methylsulfonyl)phenyl 1083 SCH.sub.3 2-F-phenyl 4-morpholino 1084 SCH.sub.3 2-F-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 1085 SCH.sub.3 2-F-phenyl 4-morpholinocarbonyl 1086 SCH.sub.3 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 1087 SCH.sub.3 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl 1088 SCH.sub.3 2,5-diF-phenyl 1-pyrrolidinocarbonyl 1089 SCH.sub.3 2,5-diF-phenyl 2-(methylsulfonyl)phenyl 1090 SCH.sub.3 2,5-diF-phenyl 4-morpholino 1091 SCH.sub.3 2,5-diF-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 1092 SCH.sub.3 2,5-diF-phenyl 4-morpholinocarbo nyl 1093 SCH.sub.3 phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1094 SCH.sub.3 phenyl 2-(N-piperidinyl-methyl)phenyl 1095 SCH.sub.3 phenyl 2-(N-morpholino-methyl)phenyl 1096 SCH.sub.3 phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 1097 SCH.sub.3 phenyl 2-(N-pyridinium-methyl)phenyl 1098 SCH.sub.3 phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 1099 SCH.sub.3 phenyl 2-(N-azatanyl-methyl)phenyl 1100 SCH.sub.3 phenyl 2-(N-azetidinyl-methyl)phenyl 1101 SCH.sub.3 phenyl 2-(N-piperazinyl-methyl)phenyl 1102 SCH.sub.3 phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 1103 SCH.sub.3 phenyl 2-(N-imidazolyl-methyl)phenyl 1104 SCH.sub.3 phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 1105 SCH.sub.3 phenyl 2-(N-pyridonyl-methyl)phenyl 1106 SCH.sub.3 phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 1107 SCH.sub.3 phenyl 2-(amidinyl)phenyl 1108 SCH.sub.3 phenyl 2-(N-guanidinyl)phenyl 1109 SCH.sub.3 phenyl 2-(imidazolyl)phenyl 1110 SCH.sub.3 phenyl 2-(imidazolidinyl)phenyl 1111 SCH.sub.3 phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 1112 SCH.sub.3 phenyl 2-(2-pyrrolidinyl)phenyl 1113 SCH.sub.3 phenyl 2-(2-piperidinyl)phenyl 1114 SCH.sub.3 phenyl 2-(amidinyl-methyl)phenyl 1115 SCH.sub.3 phenyl 2-(2-imidazolidinyl- methyl)phenyl 1116 SCH.sub.3 phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1117 SCH.sub.3 phenyl 2-dimethylaminoimidazol-1-yl 1118 SCH.sub.3 phenyl 2-(3-aminophenyl) 1119 SCH.sub.3 phenyl 2-(3-pyrrolidinylcarbonyl) 1120 SCH.sub.3 phenyl 2-glycinoyl 1121 SCH.sub.3 phenyl 2-(imidazol-1-ylacetyl) 1122 SCH.sub.3 2-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl 1123 SCH.sub.3 2-pyridyl 2-(N-piperidinyl-methyl)phenyl 1124 SCH.sub.3 2-pyridyl 2 (N-morpholino-methyl)phenyl 1125 SCH.sub.3 2-pyridyl 2-(N,N'-methylmorpholinium- methyl)phenyl 1126 SCH.sub.3 2-pyridyl 2-(N-pyridinium-methyl)phenyl 1127 SCH.sub.3 2-pyridyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 1128 SCH.sub.3 2-pyridyl 2-(N-azatanyl-methyl)phenyl 1129 SCH.sub.3 2-pyridyl 2-(N-azetidinyl-methyl)phenyl 1130 SCH.sub.3 2-pyridyl 2-(N-piperazinyl-methyl)phenyl 1131 SCH.sub.3 2-pyridyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 1132 SCH.sub.3 2-pyridyl 2-(N-imidazolyl-methyl)phenyl 1133 SCH.sub.3 2-pyridyl 2-(N-methoxy-N-methylamino- methyl)phenyl 1134 SCH.sub.3 2-pyridyl 2-(N-pyridonyl-methyl)phenyl 1135 SCH.sub.3 2-pyridyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 1136 SCH.sub.3 2-pyridyl 2-(amidinyl)phenyl 1137 SCH.sub.3 2-pyridyl 2-(N-guanidinyl)phenyl 1138 SCH.sub.3 2-pyridyl 2-(imidazolyl)phenyl 1139 SCH.sub.3 2-pyridyl 2-(imidazolidinyl)phenyl 1140 SCH.sub.3 2-pyridyl 2-(2-imidazolidinyl- sulfonyl)phenyl 1141 SCH.sub.3 2-pyridyl 2-(2-pyrrolidinyl)phenyl 1142 SCH.sub.3 2-pyridyl 2-(2-piperidinyl)phenyl 1143 SCH.sub.3 2-pyridyl 2-(amidinyl-methyl)phenyl 1144 SCH.sub.3 2-pyridyl 2-(2-imidazolidinyl- methyl)phenyl 1145 SCH.sub.3 2-pyridyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1146 SCH.sub.3 2-pyridyl 2-dimethylaminoimidazol-1-yl 1147 SCH.sub.3 2-pyridyl 2-(3-aminophenyl) 1148 SCH.sub.3 2-pyridyl 2-(3-pyrrolidinylcarbonyl) 1149 SCH.sub.3 2-pyridyl 2-glycinoyl 1150 SCH.sub.3 2-pyridyl 2-(imidazol-1-ylacetyl) 1151 SCH.sub.3 3-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl 1152 SCH.sub.3 3-pyridyl 2-(N-piperidinyl-methyl)phenyl 1153 SCH.sub.3 3-pyridyl 2-(N-morpholino-methyl)phenyl 1154 SCH.sub.3 3-pyridyl 2-(N,N'-methylmorpholinium- methyl)phenyl 1155 SCH.sub.3 3-pyridyl 2-(N-pyridinium-methyl)phenyl 1156 SCH.sub.3 3-pyridyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 1157 SCH.sub.3 3-pyridyl 2-(N-azatanyl-methyl)phenyl 1158 SCH.sub.3 3-pyridyl 2-(N-azetidinyl-methyl)phenyl 1159 SCH.sub.3 3-pyridyl 2-(N-piperazinyl-methyl)phenyl 1160 SCH.sub.3 3-pyridyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 1161 SCH.sub.3 3-pyridyl 2-(N-imidazolyl-methyl)phenyl 1162 SCH.sub.3 3-pyridyl 2-(N-methoxy-N-methylamino- methyl)phenyl 1163 SCH.sub.3 3-pyridyl 2-(N-pyridonyl-methyl)phenyl 1164 SCH.sub.3 3-pyridyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 1165 SCH.sub.3 3-pyridyl 2-(amidinyl)phenyl 1166 SCH.sub.3 3-pyridyl 2-(N-guanidinyl)phenyl 1167 SCH.sub.3 3-pyridyl 2-(imidazolyl)phenyl 1168 SCH.sub.3 3-pyridyl 2-(imidazolidinyl)phenyl 1169 SCH.sub.3 3-pyridyl 2-(2-imidazolidinyl- sulfonyl)phenyl 1170 SCH.sub.3 3-pyridyl 2-(2-pyrrolidinyl)phenyl 1171 SCH.sub.3 3-pyridyl 2-(2-piperidinyl)phenyl 1172 SCH.sub.3 3-pyridyl 2-(amidinyl-methyl)phenyl 1173 SCH.sub.3 3-pyridyl 2-(2-imidazolidinyl- methyl)phenyl 1174 SCH.sub.3 3-pyridyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1175 SCH.sub.3 3-pyridyl 2-dimethylaminoimidazol-1-yl 1176 SCH.sub.3 3-pyridyl 2-(3-aminophenyl) 1177 SCH.sub.3 3-pyridyl 2-(3-pyrrolidinylcarbonyl) 1178 SCH.sub.3 3-pyridyl 2-glycinoyl 1179 SCH.sub.3 3-pyridyl 2-(imidazol-1-ylacetyl) 1180 SCH.sub.3 2-pyrimidyl 2-(N-pyrrolidinyl-methyl)phenyl 1181 SCH.sub.3 2-pyrimidyl 2-(N-piperidinyl-methyl)phenyl 1182 SCH.sub.3 2-pyrimidyl 2-(N-morpholino-methyl)phenyl 1183 SCH.sub.3 2-pyrimidyl 2-(N,N'-methylmorpholinium- methyl)phenyl 1184 SCH.sub.3 2-pyrimidyl 2-(N-pyridinium-methyl)phenyl 1185 SCH.sub.3 2-pyrimidyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 1186 SCH.sub.3 2-pyrimidyl 2-(N-azatanyl-methyl)phenyl 1187 SCH.sub.3 2-pyrimidyl 2-(N-azetidinyl-methyl)phenyl 1188 SCH.sub.3 2-pyrimidyl 2-(N-piperazinyl-methyl)phenyl 1189 SCH.sub.3 2-pyrimidyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 1190 SCH.sub.3 2-pyrimidyl 2-(N-imidazolyl-methyl)phenyl 1191 SCH.sub.3 2-pyrimidyl 2-(N-methoxy-N-methylamino- methyl)phenyl 1192 SCH.sub.3 2-pyrimidyl 2-(N-pyridonyl-methyl)phenyl 1193 SCH.sub.3 2-pyrimidyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 1194 SCH.sub.3 2-pyrimidyl 2-(amidinyl)phenyl 1195 SCH.sub.3 2-pyrimidyl 2-(N-guanidinyl)phenyl 1196 SCH.sub.3 2-pyrimidyl 2-(imidazolyl)phenyl 1197 SCH.sub.3 2-pyrimidyl 2-(imidazolidinyl)phenyl 1198 SCH.sub.3 2-pyrimidyl 2-(2-imidazolidinyl- sulfonyl)phenyl 1199 SCH.sub.3 2-pyrinidyl 2-(2-pyrrolidinyl)phenyl 1200 SCH.sub.3 2-pyrimidyl 2-(2-piperidinyl)phenyl 1201 SCH.sub.3 2-pyrimidyl 2-(amidinyl-methyl)phenyl 1202 SCH.sub.3 2-pyrimidyl 2-(2-imidazolidinyl- methyl)phenyl 1203 SCH.sub.3 2-pyrimidyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1204 SCH.sub.3 2-pyrimidyl 2-dimethylaminoimidazol-1-yl 1205 SCH.sub.3 2-pyrimidyl 2-(3-aminophenyl) 1206 SCH.sub.3 2-pyrimidyl 2-(3-pyrrolidinylcarbonyl) 1207 SCH.sub.3 2-pyrimidyl 2-glycinoyl 1208 SCH.sub.3 2-pyrimidyl 2-(imidazol-1-ylacetyl) 1209 SCH.sub.3 2-Cl-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1210 SCH.sub.3 2-Cl-phenyl 2-(N-piperidinyl-methyl)phenyl 1211 SCH.sub.3 2-Cl-phenyl 2-(N-morpholino-methyl)phenyl 1212 SCH.sub.3 2-Cl-phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 1213 SCH.sub.3 2-Cl-phenyl 2-(N-pyridinium-methyl)phenyl 1214 SCH.sub.3 2-Cl-phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 1215 SCH.sub.3 2-Cl-phenyl 2-(N-azatanyl-methyl)phenyl 1216 SCH.sub.3 2-Cl-phenyl 2-(N-azetidinyl-methyl)phenyl 1217 SCH.sub.3 2-Cl-phenyl 2-(N-piperazinyl-methyl)phenyl 1218 SCH.sub.3 2-Cl-phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 1219 SCH.sub.3 2-Cl-phenyl 2-(N-imidazolyl-methyl)phenyl 1220 SCH.sub.3 2-Cl-phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 1221 SCH.sub.3 2-Cl-phenyl 2-(N-pyridonyl-methyl)phenyl 1222 SCH.sub.3 2-Cl-phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 1223 SCH.sub.3 2-Cl-phenyl 2-(amidinyl)phenyl 1224 SCH.sub.3 2-Cl-phenyl 2-(N-guanidinyl)phenyl 1225 SCH.sub.3 2-Cl-phenyl 2-(imidazolyl)phenyl 1226 SCH.sub.3 2-Cl-phenyl 2-(imidazolidinyl)phenyl 1227 SCH.sub.3 2-Cl-phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 1228 SCH.sub.3 2-Cl-phenyl 2-(2-pyrrolidinyl)phenyl 1229 SCH.sub.3 2-Cl-phenyl 2-(2-piperidinyl)phenyl 1230 SCH.sub.3 2-Cl-phenyl 2-(amidinyl-methyl)phenyl 1231 SCH.sub.3 2-Cl-phenyl 2-(2-imidazolidinyl- methyl)phenyl 1232 SCH.sub.3 2-Cl-phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1233 SCH.sub.3 2-Cl-phenyl 2-dimethylaminoimidazol-1-yl 1234 SCH.sub.3 2-Cl-phenyl 2-(3-aminophenyl) 1235 SCH.sub.3 2-Cl-phenyl 2-(3-pyrrolidinylcarbonyl) 1236 SCH.sub.3 2-Cl-phenyl 2-glycinoyl 1237 SCH.sub.3 2-Cl-phenyl 2-(imidazol-1-ylacetyl) 1238 SCH.sub.3 2-F-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1239 SCH.sub.3 2-F-phenyl 2-(N-piperidinyl-methyl)phenyl 1240 SCH.sub.3 2-F-phenyl 2-(N-morpholino-methyl)phenyl 1241 SCH.sub.3 2-F-phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 1242 SCH.sub.3 2-F-phenyl 2-(N-pyridinium-methyl)phenyl 1243 SCH.sub.3 2-F-phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 1244 SCH.sub.3 2-F-phenyl 2-(N-azatanyl-methyl)phenyl 1245 SCH.sub.3 2-F-phenyl 2-(N-azetidinyl-methyl)phenyl 1246 SCH.sub.3 2-F-phenyl 2-(N-piperazinyl-methyl)phenyl 1247 SCH.sub.3 2-F-phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 1248 SCH.sub.3 2-F-phenyl 2-(N-imidazolyl-methyl)phenyl 1249 SCH.sub.3 2-F-phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 1250 SCH.sub.3 2-F-phenyl 2-(N-pyridonyl-methyl)phenyl 1251 SCH.sub.3 2-F-phenyl 2-(N-(N',N'-dimethylhydrazinyl methyl)phenyl 1252 SCH.sub.3 2-F-phenyl 2-(amidinyl)phenyl 1253 SCH.sub.3 2-F-phenyl 2-(N-guanidinyl)phenyl 1254 SCH.sub.3 2-F-phenyl 2-(imidazolyl)phenyl 1255 SCH.sub.3 2-F-phenyl 2-(imidazolidinyl)phenyl 1256 SCH.sub.3 2-F-phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 1257 SCH.sub.3 2-F-phenyl 2-(2-pyrrolidinyl)phenyl 1258 SCH.sub.3 2-F-phenyl 2-(2-piperidinyl)phenyl 1259 SCH.sub.3 2-F-phenyl 2-(amidinyl-methyl)phenyl 1260 SCH.sub.3 2-F-phenyl 2-(2-imidazolidinyl- methyl)phenyl 1261 SCH.sub.3 2-F-phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1262 SCH.sub.3 2-F-phenyl 2-dimethylaminoimidazol-1-yl 1263 SCH.sub.3 2-F-phenyl 2-(3-aminophenyl) 1264 SCH.sub.3 2-F-phenyl 2-(3-pyrrolidinylcarbonyl) 1265 SCH.sub.3 2-F-phenyl 2-glycinoyl 1266 SCH.sub.3 2-F-phenyl 2-(imidazol-1-ylacetyl) 1267 SCH.sub.3 2,5-diF-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1268 SCH.sub.3 2,5-diF-phenyl 2-(N-piperidinyl-methyl)phenyl 1269 SCH.sub.3 2,5-diF-phenyl 2-(N-morpholino-methyl)phenyl 1270 SCH.sub.3 2,5-diF-phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 1271 SCH.sub.3 2,5-diF-phenyl 2-(N-pyridinium-methyl)phenyl 1272 SCH.sub.3 2,5-diF-phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 1273 SCH.sub.3 2,5-diF-phenyl 2-(N-azatanyl-methyl)phenyl 1274 SCH.sub.3 2,5-diF-phenyl 2-(N-azetidinyl-methyl)phenyl 1275 SCH.sub.3 2,5-diF-phenyl 2-(N-piperazinyl-methyl)phenyl 1276 SCH.sub.3 2,5-diF-phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 1277 SCH.sub.3 2,5-diF-phenyl 2-(N-imidazolyl-methyl)phenyl 1278 SCH.sub.3 2,5-diF-phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 1279 SCH.sub.3 2,5-diF-phenyl 2-(N-pyridonyl-methyl)phenyl 1280 SCH.sub.3 2,5-diF-phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 1281 SCH.sub.3 2,5-diF-phenyl 2-(amidinyl)phenyl 1282 SCH.sub.3 2,5-diF-phenyl 2-(N-guanidinyl)phenyl 1283 SCH.sub.3 2,5-diF-phenyl 2-(imidazolyl)phenyl 1284 SCH.sub.3 2,5-diF-phenyl 2-(imidazolidinyl)phenyl 1285 SCH.sub.3 2,5-diF-phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 1286 SCH.sub.3 2,5-diF-phenyl 2-(2-pyrrolidinyl)phenyl 1287 SCH.sub.3 2,5-diF-phenyl 2-(2-piperidinyl)phenyl 1288 SCH.sub.3 2,5-diF-phenyl 2-(amidinyl-methyl)phenyl 1289 SCH.sub.3 2,5-diF-phenyl 2-(2-imidazolidinyl- methyl)phenyl 1290 SCH.sub.3 2,5-diF-phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1291 SCH.sub.3 2,5-diF-phenyl 2-dimethylaminoimidazol-1-yl 1292 SCH.sub.3 2,5-diF-phenyl 2-(3-aminophenyl) 1293 SCH.sub.3 2,5-diF-phenyl 2-(3-pyrrolidinylcarbonyl) 1294 SCH.sub.3 2,5-diF-phenyl 2-glycinoyl 1295 SCH.sub.3 2,5-diF-phenyl 2-(imidazol-1-ylacetyl) 1296 SO.sub.2 CH.sub.3 phenyl 2-(aminosulfonyl)phenyl 1297 SO.sub.2 CH.sub.3 phenyl 2-(methylaminosulfonyl)phenyl 1298 SO.sub.2 CH.sub.3 phenyl 1-pyrrolidinocarbonyl 1299 SO.sub.2 CH.sub.3 phenyl 2-(methylsulfonyl)phenyl 1300 SO.sub.2 CH.sub.3 phenyl 4-morpholino 1301 SO.sub.2 CH.sub.3 phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 1302 SO.sub.2 CH.sub.3 phenyl 4-morpholinocarbo nyl 1303 SO.sub.2 CH.sub.3 2-pyridyl 2-(aminosulfonyl)phenyl 1304 SO.sub.2 CH.sub.3 2-pyridyl 2-(methylaminosulfonyl)phenyl 1305 SO.sub.2 CH.sub.3 2-pyridyl 1-pyrrolidinocarbonyl 1306 SO.sub.2 CH.sub.3 2-pyridyl 2-(methylsulfonyl)phenyl 1307 SO.sub.2 CH.sub.3 2-pyridyl 4-morpholino 1308 SO.sub.2 CH.sub.3 2-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 1309 SO.sub.2 CH.sub.3 2-pyridyl 4-morpholinoca rbonyl 1310 SO.sub.2 CH.sub.3 3-pyridyl 2-(aminosulfonyl)phenyl 1311 SO.sub.2 CH.sub.3 3-pyridyl 2-(methylaminosulfonyl)phenyl 1312 SO.sub.2 CH.sub.3 3-pyridyl 1-pyrrolidinocarbonyl 1313 SO.sub.2 CH.sub.3 3-pyridyl 2-(methylsulfonyl)phenyl 1314 SO.sub.2 CH.sub.3 3-pyridyl 4-morpholino 1315 SO.sub.2 CH.sub.3 3-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 1316 SO.sub.2 CH.sub.3 3-pyridyl 4-morpholinoca rbonyl 1317 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(aminosulfonyl)phenyl 1318 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(methylaminosulfonyl)phenyl 1319 SO.sub.2 CH.sub.3 2-pyrimidyl 1-pyrrolidin ocarbonyl 1320 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(methylsulfonyl)phenyl 1321 SO.sub.2 CH.sub.3 2-pyrimidyl 4-morpholino 1322 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 1323 SO.sub.2 CH.sub.3 2-pyrimidyl 4-morpholinocarbonyl 1324 SO.sub.2 CH.sub.3 5-pyrimidyl 2-(aminosulfonyl)phenyl 1325 SO.sub.2 CH.sub.3 5-pyrimidyl 2-(methylaminosulfonyl)phenyl 1326 SO.sub.2 CH.sub.3 5-pyrimidyl 1-pyrrolidin ocarbonyl 1327 SO.sub.2 CH.sub.3 5-pyrimidyl 2-(methylsulfonyl)phenyl 1328 SO.sub.2 CH.sub.3 5-pyrimidyl 4-morpholino 1329 SO.sub.2 CH.sub.3 5-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 1330 SO.sub.2 CH.sub.3 5-pyrimidyl 4-morpholinocarbonyl 1331 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(aminosulfonyl)phenyl 1332 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl 1333 SO.sub.2 CH.sub.3 2-Cl-phenyl 1-pyrrolidin ocarbonyl 1334 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(methylsulfonyl)phenyl 1335 SO.sub.2 CH.sub.3 2-Cl-phenyl 4-morpholino 1336 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 1337 SO.sub.2 CH.sub.3 2-Cl-phenyl 4-morpholinocarbonyl 1338 SO.sub.2 CH.sub.3 2-F-phenyl 2-(aminosulfonyl)phenyl 1339 SO.sub.2 CH.sub.3 2-F-phenyl 2-(methylaminosulfonyl)phenyl 1340 SO.sub.2 CH.sub.3 2-F-phenyl 1-pyrrolidino carbonyl 1341 SO.sub.2 CH.sub.3 2-F-phenyl 2-(methylsulfonyl)phenyl 1342 SO.sub.2 CH.sub.3 2-F-phenyl 4-morpholino 1343 SO.sub.2 CH.sub.3 2-F-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 1344 SO.sub.2 CH.sub.3 2-F-phenyl 4-morpholinoc arbonyl 1345 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 1346 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl 1347 SO.sub.2 CH.sub.3 2,5-diF-phenyl 1-pyrroli dinocarbonyl 1348 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(methylsulfonyl)phenyl 1349 SO.sub.2 CH.sub.3 2,5-diF-phenyl 4-morpholino 1350 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phen yl 1351 SO.sub.2 CH.sub.3 2,5-diF-phenyl 4-morpholinocarbonyl 1352 SO.sub.2 CH.sub.3 phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1353 SO.sub.2 CH.sub.3 phenyl 2-(N-piperidinyl-methyl)phenyl 1354 SO.sub.2 CH.sub.3 phenyl 2-(N-morpholino-methyl)phenyl 1355 SO.sub.2 CH.sub.3 phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 1356 SO.sub.2 CH.sub.3 phenyl 2-(N-pyridinium-methyl)phenyl 1357 SO.sub.2 CH.sub.3 phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 1358 SO.sub.2 CH.sub.3 phenyl 2-(N-azatanyl-methyl)phenyl 1359 SO.sub.2 CH.sub.3 phenyl 2-(N-azetidinyl-methyl)phenyl 1360 SO.sub.2 CH.sub.3 phenyl 2-(N-piperazinyl-methyl)phenyl 1361 SO.sub.2 CH.sub.3 phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 1362 SO.sub.2 CH.sub.3 phenyl 2-(N-imidazolyl-methyl)phenyl 1363 SO.sub.2 CH.sub.3 phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 1364 SO.sub.2 CH.sub.3 phenyl 2-(N-pyridonyl-methyl)phenyl 1365 SO.sub.2 CH.sub.3 phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 1366 SO.sub.2 CH.sub.3 phenyl 2-(amidinyl)phenyl 1367 SO.sub.2 CH.sub.3 phenyl 2-(N-guanidinyl)phenyl 1368 SO.sub.2 CH.sub.3 phenyl 2-(imidazolyl)phenyl 1369 SO.sub.2 CH.sub.3 phenyl 2-(imidazolidinyl)phenyl 1370 SO.sub.2 CH.sub.3 phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 1371 SO.sub.2 CH.sub.3 phenyl 2-(2-pyrrolidinyl)phenyl 1372 SO.sub.2 CH.sub.3 phenyl 2-(2-piperidinyl)phenyl 1373 SO.sub.2 CH.sub.3 phenyl 2-(amidinyl-methyl)phenyl 1374 SO.sub.2 CH.sub.3 phenyl 2-(2-imidazolidinyl- methyl)phenyl 1375 SO.sub.2 CH.sub.3 phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1376 SO.sub.2 CH.sub.3 phenyl 2-dimethylaminoimidazol-1-yl 1377 SO.sub.2 CH.sub.3 phenyl 2-(3-aminophenyl) 1378 SO.sub.2 CH.sub.3 phenyl 2-(3-pyrrolidinylcarbonyl) 1379 SO.sub.2 CH.sub.3 phenyl 2-glycinoyl 1380 SO.sub.2 CH.sub.3 phenyl 2-(imidazol-1-ylacetyl) 1381 SO.sub.2 CH.sub.3 2-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl 1382 SO.sub.2 CH.sub.3 2-pyridyl 2-(N-piperidin yl-methyl)phenyl 1383 SO.sub.2 CH.sub.3 2-pyridyl 2-(N-morpholino-methyl)phenyl 1384 SO.sub.2 CH.sub.3 2-pyridyl 2-(N,N'-methylmorpholinium- methyl)phenyl 1385 SO.sub.2 CH.sub.3 2-pyridyl 2-(N-pyridinium-methyl)phenyl 1386 SO.sub.2 CH.sub.3 2-pyridyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 1387 SO.sub.2 CH.sub.3 2-pyridyl 2-(N-azatanyl-methyl)phenyl 1388 SO.sub.2 CH.sub.3 2-pyridyl 2-(N-azetidinyl-methyl)phenyl 1389 SO.sub.2 CH.sub.3 2-pyridyl 2-(N-piperazinyl-methyl)phenyl 1390 SO.sub.2 CH.sub.3 2-pyridyl 2-(N,N'-BOC-pi perazinyl- methyl)phenyl 1391 SO.sub.2 CH.sub.3 2-pyridyl 2-(N-imidazolyl-methyl)phenyl 1392 SO.sub.2 CH.sub.3 2-pyridyl 2-(N-methoxy-N-methylamino- methyl)phenyl 1393 SO.sub.2 CH.sub.3 2-pyridyl 2-(N-pyridonyl-methyl)phenyl 1394 SO.sub.2 CH.sub.3 2-pyridyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 1395 SO.sub.2 CH.sub.3 2-pyridyl 2-(amidinyl)phenyl 1396 SO.sub.2 CH.sub.3 2-pyridyl 2-(N-guanidinyl)phenyl 1397 SO.sub.2 CH.sub.3 2-pyridyl 2-(imidazolyl)phenyl 1398 SO.sub.2 CH.sub.3 2-pyridyl 2-(imidazolidinyl)phenyl 1399 SO.sub.2 CH.sub.3 2-pyridyl 2-(2-imidazolidinyl- sulfonyl)phenyl 1400 SO.sub.2 CH.sub.3 2-pyridyl 2-(2-pyrrolidinyl)phenyl 1401 SO.sub.2 CH.sub.3 2-pyridyl 2-(2-piperidinyl)phenyl 1402 SO.sub.2 CH.sub.3 2-pyridyl 2-(amidinyl-methyl)phenyl 1403 SO.sub.2 CH.sub.3 2-pyridyl 2-(2-imidazolidinyl- methyl)phenyl 1404 SO.sub.2 CH.sub.3 2-pyridyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1405 SO.sub.2 CH.sub.3 2-pyridyl 2-dimethylaminoimidazol-1-yl 1406 SO.sub.2 CH.sub.3 2-pyridyl 2-(3-aminophenyl) 1407 SO.sub.2 CH.sub.3 2-pyridyl 2-(3-pyrrolidinylcarbonyl) 1408 SO.sub.2 CH.sub.3 2-pyridyl 2-glycinoyl 1409 SO.sub.2 CH.sub.3 2-pyridyl 2-(imidazol-1-ylacetyl) 1410 SO.sub.2 CH.sub.3 3-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl 1411 SO.sub.2 CH.sub.3 3-pyridyl 2-(N-piperidin yl-methyl)phenyl 1412 SO.sub.2 CH.sub.3 3-pyridyl 2-(N-morpholino-methyl)phenyl 1413 SO.sub.2 CH.sub.3 3-pyridyl 2-(N,N'-methylmorpholinium- methyl)phenyl 1414 SO.sub.2 CH.sub.3 3-pyridyl 2-(N-pyridinium-methyl)phenyl 1415 SO.sub.2 CH.sub.3 3-pyridyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 1416 SO.sub.2 CH.sub.3 3-pyridyl 2-(N-azatanyl-methyl)phenyl 1417 SO.sub.2 CH.sub.3 3-pyridyl 2-(N-azetidinyl-methyl)phenyl 1418 SO.sub.2 CH.sub.3 3-pyridyl 2-(N-piperazinyl-methyl)phenyl 1419 SO.sub.2 CH.sub.3 3-pyridyl 2-(N,N'-BOC-pi perazinyl- methyl)phenyl 1420 SO.sub.2 CH.sub.3 3-pyridyl 2-(N-imidazolyl-methyl)phenyl 1421 SO.sub.2 CH.sub.3 3-pyridyl 2-(N-methoxy-N-methylamino- methyl)phenyl 1422 SO.sub.2 CH.sub.3 3-pyridyl 2-(N-pyridonyl-methyl)phenyl 1423 SO.sub.2 CH.sub.3 3-pyridyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 1424 SO.sub.2 CH.sub.3 3-pyridyl 2-(amidinyl)phenyl 1425 SO.sub.2 CH.sub.3 3-pyridyl 2-(N-guanidinyl)phenyl 1426 SO.sub.2 CH.sub.3 3-pyridyl 2-(imidazolyl)phenyl 1427 SO.sub.2 CH.sub.3 3-pyridyl 2-(imidazolidinyl)phenyl 1428 SO.sub.2 CH.sub.3 3-pyridyl 2-(2-imidazolidinyl- sulfonyl)phenyl 1429 SO.sub.2 CH.sub.3 3-pyridyl 2-(2-pyrrolidinyl)phenyl 1430 SO.sub.2 CH.sub.3 3-pyridyl 2-(2-piperidinyl)phenyl 1431 SO.sub.2 CH.sub.3 3-pyridyl 2-(amidinyl-methyl)phenyl 1432 SO.sub.2 CH.sub.3 3-pyridyl 2-(2-imidazolidinyl- methyl)phenyl 1433 SO.sub.2 CH.sub.3 3-pyridyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1434 SO.sub.2 CH.sub.3 3-pyridyl 2-dimethylaminoimidazol-1-yl 1435 SO.sub.2 CH.sub.3 3-pyridyl 2-(3-aminophenyl) 1436 SO.sub.2 CH.sub.3 3-pyridyl 2-(3-pyrrolidinylcarbonyl) 1437 SO.sub.2 CH.sub.3 3-pyridyl 2-glycinoyl 1438 SO.sub.2 CH.sub.3 3-pyridyl 2-(imidazol-1-ylacetyl) 1439 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-pyrrolidinyl-methyl)phenyl 1440 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-piperid inyl-methyl)phenyl 1441 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-morpholino-methyl)phenyl 1442 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(N,N'-meth ylmorpholinium- methyl)phenyl 1443 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-pyridinium-methyl)phenyl 1444 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-4-(N,N' -dimethylamino)- pyridinium-methyl)phenyl 1445 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-azatanyl-methyl)phenyl 1446 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-azetidinyl-methyl)phenyl 1447 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-piperaz inyl-methyl)phenyl 1448 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 1449 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-imidazolyl-methyl)phenyl 1450 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-methoxy -N-methylamino- methyl)phenyl 1451 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-pyridonyl-methyl)phenyl 1452 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-(N',N'- dimethylhydrazinyl- methyl)phenyl 1453 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(amidinyl)phenyl 1454 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-guanidinyl)phenyl 1455 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(imidazolyl)phenyl 1456 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(imidazolidinyl)phenyl 1457 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(2-imidazolidinyl- sulfonyl)phenyl 1458 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(2-pyrrolidinyl)phenyl 1459 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(2-piperidinyl)phenyl 1460 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(amidinyl-methyl)phenyl 1461 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(2-imidazolidinyl- methyl)phenyl 1462 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1463 SO.sub.2 CH.sub.3 2-pyrimidyl 2-dimethylaminoimidazol-1-yl 1464 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(3-aminoph enyl) 1465 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(3-pyrrolidinylcarbonyl) 1466 SO.sub.2 CH.sub.3 2-pyrimidyl 2-glycinoyl 1467 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(imidazol-1-ylacetyl) 1468 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1469 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-piperid inyl-methyl)phenyl 1470 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-morpholino-methyl)phenyl 1471 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N,N'-meth ylmorpholinium- methyl)phenyl 1472 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-pyridinium-methyl)phenyl 1473 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-4-(N,N' -dimethylamino)- pyridinium-methyl)phenyl 1474 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-azatanyl-methyl)phenyl 1475 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-azetidinyl-methyl)phenyl 1476 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-piperaz inyl-methyl)phenyl 1477 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 1478 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-imidazolyl-methyl)phenyl 1479 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-methoxy -N-methylamino- methyl)phenyl 1480 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-pyridonyl-methyl)phenyl 1481 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-(N',N'- dimethylhydrazinyl- methyl)phenyl 1482 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(amidinyl)phenyl 1483 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-guanidinyl)phenyl 1484 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(imidazolyl)phenyl 1485 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(imidazolidinyl)phenyl 1486 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 1487 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(2-pyrrolidinyl)phenyl 1488 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(2-piperidinyl)phenyl 1489 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(amidinyl-methyl)phenyl 1490 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(2-imidazolidinyl- methyl)phenyl 1491 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1492 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-dimethylaminoimidazol-1-yl 1493 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(3-aminoph enyl) 1494 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(3-pyrrolidinylcarbonyl) 1495 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-glycinoyl 1496 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(imidazol-1-ylacetyl) 1497 SO.sub.2 CH.sub.3 2-F-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1498 SO.sub.2 CH.sub.3 2-F-phenyl 2-(N-piperidi nyl-methyl)phenyl 1499 SO.sub.2 CH.sub.3 2-F-phenyl 2-(N-morpholino-methyl)phenyl 1500 SO.sub.2 CH.sub.3 2-F-phenyl 2-(N,N'-methy lmorpholinium- methyl)phenyl 1501 SO.sub.2 CH.sub.3 2-F-phenyl 2-(N-pyridinium-methyl)phenyl 1502 SO.sub.2 CH.sub.3 2-F-phenyl 2-(N-4-(N,N'- dimethylamino)- pyridinium-methyl)phenyl 1503 SO.sub.2 CH.sub.3 2-F-phenyl 2-(N-azatanyl-methyl)phenyl 1504 SO.sub.2 CH.sub.3 2-F-phenyl 2-(N-azetidinyl-methyl)phenyl 1505 SO.sub.2 CH.sub.3 2-F-phenyl 2-(N-piperazi nyl-methyl)phenyl 1506 SO.sub.2 CH.sub.3 2-F-phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 1507 SO.sub.2 CH.sub.3 2-F-phenyl 2-(N-imidazolyl-methyl)phenyl 1508 SO.sub.2 CH.sub.3 2-F-phenyl 2-(N-methoxy- N-methylamino- methyl)phenyl 1509 SO.sub.2 CH.sub.3 2-F-phenyl 2-(N-pyridonyl-methyl)phenyl 1510 SO.sub.2 CH.sub.3 2-F-phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 1511 SO.sub.2 CH.sub.3 2-F-phenyl 2-(amidinyl)phenyl 1512 SO.sub.2 CH.sub.3 2-F-phenyl 2-(N-guanidinyl)phenyl 1513 SO.sub.2 CH.sub.3 2-F-phenyl 2-(imidazolyl)phenyl 1514 SO.sub.2 CH.sub.3 2-F-phenyl 2-(imidazolidinyl)phenyl 1515 SO.sub.2 CH.sub.3 2-F-phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 1516 SO.sub.2 CH.sub.3 2-F-phenyl 2-(2-pyrrolidinyl)phenyl 1517 SO.sub.2 CH.sub.3 2-F-phenyl 2-(2-piperidinyl)phenyl 1518 SO.sub.2 CH.sub.3 2-F-phenyl 2-(amidinyl-methyl)phenyl 1519 SO.sub.2 CH.sub.3 2-F-phenyl 2-(2-imidazolidinyl- methyl)phenyl 1520 SO.sub.2 CH.sub.3 2-F-phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1521 SO.sub.2 CH.sub.3 2-F-phenyl 2-dimethylaminoimidazol-1-yl 1522 SO.sub.2 CH.sub.3 2-F-phenyl 2-(3-aminophenyl) 1523 SO.sub.2 CH.sub.3 2-F-phenyl 2-(3-pyrrolidinylcarbonyl) 1524 SO.sub.2 CH.sub.3 2-F-phenyl 2-glycinoyl 1525 SO.sub.2 CH.sub.3 2-F-phenyl 2-(imidazol-1-ylacetyl) 1526 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1527 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-pipe ridinyl-methyl)phenyl 1528 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-morpholino-methyl)phenyl 1529 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N,N'-m ethylmorpholinium- methyl)phenyl 1530 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-pyridinium-methyl)phenyl 1531 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-4-(N ,N'-dimethylamino)- pyridinium-methyl)phenyl 1532 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-azatanyl-methyl)phenyl 1533 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-azet idinyl-methyl)phenyl 1534 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-piperazinyl-methyl)phenyl 1535 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N,N'-B OC-piperazinyl- methyl)phenyl 1536 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-imidazolyl-methyl)phenyl 1537 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-meth oxy-N-methylamino- methyl)phenyl 1538 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-pyridonyl-methyl)phenyl 1539 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-(N', N'-dimethylhydrazinyl- methyl)phenyl 1540 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(amidinyl)phenyl 1541 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-guanidinyl)phenyl 1542 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(imidazolyl)phenyl 1543 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(imidazolidinyl)phenyl 1544 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 1545 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(2-pyrrolidinyl)phenyl 1546 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(2-piperidinyl)phenyl 1547 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(amidinyl-methyl)phenyl 1548 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(2-imid azolidinyl- methyl)phenyl 1549 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1550 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-dimethylaminoimidazol-1-yl 1551 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(3-amin ophenyl) 1552 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(3-pyrrolidinylcarbonyl) 1553 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-glycino yl 1554 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(imidazol-1-ylacetyl) 1555 NHSO.sub.2 CH.sub.3 phenyl 2-(aminosulfonyl)phenyl 1556 NHSO.sub.2 CH.sub.3 phenyl 2-(methylaminosulfonyl)phenyl 1557 NHSO.sub.2 CH.sub.3 phenyl 1-pyrrolidinocarbonyl 1558 NHSO.sub.2 CH.sub.3 phenyl 2-(methylsulfonyl)phenyl 1559 NHSO.sub.2 CH.sub.3 phenyl 4-morpholino 1560 NHSO.sub.2 CH.sub.3 phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 1561 NHSO.sub.2 CH.sub.3 phenyl 4-morpholinocar bonyl 1562 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(aminosulfonyl)phenyl 1563 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(methylaminosulfonyl)phenyl 1564 NHSO.sub.2 CH.sub.3 2-pyridyl 1-pyrrolidin ocarbonyl 1565 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(methylsulfonyl)phenyl 1566 NHSO.sub.2 CH.sub.3 2-pyridyl 4-morpholino 1567 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 1568 NHSO.sub.2 CH.sub.3 2-pyridyl 4-morpholinocarbonyl 1569 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(aminosulfonyl)phenyl 1570 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(methylaminosulfonyl)phenyl 1571 NHSO.sub.2 CH.sub.3 3-pyridyl 1-pyrrolidin ocarbonyl 1572 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(methylsulfonyl)phenyl 1573 NHSO.sub.2 CH.sub.3 3-pyridyl 4-morpholino 1574 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 1575 NHSO.sub.2 CH.sub.3 3-pyridyl 4-morpholinocarbonyl 1576 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(aminosulfonyl)phenyl 1577 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(methylaminosulfonyl)phenyl 1578 NHSO.sub.2 CH.sub.3 2-pyrimidyl 1-pyrrolid inocarbonyl 1579 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(methylsulfonyl)phenyl 1580 NHSO.sub.2 CH.sub.3 2-pyrimidyl 4-morpholino 1581 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)pheny l 1582 NHSO.sub.2 CH.sub.3 2-pyrimidyl 4-morpholinocarbonyl 1583 NHSO.sub.2 CH.sub.3 5-pyrimidyl 2-(aminosulfonyl)phenyl 1584 NHSO.sub.2 CH.sub.3 5-pyrimidyl 2-(methylaminosulfonyl)phenyl 1585 NHSO.sub.2 CH.sub.3 5-pyrimidyl 1-pyrrolid inocarbonyl 1586 NHSO.sub.2 CH.sub.3 5-pyrimidyl 2-(methylsulfonyl)phenyl 1587 NHSO.sub.2 CH.sub.3 5-pyrimidyl 4-morpholino 1588 NHSO.sub.2 CH.sub.3 5-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)pheny l 1589 NHSO.sub.2 CH.sub.3 5-pyrimidyl 4-morpholinocarbonyl 1590 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(aminosulfonyl)phenyl 1591 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl 1592 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 1-pyrrolid inocarbonyl 1593 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(methylsulfonyl)phenyl 1594 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 4-morpholino 1595 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)pheny l 1596 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 4-morpholinocarbonyl 1597 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(aminosulfonyl)phenyl 1598 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(methylaminosulfonyl)phenyl 1599 NHSO.sub.2 CH.sub.3 2-F-phenyl 1-pyrrolidi nocarbonyl 1600 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(methylsulfonyl)phenyl 1601 NHSO.sub.2 CH.sub.3 2-F-phenyl 4-morpholino 1602 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 1603 NHSO.sub.2 CH.sub.3 2-F-phenyl 4-morpholinocarbonyl 1604 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 1605 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl 1606 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 1-pyrrolidinocarbonyl 1607 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(methylsulfonyl)phenyl 1608 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 4-morpholino 1609 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)ph enyl 1610 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 4-morpholinocarbonyl 1611 NHSO.sub.2 CH.sub.3 phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1612 NHSO.sub.2 CH.sub.3 phenyl 2-(N-piperidiny l-methyl)phenyl 1613 NHSO.sub.2 CH.sub.3 phenyl 2-(N-morpholino-methyl)phenyl 1614 NHSO.sub.2 CH.sub.3 phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 1615 NHSO.sub.2 CH.sub.3 phenyl 2-(N-pyridinium-methyl)phenyl 1616 NHSO.sub.2 CH.sub.3 phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 1617 NHSO.sub.2 CH.sub.3 phenyl 2-(N-azatanyl-methyl)phenyl 1618 NHSO.sub.2 CH.sub.3 phenyl 2-(N-azetidinyl-methyl)phenyl 1619 NHSO.sub.2 CH.sub.3 phenyl 2-(N-piperazinyl-methyl)phenyl 1620 NHSO.sub.2 CH.sub.3 phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 1621 NHSO.sub.2 CH.sub.3 phenyl 2-(N-imidazolyl-methyl)phenyl 1622 NHSO.sub.2 CH.sub.3 phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 1623 NHSO.sub.2 CH.sub.3 phenyl 2-(N-pyridonyl-methyl)phenyl 1624 NHSO.sub.2 CH.sub.3 phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 1625 NHSO.sub.2 CH.sub.3 phenyl 2-(amidinyl)phenyl 1626 NHSO.sub.2 CH.sub.3 phenyl 2-(N-guanidinyl)phenyl 1627 NHSO.sub.2 CH.sub.3 phenyl 2-(imidazolyl)phenyl 1628 NHSO.sub.2 CH.sub.3 phenyl 2-(imidazolidinyl)phenyl 1629 NHSO.sub.2 CH.sub.3 phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 1630 NHSO.sub.2 CH.sub.3 phenyl 2-(2-pyrrolidinyl)phenyl 1631 NHSO.sub.2 CH.sub.3 phenyl 2-(2-piperidinyl)phenyl 1632 NHSO.sub.2 CH.sub.3 phenyl 2-(amidinyl-methyl)phenyl 1633 NHSO.sub.2 CH.sub.3 phenyl 2-(2-imidazolidinyl- methyl)phenyl 1634 NHSO.sub.2 CH.sub.3 phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1635 NHSO.sub.2 CH.sub.3 phenyl 2-dimethylaminoimidazol-1-yl 1636 NHSO.sub.2 CH.sub.3 phenyl 2-(3-aminophenyl) 1637 NHSO.sub.2 CH.sub.3 phenyl 2-(3-pyrrolidinylcarbonyl) 1638 NHSO.sub.2 CH.sub.3 phenyl 2-glycinoyl 1639 NHSO.sub.2 CH.sub.3 phenyl 2-(imidazol-1-ylacetyl) 1640 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl 1641 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(N-piperid inyl-methyl)phenyl 1642 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(N-morpholino-methyl)phenyl 1643 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(N,N'-meth ylmorpholinium- methyl)phenyl 1644 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(N-pyridinium-methyl)phenyl 1645 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(N-4-(N,N' -dimethylamino)- pyridinium-methyl)phenyl 1646 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(N-azatanyl-methyl)phenyl 1647 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(N-azetidinyl-methyl)phenyl 1648 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(N-piperaz inyl-methyl)phenyl 1649 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 1650 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(N-imidazolyl-methyl)phenyl 1651 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(N-methoxy -N-methylamino- methyl)phenyl 1652 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(N-pyridonyl-methyl)phenyl 1653 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(N-(N',N'- dimethylhydrazinyl- methyl)phenyl1654 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(amidinyl)phenyl 1655 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(N-guanidinyl)phenyl 1656 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(imidazolyl)phenyl 1657 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(imidazolidinyl)phenyl 1658 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(2-imidazolidinyl- sulfonyl)phenyl 1659 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(2-pyrrolidinyl)phenyl 1660 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(2-piperidinyl)phenyl 1661 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(amidinyl-methyl)phenyl 1662 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(2-imidazolidinyl- methyl)phenyl 1663 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1664 NHSO.sub.2 CH.sub.3 2-pyridyl 2-dimethylaminoimidazol-1-yl 1665 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(3-aminoph enyl) 1666 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(3-pyrrolidinylcarbonyl) 1667 NHSO.sub.2 CH.sub.3 2-pyridyl 2-glycinoyl 1668 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(imidazol-1-ylacetyl) 1669 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(N-pyrrolidinyl-methyl)phenyl 1670 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(N-piperid inyl-methyl)phenyl 1671 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(N-morpholino-methyl)phenyl 1672 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(N,N'-meth ylmorpholinium- methyl)phenyl 1673 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(N-pyridiniuin-methyl)phenyl 1674 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(N-4-(N,N' -dimethylamino)- pyridinium-methyl)phenyl 1675 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(N-azatanyl-methyl)phenyl 1676 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(N-azetidinyl-methyl)phenyl 1677 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(N-piperaz inyl-methyl)phenyl 1678 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 1679 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(N-imidazolyl-methyl)phenyl 1680 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(N-methoxy -N-methylamino- methyl)phenyl 1681 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(N-pyridonyl-methyl)phenyl 1682 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(N-(N',N'- dimethylhydrazinyl- methyl)phenyl 1683 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(amidinyl)phenyl 1684 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(N-guanidinyl)phenyl 1685 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(imidazolyl)phenyl 1686 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(imidazolidinyl)phenyl 1687 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(2-imidazolidinyl- sulfonyl)phenyl 1688 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(2-pyrrolidinyl)phenyl 1689 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(2-piperidinyl)phenyl 1690 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(amidinyl-methyl)phenyl 1691 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(2-imidazolidinyl- methyl)phenyl 1692 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1693 NHSO.sub.2 CH.sub.3 3-pyridyl 2-dimethylaminoimidazol-1-yl 1694 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(3-aminoph enyl) 1695 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(3-pyrrolidinylcarbonyl) 1696 NHSO.sub.2 CH.sub.3 3-pyridyl 2-glycinoyl 1697 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(imidazol-1-ylacetyl) 1698 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-pyrrolidinyl-methyl)phenyl 1699 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-piper idinyl-methyl)phenyl 1700 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-morpholino-methyl)phenyl 1701 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(N,N'-me thylmorpholinium- methyl)phenyl 1702 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-pyridinium-methyl)phenyl 1703 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-4-(N, N'-dimethylamino)- pyridinium-methyl)phenyl 1704 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-azatanyl-methyl)phenyl 1705 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-azeti dinyl-methyl)phenyl 1706 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-piperazinyl-methyl)phenyl 1707 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(N,N'-BO C-piperazinyl- methyl)phenyl 1708 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-imidazolyl-methyl)phenyl 1709 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-metho xy-N-methylamino- methyl)phenyl 1710 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-pyridonyl-methyl)phenyl 1711 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-(N',N '-dimethylhydrazinyl- methyl)phenyl 1712 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(amidinyl)phenyl 1713 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-guanidinyl)phenyl 1714 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(imidazolyl)phenyl 1715 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(imidazolidinyl)phenyl 1716 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(2-imidazolidinyl- sulfonyl)phenyl 1717 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(2-pyrrolidinyl)phenyl 1718 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(2-piperidinyl)phenyl 1719 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(amidinyl-methyl)phenyl 1720 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(2-imidazolidinyl- methyl)phenyl 1721 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1722 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-dimethylaminoimidazol-1-yl 1723 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(3-amino phenyl) 1724 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(3-pyrrolidinylcarbonyl) 1725 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-glycinoy l 1726 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(imidazol-1-ylacetyl) 1727 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1728 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-piper idinyl-methyl)phenyl 1729 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-morpholino-methyl)phenyl 1730 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N,N'-me thylmorpholinium- methyl)phenyl 1731 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-pyridinium-methyl)phenyl 1732 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-4-(N, N'-dimethylamino)- pyridinium-methyl)phenyl 1733 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-azatanyl-methyl)phenyl 1734 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-azeti dinyl-methyl)phenyl 1735 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-piperazinyl-methyl)phenyl 1736 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N,N'-BO C-piperazinyl- methyl)phenyl 1737 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-imidazolyl-methyl)phenyl 1738 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-metho xy-N-methylamino- methyl)phenyl 1739 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-pyridonyl-methyl)phenyl 1740 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-(N',N '-dimethylhydrazinyl- methyl)phenyl 1741 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(amidinyl)phenyl 1742 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-guanidinyl)phenyl 1743 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(imidazolyl)phenyl 1744 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(imidazolidinyl)phenyl 1745 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 1746 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(2-pyrrolidinyl)phenyl 1747 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(2-piperidinyl)phenyl 1748 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(amidinyl-methyl)phenyl 1749 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(2-imidazolidinyl- methyl)phenyl 1750 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1751 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-dimethylaminoimidazol-1-yl 1752 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(3-amino phenyl) 1753 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(3-pyrrolidinylcarbonyl) 1754 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-glycinoy l 1755 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(imidazol-1-ylacetyl) 1756 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1757 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(N-piperi dinyl-methyl)phenyl 1758 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(N-morpholino-methyl)phenyl 1759 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(N,N'-met hylmorpholinium- methyl)phenyl 1760 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(N-pyridinium-methyl)phenyl 1761 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(N-4-(N,N '-dimethylamino)- pyridinium-methyl)phenyl 1762 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(N-azatanyl-methyl)phenyl 1763 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(N-azetid inyl-methyl)phenyl 1764 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(N-piperazinyl-methyl)phenyl 1765 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(N,N'-BOC -piperazinyl- methyl)phenyl 1766 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(N-imidazolyl-methyl)phenyl 1767 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(N-methox y-N-methylamino- methyl)phenyl 1768 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(N-pyridonyl-methyl)phenyl 1769 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(N-(N',N' -dimethylhydrazinyl- methyl)phenyl 1770 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(amidinyl)phenyl 1771 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(N-guanidinyl)phenyl 1772 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(imidazolyl)phenyl 1773 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(imidazolidinyl)phenyl 1774 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 1775 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(2-pyrrolidinyl)phenyl 1776 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(2-piperidinyl)phenyl 1777 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(amidinyl-methyl)phenyl 1778 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(2-imidazolidinyl- methyl)phenyl 1779 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1780 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-dimethylaminoimidazol-1-yl 1781 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(3-aminop henyl) 1782 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(3-pyrrolidinylcarbonyl) 1783 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-glycinoyl 1784 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(imidazol-1-ylacetyl) 1785 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-pyrrolidinyl-methyl)phenyl 1786 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-piperidinyl-methyl)phenyl 1787 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-morpholino-methyl)phenyl 1788 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N,N'-methylmorpholinium- methyl)phenyl 1789 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-pyridinium-methyl)phenyl 1790 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-4-(N,N'-dimethylamino)- pyridinium-methyl)phenyl 1791 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-azatanyl-methyl)phenyl 1792 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-azetidinyl-methyl)phenyl 1793 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-piperazinyl-methyl)phenyl 1794 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N,N'-BOC-piperazinyl- methyl)phenyl 1795 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-imidazolyl-methyl)phenyl 1796 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-methoxy-N-methylamino- methyl)phenyl 1797 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-pyridonyl-methyl)phenyl 1798 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-(N',N'-dimethylhydrazinyl- methyl)phenyl 1799 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(amidinyl)phenyl 1800 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-guanidinyl)phenyl 1801 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(imidazolyl)phenyl 1802 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(imidazolidinyl)phenyl 1803 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(2-imidazolidinyl- sulfonyl)phenyl 1804 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(2-pyrrolidinyl)phenyl 1805 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(2-piperidinyl)phenyl 1806 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(amidinyl-methyl)phenyl 1807 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(2-imidazolidinyl- methyl)phenyl 1808 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(N-(2-aminoimidazolyl)- methyl)phenyl 1809 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-dimethylaminoimidazol-1-yl 1810 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(3-aminophenyl) 1811 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(3-pyrrolidinylcarbonyl) 1812 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-glycinoyl 1813 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(imidazol-1-ylacetyl)______________________________________
TABLE 3__________________________________________________________________________ ##STR74##__________________________________________________________________________ #STR75## #STR76## ##STR77##__________________________________________________________________________a.sub.1 R = F, D = NH.sub.2 b.sub.1 R = F, D = NH.sub.2 c.sub.1 R = F, D = NH.sub.2 a.sub.2 R = H, D = NH.sub.2 b.sub.2 R = H, D = NH.sub.2 c.sub.2 R = H, D = NH.sub.2 a.sub.3 R = F, D = CH.sub.2 NH.sub.2 b.sub.3 R = F, D = CH.sub.2 NH.sub.2 c.sub.3 R = F, D = CH.sub.2 NH.sub.2 a.sub.4 R = H, D = CH.sub.2 NH.sub.2 b.sub.4 R = H, D = CH.sub.2 NH.sub.2 c.sub.4 R = H, D = CH.sub.2 NH.sub.2 a.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 b.sub.5 R = F, D = C(.dbd.NH)NH.su b.2 c.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 a.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 b.sub.6 R = H, D = C(.dbd.NH)NH.su b.2 c.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 a.sub.7 R = F, D = C(O)NH.sub.2 b.sub.7 R = F, D = C(O)NH.sub.2 c.sub.7 R = F, D = C(O)NH.sub.2 a.sub.8 R = H, D = C(O)NH.su b.2 b.sub.8 R = H, D = C(O)NH.sub.2 c.sub.8 R = H, D = C(O)NH.sub.2__________________________________________________________________________ #STR78## #STR79## ##STR80##__________________________________________________________________________d.sub.1 R = F, D = NH.sub.2 e.sub.1 R = F, D = NH.sub.2 f.sub.1 R = F, D = NH.sub.2 d.sub.2 R = H, D = NH.sub.2 e.sub.2 R = H, D = NH.sub.2 f.sub.2 R = H, D = NH.sub.2 d.sub.3 R = F, D = CH.sub.2 NH.sub.2 e.sub.3 R = F, D = CH.sub.2 NH.sub.2 f.sub.3 R = F, D = CH.sub.2 NH.sub.2 d.sub.4 R = H, D = CH.sub.2 NH.sub.2 e.sub.4 R = H, D = CH.sub.2 NH.sub.2 f.sub.4 R = H, D = CH.sub.2 NH.sub.2 d.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 e.sub.5 R = F, D = C(.dbd.NH)NH.su b.2 f.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 d.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 e.sub.6 R = H, D = C(.dbd.NH)NH.su b.2 f.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 d.sub.7 R = F, D = C(O)NH.sub.2 e.sub.7 R = F, D = C(O)NH.sub.2 f.sub.7 R = F, D = C(O)NH.sub.2 d.sub.8 R = H, D = C(O)NH.su b.2 e.sub.8 R = H, D = C(O)NH.sub.2 f.sub.8 R = H, D = C(O)NH.sub.2__________________________________________________________________________ #STR81## #STR82## ##STR83##__________________________________________________________________________g.sub.1 R = F, D = NH.sub.2 h.sub.1 R = F, D = NH.sub.2 i.sub.1 R = F, D = NH.sub.2 g.sub.2 R = H, D = NH.sub.2 h.sub.2 R = H, D = NH.sub.2 i.sub.2 R = H, D = NH.sub.2 g.sub.3 R = F, D = CH.sub.2 NH.sub.2 h.sub.3 R = F, D = CH.sub.2 NH.sub.2 i.sub.3 R = F, D = CH.sub.2 NH.sub.2 g.sub.4 R = H, D = CH.sub.2 NH.sub.2 h.sub.4 R = H, D = CH.sub.2 NH.sub.2 i.sub.4 R = H, D = CH.sub.2 NH.sub.2 g.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 h.sub.5 R = F, D = C(.dbd.NH)NH.su b.2 i.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 g.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 h.sub.6 R = H, D = C(.dbd.NH)NH.su b.2 i.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 g.sub.7 R = F, D = C(O)NH.sub.2 h.sub.7 R = F, D = C(O)NH.sub.2 i.sub.7 R = F, D = C(O)NH.sub.2 g.sub.8 R = H, D = C(O)NH.su b.2 h.sub.8 R = H, D = C(O)NH.sub.2 i.sub.8 R = H, D = C(O)NH.sub.2__________________________________________________________________________ #STR84## #STR85## ##STR86##__________________________________________________________________________j.sub.1 R = F, D = NH.sub.2 k.sub.1 R = F, D = NH.sub.2 l.sub.1 R = F, D = NH.sub.2 j.sub.2 R = H, D = NH.sub.2 k.sub.2 R = H, D = NH.sub.2 l.sub.2 R = H, D = NH.sub.2 j.sub.3 R = F, D = CH.sub.2 NH.sub.2 k.sub.3 R = F, D = CH.sub.2 NH.sub.2 l.sub.3 R = F, D = CH.sub.2 NH.sub.2 j.sub.4 R = H, D = CH.sub.2 NH.sub.2 k.sub.4 R = H, D = CH.sub.2 NH.sub.2 l.sub.4 R = H, D = CH.sub.2 NH.sub.2 j.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 k.sub.5 R = F, D = C(.dbd.NH)NH.su b.2 l.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 j.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 k.sub.6 R = H, D = C(.dbd.NH)NH.su b.2 l.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 j.sub.7 R = F, D = C(O)NH.sub.2 k.sub.7 R = F, D = C(O)NH.sub.2 l.sub.7 R = F, D = C(O)NH.sub.2 j.sub.8 R = H, D = C(O)NH.su b.2 k.sub.8 R = H, D = C(O)NH.sub.2 l.sub.8 R = H, D = C(O)NH.sub.2__________________________________________________________________________ #STR87## #STR88## ##STR89##__________________________________________________________________________m.sub.1 R = F, D = NH.sub.2 n.sub.1 R = F, D = NH.sub.2 o.sub.1 R = F, D = NH.sub.2 m.sub.2 R = H, D = NH.sub.2 n.sub.2 R = H, D = NH.sub.2 o.sub.2 R = H, D = NH.sub.2 m.sub.3 R = F, D = CH.sub.2 NH.sub.2 n.sub.3 R = F, D = CH.sub.2 NH.sub.2 o.sub.3 R = F, D = CH.sub.2 NH.sub.2 m.sub.4 R = H, D = CH.sub.2 NH.sub.2 n.sub.4 R = H, D = CH.sub.2 NH.sub.2 o.sub.4 R = H, D = CH.sub.2 NH.sub.2 m.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 n.sub.5 R = F, D = C(.dbd.NH)NH.su b.2 o.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 m.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 n.sub.6 R = H, D = C(.dbd.NH)NH.su b.2 o.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 m.sub.7 R = F, D = C(O)NH.sub.2 n.sub.7 R = F, D = C(O)NH.sub.2 o.sub.7 R = F, D = C(O)NH.sub.2 m.sub.8 R = H, D = C(O)NH.su b.2 n.sub.8 R = H, D = C(O)NH.sub.2 o.sub.8 R = H, D = C(O)NH.sub.2__________________________________________________________________________ #STR90## #STR91## ##STR92##__________________________________________________________________________p.sub.1 R = F, D = NH.sub.2 q.sub.1 R = F, D = NH.sub.2 r.sub.1 R = F, D = NH.sub.2 p.sub.2 R = Cl, D = NH.sub.2 q.sub.2 R = Cl, D = NH.sub.2 r.sub.2 R = Cl, D = NH.sub.2 p.sub.3 R = OMe, D = NH.sub.2 q.sub.3 R = OMe, D = NH.sub.2 r.sub.3 R = OMe, D = NH.sub.2 p.sub.4 R = F, D = CH.sub.2 NH.sub.2 q.sub.4 R = F, D = CH.sub.2 NH.sub.2 r.sub.4 R = F, D = CH.sub.2 NH.sub.2 p.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 q.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 r.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 p.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 q.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 r.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 p.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 q.sub.7 R = F, D = C(.dbd.NH)NH.su b.2 r.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 p.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 q.sub.8 R = Cl, D = C(.dbd.NH)NH. sub.2 r.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 p.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 q.sub.9 R = OMe, D = C(.dbd.NH)N H.sub.2 r.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 p.sub.10 R = F, D = C(O)NH.sub.2 q.sub.10 R = F, D = C(O)NH.sub.2 r.sub.10 R = F, D = C(O)NH.su b.2 p.sub.11 R = Cl, D = C(O)NH.sub.2 q.sub.11 R = Cl, D = C(O)NH.sub.2 r.sub.11 R = Cl, D = C(O)NH.sub.2 p.sub.12 R = OMe, D = C(O)NH.sub.2 q.sub.12 R = OMe, D = C(O)NH.sub.2 r.sub.12 R = OMe, D = C(O)NH.sub.2__________________________________________________________________________ #STR93## #STR94## ##STR95##__________________________________________________________________________s.sub.1 R = F, D = NH.sub.2 t.sub.1 R = F, D = NH.sub.2 u.sub.1 R = F, D = NH.sub.2 s.sub.2 R = Cl, D = NH.sub.2 t.sub.2 R = Cl, D = NH.sub.2 u.sub.2 R = Cl, D = NH.sub.2 s.sub.3 R = OMe, D = NH.sub.2 t.sub.3 R = OMe, D = NH.sub.2 u.sub.3 R = OMe, D = NH.sub.2 s.sub.4 R = F, D = CH.sub.2 NH.sub.2 t.sub.4 R = F, D = CH.sub.2 NH.sub.2 u.sub.4 R = F, D = CH.sub.2 NH.sub.2 s.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 t.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 u.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 s.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 t.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 u.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 s.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 t.sub.7 R = F, D = C(.dbd.NH)NH.su b.2 u.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 s.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 t.sub.8 R = Cl, D = C(.dbd.NH)NH. sub.2 u.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 s.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 t.sub.9 R = OMe, D = C(.dbd.NH)N H.sub.2 u.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 s.sub.10 R = F, D = C(O)NH.sub.2 t.sub.10 R = F, D = C(O)NH.sub.2 u.sub.10 R = F, D = C(O)NH.su b.2 s.sub.11 R = Cl, D = C(O)NH.sub.2 t.sub.11 R = Cl, D = C(O)NH.sub.2 u.sub.11 R = Cl, D = C(O)NH.sub.2 s.sub.12 R = OMe, D = C(O)NH.sub.2 t.sub.12 R = OMe, D = C(O)NH.sub.2 u.sub.12 R = OMe, D = C(O)NH.sub.2__________________________________________________________________________ #STR96## #STR97## ##STR98##__________________________________________________________________________v.sub.1 R = F, D = NH.sub.2 w.sub.1 R = F, D = NH.sub.2 x.sub.1 R = F, D = NH.sub.2 v.sub.2 R = Cl, D = NH.sub.2 w.sub.2 R = Cl, D = NH.sub.2 x.sub.2 R = Cl, D = NH.sub.2 v.sub.3 R = OMe, D = NH.sub.2 w.sub.3 R = OMe, D = NH.sub.2 x.sub.3 R = OMe, D = NH.sub.2 v.sub.4 R = F, D = CH.sub.2 NH.sub.2 w.sub.4 R = F, D = CH.sub.2 NH.sub.2 x.sub.4 R = F, D = CH.sub.2 NH.sub.2 v.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 w.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 x.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 v.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 w.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 x.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 v.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 w.sub.7 R = F, D = C(.dbd.NH)NH.su b.2 x.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 v.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 w.sub.8 R = Cl, D = C(.dbd.NH)NH. sub.2 x.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 v.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 w.sub.9 R = OMe, D = C(.dbd.NH)N H.sub.2 x.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 v.sub.10 R = F, D = C(O)NH.sub.2 w.sub.10 R = F, D = C(O)NH.sub.2 x.sub.10 R = F, D = C(O)NH.su b.2 v.sub.11 R = Cl, D = C(O)NH.sub.2 w.sub.11 R = Cl, D = C(O)NH.sub.2 x.sub.11 R = Cl, D = C(O)NH.sub.2 v.sub.12 R = OMe, D = C(O)NH.sub.2 w.sub.12 R = OMe, D = C(O)NH.sub.2 x.sub.12 R = OMe, D = C(O)NH.sub.2__________________________________________________________________________ #STR99## #STR100## ##STR101##__________________________________________________________________________y.sub.1 R = F, D = NH.sub.2 z.sub.1 R = F, D = NH.sub.2 aa.sub.1 R = F, D = NH.sub.2 y.sub.2 R = Cl, D = NH.sub.2 z.sub.2 R = Cl, D = NH.sub.2 aa.sub.2 R = Cl, D = NH.sub.2 y.sub.3 R = OMe, D = NH.sub.2 z.sub.3 R = OMe, D = NH.sub.2 aa.sub.3 R = OMe, D = NH.sub.2 y.sub.4 R = F, D = CH.sub.2 NH.sub.2 z.sub.4 R = F, D = CH.sub.2 NH.sub.2 aa.sub.4 R = F, D = CH.sub.2 NH.sub.2 y.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 z.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 aa.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 y.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 z.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 aa.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 y.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 z.sub.7 R = F, D = C(.dbd.NH)NH.su b.2 aa.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 y.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 z.sub.8 R = Cl, D = C(.dbd.NH)NH. sub.2 aa.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 y.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 z.sub.9 R = OMe, D = C(.dbd.NH)N H.sub.2 aa.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 y.sub.10 R = F, D = C(O)NH.sub.2 z.sub.10 R = F, D = C(O)NH.sub.2 aa.sub.10 R = F, D = C(O)NH.sub.2 y.sub.11 R = Cl, D = C(O)NH.sub.2 z.sub.11 R = Cl, D = C(O)NH.sub.2 aa.sub.11 R = Cl, D = C(O)NH.sub.2 y.sub.12 R = OMe, D = C(O)NH.sub.2 z.sub.12 R = OMe, D = C(O)NH.sub.2 aa.sub.12 R = OMe, D = C(O)NH.sub.2__________________________________________________________________________ #STR102## #STR103## ##STR104##__________________________________________________________________________bb.sub.1 R = F, D = NH.sub.2 cc.sub.1 R = F, D = NH.sub.2 dd.sub.1 R = F, D = NH.sub.2 bb.sub.2 R = Cl, D = NH.sub.2 cc.sub.2 R = Cl, D = NH.sub.2 dd.sub.2 R = Cl, D = NH.sub.2 bb.sub.3 R = OMe, D = NH.sub.2 cc.sub.3 R = OMe, D = NH.sub.2 dd.sub.3 R = OMe, D = NH.sub.2 bb.sub.4 R = F, D = CH.sub.2 NH.sub.2 cc.sub.4 R = F, D = CH.sub.2 NH.sub.2 dd.sub.4 R = F, D = CH.sub.2 NH.sub.2 bb.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 cc.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 dd.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 bb.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 cc.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 dd.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 bb.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 cc.sub.7 R = F, D = C(.dbd.NH)NH. sub.2 dd.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 bb.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 cc.sub.8 R = Cl, D = C(.dbd.NH)N H.sub.2 dd.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 bb.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 cc.sub.9 R = OMe, D = C(.dbd.NH )NH.sub.2 dd.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 bb.sub.10 R = F, D = C(O)NH.sub.2 cc.sub.10 R = F, D = C(O)NH.sub.2 dd.sub.10 R = F, D = C(O)NH.sub.2 bb.sub.11 R = Cl, D = C(O)NH.sub.2 cc.sub.11 R = Cl, D = C(O)NH.sub.2 dd.sub.11 R = Cl, D = C(O)NH.sub.2 bb.sub.12 R = OMe, D = C(O)NH.sub.2 cc.sub.12 R = OMe, D = C(O)NH.sub.2 dd.sub.12 R = OMe, D = C(O)NH.sub.2__________________________________________________________________________ #STR105## #STR106## ##STR107##__________________________________________________________________________ee.sub.1 R = F, D = CH.sub.2 NH.sub.2 ff.sub.1 R = F, D = CH.sub.2 NH.sub.2 gg.sub.1 R = F, D = CH.sub.2 NH.sub.2 ee.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 ff.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 gg.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 ee.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 ff.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 gg.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 ee.sub.4 R = CH.sub.2 NH.sub.2, ff.sub.4 R = CH.sub.2 NH.sub.2, gg.sub.4 R = CH.sub.2 NH.sub.2, D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2__________________________________________________________________________ #STR108## #STR109## ##STR110##__________________________________________________________________________hh.sub.1 R = F, D = CH.sub.2 NH.sub.2 ii.sub.1 R = F, D = CH.sub.2 NH.sub.2 jj.sub.1 R = F, D = CH.sub.2 NH.sub.2 hh.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 ii.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 jj.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 hh.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 ii.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 jj.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 hh.sub.4 R = CH.sub.2 NH.sub.2, ii.sub.4 R = CH.sub.2 NH.sub.2, jj.sub.4 R = CH.sub.2 NH.sub.2, D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2__________________________________________________________________________ #STR111## #STR112## ##STR113##__________________________________________________________________________kk.sub.1 R = F, D = CH.sub.2 NH.sub.2 ll.sub.1 R = F, D = CH.sub.2 NH.sub.2 mm.sub.1 R = F, D = CH.sub.2 NH.sub.2 kk.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 ll.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 mm.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 kk.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 ll.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 mm.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 kk.sub.4 R = CH.sub.2 NH.sub.2, ll.sub.4 R = CH.sub.2 NH.sub.2, mm.sub.4 R = CH.sub.2 NH.sub.2, D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2__________________________________________________________________________ #STR114## #STR115## ##STR116##__________________________________________________________________________nn.sub.1 R = F, D = CH.sub.2 NH.sub.2 oo.sub.1 R = F, D = CH.sub.2 NH.sub.2 pp.sub.1 R = F, D = CH.sub.2 NH.sub.2 nn.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 oo.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 pp.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 nn.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 oo.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 pp.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 nn.sub.4 R = CH.sub.2 NH.sub.2, oo.sub.4 R = CH.sub.2 NH.sub.2, pp.sub.4 R = CH.sub.2 NH.sub.2, D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2__________________________________________________________________________ #STR117## #STR118## ##STR119##__________________________________________________________________________qq.sub.1 R = F, D = CH.sub.2 NH.sub.2 rr.sub.1 R = F, D = CH.sub.2 NH.sub.2 ss.sub.1 R = F, D = CH.sub.2 NH.sub.2 qq.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 rr.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 ss.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 qq.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 rr.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 ss.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 qq.sub.4 R = CH.sub.2 NH.sub.2, rr.sub.4 R = CH.sub.2 NH.sub.2, ss.sub.4 R = CH.sub.2 NH.sub.2, D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2__________________________________________________________________________
______________________________________Ex# R.sup.1b A B______________________________________1 H phenyl 2-((Me).sub.2 N-methyl)phenyl 2 H phenyl 2-((Me)NH-methyl)phenyl 3 H phenyl 2-(H.sub.2 N-methyl)phenyl 4 H phenyl 2-HOCH.sub.2 -phenyl 5 H 2-F-phenyl 2-((Me).sub.2 N-methyl)phenyl 6 H 2-F-phenyl 2-((Me)NH-methyl)phenyl 7 H 2-F-phenyl 2-(H.sub.2 N-methyl)phenyl 8 H 2-F-phenyl 2-HOCH.sub.2 -phenyl 9 H phenyl 2-methylimidazol-1-yl 10 H phenyl 2-ethylimidazol-1-yl 11 H phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 12 H phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 13 H phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 14 H 2-F-phenyl 2-methylimidazol-1-yl 15 H 2-F-phenyl 2-ethylimidazol-1-yl 16 H 2-F-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 17 H 2-F-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 18 H 2-F-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 19 H 2-Cl-phenyl 2-methylimidazol-1-yl 20 H 2-Cl-phenyl 2-ethylimidazol-1-yl 21 H 2-Cl-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 22 H 2-Cl-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 23 H 2-Cl-phenyl 2-CH.sub.3 OCH.sub.2 -imidazo1-1-y1 24 H 2-(Me).sub.2 N-phenyl 2-methylimidazol-1-yl 25 H 2-(Me).sub.2 N-phenyl 2-ethylimidazol-1-yl 26 H 2-(Me).sub.2 N-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 27 H 2-(Me).sub.2 N-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 28 H 2-(Me).sub.2 N-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 29 H phenyl N-methylimidazol-2-yl 30 H phenyl 4-methylimidazol-5-yl 31 H phenyl 5-CF.sub.3 -pyrazol-1-yl 32 H 2-F-phenyl N-methylimidazol-2-yl 33 H 2-F-phenyl 4-methylimidazol-5-yl 34 H 2-F-phenyl 5-CF.sub.3 -pyrazol-1-yl 35 H phenyl guanidino 36 H phenyl 2-thiazolin-2-ylamine 37 H phenyl N-methyl-2-imidazolin-2-yl 38 H phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 39 H phenyl N-methylimidazol-2-ylthiol 40 H phenyl t-butoxycarbonylamine 41 H phenyl (N-pyrrolidino)formylimino 42 H phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 43 H 2-F-phenyl guanidino 44 H 2-F-phenyl 2-thiazolin-2-ylamine 45 H 2-F-phenyl N-methyl-2-imidazolin-2-yl 46 H 2-F-phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 47 H 2-F-phenyl N-methylimidazol-2-ylthio 48 H 2-F-phenyl t-butoxycarbonylamine 49 H 2-F-phenyl (N-pyrrolidino)formylimino 50 H 2-F-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 51 H 2-CH.sub.3 O-phenyl (N-pyrrolidino)formylimino 52 H 2-CH.sub.3 O-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 53 --CN phenyl 2-((Me).sub.2 N-methyl)phenyl 54 --CN phenyl 2-((Me)NH-methyl)phenyl 55 --CN phenyl 2-(H.sub.2 N-methyl)phenyl 56 --CN phenyl 2-HOCH.sub.2 -phenyl 57 --CN 2-F-phenyl 2-((Me).sub.2 N-methyl)phenyl 58 --CN 2-F-phenyl 2-((Me)NH-methyl)phenyl 59 --CN 2-F-phenyl 2-(H.sub.2 N-methyl)phenyl 60 --CN 2-F-phenyl 2-HOCH.sub.2 -phenyl 61 --CN phenyl 2-methylimidazol-1-yl 62 --CN phenyl 2-ethylimidazol-1-yl 63 --CN phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 64 --CN phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 65 --CN phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 66 --CN 2-F-phenyl 2-methylimidazol-1-yl 67 --CN 2-F-phenyl 2-ethylimidazol-1-yl 68 --CN 2-F-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 69 --CN 2-F-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 70 --CN 2-F-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 71 --CN 2-Cl-phenyl 2-methylimidazol-1-yl 72 --CN 2-Cl-phenyl 2-ethylimidazol-1-yl 73 --CN 2-Cl-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 74 --CN 2-Cl-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 75 --CN 2-Cl-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 76 --CN 2-(Me).sub.2 N-phenyl 2-methylimidazol-1-yl 77 --CN 2-(Me).sub.2 N-phenyl 2-ethylimidazol-1-yl 78 --CN 2-(Me).sub.2 N-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 79 --CN 2-(Me).sub.2 N-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 80 --CN 2-(Me).sub.2 N-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 81 --CN phenyl N-methylimidazol-2-yl 82 --CN phenyl 4-methylimidazol-5-yl 83 --CN phenyl 5-CF.sub.3 -pyrazol-1-yl 84 --CN 2-F-phenyl N-methylimidazol-2-yl 85 --CN 2-F-phenyl 4-methylimidazol-5-yl 86 --CN 2-F-phenyl 5-CF.sub.3 -pyrazol-1-yl 87 --CN phenyl guanidino 88 --CN phenyl 2-thiazolin-2-ylamine 89 --CN phenyl N-methyl-2-imidazolin-2-yl 90 --CN phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 91 --CN phenyl N-methylimidazol-2-ylthiol 92 --CN phenyl t-butoxycarbonylamine 93 --CN phenyl (N-pyrrolidino)formylimino 94 --CN phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 95 --CN 2-F-phenyl guanidino 96 --CN 2-F-phenyl 2-thiazolin-2-ylamine 97 --CN 2-F-phenyl N-methyl-2-imidazolin-2-yl 98 --CN 2-F-phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 99 --CN 2-F-phenyl N-methylimidazol-2-ylthio 100 --CN 2-F-phenyl t-butoxycarbonylamine 101 --CN 2-F-phenyl (N-pyrrolidino)formylimino 102 --CN 2-F-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 103 --CN 2-CH.sub.3 O-phenyl (N-pyrrolidino)formylimino 104 --CN 2-CH.sub.3 O-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 105 CF.sub.3 phenyl 2-((Me).sub.2 N-methyl)phenyl 106 CF.sub.3 phenyl 2-((Me)NH-methyl)phenyl 107 CF.sub.3 phenyl 2-(H.sub.2 N-methyl)phenyl 108 CF.sub.3 phenyl 2-HOCH.sub.2 -phenyl 109 CF.sub.3 2-F-phenyl 2-((Me).sub.2 N-methyl)phenyl 110 CF.sub.3 2-F-phenyl 2-((Me)NH-methyl)phenyl 111 CF.sub.3 2-F-phenyl 2-(H.sub.2 N-methyl)phenyl 112 CF.sub.3 2-F-phenyl 2-HOCH.sub.2 -phenyl 113 CF.sub.3 phenyl 2-methylimidazol-1-yl 114 CF.sub.3 phenyl 2-ethylimidazol-1-yl 115 CF.sub.3 phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 116 CF.sub.3 phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 117 CF.sub.3 phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 118 CF.sub.3 2-F-phenyl 2-methylimidazol-1-yl 119 CF.sub.3 2-F-phenyl 2-ethylimidazol-1-yl 120 CF.sub.3 2-F-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 121 CF.sub.3 2-F-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 122 CF.sub.3 2-F-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 123 CF.sub.3 2-Cl-phenyl 2-methylimidazol-1-yl 124 CF.sub.3 2-Cl-phenyl 2-ethylimidazol-1-yl 125 CF.sub.3 2-Cl-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 126 CF.sub.3 2-Cl-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 127 CF.sub.3 2-Cl-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 128 CF.sub.3 2-(Me).sub.2 N-phenyl 2-methylimidazol-1-yl 129 CF.sub.3 2-(Me).sub.2 N-phenyl 2-ethylimidazol-1-yl 130 CF.sub.3 2-(Me).sub.2 N-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 131 CF.sub.3 2-(Me).sub.2 N-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 132 CF.sub.3 2-(Me).sub.2 N-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 133 CF.sub.3 phenyl N-methylimidazol-2-yl 134 CF.sub.3 phenyl 4-methylimidazol-5-yl 135 CF.sub.3 phenyl 5-CF.sub.3 -pyrazol-1-yl 136 CF.sub.3 2-F-phenyl N-methylimidazol-2-yl 137 CF.sub.3 2-F-phenyl 4-methylimidazol-5-yl 138 CF.sub.3 2-F-phenyl 5-CF.sub.3 -pyrazol-1-yl 139 CF.sub.3 phenyl guanidino 140 CF.sub.3 phenyl 2-thiazolin-2-ylamine 141 CF.sub.3 phenyl N-methyl-2-imidazolin-2-yl 142 CF.sub.3 phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 143 CF.sub.3 phenyl N-methylimidazol-2-ylthiol 144 CF.sub.3 phenyl t-butoxycarbonylamine 145 CF.sub.3 phenyl (N-pyrrolidino)formylimino 146 CF.sub.3 phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 147 CF.sub.3 2-F-phenyl guanidino 148 CF.sub.3 2-F-phenyl 2-thiazolin-2-ylamine 149 CF.sub.3 2-F-phenyl N-methyl-2-imidazolin-2-yl 150 CF.sub.3 2-F-phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 151 CF.sub.3 2-F-phenyl N-methylimidazol-2-ylthio 152 CF.sub.3 2-F-phenyl t-butoxycarbonylamine 153 CF.sub.3 2-F-phenyl (N-pyrrolidino)formylimino 154 CF.sub.3 2-F-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 155 CF.sub.3 2-CH.sub.3 O-phenyl (N-pyrrolidino)formylimino 156 CF.sub.3 2-CH.sub.3 O-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 157 CONH.sub.2 phenyl 2-((Me).sub.2 N-methyl)phenyl 158 CONH.sub.2 phenyl 2-((Me)NH-methyl)phenyl 159 CONH.sub.2 phenyl 2-(H.sub.2 N-methyl)phenyl 160 CONH.sub.2 phenyl 2-HOCH.sub.2 -phenyl 161 CONH.sub.2 2-F-phenyl 2-((Me).sub.2 N-methyl)phenyl 162 CONH.sub.2 2-F-phenyl 2-((Me)NH-methyl)phenyl 163 CONH.sub.2 2-F-phenyl 2-(H.sub.2 N-methyl)phenyl 164 CONH.sub.2 2-F-phenyl 2-HOCH.sub.2 -phenyl 165 CONH.sub.2 phenyl 2-methylimidazol-1-yl 166 CONH.sub.2 phenyl 2-ethylimidazol-1-yl 167 CONH.sub.2 phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 168 CONH.sub.2 phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 169 CONH.sub.2 phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 170 CONH.sub.2 2-F-phenyl 2-methylimidazol-1-yl 171 CONH.sub.2 2-F-phenyl 2-ethylimidazol-1-yl 172 CONH.sub.2 2-F-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 173 CONH.sub.2 2-F-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 174 CONH.sub.2 2-F-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 175 CONH.sub.2 2-Cl-phenyl 2-methylimidazol-1-yl 176 CONH.sub.2 2-Cl-phenyl 2-ethylimidazol-1-yl 177 CONH.sub.2 2-Cl-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 178 CONH.sub.2 2-Cl-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 179 CONH.sub.2 2-Cl-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 180 CONH.sub.2 2-(Me).sub.2 N-phenyl 2-methylimidazol-1-yl 181 CONH.sub.2 2-(Me).sub.2 N-phenyl 2-ethylimidazol-1-yl 182 CONH.sub.2 2-(Me).sub.2 N-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-y l 183 CONH.sub.2 2-(Me).sub.2 N-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 184 CONH.sub.2 2-(Me).sub.2 N-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 185 CONH.sub.2 phenyl N-methylimidazol-2-yl 186 CONH.sub.2 phenyl 4-methylimidazol-5-yl 187 CONH.sub.2 phenyl 5-CF.sub.3 -pyrazol-1-yl 188 CONH.sub.2 2-F-phenyl N-methylimidazol-2-yl 189 CONH.sub.2 2-F-phenyl 4-methylimidazol-5-yl 190 CONH.sub.2 2-F-phenyl 5-CF.sub.3 -pyrazol-1-yl 191 CONH.sub.2 phenyl guanidino 192 CONH.sub.2 phenyl 2-thiazolin-2-ylamine 193 CONH.sub.2 phenyl N-methyl-2-imidazolin-2-yl 194 CONH.sub.2 phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 195 CONH.sub.2 phenyl N-methylimidazol-2-ylthiol 196 CONH.sub.2 phenyl t-butoxycarbonylamine 197 CONH.sub.2 phenyl (N-pyrrolidino)formylimino 198 CONH.sub.2 phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 199 CONH.sub.2 2-F-phenyl guanidino 200 CONH.sub.2 2-F-phenyl 2-thiazolin-2-ylamine 201 CONH.sub.2 2-F-phenyl N-methyl-2-imidazolin-2-yl 202 CONH.sub.2 2-F-phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 203 CONH.sub.2 2-F-phenyl N-methylimidazol-2-ylthio 204 CONH.sub.2 2-F-phenyl t-butoxycarbonylamine 205 CONH.sub.2 2-F-phenyl (N-pyrrolidino)formylimino 206 CONH.sub.2 2-F-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 207 CONH.sub.2 2-CH.sub.3 O-phenyl (N-pyrrolidino)formylimino 208 CONH.sub.2 2-CH.sub.3 O-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 209 SCH.sub.3 phenyl 2-((Me).sub.2 N-methyl)phenyl 210 SCH.sub.3 phenyl 2-((Me)NH-methyl)phenyl 211 SCH.sub.3 phenyl 2-(H.sub.2 N-methyl)phenyl 212 SCH.sub.3 phenyl 2-HOCH.sub.2 -phenyl 213 SCH.sub.3 2-F-phenyl 2-((Me).sub.2 N-methyl)phenyl 214 SCH.sub.3 2-F-phenyl 2-((Me)NH-methyl)phenyl 215 SCH.sub.3 2-F-phenyl 2-(H.sub.2 N-methyl)phenyl 216 SCH.sub.3 2-F-phenyl 2-HOCH.sub.2 -phenyl 217 SCH.sub.3 phenyl 2-methylimidazol-1-yl 218 SCH.sub.3 phenyl 2-ethylimidazol-1-yl 219 SCH.sub.3 phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 220 SCH.sub.3 phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 221 SCH.sub.3 phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 222 SCH.sub.3 2-F-phenyl 2-methylimidazol-1-yl 223 SCH.sub.3 2-F-phenyl 2-ethylimidazol-1-yl 224 SCH.sub.3 2-F-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 225 SCH.sub.3 2-F-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 226 SCH.sub.3 2-F-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 227 SCH.sub.3 2-Cl-phenyl 2-methylimidazol-1-yl 228 SCH.sub.3 2-Cl-phenyl 2-ethylimidazol-1-yl 229 SCH.sub.3 2-Cl-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 230 SCH.sub.3 2-Cl-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 231 SCH.sub.3 2-Cl-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 232 SCH.sub.3 2-(Me).sub.2 N-phenyl 2-methylimidazol-1-yl 233 SCH.sub.3 2-(Me).sub.2 N-phenyl 2-ethylimidazol-1-yl 234 SCH.sub.3 2-(Me).sub.2 N-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 235 SCH.sub.3 2-(Me).sub.2 N-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 236 SCH.sub.3 2-(Me).sub.2 N-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 237 SCH.sub.3 phenyl N-methylimidazol-2-yl 238 SCH.sub.3 phenyl 4-methylimidazol-5-yl 239 SCH.sub.3 phenyl 5-CF.sub.3 -pyrazol-1-yl 240 SCH.sub.3 2-F-phenyl N-methylimidazol-2-yl 241 SCH.sub.3 2-F-phenyl 4-methylimidazol-5-yl 242 SCH.sub.3 2-F-phenyl 5-CF.sub.3 -pyrazol-1-yl 243 SCH.sub.3 phenyl guanidino 244 SCH.sub.3 phenyl 2-thiazolin-2-ylamine 245 SCH.sub.3 phenyl N-methyl-2-imidazolin-2-yl 246 SCH.sub.3 phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 247 SCH.sub.3 phenyl N-methylimidazol-2-ylthiol 248 SCH.sub.3 phenyl t-butoxycarbonylamine 249 SCH.sub.3 phenyl (N-pyrrolidino)formylimino 250 SCH.sub.3 phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 251 SCH.sub.3 2-F-phenyl guanidino 252 SCH.sub.3 2-F-phenyl 2-thiazolin-2-ylamine 253 SCH.sub.3 2-F-phenyl N-methyl-2-imidazolin-2-yl 254 SCH.sub.3 2-F-phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 255 SCH.sub.3 2-F-phenyl N-methylimidazol-2-ylthio 256 SCH.sub.3 2-F-phenyl t-butoxycarbonylamine 257 SCH.sub.3 2-F-phenyl (N-pyrrolidino)formylimino 258 SCH.sub.3 2-F-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 259 SCH.sub.3 2-CH.sub.3 O-phenyl (N-pyrrolidino)formylimino 260 SCH.sub.3 2-CH.sub.3 O-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 261 SO.sub.2 CH.sub.3 phenyl 2-((Me).sub.2 N-methyl)phenyl 262 SO.sub.2 CH.sub.3 phenyl 2-((Me)NH-methyl)phenyl 263 SO.sub.2 CH.sub.3 phenyl 2-(H.sub.2 N-methyl)phenyl 264 SO.sub.2 CH.sub.3 phenyl 2-HOCH.sub.2 -phenyl 265 SO.sub.2 CH.sub.3 2-F-phenyl 2-((Me).sub.2 N-methyl)phenyl 266 SO.sub.2 CH.sub.3 2-F-phenyl 2-((Me)NH-methyl)phenyl 267 SO.sub.2 CH.sub.3 2-F-phenyl 2-(H.sub.2 N-methyl)phenyl 268 SO.sub.2 CH.sub.3 2-F-phenyl 2-HOCH.sub.2 -phenyl 269 SO.sub.2 CH.sub.3 phenyl 2-methylimidazol-1-yl 270 SO.sub.2 CH.sub.3 phenyl 2-ethylimidazol-1-yl 271 SO.sub.2 CH.sub.3 phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 272 SO.sub.2 CH.sub.3 phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 273 SO.sub.2 CH.sub.3 phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 274 SO.sub.2 CH.sub.3 2-F-phenyl 2-methylimida zol-1-yl 275 SO.sub.2 CH.sub.3 2-F-phenyl 2-ethylimidazol-1-yl 276 SO.sub.2 CH.sub.3 2-F-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 277 SO.sub.2 CH.sub.3 2-F-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 278 SO.sub.2 CH.sub.3 2-F-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 279 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-methylimid azol-1-yl 280 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-ethylimidazol-1-yl 281 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 282 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 283 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 284 SO.sub.2 CH.sub.3 2-(Me).sub.2 N-phenyl 2-methylimidazol-1-yl 285 SO.sub.2 CH.sub.3 2-(Me).sub.2 N-phenyl 2-ethylimidazol-1-yl 286 SO.sub.2 CH.sub.3 2-(Me).sub.2 N-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 287 SO.sub.2 CH.sub.3 2-(Me).sub.2 N-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 288 SO.sub.2 CH.sub.3 2-(Me).sub.2 N-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 289 SO.sub.2 CH.sub.3 phenyl N-methylimidazol-2-yl 290 SO.sub.2 CH.sub.3 phenyl 4-methylimidazol-5-yl 291 SO.sub.2 CH.sub.3 phenyl 5-CF.sub.3 -pyrazol-1-yl 292 SO.sub.2 CH.sub.3 2-F-phenyl N-methylimidazol-2-yl 293 SO.sub.2 CH.sub.3 2-F-phenyl 4-methylimidazol-5-yl 294 SO.sub.2 CH.sub.3 2-F-phenyl 5-CF.sub.3 -pyrazol-1-yl 295 SO.sub.2 CH.sub.3 phenyl guanidino 296 SO.sub.2 CH.sub.3 phenyl 2-thiazolin-2-ylamine 297 SO.sub.2 CH.sub.3 phenyl N-methyl-2-imidazolin-2-yl 298 SO.sub.2 CH.sub.3 phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 299 SO.sub.2 CH.sub.3 phenyl N-methylimidazol-2-ylthiol 300 SO.sub.2 CH.sub.3 phenyl t-butoxycarbonylamine 301 SO.sub.2 CH.sub.3 phenyl (N-pyrrolidino)formylimino 302 SO.sub.2 CH.sub.3 phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 303 SO.sub.2 CH.sub.3 2-F-phenyl guanidino 304 SO.sub.2 CH.sub.3 2-F-phenyl 2-thiazolin-2-ylamine 305 SO.sub.2 CH.sub.3 2-F-phenyl N-methyl-2-imidazolin-2-yl 306 SO.sub.2 CH.sub.3 2-F-phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 307 SO.sub.2 CH.sub.3 2-F-phenyl N-methylimidazol-2-ylthio 308 SO.sub.2 CH.sub.3 2-F-phenyl t-butoxycarbonylamine 309 SO.sub.2 CH.sub.3 2-F-phenyl (N-pyrrolidino)formylimino 310 SO.sub.2 CH.sub.3 2-F-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 311 SO.sub.2 CH.sub.3 2-CH.sub.3 O-phenyl (N-pyrrolidino)formylimino 312 SO.sub.2 CH.sub.3 2-CH.sub.3 O-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 313 NHSO.sub.2 CH.sub.3 phenyl 2-((Me).sub.2 N-methyl)phenyl 314 NHSO.sub.2 CH.sub.3 phenyl 2-((Me)NH-methyl)phenyl 315 NHSO.sub.2 CH.sub.3 phenyl 2-(H.sub.2 N-methyl)phenyl 316 NHSO.sub.2 CH.sub.3 phenyl 2-HOCH.sub.2 -phenyl 317 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-((Me).sub.2 N-methyl)phenyl 318 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-((Me)NH-m ethyl)phenyl 319 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(H.sub.2 N-methyl)phenyl 320 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-HOCH.sub.2 -phenyl 321 NHSO.sub.2 CH.sub.3 phenyl 2-methylimidazol-1-yl 322 NHSO.sub.2 CH.sub.3 phenyl 2-ethylimidazol-1-yl 323 NHSO.sub.2 CH.sub.3 phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 324 NHSO.sub.2 CH.sub.3 phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 325 NHSO.sub.2 CH.sub.3 phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 326 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-methylimi dazol-1-yl 327 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-ethylimidazol-1-yl 328 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 329 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 330 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 331 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-methylimidazol-1-yl 332 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-ethylimidazol-1-yl 333 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 334 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 335 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 336 NHSO.sub.2 CH.sub.3 2-(Me).sub.2 N-phenyl 2-methylimidazol-1-yl 337 NHSO.sub.2 CH.sub.3 2-(Me).sub.2 N-phenyl 2-ethylimidazol-1-yl 338 NHSO.sub.2 CH.sub.3 2-(Me).sub.2 N-phenyl 2-((Me).sub.2 N-methyl)imi dazol-1-yl 339 NHSO.sub.2 CH.sub.3 2-(Me).sub.2 N-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 340 NHSO.sub.2 CH.sub.3 2-(Me).sub.2 N-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 341 NHSO.sub.2 CH.sub.3 phenyl N-methylimidazol-2-yl 342 NHSO.sub.2 CH.sub.3 phenyl 4-methylimidazol-5-yl 343 NHSO.sub.2 CH.sub.3 phenyl 5-CF.sub.3 -pyrazol-1-yl 344 NHSO.sub.2 CH.sub.3 2-F-phenyl N-methylimidazol-2-yl 345 NHSO.sub.2 CH.sub.3 2-F-phenyl 4-methylimidazol-5-yl 346 NHSO.sub.2 CH.sub.3 2-F-phenyl 5-CF.sub.3 -pyrazol-1-yl 347 NHSO.sub.2 CH.sub.3 phenyl guanidino 348 NHSO.sub.2 CH.sub.3 phenyl 2-thiazolin-2-ylamine 349 NHSO.sub.2 CH.sub.3 phenyl N-methyl-2-imidazolin-2-yl 350 NHSO.sub.2 CH.sub.3 phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 351 NHSO.sub.2 CH.sub.3 phenyl N-methylimidazol-2-ylthiol 352 NHSO.sub.2 CH.sub.3 phenyl t-butoxycarbonylamine 353 NHSO.sub.2 CH.sub.3 phenyl (N-pyrrolidino)formylimino 354 NHSO.sub.2 CH.sub.3 phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 355 NHSO.sub.2 CH.sub.3 2-F-phenyl guanidino 356 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-thiazolin-2-ylamine 357 NHSO.sub.2 CH.sub.3 2-F-phenyl N-methyl-2-imidazolin-2-yl 358 NHSO.sub.2 CH.sub.3 2-F-phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 359 NHSO.sub.2 CH.sub.3 2-F-phenyl N-methylimidazol-2-ylthio 360 NHSO.sub.2 CH.sub.3 2-F-phenyl t-butoxycarbonylamine 361 NHSO.sub.2 CH.sub.3 2-F-phenyl (N-pyrrolidino)formylimino 362 NHSO.sub.2 CH.sub.3 2-F-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 363 NHSO.sub.2 CH.sub.3 2-CH.sub.3 O-phenyl (N-pyrrolidino)formylimino 364 NHSO.sub.2 CH.sub.3 2-CH.sub.3 O-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino______________________________________
TABLE 4__________________________________________________________________________ #STR120##__________________________________________________________________________ #STR121## #STR122## ##STR123##__________________________________________________________________________a.sub.1 R = F, D = NH.sub.2 b.sub.1 R = F, D = NH.sub.2 c.sub.1 R = F, D = NH.sub.2 a.sub.2 R = H, D = NH.sub.2 b.sub.2 R = H, D = NH.sub.2 c.sub.2 R = H, D = NH.sub.2 a.sub.3 R = F, D = CH.sub.2 NH.sub.2 b.sub.3 R = F, D = CH.sub.2 NH.sub.2 c.sub.3 R = F, D = CH.sub.2 NH.sub.2 a.sub.4 R = H, D = CH.sub.2 NH.sub.2 b.sub.4 R = H, D = CH.sub.2 NH.sub.2 c.sub.4 R = H, D = CH.sub.2 NH.sub.2 a.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 b.sub.5 R = F, D = C(.dbd.NH)NH.su b.2 c.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 a.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 b.sub.6 R = H, D = C(.dbd.NH)NH.su b.2 c.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 a.sub.7 R = F, D = C(O)NH.sub.2 b.sub.7 R = F, D = C(O)NH.sub.2 c.sub.7 R = F, D = C(O)NH.sub.2 a.sub.8 R = H, D = C(O)NH.su b.2 b.sub.8 R = H, D = C(O)NH.sub.2 c.sub.8 R = H, D = C(O)NH.sub.2__________________________________________________________________________ #STR124## #STR125## ##STR126##__________________________________________________________________________d.sub.1 R = F, D = NH.sub.2 e.sub.1 R = F, D = NH.sub.2 f.sub.1 R = F, D = NH.sub.2 d.sub.2 R = H, D = NH.sub.2 e.sub.2 R = H, D = NH.sub.2 f.sub.2 R = H, D = NH.sub.2 d.sub.3 R = F, D = CH.sub.2 NH.sub.2 e.sub.3 R = F, D = CH.sub.2 NH.sub.2 f.sub.3 R = F, D = CH.sub.2 NH.sub.2 d.sub.4 R = H, D = CH.sub.2 NH.sub.2 e.sub.4 R = H, D = CH.sub.2 NH.sub.2 f.sub.4 R = H, D = CH.sub.2 NH.sub.2 d.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 e.sub.5 R = F, D = C(.dbd.NH)NH.su b.2 f.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 d.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 e.sub.6 R = H, D = C(.dbd.NH)NH.su b.2 f.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 d.sub.7 R = F, D = C(O)NH.sub.2 e.sub.7 R = F, D = C(O)NH.sub.2 f.sub.7 R = F, D = C(O)NH.sub.2 d.sub.8 R = H, D = C(O)NH.su b.2 e.sub.8 R = H, D = C(O)NH.sub.2 f.sub.8 R = H, D = C(O)NH.sub.2__________________________________________________________________________ #STR127## #STR128## ##STR129##__________________________________________________________________________g.sub.1 R = F, D = NH.sub.2 h.sub.1 R = F, D = NH.sub.2 i.sub.1 R = F, D = NH.sub.2 g.sub.2 R = H, D = NH.sub.2 h.sub.2 R = H, D = NH.sub.2 i.sub.2 R = H, D = NH.sub.2 g.sub.3 R = F, D = CH.sub.2 NH.sub.2 h.sub.3 R = F, D = CH.sub.2 NH.sub.2 i.sub.3 R = F, D = CH.sub.2 NH.sub.2 g.sub.4 R = H, D = CH.sub.2 NH.sub.2 h.sub.4 R = H, D = CH.sub.2 NH.sub.2 i.sub.4 R = H, D = CH.sub.2 NH.sub.2 g.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 h.sub.5 R = F, D = C(.dbd.NH)NH.su b.2 i.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 g.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 h.sub.6 R = H, D = C(.dbd.NH)NH.su b.2 i.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 g.sub.7 R = F, D = C(O)NH.sub.2 h.sub.7 R = F, D = C(O)NH.sub.2 i.sub.7 R = F, D = C(O)NH.sub.2 g.sub.8 R = H, D = C(O)NH.su b.2 h.sub.8 R = H, D = C(O)NH.sub.2 i.sub.8 R = H, D = C(O)NH.sub.2__________________________________________________________________________ #STR130## #STR131## ##STR132##__________________________________________________________________________j.sub.1 R = F, D = NH.sub.2 k.sub.1 R = F, D = NH.sub.2 l.sub.1 R = F, D = NH.sub.2 j.sub.2 R = H, D = NH.sub.2 k.sub.2 R = H, D = NH.sub.2 l.sub.2 R = H, D = NH.sub.2 j.sub.3 R = F, D = CH.sub.2 NH.sub.2 k.sub.3 R = F, D = CH.sub.2 NH.sub.2 l.sub.3 R = F, D = CH.sub.2 NH.sub.2 j.sub.4 R = H, D = CH.sub.2 NH.sub.2 k.sub.4 R = H, D = CH.sub.2 NH.sub.2 l.sub.4 R = H, D = CH.sub.2 NH.sub.2 j.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 k.sub.5 R = F, D = C(.dbd.NH)NH.su b.2 l.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 j.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 k.sub.6 R = H, D = C(.dbd.NH)NH.su b.2 l.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 j.sub.7 R = F, D = C(O)NH.sub.2 k.sub.7 R = F, D = C(O)NH.sub.2 l.sub.7 R = F, D = C(O)NH.sub.2 j.sub.8 R = H, D = C(O)NH.su b.2 k.sub.8 R = H, D = C(O)NH.sub.2 l.sub.8 R = H, D = C(O)NH.sub.2__________________________________________________________________________ #STR133## #STR134## ##STR135##__________________________________________________________________________m.sub.1 R = F, D = NH.sub.2 n.sub.1 R = F, D = NH.sub.2 o.sub.1 R = F, D = NH.sub.2 m.sub.2 R = H, D = NH.sub.2 n.sub.2 R = H, D = NH.sub.2 o.sub.2 R = H, D = NH.sub.2 m.sub.3 R = F, D = CH.sub.2 NH.sub.2 n.sub.3 R = F, D = CH.sub.2 NH.sub.2 o.sub.3 R = F, D = CH.sub.2 NH.sub.2 m.sub.4 R = H, D = CH.sub.2 NH.sub.2 n.sub.4 R = H, D = CH.sub.2 NH.sub.2 o.sub.4 R = H, D = CH.sub.2 NH.sub.2 m.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 n.sub.5 R = F, D = C(.dbd.NH)NH.su b.2 o.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 m.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 n.sub.6 R = H, D = C(.dbd.NH)NH.su b.2 o.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 m.sub.7 R = F, D = C(O)NH.sub.2 n.sub.7 R = F, D = C(O)NH.sub.2 o.sub.7 R = F, D = C(O)NH.sub.2 m.sub.8 R = H, D = C(O)NH.su b.2 n.sub.8 R = H, D = C(O)NH.sub.2 o.sub.8 R = H, D = C(O)NH.sub.2__________________________________________________________________________ #STR136## #STR137## ##STR138##__________________________________________________________________________p.sub.1 R = F, D = NH.sub.2 q.sub.1 R = F, D = NH.sub.2 r.sub.1 R = F, D = NH.sub.2 p.sub.2 R = Cl, D = NH.sub.2 q.sub.2 R = Cl, D = NH.sub.2 r.sub.2 R = Cl, D = NH.sub.2 p.sub.3 R = OMe, D = NH.sub.2 q.sub.3 R = OMe, D = NH.sub.2 r.sub.3 R = OMe, D = NH.sub.2 p.sub.4 R = F, D = CH.sub.2 NH.sub.2 q.sub.4 R = F, D = CH.sub.2 NH.sub.2 r.sub.4 R = F, D = CH.sub.2 NH.sub.2 p.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 q.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 r.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 p.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 q.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 r.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 p.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 q.sub.7 R = F, D = C(.dbd.NH)NH.su b.2 r.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 p.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 q.sub.8 R = Cl, D = C(.dbd.NH)NH. sub.2 r.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 p.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 q.sub.9 R = OMe, D = C(.dbd.NH)N H.sub.2 r.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 p.sub.10 R = F, D = C(O)NH.sub.2 q.sub.10 R = F, D = C(O)NH.sub.2 r.sub.10 R = F, D = C(O)NH.su b.2 p.sub.11 R = Cl, D = C(O)NH.sub.2 q.sub.11 R = Cl, D = C(O)NH.sub.2 r.sub.11 R = Cl, D = C(O)NH.sub.2 p.sub.12 R = OMe, D = C(O)NH.sub.2 q.sub.12 R = OMe, D = C(O)NH.sub.2 r.sub.12 R = OMe, D = C(O)NH.sub.2__________________________________________________________________________ #STR139## #STR140## ##STR141##__________________________________________________________________________s.sub.1 R = F, D = NH.sub.2 t.sub.1 R = F, D = NH.sub.2 u.sub.1 R = F, D = NH.sub.2 s.sub.2 R = Cl, D = NH.sub.2 t.sub.2 R = Cl, D = NH.sub.2 u.sub.2 R = Cl, D = NH.sub.2 s.sub.3 R = OMe, D = NH.sub.2 t.sub.3 R = OMe, D = NH.sub.2 u.sub.3 R = OMe, D = NH.sub.2 s.sub.4 R = F, D = CH.sub.2 NH.sub.2 t.sub.4 R = F, D = CH.sub.2 NH.sub.2 u.sub.4 R = F, D = CH.sub.2 NH.sub.2 s.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 t.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 u.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 s.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 t.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 u.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 s.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 t.sub.7 R = F, D = C(.dbd.NH)NH.su b.2 u.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 s.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 t.sub.8 R = Cl, D = C(.dbd.NH)NH. sub.2 u.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 s.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 t.sub.9 R = OMe, D = C(.dbd.NH)N H.sub.2 u.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 s.sub.10 R = F, D = C(O)NH.sub.2 t.sub.10 R = F, D = C(O)NH.sub.2 u.sub.10 R = F, D = C(O)NH.su b.2 s.sub.11 R = Cl, D = C(O)NH.sub.2 t.sub.11 R = Cl, D = C(O)NH.sub.2 u.sub.11 R = Cl, D = C(O)NH.sub.2 s.sub.12 R = OMe, D = C(O)NH.sub.2 t.sub.12 R = OMe, D = C(O)NH.sub.2 u.sub.12 R = OMe, D = C(O)NH.sub.2__________________________________________________________________________ #STR142## #STR143## ##STR144##__________________________________________________________________________v.sub.1 R = F, D = NH.sub.2 w.sub.1 R = F, D = NH.sub.2 x.sub.1 R = F, D = NH.sub.2 v.sub.2 R = Cl, D = NH.sub.2 w.sub.2 R = Cl, D = NH.sub.2 x.sub.2 R = Cl, D = NH.sub.2 v.sub.3 R = OMe, D = NH.sub.2 w.sub.3 R = OMe, D = NH.sub.2 x.sub.3 R = OMe, D = NH.sub.2 v.sub.4 R = F, D = CH.sub.2 NH.sub.2 w.sub.4 R = F, D = CH.sub.2 NH.sub.2 x.sub.4 R = F, D = CH.sub.2 NH.sub.2 v.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 w.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 x.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 v.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 w.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 x.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 v.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 w.sub.7 R = F, D = C(.dbd.NH)NH.su b.2 x.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 v.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 w.sub.8 R = Cl, D = C(.dbd.NH)NH. sub.2 x.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 v.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 w.sub.9 R = OMe, D = C(.dbd.NH)N H.sub.2 x.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 v.sub.10 R = F, D = C(O)NH.sub.2 w.sub.10 R = F, D = C(O)NH.sub.2 x.sub.10 R = F, D = C(O)NH.su b.2 v.sub.11 R = Cl, D = C(O)NH.sub.2 w.sub.11 R = Cl, D = C(O)NH.sub.2 x.sub.11 R = Cl, D = C(O)NH.sub.2 v.sub.12 R = OMe, D = C(O)NH.sub.2 w.sub.12 R = OMe, D = C(O)NH.sub.2 x.sub.12 R = OMe, D = C(O)NH.sub.2__________________________________________________________________________ #STR145## #STR146## ##STR147##__________________________________________________________________________y.sub.1 R = F, D = NH.sub.2 z.sub.1 R = F, D = NH.sub.2 aa.sub.1 R = F, D = NH.sub.2 y.sub.2 R = Cl, D = NH.sub.2 z.sub.2 R = Cl, D = NH.sub.2 aa.sub.2 R = Cl, D = NH.sub.2 y.sub.3 R = OMe, D = NH.sub.2 z.sub.3 R = OMe, D = NH.sub.2 aa.sub.3 R = OMe, D = NH.sub.2 y.sub.4 R = F, D = CH.sub.2 NH.sub.2 z.sub.4 R = F, D = CH.sub.2 NH.sub.2 aa.sub.4 R = F, D = CH.sub.2 NH.sub.2 y.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 z.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 aa.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 y.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 z.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 aa.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 y.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 z.sub.7 R = F, D = C(.dbd.NH)NH.su b.2 aa.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 y.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 z.sub.8 R = Cl, D = C(.dbd.NH)NH. sub.2 aa.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 y.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 z.sub.9 R = OMe, D = C(.dbd.NH)N H.sub.2 aa.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 y.sub.10 R = F, D = C(O)NH.sub.2 z.sub.10 R = F, D = C(O)NH.sub.2 aa.sub.10 R = F, D = C(O)NH.sub.2 y.sub.11 R = Cl, D = C(O)NH.sub.2 z.sub.11 R = Cl, D = C(O)NH.sub.2 aa.sub.11 R = Cl, D = C(O)NH.sub.2 y.sub.12 R = OMe, D = C(O)NH.sub.2 z.sub.12 R = OMe, D = C(O)NH.sub.2 aa.sub.12 R = OMe, D = C(O)NH.sub.2__________________________________________________________________________ #STR148## #STR149## ##STR150##__________________________________________________________________________bb.sub.1 R = F, D = NH.sub.2 cc.sub.1 R = F, D = NH.sub.2 dd.sub.1 R = F, D = NH.sub.2 bb.sub.2 R = Cl, D = NH.sub.2 cc.sub.2 R = Cl, D = NH.sub.2 dd.sub.2 R = Cl, D = NH.sub.2 bb.sub.3 R = OMe, D = NH.sub.2 cc.sub.3 R = OMe, D = NH.sub.2 dd.sub.3 R = OMe, D = NH.sub.2 bb.sub.4 R = F, D = CH.sub.2 NH.sub.2 cc.sub.4 R = F, D = CH.sub.2 NH.sub.2 dd.sub.4 R = F, D = CH.sub.2 NH.sub.2 bb.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 cc.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 dd.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 bb.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 cc.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 dd.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 bb.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 cc.sub.7 R = F, D = C(.dbd.NH)NH. sub.2 dd.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 bb.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 cc.sub.8 R = Cl, D = C(.dbd.NH)N H.sub.2 dd.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 bb.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 cc.sub.9 R = OMe, D = C(.dbd.NH )NH.sub.2 dd.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 bb.sub.10 R = F, D = C(O)NH.sub.2 cc.sub.10 R = F, D = C(O)NH.sub.2 dd.sub.10 R = F, D = C(O)NH.sub.2 bb.sub.11 R = Cl, D = C(O)NH.sub.2 cc.sub.11 R = Cl, D = C(O)NH.sub.2 dd.sub.11 R = Cl, D = C(O)NH.sub.2 bb.sub.12 R = OMe, D = C(O)NH.sub.2 cc.sub.12 R = OMe, D = C(O)NH.sub.2 dd.sub.12 R = OMe, D = C(O)NH.sub.2__________________________________________________________________________ #STR151## #STR152## ##STR153##__________________________________________________________________________ee.sub.1 R = F, D = CH.sub.2 NH.sub.2 ff.sub.1 R = F, D = CH.sub.2 NH.sub.2 gg.sub.1 R = F, D = CH.sub.2 NH.sub.2 ee.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 ff.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 gg.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 ee.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 ff.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 gg.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 ee.sub.4 R = CH.sub.2 NH.sub.2, ff.sub.4 R = CH.sub.2 NH.sub.2, gg.sub.4 R = CH.sub.2 NH.sub.2, D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2__________________________________________________________________________ #STR154## #STR155## ##STR156##__________________________________________________________________________hh.sub.1 R = F, D = CH.sub.2 NH.sub.2 ii.sub.1 R = F, D = CH.sub.2 NH.sub.2 jj.sub.1 R = F, D = CH.sub.2 NH.sub.2 hh.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 ii.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 jj.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 hh.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 ii.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 jj.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 hh.sub.4 R = CH.sub.2 NH.sub.2, ii.sub.4 R = CH.sub.2 NH.sub.2, jj.sub.4 R = CH.sub.2 NH.sub.2, D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2__________________________________________________________________________ #STR157## #STR158## ##STR159##__________________________________________________________________________kk.sub.1 R = F, D = CH.sub.2 NH.sub.2 ll.sub.1 R = F, D = CH.sub.2 NH.sub.2 mm.sub.1 R = F, D = CH.sub.2 NH.sub.2 kk.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 ll.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 mm.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 kk.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 ll.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 mm.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 kk.sub.4 R = CH.sub.2 NH.sub.2, ll.sub.4 R = CH.sub.2 NH.sub.2, mm.sub.4 R = CH.sub.2 NH.sub.2, D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2__________________________________________________________________________ #STR160## #STR161## ##STR162##__________________________________________________________________________nn.sub.1 R = F, D = CH.sub.2 NH.sub.2 oo.sub.1 R = F, D = CH.sub.2 NH.sub.2 pp.sub.1 R = F, D = CH.sub.2 NH.sub.2 nn.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 oo.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 pp.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 nn.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 oo.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 pp.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 nn.sub.4 R = CH.sub.2 NH.sub.2, oo.sub.4 R = CH.sub.2 NH.sub.2, pp.sub.4 R = CH.sub.2 NH.sub.2, D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2__________________________________________________________________________ #STR163## #STR164## ##STR165##__________________________________________________________________________qq.sub.1 R = F, D = CH.sub.2 NH.sub.2 rr.sub.1 R = F, D = CH.sub.2 NH.sub.2 ss.sub.1 R = F, D = CH.sub.2 NH.sub.2 qq.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 rr.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 ss.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 qq.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 rr.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 ss.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 qq.sub.4 R = CH.sub.2 NH.sub.2, rr.sub.4 R = CH.sub.2 NH.sub.2, ss.sub.4 R = CH.sub.2 NH.sub.2, D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2__________________________________________________________________________
______________________________________Ex# R.sup.1b A B______________________________________1 H phenyl 2-(aminosulfonyl)phenyl 2 H phenyl 2-(methylaminosulfonyl)phenyl 3 H phenyl 1-pyrrolidinocarbonyl 4 H phenyl 2-(methylsulfonyl)phenyl 5 H phenyl 4-morpholino 6 H phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 7 H phenyl 4-morpholinocarbonyl 8 H 2-pyridyl 2-(aminosulfonyl)phenyl 9 H 2-pyridyl 2-(methylaminosulfonyl)phenyl 10 H 2-pyridyl 1-pyrrolidinocarbonyl 11 H 2-pyridyl 2-(methylsulfonyl)phenyl 12 H 2-pyridyl 4-morpholino 13 H 2-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 14 H 2-pyridyl 4-morpholinocarbonyl 15 H 3-pyridyl 2-(aminosulfonyl)phenyl 16 H 3-pyridyl 2-(methylaminosulfonyl)phenyl 17 H 3-pyridyl 1-pyrrolidinocarbonyl 18 H 3-pyridyl 2-(methylsulfonyl)phenyl 19 H 3-pyridyl 4-morpholino 20 H 3-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 21 H 3-pyridyl 4-morpholinocarbonyl 22 H 2-pyrimidyl 2-(aminosulfonyl)phenyl 23 H 2-pyrimidyl 2-(methylaminosulfonyl)phenyl 24 H 2-pyrimidyl 1-pyrrolidinocarbonyl 25 H 2-pyrimidyl 2-(methylsulfonyl)phenyl 26 H 2-pyrimidyl 4-morpholino 27 H 2-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 28 H 2-pyrimidyl 4-morpholinocarbonyl 29 H 5-pyrimidyl 2-(aminosulfonyl)phenyl 30 H 5-pyrimidyl 2-(methylaminosulfonyl)phenyl 31 H 5-pyrimidyl 1-pyrrolidinocarbonyl 32 H 5-pyrimidyl 2-(methylsulfonyl)phenyl 33 H 5-pyrimidyl 4-morpholino 34 H 5-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 35 H 5-pyrimidyl 4-morpholinocarbonyl 36 H 2-Cl-phenyl 2-(aminosulfonyl)phenyl 37 H 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl 38 H 2-Cl-phenyl 1-pyrrolidinocarbonyl 39 H 2-Cl-phenyl 2-(methylsulfonyl)phenyl 40 H 2-Cl-phenyl 4-morpholino 41 H 2-Cl-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 42 H 2-Cl-phenyl 4-morpholinocarbonyl 43 H 2-F-phenyl 2-(aminosulfonyl)phenyl 44 H 2-F-phenyl 2-(methylaminosulfonyl)phenyl 45 H 2-F-phenyl 1-pyrrolidinocarbonyl 46 H 2-F-phenyl 2-(methylsulfonyl)phenyl 47 H 2-F-phenyl 4-morpholino 48 H 2-F-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 49 H 2-F-phenyl 4-morpholinocarbonyl 50 H 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 51 H 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl 52 H 2,5-diF-phenyl 1-pyrrolidinocarbonyl 53 H 2,5-diF-phenyl 2-(methylsulfonyl)phenyl 54 H 2,5-diF-phenyl 4-morpholino 55 H 2,5-diF-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 56 H 2,5-diF-phenyl 4-morpholinocarbonyl 57 --CN phenyl 2-(aminosulfonyl)phenyl 58 --CN phenyl 2-(methylaminosulfonyl)phenyl 59 --CN phenyl 1-pyrrolidinocarbonyl 60 --CN phenyl 2-(methylsulfonyl)phenyl 61 --CN phenyl 4-morpholino 62 --CN phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 63 --CN phenyl 4-morpholinocarbonyl 64 --CN 2-pyridyl 2-(aminosulfonyl)phenyl 65 --CN 2-pyridyl 2-(methylaminosulfonyl)phenyl 66 --CN 2-pyridyl 1-pyrrolidinocarbonyl 67 --CN 2-pyridyl 2-(methylsulfonyl)phenyl 68 --CN 2-pyridyl 4-morpholino 69 --CN 2-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 70 --CN 2-pyridyl 4-morpholinocarbonyl 71 --CN 3-pyridyl 2-(aminosulfonyl)phenyl 72 --CN 3-pyridyl 2-(methylaminosulfonyl)phenyl 73 --CN 3-pyridyl 1-pyrrolidinocarbonyl 74 --CN 3-pyridyl 2-(methylsulfonyl)phenyl 75 --CN 3-pyridyl 4-morpholino 76 --CN 3-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 77 --CN 3-pyridyl 4-morpholinocarbonyl 78 --CN 2-pyrimidyl 2-(aminosulfonyl)phenyl 79 --CN 2-pyrimidyl 2-(methylaminosulfonyl)phenyl 80 --CN 2-pyrimidyl 1-pyrrolidinocarbonyl 81 --CN 2-pyrimidyl 2-(methylsulfonyl)phenyl 82 --CN 2-pyrimidyl 4-morpholino 83 --CN 2-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 84 --CN 2-pyrimidyl 4-morpholinocarbonyl 85 --CN 5-pyrimidyl 2-(aminosulfonyl)phenyl 86 --CN 5-pyrimidyl 2-(methylaminosulfonyl)phenyl 87 --CN 5-pyrimidyl 1-pyrrolidinocarbonyl 88 --CN 5-pyrimidyl 2-(methylsulfonyl)phenyl 89 --CN 5-pyrimidyl 4-morpholino 90 --CN 5-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 91 --CN 5-pyrimidyl 4-morpholinocarbonyl 92 --CN 2-Cl-phenyl 2-(aminosulfonyl)phenyl 93 --CN 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl 94 --CN 2-Cl-phenyl 1-pyrrolidinocarbonyl 95 --CN 2-Cl-phenyl 2-(methylsulfonyl)phenyl 96 --CN 2-Cl-phenyl 4-morpholino 97 --CN 2-Cl-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 98 --CN 2-Cl-phenyl 4-morpholinocarbonyl 99 --CN 2-F-phenyl 2-(aminosulfonyl)phenyl 100 --CN 2-F-phenyl 2-(methylaminosulfonyl)phenyl 101 --CN 2-F-phenyl 1-pyrrolidinocarbonyl 102 --CN 2-F-phenyl 2-(methylsulfonyl)phenyl 103 --CN 2-F-phenyl 4-morpholino 104 --CN 2-F-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 105 --CN 2-F-phenyl 4-morpholinocarbonyl 106 --CN 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 107 --CN 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl 108 --CN 2,5-diF-phenyl 1-pyrrolidinocarbonyl 109 --CN 2,5-diF-phenyl 2-(methylsulfonyl)phenyl 110 --CN 2,5-diF-phenyl 4-morpholino 111 --CN 2,5-diF-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 112 --CN 2,5-diF-phenyl 4-morpholinocarbonyl 113 CF.sub.3 phenyl 2-(aminosulfonyl)phenyl 114 CF.sub.3 phenyl 2-(methylaminosulfonyl)phenyl 115 CF.sub.3 phenyl 1-pyrrolidinocarbonyl 116 CF.sub.3 phenyl 2-(methylsulfonyl)phenyl 117 CF.sub.3 phenyl 4-morpholino 118 CF.sub.3 phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 119 CF.sub.3 phenyl 4-morpholinocarbonyl 120 CF.sub.3 2-pyridyl 2-(aminosulfonyl)phenyl 121 CF.sub.3 2-pyridyl 2-(methylaminosulfonyl)phenyl 122 CF.sub.3 2-pyridyl 1-pyrrolidinocarbonyl 123 CF.sub.3 2-pyridyl 2-(methylsulfonyl)phenyl 124 CF.sub.3 2-pyridyl 4-morpholino 125 CF.sub.3 2-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 126 CF.sub.3 2-pyridyl 4-morpholinocarbonyl 127 CF.sub.3 3-pyridyl 2-(aminosulfonyl)phenyl 128 CF.sub.3 3-pyridyl 2-(methylaminosulfonyl)phenyl 129 CF.sub.3 3-pyridyl 1-pyrrolidinocarbonyl 130 CF.sub.3 3-pyridyl 2-(methylsulfonyl)phenyl 131 CF.sub.3 3-pyridyl 4-morpholino 132 CF.sub.3 3-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 133 CF.sub.3 3-pyridyl 4-morpholinocarbonyl 134 CF.sub.3 2-pyrimidyl 2-(aminosulfonyl)phenyl 135 CF.sub.3 2-pyrimidyl 2-(methylaminosulfonyl)phenyl 136 CF.sub.3 2-pyrimidyl 1-pyrrolidinocarbonyl 137 CF.sub.3 2-pyrimidyl 2-(methylsulfonyl)phenyl 138 CF.sub.3 2-pyrimidyl 4-morpholino 139 CF.sub.3 2-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 140 CF.sub.3 2-pyrimidyl 4-morpholinocarbonyl 141 CF.sub.3 5-pyrimidyl 2-(aminosulfonyl)phenyl 142 CF.sub.3 5-pyrimidyl 2-(methylaminosulfonyl)phenyl 143 CF.sub.3 5-pyrimidyl 1-pyrrolidinocarbonyl 144 CF.sub.3 5-pyrimidyl 2-(methylsulfonyl)phenyl 145 CF.sub.3 5-pyrimidyl 4-morpholino 146 CF.sub.3 5-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 147 CF.sub.3 5-pyrimidyl 4-morpholinocarbonyl 148 CF.sub.3 2-Cl-phenyl 2-(aminosulfonyl)phenyl 149 CF.sub.3 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl 150 CF.sub.3 2-Cl-phenyl 1-pyrrolidinocarbonyl 151 CF.sub.3 2-Cl-phenyl 2-(methylsulfonyl)phenyl 152 CF.sub.3 2-Cl-phenyl 4-morpholino 153 CF.sub.3 2-Cl-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 154 CF.sub.3 2-Cl-phenyl 4-morpholinocarbonyl 155 CF.sub.3 2-F-phenyl 2-(aminosulfonyl)phenyl 156 CF.sub.3 2-F-phenyl 2-(methylaminosulfonyl)phenyl 157 CF.sub.3 2-F-phenyl 1-pyrrolidinocarbonyl 158 CF.sub.3 2-F-phenyl 2-(methylsulfonyl)phenyl 159 CF.sub.3 2-F-phenyl 4-morpholino 160 CF.sub.3 2-F-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 161 CF.sub.3 2-F-phenyl 4-morpholinocarbonyl 162 CF.sub.3 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 163 CF.sub.3 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl 164 CF.sub.3 2,5-diF-phenyl 1-pyrrolidinocarbonyl 165 CF.sub.3 2,5-diF-phenyl 2-(methylsulfonyl)phenyl 166 CF.sub.3 2,5-diF-phenyl 4-morpholino 167 CF.sub.3 2,5-diF-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 168 CF.sub.3 2,5-diF-phenyl 4-morpholinocarbon yl 169 CONH.sub.2 phenyl 2-(aminosulfonyl)phenyl 170 CONH.sub.2 phenyl 2-(methylaminosulfonyl)phenyl 171 CONH.sub.2 phenyl 1-pyrrolidinocarbonyl 172 CONH.sub.2 phenyl 2-(methylsulfonyl)phenyl 173 CONH.sub.2 phenyl 4-morpholino 174 CONH.sub.2 phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 175 CONH.sub.2 phenyl 4-morpholinocarbonyl 176 CONH.sub.2 2-pyridyl 2-(aminosulfonyl)phenyl 177 CONH.sub.2 2-pyridyl 2-(methylaminosulfonyl)phenyl 178 CONH.sub.2 2-pyridyl 1-pyrrolidinocarbonyl 179 CONH.sub.2 2-pyridyl 2-(methylsulfonyl)phenyl 180 CONH.sub.2 2-pyridyl 4-morpholino 181 CONH.sub.2 2-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 182 CONH.sub.2 2-pyridyl 4-morpholinocarbonyl 183 CONH.sub.2 3-pyridyl 2-(aminosulfonyl)phenyl 184 CONH.sub.2 3-pyridyl 2-(methylaminosulfonyl)phenyl 185 CONH.sub.2 3-pyridyl 1-pyrrolidinocarbonyl 186 CONH.sub.2 3-pyridyl 2-(methylsulfonyl)phenyl 187 CONH.sub.2 3-pyridyl 4-morpholino 188 CONH.sub.2 3-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 189 CONH.sub.2 3-pyridyl 4-morpholinocarbonyl 190 CONH.sub.2 2-pyrimidyl 2-(aminosulfonyl)phenyl 191 CONH.sub.2 2-pyrimidyl 2-(methylaminosulfonyl)phenyl 192 CONH.sub.2 2-pyrimidyl 1-pyrrolidinocarbonyl 193 CONH.sub.2 2-pyrimidyl 2-(methylsulfonyl)phenyl 194 CONH.sub.2 2-pyrimidyl 4-morpholino 195 CONH.sub.2 2-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 196 CONH.sub.2 2-pyrimidyl 4-morpholinocarbonyl 197 CONH.sub.2 5-pyrimidyl 2-(aminosulfonyl)phenyl 198 CONH.sub.2 5-pyrimidyl 2-(methylaminosulfonyl)phenyl 199 CONH.sub.2 5-pyrimidyl 1-pyrrolidinocarbonyl 200 CONH.sub.2 5-pyrimidyl 2-(methylsulfonyl)phenyl 201 CONH.sub.2 5-pyrimidyl 4-morpholino 202 CONH.sub.2 5-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 203 CONH.sub.2 5-pyrimidyl 4-morpholinocarbonyl 204 CONH.sub.2 2-Cl-phenyl 2-(aminosulfonyl)phenyl 205 CONH.sub.2 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl 206 CONH.sub.2 2-Cl-phenyl 1-pyrrolidinocarbonyl 207 CONH.sub.2 2-Cl-phenyl 2-(methylsulfonyl)phenyl 208 CONH.sub.2 2-Cl-phenyl 4-morpholino 209 CONH.sub.2 2-Cl-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 210 CONH.sub.2 2-Cl-phenyl 4-morpholinocarbonyl 211 CONH.sub.2 2-F-phenyl 2-(aminosulfonyl)phenyl 212 CONH.sub.2 2-F-phenyl 2-(methylaminosulfonyl)phenyl 213 CONH.sub.2 2-F-phenyl 1-pyrrolidinocarbonyl 214 CONH.sub.2 2-F-phenyl 2-(methylsulfonyl)phenyl 215 CONH.sub.2 2-F-phenyl 4-morpholino 216 CONH.sub.2 2-F-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 217 CONH.sub.2 2-F-phenyl 4-morpholinocarbonyl 218 CONH.sub.2 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 219 CONH.sub.2 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl 220 CONH.sub.2 2,5-diF-phenyl 1-pyrrolidinocarbonyl 221 CONH.sub.2 2,5-diF-phenyl 2-(methylsulfonyl)phenyl 222 CONH.sub.2 2,5-diF-phenyl 4-morpholino 223 CONH.sub.2 2,5-diF-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 224 CONH.sub.2 2,5-diF-phenyl 4-morpholinocarbo nyl 225 SCH.sub.3 phenyl 2-(aminosulfonyl)phenyl 226 SCH.sub.3 phenyl 2-(methylaminosulfonyl)phenyl 227 SCH.sub.3 phenyl 1-pyrrolidinocarbonyl 228 SCH.sub.3 phenyl 2-(methylsulfonyl)phenyl 229 SCH.sub.3 phenyl 4-morpholino 230 SCH.sub.3 phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 231 SCH.sub.3 phenyl 4-morpholinocarbonyl 232 SCH.sub.3 2-pyridyl 2-(aminosulfonyl)phenyl 233 SCH.sub.3 2-pyridyl 2-(methylaminosulfonyl)phenyl 234 SCH.sub.3 2-pyridyl 1-pyrrolidinocarbonyl 235 SCH.sub.3 2-pyridyl 2-(methylsulfonyl)phenyl 236 SCH.sub.3 2-pyridyl 4-morpholino 237 SCH.sub.3 2-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 238 SCH.sub.3 2-pyridyl 4-morpholinocarbonyl 239 SCH.sub.3 3-pyridyl 2-(aminosulfonyl)phenyl 240 SCH.sub.3 3-pyridyl 2-(methylaminosulfonyl)phenyl 241 SCH.sub.3 3-pyridyl 1-pyrrolidinocarbonyl 242 SCH.sub.3 3-pyridyl 2-(methylsulfonyl)phenyl 243 SCH.sub.3 3-pyridyl 4-morpholino 244 SCH.sub.3 3-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 245 SCH.sub.3 3-pyridyl 4-morpholinocarbonyl 246 SCH.sub.3 2-pyrimidyl 2-(aminosulfonyl)phenyl 247 SCH.sub.3 2-pyrimidyl 2-(methylaminosulfonyl)phenyl 248 SCH.sub.3 2-pyrimidyl 1-pyrrolidinocarbonyl 249 SCH.sub.3 2-pyrimidyl 2-(methylsulfonyl)phenyl 250 SCH.sub.3 2-pyrimidyl 4-morpholino 251 SCH.sub.3 2-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 252 SCH.sub.3 2-pyrimidyl 4-morpholinocarbonyl 253 SCH.sub.3 5-pyrimidyl 2-(aminosulfonyl)phenyl 254 SCH.sub.3 5-pyrimidyl 2-(methylaminosulfonyl)phenyl 255 SCH.sub.3 5-pyrimidyl 1-pyrrolidinocarbonyl 256 SCH.sub.3 5-pyrimidyl 2-(methylsulfonyl)phenyl 257 SCH.sub.3 5-pyrimidyl 4-morpholino 258 SCH.sub.3 5-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 259 SCH.sub.3 5-pyrimidyl 4-morpholinocarbonyl 260 SCH.sub.3 2-Cl-phenyl 2-(aminosulfonyl)phenyl 261 SCH.sub.3 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl 262 SCH.sub.3 2-Cl-phenyl 1-pyrrolidinocarbonyl 263 SCH.sub.3 2-Cl-phenyl 2-(methylsulfonyl)phenyl 264 SCH.sub.3 2-Cl-phenyl 4-morpholino 265 SCH.sub.3 2-Cl-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 266 SCH.sub.3 2-Cl-phenyl 4-morpholinocarbonyl 267 SCH.sub.3 2-F-phenyl 2-(aminosulfonyl)phenyl 268 SCH.sub.3 2-F-phenyl 2-(methylaminosulfonyl)phenyl 269 SCH.sub.3 2-F-phenyl 1-pyrrolidinocarbonyl 270 SCH.sub.3 2-F-phenyl 2-(methylsulfonyl)phenyl 271 SCH.sub.3 2-F-phenyl 4-morpholino 272 SCH.sub.3 2-F-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 273 SCH.sub.3 2-F-phenyl 4-morpholinocarbonyl 274 SCH.sub.3 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 275 SCH.sub.3 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl 276 SCH.sub.3 2,5-diF-phenyl 1-pyrrolidinocarbonyl 277 SCH.sub.3 2,5-diF-phenyl 2-(methylsulfonyl)phenyl 278 SCH.sub.3 2,5-diF-phenyl 4-morpholino 279 SCH.sub.3 2,5-diF-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 280 SCH.sub.3 2,5-diF-phenyl 4-morpholinocarbon yl 281 SO.sub.2 CH.sub.3 phenyl 2-(aminosulfonyl)phenyl 282 SO.sub.2 CH.sub.3 phenyl 2-(methylaminosulfonyl)phenyl 283 SO.sub.2 CH.sub.3 phenyl 1-pyrrolidinocarbonyl 284 SO.sub.2 CH.sub.3 phenyl 2-(methylsulfonyl)phenyl 285 SO.sub.2 CH.sub.3 phenyl 4-morpholino 286 SO.sub.2 CH.sub.3 phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 287 SO.sub.2 CH.sub.3 phenyl 4-morpholinocarbon yl 288 SO.sub.2 CH.sub.3 2-pyridyl 2-(aminosulfonyl)phenyl 289 SO.sub.2 CH.sub.3 2-pyridyl 2-(methylaminosulfonyl)phenyl 290 SO.sub.2 CH.sub.3 2-pyridyl 1-pyrrolidinocarbonyl 291 SO.sub.2 CH.sub.3 2-pyridyl 2-(methylsulfonyl)phenyl 292 SO.sub.2 CH.sub.3 2-pyridyl 4-morpholino 293 SO.sub.2 CH.sub.3 2-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 294 SO.sub.2 CH.sub.3 2-pyridyl 4-morpholinocar bonyl 295 SO.sub.2 CH.sub.3 3-pyridyl 2-(aminosulfonyl)phenyl 296 SO.sub.2 CH.sub.3 3-pyridyl 2-(methylaminosulfonyl)phenyl 297 SO.sub.2 CH.sub.3 3-pyridyl 1-pyrrolidinocarbonyl 298 SO.sub.2 CH.sub.3 3-pyridyl 2-(methylsulfonyl)phenyl 299 SO.sub.2 CH.sub.3 3-pyridyl 4-morpholino 300 SO.sub.2 CH.sub.3 3-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 301 SO.sub.2 CH.sub.3 3-pyridyl 4-morpholinocar bonyl 302 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(aminosulfonyl)phenyl 303 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(methylaminosulfonyl)phenyl 304 SO.sub.2 CH.sub.3 2-pyrimidyl 1-pyrrolidino carbonyl 305 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(methylsulfonyl)phenyl 306 SO.sub.2 CH.sub.3 2-pyrimidyl 4-morpholino 307 SO.sub.2 CH.sub.3 2-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 308 SO.sub.2 CH.sub.3 2-pyrimidyl 4-morpholinoc arbonyl 309 SO.sub.2 CH.sub.3 5-pyrimidyl 2-(aminosulfonyl)phenyl 310 SO.sub.2 CH.sub.3 5-pyrimidyl 2-(methylaminosulfonyl)phenyl 311 SO.sub.2 CH.sub.3 5-pyrimidyl 1-pyrrolidino carbonyl 312 SO.sub.2 CH.sub.3 5-pyrimidyl 2-(methylsulfonyl)phenyl 313 SO.sub.2 CH.sub.3 5-pyrimidyl 4-morpholino 314 SO.sub.2 CH.sub.3 5-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 315 SO.sub.2 CH.sub.3 5-pyrimidyl 4-morpholinoc arbonyl 316 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(aminosulfonyl)phenyl 317 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl 318 SO.sub.2 CH.sub.3 2-Cl-phenyl 1-pyrrolidino carbonyl 319 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(methylsulfonyl)phenyl 320 SO.sub.2 CH.sub.3 2-Cl-phenyl 4-morpholino 321 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 322 SO.sub.2 CH.sub.3 2-Cl-phenyl 4-morpholinoc arbonyl 323 SO.sub.2 CH.sub.3 2-F-phenyl 2-(aminosulfonyl)phenyl 324 SO.sub.2 CH.sub.3 2-F-phenyl 2-(methylaminosulfonyl)phenyl 325 SO.sub.2 CH.sub.3 2-F-phenyl 1-pyrrolidinocarbonyl 326 SO.sub.2 CH.sub.3 2-F-phenyl 2-(methylsulfonyl)phenyl 327 SO.sub.2 CH.sub.3 2-F-phenyl 4-morpholino 328 SO.sub.2 CH.sub.3 2-F-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 329 SO.sub.2 CH.sub.3 2-F-phenyl 4-morpholinoca rbonyl 330 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 331 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl 332 SO.sub.2 CH.sub.3 2,5-diF-phenyl 1-pyrrolid inocarbonyl 333 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(methylsulfonyl)phenyl 334 SO.sub.2 CH.sub.3 2,5-diF-phenyl 4-morpholino 335 SO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)pheny l 336 SO.sub.2 CH.sub.3 2,5-diF-phenyl 4-morpholinocarbonyl 337 NHSO.sub.2 CH.sub.3 phenyl 2-(aminosulfonyl)phenyl 338 NHSO.sub.2 CH.sub.3 phenyl 2-(methylaminosulfonyl)phenyl 339 NHSO.sub.2 CH.sub.3 phenyl 1-pyrrolidinocarbonyl 340 NHSO.sub.2 CH.sub.3 phenyl 2-(methylsulfonyl)phenyl 341 NHSO.sub.2 CH.sub.3 phenyl 4-morpholino 342 NHSO.sub.2 CH.sub.3 phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 343 NHSO.sub.2 CH.sub.3 phenyl 4-morpholinocarb onyl 344 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(aminosulfonyl)phenyl 345 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(methylaminosulfonyl)phenyl 346 NHSO.sub.2 CH.sub.3 2-pyridyl 1-pyrrolidino carbonyl 347 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(methylsulfonyl)phenyl 348 NHSO.sub.2 CH.sub.3 2-pyridyl 4-morpholino 349 NHSO.sub.2 CH.sub.3 2-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 350 NHSO.sub.2 CH.sub.3 2-pyridyl 4-morpholinoc arbonyl 351 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(aminosulfonyl)phenyl 352 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(methylaminosulfonyl)phenyl 353 NHSO.sub.2 CH.sub.3 3-pyridyl 1-pyrrolidino carbonyl 354 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(methylsulfonyl)phenyl 355 NHSO.sub.2 CH.sub.3 3-pyridyl 4-morpholino 356 NHSO.sub.2 CH.sub.3 3-pyridyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 357 NHSO.sub.2 CH.sub.3 3-pyridyl 4-morpholinoc arbonyl 358 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(aminosulfonyl)phenyl 359 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(methylaminosulfonyl)phenyl 360 NHSO.sub.2 CH.sub.3 2-pyrimidyl 1-pyrrolidi nocarbonyl 361 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(methylsulfonyl)phenyl 362 NHSO.sub.2 CH.sub.3 2-pyrimidyl 4-morpholino 363 NHSO.sub.2 CH.sub.3 2-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 364 NHSO.sub.2 CH.sub.3 2-pyrimidyl 4-morpholinocarbonyl 365 NHSO.sub.2 CH.sub.3 5-pyrimidyl 2-(aminosulfonyl)phenyl 366 NHSO.sub.2 CH.sub.3 5-pyrimidyl 2-(methylaminosulfonyl)phenyl 367 NHSO.sub.2 CH.sub.3 5-pyrimidyl 1-pyrrolidi nocarbonyl 368 NHSO.sub.2 CH.sub.3 5-pyrimidyl 2-(methylsulfonyl)phenyl 369 NHSO.sub.2 CH.sub.3 5-pyrimidyl 4-morpholino 370 NHSO.sub.2 CH.sub.3 5-pyrimidyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 371 NHSO.sub.2 CH.sub.3 5-pyrimidyl 4-morpholinocarbonyl 372 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(aminosulfonyl)phenyl 373 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(methylaminosulfonyl)phenyl 374 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 1-pyrrolidi nocarbonyl 375 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(methylsulfonyl)phenyl 376 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 4-morpholino 377 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 378 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 4-morpholinocarbonyl 379 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(aminosulfonyl)phenyl 380 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(methylaminosulfonyl)phenyl 381 NHSO.sub.2 CH.sub.3 2-F-phenyl 1-pyrrolidin ocarbonyl 382 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(methylsulfonyl)phenyl 383 NHSO.sub.2 CH.sub.3 2-F-phenyl 4-morpholino 384 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phenyl 385 NHSO.sub.2 CH.sub.3 2-F-phenyl 4-morpholinocarbonyl 386 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(aminosulfonyl)phenyl 387 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(methylaminosulfonyl)phenyl 388 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 1-pyrrolidinocarbonyl 389 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(methylsulfonyl)phenyl 390 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 4-morpholino 391 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 2-(1'-CF.sub.3 -tetrazol-2-yl)phe nyl 392 NHSO.sub.2 CH.sub.3 2,5-diF-phenyl 4-morpholinocarbonyl______________________________________
TABLE 5__________________________________________________________________________ ##STR166##__________________________________________________________________________ #STR167## #STR168## #STR169##a.sub.1 R = F, D = NH.sub.2 b.sub.1 R = F, D = NH.sub.2 c.sub.1 R = F, D = NH.sub.2__________________________________________________________________________ a.sub.2 R = H, D = NH.sub.2 b.sub.2 R = H, D = NH.sub.2 c.sub.2 R = H, D = NH.sub.2 a.sub.3 R = F, D = CH.sub.2 NH.sub.2 b.sub.3 R = F, D = CH.sub.2 NH.sub.2 c.sub.3 R = F, D = CH.sub.2 NH.sub.2 a.sub.4 R = H, D = CH.sub.2 NH.sub.2 b.sub.4 R = H, D = CH.sub.2 NH.sub.2 c.sub.4 R = H, D = CH.sub.2 NH.sub.2 a.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 b.sub.5 R = F, D = C(.dbd.NH)NH.su b.2 c.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 a.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 b.sub.6 R = H, D = C(.dbd.NH)NH.su b.2 c.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 a.sub.7 R = F, D = C(O)NH.sub.2 b.sub.7 R = F, D = C(O)NH.sub.2 c.sub.7 R = F, D = C(O)NH.sub.2 a.sub.8 R = H, D = C(O)NH.su b.2 b.sub.8 R = H, D = C(O)NH.sub.2 c.sub.8 R = H, D = C(O)NH.sub.2__________________________________________________________________________ #STR170## #STR171## #STR172##d.sub.1 R = F, D = NH.sub.2 e.sub.1 R = F, D = NH.sub.2 f.sub.1 R = F, D = NH.sub.2__________________________________________________________________________ d.sub.2 R = H, D = NH.sub.2 e.sub.2 R = H, D = NH.sub.2 f.sub.2 R = H, D = NH.sub.2 d.sub.3 R = F, D = CH.sub.2 NH.sub.2 e.sub.3 R = F, D = CH.sub.2 NH.sub.2 f.sub.3 R = F, D = CH.sub.2 NH.sub.2 d.sub.4 R = H, D = CH.sub.2 NH.sub.2 e.sub.4 R = H, D = CH.sub.2 NH.sub.2 f.sub.4 R = H, D = CH.sub.2 NH.sub.2 d.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 e.sub.5 R = F, D = C(.dbd.NH)NH.su b.2 f.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 d.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 e.sub.6 R = H, D = C(.dbd.NH)NH.su b.2 f.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 d.sub.7 R = F, D = C(O)NH.sub.2 e.sub.7 R = F, D = C(O)NH.sub.2 f.sub.7 R = F, D = C(O)NH.sub.2 d.sub.8 R = H, D = C(O)NH.su b.2 e.sub.8 R = H, D = C(O)NH.sub.2 f.sub.8 R = H, D = C(O)NH.sub.2__________________________________________________________________________ #STR173## #STR174## #STR175##g.sub.1 R = F, D = NH.sub.2 h.sub.1 R = F, D = NH.sub.2 i.sub.1 R = F, D = NH.sub.2__________________________________________________________________________ g.sub.2 R = H, D = NH.sub.2 h.sub.2 R = H, D = NH.sub.2 i.sub.2 R = H, D = NH.sub.2 g.sub.3 R = F, D = CH.sub.2 NH.sub.2 h.sub.3 R = F, D = CH.sub.2 NH.sub.2 i.sub.3 R = F, D = CH.sub.2 NH.sub.2 g.sub.4 R = H, D = CH.sub.2 NH.sub.2 h.sub.4 R = H, D = CH.sub.2 NH.sub.2 i.sub.4 R = H, D = CH.sub.2 NH.sub.2 g.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 h.sub.5 R = F, D = C(.dbd.NH)NH.su b.2 i.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 g.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 h.sub.6 R = H, D = C(.dbd.NH)NH.su b.2 i.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 g.sub.7 R = F, D = C(O)NH.sub.2 h.sub.7 R = F, D = C(O)NH.sub.2 i.sub.7 R = F, D = C(O)NH.sub.2 g.sub.8 R = H, D = C(O)NH.su b.2 h.sub.8 R = H, D = C(O)NH.sub.2 i.sub.8 R = H, D = C(O)NH.sub.2__________________________________________________________________________ #STR176## #STR177## #STR178##j.sub.1 R = F, D = NH.sub.2 k.sub.1 R = F, D = NH.sub.2 l.sub.1 R = F, D = NH.sub.2__________________________________________________________________________ j.sub.2 R = H, D = NH.sub.2 k.sub.2 R = H, D = NH.sub.2 l.sub.2 R = H, D = NH.sub.2 j.sub.3 R = F, D = CH.sub.2 NH.sub.2 k.sub.3 R = F, D = CH.sub.2 NH.sub.2 l.sub.3 R = F, D = CH.sub.2 NH.sub.2 j.sub.4 R = H, D = CH.sub.2 NH.sub.2 k.sub.4 R = H, D = CH.sub.2 NH.sub.2 l.sub.4 R = H, D = CH.sub.2 NH.sub.2 j.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 k.sub.5 R = F, D = C(.dbd.NH)NH.su b.2 l.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 j.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 k.sub.6 R = H, D = C(.dbd.NH)NH.su b.2 l.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 j.sub.7 R = F, D = C(O)NH.sub.2 k.sub.7 R = F, D = C(O)NH.sub.2 l.sub.7 R = F, D = C(O)NH.sub.2 j.sub.8 R = H, D = C(O)NH.su b.2 k.sub.8 R = H, D = C(O)NH.sub.2 l.sub.8 R = H, D = C(O)NH.sub.2__________________________________________________________________________ #STR179## #STR180## #STR181##m.sub.1 R = F, D = NH.sub.2 n.sub.1 R = F, D = NH.sub.2 o.sub.1 R = F, D = NH.sub.2__________________________________________________________________________ m.sub.2 R = H, D = NH.sub.2 n.sub.2 R = H, D = NH.sub.2 o.sub.2 R = H, D = NH.sub.2 m.sub.3 R = F, D = CH.sub.2 NH.sub.2 n.sub.3 R = F, D = CH.sub.2 NH.sub.2 o.sub.3 R = F, D = CH.sub.2 NH.sub.2 m.sub.4 R = H, D = CH.sub.2 NH.sub.2 n.sub.4 R = H, D = CH.sub.2 NH.sub.2 o.sub.4 R = H, D = CH.sub.2 NH.sub.2 m.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 n.sub.5 R = F, D = C(.dbd.NH)NH.su b.2 o.sub.5 R = F, D = C(.dbd.NH)NH.sub.2 m.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 n.sub.6 R = H, D = C(.dbd.NH)NH.su b.2 o.sub.6 R = H, D = C(.dbd.NH)NH.sub.2 m.sub.7 R = F, D = C(O)NH.sub.2 n.sub.7 R = F, D = C(O)NH.sub.2 o.sub.7 R = F, D = C(O)NH.sub.2 m.sub.8 R = H, D = C(O)NH.su b.2 n.sub.8 R = H, D = C(O)NH.sub.2 o.sub.8 R = H, D = C(O)NH.sub.2__________________________________________________________________________ #STR182## #STR183## #STR184##p.sub.1 R = F, D = NH.sub.2 q.sub.1 R = F, D = NH.sub.2 r.sub.1 R = F, D = NH.sub.2__________________________________________________________________________ p.sub.2 R = Cl, D = NH.sub.2 q.sub.2 R = Cl, D = NH.sub.2 r.sub.2 R = Cl, D = NH.sub.2 p.sub.3 R = OMe, D = NH.sub.2 q.sub.3 R = OMe, D = NH.sub.2 r.sub.3 R = OMe, D = NH.sub.2 p.sub.4 R = F, D = CH.sub.2 NH.sub.2 q.sub.4 R = F, D = CH.sub.2 NH.sub.2 r.sub.4 R = F, D = CH.sub.2 NH.sub.2 p.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 q.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 r.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 p.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 q.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 r.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 p.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 q.sub.7 R = F, D = C(.dbd.NH)NH.su b.2 r.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 p.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 q.sub.8 R = Cl, D = C(.dbd.NH)NH. sub.2 r.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 p.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 q.sub.9 R = OMe, D = C(.dbd.NH)N H.sub.2 r.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 p.sub.10 R = F, D = C(O)NH.sub.2 q.sub.10 R = F, D = C(O)NH.sub.2 r.sub.10 R = F, D = C(O)NH.su b.2 p.sub.11 R = Cl, D = C(O)NH.sub.2 q.sub.11 R = Cl, D = C(O)NH.sub.2 r.sub.11 R = Cl, D = C(O)NH.sub.2 p.sub.12 R = OMe, D = C(O)NH.sub.2 q.sub.12 R = OMe, D = C(O)NH.sub.2 r.sub.12 R = OMe, D = C(O)NH.sub.2__________________________________________________________________________ #STR185## #STR186## #STR187##s.sub.1 R = F, D = NH.sub.2 t.sub.1 R = F, D = NH.sub.2 u.sub.1 R = F, D = NH.sub.2__________________________________________________________________________ s.sub.2 R = Cl, D = NH.sub.2 t.sub.2 R = Cl, D = NH.sub.2 u.sub.2 R = Cl, D = NH.sub.2 s.sub.3 R = OMe, D = NH.sub.2 t.sub.3 R = OMe, D = NH.sub.2 u.sub.3 R = OMe, D = NH.sub.2 s.sub.4 R = F, D = CH.sub.2 NH.sub.2 t.sub.4 R = F, D = CH.sub.2 NH.sub.2 u.sub.4 R = F, D = CH.sub.2 NH.sub.2 s.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 t.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 u.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 s.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 t.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 u.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 s.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 t.sub.7 R = F, D = C(.dbd.NH)NH.su b.2 u.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 s.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 t.sub.8 R = Cl, D = C(.dbd.NH)NH. sub.2 u.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 s.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 t.sub.9 R = OMe, D = C(.dbd.NH)N H.sub.2 u.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 s.sub.10 R = F, D = C(O)NH.sub.2 t.sub.10 R = F, D = C(O)NH.sub.2 u.sub.10 R = F, D = C(O)NH.su b.2 s.sub.11 R = Cl, D = C(O)NH.sub.2 t.sub.11 R = Cl, D = C(O)NH.sub.2 u.sub.11 R = Cl, D = C(O)NH.sub.2 s.sub.12 R = OMe, D = C(O)NH.sub.2 t.sub.12 R = OMe, D = C(O)NH.sub.2 u.sub.12 R = OMe, D = C(O)NH.sub.2__________________________________________________________________________ #STR188## #STR189## #STR190##v.sub.1 R = F, D = NH.sub.2 w.sub.1 R = F, D = NH.sub.2 x.sub.1 R = F, D = NH.sub.2__________________________________________________________________________ v.sub.2 R = Cl, D = NH.sub.2 w.sub.2 R = Cl, D = NH.sub.2 x.sub.2 R = Cl, D = NH.sub.2 v.sub.3 R = OMe, D = NH.sub.2 w.sub.3 R = OMe, D = NH.sub.2 x.sub.3 R = OMe, D = NH.sub.2 v.sub.4 R = F, D = CH.sub.2 NH.sub.2 w.sub.4 R = F, D = CH.sub.2 NH.sub.2 x.sub.4 R = F, D = CH.sub.2 NH.sub.2 v.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 w.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 x.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 v.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 w.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 x.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 v.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 w.sub.7 R = F, D = C(.dbd.NH)NH.su b.2 x.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 v.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 w.sub.8 R = Cl, D = C(.dbd.NH)NH. sub.2 x.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 v.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 w.sub.9 R = OMe, D = C(.dbd.NH)N H.sub.2 x.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 v.sub.10 R = F, D = C(O)NH.sub.2 w.sub.10 R = F, D = C(O)NH.sub.2 x.sub.10 R = F, D = C(O)NH.su b.2 v.sub.11 R = Cl, D = C(O)NH.sub.2 w.sub.11 R = Cl, D = C(O)NH.sub.2 x.sub.11 R = Cl, D = C(O)NH.sub.2 v.sub.12 R = OMe, D = C(O)NH.sub.2 w.sub.12 R = OMe, D = C(O)NH.sub.2 x.sub.12 R = OMe, D = C(O)NH.sub.2__________________________________________________________________________ #STR191## #STR192## #STR193##y.sub.1 R = F, D = NH.sub.2 z.sub.1 R = F, D = NH.sub.2 aa.sub.1 R = F, D = NH.sub.2__________________________________________________________________________ y.sub.2 R = Cl, D = NH.sub.2 z.sub.2 R = Cl, D = NH.sub.2 aa.sub.2 R = Cl, D = NH.sub.2 y.sub.3 R = OMe, D = NH.sub.2 z.sub.3 R = OMe, D = NH.sub.2 aa.sub.3 R = OMe, D = NH.sub.2 y.sub.4 R = F, D = CH.sub.2 NH.sub.2 z.sub.4 R = F, D = CH.sub.2 NH.sub.2 aa.sub.4 R = F, D = CH.sub.2 NH.sub.2 y.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 z.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 aa.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 y.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 z.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 aa.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 y.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 z.sub.7 R = F, D = C(.dbd.NH)NH.su b.2 aa.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 y.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 z.sub.8 R = Cl, D = C(.dbd.NH)NH. sub.2 aa.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 y.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 z.sub.9 R = OMe, D = C(.dbd.NH)N H.sub.2 aa.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 y.sub.10 R = F, D = C(O)NH.sub.2 z.sub.10 R = F, D = C(O)NH.sub.2 aa.sub.10 R = F, D = C(O)NH.sub.2 y.sub.11 R = Cl, D = C(O)NH.sub.2 z.sub.11 R = Cl, D = C(O)NH.sub.2 aa.sub.11 R = Cl, D = C(O)NH.sub.2 y.sub.12 R = OMe, D = C(O)NH.sub.2 z.sub.12 R = OMe, D = C(O)NH.sub.2 aa.sub.12 R = OMe, D = C(O)NH.sub.2__________________________________________________________________________ #STR194## #STR195## #STR196##bb.sub.1 R = F, D = NH.sub.2 cc.sub.1 R = F, D = NH.sub.2 dd.sub.1 R = F, D = NH.sub.2__________________________________________________________________________ bb.sub.2 R = Cl, D = NH.sub.2 cc.sub.2 R = Cl, D = NH.sub.2 dd.sub.2 R = Cl, D = NH.sub.2 bb.sub.3 R = OMe, D = NH.sub.2 cc.sub.3 R = OMe, D = NH.sub.2 dd.sub.3 R = OMe, D = NH.sub.2 bb.sub.4 R = F, D = CH.sub.2 NH.sub.2 cc.sub.4 R = F, D = CH.sub.2 NH.sub.2 dd.sub.4 R = F, D = CH.sub.2 NH.sub.2 bb.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 cc.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 dd.sub.5 R = Cl, D = CH.sub.2 NH.sub.2 bb.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 cc.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 dd.sub.6 R = OMe, D = CH.sub.2 NH.sub.2 bb.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 cc.sub.7 R = F, D = C(.dbd.NH)NH. sub.2 dd.sub.7 R = F, D = C(.dbd.NH)NH.sub.2 bb.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 cc.sub.8 R = Cl, D = C(.dbd.NH)N H.sub.2 dd.sub.8 R = Cl, D = C(.dbd.NH)NH.sub.2 bb.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 cc.sub.9 R = OMe, D = C(.dbd.NH )NH.sub.2 dd.sub.9 R = OMe, D = C(.dbd.NH)NH.sub.2 bb.sub.10 R = F, D = C(O)NH.sub.2 cc.sub.10 R = F, D = C(O)NH.sub.2 dd.sub.10 R = F, D = C(O)NH.sub.2 bb.sub.11 R = Cl, D = C(O)NH.sub.2 cc.sub.11 R = Cl, D = C(O)NH.sub.2 dd.sub.11 R = Cl, D = C(O)NH.sub.2 bb.sub.12 R = OMe, D = C(O)NH.sub.2 cc.sub.12 R = OMe, D = C(O)NH.sub.2 dd.sub.12 R = OMe, D = C(O)NH.sub.2__________________________________________________________________________ #STR197## #STR198## #STR199##ee.sub.1 R = F, D = CH.sub.2 NH.sub.2 ff.sub.1 R = F, D = CH.sub.2 NH.sub.2 gg.sub.1 R = F, D = CH.sub.2 NH.sub.2__________________________________________________________________________ ee.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 ff.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 gg.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 ee.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 ff.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 gg.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 ee.sub.4 R = CH.sub.2 NH.sub.2, ff.sub.4 R = CH.sub.2 NH.sub.2, gg.sub.4 R = CH.sub.2 NH.sub.2, D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2__________________________________________________________________________ #STR200## #STR201## #STR202##hh.sub.1 R = F, D = CH.sub.2 NH.sub.2 ii.sub.1 R = F, D = CH.sub.2 NH.sub.2 jj.sub.1 R = F, D = CH.sub.2 NH.sub.2__________________________________________________________________________ hh.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 ii.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 jj.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 hh.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 ii.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 jj.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 hh.sub.4 R = CH.sub.2 NH.sub.2, ii.sub.4 R = CH.sub.2 NH.sub.2, jj.sub.4 R = CH.sub.2 NH.sub.2, D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2__________________________________________________________________________ #STR203## #STR204## #STR205##kk.sub.1 R = F, D = CH.sub.2 NH.sub.2 ll.sub.1 R = F, D = CH.sub.2 NH.sub.2 mm.sub.1 R = F, D = CH.sub.2 NH.sub.2__________________________________________________________________________ kk.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 ll.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 mm.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 kk.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 ll.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 mm.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 kk.sub.4 R = CH.sub.2 NH.sub.2, ll.sub.4 R = CH.sub.2 NH.sub.2, mm.sub.4 R = CH.sub.2 NH.sub.2, D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2__________________________________________________________________________ #STR206## #STR207## #STR208##nn.sub.1 R = F, D = CH.sub.2 NH.sub.2 oo.sub.1 R = F, D = CH.sub.2 NH.sub.2 pp.sub.1 R = F, D = CH.sub.2 NH.sub.2__________________________________________________________________________ nn.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 oo.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 pp.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 nn.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 oo.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 pp.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 nn.sub.4 R = CH.sub.2 NH.sub.2, oo.sub.4 R = CH.sub.2 NH.sub.2, pp.sub.4 R = CH.sub.2 NH.sub.2, D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2__________________________________________________________________________ #STR209## #STR210## #STR211##qq.sub.1 R = F, D = CH.sub.2 NH.sub.2 rr.sub.1 R = F, D = CH.sub.2 NH.sub.2 ss.sub.1 R = F, D = CH.sub.2 NH.sub.2__________________________________________________________________________ qq.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 rr.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 ss.sub.2 R = Cl, D = CH.sub.2 NH.sub.2 qq.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 rr.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 ss.sub.3 R = OMe, D = CH.sub.2 NH.sub.2 qq.sub.4 R = CH.sub.2 NH.sub.2, rr.sub.4 R = CH.sub.2 NH.sub.2, ss.sub.4 R = CH.sub.2 NH.sub.2, D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2 D = CH.sub.2 NH.sub.2__________________________________________________________________________
______________________________________Ex# R.sup.1b A B______________________________________1 H phenyl 2-((Me).sub.2 N-methyl)phenyl 2 H phenyl 2-((Me)NH-methyl)phenyl 3 H phenyl 2-(H.sub.2 N-methyl)phenyl 4 H phenyl 2-HOCH.sub.2 -phenyl 5 H 2-F-phenyl 2-((Me).sub.2 N-methyl)phenyl 6 H 2-F-phenyl 2-((Me)NH-methyl)phenyl 7 H 2-F-phenyl 2-(H.sub.2 N-methyl)phenyl 8 H 2-F-phenyl 2-HOCH.sub.2 -phenyl 9 H phenyl 2-methylimidazol-1-yl 10 H phenyl 2-ethylimidazol-1-yl 11 H phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 12 H phenyl 2-CH.sub.3 NHSO.sub.2 -imidazol-1-yl 13 H phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 14 H 2-F-phenyl 2-methylimidazol-1-yl 15 H 2-F-phenyl 2-ethylimidazol-1-yl 16 H 2-F-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 17 H 2-F-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 18 H 2-F-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 19 H 2-Cl-phenyl 2-methylimidazol-1-yl 20 H 2-Cl-phenyl 2-ethylimidazol-1-yl 21 H 2-Cl-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 22 H 2-Cl-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 23 H 2-Cl-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 24 H 2-(Me).sub.2 N-phenyl 2-methylimidazol-1-yl 25 H 2-(Me).sub.2 N-phenyl 2-ethylimidazol-1-yl 26 H 2-(Me).sub.2 N-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 27 H 2-(Me).sub.2 N-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 28 H 2-(Me).sub.2 N-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 29 H phenyl N-methylimidazol-2-yl 30 H phenyl 4-methylimidazol-5-yl 31 H phenyl 5-CF.sub.3 -pyrazol-1-yl 32 H 2-F-phenyl N-methylimidazol-2-yl 33 H 2-F-phenyl 4-methylimidazol-5-yl 34 H 2-F-phenyl 5-CF.sub.3 -pyrazol-1-yl 35 H phenyl guanidino 36 H phenyl 2-thiazolin-2-ylamine 37 H phenyl N-methyl-2-imidazolin-2-yl 38 H phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 39 H phenyl N-methylimidazol-2-ylthiol 40 H phenyl t-butoxycarbonylamine 41 H phenyl (N-pyrrolidino)formylimino 42 H phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 43 H 2-F-phenyl guanidino 44 H 2-F-phenyl 2-thiazolin-2-ylamine 45 H 2-F-phenyl N-methyl-2-imidazolin-2-yl 46 H 2-F-phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 47 H 2-F-phenyl N-methylimidazol-2-ylthio 48 H 2-F-phenyl t-butoxycarbonylamine 49 H 2-F-phenyl (N-pyrrolidino)formylimino 50 H 2-F-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 51 H 2-CH.sub.3 O-phenyl (N-pyrrolidino)formylimino 52 H 2-CH.sub.3 O-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 53 --CN phenyl 2-((Me).sub.2 N-methyl)phenyl 54 --CN phenyl 2-((Me)NH-methyl)phenyl 55 --CN phenyl 2-(H.sub.2 N-methyl)phenyl 56 --CN phenyl 2-HOCH.sub.2 -phenyl 57 --CN 2-F-phenyl 2-((Me).sub.2 N-methyl)phenyl 58 --CN 2-F-phenyl 2-((Me)NH-methyl)phenyl 59 --CN 2-F-phenyl 2-(H.sub.2 N-methyl)phenyl 60 --CN 2-F-phenyl 2-HOCH.sub.2 -phenyl 61 --CN phenyl 2-methylimidazol-1-yl 62 --CN phenyl 2-ethylimidazol-1-yl 63 --CN phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 64 --CN phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 65 --CN phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 66 --CN 2-F-phenyl 2-methylimidazol-1-yl 67 --CN 2-F-phenyl 2-ethylimidazol-1-yl 68 --CN 2-F-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 69 --CN 2-F-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 70 --CN 2-F-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 71 --CN 2-Cl-phenyl 2-methylimidazol-1-yl 72 --CN 2-Cl-phenyl 2-ethylimidazol-1-yl 73 --CN 2-Cl-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 74 --CN 2-Cl-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 75 --CN 2-Cl-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 76 --CN 2-(Me).sub.2 N-phenyl 2-methylimidazol-1-yl 77 --CN 2-(Me).sub.2 N-phenyl 2-ethylimidazol-1-yl 78 --CN 2-(Me).sub.2 N-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 79 --CN 2-(Me).sub.2 N-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 80 --CN 2-(Me).sub.2 N-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 81 --CN phenyl N-methylimidazol-2-yl 82 --CN phenyl 4-methylimidazol-5-yl 83 --CN phenyl 5-CF.sub.3 -pyrazol-1-yl 84 --CN 2-F-phenyl N-methylimidazol-2-yl 85 --CN 2-F-phenyl 4-methylimidazol-5-yl 86 --CN 2-F-phenyl 5-CF.sub.3 -pyrazol-1-yl 87 --CN phenyl guanidino 88 --CN phenyl 2-thiazolin-2-ylamine 89 --CN phenyl N-methyl-2-imidazolin-2-yl 90 --CN phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 91 --CN phenyl N-methylimidazol-2-ylthiol 92 --CN phenyl t-butoxycarbonylamine 93 --CN phenyl (N-pyrrolidino)formylimino 94 --CN phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 95 --CN 2-F-phenyl guanidino 96 --CN 2-F-phenyl 2-thiazolin-2-ylamine 97 --CN 2-F-phenyl N-methyl-2-imidazolin-2-yl 98 --CN 2-F-phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 99 --CN 2-F-phenyl N-methylimidazol-2-ylthio 100 --CN 2-F-phenyl t-butoxycarbonylamine 101 --CN 2-F-phenyl (N-pyrrolidino)formylimino 102 --CN 2-F-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 103 --CN 2-CH.sub.3 O-phenyl (N-pyrrolidino)formylimino 104 --CN 2-CH.sub.3 O-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 105 CF.sub.3 phenyl 2-((Me).sub.2 N-methyl)phenyl 106 CF.sub.3 phenyl 2-((Me)NH-methyl)phenyl 107 CF.sub.3 phenyl 2-(H.sub.2 N-methyl)phenyl 108 CF.sub.3 phenyl 2-HOCH.sub.2 -phenyl 109 CF.sub.3 2-F-phenyl 2-((Me).sub.2 N-methyl)phenyl 110 CF.sub.3 2-F-phenyl 2-((Me)NH-methyl)phenyl 111 CF.sub.3 2-F-phenyl 2-(H.sub.2 N-methyl)phenyl 112 CF.sub.3 2-F-phenyl 2-HOCH.sub.2 -phenyl 113 CF.sub.3 phenyl 2-methylimidazol-1-yl 114 CF.sub.3 phenyl 2-ethylimidazol-1-yl 115 CF.sub.3 phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 116 CF.sub.3 phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 117 CF.sub.3 phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 118 CF.sub.3 2-F-phenyl 2-methylimidazol-1-yl 119 CF.sub.3 2-F-phenyl 2-ethylimidazol-1-yl 120 CF.sub.3 2-F-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 121 CF.sub.3 2-F-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 122 CF.sub.3 2-F-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 123 CF.sub.3 2-Cl-phenyl 2-methylimidazol-1-yl 124 CF.sub.3 2-Cl-phenyl 2-ethylimidazol-1-yl 125 CF.sub.3 2-Cl-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 126 CF.sub.3 2-Cl-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 127 CF.sub.3 2-Cl-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 128 CF.sub.3 2-(Me).sub.2 N-phenyl 2-methylimidazol-1-yl 129 CF.sub.3 2-(Me).sub.2 N-phenyl 2-ethylimidazol-1-yl 130 CF.sub.3 2-(Me).sub.2 N-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 131 CF.sub.3 2-(Me).sub.2 N-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 132 CF.sub.3 2-(Me).sub.2 N-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 133 CF.sub.3 phenyl N-methylimidazol-2-yl 134 CF.sub.3 phenyl 4-methylimidazol-5-yl 135 CF.sub.3 phenyl 5-CF.sub.3 -pyrazol-1-yl 136 CF.sub.3 2-F-phenyl N-methylimidazol-2-yl 137 CF.sub.3 2-F-phenyl 4-methylimidazol-5-yl 138 CF.sub.3 2-F-phenyl 5-CF.sub.3 -pyrazol-1-yl 139 CF.sub.3 phenyl guanidino 140 CF.sub.3 phenyl 2-thiazolin-2-ylamine 141 CF.sub.3 phenyl N-methyl-2-imidazolin-2-yl 142 CF.sub.3 phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 143 CF.sub.3 phenyl N-methylimidazol-2-ylthiol 144 CF.sub.3 phenyl t-butoxycarbonylamine 145 CF.sub.3 phenyl (N-pyrrolidino)formylimino 146 CF.sub.3 phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 147 CF.sub.3 2-F-phenyl guanidino 148 CF.sub.3 2-F-phenyl 2-thiazolin-2-ylamine 149 CF.sub.3 2-F-phenyl N-methyl-2-imidazolin-2-yl 150 CF.sub.3 2-F-phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 151 CF.sub.3 2-F-phenyl N-methylimidazol-2-ylthio 152 CF.sub.3 2-F-phenyl t-butoxycarbonylamine 153 CF.sub.3 2-F-phenyl (N-pyrrolidino)formylimino 154 CF.sub.3 2-F-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 155 CF.sub.3 2-CH.sub.3 O-phenyl (N-pyrrolidino)formylimino 156 CF.sub.3 2-CH.sub.3 O-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 157 CONH.sub.2 phenyl 2-((Me).sub.2 N-methyl)phenyl 158 CONH.sub.2 phenyl 2-((Me)NH-methyl)phenyl 159 CONH.sub.2 phenyl 2-(H.sub.2 N-methyl)phenyl 160 CONH.sub.2 phenyl 2-HOCH.sub.2 -phenyl 161 CONH.sub.2 2-F-phenyl 2-((Me).sub.2 N-methyl)phenyl 162 CONH.sub.2 2-F-phenyl 2-((Me)NH-methyl)phenyl 163 CONH.sub.2 2-F-phenyl 2-(H.sub.2 N-methyl)phenyl 164 CONH.sub.2 2-F-phenyl 2-HOCH.sub.2 -phenyl 165 CONH.sub.2 phenyl 2-methylimidazol-1-yl 166 CONH.sub.2 phenyl 2-ethylimidazol-1-yl 167 CONH.sub.2 phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 168 CONH.sub.2 phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 169 CONH.sub.2 phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 170 CONH.sub.2 2-F-phenyl 2-methylimidazol-1-yl 171 CONH.sub.2 2-F-phenyl 2-ethylimidazol-1-yl 172 CONH.sub.2 2-F-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 173 CONH.sub.2 2-F-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 174 CONH.sub.2 2-F-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-y1 175 CONH.sub.2 2-Cl-phenyl 2-methylimidazol-1-yl 176 CONH.sub.2 2-Cl-phenyl 2-ethylimidazol-1-yl 177 CONH.sub.2 2-Cl-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 178 CONH.sub.2 2-Cl-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 179 CONH.sub.2 2-Cl-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 180 CONH.sub.2 2-(Me).sub.2 N-phenyl 2-methylimidazol-1-yl 181 CONH.sub.2 2-(Me).sub.2 N-phenyl 2-ethylimidazol-1-yl 182 CONH.sub.2 2-(Me).sub.2 N-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-y l 183 CONH.sub.2 2-(Me).sub.2 N-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 184 CONH.sub.2 2-(Me).sub.2 N-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 185 CONH.sub.2 phenyl N-methylimidazol-2-yl 186 CONH.sub.2 phenyl 4-methylimidazol-5-yl 187 CONH.sub.2 phenyl 5-CF.sub.3 -pyrazol-1-yl 188 CONH.sub.2 2-F-phenyl N-methylimidazol-2-yl 189 CONH.sub.2 2-F-phenyl 4-methylimidazol-5-yl 190 CONH.sub.2 2-F-phenyl 5-CF.sub.3 -pyrazol-1-yl 191 CONH.sub.2 phenyl guanidino 192 CONH.sub.2 phenyl 2-thiazolin-2-ylamine 193 CONH.sub.2 phenyl N-methyl-2-imidazolin-2-yl 194 CONH.sub.2 phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 195 CONH.sub.2 phenyl N-methylimidazol-2-ylthiol 196 CONH.sub.2 phenyl t-butoxycarbonylamine 197 CONH.sub.2 phenyl (N-pyrrolidino)formylimino 198 CONH.sub.2 phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 199 CONH.sub.2 2-F-phenyl guanidino 200 CONH.sub.2 2-F-phenyl 2-thiazolin-2-ylamine 201 CONH.sub.2 2-F-phenyl N-methyl-2-imidazolin-2-yl 202 CONH.sub.2 2-F-phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 203 CONH.sub.2 2-F-phenyl N-methylimidazol-2-ylthio 204 CONH.sub.2 2-F-phenyl t-butoxycarbonylamine 205 CONH.sub.2 2-F-phenyl (N-pyrrolidino)formylimino 206 CONH.sub.2 2-F-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 207 CONH.sub.2 2-CH.sub.3 O-phenyl (N-pyrrolidino)formylimino 208 CONH.sub.2 2-CH.sub.3 O-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 209 SCH.sub.3 phenyl 2-((Me).sub.2 N-methyl)phenyl 210 SCH.sub.3 phenyl 2-((Me)NH-methyl)phenyl 211 SCH.sub.3 phenyl 2-(H.sub.2 N-methyl)phenyl 212 SCH.sub.3 phenyl 2-HOCH.sub.2 -phenyl 213 SCH.sub.3 2-F-phenyl 2-((Me).sub.2 N-methyl)phenyl 214 SCH.sub.3 2-F-phenyl 2-((Me)NH-methyl)phenyl 215 SCH.sub.3 2-F-phenyl 2-(H.sub.2 N-methyl)phenyl 216 SCH.sub.3 2-F-phenyl 2-HOCH.sub.2 -phenyl 217 SCH.sub.3 phenyl 2-methylimidazol-1-yl 218 SCH.sub.3 phenyl 2-ethylimidazol-1-yl 219 SCH.sub.3 phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 220 SCH.sub.3 phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 221 SCH.sub.3 phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 222 SCH.sub.3 2-F-phenyl 2-methylimidazol-1-yl 223 SCH.sub.3 2-F-phenyl 2-ethylimidazol-1-yl 224 SCH.sub.3 2-F-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 225 SCH.sub.3 2-F-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 226 SCH.sub.3 2-F-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 227 SCH.sub.3 2-Cl-phenyl 2-methylimidazol-1-yl 228 SCH.sub.3 2-Cl-phenyl 2-ethylimidazol-1-yl 229 SCH.sub.3 2-Cl-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 230 SCH.sub.3 2-Cl-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 231 SCH.sub.3 2-Cl-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 232 SCH.sub.3 2-(Me).sub.2 N-phenyl 2-methylimidazol-1-yl 233 SCH.sub.3 2-(Me).sub.2 N-phenyl 2-ethylimidazol-1-yl 234 SCH.sub.3 2-(Me).sub.2 N-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 235 SCH.sub.3 2-(Me).sub.2 N-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 236 SCH.sub.3 2-(Me).sub.2 N-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 237 SCH.sub.3 phenyl N-methylimidazol-2-yl 238 SCH.sub.3 phenyl 4-methylimidazol-5-yl 239 SCH.sub.3 phenyl 5-CF.sub.3 -pyrazol-1-yl 240 SCH.sub.3 2-F-phenyl N-methylimidazol-2-yl 241 SCH.sub.3 2-F-phenyl 4-methylimidazol-5-yl 242 SCH.sub.3 2-F-phenyl 5-CF.sub.3 -pyrazol-1-yl 243 SCH.sub.3 phenyl guanidino 244 SCH.sub.3 phenyl 2-thiazolin-2-ylamine 245 SCH.sub.3 phenyl N-methyl-2-imidazolin-2-yl 246 SCH.sub.3 phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 247 SCH.sub.3 phenyl N-methylimidazol-2-ylthiol 248 SCH.sub.3 phenyl t-butoxycarbonylamine 249 SCH.sub.3 phenyl (N-pyrrolidino)formylimino 250 SCH.sub.3 phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 251 SCH.sub.3 2-F-phenyl guanidino 252 SCH.sub.3 2-F-phenyl 2-thiazolin-2-ylamine 253 SCH.sub.3 2-F-phenyl N-methyl-2-imidazolin-2-yl 254 SCH.sub.3 2-F-phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 255 SCH.sub.3 2-F-phenyl N-methylimidazol-2-ylthio 256 SCH.sub.3 2-F-phenyl t-butoxycarbonylamine 257 SCH.sub.3 2-F-phenyl (N-pyrrolidino)formylimino 258 SCH.sub.3 2-F-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 259 SCH.sub.3 2-CH.sub.3 O-phenyl (N-pyrrolidino)formylimino 260 SCH.sub.3 2-CH.sub.3 O-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 261 SO.sub.2 CH.sub.3 phenyl 2-((Me).sub.2 N-methyl)phenyl 262 SO.sub.2 CH.sub.3 phenyl 2-((Me)NH-methyl)phenyl 263 SO.sub.2 CH.sub.3 phenyl 2-(H.sub.2 N-methyl)phenyl 264 SO.sub.2 CH.sub.3 phenyl 2-HOCH.sub.2 -phenyl 265 SO.sub.2 CH.sub.3 2-F-phenyl 2-((Me).sub.2 N-methyl)phenyl 266 SO.sub.2 CH.sub.3 2-F-phenyl 2-((Me)NH-methyl)phenyl 267 SO.sub.2 CH.sub.3 2-F-phenyl 2-(H.sub.2 N-methyl)phenyl 268 SO.sub.2 CH.sub.3 2-F-phenyl 2-HOCH.sub.2 -phenyl 269 SO.sub.2 CH.sub.3 phenyl 2-methylimidazol-1-yl 270 SO.sub.2 CH.sub.3 phenyl 2-ethylimidazol-1-yl 271 SO.sub.2 CH.sub.3 phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 272 SO.sub.2 CH.sub.3 phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 273 SO.sub.2 CH.sub.3 phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 274 SO.sub.2 CH.sub.3 2-F-phenyl 2-methylimida zol-1-yl 275 SO.sub.2 CH.sub.3 2-F-phenyl 2-ethylimidazol-1-yl 276 SO.sub.2 CH.sub.3 2-F-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 277 SO.sub.2 CH.sub.3 2-F-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 278 SO.sub.2 CH.sub.3 2-F-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 279 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-methylimid azol-1-yl 280 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-ethylimidazol-1-yl 281 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 282 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 283 SO.sub.2 CH.sub.3 2-Cl-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 284 SO.sub.2 CH.sub.3 2-(Me).sub.2 N-phenyl 2-methylimidazol-1-yl 285 SO.sub.2 CH.sub.3 2-(Me).sub.2 N-phenyl 2-ethylimidazol-1-yl 286 SO.sub.2 CH.sub.3 2-(Me).sub.2 N-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 287 SO.sub.2 CH.sub.3 2-(Me).sub.2 N-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 288 SO.sub.2 CH.sub.3 2-(Me).sub.2 N-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 289 SO.sub.2 CH.sub.3 phenyl N-methylimidazol-2-yl 290 SO.sub.2 CH.sub.3 phenyl 4-methylimidazol-5-yl 291 SO.sub.2 CH.sub.3 phenyl 5-CF.sub.3 -pyrazol-1-yl 292 SO.sub.2 CH.sub.3 2-F-phenyl N-methylimidazol-2-yl 293 SO.sub.2 CH.sub.3 2-F-phenyl 4-methylimidazol-5-yl 294 SO.sub.2 CH.sub.3 2-F-phenyl 5-CF.sub.3 -pyrazol-1-yl 295 SO.sub.2 CH.sub.3 phenyl guanidino 296 SO.sub.2 CH.sub.3 phenyl 2-thiazolin-2-ylamine 297 SO.sub.2 CH.sub.3 phenyl N-methyl-2-imidazolin-2-yl 298 SO.sub.2 CH.sub.3 phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 299 SO.sub.2 CH.sub.3 phenyl N-methylimidazol-2-ylthiol 300 SO.sub.2 CH.sub.3 phenyl t-butoxycarbonylamine 301 SO.sub.2 CH.sub.3 phenyl (N-pyrrolidino)formylimino 302 SO.sub.2 CH.sub.3 phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 303 SO.sub.2 CH.sub.3 2-F-phenyl guanidino 304 SO.sub.2 CH.sub.3 2-F-phenyl 2-thiazolin-2-ylamine 305 SO.sub.2 CH.sub.3 2-F-phenyl N-methyl-2-imidazolin-2-yl 306 SO.sub.2 CH.sub.3 2-F-phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 307 SO.sub.2 CH.sub.3 2-F-phenyl N-methylimidazol-2-ylthio 308 SO.sub.2 CH.sub.3 2-F-phenyl t-butoxycarbonylamine 309 SO.sub.2 CH.sub.3 2-F-phenyl (N-pyrrolidino)formylimino 310 SO.sub.2 CH.sub.3 2-F-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 311 SO.sub.2 CH.sub.3 2-CH.sub.3 O-phenyl (N-pyrrolidino)formylimino 312 SO.sub.2 CH.sub.3 2-CH.sub.3 O-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 313 NHSO.sub.2 CH.sub.3 phenyl 2-((Me).sub.2 N-methyl)phenyl 314 NHSO.sub.2 CH.sub.3 phenyl 2-((Me)NH-methyl)phenyl 315 NHSO.sub.2 CH.sub.3 phenyl 2-(H.sub.2 N-methyl)phenyl 316 NHSO.sub.2 CH.sub.3 phenyl 2-HOCH.sub.2 -phenyl 317 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-((Me).sub.2 N-methyl)phenyl 318 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-((Me)NH-m ethyl)phenyl 319 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-(H.sub.2 N-methyl)phenyl 320 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-HOCH.sub.2 -phenyl 321 NHSO.sub.2 CH.sub.3 phenyl 2-methylimidazol-1-yl 322 NHSO.sub.2 CH.sub.3 phenyl 2-ethylimidazol-1-yl 323 NHSO.sub.2 CH.sub.3 phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 324 NHSO.sub.2 CH.sub.3 phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 325 NHSO.sub.2 CH.sub.3 phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 326 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-methylimi dazol-1-yl 327 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-ethylimidazol-1-yl 328 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 329 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 330 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 331 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-methylimidazol-1-yl 332 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-ethylimidazol-1-yl 333 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-((Me).sub.2 N-methyl)imidazol-1-yl 334 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 335 NHSO.sub.2 CH.sub.3 2-Cl-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 336 NHSO.sub.2 CH.sub.3 2-(Me).sub.2 N-phenyl 2-methylimidazol-1-yl 337 NHSO.sub.2 CH.sub.3 2-(Me).sub.2 N-phenyl 2-ethylimidazol-1-yl 338 NHSO.sub.2 CH.sub.3 2-(Me).sub.2 N-phenyl 2-((Me).sub.2 N-methyl)imi dazol-1-yl 339 NHSO.sub.2 CH.sub.3 2-(Me).sub.2 N-phenyl 2-CH.sub.3 SO.sub.2 -imidazol-1-yl 340 NHSO.sub.2 CH.sub.3 2-(Me).sub.2 N-phenyl 2-CH.sub.3 OCH.sub.2 -imidazol-1-yl 341 NHSO.sub.2 CH.sub.3 phenyl N-methylimidazol-2-yl 342 NHSO.sub.2 CH.sub.3 phenyl 4-methylimidazol-5-yl 343 NHSO.sub.2 CH.sub.3 phenyl 5-CF.sub.3 -pyrazol-1-yl 344 NHSO.sub.2 CH.sub.3 2-F-phenyl N-methylimidazol-2-yl 345 NHSO.sub.2 CH.sub.3 2-F-phenyl 4-methylimidazol-5-yl 346 NHSO.sub.2 CH.sub.3 2-F-phenyl 5-CF.sub.3 -pyrazol-1-yl 347 NHSO.sub.2 CH.sub.3 phenyl guanidino 348 NHSO.sub.2 CH.sub.3 phenyl 2-thiazolin-2-ylamine 349 NHSO.sub.2 CH.sub.3 phenyl N-methyl-2-imidazolin-2-yl 350 NHSO.sub.2 CH.sub.3 phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 351 NHSO.sub.2 CH.sub.3 phenyl N-methylimidazol-2-ylthiol 352 NHSO.sub.2 CH.sub.3 phenyl t-butoxycarbonylamine 353 NHSO.sub.2 CH.sub.3 phenyl (N-pyrrolidino)formylimino 354 NHSO.sub.2 CH.sub.3 phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 355 NHSO.sub.2 CH.sub.3 2-F-phenyl guanidino 356 NHSO.sub.2 CH.sub.3 2-F-phenyl 2-thiazolin-2-ylamine 357 NHSO.sub.2 CH.sub.3 2-F-phenyl N-methyl-2-imidazolin-2-yl 358 NHSO.sub.2 CH.sub.3 2-F-phenyl N-methyl-1,4,5,6- tetrahydropyrimid-2-yl 359 NHSO.sub.2 CH.sub.3 2-F-phenyl N-methylimidazol-2-ylthio 360 NHSO.sub.2 CH.sub.3 2-F-phenyl t-butoxycarbonylamine 361 NHSO.sub.2 CH.sub.3 2-F-phenyl (N-pyrrolidino)formylimino 362 NHSO.sub.2 CH.sub.3 2-F-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino 363 NHSO.sub.2 CH.sub.3 2-CH.sub.3 O-phenyl (N-pyrrolidino)formylimino 364 NHSO.sub.2 CH.sub.3 2-CH.sub.3 O-phenyl (N-pyrrolidino)formyl-N- (methanesulfamoyl)imino______________________________________
Utility
The compounds of this invention are useful as anticoagulants for the treatment or prevention of thromboembolic disorders in mammals. The term "thromboembolic disorders" as used herein includes arterial or venous cardiovascular or cerebrovascular thromboembolic disorders, including, for example, unstable angina, first or recurrent myocardial infarction, ischemic sudden death, transient ischemic attack, stroke, atherosclerosis, venous thrombosis, deep vein thrombosis, thrombophlebitis, arterial embolism, coronary and cerebral arterial thrombosis, cerebral embolism, kidney embolisms, and pulmonary embolisms. The anticoagulant effect of compounds of the present invention is believed to be due to inhibition of factor Xa or thrombin.
The effectiveness of compounds of the present invention as inhibitors of factor Xa was determined using purified human factor Xa and synthetic substrate. The rate of factor Xa hydrolysis of chromogenic substrate S2222 (Kabi Pharmacia, Franklin, Ohio) was measured both in the absence and presence of compounds of the present invention. Hydrolysis of the substrate resulted in the release of pNA, which was monitored spectrophotometrically by measuring the increase in absorbance at 405 nM. A decrease in the rate of absorbance change at 405 nm in the presence of inhibitor is indicative of enzyme inhibition. The results of this assay are expressed as inhibitory constant, K.sub.i.
Factor Xa determinations were made in 0.10 M sodium phosphate buffer, pH 7.5, containing 0.20 M NaCl, and 0.5% PEG 8000. The Michaelis constant, K.sub.m, for substrate hydrolysis was determined at 25.degree. C. using the method of Lineweaver and Burk. Values of K.sub.i were determined by allowing 0.2-0.5 nM human factor Xa (Enzyme Research Laboratories, South Bend, IN) to react with the substrate (0.20 mM-1 mM) in the presence of inhibitor. Reactions were allowed to go for 30 minutes and the velocities (rate of absorbance change vs time) were measured in the time frame of 25-30 minutes. The following relationship was used to calculate K.sub.i values:
(v.sub.o -v.sub.s)/v.sub.s =I/(K.sub.i (1+S/K.sub.m))
where:
v.sub.o is the velocity of the control in the absence of inhibitor;
v.sub.s is the velocity in the presence of inhibitor;
I is the concentration of inhibitor;
K.sub.i is the dissociation constant of the enzyme:inhibitor complex;
S is the concentration of substrate;
K.sub.m is the Michaelis constant.
Using the methodology described above, a number of compounds of the present invention were found to exhibit a K.sub.i of .ltoreq.15 .mu.M, thereby confirming the utility of the compounds of the present invention as effective Xa inhibitors.
The antithrombotic effect of compounds of the present invention can be demonstrated in a rabbit arterio-venous (AV) shunt thrombosis model. In this model, rabbits weighing 2-3 kg anesthetized with a mixture of xylazine (10 mg/kg i.m.) and ketamine (50 mg/kg i.m.) are used. A saline-filled AV shunt device is connected between the femoral arterial and the femoral venous cannulae. The AV shunt device consists of a piece of 6-cm tygon tubing which contains a piece of silk thread. Blood will flow from the femoral artery via the AV-shunt into the femoral vein. The exposure of flowing blood to a silk thread will induce the formation of a significant thrombus. After forty minutes, the shunt is disconnected and the silk thread covered with thrombus is weighed. Test agents or vehicle will be given (i.v., i.p., s.c., or orally) prior to the opening of the AV shunt. The percentage inhibition of thrombus formation is determined for each treatment group. The ID50 values (dose which produces 50% inhibition of thrombus formation) are estimated by linear regression.
The compounds of formula (I) may also be useful as inhibitors of serine proteases, notably human thrombin, plasma kallikrein and plasmin. Because of their inhibitory action, these compounds are indicated for use in the prevention or treatment of physiological reactions, blood coagulation and inflammation, catalyzed by the aforesaid class of enzymes. Specifically, the compounds have utility as drugs for the treatment of diseases arising from elevated thrombin activity such as myocardial infarction, and as reagents used as anticoagulants in the processing of blood to plasma for diagnostic and other commercial purposes.
Some compounds of the present invention were shown to be direct acting inhibitors of the serine protease thrombin by their ability to inhibit the cleavage of small molecule substrates by thrombin in a purified system. In vitro inhibition constants were determined by the method described by Kettner et al. in J. Biol. Chem. 265, 18289-18297 (1990), herein incorporated by reference. In these assays, thrombin-mediated hydrolysis of the chromogenic substrate S2238 (Helena Laboratories, Beaumont, Tex.) was monitored spectrophotometrically. Addition of an inhibitor to the assay mixture results in decreased absorbance and is indicative of thrombin inhibition. Human thrombin (Enzyme Research Laboratories, Inc., South Bend, Ind.) at a concentration of 0.2 nM in 0.10 M sodium phosphate buffer, pH 7.5, 0.20 M NaCl, and 0.5% PEG 6000, was incubated with various substrate concentrations ranging from 0.20 to 0.02 mM. After 25 to 30 minutes of incubation, thrombin activity was assayed by monitoring the rate of increase in absorbance at 405 nm which arises owing to substrate hydrolysis. Inhibition constants were derived from reciprocal plots of the reaction velocity as a function of substrate concentration using the standard method of Lineweaver and Burk. Using the methodology described above, some compounds of this invention were evaluated and found to exhibit a K.sub.i of less than 15 .mu.m, thereby confirming the utility of the compounds of the present invention as effective Xa inhibitors.
The compounds of the present invention can be administered alone or in combination with one or more additional therapeutic agents. These include other anti-coagulant or coagulation inhibitory agents, anti-platelet or platelet inhibitory agents, thrombin inhibitors, or thrombolytic or fibrinolytic agents.
The compounds are administered to a mammal in a therapeutically effective amount. By "therapeutically effective amount" it is meant an amount of a compound of Formula I that, when administered alone or in combination with an additional therapeutic agent to a mammal, is effective to prevent or ameliorate the thromboembolic disease condition or the progression of the,disease.
By "administered in combination" or "combination therapy" it is meant that the compound of Formula I and one or more additional therapeutic agents are administered concurrently to the mammal being treated. When administered in combination each component may be administered at the same time or sequentially in any order at different points in time. Thus, each component may be administered separately but sufficiently closely in time so as to provide the desired therapeutic effect. Other anticoagulant agents (or coagulation inhibitory agents) that may be used in combination with the compounds of this invention include warfarin and heparin, as well as other factor Xa inhibitors such as those described in the publications identified above under Background of the Invention.
The term anti-platelet agents (or platelet inhibitory agents), as used herein, denotes agents that inhibit platelet function such as by inhibiting the aggregation, adhesion or granular secretion of platelets. Such agents include, but are not limited to, the various known non-steroidal anti-inflammatory drugs (NSAIDS) such as aspirin, ibuprofen, naproxen, sulindac, indomethacin, mefenamate, droxicam, diclofenac, sulfinpyrazone, and piroxicam, including pharmaceutically acceptable salts or prodrugs thereof. Of the NSAIDS, aspirin (acetylsalicyclic acid or ASA), and piroxicam are preferred. Other suitable anti-platelet agents include ticlopidine, including pharmaceutically acceptable salts or prodrugs thereof. Ticlopidine is also a preferred compound since it is known to be gentle on the gastro-intestinal tract in use. Still other suitable platelet inhibitory agents include IIb/IIIa antagonists, thromboxane-A2-receptor antagonists and thromboxane-A2-synthetase inhibitors, as well as pharmaceutically acceptable salts or prodrugs thereof.
The term thrombin inhibitors (or anti-thrombin agents), as used herein, denotes inhibitors of the serine protease thrombin. By inhibiting thrombin, various thrombin-mediated processes, such as thrombin-mediated platelet activation (that is, for example, the aggregation of platelets, and/or the granular secretion of plasminogen activator inhibitor-1 and/or serotonin) and/or fibrin formation are disrupted. A number of thrombin inhibitors are known to one of skill in the art and these inhibitors are contemplated to be used in combination with the present compounds. Such inhibitors include, but are not limited to, boroarginine derivatives, boropeptides, heparins, hirudin and argatroban, including pharmaceutically acceptable salts and prodrugs thereof. Boroarginine derivatives and boropeptides include N-acetyl and peptide derivatives of boronic acid, such as C-terminal a-aminoboronic acid derivatives of lysine, ornithine, arginine, homoarginine and corresponding isothiouronium analogs thereof. The term hirudin, as used herein, includes suitable derivatives or analogs of hirudin, referred to herein as hirulogs, such as disulfatohirudin. Boropeptide thrombin inhibitors include compounds described in Kettner et al., U.S. Pat. No. 5,187,157 and European Patent Application Publication Number 293 881 A2, the disclosures of which are hereby incorporated herein by reference. Other suitable boroarginine derivatives and boropeptide thrombin inhibitors include those disclosed in PCT Application Publication Number 92/07869 and European Patent Application Publication Number 471,651 A2, the disclosures of which are hereby incorporated herein by reference.
The term thrombolytics (or fibrinolytic) agents (or thrombolytics or fibrinolytics), as used herein, denotes agents that lyse blood clots (thrombi). Such agents include tissue plasminogen activator, anistreplase, urokinase or streptokinase, including pharmaceutically acceptable salts or prodrugs thereof. The term anistreplase, as used herein, refers to anisoylated plasminogen streptokinase activator complex, as described, for example, in European Patent Application No. 028,489, the disclosure of which is hereby incorporated herein by reference herein. The term urokinase, as used herein, is intended to denote both dual and single chain urokinase, the latter also being referred to herein as prourokinase.
Administration of the compounds of Formula I of the invention in combination with such additional therapeutic agent, may afford an efficacy advantage over the compounds and agents alone, and may do so while permitting the use of lower doses of each. A lower dosage minimizes the potential of side effects, thereby providing an increased margin of safety.
The compounds of the present invention are also useful as standard or reference compounds, for example as a quality standard or control, in tests or assays involving the inhibition of factor Xa. Such compounds may be provided in a commercial kit, for example, for use in pharmaceutical research involving factor Xa. For example, a compound of the present invention could be used as a reference in an assay to compare its known activity to a compound with an unknown activity. This would ensure the experimenter that the assay was being performed properly and provide a basis for comparison, especially if the test compound was a derivative of the reference compound. When developing new assays or protocols, compounds according to the present invention could be used to test their effectiveness.
The compounds of the present invention may also be used in diagnostic assays involving factor Xa. For example, the presence of factor Xa in an unknown sample could be determined by addition of chromogenic substrate S2222 to a series of solutions containing test sample and optionally one of the compounds of the present invention. If production of pNA is observed in the solutions containing test sample, but no compound of the present invention, then one would conclude factor Xa was present.
Dosage and Formulation
The compounds of this invention can be administered in such oral dosage forms as tablets, capsules (each of which includes sustained release or timed release formulations), pills, powders, granules, elixirs, tinctures, suspensions, syrups, and emulsions. They may also be administered in intravenous (bolus or infusion), intraperitoneal, subcutaneous, or intramuscular form, all using dosage forms well known to those of ordinary skill in the pharmaceutical arts. They can be administered alone, but generally will be administered with a pharmaceutical carrier selected on the basis of the chosen route of administration and standard pharmaceutical practice.
The dosage regimen for the compounds of the present invention will, of course, vary depending upon known factors, such as the pharmacodynamic characteristics of the particular agent and its mode and route of administration; the species, age, sex, health, medical condition, and weight of the recipient; the nature and extent of the symptoms; the kind of concurrent treatment; the frequency of treatment; the route of administration, the renal and hepatic function of the patient,and the effect desired. A physician or veterinarian can determine and prescribe the effective amount of the drug required to prevent, counter, or arrest the progress of the thromboembolic disorder.
By way of general guidance, the daily oral dosage of each active ingredient, when used for the indicated effects, will range between about 0.001 to 1000 mg/kg of body weight, preferably between about 0.01 to 100 mg/kg of body weight per day, and most preferably between about 1.0 to 20 mg/kg/day. Intravenously, the most preferred doses will range from about 1 to about 10 mg/kg/minute during a constant rate infusion. Compounds of this invention may be administered in a single daily dose, or the total daily dosage may be administered in divided doses of two, three, or four times daily.
Compounds of this invention can be administered in intranasal form via topical use of suitable intranasal vehicles, or via transdermal routes, using transdermal skin patches. When administered in the form of a transdermal delivery system, the dosage administration will, of course, be continuous rather than intermittent throughout the dosage regimen.
The compounds are typically administered in admixture with suitable pharmaceutical diluents, excipients, or carriers (collectively referred to herein as pharmaceutical carriers) suitably selected with respect to the intended form of administration, that is, oral tablets, capsules, elixirs, syrups and the like, and consistent with conventional pharmaceutical practices.
For instance, for oral administration in the form of a tablet or capsule, the active drug component can be combined with an oral, non-toxic, pharmaceutically acceptable, inert carrier such as lactose, starch, sucrose, glucose, methyl callulose, magnesium stearate, dicalcium phosphate, calcium sulfate, mannitol, sorbitol and the like; for oral administration in liquid form, the oral drug components can be combined with any oral, non-toxic, pharmaceutically acceptable inert carrier such as ethanol, glycerol, water, and the like. Moreover, when desired or necessary, suitable binders, lubricants, disintegrating agents, and coloring agents can also be incorporated into the mixture. Suitable binders include starch, gelatin, natural sugars such as glucose or beta-lactose, corn sweeteners, natural and synthetic gums such as acacia, tragacanth, or sodium alginate, carboxymethylcellulose, polyethylene glycol, waxes, and the like. Lubricants used in these dosage forms include sodium oleate, sodium stearate, magnesium stearate, sodium benzoate, sodium acetate, sodium chloride, and the like. Disintegrators include, without limitation, starch, methyl cellulose, agar, bentonite, xanthan gum, and the like.
The compounds of the present invention can also be administered in the form of liposome delivery systems, such as small unilamellar vesicles, large unilamellar vesicles, and multilamellar vesicles. Liposomes can be formed from a variety of phospholipids, such as cholesterol, stearylamine, or phosphatidylcholines.
Compounds of the present invention may also be coupled with soluble polymers as targetable drug carriers. Such polymers can include polyvinylpyrrolidone, pyran copolymer, polyhydroxypropylmethacrylamide-phenol, polyhydroxyethylaspartamidephenol, or polyethyleneoxidepolylysine substituted with palmitoyl residues. Furthermore, the compounds of the present invention may be coupled to a class of biodegradable polymers useful in achieving controlled release of a drug, for example, polylactic acid, polyglycolic acid, copolymers of polylactic and polyglycolic acid, polyepsilon caprolactone, polyhydroxy butyric acid, polyorthoesters, polyacetals, polydihydropyrans, polycyanoacylates, and crosslinked or amphipathic block copolymers of hydrogels.
Dosage forms (pharmaceutical compositions) suitable for administration may contain from about 1 milligram to about 100 milligrams of active ingredient per dosage unit. In these pharmaceutical compositions the active ingredient will ordinarily be present in an amount of about 0.5-95% by weight based on the total weight of the composition.
Gelatin capsules may contain the active ingredient and powdered carriers, such as lactose, starch, cellulose derivatives, magnesium stearate, stearic acid, and the like. Similar diluents can be used to make compressed tablets. Both tablets and capsules can be manufactured as sustained release products to provide for continuous release of medication over a period of hours. Compressed tablets can be sugar coated or film coated to mask any unpleasant taste and protect the tablet from the atmosphere, or enteric coated for selective disintegration in the gastrointestinal tract.
Liquid dosage forms for oral administration can contain coloring and flavoring to increase patient acceptance.
In general, water, a suitable oil, saline, aqueous dextrose (glucose), and related sugar solutions and glycols such as propylene glycol or polyethylene glycols are suitable carriers for parenteral solutions. Solutions for parenteral administration preferably contain a water soluble salt of the active ingredient, suitable stabilizing agents, and if necessary, buffer substances. Antioxidizing agents such as sodium bisulfite, sodium sulfite, or ascorbic acid, either alone or combined, are suitable stabilizing agents. Also used are citric acid and its salts and sodium EDTA. In addition, parenteral solutions can contain preservatives, such as benzalkonium chloride, methyl- or propyl-paraben, and chlorobutanol.
Suitable pharmaceutical carriers are described in Remington's Pharmaceutical Sciences, Mack Publishing Company, a standard reference text in this field.
Representative useful pharmaceutical dosage-forms for administration of the compounds of this invention can be illustrated as follows:
Capsules
A large number of unit capsules can be prepared by filling standard two-piece hard gelatin capsules each with 100 milligrams of powdered active ingredient, 150 milligrams of lactose, 50 milligrams of cellulose, and 6 milligrams magnesium stearate.
Soft Gelatin Capsules
A mixture of active ingredient in a digestable oil such as soybean oil, cottonseed oil or olive oil may be prepared and injected by means of a positive displacement pump into gelatin to form soft gelatin capsules containing 100 milligrams of the active ingredient. The capsules should be washed and dried.
Tablets
Tablets may be prepared by conventional procedures so that the dosage unit is 100 milligrams of active ingredient, 0.2 milligrams of colloidal silicon dioxide, 5 milligrams of magnesium stearate, 275 milligrams of microcrystalline cellulose, 11 milligrams of starch and 98.8 milligrams of lactose. Appropriate coatings may be applied to increase palatability or delay absorption.
Injectable
A parenteral composition suitable for administration by injection may be prepared by stirring 1.5% by weight of active ingredient in 10% by volume propylene glycol and water. The solution should be made isotonic with sodium chloride and sterilized.
Suspension
An aqueous suspension can be prepared for oral administration so that each 5 mL contain 100 mg of finely divided active ingredient, 200 mg of sodium carboxymethyl cellulose, 5 mg of sodium benzoate, 1.0 g of sorbitol solution, U.S.P., and 0.025 mL of vanillin.
Where the compounds of this invention are combined with other anticoagulant agents, for example, a daily dosage may be about 0.1 to 100 milligrams of the compound of Formula I and about 1 to 7.5 milligrams of the second anticoagulant, per kilogram of patient body weight. For a tablet dosage form, the compounds of this invention generally may be present in an amount of about 5 to 10 milligrams per dosage unit, and the second anti-coagulant in an amount of about 1 to 5 milligrams per dosage unit.
Where the compounds of Formula I are administered in combination with an anti-platelet agent, by way of general guidance, typically a daily dosage may be about 0.01 to 25 milligrams of the compound of Formula I and about 50 to 150 milligrams of the anti-platelet agent, preferably about 0.1 to 1 milligrams of the compound of Formula I and about 1 to 3 milligrams of antiplatelet agents, per kilogram of patient body weight.
Where the compounds of Formula I are adminstered in combination with thrombolytic agent, typically a daily dosage may be about 0.1 to 1 milligrams of the compound of Formula I, per kilogram of patient body weight and, in the case of the thrombolytic agents, the usual dosage of the thrombolyic agent when administered alone may be reduced by about 70-80% when administered with a compound of Formula I.
Where two or more of the foregoing second therapeutic agents are administered with the compound of Formula I, generally the amount of each component in a typical daily dosage and typical dosage form may be reduced relative to the usual dosage of the agent when administered alone, in view of the additive or synergistic effect of the therapeutic agents when administered in combination.
Particularly when provided as a single dosage unit, the potential exists for a chemical interaction between the combined active ingredients. For this reason, when the compound of Formula I and a second therapeutic agent are combined in a single dosage unit they are formulated such that although the active ingredients are combined in a single dosage unit, the physical contact between the active ingredients is minimized (that is, reduced). For example, one active ingredient may be enteric coated. By enteric coating one of the active ingredients, it is possible not only to minimize the contact between the combined active ingredients, but also, it is possible to control the release of one of these components in the gastrointestinal tract such that one of these components is not released in the stomach but rather is released in the intestines. One of the active ingredients may also be coated with a material which effects a sustained-release throughout the gastrointestinal tract and also serves to minimize physical contact between the combined active ingredients. Furthermore, the sustained-released component can be additionally enteric coated such that the release of this component occurs only in the intestine. Still another approach would involve the formulation of a combination product in which the one component is coated with a sustained and/or enteric release polymer, and the other component is also coated with a polymer such as a lowviscosity grade of hydroxypropyl methylcellulose (HPMC) or other appropriate materials as known in the art, in order to further separate the active components. The polymer coating serves to form an additional barrier to interaction with the other component.
These as well as other ways of minimizing contact between the components of combination products of the present invention, whether administered in a single dosage form or administered in separate forms but at the same time by the same manner, will be readily apparent to those skilled in the art, once armed with the present disclosure.
Obviously, numerous modifications and variations of the present invention are possible in light of the above teachings. It is therefore to be understood that within the scope of the appended claims, the invention may be practiced otherwise that as specifically described herein.
Claims
  • 1. A compound of formula I: ##STR212## or a stereoisomer or pharmaceutically acceptable salt form thereof, wherein;
  • ring M contains from 0-1 N atoms;
  • D is selected from CN, C(.dbd.NR.sup.7)NR.sup.8 R.sup.9, NHC(.dbd.NR.sup.7)NR.sup.8 R.sup.9, NR.sup.8 CH(.dbd.NR.sup.7), C(O)NR.sup.8 R.sup.9, and (CR.sup.8 R.sup.9).sub.t NR.sup.8 R.sup.9 ;
  • E is selected from phenyl, 2-pyridyl, 4-pyridyl, pyrimidyl, and piperidinyl substituted with 1 R;
  • R is selected from H, F, Cl, Br, I, OR.sup.3, SR.sup.3, CO.sub.2 R.sup.3, NO.sub.2, and CH.sub.2 OR.sup.3, and (CR.sup.8 R.sup.9).sub.t NR.sup.8 R.sup.9 ;
  • with the proviso that if t is equal to 0 and E is selected from phenyl, then R is selected from F, Cl, Br, and I;
  • alternatively, E and R combine to form methylenedioxy or ethylenedioxy;
  • Z is selected from a bond, C.sub.1-4 alkylene, (CH.sub.2).sub.r O(CH.sub.2).sub.r, (CH.sub.2).sub.r NR.sup.3 (CH.sub.2).sub.r, (CH.sub.2).sub.r C(O) (CH.sub.2).sub.r, (CH.sub.2).sub.r C(O)O(CH.sub.2).sub.r, (CH.sub.2).sub.r OC(O)(CH.sub.2).sub.r, (CH.sub.2).sub.r C(O)NR.sup.3 (CH.sub.2).sub.r, (CH.sub.2).sub.r NR.sup.3 C(O)(CH.sub.2).sub.r, (CH.sub.2).sub.r OC(O)O(CH.sub.2).sub.r, (CH.sub.2).sub.r OC(O)NR.sup.3 (CH.sub.2).sub.r, (CH.sub.2).sub.r NR.sup.3 C(O)O(CH.sub.2).sub.r, (CH.sub.2).sub.r NR.sup.3 C(O)NR.sup.3 (CH.sub.2).sub.r, (CH.sub.2).sub.r S(O).sub.p (CH.sub.2).sub.r, (CH.sub.2).sub.r SO.sub.2 NR.sup.3 (CH.sub.2).sub.r, (CH.sub.2).sub.r NR.sup.3 S02(CH.sub.2).sub.r, and (CH.sub.2).sub.r NR.sup.3 SO.sub.2 NR.sup.3 (CH.sub.2).sub.r, provided that Z does not form a N--N, N--O, N--S, NCH.sub.2 N, NCH.sub.2 O, or NCH.sub.2 S bond with ring M or group A;
  • R.sup.1a and R.sup.1b are independently absent or selected from --(CH.sub.2).sub.r --R.sup.1', --CH.dbd.CH--R.sup.1', NCH.sub.2 R.sup.1", OCH.sub.2 R.sup.1", SCH.sub.2 R.sup.1", NH(CH.sub.2).sub.2 (CH.sub.2).sub.t R.sup.1', O(CH.sub.2).sub.2 (CH.sub.2).sub.t R.sup.1', and S(CH.sub.2).sub.2 (CH.sub.2).sub.t R.sup.1' ;
  • alternatively, R.sup.1a and R.sup.1b, when attached to adjacent carbon atoms, together with the atoms to which they are attached form a 5-8 membered saturated, partially saturated or unsaturated ring substituted with 0-2 R.sup.4 and which contains from 0-2 heteroatoms selected from the group consisting of N, O, and S;
  • alternatively, when Z is C(O)NH and R.sup.1a is attached to a ring carbon adjacent to Z, then R.sup.1a is a C(O) which replaces the amide hydrogen of Z to form a cyclic imide;
  • R.sup.1' is selected from H, C.sub.1-3 alkyl, F, Cl, Br, I, --CN, --CHO, (CF.sub.2).sub.r CF.sub.3, (CH.sub.2).sub.r OR.sup.2, NR.sup.2 R.sup.2a, C(O) R.sup.2c, OC(O)R.sup.2, (CF.sub.2).sub.r CO.sub.2 R.sup.2c, S(O).sub.p R.sup.2b, NR.sup.2 (CH.sub.2).sub.r OR.sup.2, CH(.dbd.NR.sup.2c)NR.sup.2 R.sup.2a, NR.sup.2 C(O)R.sup.2b, NR.sup.2 C(O)NHR.sup.2b, NR.sup.2 C(O).sub.2 R.sup.2a, OC(O)NR.sup.2a R.sup.2b, C(O)NR.sup.2 R.sup.2a, C(O)NR.sup.2 (CH.sub.2).sub.r OR.sup.2, SO.sub.2 NR.sup.2 R.sup.2a, NR.sup.2 SO.sub.2 R.sup.2b, C.sub.3-6 carbocyclic residue substituted with 0-2 R.sup.4, and 5-10 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4 ;
  • R.sup.1" is selected from H, CH(CH.sub.2 OR.sup.2).sub.2, C(O)R.sup.2c, C(O)NR.sup.2 R.sup.2a, S(O)R.sup.2b, S(O).sub.2 R.sup.2b, and SO.sub.2 NR.sup.2 R.sup.2a ;
  • R.sup.2, at each occurrence, is selected from H, CF.sub.3, C.sub.1-6 alkyl, benzyl, C.sub.3-6 carbocyclic residue substituted with 0-2 R.sup.4b, and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4b ;
  • R.sup.2a, at each occurrence, is selected from H, CF.sub.3, C.sub.1-6 alkyl, benzyl, phenethyl, C.sub.3-6 carbocyclic residue substituted with 0-2 R.sup.4b, and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4b ;
  • R.sup.2b, at each occurrence, is selected from CF.sub.3, C.sub.1-4 alkoxy, C.sub.1-6 alkyl, benzyl, C.sub.3-6 carbocyclic residue substituted with 0-2 R.sup.4b, and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4b ;
  • R.sup.2c, at each occurrence, is selected from CF.sub.3, OH, C.sub.1-4 alkoxy, C.sub.1-6 alkyl, benzyl, C.sub.3-6 carbocyclic residue substituted with 0-2 R.sup.4b, and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4b ;
  • alternatively, R.sup.2 and R.sup.2a, together with the atom to which they are attached, combine to form a 5 or 6 membered saturated, partially saturated or unsaturated ring substituted with 0-2 R.sup.4b and containing from 0-1 additional heteroatoms selected from the group consisting of N, O, and S;
  • R.sup.3, at each occurrence, is selected from H, C.sub.1-4 alkyl, and phenyl;
  • R.sup.3a, at each occurrence, is selected from H, C.sub.1-4 alkyl, and phenyl;
  • R.sup.3b, at each occurrence, is selected from H, C.sub.1-4 alkyl, and phenyl;
  • R.sup.3c, at each occurrence, is selected from C.sub.1-4 alkyl, and phenyl;
  • A is selected from:
  • C.sub.3-10 carbocyclic residue substituted with 0-2 R.sup.4[, and
  • - 10membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4 ];
  • B is selected from: H, Y, and X--Y;
  • X is selected from C.sub.1-4 alkylene, --CR.sup.2 (CR.sup.2 R.sup.2b)(CH.sub.2).sub.t --, --C(O)--, --C(.dbd.NR.sup.1")--, --CR.sup.2 (NR.sup.1" R.sup.2)--, --CR.sup.2 (OR.sup.2)--, --CR.sup.2 (SR.sup.2)--, --C(O)CR.sup.2 R.sup.2a --, --CR.sup.2 R.sup.2a C(O), --S(O).sub.p --, --S(O).sub.p CR.sup.2 R.sup.2a --, --CR.sup.2 R.sup.2a S(O).sub.p --, --S(O).sub.2 NR.sup.2 --, --NR.sup.2 S(O).sub.2 --, --NR.sup.2 S(O).sub.2 CR.sup.2 R.sup.2a --, --CR.sup.2 R.sup.2a S(O).sub.2 NR.sup.2 --, --NR.sup.2 S(O).sub.2 NR.sup.2 --, --C(O)NR.sup.2 --, --NR.sup.2 C(O)--, --C(O)NR.sup.2c R.sup.2 R.sup.2a --, --NR.sup.2 C(O)CR.sup.2 R.sup.2a --, --CR.sup.2 R.sup.2a C(O)NR.sup.2 --, --CR.sup.2 R.sup.2a NR.sup.2 C(O)--, --NR.sup.2 C(O)O--, --OC(O)NR.sup.2 --, --NR.sup.2 C(O)NR.sup.2 --, --NR.sup.2 --, --NR.sup.2c R.sup.2 R.sup.2a --, --CR.sup.2 R.sup.2a NR.sup.2 --, O, --CR.sup.2 R.sup.2a O--, and --OCR.sup.2 R.sup.2a --;
  • Y is selected from:
  • (CH.sub.2).sub.r NR.sup.2 R.sup.2a, provided that X--Y do not form a N--N, O--N, or S--N bond,
  • C.sub.3-10 carbocyclic residue substituted with 0-2 R.sup.4a, and
  • 5-10 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4a ;
  • R.sup.4, at each occurrence, is selected from H, .dbd.O, (CH.sub.2).sub.r OR.sup.2, F, Cl, Br, I, C.sub.1-4 alkyl, --CN, NO.sub.2, (CH.sub.2).sub.r NR.sup.2 R.sup.2a, (CH.sub.2).sub.r C(O)R.sup.2c, NR.sup.2 C(O)R.sup.2b, C(O)NR.sup.2 R.sup.2a, NR.sup.2 C(O)NR.sup.2 R.sup.2a, CH(.dbd.NR.sup.2)NR.sup.2 R.sup.2a, CH(.dbd.NS(O).sub.2 R.sup.5)NR.sup.2 R.sup.2a, NHC(.dbd.NR.sup.2)NR.sup.2 R.sup.2a, C(O)NHC(.dbd.NR.sup.2)NR.sup.2 R.sup.2a, SO.sub.2 NR.sup.2 R.sup.2a, NR.sup.2 SO.sub.2 NR.sup.2 R.sup.2a, NR.sup.2 SO.sub.2 -C.sub.1-4 alkyl, NR.sup.2 SO.sub.2 R.sup.5, S(O).sub.p R.sup.5, (CF.sub.2).sub.r CF.sub.3, NCH.sub.2 R.sup.1", OCH.sub.2 R.sup.1", SCH.sub.2 R.sup.1", N(CH.sub.2).sub.2 (CH.sub.2).sub.t R.sup.1', O(CH.sub.2).sub.2 (CH.sub.2).sub.t R.sup.1', and S(CH.sub.2).sub.2 (CH.sub.2).sub.t R.sup.1' ;
  • alternatively, one R.sup.4 is a 5-6 membered aromatic heterocycle containing from 1-4 heteroatoms selected from the group consisting of N, O, and S;
  • R.sup.4a, at each occurrence, is selected from H, .dbd.O, (CH.sub.2).sub.r OR.sup.2, (CH.sub.2).sub.r --F, (CH.sub.2).sub.r --Br, (CH.sub.2).sub.r --Cl, I, C.sub.1-4 alkyl, --CN, NO.sub.2, (CH.sub.2) rNR.sup.2 R.sup.2a, (CH.sub.2).sub.r NR.sup.2 R.sup.2b, (CH.sub.2).sub.r C(O)R.sup.2c, NR.sup.2 C(O)R.sup.2b, C(O)NR.sup.2 R.sup.2a, C(O)NH(CH.sub.2).sub.2 NR.sup.2 R.sup.2a, NR.sup.2 C(O)NR.sup.2 R.sup.2a, CH(.dbd.NR.sup.2)NR.sup.2 R.sup.2a, NHC(.dbd.NR.sup.2)NR.sup.2 R.sup.2a, SO.sub.2 NR.sup.2 R.sup.2a, NR.sup.2 SO.sub.2 NR.sup.2 SO.sub.2 R.sup.5, NR.sup.2 SO.sub.2 --C.sub.1-4 alkyl, C(O)NHSO.sub.2 --C.sub.1-4 alkyl, NR.sup.2 SO.sub.2 R.sup.5, S(O).sub.p R.sup.5, and (CF.sub.2).sub.r CF.sub.3 ;
  • alternatively, one R.sup.4a is a 5-6 membered aromatic heterocycle containing from 1-4 heteroatoms selected from the group consisting of N, O, and S and substituted with 0-1 R.sup.5 ;
  • R.sup.4b, at each occurrence, is selected from H, .dbd.O, (CH.sub.2).sub.r OR.sup.3, F, Cl, Br, I, C.sub.1-4 alkyl, --CN, NO.sub.2, (CH.sub.2).sub.r NR.sup.3 R.sup.3a, (CH.sub.2).sub.r C(O)R.sup.3, (CH.sub.2).sub.r C(O)OR.sup.3c, NR.sup.3 C(O)R.sup.3a, C(O)NR.sup.3 R.sup.3a, NR.sup.3 C(O)NR.sup.3 R.sup.3a, CH(.dbd.NR.sup.3)NR.sup.3 R.sup.3a, NH.sup.3 C(.dbd.NR.sup.3)NR.sup.3 R.sup.3a, SO.sub.2 NR.sup.3 R.sup.3a, NR.sup.3 SO.sub.2 NR.sup.3 R.sup.3a, NR.sup.3 SO.sub.2 -C.sub.1-4 alkyl, NR.sup.3 SO.sub.2 CF.sub.3, NR.sup.3 SO.sub.2 -phenyl, S(O).sub.p CF.sub.3, S(O).sub.p -C.sub.1-4 alkyl, S(O).sub.p -phenyl, and (CF.sub.2).sub.r CF.sub.3 ;
  • R.sup.5, at each occurrence, is selected from CF.sub.3, C.sub.1-6 alkyl, phenyl substituted with 0-2 R.sup.6, and benzyl substituted with 0-2 R.sup.6 ;
  • R.sup.6, at each occurrence, is selected from H, OH, (CH.sub.2).sub.r OR.sup.2, F, Cl, Br, I, C.sub.1-4 alkyl, CN, NO.sub.2, (CH.sub.2).sub.r NR.sup.2 R.sup.2a, (CH.sub.2).sub.r C(O)R.sup.2b, NR.sup.2 C(O)R.sup.2b, NR.sup.2 C(O)NR.sup.2 R.sup.2a, CH(.dbd.NH)NH.sub.2, NHC(.dbd.NH)NH.sub.2, SO.sub.2 NR.sup.2 R.sup.2a, NR.sup.2 SO.sub.2 NR.sup.2 R.sup.2a, and NR.sup.2 SO.sub.2 C.sub.1-4 alkyl;
  • R.sup.7, at each occurrence, is selected from H, OH, C.sub.1-6 alkyl, C.sub.1-6 alkylcarbonyl, C.sub.1-6 alkoxy, C.sub.1-4 alkoxycarbonyl, (CH.sub.2).sub.n -phenyl, C.sub.6-10 aryloxy, C.sub.6-10 aryloxycarbonyl, C.sub.6-10 arylmethylcarbonyl, C.sub.1-4 alkylcarbonyloxy C.sub.1-4 alkoxycarbonyl, C.sub.6-10 arylcarbonyloxy C.sub.1-4 alkoxycarbonyl, C.sub.1-6 alkylaminocarbonyl, phenylaminocarbonyl, and phenyl-C.sub.1-4 alkoxycarbonyl;
  • R.sup.8, at each occurrence, is selected from H, C.sub.1-6 alkyl and (CH.sub.2).sub.n -phenyl;
  • alternatively, R.sup.7 and R.sup.8 combine to form a 5 or 6 membered saturated, ring which contains from 0-1 additional heteroatoms selected from the group consisting of N, O, and S;
  • R.sup.9, at each occurrence, is selected from H, C.sub.1-6 alkyl and (CH.sub.2).sub.n -phenyl;
  • n is selected from 0, 1, 2, and 3;
  • m is selected from 0, 1, and 2;
  • p is selected from 0, 1, and 2;
  • r is selected from 0, 1, 2, and 3;
  • s is selected from 0, 1, and 2; and,
  • t is selected from 0 and 1.
  • 2. A compound according to claim 1, wherein is of formulae Ia-Ie: ##STR213## wherein: Z is selected from a bond, CH.sub.2 O, OCH.sub.2, CH.sub.2 NH, NHCH.sub.2, CH.sub.2 C(O), C(O)CH.sub.2, C(O)NH, C(O)NH, CH.sub.2 S(O).sub.2, S(O).sub.2 (CH.sub.2), SO.sub.2 NH, and SO.sub.2 NH;
  • B is selected from: Y, X--Y, and NR.sup.2 R.sup.2a ;
  • Y is selected from one of the following carbocyclic and heterocyclic systems which are substituted with 0-2 R.sup.4a ;
  • phenyl, piperidinyl, piperazinyl, pyridyl, pyrimidyl, furanyl, morpholinyl, thiophenyl, pyrrolyl, pyrrolidinyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, oxadiazole, thiadiazole, triazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,2,3-triazole, 1,2,4-triazole, 1,2,5-triazole, 1,3,4-triazole, benzofuran, benzothiofuran, indole, benzimidazole, benzoxazole, benzthiazole, indazole, benzisoxazole, benzisothiazole, and isoindazole;
  • Y may also be selected from the following bicyclic heteroaryl ring systems: ##STR214## K is selected from O, S, NH, and N.
  • 3. A compound according to claim 2, wherein is of formulae: ##STR215## wherein: D is selected from C(.dbd.NR.sup.7)NR.sup.8 R.sup.9 and (CR.sup.8 R.sup.9).sub.t NR.sup.8 R.sup.9 ;
  • R is selected from H, F, Cl, OR.sup.3, CH.sub.2 OR.sup.3, CH.sub.2 NH.sub.2 ;
  • A is selected from:
  • C.sub.5-6 carbocyclic residue substituted with 0-2 R.sup.4 ;
  • Y is selected from one of the following carbocyclic and heterocyclic systems which are substituted with 0-2 R.sup.4a ;
  • phenyl, piperidinyl, piperazinyl, pyridyl, pyrimidyl, furanyl, morpholinyl, thiophenyl, pyrrolyl, pyrrolidinyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, benzimidazolyl, oxadiazole, thiadiazole, triazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,2,3-triazole, 1,2,4-triazole, 1,2,5-triazole, and 1,3,4-triazole.
  • 4. A compound according to claim 3, wherein:
  • E is phenyl;
  • D is selected from C(.dbd.NH)NH.sub.2 and CH.sub.2 NH.sub.2 ;
  • R is selected from H, F, Cl, and Br;
  • A is selected from:
  • C.sub.5-6 carbocyclic residue substituted with 0-2 R.sup.4 ;
  • Y is selected from one of the following carbocyclic and heterocyclic systems which are substituted with 0-2 R.sup.4a ;
  • phenyl, piperidinyl, piperazinyl, pyridyl, pyrimidyl, furanyl, morpholinyl, thiophenyl, pyrrolyl, pyrrolidinyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrazolyl, imidazolyl, benzimidazolyl, oxadiazole, thiadiazole, triazole, 1,2,3-oxadiazole, 1,2,4-oxadiazole, 1,2,5-oxadiazole, 1,3,4-oxadiazole, 1,2,3-thiadiazole, 1,2,4-thiadiazole, 1,2,5-thiadiazole, 1,3,4-thiadiazole, 1,2,3-triazole, 1,2,4-triazole, 1,2,5-triazole, and 1,3,4-triazole;
  • R.sup.2, at each occurrence, is selected from H, CF.sub.3, C.sub.1-6 alkyl, benzyl, C.sub.5-6 carbocyclic residue substituted with 0-2 R.sup.4b, and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4b ;
  • R.sup.2a, at each occurrence, is selected from H, CF.sub.3, C.sub.1-6 alkyl, benzyl, phenethyl, C.sub.5-6 carbocyclic residue substituted with 0-2 R.sup.4b, and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4b ;
  • R.sup.2b, at each occurrence, is selected from CF.sub.3, C.sub.1-4 alkoxy, C.sub.1-6 alkyl, benzyl, C.sub.5-6 carbocyclic residue substituted with 0-2 R.sup.4b, and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4b ;
  • R.sup.2c, at each occurrence, is selected from CF.sub.3, OH, C.sub.1-4 alkoxy, C.sub.1-6 alkyl, benzyl, C.sub.5-6 carbocyclic residue substituted with 0-2 R.sup.4b, and 5-6 membered heterocyclic system containing from 1-4 heteroatoms selected from the group consisting of N, O, and S substituted with 0-2 R.sup.4b ;
  • alternatively, R.sup.2 and R.sup.2a, together with the atom to which they are attached, combine to form a ring selected from imidazolyl, morpholino, piperazinyl, pyridyl, and pyrrolidinyl, substituted with 0-2 R.sup.4b ;
  • R.sup.4, at each occurrence, is selected from H, .dbd.O, OR.sup.2, CH.sub.2 OR.sup.2, F, Cl, C.sub.1-4 alkyl, NR.sup.2 R.sup.2a, CH.sub.2 NR.sup.2 R.sup.2a, C(O)R.sup.2c, CH.sub.2 C(O)R.sup.2c, C(O)NR.sup.2 R.sup.2a, CH(.dbd.NR.sup.2)NR.sup.2 R.sup.2a, CH(.dbd.NS(O).sub.2 R.sup.5)NR.sup.2 R.sup.2a, SO.sub.2 NR.sup.2 R.sup.2a, NR.sup.2 SO.sub.2 -C.sub.1-4 alkyl, S(O).sub.2 R.sup.5, and CF.sub.3
  • provided that if B is H, then R.sup.4 is other than tetrazole, C(O)-alkoxy, and C(O)NR.sup.2 R.sup.2a ;
  • R.sup.4a, at each occurrence, is selected from H, .dbd.O, (CH.sub.2).sub.r OR.sup.2, F, Cl, C.sub.1-4 alkyl, NR.sup.2 R.sup.2a, CH.sub.2 NR.sup.2 R.sup.2a, NR.sup.2 R.sup.2b, CH.sub.2 NR.sup.2 R.sup.2b, (CH.sub.2).sub.r C(O)R.sup.2c, NR.sup.2 C(O) R.sup.2b, C(O) NR.sup.2 R.sup.2a, C(O)NH(CH.sub.2).sub.2 NR.sup.2 R.sup.2a, NR.sup.2 C(O)NR.sup.2 R.sup.2a, SO.sub.2 NR.sup.2 R.sup.2a, S(O).sub.2 R.sup.5, and CF.sub.3 ; and,
  • R.sup.4b, at each occurrence, is selected from H, .dbd.O, (CH.sub.2).sub.r OR.sup.3, F, Cl, C.sub.1-4 alkyl, NR.sup.3 R.sup.3a, CH.sub.2 NR.sup.3 R.sup.3a, C(O)R.sup.3, CH.sub.2 C(O)R.sup.3, C(O)OR.sup.3c, C(O)NR.sup.3 R.sup.3a, CH(.dbd.NR.sup.3)NR.sup.3 R.sup.3a, SO.sub.2 NR.sup.3 R.sup.3a, NR.sup.3 SO.sub.2 -C.sub.1-4 alkyl, NR.sup.3 SO.sub.2 CF.sub.3, NR.sup.3 SO.sub.2 -phenyl, S(O).sub.2 CF.sub.3, S(O).sub.2 -C.sub.1-4 alkyl, S(O).sub.2 -phenyl, and CF.sub.3.
  • 5. A compound according to claim 1, wherein the compound is selected from:
  • N-(2'-Aminosulfonyl-[1,1']biphen-4-yl)-2-(3'-amidinophenyl)nicotinamide;
  • N-[5-(2-aminosulfonyl)phenylpyrid-2-yl]-2-(3'-amidinophenyl)nicotinamide;
  • N-[5-(2-t-butylaminosulfonyl)phenylpyrid-2-yl]-2-(3'-amidinophenyl)nicotinamide; and,
  • N-[5-(2-aminosulfonyl)phenylpyrid-2-yl]-2-(3'-carboxamidophenyl)nicotinamide;
  • or a pharmaceutically acceptable salt thereof.
  • 6. A pharmaceutical composition, comprising: a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.
  • 7. A pharmaceutical composition, comprising: a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound according to claim 2 or a pharmaceutically acceptable salt thereof.
  • 8. A pharmaceutical composition, comprising: a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound according to claim 3 or a pharmaceutically acceptable salt thereof.
  • 9. A pharmaceutical composition, comprising: a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound according to claim 4 or a pharmaceutically acceptable salt thereof.
  • 10. A pharmaceutical composition, comprising: a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound according to claim 5 or a pharmaceutically acceptable salt thereof.
  • 11. A method for treating or preventing a thromboembolic disorder, comprising: administering to a patient in need thereof a therapeutically effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.
  • 12. A method for treating or preventing a thromboembolic disorder, comprising: administering to a patient in need thereof a therapeutically effective amount of a compound according to claim 2 or a pharmaceutically acceptable salt thereof.
  • 13. A method for treating or preventing a thromboembolic disorder, comprising: administering to a patient in need thereof a therapeutically effective amount of a compound according to claim 3 or a pharmaceutically acceptable salt thereof.
  • 14. A method for treating or preventing a thromboembolic disorder, comprising: administering to a patient in need thereof a therapeutically effective amount of a compound according to claim 4 or a pharmaceutically acceptable salt thereof.
  • 15. A method for treating or preventing a thromboembolic disorder, comprising: administering to a patient in need thereof a therapeutically effective amount of a compound according to claim 5 or a pharmaceutically acceptable salt thereof.
Parent Case Info

This application claims the benefit of U.S. Provisional Application No. 60/050,214, filed Jun. 19, 1997.

Foreign Referenced Citations (1)
Number Date Country
9616940 Jun 1996 WOX
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