# US 11,992,494 B2 · Cyclopentathiophene carboxamide derivatives as platelet activating factor receptor antagonists

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- Number: US 11,992,494 B2
- Document ID: US11992494B2
- Status: Granted
- Kind: B2
- Application number: 18/083,602
- Filed: 2022-12-19
- Published: 2023-06-22
- Granted: 2024-05-28
- Earliest claimed: 2021-12-22
- Assignees: Boehringer Ingelheim International GmbH
- Applicants: Boehringer Ingelheim International GmbH
- Inventors: Matthias Eckhardt; Ferenc Kontes; Christofer Siegfried Tautermann; Dieter Wiedenmayer; Marina Kristina Willwacher
- Web page: https://patentgrep.com/patent/US11992494B2

## CPC

- A61K 31/551: having two nitrogen atoms, e.g. dilazep
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 35/00: Antineoplastic agents
- C07D 495/14: Ortho-condensed systems
- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Cyclopentathiophene carboxamides of formula (I), wherein R1, R2, R3, R4, and n are as defined herein, and pharmaceutically acceptable salts thereof. The compounds of formula (I) can be used in methods for the treatment of diseases which can be influenced by antagonizing the activity mediated by the platelet activating factor receptor.

## Claims

### Claim 1

A compound of formula (I)
wherein
R1 is selected from the group consisting of C1-4-alkyl and C3-4-cycloalkyl,
wherein the C1-4-alkyl group of R1 is optionally substituted with 1 to 3 F;
n is selected from the group consisting of 0, 1, 2, and 3;
R2 is independently selected from the group consisting of F, Cl, Br, I, C1-4-alkyl, C3-4-cycloalkyl, —CN, —CONH2, —CONH(C1-4-alkyl), —CON(C1-4-alkyl)2, —COOH, —COO—C1-4-alkyl, NH2, OH, —O—C1-4-alkyl, and —S(O)r-C1-4-alkyl with r=0, 1, or 2;
wherein the C1-4-alkyl group of R2 is optionally substituted with 1 to 3 F or with 1 —CN, with 1 OH, or with 1 O—C1-4-alkyl, and
wherein the —O—C1-4-alkyl group of R2 is optionally substituted with 1 to 3 F;
R3 is selected from the group consisting of H and C1-4-alkyl optionally substituted with 1 to 5 F; and
R4 is selected from the group consisting of C1-6-alkyl
optionally substituted with 1 to 3 F or optionally substituted with 1 to 2 substituents independently selected from
—CN, —CONH2, —CONH(C1-4-alkyl), —CON(C1-4-alkyl)2, —COOH, —COO—C1-4-alkyl, C1-3-alkyl-CO—NH—, C1-3-alkyl-S(═O)2—NH—, OH, and —O—C1-3-alkyl optionally substituted with 1 to 3 F;
or
R4 is selected from the group consisting of —C0-3-alkylene-C3-10-cycloalkyl and —C0-3-alkylene-C3-10-heterocyclyl,
wherein said alkylene moiety of the —C0-3-alkylene-C3-10-cycloalkyl and —C0-3-alkylene-C3-10-heterocyclyl groups of R4 is optionally substituted with 1 to 2 substituents selected from F and CH3,
wherein 1 CH2 group of said alkylene moiety of the —C0-3-alkylene-C3-10-cycloalkyl and —C0-3-alkylene-C3-10-heterocyclyl groups of R4 is optionally replaced by a
moiety,
wherein said cycloalkyl moiety of the —C0-3-alkylene-C3-10-cycloalkyl group of R4 and said heterocyclyl moiety of the —C0-3-alkylene-C3-10-heterocyclyl group of R4 are saturated mono- or bicyclic ring systems,
wherein said heterocyclyl moiety of the —C0-3-alkylene-C3-10-heterocyclyl group of R4 contains 1 to 2 ring members independently selected from N, NH, N(C1-4-alkyl), NCO(C1-4-alkyl), NCOO(C1-4-alkyl), NS(═O)2(C1-4-alkyl), N-phenyl, N-pyridinyl, N-pyrimidinyl, and O, and optionally 1 ring member selected from C═O, and S(═O)r, with r=0, 1, or 2,
provided that said heterocyclyl moiety of the —C0-3-alkylene-C3-10-heterocyclyl group of R4 does not contain any heteroatom-heteroatom bonds other than N—N, N—O, and N—S(═O)r=1,2 between ring members, and
wherein said cycloalkyl moiety of the —C0-3-alkylene-C3-10-cycloalkyl group of R4 and said heterocyclyl moiety of the —C0-3-alkylene-C3-10-heterocyclyl group of R4 are optionally substituted with 1 to 2 F and optionally substituted with 1 to 2 substituents independently selected from
a) Cl,
b) —CN,
c) —CONH2,
d) —CONH(C1-4-alkyl),
e) —CON(C1-4-alkyl)2,
f) —COOH,
g) —COO—C1-4-alkyl,
h) OH,
i) —O—C1-3-alkyl optionally substituted with 1 to 3 F,
j) S(═O)2—C1-4-alkyl and
k) C1-4-alkyl optionally substituted with 1 to 3 F or with 1 substituent selected from —CN, OH, —O—C1-4-alkyl;
or
R4 is selected from the group consisting of —C0-3-alkylene-phenyl and —C0-3-alkylene-heteroaryl,
wherein said alkylene moiety of the —C0-3-alkylene-phenyl and —C0-3-alkylene-heteroaryl groups of R4 is optionally substituted with 1 to 2 substituents selected from F and CH3,
wherein 1 CH2 group of said alkylene moiety of the —C0-3-alkylene-phenyl and —C0-3-alkylene-heteroaryl groups of R4 is optionally replaced by a
moiety or by a
moiety, or
wherein 1 —CH2—CH2— group of said alkylene moiety of the —C0-3-alkylene-phenyl and —C0-3-alkylene-heteroaryl groups of R4 is optionally replaced by a
moiety or by a
moiety,
wherein said heteroaryl moiety of the —C0-3-alkylene-heteroaryl group of R4 is a 5-membered monocycle containing 1 ring member selected from N, NH, O, and S and optionally further containing 1 to 2 ring members N, or a 6-membered monocycle containing 1 to 2 ring members N, and
wherein said phenyl moiety of the —C0-3-alkylene-phenyl group of R4 and said heteroaryl moiety of the —C0-3-alkylene-heteroaryl group of R4 are optionally substituted with 1 to 3 substituents independently selected from
a) F, Cl, Br,
b) C3-4-cycloalkyl,
c) —CN,
d) —CONH2,
e) —CONH(C1-4-alkyl),
f) —CON(C1-4-alkyl)2,
g) —COOH,
h) —COO—C1-4-alkyl,
i) —NHCO—C1-4-alkyl,
j) —NHS(═O)2—C1-4-alkyl,
k) —S(═O)r-C1-4-alkyl with r=0, 1, or 2,
l) —O—C1-4-alkyl optionally substituted with 1 to 3 F, and
m) C1-4-alkyl optionally substituted with 1 to 3 F or with 1 substituent selected from —CN, OH, and —O—C1-4-alkyl,
or
R4 is selected from the group consisting of 7- to 12-membered fused bicyclic aryl, heteroaryl, or heterocyclyl
wherein said bicyclic aryl, heteroaryl, or heterocyclyl of R4 consists of one non-aromatic ring that is attached to the amide N atom in formula (I) and optionally contains 1 to 2 ring members independently selected from N—, NH, N(C1-4-alkyl), N(CO—C1-3-alkyl), N(S(═O)2-C1-3-alkyl), and O, and
optionally contains 1 ring member selected from C═O and S(═O)r, with r=0, 1, or 2, and of
one aromatic ring selected from phenyl, pyrrole, furan, and thiophene in each of which 1 to 2 CH ring members are optionally replaced with N,
wherein said bicyclic aryl, heteroaryl, or heterocyclyl of R4 is optionally substituted with 1 to 4 F,
is optionally substituted with 1 to 4 C1-3-alkyl optionally substituted with 1 to 4 F, and
is optionally substituted with 1 to 2 substituents selected from the group consisting of Cl, —CN, —CONH2, —CONH(C1-4-alkyl), —CON(C1-4-alkyl)2, —COOH, —COO—C1-4-alkyl, HO—C1-3-alkylene-, C1-3-alkyl-O—C1-3-alkylene-, NH2, C1-3-alkyl-CO—NH—, C1-3-alkyl-S(═O)2-NH—, OH, and C1-3-alkyl-O— optionally substituted with 1 to 3 F;
or
R3 and R4 are selected from the group in which R3 and R4, together with the amide N atom they are attached to, form a saturated 3- to 8-membered monocyclic heterocyclyl optionally further containing 1 to 2 ring members independently selected from NH, N(C1-4-alkyl), N(CO—C1-3-alkyl), N(S(═O)2-C1-3-alkyl), and O, and
optionally containing 1 ring member selected from C═O and S(═O)r, with r=0, 1, or 2, provided that said saturated 3- to 8-membered monocyclic heterocyclyl formed by R3 and R4 together with the amide N atom they are attached to does not contain any heteroatom-heteroatom bonds other than N—N, N—O, and N—S(═O)r=1,2 between ring members,
wherein said heterocyclyl formed by R3 and R4 together with the amide N atom they are attached to is optionally substituted with 1 to 4 F,
is optionally substituted with 1 to 4 C1-3-alkyl optionally substituted with 1 to 3 F, and
is optionally substituted with 1 to 2 substituents selected from Cl, —CN, —CONH2, —CONH(C1-4-alkyl), —CON(C1-4-alkyl)2, —COOH, —COO—C1-4-alkyl, HO—C1-3-alkylene-, C1-3-alkyl-O—C1-3-alkylene-, C1-3-alkyl-CO—NH—, C1-3-alkyl-S(═O)2—NH—, OH, and C1-3-alkyl-O— optionally substituted with 1 to 3 F;
or
R3 and R4 are selected from the group in which R3 and R4, together with the amide N atom they are attached to, form a saturated 5- to 12-membered bicyclic heterocyclyl optionally further containing 1 to 3 ring members independently selected from N—, NH, N(C1-4-alkyl), N(CO—C1-3-alkyl), N(S(═O)2—C1-3-alkyl), and O, and
optionally containing 1 ring member selected from C═O and S(═O)r, with r=0, 1, or 2, provided that said saturated 5- to 12-membered bicyclic heterocyclyl formed by R3 and R4 together with the amide N atom they are attached to does not contain any heteroatom-heteroatom bonds other than N—N, N—O, and N—S(═O)r=1,2 between ring members
wherein said saturated 5- to 12-membered bicyclic heterocyclyl formed by R3 and R4 together with the amide N atom they are attached to is optionally substituted with 1 to 6 F,
is optionally substituted with 1 to 4 C1-3-alkyl optionally substituted with 1 to 3 F, or is optionally substituted with 1 to 2 substituents selected from Cl, —CN, —CONH2, —CONH(C1-4-alkyl), —CON(C1-4-alkyl)2, —COOH, —COO—C1-4-alkyl, HO—C1-3-alkylene-, C1-3-alkyl-O—C1-3-alkylene-, C1-3-alkyl-CO—NH—, C1-3-alkyl-S(═O)2-NH—, OH, and C1-3-alkyl-O—;
or a salt thereof.

### Claim 2 (depends on 1)

The compound according to claim 1,
wherein R1 is selected from the group consisting of CH3, CH2CH3, CH2CH2CH3, CHF2, CF3, and cyclopropyl
or a salt thereof.

### Claim 3 (depends on 1)

The compound according to claim 1,
wherein R2 is independently selected from the group consisting of
F, Cl, Br, C1-3-alkyl, cyclopropyl, —CN, —C1-3-alkylene-OH, —C1-2-alkylene-O—C1-2-alkyl, NH2, OH, —O—C1-3-alkyl, and —S—C1-3-alkyl;
wherein the C1-3-alkyl group of R2 is optionally substituted with 2 or 3 F, and
wherein the —O—C1-3-alkyl group of R2 is optionally substituted with 2 or 3 F;
or a salt thereof.

### Claim 4 (depends on 1)

The compound according to claim 1, wherein
R3 is selected from the group consisting of H and C1-3-alkyl optionally substituted with 1 to 3 F; and
R4 is selected from the group consisting of C1-6-alkyl optionally substituted with 1 to 3 F or
optionally substituted with 1 substituent selected from —CN, —CONH2, —CONH(C1-2-alkyl), —CON(C1-2-alkyl)2, —COOH, —COO—C1-2-alkyl, C1-2-alkyl-CO—NH—, C1-2-alkyl-S(═O)2—NH—, OH, and —O—C1-2-alkyl optionally substituted with 1 to 3 F;
or
R4 is selected from the group consisting of —C0-2-alkylene-C3-8-cycloalkyl and —C0-2-alkylene-C3-9-heterocyclyl,
wherein said cycloalkyl moiety of the —C0-2-alkylene-C3-8-cycloalkyl group of R4 and said heterocyclyl moiety of the —C0-2-alkylene-C3-9-heterocyclyl group of R4 are saturated mono- or bicyclic ring systems,
wherein said heterocyclyl moiety of the —C0-2-alkylene-C3-9-heterocyclyl group of R4 contains 1 ring member selected from N, NH, NCO(CH3), NCOO(C1-2-alkyl), NS(═O)2CH3, N-pyrimidinyl, O, and S(═O)2,
wherein said cycloalkyl moiety of the —C0-2-alkylene-C3-8-cycloalkyl group of R4 and said heterocyclyl moiety of the —C0-2-alkylene-C3-9-heterocyclyl group of R4 are optionally substituted with 1 to 2 F and are optionally substituted with 1 to 2 substituents independently selected from —CN, OH, —OCH3, S(═O)2CH3 and C1-3-alkyl optionally substituted with 2 to 3 F or with 1 group selected from —CN, OH, and —O—C1-4-alkyl;
or
R4 is selected from the group consisting of —C0-2-alkylene-phenyl and —C0-2-alkylene-heteroaryl,
wherein said alkylene moiety of the —C0-2-alkylene-phenyl and —C0-2-alkylene-heteroaryl groups of R4 is optionally substituted with 1 to 2 CH3,
wherein 1 CH2 group of said alkylene moiety of the —C0-2-alkylene-phenyl and —C0-2-alkylene-heteroaryl groups of R4 is optionally replaced by a
moiety or by a
moiety or
wherein 1 —CH2—CH2— group of said alkylene moiety of the —C0-2-alkylene-phenyl and —C0-2-alkylene-heteroaryl groups of R4 is optionally replaced by a
moiety or by a
moiety,
wherein said heteroaryl moiety of the —C0-2-alkylene-heteroaryl group of R4 is a 5-membered monocycle containing 1 ring member selected from N, NH, O, and S and optionally further containing 1 ring member N, or a 6-membered monocycle containing 1 to 2 ring members N, and
wherein said phenyl moiety of the —C0-2-alkylene-phenyl 1 group of R4 and said heteroaryl moiety of the —C0-2-alkylene-heteroaryl group of R4 are optionally substituted with 1 to 2 substituents independently selected from
a) F, Cl, Br,
b) —CN,
c) —O—C1-3-alkyl optionally substituted with 1 to 3 F, and
d) C1-3-alkyl optionally substituted with 1 to 3 F or with 1 substituent selected from —CN and —O—C1-2-alkyl;
or
R4 is selected from the group consisting of 8- to 11-membered fused bicyclic aryl, heteroaryl, or heterocyclyl,
wherein said bicyclic aryl, heteroaryl, or heterocyclyl or R4 consists of one non-aromatic ring that is attached to the amide N atom in formula (I) and optionally contains 1 ring member selected from N—, NH, NCH3, NCO(CH3), NS(═O)2CH3, and O, and optionally contains 1 ring member selected from C═O and S(═O)2,
and of
one aromatic ring selected from phenyl, pyrrole, furan, and thiophene in each of which 1 CH ring member is optionally replaced with N,
wherein said bicyclic aryl, heteroaryl, or heterocyclyl of R4 is optionally substituted with 1 to 2 F,
is optionally substituted with 1 to 2 C1-2-alkyl optionally substituted with 1 to 2 F, and
is optionally substituted with 1 to 2 substituents selected from Cl, —CN, —CONH2, —CONHCH3, —CON(CH3)2, —COOH, —COO—C1-2-alkyl, HO—C1-3-alkylene-, CH3—O—C1-3-alkylene-, NH2, CH3—CO—NH—, CH3—S(═O)2—NH—, OH, and CH3—O— optionally substituted with 1 to 3 F;
or
R3 and R4 are selected from the group in which R3 and R4, together with the amide N atom they are attached to, form a saturated 4- to 7-membered monocyclic heterocyclyl optionally further containing 1 ring member selected from NH, N(C1-4-alkyl), N(CO—C1-3-alkyl), N(S(═O)2—C1-3-alkyl), and O, and optionally containing 1 ring member selected from C═O and S(═O)2,
provided that said saturated 4- to 7-membered monocyclic heterocyclyl formed by R3 and R4 together with the amide N atom they are attached to does not contain any heteroatom-heteroatom bonds other than N—S(═O)r=1,2 between ring members,
wherein said saturated 4- to 7-membered monocyclic heterocyclyl formed by R3 and R4 together with the amide N atom they are attached to is optionally substituted with 1 to 2 F,
is optionally substituted with 1 to 2 C1-3-alkyl optionally substituted with 2 to 3 F, and
is optionally substituted with 1 substituent selected from Cl, —CN, —CON(C1-3-alkyl)2, —COO—C1-3-alkyl, C1-3-alkyl-O—C1-3-alkylene-, and C1-3-alkyl-O—;
or
R3 and R4 are selected from the group in which R3 and R4, together with the amide N atom they are attached to, form a saturated 6- to 11-membered bicyclic heterocyclyl optionally further containing 1 ring member selected from N—, NH, N(C1-4-alkyl), N(CO—C1-3-alkyl), N(S(═O)2—C1-3-alkyl), and O, and
optionally containing 1 ring member selected from C═O and S(═O)r, with r=0, 1, or 2, provided that said saturated 6- to 11-membered bicyclic heterocyclyl formed by R3 and R4 together with the amide N atom they are attached to does not contain any O—S bonds between ring members
wherein said saturated 6- to 11-membered bicyclic heterocyclyl formed by R3 and R4 together with the amide N atom they are attached to is optionally substituted with 1 to 4 F,
is optionally substituted with 1 to 3 C1-3-alkyl optionally substituted with 1 to 3 F, or is optionally substituted with 1 to 2 substituents independently selected from Cl, —CN, —CONH2, —CONH(C1-4-alkyl), —CON(C1-4-alkyl)2, —COOH, —COO—C1-4-alkyl, HO—C1-3-alkylene-, C1-3-alkyl-O—C1-3-alkylene-, C1-3-alkyl-CO—NH—, C1-3-alkyl-S(═O)2—NH—, OH, and C1-3-alkyl-O—;
or a salt thereof.

### Claim 5 (depends on 1)

The compound according to claim 1, wherein
R3 is selected from the group consisting of H and C1-3-alkyl optionally substituted with 1 to 3 F; and
R4 is selected from the group consisting of C1-4-alkyl
optionally substituted with 1 to 3 F or
optionally substituted with 1 substituent selected from —CN, —CONH2, —COOH, OH, and —O—C1-2-alkyl optionally substituted with 1 to 3 F;
or
R4 is selected from the group consisting of —C0-1-alkylene-C3-7-cycloalkyl and C3-9-heterocyclyl,
wherein said cycloalkyl moiety of the —C0-1-alkylene-C3-7-cycloalkyl group of R4 and said C3-9-heterocyclyl group of R4 are saturated mono- or bicyclic ring systems, wherein said C3-9-heterocyclyl group of R4 contains 1 ring member selected from N, NH, NCO(CH3), NCOO(C1-2-alkyl), NS(═O)2CH3, N-pyrimidinyl, O, and S(═O)2, wherein said cycloalkyl moiety of the —C0-1-alkylene-C3-7-cycloalkyl group of R4 is optionally substituted with 1 to 2 F or optionally substituted with 1 to 2 CH3 groups or optionally substituted with 1 substituent selected from CH2CH3, —CN, CH2OH, C(CH3)2OH, CHF2, CF3, OH, —OCH3, and S(═O)2CH3,
wherein said C3-9-heterocyclyl group of R4 is optionally substituted with 2 F or optionally substituted with 1 to 2 CH3 groups or optionally substituted with 1 substituent selected from CH2CH3 and C(CH3)2H;
or
R4 is selected from the group consisting of —C1-2-alkylene-phenyl and —C0-1-alkylene-heteroaryl,
wherein 1 CH2 group of said alkylene moiety of the —C1-2-alkylene-phenyl and —C0-1-alkylene-heteroaryl groups of R4 is optionally replaced by a
moiety or by a
moiety, or
wherein 1 —CH2—CH2— group of said alkylene moiety of the —C1-2-alkylene-phenyl and —C0-1-alkylene-heteroaryl groups of R4 is optionally replaced by a
moiety or by a
moiety,
wherein said heteroaryl moiety of the —C0-1-alkylene-heteroaryl group of R4 is a 5-membered monocycle containing 1 ring member N and optionally containing 1 ring member independently selected from N and O, or a 6-membered monocycle containing 1 to 2 ring members N, and
wherein said phenyl moiety of the —C1-2-alkylene-phenyl group of R4 and said heteroaryl moiety of the —C0-1-alkylene-heteroaryl group of R4 are optionally substituted with 1 to 2 substituents independently selected from F, Cl, OCH3, and CH3;
or
R3 and R4 are selected from the group in which R3 and R4, together with the amide N atom they are attached to, form a saturated 4- to 6-membered monocyclic heterocyclyl optionally further containing 1 ring member O that is non-adjacent to the amide N atom, wherein said saturated 4- to 6-membered monocyclic heterocyclyl formed by R3 and R4 together with the amide N atom they are attached to is optionally substituted with 1 to 2 F or is optionally substituted with 1 to 2 CH3;
or
R3 and R4 are selected from the group in which R3 and R4, together with the amide N atom they are attached to, form a saturated 6- to 11-membered bridged or spiro bicyclic heterocyclyl
optionally further containing 1 ring member selected from N—, NH, N(C1-4-alkyl), and O that is non-adjacent to the amide N atom,
wherein said saturated 6- to 11-membered bridged or spiro bicyclic heterocyclyl R3 and R4, together with the amide N atom they are attached to is optionally substituted with 1 to 2 F,
is optionally substituted with 1 to 2 C1-3-alkyl optionally substituted with 1 to 3 F, or is optionally substituted with 1 substituent selected from Cl, —CN, —CON(C1-3-alkyl)2, —COO—C1-3-alkyl, C1-3-alkyl-O—C1-3-alkylene-, and C1-3-alkyl-O—;
or a salt thereof.

### Claim 6 (depends on 1)

The compound according to claim 1, wherein
R3 is selected from the group consisting of H and C1-3-alkyl optionally substituted with 1 to 3 F; and
R4 is selected from the group consisting of C1-4-alkyl optionally substituted with 1 group selected from F and OCF3;
or
R4 is selected from the group consisting of —C0-1-alkylene-C3-7-cycloalkyl and C3-9-heterocyclyl,
wherein said cycloalkyl moiety of the —C0-1-alkylene-C3-7-cycloalkyl group of R4 and said C3-9-heterocyclyl group of R4 are saturated mono- or bicyclic ring systems, wherein said C3-9-heterocyclyl group of R4 contains 1 ring member selected from N, NH, NCO(CH3), NCOO(C1-2-alkyl), NS(═O)2CH3, N-pyrimidinyl, O, and S(═O)2, wherein said cycloalkyl moiety of the —C0-1-alkylene-C3-7-cycloalkyl group of R4 is optionally substituted with 1 to 2 F or optionally substituted with 1 to 2 CH3 groups or optionally substituted with 1 substituent selected from CH2CH3, —CN, CH2OH, C(CH3)2OH, CHF2, CF3, OH, —OCH3, and S(═O)2CH3,
wherein said C3-9-heterocyclyl group of R4 is optionally substituted with 2 F or optionally substituted with 1 to 2 CH3 groups or optionally substituted with 1 substituent selected from CH2CH3 and C(CH3)2H;
or
R4 is selected from the group consisting of —C1-2-alkylene-phenyl and —C0-1-alkylene-heteroaryl,
wherein 1 CH2 group of said alkylene moiety of the —C1-2-alkylene-phenyl and —C0-1-alkylene-heteroaryl groups of R4 is optionally replaced by a
moiety or by a
moiety or
wherein 1 —CH2—CH2— group of said alkylene moiety of the —C1-2-alkylene-phenyl and —C0-1-alkylene-heteroaryl groups of R4 is optionally replaced by a
moiety or by a
moiety,
wherein said heteroaryl moiety of the —C0-1-alkylene-heteroaryl group of R4 is a 5-membered monocycle containing 1 ring member N and optionally containing 1 ring member independently selected from N and O, or a 6-membered monocycle containing 1 to 2 ring members N, and
wherein said phenyl moiety of the —C1-2-alkylene-phenyl group of R4 and said heteroaryl moiety of the —C0-1-alkylene-heteroaryl group of R4 are optionally substituted with 1 to 2 substituents independently selected from F, Cl, OCH3, and CH3;
or
R3 and R4 are selected from the group in which R3 and R4, together with the amide N atom they are attached to, form a saturated 4- to 6-membered monocyclic heterocyclyl optionally further containing 1 ring member O that is non-adjacent to the amide N atom,
wherein said saturated 4- to 6-membered monocyclic heterocyclyl formed by R3 and R4 together with the amide N atom they are attached to is optionally substituted with 1 to 2 F or is optionally substituted with 1 to 2 CH3;
or
R3 and R4 are selected from the group in which R3 and R4, together with the amide N atom they are attached to, form a saturated 6- to 8-membered bridged or spiro bicyclic heterocyclyl optionally containing 1 ring member O that is non-adjacent to the amide N atom;
or a salt thereof.

### Claim 7 (depends on 1)

The compound according to claim 1,
wherein
R3 is selected from the group consisting of H, CH3, CH2CH3, and CH2CH2CH3; and
R4 is selected from the group consisting of
or
R4 is selected from the group consisting of
or
R4 is selected from the group consisting of
or
R4 is selected from the group consisting of
or
R3 and R4 are selected from the group in which R3 and R4, together with the amide N atom they are attached to, form a heterocyclyl selected from the group consisting of
or
R3 and R4 are selected from the group in which R3 and R4, together with the amide N atom they are attached to, form a heterocyclyl selected from the group consisting of
or a salt thereof.

### Claim 8 (depends on 7)

The compound according to claim 7,
wherein
R3 and R4 are selected from the group in which R3 and R4, together with the amide N atom they are attached to, form a heterocyclyl selected from the group consisting of
or a salt thereof.

### Claim 9 (depends on 1)

The compound according to claim 1, wherein said compound is selected from the group consisting of:
or a salt thereof.

### Claim 10 (depends on 1)

A pharmaceutically acceptable salt of the compound according to claim 1.

### Claim 11 (depends on 1)

A pharmaceutical composition comprising one or more compounds according to claim 1, or pharmaceutically acceptable salts thereof, optionally together with one or more inert carriers and/or diluents.

### Claim 12 (depends on 1)

A pharmaceutical composition comprising one or more compounds according to claim 1, or pharmaceutically acceptable salts thereof, and one or more additional therapeutic agents, optionally together with one or more inert carriers and/or diluents.

### Claim 13 (depends on 12)

The pharmaceutical composition according to claim 12, wherein the one or more additional therapeutic agents are selected from the group consisting of antidiabetic agents, agents for the treatment of overweight and/or obesity, agents for the treatment of high blood pressure, heart failure and/or atherosclerosis, agents for the treatment of ocular diseases, and agents for the treatment of allergies and inflammation-related conditions and diseases.