ES2764660T3 - Compuestos de amida de quinuclidina sustituida geminal como agonistas de receptores alfa-7 nicotínicos de acetilcolina - Google Patents
Compuestos de amida de quinuclidina sustituida geminal como agonistas de receptores alfa-7 nicotínicos de acetilcolina Download PDFInfo
- Publication number
- ES2764660T3 ES2764660T3 ES15870786T ES15870786T ES2764660T3 ES 2764660 T3 ES2764660 T3 ES 2764660T3 ES 15870786 T ES15870786 T ES 15870786T ES 15870786 T ES15870786 T ES 15870786T ES 2764660 T3 ES2764660 T3 ES 2764660T3
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- Prior art keywords
- radical
- carboxamide
- thiophene
- benzo
- octan
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- -1 quinuclidine amide compounds Chemical class 0.000 title claims abstract description 774
- 239000000018 receptor agonist Substances 0.000 title description 3
- 229940044601 receptor agonist Drugs 0.000 title description 3
- 108010009685 Cholinergic Receptors Proteins 0.000 title 1
- 102000034337 acetylcholine receptors Human genes 0.000 title 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 95
- 150000003254 radicals Chemical group 0.000 claims abstract description 89
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 81
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 74
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 70
- 150000005840 aryl radicals Chemical class 0.000 claims abstract description 62
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 46
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 30
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000011593 sulfur Substances 0.000 claims abstract description 17
- 125000006413 ring segment Chemical group 0.000 claims abstract description 16
- IDCLTMRSSAXUNY-UHFFFAOYSA-N 5-hydroxylansoprazole Chemical group CC1=C(OCC(F)(F)F)C=CN=C1CS(=O)C1=NC2=CC(O)=CC=C2N1 IDCLTMRSSAXUNY-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 297
- 150000003839 salts Chemical class 0.000 claims description 119
- 125000004122 cyclic group Chemical group 0.000 claims description 110
- 208000010877 cognitive disease Diseases 0.000 claims description 98
- 208000024827 Alzheimer disease Diseases 0.000 claims description 70
- 208000024891 symptom Diseases 0.000 claims description 50
- 239000008194 pharmaceutical composition Substances 0.000 claims description 46
- 201000000980 schizophrenia Diseases 0.000 claims description 46
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 43
- 208000028698 Cognitive impairment Diseases 0.000 claims description 41
- 239000003085 diluting agent Substances 0.000 claims description 39
- 206010012289 Dementia Diseases 0.000 claims description 35
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 31
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 27
- 208000027061 mild cognitive impairment Diseases 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 239000003937 drug carrier Substances 0.000 claims description 16
- 230000019771 cognition Effects 0.000 claims description 13
- 208000028017 Psychotic disease Diseases 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 230000006735 deficit Effects 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 7
- 208000022610 schizoaffective disease Diseases 0.000 claims description 6
- 208000020186 Schizophreniform disease Diseases 0.000 claims description 5
- 230000001149 cognitive effect Effects 0.000 claims description 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 4
- XFXULGFHURSRNL-MRXNPFEDSA-N N-[(3R)-spiro[1-azabicyclo[2.2.2]octane-2,1'-cyclopropane]-3-yl]-1-benzofuran-5-carboxamide Chemical compound N12C3([C@@H](C(CC1)CC2)NC(=O)C=1C=CC2=C(C=CO2)C=1)CC3 XFXULGFHURSRNL-MRXNPFEDSA-N 0.000 claims description 4
- SVFXJOTZHCGIKP-MRXNPFEDSA-N N-[(3R)-spiro[1-azabicyclo[2.2.2]octane-2,1'-cyclopropane]-3-yl]-1-benzothiophene-2-carboxamide Chemical compound N12C3([C@@H](C(CC1)CC2)NC(=O)C1=CC2=C(S1)C=CC=C2)CC3 SVFXJOTZHCGIKP-MRXNPFEDSA-N 0.000 claims description 4
- HIFHKIVBOAYGIT-MRXNPFEDSA-N N-[(3R)-spiro[1-azabicyclo[2.2.2]octane-2,1'-cyclopropane]-3-yl]-1-benzothiophene-6-carboxamide Chemical compound N12C3([C@@H](C(CC1)CC2)NC(=O)C=1C=CC2=C(SC=C2)C=1)CC3 HIFHKIVBOAYGIT-MRXNPFEDSA-N 0.000 claims description 4
- CACOEYGIYDRJMG-OAHLLOKOSA-N N-[(3R)-spiro[1-azabicyclo[2.2.2]octane-2,1'-cyclopropane]-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound N12C3([C@@H](C(CC1)CC2)NC(=O)C=1C=C2C(=CN=1)OC=C2)CC3 CACOEYGIYDRJMG-OAHLLOKOSA-N 0.000 claims description 4
- GNIBIBLEGLWUTE-MRXNPFEDSA-N N-[(3R)-spiro[1-azabicyclo[2.2.2]octane-2,1'-cyclopropane]-3-yl]-1H-indole-6-carboxamide Chemical compound N12C3([C@@H](C(CC1)CC2)NC(=O)C1=CC=C2C=CNC2=C1)CC3 GNIBIBLEGLWUTE-MRXNPFEDSA-N 0.000 claims description 3
- 230000002708 enhancing effect Effects 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 392
- 239000000203 mixture Substances 0.000 description 283
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 255
- 239000007787 solid Substances 0.000 description 206
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 199
- 235000019439 ethyl acetate Nutrition 0.000 description 131
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 118
- 239000000243 solution Substances 0.000 description 116
- 238000000034 method Methods 0.000 description 100
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 95
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 86
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 84
- 239000012071 phase Substances 0.000 description 77
- 239000012074 organic phase Substances 0.000 description 76
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 70
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 68
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 66
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 64
- 239000003208 petroleum Substances 0.000 description 59
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 54
- 238000005160 1H NMR spectroscopy Methods 0.000 description 50
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 50
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 50
- 230000015572 biosynthetic process Effects 0.000 description 49
- 238000001914 filtration Methods 0.000 description 49
- 239000012267 brine Substances 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 48
- 239000011541 reaction mixture Substances 0.000 description 46
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 45
- 238000004587 chromatography analysis Methods 0.000 description 43
- 239000000741 silica gel Substances 0.000 description 43
- 229910002027 silica gel Inorganic materials 0.000 description 43
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 43
- 229910052721 tungsten Inorganic materials 0.000 description 37
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 32
- 229910000027 potassium carbonate Inorganic materials 0.000 description 32
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 31
- 239000003921 oil Substances 0.000 description 29
- 235000019198 oils Nutrition 0.000 description 29
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 23
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 23
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 23
- MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 19
- 239000000706 filtrate Substances 0.000 description 18
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 18
- 230000006999 cognitive decline Effects 0.000 description 17
- QERYCTSHXKAMIS-UHFFFAOYSA-M thiophene-2-carboxylate Chemical compound [O-]C(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-M 0.000 description 16
- 238000011282 treatment Methods 0.000 description 16
- 230000015654 memory Effects 0.000 description 15
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 15
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 14
- 239000001257 hydrogen Substances 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- 230000013016 learning Effects 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- 238000010898 silica gel chromatography Methods 0.000 description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
- 208000002193 Pain Diseases 0.000 description 11
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- 102000015296 acetylcholine-gated cation-selective channel activity proteins Human genes 0.000 description 10
- 108040006409 acetylcholine-gated cation-selective channel activity proteins Proteins 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 10
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 10
- 201000010099 disease Diseases 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- SZXBFHCOJLDTNH-UHFFFAOYSA-N spiro[1-azabicyclo[2.2.2]octane-2,1'-cyclopropane]-3-one Chemical compound N12C3(C(C(CC1)CC2)=O)CC3 SZXBFHCOJLDTNH-UHFFFAOYSA-N 0.000 description 10
- 239000003981 vehicle Substances 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 9
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- 238000000746 purification Methods 0.000 description 9
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- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- XIPUIGPNIDKXJU-UHFFFAOYSA-N [CH]1CC1 Chemical compound [CH]1CC1 XIPUIGPNIDKXJU-UHFFFAOYSA-N 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [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 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- HACJQZHGTLOKSH-UHFFFAOYSA-N thieno[2,3-d]pyrimidine-6-carboxylic acid Chemical compound N1=CN=C2SC(C(=O)O)=CC2=C1 HACJQZHGTLOKSH-UHFFFAOYSA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 239000000556 agonist Substances 0.000 description 7
- 125000005605 benzo group Chemical group 0.000 description 7
- OBRPZLIOLBMQBF-UHFFFAOYSA-N methyl 5,6-dichloro-1-benzothiophene-2-carboxylate Chemical compound ClC1=CC2=C(SC(=C2)C(=O)OC)C=C1Cl OBRPZLIOLBMQBF-UHFFFAOYSA-N 0.000 description 7
- SFDVDNLBYGHFNF-UHFFFAOYSA-N methyl 6-bromo-1-benzothiophene-2-carboxylate Chemical compound C1=C(Br)C=C2SC(C(=O)OC)=CC2=C1 SFDVDNLBYGHFNF-UHFFFAOYSA-N 0.000 description 7
- YPOXGDJGKBXRFP-UHFFFAOYSA-N pyrimidine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NC=N1 YPOXGDJGKBXRFP-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- QHKJIJXBJCOABP-UHFFFAOYSA-N 1-benzofuran-2-carboxamide Chemical compound C1=CC=C2OC(C(=O)N)=CC2=C1 QHKJIJXBJCOABP-UHFFFAOYSA-N 0.000 description 6
- COGDTUHZHIPSKA-UHFFFAOYSA-N 1-benzofuran-7-carboxamide Chemical compound NC(=O)C1=CC=CC2=C1OC=C2 COGDTUHZHIPSKA-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
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- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 6
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- RIIAHEIBOHZBED-UHFFFAOYSA-N thieno[2,3-c]pyridine-5-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC2=C1SC=C2 RIIAHEIBOHZBED-UHFFFAOYSA-N 0.000 description 6
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 description 6
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- GTWXSZIQNTUNKR-UHFFFAOYSA-N 1-benzofuran-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2OC=CC2=C1 GTWXSZIQNTUNKR-UHFFFAOYSA-N 0.000 description 5
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 5
- SPEQMFXWAHTACU-UHFFFAOYSA-N 2,2-dimethyl-1-azabicyclo[2.2.2]octan-3-one Chemical compound C1CC2CCN1C(C)(C)C2=O SPEQMFXWAHTACU-UHFFFAOYSA-N 0.000 description 5
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- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 5
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- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 5
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- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 5
- 229910000024 caesium carbonate Inorganic materials 0.000 description 5
- 230000003920 cognitive function Effects 0.000 description 5
- 125000001072 heteroaryl group Chemical group 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- JEHZRZXWHVICJQ-UHFFFAOYSA-N methyl 7-bromo-1-benzothiophene-2-carboxylate Chemical compound C1=CC(Br)=C2SC(C(=O)OC)=CC2=C1 JEHZRZXWHVICJQ-UHFFFAOYSA-N 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
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- XDYVZHUZZZKQOS-UHFFFAOYSA-N methyl 5-bromo-1-benzothiophene-2-carboxylate Chemical compound BrC1=CC=C2SC(C(=O)OC)=CC2=C1 XDYVZHUZZZKQOS-UHFFFAOYSA-N 0.000 description 4
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- DAINLPHWNUNXMR-UHFFFAOYSA-N methyl 5-cyclopropyl-1-benzothiophene-2-carboxylate Chemical compound C1(CC1)C1=CC2=C(SC(=C2)C(=O)OC)C=C1 DAINLPHWNUNXMR-UHFFFAOYSA-N 0.000 description 4
- AKMVBVDANUKAAD-UHFFFAOYSA-N methyl 6,7-difluoro-1-benzothiophene-2-carboxylate Chemical compound FC=1C=CC2=C(SC(=C2)C(=O)OC)C=1F AKMVBVDANUKAAD-UHFFFAOYSA-N 0.000 description 4
- XIUHYFQAAXIVBY-UHFFFAOYSA-N methyl 6-amino-1-benzothiophene-2-carboxylate Chemical compound C1=C(N)C=C2SC(C(=O)OC)=CC2=C1 XIUHYFQAAXIVBY-UHFFFAOYSA-N 0.000 description 4
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- HXCTZRJTPISYLZ-UHFFFAOYSA-N methyl 6-chloro-7-fluoro-1-benzothiophene-2-carboxylate Chemical compound ClC=1C=CC2=C(SC(=C2)C(=O)OC)C=1F HXCTZRJTPISYLZ-UHFFFAOYSA-N 0.000 description 4
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- JJYZASAGKBJEEI-UHFFFAOYSA-N methyl 6-cyclopropyl-1-benzothiophene-2-carboxylate Chemical compound C1(CC1)C=1C=CC2=C(SC(=C2)C(=O)OC)C=1 JJYZASAGKBJEEI-UHFFFAOYSA-N 0.000 description 4
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- NTWQXMNKLCUVKU-UHFFFAOYSA-N methyl 6-nitro-1-benzothiophene-2-carboxylate Chemical compound C1=C([N+]([O-])=O)C=C2SC(C(=O)OC)=CC2=C1 NTWQXMNKLCUVKU-UHFFFAOYSA-N 0.000 description 4
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- SGBDDYKQYZHAAO-UHFFFAOYSA-N methyl 7-chloro-6-methyl-1-benzothiophene-2-carboxylate Chemical compound ClC1=C(C=CC2=C1SC(=C2)C(=O)OC)C SGBDDYKQYZHAAO-UHFFFAOYSA-N 0.000 description 4
- AIFNICZNOPUIGX-UHFFFAOYSA-N methyl 7-cyano-1-benzothiophene-2-carboxylate Chemical compound C1=CC(C#N)=C2SC(C(=O)OC)=CC2=C1 AIFNICZNOPUIGX-UHFFFAOYSA-N 0.000 description 4
- PIKDAASNGGGPIE-UHFFFAOYSA-N methyl 7-cyclopropyl-1-benzothiophene-2-carboxylate Chemical compound C1(CC1)C1=CC=CC2=C1SC(=C2)C(=O)OC PIKDAASNGGGPIE-UHFFFAOYSA-N 0.000 description 4
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- UCKQXNORMKXVMR-UHFFFAOYSA-N methyl 7-phenyl-1-benzothiophene-2-carboxylate Chemical compound C=12SC(C(=O)OC)=CC2=CC=CC=1C1=CC=CC=C1 UCKQXNORMKXVMR-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- 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
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- 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
- A61P25/22—Anxiolytics
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- 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
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- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
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| US201462092702P | 2014-12-16 | 2014-12-16 | |
| US201562167706P | 2015-05-28 | 2015-05-28 | |
| PCT/US2015/065497 WO2016100184A1 (en) | 2014-12-16 | 2015-12-14 | Geminal substituted quinuclidine amide compounds as agonists of alpha-7 nicotinic acetylcholine receptors |
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| CA2988968A1 (en) | 2015-06-10 | 2016-12-15 | Forum Pharmaceuticals, Inc. | Aminobenzisoxazole compounds as agonists of a7-nicotinic acetylcholine receptors |
| JP6784069B2 (ja) * | 2015-07-07 | 2020-11-11 | Jnc株式会社 | 液晶性化合物、液晶組成物および液晶表示素子 |
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| CN108129430A (zh) * | 2016-11-30 | 2018-06-08 | 重庆圣华曦药业股份有限公司 | 一种立他司特中间体的合成方法 |
| CN110035995A (zh) * | 2016-12-16 | 2019-07-19 | 范德比尔特大学 | 毒蕈碱型乙酰胆碱受体m4的正向别构调节剂 |
| CR20200054A (es) | 2017-08-09 | 2020-03-21 | Denali Therapeutics Inc | Compuestos, composiciones y métodos |
| HUE062446T2 (hu) | 2017-09-01 | 2023-11-28 | Denali Therapeutics Inc | Vegyületek, készítmények és eljárások |
| MX2021000293A (es) | 2018-07-09 | 2021-07-15 | Boehringer Ingelheim Animal Health Usa Inc | Compuestos heterociclicos antihelminticos. |
| PH12021551324A1 (en) | 2019-01-08 | 2022-04-25 | Kyorin Seiyaku Kk | 15-pgdh inhibitor |
| US12304897B2 (en) | 2019-01-31 | 2025-05-20 | Kyorin Pharmaceutical Co., Ltd. | 15-PGDH inhibitors |
| MA54959A (fr) | 2019-02-13 | 2021-12-22 | Denali Therapeutics Inc | Composés, compositions et procédés |
| EP3923935A4 (en) | 2019-02-13 | 2022-10-26 | Denali Therapeutics Inc. | COMPOUNDS, COMPOSITIONS AND METHODS |
| JP7637630B2 (ja) | 2019-03-19 | 2025-02-28 | ベーリンガー インゲルハイム フェトメディカ ゲーエムベーハー | 駆虫性アザベンゾチオフェンおよびアザベンゾフラン化合物 |
| PH12022553222A1 (en) | 2020-05-29 | 2024-02-12 | Boehringer Ingelheim Animal Health Usa Inc | Anthelmintic heterocyclic compounds |
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| AU2022403203B2 (en) | 2021-12-01 | 2025-09-25 | Pfizer Inc. | 3-phenyl-1-benzothiophene-2-carboxylic acid derivatives as branched-chain alpha keto acid dehydrogenase kinase inhibitors for the treatment of diabetes, kidney diseases, nash and heart failure |
| EP4463459A1 (en) | 2022-01-10 | 2024-11-20 | Recludix Pharma, Inc. | Stat modulators and uses thereof |
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-
2015
- 2015-12-14 EP EP19200814.2A patent/EP3623371A1/en not_active Withdrawn
- 2015-12-14 US US15/536,073 patent/US10183938B2/en not_active Expired - Fee Related
- 2015-12-14 WO PCT/US2015/065497 patent/WO2016100184A1/en not_active Ceased
- 2015-12-14 JP JP2017533183A patent/JP6612874B2/ja not_active Expired - Fee Related
- 2015-12-14 EP EP15870786.9A patent/EP3233087B1/en not_active Not-in-force
- 2015-12-14 AU AU2015362790A patent/AU2015362790A1/en not_active Abandoned
- 2015-12-14 ES ES15870786T patent/ES2764660T3/es active Active
- 2015-12-14 CA CA2971413A patent/CA2971413A1/en not_active Abandoned
-
2017
- 2017-06-15 IL IL252931A patent/IL252931A0/en unknown
-
2019
- 2019-10-31 JP JP2019198132A patent/JP2020033371A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP3233087B1 (en) | 2019-10-02 |
| CA2971413A1 (en) | 2016-06-23 |
| JP6612874B2 (ja) | 2019-11-27 |
| WO2016100184A1 (en) | 2016-06-23 |
| AU2015362790A1 (en) | 2017-07-20 |
| EP3233087A1 (en) | 2017-10-25 |
| IL252931A0 (en) | 2017-08-31 |
| US10183938B2 (en) | 2019-01-22 |
| JP2017538756A (ja) | 2017-12-28 |
| JP2020033371A (ja) | 2020-03-05 |
| EP3623371A1 (en) | 2020-03-18 |
| EP3233087A4 (en) | 2018-05-30 |
| US20170369486A1 (en) | 2017-12-28 |
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