JP2014517833A5 - - Google Patents
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- JP2014517833A5 JP2014517833A5 JP2014510414A JP2014510414A JP2014517833A5 JP 2014517833 A5 JP2014517833 A5 JP 2014517833A5 JP 2014510414 A JP2014510414 A JP 2014510414A JP 2014510414 A JP2014510414 A JP 2014510414A JP 2014517833 A5 JP2014517833 A5 JP 2014517833A5
- Authority
- JP
- Japan
- Prior art keywords
- heteroaryl
- aryl
- cycloalkyl
- heterocyclyl
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 121
- 125000000217 alkyl group Chemical group 0.000 claims description 97
- 125000000623 heterocyclic group Chemical group 0.000 claims description 97
- 125000003118 aryl group Chemical group 0.000 claims description 88
- 150000001875 compounds Chemical class 0.000 claims description 69
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 64
- 125000005843 halogen group Chemical group 0.000 claims description 58
- 125000001424 substituent group Chemical group 0.000 claims description 56
- -1 -N (R 26 ) (R 28 ) Chemical group 0.000 claims description 52
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 45
- 125000005418 aryl aryl group Chemical group 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 26
- 239000011780 sodium chloride Substances 0.000 claims description 26
- 125000000304 alkynyl group Chemical group 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 9
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- GXKPZKOLTOGOTN-UHFFFAOYSA-N 2,2-dimethyl-3-(pyridin-2-ylmethyl)-6-[4-(trifluoromethoxy)phenyl]-1,3-benzoxazin-4-one Chemical compound CC1(C)OC2=CC=C(C=3C=CC(OC(F)(F)F)=CC=3)C=C2C(=O)N1CC1=CC=CC=N1 GXKPZKOLTOGOTN-UHFFFAOYSA-N 0.000 claims description 2
- IRDRGAPMRVUDIT-UHFFFAOYSA-N 2-methyl-3-(pyrimidin-2-ylmethyl)-6-[4-(trifluoromethoxy)phenyl]-2H-1,3-benzoxazin-4-one Chemical compound CC1OC2=CC=C(C=3C=CC(OC(F)(F)F)=CC=3)C=C2C(=O)N1CC1=NC=CC=N1 IRDRGAPMRVUDIT-UHFFFAOYSA-N 0.000 claims description 2
- LKIWLRFRMTVENN-UHFFFAOYSA-N 3-(pyrimidin-2-ylmethyl)-6-[4-(trifluoromethoxy)phenyl]-2H-1,3-benzoxazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(OCN(CC=2N=CC=CN=2)C2=O)C2=C1 LKIWLRFRMTVENN-UHFFFAOYSA-N 0.000 claims description 2
- SOIWRRAHACEUQO-UHFFFAOYSA-N 6-[2-fluoro-4-(trifluoromethyl)phenyl]-3-(pyrimidin-2-ylmethyl)-2H-1,3-benzoxazin-4-one Chemical compound FC1=CC(C(F)(F)F)=CC=C1C1=CC=C(OCN(CC=2N=CC=CN=2)C2=O)C2=C1 SOIWRRAHACEUQO-UHFFFAOYSA-N 0.000 claims description 2
- SUYKISAGQQPNCL-UHFFFAOYSA-N FC(F)(F)c1ccc(cc1)-c1ccc2OCN(Cc3ccccc3)C(=O)c2c1.Fc1cc(ccc1-c1ccc2OCN(Cc3ccccc3)C(=O)c2c1)C(F)(F)F Chemical compound FC(F)(F)c1ccc(cc1)-c1ccc2OCN(Cc3ccccc3)C(=O)c2c1.Fc1cc(ccc1-c1ccc2OCN(Cc3ccccc3)C(=O)c2c1)C(F)(F)F SUYKISAGQQPNCL-UHFFFAOYSA-N 0.000 claims description 2
- RKZMXFKGMJTFTP-UHFFFAOYSA-N N1=C(C=CC=C1)CN1COC2=C(C1=O)C=C(C=C2)C2=CC=C(C=C2)OC(F)(F)F.N2=C(C=CC=C2)CN2COC1=C(C2=O)C=C(C=C1)C1=CC=C(C=C1)C(F)(F)F Chemical compound N1=C(C=CC=C1)CN1COC2=C(C1=O)C=C(C=C2)C2=CC=C(C=C2)OC(F)(F)F.N2=C(C=CC=C2)CN2COC1=C(C2=O)C=C(C=C1)C1=CC=C(C=C1)C(F)(F)F RKZMXFKGMJTFTP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004350 aryl cycloalkyl group Chemical group 0.000 claims 1
- 230000001568 sexual Effects 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 201000010099 disease Diseases 0.000 description 4
- 125000005605 benzo group Chemical group 0.000 description 3
- 206010002383 Angina pectoris Diseases 0.000 description 2
- 206010007559 Cardiac failure congestive Diseases 0.000 description 2
- 208000008787 Cardiovascular Disease Diseases 0.000 description 2
- 206010061255 Ischaemia Diseases 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 125000004419 alkynylene group Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 201000006233 congestive heart failure Diseases 0.000 description 2
- 125000004367 cycloalkylaryl group Chemical group 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 229940002612 prodrugs Drugs 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- OKCXFMIRAGPOBE-UHFFFAOYSA-N (1,3-dimethylpyrazol-4-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]methanone Chemical compound CC1=NN(C)C=C1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 OKCXFMIRAGPOBE-UHFFFAOYSA-N 0.000 description 1
- OMYBLTTTXLCPBJ-UHFFFAOYSA-N (1-methylimidazol-2-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]methanone Chemical compound CN1C=CN=C1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 OMYBLTTTXLCPBJ-UHFFFAOYSA-N 0.000 description 1
- DMUHWIXKAPTSAU-UHFFFAOYSA-N (1-propan-2-ylpyrazol-4-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]methanone Chemical compound C1=NN(C(C)C)C=C1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 DMUHWIXKAPTSAU-UHFFFAOYSA-N 0.000 description 1
- QMJVNJAJVGDCTL-UHFFFAOYSA-N (2-amino-6-methylpyrimidin-4-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]methanone Chemical compound NC1=NC(C)=CC(C(=O)N2CC3=CC(=CC=C3CC2)C=2C=CC(=CC=2)C(F)(F)F)=N1 QMJVNJAJVGDCTL-UHFFFAOYSA-N 0.000 description 1
- ACZIDEGROKLYPO-UHFFFAOYSA-N (2-propan-2-ylpyrimidin-4-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]methanone Chemical compound CC(C)C1=NC=CC(C(=O)N2CC3=CC(=CC=C3CC2)C=2C=CC(=CC=2)C(F)(F)F)=N1 ACZIDEGROKLYPO-UHFFFAOYSA-N 0.000 description 1
- UKVNDDGLEBQGAQ-UHFFFAOYSA-N (3,3-difluoroazetidin-1-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(CCN(C2)C(=O)N3CC(F)(F)C3)C2=C1 UKVNDDGLEBQGAQ-UHFFFAOYSA-N 0.000 description 1
- YWTSRZSAIBLJJD-UHFFFAOYSA-N (3-amino-1H-1,2,4-triazol-5-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]methanone Chemical compound NC1=NNC(C(=O)N2CC3=CC(=CC=C3CC2)C=2C=CC(=CC=2)C(F)(F)F)=N1 YWTSRZSAIBLJJD-UHFFFAOYSA-N 0.000 description 1
- GLDISGMVFCOFDU-UHFFFAOYSA-N (3-fluoroazetidin-1-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]methanone Chemical compound C1C(F)CN1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 GLDISGMVFCOFDU-UHFFFAOYSA-N 0.000 description 1
- FPKUCEXGARYZEA-UHFFFAOYSA-N (3-fluoropyrrolidin-1-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]methanone Chemical compound C1C(F)CCN1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 FPKUCEXGARYZEA-UHFFFAOYSA-N 0.000 description 1
- ASHRRFLJDQKIRC-UHFFFAOYSA-N (3-hydroxy-3-methylazetidin-1-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]methanone Chemical compound C1C(C)(O)CN1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 ASHRRFLJDQKIRC-UHFFFAOYSA-N 0.000 description 1
- JSKYYSCMMKTJOE-UHFFFAOYSA-N (3-hydroxyazetidin-1-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]methanone Chemical compound C1C(O)CN1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 JSKYYSCMMKTJOE-UHFFFAOYSA-N 0.000 description 1
- OKHGEGPMRVXEHW-UHFFFAOYSA-N (3-hydroxypyrrolidin-1-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]methanone Chemical compound C1C(O)CCN1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 OKHGEGPMRVXEHW-UHFFFAOYSA-N 0.000 description 1
- GYUOAYKNYKPAEL-UHFFFAOYSA-N (3-methylimidazol-4-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]methanone Chemical compound CN1C=NC=C1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 GYUOAYKNYKPAEL-UHFFFAOYSA-N 0.000 description 1
- GJTKRZUDGOBUKW-UHFFFAOYSA-N (3-methylpyrrolidin-1-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]methanone Chemical compound C1C(C)CCN1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 GJTKRZUDGOBUKW-UHFFFAOYSA-N 0.000 description 1
- GKKVGDDVZPXUKK-UHFFFAOYSA-N (3-methylsulfonylazetidin-1-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]methanone Chemical compound C1C(S(=O)(=O)C)CN1C(=O)N1CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2CC1 GKKVGDDVZPXUKK-UHFFFAOYSA-N 0.000 description 1
- NJLITTFSPDEQJF-UHFFFAOYSA-N (3-pyridin-3-yloxyazetidin-1-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(CCN(C2)C(=O)N3CC(C3)OC=3C=NC=CC=3)C2=C1 NJLITTFSPDEQJF-UHFFFAOYSA-N 0.000 description 1
- LTVIHCINJDCRMN-UHFFFAOYSA-N (5-fluoro-1H-imidazol-4-yl)-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]methanone Chemical compound N1=CNC(C(=O)N2CC3=CC(=CC=C3CC2)C=2C=CC(=CC=2)C(F)(F)F)=C1F LTVIHCINJDCRMN-UHFFFAOYSA-N 0.000 description 1
- FPRIKTQPYWSEMF-UHFFFAOYSA-N 1-[4-[4-oxo-3-(2-pyrimidin-2-yloxyethyl)-1,2,3-benzotriazin-6-yl]phenyl]cyclopropane-1-carbonitrile Chemical compound N1=NC2=CC=C(C=3C=CC(=CC=3)C3(CC3)C#N)C=C2C(=O)N1CCOC1=NC=CC=N1 FPRIKTQPYWSEMF-UHFFFAOYSA-N 0.000 description 1
- AISSCWTVTWYJLD-UHFFFAOYSA-N 1-[4-oxo-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-3-yl]cyclopropane-1-carbonitrile Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(C2=O)C3(CC3)C#N)C2=C1 AISSCWTVTWYJLD-UHFFFAOYSA-N 0.000 description 1
- ZMTOTPBCIRSDAD-UHFFFAOYSA-N 1H-imidazol-2-yl-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(CCN(C2)C(=O)C=3NC=CN=3)C2=C1 ZMTOTPBCIRSDAD-UHFFFAOYSA-N 0.000 description 1
- DPTITYSAZQWYGL-UHFFFAOYSA-N 1H-pyrazol-5-yl-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(CCN(C2)C(=O)C=3NN=CC=3)C2=C1 DPTITYSAZQWYGL-UHFFFAOYSA-N 0.000 description 1
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1H-triazin-6-one Chemical compound O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 description 1
- YKXANQXQHPAABH-UHFFFAOYSA-N 2-(1-methylimidazol-4-yl)sulfonyl-7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinoline Chemical compound CN1C=NC(S(=O)(=O)N2CC3=CC(=CC=C3CC2)C=2C=CC(=CC=2)C(F)(F)F)=C1 YKXANQXQHPAABH-UHFFFAOYSA-N 0.000 description 1
- XXKVWUOUIJPXIM-UHFFFAOYSA-N 2-(pyrimidin-2-ylmethyl)-7-[2-[4-(trifluoromethyl)phenyl]ethynyl]-3,4-dihydroisoquinolin-1-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C#CC1=CC=C(CCN(CC=2N=CC=CN=2)C2=O)C2=C1 XXKVWUOUIJPXIM-UHFFFAOYSA-N 0.000 description 1
- YNGZSMBCTUWODU-UHFFFAOYSA-N 2-(pyrimidin-2-ylmethyl)-7-[4-(trifluoromethyl)phenyl]-3,4-dihydroisoquinolin-1-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(CCN(CC=2N=CC=CN=2)C2=O)C2=C1 YNGZSMBCTUWODU-UHFFFAOYSA-N 0.000 description 1
- BZHUWNKCGIIRMA-UHFFFAOYSA-N 2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one Chemical compound CC1=NOC(CN2C(C3=CC(=CC=C3C=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)=N1 BZHUWNKCGIIRMA-UHFFFAOYSA-N 0.000 description 1
- QJYIRGGTCVQALQ-UHFFFAOYSA-N 2-[(4-cyclopropylpyrimidin-2-yl)methyl]-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(C=NN(CC=2N=C(C=CN=2)C2CC2)C2=O)C2=C1 QJYIRGGTCVQALQ-UHFFFAOYSA-N 0.000 description 1
- GAIWIJWVSPMLSG-UHFFFAOYSA-N 2-[(5-pyridin-2-yl-1,2-oxazol-3-yl)methyl]-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(C=NN(CC2=NOC(=C2)C=2N=CC=CC=2)C2=O)C2=C1 GAIWIJWVSPMLSG-UHFFFAOYSA-N 0.000 description 1
- LSXVROBUHDBFTR-UHFFFAOYSA-N 2-[2-(1,2,4-triazol-1-yl)ethyl]-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(C=NN(CCN2N=CN=C2)C2=O)C2=C1 LSXVROBUHDBFTR-UHFFFAOYSA-N 0.000 description 1
- CHRJXNABLDTLAB-UHFFFAOYSA-N 2-[2-(1-methylbenzimidazol-2-yl)ethyl]-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one Chemical compound N=1C2=CC=CC=C2N(C)C=1CCN(C(C1=C2)=O)N=CC1=CC=C2C1=CC=C(OC(F)(F)F)C=C1 CHRJXNABLDTLAB-UHFFFAOYSA-N 0.000 description 1
- ZDYYRTGGVZVNQK-UHFFFAOYSA-N 2-[2-(3,5-dimethylpyrazol-1-yl)ethyl]-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one Chemical compound N1=C(C)C=C(C)N1CCN1C(=O)C2=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CC=C2C=N1 ZDYYRTGGVZVNQK-UHFFFAOYSA-N 0.000 description 1
- FZWHXZRUTBUZEW-UHFFFAOYSA-N 2-[2-(5-methylpyrazol-1-yl)ethyl]-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one Chemical compound CC1=CC=NN1CCN1C(=O)C2=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CC=C2C=N1 FZWHXZRUTBUZEW-UHFFFAOYSA-N 0.000 description 1
- PHUULIXZSQFUMZ-UHFFFAOYSA-N 2-[2-[4-(2-methoxypyrimidin-5-yl)pyrazol-1-yl]ethyl]-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one Chemical compound C1=NC(OC)=NC=C1C1=CN(CCN2C(C3=CC(=CC=C3C=N2)C=2C=CC(OC(F)(F)F)=CC=2)=O)N=C1 PHUULIXZSQFUMZ-UHFFFAOYSA-N 0.000 description 1
- VWESYXQKYFUHHT-UHFFFAOYSA-N 2-[2-[4-oxo-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-3-yl]ethoxy]pyrimidine-4-carbonitrile Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CCOC=2N=C(C=CN=2)C#N)C2=O)C2=C1 VWESYXQKYFUHHT-UHFFFAOYSA-N 0.000 description 1
- RHDGAKMQPCICPN-UHFFFAOYSA-N 2-[2-[4-oxo-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-3-yl]ethoxy]pyrimidine-5-carbonitrile Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(CCOC=2N=CC(=CN=2)C#N)C2=O)C2=C1 RHDGAKMQPCICPN-UHFFFAOYSA-N 0.000 description 1
- FRBXKOSFLJXJLT-UHFFFAOYSA-N 2-[[4-(cyclopropylmethoxy)pyrimidin-2-yl]methyl]-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(C=NN(CC=2N=C(OCC3CC3)C=CN=2)C2=O)C2=C1 FRBXKOSFLJXJLT-UHFFFAOYSA-N 0.000 description 1
- YQACCKXKBZZMLX-UHFFFAOYSA-N 2-pyridin-2-yl-1-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(CCN(C2)C(=O)CC=3N=CC=CC=3)C2=C1 YQACCKXKBZZMLX-UHFFFAOYSA-N 0.000 description 1
- UJYYAQCABPLOHM-UHFFFAOYSA-N 2-pyrimidin-2-yl-1-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl]ethanone Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=C(CCN(C2)C(=O)CC=3N=CC=CN=3)C2=C1 UJYYAQCABPLOHM-UHFFFAOYSA-N 0.000 description 1
- UQMIMGRSZZMLSM-UHFFFAOYSA-N 3-(1-pyrimidin-2-ylpiperidin-4-yl)-6-[4-(trifluoromethoxy)phenyl]-1,2,3-benzotriazin-4-one Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(N=NN(C2CCN(CC2)C=2N=CC=CN=2)C2=O)C2=C1 UQMIMGRSZZMLSM-UHFFFAOYSA-N 0.000 description 1
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2010276537B2 (en) * | 2009-07-27 | 2015-04-16 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
| MX2012015096A (es) | 2010-07-02 | 2013-05-28 | Gilead Sciences Inc | Compuestos heterociclicos fusionados como moduladores del canal ion. |
| EP2707361B1 (en) * | 2011-05-10 | 2017-08-23 | Gilead Sciences, Inc. | Fused heterocyclic compounds as sodium channel modulators |
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| TWI622583B (zh) | 2011-07-01 | 2018-05-01 | 基利科學股份有限公司 | 作為離子通道調節劑之稠合雜環化合物 |
| US20150045305A1 (en) | 2012-01-27 | 2015-02-12 | Gilead Sciences, Inc. | Combination therapies using late sodium ion channel blockers and potassium ion channel blockers |
| US8940742B2 (en) | 2012-04-10 | 2015-01-27 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| WO2015051241A1 (en) | 2013-10-04 | 2015-04-09 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| ES2900806T3 (es) | 2013-10-04 | 2022-03-18 | Infinity Pharmaceuticals Inc | Compuestos heterocíclicos y usos de los mismos |
| CA2934517C (en) * | 2013-12-19 | 2018-10-16 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
| JP6701088B2 (ja) | 2014-03-19 | 2020-05-27 | インフィニティー ファーマシューティカルズ， インコーポレイテッド | Ｐｉ３ｋ−ガンマ媒介障害の治療で使用するための複素環式化合物 |
| JO3512B1 (ar) | 2014-03-26 | 2020-07-05 | Astex Therapeutics Ltd | مشتقات كينوكسالين مفيدة كمعدلات لإنزيم fgfr كيناز |
| US9617226B2 (en) | 2014-09-05 | 2017-04-11 | AbbVie Deutschland GmbH & Co. KG | Fused heterocyclic or carbocyclic compounds carrying a substituted cycloaliphatic radical and use thereof for treating vasopressin-related diseases |
| US9708348B2 (en) | 2014-10-03 | 2017-07-18 | Infinity Pharmaceuticals, Inc. | Trisubstituted bicyclic heterocyclic compounds with kinase activities and uses thereof |
| CN104530037B (zh) * | 2015-01-21 | 2020-12-18 | 华东理工大学 | 一种具有杀线虫活性的三嗪杂环化合物及其制法和用途 |
| US10865185B2 (en) | 2015-08-21 | 2020-12-15 | Srx Cardio, Llc | Composition and methods of use of tetrahydroisoquinoline small molecules to bind and modulate PCSK9 protein activity |
| WO2017034997A1 (en) | 2015-08-21 | 2017-03-02 | Portola Pharmaceuticals, Inc. | Phenylpiperazine proprotein convertase subtilisin/kexin type 9 (pcsk9) modulators and their use |
| WO2017034994A1 (en) | 2015-08-21 | 2017-03-02 | Portola Pharmaceuticals, Inc. | Composition and methods of use of novel phenylalanine small organic compounds to directly modulate pcsk9 protein activity |
| US10160761B2 (en) | 2015-09-14 | 2018-12-25 | Infinity Pharmaceuticals, Inc. | Solid forms of isoquinolinones, and process of making, composition comprising, and methods of using the same |
| HRP20220012T1 (hr) | 2015-09-23 | 2022-04-01 | Janssen Pharmaceutica Nv | Bi-heteroaril supstituirani 1,4-benzodiazepini i njihova upotreba za liječenje raka |
| CA2996857C (en) | 2015-09-23 | 2024-05-21 | Janssen Pharmaceutica Nv | Quinoxaline, quinoline and quinazolinone derivative compounds for the treatment of cancer |
| HUE051395T2 (hu) | 2015-12-09 | 2021-03-01 | Cadent Therapeutics Inc | Heteroaromás NMDA receptor modulátorok és alkalmazásaik |
| EP3386990B1 (en) | 2015-12-09 | 2023-04-19 | Novartis AG | Thienopyrimidinone nmda receptor modulators and uses thereof |
| WO2017147328A1 (en) | 2016-02-23 | 2017-08-31 | Portola Pharmaceuticals, Inc. | Compounds for binding proprotein convertase subtilisin/kexin type 9 (pcsk9) |
| WO2017161116A1 (en) | 2016-03-17 | 2017-09-21 | Infinity Pharmaceuticals, Inc. | Isotopologues of isoquinolinone and quinazolinone compounds and uses thereof as pi3k kinase inhibitors |
| US10919914B2 (en) | 2016-06-08 | 2021-02-16 | Infinity Pharmaceuticals, Inc. | Heterocyclic compounds and uses thereof |
| CN116763791A (zh) | 2016-11-28 | 2023-09-19 | 普拉克西斯精密药物股份有限公司 | 化合物以及它们的使用方法 |
| WO2018098491A1 (en) | 2016-11-28 | 2018-05-31 | Praxis Precision Medicines, Inc. | Compounds and their methods of use |
| ES2975336T3 (es) | 2016-12-22 | 2024-07-04 | Novartis Ag | Moduladores del receptor NMDA y usos de los mismos |
| WO2018148745A1 (en) | 2017-02-13 | 2018-08-16 | Praxis Precision Medicines , Inc. | Compounds and their methods of use |
| US10266542B2 (en) | 2017-03-15 | 2019-04-23 | Mirati Therapeutics, Inc. | EZH2 inhibitors |
| WO2018187480A1 (en) | 2017-04-04 | 2018-10-11 | Praxis Precision Medicines, Inc. | Compounds and their methods of use |
| CA3066423A1 (en) * | 2017-06-14 | 2018-12-20 | Trevena, Inc. | Compounds for modulating s1p1 activity and methods of using the same |
| US11278535B2 (en) | 2017-08-15 | 2022-03-22 | Praxis Precision Medicines, Inc. | Compounds and their methods of use |
| CA3089639C (en) | 2018-01-31 | 2024-06-18 | Mirati Therapeutics, Inc. | Imidazo[1,2-c]pyrimidinyl compounds as prc2 inhibitors |
| CN108276352B (zh) * | 2018-03-13 | 2022-09-20 | 华东理工大学 | 一种具有杀线虫活性的含氮杂环化合物及其制法和用途 |
| CN117756800A (zh) | 2018-05-30 | 2024-03-26 | 普拉克西斯精密药物股份有限公司 | 离子通道调节剂 |
| PE20210948A1 (es) | 2018-08-03 | 2021-05-24 | Cadent Therapeutics Inc | Moduladores del receptor nmda heteroaromatico y usos de los mismos |
| KR102288434B1 (ko) * | 2018-10-18 | 2021-08-12 | 에이치케이이노엔 주식회사 | 신규한 (이소프로필-트리아졸릴)피리디닐 치환된 벤조옥사지논 또는 벤조티아지논 유도체 및 이의 용도 |
| US11773099B2 (en) | 2019-05-28 | 2023-10-03 | Praxis Precision Medicines, Inc. | Compounds and their methods of use |
| US11505554B2 (en) | 2019-05-31 | 2022-11-22 | Praxis Precision Medicines, Inc. | Substituted pyridines as ion channel modulators |
| US11279700B2 (en) | 2019-05-31 | 2022-03-22 | Praxis Precision Medicines, Inc. | Ion channel modulators |
| WO2021026672A1 (en) | 2019-08-09 | 2021-02-18 | Novartis Ag | Heterocyclic wdr5 inhibitors as anti-cancer compounds |
| BR112022003959A2 (pt) * | 2019-09-05 | 2022-05-24 | Trevena Inc | Métodos para tratamento de epilepsia |
| CN114727977A (zh) | 2019-11-19 | 2022-07-08 | 特维娜有限公司 | 化合物和化合物s1p1调节剂的制备方法 |
| US11767325B2 (en) | 2019-11-26 | 2023-09-26 | Praxis Precision Medicines, Inc. | Substituted [1,2,4]triazolo[4,3-a]pyrazines as ion channel modulators |
| AU2021331492A1 (en) * | 2020-08-28 | 2023-04-13 | Kumquat Biosciences Inc. | Heterocyclic compounds and uses thereof |
| US12115154B2 (en) | 2020-12-16 | 2024-10-15 | Srx Cardio, Llc | Compounds for the modulation of proprotein convertase subtilisin/kexin type 9 (PCSK9) |
| CN116265444A (zh) * | 2021-12-16 | 2023-06-20 | 华东理工大学 | 杀线虫活性的化合物及其制备方法和用途 |
Family Cites Families (220)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2867616A (en) | 1950-05-17 | 1959-01-06 | Syntex Sa | 7-dehydro diosgenin compounds and process for making same |
| US2867618A (en) * | 1957-02-14 | 1959-01-06 | Dow Chemical Co | 3, 4-dihydro-2h-1, 3-benzoxazine |
| US2826575A (en) * | 1957-05-06 | 1958-03-11 | Dow Chemical Co | 3, 3'-alkylenebis |
| NL128591C (US06653308-20031125-C00057.png) | 1965-07-02 | |||
| US3441649A (en) | 1966-08-18 | 1969-04-29 | Univ Minnesota | Suppression of cardiac ventricular fibrillation and cardiac arrhythmias with bretylium tosylate |
| US3594372A (en) | 1968-08-13 | 1971-07-20 | American Home Prod | Pyrimido(4,5-e)(1,4)oxazepin-5-ones and derivatives thereof |
| US3845770A (en) | 1972-06-05 | 1974-11-05 | Alza Corp | Osmatic dispensing device for releasing beneficial agent |
| US4062881A (en) | 1974-07-26 | 1977-12-13 | Cincinnati Milacron Chemicals, Inc. | Sulfide containing tin stabilizers |
| US4230705A (en) | 1976-09-22 | 1980-10-28 | American Cyanamid Company | 6-Phenyl-1,2,4-triazolo[4,3-b]pyridazines and their uses in treating anxiety |
| US4242515A (en) | 1979-03-28 | 1980-12-30 | American Cyanamid Company | Substituted 3-alkyl-6-phenyl-1,2,4-triazolo-[4,3-a]pyridines |
| US4244953A (en) | 1979-10-24 | 1981-01-13 | American Cyanamid Company | Substituted 6-phenyl-5,6,7,8-tetrahydro-1,2,4-triazolo-[4,3-a]pyridines |
| JPS5675428A (en) | 1979-11-21 | 1981-06-22 | Ayanori Takabe | Hypoglycemic agent containing procainamide hydrochloride |
| US4326525A (en) | 1980-10-14 | 1982-04-27 | Alza Corporation | Osmotic device that improves delivery properties of agent in situ |
| US4812565A (en) | 1982-09-30 | 1989-03-14 | A. H. Robins Company, Incorporated | Fused aromatic oxazepinones, thiazepinones, diazepinones and sulfur analogs thereof |
| US5364620A (en) | 1983-12-22 | 1994-11-15 | Elan Corporation, Plc | Controlled absorption diltiazem formulation for once daily administration |
| US4665181A (en) * | 1984-05-17 | 1987-05-12 | Pennwalt Corporation | Anti-inflammatory phthalazinones |
| US4654343A (en) | 1985-10-31 | 1987-03-31 | American Cyanamid Company | N-substituted-N[3-(1,2,4-triazolo[4,3-b]pyridazin-6-yl)phenyl]alkanamides, carbamates and ureas |
| US5023252A (en) | 1985-12-04 | 1991-06-11 | Conrex Pharmaceutical Corporation | Transdermal and trans-membrane delivery of drugs |
| US4746655A (en) | 1987-06-10 | 1988-05-24 | A. H. Robins Company, Incorporated | Fused aromatic-spiropiperidine oxazepinones(and thiones) |
| US5001139A (en) | 1987-06-12 | 1991-03-19 | American Cyanamid Company | Enchancers for the transdermal flux of nivadipine |
| US4992445A (en) | 1987-06-12 | 1991-02-12 | American Cyanamid Co. | Transdermal delivery of pharmaceuticals |
| US4902514A (en) | 1988-07-21 | 1990-02-20 | Alza Corporation | Dosage form for administering nilvadipine for treating cardiovascular symptoms |
| JPH061779Y2 (ja) | 1989-11-13 | 1994-01-19 | 株式会社新潟鐵工所 | 合成樹脂成形機におけるホッパー下部の冷却水装置 |
| DE4010488A1 (de) | 1990-03-31 | 1991-10-02 | Hoechst Ag | Benzoxazinderivate, verfahren zu ihrer herstellung und ihre verwendung zum behandeln oder zur prophylaxe von krankheiten |
| CA2044564A1 (en) | 1990-06-28 | 1991-12-29 | Quirico Branca | Amino acid derivatives |
| CN1060467A (zh) | 1990-09-25 | 1992-04-22 | 武田药品工业株式会社 | 1，3-苯并嗪衍生物、其生产方法和用途 |
| JPH04209692A (ja) | 1990-12-03 | 1992-07-31 | Asahi Glass Co Ltd | フォトクロミック材料 |
| EP0522606B1 (en) | 1991-05-10 | 1996-04-03 | Takeda Chemical Industries, Ltd. | Pyridine derivatives, their production and use |
| US5939412A (en) | 1992-06-26 | 1999-08-17 | Smithkline Beecham Corporation | Bicyclic fibrinogen antagonists |
| ZA924760B (en) | 1991-06-28 | 1993-03-31 | Smithkline Beecham Corp | Bicyclic fibrinogen antagonists |
| US5250679A (en) | 1991-10-18 | 1993-10-05 | Genentech, Inc. | Nonpeptidyl platelet aggregation inhibitors having specificity for the GPIIb III.sub. receptor |
| US5663166A (en) | 1991-10-18 | 1997-09-02 | Genentech, Inc. | Nonpeptidyl integrin inhibitors having specificity for the GPIIb IIIa receptor |
| US5272158A (en) | 1991-10-29 | 1993-12-21 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| JPH061779A (ja) | 1992-02-06 | 1994-01-11 | Wakamoto Pharmaceut Co Ltd | ベンズオキサジノン誘導体 |
| JPH06107647A (ja) | 1992-08-12 | 1994-04-19 | Takeda Chem Ind Ltd | １，３−ベンゾオキサジン誘導体の製造法 |
| US6011150A (en) | 1992-11-13 | 2000-01-04 | Tanabe Seiyaku Co., Ltd. | Azetidinone compound and process for preparation thereof |
| US5442055A (en) | 1992-11-13 | 1995-08-15 | Tanabe Seiyaku Co., Ltd. | Azetidinone compound and process for preparation thereof |
| GB9225860D0 (en) | 1992-12-11 | 1993-02-03 | Smithkline Beecham Plc | Novel treatment |
| GB9226302D0 (en) | 1992-12-17 | 1993-02-10 | Smithkline Beecham Plc | Pharmaceuticals |
| US5550229A (en) | 1993-06-23 | 1996-08-27 | Tanabe Seiyaku Co., Ltd. | Alkylation process for preparing azetidinone compound and starting compound therefor |
| DE19526173A1 (de) | 1995-07-18 | 1997-01-30 | Hoechst Ag | Polyfullerenaddukte, Verfahren zu ihrer regioselektiven Herstellung und deren Verwendung |
| JPH09157262A (ja) | 1995-12-08 | 1997-06-17 | Tanabe Seiyaku Co Ltd | アゼチジノン誘導体及びその合成中間体の製法 |
| US5773186A (en) | 1996-02-19 | 1998-06-30 | Fuji Photo Film Co., Ltd. | Heat-sensitive recording material |
| GB9619492D0 (en) | 1996-09-18 | 1996-10-30 | Smithkline Beecham Plc | Novel treatment |
| US6159979A (en) | 1997-04-18 | 2000-12-12 | Smithkline Beecham P.L.C. | Bicyclic aryl or a bicyclic heterocyclic ring containing compounds having a combined 5HT1A, 5HT1B and 5HT1D receptor antagonistic activity |
| CA2291630A1 (en) * | 1997-05-30 | 1998-12-03 | Tetsutaro Niizato | Nitrogen-containing heterocyclic compounds and therapeutic agents for hyperlipidemia comprising the same |
| JP3964053B2 (ja) | 1997-07-10 | 2007-08-22 | 三井化学株式会社 | 遷移金属化合物からなるオレフィン重合用触媒ならびに重合方法 |
| AU9257998A (en) | 1997-09-08 | 1999-03-29 | Unilever N.V. | Method for enhancing the activity of an enzyme |
| EA002755B1 (ru) | 1998-01-21 | 2002-08-29 | Мерк Шарп Энд Домэ Лимитед | Производные триазолопиридазина в качестве лигандов для гамк рецепторов |
| CA2319173A1 (en) | 1998-02-11 | 1999-08-19 | Jingwu Duan | Novel cyclic sulfonamide derivatives as metalloproteinase inhibitors |
| CA2320354A1 (en) | 1998-02-18 | 1999-08-26 | Neurosearch A/S | Novel compounds and their use as positive ampa receptor modulators |
| EP1087968A1 (en) | 1998-06-16 | 2001-04-04 | MERCK SHARP & DOHME LTD. | Triazolo-pyridine derivatives as ligands for gaba receptors |
| EP1123297A1 (en) | 1998-10-21 | 2001-08-16 | Novo Nordisk A/S | New compounds, their preparation and use |
| KR20020005662A (ko) | 1999-04-09 | 2002-01-17 | 기따자또 이찌로 | 질소함유 복소환화합물 및 벤즈아미드화합물 및 그 것을함유해서 되는 의약 |
| CA2373073A1 (en) * | 1999-05-07 | 2000-11-16 | Takeda Chemical Industries, Ltd. | Cyclic compounds and uses thereof |
| CN1382207A (zh) | 1999-08-27 | 2002-11-27 | 宝洁公司 | 利用阳离子配制组分的颜色保护性洗衣方法 |
| BR0013608A (pt) | 1999-08-27 | 2002-05-21 | Procter & Gamble | Disponibilidade controlada de componentes de formulações, composições e métodos para lavar roupa empregando os mesmos |
| AU6935700A (en) | 1999-08-27 | 2001-03-26 | Procter & Gamble Company, The | Color safe laundry methods employing zwitterionic formulation components |
| MXPA02002129A (es) | 1999-08-27 | 2002-09-18 | Procter & Gamble | Componentes de formulacion de accion rapida, composiciones y metodos para lavanderia que los emplean. |
| AU7072100A (en) | 1999-08-27 | 2001-03-26 | Procter & Gamble Company, The | Stable formulation components, compositions and laundry methods employing same |
| CZ2002720A3 (cs) | 1999-08-27 | 2002-09-11 | The Procter & Gamble Company | Složky zesilující bělení, prostředky a způsoby praní s využitím složek zesilujících bělení |
| AU6935500A (en) | 1999-08-27 | 2001-03-26 | Procter & Gamble Company, The | Stability enhancing formulation components, compositions and laundry methods employing same |
| US6469020B2 (en) | 2000-05-15 | 2002-10-22 | Darwin Discovery, Ltd. | Hydroxamic and carboxylic acid derivatives |
| MXPA03000952A (es) | 2000-08-01 | 2003-09-05 | Ono Pharmaceutical Co | Compuestos derivados de 3,4-dihidroisoquinolina y medicamentos que los contienen, como el ingrediente activo. |
| CA2419255A1 (en) | 2000-08-29 | 2002-03-07 | Ish Kumar Khanna | Compounds containing a bicyclic ring system useful as alpha v beta 3 antagonists |
| JP2002205992A (ja) | 2000-11-08 | 2002-07-23 | Takeda Chem Ind Ltd | 二環式トリアゾロン誘導体およびそれを含有する除草剤 |
| EP1695716A2 (en) | 2000-12-26 | 2006-08-30 | Sankyo Company, Limited | Medicinal compositions containing diuretics and insulin sensitizers |
| PL363959A1 (en) | 2001-03-09 | 2004-11-29 | Pfizer Products Inc. | Triazolopyridines as anti-inflammatory agents |
| US6998408B2 (en) | 2001-03-23 | 2006-02-14 | Bristol-Myers Squibb Pharma Company | 6-5, 6-6, or 6-7 Heterobicycles as factor Xa inhibitors |
| US20030114448A1 (en) | 2001-05-31 | 2003-06-19 | Millennium Pharmaceuticals, Inc. | Inhibitors of factor Xa |
| JP2005089298A (ja) | 2001-09-18 | 2005-04-07 | Japan Tobacco Inc | ナフタレン化合物及びその医薬用途 |
| ES2291538T3 (es) | 2001-11-13 | 2008-03-01 | Schering Corporation | Antagonistas de nk1. |
| US7196108B2 (en) | 2002-03-08 | 2007-03-27 | Incyte San Diego Inc. | Bicyclic heterocycles for the treatment of diabetes and other diseases |
| JP2003277384A (ja) | 2002-03-26 | 2003-10-02 | Kyorin Pharmaceut Co Ltd | 縮合ニ環式ピリジン誘導体 |
| JP2003321461A (ja) | 2002-04-25 | 2003-11-11 | Kyorin Pharmaceut Co Ltd | 縮合ビフェニル誘導体 |
| AU2003253150A1 (en) | 2002-08-13 | 2004-02-25 | Warner-Lambert Company Llc | Chromone derivatives as matrix metalloproteinase inhibitors |
| AU2003249531A1 (en) | 2002-08-13 | 2004-02-25 | Warner-Lambert Company Llc | Azaisoquinoline derivatives as matrix metalloproteinase inhibitors |
| US20040242572A1 (en) * | 2002-08-24 | 2004-12-02 | Boehringer Ingelheim International Gmbh | New carboxamide compounds having melanin concentrating hormone antagonistic activity, pharmaceutical preparations comprising these compounds and process for their manufacture |
| DE10238865A1 (de) | 2002-08-24 | 2004-03-11 | Boehringer Ingelheim International Gmbh | Neue Carbonsäureamid-Verbindungen mit MCH-antagonistischer Wirkung, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| PA8579601A1 (es) | 2002-08-30 | 2004-05-07 | Pfizer Prod Inc | Compuestos antiinflamatorios de di y trifloruro-triazolo-piridinas |
| US7005523B2 (en) | 2002-08-30 | 2006-02-28 | Pfizer Inc. | Cycloalkyl-[4-(trifluorophenyl)-oxazol-5yl]-triazolo-pyridines |
| WO2004026292A1 (ja) | 2002-09-20 | 2004-04-01 | Tsumura & Co. | 鎮咳薬 |
| US20040204404A1 (en) | 2002-09-30 | 2004-10-14 | Robert Zelle | Human N-type calcium channel blockers |
| GB0223730D0 (en) | 2002-10-11 | 2002-11-20 | Novartis Ag | Organic compounds |
| AU2003285946A1 (en) | 2002-10-22 | 2004-05-13 | The Trustees Of The University Of Pennsylvania | Identification of antimycobacterial targets and the inhibition thereof as a treatment for infectious diseases |
| CN100430386C (zh) | 2002-11-07 | 2008-11-05 | 默克公司 | 苯丙氨酸衍生物作为二肽基肽酶抑制剂用于治疗或预防糖尿病 |
| WO2004043940A1 (en) | 2002-11-07 | 2004-05-27 | Merck & Co., Inc. | Phenylalanine derivatives as dipeptidyl peptidase inhibitors for the treatment or prevention of diabetes |
| WO2004062616A2 (en) | 2003-01-13 | 2004-07-29 | Cortex Pharmaceuticals, Inc. | Method of treating cognitive decline due to sleep deprivation and stress |
| JP4209692B2 (ja) | 2003-01-28 | 2009-01-14 | 株式会社日立製作所 | 図書管理システム及び書誌情報管理方法 |
| MY142651A (en) | 2003-03-18 | 2010-12-15 | Merck Sharp & Dohme | Biaryl substituted triazoles as sodium channel blockers |
| DE10317526A1 (de) | 2003-04-16 | 2004-11-04 | Degussa Ag | Verfahren zum Delignifizieren von ligninhaltigen Faserstoffen |
| CN100384856C (zh) * | 2003-04-17 | 2008-04-30 | 麦克公司 | 趋化因子受体活性调节剂杂环基环戊基四氢异喹啉和杂环基环戊基四氢吡啶并吡啶 |
| JP2006524641A (ja) | 2003-04-25 | 2006-11-02 | ハー・ルンドベック・アクチエゼルスカベット | 置換されたインドリンおよびインドール誘導体 |
| WO2004101509A2 (en) * | 2003-05-06 | 2004-11-25 | Case Western Reserve University | Functionalized benzoxazines, polymers and copolymers thereof |
| US20060148805A1 (en) | 2003-07-01 | 2006-07-06 | Meng Hsin Chen | Opthalmic compositions for treating ocular hypertension |
| MXPA06000796A (es) | 2003-07-21 | 2006-04-07 | Solvay Pharm Gmbh | Uso de los compuestos 3,7-diazabiciclo [3,3,1]nonano para el tratamiento y/o profilaxis de eventos antiarritmicos en pacientes humanos varones. |
| AU2004263515A1 (en) | 2003-08-05 | 2005-02-17 | Vertex Pharmaceuticals Incorporated | Condensed pyrimidine compounds as inhibitors of voltage-gated ion channels |
| US20050239767A1 (en) | 2003-10-28 | 2005-10-27 | Chan Michael K | Intermolecular SNAr of the heterocycle-activated nitro and fluoro groups-application in the synthesis of polyazamacrocyclic ligands |
| EP1708709A1 (en) | 2003-12-18 | 2006-10-11 | Pfizer Products Incorporated | METHODS OF TREATING ACUTE INFLAMMATION IN ANIMALS WITH p38 MAP KINASE INHIBITORS |
| SI1731512T1 (sl) | 2004-03-05 | 2015-01-30 | Nissan Chemical Industries, Ltd. | Z izoksazolinom substituirana benzamidna spojina in sredstvo za uravnavanje škodljivih organizmov |
| US7306631B2 (en) | 2004-03-30 | 2007-12-11 | The Procter & Gamble Company | Keratin dyeing compounds, keratin dyeing compositions containing them, and use thereof |
| GB0412986D0 (en) | 2004-06-10 | 2004-07-14 | Xention Discovery Ltd | Compounds |
| WO2006002470A1 (en) | 2004-06-30 | 2006-01-12 | Monash University | Chiral ligands for asymmetric catalysis |
| JP2006063064A (ja) | 2004-07-27 | 2006-03-09 | Takeda Chem Ind Ltd | 受容体作動剤 |
| JP2007297283A (ja) | 2004-07-28 | 2007-11-15 | Santen Pharmaceut Co Ltd | 新規桂皮酸関連化合物 |
| US7572783B2 (en) | 2004-08-13 | 2009-08-11 | Amgen Inc. | Substituted benzofused heterocycles |
| US7521457B2 (en) | 2004-08-20 | 2009-04-21 | Boehringer Ingelheim International Gmbh | Pyrimidines as PLK inhibitors |
| EP1784188B1 (en) | 2004-08-23 | 2010-07-14 | Merck Sharp & Dohme Corp. | Fused triazole derivatives as dipeptidyl peptidase-iv inhibitors for the treatment or prevention of diabetes |
| AU2005285083B2 (en) | 2004-09-13 | 2011-03-10 | Merck Sharp & Dohme Corp. | Tricyclic anilide spirohydantoin CGRP receptor antagonists |
| TW200624431A (en) | 2004-09-24 | 2006-07-16 | Hoffmann La Roche | Phthalazinone derivatives, their manufacture and use as pharmaceutical agents |
| WO2006048727A1 (en) * | 2004-11-02 | 2006-05-11 | Pfizer Products Inc. | Piperazinylphenalkyl lactam/amine ligands for the 5ht1b receptor |
| US7579348B2 (en) | 2005-02-25 | 2009-08-25 | Pgxhealth, Llc | Derivatives of 8-substituted xanthines |
| CN101258134B (zh) * | 2005-03-11 | 2011-10-12 | 欧加农股份有限公司 | 2-(4-氧代-4h-喹唑啉-3-基)乙酰胺衍生物及其作为加压素v3拮抗剂的用途 |
| TW200643015A (en) * | 2005-03-11 | 2006-12-16 | Akzo Nobel Nv | 2-(4-oxo-4H-quinazolin-3-yl)acetamide derivatives |
| EP1874753A2 (en) | 2005-04-14 | 2008-01-09 | Smithkline Beecham Corporation | Compounds, compositions and methods |
| AR056317A1 (es) | 2005-04-20 | 2007-10-03 | Xenon Pharmaceuticals Inc | Compuestos de oxindol y composicion farmaceutica |
| SI2444079T1 (sl) | 2005-05-17 | 2017-05-31 | Sarcode Bioscience Inc. | Sestavki in postopki za zdravljenje očesnih motenj |
| TW200714597A (en) | 2005-05-27 | 2007-04-16 | Astrazeneca Ab | Chemical compounds |
| US7572807B2 (en) | 2005-06-09 | 2009-08-11 | Bristol-Myers Squibb Company | Heteroaryl 11-beta-hydroxysteroid dehydrogenase type I inhibitors |
| US7572808B2 (en) | 2005-06-17 | 2009-08-11 | Bristol-Myers Squibb Company | Triazolopyridine cannabinoid receptor 1 antagonists |
| JP2008543867A (ja) | 2005-06-17 | 2008-12-04 | ワイス | セロトニン阻害剤ならびに５−ｈｔ１ａアゴニストおよびアンタゴニストとして有用な三環系化合物 |
| US7632837B2 (en) | 2005-06-17 | 2009-12-15 | Bristol-Myers Squibb Company | Bicyclic heterocycles as cannabinoid-1 receptor modulators |
| WO2007004028A2 (en) | 2005-06-30 | 2007-01-11 | Ranbaxy Laboratories Limited | Processes for the preparation of penems and its intermediate |
| WO2007023750A1 (ja) | 2005-08-26 | 2007-03-01 | National University Corporation University Of Toyama | 乾燥羊膜及び羊膜の乾燥処理方法 |
| JP2009508963A (ja) | 2005-09-21 | 2009-03-05 | インサイト・コーポレイション | アミド化合物および医薬組成物としてのその使用 |
| MX2008004024A (es) | 2005-09-23 | 2009-02-27 | Schering Corp | Antagonistas de receptor de glutamato metabotropico-1 tetraciclicos fusionados como agentes terapeuticos. |
| WO2007047604A2 (en) | 2005-10-18 | 2007-04-26 | Elixir Pharmaceuticals, Inc. | Sirt1 inhibition |
| TW200804290A (en) | 2005-11-15 | 2008-01-16 | Astrazeneca Ab | Compounds and uses thereof |
| CA2629409A1 (en) | 2005-11-18 | 2007-05-31 | Merck & Co., Inc. | Spirolactam aryl cgrp receptor antagonists |
| WO2007061696A2 (en) | 2005-11-18 | 2007-05-31 | Merck & Co., Inc. | Spirolactam bicyclic cgrp receptor antagonists |
| TW200734342A (en) | 2005-12-15 | 2007-09-16 | Astrazeneca Ab | New compounds for the treatment of cardiac arrhythmias |
| CN101330914A (zh) | 2005-12-16 | 2008-12-24 | 爱尔康公司 | 使用alk5调节剂控制眼内压 |
| US8013073B2 (en) | 2005-12-30 | 2011-09-06 | Chevron Oronite Company Llc | Method for preparing polyolefins containing vinylidine end groups using nonaromatic heterocyclic compounds |
| RU2008143179A (ru) | 2006-03-31 | 2010-05-10 | Новартис АГ (CH) | Органические соединения |
| EP2018863B9 (en) | 2006-05-16 | 2015-02-18 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compound and use thereof |
| AU2007258313A1 (en) | 2006-06-12 | 2007-12-21 | Vertex Pharmaceuticals Incorporated | Thienopyrimidines useful as modulators of ion channels |
| WO2008005338A1 (en) | 2006-06-29 | 2008-01-10 | Arena Pharmaceuticals, Inc. | Modulators of the histamine h3-receptor useful for the treatment of disorders related thereto |
| ES2431466T3 (es) | 2006-06-30 | 2013-11-26 | Sunesis Pharmaceuticals, Inc. | Inhibidores de piridinonil pdk1 |
| WO2008007661A1 (fr) | 2006-07-11 | 2008-01-17 | Takeda Pharmaceutical Company Limited | Composé hétérocyclique tricycique et son utilisation |
| US20100035756A1 (en) | 2006-07-12 | 2010-02-11 | Syngenta Limited | Triazolophyridine derivatives as herbicides |
| PE20121506A1 (es) | 2006-07-14 | 2012-11-26 | Amgen Inc | Compuestos triazolopiridinas como inhibidores de c-met |
| US8217177B2 (en) | 2006-07-14 | 2012-07-10 | Amgen Inc. | Fused heterocyclic derivatives and methods of use |
| SI2074093T1 (sl) * | 2006-08-22 | 2012-12-31 | Ranbaxy Laboratories Limited | Postopek za pridobitev inhibitorjev matrične metalproteinaze in kiralni pomožnik zanj |
| WO2008063287A2 (en) | 2006-10-06 | 2008-05-29 | Abbott Laboratories | Novel imidazothiazoles and imidazoxazoles |
| WO2008118141A2 (en) | 2006-10-17 | 2008-10-02 | Acadia Pharmaceuticals Inc. | Use of cannabinoid modulating compounds in combination with other therapeutic compounds for adjunctive therapy |
| ES2633318T3 (es) | 2006-10-23 | 2017-09-20 | Cephalon, Inc. | Derivados bicíclicos fusionados de 2,4-diaminopirimidina como inhibidores de ALK y c-Met |
| CN101573333B (zh) | 2006-10-28 | 2013-06-12 | 梅特希尔基因公司 | 组蛋白脱乙酰酶抑制剂 |
| EP2128134A1 (en) * | 2006-11-02 | 2009-12-02 | Shionogi&Co., Ltd. | Sulfonylurea derivative capable of selectively inhibiting mmp-13 |
| US20080153840A1 (en) | 2006-12-21 | 2008-06-26 | Luiz Belardinelli | Reduction of cardiovascular symptoms |
| US8076350B2 (en) | 2006-12-22 | 2011-12-13 | Abbott Laboratories | Spirocyclic azaadamantane derivatives and methods of use |
| AR065081A1 (es) * | 2007-01-29 | 2009-05-13 | Xenon Pharmaceuticals Inc | Compuestos de quinazolinona y pirimidona fusionados y composicion farmaceutica |
| US20100144715A1 (en) | 2007-02-28 | 2010-06-10 | Hoyt Scott B | Substituted Benzodiazepinones, Benzoxazepinones and Benzothiazepinones as Sodium Channel Blockers |
| US8247403B2 (en) | 2007-03-07 | 2012-08-21 | Takeda Pharmaceutical Company Limited | Benzoxazepine derivatives and use thereof |
| GB0706072D0 (en) | 2007-03-28 | 2007-05-09 | Sterix Ltd | Compound |
| AU2008240202A1 (en) | 2007-04-12 | 2008-10-23 | Cv Therapeutics, Inc. | Ranolazine for enhancing insulin secretion |
| WO2008134553A1 (en) | 2007-04-26 | 2008-11-06 | Xenon Pharmaceuticals Inc. | Methods of using bicyclic compounds in treating sodium channel-mediated diseases |
| WO2008144483A2 (en) | 2007-05-18 | 2008-11-27 | Armgo Pharma, Inc. | Agents for treating disorders involving modulation of ryanodine receptors |
| WO2009005675A1 (en) | 2007-06-28 | 2009-01-08 | Abbott Laboratories | Novel triazolopyridazines |
| US20090012103A1 (en) | 2007-07-05 | 2009-01-08 | Matthew Abelman | Substituted heterocyclic compounds |
| US20090036425A1 (en) | 2007-08-02 | 2009-02-05 | Pfizer Inc | Substituted bicyclolactam compounds |
| WO2009026444A1 (en) | 2007-08-22 | 2009-02-26 | President And Fellows Of Harvard College | Ryanodine channel binders and uses thereof |
| MX2010002760A (es) * | 2007-09-12 | 2010-04-01 | Wyeth Llc | Derivados de isoquinolinilo e isoindolinilo como antagonistas de la histamina-3. |
| US8119658B2 (en) | 2007-10-01 | 2012-02-21 | Bristol-Myers Squibb Company | Triazolopyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| NZ585306A (en) | 2007-12-19 | 2012-05-25 | Genentech Inc | 8-Anilinoimidazopyridines and their use as anti-cancer and/or anti-inflammatory agents |
| PE20091339A1 (es) | 2007-12-21 | 2009-09-26 | Glaxo Group Ltd | Derivados de oxadiazol con actividad sobre receptores s1p1 |
| WO2009089027A1 (en) | 2008-01-09 | 2009-07-16 | Government Of The United States Of America As Represented By The Secretary Of The Department Of Health And Human Service, National Institutes Of Health | Phosphodiesterase inhibitors |
| BRPI0908428A2 (pt) | 2008-02-06 | 2015-12-08 | Gilead Sciences Inc | uso de ranozalina para tratar a dor. |
| MX2010008818A (es) | 2008-02-13 | 2010-09-07 | Eisai R&D Man Co Ltd | Derivado de bicicloamina. |
| JP2009286773A (ja) | 2008-03-14 | 2009-12-10 | Bayer Cropscience Ag | 殺虫性縮環式アリール類 |
| WO2009137462A2 (en) | 2008-05-05 | 2009-11-12 | Envivo Pharmaceuticals, Inc. | Methods for treating cognitive disorders using inhibitors of histone deacetylase |
| WO2009137499A1 (en) | 2008-05-05 | 2009-11-12 | Envivo Pharmaceuticals, Inc. | Inhibitors of histone deacetylase |
| DE102008024182A1 (de) | 2008-05-19 | 2009-11-26 | Merck Patent Gmbh | Verbindungen für organische elektronische Vorrichtung |
| CA2725573A1 (en) | 2008-06-06 | 2009-12-10 | Abbott Laboratories | Novel 1,2,4 oxadiazole compounds and methods of use thereof |
| CA2726508C (en) | 2008-06-17 | 2016-06-07 | Astrazeneca Ab | Pyridine compounds |
| WO2010006292A1 (en) | 2008-07-11 | 2010-01-14 | Neumedics | Tetracycline derivatives with reduced antibiotic activity and neuroprotective benefits |
| WO2010018686A1 (ja) | 2008-08-12 | 2010-02-18 | 日本曹達株式会社 | 含窒素ヘテロ環誘導体および農園芸用殺菌剤 |
| EP2323974A1 (en) | 2008-08-18 | 2011-05-25 | Ube Industries, Ltd. | Methods for preparing fluoroalkyl arylsulfinyl compounds and fluorinated compounds thereto |
| US20100056536A1 (en) | 2008-09-04 | 2010-03-04 | Charles Antzelevitch | Method of treating atrial fibrillation |
| WO2010053757A1 (en) | 2008-10-29 | 2010-05-14 | Gilead Palo Alto, Inc. | 2 -oxoquinoxalin blockers of the late sodium channel |
| WO2010074807A1 (en) | 2008-10-30 | 2010-07-01 | Gilead Palo Alto, Inc. | 3, 4-dihydroquinolin-2 ( 1h ) -one derivatives as sodium channel modulators |
| US8389500B2 (en) | 2008-10-30 | 2013-03-05 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
| US20100125091A1 (en) | 2008-11-14 | 2010-05-20 | Gilead Palo Alto, Inc. | Substituted heterocyclic compounds as ion channel modulators |
| US20100130436A1 (en) | 2008-11-25 | 2010-05-27 | Gilead Palo Alto, Inc. | Co-administration of ranolazine and cardiac glycosides |
| WO2010077686A1 (en) | 2008-12-08 | 2010-07-08 | Sirtris Pharmaceuticals, Inc. | Isoindolinone and related analogs as sirtuin modulators |
| WO2010077680A2 (en) | 2008-12-08 | 2010-07-08 | Vm Discovery Inc. | Compositions of protein receptor tyrosine kinase inhibitors |
| JP5271069B2 (ja) | 2008-12-24 | 2013-08-21 | 三和シヤッター工業株式会社 | 開閉装置 |
| FR2943342B1 (fr) | 2009-03-20 | 2011-03-04 | Servier Lab | Nouveaux derives de benzothiadiazepines,leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| KR20110131312A (ko) | 2009-03-27 | 2011-12-06 | 프레시디오 파마슈티칼스, 인코포레이티드 | 융합된 고리 ｃ형 간염 억제제 |
| US20100305093A1 (en) | 2009-04-09 | 2010-12-02 | Exelixis, Inc. | Inhibitors of mTOR and Methods of Making and Using |
| AU2010276537B2 (en) | 2009-07-27 | 2015-04-16 | Gilead Sciences, Inc. | Fused heterocyclic compounds as ion channel modulators |
| WO2011036280A1 (en) | 2009-09-28 | 2011-03-31 | F. Hoffmann-La Roche Ag | Benzoxazepin pi3k inhibitor compounds and methods of use |
| WO2011042920A1 (en) | 2009-10-07 | 2011-04-14 | Decode Genetics Ehf | Genetic variants indicative of vascular conditions |
| WO2011056985A2 (en) | 2009-11-04 | 2011-05-12 | Gilead Sciences, Inc. | Substituted heterocyclic compounds |
| CN104530079B (zh) | 2009-12-18 | 2017-10-20 | 北京凯因科技股份有限公司 | C型肝炎病毒复制的新型抑制剂 |
| TWI508726B (zh) | 2009-12-21 | 2015-11-21 | Gilead Sciences Inc | 治療心房纖維性顫動之方法 |
| MX2012015096A (es) | 2010-07-02 | 2013-05-28 | Gilead Sciences Inc | Compuestos heterociclicos fusionados como moduladores del canal ion. |
| WO2012019071A1 (en) | 2010-08-06 | 2012-02-09 | The Trustees Of Columbia University In The City Of New York | Methods of preventing and treating sarcopenia |
| WO2012019076A1 (en) | 2010-08-06 | 2012-02-09 | The Trustees Of Columbia University In The City Of New York | Compositions and methods for preventing and treating cardiac ischemia/reperfusion injury |
| WO2012037105A1 (en) | 2010-09-14 | 2012-03-22 | The Trustees Of Columbia University In The City Of New York | Methods of treating, ameliorating or preventing stress-induced neuronal disorders and diseases |
| WO2012036233A1 (ja) * | 2010-09-17 | 2012-03-22 | 塩野義製薬株式会社 | メラニン凝集ホルモン受容体アンタゴニスト活性を有する縮合へテロ環誘導体 |
| PL2619212T3 (pl) | 2010-09-21 | 2016-09-30 | Analogi buprenorfiny działające agonistycznie i/lub antagonistycznie na receptory opioidowe | |
| US8999967B2 (en) | 2010-09-29 | 2015-04-07 | Presidio Pharmaceuticals, Inc. | Tricyclic fused ring inhibitors of hepatitis C |
| EP2643316A2 (en) | 2010-11-24 | 2013-10-02 | Exelixis, Inc. | Benzoxazepines as inhibitors of p13k/mtor and methods of their use and manufacture |
| JP5675428B2 (ja) | 2011-02-25 | 2015-02-25 | サンドビック株式会社 | ベルトプレス装置 |
| MX340013B (es) | 2011-03-21 | 2016-06-22 | Hoffmann La Roche | Compuestos de benzoxazepina selectivos para fosfatidilinositol 3-cinasa (pi3k) p110 delta y metodos de uso. |
| EP2707361B1 (en) | 2011-05-10 | 2017-08-23 | Gilead Sciences, Inc. | Fused heterocyclic compounds as sodium channel modulators |
| CA2836904C (en) | 2011-06-03 | 2019-09-24 | Signpath Pharma Inc. | Liposomal mitigation of drug-induced long qt syndrome and potassium delayed-rectifier current |
| TWI622583B (zh) | 2011-07-01 | 2018-05-01 | 基利科學股份有限公司 | 作為離子通道調節劑之稠合雜環化合物 |
| NO3175985T3 (US06653308-20031125-C00057.png) | 2011-07-01 | 2018-04-28 | ||
| TWI567061B (zh) | 2011-07-01 | 2017-01-21 | 吉李德科學股份有限公司 | 用於治療成癮之化合物 |
| AU2012312266A1 (en) | 2011-09-21 | 2013-05-02 | Gilead Sciences, Inc. | Sodium channel blockers reduce glucagon secretion |
| WO2013097052A1 (en) | 2011-12-30 | 2013-07-04 | Abbott Laboratories | Bromodomain inhibitors |
| US8623860B2 (en) | 2011-12-30 | 2014-01-07 | Boehringer Ingelheim International Gmbh | Azetidine derivatives, pharmaceutical compositions and uses thereof |
| US20150045305A1 (en) | 2012-01-27 | 2015-02-12 | Gilead Sciences, Inc. | Combination therapies using late sodium ion channel blockers and potassium ion channel blockers |
| BR112014000049A2 (pt) | 2012-03-27 | 2017-02-07 | Bayer Ip Gmbh | pirrolotriazinas substituídas com hidroximelilarilo e sua utilização |
| US8969588B2 (en) | 2012-06-05 | 2015-03-03 | Gilead Pharmasset Llc | Solid forms of an antiviral compound |
| ES2805341T3 (es) | 2012-06-13 | 2021-02-11 | Acesion Pharma Aps | Composiciones farmacéuticas para terapia de combinación |
| WO2014134419A1 (en) | 2013-03-01 | 2014-09-04 | Gilead Sciences, Inc. | Use of ikach blockers for the treatment of cardiac diseases |
| CA2881544A1 (en) | 2014-02-13 | 2015-08-13 | Anna Chiu | Solid forms of a late sodium current inhibitor |
| CN104844535A (zh) | 2014-02-13 | 2015-08-19 | 吉利德科学公司 | 用于制备稠合杂环离子通道调节剂的方法 |
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- 2012-05-08 CN CN201610186640.5A patent/CN105693645B/zh not_active Expired - Fee Related
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