RU2536688C2 - Новые бензамидные производные - Google Patents
Новые бензамидные производные Download PDFInfo
- Publication number
- RU2536688C2 RU2536688C2 RU2012150037/04A RU2012150037A RU2536688C2 RU 2536688 C2 RU2536688 C2 RU 2536688C2 RU 2012150037/04 A RU2012150037/04 A RU 2012150037/04A RU 2012150037 A RU2012150037 A RU 2012150037A RU 2536688 C2 RU2536688 C2 RU 2536688C2
- Authority
- RU
- Russia
- Prior art keywords
- formula
- methyl
- amino
- chloro
- piperidin
- Prior art date
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- 150000003936 benzamides Chemical class 0.000 title description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 142
- 238000000034 method Methods 0.000 claims abstract description 26
- 239000000018 receptor agonist Substances 0.000 claims abstract description 18
- 229940044601 receptor agonist Drugs 0.000 claims abstract description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 13
- 125000001424 substituent group Chemical group 0.000 claims abstract description 13
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000004480 active ingredient Substances 0.000 claims abstract description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims abstract description 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims abstract description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000003536 tetrazoles Chemical class 0.000 claims abstract description 4
- 150000003852 triazoles Chemical class 0.000 claims abstract description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 79
- 150000003839 salts Chemical class 0.000 claims description 38
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 33
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 18
- -1 C 1 -C 4 alkylsulfonyl halide Chemical class 0.000 claims description 17
- 239000003153 chemical reaction reagent Substances 0.000 claims description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 14
- 201000006549 dyspepsia Diseases 0.000 claims description 14
- 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 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 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 description 10
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 10
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 10
- 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 description 10
- 239000003638 chemical reducing agent Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 claims description 8
- 206010003119 arrhythmia Diseases 0.000 claims description 7
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- 208000010643 digestive system disease Diseases 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 208000018685 gastrointestinal system disease Diseases 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 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 description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 5
- 206010010774 Constipation Diseases 0.000 claims description 5
- 206010019280 Heart failures Diseases 0.000 claims description 5
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 5
- 208000019695 Migraine disease Diseases 0.000 claims description 5
- 206010028813 Nausea Diseases 0.000 claims description 5
- 206010030216 Oesophagitis Diseases 0.000 claims description 5
- 208000002193 Pain Diseases 0.000 claims description 5
- 206010047700 Vomiting Diseases 0.000 claims description 5
- 239000000556 agonist Substances 0.000 claims description 5
- 230000006793 arrhythmia Effects 0.000 claims description 5
- 208000015114 central nervous system disease Diseases 0.000 claims description 5
- 208000010877 cognitive disease Diseases 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 208000006881 esophagitis Diseases 0.000 claims description 5
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 5
- 230000030135 gastric motility Effects 0.000 claims description 5
- 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 5
- 230000001939 inductive effect Effects 0.000 claims description 5
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 5
- 206010027599 migraine Diseases 0.000 claims description 5
- 230000008693 nausea Effects 0.000 claims description 5
- 201000002859 sleep apnea Diseases 0.000 claims description 5
- 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 description 5
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 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 description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 208000012902 Nervous system disease Diseases 0.000 claims description 3
- 208000025966 Neurological disease Diseases 0.000 claims description 3
- 230000001270 agonistic effect Effects 0.000 claims description 3
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- ITYJDNHFRZSTJY-UHFFFAOYSA-N methanesulfonyl bromide Chemical compound CS(Br)(=O)=O ITYJDNHFRZSTJY-UHFFFAOYSA-N 0.000 claims description 3
- KNWQLFOXPQZGPX-UHFFFAOYSA-N methanesulfonyl fluoride Chemical compound CS(F)(=O)=O KNWQLFOXPQZGPX-UHFFFAOYSA-N 0.000 claims description 3
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical group [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 2
- 125000006242 amine protecting group Chemical group 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 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
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
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- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 239000000126 substance Substances 0.000 abstract description 10
- 230000000694 effects Effects 0.000 abstract description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
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- 239000011737 fluorine Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 39
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- 238000002360 preparation method Methods 0.000 description 34
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- 239000000243 solution Substances 0.000 description 19
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- 239000007858 starting material Substances 0.000 description 16
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- 239000002585 base Substances 0.000 description 13
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- AKMFQDGGIQVKFD-UHFFFAOYSA-N 4-amino-5-chloro-2-methoxy-3-(piperidin-4-ylmethyl)benzamide Chemical compound NC1=C(Cl)C=C(C(N)=O)C(OC)=C1CC1CCNCC1 AKMFQDGGIQVKFD-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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- 125000003118 aryl group Chemical group 0.000 description 4
- 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 4
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- 208000028698 Cognitive impairment Diseases 0.000 description 3
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- 230000004526 pharmaceutical effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 108020001213 potassium channel Proteins 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000021055 solid food Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/10—Laxatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Nutrition Science (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
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 (2)
| Publication Number | Publication Date |
|---|---|
| RU2012150037A RU2012150037A (ru) | 2014-05-27 |
| RU2536688C2 true RU2536688C2 (ru) | 2014-12-27 |
Family
ID=44834616
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012150037/04A RU2536688C2 (ru) | 2010-04-23 | 2011-04-18 | Новые бензамидные производные |
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 |
Citations (5)
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| WO1999002494A1 (en) * | 1997-07-11 | 1999-01-21 | Janssen Pharmaceutica N.V. | Gastrokinetic monocyclic benzamides of 3- or 4-substituted 4-(aminomethyl)-piperidine derivatives |
| RU2003122522A (ru) * | 2000-12-23 | 2004-12-27 | АВЕНТИС ФАРМА ДОЙЧЛАНД ГмбХ (DE) | Производные оксибензамидов в качестве ингибиторов фактора ха |
| WO2008114971A1 (en) * | 2007-03-16 | 2008-09-25 | Dong-A Pharm. Co., Ltd. | Novel benzamide derivatives and process for the preparation thereof |
| RU2351596C2 (ru) * | 2003-10-17 | 2009-04-10 | Санофи-Авентис | Производные n-[гетероарил(пиперидин-2-ил)метил]бензамида и их применение в терапии |
| US20100093801A1 (en) * | 2008-10-14 | 2010-04-15 | Sk Holdings Co., Ltd. | Piperidine compounds, pharmaceutical composition comprising the same and its use |
Family Cites Families (15)
| 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 |
| KR20010081034A (ko) * | 1998-11-20 | 2001-08-25 | 프리돌린 클라우스너, 롤란드 비. 보레르 | 피페리딘 씨씨알-3 수용체 길항제 |
| KR100854211B1 (ko) | 2003-12-18 | 2008-08-26 | 동아제약주식회사 | 신규한 옥사졸리디논 유도체, 그의 제조방법 및 이를유효성분으로 하는 항생제용 약학 조성물 |
| 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 |
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| 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
-
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
-
2012
- 2012-10-16 IL IL222491A patent/IL222491A/en not_active IP Right Cessation
- 2012-10-19 ZA ZA2012/07903A patent/ZA201207903B/en unknown
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999002494A1 (en) * | 1997-07-11 | 1999-01-21 | Janssen Pharmaceutica N.V. | Gastrokinetic monocyclic benzamides of 3- or 4-substituted 4-(aminomethyl)-piperidine derivatives |
| RU2003122522A (ru) * | 2000-12-23 | 2004-12-27 | АВЕНТИС ФАРМА ДОЙЧЛАНД ГмбХ (DE) | Производные оксибензамидов в качестве ингибиторов фактора ха |
| RU2351596C2 (ru) * | 2003-10-17 | 2009-04-10 | Санофи-Авентис | Производные n-[гетероарил(пиперидин-2-ил)метил]бензамида и их применение в терапии |
| WO2008114971A1 (en) * | 2007-03-16 | 2008-09-25 | Dong-A Pharm. Co., Ltd. | Novel benzamide derivatives and process for the preparation thereof |
| US20100093801A1 (en) * | 2008-10-14 | 2010-04-15 | Sk Holdings Co., Ltd. | Piperidine compounds, pharmaceutical composition comprising the same and its use |
Non-Patent Citations (1)
| Title |
|---|
| KATSUHIKO ITON et al., "Synthesis and pharmacological evaluation of carboxamide derivatives as selective serotoninergic 5-HT4 receptor agonists", European Journal of Medicinal Chemistry, vol.34, no.4, 1999, pp.329-341. SHUJI SONDA et al., "Design and synthesis of orally active benzamide derivatives as potent serotonin 4 receptor agonist", Bioorganic and Medicinal Chemistry, vol.11, no.19, 2003, pp.4225-4234. SHUJI SONDA et al., "Synthesis and pharmacological evaluation of benzamide derivatives as selective 5-HT4 receptor agonists", Bioorganic and Medicinal Chemistry, vol.13, no.9, 2005, pp.3295-3308. . * |
Also Published As
| Publication number | Publication date |
|---|---|
| MX2012011721A (es) | 2012-12-17 |
| CA2794176C (en) | 2015-12-15 |
| BR112012026509B1 (pt) | 2021-01-19 |
| CN102844301B (zh) | 2015-04-22 |
| RU2012150037A (ru) | 2014-05-27 |
| KR101180174B1 (ko) | 2012-09-05 |
| EP2560955A4 (en) | 2013-09-11 |
| US20130085160A1 (en) | 2013-04-04 |
| MY162554A (en) | 2017-06-15 |
| AU2011243393A1 (en) | 2012-10-18 |
| WO2011132901A2 (en) | 2011-10-27 |
| AU2011243393B2 (en) | 2014-07-17 |
| ZA201207903B (en) | 2013-06-26 |
| BR112012026509A2 (pt) | 2017-10-31 |
| IL222491A0 (en) | 2012-12-31 |
| JP5564147B2 (ja) | 2014-07-30 |
| NZ602612A (en) | 2014-11-28 |
| SG184350A1 (en) | 2012-11-29 |
| CA2794176A1 (en) | 2011-10-27 |
| WO2011132901A3 (en) | 2012-01-26 |
| PH12012501843A1 (en) | 2013-01-07 |
| IL222491A (en) | 2016-07-31 |
| EP2560955B1 (en) | 2016-06-29 |
| UA107702C2 (xx) | 2015-02-10 |
| CN102844301A (zh) | 2012-12-26 |
| KR20110118446A (ko) | 2011-10-31 |
| JP2013525344A (ja) | 2013-06-20 |
| US9221790B2 (en) | 2015-12-29 |
| EP2560955A2 (en) | 2013-02-27 |
| ES2594708T3 (es) | 2016-12-22 |
| HK1176061A1 (en) | 2013-07-19 |
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