IP Library › Granted Patent US 6,852,717
Granted Patent B2
US 6,852,717 · App. 10/143,322 · Granted Feb 8, 2005

Compounds useful as anti-inflammatory agents

Assignee: Boehringer Ingelheim Pharmaceuticals, Inc.
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Quick Facts
Patent No.
US 6,852,717
App. No.
10/143,322
Granted
Feb 8, 2005
Kind
B2
Abstract

Disclosed are compounds useful in pharmaceutic compositions for treating diseases or pathological conditions involving inflammation such as chronic inflammatory diseases. Also disclosed are processes of making such compounds.

Claims (151)

1. A compound selected from the group consisting of:

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(2-isopropyl-6-methyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(2,6-dimethyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

1-(5-tert-Butyl-2-methoxy-3-[1,2,4]triazol-4-yl-phenyl)-3-[4-(pyrimidin-4-yloxy)-naphthalan-1-yl]-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(2-oxo-2H-pyran-4-yloxy)-naphthalen-1-yl]-urea;

5-tert-Butyl-2-methoxy-3-{3-[4-(6-morpholin-4-ylmethyl-pyridin-3-yl)-naphthalen-1-yl]-ureido}-benzoic acid;

Carbonic acid 5-tert-butyl-2-methoxy-3-{3-[4-(6-morpholin-4-ylmethyl-pyridin-3-yl)-naphthalen-1-yl]-ureido}-phenyl ester methyl ester;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(4-isopropylamino-[1,3,5]triazin-2-yloxy)-naphthalen-1-yl]-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[4-(cyclopropylmethyl-amino)-[1,3,5]triazin-2-yloxy]-naphthalen-1-yl}-urea;

1-[4-(4-Amino-[1,3,5]triazin-2-yloxy)-naphthalen-1-yl]-3-(5-tert-butyl-2-methoxy-phenyl)-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-([1,3,5]triazin-2-yloxy)-naphthalen-1-yl]-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(2-cyclopropylamino-6-methyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(2-methylamino-pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(2-ethylamino-pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(6-methyl-2-methylamino-pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

1-[4-(2-Amino-6-methyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-3-(5-tert-butyl-2-methoxy-phenyl)-urea;

1-[4-(2-Amino-pyrimidin-4-yloxy)-naphthalen-1-yl]-3-(5-tert-butyl-2-methoxy-phenyl)-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(2-cyclopentylamino-pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[2-(cyclopropylmethyl-amino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[2-(cyclopropylmethyl-amino)-6-methyl-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-(4-{2-[(tetrahydro-furan-2-ylmethyl)-amino]-pyrimidin-4-yloxy}-naphthalen-1-yl)-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-(4-{2-[(pyridin-2-ylmethyl)-amino]-pyrimidin-4-yloxy}-naphthalen-1-yl)-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[2-(2-morpholin-4-yl-ethylamino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

1-[4-(2-Benzylamino-pyrimidin-4-yloxy)-naphthalen-1-yl]-3-(5-tert-butyl-2-methoxy-phenyl)-urea;

1-[4-(2-sec-Butylamino-pyrimidin-4-yloxy)-naphthalen-1-yl]-3-(5-tert-butyl-2-methoxy-phenyl)-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[2-(2-methoxy-ethylamino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[2-(2-dimethylamino-ethylamino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(2-dimethylamino-pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(2-pyrrolidin-1-yl-pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(6-methyl-2-pyrrolidin-1-yl-pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(2-morpholin-4-yl-pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[2-(4-methyl-piperazin-1-yl)-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(2-ethoxy-pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[2-(2-morpholin-4-yl-ethoxy)-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[2-(2-dimethylamino-ethoxy)-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

1-[4-(2-Benzylamino-pyrimidin-4-yloxy)-naphthalen-1-yl]-3-(5-tert-butyl-2-methoxy-3-[1,2,4]triazol-4-yl-phenyl)-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(2-methanesulfinyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(2-methylsulfanyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

1-(2-Methoxy-5-trimethylsilanyl-phenyl)-3-[4-(6-morpholin-4-ylmethyl-pyridin-3-yl)-naphthalen-1-yl]-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[2-(2-methoxy-phenyl)-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[2-(3-methoxy-phenyl)-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(2-phenyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

4-{4-[3-(5-tert-Butyl-2-methoxy-phenyl)-ureido]-naphthalen-1-yloxy}-pyrimidine-2-carboxylic acid methyl ester;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(2-cyano-pyrimidin-4-yloxy)-naphthalen-1-yl]-urea; and

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(tetrahydro-pyran-4-yloxy)-naphthalen-1-yl]-urea

or the pharmaceutically acceptable salts thereof.

2. A compound selected from the group consisting of:

1-[5tert-Butyl-3-(1,1-dioxo-1-lambda-6-isothiazolidin-2-yl)-2-methoxy-phenyl]-3-[4-(6-morpholin-4-ylmethyl-pyridin-3-yl)-naphthalen-1-yl]-urea;

N-(3-{3-[4-(2-Amino-6-methyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-ureido}-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide;

N-(3-{3-[4-(2-Amino-pyrimidin-4-yloxy)-naphthalen-1-yl]-ureido}-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide;

N-(5-tert-Butyl-3-{3-[4-(2-cyano-pyrimidin-4-yloxy)-naphthalen-1-yl]-ureido}-2-methoxy-phenyl)-methanesulfonamide;

N-(5-tert-Butyl-2-methoxy-3-{3-[4-(tetrahydropyran-4-yloxy)-naphthalen-1-yl]-ureido}-phenyl)-methanesulfonamide

N-(5-tert-Butyl-2-methoxy-3-{3-[4-(pyrimidin-4-yloxy)-naphthalen-1-yl]-ureido}-phenyl)-methanesulfonamide;

N-(5-tert-Butyl-2-methoxy-3-{3-[4-(2-methylamino-pyrimidin-4-yloxy)-naphthalen-1-yl]-ureido}-phenyl)-methanesulfonamide;

N-(5-tert-Butyl-2-methoxy-3-{3-[4-(6-methyl-2-methylamino-pyrimidin-4-yloxy)-naphthalen-1-yl]-ureido}-phenyl)-methanesulfonamide;

N-[5-tert-Butyl-3-(3-{4-[2-(cyclopropylmethyl-amino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-ureido)-2-methoxy-phenyl]-methanesulfonamide;

N-[5-tert-Butyl-3-(3-{4-[2-(cyclopropylmethyl-amino)-6-methyl-pyrimidin-4-yloxy]-naphthalen-1-yl}-ureido)-2-methoxy-phenyl]-methanesulfonamide;

N-{5-tert-Butyl-2-methoxy-3-[3-(4-{2-[(tetrahydro-furan-2-ylmethyl)-amino]-pyrimidin-4-yloxy}-naphthalen-1-yl)-ureido]-phenyl}-methanesulfonamide; and

N-(5-tert-Butyl-2-methoxy-3-{3-[4-(2-pyrrolidin-1-yl-pyrimidin-4-yloxy)-naphthalen-1-yl]-ureido}-phenyl)-methanesulfonamide

or the pharmaceutically acceptable salts thereof.

3. A compound selected from the group consisting of:

1-[5-tert-butyl-2-(2-hydroxy-4-methyl-phenyl)-2H-pyrazol-3-yl]-3-[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-urea;

1-[5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl]-3-{4-[2-(hydroxy)ethoxy]-naphthalen-1-yl}-urea;

1-[5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl]-3-{4-[2-oxo-2-(morpholin-4-yl)-ethoxy]-naphthalen-1-yl}-urea; and

1-[5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl]-3-{4-[hydroxy]-naphthalen-1-yl}-urea

or the pharmaceutically acceptable salts thereof.

4. A compound selected from the group consisting of:

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(2-isopropylamino-pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(2-cyclopropylamino-pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[2-(1-phenyl-ethylamino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-(4-{2-[pyridin-3-ylmethyl)-amino]-pyrimidin-4-yloxy}-naphthalen-1-yl)-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-(4-{2-[pyridin-4-ylmethyl)-amino]-pyrimidin-4-yloxy}-naphthalen-1-yl)-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-(4-{2-[2-(4-methyl-piperazin-1-yl)-ethylamino]-pyrimidin-4-yloxy}-naphthalen-1-yl)-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[2-(2-pyrrolidin-1-yl-ethylamino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[2-(2-oxo-tetrahydro-furan-3-ylamino)-pyrimidine-4-yloxy]-naphthalen-1-yl}-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[2-(tetrahydro-furan-3-ylamino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-(4-{6-methyl-2-[(tetrahydro-furan-2-ylmethyl)-amino]-pyrimidin-4-yloxy}-naphthalen-1-yl)-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[2-(2-methoxy-1-methyl-ethylamino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

2-(4-{4-[3-(5-tert-Butyl-2-methoxy-phenyl)-ureido]-naphthalen-1-yloxy}-pyrimidin-2-ylamino)-propionamide;

2-(4-{4-[3-(5-tert-Butyl-2-methoxy-phenyl)-ureido]-naphthalen-1-yloxy}-pyrimidin-2-ylamino)-N-methyl-propionamide;

2-(4-{4-[3-(5-tert-Butyl-2-methoxy-phenyl)-ureido]-naphthalen-1-yloxy}-pyrimidin-2-ylamino)-N,N-dimethyl-propionamide;

2-(4-{4-[3-(5-tert-Butyl-2-methoxy-phenyl)-ureido]-naphthalen-1-yloxy}-pyrimidin-2-ylamino)-N,N-dimethyl-acetamide

1-(5-tert-Butyl-2-methoxy-phenyl)-3-(4-{2-[1-(3-methoxy-phenyl)-ethylamino]-pyrimidin-4-yloxy}-naphthalen-1-yl)-urea;

1-(4-{2-[1-(2-Bromo-phenyl)-ethylamino]-pyrimidin-4-yloxy}-naphthalen-1-yl)-3-(5-tert-butyl-2-methoxy-phenyl)-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[2-(4-diethylamino-1-methyl-butylamino)-pyrimidine-4-yloxy]-naphthalen-1-yl}-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[2-(4-methoxy-benzylamino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[2-(3-chloro-benzylamino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

1-{4-[2-(Benzyl-methyl-amino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-3-(5-tert-butyl-2-methoxy-phenyl)-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-(4-{2-[(2-dimethylamino-ethyl)-methyl-amino]-pyrimidin-4-yloxy}-naphthalen-1-yl)-urea;

1-[4-(2-Benzylamino-6-methyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-3-(5-tert-butyl-2-methoxy-phenyl)-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[6-methyl-2-(1-phenyl-ethylamino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-(4-{6-methyl-2-[(pyridin-2-ylmethyl)-amino]-pyrimidin-4-yloxy}-naphthalen-1-yl)-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[2-(2-dimethylamino-ethylamino)-6-methyl-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[6-methyl-2-(2-morpholin-4-yl-ethylamino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-[4-(2-dimethylamino-6-methyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

N-(5-tert-Butyl-2-methoxy-3-{3-[4-(2-morpholin-4-yl-pyrimidin-4-yloxy)-naphthalen-1-yl]-ureido}-phenyl)-methanesulfonamide;

N-[5-tert-Butyl-2-methoxy-3-(3-{4-[2-(1-phenyl-ethylamino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-ureido)-phenyl]-methanesulfonamide;

N-[5-tert-Butyl-2-methoxy-3-(3-{4-[6-methyl-2-(1-phenyl-ethylamino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-ureido)-phenyl]-methanesulfonamide;

N-{5-tert-Butyl-2-methoxy-3-[3-(4-{2-[(pyridin-3-ylmethyl)-amino]-pyrimidin-4-yloxy}-naphthalen-1-yl)-ureido]-phenyl}-methanesulfonamide;

N-[5-tert-Butyl-3-(3-{4-[2-(2-dimethylamino-ethylamino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-ureido)-2-methoxy-phenyl]-methanesulfonamide;

N-[5-tert-Butyl-3-(3-{4-[2-(2-dimethylamino-ethylamino)-6-methyl-pyrimidin-4-yloxy]-naphthalen-1-yl}-ureido)-2-methoxy-phenyl]-methanesulfonamide;

N-[5-tert-Butyl-2-methoxy-3-(3-{4-[2-(2-morpholin-4-yl-ethylamino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-ureido)-phenyl]-methanesulfonamide;

N-[5-tert-Butyl-2-methoxy-3-(3-{4-[6-methyl-2-(2-morpholin-4-yl-ethylamino)-pyrimidine-4-yloxy]-naphthalen-1-yl}-ureido)-phenyl]-methanesulfonamide;

N-(5-tert-Butyl-3-{3-[4-(2-dimethylamino-pyrimidin-4-yloxy)-naphthalen-1-yl]-ureido}-2-methoxy-phenyl)-methanesulfonamide;

N-[5-tert-Butyl-2-methoxy-3-(3-{4-[2-(4-methyl-piperazin-1-yl)-pyrimidin-4-yloxy]-naphthalen-1-yl}-ureido)-phenyl]-methanesulfonamide;

N-(5-tert-Butyl-2-methoxy-3-{3-[4-(2-piperidin-1-yl-pyrimidin-4-yloxy)-naphthalen-1-yl]-ureido}-phenyl)-methanesulfonamide;

N-{5-tert-Butyl-3-[3-(4-{2-[(2-dimethylamino-ethyl)-methyl-amino]-pyrimidin-4-yloxy}-naphthalen-1-yl)-ureido]-2-methoxy-phenyl}-methanesulfonamide;

N-[5-tert-Butyl-2-methoxy-3-(3-{4-[2-(tetrahydrofuran-3-ylamino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-ureido)-phenyl]-methanesulfonamide;

N-[5-tert-Butyl-2-methoxy-3-(3-{4-[2-(2-methoxy-1-methyl-ethylamino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-ureido)-phenyl]-methanesulfonamide;

2-(4-{4-[3-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-ureido]-naphthalen-1-yloxy}-pyrimidin-2-ylamino)-N-methyl-propionamide;

2-(4-{4-[3-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-ureido]-naphthalen-1-yloxy}-pyrimidin-2-ylamino)-N,N-dimethyl-propionamide;

N-{5-tert-Butyl-2-methoxy-3-[3-(4-{2-[(pyridin-2-ylmethyl)-amino]-pyrimidin-4-yloxy}-naphthalen-1-yl)-ureido]-phenyl}-methanesulfonamide;

N-{5-tert-Butyl-2-methoxy-3-[3-(4-{6-methyl-2-[(tetrahydro-furan-2-ylmethyl)-amino]-pyrimidin-4-yloxy}-naphthalen-1-yl)-ureido]-phenyl}-methanesulfonamide;

N-(5-tert-Butyl-2-methoxy-3-{3-[4-(6-methyl-2-pyrrolidin-1-yl-pyrimidin-4-yloxy)-naphthalen-1-yl]-ureido}-phenyl)-methanesulfonamide;

2-(5-tert-Butyl-2-methoxy-3-{3-[4-(pyridin-4-yloxy)-naphthalen-1-yl]-ureido}-phenylamino)-thiazole-4-carboxylic acid ethyl ester;

2-(5-tert-Butyl-2-methoxy-3-{3-[4-(2-pyrrolidin-1-ylmethyl-pyridin-4-yloxy)-naphthalen-1-yl]-ureido}-phenylamino)-thiazole-4-carboxylic acid ethyl ester;

2-[5-tert-Butyl-2-methoxy-3-(3-{4-[2-(pyrrolidine-1-carbonyl)-pyridin-4-yloxy]-naphthalen-1-yl}-ureido)-phenylamino]-thiazole-4-carboxylic acid ethyl ester;

2-(5-tert-Butyl-2-methoxy-3-{3-[4-(2-methylaminomethyl-pyridin-4-yloxy)-naphthalen-1-yl]-ureido }-phenylamino)-thiazole-4-carboxylic acid ethyl ester;

2-(5-tert-Butyl-2-methoxy-3-{3-[4-(2-methylcarbamoyl-pyridin-4-yloxy)-naphthalen-1-yl]-ureido}-phenylamino)-thiazole-4-carboxylic acid ethyl ester;

2-(5-tert-Butyl-2-methoxy-3-{3-[4-(2-methylamino-pyridin-4-yloxy)-naphthalen-1-yl]-ureido}-phenylamino)-thiazole-4-carboxylic acid ethyl ester;

1-{5-tert-Butyl-2-methoxy-3-[4-(pyrrolidine-1-carbonyl)-thiazol-2-ylamino]-phenyl}-3-[4-(pyridin-4-yloxy)-naphthalen-1-yl]-urea;

1-[5-tert-Butyl-2-methoxy-3-(4-pyrrolidin-1-ylmethyl-thiazol-2-ylamino)-phenyl]-3-[4-(pyridin-4-yloxy)-naphthalen-1-yl]-urea;

2-(5-tert-Butyl-2-methoxy-3-{3-[4-(pyrimidin-4-yloxy)-naphthalen-1-yl]-ureido}-phenylamino)-thiazole-4-carboxylic acid ethyl ester;

2-(3-{3-[4-(2-Amino-pyrimidin-4-yloxy)-naphthalen-1-yl]-ureido}-5-tert-butyl-2-methoxy-phenylamino)-thiazole-4-carboxylic acid ethyl ester;

2-(5-tert-Butyl-2-methoxy-3-{3-[4-(2-methylamino-pyrimidin-4-yloxy)-naphthalen-1-yl]-ureido}-phenylamino)-thiazole-4-carboxylic acid ethyl ester;

2-[5-tert-Butyl-3-(3-{4-[2-(cyclopropylmethyl-amino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-ureido)-2-methoxy-phenylamino]-thiazole-4-carboxylic acid ethyl ester;

2-(5-tert-Butyl-2-methoxy-3-{3-[4-(pyrimidin-4-yloxy)-naphthalen-1-yl]-ureido}-phenylamino)-thiazole-4-carboxylic acid (2-dimethylamino-ethyl)-methyl-amide;

1-{5-tert-Butyl-2-methoxy-3-[4-(pyrrolidine-1-carbonyl)-thiazol-2-ylamino]-phenyl}-3-[4-(pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

1-[5-tert-Butyl-2-methoxy-3-(4-pyrrolidin-1-ylmethyl-thiazol-2-ylamino)-phenyl]-3-[4-(pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

1-[5-tert-Butyl-2-methoxy-3-(4-pyrrolidin-1-ylmethyl-thiazol-2-ylamino)-phenyl]-3-[4-(2-isopropylamino-pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

1-{5-tert-Butyl-2-methoxy-3-[4-(pyrrolidine-1-carbonyl)-thiazol-2-ylamino]-phenyl}-3-{4-[2-(cyclopropylmethyl-amino)-6-methyl-pyrimidin-4-yloxy]-naphthalen-1-yl }-urea;

1-[5-tert-Butyl-2-methoxy-3-(4-pyrrolidin-1-ylmethyl-thiazol-2-ylamino)-phenyl]-3-{4-[2-(cyclopropylmethyl-amino)-6-methyl-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

1-[5-tert-Butyl-3-(3-dimethylamino-pyrrolidin-1-ylmethyl)-2-methoxy-phenyl]-3-[4-(pyridin-4-yloxy)-naphthalen-1-yl]-urea;

1-[5-tert-Butyl-3-(3-dimethylaminomethyl)-2-methoxy-phenyl]-3-[4-(pyridin-4-yloxy)-naphthalen-1-yl]-urea;

1-[5-tert-Butyl-3-(3-dimethylamino-pyrrolidin-1-ylmethyl)-2-methoxy-phenyl]-3-[4-(2-dimethylaminomethyl-pyridin-4-yloxy)-naphthalen-1-yl]-urea;

1-[5-tert-Butyl-3-(3-dimethylamino-pyrrolidin-1-ylmethyl)-2-methoxy-phenyl]-3-[4-(pyrimidin-4-yloxy)-naphthalen-1-yl]-urea;

1-[4-(2-Amino-pyrimidin-4-yloxy)-naphthalen-1-yl]-3-[5-tert-butyl-3-(3-dimethylamino-pyrrolidin-1-ylmethyl)-2-methoxy-phenyl]-urea;

1-[4-(2-Amino-6-methyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-3-[5-tert-butyl-3-(3-dimethylamino-pyrrolidin-1-ylmethyl)-2-methoxy-phenyl]-urea;

1-(5-tert-Butyl-3-dimethylaminomethyl-2-methoxy-phenyl)-3-{4-[2-(cyclopropylmethyl-amino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

1-(5-tert-Butyl-3-dimethylaminomethyl-2-methoxy-phenyl)-3-{4-[2-(cyclopropylmethyl-amino)-6-methyl-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

N-[5-tert-Butyl-2-methoxy-3-(3-{4-[2-(2-methoxy-phenyl)-pyrimidin-4-yloxy]-naphthalen-1-yl}-ureido)-phenyl]-methanesulfonamide;

4-{4-[3-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenyl)-ureido]-naphthalen-1-yloxy}-pyrimidine-2-carboxylic acid methyl ester;

1-[4-(2-Acetyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-3-(5-tert-butyl-2-methoxy-phenyl)-urea;

N-(3-{3-[4-(2-Acetyl-pyrimidin-4-yloxy)-naphthalen-1-yl]-ureido}-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide;

1-(5-tert-Butyl-2-methoxy-phenyl)-3-{4-[2-(1-pyrrolidin-1-yl-ethyl)-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea;

N-[5-tert-Butyl-2-methoxy-3-(3-{4-[2-(1-pyrrolidin-1-yl-ethyl)-pyrimidin-4-yloxy]-naphthalen-1-yl}-ureido)-phenyl]-methanesulfonamide; and

1-(2-methoxy-5-trimethylsilanyl-phenyl)-3-{4-[2-(cyclopropylmethyl-amino)-pyrimidin-4-yloxy]-naphthalen-1-yl}-urea

or the pharmaceutically acceptable salts thereof.

5. A pharmaceutical composition comprising a pharmaceutically effective amount of a compound according to claim 1 , 2 , 3 or 4 .

6. A method of treating a disease or condition selected from rheumatoid arthritis, Crohn's disease and ulcerative colitis comprising administering to a patient a therapeutically effective amount of a compound according to claim 1 , 2 , 3 or 4 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 10, 2002
From: CIRILLO, PIER F.; GOLDBERG, , DANIEL R.; HAMMACH, ABDELHAKIM; MOSS, NEIL; REGAN, JOHN ROBINSON
To: BOEHRINGER INGELHEIM PHARMACEUTICALS, INC.
Reel/Frame 012900/0624 →
Continuity (2)
Provisional Application 6029142500 · May 16, 2001
Related Publication 20030008868A1 · Jan 9, 2003