# US 2014/0194445 A1 · Substituted 3-heteroaroylamino-propionic acid derivatives and their use as pharmaceuticals

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- Number: US 2014/0194445 A1
- Document ID: US20140194445A1
- Status: Published application
- Kind: A1
- Application number: 14/202,804
- Filed: 2014-03-10
- Published: 2014-07-10
- Earliest claimed: 2011-01-26
- Assignees: Sanofi
- Inventors: Sven Ruf; Thorsten Sadowski; Klaus Wirth; Herman Schreuder; Christian Buning
- Web page: https://patentgrep.com/patent/US20140194445A1

## CPC

- C07D 413/06: linked by a carbon chain containing only aliphatic carbon atoms
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 7/02: Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A61P 7/10: Antioedematous agents; Diuretics
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 9/04: Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 9/12: Antihypertensives
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 11/06: Antiasthmatics
- A61P 13/12: of the kidneys
- A61P 17/00: Drugs for dermatological disorders
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 27/02: Ophthalmic agents
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 37/00: Drugs for immunological or allergic disorders
- A61P 37/06: Immunosuppressants, e.g. drugs for graft rejection
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 213/81: Amides; Imides
- C07D 213/82: in position 3
- 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 239/28: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D 241/24: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 405/12: linked by a chain containing hetero atoms as chain links
- C07D 413/04: directly linked by a ring-member-to-ring-member bond
- C07D 471/04: Ortho-condensed systems
- C07D 487/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention relates to compounds of the formula I, wherein A, D, E, L, G, R10, R30, R40, R50 and R60 have the meanings indicated in the claims, which are valuable pharmaceutical active compounds. They are inhibitors of the protease cathepsin A, and are useful for the treatment of diseases such as atherosclerosis, heart failure, renal diseases, liver diseases or inflammatory diseases, for example. The invention furthermore relates to processes for the preparation of the compounds of the formula I, their use and pharmaceutical compositions comprising them.

## Claims

### Claim 1

A compound of the formula I, in any of its stereoisomeric forms or a mixture of stereoisomeric forms in any ratio, or a physiologically acceptable salt thereof, or a physiologically acceptable solvate of any of them,
wherein
A is selected from the group consisting of C(R1) and N;
D is selected from the group consisting of C(R2) and N;
E is selected from the group consisting of C(R3) and N;
L is selected from the group consisting of C(R4) and N;
wherein one of A, D, E, and L is N;
G is selected from the group consisting of R71—O—C(O)—, R72—N(R73)—C(O)— and tetrazol-5-yl;
R1 is selected from the group consisting of hydrogen, halogen, (C1-C6)-alkyl, HO—, (C1-C6)-alkyl-O—, (C1-C6)-alkyl-S(O)m— and NC—;
R2 is selected from the group consisting of hydrogen, halogen, (C1-C7)-alkyl, (C1-C6)-alkyl-O—, (C1-C6)-alkyl-CO—, (C1-C6)-alkyl-CO—HN—, —NR12R13, Het2, (C3-C7)-cycloalkyl-CsH2s— and Ar—CsH2s—, wherein s is 0, 1, 2 or 3;
R3 is selected from the group consisting of hydrogen, halogen, (C1-C6)-alkyl, (C1-C6)-alkyl-S(O)m—, Het4-(O)t—, —NR12R13, Het2, R12—N(R13)—C(O)—O— and Het2-C(O)—O— and NC—, wherein s is 0, 1, 2, or 3, and t is 0 or 1;
R4 is selected from the group consisting of hydrogen, halogen, (C1-C6)-alkyl, (C1-C6)-alkyl-O—, HO—, NR12R13, Het2;
R10 is selected from the group consisting hydrogen, halogen, (C1-C6)-alkyl-O—, (C1-C6)-alkyl-S(O)m—, HO—, —NR12R13, Het2, phenyl-CsH2s—(O)t—, wherein s is 0, 1, 2 or 3, and t is 0 or 1;
or R1 and R2 or R2 and R3 form pyridyl;
or R1 and R2 are —C((C1-C3)-alkyl)═N—N((C1-C3)-alkyl)-;
or R2 and R3 are —NH—CH═N—;
with the proviso that one of R′, R2, R4 or R10 is a cyclic substituent;
R11 is selected from the group consisting of hydrogen, R14, (C3-C7)-cycloalkyl, Ar and Het3;
R12 and R13 are independently selected from the group consisting of hydrogen and R15;
R14 is (C1-C10)-alkyl, which is optionally substituted by one or more identical or different substituents selected from the group consisting of halogen, HO—, R16—O—, oxo, (C3-C7)-cycloalkyl, Ar, Het1, Het3, NC—, H2N—C(O)—, (C1-C4)-alkyl-NH—C(O)—, di((C1-C4)-alkyl)N—C(O)—, Het1-C(O)—, (C1-C4)-alkyl-C(O)—NH— and (C1-C4)-alkyl-S(O)m—;
R15 is (C1-C6)-alkyl which is optionally substituted by one or more identical or different substituents selected from the group consisting halogen, HO— and (C1-C6)-alkyl-O—;
R16 is (C1-C6)-alkyl which is optionally substituted by one or more identical or different substituents selected from the group consisting of HO—, (C1-C4)-alkyl-O— and NC—;
R30 is selected from the group consisting of R31, (C3-C7)-cycloalkyl, R32—CuH2u— and Het3-CuH2u—, wherein u is an integer selected from the group consisting of 0, 1, 2 and 3;
R31 is (C1-C10)-alkyl, which is optionally substituted by one or two identical or different substituents selected from the group consisting of halogen, (C3-C7)-cycloalkyl, HO—, (C1-C6)-alkyl-O—, (C1-C6)-alkyl-S(O)m— and NC—;
R32 is selected from the group consisting of phenyl and an aromatic 5-membered or 6-membered monocyclic heterocycle which comprises one, two or three identical or different ring heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur and is bonded via a ring carbon atom, wherein the phenyl and the heterocycle all are optionally substituted by one or more identical or different substituents selected from the group consisting of halogen, (C1-C6)-alkyl, (C3-C7)-cycloalkyl, R33, HO—, (C1-C6)-alkyl-O—, R33—O—, R33—(C1-C4)-alkyl-O—, —O—CH2—O—, —O—CF2—O—, (C1-C6)-alkyl-S(O)m—, H2N—S(O)2—, (C1-C4)-alkyl-NH—S(O)2—, di((C1-C4)-alkyl)N—S(O)2—, H2N—, NH—, di((C1-C6)-alkyl)N—, Het1, (C1-C4)-alkyl-C(O)—NH—, Ar—C(O)—NH—, (C1-C4)-alkyl-S(O)2—NH— and NC—;
R33 is selected from the group consisting of phenyl and an aromatic 5-membered or 6-membered monocyclic heterocycle which comprises one, two or three identical or different ring heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur and is bonded via a ring carbon atom, wherein the phenyl and the heterocycle all are optionally substituted by one or more identical or different substituents selected from the group consisting of halogen, (C1-C6)-alkyl, (C3-C7)-cycloalkyl, HO—, (C1-C6)-alkyl-O—, (C1-C6)-alkyl-S(O)n—, H2N—S(O)2—, (C1-C4)-alkyl-NH—S(O)2—, di((C1-C4)-alkyl)N—S(O)2— and NC—;
R40 is selected from the group consisting of hydrogen and (C1-C4)-alkyl;
or R30 and R40 together are (CH2)x which is optionally substituted by one or more identical or different (C1-C4)-alkyl substituents, wherein x is 2, 3, 4, or 5;
R50 is selected from the group consisting of hydrogen, (C1-C6)-alkyl, HO— and (C1-C6)-alkyl-O—;
R60 is selected from the group consisting of hydrogen and (C1-C6)-alkyl;
or R50 and R60 together are (CH2)y which is optionally substituted by one or more identical or different (C1-C4)-alkyl substituents, wherein y is 2, 3, 4 or 5;
R71 is selected from the group consisting of hydrogen and (C1-C8)-alkyl, which is optionally substituted by one or more identical or different substituents selected from the group consisting (C1-C6)-alkyl-O— and (C1-C6)-alkyl-C(O)—O—;
R72 is selected from the group consisting of hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, —CH2—(CH2)b—(C3-C6)-cycloalkyl, Het4 and —(CH2)b-Het4, where alkyl or cycloalkyl is optionally substituted by one or more identical or different substituents selected from the group consisting of halogen, HO—, HOOC—, (C1-C6)-alkyl-O— and (C1-C6)-alkyl-C(O)—O—, NC—, N((C1-C4)-alkyl)2, and b is 0, 1 or 2;
R73 is selected from the group consisting of hydrogen and (C1-C6)-alkyl; or
R72 and R73, together with the nitrogen atom to which they are bonded, form a saturated 4-membered to 7-membered monocyclic heterocycle, which contain optionally one further ring heteroatom selected from the group consisting of nitrogen, oxygen and sulfur, which is optionally substituted by one or more identical or different substituents selected from the group consisting of halogen, (C1-C4)-alkyl, HO— and (C1-C4)-alkyl-O—; Ar, independently of each other group Ar, is selected from the group consisting of phenyl and an aromatic 5-membered or 6-membered monocyclic heterocycle containing one, two or three identical or different ring heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur and is bonded via a ring carbon atom, wherein the phenyl and the heterocycle all are optionally substituted by one or more identical or different substituents selected from the group consisting of halogen, (C1-C6)-alkyl, HO—(C1-C6)-alkyl, Het4, —(CH2)x-Phenyl, (C1-C6)-alkyl-O—, (C3-C7)-cycloalkyl-(CH2)x—O—, —CF3, —CO—(C1-C6)-alkyl, —NR12R13, Het2, —CO—NR12R13, CO-Het2, (C1-C6)-alkyl-S(O)m—, H2N—S(O)2— and NC—; and wherein phenyl may be substituted by —CH═CH—CH═CH—, —O—CH2—O—, —O—CH2—CH2—O—, —O—CF2—O— or —N((C1-C3)-alkyl)-CH═CH—;
Het1, independently of each other group Het1, is a saturated or unsaturated 4-membered to 8-membered monocyclic heterocycle containing a ring nitrogen atom via which Het1 is bonded, and optionally, one or two identical or different further ring heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur, which is optionally substituted by one or more identical or different substituents selected from the group consisting of halogen, (C1-C4)-alkyl, HO—, (C1-C4)-alkyl-O—, oxo and NC—;
Het2 is a saturated 4-membered to 7-membered monocyclic heterocycle containing a ring nitrogen atom via which Het2 is bonded and optionally one further ring heteroatom selected from the group consisting of nitrogen, oxygen and sulfur, which is optionally substituted by one or more identical or different substituents selected from the group consisting of halogen, (C1-C4)-alkyl, HO— and (C1-C4)-alkyl-O—;
Het3, independently of each other group Het3, is a saturated 4-membered to 7-membered monocyclic heterocycle containing one or two identical or different ring heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur and is bonded via a ring carbon atom, which is optionally substituted by one or more identical or different substituents selected from the group consisting of fluorine, (C1-C4)-alkyl and oxo;
Het4, independently of each other group Het4, is a saturated or unsaturated 4-membered to 8-membered monocyclic heterocycle containing one to four ring heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur which is optionally substituted by one or more identical or different substituents selected from the group consisting of halogen, (C1-C4)-alkyl, HO—, (C1-C4)-alkyl-O—, oxo and NC—;
m, independently of each other number m, is 0, 1 or 2;
wherein all cycloalkyl groups, independently of each other, are optionally substituted by one or more identical or different substituents selected from the group consisting of fluorine and (C1-C4)-alkyl;
wherein all alkyl, CsH2s, CuH2u, (CH2)x and (CH2)y groups, independently of each other, and independently of any other substituents, are optionally substituted by one or more fluorine substituents.

### Claim 2 (depends on 1)

A compound of the formula I in any of its stereoisomeric forms or a mixture of stereoisomeric forms in any ratio, or a physiologically acceptable salt thereof, or a physiologically acceptable solvate of any of them, as claimed in claim 1, wherein
G is selected from the group consisting of R71—O—C(O)— and R72—N(R73)—C(O)—;
R30 is R32—CuH2u—, wherein u is 0 or 1;
R32 is selected from the group consisting of phenyl and an aromatic 6-membered monocyclic heterocycle which comprises one or two nitrogen atoms as ring heteroatoms, wherein the phenyl and the heterocycle all are optionally substituted by one or more identical or different substituents selected from the group consisting of halogen, (C1-C6)-alkyl, (C3-C7)-cycloalkyl, R33, HO—, (C1-C6)-alkyl-O—, R33—O—, R33—(C1-C4)-alkyl-O—, —O—CH2—O—, —O—CF2—O—, (C1-C6)-alkyl-S(O)n—, di((C1-C4)-alkyl)N—S(O)2—, H2N—, di((C1-C6)-alkyl)N—, Het1, (C1-C4)-alkyl-C(O)—NH—, Ar—C(O)—NH— and NC—;
R33 is selected from the group consisting of phenyl and an aromatic 6-membered monocyclic heterocycle which comprises one or two nitrogen atoms as ring heteroatoms, wherein the phenyl and the heterocycle all are optionally substituted by one or more identical or different substituents selected from the group consisting of halogen, (C1-C6)-alkyl, (C3-C7)-cycloalkyl, HO—, (C1-C6)-alkyl-O—, (C1-C6)-alkyl-S(O)n—, H2N—S(O)2—, di((C1-C4)-alkyON—S(O)2— and NC—; and
R40 is hydrogen.

### Claim 3 (depends on 1)

A compound of the formula I in any of its stereoisomeric forms or a mixture of stereoisomeric forms in any ratio, or a physiologically acceptable salt thereof, or a physiologically acceptable solvate of any of them, as claimed in claim 1, wherein
G is R71—O—C(O)—;
R30 is R32—CuH2u—, wherein u is 0;
R32 is phenyl, wherein the phenyl is optionally substituted by one or more identical or different substituents chosen from the series consisting of halogen, (C1-C6)-alkyl, (C3-C7)-cycloalkyl, R33, HO—, (C1-C6)-alkyl-O—, R33—O—, R33—(C1-C4)-alkyl-O—, —O—CH2—O—, —O—CF2—O—, (C1-C6)-alkyl-S(O)m—, di((C1-C4)-alkyl)N—S(O)2—, H2N—, di((C1-C6)-alkyl)N—, Het1, (C1-C4)-alkyl-C(O)—NH—, Ar—C(O)—NH— and NC—;
R33 is phenyl, wherein the phenyl is optionally substituted by one or more identical or different substituents chosen from the series consisting of halogen, (C1-C6)-alkyl, (C3-C7)-cycloalkyl, HO—, (C1-C6)-alkyl-O—, (C1-C6)-alkyl-S(O)m—, H2N—S(O)2—, di((C1-C4)-alkyl)N—S(O)2— and NC—; and
R40 is hydrogen.

### Claim 4 (depends on 1)

A compound of the formula I in any of its stereoisomeric forms or a mixture of stereoisomeric forms in any ratio, or a physiologically acceptable salt thereof, or a physiologically acceptable solvate of any of them, as claimed in claim 1, wherein R50 and R60 are both hydrogen.

### Claim 5 (depends on 1)

A compound of the formula I in any of its stereoisomeric forms or a mixture of stereoisomeric forms in any ratio, or a physiologically acceptable salt thereof, or a physiologically acceptable solvate of any of them, as claimed in claim 1, selected from the subformulae:
wherein R1, R2, R3, R4, R10, R30, R40, R50, and R60 are as defined in claim 1.

### Claim 6 (depends on 5)

A compound of the formula I-1, in any of its stereoisomeric forms or a mixture of stereoisomeric forms in any ratio, or a physiologically acceptable salt thereof, or a physiologically acceptable solvate of any of them, as claimed in claim 5, according to the formula:
wherein R2 is Ar—CsH2s—, wherein s is 0;
R3 is selected from the group consisting of hydrogen, halogen, and (C1-C6)-alkyl;
R4 is hydrogen; and
R10 is hydrogen.

### Claim 7 (depends on 1)

A compound of the formula I, or a physiologically acceptable salt thereof, or a physiologically acceptable solvate of any of them, as claimed in claim 1, selected from:
(S)-3-{[3-(4,6-Dimethoxy-pyrimidin-2-yloxy)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[4-(Pyrimidin-2-ylsulfanyl)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-[(6-Phenyl-pyridine-2-carbonyl)-amino]-3-o-tolyl-propionic acid
(S)-3-[(5-Phenyl-pyridine-2-carbonye-amino]-3-o-tolyl-propionic acid
(S)-3-{[5-(2-Chloro-phenyl)-pyridine-3-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[5-(2,3-Dichloro-phenyl)-pyridine-3-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[5-(2,3-Dimethyl-phenyl)-pyridine-3-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-o-Tolyl-3-[(6-m-tolyl-pyridine-2-carbonyl)-amino]-propionic acid
(S)-3-{[6-(2-Chloro-phenyl)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[6-(2-Fluoro-phenyl)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[6-(2,3-Difluoro-phenye-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[6-(2,5-Difluoro-phenyl)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[6-(4-Fluoro-2-methyl-phenyl)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[6-(2,3-Dimethyl-phenyl)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[6-(5-Fluoro-2-methyl-phenyl)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[6-(2-Methoxy-4-trifluoromethyl-phenyl)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[6-(4-Chloro-2-methoxy-phenyl)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[6-(2-Fluoro-5-methoxy-phenyl)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[6-(2-Fluoro-5-methyl-phenyl)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-[(3,2′-Dimethoxy-[2,3′]bipyridinyl-6-carbonyl)-amino]-3-p-tolyl-propionic acid
(S)-3-(2-Fluoro-phenyl)-3-[(5-methoxy-6-o-tolyl-pyridine-2-carbonyl)-amino]-propionic acid
(S)-3-[(3,2′-Dimethoxy-[2,3′]bipyridinyl-6-carbonyl)-amino]-3-(2-fluoro-phenyl)-propionic acid
(S)-3-(2-Chloro-phenyl)-3-[(6-methoxy-5-o-tolyl-pyridine-3-carbonyl)-amino]-propionic acid
(S)-3-(2-Chloro-phenyl)-3-[(3,2′-dimethoxy-[2,3′]bipyridinyl-6-carbonyl)-amino]-propionic acid
(S)-3-(2-Chloro-phenyl)-3-[(3′-fluoro-3-methoxy-[2,4′]bipyridinyl-6-carbonyl)-amino]-propionic acid
3-Biphenyl-4-yl-3-[(6-chloro-pyridine-2-carbonyl)-amino]-propionic acid
(S)-3-[(6-Chloro-pyridine-2-carbonyl)-amino]-3-o-tolyl-propionic acid
(S)-3-{[6-(2-Fluoro-phenyl)-pyridine-2-carbonyl]-amino}-3-phenyl-propionic acid
(S)-3-(3-Fluoro-phenyl)-3-{[6-(2-fluoro-phenyl)-pyridine-2-carbonyl]-amino}-propionic acid
(S)-3-(2-Fluoro-phenyl)-3-{[6-(2-fluoro-phenyl)-pyridine-2-carbonyl]-amino}-propionic acid
(S)-3-(4-Fluoro-phenyl)-3-{[6-(2-fluoro-phenyl)-pyridine-2-carbonyl]-amino}-propionic acid
(S)-3-{[6-(2-Chloro-phenyl)-pyridine-2-carbonyl]-amino}-3-m-tolyl-propionic acid
(S)-3-{[6-(2-Fluoro-phenyl)-pyridine-2-carbonyl]-amino}-3-(4-methoxy-phenyl)-propionic acid
(S)-3-{[6-(2-Chloro-phenyl)-pyridine-2-carbonyl]-amino}-3-(2-fluoro-phenyl)-propionic acid
(S)-3-{[6-(2-Chloro-phenyl)-pyridine-2-carbonyl]-amino}-3-(4-fluoro-phenyl)-propionic acid
(S)-3-(3-Chloro-phenyl)-3-{[6-(2-fluoro-phenyl)-pyridine-2-carbonyl]-amino}-propionic acid
(S)-3-(4-Chloro-phenyl)-3-{[6-(2-fluoro-phenyl)-pyridine-2-carbonyl]-amino}-propionic acid
(S)-3-(4-Chloro-phenyl)-3-{[6-(2-chloro-phenyl)-pyridine-2-carbonyl]-amino}-propionic acid
(S)-3-(3-Chloro-phenyl)-3-{[6-(2-chloro-phenyl)-pyridine-2-carbonyl]-amino}-propionic acid
3-(2-Chloro-phenyl)-3-{[6-(2-chloro-phenyl)-pyridine-2-carbonyl]-amino}-propionic acid
(S)-3-{[6-(2-Fluoro-phenyl)-pyridine-2-carbonyl]-amino}-3-(3-trifluoromethyl-phenyl)-propionic acid
(S)-3-{[6-(2-Chloro-phenyl)-pyridine-2-carbonyl]-amino}-3-(2,4-dichloro-phenyl)-propionic acid
(S)-3-{[6-(2-Chloro-phenyl)-pyridine-2-carbonyl]-amino}-3-(4-trifluoromethyl-phenyl)-propionic acid
(S)-3-{[6-(2-Chloro-phenyl)-pyridine-2-carbonyl]-amino}-3-(3-trifluoromethyl-phenye-propionic acid, and
(S)-3-{[6-Bromo-5-(3,3-dimethyl-2-oxo-butoxy)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid.

### Claim 8 (depends on 1)

A compound of the formula I, or a physiologically acceptable salt thereof, or a physiologically acceptable solvate of any of them, as claimed in claim 1, selected from:
(S)-3-{[6-(2,3-D imethyl-phenyl)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[6-(2-Chloro-phenyl)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[6-(2-Fluoro-phenyl)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[6-(5-Fluoro-2-methyl-phenyl)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-o-Tolyl-3-[(6-m-tolyl-pyridine-2-carbonyl)-amino]-propionic acid
(S)-3-({6-[3-(1-Hydroxy-1-methyl-ethyl)-phenyl]-pyridine-2-carbonyl}-amino)-3-o-tolyl-propionic acid
(S)-3-[(5-Phenyl-pyridine-2-carbonyl)-amino]-3-o-tolyl-propionic acid
(S)-3-{[3-(4,6-Dimethoxy-pyrimidin-2-yloxy)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[4-(Pyrimidin-2-ylsulfanyl)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[5-(2,3-Dichloro-phenyl)-pyridine-3-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[5-(2,3-Dimethyl-phenyl)-pyridine-3-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[5-(2-Chloro-phenyl)-pyridine-3-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[6-(2,3-Difluoro-phenyl)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[6-(2-Fluoro-5-methoxy-phenyl)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid
(S)-3-{[6-(2-Fluoro-5-methyl-phenyl)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid, and
(S)-3-{[6-(2-Methoxy-4-trifluoromethyl-phenyl)-pyridine-2-carbonyl]-amino}-3-o-tolyl-propionic acid.

### Claim 9 (depends on 1)

A process for preparing the compound of formula I or a physiologically acceptable salt thereof or a physiologically solvate of any of them as claimed in claim 1, comprising reacting a compound of the formula II with a compound of the formula III,
wherein the groups A, D, E, L, G, R10, R30, R40, R50 and R60 in the compounds of the formulae II and III are defined as in the compounds of the formula I and additionally functional groups can be present in protected form or in the form of a precursor group, and the group J in the compound of the formula II is HO—, (C1-C4)-alkyl-O— or halogen.

### Claim 10 (depends on 1)

A pharmaceutical composition comprising the compound of claim 1 or a physiologically acceptable salt thereof or a physiologically acceptable solvate of any of them.

### Claim 11 (depends on 10)

The pharmaceutical composition of claim 10, further comprising a pharmaceutically acceptable carrier.

### Claim 12 (depends on 10)

A method of treating heart failure, congestive heart failure, cardiomyopathy, myocardial infarction, left ventricular dysfunction, cardiac hypertrophy, valvular heart diseases, hypertension, atherosclerosis, peripheral arterial occlusive disease, restenosis, vasvular permeability disorders, treatment of edema, thrombosis, rheumatoid arthritis, osteoarthritis, renal failure, cystic fibrosis, chronic bronchitis, chronic obstructive pulmonary disease, asthma, immunological diseases, diabetic complications, fibrotic diseases, pain, ischemia or reperfusion damage or neurodegenerative diseases, or for cardioprotection or renoprotection or as a diuretic (stand-alone treatment or in combination with established diuretics) in a patient in need thereof comprising administering to said patient a therapeutically effective amount of the pharmaceutical composition of claim 10.