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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| PL2858647T3 (pl) | 2012-06-08 | 2018-10-31 | Sensorion | Inhibitory receptora h4 do leczenia szumów usznych |
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| CN118684652A (zh) * | 2017-09-11 | 2024-09-24 | 克鲁松制药公司 | SHP2的八氢环戊二烯并[c]吡咯别构抑制剂 |
| DK3486243T3 (da) * | 2017-11-15 | 2020-06-08 | Bioprojet Soc Civ | Benzimidazolderivater som dobbelthistamin H1 og histamin H4-receptorligander |
| 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 |
|---|---|---|---|---|
| FI803127L (fi) * | 1979-10-03 | 1981-04-04 | Glaxo Group Ltd | Heterocykliska foereningar |
| 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 |
| CN1596255A (zh) | 2001-12-21 | 2005-03-16 | 阿诺麦德股份有限公司 | 具有强效的与趋化因子受体结合的杂环化合物 |
| JP4767857B2 (ja) * | 2003-09-30 | 2011-09-07 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | ベンゾイミダゾール化合物 |
| NZ546259A (en) * | 2003-09-30 | 2009-05-31 | Janssen Pharmaceutica Nv | Benzoimidazole compounds |
| 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 |
| CA2707441A1 (en) | 2008-01-09 | 2009-07-16 | Renovis, Inc. | Amide derivatives as ion-channel ligands and pharmaceutical compositions and methods of using the same |
-
2010
- 2010-09-27 EP EP20100306038 patent/EP2447263A1/en not_active Withdrawn
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2011
- 2011-09-27 ES ES11761383T patent/ES2571335T3/es active Active
- 2011-09-27 DK DK11761383.6T patent/DK2621916T3/en active
- 2011-09-27 US US13/825,989 patent/US8802664B2/en active Active
- 2011-09-27 HU HUE11761383A patent/HUE027252T2/en unknown
- 2011-09-27 EP EP11761383.6A patent/EP2621916B1/en active Active
- 2011-09-27 CN CN201180057036.8A patent/CN103228643B/zh active Active
- 2011-09-27 WO PCT/EP2011/066782 patent/WO2012041860A1/en not_active Ceased
- 2011-09-27 CA CA2812686A patent/CA2812686C/en active Active
- 2011-09-27 RS RS20160297A patent/RS54737B1/sr unknown
- 2011-09-27 PL PL11761383T patent/PL2621916T3/pl unknown
- 2011-09-27 SI SI201130817A patent/SI2621916T1/sl unknown
- 2011-09-27 JP JP2013529673A patent/JP5922128B2/ja active Active
- 2011-09-27 MX MX2013003479A patent/MX339460B/es active IP Right Grant
- 2011-09-27 HR HRP20160398TT patent/HRP20160398T1/hr unknown
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2014
- 2014-06-27 US US14/317,024 patent/US9029357B2/en active Active
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2016
- 2016-04-26 CY CY20161100339T patent/CY1117416T1/el unknown
- 2016-08-03 SM SM201600262T patent/SMT201600262B/it unknown
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