2-Aminoethoxyacetic Acid Derivatives and Their Use

• US 20090036504A1
• Filed: 09/14/2006
• Published: 02/05/2009
• Est. Priority Date: 09/23/2005
• Status: Active Grant

• Current Assignee: Bayer Intellectual Property GmbH (Bayer AG)
• Original Assignee: Bayer Healthcare AG (Bayer AG)
• Inventors: Perzborn, Elisabeth, Thomas, Christian R., Rohrig, Susanne
• Granted Patent: US 7,932,278 B2
• Time in Patent Office: Days
• US Class Current: 514/376
• CPC Class Codes: A61P 7/00 Drugs for disorders of the blood or the extracellular fluid
• CPC Class Codes: A61P 7/02 Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
• CPC Class Codes: C07D 413/12 linked by a chain containing hetero atoms as chain links

Abstract

The present application relates to novel 2-aminoethoxyacetic acid derivatives, to processes for their preparation, to their use for the treatment and/or prophylaxis of diseases and also to their use for preparing medicaments for the treatment and/or prophylaxis of diseases, in particular thromboembolic disorders.

Claims

1. A compound of the formula (I)

in which

R represents hydrogen, (C₁-C₆)-alkyl, (C₁-C₆)-alkanoyl, (C₁-C₆)-alkoxycarbonyl, mono- or di-(C₁-C₆)-alkylaminocarbonyl, benzoyl or heteroaroyl, where

benzoyl and heteroaroyl for their part may be substituted by halogen, cyano, (C₁-C₄)-alkyl or (C₁-C₄)-alkoxy,

or a salt, solvate, or solvate of a salt thereof.

2. The compound of the formula (I) as claimed in claim 1 in which

R is hydrogen, isobutylaminocarbonyl or 5-chloro-2-thienylcarbonyl,

or a salt, solvate, or solvate of a salt thereof.

3. The compound of the formula (I) as claimed in claim 1 having the structure below:

or a salt, solvate, or solvate of a salt thereof.

4. A process for preparing compounds of the formula (I), as defined in claim 1, characterized in that the compound of the formula (II)

is converted by hydrolysis into the compound of the formula (I-A)

and this is then, in an inert solvent, if appropriate in the presence of a base, reacted with a compound of the formula (III)

R^A—

X 

 

(III),

in which

R^A represents (C₁-C₆)-alkyl, (C₁-C₆)-alkanoyl, (C₁-C₆)-alkoxycarbonyl, di-(C₁-C₆)-alkylaminocarbonyl, benzoyl or heteroaroyl, where

benzoyl and heteroaroyl for their part may be substituted by halogen, cyano, (C₁-C₄)-alkyl or (C₁-C₄)-alkoxy,

and

X represents a leaving group, such as, for example, halogen,

or, if R represents mono-(C₁-C₆)-alkylaminocarbonyl, with a compound of the formula (IV)

R^B—

N═

C═

O 

 

(IV),

in which

R^B represents (C₁-C₆)-alkyl,

and the resulting compound of the formula (I) or (I-A) is, if appropriate, converted with the appropriate (i) solvent and/or (ii) base or acid into a salt, solvate, or solvate of a salt.

8. A pharmaceutical composition comprising a compound of the formula (I) as defined in claim 1 in combination with an inert non-toxic, pharmaceutically suitable auxiliary.

9. A pharmaceutical composition comprising a compound of the formula (I) as defined in claim 1 in combination with a further active compound.

11. A method for the treatment and/or prophylaxis of thromboembolic disorders in humans and animals, which comprises administering an anticoagulatory effective amount of at least one compound of the formula (I) as defined in claim 1 or a pharmaceutical composition as defined in claim 8 or 9.

12. A method for preventing blood coagulation in vitro, characterized in that an anticoagulatory effective amount of a compound of the formula (I) as defined in claim 1 is added.

5. (canceled)

6. (canceled)

7. (canceled)

10. (canceled)