# US 5,707,994 A · 2,3-diaminopropionic acid derivative

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- Number: US 5,707,994 A
- Document ID: US5707994A
- Status: Granted
- Kind: A
- Application number: 08/633,800
- Filed: 1996-04-19
- Granted: 1998-01-13
- Earliest claimed: 1993-10-19
- Assignees: Sumitomo Pharmaceuticals Company, Limited
- Inventors: Yoshihara Ikeda; Yasuyuki Ueki; Hisakazu Kishimoto; Toshio Nishihara; Yumiko Kamikawa
- Web page: https://patentgrep.com/patent/US5707994A

## CPC

- C07D 213/78: Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07C 311/06: to acyclic carbon atoms of hydrocarbon radicals substituted by carboxyl groups
- C07C 311/19: to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C 311/29: having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C07C 311/39: having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C 311/42: to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07D 211/22: by oxygen atoms
- C07D 211/26: with hydrocarbon radicals, substituted by nitrogen atoms
- C07D 211/34: with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D 211/58: attached in position 4
- C07D 211/60: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D 211/62: attached in position 4
- C07D 217/22: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D 217/26: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D 295/185: from aliphatic carboxylic acids
- C07D 295/192: from aromatic carboxylic acids
- C07C 2602/08: the other ring being five-membered, e.g. indane
- C07C 2603/18: Fluorenes; Hydrogenated fluorenes
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present invention relates to a 2,3-diaminopropionic acid derivative of the formula (1): ##STR1## or a pharmaceutically acceptable salt thereof. The compounds of the present invention are useful as a platelet aggregation inhibitor, a cancer metastasis inhibitor, a wound healing agent or a bone resorption inhibitor.

## Claims

### Claim 1

A compound of the formula (1): ##STR215## wherein R.sup.1 is a hydrogen atom, a lower alkyl group, a cycloalkyl group, a lower alkenyl group, a lower alkynyl group, an aryl group, a heterocyclic group, a substituted lower alkyl group, a substituted cycloalkyl group, a substituted lower alkenyl group, a substituted lower alkynyl group, a substituted aryl group or a substituted heterocyclic group;
R.sup.2 is a lower alkyl group, a cycloalkyl group, a lower alkenyl group, a lower alkynyl group, an aryl group, a heterocyclic group, a substituted lower alkyl group, a substituted cycloalkyl group, a substituted lower alkenyl group, a substituted lower alkynyl group, a substituted aryl group or a substituted heterocyclic group;
V.sup.3 and V.sup.4 are the same or different and each a hydrogen atom, an alkyl group, a substituted lower alkyl group, a cycloalkyl group, an amino group, an acylamino group, a lower alkyloxycarbonyl group or a lower alkyloxycarbonyl group substituted by an aryl group;
V.sup.5 is an imino group or an oxygen atom;
V.sup.6 and V.sup.7 are a hydrogen atom or a lower alkyl group;
A.sup.6 is a divalent group selected from the following groups:
--(CH.sub.2).sub.f --CONR.sup.10 --CH.sub.2 --CHR.sup.9 -- (R.sup.9 and R.sup.10 are the same or different and each are a hydrogen atom or a lower alkyl group, f is 0 or 1);
--Y.sup.4 --(CH.sub.2).sub.d -- (Y.sup.4 is an oxygen atom, and d is 3 or 4);
--(CH.sub.2).sub.f --CO--(CH.sub.2).sub.d -- (f and d are the same as defined above);
--(CH.sub.2).sub.f --CH(OH)--(CH.sub.2).sub.d -- (f and d are the same as defined above);
--NR.sup.10 CO--(CH.sub.2).sub.d -- (R.sup.10 and d are the same as defined above);
--Y.sup.4 --(CH.sub.2).sub.g --Y.sup.5 -- (Y.sup.4 is the same as defined above, Y.sup.5 is an oxygen atom or --NR.sup.11 -- (R.sup.11 is a hydrogen atom or a lower alkyl group), and g is 2 to 4);
a group of the formula: ##STR216## wherein a is 1 or 2, and f is the same as defined above; a group of the formula: ##STR217## wherein f is the same as defined above, Y.sup.6 is a methine group or a nitrogen atom;
a group of the formula: ##STR218## wherein Y.sup.5 and f are the same as defined above, and h is 0 or 1; a group of the formula: ##STR219## wherein Y.sup.4, Y.sup.5 and h are the same as defined above, or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein A.sup.6 is a divalent group selected from the following groups:
--(CH.sub.2).sub.f --CONR.sup.10 --CH.sub.2 --CHR.sup.9 -- (R.sup.9, R.sup.10 and f are the same as defined above);
Y.sup.4 --(CH.sub.2).sub.d -- (Y.sup.4 and d are the same as defined above);
--(CH.sub.2).sub.f --CO--(CH.sub.2).sub.d -- (f and d are the same as defined above);
a group of the formula: ##STR220## wherein a and f are the same as defined above; a group of the formula: ##STR221## wherein f and Y.sup.6 are the same as defined above, V.sup.5 is an imino group;
V.sup.6 and V.sup.7 are a hydrogen atom;
or a pharmaceutically acceptable salt thereof.

### Claim 3

(2S)-3-(3-(4-Amidinobenzoylamio)propanoylam ino)-2-(4-ethyl)benzenesulfonylaminopropanoic acid, or a pharmaceutically acceptable salt thereof.

### Claim 4 (depends on 1)

The compound according to claim 1, wherein V.sup.5 is an imino group, and V.sup.6 and V.sup.7 are a hydrogen atom, or a pharmaceutically acceptable salt thereof.

### Claim 5 (depends on 1, 2)

The compound according to claim 1 or 2, herein V.sup.3 and V.sup.4 are a hydrogen atom, and A.sup.6 is --CO--NH--CH.sub.2 --CH.sub.2 -- or --O--(CH.sub.2).sub.3 --, or a pharmaceutically acceptable salt thereof.

### Claim 6 (depends on 1, 2, 4)

The compound according to any one of claims 4, 1 and 2, wherein the stereoconfiguration of the 2-position thereof is S-configuration, or a pharmaceutically acceptable salt thereof.

### Claim 7 (depends on 1, 2, 4)

A platelet aggregation inhibitor which contains the compound as set forth in any one of claims 4, 1 and 2, or a pharmaceutically acceptable salt thereof.

### Claim 8 (depends on 1, 2, 4)

A cancer metastasis inhibitor which contains the compound as set forth in any one of claims 4, 1 and 2, or a pharmaceutically acceptable salt thereof.

### Claim 9 (depends on 1, 2, 4)

A wound healing agent which contains the compound as set forth in any one of claims 4, 1 and 2, or a pharmaceutically acceptable salt thereof.

### Claim 10 (depends on 1, 2, 4)

A bone resorption inhibitor which contains the compound as set forth in any one of claims 4, 1 and 2, or a pharmaceutically acceptable salt thereof.