JP5358571B2 - セロトニン作動性調節因子としての１，２，４−トリアゾール誘導体 - Google Patents
セロトニン作動性調節因子としての１，２，４−トリアゾール誘導体 Download PDFInfo
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- JP5358571B2 JP5358571B2 JP2010519520A JP2010519520A JP5358571B2 JP 5358571 B2 JP5358571 B2 JP 5358571B2 JP 2010519520 A JP2010519520 A JP 2010519520A JP 2010519520 A JP2010519520 A JP 2010519520A JP 5358571 B2 JP5358571 B2 JP 5358571B2
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- compound
- ethyl
- dihydro
- triazol
- formula
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- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical class C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 title 1
- 230000000862 serotonergic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 138
- 238000011282 treatment Methods 0.000 claims abstract description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 43
- 150000003839 salts Chemical class 0.000 claims description 24
- -1 cyclooctyl compound Chemical class 0.000 claims description 23
- 239000000460 chlorine Substances 0.000 claims description 22
- 208000035475 disorder Diseases 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 239000012453 solvate Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- FJRAORURQAFYNK-UHFFFAOYSA-N n-[3-[4-[2-[4-(cyclohexylmethyl)-1-methyl-5-oxo-1,2,4-triazol-3-yl]ethyl]piperazin-1-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(N2CCN(CCC=3N(C(=O)N(C)N=3)CC3CCCCC3)CC2)=C1 FJRAORURQAFYNK-UHFFFAOYSA-N 0.000 claims description 7
- 208000019901 Anxiety disease Diseases 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- ZWLCYOWQGKARQR-UHFFFAOYSA-N 4-(cyclohexylmethyl)-5-[2-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2-methyl-1,2,4-triazol-3-one Chemical compound COC1=CC=CC=C1N1CCN(C(C)CC=2N(C(=O)N(C)N=2)CC2CCCCC2)CC1 ZWLCYOWQGKARQR-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 230000036506 anxiety Effects 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- HZWXCIJANPHNHI-UHFFFAOYSA-N 4-(cyclohexylmethyl)-2-ethyl-5-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-1,2,4-triazol-3-one Chemical compound C1CCCCC1CN1C(=O)N(CC)N=C1CCN(CC1)CCN1C1=CC=CC=C1OC HZWXCIJANPHNHI-UHFFFAOYSA-N 0.000 claims description 3
- RAOZDGXYGZWMRD-UHFFFAOYSA-N 4-(cyclohexylmethyl)-5-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-2-methyl-1,2,4-triazol-3-one Chemical compound COC1=CC=CC=C1N1CCN(CCC=2N(C(=O)N(C)N=2)CC2CCCCC2)CC1 RAOZDGXYGZWMRD-UHFFFAOYSA-N 0.000 claims description 3
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 238000010511 deprotection reaction Methods 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 abstract description 70
- 230000009471 action Effects 0.000 abstract description 7
- 229940075993 receptor modulator Drugs 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000007787 solid Substances 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 201000010099 disease Diseases 0.000 description 24
- 238000000034 method Methods 0.000 description 24
- 239000000203 mixture Substances 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 239000000543 intermediate Substances 0.000 description 18
- 230000014759 maintenance of location Effects 0.000 description 17
- 239000002904 solvent Substances 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
- 239000000725 suspension Substances 0.000 description 16
- 230000002829 reductive effect Effects 0.000 description 13
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 239000003814 drug Substances 0.000 description 11
- 102000004980 Dopamine D2 Receptors Human genes 0.000 description 10
- 108090001111 Dopamine D2 Receptors Proteins 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 102000005962 receptors Human genes 0.000 description 10
- 108020003175 receptors Proteins 0.000 description 10
- PYRFHJUXDGQZPM-UHFFFAOYSA-N 1,2,4-triazole-3-thione Chemical compound S=C1N=CN=N1 PYRFHJUXDGQZPM-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- WIEZWEYWUAGSRI-UHFFFAOYSA-N 4-cyclooctyl-3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-1h-1,2,4-triazol-5-one Chemical compound COC1=CC=CC=C1N1CCN(CCC=2N(C(=O)NN=2)C2CCCCCCC2)CC1 WIEZWEYWUAGSRI-UHFFFAOYSA-N 0.000 description 8
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000003556 assay Methods 0.000 description 8
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 8
- 239000000546 pharmaceutical excipient Substances 0.000 description 8
- 239000002002 slurry Substances 0.000 description 8
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 238000003818 flash chromatography Methods 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- JWUUJJNTHNKVQG-UHFFFAOYSA-N 3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-4-phenyl-1h-1,2,4-triazol-5-one Chemical compound COC1=CC=CC=C1N1CCN(CCC=2N(C(=O)NN=2)C=2C=CC=CC=2)CC1 JWUUJJNTHNKVQG-UHFFFAOYSA-N 0.000 description 6
- LVRNRCAWRVYYTF-UHFFFAOYSA-N 4-(cyclohexylmethyl)-3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-1h-1,2,4-triazol-5-one Chemical compound COC1=CC=CC=C1N1CCN(CCC=2N(C(=O)NN=2)CC2CCCCC2)CC1 LVRNRCAWRVYYTF-UHFFFAOYSA-N 0.000 description 6
- IAYJXGHICTUMOA-UHFFFAOYSA-N 4-(cyclohexylmethyl)-3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-1h-1,2,4-triazol-5-one Chemical compound COC1=CC=CC=C1N1CCN(C(C)CC=2N(C(=O)NN=2)CC2CCCCC2)CC1 IAYJXGHICTUMOA-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 208000024827 Alzheimer disease Diseases 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 230000027455 binding Effects 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 239000000796 flavoring agent Substances 0.000 description 6
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- 125000005647 linker group Chemical group 0.000 description 6
- YQGMTFYBYOYNMH-UHFFFAOYSA-N n-[3-[4-[2-[4-(cyclohexylmethyl)-5-oxo-1h-1,2,4-triazol-3-yl]ethyl]piperazin-1-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(N2CCN(CCC=3N(C(=O)NN=3)CC3CCCCC3)CC2)=C1 YQGMTFYBYOYNMH-UHFFFAOYSA-N 0.000 description 6
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([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
- 238000000746 purification Methods 0.000 description 6
- 229940076279 serotonin Drugs 0.000 description 6
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- GNJLPKLSZRALOF-UHFFFAOYSA-N 3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-4-[(4-methylphenyl)methyl]-1h-1,2,4-triazol-5-one Chemical compound COC1=CC=CC=C1N1CCN(CCC=2N(C(=O)NN=2)CC=2C=CC(C)=CC=2)CC1 GNJLPKLSZRALOF-UHFFFAOYSA-N 0.000 description 5
- DILZZWHTUQZRGC-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propanehydrazide Chemical compound COC1=CC=CC=C1N1CCN(CCC(=O)NN)CC1 DILZZWHTUQZRGC-UHFFFAOYSA-N 0.000 description 5
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- MDTUWBLTRPRXBX-UHFFFAOYSA-N 1,2,4-triazol-3-one Chemical class O=C1N=CN=N1 MDTUWBLTRPRXBX-UHFFFAOYSA-N 0.000 description 4
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- 150000003904 phospholipids Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 239000000661 sodium alginate Substances 0.000 description 1
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- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
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- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 230000000392 somatic effect Effects 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 201000001716 specific phobia Diseases 0.000 description 1
- DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 1
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- 238000010561 standard procedure Methods 0.000 description 1
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- 230000035882 stress Effects 0.000 description 1
- 201000009032 substance abuse Diseases 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
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- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- CEIJFEGBUDEYSX-FZDBZEDMSA-N tandospirone Chemical compound O=C([C@@H]1[C@H]2CC[C@H](C2)[C@@H]1C1=O)N1CCCCN(CC1)CCN1C1=NC=CC=N1 CEIJFEGBUDEYSX-FZDBZEDMSA-N 0.000 description 1
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- 239000011975 tartaric acid Substances 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
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- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 229950002929 trinitrophenol Drugs 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
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- AERLHOTUXIJQFV-RCPZPFRWSA-N zalospirone Chemical compound O=C([C@@H]1[C@@H]([C@@H]2C=C[C@H]1[C@H]1C=C[C@H]12)C1=O)N1CCCCN(CC1)CCN1C1=NC=CC=N1 AERLHOTUXIJQFV-RCPZPFRWSA-N 0.000 description 1
- 229950005255 zalospirone Drugs 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
-
- 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
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
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- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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- 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
- A61P25/16—Anti-Parkinson drugs
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A61P25/24—Antidepressants
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- A61P25/32—Alcohol-abuse
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
-
- 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
- C07D401/12—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 chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Addiction (AREA)
- Reproductive Health (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0715378.6 | 2007-08-07 | ||
| GB0715378A GB0715378D0 (en) | 2007-08-07 | 2007-08-07 | Novel serotonergic modulators |
| GB0810168A GB0810168D0 (en) | 2008-06-04 | 2008-06-04 | Novel serotonergic modulators |
| GB0810168.5 | 2008-06-04 | ||
| PCT/GB2008/002669 WO2009019472A1 (en) | 2007-08-07 | 2008-08-06 | 1, 2, 4 -triazole derivatives as serotonergic modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010535751A JP2010535751A (ja) | 2010-11-25 |
| JP2010535751A5 JP2010535751A5 (enExample) | 2011-09-22 |
| JP5358571B2 true JP5358571B2 (ja) | 2013-12-04 |
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| Application Number | Title | Priority Date | Filing Date |
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| JP2010519520A Expired - Fee Related JP5358571B2 (ja) | 2007-08-07 | 2008-08-06 | セロトニン作動性調節因子としての１，２，４−トリアゾール誘導体 |
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| US (1) | US8222254B2 (enExample) |
| EP (1) | EP2183227B1 (enExample) |
| JP (1) | JP5358571B2 (enExample) |
| CN (1) | CN101827828B (enExample) |
| CA (1) | CA2694621C (enExample) |
| GB (1) | GB2454290B (enExample) |
| WO (1) | WO2009019472A1 (enExample) |
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| JP5787237B2 (ja) * | 2010-10-01 | 2015-09-30 | 大正製薬株式会社 | １，２，４−トリアゾロン誘導体 |
| EP2822931B1 (en) | 2012-03-09 | 2017-05-03 | Inception 2, Inc. | Triazolone compounds and uses thereof |
| JP6404230B2 (ja) | 2012-12-20 | 2018-10-10 | インセプション ２、 インコーポレイテッド | トリアゾロン化合物およびその使用 |
| CA2921420A1 (en) | 2013-09-06 | 2015-03-12 | Inception 2, Inc. | Triazolone compounds and uses thereof |
| US12459965B2 (en) | 2017-10-09 | 2025-11-04 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| GB2571696B (en) | 2017-10-09 | 2020-05-27 | Compass Pathways Ltd | Large scale method for the preparation of Psilocybin and formulations of Psilocybin so produced |
| WO2020212951A1 (en) | 2019-04-17 | 2020-10-22 | Compass Pathfinder Limited | Methods for treating anxiety disorders, headache disorders, and eating disorders with psilocybin |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4166452A (en) | 1976-05-03 | 1979-09-04 | Generales Constantine D J Jr | Apparatus for testing human responses to stimuli |
| US4182763A (en) | 1978-05-22 | 1980-01-08 | Mead Johnson & Company | Buspirone anti-anxiety method |
| US4356108A (en) | 1979-12-20 | 1982-10-26 | The Mead Corporation | Encapsulation process |
| US4265874A (en) | 1980-04-25 | 1981-05-05 | Alza Corporation | Method of delivering drug with aid of effervescent activity generated in environment of use |
| US4487773A (en) * | 1981-03-16 | 1984-12-11 | Mead Johnson & Company | 1,2,4-Triazol-3-one antidepressants |
| US4338317A (en) * | 1981-03-16 | 1982-07-06 | Mead Johnson & Company | Phenoxyethyl-1,2,4,-triazol-3-one antidepressants |
| DE4425144A1 (de) * | 1994-07-15 | 1996-01-18 | Basf Ag | Triazolverbindungen und deren Verwendung |
| AU6517196A (en) * | 1995-07-13 | 1997-02-10 | Knoll Aktiengesellschaft | Piperazine derivatives as therapeutic agents |
| FR2841544B1 (fr) | 2002-06-27 | 2004-08-27 | Heurgue Conseil S A | Dispositif de vidange de silo |
| US7153858B2 (en) | 2003-01-31 | 2006-12-26 | Epix Delaware, Inc. | Arylpiperazinyl compounds |
-
2008
- 2008-08-06 CN CN2008801021328A patent/CN101827828B/zh not_active Expired - Fee Related
- 2008-08-06 GB GB0814351A patent/GB2454290B/en not_active Expired - Fee Related
- 2008-08-06 JP JP2010519520A patent/JP5358571B2/ja not_active Expired - Fee Related
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- 2008-08-06 WO PCT/GB2008/002669 patent/WO2009019472A1/en not_active Ceased
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- 2008-08-06 EP EP08776140.9A patent/EP2183227B1/en not_active Not-in-force
Also Published As
| Publication number | Publication date |
|---|---|
| CA2694621A1 (en) | 2009-02-12 |
| CA2694621C (en) | 2015-01-06 |
| US8222254B2 (en) | 2012-07-17 |
| GB2454290A (en) | 2009-05-06 |
| EP2183227A1 (en) | 2010-05-12 |
| JP2010535751A (ja) | 2010-11-25 |
| US20100261732A1 (en) | 2010-10-14 |
| GB0814351D0 (en) | 2008-09-10 |
| CN101827828A (zh) | 2010-09-08 |
| CN101827828B (zh) | 2013-02-27 |
| EP2183227B1 (en) | 2014-09-24 |
| WO2009019472A1 (en) | 2009-02-12 |
| WO2009019472A4 (en) | 2009-04-09 |
| GB2454290B (en) | 2009-09-30 |
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