JP2010508307A5 - - Google Patents
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- JP2010508307A5 JP2010508307A5 JP2009534950A JP2009534950A JP2010508307A5 JP 2010508307 A5 JP2010508307 A5 JP 2010508307A5 JP 2009534950 A JP2009534950 A JP 2009534950A JP 2009534950 A JP2009534950 A JP 2009534950A JP 2010508307 A5 JP2010508307 A5 JP 2010508307A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- fluoro
- methyl
- iodophenylamino
- pyrrole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- 102000043136 MAP kinase family Human genes 0.000 claims description 5
- 108091054455 MAP kinase family Proteins 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 230000000694 effects Effects 0.000 claims description 3
- 230000003463 hyperproliferative effect Effects 0.000 claims description 3
- 239000003102 growth factor Substances 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 30
- 150000001875 compounds Chemical class 0.000 claims 23
- 125000005842 heteroatom Chemical group 0.000 claims 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 10
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- -1 hydroxy, amino Chemical group 0.000 claims 8
- 150000001602 bicycloalkyls Chemical group 0.000 claims 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 150000002148 esters Chemical class 0.000 claims 3
- 239000000651 prodrug Substances 0.000 claims 3
- 229940002612 prodrug Drugs 0.000 claims 3
- 230000005856 abnormality Effects 0.000 claims 2
- 125000000033 alkoxyamino group Chemical group 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 2
- 238000001727 in vivo Methods 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 2
- XAFMIDMQPXYJKC-UHFFFAOYSA-N 1-[4-(3-aminoazetidine-1-carbonyl)-5-(2-fluoro-4-iodoanilino)-1-methylpyrrol-2-yl]ethanone Chemical compound C=1C=C(I)C=C(F)C=1NC=1N(C)C(C(=O)C)=CC=1C(=O)N1CC(N)C1 XAFMIDMQPXYJKC-UHFFFAOYSA-N 0.000 claims 1
- CJGSFRHGLCJMLT-UHFFFAOYSA-N 1-[4-(azetidine-1-carbonyl)-5-(2-fluoro-4-iodoanilino)-1-methylpyrrol-2-yl]ethanone Chemical compound C=1C=C(I)C=C(F)C=1NC=1N(C)C(C(=O)C)=CC=1C(=O)N1CCC1 CJGSFRHGLCJMLT-UHFFFAOYSA-N 0.000 claims 1
- TZHMUORSMKVYHD-IKGGRYGDSA-N 1-[4-[(2r,3s,4s)-3,4-dihydroxy-2-(hydroxymethyl)pyrrolidine-1-carbonyl]-5-(2-fluoro-4-iodoanilino)-1-methylpyrrol-2-yl]ethanone Chemical compound C=1C=C(I)C=C(F)C=1NC=1N(C)C(C(=O)C)=CC=1C(=O)N1C[C@H](O)[C@@H](O)[C@H]1CO TZHMUORSMKVYHD-IKGGRYGDSA-N 0.000 claims 1
- HVYMACHGKWXTGT-GFCCVEGCSA-N 1-[4-[(3r)-3-aminopyrrolidine-1-carbonyl]-5-(2-fluoro-4-iodoanilino)-1-methylpyrrol-2-yl]ethanone Chemical compound C=1C=C(I)C=C(F)C=1NC=1N(C)C(C(=O)C)=CC=1C(=O)N1CC[C@@H](N)C1 HVYMACHGKWXTGT-GFCCVEGCSA-N 0.000 claims 1
- SHKBYXXQCRZWOT-UHFFFAOYSA-N 1-[4-[3-(dimethylamino)azetidine-1-carbonyl]-5-(2-fluoro-4-iodoanilino)-1-methylpyrrol-2-yl]ethanone Chemical compound C1C(N(C)C)CN1C(=O)C1=C(NC=2C(=CC(I)=CC=2)F)N(C)C(C(C)=O)=C1 SHKBYXXQCRZWOT-UHFFFAOYSA-N 0.000 claims 1
- TXDZTYMSVDUYNZ-UHFFFAOYSA-N 1-[5-(2-fluoro-4-iodoanilino)-1-methyl-4-(pyrrolidine-1-carbonyl)pyrrol-2-yl]ethanone Chemical compound C=1C=C(I)C=C(F)C=1NC=1N(C)C(C(=O)C)=CC=1C(=O)N1CCCC1 TXDZTYMSVDUYNZ-UHFFFAOYSA-N 0.000 claims 1
- VXNQKYVWQDMTFL-UHFFFAOYSA-N 1-[5-(2-fluoro-4-iodoanilino)-4-(3-hydroxyazetidine-1-carbonyl)-1-methylpyrrol-2-yl]ethanone Chemical compound C=1C=C(I)C=C(F)C=1NC=1N(C)C(C(=O)C)=CC=1C(=O)N1CC(O)C1 VXNQKYVWQDMTFL-UHFFFAOYSA-N 0.000 claims 1
- UPAOPZRCMMWOCI-UHFFFAOYSA-N 1-[5-(2-fluoro-4-iodoanilino)-4-(4-hydroxy-1,2-oxazolidine-2-carbonyl)-1-methylpyrrol-2-yl]ethanone Chemical compound C=1C=C(I)C=C(F)C=1NC=1N(C)C(C(=O)C)=CC=1C(=O)N1CC(O)CO1 UPAOPZRCMMWOCI-UHFFFAOYSA-N 0.000 claims 1
- WRGISVIVGNSNTA-CYBMUJFWSA-N 1-[5-(2-fluoro-4-iodoanilino)-4-[(2r)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]-1-methylpyrrol-2-yl]ethanone Chemical compound C=1C=C(I)C=C(F)C=1NC=1N(C)C(C(=O)C)=CC=1C(=O)N1CCC[C@@H]1CO WRGISVIVGNSNTA-CYBMUJFWSA-N 0.000 claims 1
- WRGISVIVGNSNTA-ZDUSSCGKSA-N 1-[5-(2-fluoro-4-iodoanilino)-4-[(2s)-2-(hydroxymethyl)pyrrolidine-1-carbonyl]-1-methylpyrrol-2-yl]ethanone Chemical compound C=1C=C(I)C=C(F)C=1NC=1N(C)C(C(=O)C)=CC=1C(=O)N1CCC[C@H]1CO WRGISVIVGNSNTA-ZDUSSCGKSA-N 0.000 claims 1
- BQRLTUJLGDOGGH-GFCCVEGCSA-N 1-[5-(2-fluoro-4-iodoanilino)-4-[(3r)-3-(hydroxymethyl)pyrrolidine-1-carbonyl]-1-methylpyrrol-2-yl]ethanone Chemical compound C=1C=C(I)C=C(F)C=1NC=1N(C)C(C(=O)C)=CC=1C(=O)N1CC[C@@H](CO)C1 BQRLTUJLGDOGGH-GFCCVEGCSA-N 0.000 claims 1
- HOHLPTJEIQIUPM-GFCCVEGCSA-N 1-[5-(2-fluoro-4-iodoanilino)-4-[(3r)-3-hydroxypyrrolidine-1-carbonyl]-1-methylpyrrol-2-yl]ethanone Chemical compound C=1C=C(I)C=C(F)C=1NC=1N(C)C(C(=O)C)=CC=1C(=O)N1CC[C@@H](O)C1 HOHLPTJEIQIUPM-GFCCVEGCSA-N 0.000 claims 1
- BQRLTUJLGDOGGH-LBPRGKRZSA-N 1-[5-(2-fluoro-4-iodoanilino)-4-[(3s)-3-(hydroxymethyl)pyrrolidine-1-carbonyl]-1-methylpyrrol-2-yl]ethanone Chemical compound C=1C=C(I)C=C(F)C=1NC=1N(C)C(C(=O)C)=CC=1C(=O)N1CC[C@H](CO)C1 BQRLTUJLGDOGGH-LBPRGKRZSA-N 0.000 claims 1
- HOHLPTJEIQIUPM-LBPRGKRZSA-N 1-[5-(2-fluoro-4-iodoanilino)-4-[(3s)-3-hydroxypyrrolidine-1-carbonyl]-1-methylpyrrol-2-yl]ethanone Chemical compound C=1C=C(I)C=C(F)C=1NC=1N(C)C(C(=O)C)=CC=1C(=O)N1CC[C@H](O)C1 HOHLPTJEIQIUPM-LBPRGKRZSA-N 0.000 claims 1
- NRFDDDNPYGSVDV-UHFFFAOYSA-N 1-[5-(2-fluoro-4-iodoanilino)-4-[2-(hydroxymethyl)azetidine-1-carbonyl]-1-methylpyrrol-2-yl]ethanone Chemical compound C=1C=C(I)C=C(F)C=1NC=1N(C)C(C(=O)C)=CC=1C(=O)N1CCC1CO NRFDDDNPYGSVDV-UHFFFAOYSA-N 0.000 claims 1
- GELWSZMAGAQNPW-UHFFFAOYSA-N 1-[5-(2-fluoro-4-iodoanilino)-4-[3-(2-hydroxyethylamino)azetidine-1-carbonyl]-1-methylpyrrol-2-yl]ethanone Chemical compound C=1C=C(I)C=C(F)C=1NC=1N(C)C(C(=O)C)=CC=1C(=O)N1CC(NCCO)C1 GELWSZMAGAQNPW-UHFFFAOYSA-N 0.000 claims 1
- OLBGKOYAPOIFPH-UHFFFAOYSA-N 1-[5-(2-fluoro-4-iodoanilino)-4-[3-[2-hydroxyethyl(methyl)amino]azetidine-1-carbonyl]-1-methylpyrrol-2-yl]ethanone Chemical compound C1C(N(CCO)C)CN1C(=O)C1=C(NC=2C(=CC(I)=CC=2)F)N(C)C(C(C)=O)=C1 OLBGKOYAPOIFPH-UHFFFAOYSA-N 0.000 claims 1
- CKANXRABZSFDNL-UHFFFAOYSA-N 1-[5-(2-fluoro-4-iodoanilino)-4-[3-hydroxy-3-(hydroxymethyl)azetidine-1-carbonyl]-1-methylpyrrol-2-yl]ethanone Chemical compound C=1C=C(I)C=C(F)C=1NC=1N(C)C(C(=O)C)=CC=1C(=O)N1CC(O)(CO)C1 CKANXRABZSFDNL-UHFFFAOYSA-N 0.000 claims 1
- KSOJJARHPWCALR-UHFFFAOYSA-N 5-acetyl-2-(2-fluoro-4-iodoanilino)-1-methylpyrrole-3-carboxamide Chemical compound CN1C(C(=O)C)=CC(C(N)=O)=C1NC1=CC=C(I)C=C1F KSOJJARHPWCALR-UHFFFAOYSA-N 0.000 claims 1
- UFESGHZZXNELFW-UHFFFAOYSA-N 5-acetyl-2-(2-fluoro-4-iodoanilino)-1-methylpyrrole-3-carboxylic acid Chemical compound CN1C(C(=O)C)=CC(C(O)=O)=C1NC1=CC=C(I)C=C1F UFESGHZZXNELFW-UHFFFAOYSA-N 0.000 claims 1
- MXNXNGVHTQLCRO-UHFFFAOYSA-N 5-acetyl-2-(2-fluoro-4-iodoanilino)-1h-pyrrole-3-carboxylic acid Chemical compound N1C(C(=O)C)=CC(C(O)=O)=C1NC1=CC=C(I)C=C1F MXNXNGVHTQLCRO-UHFFFAOYSA-N 0.000 claims 1
- WRHOGNMBUWCIAC-UHFFFAOYSA-N 5-acetyl-2-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)-1-methylpyrrole-3-carboxamide Chemical compound CN1C(C(=O)C)=CC(C(=O)NOCCO)=C1NC1=CC=C(I)C=C1F WRHOGNMBUWCIAC-UHFFFAOYSA-N 0.000 claims 1
- NKOXCYPBNNENTF-UHFFFAOYSA-N 5-acetyl-2-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)-1h-pyrrole-3-carboxamide Chemical compound N1C(C(=O)C)=CC(C(=O)NOCCO)=C1NC1=CC=C(I)C=C1F NKOXCYPBNNENTF-UHFFFAOYSA-N 0.000 claims 1
- ACMFHCYKNJMZTC-UHFFFAOYSA-N 5-acetyl-2-(2-fluoro-4-iodoanilino)-n-(3-hydroxypropoxy)-1-methylpyrrole-3-carboxamide Chemical compound CN1C(C(=O)C)=CC(C(=O)NOCCCO)=C1NC1=CC=C(I)C=C1F ACMFHCYKNJMZTC-UHFFFAOYSA-N 0.000 claims 1
- PDOUTEFXQAGLBZ-UHFFFAOYSA-N 5-acetyl-2-(2-fluoro-4-iodoanilino)-n-(3-hydroxypropyl)-1-methylpyrrole-3-carboxamide Chemical compound CN1C(C(=O)C)=CC(C(=O)NCCCO)=C1NC1=CC=C(I)C=C1F PDOUTEFXQAGLBZ-UHFFFAOYSA-N 0.000 claims 1
- BWASMQQEXIBLSG-UHFFFAOYSA-N 5-acetyl-2-(2-fluoro-4-iodoanilino)-n-[3-hydroxy-2-(hydroxymethyl)propoxy]-1-methylpyrrole-3-carboxamide Chemical compound CN1C(C(=O)C)=CC(C(=O)NOCC(CO)CO)=C1NC1=CC=C(I)C=C1F BWASMQQEXIBLSG-UHFFFAOYSA-N 0.000 claims 1
- YZQAHNQQEZDSGH-UHFFFAOYSA-N 5-acetyl-2-(2-fluoro-4-iodoanilino)-n-methoxy-n,1-dimethylpyrrole-3-carboxamide Chemical compound C1=C(C(C)=O)N(C)C(NC=2C(=CC(I)=CC=2)F)=C1C(=O)N(C)OC YZQAHNQQEZDSGH-UHFFFAOYSA-N 0.000 claims 1
- ORCOEDMGSBQIQZ-UHFFFAOYSA-N 5-acetyl-4-chloro-2-(2-fluoro-4-iodoanilino)-1-methylpyrrole-3-carboxylic acid Chemical compound CN1C(C(=O)C)=C(Cl)C(C(O)=O)=C1NC1=CC=C(I)C=C1F ORCOEDMGSBQIQZ-UHFFFAOYSA-N 0.000 claims 1
- QNOSXWRXEWRKNE-UHFFFAOYSA-N 5-acetyl-4-chloro-2-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)-1-methylpyrrole-3-carboxamide Chemical compound CN1C(C(=O)C)=C(Cl)C(C(=O)NOCCO)=C1NC1=CC=C(I)C=C1F QNOSXWRXEWRKNE-UHFFFAOYSA-N 0.000 claims 1
- KMEPHBWIHCXVBJ-SNVBAGLBSA-N 5-acetyl-4-chloro-n-[(2r)-2,3-dihydroxypropoxy]-2-(2-fluoro-4-iodoanilino)-1-methylpyrrole-3-carboxamide Chemical compound CN1C(C(=O)C)=C(Cl)C(C(=O)NOC[C@H](O)CO)=C1NC1=CC=C(I)C=C1F KMEPHBWIHCXVBJ-SNVBAGLBSA-N 0.000 claims 1
- KMEPHBWIHCXVBJ-JTQLQIEISA-N 5-acetyl-4-chloro-n-[(2s)-2,3-dihydroxypropoxy]-2-(2-fluoro-4-iodoanilino)-1-methylpyrrole-3-carboxamide Chemical compound CN1C(C(=O)C)=C(Cl)C(C(=O)NOC[C@@H](O)CO)=C1NC1=CC=C(I)C=C1F KMEPHBWIHCXVBJ-JTQLQIEISA-N 0.000 claims 1
- USGMSBMFIPIFPP-UHFFFAOYSA-N 5-acetyl-4-fluoro-2-(2-fluoro-4-iodoanilino)-1-methylpyrrole-3-carboxylic acid Chemical compound CN1C(C(=O)C)=C(F)C(C(O)=O)=C1NC1=CC=C(I)C=C1F USGMSBMFIPIFPP-UHFFFAOYSA-N 0.000 claims 1
- RIMOLPWIINBFAW-UHFFFAOYSA-N 5-acetyl-n-(1,3-dihydroxypropan-2-yloxy)-2-(2-fluoro-4-iodoanilino)-1-methylpyrrole-3-carboxamide Chemical compound CN1C(C(=O)C)=CC(C(=O)NOC(CO)CO)=C1NC1=CC=C(I)C=C1F RIMOLPWIINBFAW-UHFFFAOYSA-N 0.000 claims 1
- PSLMLUNXPJDORF-UHFFFAOYSA-N 5-acetyl-n-(2,3-dihydroxypropyl)-2-(2-fluoro-4-iodoanilino)-1-methylpyrrole-3-carboxamide Chemical compound CN1C(C(=O)C)=CC(C(=O)NCC(O)CO)=C1NC1=CC=C(I)C=C1F PSLMLUNXPJDORF-UHFFFAOYSA-N 0.000 claims 1
- CVWGXRGATRNFPQ-LLVKDONJSA-N 5-acetyl-n-[(2r)-2,3-dihydroxypropoxy]-2-(2-fluoro-4-iodoanilino)-1-methylpyrrole-3-carboxamide Chemical compound CN1C(C(=O)C)=CC(C(=O)NOC[C@H](O)CO)=C1NC1=CC=C(I)C=C1F CVWGXRGATRNFPQ-LLVKDONJSA-N 0.000 claims 1
- OFRNQBJOWHENNK-SNVBAGLBSA-N 5-acetyl-n-[(2r)-2,3-dihydroxypropoxy]-4-fluoro-2-(2-fluoro-4-iodoanilino)-1-methylpyrrole-3-carboxamide Chemical compound CN1C(C(=O)C)=C(F)C(C(=O)NOC[C@H](O)CO)=C1NC1=CC=C(I)C=C1F OFRNQBJOWHENNK-SNVBAGLBSA-N 0.000 claims 1
- KUWQJHQBRURJTI-GFCCVEGCSA-N 5-acetyl-n-[(2r)-2,4-dihydroxybutoxy]-2-(2-fluoro-4-iodoanilino)-1-methylpyrrole-3-carboxamide Chemical compound CN1C(C(=O)C)=CC(C(=O)NOC[C@H](O)CCO)=C1NC1=CC=C(I)C=C1F KUWQJHQBRURJTI-GFCCVEGCSA-N 0.000 claims 1
- CVWGXRGATRNFPQ-NSHDSACASA-N 5-acetyl-n-[(2s)-2,3-dihydroxypropoxy]-2-(2-fluoro-4-iodoanilino)-1-methylpyrrole-3-carboxamide Chemical compound CN1C(C(=O)C)=CC(C(=O)NOC[C@@H](O)CO)=C1NC1=CC=C(I)C=C1F CVWGXRGATRNFPQ-NSHDSACASA-N 0.000 claims 1
- OFRNQBJOWHENNK-JTQLQIEISA-N 5-acetyl-n-[(2s)-2,3-dihydroxypropoxy]-4-fluoro-2-(2-fluoro-4-iodoanilino)-1-methylpyrrole-3-carboxamide Chemical compound CN1C(C(=O)C)=C(F)C(C(=O)NOC[C@@H](O)CO)=C1NC1=CC=C(I)C=C1F OFRNQBJOWHENNK-JTQLQIEISA-N 0.000 claims 1
- KUWQJHQBRURJTI-LBPRGKRZSA-N 5-acetyl-n-[(2s)-2,4-dihydroxybutoxy]-2-(2-fluoro-4-iodoanilino)-1-methylpyrrole-3-carboxamide Chemical compound CN1C(C(=O)C)=CC(C(=O)NOC[C@@H](O)CCO)=C1NC1=CC=C(I)C=C1F KUWQJHQBRURJTI-LBPRGKRZSA-N 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
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- 206010033645 Pancreatitis Diseases 0.000 claims 1
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- 210000001744 T-lymphocyte Anatomy 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- GXPWXPBHBVZFKZ-UHFFFAOYSA-N ethyl 5-acetyl-4-fluoro-2-(2-fluoro-4-iodoanilino)-1-methylpyrrole-3-carboxylate Chemical compound FC1=C(C(C)=O)N(C)C(NC=2C(=CC(I)=CC=2)F)=C1C(=O)OCC GXPWXPBHBVZFKZ-UHFFFAOYSA-N 0.000 claims 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000011242 neutrophil chemotaxis Effects 0.000 claims 1
- 230000007170 pathology Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000004044 response Effects 0.000 claims 1
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- 206010028980 Neoplasm Diseases 0.000 description 7
- 108090000695 Cytokines Proteins 0.000 description 4
- 102000004127 Cytokines Human genes 0.000 description 4
- 101001012157 Homo sapiens Receptor tyrosine-protein kinase erbB-2 Proteins 0.000 description 4
- 102100030086 Receptor tyrosine-protein kinase erbB-2 Human genes 0.000 description 4
- 239000000427 antigen Substances 0.000 description 3
- 102000036639 antigens Human genes 0.000 description 3
- 108091007433 antigens Proteins 0.000 description 3
- 229940022353 herceptin Drugs 0.000 description 3
- 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 description 3
- 206010055113 Breast cancer metastatic Diseases 0.000 description 2
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- 108090000394 Erythropoietin Proteins 0.000 description 1
- 102000003951 Erythropoietin Human genes 0.000 description 1
- 108010029961 Filgrastim Proteins 0.000 description 1
- 102100039619 Granulocyte colony-stimulating factor Human genes 0.000 description 1
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- 230000004054 inflammatory process Effects 0.000 description 1
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- 208000037819 metastatic cancer Diseases 0.000 description 1
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- 230000003525 myelopoietic effect Effects 0.000 description 1
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- OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 description 1
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86374806P | 2006-10-31 | 2006-10-31 | |
| PCT/US2007/083240 WO2008055236A2 (en) | 2006-10-31 | 2007-10-31 | Mapk/erk kinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010508307A JP2010508307A (ja) | 2010-03-18 |
| JP2010508307A5 true JP2010508307A5 (https=) | 2010-12-16 |
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| JP2009534950A Withdrawn JP2010508307A (ja) | 2006-10-31 | 2007-10-31 | Ｍａｐｋ／ｅｒｋキナーゼ阻害剤 |
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| US (1) | US7943659B2 (https=) |
| EP (2) | EP2089359A2 (https=) |
| JP (1) | JP2010508307A (https=) |
| CA (1) | CA2667961A1 (https=) |
| WO (1) | WO2008055236A2 (https=) |
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| WO2009064675A1 (en) * | 2007-11-12 | 2009-05-22 | Takeda Pharmaceutical Company Limited | Mapk/erk kinase inhibitors |
| EP2370568B1 (en) | 2008-12-10 | 2017-07-19 | Dana-Farber Cancer Institute, Inc. | Mek mutations conferring resistance to mek inhibitors |
| MX336731B (es) | 2010-01-28 | 2016-01-28 | Harvard College | Composiciones y metodos para potenciar la actividad de proteasoma. |
| EP3028699B1 (en) | 2010-02-25 | 2018-03-21 | Dana-Farber Cancer Institute, Inc. | Braf mutations conferring resistance to braf inhibitors |
| CN103038364A (zh) | 2010-03-09 | 2013-04-10 | 达纳－法伯癌症研究所公司 | 诊断和治疗具有或发展对于第一种癌症治疗的抗性的患者中的癌症的方法 |
| ES2616005T3 (es) * | 2010-04-23 | 2017-06-09 | Bayer Intellectual Property Gmbh | Procedimiento para la preparación de cloruros y fluoruros de ácido 5-fluoro-1-alquil-3-fluoroalquil-1H-pirazol-4-carboxílico |
| DK2707101T3 (da) * | 2011-05-12 | 2019-05-13 | Proteostasis Therapeutics Inc | Proteostaseregulatorer |
| WO2013109142A1 (en) | 2012-01-16 | 2013-07-25 | Stichting Het Nederlands Kanker Instituut | Combined pdk and mapk/erk pathway inhibition in neoplasia |
| US20150141470A1 (en) | 2012-05-08 | 2015-05-21 | The Broad Institute, Inc. | Diagnostic and treatment methods in patients having or at risk of developing resistance to cancer therapy |
| US20150265679A1 (en) | 2012-11-02 | 2015-09-24 | The United States Of America, As Represented By Secretary, Department Of Health And Human Services | Method of reducing adverse effects in a cancer patient undregoing treatment with a mek inhibitor |
| US9849135B2 (en) | 2013-01-25 | 2017-12-26 | President And Fellows Of Harvard College | USP14 inhibitors for treating or preventing viral infections |
| EP3046557A1 (en) | 2013-09-20 | 2016-07-27 | Stichting Het Nederlands Kanker Instituut | Rock in combination with mapk-pathway |
| WO2015041534A1 (en) | 2013-09-20 | 2015-03-26 | Stichting Het Nederlands Kanker Instituut | P90rsk in combination with raf/erk/mek |
| WO2015073528A1 (en) | 2013-11-12 | 2015-05-21 | Proteostasis Therapeutics, Inc. | Proteasome activity enhancing compounds |
| US20170027940A1 (en) | 2014-04-10 | 2017-02-02 | Stichting Het Nederlands Kanker Instituut | Method for treating cancer |
| WO2015178770A1 (en) | 2014-05-19 | 2015-11-26 | Stichting Het Nederlands Kanker Instituut | Compositions for cancer treatment |
| US20170114323A1 (en) | 2014-06-19 | 2017-04-27 | Whitehead Institute For Biomedical Research | Uses of kinase inhibitors for inducing and maintaining pluripotency |
| WO2016187028A1 (en) * | 2015-05-15 | 2016-11-24 | Celgene Avilomics Research, Inc. | Heteroaryl compounds, synthesis thereof, and intermediates thereto |
| WO2017058007A1 (en) | 2015-10-01 | 2017-04-06 | Stichting Het Nederlands Kanker Instituut-Antoni van Leeuwenhoek Ziekenhuis | Histone deacetylase inhibitors for the use in the treatment of drug resistant melanoma |
| WO2017099591A1 (en) | 2015-12-07 | 2017-06-15 | Stichting Het Nederlands Kanker Instituut-Antoni van Leeuwenhoek Ziekenhuis | Treatment of inhibitor resistant braf-mutant cancers |
| WO2017204626A1 (en) | 2016-05-24 | 2017-11-30 | Stichting Het Nederlands Kanker Instituut-Antoni van Leeuwenhoek Ziekenhuis | Combination therapy - combined map2k4/map3k1 and mek/erk inhibition |
| MX2019013562A (es) | 2017-05-19 | 2020-08-03 | Nflection Therapeutics Inc | Compuestos de anilina heteroaromatica o fusionados para el tratamiento de trastornos dermicos. |
| US11161845B2 (en) | 2017-05-19 | 2021-11-02 | Nflection Therapeutics, Inc. | Pyrrolopyridine-aniline compounds for treatment of dermal disorders |
| AU2019383311B2 (en) | 2018-11-20 | 2024-12-05 | Nflection Therapeutics, Inc. | Cyanoaryl-aniline compounds for treatment of dermal disorders |
| US12466818B2 (en) | 2018-11-20 | 2025-11-11 | Nflection Therapeutics, Inc. | Thienyl-aniline compounds for treatment of dermal disorders |
| MA55143A (fr) * | 2018-11-20 | 2021-09-29 | H Lee Moffitt Cancer Center & Res Institute Inc | Composés aryl-aniline et hétéroaryl-aniline pour le traitement de cancers de la peau |
| CN113473986B (zh) | 2018-11-20 | 2024-10-11 | 恩福莱克逊治疗有限公司 | 用于治疗皮肤疾病萘啶酮苯胺化合物 |
| US12371667B2 (en) | 2021-05-13 | 2025-07-29 | Washington University | Enhanced methods for inducing and maintaining naive human pluripotent stem cells |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3710795A (en) | 1970-09-29 | 1973-01-16 | Alza Corp | Drug-delivery device with stretched, rate-controlling membrane |
| GB1429184A (en) | 1972-04-20 | 1976-03-24 | Allen & Hanburys Ltd | Physically anti-inflammatory steroids for use in aerosols |
| US4044126A (en) | 1972-04-20 | 1977-08-23 | Allen & Hanburys Limited | Steroidal aerosol compositions and process for the preparation thereof |
| USRE28819E (en) | 1972-12-08 | 1976-05-18 | Syntex (U.S.A.) Inc. | Dialkylated glycol compositions and medicament preparations containing same |
| US4410545A (en) | 1981-02-13 | 1983-10-18 | Syntex (U.S.A.) Inc. | Carbonate diester solutions of PGE-type compounds |
| US4328245A (en) | 1981-02-13 | 1982-05-04 | Syntex (U.S.A.) Inc. | Carbonate diester solutions of PGE-type compounds |
| US4358603A (en) | 1981-04-16 | 1982-11-09 | Syntex (U.S.A.) Inc. | Acetal stabilized prostaglandin compositions |
| US4409239A (en) | 1982-01-21 | 1983-10-11 | Syntex (U.S.A.) Inc. | Propylene glycol diester solutions of PGE-type compounds |
| EP1666485A1 (en) | 2003-09-16 | 2006-06-07 | Banyu Pharmaceutical Co., Ltd. | Novel indolopyrrolocarbazole derivative with antitumor activity |
| EP1753428A4 (en) | 2004-05-14 | 2010-09-15 | Abbott Lab | INHIBITORS OF KINASES AS THERAPEUTIC AGENTS |
| JP2008521858A (ja) | 2004-12-01 | 2008-06-26 | ラボラトワール セローノ ソシエテ アノニム | 過増殖性疾患を処置するための［１，２，４］トリアゾロ［４，３−ａ］ピリジン誘導体 |
| US7429667B2 (en) | 2005-01-20 | 2008-09-30 | Ardea Biosciences, Inc. | Phenylamino isothiazole carboxamidines as MEK inhibitors |
| HRP20110498T1 (hr) | 2005-10-07 | 2011-08-31 | Exelixis | Azetidini kao inhibitori mek za liječenje proliferativnih bolesti |
-
2007
- 2007-10-31 EP EP07854546A patent/EP2089359A2/en not_active Withdrawn
- 2007-10-31 CA CA002667961A patent/CA2667961A1/en not_active Abandoned
- 2007-10-31 JP JP2009534950A patent/JP2010508307A/ja not_active Withdrawn
- 2007-10-31 EP EP09075386A patent/EP2113500A1/en not_active Withdrawn
- 2007-10-31 WO PCT/US2007/083240 patent/WO2008055236A2/en not_active Ceased
- 2007-10-31 US US11/932,615 patent/US7943659B2/en not_active Expired - Fee Related
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