# US 2014/0194452 A1 · Pyrazolyl-Based Carboxamides II

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- Number: US 2014/0194452 A1
- Document ID: US20140194452A1
- Status: Published application
- Kind: A1
- Application number: 14/152,716
- Filed: 2014-01-10
- Published: 2014-07-10
- Earliest claimed: 2013-01-10
- Assignees: GrüNenthal GmbH
- Applicants: Grünenthal GmbH
- Inventors: Sonja Nordhoff; Sebastian Wachten; Achim Kless; Felix Voss; Stefanie Ritter
- Web page: https://patentgrep.com/patent/US20140194452A1

## CPC

- A61K 31/506: not condensed and containing further heterocyclic rings
- A61K 31/415: 1,2-Diazoles
- A61K 31/4439: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole (nicotine A61K31/465)
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 11/06: Antiasthmatics
- A61P 17/06: Antipsoriatics
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- 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 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 231/14: 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 ring carbon atoms
- 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 401/14: containing three or more hetero rings
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- 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

The invention relates to pyrazolyl-based carboxamide compounds useful as ICRAC inhibitors, to pharmaceutical compositions containing these compounds and to these compounds for the use in the treatment and/or prophylaxis of diseases and/or disorders, in particular inflammatory diseases and/or inflammatory disorders.

## Claims

### Claim 1

A compound of general formula (I),
wherein
R1 denotes
C1-4-aliphatic residue, unsubstituted or mono- or polysubstituted; or
C3-6-cycloaliphatic residue or a 3 to 7 membered heterocycloaliphatic residue, in each case unsubstituted or mono- or polysubstituted and in each case optionally connected via a C1-4 aliphatic group, which in turn may be unsubstituted or mono- or polysubstituted; with the proviso that if R1 represents a 3 to 7 membered heterocycloaliphatic residue, said 3 to 7 membered heterocycloaliphatic residue is connected to the remaining part of the structure according to general formula (I) via a carbon atom of the 3 to 7 membered heterocycloaliphatic residue;
R2 denotes H; F; Cl; Br; I; NO2; CN; CF3; CF2H; CFH2; R13; OH; O—R13; NH2; N(H)R13; N(R13)2;
U represents C—R4 or N or N+—O−, V represents C—R5 or N or N+—O−, W represents C—R6 or N or N+—O−, and X represents C—R7 or N or N+—O−,
with the proviso that 0, 1, 2 or 3 of variables T, U, V, W and X independently of one another represent(s) either N or N+—O−, whereof 0 or 1 of variables T, U, V, W and X independently of one another represent(s) N+—O− and
with the proviso that at least one of U, V and W does not represent N,
wherein
R4, R5 and R6 are independently of one another selected from the group consisting of H; F; Cl; Br; I; NO2; CN; CF3; CF2H; CFH2; CF2Cl; CFCl2; C1-8-aliphatic residue, unsubstituted or mono- or polysubstituted; C(═O)OH; C(═O)—R13; C(═O)R14; C(═O)—OR13; C(═O)—OR14; C(═O)—N(H)(OH); C(═N—OH)—H; C(═N—OH)—R13; C(═N—OH)—R14; C(═N—O—R13)—H; C(═N—O—R13)—R13; C(═N—O—R13)—R14; C(═O)NH2; C(═O)—N(H)R13; C(═O)—N(R13)2; C(═O)—N(H)R14; C(═O)—N(R14)2; C(═O)—N(R13)(R14); C(═O)—N(Ra)(Rb); OH; OR13; OCF3; OCF2H; OCFH2; OCF2Cl; OCFCl2; OR14; O—C(═O)R13; O—C(═O)R14; O—C(═O)—N(H)R13; O—C(═O)—N(H)R14; O—C(═O)—N(R13)2; O—C(═O)—N(R14)2; O—C(═O)—N(R13)(R14); O—C(═O)—N(Ra)(Rb); NH2; N(H)R13; N(R13)2; N(H)R14; N(R14)2; N(R13)(R14); N(Ra)(Rb); NH—C(═O)—R14; NH—C(═O)—R13; N(R13)—C(═O)—R13; N(R13)—C(═O)—R14; NH—S(═O)2—R13; N(R13)—S(═O)2—R13; NH—S(═O)2—R14; N(R13)—S(═O)2—R14; N(H)—C(═O)—OR13; N(H)—C(═O)—OR14; N(R13)—C(═O)—OR13; N(R13)—C(═O)—OR14; N(H)—C(═O)—NH2; N(H)—C(═O)—N(H)R13; N(H)—C(═O)—N(H)R14; N(H)—C(═O)—N(R13)2; N(H)—C(═O)—N(R14)2; N(H)—C(═O)—N(R13)(R14); N(H)—C(═O)—N(Ra)(Rb); N(R13)—C(═O)—NH2; N(R13)—C(═O)—N(H)R13; N(R13)—C(═O)—N(H)R14; N(R13)—C(═O)—N(R13)2; N(R13)—C(═O)—N(R14)2; N(R13)—C(═O)—N(R13)(R14); N(R13)—C(═O)—N(Ra)(Rb); SH; S—R13; SCF3; S—R14; S(═O)2OH; S(═O)2—R13; S(═O)2—R14; S(═O)—R13; S(═O)—R14; S(═O)2—OR13; S(═O)2—OR14; S(═O)2—N(H)(R13); S(═O)2—N(R13)2; S(═O)2—N(H)(R14); S(═O)2—N(R13)(R14); S(═O)2—N(Ra)(Rb);
and R3 and R7 are independently of one another selected from the group consisting of H; F; Cl; Br; I; NO2; CN; CF3; CF2H; CFH2; CF2Cl; CFCl2; R13; R14; C(═O)OH; C(═O)—R13; C(═O)R14; C(═O)—OR13; C(═O)—OR14; C(═O)—N(H)(OH); C(═N—OH)—H; C(═N—OH)—R13; C(═N—OH)—R14; C(═N—O—R13)—H; C(═N—O—R13)—R13; C(═N—O—R13)—R14; C(═O)NH2; C(═O)—N(H)R13; C(═O)—N(R13)2; C(═O)—N(H)R14; C(═O)—N(R14)2; C(═O)—N(R13)(R14); C(═O)—N(Ra)(Rb); OH; OR13; OCF3; OCF2H; OCFH2; OCF2Cl; OCFCl2; OR14; O—C(═O)R13; O—C(═O)R14; O—C(═O)—N(H)R13; O—C(═O)—N(H)R14; O—C(═O)—N(R13)2; O—C(═O)—N(R14)2; O—C(═O)—N(R13)(R14); O—C(═O)—N(Ra)(Rb); NH2; N(H)R13; N(R13)2; N(H)R14; N(R14)2; N(R13)(R14); N(Ra)(Rb); NH—C(═O)—R14; NH—C(═O)—R13; N(R13)—C(═O)—R13; N(R13)—C(═O)—R14; NH—S(═O)2—R13; N(R13)—S(═O)2—R13; NH—S(═O)2—R14; N(R13)—S(═O)2—R14; N(H)—C(═O)—OR13; N(H)—C(═O)—OR14; N(R13)—C(═O)—OR13; N(R13)—C(═O)—OR14; N(H)—C(═O)—NH2; N(H)—C(═O)—N(H)R13; N(H)—C(═O)—N(H)R14; N(H)—C(═O)—N(R13)2; N(H)—C(═O)—N(R14)2; N(H)—C(═O)—N(R13)(R14); N(H)—C(═O)—N(Ra)(Rb); N(R13)—C(═O)—NH2; N(R13)—C(═O)—N(H)R13; N(R13)—C(═O)—N(H)R14; N(R13)—C(═O)—N(R13)2; N(R13)—C(═O)—N(R14)2; N(R13)—C(═O)—N(R13)(R14); N(R13)—C(═O)—N(Ra)(Rb); SH; S—R13; SCF3; S—R14; S(═O)2OH; S(═O)2—R13; S(═O)2—R14; S(═O)—R13; S(═O)—R14; S(═O)2—OR13; S(═O)2—OR14; S(═O)2—N(H)(R13); S(═O)2—N(R13)2; S(═O)2—N(H)(R14); S(═O)2—N(R13)(R14); S(═O)2—N(Ra)(Rb);
with the proviso that R3 does not represent H;
n represents 0 or 1,
wherein, if n represents 1, then
K represents C—R9 or N or N+—O−,
M represents C—R10 or N or N+—O−,
Q represents C—R11 or N or N+—O−, and
R represents C—R12 or N or N+—O−,
with the proviso that 0, 1, 2 or 3 of variables K, M, Q and R independently of one another represent(s) either N or N+—O−, whereof 0 or 1 of variables K, M, Q and R independently represents N+—O−,
wherein, if n represents 0, then
K represents C—R9 or N or N+—O− or O or S or NH or N(C1-4-aliphatic residue),
M represents C—R10 or N or N+—O− or O or S or NH or N(C1-4-aliphatic residue) and
Q represents C—R11 or N or N+—O− or O or S or NH or N(C1-4-aliphatic residue),
with the proviso that
one of K, M and Q represents O or S or NH or N(C1-4-aliphatic residue) and the remaining of K, M and Q independently represent C—R9, respectively C—R10, respectively C—R11 or N or N+—O− and
with the proviso that 0, 1 or 2 of variables K, M and Q independently of one another represent either N or N+—O−, whereof 0 or 1 of variables K, M and Q represents N+—O−,
wherein R8 is selected from F, Cl, CF3, CF2H, CFH2, CH3, CN, OCF2H, OCFH2, and OCF3,
and wherein
R9, R10, R11 and R12 are independently of one another selected from the group consisting of H; F; Cl; Br; I; NO2; CN; CF3; CF2H; CFH2; CF2Cl; CFCl2; R13; R14; C(═O)OH; C(═O)—R13; C(═O)R14; C(═O)—OR13; C(═O)—OR14; C(═O)—N(H)(OH); C(═N—OH)—H; C(═N—OH)—R13; C(═N—OH)—R14; C(═N—O—R13)—H; C(═N—O—R13)—R13; C(═N—O—R13)—R14; C(═O)NH2; C(═O)—N(H)R13; C(═O)—N(R13)2; C(═O)—N(H)R14; C(═O)—N(R14)2; C(═O)—N(R13)(R14); C(═O)—N(Ra)(Rb); OH; OR13; OCF3; OCF2H; OCFH2; OCF2Cl; OCFCl2; OR14; O—C(═O)R13; O—C(═O)R14; O—C(═O)—N(H)R13; O—C(═O)—N(H)R14; O—C(═O)—N(R13)2; O—C(═O)—N(R14)2; O—C(═O)—N(R13)(R14); O—C(═O)—N(Ra)(Rb); NH2; N(H)R13; N(R13)2; N(H)R14; N(R14)2; N(R13)(R14); N(Ra)(Rb); NH—C(═O)—R14; NH—C(═O)—R13; N(R13)—C(═O)—R13; N(R13)—C(═O)—R14; NH—S(═O)2—R13; N(R13)—S(═O)2—R13; NH—S(═O)2—R14; N(R13)—S(═O)2—R14; N(H)—C(═O)—OR13; N(H)—C(═O)—OR14; N(R13)—C(═O)—OR13; N(R13)—C(═O)—OR14; N(H)—C(═O)—NH2; N(H)—C(═O)—N(H)R13; N(H)—C(═O)—N(H)R14; N(H)—C(═O)—N(R13)2; N(H)—C(═O)—N(R14)2; N(H)—C(═O)—N(R13)(R14); N(H)—C(═O)—N(Ra)(Rb); N(R13)—C(═O)—NH2; N(R13)—C(═O)—N(H)R13; N(R13)—C(═O)—N(H)R14; N(R13)—C(═O)—N(R13)2; N(R13)—C(═O)—N(R14)2; N(R13)—C(═O)—N(R13)(R14); N(R13)—C(═O)—N(Ra)(Rb); SH; S—R13; SCF3; S—R14; S(═O)2OH; S(═O)2—R13; S(═O)2—R14; S(═O)—R13; S(═O)—R14; S(═O)2—OR13; S(═O)2—OR14; S(═O)2—N(H)(R13); S(═O)2—N(R13)2; S(═O)2—N(R13)(R14); S(═O)2—N(R13)(R14); S(═O)2—N(Ra)(Rb);
wherein
each R13 independently of each other denotes
C1-8-aliphatic residue, unsubstituted or mono- or polysubstituted;
or
C3-6-cycloaliphatic residue or 3 to 7 membered heterocycloaliphatic residue, in each case unsubstituted or mono- or polysubstituted;
or
C3-6-cycloaliphatic residue or 3 to 7 membered heterocycloaliphatic residue, in each case unsubstituted or mono- or polysubstituted, and in each case connected via a C1-4-aliphatic residue, unsubstituted or mono- or polysubstituted;
each R14 independently of each other denotes
aryl and heteroaryl residue, in each case independently of one another unsubstituted or mono- or polysubstituted,
or
aryl and heteroaryl residue, in each case independently of one another unsubstituted or mono- or polysubstituted and in each case connected via a C1-4-aliphatic group, unsubstituted or mono- or polysubstituted;
Ra and Rb together with the N-atom connecting them form a 3 to 7 membered heterocyclic residue, unsubstituted or mono- or polysubstituted;
optionally in the form of a single stereoisomer or a mixture of stereoisomers, in the form of the free compound and/or a physiologically acceptable salt thereof and/or a physiologically acceptable solvate thereof,
with the proviso that the compound according to general formula (I) does not represent
N-(2-Cyanophenyl)-5-(2-methoxy-5-methylphenyl)-1-methyl-1H-pyrazole-3-carboxamide,
5-(2-Fluoro-4-methoxyphenyl)-N-(2-fluorophenyl)-1-methyl-1H-pyrazole-3-carboxamide,
1-Ethyl-5-(2-fluoro-4-methoxyphenyl)-N-(2-fluorophenyl) 1H-pyrazole-3-carboxamide

### Claim 2 (depends on 1)

A compound according to claim 1, wherein R2 is selected from the group consisting of H; F; Cl; Br; CN; CF3; CF2H; CFH2; R13; OH; O—R13; NH2; N(H)R13; N(R13)2,
wherein R13 independently of each other denotes an unsubstituted or mono- or polysubstituted C1-4 aliphatic residue.

### Claim 3 (depends on 1)

A compound according to claim 1 wherein R1 is selected from the group consisting of unsubstituted C1-4-aliphatic residue and unsubstituted cyclopropyl.

### Claim 4 (depends on 1)

A compound according to claim 1 wherein
n represents 1, and
K represents C—R9, M represents C—R10 or N or or N+—O−, Q represents C—R11 and R represents C-R12
or
n represents 1, and
K represents C—R9, M represents N, Q represents C—R11 and R represents N.

### Claim 5 (depends on 1)

A compound according to claim 1 wherein
n represents 1,
R represents C—R12,
wherein R12 is selected from the group consisting of H; CH3; CF3; CF2H; CFH2; CF2Cl; CFCl2; CH2CH3; CN; OH; OCH3; OCHF2; OCH2F; OCHF2; OCF3; NH2; NHCH3; N(CH3)2; NH(C═O)CH3; F; Cl and Br.

### Claim 6 (depends on 1)

A compound according to claim 1 wherein
n represents 1,
M represents N or N+—O− or C—R10,
wherein R10 is selected from the group consisting of
H; F; Cl; CN; CF3; CF2H; CFH2; CF2Cl; CFCl2; C1-8-aliphatic residue; C(═O)OH; C(═O)—NH2; C(═O)—C1-8-aliphatic residue; C(═O)O—C1-8-aliphatic residue; C(═O)NH—C1-8-aliphatic residue; C(═O)N(C1-8-aliphatic residue)2; OH; O—C1-8-aliphatic residue; OCF3; OCF2H; OCFH2; O—C(═O)—C1-8-aliphatic residue; NH2; N(H)—C1-8-aliphatic residue; N(C1-8-aliphatic residue)2; N(H)—C(═O)—C1-8-aliphatic residue; N(C1-8-aliphatic residue)-S(═O)2—C1-8-aliphatic residue; N(H)—S(═O)2—NH2; S(═O)2—C1-8-aliphatic residue.

### Claim 7 (depends on 1)

A compound according to claim 1 wherein
U represents C—R4, V represents C—R5, W represents C—R6, and X represents C—R7.

### Claim 8 (depends on 1)

A compound according to claim 1 wherein
R3 is selected from the group consisting of
F; Cl; CN; CF3; CF2H; CFH2; CF2Cl; CFCl2; OCHF2; OCFH2; OCF3; C1-8-aliphatic residue; C(═O)OH; C(═O)—NH2; C(═O)—C1-8-aliphatic residue; C(═O)O—C1-8-aliphatic residue; C(═O)NH—C1-8-aliphatic residue; C(═O)N(C1-8-aliphatic residue)2; OH; O—C1-8-aliphatic residue; OCF3; OCF2H; OCFH2; O—C(═O)—C1-8-aliphatic residue; NH2; N(H)—C1-8-aliphatic residue; N(C1-8-aliphatic residue)2; N(H)—O(═O)—C1-8-aliphatic residue; N(C1-8-aliphatic residue)-S(═O)2—C1-8-aliphatic residue; N(H)—S(═O)2—NH2; S(═O)2—C1-8-aliphatic residue; C3-6-cycloaliphatic residue; 3 to 7 membered heterocycloaliphatic residue,
and
X represents C—R7 and
R7 represents H or F or CH3 or CF3.

### Claim 9 (depends on 1)

A compound according to claim 1 wherein
R4, R5 and R6 are selected from the group consisting of
H; F; Cl; CN; CF3; CF2H; CFH2; CF2Cl; CFCl2; OCHF2; OCFH2; OCF3; C1-8-aliphatic residue; C(═O)—NH2; C(═O)—C1-8-aliphatic residue; C(═O)O—C1-8-aliphatic residue; C(═O)NH—C1-8-aliphatic residue; C(═O)N(C1-8-aliphatic residue)2; OH; O—C1-8-aliphatic residue; OCF3; OCF2H; OCFH2; O—C(═O)—C1-8-aliphatic residue; NH2; N(H)—C1-8-aliphatic residue; N(C1-8-aliphatic residue)2; N(H)—O(═O)—C1-8-aliphatic residue; N(C1-8-aliphatic residue)-S(═O)2—C1-8-aliphatic residue; N(H)—S(═O)2—NH2; S(═O)2—C1-8-aliphatic residue;
preferably from the group consisting of H; F; Cl; OCH3; OCHF2; OCFH2; OCF3; CN; CH3; CF3; CF2H and CFH2.

### Claim 10 (depends on 1)

A compound according to claim 1 wherein
R1 denotes unsubstituted C1-4-aliphatic residue;
R2 denotes H; F; Cl, OH, NH2, NHCH3, N(CH3)2, CH2NH2, CH2—N(CH3)2, CH2OH; or unsubstituted C1-4 aliphatic residue; preferably denotes H, C1, NH2, CH3, CH2OH and CH2CH3;
U represents C—R4 or N, V represents C—R5 or N, W represents C—R6 or N, and X represents C—R7, with the proviso that 0, 1, 2 or 3 of variables U, V, W and X independently of one another represent(s) N,
and with the proviso that at least one of U, V and W does not represent N,
R3 denotes F; Cl; CN; CF3; CF2H; CFH2; OCF3; OCF2H; OCFH2; cyclopropyl; unsubstituted C1-4-aliphatic residue; OH or unsubstituted O—C1-4-aliphatic residue;
R7 denotes H, F, CH3 or CF3; and
R4, R5 and R6 are independently selected from the group consisting of H; F; Cl; CN; CF3; CF2H; CFH2; CF2Cl; CFCl2; OCHF2; OCFH2; OCF3; C1-8-aliphatic residue; C(═O)—NH2; C(═O)—C1-8-aliphatic residue; C(═O)O—C1-8-aliphatic residue; C(═O)NH—C1-8-aliphatic residue; C(═O)N(C1-8-aliphatic residue)2; OH; O—C1-8-aliphatic residue; OCF3; OCF2H; OCFH2; O—C(═O)—C1-8-aliphatic residue; NH2; N(H)—C1-8-aliphatic residue; N(C1-8-aliphatic residue)2; N(H)—O(═O)—C1-8-aliphatic residue; N(C1-8-aliphatic residue)-S(═O)2—C1-8-aliphatic residue; N(H)—S(═O)2—NH2; S(═O)2—C1-8-aliphatic residue;
n represents 1,
K represents C—R9 and Q represents C—R11,
wherein R9 and R11 are independently of one another selected from the group consisting of H; F; Cl; CN; CF3; CF2H; CFH2; OCF3; OCF2H; OCFH2; CH3; OH; and OCH3; and
M represents N or N+—O− or C—R19,
wherein R10 is selected from the group consisting of H; F; Cl; OCH3; CN; CH3; CF3; CF2H; CFH2 or S(═O)2—CH3
R represents C—R12,
wherein R12 is selected from the group consisting of H; CH3; CF3; CF2H; CFH2; CH2CH3; CN; OH; OCH3; OCHF2; OCH2F; OCHF2; OCF3; F and Cl.

### Claim 11 (depends on 1)

A compound according to claim 1 wherein the compound has general formula (Iaa),
wherein
R1, R2, U, V, W and X are defined as before,
R8 denotes F, Cl, CN, CF3, CF2H, CFH2, CH3 or O—CH3
and
K, M, Q and R independently represent N, CH or C—R8a,
wherein R8a denotes F, Cl, CN, CF3, CF2H, CFH2, CH3, CH2CH3, O—CH3 or O—CH2CH3, with the proviso, that 0 or 1 of the substituents K, M, Q and R represent N.

### Claim 12 (depends on 1)

A compound according to claim 1 wherein the compound is selected from the group consisting of
1 N-(2,6-Difluoro-phenyl)-5-(2-methoxyphenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
2 N-(2,4-Difluoro-phenyl)-5-(2,5-dimethoxyphenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
3 5-(2-Ethoxy-5-methoxy-phenyl)-N-(3-fluoro-pyridin-4-yl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
4 N-(2,6-Difluoro-phenyl)-5-(2-ethoxy-5-methoxy-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
5-(2,5-Difluoro-phenyl)-N-(2,6-difluoro-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
6 N-(2,6-Difluoro-phenyl)-5-[2-fluoro-5-(trifluoromethyl)-phenyl]-1-methyl-1H-pyrazole-3-carboxylic acid amide;
7 N-(2,6-Difluoro-phenyl)-1-methyl-5-[2-(trifluoromethyl)-phenyl]-1H-pyrazole-3-carboxylic acid amide;
8 N-(2,6-Difluoro-phenyl)-5-[5-methoxy-2-(trifluoromethyloxy)-phenyl]-1-methyl-1H-pyrazole-3-carboxylic acid amide;
9 N-(3-Fluoro-pyridin-4-yl)-5-[5-methoxy-2-(trifluoromethyloxy)-phenyl]-1-methyl-1H-pyrazole-3-carboxylic acid amide;
10 N-(2,6-Difluoro-phenyl)-5-(5-fluoro-2-methoxy-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
11 5-[2-Chloro-4-(trifluoromethyloxy)-phenyl]-N-(3-fluoro-pyridin-4-yl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
12 5-[2-Chloro-4-(trifluoromethyloxy)-phenyl]-N-(2,6-difluoro-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
13 5-(2,5-Dimethoxyphenyl)-N-(2-fluoro-4-methylsulfonyl-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
14 5-(2,5-Dimethoxyphenyl)-1-methyl-N-[3-(trifluoromethyl)-pyridin-4-yl]-1H-pyrazole-3-carboxylic acid amide;
15 N-(3-Cyano-pyridin-4-yl)-5-(2,5-dimethoxyphenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
16 5-(2,5-Dimethoxyphenyl)-1-methyl-N-(4-methyl-pyridin-3-yl)-1H-pyrazole-3-carboxylic acid amide;
17 5-(2,5-Dimethoxyphenyl)-N-(4,6-dimethyl-pyridin-3-yl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
18 5-(2,5-Dimethoxyphenyl)-1-methyl-N-(5-methyl-pyrimidin-4-yl)-1H-pyrazole-3-carboxylic acid amide;
19 5-(2,5-Dimethoxyphenyl)-N-(3-fluoro-pyridin-4-yl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
20 5-(2,5-Dimethoxyphenyl)-1-methyl-N-(3-methyl-pyridin-4-yl)-1H-pyrazole-3-carboxylic acid amide;
21 N-(2,6-Difluoro-phenyl)-5-(2,5-dimethoxyphenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
22 5-(5-Chloro-2-methoxy-phenyl)-N-(3-fluoro-pyridin-4-yl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
23 5-(5-Chloro-2-methyl-phenyl)-N-(3-fluoro-pyridin-4-yl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
24 N-(3-Fluoro-pyridin-4-yl)-5-(4-methoxy-2-methyl-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
25 5-(2,5-Dimethoxyphenyl)-N-(3-fluoro-pyridin-4-yl)-1,4-dimethyl-1H-pyrazole-3-carboxylic acid amide;
26 5-(5-Chloro-2-methyl-phenyl)-N-(2,6-difluoro-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
27 5-(2,5-Dimethoxyphenyl)-1-methyl-N-(o-tolyl)-1H-pyrazole-3-carboxylic acid amide;
28 5-(5-Chloro-2-methyl-phenyl)-1-methyl-N-(3-methyl-pyridin-4-yl)-1H-pyrazole-3-carboxylic acid amide;
29 N-(3-Fluoro-pyridin-4-yl)-1-methyl-5-[2-methyl-5-(trifluoromethyl)-phenyl]-1H-pyrazole-3-carboxylic acid amide;
30 N-(2,6-Difluoro-phenyl)-1-methyl-5-[2-methyl-5-(trifluoromethyl)-phenyl]-1H-pyrazole-3-carboxylic acid amide;
31 N-(2,6-Difluoro-4-methoxy-phenyl)-5-(2,5-dimethoxyphenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
32 5-(2,5-Dimethoxyphenyl)-N-(2-fluoro-6-methyl-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
33 5-(2,5-Dimethoxyphenyl)-N-(2-fluorophenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
34 N-(3,5-Difluoro-pyridin-4-yl)-5-(2,5-dimethoxyphenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
35 N-(2-Chloro-6-fluoro-phenyl)-5-(2,5-dimethoxyphenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
36 5-[2-Chloro-5-(trifluoromethyl)-phenyl]-N-(2,6-difluoro-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
37 N-(2,6-Difluoro-phenyl)-5-(2,5-dimethoxyphenyl)-1-ethyl-1H-pyrazole-3-carboxylic acid amide;
38 5-[2-Cyano-5-(trifluoromethyl)-phenyl]-N-(2,6-difluoro-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
39 4-Chloro-N-(2,6-difluoro-phenyl)-5-(2,5-dimethoxyphenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
40 4-Chloro-5-(2,5-dimethoxyphenyl)-N-(3-fluoro-pyridin-4-yl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
41 N-(2,6-Difluoro-phenyl)-5-(2,5-dimethoxyphenyl)-1H-pyrazole-3-carboxylic acid amide;
42 N-(2,6-Difluoro-phenyl)-5-(2,5-dimethoxyphenyl)-4-ethyl-1-methyl-1H-pyrazole-3-carboxylic acid amide;
43 N-(2,6-Difluoro-phenyl)-5-(2,5-dimethoxyphenyl)-4-(hydroxymethyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
44 4-Amino-N-(2,6-difluoro-phenyl)-5-(2,5-dimethoxyphenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
45 5-[2-Cyclopropyl-5-(trifluoromethyloxy)-phenyl]-N-(2,6-difluoro-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
46 5-[2-Cyclopropyl-5-(trifluoromethyloxy)-phenyl]-N-(3,5-difluoro-pyridin-4-yl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
47 5-[2-Cyclopropyl-5-(trifluoromethyloxy)-phenyl]-N-(3-fluoro-pyridin-4-yl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
48 4-Amino-5-(2,5-dimethoxyphenyl)-N-(3-fluoro-pyridin-4-yl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
49 N-(3,5-Difluoro-pyridin-4-yl)-5-[2-fluoro-6-(trifluoromethyl)-phenyl]-1-methyl-1H-pyrazole-3-carboxylic acid amide;
50 N,5-Bis(2,6-difluoro-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
51 N-(2,6-Difluoro-phenyl)-5-[2-fluoro-6-(trifluoromethyl)-phenyl]-1-methyl-1H-pyrazole-3-carboxylic acid amide;
52 N-(2-Chloro-6-methyl-phenyl)-5-(2,6-difluoro-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
53 5-(2,6-Difluoro-phenyl)-N-(3-fluoro-5-methyl-pyridin-4-yl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
54 5-[2-Fluoro-6-(trifluoromethyl)-phenyl]-1-methyl-N-[2-(trifluoromethyloxy)-phenyl]-1H-pyrazole-3-carboxylic acid amide;
55 N-(2,4-Difluoro-phenyl)-5-[2-fluoro-6-(trifluoromethyl)-phenyl]-1-methyl-1H-pyrazole-3-carboxylic acid amide;
56 N-(2-Cyano-phenyl)-5-[2-fluoro-6-(trifluoromethyl)-phenyl]-1-methyl-1H-pyrazole-3-carboxylic acid amide;
57 N-(2,4-Dichlorophenyl)-5-[2-fluoro-6-(trifluoromethyl)-phenyl]-1-methyl-1H-pyrazole-3-carboxylic acid amide;
58 N-(2,6-Difluoro-4-methoxy-phenyl)-5-[2-fluoro-6-(trifluoromethyl)-phenyl]-1-methyl-1H-pyrazole-3-carboxylic acid amide;
59 N-(2-Fluoro-6-methyl-phenyl)-5-[2-fluoro-6-(trifluoromethyl)-phenyl]-1-methyl-1H-pyrazole-3-carboxylic acid amide;
60 5-[2-Fluoro-6-(trifluoromethyl)-phenyl]-1-methyl-N-[2-(trifluoromethyl)-phenyl]-1H-pyrazole-3-carboxylic acid amide;
61 N-(2-Fluorophenyl)-5-[2-fluoro-6-(trifluoromethyl)-phenyl]-1-methyl-1H-pyrazole-3-carboxylic acid amide;
62 N-(3-Fluoro-pyridin-4-yl)-5-[2-fluoro-6-(trifluoromethyl)-phenyl]-1-methyl-1H-pyrazole-3-carboxylic acid amide;
63 N-(3-Fluoro-5-methyl-pyridin-4-yl)-5-[2-fluoro-6-(trifluoromethyl)-phenyl]-1-methyl-1H-pyrazole-3-carboxylic acid amide;
64 1-Methyl-5-(4-methyl-pyridin-3-yl)-N-[2-(trifluoromethyl)-phenyl]-1H-pyrazole-3-carboxylic acid amide;
65 N-(3-Fluoro-5-methyl-pyridin-4-yl)-1-methyl-5-(4-methyl-pyridin-3-yl)-1H-pyrazole-3-carboxylic acid amide;
66 N-(2,6-Difluoro-phenyl)-5-(2-methoxy-4-methylsulfonyl-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide;
67 N-(3,5-Difluoro-pyridin-4-yl)-5-(2,5-dimethoxyphenyl)-1-methyl-4-methylamino-1H-pyrazole-3-carboxylic acid amide;
optionally in the form of the free compound and/or a physiologically acceptable salt thereof and/or a physiologically acceptable solvate thereof.

### Claim 13 (depends on 1)

A pharmaceutical composition comprising at least one compound according claim 1 and optionally one or more suitable, pharmaceutically compatible auxiliaries and/or, if appropriate, one or more further pharmacologically active compounds.

### Claim 14 (depends on 1)

A method for the treatment and/or prophylaxis of one or more disorders selected from the group consisting of inflammatory disorders and/or autoimmune diseases and/or allergic disorders comprising administering to a patient in need thereof an effective amound of a compound according to claim 1.

### Claim 15 (depends on 1)

A method for the treatment and/or prophylaxis of psoriasis and/or psoriatic arthritis and/or rheumatoid arthritis and/or inflammatory bowel disease and/or asthma and/or allergic rhinitis comprising administering to a patient in need thereof an effective amount of a compound according to claim 1.

### Claim 16 (depends on 2)

A compound according to claim 2 wherein R2 is selected from the group consisting of H, Cl, NH2, CH3, CH2OH and CH2CH3.

### Claim 17 (depends on 3)

A compound according to claim 3 wherein R1 denotes CH3 or CH2CH3.

### Claim 18 (depends on 6)

A compound according to claim 6 wherein R10 is selected from the group consisting of the group consisting of H; F; Cl; OCH3; CN; CH3; CF3; CF2H; CFH2 and S(═O)2—CH.

### Claim 19 (depends on 9)

A compound according to claim 9 wherein R4, R5 and R6 are selected from the group consisting of the group consisting of H; F; Cl; OCH3; OCHF2; OCFH2; OCF3; CN; CH3; CF3; CF2H and CFH2.