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 122
- 125000003118 aryl group Chemical group 0.000 claims description 116
- 125000000217 alkyl group Chemical group 0.000 claims description 97
- 125000000623 heterocyclic group Chemical group 0.000 claims description 97
- 150000001875 compounds Chemical class 0.000 claims description 69
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 66
- 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 48
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 45
- 150000003839 salts Chemical class 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 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 atom 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
- SUYKISAGQQPNCL-UHFFFAOYSA-N 3-benzyl-6-[2-fluoro-4-(trifluoromethyl)phenyl]-2H-1,3-benzoxazin-4-one 3-benzyl-6-[4-(trifluoromethyl)phenyl]-2H-1,3-benzoxazin-4-one 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
- 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
- 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 atom 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
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
- 230000001568 sexual effect Effects 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 206010007559 Cardiac failure congestive Diseases 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 125000005605 benzo group Chemical group 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 206010002383 Angina Pectoris Diseases 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- 206010019280 Heart failures Diseases 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 125000004419 alkynylene 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
- 208000028867 ischemia Diseases 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 229940002612 prodrug 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
- 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
- WODBRDZPPBUNAC-UHFFFAOYSA-N 2-(2-pyrazin-2-yloxyethyl)-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one 2-(2-pyridin-2-yloxyethyl)-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one Chemical compound N1=C(C=CC=C1)OCCN1C(C2=CC(=CC=C2C=N1)C1=CC=C(C=C1)OC(F)(F)F)=O.N1=C(C=NC=C1)OCCN1C(C2=CC(=CC=C2C=N1)C1=CC=C(C=C1)OC(F)(F)F)=O WODBRDZPPBUNAC-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
- CEDFXPQRXCHUDD-UHFFFAOYSA-N 2-[(4,6-dimethoxypyrimidin-2-yl)methyl]-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one 2-[2-(6-methylpyridin-2-yl)ethyl]-7-[4-(trifluoromethoxy)phenyl]phthalazin-1-one Chemical compound COC1=NC(=NC(=C1)OC)CN1C(C2=CC(=CC=C2C=N1)C1=CC=C(C=C1)OC(F)(F)F)=O.CC1=CC=CC(=N1)CCN1C(C2=CC(=CC=C2C=N1)C1=CC=C(C=C1)OC(F)(F)F)=O CEDFXPQRXCHUDD-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
- ZSIVVPXRCFYFJK-UHFFFAOYSA-N 2-[4-[7-[4-(trifluoromethyl)phenyl]-3,4-dihydro-1H-isoquinoline-2-carbonyl]triazol-1-yl]acetic acid Chemical compound OC(=O)Cn1cc(nn1)C(=O)N1CCc2ccc(cc2C1)-c1ccc(cc1)C(F)(F)F ZSIVVPXRCFYFJK-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
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- 2012-05-08 EP EP12722595.1A patent/EP2707361B1/en active Active
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