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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Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011502148A (ja) * | 2007-10-31 | 2011-01-20 | メルク・シャープ・エンド・ドーム・コーポレイション | 疼痛の治療用としてのｐ２ｘ３受容体アンタゴニスト |
| CA2715835C (en) * | 2008-02-29 | 2017-03-21 | Renovis, Inc. | Amide compounds, compositions and uses thereof |
| WO2010050445A1 (ja) * | 2008-10-27 | 2010-05-06 | 武田薬品工業株式会社 | 二環性化合物 |
| CN105254557A (zh) * | 2009-05-29 | 2016-01-20 | 拉夸里亚创药株式会社 | 作为钙或钠通道阻滞剂的芳基取代羧酰胺衍生物 |
| ES2882807T3 (es) | 2011-09-16 | 2021-12-02 | Novartis Ag | Heterociclil carboxamidas N-sustituidas |
| US9133131B2 (en) | 2011-11-15 | 2015-09-15 | Purdue Pharma L.P. | Pyrimidine diol amides as sodium channel blockers |
| KR20150000882A (ko) * | 2012-04-05 | 2015-01-05 | 씨에이치디아이 파운데이션, 인코포레이티드 | 키뉴레닌-3-모노산소첨가효소 억제제들, 약학 조성물들 및 이의 사용 방법 |
| EP2774911A1 (de) * | 2013-03-06 | 2014-09-10 | LANXESS Deutschland GmbH | Verfahren zur Herstellung von Halogen-N,N-dimethylbenzylaminen |
| WO2014135508A1 (de) * | 2013-03-06 | 2014-09-12 | Lanxess Deutschland Gmbh | Verfahren zur herstellung von halogen-n,n-dimethylbenzylaminen |
| WO2014153100A2 (en) | 2013-03-14 | 2014-09-25 | Epizyme, Inc. | Arginine methyltransferase inhibitors and uses thereof |
| US9765035B2 (en) | 2013-03-14 | 2017-09-19 | Epizyme, Inc. | Arginine methyltransferase inhibitors and uses thereof |
| WO2014153172A1 (en) | 2013-03-14 | 2014-09-25 | Epizyme, Inc. | Pyrazole derivatives as prmt1 inhibitors and uses thereof |
| EP2970135B1 (en) | 2013-03-14 | 2018-07-18 | Epizyme, Inc. | Pyrazole derivatives as prmt1 inhibitors and uses thereof |
| WO2014153208A1 (en) | 2013-03-14 | 2014-09-25 | Epizyme, Inc. | Arginine methyltransferase inhibitors and uses thereof |
| US9120757B2 (en) | 2013-03-14 | 2015-09-01 | Epizyme, Inc. | Arginine methyltransferase inhibitors and uses thereof |
| WO2014153214A1 (en) | 2013-03-14 | 2014-09-25 | Epizyme, Inc. | Arginine methyl transferase inhibtors and uses thereof |
| EP2970137A1 (en) | 2013-03-14 | 2016-01-20 | Epizyme, Inc. | Pyrazole derivatives as arginine methyltransferase inhibitors and uses thereof |
| KR102028793B1 (ko) | 2013-03-14 | 2019-10-07 | 에피자임, 인코포레이티드 | 아르기닌 메틸기 전이효소 억제제 및 이의 용도 |
| CA2903813C (en) | 2013-03-15 | 2023-08-29 | Epizyme, Inc. | Carm1 inhibitors and uses thereof |
| WO2014144455A1 (en) | 2013-03-15 | 2014-09-18 | Epizyme, Inc. | 1 -phenoxy-3-(alkylamino)-propan-2-ol derivatives as carm1 inhibitors and uses thereof |
| US9346802B2 (en) | 2013-03-15 | 2016-05-24 | Epizyme, Inc. | CARM1 inhibitors and uses thereof |
| ES2754473T3 (es) | 2013-09-26 | 2020-04-17 | Chdi Foundation Inc | Inhibidores de quinurenina-3-monooxigenasa, composiciones farmacéuticas, y método de uso de los mismos |
| EP3049077A4 (en) | 2013-09-26 | 2017-02-15 | CHDI Foundation, Inc. | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| CR20160296A (es) * | 2013-11-27 | 2016-09-20 | Genentech Inc | Benzamidas sustituidas y métodos para usarlas |
| EP2905282A1 (en) * | 2014-02-05 | 2015-08-12 | AXXAM S.p.A. | Substituted thiazole or oxazole as P2X7 receptor antagonists |
| WO2015170218A1 (en) | 2014-05-07 | 2015-11-12 | Pfizer Inc. | Tropomyosin-related kinase inhibitors |
| WO2016044641A2 (en) * | 2014-09-17 | 2016-03-24 | Epizyme, Inc. | Carm1 inhibitors and uses thereof |
| US20170280720A1 (en) * | 2014-09-17 | 2017-10-05 | Epizyme, Inc. | Arginine methyltransferase inhibitors and uses thereof |
| EP3230281B1 (en) | 2014-12-09 | 2021-05-26 | Bayer Aktiengesellschaft | 1,3-thiazol-2-yl substituted benzamides |
| US10183937B2 (en) * | 2014-12-09 | 2019-01-22 | Bayer Aktiengesellschaft | 1,3-thiazol-2-yl substituted benzamides |
| WO2017112576A1 (en) * | 2015-12-21 | 2017-06-29 | Dow Global Technologies Llc | Methods for external base-free suzuki couplings |
| CN106349153B (zh) * | 2016-08-25 | 2019-03-05 | 西安天一生物技术股份有限公司 | 2-甲基-5-乙烯基吡啶合成方法 |
| RU2679892C1 (ru) * | 2017-11-01 | 2019-02-14 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Пермская государственная фармацевтическая академия" Министерства здравоохранения Российской Федерации (ФГБОУ ВО ПГФА Минздрава России) | 4-метилфениламид n-бензоил-5-бром антраниловой кислоты, проявляющий противовоспалительную активность |
| 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 |
| EA202092678A1 (ru) * | 2018-05-15 | 2021-04-12 | Байер Акциенгезельшафт | 1,3-тиазол-2-ил-замещенные бензамиды для лечения заболеваний, ассоциированных с сенситизацией нервных волокон |
| US10844044B2 (en) | 2018-06-14 | 2020-11-24 | Vanderbilt University | WDR5 inhibitors and modulators |
| US10807959B2 (en) * | 2018-08-16 | 2020-10-20 | Vanderbilt University | WDR5-MLL1 inhibitors and modulators |
| US12186307B2 (en) | 2019-02-13 | 2025-01-07 | Yale University | Methods of treating epilepsy |
| JP7797204B2 (ja) | 2019-05-31 | 2026-01-13 | キエシ・フアルマチエウテイチ・ソチエタ・ペル・アチオニ | Ｐ２ｘ３阻害剤としてのピリドピリミジン誘導体 |
| CA3139018A1 (en) | 2019-05-31 | 2020-12-03 | Chiesi Farmaceutici S.P.A. | Amino quinazoline derivatives as p2x3 inhibitors |
| JP2022116370A (ja) * | 2019-06-13 | 2022-08-10 | アグロカネショウ株式会社 | 新規な１－ベンジルアミン誘導体及びこれを有効成分とする農園芸用薬剤 |
| EP3757103A1 (en) * | 2019-06-27 | 2020-12-30 | Bayer AG | Analogues of 3-(5-methyl-1,3-thiazol-2-yl)-n-{(1r)-1-[2-(trifluoro-methyl)pyrimidin-5-yl]ethyl}benzamide for the treatment of neurogenic diseases |
| WO2021209473A1 (en) * | 2020-04-16 | 2021-10-21 | F. Hoffmann-La Roche Ag | Biphenyl derivatives |
| WO2021238834A1 (zh) * | 2020-05-25 | 2021-12-02 | 中国医药研究开发中心有限公司 | 芳甲酰胺类化合物及其制备方法和医药用途 |
| WO2022112490A1 (en) | 2020-11-27 | 2022-06-02 | Chiesi Farmaceutici S.P.A. | Amino quinazoline derivatives as p2x3 inhibitors |
| CA3196335A1 (en) | 2020-11-27 | 2022-06-02 | Chiesi Farmaceutici S.P.A. | Phthalazine derivatives as p2x3 inhibitors |
| JP2023550830A (ja) | 2020-11-27 | 2023-12-05 | キエシ・フアルマチエウテイチ・ソチエタ・ペル・アチオニ | Ｐ２ｘ３阻害剤としての（アザ）キノリン４－アミン誘導体 |
| AU2024282595A1 (en) * | 2023-05-30 | 2026-01-22 | Samjin Pharmaceutical Co., Ltd. | Novel benzamide derivative compound and pharmaceutical composition comprising same |
Family Cites Families (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2731469A (en) | 1953-10-23 | 1956-01-17 | Searle & Co | N-dialkylaminoalkyl derivatives of diarylisonicotinamides |
| US3424760A (en) | 1966-03-07 | 1969-01-28 | Robins Co Inc A H | 3-ureidopyrrolidines |
| US3424761A (en) | 1966-03-07 | 1969-01-28 | Robins Co Inc A H | 3-ureidopyrrolidines |
| DE2502588A1 (de) | 1975-01-23 | 1976-07-29 | Troponwerke Dinklage & Co | Basisch substituierte derivate des 7-amino-2-chinolons, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| CA1316920C (en) | 1987-06-12 | 1993-04-27 | Terry N. Myers | Hindered amine light stabilizers containing aromatic carboxy groups and derivatives |
| JPS6413083A (en) | 1987-07-07 | 1989-01-17 | Akishiro Nakamura | Streptonigrin derivative and medicinal composition |
| US4916145A (en) | 1987-07-10 | 1990-04-10 | Hoffmann-La Roche Inc. | Substituted n-[(pyridyl)alkyl]aryl-carboxamide |
| GB9600063D0 (en) | 1996-01-03 | 1996-03-06 | Fujisawa Pharmaceutical Co | Guaridine derivatives |
| US6037324A (en) | 1996-01-04 | 2000-03-14 | Leukosite, Inc. | Inhibitors of MAdCAM-1-mediated interactions and methods of use therefor |
| AU778393B2 (en) | 1999-05-12 | 2004-12-02 | Ortho-Mcneil Pharmaceutical, Inc. | Pyrazole carboxamides useful for the treatment of obesity and other disorders |
| US6531478B2 (en) | 2000-02-24 | 2003-03-11 | Cheryl P. Kordik | Amino pyrazole derivatives useful for the treatment of obesity and other disorders |
| AU2001294557A1 (en) | 2000-09-11 | 2002-03-26 | Merck And Co., Inc. | Thrombin inhibitors |
| WO2002070469A2 (en) | 2001-03-05 | 2002-09-12 | Icos Corporation | Selective pde3b inhibitors and use of the same in therapy |
| WO2002088079A2 (en) | 2001-05-01 | 2002-11-07 | Bristol-Myers Squibb Company | Dual inhibitors of pde 7 and pde 4 |
| DK1392643T3 (da) * | 2001-05-18 | 2006-01-30 | Abbott Lab | (1S)-1,2,3,4-tetrahydro-1-naphthalenylbenzamider, der er trisubstituerede ved N, og som inhiberer receptorer indeholdende P2X3 og P2X2/3 |
| WO2008011131A2 (en) | 2006-07-21 | 2008-01-24 | Takeda Pharmaceutical Company Limited | Amide compounds |
| AR037460A1 (es) | 2001-11-30 | 2004-11-10 | Smithkline Beecham Plc | Compuesto de hidroxietileno, composicion farmaceutica que lo comprende, uso del mismo para la fabricacion de un medicamento y procedimiento para su preparacion |
| US20050288336A1 (en) | 2002-05-14 | 2005-12-29 | Axys Pharmaceuticals, Inc. | Cysteine protease inhibitors |
| JPWO2003104230A1 (ja) | 2002-06-07 | 2005-10-06 | 協和醗酵工業株式会社 | 二環性ピリミジン誘導体 |
| GB0225548D0 (en) * | 2002-11-01 | 2002-12-11 | Glaxo Group Ltd | Compounds |
| WO2004052921A1 (en) | 2002-12-05 | 2004-06-24 | Axys Pharmaceuticals, Inc. | Cyanomethyl derivatives as cysteine protease inhibitors |
| WO2004056774A2 (en) | 2002-12-19 | 2004-07-08 | Neurogen Corporation | Substituted biphenyl-4-carboxylic acid arylamide analogues as capsaicin receptor modulators |
| EP1673078B1 (en) | 2003-10-03 | 2008-05-28 | Merck & Co., Inc. | Benzylether and benzylamino beta-secretase inhibitors for the treatment of alzheimer's disease |
| US7550481B2 (en) | 2003-12-19 | 2009-06-23 | Merck & Co., Inc. | Phenylamide and pyridylamide beta-secretase inhibitors for the treatment of Alzheimer's disease |
| WO2005073193A1 (en) * | 2004-01-23 | 2005-08-11 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| EP1756040A4 (en) * | 2004-05-13 | 2008-04-30 | Merck & Co Inc | ALS-SEKRETASE INHIBITORS FOR THE TREATMENT OF ALZHEIMER DISEASE, PHENYL ACETIC ACID AMID COMPOUNDS SUITABLE |
| TW200640877A (en) | 2005-04-28 | 2006-12-01 | Actelion Pharmaceuticals Ltd | Pyrimidine derivatives |
| MX2007013595A (es) | 2005-05-04 | 2008-01-24 | Renovis Inc | Compuestos heterociclicos fusionados y composiciones y usos de estos. |
| US20100168070A1 (en) | 2005-08-11 | 2010-07-01 | Niklas Heine | Compounds for the treatment of alzheimer's disease |
| US20100144681A1 (en) | 2005-08-11 | 2010-06-10 | Klaus Fuchs | Compounds for the treatment of alzheimer's disease |
| MX2008002014A (es) * | 2005-08-15 | 2008-03-27 | Hoffmann La Roche | Derivados de piperidina y piperazina como antagonistas de p2x3. |
| CN101300012B (zh) | 2005-09-01 | 2011-09-14 | 弗·哈夫曼-拉罗切有限公司 | 作为p2x3和p2x2/3调节剂的二氨基嘧啶类化合物在制备治疗呼吸系统疾病的药物中的应用 |
| ES2562056T3 (es) | 2005-09-01 | 2016-03-02 | F. Hoffmann-La Roche Ag | Diaminopirimidinas como moduladores P2X3 y P2X2/3 |
| MX2008002731A (es) | 2005-09-01 | 2008-03-26 | Hoffmann La Roche | Diaminopirimidinas como moduladores de p2x3 y p3x2/3. |
| EP1924564B1 (en) | 2005-09-01 | 2016-11-09 | F.Hoffmann-La Roche Ag | Diaminopyrimidines as p2x3 and p2x2/3 modulators |
| US7838676B2 (en) | 2005-11-21 | 2010-11-23 | Amgen Inc. | Beta-secretase modulators and methods of use |
| CA2652307A1 (en) | 2006-04-10 | 2007-10-18 | Painceptor Pharma Corporation | Compositions and methods for modulating gated ion channels |
| EP2038264B1 (en) | 2006-06-29 | 2016-10-26 | F.Hoffmann-La Roche Ag | Tetrazole-substituted arylamides |
| AU2007287428B2 (en) | 2006-08-24 | 2011-08-11 | Astrazeneca Ab | Morpholino pyrimidine derivatives useful in the treatment of proliferative disorders |
| CL2007002920A1 (es) | 2006-10-13 | 2008-06-06 | Actelion Pharmaceuticals Ltd | Compuestos derivados de 2-aminocarbonilpiridina; composicion farmaceutica; y uso para el tratamiento de trastornos vasculares oclusivos. |
| CN101528717B (zh) | 2006-11-09 | 2013-04-24 | 弗·哈夫曼-拉罗切有限公司 | 噻唑和*唑-取代的芳基酰胺类化合物 |
| WO2008119773A1 (en) | 2007-03-30 | 2008-10-09 | Medivir Ab | Amide derivatives as inhibitors of aspartyl proteases |
| PT2139334E (pt) | 2007-04-17 | 2013-10-02 | Evotec Ag | Compostos heterocíclicos fusionados de 2-cianofenilo, e composições e utilizações dos mesmos |
| CA2703915C (en) | 2007-10-31 | 2015-02-24 | Merck Sharp & Dohme Corp. | P2x3 receptor antagonists for treatment of pain |
| JP2011502148A (ja) * | 2007-10-31 | 2011-01-20 | メルク・シャープ・エンド・ドーム・コーポレイション | 疼痛の治療用としてのｐ２ｘ３受容体アンタゴニスト |
| US7989454B2 (en) * | 2007-12-17 | 2011-08-02 | Hoffmann-La Roche Inc. | Leukotriene B4 inhibitors |
| DK2234976T3 (da) | 2007-12-17 | 2013-06-24 | Hoffmann La Roche | Nye pyrazol-substituerede arylamider |
| CA2708791C (en) | 2007-12-17 | 2016-06-21 | F. Hoffmann-La Roche Ag | Imidazole-substituted arylamides and uses thereof as p2x receptor antagonists |
| ES2541662T3 (es) | 2007-12-17 | 2015-07-23 | F. Hoffmann-La Roche Ag | Derivados arilamida sustituidos con triazol y utilización de los mismos como antagonistas de receptores purinérgicos P2X3 y/o P2X2/3 |
| WO2009077371A1 (en) | 2007-12-17 | 2009-06-25 | F. Hoffmann-La Roche Ag | Tetrazole-substituted arylamide derivatives and their use as p2x3 and/or p2x2/3 purinergic receptor antagonists |
| CA2715835C (en) * | 2008-02-29 | 2017-03-21 | Renovis, Inc. | Amide compounds, compositions and uses thereof |
| JP5608655B2 (ja) * | 2008-09-18 | 2014-10-15 | エヴォテック アーゲー | Ｐ２ｘ３受容体活性のモジュレーター |
| MX2011004570A (es) | 2008-10-31 | 2011-06-17 | Merck Sharp & Dohme | Antagonistas del receptor p2x3 para el tratamiento del dolor. |
| WO2010069794A1 (en) | 2008-12-16 | 2010-06-24 | F. Hoffmann-La Roche Ag | Thiadiazole-substituted arylamides |
| WO2010111059A1 (en) | 2009-03-23 | 2010-09-30 | Merck Sharp & Dohme Corp. | P2x3 receptor antagonists for treatment of pain |
| US8569512B2 (en) | 2009-03-23 | 2013-10-29 | Merck Sharp & Dohme Corp. | P2X3 receptor antagonists for treatment of pain |
| AU2010229142A1 (en) | 2009-03-23 | 2011-10-13 | Merck Sharp & Dohme Corp. | P2X3, receptor antagonists for treatment of pain |
| US20100320456A1 (en) * | 2009-06-19 | 2010-12-23 | Epv Solar, Inc. | Method for Fabricating a Doped and/or Alloyed Semiconductor |
| CN102438989B (zh) | 2009-06-22 | 2015-05-27 | 霍夫曼-拉罗奇有限公司 | 噁唑酮和吡咯烷酮取代的芳基酰胺 |
| SG177308A1 (en) | 2009-06-22 | 2012-02-28 | Hoffmann La Roche | Novel biphenyl and phenyl-pyridine amides |
-
2009
- 2009-02-27 CA CA2715835A patent/CA2715835C/en not_active Expired - Fee Related
- 2009-02-27 MX MX2010009561A patent/MX2010009561A/es active IP Right Grant
- 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 JP JP2010548731A patent/JP5539235B2/ja not_active Expired - Fee Related
- 2009-02-27 CN CN201410266032.6A patent/CN104058999A/zh active Pending
- 2009-02-27 CN CN200980111248.2A patent/CN101981003B/zh 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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