# US 2014/0194443 A1 · Pyrazolyl-Based Carboxamides I

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- Number: US 2014/0194443 A1
- Document ID: US20140194443A1
- Status: Published application
- Kind: A1
- Application number: 14/152,695
- 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/US20140194443A1

## CPC

- 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
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 5/14: of the thyroid hormones, e.g. T3, T4
- A61P 7/04: Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
- A61P 7/06: Antianaemics
- A61P 9/00: Drugs for disorders of the cardiovascular system
- 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 11/00: Drugs for disorders of the respiratory system
- A61P 11/02: Nasal agents, e.g. decongestants
- A61P 11/06: Antiasthmatics
- A61P 13/12: of the kidneys
- A61P 15/08: for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
- A61P 17/06: Antipsoriatics
- A61P 17/14: for baldness or alopecia
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 21/00: Drugs for disorders of the muscular or neuromuscular system
- A61P 21/04: for myasthenia gravis
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/14: for treating abnormal movements, e.g. chorea, dyskinesia
- A61P 25/16: Anti-Parkinson drugs
- 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 27/16: Otologicals
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 31/06: for tuberculosis
- A61P 31/08: for leprosy
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- 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 401/10: linked by a carbon chain containing aromatic rings
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 401/14: containing three or more hetero rings
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 403/10: linked by a carbon chain containing aromatic rings
- C07D 405/10: linked by a carbon chain containing aromatic rings
- C07D 405/14: containing three or more hetero rings
- C07D 413/10: linked by a carbon chain containing aromatic rings
- C07D 413/14: containing three or more hetero rings
- C07D 417/10: linked by a carbon chain containing aromatic rings
- C07D 417/14: containing three or more hetero rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## 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 H; 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;
T represents C—R3 or N or N+—O−, 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 at least one of R4, R5 and R6 is selected from the group consisting of
an unsubstituted or mono- or polysubstituted C3-6-cycloaliphatic residue;
an unsubstituted or mono- or polysubstituted 3 to 7 membered heterocycloaliphatic residue;
an unsubstituted or mono- or polysubstituted aryl;
and an unsubstituted or mono- or polysubstituted heteroaryl,
and the remaining substituents of R3, R4, R5, R6 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; —O—R13)—R13; C(═N—)—R; 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);
n represents 0 or 1,
wherein, if n represents 1, then
J represents C—R8 or N or N+—O−,
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 J, K, M, Q and R independently of one another represent(s) either N or N+—O−, whereof 0 or 1 of variables J, K, M, Q and R independently represents N+—O−,
wherein, if n represents 0, then
J represents C—R8 or N or N—O− or O or S or NH or N(C1-4-aliphatic residue),
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 J, K, M and Q represents O or S or NH or N(C1-4-aliphatic residue) and the
remaining of J, K, M and Q independently represent C—R8, respectively C—R9, respectively C—R10, respectively C—R11 or N or N+—O− and
with the proviso that 0, 1, 2 or 3 of J, K, M and Q independently of one another represent
either N or N+—O−, whereof 0 or 1 of variables J, K, M and Q represents N+—O−,
wherein R8, 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(R1)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 at least one of R8, R9, R10, R11 and R12 does not denote H;
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.

### 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; and N(R13)2,
wherein R13 independently of each other denotes C1-4 aliphatic residue, unsubstituted or mono- or polysubstituted.

### 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 J represents C—R8, K represents C—R9, M represents C—R10 or N or or N+—O−, Q represents C—R11 and R represents C—R12.

### Claim 5 (depends on 1)

A compound according to claim 1 wherein n represents 1, J represents C—R8 and/or R represents C—R12, wherein R and R12 are independently of one another 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, with the proviso that at least one of R8 and R12 does not denote H.

### 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; a 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(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; and N(H)—S(═O)2—NH2.

### Claim 7 (depends on 1)

A compound according to claim 1 wherein T represents C—R3, 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 one of R4, R5 and R6 is selected from the group consisting of
an unsubstituted or mono- or polysubstituted C3-6-cycloaliphatic residue,
an unsubstituted or mono- or polysubstituted 3 to 7 membered heterocycloaliphatic residue, and
an unsubstituted or mono- or polysubstituted heteroaryl.

### Claim 9 (depends on 8)

A compound according to claim 8 wherein one of R4, R5 and R6 is selected from the group consisting of
cyclopropyl,
a 3 to 7 membered heterocycloaliphatic residue selected from the group consisting of pyrrolidinyl, pyrrolinyl, pyrazolinyl, isoxazolinyl, oxazolinyl, isoxazolinyl, oxadiazolinyl, tetrahydropyranyl, dihydropyrazinyl, pyrazinyl and morpholinyl, wherein the 3 to 7 membered heterocycloaliphatic residue is unsubstituted or mono- or di-substituted with at least one substituent selected from the group consisting of ═O, CH3, and CH2CH3, and
heteroaryl selected from the group consisting of thiazolyl, thiadiazolyl, oxazolyl, isoxazolyl, thienyl, pyrrolyl, pyrazolyl, oxadiazolyl, tetrazolyl, triazolyl, pyridyl and pyrimidinyl, wherein the heteroaryl is unsubstituted or mono- or di-substituted with at least one substituent selected from the group consisting of OH, NH2, CH3, and CH2CH3,
and the remaining substituents of R3, R4, R5, R6 and R7 are independently of one another selected from the group consisting of H; F; Cl; Br; I; CN; CF3; CF2H; CFH2; OCF3; OCF2H; OCFH2; an unsubstituted C1-4-aliphatic residue; cyclopropyl; OH; and an unsubstituted O—C1-4-aliphatic residue,
with the proviso that at least one of the remaining substituents of R3, R4, R5, R6 and R7 does not denote H.

### Claim 10 (depends on 1)

A compound according to claim 1 wherein
R1 denotes an unsubstituted C1-4-aliphatic residue;
R2 denotes H; F; Cl, OH, NH2, N(CH3)2, CH2NH2, CH2—N(CH3)2, CH2OH; or an unsubstituted C1-4 aliphatic residue;
T represents C—R3 or N, U represents C—R4 or N, V represents C—R5 or N, W represents C—R6 or N, and X represents C—R7 or N,
with the proviso that 0, 1, 2 or 3 of variables T, 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, wherein one of R4, R5 and R6 is selected from the group consisting of
a C3-6-cycloaliphatic residue,
a 3 to 7 membered heterocycloaliphatic residue, wherein the 3 to 7 membered heterocycloaliphatic residue is unsubstituted or mono- or di-substituted with at least one substituent, selected from the group consisting of ═O, CH3, and CH2CH3, and
a heteroaryl,
and the remaining substituents of R3, R4, R5, R6 and R7 are independently of one another selected from the group consisting of H; F; Cl; Br; I; CN; CF3; CF2H; CFH2; OCF3; OCF2H; OCFH2; an unsubstituted C1-4-aliphatic residue; cyclopropyl; OH; and an unsubstituted O—C1-4-aliphatic residue,
with the proviso that at least one of the remaining substituents of R3, R4, R5, R6 and R7 does not denote H;
n represents 1,
J represents C—R8 and/or R represents C—R12,
wherein R8 and R12 are independently of one another 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, with the proviso that at least one of R8 and R12 does not denote H;
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; Br; I; CN; CF3; CF2H; CFH2; OCF3; OCF2H; OCFH2; an unsubstituted C1-4-aliphatic residue; OH; and an unsubstituted O—C1-4-aliphatic residue;
and
M represents N or N+—O− or C—R10,
wherein R10 is selected from the group consisting of H; F; Cl; OCH3; CN; CH3; CF3; CF2H and CFH2,
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 and/or a physiologically acceptable solvate thereof.

### Claim 11 (depends on 1)

A compound according to claim 1, selected from the group consisting of
1 N-(3-Fluoro-pyridin-4-yl)-1-methyl-5-(2-methyl-5-thiazol-2-yl-phenyl)-1H-pyrazole-3-carboxylic acid amide
2 N-(3-Fluoro-pyridin-4-yl)-1-methyl-5-(2-methyl-5-oxazol-2-yl-phenyl)-1H-pyrazole-3-carboxylic acid amide
3 N-(2,6-Difluoro-phenyl)-1-methyl-5-(2-methyl-5-thiazol-2-yl-phenyl)-1H-pyrazole-3-carboxylic acid amide
4 N-(4-Methoxyphenyl)-1-methyl-5-(2-methyl-5-thiazol-2-yl-phenyl)-1H-pyrazole-3-carboxylic acid amide
5 N-(4-Fluorophenyl)-1-methyl-5-(2-methyl-5-thiazol-2-yl-phenyl)-1H-pyrazole-3-carboxylic acid amide
6 1-Methyl-N-(3-methyl-pyridin-4-yl)-5-(2-methyl-5-thiazol-2-yl-phenyl)-1H-pyrazole-3-carboxylic acid amide
7 N-(3-Fluoro-pyridin-4-yl)-5-(2-methoxy-5-thiazol-2-yl-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide
8 N-(2,6-Difluoro-phenyl)-5-(2-methoxy-5-thiazol-2-yl-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide
9 5-(2-Chloro-5-thiazol-2-yl-phenyl)-N-(3-fluoro-pyridin-4-yl)-1-methyl-1H-pyrazole-3-carboxylic acid amide
10 5-(2-Chloro-5-thiazol-2-yl-phenyl)-N-(2,6-difluoro-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide
11 N-(3-Fluoro-pyridin-4-yl)-1-methyl-5-(2-methyl-5-pyridin-4-yl-phenyl)-1H-pyrazole-3-carboxylic acid amide
12 N-(2,6-Difluoro-phenyl)-1-methyl-5-(2-methyl-5-pyridin-4-yl-phenyl)-1H-pyrazole-3-carboxylic acid amide
13 N-(2,6-Difluoro-phenyl)-1-methyl-5-(2-methyl-5-pyrimidin-5-yl-phenyl)-1H-pyrazole-3-carboxylic acid amide
14 N-(2,6-Difluoro-phenyl)-1-methyl-5-(3-thiazol-2-yl-phenyl)-1H-pyrazole-3-carboxylic acid amide
15 5-(5-Cyclopropyl-2-methoxy-phenyl)-N-(3-fluoro-pyridin-4-yl)-1-methyl-1H-pyrazole-3-carboxylic acid amide
16 5-(5-Cyclopropyl-2-methoxy-phenyl)-N-(2,6-difluoro-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide
17 5-(2-Cyclopropyl-5-methyl-pyrimidin-4-yl)-N-(2,6-difluoro-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide
18 N-(2,6-Difluoro-phenyl)-1-methyl-5-(2-methyl-5-oxazol-2-yl-phenyl)-1H-pyrazole-3-carboxylic acid amide
19 N-(2,6-Difluoro-phenyl)-1-methyl-5-[2-methyl-5-(3-methyl-[1,2,4]oxadiazol-5-yl)-phenyl]-1H-pyrazole-3-carboxylic acid amide
20 5-[5-(2-Amino-pyridin-4-yl)-2-methyl-phenyl]-N-(2,6-difluoro-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide
21 N-(3-Fluoro-pyridin-4-yl)-1-methyl-5-(2-methyl-5-tetrahydro-pyran-4-yl-phenyl)-1H-pyrazole-3-carboxylic acid amide
22 N-(2,6-Difluoro-phenyl)-1-methyl-5-(2-methyl-5-tetrahydro-pyran-4-yl-phenyl)-1H-pyrazole-3-carboxylic acid amide
23 N-(2,6-Difluoro-phenyl)-1-methyl-5-[2-methyl-5-(1-methyl-1H-[1,2,4]triazol-3-yl)-phenyl]-1H-pyrazole-3-carboxylic acid amide
24 N-(2,6-Difluoro-phenyl)-1-methyl-5-(2-methyl-4-thiazol-2-yl-phenyl)-1H-pyrazole-3-carboxylic acid amide
25 N-(2,6-Difluoro-phenyl)-1,4-dimethyl-5-(2-methyl-5-thiazol-2-yl-phenyl)-1H-pyrazole-3-carboxylic acid amide
26 N-(3-Fluoro-pyridin-4-yl)-1,4-dimethyl-5-(2-methyl-5-thiazol-2-yl-phenyl)-1H-pyrazole-3-carboxylic acid amide
27 N-(2,6-Difluoro-phenyl)-1,4-dimethyl-5-(3-thiazol-2-yl-phenyl)-1H-pyrazole-3-carboxylic acid amide
28 N-(2,6-Difluoro-phenyl)-1-methyl-5-[2-methyl-5-(5-methyl-4H-[1,2,4]triazol-3-yl)-phenyl]-1H-pyrazole-3-carboxylic acid amide
29 N-(3-Fluoro-pyridin-4-yl)-1,4-dimethyl-5-(3-thiazol-2-yl-phenyl)-1H-pyrazole-3-carboxylic acid amide
30 N-(2,6-Difluoro-phenyl)-1-methyl-5-[5-oxazol-2-yl-2-(trifluoromethyloxy)-phenyl]-1H-pyrazole-3-carboxylic acid amide
31 N-(3-Fluoro-pyridin-4-yl)-1-methyl-5-[5-oxazol-2-yl-2-(trifluoromethyloxy)-phenyl]-1H-pyrazole-3-carboxylic acid amide
32 N-(2,6-Difluoro-phenyl)-1-methyl-5-[2-methyl-5-(4H-[1,2,4]triazol-3-yl)-phenyl]-1H-pyrazole-3-carboxylic acid amide
33 N-(3,5-Difluoro-pyridin-4-yl)-1-methyl-5-[5-oxazol-2-yl-2-(trifluoromethyloxy)-phenyl]-1H-pyrazole-3-carboxylic acid amide
34 5-(5-Cyclopropyl-2-methoxy-phenyl)-N-(2,6-difluoro-phenyl)-1,4-dimethyl-1H-pyrazole-3-carboxylic acid amide
35 5-(5-Cyclopropyl-2-methoxy-phenyl)-N-(3,5-difluoro-pyridin-4-yl)-1,4-dimethyl-1H-pyrazole-3-carboxylic acid amide
36 5-[5-Cyclopropyl-2-(trifluoromethyloxy)-phenyl]-N-(2,6-difluoro-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide
37 5-[5-Cyclopropyl-2-(trifluoromethyloxy)-phenyl]-N-(3,5-difluoro-pyridin-4-yl)-1-methyl-1H-pyrazole-3-carboxylic acid amide
38 5-[5-Cyclopropyl-2-(trifluoromethyloxy)-phenyl]-N-(3-fluoro-pyridin-4-yl)-1-methyl-1H-pyrazole-3-carboxylic acid amide
39 5-[4-Cyclopropyl-2-(trifluoromethyloxy)-phenyl]-N-(2,6-difluoro-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide
40 5-[4-Cyclopropyl-2-(trifluoromethyloxy)-phenyl]-N-(3,5-difluoro-pyridin-4-yl)-1-methyl-1H-pyrazole-3-carboxylic acid amide
41 5-[4-Cyclopropyl-2-(trifluoromethyloxy)-phenyl]-N-(3-fluoro-pyridin-4-yl)-1-methyl-1H-pyrazole-3-carboxylic acid amide
42 2,6-Difluoro-N-[1-methyl-5-(3-thiazol-2-yl-phenyl)-1H-pyrazol-3-yl]-benzamide,
43 4-Amino-N-(3,5-difluoro-pyridin-4-yl)-1-methyl-5-(2-methyl-5-oxazol-2-yl-phenyl)-1H-pyrazole-3-carboxylic acid amide
44 4-Amino-N-(2,6-difluoro-phenyl)-5-(2-methoxy-5-thiazol-2-yl-phenyl)-1-methyl-1H-pyrazole-3-carboxylic acid amide
45 4-amino-N-(3,5-difluoropyridin-4-yl)-5-(2-methoxy-5-(oxazol-2-yl)phenyl)-1-methyl-1H-pyrazole-3-carboxamide
46 4-amino-N-(2,6-difluorophenyl)-5-(2-methoxy-5-(oxazol-2-yl)phenyl)-1-methyl-1H-pyrazole-3-carboxamide
47 4-amino-N-(3,5-difluoropyridin-4-yl)-5-(2-methoxy-5-(thiazol-2-yl)phenyl)-1-methyl-1H-pyrazole-3-carboxamide
48 4-amino-N-(2,6-difluorophenyl)-5-(5-(5,5-dimethyl-4-oxo-4,5-dihydroisoxazol-3-yl)-2-methoxyphenyl)-1-methyl-1H-pyrazole-3-carboxamide
49 4-amino-N-(2,6-difluorophenyl)-1-methyl-5-(5-(oxazol-2-yl)-2-(trifluoromethoxy)phenyl)-1H-pyrazole-3-carboxamide
50 4-amino-N-(3,5-difluoropyridin-4-yl)-1-methyl-5-(5-(oxazol-2-yl)-2-(trifluoromethoxy)phenyl)-1H-pyrazole-3-carboxamide
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 or solvate thereof.

### Claim 12 (depends on 1)

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

### Claim 13 (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 a compound according to claim 1 to a patient in need thereof.

### Claim 14 (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 a compound according to claim 1 to a patient in need thereof.

### Claim 15 (depends on 2)

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

### Claim 16 (depends on 3)

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

### Claim 17 (depends on 6)

A compound according to claim 6 wherein R10 is selected from the group consisting of H; F; Cl; CN; CF3; CF2H; CFH2.