US4104392A
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N2 -naphthalenesulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof, and antithrombotic compositions and methods employing them
Assignee: Mitsubishi Chemical Corp
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Filing: 1976-09-30
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Granted: 1978-08-01
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Expires: 1996-09-30
Abstract
Abstract N2-naphthalenesulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof have been found to be effective as pharmaceutical agents for the inhibition and suppression of thrombosis.
Inventors
- 👤 Shosuke Okamoto
- 👤 Akiko Hijikata
- 👤 Ryoji Kikumoto
- 👤 Yoshikuni Tamao
- 👤 Kazuo Ohkubo
- 👤 Tohru Tezuka
- 👤 Shinji Tonomura
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 13:49
CPC Classifications
C; C07; C07D; C07D295/00; C07D295/16; C07D295/18; C07D295/182; C07D295/185; A; A61; A61K; A61K31/00; A61K31/16; A61K31/18; A61K31/185; A61K31/19; A61K31/195; A61K31/33; A61K31/335; A61K31/395; A61K31/435; A61K31/44; A61K31/445; C07C; C07C311/00; C07C311/15; C07C311/16; C07D211/00; C07D211/04; C07D211/06; C07D211/08; C07D211/10; C07D211/16; C07D211/18; C07D211/30; C07D211/32; C07D211/36; C07D211/40; C07D211/44; C07D211/46; C07D211/60; C07D211/80; C07D211/84; C07D211/90; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/78; C07D213/79; C07D307/00; C07D307/02; C07D307/04; C07D307/10; C07D307/14; C07D307/34; C07D307/38; C07D307/52; C07D307/77; C07D307/91; C07D319/00; C07D319/10; C07D319/14; C07D319/22; A61K38/00
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
114 words
N 2 -naphthalenesulfonyl-L-argininamides having the formula ##STR15## and the pharmaceutically acceptable salts thereof, wherein R 1 is selected from the group consisting of naphthyl, 5,6,7,8-tetrahydronaphthyl and naphthyl substituted with at least one substituent selected from the group consisting of halo, nitro, cyano, hydroxy, C 1 -C 10 alkyl, C 1 -C 10 alkoxy and C 2 -C 20 dialkylamino; R 2 is selected from the group consisting of hydrogen, C 1 -C 10 alkyl, C 6 -C 10 aryl and C 7 -C 12 aralkyl; m is an integer of 0, 1 or 2; n is an integer of 0, 1 or 2; and m + n is an integer of 1 or 2.
Claim 2
Dependent Claim
114 words
N 2 -naphthalenesulfonyl-L-argininamides having the formula ##STR15## and the pharmaceutically acceptable salts thereof, wherein R 1 is selected from the group consisting of naphthyl, 5,6,7,8-tetrahydronaphthyl and naphthyl substituted with at least one substituent selected from the group consisting of halo, nitro, cyano, hydroxy, C 1 -C 10 alkyl, C 1 -C 10 alkoxy and C 2 -C 20 dialkylamino; R 2 is selected from the group consisting of hydrogen, C 1 -C 10 alkyl, C 6 -C 10 aryl and C 7 -C 12 aralkyl; m is an integer of 0, 1 or 2; n is an integer of 0, 1 or 2; and m + n is an integer of 1 or 2.
Claim 3
Dependent Claim
71 words
The compound of claim 1, wherein R 1 is selected from the group consisting of naphthyl, 5,6,7,8-tetrahydronaphthyl and naphthyl substituted with at least one substituent selected from the group consising of halo, hydroxy, C 1 -C 5 alkyl, C 1 -C 5 alkoxy and C 2 -C 10 dialkylamino; R 2 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, phenyl and C 7 -C 10 aralkyl.
Claim 4
Dependent Claim
53 words
The compound of claim 2, wherein R 1 is selected from the group consisting of 1-naphthyl, 2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, 5,6,7,8-tetrahydro-2-naphthyl, 6-methyl-2-naphthyl, 6-methyl-1-naphthyl, 7-methyl-1-naphthyl, 7-methyl-2-naphthyl, 6-ethyl-2-naphthyl, 6,7-dimethyl-1-naphthyl, 6,7-dimethyl-2-naphthyl, 6-isopropyl-2-naphthyl, 5-chloro-1-naphthyl, 6-chloro-2-naphthyl, 6-bromo-1-naphthyl, 5-hydroxy-1-naphthyl, 7-hydroxy-2-naphthyl, 5-dimethylamino-1-naphthyl, 5-dimethylamino-2-naphthyl, 5-diethylamino-1-naphthyl, 6-dimethylamino-1-naphthyl, 6-dimethylamino-2-naphthyl, 5-methoxy-1-naphthyl, 6-methoxy-2-naphthyl, 7-methoxy-2-naphthyl, 4,6-dimethoxy-2-naphthyl, 6,7-dimethoxy-2-naphthyl and 6,7-diethoxy-2-naphthyl; and R 2 is hydrogen, methyl, ethyl or tert-butyl.
Claim 5
Dependent Claim
10 words
The compound of claim 3, wherein R 2 is hydrogen.
Claim 6
Dependent Claim
13 words
The compound of claim 3, wherein m is 1 and n is 1.
Claim 7
Dependent Claim
13 words
The compound of claim 3, wherein m is 1 and n is 0.
Claim 8
Dependent Claim
11 words
A compound of claim 4, which is 2-[N 2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid.
Claim 9
Dependent Claim
11 words
A compound of claim 4, which is 2-[N 2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginyl]isoindoline-1-carboxylic acid.
Claim 10
Dependent Claim
11 words
A compound of claim 4, which is 2-[N 2 -(7-methoxy-2-naphthalenesulfonyl)-L-arginyl]isoindoline-1-carboxylic acid.
Claim 11
Dependent Claim
11 words
A compound of claim 4, which is 2-[N 2 -(7-methyl-2-naphthalenesulfonyl)-L-arginyl]isoindoline-1-carboxylic acid.
Claim 12
Independent Claim
138 words
A method for inhibiting activity and suppressing activation of thrombin in vivo, which comprises administering to a patient a pharmaceutically effective amount of an N 2 -naphthalenesulfonyl-L-argininamide having the formula ##STR16## or the pharmaceutically acceptable salt thereof, wherein R 1 is selected from the group consisting of naphthyl, 5,6,7,8-tetrahydronaphthyl and naphthyl substituted with at least one substituent selected from the group consisting of halo, nitro, cyano, hydroxy, C 1 -C 10 alkyl, C 1 -C 10 alkoxy and C 2 -C 20 dialkylamino; R 2 is selected from the group consisting of hydrogen, C 1 -C 10 alkyl, C 6 -C 10 aryl and C 7 -C 12 aralkyl, m is an integer of 0, 1 or 2; n is an integer of 0, 1 or 2; and m + n is an integer of 1 or 2.
Claim 13
Independent Claim
138 words
A method for inhibiting activity and suppressing activation of thrombin in vivo, which comprises administering to a patient a pharmaceutically effective amount of an N 2 -naphthalenesulfonyl-L-argininamide having the formula ##STR16## or the pharmaceutically acceptable salt thereof, wherein R 1 is selected from the group consisting of naphthyl, 5,6,7,8-tetrahydronaphthyl and naphthyl substituted with at least one substituent selected from the group consisting of halo, nitro, cyano, hydroxy, C 1 -C 10 alkyl, C 1 -C 10 alkoxy and C 2 -C 20 dialkylamino; R 2 is selected from the group consisting of hydrogen, C 1 -C 10 alkyl, C 6 -C 10 aryl and C 7 -C 12 aralkyl, m is an integer of 0, 1 or 2; n is an integer of 0, 1 or 2; and m + n is an integer of 1 or 2.
Claim 14
Dependent Claim
20 words
A pharmaceutical composition which comprises an antithrombotically effective amount of a compound of claim 1 and a pharmaceutically acceptable adjuvant.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-07-31 | 1982-01-30 | 1982-08-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-07-31 | 1986-01-30 | 1986-08-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-07-31 | 1990-01-30 | 1990-08-01 | $7700.00 | Window Closed / Lapsed |