CA2729220A1 - Di-substituted phenyl compounds - Google Patents
Di-substituted phenyl compounds Download PDFInfo
- Publication number
- CA2729220A1 CA2729220A1 CA2729220A CA2729220A CA2729220A1 CA 2729220 A1 CA2729220 A1 CA 2729220A1 CA 2729220 A CA2729220 A CA 2729220A CA 2729220 A CA2729220 A CA 2729220A CA 2729220 A1 CA2729220 A1 CA 2729220A1
- Authority
- CA
- Canada
- Prior art keywords
- och2
- quinolinyl
- pyridinyl
- compound
- phenyl
- 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.)
- Abandoned
Links
- -1 Di-substituted phenyl compounds Chemical class 0.000 title claims abstract description 1650
- 150000001875 compounds Chemical class 0.000 claims abstract description 152
- 238000011282 treatment Methods 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 273
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 88
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 76
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 73
- 125000000217 alkyl group Chemical group 0.000 claims description 68
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 67
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 62
- 229910052736 halogen Inorganic materials 0.000 claims description 59
- 150000002367 halogens Chemical class 0.000 claims description 59
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 50
- 125000003545 alkoxy group Chemical group 0.000 claims description 40
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 39
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
- 125000006413 ring segment Chemical group 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 34
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 32
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 29
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 27
- 125000005605 benzo group Chemical group 0.000 claims description 23
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 22
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000003282 alkyl amino group Chemical group 0.000 claims description 18
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 18
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
- 201000000980 schizophrenia Diseases 0.000 claims description 15
- 125000004001 thioalkyl group Chemical group 0.000 claims description 14
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000003368 amide group Chemical group 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 208000008589 Obesity Diseases 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 235000020824 obesity Nutrition 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 208000023105 Huntington disease Diseases 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 5
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 208000030814 Eating disease Diseases 0.000 claims description 3
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 3
- 206010034158 Pathological gambling Diseases 0.000 claims description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 208000015114 central nervous system disease Diseases 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 235000014632 disordered eating Nutrition 0.000 claims description 3
- 230000000632 dystonic effect Effects 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 3
- 201000003631 narcolepsy Diseases 0.000 claims description 3
- 208000012201 sexual and gender identity disease Diseases 0.000 claims description 3
- 208000015891 sexual disease Diseases 0.000 claims description 3
- 208000019116 sleep disease Diseases 0.000 claims description 3
- 230000005586 smoking cessation Effects 0.000 claims description 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 17
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 16
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract description 10
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract description 8
- 210000003169 central nervous system Anatomy 0.000 abstract description 7
- 239000003112 inhibitor Substances 0.000 abstract description 7
- 208000024891 symptom Diseases 0.000 abstract description 7
- 241000124008 Mammalia Species 0.000 abstract description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 5
- 208000015122 neurodegenerative disease Diseases 0.000 abstract description 5
- 208000012902 Nervous system disease Diseases 0.000 abstract description 3
- 208000025966 Neurological disease Diseases 0.000 abstract description 3
- 230000000626 neurodegenerative effect Effects 0.000 abstract description 3
- 230000000926 neurological effect Effects 0.000 abstract description 3
- 230000008569 process Effects 0.000 abstract description 3
- 208000020016 psychiatric disease Diseases 0.000 abstract description 3
- 230000007278 cognition impairment Effects 0.000 abstract description 2
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 2
- 230000000698 schizophrenic effect Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 289
- 101150041968 CDC13 gene Proteins 0.000 description 231
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 231
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 207
- 239000000203 mixture Substances 0.000 description 207
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 183
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 158
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 138
- 239000000243 solution Substances 0.000 description 138
- 235000019439 ethyl acetate Nutrition 0.000 description 127
- 235000019256 formaldehyde Nutrition 0.000 description 124
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 109
- 238000005160 1H NMR spectroscopy Methods 0.000 description 102
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 88
- 229910052786 argon Inorganic materials 0.000 description 79
- 239000002904 solvent Substances 0.000 description 74
- 239000007787 solid Substances 0.000 description 71
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 70
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 68
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 65
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 64
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 63
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 59
- 239000000741 silica gel Substances 0.000 description 58
- 229910002027 silica gel Inorganic materials 0.000 description 58
- 239000011541 reaction mixture Substances 0.000 description 56
- 125000002757 morpholinyl group Chemical group 0.000 description 55
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 54
- 238000000746 purification Methods 0.000 description 52
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 50
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 45
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 44
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 44
- 238000003818 flash chromatography Methods 0.000 description 41
- 238000010992 reflux Methods 0.000 description 41
- 238000004587 chromatography analysis Methods 0.000 description 39
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 38
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 34
- 235000019341 magnesium sulphate Nutrition 0.000 description 34
- NFHFRUOZVGFOOS-UHFFFAOYSA-N Pd(PPh3)4 Substances [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 33
- 229910000029 sodium carbonate Inorganic materials 0.000 description 32
- 235000017550 sodium carbonate Nutrition 0.000 description 32
- 238000003786 synthesis reaction Methods 0.000 description 32
- 239000000706 filtrate Substances 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 230000015572 biosynthetic process Effects 0.000 description 28
- 239000012074 organic phase Substances 0.000 description 26
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 26
- 235000017557 sodium bicarbonate Nutrition 0.000 description 23
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 23
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 22
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000012267 brine Substances 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 20
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 20
- 238000001704 evaporation Methods 0.000 description 19
- 230000008020 evaporation Effects 0.000 description 19
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 18
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 17
- YVZLJKWEWSSNCP-UHFFFAOYSA-N 2-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]methyl]quinoline Chemical compound O1C(C)(C)C(C)(C)OB1C(C=C1)=CC=C1OCC1=CC=C(C=CC=C2)C2=N1 YVZLJKWEWSSNCP-UHFFFAOYSA-N 0.000 description 17
- 238000001914 filtration Methods 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- 239000007832 Na2SO4 Substances 0.000 description 16
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- 229910000024 caesium carbonate Inorganic materials 0.000 description 16
- 238000010898 silica gel chromatography Methods 0.000 description 16
- 229910052938 sodium sulfate Inorganic materials 0.000 description 16
- 235000011152 sodium sulphate Nutrition 0.000 description 16
- 239000001993 wax Substances 0.000 description 16
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- 229920006395 saturated elastomer Polymers 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 11
- 238000004293 19F NMR spectroscopy Methods 0.000 description 10
- VNLSTUJKUKLXCE-UHFFFAOYSA-N 2-[[4-(2-nitro-6-pyridin-4-ylphenyl)phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C=1C([N+](=O)[O-])=CC=CC=1C1=CC=NC=C1 VNLSTUJKUKLXCE-UHFFFAOYSA-N 0.000 description 10
- KPMBJFBCGUKSKZ-UHFFFAOYSA-N 3-pyridin-4-yl-2-[4-(quinolin-2-ylmethoxy)phenyl]aniline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C=1C(N)=CC=CC=1C1=CC=NC=C1 KPMBJFBCGUKSKZ-UHFFFAOYSA-N 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 10
- 239000012230 colorless oil Substances 0.000 description 10
- 229910052740 iodine Inorganic materials 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 229910017711 NHRa Inorganic materials 0.000 description 9
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 description 8
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 8
- 101100272976 Panax ginseng CYP716A53v2 gene Proteins 0.000 description 8
- 208000028017 Psychotic disease Diseases 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 239000006260 foam Substances 0.000 description 8
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 229910052701 rubidium Inorganic materials 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- WUZBJBRSKNHZJA-UHFFFAOYSA-N 3-nitro-2-(4-phenylmethoxyphenyl)phenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1C(C=C1)=CC=C1OCC1=CC=CC=C1 WUZBJBRSKNHZJA-UHFFFAOYSA-N 0.000 description 7
- UISDUKOOLHTIRD-UHFFFAOYSA-N 4-[3-nitro-2-(4-phenylmethoxyphenyl)phenyl]pyridine Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1C=1C([N+](=O)[O-])=CC=CC=1C1=CC=NC=C1 UISDUKOOLHTIRD-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 125000005412 pyrazyl group Chemical group 0.000 description 7
- HRVRWIBVVHOHNN-UHFFFAOYSA-N 2-bromo-3-nitrophenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1Br HRVRWIBVVHOHNN-UHFFFAOYSA-N 0.000 description 6
- QRXVNOWBXUNHIE-UHFFFAOYSA-N 3-pyridin-4-yl-2-[4-(quinolin-2-ylmethoxy)phenyl]benzonitrile Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C=1C(C#N)=CC=CC=1C1=CC=NC=C1 QRXVNOWBXUNHIE-UHFFFAOYSA-N 0.000 description 6
- SVIAEKFXYHOOIZ-UHFFFAOYSA-N 4-(2-nitro-6-pyridin-4-ylphenyl)phenol Chemical compound C1=CC(O)=CC=C1C1=C(C=2C=CN=CC=2)C=CC=C1[N+]([O-])=O SVIAEKFXYHOOIZ-UHFFFAOYSA-N 0.000 description 6
- UBIPSBARSLMFLM-UHFFFAOYSA-N [2-[4-(quinolin-2-ylmethoxy)phenyl]phenyl] trifluoromethanesulfonate Chemical compound FC(F)(F)S(=O)(=O)OC1=CC=CC=C1C(C=C1)=CC=C1OCC1=CC=C(C=CC=C2)C2=N1 UBIPSBARSLMFLM-UHFFFAOYSA-N 0.000 description 6
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 238000001425 electrospray ionisation time-of-flight mass spectrometry Methods 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 6
- PWELSANIKKMMAM-UHFFFAOYSA-N 2-[[4-(5-methyl-2-pyridin-4-ylphenyl)phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=CC(C)=CC=C1C1=CC=NC=C1 PWELSANIKKMMAM-UHFFFAOYSA-N 0.000 description 5
- UIUPYFMJPNQPRI-UHFFFAOYSA-N 2-[[4-[2-(1,3-dioxan-2-yl)-6-pyridin-4-ylphenyl]phenoxy]methyl]quinoline Chemical compound C=1C=C2C=CC=CC2=NC=1COC(C=C1)=CC=C1C1=C(C2OCCCO2)C=CC=C1C1=CC=NC=C1 UIUPYFMJPNQPRI-UHFFFAOYSA-N 0.000 description 5
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- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- JTJMJGYZQZDUJJ-UHFFFAOYSA-N phencyclidine Chemical compound C1CCCCN1C1(C=2C=CC=CC=2)CCCCC1 JTJMJGYZQZDUJJ-UHFFFAOYSA-N 0.000 description 1
- 229950010883 phencyclidine Drugs 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 125000005542 phthalazyl group Chemical group 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 208000028173 post-traumatic stress disease Diseases 0.000 description 1
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 210000002637 putamen Anatomy 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- CXHVEWNQMCXEGM-UHFFFAOYSA-N pyrazolo[1,5-b]pyridazine Chemical compound C1=CC=NN2N=CC=C21 CXHVEWNQMCXEGM-UHFFFAOYSA-N 0.000 description 1
- LNTIZOKGHGTDTL-UHFFFAOYSA-N pyrazolo[1,5-c]pyrimidine Chemical compound C1=CN=CN2N=CC=C21 LNTIZOKGHGTDTL-UHFFFAOYSA-N 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
- 125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 description 1
- 229960004431 quetiapine Drugs 0.000 description 1
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000014786 regulation of synaptic transmission Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- GZKLJWGUPQBVJQ-UHFFFAOYSA-N sertindole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 GZKLJWGUPQBVJQ-UHFFFAOYSA-N 0.000 description 1
- 229960000652 sertindole Drugs 0.000 description 1
- 231100000872 sexual dysfunction Toxicity 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical class [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
- LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- HBDDRESWUAFAHY-UHFFFAOYSA-N thiomorpholin-3-one Chemical compound O=C1CSCCN1 HBDDRESWUAFAHY-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 230000036964 tight binding Effects 0.000 description 1
- 238000001269 time-of-flight mass spectrometry Methods 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 208000018724 torsion dystonia Diseases 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229960000607 ziprasidone Drugs 0.000 description 1
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Psychiatry (AREA)
- Emergency Medicine (AREA)
- Anesthesiology (AREA)
- Child & Adolescent Psychology (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Reproductive Health (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7559908P | 2008-06-25 | 2008-06-25 | |
| US61/075,599 | 2008-06-25 | ||
| US13885608P | 2008-12-18 | 2008-12-18 | |
| US61/138,856 | 2008-12-18 | ||
| PCT/US2009/048608 WO2009158467A2 (en) | 2008-06-25 | 2009-06-25 | Di-substituted phenyl compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2729220A1 true CA2729220A1 (en) | 2009-12-30 |
Family
ID=41137470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2729220A Abandoned CA2729220A1 (en) | 2008-06-25 | 2009-06-25 | Di-substituted phenyl compounds |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20110224204A1 (https=) |
| EP (1) | EP2297131A2 (https=) |
| JP (1) | JP2011526294A (https=) |
| KR (1) | KR20110025984A (https=) |
| CN (1) | CN102131798A (https=) |
| AU (1) | AU2009262150A1 (https=) |
| BR (1) | BRPI0914775A2 (https=) |
| CA (1) | CA2729220A1 (https=) |
| MX (1) | MX2011000177A (https=) |
| RU (1) | RU2011102587A (https=) |
| WO (1) | WO2009158467A2 (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP5778164B2 (ja) * | 2009-10-30 | 2015-09-16 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプＪａｎｓｓｅｎ Ｐｈａｒｍａｃｅｕｔｉｃａ Ｎａａｍｌｏｚｅ Ｖｅｎｎｏｏｔｓｃｈａｐ | 放射標識ｐｄｅ１０リガンド |
| EP2423181A1 (en) | 2010-07-28 | 2012-02-29 | Prous Institute For Biomedical Research S.A. | Multitarget substituted biphenyl diol derivatives |
| CN107141309A (zh) | 2011-01-11 | 2017-09-08 | 桑诺维恩药品公司 | 杂芳基化合物及其使用方法 |
| CN103476757A (zh) | 2011-02-18 | 2013-12-25 | 阿勒根公司 | 作为磷酸二酯酶10(pde10a)的抑制剂的取代的6,7-二烷氧基-3-异喹啉醇衍生物 |
| US20120309796A1 (en) | 2011-06-06 | 2012-12-06 | Fariborz Firooznia | Benzocycloheptene acetic acids |
| GB201113538D0 (en) * | 2011-08-04 | 2011-09-21 | Karobio Ab | Novel estrogen receptor ligands |
| WO2014007228A1 (ja) * | 2012-07-03 | 2014-01-09 | 小野薬品工業株式会社 | ソマトスタチン受容体作動活性を有する化合物およびその医薬用途 |
| WO2014009305A1 (en) * | 2012-07-09 | 2014-01-16 | Janssen Pharmaceutica Nv | Inhibitors of phosphodiesterase 10 enzyme |
| WO2014071044A1 (en) | 2012-11-01 | 2014-05-08 | Allergan, Inc. | Substituted 6,7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (pde10a) |
| US9198898B2 (en) | 2013-06-24 | 2015-12-01 | Tigercat Pharma, Inc. | Use of NK-1 receptor antagonists in pruritus |
| US8906951B1 (en) | 2013-06-24 | 2014-12-09 | Tigercat Pharma, Inc. | Use of NK-1 receptor antagonists in pruritus |
| EP2860177A3 (en) * | 2013-09-20 | 2015-06-10 | Bayer Intellectual Property GmbH | Synthesis of functionalized arenes |
| US9200016B2 (en) | 2013-12-05 | 2015-12-01 | Allergan, Inc. | Substituted 6, 7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (PDE 10A) |
| WO2018170284A1 (en) | 2017-03-16 | 2018-09-20 | Crinetics Pharmaceuticals, Inc. | Somatostatin modulators and uses thereof |
| EP3752498B1 (en) | 2018-02-12 | 2023-06-28 | Crinetics Pharmaceuticals, Inc. | Somatostatin modulators and uses thereof |
| BR112020018094A2 (pt) | 2018-03-08 | 2020-12-22 | Incyte Corporation | Compostos de aminopirazina diol como inibidores de pi3k-¿ |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
| AR116424A1 (es) | 2018-09-18 | 2021-05-05 | Crinetics Pharmaceuticals Inc | Moduladores de la somatostatina y usos de los mismos |
| TWI841768B (zh) * | 2019-08-14 | 2024-05-11 | 美商克林提克斯醫藥股份有限公司 | 非肽生長抑制素(somatostatin)5型受體激動劑及其用途 |
| KR102811543B1 (ko) | 2019-10-16 | 2025-05-23 | 삼성디스플레이 주식회사 | 유기 전계 발광 소자 및 유기 전계 발광 소자용 다환 화합물 |
| CA3187998A1 (en) * | 2020-08-04 | 2022-02-10 | Angela ZAMPELLA | Quinoline compounds as selective and/or dual modulators of bile acid receptors and leukotriene cysteinyl receptors |
| EP4294797A1 (en) | 2021-02-17 | 2023-12-27 | Crinetics Pharmaceuticals, Inc. | Crystalline forms of a somatostatin modulator |
| JP2026500913A (ja) | 2022-12-13 | 2026-01-09 | クリネティックス ファーマシューティカルズ，インク． | ソマトスタチンサブタイプ－２受容体（ｓｓｔ２ｒ）標的化治療薬及びその使用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0453210A3 (en) * | 1990-04-19 | 1993-01-13 | Imperial Chemical Industries Plc | Pyridine derivatives |
| CN1034934C (zh) * | 1990-06-19 | 1997-05-21 | 明治制果株式会社 | 血管紧张素ii拮抗性吡啶衍生物的制备方法 |
| GB2264710A (en) * | 1992-03-04 | 1993-09-08 | Merck & Co Inc | Quinoline and azaquinoline angiotensin ii antagonists incorporating a substituted biphenyl element |
| EP1541149A1 (en) * | 2002-06-26 | 2005-06-15 | Kyowa Hakko Kogyo Co., Ltd. | Phosphodiesterase inhibitor |
| US7524870B2 (en) * | 2004-12-03 | 2009-04-28 | Hoffmann-La Roche Inc. | Biaryloxymethylarenecarboxylic acids as glycogen synthase activators |
| JP2009535394A (ja) * | 2006-05-02 | 2009-10-01 | ファイザー・プロダクツ・インク | Ｐｄｅ１０阻害剤としての二環式ヘテロアリール化合物 |
| WO2008033455A2 (en) * | 2006-09-13 | 2008-03-20 | The Institutes For Pharmaceutical Discovery, Llc | Biphenyl and heteroaryl phenyl derivatives as protein tyrosine phosphatases inhibitors |
-
2009
- 2009-06-25 CA CA2729220A patent/CA2729220A1/en not_active Abandoned
- 2009-06-25 MX MX2011000177A patent/MX2011000177A/es not_active Application Discontinuation
- 2009-06-25 EP EP09770999A patent/EP2297131A2/en not_active Withdrawn
- 2009-06-25 KR KR1020117001927A patent/KR20110025984A/ko not_active Ceased
- 2009-06-25 BR BRPI0914775A patent/BRPI0914775A2/pt not_active IP Right Cessation
- 2009-06-25 US US13/001,361 patent/US20110224204A1/en not_active Abandoned
- 2009-06-25 AU AU2009262150A patent/AU2009262150A1/en not_active Abandoned
- 2009-06-25 WO PCT/US2009/048608 patent/WO2009158467A2/en not_active Ceased
- 2009-06-25 JP JP2011516646A patent/JP2011526294A/ja active Pending
- 2009-06-25 CN CN2009801332872A patent/CN102131798A/zh active Pending
- 2009-06-25 RU RU2011102587/04A patent/RU2011102587A/ru not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20110025984A (ko) | 2011-03-14 |
| CN102131798A (zh) | 2011-07-20 |
| MX2011000177A (es) | 2011-06-20 |
| RU2011102587A (ru) | 2012-07-27 |
| US20110224204A1 (en) | 2011-09-15 |
| EP2297131A2 (en) | 2011-03-23 |
| AU2009262150A1 (en) | 2009-12-30 |
| JP2011526294A (ja) | 2011-10-06 |
| BRPI0914775A2 (pt) | 2015-10-20 |
| WO2009158467A3 (en) | 2010-07-29 |
| WO2009158467A2 (en) | 2009-12-30 |
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| EP2427454B1 (en) | Phenoxymethyl heterocyclic compounds | |
| HK1186981B (en) | Phenoxymethyl heterocyclic compounds | |
| HK1167402B (en) | Phenoxymethyl heterocyclic compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20150625 |