Claims
- 1. A compound having the formula
- 2. A compound according to claim 1 wherein
A and C are hydrogen and B is —LBRB.
- 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 —LCRC.
- 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 —LARA, B is —LBRB, 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 —LARA; B is hydrogen; and C is —LCRC.
- 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 —LARA, B is —LBRB, and C is —LCRC.
- 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 —LBRB; and C is LCRC.
- 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.
CROSS REFERENCE TO RELATED APPLICATIONS
[0001] This application is a continuation-in-part of U.S. application Ser. No. 08/901,040, filed Jul. 25, 1997, pending.
Provisional Applications (1)
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Number |
Date |
Country |
|
60054982 |
Aug 1997 |
US |
Divisions (1)
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Number |
Date |
Country |
Parent |
09129989 |
Aug 1998 |
US |
Child |
09850826 |
May 2001 |
US |