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US 4,069,317 AGranted
N.sup.2 -Arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof
AssigneesMitsubishi Chemical Industries Limited, Shosuke Okamoto
InventorsShosuke Okamoto, Akiko Hijikata, Ryoji Kikumoto, Yoshikuni Tamao, Kazuo Ohkubo, Tohru Tezuka, Shinji Tonomura
Life of this patent
Estimating the term…
Abstract
N.sup.2 -arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof have been found to be effective as pharmaceutical agents for the inhibition and suppression of thrombosis in mammals.
Claims9
N.sup.2 -arylsulfonyl-L-argininamides having the formula (I):
- ##STR62## and the pharmaceutically acceptable salts thereof, wherein R.sub.1 is selected from the group consisting of naphthyl, 5,6,7,8-tetrahydronaphthyl, naphthyl substituted with at least one substituent selected from the group consisting of halo, nitro, cyano, hydroxy, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxy and C.sub.2 -C.sub.20 dialkylamino, phenyl, phenyl substituted with at least one substituent selected from the group consisting of halo, nitro, cyano, hydroxy, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxy and C.sub.2 -C.sub.20 dialkylamino, C.sub.7 -C.sub.12 aralkyl, ##STR63## wherein R.sub.5 is hydrogen, C.sub.1 -C.sub.10 alkyl or C.sub.1 -C.sub.10 alkoxy;
- R.sub.2 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.10 alkenyl, C.sub.3 -C.sub.10 alkynyl, C.sub.2 -C.sub.10 alkoxyalkyl, C.sub.2 -C.sub.10 alkylthioalkyl, C.sub.2 -C.sub.10 alkylsulfinylalkyl, C.sub.1 -C.sub.10 hydroxyalkyl, C.sub.2 -C.sub.10 carboxyalkyl, C.sub.3 -C.sub.10 alkoxycarbonylalkyl, C.sub.1 -C.sub.10 haloalkyl, C.sub.7 -C.sub.15 aralkyl, C.sub.8 -C.sub.15 .alpha.-carboxyaralkyl, C.sub.3 -C.sub.10 cycloalkyl and C.sub.4 -C.sub.10 cycloalkylalkyl;
- R.sub.3 is selected from the group consisting of C.sub.1 -C.sub.5 alkyl, carboxy, C.sub.2 -C.sub.10 alkoxycarbonyl, phenyl, C.sub.7 -C.sub.12 aralkyl and ring substituted benzyl wherein said substituent is C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy;
- R.sub.4 is hydrogen;
- and n is an integer of 0, 1 or 2.
2 more elements
A method of inhibiting activity and suppressing activation of thrombin in vivo, which comprises administring to a mammal a pharmaceutically effective amount of an N.sup.2 -arylsulfonyl-L-argininamide having the formula (I):
- ##STR66## or the pharmaceutically acceptable salt thereof wherein R.sub.1 is selected from the group consisting of naphthyl, 5,6,7,8-tetrahydronaphthyl, naphthyl substituted with at least one substituent selected from the group consisting of halo, nitro, cyano, hydroxy, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxy and C.sub.2 -C.sub.20 dialkylamino, phenyl, phenyl substituted with at least one substituent selected from the group consisting of halo, nitro, cyano, hydroxy, C.sub.1 -C.sub.10 alkyl, C.sub.1 -C.sub.10 alkoxy and C.sub.2 -C.sub.20 dialkylamino, C.sub.7 -C.sub.12 aralkyl, ##STR67## wherein R.sub.5 is hydrogen, C.sub.1 -C.sub.10 alkyl or C.sub.1 -C.sub.10 alkoxy:
- R.sub.2 is selected from the group consisting of hydrogen, C.sub.1 -C.sub.10 alkyl, C.sub.3 -C.sub.10 alkenyl, C.sub.3 -C.sub.10 alkynyl, C.sub.2 -C.sub.10 alkoxyalkyl, C.sub.2 -C.sub.10 alkylthioalkyl, C.sub.2 -C.sub.10 alkylsulfinylalkyl, C.sub.1 -C.sub.10 hydroxyalkyl, C.sub.2 -C.sub.10 carboxyalkyl, C.sub.3 -C.sub.10 alkoxycarbonylalkyl, C.sub.1 -C.sub.10 haloalkyl, C.sub.7 -C.sub.15 aralkyl, C.sub.8 -C.sub.15 .alpha.-carboxyaralkyl, C.sub.3 -C.sub.10 cycloalkyl and C.sub.4 -C.sub.10 cycloalkylalkyl;
- R.sub.3 is selected from the group consisting of C.sub.1 -C.sub.5 alkyl, carboxy, C.sub.2 -C.sub.10 alkoxycarbonyl, phenyl, C.sub.7 -C.sub.12 aralkyl and ring substituted benzyl wherein said substituent is C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy;
- R.sub.4 is hydrogen;
- and n is an integer of 0, 1 or 2.
2 more elements
Dependencies are inferred from the claim text.