JP2019532929A5 - - Google Patents
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- JP2019532929A5 JP2019532929A5 JP2019515286A JP2019515286A JP2019532929A5 JP 2019532929 A5 JP2019532929 A5 JP 2019532929A5 JP 2019515286 A JP2019515286 A JP 2019515286A JP 2019515286 A JP2019515286 A JP 2019515286A JP 2019532929 A5 JP2019532929 A5 JP 2019532929A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkyloxy
- methyl
- fluorophenyl
- triazole
- 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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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 198
- 125000003545 alkoxy group Chemical group 0.000 claims description 183
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 120
- 235000019000 fluorine Nutrition 0.000 claims description 95
- 150000001875 compounds Chemical class 0.000 claims description 91
- 229910052736 halogen Inorganic materials 0.000 claims description 88
- 150000002367 halogens Chemical class 0.000 claims description 88
- 150000003839 salts Chemical class 0.000 claims description 74
- 125000001153 fluoro group Chemical group F* 0.000 claims description 70
- 229910052757 nitrogen Inorganic materials 0.000 claims description 64
- 125000003118 aryl group Chemical group 0.000 claims description 55
- 229910052731 fluorine Inorganic materials 0.000 claims description 49
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 47
- 125000001424 substituent group Chemical group 0.000 claims description 40
- 239000011737 fluorine Substances 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 125000005842 heteroatom Chemical group 0.000 claims description 29
- 229910052760 oxygen Inorganic materials 0.000 claims description 29
- 229910052717 sulfur Inorganic materials 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 27
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 16
- -1 4-Chloro-3-fluorophenyl Chemical group 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 9
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 6
- 208000002814 Autosomal Recessive Polycystic Kidney Diseases 0.000 claims description 6
- 208000017354 Autosomal recessive polycystic kidney disease Diseases 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 208000010061 Autosomal Dominant Polycystic Kidney Diseases 0.000 claims description 5
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 claims description 5
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 claims description 5
- 208000022185 autosomal dominant polycystic kidney disease Diseases 0.000 claims description 5
- 229940095074 cyclic amp Drugs 0.000 claims description 5
- 230000003834 intracellular effect Effects 0.000 claims description 5
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 4
- OJESRSWCSIFOBF-UHFFFAOYSA-N 5-(4-chloro-3-fluorophenyl)-2-[2-(1H-indazol-5-ylmethylamino)-2-oxoethyl]-N-methyl-1,2,4-triazole-3-carboxamide Chemical compound ClC1=C(C=C(C=C1)C1=NN(C(=N1)C(=O)NC)CC(NCC=1C=C2C=NNC2=CC=1)=O)F OJESRSWCSIFOBF-UHFFFAOYSA-N 0.000 claims description 4
- BIVRGRQCQIKJLG-UHFFFAOYSA-N 5-(4-chloro-3-fluorophenyl)-2-[2-[(3-fluorophenyl)methylamino]-2-oxoethyl]-1,2,4-triazole-3-carboxamide Chemical compound ClC1=C(C=C(C=C1)C1=NN(C(=N1)C(=O)N)CC(NCC1=CC(=CC=C1)F)=O)F BIVRGRQCQIKJLG-UHFFFAOYSA-N 0.000 claims description 4
- JVALGWBMYZWXPL-UHFFFAOYSA-N 5-(4-chloro-3-fluorophenyl)-2-[2-[(3-fluorophenyl)methylamino]-2-oxoethyl]-1,2,4-triazole-3-carboxylic acid Chemical compound ClC1=C(C=C(C=C1)C1=NN(C(=N1)C(=O)O)CC(NCC1=CC(=CC=C1)F)=O)F JVALGWBMYZWXPL-UHFFFAOYSA-N 0.000 claims description 4
- FCAAUDJUQRSNGP-UHFFFAOYSA-N 5-(4-chloro-3-fluorophenyl)-2-[2-[(3-fluorophenyl)methylamino]-2-oxoethyl]-N,N-dimethyl-1,2,4-triazole-3-carboxamide Chemical compound ClC1=C(C=C(C=C1)C1=NN(C(=N1)C(=O)N(C)C)CC(NCC1=CC(=CC=C1)F)=O)F FCAAUDJUQRSNGP-UHFFFAOYSA-N 0.000 claims description 4
- FXSLHRDRLRGPNZ-UHFFFAOYSA-N 5-(4-chloro-3-fluorophenyl)-2-[2-[(3-fluorophenyl)methylamino]-2-oxoethyl]-N-(2-methoxyethyl)-1,2,4-triazole-3-carboxamide Chemical compound ClC1=C(C=C(C=C1)C1=NN(C(=N1)C(=O)NCCOC)CC(NCC1=CC(=CC=C1)F)=O)F FXSLHRDRLRGPNZ-UHFFFAOYSA-N 0.000 claims description 4
- OCNMPFKLAXTBSH-UHFFFAOYSA-N 5-(4-chloro-3-fluorophenyl)-2-[2-[(3-fluorophenyl)methylamino]-2-oxoethyl]-N-methyl-1,2,4-triazole-3-carboxamide Chemical compound ClC1=C(C=C(C=C1)C1=NN(C(=N1)C(=O)NC)CC(NCC1=CC(=CC=C1)F)=O)F OCNMPFKLAXTBSH-UHFFFAOYSA-N 0.000 claims description 4
- QTNLWFBOFIMGAZ-UHFFFAOYSA-N 5-(4-chloro-3-fluorophenyl)-2-[2-[(3-fluorophenyl)methylamino]-2-oxoethyl]-N-methylpyrazole-3-carboxamide Chemical compound ClC1=C(C=C(C=C1)C1=NN(C(=C1)C(=O)NC)CC(NCC1=CC(=CC=C1)F)=O)F QTNLWFBOFIMGAZ-UHFFFAOYSA-N 0.000 claims description 4
- AWNBCYHBQWZMRN-UHFFFAOYSA-N 5-(4-chloro-3-fluorophenyl)-2-[2-[(3-methoxyphenyl)methylamino]-2-oxoethyl]-1,2,4-triazole-3-carboxylic acid Chemical compound ClC1=C(C=C(C=C1)C1=NN(C(=N1)C(=O)O)CC(NCC1=CC(=CC=C1)OC)=O)F AWNBCYHBQWZMRN-UHFFFAOYSA-N 0.000 claims description 4
- JOOVUIRKXINRSO-UHFFFAOYSA-N 5-(4-chloro-3-fluorophenyl)-2-[2-[(3-methoxyphenyl)methylamino]-2-oxoethyl]-N,N-dimethyl-1,2,4-triazole-3-carboxamide Chemical compound ClC1=C(C=C(C=C1)C1=NN(C(=N1)C(=O)N(C)C)CC(NCC1=CC(=CC=C1)OC)=O)F JOOVUIRKXINRSO-UHFFFAOYSA-N 0.000 claims description 4
- JDOKNASIVMZGOT-UHFFFAOYSA-N 5-(4-chloro-3-fluorophenyl)-2-[2-[(3-methoxyphenyl)methylamino]-2-oxoethyl]-N-methyl-1,2,4-triazole-3-carboxamide Chemical compound ClC1=C(C=C(C=C1)C1=NN(C(=N1)C(=O)NC)CC(NCC1=CC(=CC=C1)OC)=O)F JDOKNASIVMZGOT-UHFFFAOYSA-N 0.000 claims description 4
- QZYIADZWPUHDMJ-UHFFFAOYSA-N 5-(4-chloro-3-fluorophenyl)-2-[2-[(3-methoxyphenyl)methylamino]-2-oxoethyl]-N-methylpyrazole-3-carboxamide Chemical compound ClC1=C(C=C(C=C1)C1=NN(C(=C1)C(=O)NC)CC(NCC1=CC(=CC=C1)OC)=O)F QZYIADZWPUHDMJ-UHFFFAOYSA-N 0.000 claims description 4
- XJHODZRDLGBLNZ-UHFFFAOYSA-N 5-(4-chloro-3-fluorophenyl)-2-[2-[(3-methoxyphenyl)methylamino]-2-oxoethyl]-N-propan-2-yl-1,2,4-triazole-3-carboxamide Chemical compound ClC1=C(C=C(C=C1)C1=NN(C(=N1)C(=O)NC(C)C)CC(NCC1=CC(=CC=C1)OC)=O)F XJHODZRDLGBLNZ-UHFFFAOYSA-N 0.000 claims description 4
- QRDARZAMJDNDDN-UHFFFAOYSA-N 5-(4-chloro-3-fluorophenyl)-N-(2-methoxyethyl)-2-[2-[(3-methoxyphenyl)methylamino]-2-oxoethyl]-1,2,4-triazole-3-carboxamide Chemical compound ClC1=C(C=C(C=C1)C1=NN(C(=N1)C(=O)NCCOC)CC(NCC1=CC(=CC=C1)OC)=O)F QRDARZAMJDNDDN-UHFFFAOYSA-N 0.000 claims description 4
- HPDJIOGCSFUCPL-UHFFFAOYSA-N 5-(4-chloro-3-fluorophenyl)-N-cyclohexyl-2-[2-[(3-fluorophenyl)methylamino]-2-oxoethyl]-1,2,4-triazole-3-carboxamide Chemical compound ClC1=C(C=C(C=C1)C1=NN(C(=N1)C(=O)NC1CCCCC1)CC(NCC1=CC(=CC=C1)F)=O)F HPDJIOGCSFUCPL-UHFFFAOYSA-N 0.000 claims description 4
- GELNTJMQFLMPAM-UHFFFAOYSA-N 5-(4-chloro-3-fluorophenyl)-N-ethyl-2-[2-[(3-fluorophenyl)methylamino]-2-oxoethyl]-1,2,4-triazole-3-carboxamide Chemical compound ClC1=C(C=C(C=C1)C1=NN(C(=N1)C(=O)NCC)CC(NCC1=CC(=CC=C1)F)=O)F GELNTJMQFLMPAM-UHFFFAOYSA-N 0.000 claims description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
- 108091006027 G proteins Proteins 0.000 claims description 4
- 102000030782 GTP binding Human genes 0.000 claims description 4
- 108091000058 GTP-Binding Proteins 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 206010060862 Prostate cancer Diseases 0.000 claims description 4
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- VLMFIBVSDIFJNS-UHFFFAOYSA-N ethyl 2-[2-(benzylamino)-2-oxoethyl]-5-(4-chloro-3-fluorophenyl)-1,2,4-triazole-3-carboxylate Chemical compound C(C1=CC=CC=C1)NC(=O)CN1N=C(N=C1C(=O)OCC)C1=CC(=C(C=C1)Cl)F VLMFIBVSDIFJNS-UHFFFAOYSA-N 0.000 claims description 4
- PNDORJQDFBXYIY-UHFFFAOYSA-N ethyl 5-(4-chloro-3-fluorophenyl)-2-[2-[(3-fluorophenyl)methylamino]-2-oxoethyl]-1,2,4-triazole-3-carboxylate Chemical compound ClC1=C(C=C(C=C1)C1=NN(C(=N1)C(=O)OCC)CC(NCC1=CC(=CC=C1)F)=O)F PNDORJQDFBXYIY-UHFFFAOYSA-N 0.000 claims description 4
- VNHUUMMAEDBYDJ-UHFFFAOYSA-N ethyl 5-(4-chloro-3-fluorophenyl)-2-[2-[(3-methoxyphenyl)methylamino]-2-oxoethyl]-1,2,4-triazole-3-carboxylate Chemical compound ClC1=C(C=C(C=C1)C1=NN(C(=N1)C(=O)OCC)CC(NCC1=CC(=CC=C1)OC)=O)F VNHUUMMAEDBYDJ-UHFFFAOYSA-N 0.000 claims description 4
- DMURHOFPENMMSF-UHFFFAOYSA-N ethyl 5-(4-chlorophenyl)-2-[2-[(3-fluorophenyl)methylamino]-2-oxoethyl]pyrazole-3-carboxylate Chemical compound ClC1=CC=C(C=C1)C1=NN(C(=C1)C(=O)OCC)CC(NCC1=CC(=CC=C1)F)=O DMURHOFPENMMSF-UHFFFAOYSA-N 0.000 claims description 4
- KCEMKRDRPILCLR-UHFFFAOYSA-N ethyl 5-(4-chlorophenyl)-2-[2-[(3-methoxyphenyl)methylamino]-2-oxoethyl]pyrazole-3-carboxylate Chemical compound ClC1=CC=C(C=C1)C1=NN(C(=C1)C(=O)OCC)CC(NCC1=CC(=CC=C1)OC)=O KCEMKRDRPILCLR-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- OZJDOUPBBXPBCB-UHFFFAOYSA-N methyl 2-[2-(benzylamino)-2-oxoethyl]-5-(4-chloro-3-fluorophenyl)-1,2,4-triazole-3-carboxylate Chemical compound C(C1=CC=CC=C1)NC(=O)CN1N=C(N=C1C(=O)OC)C1=CC(=C(C=C1)Cl)F OZJDOUPBBXPBCB-UHFFFAOYSA-N 0.000 claims description 4
- ODFDNEYAAMFUFQ-UHFFFAOYSA-N methyl 2-[2-[(3-fluorophenyl)methylamino]-2-oxoethyl]-5-(3-methoxyphenyl)pyrazole-3-carboxylate Chemical compound FC=1C=C(CNC(=O)CN2N=C(C=C2C(=O)OC)C2=CC(=CC=C2)OC)C=CC=1 ODFDNEYAAMFUFQ-UHFFFAOYSA-N 0.000 claims description 4
- RXOBNHDCMSGHQQ-UHFFFAOYSA-N methyl 5-(4-chloro-3-fluorophenyl)-2-[2-[(3-fluorophenyl)methylamino]-2-oxoethyl]-1,2,4-triazole-3-carboxylate Chemical compound ClC1=C(C=C(C=C1)C1=NN(C(=N1)C(=O)OC)CC(NCC1=CC(=CC=C1)F)=O)F RXOBNHDCMSGHQQ-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- NMSZASKPGBJWEN-UHFFFAOYSA-N methyl 5-(4-cyanophenyl)-2-[2-[(3-methoxyphenyl)methylamino]-2-oxoethyl]-1,2,4-triazole-3-carboxylate Chemical compound C(#N)C1=CC=C(C=C1)C1=NN(C(=N1)C(=O)OC)CC(NCC1=CC(=CC=C1)OC)=O NMSZASKPGBJWEN-UHFFFAOYSA-N 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- BMWCVQCVRVGRTD-UHFFFAOYSA-N 5-(4-chloro-3-fluorophenyl)-2-[2-[(3-methoxyphenyl)methylamino]-2-oxoethyl]-1,2,4-triazole-3-carboxamide Chemical compound ClC1=C(C=C(C=C1)C1=NN(C(=N1)C(=O)N)CC(NCC1=CC(=CC=C1)OC)=O)F BMWCVQCVRVGRTD-UHFFFAOYSA-N 0.000 claims description 2
- 208000030507 AIDS Diseases 0.000 claims description 2
- 208000003200 Adenoma Diseases 0.000 claims description 2
- 208000006468 Adrenal Cortex Neoplasms Diseases 0.000 claims description 2
- 208000028060 Albright disease Diseases 0.000 claims description 2
- 241000193738 Bacillus anthracis Species 0.000 claims description 2
- 231100000699 Bacterial toxin Toxicity 0.000 claims description 2
- 206010007572 Cardiac hypertrophy Diseases 0.000 claims description 2
- 208000006029 Cardiomegaly Diseases 0.000 claims description 2
- 201000005947 Carney Complex Diseases 0.000 claims description 2
- 206010008631 Cholera Diseases 0.000 claims description 2
- 201000003874 Common Variable Immunodeficiency Diseases 0.000 claims description 2
- 206010058314 Dysplasia Diseases 0.000 claims description 2
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 claims description 2
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 claims description 2
- 206010064571 Gene mutation Diseases 0.000 claims description 2
- 101001014590 Homo sapiens Guanine nucleotide-binding protein G(s) subunit alpha isoforms XLas Proteins 0.000 claims description 2
- 101001014594 Homo sapiens Guanine nucleotide-binding protein G(s) subunit alpha isoforms short Proteins 0.000 claims description 2
- 101001014610 Homo sapiens Neuroendocrine secretory protein 55 Proteins 0.000 claims description 2
- 101000797903 Homo sapiens Protein ALEX Proteins 0.000 claims description 2
- 201000002980 Hyperparathyroidism Diseases 0.000 claims description 2
- 206010020850 Hyperthyroidism Diseases 0.000 claims description 2
- 206010061598 Immunodeficiency Diseases 0.000 claims description 2
- 208000029462 Immunodeficiency disease Diseases 0.000 claims description 2
- 201000001853 McCune-Albright syndrome Diseases 0.000 claims description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
- 201000005702 Pertussis Diseases 0.000 claims description 2
- 208000010067 Pituitary ACTH Hypersecretion Diseases 0.000 claims description 2
- 208000007913 Pituitary Neoplasms Diseases 0.000 claims description 2
- 201000005746 Pituitary adenoma Diseases 0.000 claims description 2
- 206010061538 Pituitary tumour benign Diseases 0.000 claims description 2
- 208000020627 Pituitary-dependent Cushing syndrome Diseases 0.000 claims description 2
- 208000024313 Testicular Neoplasms Diseases 0.000 claims description 2
- 206010057644 Testis cancer Diseases 0.000 claims description 2
- 230000004913 activation Effects 0.000 claims description 2
- 208000021033 autosomal dominant polycystic liver disease Diseases 0.000 claims description 2
- 239000000688 bacterial toxin Substances 0.000 claims description 2
- 210000000845 cartilage Anatomy 0.000 claims description 2
- 230000000295 complement effect Effects 0.000 claims description 2
- 229940088597 hormone Drugs 0.000 claims description 2
- 239000005556 hormone Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 230000007813 immunodeficiency Effects 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
- 230000035772 mutation Effects 0.000 claims description 2
- 201000002528 pancreatic cancer Diseases 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 208000021310 pituitary gland adenoma Diseases 0.000 claims description 2
- 208000028589 polycystic liver disease Diseases 0.000 claims description 2
- 208000001061 polyostotic fibrous dysplasia Diseases 0.000 claims description 2
- 208000006155 precocious puberty Diseases 0.000 claims description 2
- 208000029141 primary pigmented nodular adrenocortical disease Diseases 0.000 claims description 2
- 102000005962 receptors Human genes 0.000 claims description 2
- 108020003175 receptors Proteins 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 201000003120 testicular cancer Diseases 0.000 claims description 2
- 201000008827 tuberculosis Diseases 0.000 claims description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 2
- NARMWWWLSZSJDL-UHFFFAOYSA-N 5-(4-cyanophenyl)-2-[2-[(3-methoxyphenyl)methylamino]-2-oxoethyl]-N-methyl-1,2,4-triazole-3-carboxamide Chemical compound C(#N)C1=CC=C(C=C1)C1=NN(C(=N1)C(=O)NC)CC(NCC1=CC(=CC=C1)OC)=O NARMWWWLSZSJDL-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000003902 lesion Effects 0.000 claims 1
- 238000000034 method Methods 0.000 description 7
- 230000009537 cortical lesion Effects 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1616439.4A GB201616439D0 (en) | 2016-09-28 | 2016-09-28 | Compounds and uses |
| GB1616439.4 | 2016-09-28 | ||
| PCT/GB2017/052898 WO2018060704A1 (en) | 2016-09-28 | 2017-09-28 | Compounds and their use as pde4 activators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019532929A JP2019532929A (ja) | 2019-11-14 |
| JP2019532929A5 true JP2019532929A5 (OSRAM) | 2020-11-05 |
| JP7062643B2 JP7062643B2 (ja) | 2022-05-06 |
Family
ID=57539742
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019515286A Active JP7062643B2 (ja) | 2016-09-28 | 2017-09-28 | 化合物およびｐｄｅ４活性剤としてのそれらの使用 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US11046660B2 (OSRAM) |
| EP (1) | EP3519403B1 (OSRAM) |
| JP (1) | JP7062643B2 (OSRAM) |
| GB (1) | GB201616439D0 (OSRAM) |
| WO (1) | WO2018060704A1 (OSRAM) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201504763D0 (en) | 2015-03-20 | 2015-05-06 | Mironid Ltd | Compounds and uses |
| GB201616439D0 (en) | 2016-09-28 | 2016-11-09 | Mironid Limited | Compounds and uses |
| GB201805527D0 (en) | 2018-04-04 | 2018-05-16 | Mironid Ltd | Compounds and their use as pde4 activators |
| GB202102088D0 (en) | 2021-02-15 | 2021-03-31 | Mironid Ltd | Compounds and their use as pde4 activators |
| GB202212000D0 (en) | 2022-08-17 | 2022-09-28 | Mironid Ltd | Compounds and their use as PDE4 activators |
| GB202211999D0 (en) | 2022-08-17 | 2022-09-28 | Mironid Ltd | Compounds and their use as PDE4 activators |
| WO2025157695A1 (en) | 2024-01-24 | 2025-07-31 | Syngenta Crop Protection Ag | Herbicidal pyrazole and triazole compounds |
| WO2026041514A1 (en) | 2024-08-20 | 2026-02-26 | Syngenta Crop Protection Ag | Herbicidal compounds |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ178996A (en) * | 1974-11-15 | 1978-06-02 | Kornis G | Pyrfazole amides and thioamides;herbicidal compositions |
| JP3890453B2 (ja) | 1996-09-18 | 2007-03-07 | リードケミカル株式会社 | 新規２，４−ジオキソピロリジンおよび２，４−ジオキソテトラヒドロフラン誘導体及び該化合物を有効成分とする医薬 |
| JP2006518738A (ja) * | 2003-02-12 | 2006-08-17 | トランス テック ファーマ，インコーポレイテッド | 治療薬としての置換アゾール誘導体 |
| KR20060005375A (ko) * | 2003-04-18 | 2006-01-17 | 메모리 파마슈티칼스 코포레이션 | 포스포디에스테라제 4 억제제로서의 피라졸 유도체 |
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| EP2057152A1 (de) | 2006-08-07 | 2009-05-13 | Boehringer Ingelheim International GmbH | Enantiomerenreine betaagonisten, verfahren zu deren herstellung und deren verwendung als arzneimittel |
| WO2009131956A1 (en) | 2008-04-21 | 2009-10-29 | Institute For Oneworld Health | Compounds, compositions and methods comprising triazole derivatives |
| US20100144733A1 (en) | 2008-04-28 | 2010-06-10 | Institute For Oneworld Health | Compounds, compositions and methods comprising heteroaromatic derivatives |
| WO2010059838A2 (en) | 2008-11-20 | 2010-05-27 | Decode Genetics Ehf | Pde4 inhibitors selective for the long form of pde4 for treating inflammation and avoiding side effects |
| DE102009013642A1 (de) | 2009-03-18 | 2010-09-23 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Phenylalaninderivate und deren Verwendung |
| US8343976B2 (en) | 2009-04-20 | 2013-01-01 | Institute For Oneworld Health | Compounds, compositions and methods comprising pyrazole derivatives |
| KR20120036842A (ko) | 2009-05-12 | 2012-04-18 | 코닌클리케 필립스 일렉트로닉스 엔.브이. | 악성의 호르몬 민감성 전립선 암에 대한 마커로서의 포스포디에스테라제 4ｄ7 |
| US8753892B2 (en) | 2009-05-12 | 2014-06-17 | Koninklijke Philips N.V. | Phosphodiesterase 4D7 as prostate cancer marker |
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| JP6042433B2 (ja) | 2011-08-11 | 2016-12-14 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | １，２，４−トリアゾリル置換されたケトエノール類 |
| US8642774B2 (en) | 2011-12-08 | 2014-02-04 | Boehringer Ingelheim International Gmbh | Compounds |
| US8889677B2 (en) | 2012-01-17 | 2014-11-18 | Boehringer Ingellheim International GmbH | Substituted triazoles useful as mGlu5 receptor modulators |
| JP2016512825A (ja) | 2013-03-15 | 2016-05-09 | シファ・バイオメディカル・コーポレイションＳｈｉｆａ Ｂｉｏｍｅｄｉｃａｌ Ｃｏｒｐｏｒａｔｉｏｎ | 抗プロタンパク質転換酵素サブチリシン／ケキシン９型（抗ｐｃｓｋ９）化合物および心血管疾患の治療および／または予防におけるその使用方法 |
| US20170087129A1 (en) | 2014-05-16 | 2017-03-30 | Celgene Corporation | Compositions and methods for the treatment of atherosclerotic cardiovascular diseases with pde4 modulators |
| GB201504763D0 (en) | 2015-03-20 | 2015-05-06 | Mironid Ltd | Compounds and uses |
| CN108472284A (zh) | 2015-09-11 | 2018-08-31 | 维纳拓尔斯制药公司 | β-内酰胺酶抑制剂 |
| GB201616439D0 (en) | 2016-09-28 | 2016-11-09 | Mironid Limited | Compounds and uses |
| WO2019081477A1 (de) * | 2017-10-26 | 2019-05-02 | Bayer Cropscience Aktiengesellschaft | Substituierte pyrazole sowie deren salze und ihre verwendung als herbizide wirkstoffe |
-
2016
- 2016-09-28 GB GBGB1616439.4A patent/GB201616439D0/en not_active Ceased
-
2017
- 2017-09-28 JP JP2019515286A patent/JP7062643B2/ja active Active
- 2017-09-28 WO PCT/GB2017/052898 patent/WO2018060704A1/en not_active Ceased
- 2017-09-28 US US16/337,344 patent/US11046660B2/en active Active
- 2017-09-28 EP EP17780158.6A patent/EP3519403B1/en active Active
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