# US 7,410,986 B2 · 4-6-diphenyl pyridine derivatives as antiinflammatory agents

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- Number: US 7,410,986 B2
- Document ID: US7410986B2
- Status: Granted
- Kind: B2
- Application number: 10/433,377
- Filed: 2001-11-19
- Published: 2004-05-20
- Granted: 2008-08-12
- Earliest claimed: 2000-12-01
- Assignees: Bayer Aktiengesellschaft
- Inventors: Toshiki Murata; Sachiko Sasaki; Takashi Yoshino; Yuka Ikegami; Tsutomu Masuda; Mitsuyuki Shimada; Takuya Shintani; Makoto Shimazaki; Timothy B. Lowinger; Karl B. Ziegelbauer; Kinji Fuchikami; Masaomi Umeda; Hiroshi Komura; Nagahiro Yoshida
- Web page: https://patentgrep.com/patent/US7410986B2

## CPC

- C07D 213/73: Unsubstituted amino or imino radicals
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- 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 11/02: Nasal agents, e.g. decongestants
- A61P 11/06: Antiasthmatics
- A61P 17/00: Drugs for dermatological disorders
- A61P 17/04: Antipruritics
- A61P 17/06: Antipsoriatics
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 19/06: Antigout agents, e.g. antihyperuricemic or uricosuric agents
- A61P 21/00: Drugs for disorders of the muscular or neuromuscular system
- A61P 27/02: Ophthalmic agents
- A61P 27/14: Decongestants or antiallergics
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 31/04: Antibacterial agents
- A61P 35/00: Antineoplastic agents
- A61P 37/00: Drugs for immunological or allergic disorders
- A61P 37/02: Immunomodulators
- 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 213/80: in position 3
- C07D 213/82: in position 3
- C07D 213/85: in position 3
- 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 405/12: linked by a chain containing hetero atoms as chain links
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

4-aryl pyrimidine compounds of general formula and salts thereof: wherein X is CH or N; R1 is hydrogen, halogen, C1-6 alkyl, C1-6 alkoxy, etc.; R2 is hydrogen or hydroxy; R3 is hydrogen, C1-6 alkyl, etc.; R4 is hydrogen, hydroxy, halogen, amino, etc.; R5 is hydroxy, amino, carboxy, etc.; R6 is hydrogen, carbamoyl, cyano, carboxy, C1-6 alkoxycarbonyl, etc. and R7 is amino or C1-6 alkanoylamino. The compounds (I) or the salts thereof have an excellent anti-inflammatory activity and the like.

## Claims

### Claim 1

A 4-aryl pyridine derivative of the formula (I):
wherein
X is CH;
R1 is hydrogen, hydroxy, halogen, C1-6 alkyl, C1-6 alkoxy, C1-6 alkoxycarbonyl, nitro, amino, mono or di (C1-6 alkyl)amino, phenylsulfonylamino, —NHR11 or —O—(CH2)n—R12,
wherein
R11 is phenyl substituted C1-6 alkyl, C1-6 alkanoyl or C1-6alkylsulfonyl,
n represents an integer selected from 0 to 6, and
R12 is C2-6 alkenyl, benzoyl, mono or di phenyl, mono or di (C1-6 alkyl)-amino, C1-6 alkanoyl, C1-6 alkoxycarbonyl, or a 3 to 10 membered saturated or unsaturated ring having 0 to 3 heteroatoms selected from the group consisting of S, O and N, and said ring is optionally substituted by hydroxy, nitro, cyano, mono or di halogen, C1-6 alkyl, halogen substituted C1-6 alkyl, amino, mono or di (C1-6 alkyl)amino, C1-6 alkanoylamino, carbamoyl, C1-6 alkoxy, C1-6 alkoxycarbonyl, or phenyl;
R2 is hydrogen, hydroxy, halogen, or C1-6 alkyl;
R3 is hydrogen, hydroxy, halogen, C1-6 alkoxy, C3-6 cycloalkyl substituted C1-6 alkyloxy, —N R31R32, or a 3 to 6 membered saturated ring having 0 to 3 heteroatoms selected from the group consisting of O and N, and said ring is optionally substituted by R33;
wherein
R31 is hydrogen or C1-6 alkyl
R32 is hydrogen, C1-6 alkanoyl, or C1-6 alkyl optionally substituted by hydroxy or phenyl,
R33 is nitro, cyano, C1-6 alkyl optionally substituted by hydroxy or amino, C1-6 alkoxy, hydroxy substituted C1-6 alkyloxy, amino substituted C1-6 alkyloxy, C1-6 alkanoyl, carbamoyl or —NR33aR33b
wherein
R33a is hydrogen or C1-6 alkyl
R33b is hydrogen, C1-6 alkyl optionally substituted by hydroxy or phenyl, C1-6 alkanoyl, C1-6 alkylsulfonyl, or trifluoroacetyl,
R4 is —NH—COR41,
wherein
R41 is C1-6 alkyl optionally substituted by R41a, C1-6 alkoxy, oxotetrahydrofuryl, oxopyrrolidinyl, —CH(OH)R41b, —CH(NH2)R41c, —NHR41c, or piperazino optionally substituted by R41d,
wherein
R41a is carboxy, C1-6 alkoxy, —CH(NH2)carboxy, —NR41a-1R41a-2, or a 3 to 10 membered saturated ring having 0 to 3 heteroatoms selected from the group consisting of O and N, and said ring is optionally substituted by carboxy, C1-6 alkyl optionally substituted by hydroxy or benzodioxane, C3-6 cycloalkyl, C1-6 alkanoyl, carboxy, benzyl, C1-6 alkoxycarbonyl, or furoyl,
wherein
R41a-1 is hydrogen or C1-6 alkyl optionally substituted by hydroxy, C1-6 alkyloxy, C3-8 cycloalkyl, or piperidino,
R41a-2 is hydrogen or C1-6 alkyl optionally substituted by hydroxy, C1-6 alkyloxy or C3-6 cycloalkyl, C1-6 alkoxy or a 3 to 6 membered saturated ring having 0 to 3 heteroatoms selected from the group consisting of O and N, and said ring is optionally substituted by carboxy, C1-6 alkyl, C1-6 alkanoyl, or C1-6 alkyloxy,
R41b is C1-6 alkyl optionally substituted by carboxy or C1-6 alkyloxy, C1-6 alkoxy, or C1-6 alkoxycarbonyl,
R41c is carboxy, C1-6 alkyl optionally substituted by carboxy or a 3 to 6 membered saturated ring having 0 to 3 heteroatoms selected from the group consisting of O and N, or
R41d is C1-6 alkyl optionally substituted by carboxy or C1-6 alkyloxy, or C1-6 alkoxy
R42 is C1-6 alkoxy, carboxy, amino, —CH(NH2)-carboxy or a 5 to 7 membered saturated or unsaturated ring having 0 to 3 heteroatoms selected from the group consisting of O and N, and said ring is optionally substituted by hydroxy, nitro, mono or di halogen, C1-6 alkyl, halogen substituted C1-6 alkyl, amino, mono or di (C1-6 alkyl)amino,or carbamoyl;
R43 is carboxy, amino, —CH(NH2)-carboxy or a 5 to 7 membered saturated or unsaturated ring having 0 to 3 heteroatoms selected from the group consisting of O and N, and said ring is optionally substituted by hydroxy, nitro, mono or di halogen, C1-6 alkyl, halogen substituted C1-6 alkyl, amino, mono or di (C1-6 alkyl)amino, or carbamoyl;
or
R3 and R4 may form, together with the carbon atoms in the benzene ring, a 4 to 6 membered saturated ring having 0 to 3 heteroatoms selected from the group consisting of O and N, and said ring is optionally substituted by one or more substituents selected from the group consisting of hydroxy, nitro, mono or di halogen, C1-6 alkyl, halogen substituted C1-6 alkyl, oxo, amino, mono or di (C1-6 alkyl)amino, and carbamoyl;
R5 is hydrogen, cyano, carboxy, carbamoyl, C1-6 alkyl optionally substituted by hydroxy or carbamoyl, and C1-6 alkoxycarbonyl, and
R6 is amino or acetamido
or
R5 and R6 may form, together with the carbon atoms in the pyridine ring, a 5 to 7 membered saturated or unsaturated ring having 0 to 3 heteroatoms selected from the group consisting of O, S and N, and said ring optionally having substituents selected from the group consisting of halogen, nitro, cyano, oxo, thioxo, C1-6 alkyl, C1-6 alkylsulfonyl, C1-6 alkoxy, C1-6 alkoxycarbonyl, phenyl, C1-6 alkanoyl, amino, C1-6 alkylamino, C1-6 alkanoylamino, carbamoyl, C3-8 cycloalkylaminocarbonyl, C1-6 alkylaminocarbonyl, halogen substituted C1-6 alkylaminocarbonyl, di (C1-6 alkyl)aminocarbonyl, benzoylamino, phenylsulfonyl, di(C1-6 alkyl)aminoC1-6 alkylaminocarbonyl, hydroindenylaminocarbonyl, diphenylmethylaminocarbonyl, pyrrolidinocarbonyl, C1-6 alkyloxy C1-6 alkyl amino carbonyl, morpholinocarbonyl, piperazinocarbonyl, phenylC1-6 alkylaminocarbonyl, carboxyC1-6 alkylaminocarbonyl, C3-8 cycloalkylC1-6 alkylaminocarbonyl, hydroxy C1-6alkylaminocarbonyl, and methylsulfonylaminocarbonyl
or a salt thereof.

### Claim 2 (depends on 1)

The compound or a salt thereof as claimed in claim 1,
wherein
X is CH;
R1 is hydrogen, halogen, C1-6 alkyl, C1-6 alkoxy or C3-6 cycloalkyl substituted C1-6 alkyloxy;
R2 is hydrogen or halogen;
R3 is hydrogen, hydroxy, halogen, C1-6 alkoxy, C3-6 cycloalkyl substituted C1-6alkyloxy, amino, mono or di (C1-6 alkyl)amino, C1-6 alkanoylamino, C1-6 alkyl(hydroxy substituted C1-6 alkyl)amino, C1-6 alkyl(benzyl)amino, morpholino, piperidino, or pyrrolidino optionally substituted by C1-6 alkyl, C1-6 alkyloxy or hydroxy substituted C1-6 alkyl, amino, di(C1-6 alkyl)amino, or trifluoroacetylamino;
R4 is —NH—COR41,
wherein
R41 is C1-6 alkyl optionally substituted by R41a, C1-6 alkoxy, C1-6 alkyloxy substituted C1-6 alkyl, oxotetrahydrofuryl, oxopyrrolidinyl, —CH(OH)R41b, —CH(NH2)R41c, or —NHR41c
wherein
R41a is C1-6 alkoxy, carboxy, —NHR41a-1 (wherein R41a-1 is hydrogen, or C1-6 alkyl optionally substituted by hydroxy, C1-6 alkyloxy, C3-8 cycloalkyl, or piperidino), —CH(NH2)—N(C1-6 alkyl)R41a-2 (wherein R41a-2 is C1-6 alkyl or C1-6 alkyl substituted pyrrolidinyl), pyrrolidinyl, piperidino optionally substituted by carboxy or C1-6 alkoxycarbonyl, piperidino optionally fused with C3-6 cycloalkyl, or piperazino optionally substituted by C1-6 alkyl, hydroxy substituted C1-6 alkyl, benzodioxane substituted C1-6 alkyl, C1-6 alkanoyl, C3-6 cycloalkyl, benzyl, or furoyl,
R41b is C1-6 alkyl optionally substituted by carboxy, or C1-6 alkoxycarbonyl,
R41c is C1-6 alkyl optionally substituted by carboxy or piperidino,
or
R3 and R4 may form, together with the carbon atoms in the benzene ring, a 5 membered saturated ring having 0 to 2 heteroatoms selected from the group consisting of O and N, and said ring is optionally substituted by C1-6 alkyl, or oxo;
R5 is hydrogen, carbamoyl, cyano, carboxy, C1-6 alkoxycarbonyl, or hydroxy substituted C1-6 alkyl; and
R6 is amino or C1-6 alkanoylamino,
or
R5 and R6 may form, together with the carbon atoms in the pyridine ring, a 6 membered saturated or unsaturated ring having 0 to 3 heteroatoms selected from the group consisting of O, S and N, and said ring optionally having substituents selected from the group consisting of halogen, nitro, cyano, oxo, thioxo, C1-6 alkyl, C1-6 alkylsulfonyl, C1-6 alkoxy, C1-6 alkoxycarbonyl, phenyl, C1-6 alkanoyl, amino, C1-6 alkylamino, C1-6 alkanoylamino, carbamoyl, C3-8 cycloalkylaminocarbonyl, C1-6 alkylaminocarbonyl, halogen substituted C1-6 alkylaminocarbonyl, and di (C1-6 alkyl)aminocarbonyl
or a salt thereof.

### Claim 3 (depends on 1)

The compound or a salt thereof as claimed in claim 1,
wherein
X is CH;
R1 is hydrogen, halogen, C1-6 alkoxy, or cyclopropyl methoxy;
R2 is hydrogen;
R3 is hydrogen, hydroxy, halogen, amino, mono or di(C1-6 alkyl)amino, acetamido, C1-6alkoxy, cyclopropyl methoxy, C1-6 alkyl(hydroxy substituted C1-6 alkyl)amino, C1-6 alkyl(benzyl)amino, morpholino, piperidino, or pyrrolidino optionally substituted by C1-6 alkyl, hydroxy substituted C1-6 alkyl, amino, di (C1-6 alkyl)amino, or trifluoroacetylamino;
R4 is —NH—COR41,
wherein
R41 is C1-6 alkyl optionally substituted by R41a, C1-6 alkoxy, oxotetrahydrofuryl, oxopyrrolidinyl, —CH(OH)R41b, or —CH(NH2)R41c,
wherein
R41a is C1-6 alkoxy, carboxy, —CH(NH2)-carboxy, —NHR41a-1 (wherein R41a-1 is hydrogen, C1-6 alkyl optionally substituted by hydroxy, C3-8 cycloalkyl, C1-6 alkoxy, or piperidino), —N(C1-6 alkyl)R41a-2 (wherein R41a-2 is C1-6 alkyl or C1-6 alkyl substituted pyrrolidinyl), pyrrolidinyl, piperidino optionally substituted by carboxy or C1-6 alkoxycarbonyl, piperidino fused with cyclohexane, or piperazino optionally substituted by C1-6 alkyl, hydroxy substituted C1-6 alkyl, benzodioxane substituted C1-6 alkyl, benzyl, C1-6 alkanoyl, cyclohexyl, or furoyl,
R41b is C1-6 alkyl optionally substituted by carboxy or C1-6 alkoxycarbonyl,
R41c is C1-6 alkyl optionally substituted by carboxy,
or
R3 and R4 may form —NR401—CO—O-(wherein R401 is hydrogen or C1-6 alkyl);
R5 is hydrogen, carbamoyl, cyano, carboxy, or hydroxymethyl; and
R6 is amino or acetamido
or
R5 and R6 may form —R50—CH2—NH—, —R50—CO—NH—, —R50—SO2—NH—, or —R50—C(═S)—NH—
wherein
R50 is —CHR501—O—, —CH2—N R501—, —CO—NR501—, (wherein R501 is hydrogen, C1-6 alkyl, C1-6 alkanoyl, C1-6 alkoxycarbonyl, carbamoyl, C1-6 alkylsulfonyl, C3-8 cycloalkylaminocarbonyl, C1-6 alkylaminocarbonyl, di (C1-6 alkyl)aminocarbonyl or phenyl)
or a salt thereof.

### Claim 4 (depends on 1)

The compound as claimed in claim 1 selected from the group consisting of:
5-({3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}amino)-4-hydroxy-5-oxopentanoate;
N-{3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-5-oxotetrahydro-2-furancarboxamide;
N4-{3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-L-asparagine;
N1-{3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-L-asparagine;
N-{3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-3-(1-piperidinyl)propanamide;
5-({4-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}amino)-4-hydroxy-5-oxopentanoate;
5-({5-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-2-chlorophenyl}amino)-4-hydroxy-5-oxopentanoate;
N-{3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-2-[4-(2-furoyl)-1-piperazinyl]acetamide;
N-{3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-3-(4-ethyl-1-piperazinyl)propanamide;
N-{3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-3-octahydro-1(2H)-quinolinylpropanamide;
N1-{3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-N2-cyclopentylglycinamide;
N1-{3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-N2-(cyclopropylmethyl)glycinamide;
N1-{3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-N2-propylglycinamide;
N1-{3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-N2-(3-hydroxypropyl)glycinamide;
N1-{3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-N3-(cyclopropylmethyl)-β-alaninamide;
N1-{3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-N2,N2-dimethylglycinamide;
N-{3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-2-(1-pyrrolidinyl)acetamide;
N1-{3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]phenyl}-N2-[2(methyloxy)ethyl]glycinamide;
N1-[5-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-2-(3-amino-1-pyrrolidinyl)phenyl]-β-alaninamide;
N1-[5-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-2-(1-piperidinyl)phenyl]-β-alaninamide;
N1-[5-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-4-pyridinyl]-2-(1-pyrrolidinyl)phenyl]-β-alaninamide;
N1-{5-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-2-[ethyl(2-hydroxyethyl)amino]phenyl}-β-alaninamide;
N1-[5-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-2-(4-morpholinyl)phenyl]-β-alaninamide;
N1-[5-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-2-(dimethylamino)phenyl]-β-alaninamide;
N-{3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-4-chlorophenyl}-3-(1-piperidinyl)propanamide;
N1-{5-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-2-chlorophenyl}-N2-(cyclopropylmethyl)glycinamide;
N1-{5-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-2-chlorophenyl}-N2-(2-methoxyethyl)glycinamide;
N1-{5-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-2-chlorophenyl}-β-alaninamide;
N-{4-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-2-hydroxyphenyl}acetamide;
N-{5-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-2-chlorophenyl}-3-(1-piperidinyl)propanamide;
N1-[5-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-2-(dimethylamino)phenyl]-N2-(cyclopropylmethyl)glycinamide;
N-[5-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-2-(dimethylamino)phenyl]-3-(1-piperidinyl)propanamide;
N1-{5-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-2-[(2S)-2-(hydroxymethyl)-1-pyrrolidinyl]phenyl}-L-leucinamide;
N1-{5-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-2-[(3S)-3-(dimethylamino)-1-pyrrolidinyl]phenyl}-N2-(cyclopropylmethyl)glycinamide;
N1-(5-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-2-{3-[(trifluoroacetyl)amino]-1-pyrrolidinyl}phenyl)-L-leucinamide;
N-(5-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-2-{3-[(trifluoroacetyl)amino]-1-pyrrolidinyl}phenyl)-3-(1-piperidinyl)propanamide;
N1-(5-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-2-{3-[(trifluoroacetyl)amino]-1-pyrrolidinyl}phenyl)-N2-(2-methoxyethyl)glycinamide;
N1-(5-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-2-{3-[(trifluoroacetyl)amino]-1-pyrrolidinyl}phenyl)-N2-(cyclopropylmethyl)glycinamide;
N-{4-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-2-[2-(1-piperidinyl)ethoxy]phenyl}acetamide;
N-{4-[2-amino-3-(hydroxymethyl)-6-(2-hydroxyphenyl)-4-pyridinyl]-2-hydroxyphenyl}acetamide;
N-{4-[2-amino-6-[2-(cyclopropylmethoxy)-6-hydroxyphenyl]-3-(hydroxymethyl)-4-pyridinyl]-2-hydroxyphenyl}acetamide; and
7-[2-(cyclopropylmethoxy)-6-hydroxyphenyl]-5-(3-ethyl-2-oxo-2,3-dihydro-1,3-benzoxazol-6-yl)-1,4-dihydro-2H-pyrido[2,3-d][1,3]oxazin-2-one.

### Claim 5 (depends on 1)

A pharmaceutical composition comprising the compound or a salt thereof as claimed in claim 1 as an active ingredient.

### Claim 6 (depends on 1)

A pharmaceutical composition comprising the compound or a salt thereof as claimed in claim 1 together with one or more pharmaceutically acceptable excipients.

### Claim 7 (depends on 1)

A method of treating an inflammatory disease in a subiect comprising administering to a subject in need thereof, a therapeutically effective amount of one or more compounds of claim 1, wherein the disease is asthma, allergic rhinitis, atopic dermatitis, hives, conjunctivitis, vernal catarrh, chronic arthrorheumatism, systemic lupus erythematosus, psoriasis, diabrotic colitis, systemic inflammatory response syndrome, sepsis, polymyositis, dermatomyositis, polyarthritis nodosa, mixed connective tissue disease, Sjoegren's syndrome, or gout.

### Claim 8 (depends on 1)

A method of treating ischemia in a subject comprising administering to a subject in need thereof, a therapeutically effective amount of one or more compounds of claim 1.

### Claim 9 (depends on 1)

A method of treating a tumor in a subject comprising administering to a subject in need thereof, a therapeutically effective amount of one or more compounds of claim 1, wherein the tumor is a colorectal cancer tumor.