JP2013537898A5 - - Google Patents
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- Publication number
- JP2013537898A5 JP2013537898A5 JP2013529673A JP2013529673A JP2013537898A5 JP 2013537898 A5 JP2013537898 A5 JP 2013537898A5 JP 2013529673 A JP2013529673 A JP 2013529673A JP 2013529673 A JP2013529673 A JP 2013529673A JP 2013537898 A5 JP2013537898 A5 JP 2013537898A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- methylpiperidin
- yloxy
- benzimidazol
- phenyl
- 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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- -1 cyano, amino Chemical group 0.000 claims 515
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 243
- 150000001412 amines Chemical class 0.000 claims 76
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 71
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 67
- 125000000217 alkyl group Chemical group 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 25
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims 24
- IOJUPLGTWVMSFF-UHFFFAOYSA-N cyclobenzothiazole Natural products C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 24
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000001475 halogen functional group Chemical group 0.000 claims 13
- 125000004414 alkyl thio group Chemical group 0.000 claims 12
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
- 125000003282 alkyl amino group Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 7
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 6
- 125000004104 aryloxy group Chemical group 0.000 claims 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000001188 haloalkyl group Chemical group 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- 125000004043 oxo group Chemical group O=* 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 3
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 3
- 125000004442 acylamino group Chemical group 0.000 claims 3
- 125000004423 acyloxy group Chemical group 0.000 claims 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims 3
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 3
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims 3
- 125000005122 aminoalkylamino group Chemical group 0.000 claims 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 3
- 150000001540 azides Chemical class 0.000 claims 3
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 3
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 3
- 150000004677 hydrates Chemical class 0.000 claims 3
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical group C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 claims 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
- 102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 claims 2
- 108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 claims 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000005096 aminoalkylaminocarbonyl group Chemical group 0.000 claims 2
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims 2
- 206010006451 bronchitis Diseases 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 230000004064 dysfunction Effects 0.000 claims 2
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 150000002989 phenols Chemical class 0.000 claims 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical group O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims 2
- 229940075420 xanthine Drugs 0.000 claims 2
- OSRUGVAWNJQIOT-UHFFFAOYSA-N 1-[3-[1,3-benzothiazol-2-yl-(1-methylpiperidin-4-yl)oxymethyl]phenyl]pyrrolidin-3-one dihydrochloride Chemical compound Cl.Cl.CN1CCC(CC1)OC(C1=NC2=CC=CC=C2S1)C1=CC=CC(=C1)N1CCC(=O)C1 OSRUGVAWNJQIOT-UHFFFAOYSA-N 0.000 claims 1
- PDNHLCRMUIGNBV-UHFFFAOYSA-N 1-pyridin-2-ylethanamine Chemical compound CC(N)C1=CC=CC=N1 PDNHLCRMUIGNBV-UHFFFAOYSA-N 0.000 claims 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 claims 1
- KJSWRLHLUPFZAD-UHFFFAOYSA-N 2-[(1-methylpiperidin-4-yl)oxy-[3-(trifluoromethylsulfanyl)phenyl]methyl]-1H-benzimidazole oxalic acid Chemical compound CN1CCC(CC1)OC(C1=NC2=C(N1)C=CC=C2)C2=CC(=CC=C2)SC(F)(F)F.C(C(=O)O)(=O)O KJSWRLHLUPFZAD-UHFFFAOYSA-N 0.000 claims 1
- WLLJCHGIPDMWPP-UHFFFAOYSA-N 2-[(1-methylpiperidin-4-yl)oxy-thiophen-2-ylmethyl]-1h-benzimidazole Chemical compound C1CN(C)CCC1OC(C=1NC2=CC=CC=C2N=1)C1=CC=CS1 WLLJCHGIPDMWPP-UHFFFAOYSA-N 0.000 claims 1
- IERXMFRSUIPJFP-UHFFFAOYSA-N 2-[(2,6-difluoro-4-methylphenyl)-(1-methylpiperidin-4-yl)oxymethyl]-1,3-benzoxazole 2-[(3-ethoxy-2,6-difluorophenyl)-(1-methylpiperidin-4-yl)oxymethyl]-1H-benzimidazole oxalic acid Chemical compound FC1=C(C(=CC(=C1)C)F)C(C=1OC2=C(N1)C=CC=C2)OC2CCN(CC2)C.C(C)OC=2C(=C(C(=CC2)F)C(C2=NC1=C(N2)C=CC=C1)OC1CCN(CC1)C)F.C(C(=O)O)(=O)O IERXMFRSUIPJFP-UHFFFAOYSA-N 0.000 claims 1
- VLOPLJQJEGQLBO-UHFFFAOYSA-N 2-[(2,6-difluoro-4-methylphenyl)-(1-methylpiperidin-4-yl)oxymethyl]-1H-benzimidazole oxalic acid Chemical compound FC1=C(C(=CC(=C1)C)F)C(C1=NC2=C(N1)C=CC=C2)OC2CCN(CC2)C.C(C(=O)O)(=O)O VLOPLJQJEGQLBO-UHFFFAOYSA-N 0.000 claims 1
- KNMXRHHEUBGBAE-UHFFFAOYSA-N 2-[(3-bromophenyl)-[(1-methylpyrrolidin-3-yl)methoxy]methyl]-6-fluoro-1H-benzimidazole oxalic acid Chemical compound BrC=1C=C(C=CC1)C(C1=NC2=C(N1)C=CC(=C2)F)OCC2CN(CC2)C.C(C(=O)O)(=O)O KNMXRHHEUBGBAE-UHFFFAOYSA-N 0.000 claims 1
- MIOWLTJHTLRQGH-UHFFFAOYSA-N 2-[1-benzothiophen-6-yl-(1-methylpiperidin-4-yl)oxymethyl]-1h-benzimidazole;oxalic acid Chemical compound OC(=O)C(O)=O.C1CN(C)CCC1OC(C=1C=C2SC=CC2=CC=1)C1=NC2=CC=CC=C2N1 MIOWLTJHTLRQGH-UHFFFAOYSA-N 0.000 claims 1
- MEXRXWKQEHPMCF-UHFFFAOYSA-N 2-[[2-fluoro-5-(2-fluoroethoxy)phenyl]-(1-methylpiperidin-4-yl)oxymethyl]-1H-benzimidazole oxalic acid Chemical compound FC1=C(C=C(C=C1)OCCF)C(C1=NC2=C(N1)C=CC=C2)OC2CCN(CC2)C.C(C(=O)O)(=O)O MEXRXWKQEHPMCF-UHFFFAOYSA-N 0.000 claims 1
- OLCJZDALJASXDU-UHFFFAOYSA-N 2-[[2-fluoro-5-(trifluoromethoxy)phenyl]-(1-methylpiperidin-4-yl)oxymethyl]-1,3-benzothiazole oxalic acid Chemical compound FC1=C(C=C(C=C1)OC(F)(F)F)C(C=1SC2=C(N1)C=CC=C2)OC2CCN(CC2)C.C(C(=O)O)(=O)O OLCJZDALJASXDU-UHFFFAOYSA-N 0.000 claims 1
- IJBUNLUGCLPARD-UHFFFAOYSA-N 2-[[3,5-bis(trifluoromethyl)phenyl]-(1-methylpiperidin-4-yl)oxymethyl]-1H-benzimidazole oxalic acid Chemical compound FC(C=1C=C(C=C(C1)C(F)(F)F)C(C1=NC2=C(N1)C=CC=C2)OC2CCN(CC2)C)(F)F.C(C(=O)O)(=O)O IJBUNLUGCLPARD-UHFFFAOYSA-N 0.000 claims 1
- KXHDPASARHXTSO-UHFFFAOYSA-N 2-[[3-(3-fluoropyrrolidin-1-yl)phenyl]-(1-methylpiperidin-4-yl)oxymethyl]-1,3-benzothiazole oxalic acid Chemical compound FC1CN(CC1)C=1C=C(C=CC1)C(C=1SC2=C(N1)C=CC=C2)OC2CCN(CC2)C.C(C(=O)O)(=O)O KXHDPASARHXTSO-UHFFFAOYSA-N 0.000 claims 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000001331 3-methylbutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims 1
- JYLOICJEZROGMN-UHFFFAOYSA-N 4-[1H-benzimidazol-2-yl-(1-methylpiperidin-4-yl)oxymethyl]phenol 2-[[3-(3,3-difluoropyrrolidin-1-yl)phenyl]-(1-methylpiperidin-4-yl)oxymethyl]-1H-benzimidazole oxalic acid Chemical compound FC1(CN(CC1)C=1C=C(C=CC1)C(C1=NC2=C(N1)C=CC=C2)OC2CCN(CC2)C)F.N2C(=NC1=C2C=CC=C1)C(C1=CC=C(C=C1)O)OC1CCN(CC1)C.C(C(=O)O)(=O)O JYLOICJEZROGMN-UHFFFAOYSA-N 0.000 claims 1
- PBZHPSHIZGZTAC-UHFFFAOYSA-N 4-[3-[(1-methylpiperidin-4-yl)oxy-(4,5,6-trifluoro-1H-benzimidazol-2-yl)methyl]phenyl]sulfanylbutan-1-amine oxalic acid Chemical compound CN1CCC(CC1)OC(C=1C=C(C=CC1)SCCCCN)C1=NC2=C(N1)C(=C(C(=C2)F)F)F.C(C(=O)O)(=O)O PBZHPSHIZGZTAC-UHFFFAOYSA-N 0.000 claims 1
- AVIPAJNDABZYBC-UHFFFAOYSA-N 4-[3-[1,3-benzothiazol-2-yl-(1-methylpiperidin-4-yl)oxymethyl]phenoxy]cyclohexan-1-amine oxalic acid Chemical compound S1C(=NC2=C1C=CC=C2)C(C=2C=C(OC1CCC(CC1)N)C=CC2)OC2CCN(CC2)C.C(C(=O)O)(=O)O AVIPAJNDABZYBC-UHFFFAOYSA-N 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
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- 125000000439 4-methylpentoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims 1
- BKAWJIRCKVUVED-UHFFFAOYSA-N 5-(2-hydroxyethyl)-4-methylthiazole Chemical compound CC=1N=CSC=1CCO BKAWJIRCKVUVED-UHFFFAOYSA-N 0.000 claims 1
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- SYFMPENOKMUXFI-UHFFFAOYSA-N CN1CCC(CC1)OC(C1=NC2=C(N1)C=CC=C2)C2=CC(=CC=C2)OC2CNCC2.C(C(=O)O)(=O)O Chemical compound CN1CCC(CC1)OC(C1=NC2=C(N1)C=CC=C2)C2=CC(=CC=C2)OC2CNCC2.C(C(=O)O)(=O)O SYFMPENOKMUXFI-UHFFFAOYSA-N 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- ZKLPARSLTMPFCP-UHFFFAOYSA-N Cetirizine Chemical group C1CN(CCOCC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 ZKLPARSLTMPFCP-UHFFFAOYSA-N 0.000 claims 1
- 208000017667 Chronic Disease Diseases 0.000 claims 1
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| RS60320B1 (sr) * | 2017-11-15 | 2020-07-31 | Bioprojet Soc Civ | Derivati benzimidazola kao dvostruki ligandi histaminskog h1 i histaminskog h4 receptora |
| CN113278409B (zh) * | 2021-06-22 | 2022-04-29 | 西南石油大学 | 一种高温酸化缓蚀剂 |
| CN119086786B (zh) * | 2024-11-08 | 2025-02-14 | 南京恒远科技开发有限公司 | 叔丁基-(s)-[2-(2-氰基-4,4-二氟吡咯烷-1-基)-2-氧乙基]氨基甲酸酯光学异构体的检测方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI803127A7 (fi) * | 1979-10-03 | 1981-04-04 | Glaxo Group Ltd | Heterosyklisiä yhdisteitä. |
| IT1154888B (it) * | 1980-11-12 | 1987-01-21 | Menarini Sas | Derivati del benzofurano 2-sostituiti e relativi metodi di preparazione |
| US4908372A (en) * | 1988-10-13 | 1990-03-13 | Merrell Dow Pharmaceuticals Inc. | Antihistaminic piperidinyl benzimidazoles |
| JPH05339266A (ja) * | 1992-06-05 | 1993-12-21 | Kaken Pharmaceut Co Ltd | 新規なピペリジン誘導体 |
| US6476041B1 (en) | 1999-10-29 | 2002-11-05 | Merck & Co., Inc. | 1,4 substituted piperidinyl NMDA/NR2B antagonists |
| KR20040068339A (ko) | 2001-12-21 | 2004-07-30 | 아노르메드 인코포레이티드 | 효능이 강화된 케모카인 수용체 결합 헤테로사이클릭 화합물 |
| NZ546259A (en) * | 2003-09-30 | 2009-05-31 | Janssen Pharmaceutica Nv | Benzoimidazole compounds |
| US20060127404A1 (en) * | 2003-09-30 | 2006-06-15 | Chichi Huang | Hinge core mimetibodies, compositions, methods and uses |
| EP1642577A1 (en) * | 2004-09-07 | 2006-04-05 | Laboratorios del Dr. Esteve S.A. | Derivatives of aryl (or heteroaryl) azolylcarbinols for the treatment of central neuropathic pain |
| US7557103B2 (en) | 2005-04-05 | 2009-07-07 | Eli Lilly And Company | Imidazopyridazine compounds |
| JP2011509296A (ja) | 2008-01-09 | 2011-03-24 | レノビス， インコーポレイテッド | イオンチャネルリガンドとしてのアミド誘導体およびそれを使用する薬学的組成物および方法 |
-
2010
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2011
- 2011-09-27 HR HRP20160398TT patent/HRP20160398T1/hr unknown
- 2011-09-27 CN CN201180057036.8A patent/CN103228643B/zh active Active
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- 2011-09-27 JP JP2013529673A patent/JP5922128B2/ja active Active
- 2011-09-27 WO PCT/EP2011/066782 patent/WO2012041860A1/en not_active Ceased
- 2011-09-27 MX MX2013003479A patent/MX339460B/es active IP Right Grant
- 2011-09-27 ES ES11761383T patent/ES2571335T3/es active Active
- 2011-09-27 US US13/825,989 patent/US8802664B2/en active Active
- 2011-09-27 PL PL11761383T patent/PL2621916T3/pl unknown
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