CA2809779A1 - Fused triazoles for the treatment or prophylaxis of mild cognitive impairment - Google Patents
Fused triazoles for the treatment or prophylaxis of mild cognitive impairment Download PDFInfo
- Publication number
- CA2809779A1 CA2809779A1 CA2809779A CA2809779A CA2809779A1 CA 2809779 A1 CA2809779 A1 CA 2809779A1 CA 2809779 A CA2809779 A CA 2809779A CA 2809779 A CA2809779 A CA 2809779A CA 2809779 A1 CA2809779 A1 CA 2809779A1
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- Prior art keywords
- optionally substituted
- compound
- group
- salt
- ring
- 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
- 208000010877 cognitive disease Diseases 0.000 title claims description 18
- 208000027061 mild cognitive impairment Diseases 0.000 title claims description 18
- 238000011282 treatment Methods 0.000 title claims description 15
- 238000011321 prophylaxis Methods 0.000 title claims description 12
- 150000003852 triazoles Chemical class 0.000 title description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 577
- 150000003839 salts Chemical class 0.000 claims abstract description 114
- 238000004519 manufacturing process Methods 0.000 claims abstract description 54
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims description 170
- 125000001424 substituent group Chemical group 0.000 claims description 160
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 140
- 238000000034 method Methods 0.000 claims description 90
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 80
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 76
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 57
- 239000003795 chemical substances by application Substances 0.000 claims description 48
- 239000003814 drug Substances 0.000 claims description 48
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 45
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 42
- 229940079593 drug Drugs 0.000 claims description 33
- 125000002883 imidazolyl group Chemical group 0.000 claims description 30
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 28
- 208000024827 Alzheimer disease Diseases 0.000 claims description 25
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 18
- 230000036961 partial effect Effects 0.000 claims description 17
- 125000001425 triazolyl group Chemical group 0.000 claims description 17
- 241000124008 Mammalia Species 0.000 claims description 13
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 12
- 239000003112 inhibitor Substances 0.000 claims description 11
- 150000001555 benzenes Chemical group 0.000 claims description 10
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 9
- NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical group C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 claims description 9
- 150000002916 oxazoles Chemical group 0.000 claims description 7
- 230000005764 inhibitory process Effects 0.000 claims description 3
- TYZSJCRDLQKNAA-AREMUKBSSA-N 2-[(8r)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-(3,4,5-trifluorophenoxy)-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyridin-8-yl]propan-2-ol Chemical compound COC1=CC(C=2N3C([C@@](CCC3)(OC=3C=C(F)C(F)=C(F)C=3)C(C)(C)O)=NN=2)=CC=C1C1=CN=C(C)O1 TYZSJCRDLQKNAA-AREMUKBSSA-N 0.000 claims description 2
- FUNFAPKBEIRFLV-UHFFFAOYSA-N 2-[8-(4-chloro-3-fluorophenoxy)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyridin-8-yl]propan-2-ol Chemical compound COC1=CC(C=2N3C(C(CCC3)(OC=3C=C(F)C(Cl)=CC=3)C(C)(C)O)=NN=2)=CC=C1C1=CN=C(C)O1 FUNFAPKBEIRFLV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- WWFFQXDRJZKGDS-RUZDIDTESA-N 2-[(8r)-3-[6-methoxy-5-(4-methylimidazol-1-yl)pyridin-2-yl]-8-(3,4,5-trifluorophenoxy)-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyridin-8-yl]propan-2-ol Chemical compound COC1=NC(C=2N3C([C@@](CCC3)(OC=3C=C(F)C(F)=C(F)C=3)C(C)(C)O)=NN=2)=CC=C1N1C=NC(C)=C1 WWFFQXDRJZKGDS-RUZDIDTESA-N 0.000 claims 1
- RIXAYKFZSRGVTI-UHFFFAOYSA-N 2-[3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-[3-(trifluoromethyl)phenoxy]-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyridin-8-yl]propan-2-ol Chemical compound COC1=CC(C=2N3C(C(CCC3)(OC=3C=C(C=CC=3)C(F)(F)F)C(C)(C)O)=NN=2)=CC=C1C1=CN=C(C)O1 RIXAYKFZSRGVTI-UHFFFAOYSA-N 0.000 claims 1
- CSZXOHDAQYOWJT-UHFFFAOYSA-N 2-[3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-[4-(trifluoromethyl)phenoxy]-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyridin-8-yl]propan-2-ol Chemical compound COC1=CC(C=2N3C(C(CCC3)(OC=3C=CC(=CC=3)C(F)(F)F)C(C)(C)O)=NN=2)=CC=C1C1=CN=C(C)O1 CSZXOHDAQYOWJT-UHFFFAOYSA-N 0.000 claims 1
- 241001367053 Autographa gamma Species 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 11
- 102000013455 Amyloid beta-Peptides Human genes 0.000 abstract 1
- 108010090849 Amyloid beta-Peptides Proteins 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 386
- -1 cinnamide compound Chemical class 0.000 description 230
- 238000006243 chemical reaction Methods 0.000 description 228
- 239000002904 solvent Substances 0.000 description 223
- 239000000203 mixture Substances 0.000 description 214
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 150
- 239000011541 reaction mixture Substances 0.000 description 92
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
- 229910052731 fluorine Inorganic materials 0.000 description 82
- 125000001153 fluoro group Chemical group F* 0.000 description 78
- 230000002829 reductive effect Effects 0.000 description 75
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 74
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 69
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
- 239000002585 base Substances 0.000 description 59
- 239000000243 solution Substances 0.000 description 58
- 101150041968 CDC13 gene Proteins 0.000 description 53
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 53
- 238000010898 silica gel chromatography Methods 0.000 description 51
- 229910052751 metal Inorganic materials 0.000 description 50
- 239000002184 metal Substances 0.000 description 50
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 47
- 239000003153 chemical reaction reagent Substances 0.000 description 44
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 41
- 150000001408 amides Chemical class 0.000 description 40
- 229910052801 chlorine Inorganic materials 0.000 description 40
- 125000001309 chloro group Chemical group Cl* 0.000 description 39
- 150000002170 ethers Chemical class 0.000 description 36
- 230000035484 reaction time Effects 0.000 description 36
- 239000012046 mixed solvent Substances 0.000 description 35
- 150000008282 halocarbons Chemical class 0.000 description 33
- 150000002825 nitriles Chemical class 0.000 description 33
- 229930195734 saturated hydrocarbon Natural products 0.000 description 33
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 32
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 32
- 125000003545 alkoxy group Chemical group 0.000 description 32
- 125000000217 alkyl group Chemical group 0.000 description 32
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 32
- 229920006395 saturated elastomer Polymers 0.000 description 32
- 239000003054 catalyst Substances 0.000 description 31
- 238000001816 cooling Methods 0.000 description 31
- 238000002360 preparation method Methods 0.000 description 31
- 229940002612 prodrug Drugs 0.000 description 31
- 239000000651 prodrug Substances 0.000 description 31
- 150000003462 sulfoxides Chemical class 0.000 description 30
- 239000000126 substance Substances 0.000 description 29
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 125000002947 alkylene group Chemical group 0.000 description 27
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- 239000002253 acid Substances 0.000 description 24
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 23
- 150000007530 organic bases Chemical class 0.000 description 21
- 125000002971 oxazolyl group Chemical group 0.000 description 21
- 125000003118 aryl group Chemical group 0.000 description 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 19
- 239000007787 solid Substances 0.000 description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 18
- 238000001914 filtration Methods 0.000 description 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 18
- 239000012312 sodium hydride Substances 0.000 description 18
- 229910000104 sodium hydride Inorganic materials 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 17
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- 150000001298 alcohols Chemical class 0.000 description 16
- 150000001447 alkali salts Chemical class 0.000 description 16
- 125000003277 amino group Chemical group 0.000 description 16
- 235000019270 ammonium chloride Nutrition 0.000 description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 16
- 235000017557 sodium bicarbonate Nutrition 0.000 description 16
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 15
- 150000007529 inorganic bases Chemical class 0.000 description 15
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 14
- 201000010099 disease Diseases 0.000 description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 101100020289 Xenopus laevis koza gene Proteins 0.000 description 13
- 238000006482 condensation reaction Methods 0.000 description 13
- 150000007522 mineralic acids Chemical class 0.000 description 13
- 150000007524 organic acids Chemical class 0.000 description 13
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 13
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
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- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000007254 oxidation reaction Methods 0.000 description 12
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 12
- 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 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 11
- 150000008046 alkali metal hydrides Chemical class 0.000 description 11
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- WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 description 11
- 125000004093 cyano group Chemical group *C#N 0.000 description 11
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- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 11
- 125000004076 pyridyl group Chemical group 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 10
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
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- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 8
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- 235000011054 acetic acid Nutrition 0.000 description 8
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- 230000002140 halogenating effect Effects 0.000 description 8
- 230000014759 maintenance of location Effects 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 8
- 239000012299 nitrogen atmosphere Substances 0.000 description 8
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- 241000894007 species Species 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 230000006209 tert-butylation Effects 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- KBLZDCFTQSIIOH-UHFFFAOYSA-M tetrabutylazanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC KBLZDCFTQSIIOH-UHFFFAOYSA-M 0.000 description 1
- 125000005887 tetrahydrobenzofuranyl group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- AWDBHOZBRXWRKS-UHFFFAOYSA-N tetrapotassium;iron(6+);hexacyanide Chemical compound [K+].[K+].[K+].[K+].[Fe+6].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] AWDBHOZBRXWRKS-UHFFFAOYSA-N 0.000 description 1
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- PHWBOXQYWZNQIN-UHFFFAOYSA-N ticlopidine Chemical compound ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 PHWBOXQYWZNQIN-UHFFFAOYSA-N 0.000 description 1
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- 125000004306 triazinyl group Chemical group 0.000 description 1
- JOFWLTCLBGQGBO-UHFFFAOYSA-N triazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1Cl JOFWLTCLBGQGBO-UHFFFAOYSA-N 0.000 description 1
- 229960003386 triazolam Drugs 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- DWCSXQCXXITVKE-UHFFFAOYSA-N triethyloxidanium Chemical compound CC[O+](CC)CC DWCSXQCXXITVKE-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
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- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- 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
- A61P25/28—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010-197064 | 2010-09-02 | ||
| JP2010197064 | 2010-09-02 | ||
| JP2011-143548 | 2011-06-28 | ||
| JP2011143548 | 2011-06-28 | ||
| PCT/JP2011/070419 WO2012029991A1 (en) | 2010-09-02 | 2011-09-01 | Fused triazoles for the treatment or prophylaxis of mild cognitive impairment |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2809779A1 true CA2809779A1 (en) | 2012-03-08 |
Family
ID=45094181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2809779A Abandoned CA2809779A1 (en) | 2010-09-02 | 2011-09-01 | Fused triazoles for the treatment or prophylaxis of mild cognitive impairment |
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| EP (1) | EP2611805A1 (enExample) |
| JP (1) | JP5871909B2 (enExample) |
| KR (1) | KR20130139895A (enExample) |
| CN (1) | CN103249733A (enExample) |
| AR (1) | AR082865A1 (enExample) |
| AU (1) | AU2011296887A1 (enExample) |
| BR (1) | BR112013004746A2 (enExample) |
| CA (1) | CA2809779A1 (enExample) |
| CL (1) | CL2013000575A1 (enExample) |
| DO (1) | DOP2013000051A (enExample) |
| EA (1) | EA201390333A1 (enExample) |
| EC (1) | ECSP13012535A (enExample) |
| MA (1) | MA34556B1 (enExample) |
| MX (1) | MX2013002511A (enExample) |
| PE (1) | PE20131305A1 (enExample) |
| PH (1) | PH12013500403A1 (enExample) |
| SG (1) | SG187917A1 (enExample) |
| TW (1) | TW201213327A (enExample) |
| UY (1) | UY33586A (enExample) |
| WO (1) | WO2012029991A1 (enExample) |
| ZA (1) | ZA201301929B (enExample) |
Families Citing this family (7)
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| WO2011007756A1 (ja) * | 2009-07-13 | 2011-01-20 | 武田薬品工業株式会社 | 複素環化合物及びその用途 |
| US8822699B2 (en) * | 2010-09-02 | 2014-09-02 | Takeda Pharmaceutical Company Limited | Heterocyclic compound and use thereof |
| EP2687528A1 (en) * | 2012-07-17 | 2014-01-22 | Ares Trading S.A. | Fused triazole derivatives as gamma secretase modulators |
| RU2563254C2 (ru) * | 2013-07-08 | 2015-09-20 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Московский государственный университет имени М.В. Ломоносова" (МГУ) | Способ получения производных 7-(гетеро)арил-4,5,6,7-тетрагидро[1,2,3]триазоло[1,5-a]пиридина |
| PL3294743T3 (pl) * | 2015-05-12 | 2020-03-31 | Fmc Corporation | Podstawione arylem związki bicykliczne jako środki chwastobójcze |
| US20210079182A1 (en) * | 2019-09-12 | 2021-03-18 | Dupont Electronics, Inc. | Polyimide films and electronic devices |
| WO2023114456A1 (en) * | 2021-12-17 | 2023-06-22 | Athira Pharma, Inc. | Uses of bicyclic compounds for the treatment of diseases |
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| JP2003523345A (ja) | 2000-02-17 | 2003-08-05 | ブリストル−マイヤーズ スクイブ ファーマ カンパニー | Ａβタンパク質産生の阻害剤としてのスクシノイルアミノ炭素環および複素環 |
| US7244739B2 (en) | 2003-05-14 | 2007-07-17 | Torreypines Therapeutics, Inc. | Compounds and uses thereof in modulating amyloid beta |
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-
2011
- 2011-09-01 US US13/223,455 patent/US8822699B2/en not_active Expired - Fee Related
- 2011-09-01 MA MA35785A patent/MA34556B1/fr unknown
- 2011-09-01 CA CA2809779A patent/CA2809779A1/en not_active Abandoned
- 2011-09-01 EA EA201390333A patent/EA201390333A1/ru unknown
- 2011-09-01 PH PH1/2013/500403A patent/PH12013500403A1/en unknown
- 2011-09-01 KR KR1020137008170A patent/KR20130139895A/ko not_active Withdrawn
- 2011-09-01 BR BR112013004746A patent/BR112013004746A2/pt not_active IP Right Cessation
- 2011-09-01 AU AU2011296887A patent/AU2011296887A1/en not_active Abandoned
- 2011-09-01 UY UY0001033586A patent/UY33586A/es unknown
- 2011-09-01 EP EP11791058.8A patent/EP2611805A1/en not_active Withdrawn
- 2011-09-01 JP JP2013510386A patent/JP5871909B2/ja not_active Expired - Fee Related
- 2011-09-01 PE PE2013000360A patent/PE20131305A1/es not_active Application Discontinuation
- 2011-09-01 WO PCT/JP2011/070419 patent/WO2012029991A1/en not_active Ceased
- 2011-09-01 MX MX2013002511A patent/MX2013002511A/es not_active Application Discontinuation
- 2011-09-01 CN CN2011800518621A patent/CN103249733A/zh active Pending
- 2011-09-01 SG SG2013012604A patent/SG187917A1/en unknown
- 2011-09-01 AR ARP110103195A patent/AR082865A1/es unknown
- 2011-09-01 TW TW100131443A patent/TW201213327A/zh unknown
- 2011-09-01 US US13/819,239 patent/US8901309B2/en not_active Expired - Fee Related
-
2013
- 2013-02-28 CL CL2013000575A patent/CL2013000575A1/es unknown
- 2013-03-01 DO DO2013000051A patent/DOP2013000051A/es unknown
- 2013-03-14 ZA ZA2013/01929A patent/ZA201301929B/en unknown
- 2013-03-28 EC ECSP13012535 patent/ECSP13012535A/es unknown
-
2014
- 2014-08-08 US US14/454,993 patent/US20140350260A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| PH12013500403A1 (en) | 2013-03-25 |
| SG187917A1 (en) | 2013-04-30 |
| KR20130139895A (ko) | 2013-12-23 |
| JP5871909B2 (ja) | 2016-03-01 |
| MX2013002511A (es) | 2013-07-29 |
| AU2011296887A1 (en) | 2013-04-11 |
| ZA201301929B (en) | 2013-11-27 |
| UY33586A (es) | 2012-03-30 |
| DOP2013000051A (es) | 2013-04-30 |
| EA201390333A1 (ru) | 2013-08-30 |
| CL2013000575A1 (es) | 2013-08-23 |
| US20130178497A1 (en) | 2013-07-11 |
| CN103249733A (zh) | 2013-08-14 |
| AR082865A1 (es) | 2013-01-16 |
| US8901309B2 (en) | 2014-12-02 |
| US8822699B2 (en) | 2014-09-02 |
| WO2012029991A1 (en) | 2012-03-08 |
| EP2611805A1 (en) | 2013-07-10 |
| TW201213327A (en) | 2012-04-01 |
| US20120059030A1 (en) | 2012-03-08 |
| BR112013004746A2 (pt) | 2016-06-07 |
| MA34556B1 (fr) | 2013-09-02 |
| ECSP13012535A (es) | 2013-06-28 |
| US20140350260A1 (en) | 2014-11-27 |
| JP2013536798A (ja) | 2013-09-26 |
| PE20131305A1 (es) | 2013-10-31 |
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