Urokinase inhibitors

Abstract

Compounds having the formula are inhibitors of urokinase and are useful in the treatment of diseases in which urokinase plays a role. Also disclosed are urokinase-inhibiting compositions and a method of inhibiting urokinase in a mammal.

What is claimed is:  
     
         1 . A compound having the formula  
       
         
           
           
               
               
           
         
         Z is selected from the group consisting of 
 (1) nitrogen;  
 (2) methine; and  
 (3) methine substituted with —NR 1 R 2 ;  
 
         A is selected from the group consisting of 
 (1) hydrogen and  
 (2) —L A R A ;  
 
         B is selected from the group consisting of 
 (1) hydrogen and  
 (2) —L B R B  and  
 
         C is selected from the group consisting of 
 (1) hydrogen and  
 (2) —L C R C ,  
 with the proviso that at least one of A, B or C is other than hydrogen; and with the proviso that when A is other than hydrogen, at least one of B or C is other than hydrogen,  
 wherein for A, B, and C, L A , L B  and L C  are independently selected from the group consisting of  
 (1) a covalent bond,  
 (2) —(CH 2 ) m —,  
 (3) —NR 1 —,  
 (4) —NR 2 C(X)NR 3 —,  
 (5) —C(X)—,  
 (6) —NR 1 C(X)— 
 (7) —C(X)NR 2 —,  
 (8) —CH═CH—,  
 (9) —C≡C—,  
 (10) —O— 
 (11) —S(O) t —,  
 (12) —C≡C(CH 2 ) n NR 2 C(X)—,  
 (13) —C(X)NR 2 (CH 2 ) n C≡C—,  
 (14) —(CH 2 ) n NSO 2 —,  
 (15) —NR 2 SO 2 (CH 2 ) n C≡C—,  
 (16) —C≡C(CH 2 ) n NR 2 SO 2 NR 3 —,  
 (17) —NR 2 SO 2 NR 3 (CH 2 ) n C≡C—,  
 (18) —SO 2 NR 2 —,  
 (19) —NR 2 SO 2 —,  
 (20) —NR 2 SO 2 NR 3 —,  
 (21) —N═N—,  
 (22) —C(X)N(OR 2 )—,  
 (23) —N(OR 2 )C(X)—,  
 (24) —HC═CH(CH 2 ) n NR 2 C(X)—,  
 (25) —(CH 2 ) n NR 2 C(X)CH═CH—,  
 (26) —CH═CH(CH 2 ) n NSO 2 —,  
 (27) —NR 2 SO 2 (CH 2 ) n CH═CH—,  
 (28) —(CH 2 ) n NR 2 SO 2 NR 3 —,  
 (29) —NR 2 SO 2 NR 3 (CH 2 ) n CH═CH—,  
 (30) —NR 2 C(O)O—,  
 (31) —OC(O)NR 2 —,  
 (32) —CH═NO—,  
 (33) —ON═CH— and  
 (34)  
                     
 wherein W is selected from the group consisting of 
 (a) —O—,  
 (b) —S—,  
 (c) —NR 1 — and  
 (d) —(CH 2 ) m —,  
 wherein each functional group is depicted with its right-hand end being the end which is attached to the naphthyl or quinolyl ring and its left-hand end being the end which is attached to R A , R B  or R C ;  
 
 
         R A , R B  and R C  are independently selected from the group consisting of  
         (1) aryl;  
         (2) arylalkoxy, wherein the alkylene group is of one to six carbon atoms;  
         (3) alkyl of one to ten carbon atoms;  
         (4) alkenyl of two to ten carbon atoms;  
         (5) alkoxycarbonyl of one to six carbon atoms;  
         (6) alkynyl of two to ten carbon atoms;  
         (7) halogen;  
         (8) —NR 1 R 2 ;  
         (9) heterocycle;  
         (10) cycloalkenyl of four to twelve carbon atoms;  
         (11) cycloalkyl of three to twelve carbon atoms;  
         (12) —NR 1 C(O)NR 2 R 3 ; and  
         (13) —NR 1 C(O)R 50 , wherein R 50  is alkyl of one to six carbon atoms; wherein, at each occurence, R 1  is selected from the group consisting of  
         (1) hydrogen;  
         (2) an N-protecting group;  
         (3) alkyl of one to six carbon atoms;  
         (4) alkenyl of two to six carbon atoms;  
         (5) alkynyl of two to six carbon atoms;  
         (6) aryl;  
         (7) arylalkyl, wherein the alkylene group is of one to six carbon atoms;  
         (8) cycloalkyl of three to eight carbon atoms and  
         (9) cycloalkylalkyl, wherein the cycloalkyl group is of three to eight carbon atoms, and the alkylene group is of one to ten carbon atoms; and  
         wherein, at each occurence, R 2  and R 3  are independently selected from the group consisting of  
         (1) hydrogen;  
         (2) alkyl of one to six carbon atoms;  
         (3) alkenyl of two to six carbon atoms;  
         (4) alkynyl of two to six carbon atoms;  
         (5) aryl;  
         (6) arylalkyl, wherein the alkylene group is of one to six carbon atoms  
         (7) cycloalkyl of three to eight carbon atoms and  
         (8) cycloalkylalkyl, wherein the cycloalkyl group is of three to eight carbon atoms, and the alkylene group is of one to ten carbon atoms; and  
         wherein, at each occurence, X is selected from the group consisting of  
         (1) O and  
         (2) S; and  
         wherein, at each occurence,  
         m is one to five,  
         n is zero to four and  
         t is zero to two; and  
         wherein, at each occurence, the alkyl, alkenyl, alkynyl, aryl, heterocycle, cycloalkyl, and cycloalkenyl groups are optionally substituted.  
       
     
     
         2 . A compound according to    claim 1    wherein 
 A and C are hydrogen and  
 B is —L B R B .  
 
     
     
         3 . A compound according to    claim 2    selected from the group consisting of 
 7-(2-hydroxyethoxy)-2-naphthalenecarboximidamide mono(trifluoroacetate) salt; methyl 5-[7-[(aminoiminomethyl)-2-naphthalenyl]oxy]pentanoate; mono(trifluoroacetate) salt;  
 5-[[6-(aminoiminomethyl)-2-naphthalenyl]oxy]pentanoic acid, mono(trifluoroacetate) salt;  
 methyl 4-[[[7-amino(hydroxyimino)methyl]-2-naphthalenyl] oxy]methyl]benzoate;  
 methyl 2-[[6-(aminoiminomethyl)-2-naphthalenyl]oxy]acetate, mono(trifluoroacetate) salt;  
 7-[2-(4-morpholinyl)ethoxy]-2-naphthalenecarboximidamide, bis(trifluoroacetate) salt;  
 2-[[6-(aminoiminomethyl)-2-naphthalenyl]oxy]acetic acid, mono(trifluoroacetate) salt; and  
 methyl 4-[6-(aminoiminomethyl)-2-naphthalenyl]oxy]methyl]benzoate, mono(trifluoroacetate) salt.  
 
     
     
         4 . A compound according to    claim 1    wherein 
 A and B are hydrogen; and  
 C is —L C R C .  
 
     
     
         5 . A compound according to    claim 4    selected from the group consisting of 
 8-(carbonylbenzyloxy)amino-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;  
 N-[7-(aminoiminomethyl)-1-naphthalenyl)acetamide mono(trifluoroacetate) salt;  
 methyl [7-(aminoiminomethyl)-1-naphthalenyl)carbamate mono(trifluoroacetate) salt;  
 methyl 3-[[7-(aminoiminomethyl)-1-naphthalenyl]amino]-3-oxopropionate mono(trifluoroacetate) salt;  
 N-[7-(aminoiminomethyl)-1-naphthalenyl]-2-(phenylmethoxy)acetamide mono(trifluoroacetate) salt;  
 N-[7-(aminoiminomethyl)-1-naphthalenyl]-1,3-benzodioxole-5-carboxamide mono(trifluoroacetate) salt,  
 N-[7-(aminoiminomethyl)-1-naphthalenyl]benzenemethanesulfonamide mono(trifluoroacetate) salt,  
 methyl [7-(aminoiminomethyl)-1-naphthalenyl]methylcarbamate, mono(trifluoroacetate) salt;  
 propyl [7-(aminoiminomethyl)-1-naphthalenyl]carbamate, mono(trifluoroacetate) salt;  
 N-[7-(aminoiminomethyl)-1-naphthalenyl]-N′-methylurea, mono(trifluoroacetate) salt;  
 ethyl [7-(aminoiminomethyl)-1-naphthalenyl)carbamate, mono(trifluoroacetate) salt;  
 N-[7-(aminoiminomethyl)-1-naphthalenyl)propanamide, mono (trifluoroacetate) salt;  
 N-[7-(aminoiminomethyl)-1-naphthalenyl)-2-methoxyacetamide, mono(trifluoroacetate) salt;  
 N-[7-(aminoiminomethyl)-1-naphthalenyl]urea, mono(trifluoroacetate) salt;  
 N-[7-(aminoiminomethyl)-1-naphthalenyl]-2-hydroxyacetamide, mono(trifluoroacetate) salt;  
 8-(2-pyrimidinylamino)-2-naphthalenecarboximidamide, bis(trifluoroacetate) salt;  
 8-amino-2-naphthalenecarboximidamide, bis(trifluoroacetate) salt;  
 8-(2-pyridinylamino)-2-naphthalenecarboximidamide, bis(trifluoroacetate) salt; and 
 N-hydroxy-8-(2-pyrimidinylamino)-2-naphthalenecarboximidamide, mono(trifluoroacetate) salt.  
 
 
     
     
         6 . A compound according to    claim 1    wherein 
 A is —L A R A ,  
 B is —L B R B , and  
 C is hydrogen.  
 
     
     
         7 . A compound according to    claim 6    which is 
 6, 7-dimethoxy-2-naphthalenecarboximidamide mono(trifluoroacetate) salt.  
 
     
     
         8 . A compound according to    claim 1    wherein 
 A is —L A R A ;  
 B is hydrogen; and  
 C is —L C R C .  
 
     
     
         9 . A compound according to    claim 8    selected from the group consisting of 
 methyl 6-(aminoiminomethyl)-4-[(methoxycarbonyl)amino]-2-naphthalenecarboxylate mono(trifluoroacetate) salt;  
 6-methoxy-8-benzyloxy-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;  
 2-[(7-aminoiminomethyl-3-methoxy-I -naphthalenyl)oxy]acetamide mono(trifluoroacetate) salt;  
 6-(aminoiminomethyl)-4-(3-furanyl)-N- [4-(trifluoromethyl)phenyl]-2-naphthalenecarboxamide, mono(trifluoroacetate) salt;  
 6-(aminoiminomethyl)-4-(3-furanyl)-N-(4-pyridinyl)-2-naphthalenecarboxamide, dihydrochloride;  
 6-(aminoiminomethyl)-4-(3-furanyl)-N-(1H, pyrazol-3-yl)-2-naphthalenecarboxamide, dihydrochloride;  
 6-(aminoiminomethyl)-4-(3-furanyl)-N-(3-pyridinyl)-2-naphthalenecarboxamide, dihydrochloride;  
 methyl [7-(aminoiminomethyl)-3-[[[4-(aminomethyl)phenyl]amino]carbonyl]-1-naphathalenyl]carbamate, bis(trifluoroacetate) salt;  
 6-(aminoiminomethyl)-4-(3-furanyl)-N-(2-pyridinyl)-2-naphthalenecarboxamide, dihydrochloride;  
 6-(aminoiminomethyl)-4-(3-furanyl)-N-phenyl-2-naphthalenecarboxamide, monohydrochloride;  
 6-(aminoiminomethyl)-4-[1-(methylsulfonyl)-1H-pyrazol-4-yl]-N-phenyl-2-naphthalenecarboxamide, monohydrochloride;  
 6-(aminoiminomethyl)-4-[5-(methylthio)-3-furanyl)]-N-phenyl-2-naphthalenecarboxamide, monohydrochloride;  
 6-(aminoiminomethyl)-N-[4-(aminomethyl)phenyl]-4-(2-pyrimidinylamino)-2-naphthalenecarboxamide, tris(trifluoroacetate) salt;  
 6-(aminoiminomethyl)-N-phenyl-4-(2-pyrimidinylamino)-2naphthalenecarboxamide, mono(trifluoroacetate) salt;  
 N-[(4-(aminomethyl)phenyl]-6-[amino(hydroxyimino)methyl]-4-(2-pyrimidinylamino)-2-naphthalenecarboxamide, bis(trifluoroacetate) salt;  
 6-(aminoiminomethyl)-N-[4-(hydroxymethyl)phenyl]-4-(2-pyrimidinylamino)-2-naphthalenecarboxamide, mono(trifluoroacetate) salt;  
 methyl [3-[[[4-(aminomethyl)phenyl]amino]carbonyl]-7-[4-amino(hydroxyimino)methyl]-1-naphthalenyl]carbamate, bis(trifluoroacetate) salt;  
 6-(aminoiminomethyl)-N-phenyl-4-(tetrahydro-3-furanyl)-2-naphthalenecarboxamide,monohydrochloride;  
 6-[amino(hydroxyimino)methyl]-N-phenyl-4-(2-pyrimidinylamino)-2-naphthalenecarboxamide;  
 6-(aminoiminomethyl)-4-[5-(ethylthio)-3-furanyl]-N-phenyl-2-naphthalenecarboxamide,monohydrochloride;  
 6-(aminoiminomethyl)-4-[5-(propylthio)-3-furanyl]-N-phenyl-2-naphthalenecarboxamide,monohydrochloride;  
 6-(aminoiminomethyl)-N-phenyl-4-(2-pyrrolidinyl)-2-naphthalenecarboxamide, mono(trifluoroacetate) salt;  
 6-(aminoiminomethyl)-4-[5-(propylsulfonyl)-3-furanyl]-N-phenyl-2-naphthalenecarboxamide, monohydrochloride;  
 6-(aminoiminomethyl)-4-[5-[methylthio)methyl]-3-furanyl]-N-phenyl-2-naphthalenecarboxamide, monohydrochloride;  
 6-(aminoiminomethyl)-4-[5-(methoxymethyl)-3-furanyl]-N-phenyl-2-naphthalenecarboxamide, monohydrochloride;  
 naphthalenecarboxamide, mono(trifluoroacetate) salt; and  
 6-(aminoiminomethyl)-4-[5-(ethythio)tetrahydro-3-furanyl]-N-phenyl-2-naphthalenecarboxamide, monohydrochloride.  
 
     
     
         10 . A compound according to    claim 1    wherein 
 A is —L A R A ,  
 B is —L B R B , and  
 C is —L C R C .  
 
     
     
         11 . A compound according to    claim 10    which is 
 6, 7, 8-trimethoxy-2-naphthalenecarboximidamide mono(trifluoroacetate) salt.  
 
     
     
         12 . A compound according to    claim 1    wherein 
 A is hydrogen;  
 B is —L B R B ; and  
 C is L C R C .  
 
     
     
         13 . A compound according to    claim 12    selected from the group consisting of 
 7, 8-Dimethoxy-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;  
 2-[(7-aminoiminomethyl)-2-methoxy-1-naphthalenyl)oxy]acetamide mono(trifluoroacetate) salt;  
 7-benzyloxy-8-iodo-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;  
 methyl [(7-aminoiminomethyl-2-methoxy-1-naphthalenyl)oxy]acetate mono(trifluoroacetate) salt;  
 2-[(7-aminoiminomethyl-2-methoxy-1-naphthalenyl)oxy]-yl-acetic acid mono(trifluoroacetate) salt;  
 1-[(7-aminoiminomethyl-2-methoxy-1-naphthalenyl)oxy]-3-hydroxypropane mono(trifluoroacetate) salt;  
 1-[(7-aminoiminomethyl-2-methoxy-1-naphthalenyl)oxy]-3-bromopropane mono(hydrochloride) salt;  
 3-[(7-aminoiminomethyl-2-methoxy-1-naphthalenyl)oxy]propene mono(trifluoroacetate) salt;  
 1-[(7-aminoiminomethyl-2-methoxy-1-naphthalenyl)oxy]-3-phenylpropane mono(hydrochloride) salt;  
 1-[(7-aminoiminomethyl-2-methoxy-1-naphthalenyl)oxy]-3-[1-(3,4-dimethoxy)phenyl]propane mono(hydrochloride) salt;  
 7-methoxy-8-(2-furanyl)-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;  
 (E)- {7-methoxy-8-[2-(phenyl)ethenyl] } -2-naphthaleneimidamide mono(trifluoroacetate) salt  
 7-(2 hydroxyethoxy)-8-iodo-2-naphthalenecarboximidamide mono(trifluoroacetate, salt,  
 7-propoxy-8-iodo-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;  
 7-methoxy-8-(1H-pyrazol-4-yl)-2-naphthalenecarboximidamide bis(trifluoroacetate) salt;  
 7-methoxy-8-iodo-2-naphthalenecarboximidamide mono(trifluoroacetate) salt  
 7-methoxy-8-(3-furanyl)-2-naphthalenecarboximidamide mono(methanesulfonate) salt;  
 7-methoxy-8-(2-benzofuranyl)naphthalene-2-carboximidamide mono(methanesulfonate) salt;  
 (E)-8-[2-(1 ,3-benzodioxol-5-yl)ethenyl]-2-naphthalenecarboximidamide mono(methanesulfonate) salt;  
 (±)-7-methoxy-8-(tetrahydro-3-furanyl)-2-naphthalenecarboximidamide mono(methanesulfonate) salt;  
 7-methoxy-8-[2-pyrimidinyl(oxy)]-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;  
 7-methoxy-8-[2-thiazoyl(oxy)]naphthalene-2-carboximidamide mono(trifluoroacetate) salt;  
 7-methoxy-8-(4-nitrophenoxy)-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;  
 7-methoxy-8-pentafluorophenoxy-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;  
 7-methoxy-8-[N-2-pyrimidinyl(amino)]-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;  
 4-[7-(aminoiminomethyl)-2-methoxy-1-naphthalenyl]dihydro-2(3 H)-fiuranone mono(trifluoroacetate) salt;  
 7-methoxy-8-(1-acetyl-1H-pyrazolyl)-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;  
 7-methoxy-8-[1-(methylsulfonyl)-1H-4-pyrazolyl]-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;  
 6-[2-(4-aminophenyl)ethoxy]-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;  
 methyl [3-methoxy-6-(aminoiminomethyl)-4-naphthalenyl]carbamate mono(trifluoroacetate) salt;  
 7-methoxy-8-[2-pyrimidinyl(amino)]-2-naphthalenecarboximidamide bis(trifluoroacetate) salt;  
 methyl [7-(aminoiminomethyl)-2-methoxy-1-naphthalenyl)carbamate, mono(trifluoroacetate) salt;  
 7-methoxy-8-(2-pyrimidinylamino)-2-naphthalenecarboximidamide, bis(trifluoroacetate) salt;  
 7-methoxy-8-[(phenylmethyl)amino]-2-naphthalenecarboximidamide, mono(trifluoroacetate) salt,  
 7-methoxy-8-(phenylamino)-2-naphthalenecarboximidamide, mono(trifluoroacetate) salt;  
 7-methoxy-8-[(4-methoxyphenyl)amino]-2-naphthalenecarboximidamide, mono(trifluoroacetate) salt;  
 (E)-3-[7-(aminoiminomethyl)-2-methoxy-1-naphthalenyl)-2-propenamide, mono(trifluoroacetate) salt;  
 7-methoxy-8-(3-oxo-1-cyclopenten-1-yl)-2-naphthalenecarboximidamide, mono(trifluoroacetate) salt;  
 methyl 4-[[[7-(aminoiminomethyl)-1-(2-pyrimidinylamino)-2-naphthalenyl]oxy]methyl]benzoate, mono(trifluoroacetate) salt;  
 4-[[[7-(aminoiminomethyl)-1-(2-pyrimidinylamino)-2-naphthalenyl]oxy]methyl] benzoic acid, mono(trifluoroacetate) salt;  
 7-methoxy-8-(pyrazinyloxy)-2-naphthalenecarboximidamide, dimethanesulfonate salt;  
 7-methoxy-8-(phenylthio)-2-naphthalenecarboximidamide, methanesulfonate; and  
 7-methoxy-8-(pyrazinylamino)-2-naphthalenecarboximidamide, bis(trifluoroacetate) salt.  
 
     
     
         14 . A compound selected from the group consisting of 
 7, 8-dimethoxy-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;    6, 7, 8-trimethoxy-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;    6, 7-dimethoxy-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;    2-[(7-aminoiminomethyl-2-methoxy-1-naphthalenyl)oxy]acetamide mono(trifluoroacetate) salt;    7-benzyloxy-8-iodo-2-naphthalenecarboximidamide mono(trifluoroacetate) salt; methyl [(7-aminoiminomethyl-2-methoxy-1-naphthalenyl)oxy]acetate mono(trifluoroacetate) salt;    2-[(7-aminoiminomethyl-2-methoxy-1-naphthalenyl)oxy]-yl-acetic acid mono(trifluoroacetate) salt;    1-[(7-aminoiminomethyl-2-methoxy-1-naphthalenyl)oxy]-3-hydroxypropane mono(trifluoroacetate) salt;    phenylmethyl [7-(aminoiminomethyl)-1-naphthalenyl)carbamate mono(trifluoroacetate) salt;    N-[7-(aminoiminomethyl)-1-naphthialenyl)acetamide mono(trifluoroacetate) salt; methyl [7-(aminoiminomethyl)-1-naphthalenlyl)carbamate mono(trifluoroacetate) salt; methyl 3-[[7-(aminoiminomethyl)-1-naphthalenyljamino]-3-oxopropanoate mono(trifluoroacetate) salt;    N-[7-(aminoiminomethyl)-1-naphthalenyl1-2-(phenylmethoxy)acetamide mono(trifluoroacetate) salt;    N-[7-(aminoiminomethyl)-1-naphthalenyl]-1,3-benzodioxide-3-carboxamide mono(trifluoroacetate) salt;    N-[7-(aminoiminomethyl)-1-naphthalenyl]benzenemethanesulfonamide mono(trifluoroacetate) salt;    1-[(7-aminoiminomethyl-2-methoxy-1-naphthalenyl)oxy]-3-bromopropane mono(hydrochloride) salt;    3-[(7-aminoiminomethyl-2-methoxy-1-naphthalenyl)oxy]propene mono(trifluoroacetate) salt;    1-[(7-aminoiminomethyl-2-methoxy-1-naphthalenyl)oxy]-3-phenylpropane mono(hydrochloride) salt;    1-[(7-aminoiminomethyl-2-methoxy-1-naphthalenyl)oxy]-3- [1-(3,4-dimethoxy)phenyl]-propane mono(hydrochloride) salt;    7-methoxy-8-(2-furanyl)-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;    methyl 6-(aminoiminomethyl)-4-[(methoxycarbonyl)amino]-2-naphthalenecarboxylate mono(trifluoroacetate) salt;    (E)-6-[2-(phenyl)ethenyl]-2-naphthaleneimidamide mono(trifluoroacetate) salt;    7-(2-hydroxyethoxy)-8-iodo-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;    7-(2-hydroxyethoxy)-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;    6-methoxy-8-benzyloxy-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;    2-[(7-aminoiminomethyl-3-methoxy-1-naphthalenyl)oxy]acetamide mono(trifluoroacetate) salt;    7-propoxy-8-iodo-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;    7-methoxy-8-(l H-pyrazol-4-yl)-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;    7-methoxy-8-iodo-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;    7-methoxy-8-(3-furanyl)-2-naphthalenecarboximidamide mono(methanesulfonate) salt;    7-methoxy-8-(2-benzofuranyl)naphthalene-2-carboximidamide mono(methanesulfonate) salt;    (E)-8-[2-(1,3-benzodioxol-5-yl)ethenyl]-2-naphthalenecarboximidamide mono(methanesulfonate) salt;    (±)-7-methoxy-8-(tetrahydro-3-furanyl)-2-naphthalenecarboximidamide mono(methanesulfonate) salt;    7-methoxy-8-[2-pyrimidinyl(oxy)]-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;    7-methoxy-8-[2-thiazoyl(oxy)]naphthalene-2-carboximidamide mono(trifluoroacetate) salt;    7-methoxy-8-(4-nitrophenoxy)-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;    7-methoxy-8-pentafluorophenoxy-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;    7-methoxy-8-[N-2-pyrimidinyl(amino)]-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;    N-(6-aminoiminomethyl-2-naphthalenyl)-N′-benzylurea mono(trifluoroacetate) salt;    N-(6-aminoiminomethyl-2-naphthalenyl)-N′-methylurea mono(trifluoroacetate) salt;    N-(6-aminoiminomethyl-2-naphthalenyl)-N′-isopropylurea mono(trifluoroacetate) salt;    N-(6-aminoiminomethyl-2-naphthalenyl)-N′-phenyl-N′-methylurea mono(trifluoroacetate) salt;    6-aminonaphthalene-2-carboximidamide mono(trifluoroacetate) salt;    N-(6-aminoiminomethyl-2-naphthalenyl)-N′-cyclohexylurea mono(trifluoroacetate) salt;    N-(6-aminoiminomethyl-2-naphthalenyl)-N′-benzyloxyurea mono(trifluoroacetate) salt;    1, 1-dimethylethyl [4-[[(6-cyano-2-naphthalenyl)amino]carbonyl]phenyl]carbamate mono(trifluoroacetate) salt    N-[6-(aminoiminomethyl)-2-naphthalenyl]-4-(aminomethyl)benzamide mono(trifluoroacetate) salt;    4-[7-(aminoiminomethyl)-2-methoxy-1-naphthalenyl]dihydro-2(3H)-furanone mono(trifluoroacetate) salt;    7-methoxy-8-(1-acetyl-1H-pyrazolyl)-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;    7-methoxy-8- [1-(methylsulfonyl)-1H-4-pyrazolyl]-2-naphthalenecarboximidamide mono(trifluoroacetate) salt;    methyl [3-methoxy-6-(aminoiminomethyl)-4-naphthalenyl]carbamate mono(trifluoroacetate) salt;    7-methoxy-8-[2-pyrimidinyl(amino)]-2-naphthalenecarboximidamide; and bis(trifluoroacetate) salt.    
     
     
         15 . A method for inhibiting urokinase in a mammal in need of such treatment, comprising adminstering to the mammal a therapeutically effective amount of a compound of    claim 1   .  
     
     
         16 . A composition for inhibiting urokinase comprising both a pharmaceutical carrier and a therapeutically effective amount of a compound of    claim 1   .