JP2006526656A5 - - Google Patents
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- JP2006526656A5 JP2006526656A5 JP2006515154A JP2006515154A JP2006526656A5 JP 2006526656 A5 JP2006526656 A5 JP 2006526656A5 JP 2006515154 A JP2006515154 A JP 2006515154A JP 2006515154 A JP2006515154 A JP 2006515154A JP 2006526656 A5 JP2006526656 A5 JP 2006526656A5
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- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- methyl
- aryl
- cycloalkyl
- 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.)
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- -1 SO 3 R 7 Inorganic materials 0.000 claims description 187
- 125000000217 alkyl group Chemical group 0.000 claims description 157
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 124
- 125000003118 aryl group Chemical group 0.000 claims description 110
- 125000000623 heterocyclic group Chemical group 0.000 claims description 87
- 229910052739 hydrogen Inorganic materials 0.000 claims description 81
- 150000001875 compounds Chemical class 0.000 claims description 72
- 125000001072 heteroaryl group Chemical group 0.000 claims description 61
- 239000001257 hydrogen Substances 0.000 claims description 52
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 37
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 25
- 125000000304 alkynyl group Chemical group 0.000 claims description 21
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 10
- 108090000695 Cytokines Proteins 0.000 claims description 5
- 102000004127 Cytokines Human genes 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 3
- 108091000080 Phosphotransferase Proteins 0.000 claims description 3
- WTQSZUPMNGWJGE-UHFFFAOYSA-N n-benzyl-4-[4-(cyanomethyl)phenyl]-2-[5-(cyclopropylcarbamoyl)-2-methylanilino]-1,3-thiazole-5-carboxamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(S1)=NC(C=2C=CC(CC#N)=CC=2)=C1C(=O)NCC1=CC=CC=C1 WTQSZUPMNGWJGE-UHFFFAOYSA-N 0.000 claims description 3
- WPTHXTIVDNEWDS-UHFFFAOYSA-N n-methoxy-4-methyl-3-[(5-phenyl-1h-1,2,4-triazol-3-yl)amino]benzamide Chemical compound CONC(=O)C1=CC=C(C)C(NC=2NC(=NN=2)C=2C=CC=CC=2)=C1 WPTHXTIVDNEWDS-UHFFFAOYSA-N 0.000 claims description 3
- 102000020233 phosphotransferase Human genes 0.000 claims description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- 101000628954 Homo sapiens Mitogen-activated protein kinase 12 Proteins 0.000 claims description 2
- 102100026932 Mitogen-activated protein kinase 12 Human genes 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- OZTYUWVDJAFMQE-UHFFFAOYSA-N n-benzyl-2-[5-(cyclopropylcarbamoyl)-2-methylanilino]-4-(4-morpholin-4-ylphenyl)-1,3-thiazole-5-carboxamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(S1)=NC(C=2C=CC(=CC=2)N2CCOCC2)=C1C(=O)NCC1=CC=CC=C1 OZTYUWVDJAFMQE-UHFFFAOYSA-N 0.000 claims description 2
- QNQQSWPDHZLEEZ-UHFFFAOYSA-N n-cyclopropyl-4-methyl-3-[(4-phenyl-1,3-thiazol-2-yl)amino]benzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(SC=1)=NC=1C1=CC=CC=C1 QNQQSWPDHZLEEZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims 59
- 125000005843 halogen group Chemical group 0.000 claims 46
- 125000001188 haloalkyl group Chemical group 0.000 claims 42
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 40
- 150000002431 hydrogen Chemical class 0.000 claims 40
- 125000000547 substituted alkyl group Chemical group 0.000 claims 38
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 35
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 32
- 229910052760 oxygen Inorganic materials 0.000 claims 32
- 229910052757 nitrogen Inorganic materials 0.000 claims 29
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 28
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 28
- 239000003795 chemical substances by application Substances 0.000 claims 28
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 27
- 125000004093 cyano group Chemical group *C#N 0.000 claims 24
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 24
- 125000003545 alkoxy group Chemical group 0.000 claims 23
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 23
- 125000004043 oxo group Chemical group O=* 0.000 claims 23
- 201000010099 disease Diseases 0.000 claims 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 21
- 125000005236 alkanoylamino group Chemical group 0.000 claims 21
- 125000004414 alkyl thio group Chemical group 0.000 claims 21
- 125000001769 aryl amino group Chemical group 0.000 claims 21
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 21
- 229910052799 carbon Inorganic materials 0.000 claims 21
- 125000004438 haloalkoxy group Chemical group 0.000 claims 21
- 125000003107 substituted aryl group Chemical group 0.000 claims 21
- 229910052717 sulfur Inorganic materials 0.000 claims 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 19
- 125000005842 heteroatom Chemical group 0.000 claims 18
- 208000035475 disorder Diseases 0.000 claims 17
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 14
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 14
- RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims 14
- 125000004423 acyloxy group Chemical group 0.000 claims 14
- 125000003282 alkyl amino group Chemical group 0.000 claims 14
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 14
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims 14
- 125000004104 aryloxy group Chemical group 0.000 claims 14
- 125000001589 carboacyl group Chemical group 0.000 claims 14
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 14
- 229940124530 sulfonamide Drugs 0.000 claims 14
- 150000003456 sulfonamides Chemical class 0.000 claims 14
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 14
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 12
- 125000000335 thiazolyl group Chemical group 0.000 claims 12
- 239000003814 drug Substances 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 10
- 229940079593 drug Drugs 0.000 claims 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 10
- 125000001544 thienyl group Chemical group 0.000 claims 9
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 8
- 125000002541 furyl group Chemical group 0.000 claims 8
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 8
- 125000002950 monocyclic group Chemical group 0.000 claims 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 8
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 7
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 7
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 7
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 7
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 7
- 101100516563 Caenorhabditis elegans nhr-6 gene Proteins 0.000 claims 7
- 206010040070 Septic Shock Diseases 0.000 claims 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims 7
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims 7
- 125000005239 aroylamino group Chemical group 0.000 claims 7
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims 7
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims 7
- 125000005110 aryl thio group Chemical group 0.000 claims 7
- 229910052794 bromium Inorganic materials 0.000 claims 7
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 7
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 7
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 7
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 7
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims 7
- 229910052731 fluorine Inorganic materials 0.000 claims 7
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000002883 imidazolyl group Chemical group 0.000 claims 7
- 125000001041 indolyl group Chemical group 0.000 claims 7
- 208000015181 infectious disease Diseases 0.000 claims 7
- 125000005322 morpholin-1-yl group Chemical group 0.000 claims 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 7
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 7
- 238000006467 substitution reaction Methods 0.000 claims 7
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims 7
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 7
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 7
- JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 claims 6
- 201000008482 osteoarthritis Diseases 0.000 claims 5
- 230000000770 proinflammatory effect Effects 0.000 claims 5
- 102000004169 proteins and genes Human genes 0.000 claims 5
- 108090000623 proteins and genes Proteins 0.000 claims 5
- 208000020084 Bone disease Diseases 0.000 claims 4
- 206010006895 Cachexia Diseases 0.000 claims 4
- 206010009900 Colitis ulcerative Diseases 0.000 claims 4
- 201000005569 Gout Diseases 0.000 claims 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 4
- 208000034578 Multiple myelomas Diseases 0.000 claims 4
- 208000002193 Pain Diseases 0.000 claims 4
- 206010035226 Plasma cell myeloma Diseases 0.000 claims 4
- 206010037660 Pyrexia Diseases 0.000 claims 4
- 206010063837 Reperfusion injury Diseases 0.000 claims 4
- 206010040047 Sepsis Diseases 0.000 claims 4
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 4
- 208000036142 Viral infection Diseases 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 230000001939 inductive effect Effects 0.000 claims 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims 4
- 230000036407 pain Effects 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 4
- 208000024891 symptom Diseases 0.000 claims 4
- 230000009385 viral infection Effects 0.000 claims 4
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 208000011231 Crohn disease Diseases 0.000 claims 3
- 206010018364 Glomerulonephritis Diseases 0.000 claims 3
- 108010002352 Interleukin-1 Proteins 0.000 claims 3
- 201000004681 Psoriasis Diseases 0.000 claims 3
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 3
- 206010044248 Toxic shock syndrome Diseases 0.000 claims 3
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims 3
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 3
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 3
- 230000002917 arthritic effect Effects 0.000 claims 3
- 206010003246 arthritis Diseases 0.000 claims 3
- 208000006673 asthma Diseases 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 208000027866 inflammatory disease Diseases 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 230000004770 neurodegeneration Effects 0.000 claims 3
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 230000036303 septic shock Effects 0.000 claims 3
- 230000003612 virological effect Effects 0.000 claims 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
- 208000030507 AIDS Diseases 0.000 claims 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 206010055128 Autoimmune neutropenia Diseases 0.000 claims 2
- 210000002237 B-cell of pancreatic islet Anatomy 0.000 claims 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 2
- 208000023328 Basedow disease Diseases 0.000 claims 2
- 201000006474 Brain Ischemia Diseases 0.000 claims 2
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 2
- 206010063094 Cerebral malaria Diseases 0.000 claims 2
- 206010008909 Chronic Hepatitis Diseases 0.000 claims 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 2
- 208000035473 Communicable disease Diseases 0.000 claims 2
- 206010048843 Cytomegalovirus chorioretinitis Diseases 0.000 claims 2
- 206010012438 Dermatitis atopic Diseases 0.000 claims 2
- 208000037487 Endotoxemia Diseases 0.000 claims 2
- 206010018634 Gouty Arthritis Diseases 0.000 claims 2
- 208000015023 Graves' disease Diseases 0.000 claims 2
- 208000031886 HIV Infections Diseases 0.000 claims 2
- 208000037357 HIV infectious disease Diseases 0.000 claims 2
- 208000035186 Hemolytic Autoimmune Anemia Diseases 0.000 claims 2
- 208000005176 Hepatitis C Diseases 0.000 claims 2
- 206010019755 Hepatitis chronic active Diseases 0.000 claims 2
- 206010020751 Hypersensitivity Diseases 0.000 claims 2
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 claims 2
- 108090001007 Interleukin-8 Proteins 0.000 claims 2
- 208000007766 Kaposi sarcoma Diseases 0.000 claims 2
- 206010027480 Metastatic malignant melanoma Diseases 0.000 claims 2
- 102000056248 Mitogen-activated protein kinase 13 Human genes 0.000 claims 2
- 108700015928 Mitogen-activated protein kinase 13 Proteins 0.000 claims 2
- 208000000112 Myalgia Diseases 0.000 claims 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- 206010033645 Pancreatitis Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 claims 2
- 108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 claims 2
- 102000001253 Protein Kinase Human genes 0.000 claims 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims 2
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims 2
- 208000033464 Reiter syndrome Diseases 0.000 claims 2
- 206010039710 Scleroderma Diseases 0.000 claims 2
- 201000010001 Silicosis Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 208000007536 Thrombosis Diseases 0.000 claims 2
- 206010043781 Thyroiditis chronic Diseases 0.000 claims 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims 2
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims 2
- 241000700605 Viruses Species 0.000 claims 2
- 231100000354 acute hepatitis Toxicity 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 230000007815 allergy Effects 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 201000008937 atopic dermatitis Diseases 0.000 claims 2
- 201000000448 autoimmune hemolytic anemia Diseases 0.000 claims 2
- 230000001580 bacterial effect Effects 0.000 claims 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 2
- 208000019664 bone resorption disease Diseases 0.000 claims 2
- 206010008118 cerebral infarction Diseases 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 208000001763 cytomegalovirus retinitis Diseases 0.000 claims 2
- 230000001066 destructive effect Effects 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 208000001848 dysentery Diseases 0.000 claims 2
- 239000002158 endotoxin Substances 0.000 claims 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 2
- 208000006454 hepatitis Diseases 0.000 claims 2
- 208000005252 hepatitis A Diseases 0.000 claims 2
- 208000002672 hepatitis B Diseases 0.000 claims 2
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 claims 2
- 230000028709 inflammatory response Effects 0.000 claims 2
- 206010022000 influenza Diseases 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 208000011379 keloid formation Diseases 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 208000021039 metastatic melanoma Diseases 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 208000013465 muscle pain Diseases 0.000 claims 2
- 206010028417 myasthenia gravis Diseases 0.000 claims 2
- FVTLNLZIDGYJGR-UHFFFAOYSA-N n-benzyl-2-[5-(cyclopropylcarbamoyl)-2-methylanilino]-4-(4-fluoro-3-methylphenyl)-1,3-thiazole-5-carboxamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(S1)=NC(C=2C=C(C)C(F)=CC=2)=C1C(=O)NCC1=CC=CC=C1 FVTLNLZIDGYJGR-UHFFFAOYSA-N 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 230000002062 proliferating effect Effects 0.000 claims 2
- 108060006633 protein kinase Proteins 0.000 claims 2
- 230000002685 pulmonary effect Effects 0.000 claims 2
- 208000002574 reactive arthritis Diseases 0.000 claims 2
- 201000005404 rubella Diseases 0.000 claims 2
- 231100000241 scar Toxicity 0.000 claims 2
- 201000004595 synovitis Diseases 0.000 claims 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 206010043554 thrombocytopenia Diseases 0.000 claims 2
- 230000009772 tissue formation Effects 0.000 claims 2
- 230000008733 trauma Effects 0.000 claims 2
- 201000008827 tuberculosis Diseases 0.000 claims 2
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical group C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical group C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 claims 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical group C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 claims 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- NWUBXHJULBWGIM-UHFFFAOYSA-N 2-[5-(cyclopropylcarbamoyl)-2-methylanilino]-1,3-thiazole-5-carboxylic acid Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC1=NC=C(C(O)=O)S1 NWUBXHJULBWGIM-UHFFFAOYSA-N 0.000 claims 1
- OCGLEDQGYPNHDV-UHFFFAOYSA-N 2-[5-(cyclopropylcarbamoyl)-2-methylanilino]-n-(cyclopropylmethyl)-4-phenyl-1,3-thiazole-5-carboxamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(S1)=NC(C=2C=CC=CC=2)=C1C(=O)NCC1CC1 OCGLEDQGYPNHDV-UHFFFAOYSA-N 0.000 claims 1
- IHRQWVMNOWRFCP-UHFFFAOYSA-N 2-[5-(cyclopropylcarbamoyl)-2-methylanilino]-n-phenyl-1,3-thiazole-4-carboxamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(SC=1)=NC=1C(=O)NC1=CC=CC=C1 IHRQWVMNOWRFCP-UHFFFAOYSA-N 0.000 claims 1
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 1
- CNSPTSKZQDDULZ-UHFFFAOYSA-N 3-[[4-(4-cyanophenyl)-1,3-thiazol-2-yl]amino]-n-cyclopropyl-4-methylbenzamide Chemical compound CC1=CC=C(C(=O)NC2CC2)C=C1NC(SC=1)=NC=1C1=CC=C(C#N)C=C1 CNSPTSKZQDDULZ-UHFFFAOYSA-N 0.000 claims 1
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- 2004-06-02 AU AU2004251668A patent/AU2004251668B2/en not_active Ceased
- 2004-06-02 AT AT04754233T patent/ATE439837T1/de not_active IP Right Cessation
- 2004-06-02 EP EP04754233A patent/EP1635824B1/en not_active Expired - Lifetime
- 2004-06-02 JP JP2006515154A patent/JP2006526656A/ja active Pending
- 2004-06-02 PT PT04754233T patent/PT1635824E/pt unknown
- 2004-06-02 WO PCT/US2004/017580 patent/WO2005000298A2/en not_active Ceased
- 2004-06-02 CA CA002528438A patent/CA2528438A1/en not_active Abandoned
- 2004-06-02 PL PL04754233T patent/PL1635824T3/pl unknown
- 2004-06-02 BR BRPI0410905-8A patent/BRPI0410905A/pt not_active IP Right Cessation
- 2004-06-02 ES ES04754233T patent/ES2332135T3/es not_active Expired - Lifetime
- 2004-06-02 DE DE602004022668T patent/DE602004022668D1/de not_active Expired - Lifetime
- 2004-06-02 US US10/860,768 patent/US7652044B2/en not_active Expired - Fee Related
- 2004-06-02 MX MXPA05013075A patent/MXPA05013075A/es active IP Right Grant
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2009
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