JP2011514894A5 - - Google Patents
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- JP2011514894A5 JP2011514894A5 JP2010548731A JP2010548731A JP2011514894A5 JP 2011514894 A5 JP2011514894 A5 JP 2011514894A5 JP 2010548731 A JP2010548731 A JP 2010548731A JP 2010548731 A JP2010548731 A JP 2010548731A JP 2011514894 A5 JP2011514894 A5 JP 2011514894A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- pyridin
- biphenyl
- amide
- carboxylic acid
- 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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- 150000001875 compounds Chemical class 0.000 claims description 90
- -1 thiomorpholin-1-yl Chemical group 0.000 claims description 64
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
- 125000001475 halogen functional group Chemical group 0.000 claims description 19
- 208000004296 neuralgia Diseases 0.000 claims description 17
- 208000002193 Pain Diseases 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 13
- 239000000651 prodrug Substances 0.000 claims description 13
- 229940002612 prodrug Drugs 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000012453 solvate Substances 0.000 claims description 13
- 150000001408 amides Chemical class 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 12
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 11
- 230000000155 isotopic effect Effects 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- VLHCBYKYPDIQQV-UHFFFAOYSA-N 5-(4-methylphenyl)benzene-1,3-dicarboxylic acid Chemical compound C1=CC(C)=CC=C1C1=CC(C(O)=O)=CC(C(O)=O)=C1 VLHCBYKYPDIQQV-UHFFFAOYSA-N 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 230000001404 mediated effect Effects 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 8
- 208000023275 Autoimmune disease Diseases 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 208000037765 diseases and disorders Diseases 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 206010061218 Inflammation Diseases 0.000 claims description 6
- 150000001204 N-oxides Chemical class 0.000 claims description 6
- 208000003251 Pruritus Diseases 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000004442 acylamino group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 6
- 150000001540 azides Chemical class 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 230000004054 inflammatory process Effects 0.000 claims description 6
- QKYWADPCTHTJHQ-UHFFFAOYSA-N n,2-dimethylpropan-1-amine Chemical compound CNCC(C)C QKYWADPCTHTJHQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
- 206010015037 epilepsy Diseases 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 208000021722 neuropathic pain Diseases 0.000 claims description 5
- SDVPSCPQWOQATE-UHFFFAOYSA-N 3-(2-cyano-4-methylphenyl)-5-(oxolan-3-yloxy)benzoic acid Chemical compound N#CC1=CC(C)=CC=C1C1=CC(OC2COCC2)=CC(C(O)=O)=C1 SDVPSCPQWOQATE-UHFFFAOYSA-N 0.000 claims description 4
- ZCXYTMGHGRBTOT-UHFFFAOYSA-N 3-(4-methylphenyl)-5-(pyrrolidine-1-carbonyl)benzoic acid Chemical compound C1=CC(C)=CC=C1C1=CC(C(O)=O)=CC(C(=O)N2CCCC2)=C1 ZCXYTMGHGRBTOT-UHFFFAOYSA-N 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000019695 Migraine disease Diseases 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 208000012902 Nervous system disease Diseases 0.000 claims description 4
- 208000025966 Neurological disease Diseases 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- 206010043269 Tension headache Diseases 0.000 claims description 4
- 208000008548 Tension-Type Headache Diseases 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 206010027599 migraine Diseases 0.000 claims description 4
- 230000004770 neurodegeneration Effects 0.000 claims description 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
- 230000000926 neurological effect Effects 0.000 claims description 4
- 201000008482 osteoarthritis Diseases 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
- 208000004371 toothache Diseases 0.000 claims description 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 208000019901 Anxiety disease Diseases 0.000 claims description 3
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 3
- 208000020925 Bipolar disease Diseases 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 208000000094 Chronic Pain Diseases 0.000 claims description 3
- 208000006561 Cluster Headache Diseases 0.000 claims description 3
- 208000034347 Faecal incontinence Diseases 0.000 claims description 3
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 3
- 206010020751 Hypersensitivity Diseases 0.000 claims description 3
- 206010065390 Inflammatory pain Diseases 0.000 claims description 3
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 3
- 206010046543 Urinary incontinence Diseases 0.000 claims description 3
- 230000001154 acute effect Effects 0.000 claims description 3
- 208000005298 acute pain Diseases 0.000 claims description 3
- 201000009961 allergic asthma Diseases 0.000 claims description 3
- 208000026935 allergic disease Diseases 0.000 claims description 3
- 201000010105 allergic rhinitis Diseases 0.000 claims description 3
- 230000036506 anxiety Effects 0.000 claims description 3
- 206010003246 arthritis Diseases 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 210000003169 central nervous system Anatomy 0.000 claims description 3
- 208000018912 cluster headache syndrome Diseases 0.000 claims description 3
- 208000010877 cognitive disease Diseases 0.000 claims description 3
- 206010014599 encephalitis Diseases 0.000 claims description 3
- 230000009610 hypersensitivity Effects 0.000 claims description 3
- 230000002757 inflammatory effect Effects 0.000 claims description 3
- 150000002632 lipids Chemical class 0.000 claims description 3
- 125000005322 morpholin-1-yl group Chemical group 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 230000003959 neuroinflammation Effects 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 210000002307 prostate Anatomy 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 208000036273 reactive airway disease Diseases 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 208000019116 sleep disease Diseases 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- ZEIBSXHCAJBXJZ-UHFFFAOYSA-N 2-methyl-3-(4-methylphenyl)-n-[(2-methylpyrimidin-5-yl)methyl]-5-pyrrolidin-1-ylsulfonylbenzamide Chemical compound C1=CC(C)=CC=C1C1=CC(S(=O)(=O)N2CCCC2)=CC(C(=O)NCC=2C=NC(C)=NC=2)=C1C ZEIBSXHCAJBXJZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- FSEGARGJNQWUER-OEPVSBQMSA-N 3-(1,2-dimethoxyethyl)-5-(4-methylphenyl)-n-[(1r)-1-(6-methylpyridin-3-yl)ethyl]benzamide Chemical compound C=1C(C(OC)COC)=CC(C(=O)N[C@H](C)C=2C=NC(C)=CC=2)=CC=1C1=CC=C(C)C=C1 FSEGARGJNQWUER-OEPVSBQMSA-N 0.000 claims description 2
- PRRPPWPGDIOZCX-LJQANCHMSA-N 3-(1,3-benzothiazol-2-yloxy)-5-(5-methylpyridin-2-yl)-n-[(1r)-1-(6-methylpyridin-3-yl)ethyl]benzamide Chemical compound N([C@H](C)C=1C=NC(C)=CC=1)C(=O)C(C=1)=CC(OC=2SC3=CC=CC=C3N=2)=CC=1C1=CC=C(C)C=N1 PRRPPWPGDIOZCX-LJQANCHMSA-N 0.000 claims description 2
- MHEWVNGVDZVUHK-UHFFFAOYSA-N 3-(1-hydroxy-2-morpholin-4-ylethyl)-5-(4-methylphenyl)-n-[(6-methylpyridin-3-yl)methyl]benzamide Chemical compound C1=CC(C)=CC=C1C1=CC(C(O)CN2CCOCC2)=CC(C(=O)NCC=2C=NC(C)=CC=2)=C1 MHEWVNGVDZVUHK-UHFFFAOYSA-N 0.000 claims description 2
- PSOFVBXHRBTMBN-OEPVSBQMSA-N 3-(1-hydroxy-3-methoxypropan-2-yl)oxy-5-(4-methylphenyl)-n-[(1r)-1-(6-methylpyridin-3-yl)ethyl]benzamide Chemical compound C=1C(OC(CO)COC)=CC(C(=O)N[C@H](C)C=2C=NC(C)=CC=2)=CC=1C1=CC=C(C)C=C1 PSOFVBXHRBTMBN-OEPVSBQMSA-N 0.000 claims description 2
- WOUUEQBJBVMSFA-FKSKYRLFSA-N 3-(1-hydroxy-3-methoxypropan-2-yl)oxy-5-(5-methylpyridin-2-yl)-n-[(1r)-1-(6-methylpyridin-3-yl)ethyl]benzamide Chemical compound C=1C(OC(CO)COC)=CC(C(=O)N[C@H](C)C=2C=NC(C)=CC=2)=CC=1C1=CC=C(C)C=N1 WOUUEQBJBVMSFA-FKSKYRLFSA-N 0.000 claims description 2
- ZFIPHACOYRAJGJ-QNSVNVJESA-N 3-(1-hydroxyethyl)-5-(4-methylphenyl)-n-[(1r)-1-(6-methylpyridin-3-yl)ethyl]benzamide Chemical compound C=1C(C(O)C)=CC(C(=O)N[C@H](C)C=2C=NC(C)=CC=2)=CC=1C1=CC=C(C)C=C1 ZFIPHACOYRAJGJ-QNSVNVJESA-N 0.000 claims description 2
- XRAKFHPWUWIXCC-TZHYSIJRSA-N 3-(1-hydroxyethyl)-5-(5-methylpyridin-2-yl)-n-[(1r)-1-(6-methylpyridin-3-yl)ethyl]benzamide Chemical compound C=1C(C(O)C)=CC(C(=O)N[C@H](C)C=2C=NC(C)=CC=2)=CC=1C1=CC=C(C)C=N1 XRAKFHPWUWIXCC-TZHYSIJRSA-N 0.000 claims description 2
- IOUUWXXIVONMPI-MUMRKEEXSA-N 3-(1-hydroxypropan-2-yloxy)-5-(4-methylphenyl)-n-[(1r)-1-(6-methylpyridin-3-yl)ethyl]benzamide Chemical compound C=1C(OC(CO)C)=CC(C(=O)N[C@H](C)C=2C=NC(C)=CC=2)=CC=1C1=CC=C(C)C=C1 IOUUWXXIVONMPI-MUMRKEEXSA-N 0.000 claims description 2
- LMGGUFSUEWTEQZ-QRWMCTBCSA-N 3-(1-hydroxypropan-2-yloxy)-5-(5-methylpyridin-2-yl)-n-[(1r)-1-(6-methylpyridin-3-yl)ethyl]benzamide Chemical compound C=1C(OC(CO)C)=CC(C(=O)N[C@H](C)C=2C=NC(C)=CC=2)=CC=1C1=CC=C(C)C=N1 LMGGUFSUEWTEQZ-QRWMCTBCSA-N 0.000 claims description 2
- UGIWXQMYHSFLQM-QFADGXAASA-N 3-(1-hydroxypropyl)-5-(4-methylphenyl)-n-[(1r)-1-(6-methylpyridin-3-yl)ethyl]benzamide Chemical compound C=1C(C(O)CC)=CC(C(=O)N[C@H](C)C=2C=NC(C)=CC=2)=CC=1C1=CC=C(C)C=C1 UGIWXQMYHSFLQM-QFADGXAASA-N 0.000 claims description 2
- SPKYTUIZLNBAOK-GFOWMXPYSA-N 3-(1-methoxypropan-2-yloxy)-5-(4-methylphenyl)-n-[(1r)-1-(6-methylpyridin-3-yl)ethyl]benzamide Chemical compound C=1C(OC(C)COC)=CC(C(=O)N[C@H](C)C=2C=NC(C)=CC=2)=CC=1C1=CC=C(C)C=C1 SPKYTUIZLNBAOK-GFOWMXPYSA-N 0.000 claims description 2
- HRINISPHVKSZEB-UHFFFAOYSA-N 3-(1-methoxypropan-2-yloxy)-5-(4-methylphenyl)-n-[(6-methylpyridin-3-yl)methyl]benzamide Chemical compound C=1C(OC(C)COC)=CC(C(=O)NCC=2C=NC(C)=CC=2)=CC=1C1=CC=C(C)C=C1 HRINISPHVKSZEB-UHFFFAOYSA-N 0.000 claims description 2
- NSFTVMDHZQNDRS-MUMRKEEXSA-N 3-(1-methoxypropan-2-yloxy)-5-(5-methylpyridin-2-yl)-n-[(1r)-1-(6-methylpyridin-3-yl)ethyl]benzamide Chemical compound C=1C(OC(C)COC)=CC(C(=O)N[C@H](C)C=2C=NC(C)=CC=2)=CC=1C1=CC=C(C)C=N1 NSFTVMDHZQNDRS-MUMRKEEXSA-N 0.000 claims description 2
- IXAPUUQGOICQMV-FKSKYRLFSA-N 3-(2,3-dihydroxypropoxy)-5-(4-methylphenyl)-n-[(1r)-1-(6-methylpyridin-3-yl)ethyl]benzamide Chemical compound N([C@H](C)C=1C=NC(C)=CC=1)C(=O)C(C=1)=CC(OCC(O)CO)=CC=1C1=CC=C(C)C=C1 IXAPUUQGOICQMV-FKSKYRLFSA-N 0.000 claims description 2
- OAKRDZWHGYIQNQ-UHFFFAOYSA-N 3-(2,5-dimethylpyrrolidine-1-carbonyl)-5-(4-methylphenyl)-n-[(6-methylpyridin-3-yl)methyl]benzamide Chemical compound CC1CCC(C)N1C(=O)C1=CC(C(=O)NCC=2C=NC(C)=CC=2)=CC(C=2C=CC(C)=CC=2)=C1 OAKRDZWHGYIQNQ-UHFFFAOYSA-N 0.000 claims description 2
- DMFWXWWOYZURGU-UHFFFAOYSA-N 3-(2-cyano-4-methylphenyl)-5-(1,2-dihydroxyethyl)benzoic acid Chemical compound N#CC1=CC(C)=CC=C1C1=CC(C(O)CO)=CC(C(O)=O)=C1 DMFWXWWOYZURGU-UHFFFAOYSA-N 0.000 claims description 2
- OFKQEDKKEPVYCK-TUHVGIAZSA-N 3-(2-cyano-4-methylphenyl)-5-(1,4-dioxan-2-ylmethoxy)-n-[(1r)-1-(6-methylpyridin-3-yl)ethyl]benzamide Chemical compound N([C@H](C)C=1C=NC(C)=CC=1)C(=O)C(C=C(C=1)C=2C(=CC(C)=CC=2)C#N)=CC=1OCC1COCCO1 OFKQEDKKEPVYCK-TUHVGIAZSA-N 0.000 claims description 2
- GYNYJFPVUQFVKV-OEPVSBQMSA-N 3-(2-cyano-4-methylphenyl)-5-(1-hydroxy-3-methoxypropan-2-yl)oxy-n-[(1r)-1-(6-methylpyridin-3-yl)ethyl]benzamide Chemical compound C=1C(OC(CO)COC)=CC(C(=O)N[C@H](C)C=2C=NC(C)=CC=2)=CC=1C1=CC=C(C)C=C1C#N GYNYJFPVUQFVKV-OEPVSBQMSA-N 0.000 claims description 2
- NAPVZCZEVSRKSV-QNSVNVJESA-N 3-(2-cyano-4-methylphenyl)-5-(1-hydroxyethyl)-n-[(1r)-1-(6-methylpyridin-3-yl)ethyl]benzamide Chemical compound C=1C(C(O)C)=CC(C(=O)N[C@H](C)C=2C=NC(C)=CC=2)=CC=1C1=CC=C(C)C=C1C#N NAPVZCZEVSRKSV-QNSVNVJESA-N 0.000 claims description 2
- WNLWDLLCOFYUOV-MUMRKEEXSA-N 3-(2-cyano-4-methylphenyl)-5-(1-hydroxypropan-2-yloxy)-n-[(1r)-1-(6-methylpyridin-3-yl)ethyl]benzamide Chemical compound C=1C(OC(CO)C)=CC(C(=O)N[C@H](C)C=2C=NC(C)=CC=2)=CC=1C1=CC=C(C)C=C1C#N WNLWDLLCOFYUOV-MUMRKEEXSA-N 0.000 claims description 2
- NPEKMIDJPRHBND-GFOWMXPYSA-N 3-(2-cyano-4-methylphenyl)-5-(1-methoxypropan-2-yloxy)-n-[(1r)-1-(6-methylpyridin-3-yl)ethyl]benzamide Chemical compound C=1C(OC(C)COC)=CC(C(=O)N[C@H](C)C=2C=NC(C)=CC=2)=CC=1C1=CC=C(C)C=C1C#N NPEKMIDJPRHBND-GFOWMXPYSA-N 0.000 claims description 2
- SBGMZVVRQWHOAN-GOSISDBHSA-N 3-(2-cyano-4-methylphenyl)-5-(2-hydroxyethoxy)-n-[(1r)-1-(6-methylpyridin-3-yl)ethyl]benzamide Chemical compound N([C@H](C)C=1C=NC(C)=CC=1)C(=O)C(C=1)=CC(OCCO)=CC=1C1=CC=C(C)C=C1C#N SBGMZVVRQWHOAN-GOSISDBHSA-N 0.000 claims description 2
- IWNNSJFGZXZJSQ-QGZVFWFLSA-N 3-(2-cyano-4-methylphenyl)-5-(2-methoxyethoxy)-n-[(1r)-1-(2-methylpyrimidin-5-yl)ethyl]benzamide Chemical compound C=1C(OCCOC)=CC(C(=O)N[C@H](C)C=2C=NC(C)=NC=2)=CC=1C1=CC=C(C)C=C1C#N IWNNSJFGZXZJSQ-QGZVFWFLSA-N 0.000 claims description 2
- FTBRMGCHAZHYQV-LJQANCHMSA-N 3-(2-cyano-4-methylphenyl)-5-(2-methoxyethoxy)-n-[(1r)-1-(6-methylpyridin-3-yl)ethyl]benzamide Chemical compound C=1C(OCCOC)=CC(C(=O)N[C@H](C)C=2C=NC(C)=CC=2)=CC=1C1=CC=C(C)C=C1C#N FTBRMGCHAZHYQV-LJQANCHMSA-N 0.000 claims description 2
- DIELSGCRXKURQF-UHFFFAOYSA-N 3-(2-cyano-4-methylphenyl)-5-(3-hydroxyazetidine-1-carbonyl)-n-[(6-methylpyridin-3-yl)methyl]benzamide Chemical compound N#CC1=CC(C)=CC=C1C1=CC(C(=O)NCC=2C=NC(C)=CC=2)=CC(C(=O)N2CC(O)C2)=C1 DIELSGCRXKURQF-UHFFFAOYSA-N 0.000 claims description 2
- PAMQNYNEUJDYAN-UHFFFAOYSA-N 3-(2-cyano-4-methylphenyl)-5-(3-hydroxyazetidine-1-carbonyl)-n-[[6-(trifluoromethyl)pyridin-3-yl]methyl]benzamide Chemical compound N#CC1=CC(C)=CC=C1C1=CC(C(=O)NCC=2C=NC(=CC=2)C(F)(F)F)=CC(C(=O)N2CC(O)C2)=C1 PAMQNYNEUJDYAN-UHFFFAOYSA-N 0.000 claims description 2
- MDVWELAQDPETEN-FCCBGLEOSA-N 3-(2-cyano-4-methylphenyl)-5-(4-hydroxyoxolan-3-yl)oxy-n-[(1r)-1-(2-methylpyrimidin-5-yl)ethyl]benzamide Chemical compound N([C@H](C)C=1C=NC(C)=NC=1)C(=O)C(C=C(C=1)C=2C(=CC(C)=CC=2)C#N)=CC=1OC1COCC1O MDVWELAQDPETEN-FCCBGLEOSA-N 0.000 claims description 2
- NQXZNFWECNNWHF-GTANCFNGSA-N 3-(2-cyano-4-methylphenyl)-5-(4-hydroxyoxolan-3-yl)oxy-n-[(1r)-1-(6-methylpyridin-3-yl)ethyl]benzamide Chemical compound N([C@H](C)C=1C=NC(C)=CC=1)C(=O)C(C=C(C=1)C=2C(=CC(C)=CC=2)C#N)=CC=1OC1COCC1O NQXZNFWECNNWHF-GTANCFNGSA-N 0.000 claims description 2
- NWWMCTBEBQFXHM-QGZVFWFLSA-N 3-(2-cyano-4-methylphenyl)-5-(hydroxymethyl)-n-[(1r)-1-(6-methylpyridin-3-yl)ethyl]benzamide Chemical compound N([C@H](C)C=1C=NC(C)=CC=1)C(=O)C(C=1)=CC(CO)=CC=1C1=CC=C(C)C=C1C#N NWWMCTBEBQFXHM-QGZVFWFLSA-N 0.000 claims description 2
- NGGMJOQRIJFRAT-UHFFFAOYSA-N 3-(2-cyano-4-methylphenyl)-5-(oxolan-2-ylmethoxy)benzoic acid Chemical compound N#CC1=CC(C)=CC=C1C1=CC(OCC2OCCC2)=CC(C(O)=O)=C1 NGGMJOQRIJFRAT-UHFFFAOYSA-N 0.000 claims description 2
- YFOICYMIEHHZEK-UHFFFAOYSA-N 3-(2-cyano-4-methylphenyl)-5-(oxolan-3-ylmethoxy)benzoic acid Chemical compound N#CC1=CC(C)=CC=C1C1=CC(OCC2COCC2)=CC(C(O)=O)=C1 YFOICYMIEHHZEK-UHFFFAOYSA-N 0.000 claims description 2
- HPADTRCSOGTHJL-YAOANENCSA-N 3-(2-cyano-4-methylphenyl)-5-[hydroxy(1,3-thiazol-2-yl)methyl]-n-[(1r)-1-(2-methylpyrimidin-5-yl)ethyl]benzamide Chemical compound N([C@H](C)C=1C=NC(C)=NC=1)C(=O)C(C=1)=CC(C(O)C=2SC=CN=2)=CC=1C1=CC=C(C)C=C1C#N HPADTRCSOGTHJL-YAOANENCSA-N 0.000 claims description 2
- RHFLHHJHOIUCIM-YDONVPIESA-N 3-(2-cyano-4-methylphenyl)-5-[hydroxy(1,3-thiazol-2-yl)methyl]-n-[(1r)-1-(6-methylpyridin-3-yl)ethyl]benzamide Chemical compound N([C@H](C)C=1C=NC(C)=CC=1)C(=O)C(C=1)=CC(C(O)C=2SC=CN=2)=CC=1C1=CC=C(C)C=C1C#N RHFLHHJHOIUCIM-YDONVPIESA-N 0.000 claims description 2
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-
2009
- 2009-02-27 CN CN201410266032.6A patent/CN104058999A/zh active Pending
- 2009-02-27 MX MX2010009561A patent/MX2010009561A/es active IP Right Grant
- 2009-02-27 CN CN200980111248.2A patent/CN101981003B/zh not_active Expired - Fee Related
- 2009-02-27 JP JP2010548731A patent/JP5539235B2/ja not_active Expired - Fee Related
- 2009-02-27 US US12/312,749 patent/US8946439B2/en not_active Expired - Fee Related
- 2009-02-27 ES ES09716825.6T patent/ES2557281T3/es active Active
- 2009-02-27 EP EP09716825.6A patent/EP2262766B1/en not_active Not-in-force
- 2009-02-27 CA CA2715835A patent/CA2715835C/en not_active Expired - Fee Related
- 2009-02-27 WO PCT/US2009/001249 patent/WO2009110985A2/en not_active Ceased
-
2013
- 2013-12-27 JP JP2013272289A patent/JP5916700B2/ja not_active Expired - Fee Related
-
2014
- 2014-12-14 US US14/569,720 patent/US20150266822A1/en not_active Abandoned
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