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US 7,030,112 B2Granted
Pyrrolopyridazine compounds and methods of use thereof for the treatment of proliferative disorders
AssigneeBristol-Myers Squibb Company
InventorsMark E. Salvati, Carl R. Illig, Kenneth Jerome Wilson, Jinsheng Chen, Sanath K. Meegalla, Mark James Wall
Life of this patent
Estimating the term…
Abstract
Disclosed are pyrrolopyridazine compounds of the formula, wherein the substituents are defined herein, methods of preparing such compounds, and their use for the treatment of proliferative, inflammatory, and other disorders.
Claims2
A compound selected from the group consisting of
- 3-Cyano-4-[4-(cyano-phenyl-methyl)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 2-[3-Cyano-6-ethoxycarbonyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-5-ylmethyl]-malonic acid diethyl ester,
- 5-Methyl-4-(4-phenoxy-phenylamino)-6-phenylamino-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 3-Cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid (2-amino-phenyl)-amide,
- 6-(1H-Benzoimidazol-2-yl)-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- N-[3-Cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-yl]-2-fluoro-benzamide,
- 5-Methyl-6-(2-methyl-4-oxo-4H-quinazolin-3-yl)-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 6-Benzylamino-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- N-[3-Cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-yl]-benzenesulfonamide,
- 6-[bis(phenylsulfonyl)amino]-5-methyl-4-[(4-phenoxyphenyl)amino]-7a-hydropyrrolo[1,2-e]pyridazine-3-carbonitrile,
- 6-(Benzothiazol-2-ylamino)-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- {4-[4-(6-Chloro-pyridazin-3-yloxy)-phenylamino]-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-carbamic acid 2-morpholin-4-yl-ethyl ester,
- {3-Cyano-5-methyl-4-[4-(1-phenyl-1H-tetrazol-5-yloxy)-phenylamino]-pyrrolo[1,2-b]pyridazin-6-yl}-carbamic acid 2-morpholin-4-yl-ethyl ester,
- {3-Cyano-5-methyl-4-[4-(2-nitro-phenoxy)-phenylamino]-pyrrolo[1,2-b]pyridazin-6-yl}-carbamic acid 2-morpholin-4-yl-ethyl ester,
- {4-[4-(2-Amino-phenoxy)-phenylamino]-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-carbamic acid 2-morpholin-4-yl-ethyl ester,
- {4-[4-(2-Acetylamino-phenoxy)-phenylamino]-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-carbamic acid 2-morpholin-4-yl-ethyl ester,
- 5-Methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- [4-(4-Bromo-phenylamino)-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl]-carbamic acid 2-morpholin-4-yl-ethyl ester,
- {3-Cyano-4-[4-(2,2-dimethyl-3-oxo-2,3-dihydro-benzofuran-7-yloxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-carbamic acid 2-morpholin-4-yl-ethyl ester,
- 4-(4-{2-[1-(tert-Butoxycarbonylmethyl-carbamoyl)-1-methyl-ethoxy]-phenoxy}-phenylamino)-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester,
- 4-(4-{2-[1-(Carboxymethyl-carbamoyl)-1-methyl-ethoxy]-phenoxy}-phenylamino)-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester,
- 3-Cyano-4-(4-{2-[1-(ethylcarbamoylmethyl-carbamoyl)-1-methyl-ethoxy]-phenoxy}-phenylamino)-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester,
- 4-(1-Benzyl-piperidin-4-ylamino)-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester,
- 3-Cyano-5-methyl-4-(4-phenoxy-benzenesulfonyl)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethylester,
- 3-Cyano-5-methoxy-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 3-Cyano-5-methyl-4-[4-phenoxy-3-(tetrahydro-pyran-2-yloxymethyl)-phenylamino]-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 3-Cyano-4-(3-hydroxymethyl-4-phenoxy-phenylamino)-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 6-(1-Hydroxy-1-methyl-ethyl)-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- Trifluoro-methanesulfonic acid 3-cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-yl ester,
- 6-(1-Hydroxy-1methyl-ethyl)-5-methoxy-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 6-Hydroxy-5-methoxy-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 5,6-Dimethoxy-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 6-(4-Methoxy-phenyl)-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 5-Methyl-4-(4-phenoxy-phenylamino)-6-phenyl-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 3-Cyano-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 7-Bromo-3-cyano-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 7-Chloro-3-cyano-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 3-Cyano-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-7-carboxylic acid ethyl ester,
- 7-Hydroxymethyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 3-Cyano-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-7-carboxylic acid,
- 3-Cyano-5,7-dimethyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 5-Methyl-6-(4-methyl-piperazin-1-ylmethyl)-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile
- [3-Cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-ylmethoxy]-acetic acid ethylester,
- 3-cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carbonyl-N-hydroxylacetamidine,
- 6-(Hydroxyimino-methyl)-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- N-Benzyl-N-[3-cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-ylmethyl]-acetamide,
- N-[3-Cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-yl]-methanesulfonamide,
- 5-Methyl-6-(3-methyl-[1,2,4]oxadiazol-5-yl)-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 3-Cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methoxy-methyl-amide,
- 5-Methyl-4-(4-phenoxy-phenylamino)-6-propynoyl-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 3-cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carbonyl-N-hydroxymorpholinyl-acetamidine,
- 5-Methyl-6-(3-morpholin-4-yl-[1,2,4]oxadiazol-5-yl)-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 6-(3-Methanesulfonylmethyl-[1,2,4]oxadiazol-5-yl)-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 3-(Imino-hydrazino-methyl)-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 5-Methyl-4-(4-phenoxy-phenylamino)-6-(4-phenyl-thiazol-2-yl)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 6-(4,5-Dihydro-1H-imidazol-2-ylamino)-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 6-(2-Amino-4-hydroxy-4,5-dihydro-thiazol-4-ylamino)-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 4-[3-Chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)-phenylamino]-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ether ester,
- 3-Cyano-4-[2-fluoro-4-(thiazol-2-yloxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 1-{4-[3-Chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)-phenylamino]-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-3-(2-morpholin-4-yl-ethyl)-urea,
- 3-Cyano-5-methyl-4-(5-phenoxy-pyridin-2-ylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 3-Acetylamino-N-{3-cyano-4-[5-(2-methoxy-phenoxy)-pyridin-2-ylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-benzamide,
- 3-Acetylamino-N-{3-cyano-4-[5-(2-methoxy-phenoxy)-pyridin-2-ylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-benzamide,
- {3-Cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-methyl-carbamic acid 2-morpholin-4-yl-ethyl ester,
- [3-Cyano-4-(4-{2-[1-(2-hydroxy-ethylcarbamoyl)-1-methoxy-ethoxy]-phenoxy}-phenylamino)-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl]-carbamic acid 2-morpholin-4-yl-ethyl ester,
- N-{3-Cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-3-methanesulfonylamino-benzamide,
- 5-Methyl-6-morpholin-4-ylmethyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 1-{3-Cyano-4-[2-fluoro-4-(thiazol-2-yloxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-3-(2-morpholin-4-yl-ethyl)-urea,
- 3-Cyano-4-(4-{2-[1-(2-hydroxy-ethylcarbamoyl)-1-methyl-ethoxy]-phenoxy}-phenylamino)-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- {4-[3-Chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)-phenylamino]-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-carbamic acid 2-morpholin-4-yl-ethyl ester,
- 3-Cyano-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid,
- {3-Cyano-4-[2-fluoro-4-(thiazol-2-yloxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-carbamic acid 2-morpholin-4-yl-ethyl ester,
- 3-Cyano-5-methyl-4-(2-methyl-4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 3-Cyano-4-(2-fluoro-4-phenoxy-phenylamino)-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 3-Cyano-4-(4-{2-[1-(2-hydroxy-ethylcarbamoyl)-1-methyl-ethoxy]-phenoxy}-phenylamino)-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 3-Cyano-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-7-carboxylic acid,
- 4-[3-Chloro-4-(1-methyl-1H-imidazol-2-ylsulfanyl)-phenylamino]-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid (2-morpholin-4-yl-ethyl)-amide,
- 4-(5-Bromo-pyridin-2-ylamino)-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester,
- [3-Cyano-4-(4-{2-[1-(2-hydroxy-ethylcarbamoyl)-1-methyl-ethoxy]-phenoxy}-phenylamino)-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl]-carbamic acid 2-morpholin-4-yl-ethyl ester,
- 3-Cyano-4-(4-hydroxy-cyclohexylamino)-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 4-(7-Aza-bicyclo[2.2.1]hept-7-yl)-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 4-(4-tert-Butoxycarbonyl-piperazin-1-yl)-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 3-Cyano-5-methyl-4-piperazin-1-yl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 4-(4-Benzoyl-piperazin-1-yl)-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 4-(1-tert-Butoxycarbonyl-piperidin-4-ylamino)-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 3-Cyano-4-(4-methanesulfonyl-piperazin-1-yl)-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 3-Cyano-5-methyl-4-(piperidin-4-ylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 4-(1-Acetyl-piperidin-4-ylamino)-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 6-Formyl-7-iodo-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- [3-Cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-yl]-carbamic acid 4-methanesulfonyl-butyl ester,
- 3-Cyano-4-(4-{3-[1-(2-hydroxy-ethylcarbamoyl)-1-methyl-ethoxy]-phenoxy}-phenylamino)-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- [3-Cyano-4-(4-{3-[1-(2-hydroxy-ethylcarbamoyl)-1-methyl-ethoxy]-phenoxy}-phenylamino)-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl]-carbamic acid 2-morpholin-4-yl-ethyl ester,
- 4-{4-[2-(1-tert-Butoxycarbonyl-1-methyl-ethoxy)-phenoxy]-phenylamino}-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester,
- 4-{4-[2-(1-Carboxy-1-methyl-ethoxy)-phenoxy]-phenylamino}-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester,
- 3-Acetylamino-N-[3-cyano-4-(4-{3-[1-(2-hydroxy-ethylcarbamoyl)-1-methyl-ethoxy]-phenoxy}-phenylamino)-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl]-benzamide,
- 3-Cyano-4-(4-{2-[1-(ethylcarbamoylmethyl-carbamoyl)-1-methyl-ethoxy]-phenoxy}-phenylamino)-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester,
- 3-Cyano-4-(4-{2-[1-(ethoxycarbonylmethyl-carbamoyl)-1-methyl-ethoxy]-phenoxy}-phenylamino)-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester,
- 3-Cyano-5-methyl-4-[4-phenoxy-3-(2,2,2-trifluoro-acetoxymethyl)-phenylamino]-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 5-Amino-3-cyano-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 4-(4-{2-[1-(tert-Butoxycarbonylmethyl-carbamoyl)-1-methyl-ethoxy]-phenoxy}-phenylamino)-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester,
- 6-Hydroxy-5-methoxy-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 7-Chloro-3-cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester,
- 7-Bromo-3-cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester,
- 3-Cyano-4-{4-[2-(2,3-dihydroxy-propoxy)-phenoxy]-phenylamino}-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester,
- 3-Cyano-5-methyl-4-(4-phenoxy-benzoylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester,
- 3-Cyano-5-methyl-4-(4-phenoxy-benzenesulfonylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 6-{3-[2-(1,1-Dioxo-1l6-thiomorpholin-4-yl)-ethyl]-2-oxo-imidazoline-1-carbonyl]-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 3-Cyano-5-methyl-4-[4-(pyridin-2-yloxy)-phenylamino]-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 3-Cyano-5-methyl-4-[4-(pyridin-4-yloxy)-phenylamino]-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 3-Cyano-5-methyl-4-[4-(pyridin-3-yloxy)-phenylamino]-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 4-Acetylamino-N-{3-cyano-4-[4-(3-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-benzamide,
- 3-Acetylamino-N-{3-cyano-4-[4-(3-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-benzamide,
- N-{3-Cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-3-dimethylamino-benzamide,
- N-{3-Cyano-4-[4-(3-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-3-dimethylamino-benzamide,
- 1H-Benzoimidazole-5-carboxylic acid {3-cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-amide,
- 1H-Benzoimidazole-5-carboxylic acid {3-cyano-4-[4-(3-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-amide,
- 3-Cyano-4-(4-{2-[1-(ethylcarbamoylmethyl-carbamoyl)-1-methyl-ethoxy]-phenoxy}-phenylamino)-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester,
- 4-Benzenesulfonyl-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 6-Isopropenyl-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 3-[3-Cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-yloxy]-propane-1-sulfonic acid,
- (3-Morpholin-4-yl-propyl)-carbamic acid 3-cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-yl ester,
- 5-Methyl-4-(4-phenoxy-phenylamino)-6-pyridin-2-yl-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 3-Cyano-5-methoxy-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid,
- (2-Morpholin-4-yl-ethyl)-carbamic acid 3-cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-yl ester,
- (2-Morpholin-4-yl-ethyl)-carbamic acid 3-cyano-5-methoxy-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-yl ester,
- 3-[3-Cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-yloxycarbonylamino]-propionic acid,
- 6-(3H-Imidazol-4-yl)-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo]1,2-b]pyridazine-3-carbonitrile,
- Furan-2-carboxylic acid {3-cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-amide,
- Thiophene-2-carboxylic acid {3-cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-amide,
- 3-Cyano-4-{4-[2-(3-hydroxy-2,2-bis-hydroxymethyl-propoxy)-phenoxy]-phenylamino}-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester,
- N-{3-Cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-4-morpholin-4-yl-benzamide,
- N-{3-Cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-2-methanesulfonyl-benzamide,
- 2-Oxo-imidazolidine-1-carboxylic acid {3-cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-amide,
- Benzo[1,2,5]thiadiazole-5-carboxylic acid {3-cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-amide,
- 5-Methanesulfonyl-thiophene-2-carboxylic acid {3-cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-amide
- 3-Chloro-4-methanesulfonyl-thiophene-2-carboxylic acid {3-cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-amide,
- [1,2,3Thiadiazole-4-carboxylic acid {3-cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-amide,
- 3,5-Bis-acetylamino-N-{3-cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-d]pyridazin-6-yl}-benzamide,
- N-{3-Cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-4-guanidino-benzamide;
- trifluoro-acetic acid salt,
- N-{3-Cyano-4-[4-(3-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-3-nitro-benzamide,
- N-{3-Cyano-4-[4-(3-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-4-nitro-benzamide,
- N-{3-Cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-3-guanidino-benzamide;
- trifluoro-acetic acid salt,
- 3-Amino-N-{3-cyano-4-[4-(3-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-benzamide,
- N-{3-Cyano-4-[4-(3-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-3-ureido-benzamide,
- N-{3-Cyano-4-[4-(3-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-4-guanidino-benzamide,
- N-{3-Cyano-4-[4-(3-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-3-ureido-benzamide, trifluoro-acetic acid salt,
- N-{3-Cyano-4-[4-(3-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-4-guanidino-benzamide, trifluoro-acetic acid salt,
- 3,4-Bis-acetylamino-N-{3-cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-benzamide,
- 2-Oxo-2,3-dihydro-1H-indole-6-carboxylic acid {3-cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-amide,
- 2-Oxo-2,3-dihydro-1H-benzoimidazole-5-carboxylic acid {3-cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-amide,
- 2,3-Dioxo-1,2,3,4-tetrahydro-quinoxaline-6-carboxylic acid {3-cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-amide,
- Thiophene-2-carboxylic acid {3-cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-amide,
- 1H-Imidazole-2-carboxylic acid [3-cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazin-6-yl]-amide,
- 5-Methyl-4-(4-phenoxy-phenylamino)-7-phenyl-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 4-[4-(2-Methoxy-phenoxy)-phenylamino]-5-methyl-6-(pyrimidin-2-ylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- N-{3-Cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-guanidine;
- trifluoro-acetic acid salt,
- 4-[4-(2-Methoxy-phenoxy)-phenylamino]-5-methyl-6-(pyridin-2-ylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 6-(Di-pyrazin-2-yl-amino)-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- 4-[4-(2-Methoxy-phenoxy)-phenylamino]-5-methyl-6-(pyrazin-2-ylamino)-pyrrolo[1,2-b]pyridazine-3-carbonitrile,
- Acetic acid (3-{3-cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-ylcarbamoyl}-phenylcarbamoyl)-methyl ester,
- N-{3-Cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-3-nitro-benzamide,
- 4-(1-Benzoyl-piperidin-4-ylamino)-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 4-(4-Acetyl-piperazin-1-yl)-3-cyano-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- N-{3-Cyano-4-[4-(2-methoxy-phenoxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazin-6-yl}-3-(3-ethyl-ureido)-benzamide,
- 3-Cyano-5,7-dimethyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester,
- 7-Chloro-3-cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester,
- 7-Bromo-3-cyano-5-methyl-4-(4-phenoxy-phenylamino)-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester,
- 3-Cyano-4-{4-[2-(2,3-dihydroxy-propoxy)-phenoxy]-phenylamino}-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester,
- 3-Cyano-4-{4-[2-(3-hydroxy-2,2-bis-hydroxymethyl-propoxy)-phenoxy]-phenylamino}-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester,
- 3-Cyano-4-{4-[2-(2-hydroxy-ethoxy)phenoxy]-phenylamino}-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester, and
- 3-Cyano-4-(4-{2-[2-(2-hydroxy-ethoxy)-ethoxy]-phenoxy}-phenylamino)-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid methyl ester,
- or a pharmaceutically acceptable salt thereof.
172 more elements
Dependencies are inferred from the claim text.