JP2013525344A5 - - Google Patents
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- Publication number
- JP2013525344A5 JP2013525344A5 JP2013506071A JP2013506071A JP2013525344A5 JP 2013525344 A5 JP2013525344 A5 JP 2013525344A5 JP 2013506071 A JP2013506071 A JP 2013506071A JP 2013506071 A JP2013506071 A JP 2013506071A JP 2013525344 A5 JP2013525344 A5 JP 2013525344A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- piperidin
- chloro
- amino
- methoxybenzamide
- 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 46
- 150000003839 salts Chemical class 0.000 claims description 29
- 239000000126 substance Substances 0.000 claims description 29
- 239000000018 receptor agonist Substances 0.000 claims description 20
- 229940044601 receptor agonist Drugs 0.000 claims description 20
- 201000006549 dyspepsia Diseases 0.000 claims description 12
- -1 C1-C4 alkylsulfonyl halide Chemical class 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
- 208000028698 Cognitive impairment Diseases 0.000 claims description 4
- 206010010774 Constipation Diseases 0.000 claims description 4
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 4
- 206010019280 Heart failures Diseases 0.000 claims description 4
- 208000019695 Migraine disease Diseases 0.000 claims description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
- 208000012902 Nervous system disease Diseases 0.000 claims description 4
- 208000025966 Neurological disease Diseases 0.000 claims description 4
- 208000002193 Pain Diseases 0.000 claims description 4
- 206010047700 Vomiting Diseases 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 206010003119 arrhythmia Diseases 0.000 claims description 4
- 208000015114 central nervous system disease Diseases 0.000 claims description 4
- 208000010877 cognitive disease Diseases 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 230000030135 gastric motility Effects 0.000 claims description 4
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 206010025482 malaise Diseases 0.000 claims description 4
- 206010027599 migraine Diseases 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 208000000689 peptic esophagitis Diseases 0.000 claims description 4
- 201000002859 sleep apnea Diseases 0.000 claims description 4
- 230000008673 vomiting Effects 0.000 claims description 4
- 206010030216 Oesophagitis Diseases 0.000 claims description 3
- 238000010976 amide bond formation reaction Methods 0.000 claims description 3
- 208000010643 digestive system disease Diseases 0.000 claims description 3
- 208000006881 esophagitis Diseases 0.000 claims description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 3
- 208000018685 gastrointestinal system disease Diseases 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 230000001939 inductive effect Effects 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 5
- 239000003638 chemical reducing agent Substances 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 125000006242 amine protecting group Chemical group 0.000 claims 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims 3
- HIOGWWRSBGQSBU-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-n-[[1-(pyridin-3-ylmethyl)piperidin-4-yl]methyl]benzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NCC1CCN(CC=2C=NC=CC=2)CC1 HIOGWWRSBGQSBU-UHFFFAOYSA-N 0.000 claims 2
- HJDQPKAAQATROQ-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-n-[[1-[(1-methylindol-3-yl)methyl]piperidin-4-yl]methyl]benzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NCC1CCN(CC=2C3=CC=CC=C3N(C)C=2)CC1 HJDQPKAAQATROQ-UHFFFAOYSA-N 0.000 claims 2
- WMGVNRQNHSLGDW-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-n-[[1-[(1-methylindol-3-yl)methyl]piperidin-4-yl]methyl]benzamide;hydrochloride Chemical compound Cl.COC1=CC(N)=C(Cl)C=C1C(=O)NCC1CCN(CC=2C3=CC=CC=C3N(C)C=2)CC1 WMGVNRQNHSLGDW-UHFFFAOYSA-N 0.000 claims 2
- SLPBYWRCHKGLEO-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-n-[[1-[(1-methylpyrrol-2-yl)methyl]piperidin-4-yl]methyl]benzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NCC1CCN(CC=2N(C=CC=2)C)CC1 SLPBYWRCHKGLEO-UHFFFAOYSA-N 0.000 claims 2
- PWNAZRVHQRXONZ-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-n-[[1-[3-(1,2,4-triazol-1-yl)propyl]piperidin-4-yl]methyl]benzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NCC1CCN(CCCN2N=CN=C2)CC1 PWNAZRVHQRXONZ-UHFFFAOYSA-N 0.000 claims 2
- UADHNYVTEMZKEG-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-n-[[1-[3-(2-methylimidazol-1-yl)propyl]piperidin-4-yl]methyl]benzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NCC1CCN(CCCN2C(=NC=C2)C)CC1 UADHNYVTEMZKEG-UHFFFAOYSA-N 0.000 claims 2
- DOHQLPJVYWFFDT-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-n-[[1-[3-(tetrazol-1-yl)propyl]piperidin-4-yl]methyl]benzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NCC1CCN(CCCN2N=NN=C2)CC1 DOHQLPJVYWFFDT-UHFFFAOYSA-N 0.000 claims 2
- YUWFZRKFVMTIQA-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-n-[[1-[3-(tetrazol-1-yl)propyl]piperidin-4-yl]methyl]benzamide;hydrochloride Chemical compound Cl.COC1=CC(N)=C(Cl)C=C1C(=O)NCC1CCN(CCCN2N=NN=C2)CC1 YUWFZRKFVMTIQA-UHFFFAOYSA-N 0.000 claims 2
- AULLTYAISZREAX-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-n-[[1-[3-(triazol-1-yl)propyl]piperidin-4-yl]methyl]benzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NCC1CCN(CCCN2N=NC=C2)CC1 AULLTYAISZREAX-UHFFFAOYSA-N 0.000 claims 2
- JPPDVIYHBBLDDI-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-n-[[1-[3-(triazol-1-yl)propyl]piperidin-4-yl]methyl]benzamide;hydrochloride Chemical compound Cl.COC1=CC(N)=C(Cl)C=C1C(=O)NCC1CCN(CCCN2N=NC=C2)CC1 JPPDVIYHBBLDDI-UHFFFAOYSA-N 0.000 claims 2
- LFVXLLHJVXPAOI-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-n-[[1-[3-(triazol-2-yl)propyl]piperidin-4-yl]methyl]benzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NCC1CCN(CCCN2N=CC=N2)CC1 LFVXLLHJVXPAOI-UHFFFAOYSA-N 0.000 claims 2
- XBHOSNAFUQCYOB-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-n-[[1-[5-(triazol-1-yl)pentyl]piperidin-4-yl]methyl]benzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NCC1CCN(CCCCCN2N=NC=C2)CC1 XBHOSNAFUQCYOB-UHFFFAOYSA-N 0.000 claims 2
- MMQUYCLQMIWDMD-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-n-[[1-[5-(triazol-1-yl)pentyl]piperidin-4-yl]methyl]benzamide;hydrochloride Chemical compound Cl.COC1=CC(N)=C(Cl)C=C1C(=O)NCC1CCN(CCCCCN2N=NC=C2)CC1 MMQUYCLQMIWDMD-UHFFFAOYSA-N 0.000 claims 2
- JANPLEIOOUTRAY-UHFFFAOYSA-N 4-amino-5-chloro-n-[[1-(1h-imidazol-2-ylmethyl)piperidin-4-yl]methyl]-2-methoxybenzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NCC1CCN(CC=2NC=CN=2)CC1 JANPLEIOOUTRAY-UHFFFAOYSA-N 0.000 claims 2
- BACJEQJZMAJMGA-UHFFFAOYSA-N 4-amino-5-chloro-n-[[1-(3-indol-1-ylpropyl)piperidin-4-yl]methyl]-2-methoxybenzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NCC1CCN(CCCN2C3=CC=CC=C3C=C2)CC1 BACJEQJZMAJMGA-UHFFFAOYSA-N 0.000 claims 2
- PRFWBAVJZPTKCH-UHFFFAOYSA-N 4-amino-5-chloro-n-[[1-(5-indol-1-ylpentyl)piperidin-4-yl]methyl]-2-methoxybenzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NCC1CCN(CCCCCN2C3=CC=CC=C3C=C2)CC1 PRFWBAVJZPTKCH-UHFFFAOYSA-N 0.000 claims 2
- PTDMPQVDDGTRSH-UHFFFAOYSA-N 4-amino-5-chloro-n-[[1-[(4-fluorophenyl)methyl]piperidin-4-yl]methyl]-2-methoxybenzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NCC1CCN(CC=2C=CC(F)=CC=2)CC1 PTDMPQVDDGTRSH-UHFFFAOYSA-N 0.000 claims 2
- OYTUIXYZPOGFSW-UHFFFAOYSA-N 4-amino-5-chloro-n-[[1-[(4-fluorophenyl)methyl]piperidin-4-yl]methyl]-2-methoxybenzamide;hydrochloride Chemical compound Cl.COC1=CC(N)=C(Cl)C=C1C(=O)NCC1CCN(CC=2C=CC(F)=CC=2)CC1 OYTUIXYZPOGFSW-UHFFFAOYSA-N 0.000 claims 2
- ZSJSMKAHAOZHME-UHFFFAOYSA-N 4-amino-5-chloro-n-[[1-[(4-hydroxyphenyl)methyl]piperidin-4-yl]methyl]-2-methoxybenzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NCC1CCN(CC=2C=CC(O)=CC=2)CC1 ZSJSMKAHAOZHME-UHFFFAOYSA-N 0.000 claims 2
- NAOAJXZHAQIWLO-UHFFFAOYSA-N 4-amino-5-chloro-n-[[1-[(4-hydroxyphenyl)methyl]piperidin-4-yl]methyl]-2-methoxybenzamide;hydrochloride Chemical compound Cl.COC1=CC(N)=C(Cl)C=C1C(=O)NCC1CCN(CC=2C=CC(O)=CC=2)CC1 NAOAJXZHAQIWLO-UHFFFAOYSA-N 0.000 claims 2
- QGHBSVOLNZRZIF-UHFFFAOYSA-N 4-amino-5-chloro-n-[[1-[2-(1h-indol-3-yl)ethyl]piperidin-4-yl]methyl]-2-methoxybenzamide Chemical compound COC1=CC(N)=C(Cl)C=C1C(=O)NCC1CCN(CCC=2C3=CC=CC=C3NC=2)CC1 QGHBSVOLNZRZIF-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 239000012279 sodium borohydride Substances 0.000 claims 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000012280 lithium aluminium hydride Substances 0.000 claims 1
- ITYJDNHFRZSTJY-UHFFFAOYSA-N methanesulfonyl bromide Chemical compound CS(Br)(=O)=O ITYJDNHFRZSTJY-UHFFFAOYSA-N 0.000 claims 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims 1
- KNWQLFOXPQZGPX-UHFFFAOYSA-N methanesulfonyl fluoride Chemical compound CS(F)(=O)=O KNWQLFOXPQZGPX-UHFFFAOYSA-N 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims 1
- 229910000105 potassium hydride Inorganic materials 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 150000003936 benzamides Chemical class 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 208000029493 gastroesophageal disease Diseases 0.000 description 3
- 206010022998 Irritability Diseases 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- DCSUBABJRXZOMT-IRLDBZIGSA-N cisapride Chemical compound C([C@@H]([C@@H](CC1)NC(=O)C=2C(=CC(N)=C(Cl)C=2)OC)OC)N1CCCOC1=CC=C(F)C=C1 DCSUBABJRXZOMT-IRLDBZIGSA-N 0.000 description 2
- 229960005132 cisapride Drugs 0.000 description 2
- DCSUBABJRXZOMT-UHFFFAOYSA-N cisapride Natural products C1CC(NC(=O)C=2C(=CC(N)=C(Cl)C=2)OC)C(OC)CN1CCCOC1=CC=C(F)C=C1 DCSUBABJRXZOMT-UHFFFAOYSA-N 0.000 description 2
- 230000006806 disease prevention Effects 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000008512 biological response Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000002651 drug therapy Methods 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 238000001794 hormone therapy Methods 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- OQYITJFGEOOJPO-UHFFFAOYSA-N n-(3-hydroxypiperidin-4-yl)benzamide Chemical compound OC1CNCCC1NC(=O)C1=CC=CC=C1 OQYITJFGEOOJPO-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2010-0038039 | 2010-04-23 | ||
| KR1020100038039A KR101180174B1 (ko) | 2010-04-23 | 2010-04-23 | 신규한 벤즈아미드 유도체 |
| PCT/KR2011/002759 WO2011132901A2 (en) | 2010-04-23 | 2011-04-18 | Novel benzamide derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013525344A JP2013525344A (ja) | 2013-06-20 |
| JP2013525344A5 true JP2013525344A5 (enExample) | 2014-06-26 |
| JP5564147B2 JP5564147B2 (ja) | 2014-07-30 |
Family
ID=44834616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013506071A Expired - Fee Related JP5564147B2 (ja) | 2010-04-23 | 2011-04-18 | 新規なベンズアミド誘導体 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US9221790B2 (enExample) |
| EP (1) | EP2560955B1 (enExample) |
| JP (1) | JP5564147B2 (enExample) |
| KR (1) | KR101180174B1 (enExample) |
| CN (1) | CN102844301B (enExample) |
| AU (1) | AU2011243393B2 (enExample) |
| BR (1) | BR112012026509B1 (enExample) |
| CA (1) | CA2794176C (enExample) |
| ES (1) | ES2594708T3 (enExample) |
| IL (1) | IL222491A (enExample) |
| MX (1) | MX2012011721A (enExample) |
| MY (1) | MY162554A (enExample) |
| NZ (1) | NZ602612A (enExample) |
| PH (1) | PH12012501843A1 (enExample) |
| RU (1) | RU2536688C2 (enExample) |
| SG (1) | SG184350A1 (enExample) |
| UA (1) | UA107702C2 (enExample) |
| WO (1) | WO2011132901A2 (enExample) |
| ZA (1) | ZA201207903B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101341693B1 (ko) | 2011-03-16 | 2013-12-16 | 동아에스티 주식회사 | 생약추출물을 함유하는 퇴행성 신경질환의 치료 및 예방을 위한 조성물 |
| KR101341692B1 (ko) | 2011-03-16 | 2013-12-20 | 동아에스티 주식회사 | 복합생약추출물을 함유하는 당뇨병성 말초 신경병증의 치료 및 예방을 위한 조성물 |
| KR101457789B1 (ko) | 2013-02-13 | 2014-11-03 | 동아제약 주식회사 | 상처 치료용 필름형성 약제학적 조성물 및 그의 제조방법 |
| US9771348B2 (en) | 2013-07-25 | 2017-09-26 | Dong-A St Co., Ltd | Method for preparing benzamide derivative, novel intermediate used in preparation of benzamide, and method for preparing novel intermediate |
| CN104230889A (zh) * | 2014-08-29 | 2014-12-24 | 南京大学 | 环丙沙星衍生物及其制备方法与用途 |
| KR102394635B1 (ko) * | 2015-03-31 | 2022-05-09 | (주)아모레퍼시픽 | 5-아다만탄-1-일-n-(2,4-다이하이드록시벤질)-2,4-다이메톡시벤즈아마이드를 함유하는 항산화 또는 항노화 조성물 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1507462A (en) | 1974-03-21 | 1978-04-12 | Gallardo Antonio Sa | N-heterocyclic substituted benzamides methods for their preparation and compositions containing them |
| US4962115A (en) | 1981-10-01 | 1990-10-09 | Janssen Pharmaceutica N.V. | Novel N-(3-hydroxy-4-piperidinyl)benzamide derivatives |
| US5057525A (en) | 1981-10-01 | 1991-10-15 | Janssen Pharmaceutica N.V. | Novel N-(3-hydroxy-4-piperidinyl) benzamide derivatives |
| US5137896A (en) | 1981-10-01 | 1992-08-11 | Janssen Pharmaceutica N.V. | N-(3-hydroxy-4-piperidinyl)benzamide derivatives |
| EP0774460A1 (en) | 1994-03-30 | 1997-05-21 | Yoshitomi Pharmaceutical Industries, Ltd. | Benzoic acid compound and use thereof as medicine |
| US5864039A (en) * | 1994-03-30 | 1999-01-26 | Yoshitomi Pharmaceutical Industries, Ltd. | Benzoic acid compounds and use thereof as medicaments |
| TW402591B (en) | 1997-07-11 | 2000-08-21 | Janssen Pharmaceutica Nv | Monocyclic benzamides of 3- or 4-substituted 4-(aminomethyl)-piperidine derivatives |
| KR20010081034A (ko) * | 1998-11-20 | 2001-08-25 | 프리돌린 클라우스너, 롤란드 비. 보레르 | 피페리딘 씨씨알-3 수용체 길항제 |
| EP1217000A1 (en) * | 2000-12-23 | 2002-06-26 | Aventis Pharma Deutschland GmbH | Inhibitors of factor Xa and factor VIIa |
| FR2861073B1 (fr) * | 2003-10-17 | 2006-01-06 | Sanofi Synthelabo | Derives de n-[heteroaryl(piperidin-2-yl)methyl]benzamide, leur preparation et leur application en therapeutique |
| KR100854211B1 (ko) | 2003-12-18 | 2008-08-26 | 동아제약주식회사 | 신규한 옥사졸리디논 유도체, 그의 제조방법 및 이를유효성분으로 하는 항생제용 약학 조성물 |
| KR100976063B1 (ko) | 2007-03-16 | 2010-08-17 | 동아제약주식회사 | 신규한 벤즈아미드 유도체 화합물 및 그의 제조방법 |
| ES2526338T3 (es) | 2007-04-19 | 2015-01-09 | Dong-A Pharm.Co., Ltd. | Inhibidor de DPP-IV que incluye grupo beta-amino, método de preparación del mismo y composición farmacéutica que contiene el mismo para prevernir y tratar diabetes u obesidad |
| US8642772B2 (en) * | 2008-10-14 | 2014-02-04 | Sk Biopharmaceuticals Co., Ltd. | Piperidine compounds, pharmaceutical composition comprising the same and its use |
| WO2010062959A1 (en) | 2008-11-26 | 2010-06-03 | Aryx Therapeutics, Inc. | 5-ht4 receptor agonists for treating irritable bowel syndrome and colonic hypersensitivity |
| BR112012023139A2 (pt) | 2010-03-24 | 2018-06-26 | Dong A Pharm Co Ltd | composição farmacêutica para a prevenção ou o tratamento de doença do fígado gordo não alcóolico e o método para a prevenção ou tratamento de doença do fígado gordo não alcóolico usando a mesma. |
| SG190415A1 (en) | 2010-11-24 | 2013-06-28 | Dong A St Co Ltd | Quinoline derivative compound, method for preparing same, and pharmaceutical composition containing same |
| JP5599519B2 (ja) | 2010-11-24 | 2014-10-01 | ドン−ア エスティ カンパニー リミテッド | キノリン誘導体化合物、その製造方法およびそれを含む薬学組成物 |
| KR101341693B1 (ko) | 2011-03-16 | 2013-12-16 | 동아에스티 주식회사 | 생약추출물을 함유하는 퇴행성 신경질환의 치료 및 예방을 위한 조성물 |
| KR101341692B1 (ko) | 2011-03-16 | 2013-12-20 | 동아에스티 주식회사 | 복합생약추출물을 함유하는 당뇨병성 말초 신경병증의 치료 및 예방을 위한 조성물 |
-
2010
- 2010-04-23 KR KR1020100038039A patent/KR101180174B1/ko active Active
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2011
- 2011-04-18 US US13/641,867 patent/US9221790B2/en active Active
- 2011-04-18 EP EP11772189.4A patent/EP2560955B1/en not_active Not-in-force
- 2011-04-18 RU RU2012150037/04A patent/RU2536688C2/ru not_active IP Right Cessation
- 2011-04-18 BR BR112012026509-1A patent/BR112012026509B1/pt not_active IP Right Cessation
- 2011-04-18 WO PCT/KR2011/002759 patent/WO2011132901A2/en not_active Ceased
- 2011-04-18 MX MX2012011721A patent/MX2012011721A/es not_active Application Discontinuation
- 2011-04-18 CA CA2794176A patent/CA2794176C/en active Active
- 2011-04-18 SG SG2012072450A patent/SG184350A1/en unknown
- 2011-04-18 CN CN201180020476.6A patent/CN102844301B/zh not_active Expired - Fee Related
- 2011-04-18 PH PH1/2012/501843A patent/PH12012501843A1/en unknown
- 2011-04-18 MY MYPI2012004698A patent/MY162554A/en unknown
- 2011-04-18 JP JP2013506071A patent/JP5564147B2/ja not_active Expired - Fee Related
- 2011-04-18 NZ NZ602612A patent/NZ602612A/en not_active IP Right Cessation
- 2011-04-18 AU AU2011243393A patent/AU2011243393B2/en not_active Ceased
- 2011-04-18 UA UAA201213255A patent/UA107702C2/ru unknown
- 2011-04-18 ES ES11772189.4T patent/ES2594708T3/es active Active
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2012
- 2012-10-16 IL IL222491A patent/IL222491A/en not_active IP Right Cessation
- 2012-10-19 ZA ZA2012/07903A patent/ZA201207903B/en unknown
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