JP2005508972A5 - - Google Patents
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- Publication number
- JP2005508972A5 JP2005508972A5 JP2003538142A JP2003538142A JP2005508972A5 JP 2005508972 A5 JP2005508972 A5 JP 2005508972A5 JP 2003538142 A JP2003538142 A JP 2003538142A JP 2003538142 A JP2003538142 A JP 2003538142A JP 2005508972 A5 JP2005508972 A5 JP 2005508972A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- alkyl
- imidazol
- iodo
- ylmethyl
- 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 72
- 125000001072 heteroaryl group Chemical group 0.000 claims 38
- 229910052799 carbon Inorganic materials 0.000 claims 37
- 150000001875 compounds Chemical class 0.000 claims 36
- 229910052739 hydrogen Inorganic materials 0.000 claims 27
- 125000003118 aryl group Chemical group 0.000 claims 23
- 229910052736 halogen Inorganic materials 0.000 claims 23
- 150000002367 halogens Chemical class 0.000 claims 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 14
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims 11
- 125000004404 heteroalkyl group Chemical group 0.000 claims 11
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 11
- 125000000547 substituted alkyl group Chemical group 0.000 claims 11
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 11
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 8
- 125000002723 alicyclic group Chemical group 0.000 claims 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 7
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- 125000006413 ring segment Chemical group 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- -1 1-imidazol-1-ylmethyl Chemical group 0.000 claims 3
- 125000001589 carboacyl group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 208000035143 Bacterial infection Diseases 0.000 claims 2
- 208000023328 Basedow disease Diseases 0.000 claims 2
- 206010007572 Cardiac hypertrophy Diseases 0.000 claims 2
- 208000006029 Cardiomegaly Diseases 0.000 claims 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 208000007882 Gastritis Diseases 0.000 claims 2
- 206010018364 Glomerulonephritis Diseases 0.000 claims 2
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 2
- 208000015023 Graves' disease Diseases 0.000 claims 2
- 206010020751 Hypersensitivity Diseases 0.000 claims 2
- 206010021143 Hypoxia Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 206010029113 Neovascularisation Diseases 0.000 claims 2
- 206010030113 Oedema Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 206010033645 Pancreatitis Diseases 0.000 claims 2
- 208000005107 Premature Birth Diseases 0.000 claims 2
- 206010036590 Premature baby Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 206010037660 Pyrexia Diseases 0.000 claims 2
- 206010039710 Scleroderma Diseases 0.000 claims 2
- 206010040070 Septic Shock Diseases 0.000 claims 2
- 108090000190 Thrombin Proteins 0.000 claims 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 230000007815 allergy Effects 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 230000001580 bacterial effect Effects 0.000 claims 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 208000001848 dysentery Diseases 0.000 claims 2
- 208000024908 graft versus host disease Diseases 0.000 claims 2
- 201000011066 hemangioma Diseases 0.000 claims 2
- 208000007475 hemolytic anemia Diseases 0.000 claims 2
- 206010020718 hyperplasia Diseases 0.000 claims 2
- 208000018875 hypoxemia Diseases 0.000 claims 2
- 208000000509 infertility Diseases 0.000 claims 2
- 230000036512 infertility Effects 0.000 claims 2
- 231100000535 infertility Toxicity 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 208000028867 ischemia Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 210000000056 organ Anatomy 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 150000003180 prostaglandins Chemical class 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 230000036303 septic shock Effects 0.000 claims 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims 2
- 229960004072 thrombin Drugs 0.000 claims 2
- 206010043778 thyroiditis Diseases 0.000 claims 2
- 230000002792 vascular Effects 0.000 claims 2
- UHZIEFLWILBLGZ-UHFFFAOYSA-N (1-imidazol-1-yl-3-methoxypropan-2-yl) 4-iodobenzoate Chemical compound C=1C=C(I)C=CC=1C(=O)OC(COC)CN1C=CN=C1 UHZIEFLWILBLGZ-UHFFFAOYSA-N 0.000 claims 1
- CVSDGUSPTSMQBJ-UHFFFAOYSA-N (1-imidazol-1-yl-3-phenoxypropan-2-yl) 3-methoxybenzoate Chemical compound COC1=CC=CC(C(=O)OC(COC=2C=CC=CC=2)CN2C=NC=C2)=C1 CVSDGUSPTSMQBJ-UHFFFAOYSA-N 0.000 claims 1
- WXGSSMRODDWZFH-UHFFFAOYSA-N (1-imidazol-1-yl-3-phenoxypropan-2-yl) 4-(trifluoromethyl)benzoate Chemical compound C1=CC(C(F)(F)F)=CC=C1C(=O)OC(CN1C=NC=C1)COC1=CC=CC=C1 WXGSSMRODDWZFH-UHFFFAOYSA-N 0.000 claims 1
- FULGRUKJYJWJDF-UHFFFAOYSA-N (1-imidazol-1-yl-3-phenoxypropan-2-yl) 4-bromo-2-chlorobenzoate Chemical compound ClC1=CC(Br)=CC=C1C(=O)OC(CN1C=NC=C1)COC1=CC=CC=C1 FULGRUKJYJWJDF-UHFFFAOYSA-N 0.000 claims 1
- FCNIAPWYVGTYIT-UHFFFAOYSA-N (1-imidazol-1-yl-3-phenoxypropan-2-yl) 4-bromobenzoate Chemical compound C1=CC(Br)=CC=C1C(=O)OC(CN1C=NC=C1)COC1=CC=CC=C1 FCNIAPWYVGTYIT-UHFFFAOYSA-N 0.000 claims 1
- ZRFIFBBEQSGQFS-UHFFFAOYSA-N (1-imidazol-1-yl-3-phenoxypropan-2-yl) 4-fluorobenzoate Chemical compound C1=CC(F)=CC=C1C(=O)OC(CN1C=NC=C1)COC1=CC=CC=C1 ZRFIFBBEQSGQFS-UHFFFAOYSA-N 0.000 claims 1
- QQRKJVIRHXDXHB-UHFFFAOYSA-N (1-imidazol-1-yl-3-phenoxypropan-2-yl) 4-methoxybenzoate Chemical compound C1=CC(OC)=CC=C1C(=O)OC(CN1C=NC=C1)COC1=CC=CC=C1 QQRKJVIRHXDXHB-UHFFFAOYSA-N 0.000 claims 1
- SJCCMELPLHYEQU-UHFFFAOYSA-N (1-imidazol-1-yl-3-phenoxypropan-2-yl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC(CN1C=NC=C1)COC1=CC=CC=C1 SJCCMELPLHYEQU-UHFFFAOYSA-N 0.000 claims 1
- CTQRYNQVNOXJOQ-UHFFFAOYSA-N (1-imidazol-1-yl-3-pyridin-3-yloxypropan-2-yl) 4-iodobenzoate Chemical compound C1=CC(I)=CC=C1C(=O)OC(CN1C=NC=C1)COC1=CC=CN=C1 CTQRYNQVNOXJOQ-UHFFFAOYSA-N 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims 1
- HJMOACBJSLAGME-UHFFFAOYSA-N 2-chloro-n-(1-imidazol-1-yl-3-pyridin-3-yloxypropan-2-yl)-4-iodobenzamide Chemical compound ClC1=CC(I)=CC=C1C(=O)NC(CN1C=NC=C1)COC1=CC=CN=C1 HJMOACBJSLAGME-UHFFFAOYSA-N 0.000 claims 1
- DKDCTJRPQBGCFM-UHFFFAOYSA-N 2-chloro-n-[1-(4-fluorophenoxy)-3-imidazol-1-ylpropan-2-yl]-4-iodobenzamide Chemical compound C1=CC(F)=CC=C1OCC(NC(=O)C=1C(=CC(I)=CC=1)Cl)CN1C=NC=C1 DKDCTJRPQBGCFM-UHFFFAOYSA-N 0.000 claims 1
- AQABPIBXKWPEIJ-UHFFFAOYSA-N [1-(2-methylimidazol-1-yl)-3-(oxan-2-yloxy)propan-2-yl] 4-iodobenzoate Chemical compound CC1=NC=CN1CC(OC(=O)C=1C=CC(I)=CC=1)COC1OCCCC1 AQABPIBXKWPEIJ-UHFFFAOYSA-N 0.000 claims 1
- VTSBOMMVBCCYNZ-UHFFFAOYSA-N [1-(4-acetamidophenoxy)-3-imidazol-1-ylpropan-2-yl] 4-iodobenzoate Chemical compound C1=CC(NC(=O)C)=CC=C1OCC(OC(=O)C=1C=CC(I)=CC=1)CN1C=NC=C1 VTSBOMMVBCCYNZ-UHFFFAOYSA-N 0.000 claims 1
- DKQCXNIDGIPIBX-UHFFFAOYSA-N [1-(4-cyanophenoxy)-3-(2-methylimidazol-1-yl)propan-2-yl] 4-iodobenzoate Chemical compound CC1=NC=CN1CC(OC(=O)C=1C=CC(I)=CC=1)COC1=CC=C(C#N)C=C1 DKQCXNIDGIPIBX-UHFFFAOYSA-N 0.000 claims 1
- GVKYQAMIWRBSJC-UHFFFAOYSA-N [1-(4-cyanophenoxy)-3-imidazol-1-ylpropan-2-yl] 4-iodobenzoate Chemical compound C1=CC(I)=CC=C1C(=O)OC(CN1C=NC=C1)COC1=CC=C(C#N)C=C1 GVKYQAMIWRBSJC-UHFFFAOYSA-N 0.000 claims 1
- JTNXYKMQMWRALS-UHFFFAOYSA-N [1-(4-fluorophenoxy)-3-(1,2,4-triazol-1-yl)propan-2-yl] 4-iodobenzoate Chemical compound C1=CC(F)=CC=C1OCC(OC(=O)C=1C=CC(I)=CC=1)CN1N=CN=C1 JTNXYKMQMWRALS-UHFFFAOYSA-N 0.000 claims 1
- MYYLIMLHXIIIMZ-UHFFFAOYSA-N [1-(4-fluorophenoxy)-3-imidazol-1-ylpropan-2-yl] 2,4-dichlorobenzoate Chemical compound C1=CC(F)=CC=C1OCC(OC(=O)C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 MYYLIMLHXIIIMZ-UHFFFAOYSA-N 0.000 claims 1
- SGWCLRZNWVPFJX-UHFFFAOYSA-N [1-(4-fluorophenoxy)-3-imidazol-1-ylpropan-2-yl] 4-iodobenzoate Chemical compound C1=CC(F)=CC=C1OCC(OC(=O)C=1C=CC(I)=CC=1)CN1C=NC=C1 SGWCLRZNWVPFJX-UHFFFAOYSA-N 0.000 claims 1
- VUIUMNPJDNTIKP-UHFFFAOYSA-N [1-(4-fluorophenoxy)-3-imidazol-1-ylpropan-2-yl] 4-methoxybenzoate Chemical compound C1=CC(OC)=CC=C1C(=O)OC(CN1C=NC=C1)COC1=CC=C(F)C=C1 VUIUMNPJDNTIKP-UHFFFAOYSA-N 0.000 claims 1
- ZQSZSWQNEFVKGG-UHFFFAOYSA-N [1-(cyclopropylmethoxy)-3-(2-methylimidazol-1-yl)propan-2-yl] 2-chloro-4-iodobenzoate Chemical compound CC1=NC=CN1CC(OC(=O)C=1C(=CC(I)=CC=1)Cl)COCC1CC1 ZQSZSWQNEFVKGG-UHFFFAOYSA-N 0.000 claims 1
- GUUSBVNDBCVAIS-UHFFFAOYSA-N [1-imidazol-1-yl-3-(2-nitrophenoxy)propan-2-yl] 4-iodobenzoate Chemical compound [O-][N+](=O)C1=CC=CC=C1OCC(OC(=O)C=1C=CC(I)=CC=1)CN1C=NC=C1 GUUSBVNDBCVAIS-UHFFFAOYSA-N 0.000 claims 1
- YOPNHJJETCAFCE-UHFFFAOYSA-N [1-imidazol-1-yl-3-(3-nitrophenoxy)propan-2-yl] 4-iodobenzoate Chemical compound [O-][N+](=O)C1=CC=CC(OCC(CN2C=NC=C2)OC(=O)C=2C=CC(I)=CC=2)=C1 YOPNHJJETCAFCE-UHFFFAOYSA-N 0.000 claims 1
- XCWWZSYUAYVVMT-UHFFFAOYSA-N [1-imidazol-1-yl-3-(4-iodophenoxy)propan-2-yl] 4-bromo-2-chlorobenzoate Chemical compound C1=CC(=CC=C1OCC(CN2C=CN=C2)OC(=O)C3=C(C=C(C=C3)Br)Cl)I XCWWZSYUAYVVMT-UHFFFAOYSA-N 0.000 claims 1
- CCKLUXJAXAWORF-UHFFFAOYSA-N [1-imidazol-1-yl-3-(4-iodophenoxy)propan-2-yl] 4-iodobenzoate Chemical compound C1=CC(I)=CC=C1OCC(OC(=O)C=1C=CC(I)=CC=1)CN1C=NC=C1 CCKLUXJAXAWORF-UHFFFAOYSA-N 0.000 claims 1
- LZBOKYSSRYQASV-UHFFFAOYSA-N [1-imidazol-1-yl-3-(4-iodophenoxy)propan-2-yl] 4-methoxybenzoate Chemical compound COC1=CC=C(C=C1)C(=O)OC(CN2C=CN=C2)COC3=CC=C(C=C3)I LZBOKYSSRYQASV-UHFFFAOYSA-N 0.000 claims 1
- DPTLLKCIWYDYRY-UHFFFAOYSA-N [1-imidazol-1-yl-3-(4-methoxyphenoxy)propan-2-yl] 4-methoxybenzoate Chemical compound C1=CC(OC)=CC=C1OCC(OC(=O)C=1C=CC(OC)=CC=1)CN1C=NC=C1 DPTLLKCIWYDYRY-UHFFFAOYSA-N 0.000 claims 1
- JTWITXSRBQCTHA-UHFFFAOYSA-N [1-imidazol-1-yl-3-(4-nitrophenoxy)propan-2-yl] 4-iodobenzoate Chemical compound C1=CC([N+](=O)[O-])=CC=C1OCC(OC(=O)C=1C=CC(I)=CC=1)CN1C=NC=C1 JTWITXSRBQCTHA-UHFFFAOYSA-N 0.000 claims 1
- DRHNPUWRASFLHB-UHFFFAOYSA-N [3-imidazol-1-yl-2-(4-iodobenzoyl)oxy-2-methylpropyl] 4-nitrobenzoate Chemical compound C1=CN=CN1CC(OC(=O)C=1C=CC(I)=CC=1)(C)COC(=O)C1=CC=C([N+]([O-])=O)C=C1 DRHNPUWRASFLHB-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- DLSUFMMWXXPUHP-UHFFFAOYSA-N n-(1-imidazol-1-yl-3-phenoxypropan-2-yl)-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC(CN1C=NC=C1)COC1=CC=CC=C1 DLSUFMMWXXPUHP-UHFFFAOYSA-N 0.000 claims 1
- QAWIWTFXLCFEOO-UHFFFAOYSA-N n-(1-imidazol-1-yl-3-pyridin-3-yloxypropan-2-yl)-4-iodobenzamide Chemical compound C1=CC(I)=CC=C1C(=O)NC(CN1C=NC=C1)COC1=CC=CN=C1 QAWIWTFXLCFEOO-UHFFFAOYSA-N 0.000 claims 1
- SVOVZDKVCARNGV-UHFFFAOYSA-N n-(3-imidazol-1-yl-2-phenoxypropyl)-4-iodo-n-methylbenzamide Chemical compound C=1C=C(I)C=CC=1C(=O)N(C)CC(OC=1C=CC=CC=1)CN1C=CN=C1 SVOVZDKVCARNGV-UHFFFAOYSA-N 0.000 claims 1
- IQBUWEXLNJURKA-UHFFFAOYSA-N n-[1-(2-chloroimidazol-1-yl)-3-(4-cyanophenoxy)propan-2-yl]-4-iodobenzamide Chemical compound ClC1=NC=CN1CC(NC(=O)C=1C=CC(I)=CC=1)COC1=CC=C(C#N)C=C1 IQBUWEXLNJURKA-UHFFFAOYSA-N 0.000 claims 1
- ZBIMAVFHIWZMKT-UHFFFAOYSA-N n-[1-(2-chloroimidazol-1-yl)-3-(4-fluorophenoxy)propan-2-yl]-4-iodobenzamide Chemical compound C1=CC(F)=CC=C1OCC(NC(=O)C=1C=CC(I)=CC=1)CN1C(Cl)=NC=C1 ZBIMAVFHIWZMKT-UHFFFAOYSA-N 0.000 claims 1
- QFSOXHYEFJFLIL-UHFFFAOYSA-N n-[1-(3-cyanopyridin-2-yl)oxy-3-imidazol-1-ylpropan-2-yl]-4-iodobenzamide Chemical compound C1=CC(I)=CC=C1C(=O)NC(CN1C=NC=C1)COC1=NC=CC=C1C#N QFSOXHYEFJFLIL-UHFFFAOYSA-N 0.000 claims 1
- AQPCOTGUGIETJG-UHFFFAOYSA-N n-[1-(4-cyanophenoxy)-3-(2-methylimidazol-1-yl)propan-2-yl]-4-iodobenzamide Chemical compound CC1=NC=CN1CC(NC(=O)C=1C=CC(I)=CC=1)COC1=CC=C(C#N)C=C1 AQPCOTGUGIETJG-UHFFFAOYSA-N 0.000 claims 1
- VNJZUFANCKZCQJ-UHFFFAOYSA-N n-[1-(4-cyanophenoxy)-3-imidazol-1-ylpropan-2-yl]-4-iodobenzamide Chemical compound C1=CC(I)=CC=C1C(=O)NC(CN1C=NC=C1)COC1=CC=C(C#N)C=C1 VNJZUFANCKZCQJ-UHFFFAOYSA-N 0.000 claims 1
- NCRBSVCFQVEWOV-UHFFFAOYSA-N n-[1-(4-fluorophenoxy)-3-(1,2,4-triazol-1-yl)propan-2-yl]-4-iodobenzamide Chemical compound C1=CC(F)=CC=C1OCC(NC(=O)C=1C=CC(I)=CC=1)CN1N=CN=C1 NCRBSVCFQVEWOV-UHFFFAOYSA-N 0.000 claims 1
- QLLXRCLKWKJALI-UHFFFAOYSA-N n-[1-(4-fluorophenoxy)-3-(2-phenylimidazol-1-yl)propan-2-yl]-4-iodobenzamide Chemical compound C1=CC(F)=CC=C1OCC(NC(=O)C=1C=CC(I)=CC=1)CN1C(C=2C=CC=CC=2)=NC=C1 QLLXRCLKWKJALI-UHFFFAOYSA-N 0.000 claims 1
- FDVQXBWOPAKJQL-UHFFFAOYSA-N n-[1-(4-fluorophenoxy)-3-(tetrazol-1-yl)propan-2-yl]-4-iodobenzamide Chemical compound C1=CC(F)=CC=C1OCC(NC(=O)C=1C=CC(I)=CC=1)CN1N=NN=C1 FDVQXBWOPAKJQL-UHFFFAOYSA-N 0.000 claims 1
- KQZATCYBCYMUDZ-UHFFFAOYSA-N n-[1-(4-fluorophenoxy)-3-imidazol-1-ylpropan-2-yl]-3-iodobenzamide Chemical compound C1=CC(F)=CC=C1OCC(NC(=O)C=1C=C(I)C=CC=1)CN1C=NC=C1 KQZATCYBCYMUDZ-UHFFFAOYSA-N 0.000 claims 1
- YKSRQAMHHKDSQI-UHFFFAOYSA-N n-[1-(4-fluorophenoxy)-3-imidazol-1-ylpropan-2-yl]-4-iodobenzamide Chemical compound C1=CC(F)=CC=C1OCC(NC(=O)C=1C=CC(I)=CC=1)CN1C=NC=C1 YKSRQAMHHKDSQI-UHFFFAOYSA-N 0.000 claims 1
- HWDXDASZYYWECJ-UHFFFAOYSA-N n-[1-(4-tert-butylphenoxy)-3-imidazol-1-ylpropan-2-yl]-4-iodobenzamide Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC(NC(=O)C=1C=CC(I)=CC=1)CN1C=NC=C1 HWDXDASZYYWECJ-UHFFFAOYSA-N 0.000 claims 1
- ASKHKPOODHCNAG-UHFFFAOYSA-N n-[1-(5-cyanopyridin-2-yl)oxy-3-imidazol-1-ylpropan-2-yl]-4-iodobenzamide Chemical compound C1=CC(I)=CC=C1C(=O)NC(CN1C=NC=C1)COC1=CC=C(C#N)C=N1 ASKHKPOODHCNAG-UHFFFAOYSA-N 0.000 claims 1
- GCMCUFFVCDXDEZ-UHFFFAOYSA-N n-[1-[2-(difluoromethyl)imidazol-1-yl]-3-(4-fluorophenoxy)propan-2-yl]-4-iodobenzamide Chemical compound FC(F)C1=NC=CN1CC(NC(=O)C=1C=CC(I)=CC=1)COC1=CC=C(F)C=C1 GCMCUFFVCDXDEZ-UHFFFAOYSA-N 0.000 claims 1
- WRRJDCHXJQQHLW-UHFFFAOYSA-N n-[1-imidazol-1-yl-3-(3-nitropyridin-2-yl)oxypropan-2-yl]-4-iodobenzamide Chemical compound [O-][N+](=O)C1=CC=CN=C1OCC(NC(=O)C=1C=CC(I)=CC=1)CN1C=NC=C1 WRRJDCHXJQQHLW-UHFFFAOYSA-N 0.000 claims 1
- VDXFXTGIYZVGPA-UHFFFAOYSA-N n-[1-imidazol-1-yl-3-(4-nitrophenoxy)propan-2-yl]-4-iodobenzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1OCC(NC(=O)C=1C=CC(I)=CC=1)CN1C=NC=C1 VDXFXTGIYZVGPA-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33604001P | 2001-10-23 | 2001-10-23 | |
| PCT/US2002/033963 WO2003035626A2 (en) | 2001-10-23 | 2002-10-23 | Azole derivatives and pharmaceutical compositions containing them |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005508972A JP2005508972A (ja) | 2005-04-07 |
| JP2005508972A5 true JP2005508972A5 (https=) | 2006-01-05 |
| JP4602667B2 JP4602667B2 (ja) | 2010-12-22 |
Family
ID=23314305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003538142A Expired - Fee Related JP4602667B2 (ja) | 2001-10-23 | 2002-10-23 | アゾール誘導体および該アゾール誘導体を含有する医薬組成物 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US7253199B2 (https=) |
| EP (2) | EP1438295B1 (https=) |
| JP (1) | JP4602667B2 (https=) |
| AU (2) | AU2002359291C1 (https=) |
| CA (1) | CA2463101A1 (https=) |
| ES (1) | ES2393186T3 (https=) |
| IL (1) | IL161580A0 (https=) |
| WO (1) | WO2003035626A2 (https=) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4602667B2 (ja) * | 2001-10-23 | 2010-12-22 | メルク セローノ ソシエテ アノニム | アゾール誘導体および該アゾール誘導体を含有する医薬組成物 |
| ZA200703912B (en) | 2004-10-20 | 2008-09-25 | Serono Lab | 3-arylamino pyridine derivatives |
| US8546404B2 (en) | 2005-12-13 | 2013-10-01 | Merck Sharp & Dohme | Compounds that are ERK inhibitors |
| JP2009528280A (ja) | 2006-02-16 | 2009-08-06 | シェーリング コーポレイション | Ｅｒｋインヒビターとしてのピロリジン誘導体 |
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| BR112012022801B8 (pt) | 2010-03-09 | 2019-10-29 | Dana Farber Cancer Inst Inc | método de identificar um indivíduo que tem câncer que é provável beneficiar-se do tratamento com uma terapia de combinação com um inibidor de raf e um segundo inibidor e uso de um inibidor de raf e um segundo inibidor para a fabricação de um medicamento para tratar câncer |
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| 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 |
| WO2015156674A2 (en) | 2014-04-10 | 2015-10-15 | Stichting Het Nederlands Kanker Instituut | Method for treating cancer |
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| 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 |
| BR112022001678A2 (pt) * | 2019-07-30 | 2022-05-03 | Edvince Ab | Inibidor mek, uso de um inibidor mek, método de tratar ou reduzir o risco de desenvolver um acidente vascular cerebral em um sujeito, composição, e, kit de partes |
| CN110845703A (zh) * | 2019-10-28 | 2020-02-28 | 上海瀚岱化学有限公司 | 一种水性环氧树脂及其制备方法 |
| CN110903735A (zh) * | 2019-11-11 | 2020-03-24 | 上海瀚岱化学有限公司 | 一种水性环氧涂料及其制备方法与应用 |
| EP4142878B1 (en) | 2020-04-28 | 2024-06-26 | The Regents of The University of Michigan | Pyridine inhibitors of glucosylceramide synthase and therapeutic methods using the same |
| CN112794989A (zh) * | 2020-12-18 | 2021-05-14 | 江西瀚泰新材料科技有限公司 | 一种增韧阻燃水性环氧树脂及其制备方法 |
| CN112646123A (zh) * | 2020-12-18 | 2021-04-13 | 江西瀚泰新材料科技有限公司 | 一种低粘度水性环氧树脂及其制备方法 |
| CN112759742A (zh) * | 2020-12-18 | 2021-05-07 | 江西瀚泰新材料科技有限公司 | 一种增韧型水性环氧树脂及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1271477A (en) * | 1983-11-18 | 1990-07-10 | John F. Gerster | 1h-imidazo[4,5-c]quinolin-4-amines |
| PL195600B1 (pl) | 1998-05-15 | 2007-10-31 | Astrazeneca Ab | Pochodne benzamidowe, sposób ich wytwarzania, zawierające je kompozycje farmaceutyczne oraz ich zastosowanie do wytwarzania leku do leczenia stanów medycznych powstających za pośrednictwem cytokin |
| CA2341370A1 (en) * | 1998-08-20 | 2000-03-02 | Smithkline Beecham Corporation | Novel substituted triazole compounds |
| DE69926914T2 (de) * | 1999-01-13 | 2006-06-29 | Warner-Lambert Co. Llc | 1-heterozyklus-substituierte diarylaminen |
| JP4602667B2 (ja) * | 2001-10-23 | 2010-12-22 | メルク セローノ ソシエテ アノニム | アゾール誘導体および該アゾール誘導体を含有する医薬組成物 |
-
2002
- 2002-10-23 JP JP2003538142A patent/JP4602667B2/ja not_active Expired - Fee Related
- 2002-10-23 EP EP02793814A patent/EP1438295B1/en not_active Expired - Lifetime
- 2002-10-23 ES ES02793814T patent/ES2393186T3/es not_active Expired - Lifetime
- 2002-10-23 EP EP10075495A patent/EP2332922A1/en not_active Withdrawn
- 2002-10-23 AU AU2002359291A patent/AU2002359291C1/en not_active Ceased
- 2002-10-23 CA CA002463101A patent/CA2463101A1/en not_active Abandoned
- 2002-10-23 US US10/491,902 patent/US7253199B2/en not_active Expired - Fee Related
- 2002-10-23 IL IL16158002A patent/IL161580A0/xx unknown
- 2002-10-23 WO PCT/US2002/033963 patent/WO2003035626A2/en not_active Ceased
-
2007
- 2007-07-24 US US11/782,251 patent/US7541375B2/en not_active Expired - Fee Related
-
2008
- 2008-06-20 AU AU2008202731A patent/AU2008202731A1/en not_active Abandoned
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