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 |
|---|---|---|---|---|
| EP1438295B1 (en) * | 2001-10-23 | 2012-08-15 | Merck Serono SA | Azole derivatives and pharmaceutical compositions containing them |
| MX2007004781A (es) | 2004-10-20 | 2007-05-11 | Applied Research Systems | Derivados de 3-arilamino piridina. |
| US8546404B2 (en) | 2005-12-13 | 2013-10-01 | Merck Sharp & Dohme | Compounds that are ERK inhibitors |
| MX2008010635A (es) | 2006-02-16 | 2008-10-28 | Schering Corp | Derivados de pirrolidina como inhibidores de cinasa regulada por señales extracelulares. |
| WO2009105500A1 (en) | 2008-02-21 | 2009-08-27 | Schering Corporation | Compounds that are erk inhibitors |
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| WO2015041534A1 (en) | 2013-09-20 | 2015-03-26 | Stichting Het Nederlands Kanker Instituut | P90rsk in combination with raf/erk/mek |
| EP3046557A1 (en) | 2013-09-20 | 2016-07-27 | Stichting Het Nederlands Kanker Instituut | Rock in combination with mapk-pathway |
| US20170027940A1 (en) | 2014-04-10 | 2017-02-02 | 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 |
| JP7725076B2 (ja) | 2020-04-28 | 2025-08-19 | ザ・リージェンツ・オブ・ザ・ユニバーシティ・オブ・ミシガン | グルコシルセラミド合成酵素のピリジン阻害剤及びそれらを使用する治療方法 |
| 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 |
| 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 |
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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 |
| CA2328927C (en) | 1998-05-15 | 2008-02-19 | Astrazeneca Ab | Benzamide derivatives for the treatment of diseases mediated by cytokines |
| JP2003525201A (ja) * | 1998-08-20 | 2003-08-26 | スミスクライン・ビーチャム・コーポレイション | 新規な置換トリアゾール化合物 |
| HUP0105092A3 (en) * | 1999-01-13 | 2003-12-29 | Warner Lambert Co | 1-heterocycle substituted diarylamines and medicaments containing them |
| EP1438295B1 (en) * | 2001-10-23 | 2012-08-15 | Merck Serono SA | Azole derivatives and pharmaceutical compositions containing them |
-
2002
- 2002-10-23 EP EP02793814A patent/EP1438295B1/en not_active Expired - Lifetime
- 2002-10-23 IL IL16158002A patent/IL161580A0/xx unknown
- 2002-10-23 JP JP2003538142A patent/JP4602667B2/ja not_active Expired - Fee Related
- 2002-10-23 WO PCT/US2002/033963 patent/WO2003035626A2/en not_active Ceased
- 2002-10-23 EP EP10075495A patent/EP2332922A1/en not_active Withdrawn
- 2002-10-23 US US10/491,902 patent/US7253199B2/en not_active Expired - Fee Related
- 2002-10-23 ES ES02793814T patent/ES2393186T3/es not_active Expired - Lifetime
- 2002-10-23 AU AU2002359291A patent/AU2002359291C1/en not_active Ceased
- 2002-10-23 CA CA002463101A patent/CA2463101A1/en not_active Abandoned
-
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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