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 (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009058298A1 (en) * | 2007-10-31 | 2009-05-07 | Merck & Co., Inc. | P2x3, receptor antagonists for treatment of pain |
| WO2009110985A2 (en) * | 2008-02-29 | 2009-09-11 | Renovis, Inc. | Amide compounds, compositions and uses thereof |
| JP5535931B2 (ja) * | 2008-10-27 | 2014-07-02 | 武田薬品工業株式会社 | 二環性化合物 |
| KR101605061B1 (ko) | 2009-05-29 | 2016-03-21 | 라퀄리아 파마 인코포레이티드 | 칼슘 또는 나트륨 채널 차단제로서의 아릴 치환된 카복사미드 유도체 |
| JP6165733B2 (ja) | 2011-09-16 | 2017-07-19 | ノバルティス アーゲー | Ｎ−置換ヘテロシクリルカルボキサミド類 |
| WO2013072758A1 (en) * | 2011-11-15 | 2013-05-23 | Purdue Pharma L.P. | Pyrimidine diol amides as sodium channel blockers |
| JP6275690B2 (ja) * | 2012-04-05 | 2018-02-07 | シーエイチディーアイ ファウンデーション，インコーポレーテッド | キヌレニン−３−モノオキシゲナーゼインヒビターおよびその医薬組成物ならびにこれらの使用方法 |
| EP2774911A1 (de) * | 2013-03-06 | 2014-09-10 | LANXESS Deutschland GmbH | Verfahren zur Herstellung von Halogen-N,N-dimethylbenzylaminen |
| ES2688452T3 (es) | 2013-03-06 | 2018-11-02 | Lanxess Deutschland Gmbh | Procedimiento para la preparación de halo-N,N-dimetilbencilaminas |
| EP2970135B1 (en) | 2013-03-14 | 2018-07-18 | Epizyme, Inc. | Pyrazole derivatives as prmt1 inhibitors and uses thereof |
| CA2903394C (en) | 2013-03-14 | 2021-08-31 | Epizyme, Inc. | Arginine methyltransferase inhibitors and uses thereof |
| US9394258B2 (en) | 2013-03-14 | 2016-07-19 | 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 |
| JP2016514164A (ja) | 2013-03-14 | 2016-05-19 | エピザイム，インコーポレイティド | アルギニンメチルトランスフェラーゼ阻害剤としてのピラゾール誘導体およびその使用 |
| US9120757B2 (en) | 2013-03-14 | 2015-09-01 | Epizyme, Inc. | Arginine methyltransferase inhibitors and uses thereof |
| EP2970181B1 (en) | 2013-03-14 | 2017-06-07 | Epizyme, Inc. | Arginine methyltransferase inhibitors and uses thereof |
| EP3363434A1 (en) | 2013-03-14 | 2018-08-22 | Epizyme Inc | Arginine methyltransferase inhibitors and uses thereof |
| US9133189B2 (en) | 2013-03-14 | 2015-09-15 | Epizyme, Inc. | Arginine methyltransferase inhibitors and uses thereof |
| US9346802B2 (en) | 2013-03-15 | 2016-05-24 | Epizyme, Inc. | CARM1 inhibitors and uses thereof |
| WO2014144169A1 (en) | 2013-03-15 | 2014-09-18 | Epizyme, Inc. | Carm1 inhibitors and uses thereof |
| EP2970266B1 (en) | 2013-03-15 | 2018-01-31 | Epizyme, Inc. | 1-phenoxy-3-(alkylamino)-propan-2-ol derivatives as carm1 inhibitors and uses thereof |
| JP2016536350A (ja) | 2013-09-26 | 2016-11-24 | シーエイチディーアイ ファウンデーション，インコーポレーテッド | キヌレニン−３−モノオキシゲナーゼ阻害薬、医薬組成物、及びこれらの使用方法 |
| JP6449893B2 (ja) | 2013-09-26 | 2019-01-09 | シーエイチディーアイ ファウンデーション，インコーポレーテッド | キヌレニン−３−モノオキシゲナーゼ阻害薬、医薬組成物、及びこれらの使用方法 |
| JP6383418B2 (ja) * | 2013-11-27 | 2018-08-29 | ジェネンテック， インコーポレイテッド | 置換ベンズアミド及びその使用方法 |
| EP2905282A1 (en) * | 2014-02-05 | 2015-08-12 | AXXAM S.p.A. | Substituted thiazole or oxazole as P2X7 receptor antagonists |
| EP3140298A1 (en) | 2014-05-07 | 2017-03-15 | Pfizer Inc. | Tropomyosin-related kinase inhibitors |
| US20170280720A1 (en) * | 2014-09-17 | 2017-10-05 | Epizyme, Inc. | Arginine methyltransferase inhibitors and uses thereof |
| WO2016044641A2 (en) * | 2014-09-17 | 2016-03-24 | Epizyme, Inc. | Carm1 inhibitors and uses thereof |
| US10183937B2 (en) * | 2014-12-09 | 2019-01-22 | Bayer Aktiengesellschaft | 1,3-thiazol-2-yl substituted benzamides |
| CU24411B1 (es) | 2014-12-09 | 2019-05-03 | Bayer Ag | Compuesto derivado de benzamida sustituida con 1,3-tiazol-2-ilo útil para el tratamiento de trastornos neurogénicos |
| 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 |
| SG11202011010YA (en) * | 2018-05-15 | 2020-12-30 | Bayer Ag | 1,3-thiazol-2-yl substituted benzamides for the treatment of diseases associated with nerve fiber sensitization |
| 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 |
| 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 |
| MA56022A (fr) | 2019-05-31 | 2022-04-06 | Chiesi Farm Spa | Dérivés d'amino quinazoline servant d'inhibiteurs de p2x3 |
| KR102923602B1 (ko) | 2019-05-31 | 2026-02-06 | 키에시 파르마슈티시 엣스. 피. 에이. | P2x3 억제제로서 피리도피리미딘 유도체 |
| 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 |
| US20230192631A1 (en) * | 2020-04-16 | 2023-06-22 | Hoffmann-La Roche Inc. | 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 |
| CN116745284A (zh) | 2020-11-27 | 2023-09-12 | 奇斯药制品公司 | 作为p2x3抑制剂的酞嗪衍生物 |
| WO2022112490A1 (en) | 2020-11-27 | 2022-06-02 | Chiesi Farmaceutici S.P.A. | Amino quinazoline 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 |
| KR20260084522A (ko) * | 2024-11-29 | 2026-06-05 | 삼진제약주식회사 | 벤즈아미드 유도체 화합물을 포함하는 항체-약물 접합체 |
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 |
| EP1177188B1 (en) | 1999-05-12 | 2005-10-12 | 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 |
| AU2002247208A1 (en) * | 2001-03-05 | 2002-09-19 | 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 |
| EP1392643B1 (en) * | 2001-05-18 | 2005-09-14 | Abbott Laboratories | Trisubstituted-n- (1s)-1,2,3,4-tetrahydro-1-naphthalenyl] benzamides which inhibit p2x3 and p2x2/3 containing receptors |
| WO2008011131A2 (en) | 2006-07-21 | 2008-01-24 | Takeda Pharmaceutical Company Limited | Amide compounds |
| TW200304374A (en) | 2001-11-30 | 2003-10-01 | Smithkline Beecham Plc | Novel compounds |
| EP1503997A1 (en) | 2002-05-14 | 2005-02-09 | Axys Pharmaceuticals, Inc. | Cysteine protease inhibitors |
| AU2003242252A1 (en) | 2002-06-07 | 2003-12-22 | Kyowa Hakko Kogyo Co., Ltd. | Bicyclic pyrimidine derivatives |
| GB0225548D0 (en) | 2002-11-01 | 2002-12-11 | Glaxo Group Ltd | Compounds |
| US20060122184A1 (en) | 2002-12-05 | 2006-06-08 | Axys Pharmaceuticals, Inc. | Cyanomethyl derivatives as cysteine protease inhibitors |
| US20060100245A1 (en) | 2002-12-19 | 2006-05-11 | Neurogen Corporation | Substituted biphenyl-4-carboxylic acid arylamide analogues |
| WO2005032471A2 (en) | 2003-10-03 | 2005-04-14 | Merck & Co., Inc. | Benzylether and benzylamino beta-secretase inhibitors for the treatment of alzheimer's disease |
| JP2007517781A (ja) | 2003-12-19 | 2007-07-05 | メルク エンド カムパニー インコーポレーテッド | アルツハイマー病治療用のフェニルアミドおよびピリジルアミド系β−セクレターゼ阻害薬 |
| WO2005073193A1 (en) * | 2004-01-23 | 2005-08-11 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| JP2007537257A (ja) * | 2004-05-13 | 2007-12-20 | メルク エンド カムパニー インコーポレーテッド | アルツハイマー病の治療用ベータセクレターゼ阻害剤として有用なフェニルカルボキサミド化合物 |
| TW200640877A (en) | 2005-04-28 | 2006-12-01 | Actelion Pharmaceuticals Ltd | Pyrimidine derivatives |
| JP5198256B2 (ja) | 2005-05-04 | 2013-05-15 | エボテク エージー | 縮合複素環式化合物、並びにそれらの組成物及び使用 |
| EP1919861A2 (de) | 2005-08-11 | 2008-05-14 | Boehringer Ingelheim International GmbH | Verbindungen zur behandlung der alzheimer erkrankung |
| CA2618474A1 (en) * | 2005-08-11 | 2007-02-15 | Boehringer Ingelheim International Gmbh | Compounds for treating alzheimer's disease |
| MX2008002014A (es) * | 2005-08-15 | 2008-03-27 | Hoffmann La Roche | Derivados de piperidina y piperazina como antagonistas de p2x3. |
| ES2612890T3 (es) | 2005-09-01 | 2017-05-19 | F. Hoffmann-La Roche Ag | Diaminopirimidinas como moduladores de P2X3 y P2X2/3 |
| ES2562056T3 (es) | 2005-09-01 | 2016-03-02 | F. Hoffmann-La Roche Ag | Diaminopirimidinas como moduladores P2X3 y P2X2/3 |
| SI1924264T1 (sl) | 2005-09-01 | 2013-12-31 | F. Hoffmann-La Roche Ag | Diaminopirimidini kot modulatorji p2x3 in p2x2/3 |
| AU2006286576B2 (en) | 2005-09-01 | 2012-06-14 | F. Hoffmann-La Roche Ag | Diaminopyrimidines as P2X3 and P3X2/3 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 |
| ES2596706T3 (es) | 2006-06-29 | 2017-01-11 | F. Hoffmann-La Roche Ag | Arilamidas con sustitución de tetrazol |
| WO2008023159A1 (en) | 2006-08-24 | 2008-02-28 | 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. |
| JP5084839B2 (ja) * | 2006-11-09 | 2012-11-28 | エフ．ホフマン−ラ ロシュ アーゲー | チアゾール及びオキサゾール置換アリールアミド |
| WO2008119773A1 (en) | 2007-03-30 | 2008-10-09 | Medivir Ab | Amide derivatives as inhibitors of aspartyl proteases |
| US8076345B2 (en) | 2007-04-17 | 2011-12-13 | Evotec Ag | 2-cyanophenyl-7,8-dihydro-5H-pyrido[4,3-d]pyrimidine compounds, compositions and uses thereof |
| WO2009058298A1 (en) | 2007-10-31 | 2009-05-07 | Merck & Co., Inc. | P2x3, receptor antagonists for treatment of pain |
| EP2215048B1 (en) | 2007-10-31 | 2015-10-28 | Merck Sharp & Dohme Corp. | P2x3 receptor antagonists for treatment of pain |
| US7989454B2 (en) * | 2007-12-17 | 2011-08-02 | Hoffmann-La Roche Inc. | Leukotriene B4 inhibitors |
| KR101405746B1 (ko) | 2007-12-17 | 2014-06-10 | 에프. 호프만-라 로슈 아게 | 트리아졸 치환된 아릴아미드 유도체 및 ｐ２ｘ３ 및/또는 ｐ２ｘ２／３ 퓨린성 수용체 길항제로서의 용도 |
| DK2234976T3 (da) | 2007-12-17 | 2013-06-24 | Hoffmann La Roche | Nye pyrazol-substituerede arylamider |
| BR122019016794B8 (pt) | 2007-12-17 | 2021-07-27 | Hoffmann La Roche | derivados de arilamida substituídos por tetrazol, composição farmacêutica que os compreende e seu uso no tratamento de uma condição inflamatória e/ou autoimune |
| ES2570628T3 (es) | 2007-12-17 | 2016-05-19 | Hoffmann La Roche | Nuevas arilamidas con sustitución imidazol |
| WO2009110985A2 (en) * | 2008-02-29 | 2009-09-11 | Renovis, Inc. | Amide compounds, compositions and uses thereof |
| US20110237578A1 (en) * | 2008-09-18 | 2011-09-29 | Zhi-Liang Wei | Amide compounds, compositions and uses thereof |
| CA2741666C (en) | 2008-10-31 | 2017-04-11 | Merck Sharp & Dohme Corp. | P2x3, receptor antagonists for treatment of pain |
| BRPI0922645A2 (pt) | 2008-12-16 | 2019-09-24 | Hoffmann La Roche | "arilamidas tiadiazol substituídas". |
| US8946231B2 (en) | 2009-03-23 | 2015-02-03 | Merck Sharp & Dohme Corp. | P2X3, receptor antagonists for treatment of pain |
| JP2012521429A (ja) | 2009-03-23 | 2012-09-13 | メルク・シャープ・エンド・ドーム・コーポレイション | 疼痛治療用のｐ２ｘ３受容体アンタゴニスト |
| WO2010111058A1 (en) | 2009-03-23 | 2010-09-30 | 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 |
| EP2445868B1 (en) | 2009-06-22 | 2013-12-18 | F.Hoffmann-La Roche Ag | Biphenyl amides useful as p2x3 and/or p2x2/3 receptors modulators |
| CA2754654A1 (en) | 2009-06-22 | 2010-12-29 | F. Hoffmann-La Roche Ag | Novel oxazolone and pyrrolidinone-substituted arylamides |
-
2009
- 2009-02-27 WO PCT/US2009/001249 patent/WO2009110985A2/en not_active Ceased
- 2009-02-27 CN CN200980111248.2A patent/CN101981003B/zh not_active Expired - Fee Related
- 2009-02-27 CA CA2715835A patent/CA2715835C/en not_active Expired - Fee Related
- 2009-02-27 EP EP09716825.6A patent/EP2262766B1/en not_active Not-in-force
- 2009-02-27 CN CN201410266032.6A patent/CN104058999A/zh active Pending
- 2009-02-27 US US12/312,749 patent/US8946439B2/en not_active Expired - Fee Related
- 2009-02-27 MX MX2010009561A patent/MX2010009561A/es active IP Right Grant
- 2009-02-27 JP JP2010548731A patent/JP5539235B2/ja not_active Expired - Fee Related
- 2009-02-27 ES ES09716825.6T patent/ES2557281T3/es active Active
-
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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