JP2017519836A5 - - Google Patents
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- JP2017519836A5 JP2017519836A5 JP2017520036A JP2017520036A JP2017519836A5 JP 2017519836 A5 JP2017519836 A5 JP 2017519836A5 JP 2017520036 A JP2017520036 A JP 2017520036A JP 2017520036 A JP2017520036 A JP 2017520036A JP 2017519836 A5 JP2017519836 A5 JP 2017519836A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyrazole
- carboxylic acid
- trifluoromethyl
- pyridin
- 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.)
- Ceased
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 52
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 48
- 150000003839 salts Chemical class 0.000 claims description 45
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 31
- 150000002431 hydrogen Chemical group 0.000 claims description 21
- -1 C 1 -C 4 alkyl Chemical group 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 12
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 238000002347 injection Methods 0.000 claims description 12
- 239000007924 injection Substances 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 208000010412 Glaucoma Diseases 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 239000002590 phosphodiesterase V inhibitor Substances 0.000 claims description 6
- BNRNXUUZRGQAQC-UHFFFAOYSA-N sildenafil Chemical compound CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 BNRNXUUZRGQAQC-UHFFFAOYSA-N 0.000 claims description 6
- 238000002513 implantation Methods 0.000 claims description 5
- 230000004410 intraocular pressure Effects 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- SECKRCOLJRRGGV-UHFFFAOYSA-N Vardenafil Chemical compound CCCC1=NC(C)=C(C(N=2)=O)N1NC=2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CC)CC1 SECKRCOLJRRGGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000000674 adrenergic antagonist Substances 0.000 claims description 3
- 239000000556 agonist Substances 0.000 claims description 3
- 102000012740 beta Adrenergic Receptors Human genes 0.000 claims description 3
- 108010079452 beta Adrenergic Receptors Proteins 0.000 claims description 3
- 239000003489 carbonate dehydratase inhibitor Substances 0.000 claims description 3
- 239000003604 miotic agent Substances 0.000 claims description 3
- 239000004090 neuroprotective agent Substances 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 150000003180 prostaglandins Chemical class 0.000 claims description 3
- 229960003310 sildenafil Drugs 0.000 claims description 3
- 229960000835 tadalafil Drugs 0.000 claims description 3
- IEHKWSGCTWLXFU-IIBYNOLFSA-N tadalafil Chemical compound C1=C2OCOC2=CC([C@@H]2C3=C([C]4C=CC=CC4=N3)C[C@H]3N2C(=O)CN(C3=O)C)=C1 IEHKWSGCTWLXFU-IIBYNOLFSA-N 0.000 claims description 3
- 229960002381 vardenafil Drugs 0.000 claims description 3
- 229940122072 Carbonic anhydrase inhibitor Drugs 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 238000007918 intramuscular administration Methods 0.000 claims description 2
- 238000001990 intravenous administration Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 210000003786 sclera Anatomy 0.000 claims description 2
- 238000007920 subcutaneous administration Methods 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 5
- MCLKZJLGDFGFLI-UHFFFAOYSA-N 1-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound OC(=O)C=1C=NN(C(F)(F)F)C=1 MCLKZJLGDFGFLI-UHFFFAOYSA-N 0.000 claims 3
- PTVHGLSWQQDLFD-YANBTOMASA-N 1-[6-[2-[[3-ethyl-4-[1-[(2S)-2-hydroxypropanoyl]piperidin-4-yl]phenoxy]methyl]-3-methylcyclohexen-1-yl]pyridin-2-yl]-5-methylpyrazole-4-carboxylic acid Chemical compound C(C)C=1C=C(OCC2=C(CCCC2C)C2=CC=CC(=N2)N2N=CC(=C2C)C(=O)O)C=CC=1C1CCN(CC1)C([C@H](C)O)=O PTVHGLSWQQDLFD-YANBTOMASA-N 0.000 claims 2
- WGLPLGFIOZBTKQ-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(cyclopropanecarbonyl)piperidin-4-yl]-2-methylphenoxy]methyl]-3-methylcyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound C1(CC1)C(=O)N1CCC(CC1)C1=CC(=C(OCC2=C(CCCC2C)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)C WGLPLGFIOZBTKQ-UHFFFAOYSA-N 0.000 claims 2
- VGOKNANPAQUEEG-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(cyclopropanecarbonyl)piperidin-4-yl]-2-methylphenoxy]methyl]-5-methylcyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound C1(CC1)C(=O)N1CCC(CC1)C1=CC(=C(OCC2=C(CC(CC2)C)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)C VGOKNANPAQUEEG-UHFFFAOYSA-N 0.000 claims 2
- WGHDZXSKJPEPMY-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(cyclopropanecarbonyl)piperidin-4-yl]-3-ethylphenoxy]methyl]-3-methylcyclohexen-1-yl]pyridin-2-yl]-5-(difluoromethyl)pyrazole-4-carboxylic acid Chemical compound C1(CC1)C(=O)N1CCC(CC1)C1=C(C=C(OCC2=C(CCCC2C)C2=CC=CC(=N2)N2N=CC(=C2C(F)F)C(=O)O)C=C1)CC WGHDZXSKJPEPMY-UHFFFAOYSA-N 0.000 claims 2
- BSBQDUABNFPDND-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(cyclopropanecarbonyl)piperidin-4-yl]-3-ethylphenoxy]methyl]-3-methylcyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound C1(CC1)C(=O)N1CCC(CC1)C1=C(C=C(OCC2=C(CCCC2C)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)CC BSBQDUABNFPDND-UHFFFAOYSA-N 0.000 claims 2
- XMRNTTICFHANRN-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(cyclopropanecarbonyl)piperidin-4-yl]-3-ethylphenoxy]methyl]-3-methylcyclohexen-1-yl]pyridin-2-yl]-5-ethylpyrazole-4-carboxylic acid Chemical compound C1(CC1)C(=O)N1CCC(CC1)C1=C(C=C(OCC2=C(CCCC2C)C2=CC=CC(=N2)N2N=CC(=C2CC)C(=O)O)C=C1)CC XMRNTTICFHANRN-UHFFFAOYSA-N 0.000 claims 2
- FNEBNVRWTSBLMP-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(cyclopropanecarbonyl)piperidin-4-yl]-3-ethylphenoxy]methyl]-3-methylcyclohexen-1-yl]pyridin-2-yl]-5-methylpyrazole-4-carboxylic acid Chemical compound C1(CC1)C(=O)N1CCC(CC1)C1=C(C=C(OCC2=C(CCCC2C)C2=CC=CC(=N2)N2N=CC(=C2C)C(=O)O)C=C1)CC FNEBNVRWTSBLMP-UHFFFAOYSA-N 0.000 claims 2
- XYUPMURFBLEIKR-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(cyclopropanecarbonyl)piperidin-4-yl]-3-ethylphenoxy]methyl]-3-methylcyclopenten-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound C1(CC1)C(=O)N1CCC(CC1)C1=C(C=C(OCC2=C(CCC2C)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)CC XYUPMURFBLEIKR-UHFFFAOYSA-N 0.000 claims 2
- NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- RKUBLOVENWTXKK-WCSIJFPASA-N 5-ethyl-1-[6-[2-[[3-ethyl-4-[1-[(2S)-2-hydroxypropanoyl]piperidin-4-yl]phenoxy]methyl]-3-methylcyclohexen-1-yl]pyridin-2-yl]pyrazole-4-carboxylic acid Chemical compound C(C)C1=C(C=NN1C1=NC(=CC=C1)C1=C(C(CCC1)C)COC1=CC(=C(C=C1)C1CCN(CC1)C([C@H](C)O)=O)CC)C(=O)O RKUBLOVENWTXKK-WCSIJFPASA-N 0.000 claims 2
- YKIOZIKSMAVYLM-UHFFFAOYSA-N 1-[3-[2-[[4-[1-(cyclopropanecarbonyl)piperidin-4-yl]-2-methylphenoxy]methyl]-5-methylcyclohexen-1-yl]phenyl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound C1(CC1)C(=O)N1CCC(CC1)C1=CC(=C(OCC=2CCC(CC=2C2=CC(=CC=C2)N2N=CC(=C2C(F)(F)F)C(=O)O)C)C=C1)C YKIOZIKSMAVYLM-UHFFFAOYSA-N 0.000 claims 1
- GLYLOKJCTYNIMV-UHFFFAOYSA-N 1-[3-[2-[[4-[1-(cyclopropanecarbonyl)piperidin-4-yl]-2-methylphenoxy]methyl]cyclohexen-1-yl]phenyl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound C1(CC1)C(=O)N1CCC(CC1)C1=CC(=C(OCC=2CCCCC=2C2=CC(=CC=C2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)C GLYLOKJCTYNIMV-UHFFFAOYSA-N 0.000 claims 1
- SZCTZERBRRNWBV-UHFFFAOYSA-N 1-[6-[2-[[2-(pyridin-2-ylmethyl)-3,4-dihydro-1H-isoquinolin-6-yl]oxymethyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound N1=C(C=CC=C1)CN1CC2=CC=C(C=C2CC1)OCC1=C(CCCC1)C1=CC=CC(=N1)N1N=CC(=C1C(F)(F)F)C(=O)O SZCTZERBRRNWBV-UHFFFAOYSA-N 0.000 claims 1
- SZHVIFSNTGUKRT-UHFFFAOYSA-N 1-[6-[2-[[2-(quinolin-2-ylmethyl)-3,4-dihydro-1H-isoquinolin-6-yl]oxymethyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound N1=C(C=CC2=CC=CC=C12)CN1CC2=CC=C(C=C2CC1)OCC1=C(CCCC1)C1=CC=CC(=N1)N1N=CC(=C1C(F)(F)F)C(=O)O SZHVIFSNTGUKRT-UHFFFAOYSA-N 0.000 claims 1
- VGVPHERVGNZQCV-UHFFFAOYSA-N 1-[6-[2-[[2-[(6-methylpyridin-2-yl)methyl]-3,4-dihydro-1H-isoquinolin-6-yl]oxymethyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound CC1=CC=CC(=N1)CN1CC2=CC=C(C=C2CC1)OCC1=C(CCCC1)C1=CC=CC(=N1)N1N=CC(=C1C(F)(F)F)C(=O)O VGVPHERVGNZQCV-UHFFFAOYSA-N 0.000 claims 1
- NHICNESPVXQMBH-UHFFFAOYSA-N 1-[6-[2-[[2-methyl-4-(1-methylsulfonylpiperidin-4-yl)phenoxy]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound CC1=C(OCC2=C(CCCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=CC(=C1)C1CCN(CC1)S(=O)(=O)C NHICNESPVXQMBH-UHFFFAOYSA-N 0.000 claims 1
- MCNCGQATCKCKFB-UHFFFAOYSA-N 1-[6-[2-[[2-methyl-4-(1-methylsulfonylpiperidin-4-yl)phenoxy]methyl]cyclopenten-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound CC1=C(OCC2=C(CCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=CC(=C1)C1CCN(CC1)S(=O)(=O)C MCNCGQATCKCKFB-UHFFFAOYSA-N 0.000 claims 1
- ZDPZRZFOMHOJFT-UHFFFAOYSA-N 1-[6-[2-[[2-methyl-4-[1-(2,2,2-trifluoroethyl)piperidin-4-yl]phenoxy]methyl]cyclopenten-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound CC1=C(OCC2=C(CCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=CC(=C1)C1CCN(CC1)CC(F)(F)F ZDPZRZFOMHOJFT-UHFFFAOYSA-N 0.000 claims 1
- RFVPRAIRUZAGKU-UHFFFAOYSA-N 1-[6-[2-[[2-methyl-4-[1-(2-methylpropanoyl)piperidin-4-yl]phenoxy]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound C(C(C)C)(=O)N1CCC(CC1)C1=CC(=C(OCC2=C(CCCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)C RFVPRAIRUZAGKU-UHFFFAOYSA-N 0.000 claims 1
- FXLXCMBHCTXXLG-UHFFFAOYSA-N 1-[6-[2-[[2-methyl-4-[1-(pyridine-2-carbonyl)piperidin-4-yl]phenoxy]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound CC1=C(OCC2=C(CCCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=CC(=C1)C1CCN(CC1)C(C1=NC=CC=C1)=O FXLXCMBHCTXXLG-UHFFFAOYSA-N 0.000 claims 1
- CPSQLMJQAXZSFZ-UHFFFAOYSA-N 1-[6-[2-[[2-methyl-4-[1-[(2-methylpropan-2-yl)oxycarbonyl]piperidin-4-yl]phenoxy]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound C(C)(C)(C)OC(=O)N1CCC(CC1)C1=CC(=C(OCC2=C(CCCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)C CPSQLMJQAXZSFZ-UHFFFAOYSA-N 0.000 claims 1
- IPUYHVRTXNEKJK-UHFFFAOYSA-N 1-[6-[2-[[4-(1-cyclopropylsulfonylpiperidin-4-yl)-2-methylphenoxy]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound C1(CC1)S(=O)(=O)N1CCC(CC1)C1=CC(=C(OCC2=C(CCCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)C IPUYHVRTXNEKJK-UHFFFAOYSA-N 0.000 claims 1
- ORIVIIPJBYFNCQ-UHFFFAOYSA-N 1-[6-[2-[[4-(1-ethylsulfonylpiperidin-4-yl)-2-methylphenoxy]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound C(C)S(=O)(=O)N1CCC(CC1)C1=CC(=C(OCC2=C(CCCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)C ORIVIIPJBYFNCQ-UHFFFAOYSA-N 0.000 claims 1
- UNSGQHOGYGYWDY-UHFFFAOYSA-N 1-[6-[2-[[4-(1-methoxycarbonylpiperidin-4-yl)-2-methylphenoxy]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound COC(=O)N1CCC(CC1)C1=CC(=C(OCC2=C(CCCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)C UNSGQHOGYGYWDY-UHFFFAOYSA-N 0.000 claims 1
- XBXJLEFYZDMSSD-UHFFFAOYSA-N 1-[6-[2-[[4-(1-methoxycarbonylpiperidin-4-yl)-2-methylphenoxy]methyl]cyclopenten-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound COC(=O)N1CCC(CC1)C1=CC(=C(OCC2=C(CCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)C XBXJLEFYZDMSSD-UHFFFAOYSA-N 0.000 claims 1
- MXRGDVVKMQGCRQ-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(2-aminoacetyl)piperidin-4-yl]-2-methylphenoxy]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound NCC(=O)N1CCC(CC1)C1=CC(=C(OCC2=C(CCCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)C MXRGDVVKMQGCRQ-UHFFFAOYSA-N 0.000 claims 1
- JFUGOXVEGMWQHR-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(2-hydroxyacetyl)piperidin-4-yl]-2-methylphenoxy]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound OCC(=O)N1CCC(CC1)C1=CC(=C(OCC2=C(CCCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)C JFUGOXVEGMWQHR-UHFFFAOYSA-N 0.000 claims 1
- DUYYZGPDRBHSQQ-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(2-hydroxyacetyl)piperidin-4-yl]-2-methylphenoxy]methyl]cyclopenten-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound OCC(=O)N1CCC(CC1)C1=CC(=C(OCC2=C(CCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)C DUYYZGPDRBHSQQ-UHFFFAOYSA-N 0.000 claims 1
- XMALFZJQJQRJLC-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(cyclobutanecarbonyl)piperidin-4-yl]-2-methylphenoxy]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound C1(CCC1)C(=O)N1CCC(CC1)C1=CC(=C(OCC2=C(CCCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)C XMALFZJQJQRJLC-UHFFFAOYSA-N 0.000 claims 1
- ODLLZCIPYSQNFR-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(cyclopropanecarbonyl)piperidin-4-yl]-2-ethylphenoxy]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound C1(CC1)C(=O)N1CCC(CC1)C1=CC(=C(OCC2=C(CCCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)CC ODLLZCIPYSQNFR-UHFFFAOYSA-N 0.000 claims 1
- PWQAGYOUSXOWGG-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(cyclopropanecarbonyl)piperidin-4-yl]-2-methylanilino]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound C1(CC1)C(=O)N1CCC(CC1)C1=CC(=C(C=C1)NCC1=C(CCCC1)C1=CC=CC(=N1)N1N=CC(=C1C(F)(F)F)C(=O)O)C PWQAGYOUSXOWGG-UHFFFAOYSA-N 0.000 claims 1
- RMJUZJQMBKKGFC-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(cyclopropanecarbonyl)piperidin-4-yl]-2-methylphenoxy]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound C1(CC1)C(=O)N1CCC(CC1)C1=CC(=C(OCC2=C(CCCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)C RMJUZJQMBKKGFC-UHFFFAOYSA-N 0.000 claims 1
- IHEPPIYXUAWLDV-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(cyclopropanecarbonyl)piperidin-4-yl]-2-methylphenoxy]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-ethylpyrazole-4-carboxylic acid Chemical compound C1(CC1)C(=O)N1CCC(CC1)C1=CC(=C(OCC2=C(CCCC2)C2=CC=CC(=N2)N2N=CC(=C2CC)C(=O)O)C=C1)C IHEPPIYXUAWLDV-UHFFFAOYSA-N 0.000 claims 1
- FWIQJXYAPVUMQM-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(cyclopropanecarbonyl)piperidin-4-yl]-2-methylphenoxy]methyl]cyclopenten-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound C1(CC1)C(=O)N1CCC(CC1)C1=CC(=C(OCC2=C(CCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)C FWIQJXYAPVUMQM-UHFFFAOYSA-N 0.000 claims 1
- RAJCOYAQBRSKHA-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(cyclopropanecarbonyl)piperidin-4-yl]-3-ethylanilino]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound C1(CC1)C(=O)N1CCC(CC1)C1=C(C=C(C=C1)NCC1=C(CCCC1)C1=CC=CC(=N1)N1N=CC(=C1C(F)(F)F)C(=O)O)CC RAJCOYAQBRSKHA-UHFFFAOYSA-N 0.000 claims 1
- BHKWPWKZKLOKCX-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(cyclopropanecarbonyl)piperidin-4-yl]-3-ethylphenoxy]methyl]-3,3-dimethylcyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound C1(CC1)C(=O)N1CCC(CC1)C1=C(C=C(OCC2=C(CCCC2(C)C)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)CC BHKWPWKZKLOKCX-UHFFFAOYSA-N 0.000 claims 1
- YXXRNZRFKTUPPI-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(cyclopropanecarbonyl)piperidin-4-yl]-3-ethylphenoxy]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound C1(CC1)C(=O)N1CCC(CC1)C1=C(C=C(OCC2=C(CCCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)CC YXXRNZRFKTUPPI-UHFFFAOYSA-N 0.000 claims 1
- CIKNNYSIMIDHJL-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(cyclopropanecarbonyl)piperidin-4-yl]anilino]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound C1(CC1)C(=O)N1CCC(CC1)C1=CC=C(C=C1)NCC1=C(CCCC1)C1=CC=CC(=N1)N1N=CC(=C1C(F)(F)F)C(=O)O CIKNNYSIMIDHJL-UHFFFAOYSA-N 0.000 claims 1
- WSONHUXIPHAIOH-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(cyclopropylmethyl)piperidin-4-yl]-2-methylphenoxy]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound C1(CC1)CN1CCC(CC1)C1=CC(=C(OCC2=C(CCCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)C WSONHUXIPHAIOH-UHFFFAOYSA-N 0.000 claims 1
- FAZZQRWLAUVYFP-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(diethylcarbamoyl)piperidin-4-yl]-2-methylphenoxy]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound C(C)N(C(=O)N1CCC(CC1)C1=CC(=C(OCC2=C(CCCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)C)CC FAZZQRWLAUVYFP-UHFFFAOYSA-N 0.000 claims 1
- BGEYJVCNVYBYMZ-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(dimethylcarbamoyl)piperidin-4-yl]-2-methylphenoxy]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound CN(C(=O)N1CCC(CC1)C1=CC(=C(OCC2=C(CCCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)C)C BGEYJVCNVYBYMZ-UHFFFAOYSA-N 0.000 claims 1
- PFYQDAFJVVEUES-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(dimethylcarbamoyl)piperidin-4-yl]-2-methylphenoxy]methyl]cyclopenten-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound CN(C(=O)N1CCC(CC1)C1=CC(=C(OCC2=C(CCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)C)C PFYQDAFJVVEUES-UHFFFAOYSA-N 0.000 claims 1
- CGOGFJHZZLJTAR-UHFFFAOYSA-N 1-[6-[2-[[4-[1-(ethylcarbamoyl)piperidin-4-yl]-2-methylphenoxy]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound C(C)NC(=O)N1CCC(CC1)C1=CC(=C(OCC2=C(CCCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)C CGOGFJHZZLJTAR-UHFFFAOYSA-N 0.000 claims 1
- DLVVENNQSQEFHO-HXUWFJFHSA-N 1-[6-[2-[[4-[1-[(2R)-2-hydroxypropanoyl]piperidin-4-yl]-2-methylphenoxy]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound O[C@@H](C(=O)N1CCC(CC1)C1=CC(=C(OCC2=C(CCCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)C)C DLVVENNQSQEFHO-HXUWFJFHSA-N 0.000 claims 1
- DLVVENNQSQEFHO-FQEVSTJZSA-N 1-[6-[2-[[4-[1-[(2S)-2-hydroxypropanoyl]piperidin-4-yl]-2-methylphenoxy]methyl]cyclohexen-1-yl]pyridin-2-yl]-5-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound O[C@H](C(=O)N1CCC(CC1)C1=CC(=C(OCC2=C(CCCC2)C2=CC=CC(=N2)N2N=CC(=C2C(F)(F)F)C(=O)O)C=C1)C)C DLVVENNQSQEFHO-FQEVSTJZSA-N 0.000 claims 1
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| TW201625584A (zh) | 2014-07-02 | 2016-07-16 | 諾華公司 | 茚滿及吲哚啉衍生物及其作為可溶性鳥苷酸環化酶活化劑之用途 |
| EP3371167A1 (en) * | 2015-10-06 | 2018-09-12 | GlaxoSmithKline Intellectual Property Development Limited | Arylcyclohexyl pyrazoles as nrf2 regulators |
| US10364256B2 (en) | 2015-10-06 | 2019-07-30 | Glaxosmithkline Intellectual Property Development Limited | Biaryl pyrazoles as NRF2 regulators |
| RU2018126349A (ru) | 2015-12-18 | 2020-01-20 | Новартис Аг | Индановые производные и их применение в качестве активаторов растворимой гуанилатциклазы |
| EP3489219B1 (en) * | 2016-07-22 | 2020-12-16 | TOA Eiyo Ltd. | Therapeutic agent for glaucoma |
| WO2018069148A1 (de) | 2016-10-11 | 2018-04-19 | Bayer Pharma Aktiengesellschaft | Kombination enthaltend sgc aktivatoren und mineralocorticoid-rezeptor-antagonisten |
| WO2019081456A1 (en) | 2017-10-24 | 2019-05-02 | Bayer Aktiengesellschaft | USE OF SGC ACTIVATORS AND STIMULATORS COMPRISING A BETA2 SUBUNIT |
| EP3498298A1 (en) | 2017-12-15 | 2019-06-19 | Bayer AG | The use of sgc stimulators and sgc activators alone or in combination with pde5 inhibitors for the treatment of bone disorders including osteogenesis imperfecta (oi) |
| US20210052528A1 (en) | 2018-04-30 | 2021-02-25 | Bayer Aktiengesellschaft | The use of sgc activators and sgc stimulators for the treatment of cognitive impairment |
| EP3793553A1 (en) | 2018-05-15 | 2021-03-24 | Bayer Aktiengesellschaft | 1,3-thiazol-2-yl substituted benzamides for the treatment of diseases associated with nerve fiber sensitization |
| US11508483B2 (en) | 2018-05-30 | 2022-11-22 | Adverio Pharma Gmbh | Method of identifying a subgroup of patients suffering from dcSSc which benefits from a treatment with sGC stimulators and sGC activators in a higher degree than a control group |
| EP3911675A1 (en) | 2019-01-17 | 2021-11-24 | Bayer Aktiengesellschaft | Methods to determine whether a subject is suitable of being treated with an agonist of soluble guanylyl cyclase (sgc) |
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| EP1420023B1 (en) | 2001-01-24 | 2006-12-06 | Yung Shin Pharmaceutical Ind. Co., Ltd. | Use of fused pyrazolyl compounds for the preparation of a medicament for treating hypertension |
| DE10110750A1 (de) | 2001-03-07 | 2002-09-12 | Bayer Ag | Neuartige Aminodicarbonsäurederivate mit pharmazeutischen Eigenschaften |
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| EP1631260A2 (en) | 2003-02-28 | 2006-03-08 | Transform Pharmaceuticals, Inc. | Pharmaceutical co-crystal compositions of drugs such as carbamazepine, celecoxib, olanzapine, itraconazole, topiramate, modafinil, 5-fluorouracil, hydrochlorothazide, acetaminophen, aspirin, flurbiprofen, phenytoin and ibuprofen |
| RU2478619C2 (ru) | 2006-12-11 | 2013-04-10 | Ривайва Фармасьютикалс, Инк. | Композиции, синтез и способы применения ингибиторов холинэстеразы на основе инданона |
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| AU2008296974B2 (en) * | 2007-09-06 | 2013-10-10 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| WO2009068652A1 (en) | 2007-11-30 | 2009-06-04 | Smithkline Beecham Corporation | 2, 6-disubstituted pyridines and 2, 4-disubstituted pyrimidines as soluble guanylate cyclase activators |
| WO2009071504A1 (en) | 2007-12-03 | 2009-06-11 | Smithkline Beecham Corporation | 2,6-disubstituted pyridines as soluble guanylate cyclase activators |
| EP2264017A4 (en) | 2008-04-04 | 2011-07-27 | Takeda Pharmaceutical | Heterocyclic derivative and its use |
| DE102008018675A1 (de) | 2008-04-14 | 2009-10-15 | Bayer Schering Pharma Aktiengesellschaft | Oxo-heterocyclisch substituierte Carbonsäure-Derivate und ihre Verwendung |
| KR20110133034A (ko) * | 2009-02-26 | 2011-12-09 | 머크 샤프 앤드 돔 코포레이션 | 가용성 구아닐레이트 시클라제 활성화제 |
| DE102009012314A1 (de) | 2009-03-09 | 2010-09-16 | Bayer Schering Pharma Aktiengesellschaft | Oxo-heterocyclisch substituierte Alkylcarbonsäuren und ihre Verwendung |
| DE102009046115A1 (de) | 2009-10-28 | 2011-09-08 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 3-Phenylpropansäuren und ihre Verwendung |
| US8895583B2 (en) | 2010-10-28 | 2014-11-25 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| AP2013006953A0 (en) | 2010-12-07 | 2013-06-30 | Bayer Ip Gmbh | Substituted 1-benzylcycloalkylcarboxlic acids and use thereof |
| EP2683710B1 (en) | 2011-03-10 | 2017-07-19 | Boehringer Ingelheim International GmbH | Soluble guanylate cyclase activators |
| DE102011007272A1 (de) | 2011-04-13 | 2012-10-18 | Bayer Pharma Aktiengesellschaft | Verzweigte 3-Phenylpropionsäure-Derivate und ihre Verwendung |
| WO2013025425A1 (en) | 2011-08-12 | 2013-02-21 | Boehringer Ingelheim International Gmbh | Soluble guanylate cyclase activators |
| WO2014057740A1 (ja) | 2012-10-09 | 2014-04-17 | Dic株式会社 | バンプクッション |
| US10265314B2 (en) | 2013-07-25 | 2019-04-23 | Bayer Pharma Aktiengesellschaft | SGC stimulators in combination with additional treatment for the therapy of cystic fibrosis |
| JP2016530292A (ja) | 2013-09-05 | 2016-09-29 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドＧｌａｘｏｓｍｉｔｈｋｌｉｎｅ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ Ｄｅｖｅｌｏｐｍｅｎｔ Ｌｉｍｉｔｅｄ | 新規な可溶性グアニル酸シクラーゼ活性剤およびそれらの使用 |
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