JP2017519836A5 - - Google Patents
Download PDFInfo
- Publication number
- 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
Links
- 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
- FWARWZGHKBEHCD-UHFFFAOYSA-N 1-[6-[3-methyl-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 CC1C(=C(CCC1)C1=CC=CC(=N1)N1N=CC(=C1C(F)(F)F)C(=O)O)COC=1C=C2CCN(CC2=CC=1)CC1=NC=CC=C1 FWARWZGHKBEHCD-UHFFFAOYSA-N 0.000 claims 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 210000005036 nerve Anatomy 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
- 229940125526 sGC activator Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- 239000003590 rho kinase inhibitor Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- SNIOPGDIGTZGOP-UHFFFAOYSA-N Nitroglycerin Chemical compound [O-][N+](=O)OCC(O[N+]([O-])=O)CO[N+]([O-])=O SNIOPGDIGTZGOP-UHFFFAOYSA-N 0.000 description 1
- 239000000006 Nitroglycerin Substances 0.000 description 1
- 229940006133 antiglaucoma drug and miotics carbonic anhydrase inhibitors Drugs 0.000 description 1
- 229960000307 avanafil Drugs 0.000 description 1
- WEAJZXNPAWBCOA-INIZCTEOSA-N avanafil Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NC(N2[C@@H](CCC2)CO)=NC=C1C(=O)NCC1=NC=CC=N1 WEAJZXNPAWBCOA-INIZCTEOSA-N 0.000 description 1
- 229960003711 glyceryl trinitrate Drugs 0.000 description 1
- 230000003547 miosis Effects 0.000 description 1
- MIJFNYMSCFYZNY-UHFFFAOYSA-N mirodenafil Chemical compound C1=C(C=2NC=3C(CCC)=CN(CC)C=3C(=O)N=2)C(OCCC)=CC=C1S(=O)(=O)N1CCN(CCO)CC1 MIJFNYMSCFYZNY-UHFFFAOYSA-N 0.000 description 1
- 229950002245 mirodenafil Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003169 prostaglandin F2α derivatives Chemical class 0.000 description 1
- WXXSNCNJFUAIDG-UHFFFAOYSA-N riociguat Chemical compound N1=C(N)C(N(C)C(=O)OC)=C(N)N=C1C(C1=CC=CN=C11)=NN1CC1=CC=CC=C1F WXXSNCNJFUAIDG-UHFFFAOYSA-N 0.000 description 1
- 229960000529 riociguat Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940127296 soluble guanylate cyclase stimulator Drugs 0.000 description 1
- MKPLKVHSHYCHOC-AHTXBMBWSA-N travoprost Chemical compound CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)COC1=CC=CC(C(F)(F)F)=C1 MKPLKVHSHYCHOC-AHTXBMBWSA-N 0.000 description 1
- 229960002368 travoprost Drugs 0.000 description 1
- 229960000438 udenafil Drugs 0.000 description 1
- IYFNEFQTYQPVOC-UHFFFAOYSA-N udenafil Chemical compound C1=C(C=2NC=3C(CCC)=NN(C)C=3C(=O)N=2)C(OCCC)=CC=C1S(=O)(=O)NCCC1CCCN1C IYFNEFQTYQPVOC-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462020187P | 2014-07-02 | 2014-07-02 | |
| US62/020,187 | 2014-07-02 | ||
| US201562127535P | 2015-03-03 | 2015-03-03 | |
| US62/127,535 | 2015-03-03 | ||
| US201562168651P | 2015-05-29 | 2015-05-29 | |
| US62/168,651 | 2015-05-29 | ||
| PCT/IB2015/055009 WO2016001878A1 (en) | 2014-07-02 | 2015-07-02 | Cyclohexen-1-yl-pyridin-2-yl-1h-pyrazole-4-carboxylic acid derivatives and the use thereof as soluble guanylate cyclase activators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2017519836A JP2017519836A (ja) | 2017-07-20 |
| JP2017519836A5 true JP2017519836A5 (enExample) | 2018-08-09 |
Family
ID=53724404
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017520036A Ceased JP2017519836A (ja) | 2014-07-02 | 2015-07-02 | シクロヘキセン−１−イル−ピリジン−２−イル−１ｈ−ピラゾール−４−カルボン酸誘導体、および可溶性グアニル酸シクラーゼ活性化剤としてのその使用 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US9957254B2 (enExample) |
| EP (1) | EP3164396B1 (enExample) |
| JP (1) | JP2017519836A (enExample) |
| CN (1) | CN106470986A (enExample) |
| TW (1) | TW201625586A (enExample) |
| WO (1) | WO2016001878A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US10351530B2 (en) * | 2015-10-06 | 2019-07-16 | 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 |
| CN108473470A (zh) | 2015-12-18 | 2018-08-31 | 诺华股份有限公司 | 作为可溶性鸟苷酸环化酶激活剂的茚满衍生物及其用途 |
| EP3489219B1 (en) | 2016-07-22 | 2020-12-16 | TOA Eiyo Ltd. | Therapeutic agent for glaucoma |
| US11331308B2 (en) | 2016-10-11 | 2022-05-17 | Bayer Pharma Aktiengesellschaft | Combination containing sGC activators and mineralocorticoid receptor antagonists |
| 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) |
| CN112055584A (zh) | 2018-04-30 | 2020-12-08 | 拜耳公司 | sGC活化剂和sGC刺激剂用于治疗认知障碍的用途 |
| MA52616A (fr) | 2018-05-15 | 2021-03-24 | Bayer Ag | Benzamides à substitution 1,3-thiazol-2-yl pour le traitement de maladies associées à la sensibilisation de fibres nerveuses |
| 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 |
| WO2020148379A1 (en) | 2019-01-17 | 2020-07-23 | Bayer Aktiengesellschaft | Methods to determine whether a subject is suitable of being treated with an agonist of soluble guanylyl cyclase (sgc) |
| CN119300815A (zh) | 2022-06-09 | 2025-01-10 | 拜耳公司 | 用于治疗女性射血分数保留型心力衰竭的可溶性鸟苷酸环化酶激活剂 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ302691B6 (cs) | 1998-07-08 | 2011-09-07 | Sanofi - Aventis Deutschland GmbH | N-Arylamidová sloucenina, zpusob její prípravy, farmaceutický prostredek tuto slouceninu obsahující, tato sloucenina pro použití jako aktivátor a pro použití k terapii nebo profylaxi |
| 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 |
| DE10110749A1 (de) | 2001-03-07 | 2002-09-12 | Bayer Ag | Substituierte Aminodicarbonsäurederivate |
| WO2004078163A2 (en) | 2003-02-28 | 2004-09-16 | Transform Pharmaceuticals, Inc. | Pharmaceutical co-crystal compositions of drugs such as carbamazepine, celecoxib, olanzapine, itraconazole, topiramate, modafinil, 5-fluorouracil, hydrochlorothiazide, acetaminophen, aspirin, flurbiprofen, phenytoin and ibuprofen |
| DE10216145A1 (de) | 2002-04-12 | 2003-10-23 | Bayer Ag | Verwendung von Stimulatoren der löslichen Guanylatcyclase zur Behandlung von Glaukom |
| RU2478619C2 (ru) | 2006-12-11 | 2013-04-10 | Ривайва Фармасьютикалс, Инк. | Композиции, синтез и способы применения ингибиторов холинэстеразы на основе инданона |
| DE102007015035A1 (de) | 2007-03-29 | 2008-10-02 | Bayer Healthcare Ag | Substituierte Dibenzoesäure-Derivate und ihre Verwendung |
| CN101939053A (zh) * | 2007-09-06 | 2011-01-05 | 默沙东公司 | 可溶性的鸟苷酸环化酶活化剂 |
| 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 |
| PE20091258A1 (es) | 2007-12-03 | 2009-09-12 | Smithkline Beecham Corp | Derivados de piridina como activadores de la guanilato ciclasa soluble |
| CN102056907B (zh) | 2008-04-04 | 2014-12-31 | 武田药品工业株式会社 | 杂环衍生物及其用途 |
| DE102008018675A1 (de) | 2008-04-14 | 2009-10-15 | Bayer Schering Pharma Aktiengesellschaft | Oxo-heterocyclisch substituierte Carbonsäure-Derivate und ihre Verwendung |
| CA2753434C (en) | 2009-02-26 | 2014-07-15 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| 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 |
| WO2012058132A1 (en) | 2010-10-28 | 2012-05-03 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| JP5989660B2 (ja) | 2010-12-07 | 2016-09-07 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 置換１−ベンジルシクロアルキルカルボン酸およびその使用 |
| US8569339B2 (en) | 2011-03-10 | 2013-10-29 | 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 |
| JP5565645B1 (ja) | 2012-10-09 | 2014-08-06 | Ｄｉｃ株式会社 | バンプクッション |
| WO2015011086A1 (en) | 2013-07-25 | 2015-01-29 | Bayer Pharma Aktiengesellschaft | Sgc stimulators or sgc activators and pde5 inhibitors in combination with additional treatment for the therapy of cystic fibrosis |
| RU2016112542A (ru) | 2013-09-05 | 2017-10-06 | Глэксосмитклайн Интеллекчуал Проперти Дивелопмент Лимитед | Новые активаторы растворимой гуанилатциклазы и их применение |
-
2015
- 2015-07-01 TW TW104121396A patent/TW201625586A/zh unknown
- 2015-07-02 CN CN201580036309.9A patent/CN106470986A/zh active Pending
- 2015-07-02 WO PCT/IB2015/055009 patent/WO2016001878A1/en not_active Ceased
- 2015-07-02 US US15/320,815 patent/US9957254B2/en active Active
- 2015-07-02 JP JP2017520036A patent/JP2017519836A/ja not_active Ceased
- 2015-07-02 EP EP15742105.8A patent/EP3164396B1/en not_active Not-in-force
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2017519835A5 (enExample) | ||
| US20240374571A1 (en) | Pharmaceutical combinations comprising a tead inhibitor and uses thereof for the treatment of cancers | |
| JP2017519025A5 (enExample) | ||
| TWI827037B (zh) | 作為nav1.8抑制劑之環烷基3-側氧基哌甲醯胺及環雜烷基3-側氧基哌甲醯胺 | |
| US7999006B2 (en) | Methods of using MEK inhibitors | |
| IL295799A (en) | Trophomyosin receptor kinase (trk) degradation compounds and methods of use | |
| TWI378098B (en) | Hydroxymethyl pyrrolidines as beta 3 adrenergic receptor agonists | |
| TW202146021A (zh) | 包含達拉菲尼、erk抑制劑和shp2抑制劑之三重藥物組合 | |
| RU2012127808A (ru) | Производные 2-пиридона | |
| JP2016516791A5 (enExample) | ||
| CA2984259A1 (en) | Combinations of inhibitors of irak4 with inhibitors of btk | |
| JP2023536462A5 (enExample) | ||
| WO2013080120A1 (en) | Novel trifluoromethyl-oxadiazole derivatives and their use in the treatment of disease | |
| JP2005536475A5 (enExample) | ||
| JP2016538313A5 (enExample) | ||
| RU2012116877A (ru) | Соединения 2-пиридона, применяемые в качестве ингибиторов нейтрофильной эластазы | |
| JP2010520199A (ja) | ピペリジン誘導体およびその使用方法 | |
| JP2021501145A5 (enExample) | ||
| JP2017519835A (ja) | インダンおよびインドリン誘導体、ならびに可溶性グアニル酸シクラーゼ活性化剤としてのその使用 | |
| JP2013531070A5 (enExample) | ||
| JP2022500428A5 (enExample) | ||
| CA3241001A1 (en) | Methods and dosing regimens comprising a cdk2 inhibitor and a cdk4 inhibitor for treating cancer | |
| JP2020535172A5 (enExample) | ||
| EP2455080A1 (en) | S1P1 receptor agonists for use in the treatment of multiple sclerosis | |
| RU2018126349A (ru) | Индановые производные и их применение в качестве активаторов растворимой гуанилатциклазы |