JP2006514940A5 - - Google Patents
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- JP2006514940A5 JP2006514940A5 JP2004557232A JP2004557232A JP2006514940A5 JP 2006514940 A5 JP2006514940 A5 JP 2006514940A5 JP 2004557232 A JP2004557232 A JP 2004557232A JP 2004557232 A JP2004557232 A JP 2004557232A JP 2006514940 A5 JP2006514940 A5 JP 2006514940A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- methyl
- methoxy
- tert
- butyl
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 23
- -1 hydroxy, hydroxy Chemical group 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- XOZZYNPAVVPHRQ-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]triazole-4-carboxylic acid Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(O)=O)=C1 XOZZYNPAVVPHRQ-UHFFFAOYSA-N 0.000 claims 9
- 150000002431 hydrogen Chemical class 0.000 claims 9
- 239000002253 acid Substances 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical class 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- VLHZHHLVRNKJKP-UHFFFAOYSA-N 5-amino-1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]triazole-4-carboxylic acid Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2C(=C(C(O)=O)N=N2)N)=C1 VLHZHHLVRNKJKP-UHFFFAOYSA-N 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 230000001154 acute effect Effects 0.000 claims 6
- 125000002252 acyl group Chemical group 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 125000004442 acylamino group Chemical group 0.000 claims 5
- 125000004423 acyloxy group Chemical group 0.000 claims 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 5
- 150000002148 esters Chemical class 0.000 claims 5
- 125000002757 morpholinyl group Chemical group 0.000 claims 5
- 125000003386 piperidinyl group Chemical group 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 4
- 208000002193 Pain Diseases 0.000 claims 4
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 4
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 4
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 208000011580 syndromic disease Diseases 0.000 claims 4
- 238000002560 therapeutic procedure Methods 0.000 claims 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 230000008878 coupling Effects 0.000 claims 3
- 238000010168 coupling process Methods 0.000 claims 3
- 238000005859 coupling reaction Methods 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 150000002825 nitriles Chemical class 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 3
- WCNFFKHKJLERFM-UHFFFAOYSA-N thiomorpholinyl sulfone group Chemical group N1(CCSCC1)S(=O)(=O)N1CCSCC1 WCNFFKHKJLERFM-UHFFFAOYSA-N 0.000 claims 3
- ZCAGUOCUDGWENZ-UHFFFAOYSA-N thiomorpholinyl sulfoxide group Chemical group N1(CCSCC1)S(=O)N1CCSCC1 ZCAGUOCUDGWENZ-UHFFFAOYSA-N 0.000 claims 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- MYKHBWFULXPPPE-UHFFFAOYSA-N 1-[5-[(3-amino-5-tert-butyl-2-methoxyphenyl)carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound COC1=C(N)C=C(C(C)(C)C)C=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC(C)(C)C)=C1 MYKHBWFULXPPPE-UHFFFAOYSA-N 0.000 claims 2
- QOEOCMUCZLZNLQ-HXUWFJFHSA-N 1-[5-[(5-tert-butyl-2-methoxyphenyl)carbamoyl]-2-methylphenyl]-n-[(1r)-1-phenylethyl]triazole-4-carboxamide Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)N[C@H](C)C=2C=CC=CC=2)=C1 QOEOCMUCZLZNLQ-HXUWFJFHSA-N 0.000 claims 2
- XBUJGHAGSRFSEN-GOSISDBHSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-chlorophenyl]-n-[(1r)-1-phenylethyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(Cl)C(N2N=NC(=C2)C(=O)N[C@H](C)C=2C=CC=CC=2)=C1 XBUJGHAGSRFSEN-GOSISDBHSA-N 0.000 claims 2
- WLQPPEXYIUYGHM-HSZRJFAPSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-chlorophenyl]-n-[(1r)-1-phenylpropyl]triazole-4-carboxamide Chemical compound N([C@H](CC)C=1C=CC=CC=1)C(=O)C(N=N1)=CN1C(C(=CC=1)Cl)=CC=1C(=O)NC1=CC(C(C)(C)C)=CC(NS(C)(=O)=O)=C1OC WLQPPEXYIUYGHM-HSZRJFAPSA-N 0.000 claims 2
- KNMFMVBWDXPKBO-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-(1-pyridin-3-ylethyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NC(C)C=2C=NC=CC=2)=C1 KNMFMVBWDXPKBO-UHFFFAOYSA-N 0.000 claims 2
- NSNSJQAJKXHCJR-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-(2-hydroxy-2-methylpropyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC(C)(C)O)=C1 NSNSJQAJKXHCJR-UHFFFAOYSA-N 0.000 claims 2
- QMYIHPBIEQXPDM-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-(cyclopentylmethyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC2CCCC2)=C1 QMYIHPBIEQXPDM-UHFFFAOYSA-N 0.000 claims 2
- GQEQCKCNBUCAMO-HXUWFJFHSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[(1r)-1-cyclohexylethyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)N[C@H](C)C2CCCCC2)=C1 GQEQCKCNBUCAMO-HXUWFJFHSA-N 0.000 claims 2
- DBGHYGSALMWLLM-XMMPIXPASA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[(1r)-1-phenylpropyl]triazole-4-carboxamide Chemical compound N([C@H](CC)C=1C=CC=CC=1)C(=O)C(N=N1)=CN1C(C(=CC=1)C)=CC=1C(=O)NC1=CC(C(C)(C)C)=CC(NS(C)(=O)=O)=C1OC DBGHYGSALMWLLM-XMMPIXPASA-N 0.000 claims 2
- RZLBVMIOOFAEBX-HHHXNRCGSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[(1s)-2-(dimethylamino)-1-phenylethyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)N[C@H](CN(C)C)C=2C=CC=CC=2)=C1 RZLBVMIOOFAEBX-HHHXNRCGSA-N 0.000 claims 2
- MOYBVQRLCMRPHZ-HHHXNRCGSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[(1s)-2-methoxy-1-phenylethyl]triazole-4-carboxamide Chemical compound N([C@H](COC)C=1C=CC=CC=1)C(=O)C(N=N1)=CN1C(C(=CC=1)C)=CC=1C(=O)NC1=CC(C(C)(C)C)=CC(NS(C)(=O)=O)=C1OC MOYBVQRLCMRPHZ-HHHXNRCGSA-N 0.000 claims 2
- BCZVTYMHNFUTNX-GOSISDBHSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[(2r)-3,3-dimethylbutan-2-yl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)N[C@H](C)C(C)(C)C)=C1 BCZVTYMHNFUTNX-GOSISDBHSA-N 0.000 claims 2
- UGWSSKXHAHYOAM-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[3-(dimethylamino)-2,2-dimethylpropyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC(C)(C)CN(C)C)=C1 UGWSSKXHAHYOAM-UHFFFAOYSA-N 0.000 claims 2
- XDIAMRVROCPPBK-UHFFFAOYSA-N 2,2-dimethylpropan-1-amine Chemical compound CC(C)(C)CN XDIAMRVROCPPBK-UHFFFAOYSA-N 0.000 claims 2
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 claims 2
- GLZIQUGSLFRMPD-KRWDZBQOSA-N 5-amino-1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[(2s)-3,3-dimethylbutan-2-yl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2C(=C(C(=O)N[C@@H](C)C(C)(C)C)N=N2)N)=C1 GLZIQUGSLFRMPD-KRWDZBQOSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 206010007559 Cardiac failure congestive Diseases 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 208000000094 Chronic Pain Diseases 0.000 claims 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 102000004127 Cytokines Human genes 0.000 claims 2
- 108090000695 Cytokines Proteins 0.000 claims 2
- 201000004624 Dermatitis Diseases 0.000 claims 2
- 206010012442 Dermatitis contact Diseases 0.000 claims 2
- 206010018366 Glomerulonephritis acute Diseases 0.000 claims 2
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 2
- 208000035895 Guillain-Barré syndrome Diseases 0.000 claims 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 201000009906 Meningitis Diseases 0.000 claims 2
- 206010049567 Miller Fisher syndrome Diseases 0.000 claims 2
- 206010051606 Necrotising colitis Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 206010063837 Reperfusion injury Diseases 0.000 claims 2
- 206010040047 Sepsis Diseases 0.000 claims 2
- 206010040070 Septic Shock Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 206010044248 Toxic shock syndrome Diseases 0.000 claims 2
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims 2
- 206010048873 Traumatic arthritis Diseases 0.000 claims 2
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 2
- 208000027418 Wounds and injury Diseases 0.000 claims 2
- 231100000851 acute glomerulonephritis Toxicity 0.000 claims 2
- 208000005298 acute pain Diseases 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 239000003146 anticoagulant agent Substances 0.000 claims 2
- 125000003435 aroyl group Chemical group 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 150000001540 azides Chemical class 0.000 claims 2
- 125000004069 aziridinyl group Chemical group 0.000 claims 2
- 208000019664 bone resorption disease Diseases 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 208000010247 contact dermatitis Diseases 0.000 claims 2
- 238000007887 coronary angioplasty Methods 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 230000006378 damage Effects 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 208000024908 graft versus host disease Diseases 0.000 claims 2
- 210000003714 granulocyte Anatomy 0.000 claims 2
- 238000001631 haemodialysis Methods 0.000 claims 2
- 230000000322 hemodialysis Effects 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims 2
- 210000000265 leukocyte Anatomy 0.000 claims 2
- 206010025135 lupus erythematosus Diseases 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- ZVNDOKIIMUJRSN-UHFFFAOYSA-N n-(2,2-dimethylpropyl)-1-[5-[[3-(methanesulfonamido)-2-methoxy-5-(1-methylcyclopropyl)phenyl]carbamoyl]-2-methylphenyl]triazole-4-carboxamide Chemical compound C1=C(C2(C)CC2)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C(C=1)=CC=C(C)C=1N1C=C(C(=O)NCC(C)(C)C)N=N1 ZVNDOKIIMUJRSN-UHFFFAOYSA-N 0.000 claims 2
- ZQJWVDFJLKWVCM-UHFFFAOYSA-N n-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-(cyclohexanecarbonyl)triazol-1-yl]-4-methylbenzamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)C2CCCCC2)=C1 ZQJWVDFJLKWVCM-UHFFFAOYSA-N 0.000 claims 2
- HOPHKMATGGUWCH-HSZRJFAPSA-N n-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-[(2s)-3-hydroxy-2-phenylpropanoyl]triazol-1-yl]-4-methylbenzamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)[C@H](CO)C=2C=CC=CC=2)=C1 HOPHKMATGGUWCH-HSZRJFAPSA-N 0.000 claims 2
- PIVITOMPTXKKRX-HXUWFJFHSA-N n-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-4-methyl-3-[4-[(2r)-2-phenylpropanoyl]triazol-1-yl]benzamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)[C@H](C)C=2C=CC=CC=2)=C1 PIVITOMPTXKKRX-HXUWFJFHSA-N 0.000 claims 2
- 208000004995 necrotizing enterocolitis Diseases 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 201000006195 perinatal necrotizing enterocolitis Diseases 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 208000037803 restenosis Diseases 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- 230000002537 thrombolytic effect Effects 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 claims 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- CRCTZWNJRMZUIO-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical group FC(F)(F)[CH]C(F)(F)F CRCTZWNJRMZUIO-UHFFFAOYSA-N 0.000 claims 1
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims 1
- OBAHWSLSHGVOTK-LJQANCHMSA-N 1-[3-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]phenyl]-n-[(1r)-1-phenylethyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=CC(N2N=NC(=C2)C(=O)N[C@H](C)C=2C=CC=CC=2)=C1 OBAHWSLSHGVOTK-LJQANCHMSA-N 0.000 claims 1
- FFDIGMODELFUPV-UHFFFAOYSA-N 1-[5-[(5-tert-butyl-2-methoxyphenyl)carbamoyl]-2-methylphenyl]-n-(2-morpholin-4-ylethyl)triazole-4-carboxamide Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCCN2CCOCC2)=C1 FFDIGMODELFUPV-UHFFFAOYSA-N 0.000 claims 1
- VRZHJBDQJUZDEO-QGZVFWFLSA-N 1-[5-[[5-(1,1,1,3,3,3-hexafluoropropan-2-yl)-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[(1r)-1-phenylethyl]triazole-4-carboxamide Chemical compound C1=C(C(C(F)(F)F)C(F)(F)F)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)N[C@H](C)C=2C=CC=CC=2)=C1 VRZHJBDQJUZDEO-QGZVFWFLSA-N 0.000 claims 1
- OAHPEUSJDOZCAG-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2,3-dimethylphenyl]-n-(2-morpholin-4-ylethyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC(C)=C(C)C(N2N=NC(=C2)C(=O)NCCN2CCOCC2)=C1 OAHPEUSJDOZCAG-UHFFFAOYSA-N 0.000 claims 1
- VTRVTYITLGKQKR-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-chlorophenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(Cl)C(N2N=NC(=C2)C(=O)NCC(C)(C)C)=C1 VTRVTYITLGKQKR-UHFFFAOYSA-N 0.000 claims 1
- IEDNIQALLRPMFJ-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-chlorophenyl]-n-(pyridin-3-ylmethyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(Cl)C(N2N=NC(=C2)C(=O)NCC=2C=NC=CC=2)=C1 IEDNIQALLRPMFJ-UHFFFAOYSA-N 0.000 claims 1
- BSCPSIHMYYIRHZ-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-fluorophenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(F)C(N2N=NC(=C2)C(=O)NCC(C)(C)C)=C1 BSCPSIHMYYIRHZ-UHFFFAOYSA-N 0.000 claims 1
- TWMNPSJTUSFPEC-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-(2,2-dimethylpropyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC(C)(C)C)=C1 TWMNPSJTUSFPEC-UHFFFAOYSA-N 0.000 claims 1
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- HPGQOUXJTRWYTC-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-(2-piperidin-1-ylethyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCCN2CCCCC2)=C1 HPGQOUXJTRWYTC-UHFFFAOYSA-N 0.000 claims 1
- QFXBWQVIBRTSLX-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-(piperidin-4-ylmethyl)triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC2CCNCC2)=C1 QFXBWQVIBRTSLX-UHFFFAOYSA-N 0.000 claims 1
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- CPPRGDCVJNIOIR-UHFFFAOYSA-N 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-phenyltriazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NC=2C=CC=CC=2)=C1 CPPRGDCVJNIOIR-UHFFFAOYSA-N 0.000 claims 1
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- MPFDLGZRXMLAAA-UHFFFAOYSA-N 5-amino-1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]-n-[3-(dimethylamino)-2,2-dimethylpropyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2C(=C(C(=O)NCC(C)(C)CN(C)C)N=N2)N)=C1 MPFDLGZRXMLAAA-UHFFFAOYSA-N 0.000 claims 1
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- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
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- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 1
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
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- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
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- MKSRIAPRXGGSJY-UHFFFAOYSA-N ethyl 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-chlorophenyl]triazole-4-carboxylate Chemical compound N1=NC(C(=O)OCC)=CN1C1=CC(C(=O)NC=2C(=C(NS(C)(=O)=O)C=C(C=2)C(C)(C)C)OC)=CC=C1Cl MKSRIAPRXGGSJY-UHFFFAOYSA-N 0.000 claims 1
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- MUSXKAUTAHERDY-UHFFFAOYSA-N methyl 1-[5-[(5-tert-butyl-2-methoxyphenyl)carbamoyl]-2-methylphenyl]triazole-4-carboxylate Chemical compound N1=NC(C(=O)OC)=CN1C1=CC(C(=O)NC=2C(=CC=C(C=2)C(C)(C)C)OC)=CC=C1C MUSXKAUTAHERDY-UHFFFAOYSA-N 0.000 claims 1
- OSZZMYWVIGDKMW-UHFFFAOYSA-N methyl 1-[5-[[3-(methanesulfonamido)-2-methoxy-5-(trifluoromethyl)phenyl]carbamoyl]-2-methylphenyl]triazole-4-carboxylate Chemical compound N1=NC(C(=O)OC)=CN1C1=CC(C(=O)NC=2C(=C(NS(C)(=O)=O)C=C(C=2)C(F)(F)F)OC)=CC=C1C OSZZMYWVIGDKMW-UHFFFAOYSA-N 0.000 claims 1
- KSRCYOQOGDWUNY-UHFFFAOYSA-N methyl 1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-chlorophenyl]triazole-4-carboxylate Chemical compound N1=NC(C(=O)OC)=CN1C1=CC(C(=O)NC=2C(=C(NS(C)(=O)=O)C=C(C=2)C(C)(C)C)OC)=CC=C1Cl KSRCYOQOGDWUNY-UHFFFAOYSA-N 0.000 claims 1
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- GAQFDOSNIHMESR-UHFFFAOYSA-N methyl 3-[1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]triazole-4-carbonyl]benzoate Chemical compound COC(=O)C1=CC=CC(C(=O)C=2N=NN(C=2)C=2C(=CC=C(C=2)C(=O)NC=2C(=C(NS(C)(=O)=O)C=C(C=2)C(C)(C)C)OC)C)=C1 GAQFDOSNIHMESR-UHFFFAOYSA-N 0.000 claims 1
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- UEBKINPAGUSUBV-UHFFFAOYSA-N n-[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]-3-[4-(2,6-dimethylbenzoyl)triazol-1-yl]-4-methylbenzamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)C=2C(=CC=CC=2C)C)=C1 UEBKINPAGUSUBV-UHFFFAOYSA-N 0.000 claims 1
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- KAWCXOHGUGNDJC-UHFFFAOYSA-N n-benzyl-1-[3-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]phenyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=CC(N2N=NC(=C2)C(=O)NCC=2C=CC=CC=2)=C1 KAWCXOHGUGNDJC-UHFFFAOYSA-N 0.000 claims 1
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- JJDIIKNVGLYKMW-UHFFFAOYSA-N n-benzyl-1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-fluorophenyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(F)C(N2N=NC(=C2)C(=O)NCC=2C=CC=CC=2)=C1 JJDIIKNVGLYKMW-UHFFFAOYSA-N 0.000 claims 1
- YVIHJEHDPKKGMU-UHFFFAOYSA-N n-benzyl-1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]triazole-4-carboxamide Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC=2C=CC=CC=2)=C1 YVIHJEHDPKKGMU-UHFFFAOYSA-N 0.000 claims 1
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- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims 1
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- SUUUBXOVOSRGAM-UHFFFAOYSA-N tert-butyl 3-[[[1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]triazole-4-carbonyl]amino]methyl]piperidine-1-carboxylate Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC2CN(CCC2)C(=O)OC(C)(C)C)=C1 SUUUBXOVOSRGAM-UHFFFAOYSA-N 0.000 claims 1
- CPXCJMGYKWMJBM-UHFFFAOYSA-N tert-butyl 4-[[[1-[5-[[5-tert-butyl-3-(methanesulfonamido)-2-methoxyphenyl]carbamoyl]-2-methylphenyl]triazole-4-carbonyl]amino]methyl]piperidine-1-carboxylate Chemical compound C1=C(C(C)(C)C)C=C(NS(C)(=O)=O)C(OC)=C1NC(=O)C1=CC=C(C)C(N2N=NC(=C2)C(=O)NCC2CCN(CC2)C(=O)OC(C)(C)C)=C1 CPXCJMGYKWMJBM-UHFFFAOYSA-N 0.000 claims 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims 1
- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 claims 1
- BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 claims 1
- NNLBRYQGMOYARS-UHFFFAOYSA-N thiane 1-oxide Chemical compound O=S1CCCCC1 NNLBRYQGMOYARS-UHFFFAOYSA-N 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 150000003852 triazoles Chemical class 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43051902P | 2002-11-27 | 2002-11-27 | |
| US60/430,519 | 2002-11-27 | ||
| PCT/US2003/037104 WO2004050642A1 (en) | 2002-11-27 | 2003-11-20 | 1, 2, 3- triazole amide derivatives as cytokine inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006514940A JP2006514940A (ja) | 2006-05-18 |
| JP2006514940A5 true JP2006514940A5 (cg-RX-API-DMAC7.html) | 2007-01-18 |
| JP4926402B2 JP4926402B2 (ja) | 2012-05-09 |
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| JP2004557232A Expired - Lifetime JP4926402B2 (ja) | 2002-11-27 | 2003-11-20 | サイトカインインヒビターとしての１，２，３−トリアゾールアミド誘導体 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US7166628B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1567507B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP4926402B2 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE329909T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU2003294388A1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2507184C (cg-RX-API-DMAC7.html) |
| DE (1) | DE60306193T2 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2265596T3 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2004050642A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7591994B2 (en) * | 2002-12-13 | 2009-09-22 | Immunomedics, Inc. | Camptothecin-binding moiety conjugates |
| ATE501128T1 (de) | 2003-12-03 | 2011-03-15 | Boehringer Ingelheim Pharma | 1,2,3-triazolamidderivate als inhibitoren der cytokinproduktion |
| US7485657B2 (en) | 2004-05-12 | 2009-02-03 | Boehringer Ingelheim Pharmaceuticals, Inc. | Anti-cytokine heterocyclic compounds |
| WO2006109846A1 (ja) * | 2005-04-06 | 2006-10-19 | Takeda Pharmaceutical Company Limited | トリアゾール誘導体およびその用途 |
| CA2608258A1 (en) * | 2005-05-12 | 2006-11-23 | Boehringer Ingelheim International Gmbh | Bis-amination of aryl halides |
| EP1910316B1 (en) * | 2005-07-25 | 2010-11-10 | F. Hoffmann-La Roche AG | Substituted triazole derivatives and their use as neurokinin 3 receptor antagonists |
| MX2008015457A (es) * | 2006-07-07 | 2009-01-16 | Boehringer Ingelheim Int | Derivados de heteroaril substituido en fenil y el uso de los mismos como agentes anti-tumorales. |
| CL2008001943A1 (es) | 2007-07-02 | 2009-09-11 | Boehringer Ingelheim Int | Compuestos derivados de fenil-triazol, inhibidores de enzimas de señales especificas que participan del control de la proliferacion celular; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar cancer, infecciones, enfermedades inflamatorias y autoinmunes. |
| US20100240657A1 (en) * | 2007-07-02 | 2010-09-23 | Boehringer Ingelheim International Gmbh | Chemical compounds |
| AR073501A1 (es) | 2008-09-08 | 2010-11-10 | Boehringer Ingelheim Int | Derivados de pirimido[5,4-d]pirimidina inhibidores de la tirosinoquinasa |
| AU2009295855A1 (en) | 2008-09-29 | 2010-04-01 | Boehringer Ingelheim International Gmbh | Antiproliferative compounds |
| EP2398797B1 (en) | 2009-02-17 | 2013-11-06 | Boehringer Ingelheim International GmbH | Pyrimido[5,4-d]pyrimidine derivatives for the inhibition of tyrosine kinases |
| JP2011057661A (ja) | 2009-08-14 | 2011-03-24 | Bayer Cropscience Ag | 殺虫性カルボキサミド類 |
| EP2552905B1 (en) | 2010-03-26 | 2016-10-05 | Boehringer Ingelheim International GmbH | B-Raf kinase inhibitors |
| EP2552907B1 (en) | 2010-03-26 | 2014-10-22 | Boehringer Ingelheim International GmbH | Pyridyltriazoles |
| US8710055B2 (en) | 2010-12-21 | 2014-04-29 | Boehringer Ingelheim International Gmbh | Triazolylphenyl sulfonamides as serine/threonine kinase inhibitors |
| US8889684B2 (en) | 2011-02-02 | 2014-11-18 | Boehringer Ingelheim International Gmbh | Azaindolylphenyl sulfonamides as serine/threonine kinase inhibitors |
| BR112015012885A2 (pt) * | 2012-12-03 | 2017-07-11 | Hoffmann La Roche | composições triazol e imidazol substituídas |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4302051A1 (de) | 1993-01-26 | 1994-07-28 | Thomae Gmbh Dr K | 5-gliedrige Heterocyclen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| FR2732967B1 (fr) | 1995-04-11 | 1997-07-04 | Sanofi Sa | 1-phenylpyrazole-3-carboxamides substitues, actifs sur la neurotensine, leur preparation, les compositions pharmaceutiques en contenant |
| HUP0104060A3 (en) | 1998-09-25 | 2002-04-29 | Astrazeneca Ab | Benzamide derivatives and their use as cytokine inhibitors, process for their preparation and medicaments containing them |
| PT1123287E (pt) | 1998-10-23 | 2003-12-31 | Dow Agrosciences Llc | 1-(piridil substituido)-1,2,4-triazoles insecticidas |
| UA73492C2 (en) * | 1999-01-19 | 2005-08-15 | Aromatic heterocyclic compounds as antiinflammatory agents | |
| US20010044445A1 (en) | 1999-04-08 | 2001-11-22 | Bamaung Nwe Y. | Azole inhibitors of cytokine production |
| US7297708B2 (en) | 2001-09-06 | 2007-11-20 | Bristol-Myers Squibb Company | Heteroaromatic substituted cyclopropane as corticotropin releasing hormone ligands |
| US7253190B2 (en) | 2001-10-04 | 2007-08-07 | Merck & Co., Inc. | Heteroaryl substituted tetrazole modulators of metabotrophic glutamate receptor-5 |
| ATE511840T1 (de) | 2001-10-09 | 2011-06-15 | Amgen Inc | Imidazolderivate als entzündungshemmende mittel |
| AU2003209388A1 (en) | 2002-01-29 | 2003-09-02 | Merck And Co., Inc. | Substituted imidazoles as cannabinoid receptor modulators |
| ATE501128T1 (de) * | 2003-12-03 | 2011-03-15 | Boehringer Ingelheim Pharma | 1,2,3-triazolamidderivate als inhibitoren der cytokinproduktion |
| US7485657B2 (en) * | 2004-05-12 | 2009-02-03 | Boehringer Ingelheim Pharmaceuticals, Inc. | Anti-cytokine heterocyclic compounds |
-
2003
- 2003-11-20 ES ES03789871T patent/ES2265596T3/es not_active Expired - Lifetime
- 2003-11-20 AT AT03789871T patent/ATE329909T1/de active
- 2003-11-20 JP JP2004557232A patent/JP4926402B2/ja not_active Expired - Lifetime
- 2003-11-20 WO PCT/US2003/037104 patent/WO2004050642A1/en not_active Ceased
- 2003-11-20 EP EP03789871A patent/EP1567507B1/en not_active Expired - Lifetime
- 2003-11-20 DE DE60306193T patent/DE60306193T2/de not_active Expired - Lifetime
- 2003-11-20 US US10/718,380 patent/US7166628B2/en not_active Expired - Lifetime
- 2003-11-20 AU AU2003294388A patent/AU2003294388A1/en not_active Abandoned
- 2003-11-20 CA CA2507184A patent/CA2507184C/en not_active Expired - Lifetime
-
2006
- 2006-09-07 US US11/470,849 patent/US7569568B2/en not_active Expired - Lifetime
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