US 6,855,726 B1Granted

Quinolones as serine protease inhibitors

AssigneeWarner-Lambert Company

InventorsDanette Andrea Dudley, Jeremy John Edmunds

Life of this patent

Estimating the term…

Abstract

The invention discloses quinolinones which display inhibitory effects on serine proteases such as factor Xa, thrombin and/or factor VIIa. The invention also discloses pharmaceutically acceptable salts and prodrugs of the compounds, pharmaceutically acceptable compositions comprising the compounds, their salts or prodrugs, and methods of using them a therapeutic agents for treating or preventing disease states in mammals characterized by abnormal thrombosis.

Claims30

Dependent claims

A compound according to Formula I

or a stereoisomers or pharmaceutically acceptable salts, esters, or amides thereof, wherein:
A is selected from CH2, CH, C(alkyl);
B is selected from H, alkyl, cycloalkyl, heteroalkyl, cycloalkylalkyl, heteroalkylalkyl, aryl, arylalkyl, heterocycle, heterocycloalkyl, each optionally substituted with R1 and R2;
D is selected from H, alkyl, cycloalkyl, heteroalkyl, cycloalkylalkyl, heteroalkylalkyl, aryl, arylalkyl, heterocycle, heterocycloalkyl, each optionally substituted with R1 and R2;
E is absent or selected from O, S, NH;
F is selected from N or NCH2;
G is selected from alkyl, alkyl interrupted by one or more heteroatoms, cycloalkyl, cycloalkyl interrupted by one or more heteroatoms;
J is heterocycle optionally substituted with R1 and R2;
K is absent or selected from an alkyl, alkyl interrupted by one or more heteroatoms, cycloalkyl interrupted by one or more heteroatoms, cycloalkylalkyl interrupted by one or more heteroatoms, each optionally substituted with R1 and R2;
L is selected from H, chlorine, fluorine, bromine, iodine, OH, O(alkyl), alkyl, fluoroalkyl, NO2, SH, S(O)n(alkyl), SO3H, SO3alkyl, C(═O)heteroaryl, C(═O)heteroarylalkyl, C(═O)OH, NC(═O)alkyl, NC(═O)aryl, NC(═O)cycloalkyl, NC(═O)cycloalkylalkyl, NC(═O) alkylaryl, R1, R2;
R1 is selected from H, C(═NH)NHNH2, alkylC(═NH)NHNH2, C(═NH)NHOH, alkylC(═NH)NHOH, NHC(═NH)NH2, alkylNHC(═NH)NR2, C(═S)NH2, alkylC(═S)NH2, C(═NH)alkyl, alkylC(═NH)alkyl, C(═NR3)N(R4)(R5), alkylC(═NR3)N(R4)(R5);
R2 is selected from H, chlorine, fluorine, bromine, iodine, OH, Oalkyl, NC(═O)alkyl, NC(═O)aryl, NC(═O)cycloalkyl, NC(═O)alkylaryl, C(═O)alkyl, C(═O)cycloalkyl. C(═O)cycloalkyl, C(═O)aryl, C(═O)alkyl, C(═O)heteroaryl and C(═O)heteroarylalkyl, NO2, SH, S(O)n(C1-10alkyl), SO3H, SO3alkyl, CHO, C(═O)OH, alkyl, C(═NH)alkyl, C(═NH)NHNH2, alkylC(═NH)NHNH2, C(═NH)NHOH, alkylC(═NH)NHOH, NHC(═NH)NH2, alkylNHC(═NH)NHNH2, C(═S)NH2, alkylC(═S)NH2, alkylC(—NH)alkyl, C(═NR3)N(R4)(R5), alkylC(═NR3)N(R4)(R5);
R3, R4, and R5 are a hydrogen atom, alkyl group having 1 to 4 carbon atoms optionally interrupted by a heteroatom, or R4 and R5 arc bonded to form —(CH2)p—W—(CH2)q-, wherein p and q are an integer of 2 or 3, a certain position on the methylene chain is unsubstituted or substituted by an alkyl group having 1 to 4 carbon atoms, W is a direct bond, —CH2—, —O—, —N(R6)—, or —S(O)2— wherein R6 is H or alkyl, and r is 0 or 1 or 2;
n is selected from 0, 1, 2;
X1 is C;
X2 is C;
X3 is C;
X4 is C;
and
--- represents an optional additional bond.

17 more elements

A compound according to Formula III

or a stereoisomer or pharmaceutically acceptable salts, esters, or amide thereof, wherein X, Y, R7, R9, and --- are as follows:
X is selected from (CH2)5,
(CH2)4,
(CH2)6,
CH2C(═O)NHCH2CH2,
CH2CH2NHC(═O)CH2,
(CH2)2NH(CH2)2,
(CH2)2O(CH2),
C6H4,
CH2C6,
C6H4CH2,
C6H10,
CH2C6H10,
C5H8,
CH2C5H8,
C5H8CH2, and
CH2CH═CHCH2CH2;
Y is selected from 2,6-dimethylpiperidinyl,
piperidinyl,
2,2,6,6-tetramethyl-piperidinyl-4-one,
(2-carboxy)piperidinyl,
(3-carboxy)piperidinyl,
(4-carboxy)piperidinyl,
3,5-dimethylpiperidinyl,
(4-hydroxy)piperidinyl,
(2-imino)piperidinyl,
piperidin-4-one-yl,
(2-dimethylaminomethyl)-piperidinyl,
(4-dimethylamino)-piperidinyl,
(4-sulphonyloxy)piperidinyl,
(2-phenyl)piperidinyl,
2,5-dimethylpyrrolidinyl,
pyrrolidinyl,
(2-carboxy)pyrrolidinyl,
(3-N-acetyl-N-methyl)pyrrolidinyl,
(3-amino)pyrrolidinyl,
(2,5-bis-methoxymethyl)-pyrrolidinyl,
2-hydroxymethyl-pyrrolidinyl,
2-hydroxymethyl-5-methyl-pyrrolidinyl,
diisopropylamino,
diethylamino,
methylamino,
1-methyl-4,5-dihydro-1H-imidazol-2-yl,
2,5-dimethyl-1H-1-imidazolyl,
morpholinyl,
2,6-dimethylmorpholinyl,
piperazinyl,
2,6-dimethylpiperazinyl,
1H-pyrazolyl,
tetrahydro-1H-pyrazolyl,
2,5-dimethyltetrahydro-1H-1-pyrazolyl, and
1,2,3,4-tetrahydro-2-oxo-3-phenyl-1-quinolinyl;
R7 is selected from (3-amidino)phenyl,
phenyl,
4-methoxyphenyl,
4-(amidino)phenyl,
3-(aminocarbonyl)phenyl,
3(methoxycarbonyl)phenyl,
(3-hydroxy)phenyl,
[3-hydroxyamino(imino)methyl]-phenyl,
[3-hydrazino(imino)methyl]-phenyl
(3-aminomethyl)phenyl, (3-amino)phenyl,
(3-methylamino)phenyl,
(3-dimethylamino)phenyl,
(5-amidino-2-hydroxy)phenyl,
(1-amidino)piperid-3-yl,
(1-amidino)pyrrolid-3-yl,
(5-amidino)thien-2-yl,
(5-amidino)furan-2-yl,
(5-amidino)-1,3-oxazol-2-yl,
(2-amidino)-1,3-oxazol-5-yl,
1H-pyrazol-5-yl,
tetrahydro-1H-pyrazol-3-yl,
(1-amidino)tetrahydro-1H-pyrazol-3-yl,
(2-amidino)-1H-imidazol-4-yl,
(2-amino)-1H-imidazol-4-yl,
(5-amidino)-1H-imidazol-2-yl,
(5-amino)-1H-imidazol-2-yl,
pyridin-3-yl,
(4-amino)pyridin-3-yl,
(4-dimethylamino)pyridin-3-yl,
(6-amino)pyridin-2-yl,
(6-amidino)pyridin-2-yl,
(2-amino)pyridin-4-yl,
(2-amidino)pyridin-4-yl,
(2-amidino)pyrimid-4-yl,
(2-amino)pyrimidin-4-yl,
(4-amidino)pyrimid-2-yl,
(4-amino)pyridin-2-yl
(6-amidino)pyrazin-2-yl,
(6-amino)pyrazin-2-yl,
(4-amidino)-1,3,5-triazin-2-yl,
(4-amino)-1,3,5-triazin-2-yl,
(3-amidino)1,2,4-triazin-5-yl,
(3-amino)-1,2,4-pyridin-5-yl,
(3-amidino)benzyl,
(3-amino)benzyl,
(3-aminomethyl)benzyl,
(1-amidino)piperid-3-ylmethyl,
(1-amidino)pyrrolid-3-ylmethyl,
(5-amidino)thien-2-ylmethyl,
(5-amidino)furan-2-ylmethyl,
(5-amidino)oxazol-2-ylmethyl,
(2-amidino)imidazol-5-ylmethyl,
(5-amidino)imidazol-2-ylmethyl,
(6-amidino)pyridin-2-ylmethyl,
(6-amidino)pyridin-2-ylmethyl,
(2-amidino)pyridin-4-ylmethyl,
(2-amino)pyrimidin-4-ylmethyl,
(4-amidino)pyrimidin-2-ylmethyl,
(4-amino)pyrimidin-2-ylmethyl,
(6-amidino)pyrazin-2-ylmethyl,
(6-amino)pyrazin-2-ylmethyl,
3-aminocyclohexyl,
3-amidinocyclohexyl,
3-aminocyclohexylmethyl,
3-amidinocyclohexylmethyl,
3-aminocyclopentyl,
3-amidinocyclopentyl,
3-aminocyclopentylmethyl, and
3-amidinocyclopentylmethyl;
and
R8 is selected from H,
Cl,
F,
SH,
SMe,
CF3,
CH3,
CO2H,
CO2Me,
CN,
C(═NH)NH2,
C(═NH)NHOH,
C(═O)NH2,
C(═O)NH2,
CH2OH,
CH2NH2,
NO2,
OH,
OMe,
OCH2Ph,
OCH2CO2H,
O(CH2)2CO2H,
O(CH2)3CO2H,
NHCH2CO2H,
NH(CH2)2CO2H,
NH(CH2)3CO2H,
OCH2CH2OH,
OCH2(1H-tetrazol-5-yl),
NH2,
NHButyl,
NMe2,
NHCH2Ph,
NHC(═O)Me,
NHC(═O)c-Hexyl,
NHC(═O)CH2c-Hexyl,
NHC(═O)Ph,
NHC(═O)CH2Ph,
NHS(═O)2Me,
NHS(═O)2c-Hexyl,
NHS(═O)2CH2c-Hexyl,
NHS(═O)2Ph, and
NHS(═O)2CH2Ph;
and
--- represents an optional additional end.

163 more elements

A compound according to Formula IV

or a stereoisomers or pharmaceutically acceptable salts, esters, or amides thereof, wherein X, Y, R7, R8, and --- are as follows:
X is selected from (CH2)5,
(CH2)4,
(CH2)6,
CH2C(═O)NHCH2CH2,
CH2CH2NHC(O)CH2,
(CH2)2NH(CH2)2,
(CH2)2O(CH2)2,
C6H4,
CH2C6H4,
C6H4CH2,
C6H10,
CH2C6H10,
C6H10CH2,
C5H8,
CH2C5H8,
C5H8CH2, and
CH2CH═CHCH2CH2;
Y is selected from 2,6-dimethylpiperidinyl,
piperidinyl,
2,2,6,6-tetramethyl-piperidinyl-4-one,
(2-carboxy)piperidinyl
(3-carboxy)piperidinyl,
(4-carboxy)piperidinyl,
3,5-dimethylpiperidinyl,
(4-hydroxy)piperidinyl,
(2-imino)piperidinyl,
piperidin-4-one-yl,
(2-dimethylaminomethyl)-piperidinyl,
(4 dimethylamino)-piperidinyl,
(4-sulphonyloxy)-piperidinyl,
(2-phenyl)piperidinyl,
2,5-dimethylpyrrolidinyl,
pyrrolidinyl,
(2-carboxy)pyrrolidinyl,
(3-N-acetyl-N-methyl)pyrrolidinyl,
(3-amino)pyrrolidinyl,
(2,5-bis-methoxymethyl)-pyrrolidinyl,
2-hydroxymethyl-pyrrolidinyl,
2-hydroxymethyl-5-methyl-pyrrolidinyl,
diisopropylamino,
diethylamino,
methylamino,
1-methyl-4,5-dihydro-1H-imidazol-2-yl,
2,5-dimethyl-1H-1-imidazolyl,
morpholinyl,
2,6-dimethylmorpholinyl,
piperazinyl,
2,6-dimethylpiperazinyl
1H-pyrazolyl,
tetrahydro-1H-pyrazolyl, and
2,5-dimethyltetrahydro-1H-1-pyrazolyl;
R7 is selected from (3-amidino)phenyl,
(3-hydroxy)phenyl,
[3-hydroxy]amino(imino)methyl-phenyl,
[3-hydrazino(imino)methyl)-phenyl,
(3-aminomethyl)phenyl
(3-methylamino)phenyl,
(3-dimethylamino)phenyl,
(5-amidino-2-hydroxy)phenyl,
(1-amidino)piperid-3-yl,
(1-amidino)pyrrolid-3-yl,
(5-amidino)thien-2-yl,
(5-amidino)film-2-yl,
(5-amidino)-1,3-oxazol-2-yl,
(2-amidino)-1,3-oxazol-5-yl,
1H-pyrazol-5-yl,
tetrahydro-1H-pyrazol-3-yl,
(1-amidino)tetrahydro-1H-pyrazol-3-yl,
(2-amidino)-1H-imidazol-4-yl,
(2-amidino)-1H-imidazol-4-yl,
(5-amidino)-1H-imidazol-2-yl,
(5-amino)-1H-imidazol-2-yl,
pyridin-3-yl,
(4-amino)pyridin-3-yl
(4-dimethylamino)pyridin-3-yl,
(6-amino)pyridin-2-yl,
(6-amidino)pyridin-2-yl,
(2-amino)pyridinyl,
(2-amidino)pyridin-4-yl,
(2-amidino)pyridine-4-yl,
(2-amino)pyrimidin-4-yl,
(4-amidino)pyrimid-2-yl
(4-amino)pyrimidin-2-yl,
(6-amino)pyrazin-2-yl,
(6-amidino)pyrazin-2-yl,
(4-amidino)-1,3,5-triazin-2-yl,
(4-amino)-1,3,5-triazin-2-yl,
(3-amidino)-1,2,4-triazin-5-yl,
(3-amino)-1,2,4-triazin-5-yl,
(3 amidino)benzyl, (3-amino)benzyl,
(3-aminomethyl)benzyl,
(1-amidino)piperid-3-ylmethyl,
(1-amidino)pyrrolid-3-ylmethyl,
(5-amidino)thien-2-ylmethyl,
(5-amidino)furan-2-ylmethyl,
(5-amidino)oxazol-2-ylmethyl,
(2-amidino)imidazol-5-ylmethyl,
(5-amidino)imidazol-2-ylmethyl,
(6-amidino)pyridin-2-ylmethyl,
(6-amino)pyridin-2-ylmethyl,
(2-amidino)pyrimidin-4-ylmethyl,
(2-amino)pyrimidin-4-ylmethyl,
(4-amidino)pyrimidin-2-ylmethyl,
(4-amino)pyrimidin-2-ylmethyl,
(6-amidino)pyrazin-2-ylmethyl,
(6-amino)pyrazin-2-ylmethyl,
3-aminocyclohexyl,
3-amidinocyclohexyl,
3-aminocyclohexylmethyl,
3-amidinocyclohexylmethyl,
3-aminocyclopentyl
3-amidinocyclopentyl
3-aminocyclopentylmethyl, and
3-amidinocyclopentylmethyl;
and
R8 is selected from H,
Cl,
F,
SH,
SMe,
CF3,
CH3,
CO2H,
CO2Me,
CN,
C(═NH)NH2,
C(═NH)NHOH,
C(═NH)NHNH2,
C(═O)NH2,
CH2OH,
CH2NH2,
NO2,
OH,
OMe,
OCH2Ph,
OCH2CO2H,
O(CH2)2CO2H,
O(CH2)3CO2H,
NHCH2CO2H,
NH(CH2)2CO2H,
NH(CH2)3CO2H,
OCH2CH2OH,
OCH2(1H-tetrazol-5-yl),
NH2,
NHButyl,
NMe2,
NHPh,
NHCH2Ph,
NHC(═O)Me,
NHC(═O)c-Hexyl,
NHC(═O)CH2c-Hexyl,
NHC(═O)Ph,
NHC(═O)CH2Ph,
NHS(═O)2Me,
NHS(═O)2c-Hexyl,
NHS(═O)2CH2c-Hexyl,
NHS(═O)2P, and
NHS(═O)2CH2Ph;
and
--- represents an optional additional bond.

158 more elements

A compound which is:

3-(1-5-[(2)-2,6-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
1-5-[(2R,6S)-2,6-Dimethyltetrahydro-[(2H)-pyridinyl]pentyl-33-hydroxyphenyl)-2(1H)-quinolinone;
3-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)pyridinyl)pentyl-2-oxo-1,2-dihydro-3-quinolinyl)-N-hydroxybenzenecarboxamide;
3-(1-S-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidohydrazide;
3-[3-(Aminomethyl)phenyl]-1-5-[(2R,6S)-2,6 dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2(1H)-quinolinone;
3-(3-Aminophenyl)-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2(1H)-quinolinone;
1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-3-[3-(methylamino)phenyl]-2(1H)-quinolinone;
3-[3-Dimethylamino)phenyl]-1-5-[(2R,6S)2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2(1H)-quinolinone;
3-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo 1,2-dihydro-3-quinolinyl)-4-hydroxybenzenecarboximidamide;
3-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)tetrahydro-[(2H)-pyridinecarboximidamide;
3-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl-1-pyrrolidinecarboximidamide;
5-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolyl)-2-thiophenecarboximidamide;
5-(1-S-(2R,6S) 2-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)2-furancarboximidamide;
2-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)-1,3-oxazole-5-carboximidamide;
5-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl-pentyl-2-oxo-1,2-dihydro-3-quinolinyl)-1,3-oxazole-2-carboximidamide;
1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-1H-pyrazol-3-yl)-2(1H)-quinolinone;
1-5-(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-3-tetrahydro-1H-pyrazol-3-yl-2(1-quinolinone;
3-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)-1-pyrazolidinecarboximidamide;
5-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3 quinolinyl)-1H-imidazole-2-carboximidamide;
3(2-Amino-1H-imidazol-5-yl)-1-5-[(2R,6S)-2,6-dimethyltetrahydro-[(2H)-pyridinyl]pentyl-2(1H)-quinolinone;
2-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl-pentyl-2-oxo-1,2-dihydro-3-quinolinyl)1H-imidazole-5-carboximidamide;
3-(5-Amino-1H-imidazol-2-yl)-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2(1H)-quinolinone;
1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-3-(3-pyridinyl)-2(1H)quinolinone;
3-(6-Amino-3-pyridinyl)-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2(1H)-quinolinone;
3-[6(Dimethylamino)-3-pyridinyl]-1-5-1(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2(1H)-quinolinone;
3-(6-Amino-2-pyridinyl)-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2(1H)quinolinone;
(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)-2-pyridinecarboximidamide;
(2-Amino-4-pyridinyl)-1-5-[(2R,6S)-2,6-dimethyltetrahydro-[(2H)-pyridinyl]pentyl-2(1H)-quinolinone;
4-1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)-2-pyridinecarboximidamide;
4-(1-S-[(2R,6S)-2,6-Dimethyltetrahydro-1-(2H)-pyridinyl]pentyl-2-oxo 1,2-dihydro-3-quinolinyl)2-pyridinecarboximidamide;
3-(2-Amino-4-pyridyl)-1-5-[(2R6S)-2,6-methyltetrahydro-(2H)-pyridinyl]pentyl-2(1H)-quinolinone;
2-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)-4-pyrimidinecarboximidamide;
3-(4-Amino-2-pyrimidinyl)-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(21)-pyridinyl]pentyl-2(1H)-quinolinone;
6-(1-5-[((2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl-pentyl-2-oxo-1,2-dihydro-3-quinolinyl)-2-triazine-3-carboximidamide;
3-(6-Amino-2-pyrazinyl)-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2(1H)-quinolinone;
4-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)-1,3,5-triazine-2-carboximidamide;
3-(4-Amino-1,3,5-triazin-2-yl)-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2(1H)-quinolinone;
5-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)-1,2,4-triazine-3-carboximidamide;
3-(3-Amino-1,2,4-triazine-5-yl)-1-5-(2R,6S)-2,6-dimethyltetrahydro-1-(2H)-pyridinyl]pentyl-2(1H)-quinolinone;
3-[1-5-[(2R,6S)-2,6-Dimethyltetrahydro-[(2-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)methyl]benzenecarboximidamide;
3-(3-Aminobenzyl)-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2(1H)quinolinone;
3-[3-(Aminomethyl)benzyl]-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H) pyridinyl]pentyl-2(1H)-quinolinone;
3-[(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)methyl]tetrahydro-1(2H)-pyridinecarboximidamide;
3-[(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)methyl]-1-pyrrolidinecarboximidamide;
5-[(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)methyl]-2-thiophenecarboximidamide;
5-[(1-5-[(2R,6S)-2,6 Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3 quinolinyl)methyl)-2-furancarboximidamide;
2-[(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)methyl]-1,3-oxazole-5-carboximidamide;
5-[(1-5-[(2R16S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)methyl]-1H-imidazole-2-carboximidamide;
2-[(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)methyl]-1H-imidazole-5-carboximidamide;
6-[(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)methyl]-2-pyridinecarboximidamide;
3-[(6-Amino-2-pyridinyl)methyl]-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2(1H)-quinolinone;
4-[(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)methyl]-2-pyrimidinecarboximidamide;
3-[(2-Amino-4-pyrimidinyl)methyl]-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2(1H)-quinolinone;
2-[(1-5-((2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinone)methyl]4-pyrimidinecarboximidamide;
3-[(4-Amino-2-pyrimidinyl)methyl]-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2(1H)-quinolinone;
6-[(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)methyl]-2-pyrazinecarboxamide;
3-[(6-Amino-2-pyrazinyl)methyl]-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1-(2H)-pyridinyl]pentyl-2(1H)-quinolinone;
3-(3-Aminocyclohexyl)-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl)pentyl-2(1H)-quinolinone;
3-[(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-[(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)cyclohexanecarboximidamide;
3-[(3-Aminocyclohexyl)methyl]-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2(1H)-quinolinone;
3-[(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)methyl]cyclohexanecarboximidamide;
3-(3-Aminocyclopentyl)-1-S-(2R,6S)2,6-dimethyltetrahydro-1-(2H)-pyridinyl]pentyl-2(1H)-quinolinone;
3-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)cyclopentanecarboximidamide;
3-[(3-Aminocyclopentyl)methyl]-1-5-[(2R,6S)2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2(1H) quinolinone;
3-[(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)methyl)cyclopentanecarboximidamide;
3-(1-4[(2R,6S)-2,6-Dimethyltetrahydro-[(2H)-pyridinyl]butyl-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-(1-6[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]hexyl-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
2-[3-3-[Amino(imino)methyl]phenyl-2-oxo-1(2H)-quinolinyl]-N-2-[(2R,6S)-2,6-Dimethyltetrahydro-1(2)-pyridinyl]ethylacetamide;
3-[3-3-[Amino(imino)methyl]phenyl-2-oxo-1(2H)-quinolinyl]-N-[(2R,6S)-2,6-Dimethyltetrahydro-1(2)pyridinyl]methylpropanamide;
3-1-[2-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]ethylamino)ethyl]-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-[1-[(2R,6S)-2,6-Dimethyltetrahydro-[(2H)-pyridinyl]ethoxyethyl)-2-oxo-1,2dihydro-3-quinolinyl)benzenecarboximidamide;
3-(1-4[(2R,6S)-2,6-Dimethyltetrahydro-[(2H)-pyridinyl]phenyl-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-(4-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]benzyl-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-(1-4-(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]methylphenyl)-2-oxo 1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-[1-(4-[(2R,6S)-2,6-Dimethyltetrahydro-[(2H)-pyridinyl)cyclohexylmethyl)-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-[1-(4-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]cyclohexylmethyl)2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-[1-(4-((2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]methylcyclopentyl)-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-(1-3-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]cyclopentyl-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-[1-(3-[(2R,6S)2,6-Dimethyltetrahydro-1(2H)-pyridinyl]cyclopentylmethyl)-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-[1-(3-[(2R,6S)2,6-]Dimethyltetrahydro-[(2H)-pyridinyl]methylcyclopentyl)-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-(1-(E5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]-2-pentenyl-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-[2-Oxo 1-(5-piperidinopentyl)-1,2-dihydro-3-quinolinyl]benzenecarboximidamide;
3-2-oxo-1-[5-(2,2,6,6-tetramethylpiperidino)pentyl]-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
1-5-[3-3-[Amino(imino)methyl]phenyl-2-oxo-[(2H)-quinolinyl]pentyl-2-piperidinecarboxylic acid;
1-5-3-3[Amino(imino)methyl]phenyl-2-oxo-1(2H)-quinolinyl]pentyl-3-piperidinecarboxylic acid;
1-5-3-3[Amino(imino)methyl]phenyl-2-oxo-1(2H)-quinolinyl]pentyl-3-piperidinecarboxylic acid;
3-1-[5-(3,5-Dimethylpiperidino)pentyl]-2-oxo-2-dihydro-3-quinolinylbenzenecarboxamide;
3-1-[5-(4-Hydroxypiperidino)pentyl]-2-oxo-1,2-dihydro-3-quinolinylbenzenecarboxamide;
3-1-[5-(2-Iminopiperidino)pentyl]-2-oxo-1,2-dihydro-3-quinolinylbenzenecarboxamide;
3-2-Oxo-1-[5-(4-oxopiperidino)pentyl]-1,2-dihydro-3-quinolinylbenzenecarboxamide;
3-[1-(5-2-[(Dimethylamino)methyl]piperidinopentyl)-2-oxo-1,2-dihydro-3-quinolinyl]benzenecarboxamide;
3(1-5-[4-(Diethylamino)piperidino]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboxamide;
1-5-[3-3-[Amino(imino)methyl]phenyl-2-oxo-1(2H)-quinolinyl]pentyl-4-piperidinesulfonic acid;
3-2-Oxo-1-[5-(2-phenylpiperidino)pentyl]-1,2-dihydro-3-quinolinylbenzenecarboximidamide;
3-1-[5-(2,5-Dimethyl-1-pyrrolidinyl)pentyl]-2-oxo-1,2-dihydro-3-quinolinylbenzenecarboximidamide;
3-2-Oxo-1-[5-(1-pyrrolidinyl)pentyl]-1,2-dihydro-3-quinolinylbenzenecarboximidamide;
1-5-[3-3-[Amino(imino)methyl]phenyl-2-oxo-1(2H)-quinolinyl]pentyl-2-pyrrolidinecarboxylic acid;
N-(1-5-[3-3-[Amino(imino)methyl]phenyl-2-oxo-1(2H)-quinolinyl]pentyltetrahydro-1H-pyrrol-3-yl)N-methylacetamide;
3-1-[5-(3-Amino-1-pyrrolidinyl)pentyl]-2-oxo-1,2-dihydro-3-quinolinylbenzenecarboximidamide;
3-(1-5-[2,5-bis(Methoxymethyl)-1-pyrrolidinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-(1-S-[2-(Hydroxymethyl)-1-pyrrolidinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-(1-5-[2-(Hydroxymethyl)-5-methyl-1-pyrrolidinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-1-[5-(Diisopropylamino)pentyl]-2-oxo-1,2-dihydro-3-quinolinylbenzenecarboximidamide;
3-1-[5-(Diethylamino)pentyl]-2-oxo-1,2-dihydro-3-quinolinylbenzenecarboximidamide;
3-1-[5-(Methylamino)pentyl]-2-oxo-1,2-dihydro-3-quinolinylbenzenecarboximidamide;
3-1-[5-(1-Methyl-1H-imidazol-2-yl)pentyl]-2-oxo-1,2-dihydro-3-quinolinylbenzenecarboximidamide;
3-1-[5-(2,5-Dimethyl-1H-imidazol-1-yl)pentyl]-2-oxo-1,2-dihydro-3-quinolinylbenzenecarboximidamide;
3-[1-(5-Morpholinopentyl)-2-oxo-1,2-dihydro-3-quinolinyl]benzenecarboximidamide;
3-1-[5-(3,5-Dimethylmorpholino)pentyl-2-oxo-1,2-dihydro-3-quinolinylbenzenecarboximidamide;
3-[2-oxo-1-(5-Piperazinopentyl)-1,2-dihydro-3-quinolinylbenzenecarboximidamide;
3-1-[5-(2,6-Dimethylpiperazino)pentyl]-2-oxo-1,2-dihydro-3-quinolinylbenzenecarboximidamide;
3-2-Oxo-1-5-(1H-pyrazol-1-yl)pentyl]-1,2-dihydro-3-quinolinylbenzenecarboximidamide;
3-[2-Oxo-1-(5-tetrahydro-1H-pyrazol-1-yl)pentyl)-1,2-dihydro-3-quinolinyl]benzenecarboximidamide;
3-1-[5-(2,5-Dimethyltetrahydro-1H-pyrazol-1-yl)pentyl]-2-oxo-1,2-dihydro-3-quinolinylbenzenecarboximidamide;
3-(7-Chloro-1-5-[(2R,6S)-2,6-dimethyltetrahydro 1(2H)pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-(1-5-(2R,6S)2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-7-fluoro-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-(1-5-[(2R,6S)-2,6 Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-7-sulfanyl-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-[(2H)-pyridinyl]pentyl-7-(methylsulfonyl)2-oxo-1,2-dihydro-3-quinolyl]benzenecarboximidamide;
3-[1-5-[(2R,6S)-2,6-Dimethyltetrahydro-[(2H)pyridinyl]pentyl-2-oxo-7-(trifluoromethyl)-1,2-dihydro-3-quinolinyl]benzenecarboximidamide;
3-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-7-methyl-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-3-[Amino(imino)methyl]phenyl-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1( ) pyridinyl]pentyl-2-oxo-1,2-dihydro-7-quinolinecarboxylic acid;
Methyl 3-3-[amino(imino)methyl]phenyl-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-7-quinolinecarboxylate;
3-(7-Cyano-1-5-[(2R,6S)-2,6 dimethyltetrahydro-(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-3-(Amino(imino)methyl]phenyl-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinecarboximidamide;
3-3-[Amino(imino)methyl]phenyl-1-5-(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-N-hydroxy-2-oxo-1,2-dihydro-7-quinolinecarboximidamide;
3-1-5-((2R,6S)-2,6-Dimethyltetrahydro-1(2H)pyridinyl]phenyl-7-hydrazino(imino)methyl]-2-oxo-1,2-dihydro-3-quinolinylbenzenecarboxamide;
3-3-(Amino(imino)methyl]phenyl-1-5-((2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-7-quinolinecarboxamide;
3-{[1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-7-(hydroxymethyl)-2-oxo-1,2-dihydro-3-quinolinyl]benzenecarboximidamide;
3-(7-(Aminomethyl)-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-(1-5-[[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-7-nitro-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(21)pyridinyl]pentyl-7-hydroxy-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-1,5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-7-methoxy-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-(7-(Benzyloxy)-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
2-[(3-3-[Amino(imino)methyl]phenyl-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2-pyridinyl]pentyl-2-oxo-1,2-dihydro-7-quinolinyl)oxy]acetic acid,
3-[(3-3-[Amino(imino)methyl]phenyl-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(S)-pyridinyl]pentyl-2-oxo-1,2-dihydro-7-quinolinyl)oxy]propanoic acid;
4-[(3-3-[Amino(imino)methyl]phenyl-1-5-[(2R,6S)2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-7-quinolinyl)oxy]butanoic acid;
2-[(3-3-[Amino(imino)methyl]phenyl-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-7-quinolinyl)amino]acetic acid;
3-[(3-3-[Amino(imino)methyl]phenyl-1-5-[(2R,6S)2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-7-quinolinyl)amino]propanoic acid;
4-((3-3-[Amino(imino)methyl]phenyl-1-S-((2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-7-quinolinyl)amino]butanoic acid;
3-[1-5-[(2H)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-7-(2-hydroxyethoxy)-2-oxo-1,2 dihydro-3-quinolinyl)benzenecarboximidamide;
3-[1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(21H)-pyridinyl]pentyl-2-oxo-7-(1H-1,2,3,4-tetrazol-5-ylmethoxy)-1,2-dihydro quinolinyl]benzenecarboximidamide;
3-(7-Amino-1-5-(2R,6S)-2,6-dimethyltetrahydro-[(2-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-(7-Butylamino)-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl 2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-(7-(imino)methyl-1-5-(2R,6S)-2,6-dimethyltetrahydro-1(21H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-(7-Anilino 1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-(7-(Benzylamino)-1-S-[(2R,6S)-2,6-dimethyltetrahydro-1(2H) pyridinyl]pentyl-2-oxo-1,2-dihydro 3-quinolinyl) benzenecarboxamide;
N-(3-3-[Amino(imino)methyl]phenyl-1-5-((2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-7-quinolinyl)acetamide;
N-(3-3-[Amino(imino)methyl]phenyl-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-7-quinolinyl)cyclohexanecarboxamide;
N-(3-3-[Amino(imino)methyl]phenyl-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2-pyridinyl]pentyl-2-oxo-1,2 dihydro-7-quinolinyl)-2-cyclohexylacetamide;
N-(3-3-[Amino(imino)methyl]phenyl-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-7-quinolinyl)benzenecarboximidamide;
N-(3-3-[Amino(imino)methyl]phenyl-1-5-((2R,6S)-2,6-dimethyltetrahydro-[(2)-pyridinyl]pentyl-2-oxo-1,2-dihydro-7-quinolinyl)-2-phenylacetamide;
3-1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-7-[(methylsulfonyl)amino]-2-oxo-1,2-dihydro-3-quinolinylbenzenecarboximidamide;
3-(7-[(Cyclohexylsulfonyl)amino)-1-5-((2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl)phenyl-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-(7-((Cyclohexylmethyl)sulfonyl]amino-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)pyridinyl]pentyl-2-oxo-1,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)pyridinyl]pentyl-2-oxo-7-[(phenylsulfonyl)amino]-1,2 dihydro-3-quinolinylbenzenecarboximidamide;
3-(7-[(Benzylsulfonyl)amino]-1-5-C(2R,6S)-2,6-dimethyltetrahydro-[(2H)-pyridinyl]pentyl-2-oxo-1 ,2-dihydro-3-quinolinyl)benzenecarboximidamide;
3-(1-5-[(2R,6S)2,6-Dimethyltetrahydro-1(28)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidamide;
1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-3-(3-hydroxyphenyl)3,4-dihydro-2(1H)-quinolinone;
3-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)N-hydroxybenzenecarboximidamide;
3-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidohydrazide;
3-[3-(Aminomethyl)phenyl]-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl pentyl-3,4-dihydro-2(1H)-quinolinone;
3-(3-Aminophenyl)-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-3,4-dihydro-2(1H)-quinolinone;
1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-3-[3-(methylamino)phenyl]-3,4-dihydro-2(1H)-quinolinone;
3-[3-(Dimethylamino)phenyl]-1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-3,4-dihydro-2(1H)quinolinone;
3-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-[(2)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)-N-hydroxybenzenecarboximidamide;
3-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)tetrahydro-1(2-pyrrolidinecarboximidamide;
3-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-[(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)-1-pyrrolidinecarboximidamide;
1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)-2-thiophenecarboximidamide;
5-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)-2-furancarboximidamide;
2-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-[(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl) 1,3-oxazole-carboximidamide;
5-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)-1,3-oxazole-2-carboximidamide;
1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-3-(1H-pyrazol-3-yl)-3,4-dihydro-2(1H)quinolinone;
1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)pyridinyl]pentyl-3-tetrahydro-1H-pyrazol-3-yl-3,4-dihydro-2(1H)-quinolinone;
3-(1-5-((2R,6S)-2,6-Dimethyltetrahydro 1 (2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)-1-pyrazolidinecarboximidamide;
5-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl) 1H-imidazole-2-carboximidamide;
3-(2-Amino-1H-imidazol-5-yl)-1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-3,4-dihydro-2(1H)quinolinone;
2-(15-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo 1,2,3,4-tetrahydro-3-quinolinyl) 1H-imidazole-5-carboximidamide;
3-(5-Amino-1H-imidazol-2-yl)-1-5-[(2R,6S)-2,6 Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-3,4-dihydro-2(1H)-quinolinone;
1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)pyridinyl]pentyl-3-(3-pyridinyl)-3,4-dihydro-2(1H)-quinolinone;
3-(6-Amino-3-pyridinyl)-1-5-[(2R,6S)-2,6-Dimethyltetrahydro-[(2H)-pyridinyl]pentyl-3,4-dihydro-2(1H)quinolinone;
3-(6-(Dimethylamino)-3-pyridinyl]-1-5-[(2R,6S)-2,6-dimethyltetrahydro- 1(2-pyridinyl]pentyl-3,4-dihydro-2(1H)quinolinone;
3-(6-Amino-2-pyridinyl)-1-5-[2R,6S)-2,6Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-3,4-dihydro-2(1}1)quinolinone;
6-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)-2-pyridinecarboximidamide;
3-(2-Amino-4-pyridinyl)-1-S-(2R,6S)-2,6-dimethyltetrahydro-[(M-pyridinyl]pentyl-3,4-dihydro-2(1H)quinolinone;
4-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)-2-pyridinecarboximidamide;
(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)2-pyrimidinecarboximidamide;
3-Amino-4-pyrimidinyl)-1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-3,4-dihydro-2(1H)-quinolinone;
2-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)-4-pyrimidinecarboximidamide;
3-(4-Amino-2-pyrimidinyl)-1-S-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-3,4-dihydro-2(1H)-quinolinone;
6-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H1)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)-2-pyrazinecarboximidamide;
3-(6-Amino-2-pyrazinyl)-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl-pentyl-3,4-dihydro-(2H)-quinolinone;
4-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)-1,3,5-triazine-2-carboximidamide;
3-(4-Amino-1,3,5-triazin-2-yl)-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-3,4-dihydro-2(1)quinolinone;
6-(1-5-(1-5-((2R,6S)-2,6-Dimethyltetrahydro-[(2>pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)-1,2,4-triazine-3-carboximidamide;
3-(3-Amino-1,2,4-triazin-5-yl)-1-5-[(2R,6S)-2,&dimethyltetrahydro 1 (2H)-pyridinyl)pentyl-3,4-dihydro-2(1H)quinolinone;
3-[(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-(2H)-pyridinyl]pentyl-2-oxo 1,2,3,4-tetrahydro-3-quinolinyl)methyl]benzenecarboximidamide;
3-(3-Aminobenzyl)-1-5-((2R,6S)-2,6-dimethyltetrahydro-[(2H)-pyridinyl]pentyl-3,4-dihydro-2(1H)-quinolinone;
3-[3-(Aminomethyl)benzyl]-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-3,4-dihydro-2(1H)-quinolinone;
3-[(1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)methyl]tetrahydro (2H)-pyridinecarboximidamide;
3-[(1-5-[(2R,6S)-2,6-dimethyltetrahydro(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)methyl]-1-pyrrolidinecarboximidamide;
5-[(1-5-[(2R,6S)-2,6-dimethyltetrahydro-[(2H)pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)methyl]-2-thiophenecarboximidamide;
5-[(1-S-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)methyl]-2-furancarboximidamide;
2-[(1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)methyl]-1,3-oxazole-5-carboximidamide;
5-[(1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)methyl]-1H-imidazole-2-carboximidamide;
2-[(1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)methyl]-1H-imidazole-5-carboximidamide;
6-[(1-5-[(2R,6S)-2,6-dimethyltetrahydro-1H-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)methyl]-2-pyrazinecarboximidamide;
3-[(6-Amino-2-pyridinyl)methyl]-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-3,4-dihydro-2(1 quinolinone;
4-[(1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)methyl]-2-pyrazinecarboximidamide;
3-[(2-Amino-4-pyrimidinyl)methyl-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-3,4-dihydro-2(1H)quinolinone;
2-[(1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)methyl]4-pyrazinecarboximidamide;
3-[(4-Amino-2-pyridinyl)methyl]-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-3,4-dihydro-2(1H)-quinolinone;
6-[(1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3 quinolinyl)methyl]-2-pyrazinecarboximidamide;
3-[(6-Amino-2-pyrazinyl)methyl]-1-5-[(2R,6S)-2.6 dimethyltetrahydro-1(2H)-pyridinyl]pentyl-3,4-dihydro-2(1H)-quinolinone;
3-(3-Aminocyclohexyl)-1-5-[(2R,6S)-2,6-dimethyltetrahydro-[(2H)-pyridinyl]pentyl-2-yl-3,4-dihydro-2(1H)-quinolinone;
3-(1-S—C(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)cyclohexanecarboximidamide;
3-[(3-Aminocyclohexyl)methyl]-1-5-[(2R,6S)2,6-dimethyltetrahydro-1(2H)-pyridinyl)pentyl-3,4-dihydro-2(1H)-quinolinone;
3-[(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)methyl]cyclohexanecarboximidamide;
3-(3-Aminocyclopentyl)-1-S-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-3,4-dihydro-2(1H)-quinolinone;
3-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-[(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl]cyclohexanecarboximidamide;
3-[(3-Aminocyclopentyl)methyl]-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-3,4-dihydro-2(1H)-quinolinone;
3-[(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl 2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)methyl]cyclopentanecarboximidamide;
3-(1-4[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)pyridinyl]butyl-2-oxo-1,2,3,4 tetrahydro-3-quinolinyl)benzenecarboximidamide;
3-(1-6-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]hexyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidamide;
2-[3-3-[Amino(imino)methyl]phenyl-2-oxo-1(2H)-quinolinyl]-N-2-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]ethylacetamide;
3-[3-3-(Amino(imino)methyl]phenyl-2-oxo-1(2H)quinolinyl]-N-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]methylpropanamide;
3-1-[2-(2-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]ethylamino)ethyl]2-oxo-1,2,3,4-tetrahydro-3-quinolinyl]benzenecarboximidamide;
3-[1-2-2-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]ethoxyethyl)-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl]benzenecarboximidamide;
3-(1-4-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]phenyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl]benzenecarboximidamide;
3-(1-4-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]benzyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl]benzenecarboximidamide;
3-[14-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]methylphenyl)-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl]benzenecarboximidamide;
3-(1-4-[(2R,6S)2,6-Dimethyltetrahydro-1(2H)-pyridinyl]cyclohexyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl]benzenecarboximidamide;
3-(1-4(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]cyclohexylmethyl)2-oxo-1,2,3,4-tetrahydro-3-quinolinyl]benzenecarboximidamide;
3-[1-(4-[(2R,6S)-2,6-Dimethyltetrahydro-[(2H)-pyridinyl]methylcyclohexyl)-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl]benzenecarboximidamide;
3-(1-3(2R,6S)-2,6-Dimethyltetrahydro-1(pyridinyl]cyclopentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl]benzenecarboximidamide;
3-[1-(3-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)pyridinyl]cyclopentylmethyl)-2-oxo-1,2,3,4-tetrahydro-3-quinolyl]benzenecarboximidamide;
3-[1-(3-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]methylcyclopentyl)-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl]benzenecarboximidamide;
3-[1-(E)-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]-2-pentenyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl]benzenecarboximidamide;
3-[2-Oxo-1-(5-piperidinopentyl)-1,2,3,4-tetrahydro-3-quinolinyl]benzenecarboximidamide;
3-2-Oxo-1-1-[5-(2,2,6,6-tetramethylpiperidino)pentyl]-1,2,3,4-tetrahydro-3-quinolinylbenzenecarboximidamide;
1-5-[3-3-[Amino(imino)methyl]phenyl-2-oxo-[(2H)-quinolinyl]pentyl-2-piperidinecarboxylic acid;
1-5-[3-3-[Amino(imino)methyl]phenyl-2-oxo-[(2H)-quinolinyl]pentyl-3-piperidinecarboxylic acid;
1-5-3-3[Amino(imino)methyl]phenyl-2-oxo-[(2H)-quinolinyl]pentyl-4-piperidinecarboxylic acid;
3-1-[5-(3,5-Dimethylpiperidino)pentyl]-2-oxo-1,2,3,4-tetrahydro-3-quinolinylbenzenecarboximidamide;
3-1-[5-(4-Hydroxypiperidino)pentyl]-2-oxo-1,2,3,4-tetrahydro-3-quinolinylbenzenecarboximidamide;
3-1-[5-(2-Iminopiperidino)pentyl]-2-oxo-1,2,3,4-tetrahydro-3-quinolinylbenzenecarboximidamide;
3-2-Oxo-1-[5-(4-oxopiperidino)pentyl]-1,2,3,4-tetrahydro-3-quinolinylbenzenecarboximidamide;
3-1-(5-2-[(Dimethylamino)methyl]piperidinopentyl)-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl]benzenecarboximidamide;
3-(1-5-[4-(Dimethylamino)piperidino)pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidamide;
1-5-[3-3-[amino(imino)methyl]phenyl-2-oxo 1(2H)-quinolinyl]pentyl-4-piperidinesulfonic acid;
3-2-Oxo-1-[5-(2-phenylpiperidino)pentyl]-1,2,3,4-tetrahydro-3-quinolinylbenzenecarboximidamide;
3-1-[5-(2,5-Dimethyl-1-pyrolidinyl)pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinylbenzenecarboximidamide;
3-2-oxo-1-[5-(1-pyrrolidinyl)pentyl]-1,2,3,4-tetrahydro-3-quinolinylbenzenecarboximidamide;
1-5-[3-3-[no(imino)methyl]phenyl-2-oxo-1(2H)-quinolinyl]pentyl-2-pyrrolidinecarboxylic acid;
N-(−5-[3-3-[Amino(imino)methyl]phenyl-2-oxo-1(2H)-quinolinyl]pentyl-tetrahydro-1H-pyrrol-3-yl)-N-methylacetamide;
3-1 [5-(3-Amino-1-pyrrolidinyl]pentyl]-2-oxo-1,2,3,4-tetrahydro-3-quinolinylbenzenecarboximidamide;
3-(1-S-[2,5-bis(Methoxymethyl)-1-pyrrolidinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidamide;
3-(1-5-[2-(Hydroxymethyl)-1-pyrrolidinyl]pentyl-2-oxo 1,2,3,4-tetrahydro 3-quinolinyl)benzenecarboximidamide;
3-(1-5-[2-(Hydroxymethyl)-5-methyl-1-pyrrolidinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidamide;
3-1-[5-(Diisopropylamino)pentyl]-2-oxo-1,2,3,4-tetrahydro-3-quinolinylbenzenecarboximidamide;
3-1-[S-(Diethylamino)pentyl]-2-oxo-1,2,3,4-tetrahydro-3-quinolinylbenzenecarboximidamide;
3-1-[5-(Methylamino)pentyl]-2-oxo-1,2,3,4-tetrahydro-3-quinolinylbenzenecarboximidamide;
3-1-[5-(1-Methyl-1H-imidazol-2-yl)pentyl]-2-oxo-1,2,3,4-tetrahydro-3-quinolinylbenzenecarboximidamide;
3-1-[5-(2,5-Dimethyl-1H-imidazol-1-yl)pentyl)-2-oxo-1,2,3,4-tetrahydro-3-quinolinylbenzenecarboximidamide;
3-[1-(5-Morpholinopentyl)-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl]benzenecarboximidamide;
3-1-[5-(3,5-Dimethylmorpholino)pentyl]-2-oxo-1,2,3,4-tetrahydro-3-quinolinylbenzenecarboximidamide;
3-[2-oxo-1 1-5-piperazino)pentyl]-1,2,3,4-tetrahydro-3-quinolinylbenzenecarboximidamide;
3-1-[5-(2,6-Dimethylpiperazino)pentyl]-2-oxo-1,2,3,4-tetrahydro-3-quinolinylbenzenecarboximidamide;
3-2-oxo-1-[5-(1H-pyrazol-1-yl)pentyl]-1,2,3,4-tetrahydro-3-quinolinylbenzenecarboximidamide;
3-[2-Oxo-1-(5-tetrahydro-H-pyrazol-1-yl)pentyl]-1,2,3,4-tetrahydro-3-quinolinyl]benzenecarboximidamide;
3-1-(5-(2,5-dimethyltetrahydro-1H-pyrazol-1-yl)pentyl]-2-oxo-1,2,3,4-tetrahydro-3-quinolinylbenzenecarboximidamide;
3-(7-Chloro-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidamide;
3-(1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-7-fluoro-2-oxo 1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidamide;
3-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-7-sulfanyl-1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidamide;
3-[1-5-[(2R,6S)-2,6-Dimethyltetrahydro-[(2H)-pyridinyl]pentyl-7-(methylsulfanyl)-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl]benzenecarboximidamide;
3-[1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-7-(trifluoromethyl)-1,2,3,4-tetra-3-quinolinyl)benzenecarboximidamide;
3-(1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-7-methyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidamide;
3-3-[Amino(imino)methyl]phenyl-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-7-quinolinecarboxylic acid;
methyl 3-3-(Amino(imino)methyl]phenyl-1-S-[(2R,6S)-2,6-dimethyltetrahydro 1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-7-quinolinecarboxylate;
3-(7-Cyano-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidamide;
3-3-[Amino(imino)methyl-3-phenyl-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-7-quinolinecarboximidamide;
3-3-[Amino(imino)methyl]phenyl-1-5-[(2R,6S)-2,6-dimethyltetrahydro-[(21)-pyridinyl]pentyl-N-hydroxy-2-oxo 1,2,3,4-tetrahydro-7-quinolinecarboximidamide;
3-1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)pyridinyl]pentyl-7-[hydrazino(imino)methyl]-2-oxo-1,2,3,4-tetrahydro-3-quinolinylbenzenecarboximidamide;
3-3-[Amino(imino)methyl]phenyl-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-7-quinolinecarboxamide;
3-[1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(pyridinyl]pentyl-7-(hydroxymethyl)-2-oxo-1,2,3,4-tetrahydro-3-quinolyl]benzenecarboximidamide;
3-(7-(Aminomethyl)-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidamide;
3-(1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-7-nitro-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidamide;
3-(1-[(2R, 6S)-2,6-Dimethyltetrahydro-1(2-pyridinyl]pentyl-7-hydroxy-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidamide;
3-(1-5-((2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pyridinyl-7-methoxy-2-oxo-1,2,3-tetrahydro-3-quinolinyl)benzenecarboximidamide;
3-(7-(Benzyloxy)-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidamide;
2-[(3-3-[Amino(imino)methyl]phenyl-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-quinolinyl)oxy]acetic acid;
3-[(3-3-[Amino(imino)methyl]phenyl--5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-7-quinolinyl)oxy]propanoic acid;
4-[(3-3-[Amino(imino)methyl]phenyl-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-7-quinolinyl)oxy]butanoic acid;
2-[(3-3-(Amino(imino)methyl]phenyl-1-5-[(2R6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-7-quinolinyl)amino]acetic acid;
3-[(3-3-[Amino(imino)methyl]phenyl-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(pyridinyl-pentyl-2-oxo-1,2-dihydro-7-quinolinyl)amino]propanoic acid;
4-(3-3-[Amino(imino)methyl]phenyl-1-5-[(2R,6S)-2-dimethyltetrahydro-1(2H)pyridinyl]pentyl-2-oxo-1,2-dihydro-7-quinolinyl)amino]butanoic acid;
3-[1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(pyridinyl]pentyl-7-(2-hydroxyethoxy)-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl]benzenecarboximidamide;
3-[1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2-pyridinyl]pentyl-2-oxo-7-(1H-1,2,3,4-tetrahydro-1-5-ylmethoxy)-1,2,3,4-tetrahydro-3-quinolinyl]benzenecarboximidamide;
3-(7-Amino-1-5-[(2R,6S)-2,6-dimethyltetrahydro(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidamide;
3-(7-(Butylamino)-1-5-(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidamide;
3-(7-(Dimethylamino)-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidamide;
3-(7-Anilino-1-5-t(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidamide;
3-(7(Benzylamino)-1-5-[(2R,6S)-2,6 dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo 1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidamide;
N3-3-[Amino(no)methyl]phenyl-1-5-[(2R,6S)-2,6,4-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo 1,2-dihydro-7-quinolinyl)acetamide;
N-(3-3-[Amino(imino)methyl]phenyl-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)pyridinyl]pentyl-2-oxo-1,2-dihydro-7-quinolinyl)cyclohexanecarboxamide;
N-(3-3-[Amino(imino)methyl]phenyl-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-7-quinolinyl)-2-cyclohexylacetamide;
N-(3-3-[Amino(imino)methyl]phenyl-1-5-[(2R,6S)-2,6-dimethyltetrahydro 1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-quinolinyl)benzenecarboxamide;
N-(3-3-[Amino(imino)methyl]phenyl-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2-dihydro-7-quinolyl)-2-phenylacetamide;
3-1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-7-[(methylsulfonyl)amino]-2-oxo-1,2,3,4-tetrahydro-3-quinolinylbenzenecarboximidamide;
3-(7-[(Cyclohexylsulfonyl)amino]-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidamide;
3-(7-[(Cyclohexylmethyl)sulfonyl]amino-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidamide;
1-[5-(2,6-Dimethyl-piperidin-1-yl)-pentyl]-3-(4-methoxy-phenyl)-3,4-dihydro-1H-quinolin-2-one;
3-1-5-[(2R,6S)-2,6-Dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-7-[(phenylsulfonyl)amino]-1,2,3,4-tetrahydro-3-quinolinylbenzenecarboximidamide;
or
3-(7-[(Benzylsulfonyl)amino]-1-5-[(2R,6S)-2,6-dimethyltetrahydro-1(2H)-pyridinyl]pentyl-2-oxo-1,2,3,4-tetrahydro-3-quinolinyl)benzenecarboximidamide.

311 more elements

Dependencies are inferred from the claim text.

Facts

Application: 09/601,479Filed 15 Dec 1998 · us provisional application
Priority: 31 Mar 1998
Granted: 15 Feb 2005
Term ends: Not estimatedThe source records don’t support an estimate.

Classification15 codes

C07D 215/227
Attached in position 2 or 4: only one oxygen atom which is attached in position 2
A61P 7/00
Drugs for disorders of the blood or the extracellular fluid
A61P 7/02
Drugs for disorders of the blood or the extracellular fluid: antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
A61P 9/00
Drugs for disorders of the cardiovascular system

Family

Application60/080,090Us provisional application · filed 31 Mar 1998
US 6,855,726 B1This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound according to Formula I

or a stereoisomers or pharmaceutically acceptable salts, esters, or amides thereof, wherein:
A is selected from CH2, CH, C(alkyl);
B is selected from H, alkyl, cycloalkyl, heteroalkyl, cycloalkylalkyl, heteroalkylalkyl, aryl, arylalkyl, heterocycle, heterocycloalkyl, each optionally substituted with R1 and R2;
D is selected from H, alkyl, cycloalkyl, heteroalkyl, cycloalkylalkyl, heteroalkylalkyl, aryl, arylalkyl, heterocycle, heterocycloalkyl, each optionally substituted with R1 and R2;
E is absent or selected from O, S, NH;
F is selected from N or NCH2;
G is selected from alkyl, alkyl interrupted by one or more heteroatoms, cycloalkyl, cycloalkyl interrupted by one or more heteroatoms;
J is heterocycle optionally substituted with R1 and R2;
K is absent or selected from an alkyl, alkyl interrupted by one or more heteroatoms, cycloalkyl interrupted by one or more heteroatoms, cycloalkylalkyl interrupted by one or more heteroatoms, each optionally substituted with R1 and R2;
L is selected from H, chlorine, fluorine, bromine, iodine, OH, O(alkyl), alkyl, fluoroalkyl, NO2, SH, S(O)n(alkyl), SO3H, SO3alkyl, C(═O)heteroaryl, C(═O)heteroarylalkyl, C(═O)OH, NC(═O)alkyl, NC(═O)aryl, NC(═O)cycloalkyl, NC(═O)cycloalkylalkyl, NC(═O) alkylaryl, R1, R2;
R1 is selected from H, C(═NH)NHNH2, alkylC(═NH)NHNH2, C(═NH)NHOH, alkylC(═NH)NHOH, NHC(═NH)NH2, alkylNHC(═NH)NR2, C(═S)NH2, alkylC(═S)NH2, C(═NH)alkyl, alkylC(═NH)alkyl, C(═NR3)N(R4)(R5), alkylC(═NR3)N(R4)(R5);
R2 is selected from H, chlorine, fluorine, bromine, iodine, OH, Oalkyl, NC(═O)alkyl, NC(═O)aryl, NC(═O)cycloalkyl, NC(═O)alkylaryl, C(═O)alkyl, C(═O)cycloalkyl. C(═O)cycloalkyl, C(═O)aryl, C(═O)alkyl, C(═O)heteroaryl and C(═O)heteroarylalkyl, NO2, SH, S(O)n(C1-10alkyl), SO3H, SO3alkyl, CHO, C(═O)OH, alkyl, C(═NH)alkyl, C(═NH)NHNH2, alkylC(═NH)NHNH2, C(═NH)NHOH, alkylC(═NH)NHOH, NHC(═NH)NH2, alkylNHC(═NH)NHNH2, C(═S)NH2, alkylC(═S)NH2, alkylC(—NH)alkyl, C(═NR3)N(R4)(R5), alkylC(═NR3)N(R4)(R5);
R3, R4, and R5 are a hydrogen atom, alkyl group having 1 to 4 carbon atoms optionally interrupted by a heteroatom, or R4 and R5 arc bonded to form —(CH2)p—W—(CH2)q-, wherein p and q are an integer of 2 or 3, a certain position on the methylene chain is unsubstituted or substituted by an alkyl group having 1 to 4 carbon atoms, W is a direct bond, —CH2—, —O—, —N(R6)—, or —S(O)2— wherein R6 is H or alkyl, and r is 0 or 1 or 2;
n is selected from 0, 1, 2;
X1 is C;
X2 is C;
X3 is C;
X4 is C;
and
--- represents an optional additional bond.

17 more elements

Facts

Application

09/601,479Filed 15 Dec 1998 · us provisional application

Priority

31 Mar 1998

Granted

15 Feb 2005

Term ends

Not estimatedThe source records don’t support an estimate.

Classification15 codes

C07D 215/227
Attached in position 2 or 4: only one oxygen atom which is attached in position 2
A61P 7/00
Drugs for disorders of the blood or the extracellular fluid
A61P 7/02
Drugs for disorders of the blood or the extracellular fluid: antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
A61P 9/00
Drugs for disorders of the cardiovascular system