N.sup.2 -alkoxynaphthalenesulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof
AssigneesMitsubishi Chemical Industries Limited, Shosuke Okamoto
InventorsShosuke Okamoto, Ryoji Kikumoto, Kazuo Ohkubo, Tohru Tezuka, Shinji Tonomura, Yoshikuni Tamao, Akiko Hijikata
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Abstract
N.sup.2 -alkoxynaphthalenesulfonyl-L-arginiamides and the pharmaceutically acceptable salts thereof have been found to be effective as pharmaceutical agents for the inhibition and suppression of thrombosis, and are prepared by reacting N.sup.2 -alkoxynaphthalenesulfonyl-L-arginyl halide with a secondary amine.
Claims10
N.sup.2 -alkoxynaphthalenesulfonyl-L-argininamides having the formula:
- ##STR22## and the pharmaceutically acceptable salts thereof, wherein R.sub.1 is a naphtyl substituted with at least one C.sub.1 -C.sub.5 alkoxy;
- R.sub.2 is C.sub.2 -C.sub.10 alkyl or C.sub.2 -C.sub.10 alkoxyalkyl;
- R.sub.3 is hydrogen or C.sub.1 -C.sub.10 alkyl;
- and n is an integer of 1, 2 or 3.
A method for inhibiting activity and suppressing activation of thrombin in vivo in mammals which comprises introducing into a living body a pharmaceutically effective amount of an N.sup.2 -alkoxynaphthalenesulfonyl-L-argininamide having the formula:
- ##STR23## or the pharmaceutically acceptable salts thereof wherein R.sub.1 is naphthyl substituted with at least one C.sub.1 -C.sub.5 alkoxy;
- R.sub.2 is C.sub.2 -C.sub.10 alkyl or C.sub.2 -C.sub.10 alkoxyalkyl, R.sub.3 is hydrogen or C.sub.1 -C.sub.10 alkyl;
- and n is an integer of 1, 2 or 3.
A process for producing an N.sup.2 -alkoxynaphthalenesulfonyl-L-argininamide having the formula (I):
- ##STR24## and the pharmaceutically acceptable salts thereof, wherein R.sub.1 is alkoxynaphthyl wherein each alkoxy substituent contains 1-5 carbon atoms;
- R.sub.2 is C.sub.2 -C.sub.10 alkyl or C.sub.2 -C.sub.10 alkoxyalkyl;
- R.sub.3 is hydrogen or C.sub.1 -C.sub.10 alkyl;
- and n is an integer of 1, 2 or 3, which comprises reacting an N.sup.2 -alkoxynaphthalenesulfonyl-L-arginyl halide having the formula (II):
- ##STR25## wherein R.sub.1 is defined herein above, and X is halogen, with a secondary amine having the formula (III):
- ##STR26## wherein R.sub.2, R.sub.3 and n are defined herein above.
Dependencies are inferred from the claim text.