US 8,772,498 B2Granted

Alkylamine-substituted dicyanopyridine and amino acid ester prodrugs thereof

AssigneeBayer Intellectual Property GmbH

InventorsAlexandros Vakalopoulos, Daniel Meibom, Barbara Albrecht-Küpper, Katja Zimmermann, Jörg Keldenich, Hans-Georg Lerchen, Peter Nell, Frank Süβmeier, Ursula Krenz

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Abstract

The present application relates to novel 6-alkylamino-substituted dicyanopyridines, to their amino acid ester prodrugs, to processes for their preparation, to their use for the treatment and/or prophylaxis of diseases and to their use for preparing medicaments for the treatment and/or prophylaxis of diseases, preferably for the treatment and/or prevention of cardiovascular disorders.

Claims7

Dependent claims

A compound of formula (VII)

wherein,
R1 represents hydrogen or (C1-C4)-alkyl,
R2 represents (C1-C6)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl or (C3-C7)-cycloalkyl,
where (C1-C6)-alkyl may be substituted by 1 to 3 substituents selected independently of one another from the group consisting of fluorine, chlorine, trifluoromethyl, trifluoromethoxy, (C1-C4)-alkoxy, (C3-C7)-cycloalkyl, (C3-C7)-cycloalkoxy, (C1-C4)-alkylsulfanyl and (C1-C4)-alkylsulfonyl,
and
where (C2-C4)-alkenyl and (C2-C4)-alkynyl may be substituted by 1 or 2 substituents selected independently of one another from the group consisting of fluorine, trifluoromethyl, (C1-C4)-alkyl, trifluoromethoxy and (C1-C4)-alkoxy,
and
where (C3-C7)-cycloalkyl may be substituted by 1 or 2 substituents selected independently of one another from the group consisting of fluorine, chlorine, trifluoromethyl, (C1-C4)-alkyl, trifluoromethoxy and (C1-C4)-alkoxy,
or
R1 and R2 together with the nitrogen atom to which they are attached form a 4- to 7-membered heterocycle which may contain a further heteroatom from the group consisting of N, O and S,
where the 4- to 7-membered heterocycle may be substituted by 1 or 2 substituents selected independently of one another from the group consisting of fluorine, chlorine, oxo, trifluoromethyl, (C1-C4)-alkyl, trifluoromethoxy and (C1-C4)-alkoxy,
R4 represents hydrogen or the side group of a natural α-amino acid or its homologs or isomers,
R5 represents hydrogen or methyl,
R6A represents hydrogen, (C1-C4)-alkyl, or an amino protective group,
R7A represents hydrogen, (C1-C4)-alkyl, or an amino protective group,
or
R6A and R7A together with the nitrogen atom to which they are attached form a 5- or 6-membered heterocycle,
where the 5- or 6-membered heterocycle may be substituted by 1 or 2 substituents independently selected from the group consisting of (C1-C4)-alkyl, amino, hydroxyl and (C1-C4)-alkoxy,
or
R7A together with R4 and the atoms, to which they are attached, forms a pyrrolidine or piperidine ring,
or a salt thereof.

18 more elements

A compound of formula (VIII)

wherein
R1 represents hydrogen or (C1-C4)-alkyl,
R2 represents (C1-C6)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl or (C3-C7)-cycloalkyl,
where (C1-C6)-alkyl may be substituted by 1 to 3 substituents selected independently of one another from the group consisting of fluorine, chlorine, trifluoromethyl, trifluoromethoxy, (C1-C4)-alkoxy, (C3-C7)-cycloalkyl, (C3-C7)-cycloalkoxy, (C1-C4)-alkylsulfanyl and (C1-C4)-alkylsulfonyl,
where (C2-C4)-alkenyl and (C2-C4)-alkynyl may be substituted by 1 or 2 substituents selected independently of one another from the group consisting of fluorine, trifluoromethyl, (C1-C4)-alkyl, trifluoromethoxy and (C1-C4)-alkoxy,
and
where (C3-C7)-cycloalkyl may be substituted by 1 or 2 substituents selected independently of one another from the group consisting of fluorine, chlorine, trifluoromethyl, (C1-C4)-alkyl, trifluoromethoxy and (C1-C4)-alkoxy,
or
R1 and R2 together with the nitrogen atom to which they are attached form a 4- to 7-membered heterocycle which may contain a further heteroatom from the group consisting of N, O and S,
where the 4- to 7-membered heterocycle may be substituted by 1 or 2 substituents selected independently of one another from the group consisting of fluorine, chlorine, oxo, trifluoromethyl, (C1-C4)-alkyl, trifluoromethoxy and (C1-C4)-alkoxy;
L2 represents (C2-C6)-alkanediyl;
R17A represents hydrogen, (C1-C4)-alkyl, or an amino protective group, and
R18A represents hydrogen, (C1-C4)-alkyl, or an amino protective group;
or
R17 and R18 together with the nitrogen atom to which they are attached form a 5- or 6-membered heterocycle, where the 5- or 6-membered heterocycle may be substituted by 1 or 2 substituents independently selected from the group consisting of (C1-C4)-alkyl, amino, hydroxyl, and (C1-C4)-alkoxy.

12 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/801,484Filed 13 Mar 2013 · continuation
Priority: DE 10 2009 006 60229 Jan 2009
Published: US 2013/0267700 A110 Oct 2013
Granted: 8 Jul 2014
Term ends: Not estimatedThe source records don’t support an estimate.

Classification23 codes

C07D 417/14
Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms,…
A61K 47/64
The modifying agent being a protein, peptide or polyamino acid: drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying…
A61P 3/00
Drugs for disorders of the metabolism
A61P 3/04
Drugs for disorders of the metabolism: anorexiants; Antiobesity agents

Family

Application12/697,000Parent of this continuation · filed 29 Jan 2010
US 2013/0267700 A1Pre-grant publication · published 10 Oct 2013
US 8,420,825 B2Parent of this continuation
US 2010/0197609 A1Published application
US 8,772,498 B2This patent

From the US filing history. Foreign family members aren’t listed.

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