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- Withdrawn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 |
|---|---|
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| WO (1) | WO2008055236A2 (enExample) |
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| US8022057B2 (en) * | 2007-11-12 | 2011-09-20 | 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 |
| KR20120117905A (ko) | 2010-01-28 | 2012-10-24 | 프레지던트 앤드 펠로우즈 오브 하바드 칼리지 | 프로테아좀 활성을 향상시키는 조성물 및 방법 |
| CA2789696C (en) | 2010-02-25 | 2017-11-07 | Dana-Farber Cancer Institute, Inc. | Braf mutations conferring resistance to braf inhibitors |
| EP2545187B1 (en) | 2010-03-09 | 2018-09-05 | Dana-Farber Cancer Institute, Inc. | Methods of diagnosing and treating cancer in patients having or developing resistance to a first cancer therapy |
| CN103140477B (zh) * | 2010-04-23 | 2015-07-15 | 拜耳知识产权股份有限公司 | 制备5-氟-1-烷基-3-氟烷基-1h-吡唑-4-酰氯和酰氟的方法 |
| TR201906779T4 (tr) | 2011-05-12 | 2019-05-21 | Proteostasis Therapeutics Inc | Proteostaz regülatörleri. |
| WO2013109142A1 (en) | 2012-01-16 | 2013-07-25 | Stichting Het Nederlands Kanker Instituut | Combined pdk and mapk/erk pathway inhibition in neoplasia |
| WO2013169858A1 (en) | 2012-05-08 | 2013-11-14 | The Broad Institute, Inc. | Diagnostic and treatment methods in patients having or at risk of developing resistance to cancer therapy |
| WO2014071183A1 (en) | 2012-11-02 | 2014-05-08 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Method of reducing adverse effects in a cancer patient undergoing treatment with a mek inhibitor |
| WO2014116228A1 (en) | 2013-01-25 | 2014-07-31 | President And Fellows Of Harvard College | Usp14 inhibitors for treating or preventing viral infections |
| WO2015041534A1 (en) | 2013-09-20 | 2015-03-26 | Stichting Het Nederlands Kanker Instituut | P90rsk in combination with raf/erk/mek |
| US9629851B2 (en) | 2013-09-20 | 2017-04-25 | Stitching Het Nederlands Kanker Institut—Antoni Van Leeuwenhoek Ziekenhuis | ROCK in combination with MAPK pathway |
| 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 |
| ES2913213T3 (es) | 2017-05-19 | 2022-06-01 | Nflection Therapeutics Inc | Compuestos heteroaromáticos de anilina condensados para el tratamiento de trastornos dérmicos |
| JP7212956B2 (ja) | 2017-05-19 | 2023-01-26 | エヌフレクション セラピューティクス インコーポレイテッド | 皮膚障害の処置用のピロロピリジン－アニリン化合物 |
| CN113660931B (zh) * | 2018-11-20 | 2024-10-11 | 恩福莱克逊治疗有限公司 | 用于治疗皮肤癌的芳基苯胺和杂芳基苯胺化合物 |
| EP3883552B1 (en) | 2018-11-20 | 2025-04-09 | NFlection Therapeutics, Inc. | Cyanoaryl-aniline compounds for treatment of dermal disorders |
| 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 |
| WO2020106305A1 (en) | 2018-11-20 | 2020-05-28 | Nflection Therapeutics, Inc. | Thienyl-aniline compounds for treatment of dermal disorders |
| CN117157065A (zh) | 2021-01-21 | 2023-12-01 | 恩福莱克逊治疗有限公司 | 吡咯并吡啶-苯胺化合物的晶型 |
| 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 |
| US4044126A (en) | 1972-04-20 | 1977-08-23 | Allen & Hanburys Limited | Steroidal aerosol compositions and process for the preparation thereof |
| GB1429184A (en) | 1972-04-20 | 1976-03-24 | Allen & Hanburys Ltd | Physically anti-inflammatory steroids for use in aerosols |
| USRE28819E (en) | 1972-12-08 | 1976-05-18 | Syntex (U.S.A.) Inc. | Dialkylated glycol compositions and medicament preparations containing same |
| US4328245A (en) | 1981-02-13 | 1982-05-04 | Syntex (U.S.A.) Inc. | Carbonate diester solutions of PGE-type compounds |
| US4410545A (en) | 1981-02-13 | 1983-10-18 | 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 |
| AU2004272457A1 (en) | 2003-09-16 | 2005-03-24 | Banyu Pharmaceutical Co., Ltd. | Novel indolopyrrolocarbazole derivative with antitumor activity |
| MXPA06013250A (es) | 2004-05-14 | 2007-02-28 | Abbott Lab | Inhibidores de quinasa como agentes terapeuticos. |
| ES2330872T3 (es) | 2004-12-01 | 2009-12-16 | Merck Serono Sa | Derivados de (1,2,4)triazolo(4,3-a)piridina para el tratamiento de enfermedades hiperproliferativas. |
| US7429667B2 (en) | 2005-01-20 | 2008-09-30 | Ardea Biosciences, Inc. | Phenylamino isothiazole carboxamidines as MEK inhibitors |
| NZ567140A (en) | 2005-10-07 | 2011-09-30 | Exelixis Inc | Azetidines as MEK inhibitors for the treatment of proliferative diseases |
-
2007
- 2007-10-31 EP EP09075386A patent/EP2113500A1/en not_active Withdrawn
- 2007-10-31 CA CA002667961A patent/CA2667961A1/en not_active Abandoned
- 2007-10-31 US US11/932,615 patent/US7943659B2/en not_active Expired - Fee Related
- 2007-10-31 JP JP2009534950A patent/JP2010508307A/ja not_active Withdrawn
- 2007-10-31 WO PCT/US2007/083240 patent/WO2008055236A2/en not_active Ceased
- 2007-10-31 EP EP07854546A patent/EP2089359A2/en not_active Withdrawn
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