TW201213327A - Heterocyclic compound and use thereof - Google Patents
Heterocyclic compound and use thereof Download PDFInfo
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- TW201213327A TW201213327A TW100131443A TW100131443A TW201213327A TW 201213327 A TW201213327 A TW 201213327A TW 100131443 A TW100131443 A TW 100131443A TW 100131443 A TW100131443 A TW 100131443A TW 201213327 A TW201213327 A TW 201213327A
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- group
- compound
- optionally substituted
- ring
- salt
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- 150000002391 heterocyclic compounds Chemical class 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 530
- 150000003839 salts Chemical class 0.000 claims abstract description 117
- 238000004519 manufacturing process Methods 0.000 claims abstract description 44
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 17
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 12
- -1 difluoroindolyl Chemical group 0.000 claims description 223
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 171
- 125000001424 substituent group Chemical group 0.000 claims description 154
- 125000005843 halogen group Chemical group 0.000 claims description 136
- 125000000217 alkyl group Chemical group 0.000 claims description 106
- 238000000034 method Methods 0.000 claims description 77
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 64
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 63
- 239000003814 drug Substances 0.000 claims description 52
- 125000003118 aryl group Chemical group 0.000 claims description 46
- 229940079593 drug Drugs 0.000 claims description 38
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 35
- 239000000126 substance Substances 0.000 claims description 29
- 208000024827 Alzheimer disease Diseases 0.000 claims description 21
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- 208000010877 cognitive disease Diseases 0.000 claims description 16
- 125000002883 imidazolyl group Chemical group 0.000 claims description 16
- 208000027061 mild cognitive impairment Diseases 0.000 claims description 15
- 239000003112 inhibitor Substances 0.000 claims description 13
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 13
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 7
- 210000003296 saliva Anatomy 0.000 claims description 6
- 102000009091 Amyloidogenic Proteins Human genes 0.000 claims description 5
- 108010048112 Amyloidogenic Proteins Proteins 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 4
- 150000002916 oxazoles Chemical group 0.000 claims description 4
- 230000033228 biological regulation Effects 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 2
- 230000003942 amyloidogenic effect Effects 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 10
- 102000002659 Amyloid Precursor Protein Secretases Human genes 0.000 abstract description 7
- 108010043324 Amyloid Precursor Protein Secretases Proteins 0.000 abstract description 7
- 102000013455 Amyloid beta-Peptides Human genes 0.000 abstract description 3
- 108010090849 Amyloid beta-Peptides Proteins 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 383
- 239000000203 mixture Substances 0.000 description 226
- 238000006243 chemical reaction Methods 0.000 description 212
- 239000002904 solvent Substances 0.000 description 171
- 235000019439 ethyl acetate Nutrition 0.000 description 159
- 239000002585 base Substances 0.000 description 105
- 235000002639 sodium chloride Nutrition 0.000 description 93
- 239000011541 reaction mixture Substances 0.000 description 88
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 77
- 229910052731 fluorine Inorganic materials 0.000 description 72
- 125000001153 fluoro group Chemical group F* 0.000 description 71
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 61
- 125000003545 alkoxy group Chemical group 0.000 description 61
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 61
- 125000004429 atom Chemical group 0.000 description 55
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 53
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 49
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- 238000005481 NMR spectroscopy Methods 0.000 description 42
- 229910052751 metal Inorganic materials 0.000 description 41
- 239000002184 metal Substances 0.000 description 41
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 40
- 235000019441 ethanol Nutrition 0.000 description 39
- 239000002253 acid Substances 0.000 description 37
- 238000002360 preparation method Methods 0.000 description 36
- 239000007789 gas Substances 0.000 description 35
- 229920006395 saturated elastomer Polymers 0.000 description 35
- 239000003795 chemical substances by application Substances 0.000 description 33
- 230000035484 reaction time Effects 0.000 description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 29
- 229910052801 chlorine Inorganic materials 0.000 description 29
- 150000002825 nitriles Chemical class 0.000 description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 125000001309 chloro group Chemical group Cl* 0.000 description 27
- 238000001816 cooling Methods 0.000 description 27
- 229940002612 prodrug Drugs 0.000 description 27
- 239000000651 prodrug Substances 0.000 description 27
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 26
- 238000012360 testing method Methods 0.000 description 26
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 25
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 25
- 239000000243 solution Substances 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 24
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 23
- 239000012046 mixed solvent Substances 0.000 description 23
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 23
- 239000007864 aqueous solution Substances 0.000 description 22
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- 125000003396 thiol group Chemical class [H]S* 0.000 description 22
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 21
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 21
- 125000003277 amino group Chemical group 0.000 description 20
- 230000002829 reductive effect Effects 0.000 description 20
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 19
- 150000002430 hydrocarbons Chemical group 0.000 description 19
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 19
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 19
- 229930195734 saturated hydrocarbon Natural products 0.000 description 19
- 235000011054 acetic acid Nutrition 0.000 description 18
- 125000006612 decyloxy group Chemical group 0.000 description 18
- 239000001301 oxygen Substances 0.000 description 18
- 229910052760 oxygen Inorganic materials 0.000 description 18
- 239000012312 sodium hydride Substances 0.000 description 18
- 229910000104 sodium hydride Inorganic materials 0.000 description 18
- 125000005577 anthracene group Chemical group 0.000 description 17
- 125000000753 cycloalkyl group Chemical group 0.000 description 17
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 16
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 16
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 16
- 229960004756 ethanol Drugs 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 15
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- 239000007787 solid Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 150000003462 sulfoxides Chemical class 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 14
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- 230000008569 process Effects 0.000 description 14
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- 150000003852 triazoles Chemical group 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 13
- 101100020289 Xenopus laevis koza gene Proteins 0.000 description 13
- 150000001412 amines Chemical class 0.000 description 13
- 239000004305 biphenyl Substances 0.000 description 13
- 125000002704 decyl group Chemical group [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])* 0.000 description 13
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 13
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 13
- 238000004949 mass spectrometry Methods 0.000 description 13
- 150000002752 molybdenum compounds Chemical class 0.000 description 13
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- 125000006239 protecting group Chemical group 0.000 description 13
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 101150041968 CDC13 gene Proteins 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
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- 229910052786 argon Inorganic materials 0.000 description 12
- SORXVYYPMXPIFD-UHFFFAOYSA-N iron palladium Chemical compound [Fe].[Pd] SORXVYYPMXPIFD-UHFFFAOYSA-N 0.000 description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 12
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
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- 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 6
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- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- PLLQWNRUYOYAJH-UHFFFAOYSA-H trimagnesium 2-hydroxypropane-1,2,3-tricarboxylate hexahydrate Chemical compound O.O.O.O.O.O.C(CC(O)(C(=O)[O-])CC(=O)[O-])(=O)[O-].[Mg+2].C(CC(O)(C(=O)[O-])CC(=O)[O-])(=O)[O-].[Mg+2].[Mg+2] PLLQWNRUYOYAJH-UHFFFAOYSA-H 0.000 description 1
- SOBHUZYZLFQYFK-UHFFFAOYSA-K trisodium;hydroxy-[[phosphonatomethyl(phosphonomethyl)amino]methyl]phosphinate Chemical compound [Na+].[Na+].[Na+].OP(O)(=O)CN(CP(O)([O-])=O)CP([O-])([O-])=O SOBHUZYZLFQYFK-UHFFFAOYSA-K 0.000 description 1
- RDOVSPPEPGMKEB-UHFFFAOYSA-L trisodium;sulfate Chemical compound [Na+].[Na+].[Na+].[O-]S([O-])(=O)=O RDOVSPPEPGMKEB-UHFFFAOYSA-L 0.000 description 1
- KBMBVTRWEAAZEY-UHFFFAOYSA-N trisulfane Chemical compound SSS KBMBVTRWEAAZEY-UHFFFAOYSA-N 0.000 description 1
- 229940046728 tumor necrosis factor alpha inhibitor Drugs 0.000 description 1
- 239000002451 tumor necrosis factor inhibitor Substances 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
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- 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
- 229960000604 valproic acid Drugs 0.000 description 1
- ACWBQPMHZXGDFX-QFIPXVFZSA-N valsartan Chemical compound C1=CC(CN(C(=O)CCCC)[C@@H](C(C)C)C(O)=O)=CC=C1C1=CC=CC=C1C1=NN=NN1 ACWBQPMHZXGDFX-QFIPXVFZSA-N 0.000 description 1
- 229960004699 valsartan Drugs 0.000 description 1
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- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- PJDFLNIOAUIZSL-UHFFFAOYSA-N vigabatrin Chemical compound C=CC(N)CCC(O)=O PJDFLNIOAUIZSL-UHFFFAOYSA-N 0.000 description 1
- 229960005318 vigabatrin Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
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- ZAFYATHCZYHLPB-UHFFFAOYSA-N zolpidem Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 ZAFYATHCZYHLPB-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
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| JP2010197064 | 2010-09-02 | ||
| JP2011143548 | 2011-06-28 |
Publications (1)
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| TW201213327A true TW201213327A (en) | 2012-04-01 |
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| 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)
| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
| SI1678172T1 (sl) * | 2003-10-15 | 2010-04-30 | Targacept Inc | AzabicikliŽŤne spojine za lajšanje boleŽŤine in zdravljenje motenj centralnega ĹľivŽŤnega sistema |
| US7667041B2 (en) | 2004-05-26 | 2010-02-23 | Eisai R&D Management Co., Ltd. | Cinnamide compound |
| ATE458729T1 (de) | 2004-10-26 | 2010-03-15 | Eisai R&D Man Co Ltd | Amorphe form einer zimtsäureamidverbindung |
| EP1976527A4 (en) | 2006-01-11 | 2009-04-22 | Merck & Co Inc | CONDENSED TRIAZOL TACHYKININE RECEPTOR ANTAGONISTS |
| TWI378091B (en) | 2006-03-09 | 2012-12-01 | Eisai R&D Man Co Ltd | Multi-cyclic cinnamide derivatives |
| PL1992618T3 (pl) * | 2006-03-09 | 2012-06-29 | Eisai R&D Man Co Ltd | Policykliczna pochodna cynamidowa |
| TW200808800A (en) | 2006-05-05 | 2008-02-16 | Astrazeneca Ab | MGluR5 modulators V |
| EP2119719A1 (en) | 2006-12-26 | 2009-11-18 | Daiichi Sankyo Company, Limited | Thiazepine derivative |
| WO2008077649A1 (en) | 2006-12-26 | 2008-07-03 | Gilead Sciences, Inc. | Pyrido(3,2-d)pyrimidines useful for treating viral infectons |
| CA2677296A1 (en) | 2007-02-08 | 2008-08-14 | Merck & Co., Inc. | Therapeutic agents |
| CA2707712A1 (en) | 2007-12-06 | 2009-06-11 | Schering Corporation | Gamma secretase modulators |
| TW201030002A (en) | 2009-01-16 | 2010-08-16 | Bristol Myers Squibb Co | Bicyclic compounds for the reduction of beta-amyloid production |
| JP2010197064A (ja) | 2009-02-23 | 2010-09-09 | Chugoku Electric Power Co Inc:The | 直下位置測定装置 |
| JP2012051806A (ja) | 2009-02-26 | 2012-03-15 | Eisai R & D Management Co Ltd | イミダゾリルピラジン誘導体 |
| EP2401276B1 (en) * | 2009-02-26 | 2013-06-05 | Eisai R&D Management Co., Ltd. | Nitrogen-containing fused heterocyclic compounds and their use as beta amyloid production inhibitors |
| JP2012051807A (ja) | 2009-02-26 | 2012-03-15 | Eisai R & D Management Co Ltd | アリールイミダゾール化合物 |
| WO2011002067A1 (ja) | 2009-07-02 | 2011-01-06 | 武田薬品工業株式会社 | 複素環化合物およびその用途 |
| 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 |
| NZ597505A (en) | 2009-07-15 | 2013-05-31 | Janssen Pharmaceuticals Inc | Substituted triazole and imidazole derivatives as gamma secretase modulators |
| US8637525B2 (en) | 2009-07-31 | 2014-01-28 | Bristol-Myers Squibb Company | Compounds for the reduction of beta-amyloid production |
| TWI468402B (zh) | 2009-07-31 | 2015-01-11 | 必治妥美雅史谷比公司 | 降低β－類澱粉生成之化合物 |
| WO2011016559A1 (ja) | 2009-08-07 | 2011-02-10 | 武田薬品工業株式会社 | 複素環化合物およびその用途 |
| JP2011143548A (ja) | 2010-01-12 | 2011-07-28 | Panasonic Corp | スクリーン印刷機及びスクリーン印刷方法 |
| US9145399B2 (en) | 2010-01-15 | 2015-09-29 | Janssen Pharmaceuticals, Inc. | Substituted bicyclic triazole derivatives as gamma secretase modulators |
| US8822699B2 (en) * | 2010-09-02 | 2014-09-02 | Takeda Pharmaceutical Company Limited | Heterocyclic compound and use thereof |
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2011
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- 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
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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
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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 |
| CA2809779A1 (en) | 2012-03-08 |
| 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 |
| 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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