KR20120124064A - 전압-개폐 나트륨 채널 차단제 - Google Patents
전압-개폐 나트륨 채널 차단제 Download PDFInfo
- Publication number
- KR20120124064A KR20120124064A KR1020127021186A KR20127021186A KR20120124064A KR 20120124064 A KR20120124064 A KR 20120124064A KR 1020127021186 A KR1020127021186 A KR 1020127021186A KR 20127021186 A KR20127021186 A KR 20127021186A KR 20120124064 A KR20120124064 A KR 20120124064A
- Authority
- KR
- South Korea
- Prior art keywords
- methyl
- phenyl
- methylethyl
- pyridinecarboxylate
- piperazinyl
- 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.)
- Withdrawn
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- 239000000664 voltage gated sodium channel blocking agent Substances 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 332
- 238000000034 method Methods 0.000 claims abstract description 60
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 46
- 208000023504 respiratory system disease Diseases 0.000 claims abstract description 35
- 239000000539 dimer Substances 0.000 claims abstract description 28
- 238000011282 treatment Methods 0.000 claims abstract description 21
- 230000000241 respiratory effect Effects 0.000 claims abstract description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 280
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 249
- -1 dibenzofuranyl Chemical class 0.000 claims description 216
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 172
- 125000000217 alkyl group Chemical group 0.000 claims description 171
- 239000000203 mixture Substances 0.000 claims description 166
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 121
- 238000006243 chemical reaction Methods 0.000 claims description 95
- 150000003839 salts Chemical class 0.000 claims description 94
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 89
- 125000001424 substituent group Chemical group 0.000 claims description 84
- 125000001072 heteroaryl group Chemical group 0.000 claims description 81
- 229910052736 halogen Inorganic materials 0.000 claims description 66
- 239000003814 drug Substances 0.000 claims description 57
- 150000002367 halogens Chemical class 0.000 claims description 53
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 50
- 125000003118 aryl group Chemical group 0.000 claims description 47
- 206010011224 Cough Diseases 0.000 claims description 40
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 31
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 31
- 125000001544 thienyl group Chemical group 0.000 claims description 30
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 125000002541 furyl group Chemical group 0.000 claims description 24
- 125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 23
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 22
- 150000007942 carboxylates Chemical class 0.000 claims description 21
- DIARDWDIBROFST-UHFFFAOYSA-N propan-2-yl 2-piperazin-1-ylpyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCNCC1 DIARDWDIBROFST-UHFFFAOYSA-N 0.000 claims description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 18
- 206010057190 Respiratory tract infections Diseases 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 17
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 14
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 14
- PVNIIMVLHYAWGP-UHFFFAOYSA-M nicotinate Chemical compound [O-]C(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-M 0.000 claims description 14
- GEXJFIOPGAASTP-UHFFFAOYSA-N $l^{1}-azanylethane Chemical compound CC[N] GEXJFIOPGAASTP-UHFFFAOYSA-N 0.000 claims description 13
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000004193 piperazinyl group Chemical class 0.000 claims description 9
- 125000003386 piperidinyl group Chemical group 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 8
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 8
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 8
- 125000001246 bromo group Chemical group Br* 0.000 claims description 8
- 125000002346 iodo group Chemical group I* 0.000 claims description 8
- IBETXKOHKDSBSP-NSHDSACASA-N propan-2-yl 2-[(3s)-3-(methylamino)pyrrolidin-1-yl]pyridine-3-carboxylate Chemical compound C1[C@@H](NC)CCN1C1=NC=CC=C1C(=O)OC(C)C IBETXKOHKDSBSP-NSHDSACASA-N 0.000 claims description 8
- IMOVIMGSLCKDOP-JTQLQIEISA-N propan-2-yl 2-[(3s)-3-aminopyrrolidin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1C[C@@H](N)CC1 IMOVIMGSLCKDOP-JTQLQIEISA-N 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 239000011593 sulfur Substances 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- IKRGNKASNPEASH-UHFFFAOYSA-N propan-2-yl 2-[4-[(4-formylphenyl)methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(C=O)=CC=2)CC1 IKRGNKASNPEASH-UHFFFAOYSA-N 0.000 claims description 7
- 230000001225 therapeutic effect Effects 0.000 claims description 7
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- BEQBIRAUYZOTLY-UHFFFAOYSA-N 2-fluoro-1h-pyridine-2-carboxylic acid Chemical compound OC(=O)C1(F)NC=CC=C1 BEQBIRAUYZOTLY-UHFFFAOYSA-N 0.000 claims description 6
- 208000006673 asthma Diseases 0.000 claims description 6
- 206010006451 bronchitis Diseases 0.000 claims description 6
- UQWYJBXBIWMKTO-UHFFFAOYSA-N propan-2-yl 2-[4-[(4-nitrophenyl)methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(=CC=2)[N+]([O-])=O)CC1 UQWYJBXBIWMKTO-UHFFFAOYSA-N 0.000 claims description 6
- DAOXFMXRJCEJRK-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[(4-ethoxyphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C1=CC(OCC)=CC=C1COC1=CC=CC(CN2CCN(CC2)C=2C(=CC=CN=2)C(=O)OC(C)C)=C1 DAOXFMXRJCEJRK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- ZKDZAMNSLYVQKF-CQSZACIVSA-N tert-butyl n-ethyl-n-[(3r)-1-[3-(hydroxymethyl)pyridin-2-yl]pyrrolidin-3-yl]carbamate Chemical compound C1[C@H](N(CC)C(=O)OC(C)(C)C)CCN1C1=NC=CC=C1CO ZKDZAMNSLYVQKF-CQSZACIVSA-N 0.000 claims description 6
- HNTZKNJGAFJMHQ-UHFFFAOYSA-N 2-methylpyridine-3-carboxylic acid Chemical compound CC1=NC=CC=C1C(O)=O HNTZKNJGAFJMHQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000002671 adjuvant Substances 0.000 claims description 5
- 239000011664 nicotinic acid Substances 0.000 claims description 5
- UMWJMSJBMRJRSX-OAHLLOKOSA-N propan-2-yl 2-[(3r)-3-[ethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pyrrolidin-1-yl]pyridine-3-carboxylate Chemical compound C1[C@H](N(CC)C(=O)OC(C)(C)C)CCN1C1=NC=CC=C1C(=O)OC(C)C UMWJMSJBMRJRSX-OAHLLOKOSA-N 0.000 claims description 5
- MTRUSKITRXAUAY-UHFFFAOYSA-N propan-2-yl 2-[4-[(3-aminophenyl)methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(N)C=CC=2)CC1 MTRUSKITRXAUAY-UHFFFAOYSA-N 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- FRFSNMMCRWYRIT-UHFFFAOYSA-N 2-methyl-1h-pyridine-2-carboxylic acid Chemical compound OC(=O)C1(C)NC=CC=C1 FRFSNMMCRWYRIT-UHFFFAOYSA-N 0.000 claims description 4
- DEOXUDSLDSKOEA-FSRHSHDFSA-N Cl.CC(CC(=O)O[C@H]1C(N(CC1)C1=NC=CC=C1C(=NCC)OC(CC(C)(C)C)=O)=C)(C)C Chemical compound Cl.CC(CC(=O)O[C@H]1C(N(CC1)C1=NC=CC=C1C(=NCC)OC(CC(C)(C)C)=O)=C)(C)C DEOXUDSLDSKOEA-FSRHSHDFSA-N 0.000 claims description 4
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 4
- 206010035664 Pneumonia Diseases 0.000 claims description 4
- 201000010001 Silicosis Diseases 0.000 claims description 4
- IJGULRDALPCDDC-OAHLLOKOSA-N [2-[(3r)-3-(ethylamino)pyrrolidin-1-yl]pyridin-3-yl]methyl 3,3-dimethylbutanoate Chemical compound C1[C@H](NCC)CCN1C1=NC=CC=C1COC(=O)CC(C)(C)C IJGULRDALPCDDC-OAHLLOKOSA-N 0.000 claims description 4
- 206010006475 bronchopulmonary dysplasia Diseases 0.000 claims description 4
- 230000001684 chronic effect Effects 0.000 claims description 4
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 4
- 229960003512 nicotinic acid Drugs 0.000 claims description 4
- VVILGPAGWBSXPW-RUZDIDTESA-N propan-2-yl 2-[(3r)-3-[ethyl-[(2-phenylmethoxyphenyl)methyl]amino]pyrrolidin-1-yl]pyridine-3-carboxylate Chemical compound CCN([C@H]1CN(CC1)C=1C(=CC=CN=1)C(=O)OC(C)C)CC1=CC=CC=C1OCC1=CC=CC=C1 VVILGPAGWBSXPW-RUZDIDTESA-N 0.000 claims description 4
- GXEOJKGTIKJEEU-FQLXRVMXSA-N propan-2-yl 2-[(3r)-3-[ethyl-[[4-[[ethyl-[(3r)-1-(2-methylpropanoyl)pyrrolidin-3-yl]amino]methyl]phenyl]methyl]amino]pyrrolidin-1-yl]pyridine-3-carboxylate Chemical compound C([C@H](C1)N(CC)CC2=CC=C(C=C2)CN(CC)[C@H]2CN(CC2)C(=O)C(C)C)CN1C1=NC=CC=C1C(=O)OC(C)C GXEOJKGTIKJEEU-FQLXRVMXSA-N 0.000 claims description 4
- LHQJKVKGIVRUHO-UHFFFAOYSA-N propan-2-yl 2-[4-[(3-benzamidophenyl)methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(NC(=O)C=3C=CC=CC=3)C=CC=2)CC1 LHQJKVKGIVRUHO-UHFFFAOYSA-N 0.000 claims description 4
- MPPMTMZYPVHFAZ-UHFFFAOYSA-N propan-2-yl 2-[4-[(3-nitrophenyl)methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(C=CC=2)[N+]([O-])=O)CC1 MPPMTMZYPVHFAZ-UHFFFAOYSA-N 0.000 claims description 4
- VWOGUHCAFQEAEK-UHFFFAOYSA-N propan-2-yl 2-[4-[(3-phenoxyphenyl)methyl]piperazin-1-yl]-4-phenylpyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=C(N2CCN(CC=3C=C(OC=4C=CC=CC=4)C=CC=3)CC2)N=CC=C1C1=CC=CC=C1 VWOGUHCAFQEAEK-UHFFFAOYSA-N 0.000 claims description 4
- QCNUTVDMWXVCJE-UHFFFAOYSA-N propan-2-yl 2-[4-[(4-aminophenyl)methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(N)=CC=2)CC1 QCNUTVDMWXVCJE-UHFFFAOYSA-N 0.000 claims description 4
- PBBHQGRXHOFYLY-UHFFFAOYSA-N propan-2-yl 2-[4-[(5-ethylthiophen-2-yl)methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound S1C(CC)=CC=C1CN1CCN(C=2C(=CC=CN=2)C(=O)OC(C)C)CC1 PBBHQGRXHOFYLY-UHFFFAOYSA-N 0.000 claims description 4
- RKRDCCXQAQGLNW-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-(4-methoxyphenoxy)phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C1=CC(OC)=CC=C1OC1=CC=CC(CN2CCN(CC2)C=2C(=CC=CN=2)C(=O)OC(C)C)=C1 RKRDCCXQAQGLNW-UHFFFAOYSA-N 0.000 claims description 4
- LYWVATFOLZEDBP-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[(2-chloro-6-fluorophenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(OCC=3C(=CC=CC=3F)Cl)C=CC=2)CC1 LYWVATFOLZEDBP-UHFFFAOYSA-N 0.000 claims description 4
- SXCSZIHBACXNPK-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[(2-methoxyphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound COC1=CC=CC=C1COC1=CC=CC(CN2CCN(CC2)C=2C(=CC=CN=2)C(=O)OC(C)C)=C1 SXCSZIHBACXNPK-UHFFFAOYSA-N 0.000 claims description 4
- HEIDSKRZLCNLNR-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-(diethoxymethyl)phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C1=CC(C(OCC)OCC)=CC=C1CN1CCN(C=2C(=CC=CN=2)C(=O)OC(C)C)CC1 HEIDSKRZLCNLNR-UHFFFAOYSA-N 0.000 claims description 4
- DRGIMGJIXDAWNO-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-(ethylaminomethyl)phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C1=CC(CNCC)=CC=C1CN1CCN(C=2C(=CC=CN=2)C(=O)OC(C)C)CC1 DRGIMGJIXDAWNO-UHFFFAOYSA-N 0.000 claims description 4
- WMGCNNNXUJMDHT-UHFFFAOYSA-N propan-2-yl 4-phenyl-2-[4-[(2-propan-2-yloxyphenyl)methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=C(N2CCN(CC=3C(=CC=CC=3)OC(C)C)CC2)N=CC=C1C1=CC=CC=C1 WMGCNNNXUJMDHT-UHFFFAOYSA-N 0.000 claims description 4
- WCYMWHIPNOFARR-UHFFFAOYSA-N propan-2-yl 4-phenyl-2-[4-[(3-phenylmethoxyphenyl)methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=C(N2CCN(CC=3C=C(OCC=4C=CC=CC=4)C=CC=3)CC2)N=CC=C1C1=CC=CC=C1 WCYMWHIPNOFARR-UHFFFAOYSA-N 0.000 claims description 4
- 201000003651 pulmonary sarcoidosis Diseases 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- HSMFERWIKQDSGX-UHFFFAOYSA-N tert-butyl 4-(3-propan-2-yloxycarbonylpyridin-2-yl)piperazine-1-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(C(=O)OC(C)(C)C)CC1 HSMFERWIKQDSGX-UHFFFAOYSA-N 0.000 claims description 4
- TXXXAAPSSKSRTC-SNVBAGLBSA-N tert-butyl n-[(3r)-1-(2-methylpropanoyl)pyrrolidin-3-yl]carbamate Chemical compound CC(C)C(=O)N1CC[C@@H](NC(=O)OC(C)(C)C)C1 TXXXAAPSSKSRTC-SNVBAGLBSA-N 0.000 claims description 4
- RBRPZIKADUQLIH-GFCCVEGCSA-N tert-butyl n-ethyl-n-[(3r)-1-(2-methylpropanoyl)pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N(CC)[C@@H]1CCN(C(=O)C(C)C)C1 RBRPZIKADUQLIH-GFCCVEGCSA-N 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 4
- LMXXTTACMKHJBV-UHFFFAOYSA-N 3-[[4-(3-propan-2-yloxycarbonylpyridin-2-yl)piperazin-1-yl]methyl]benzoic acid Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(C=CC=2)C(O)=O)CC1 LMXXTTACMKHJBV-UHFFFAOYSA-N 0.000 claims description 3
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 3
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 3
- 208000004852 Lung Injury Diseases 0.000 claims description 3
- 206010069363 Traumatic lung injury Diseases 0.000 claims description 3
- 208000010285 Ventilator-Induced Lung Injury Diseases 0.000 claims description 3
- MSWDOLBRGZSHBC-QGZVFWFLSA-N [2-[(3r)-3-(ethylamino)pyrrolidin-1-yl]pyridin-3-yl]methyl benzoate Chemical compound C1[C@H](NCC)CCN1C1=NC=CC=C1COC(=O)C1=CC=CC=C1 MSWDOLBRGZSHBC-QGZVFWFLSA-N 0.000 claims description 3
- VGKVKHILOHMWFE-HXUWFJFHSA-N [2-[(3r)-3-[ethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pyrrolidin-1-yl]pyridin-3-yl]methyl benzoate Chemical compound C1[C@H](N(CC)C(=O)OC(C)(C)C)CCN1C1=NC=CC=C1COC(=O)C1=CC=CC=C1 VGKVKHILOHMWFE-HXUWFJFHSA-N 0.000 claims description 3
- 239000013566 allergen Substances 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 3
- 208000007451 chronic bronchitis Diseases 0.000 claims description 3
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 230000006698 induction Effects 0.000 claims description 3
- 231100000515 lung injury Toxicity 0.000 claims description 3
- PPYLCKRAZROZIS-UHFFFAOYSA-N propan-2-yl 2-(4-benzylpiperazin-1-yl)-4-iodopyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=C(I)C=CN=C1N1CCN(CC=2C=CC=CC=2)CC1 PPYLCKRAZROZIS-UHFFFAOYSA-N 0.000 claims description 3
- LZXDJLAONZQDKJ-QGZVFWFLSA-N propan-2-yl 2-[(3r)-3-(ethylamino)pyrrolidin-1-yl]-4-phenylpyridine-3-carboxylate Chemical compound C1[C@H](NCC)CCN1C1=NC=CC(C=2C=CC=CC=2)=C1C(=O)OC(C)C LZXDJLAONZQDKJ-QGZVFWFLSA-N 0.000 claims description 3
- SFAGXOISCYWPOQ-LBPRGKRZSA-N propan-2-yl 2-[(3s)-3-(ethylamino)pyrrolidin-1-yl]pyridine-3-carboxylate Chemical compound C1[C@@H](NCC)CCN1C1=NC=CC=C1C(=O)OC(C)C SFAGXOISCYWPOQ-LBPRGKRZSA-N 0.000 claims description 3
- JVTHEFFEJCJICF-FQEVSTJZSA-N propan-2-yl 2-[(3s)-3-[(2-ethylphenyl)methyl-methylamino]pyrrolidin-1-yl]pyridine-3-carboxylate Chemical compound CCC1=CC=CC=C1CN(C)[C@@H]1CN(C=2C(=CC=CN=2)C(=O)OC(C)C)CC1 JVTHEFFEJCJICF-FQEVSTJZSA-N 0.000 claims description 3
- YVJPLBDEYNOFFF-IBGZPJMESA-N propan-2-yl 2-[(3s)-3-[(2-ethylphenyl)methylamino]pyrrolidin-1-yl]pyridine-3-carboxylate Chemical compound CCC1=CC=CC=C1CN[C@@H]1CN(C=2C(=CC=CN=2)C(=O)OC(C)C)CC1 YVJPLBDEYNOFFF-IBGZPJMESA-N 0.000 claims description 3
- OTCNNXNYAHLHIN-ZDUSSCGKSA-N propan-2-yl 2-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1C[C@@H](NC(=O)OC(C)(C)C)CC1 OTCNNXNYAHLHIN-ZDUSSCGKSA-N 0.000 claims description 3
- AGTPMINTWVVUJL-FQEVSTJZSA-N propan-2-yl 2-[(3s)-3-[(3-ethylphenyl)methyl-methylamino]pyrrolidin-1-yl]pyridine-3-carboxylate Chemical compound CCC1=CC=CC(CN(C)[C@@H]2CN(CC2)C=2C(=CC=CN=2)C(=O)OC(C)C)=C1 AGTPMINTWVVUJL-FQEVSTJZSA-N 0.000 claims description 3
- WMLOTXGALDCQLM-IBGZPJMESA-N propan-2-yl 2-[(3s)-3-[(3-ethylphenyl)methylamino]pyrrolidin-1-yl]pyridine-3-carboxylate Chemical compound CCC1=CC=CC(CN[C@@H]2CN(CC2)C=2C(=CC=CN=2)C(=O)OC(C)C)=C1 WMLOTXGALDCQLM-IBGZPJMESA-N 0.000 claims description 3
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- QKNQALZHYPAHDD-XMMPIXPASA-N propan-2-yl 2-[(3r)-3-[ethyl-[(3-fluorophenyl)methyl]amino]pyrrolidin-1-yl]-4-phenylpyridine-3-carboxylate Chemical compound CCN([C@H]1CN(CC1)C=1C(=C(C=2C=CC=CC=2)C=CN=1)C(=O)OC(C)C)CC1=CC=CC(F)=C1 QKNQALZHYPAHDD-XMMPIXPASA-N 0.000 claims description 2
- QOBVMJMQPMEILB-HXUWFJFHSA-N propan-2-yl 2-[(3r)-3-[ethyl-[(3-methoxyphenyl)methyl]amino]pyrrolidin-1-yl]-4-methylpyridine-3-carboxylate Chemical compound CCN([C@H]1CN(CC1)C=1C(=C(C)C=CN=1)C(=O)OC(C)C)CC1=CC=CC(OC)=C1 QOBVMJMQPMEILB-HXUWFJFHSA-N 0.000 claims description 2
- PBYHAFQMUIBWAS-XMMPIXPASA-N propan-2-yl 2-[(3r)-3-[ethyl-[(3-methoxyphenyl)methyl]amino]pyrrolidin-1-yl]-4-phenylpyridine-3-carboxylate Chemical compound CCN([C@H]1CN(CC1)C=1C(=C(C=2C=CC=CC=2)C=CN=1)C(=O)OC(C)C)CC1=CC=CC(OC)=C1 PBYHAFQMUIBWAS-XMMPIXPASA-N 0.000 claims description 2
- ADZOMLMHPROJIV-XMMPIXPASA-N propan-2-yl 2-[(3r)-3-[ethyl-[(3-phenoxyphenyl)methyl]amino]pyrrolidin-1-yl]-4-methylpyridine-3-carboxylate Chemical compound CCN([C@H]1CN(CC1)C=1C(=C(C)C=CN=1)C(=O)OC(C)C)CC(C=1)=CC=CC=1OC1=CC=CC=C1 ADZOMLMHPROJIV-XMMPIXPASA-N 0.000 claims description 2
- RQDGEJAOFWQJFF-HSZRJFAPSA-N propan-2-yl 2-[(3r)-3-[ethyl-[(3-phenoxyphenyl)methyl]amino]pyrrolidin-1-yl]pyridine-3-carboxylate Chemical class CCN([C@H]1CN(CC1)C=1C(=CC=CN=1)C(=O)OC(C)C)CC(C=1)=CC=CC=1OC1=CC=CC=C1 RQDGEJAOFWQJFF-HSZRJFAPSA-N 0.000 claims description 2
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- HETOHFJKHIZXEH-LJQANCHMSA-N propan-2-yl 2-[(3r)-3-[ethyl-[(4-methoxyphenyl)methyl]amino]pyrrolidin-1-yl]pyridine-3-carboxylate Chemical compound CCN([C@H]1CN(CC1)C=1C(=CC=CN=1)C(=O)OC(C)C)CC1=CC=C(OC)C=C1 HETOHFJKHIZXEH-LJQANCHMSA-N 0.000 claims description 2
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- XALHPDZQLPOCCP-JOCHJYFZSA-N propan-2-yl 2-[(3r)-3-[ethyl-[(4-propoxyphenyl)methyl]amino]pyrrolidin-1-yl]-4-methylpyridine-3-carboxylate Chemical compound C1=CC(OCCC)=CC=C1CN(CC)[C@H]1CN(C=2C(=C(C)C=CN=2)C(=O)OC(C)C)CC1 XALHPDZQLPOCCP-JOCHJYFZSA-N 0.000 claims description 2
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- VWRFDSCVDYKSIC-XMMPIXPASA-N propan-2-yl 2-[(3r)-3-[ethyl-[(4-pyridin-3-ylphenyl)methyl]amino]pyrrolidin-1-yl]pyridine-3-carboxylate Chemical compound CCN([C@H]1CN(CC1)C=1C(=CC=CN=1)C(=O)OC(C)C)CC(C=C1)=CC=C1C1=CC=CN=C1 VWRFDSCVDYKSIC-XMMPIXPASA-N 0.000 claims description 2
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- UDCLQOSMWWMDPV-VWLOTQADSA-N propan-2-yl 2-[(3s)-3-[ethyl-[(3-phenylmethoxyphenyl)methyl]amino]pyrrolidin-1-yl]pyridine-3-carboxylate Chemical compound CCN([C@@H]1CN(CC1)C=1C(=CC=CN=1)C(=O)OC(C)C)CC(C=1)=CC=CC=1OCC1=CC=CC=C1 UDCLQOSMWWMDPV-VWLOTQADSA-N 0.000 claims description 2
- IUVCNSLCVZZKBB-NRFANRHFSA-N propan-2-yl 2-[(3s)-3-[ethyl-[(4-ethylphenyl)methyl]amino]pyrrolidin-1-yl]pyridine-3-carboxylate Chemical compound CCN([C@@H]1CN(CC1)C=1C(=CC=CN=1)C(=O)OC(C)C)CC1=CC=C(CC)C=C1 IUVCNSLCVZZKBB-NRFANRHFSA-N 0.000 claims description 2
- GGGDEBKOAHSRTJ-QHCPKHFHSA-N propan-2-yl 2-[(3s)-3-[ethyl-[(4-phenoxyphenyl)methyl]amino]pyrrolidin-1-yl]pyridine-3-carboxylate Chemical compound CCN([C@@H]1CN(CC1)C=1C(=CC=CN=1)C(=O)OC(C)C)CC(C=C1)=CC=C1OC1=CC=CC=C1 GGGDEBKOAHSRTJ-QHCPKHFHSA-N 0.000 claims description 2
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- HZPJISZBPYJIIS-KRWDZBQOSA-N propan-2-yl 2-[(3s)-3-[ethyl-[(5-ethylthiophen-2-yl)methyl]amino]pyrrolidin-1-yl]pyridine-3-carboxylate Chemical compound CCN([C@@H]1CN(CC1)C=1C(=CC=CN=1)C(=O)OC(C)C)CC1=CC=C(CC)S1 HZPJISZBPYJIIS-KRWDZBQOSA-N 0.000 claims description 2
- GNYULZARAHHFPZ-QHCPKHFHSA-N propan-2-yl 2-[(3s)-3-[ethyl-[[2-(4-fluorophenoxy)phenyl]methyl]amino]pyrrolidin-1-yl]pyridine-3-carboxylate Chemical compound CCN([C@@H]1CN(CC1)C=1C(=CC=CN=1)C(=O)OC(C)C)CC1=CC=CC=C1OC1=CC=C(F)C=C1 GNYULZARAHHFPZ-QHCPKHFHSA-N 0.000 claims description 2
- NVLYUMUVDXSGKX-QHCPKHFHSA-N propan-2-yl 2-[(3s)-3-[ethyl-[[4-(4-fluorophenoxy)phenyl]methyl]amino]pyrrolidin-1-yl]pyridine-3-carboxylate Chemical compound CCN([C@@H]1CN(CC1)C=1C(=CC=CN=1)C(=O)OC(C)C)CC(C=C1)=CC=C1OC1=CC=C(F)C=C1 NVLYUMUVDXSGKX-QHCPKHFHSA-N 0.000 claims description 2
- XUENMGQPZGCSPT-AWEZNQCLSA-N propan-2-yl 2-[(3s)-3-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pyrrolidin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1C[C@@H](N(C)C(=O)OC(C)(C)C)CC1 XUENMGQPZGCSPT-AWEZNQCLSA-N 0.000 claims description 2
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- RRGVUTJZMPZCGI-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[(3,5-dimethoxyphenoxy)methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound COC1=CC(OC)=CC(OCC=2C=C(CN3CCN(CC3)C=3C(=CC=CN=3)C(=O)OC(C)C)C=CC=2)=C1 RRGVUTJZMPZCGI-UHFFFAOYSA-N 0.000 claims description 2
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- NJLUIWJXMZFGIY-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[(3-chlorophenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(OCC=3C=C(Cl)C=CC=3)C=CC=2)CC1 NJLUIWJXMZFGIY-UHFFFAOYSA-N 0.000 claims description 2
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- QFWDZWDNMHEJID-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[(3-methoxyphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate;hydrochloride Chemical compound Cl.COC1=CC=CC(COC=2C=C(CN3CCN(CC3)C=3C(=CC=CN=3)C(=O)OC(C)C)C=CC=2)=C1 QFWDZWDNMHEJID-UHFFFAOYSA-N 0.000 claims description 2
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- GKMGDJLSDBBUOM-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[(4-chlorophenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(OCC=3C=CC(Cl)=CC=3)C=CC=2)CC1 GKMGDJLSDBBUOM-UHFFFAOYSA-N 0.000 claims description 2
- KUMNORXCRYZRBK-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[(4-cyanophenoxy)methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(COC=3C=CC(=CC=3)C#N)C=CC=2)CC1 KUMNORXCRYZRBK-UHFFFAOYSA-N 0.000 claims description 2
- VASGDQZGTWLYCI-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[(4-cyanophenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(OCC=3C=CC(=CC=3)C#N)C=CC=2)CC1 VASGDQZGTWLYCI-UHFFFAOYSA-N 0.000 claims description 2
- TWAUKXPDZCDYOU-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[(4-ethoxyphenoxy)methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C1=CC(OCC)=CC=C1OCC1=CC=CC(CN2CCN(CC2)C=2C(=CC=CN=2)C(=O)OC(C)C)=C1 TWAUKXPDZCDYOU-UHFFFAOYSA-N 0.000 claims description 2
- SMSBUNYPDOGWSW-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[(4-ethylphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C1=CC(CC)=CC=C1COC1=CC=CC(CN2CCN(CC2)C=2C(=CC=CN=2)C(=O)OC(C)C)=C1 SMSBUNYPDOGWSW-UHFFFAOYSA-N 0.000 claims description 2
- DWVDWFSUIXVNGH-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[(4-fluorophenoxy)methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(COC=3C=CC(F)=CC=3)C=CC=2)CC1 DWVDWFSUIXVNGH-UHFFFAOYSA-N 0.000 claims description 2
- ROHCREIVCYNOHF-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[(4-fluorophenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(OCC=3C=CC(F)=CC=3)C=CC=2)CC1 ROHCREIVCYNOHF-UHFFFAOYSA-N 0.000 claims description 2
- CLSMZVFGPJNYKG-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[(4-methoxycarbonylphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C1=CC(C(=O)OC)=CC=C1COC1=CC=CC(CN2CCN(CC2)C=2C(=CC=CN=2)C(=O)OC(C)C)=C1 CLSMZVFGPJNYKG-UHFFFAOYSA-N 0.000 claims description 2
- FRDCOWDYIPGSAQ-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[(4-methoxyphenoxy)methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C1=CC(OC)=CC=C1OCC1=CC=CC(CN2CCN(CC2)C=2C(=CC=CN=2)C(=O)OC(C)C)=C1 FRDCOWDYIPGSAQ-UHFFFAOYSA-N 0.000 claims description 2
- UNQPGLLTNVHTPR-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[(4-methoxyphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C1=CC(OC)=CC=C1COC1=CC=CC(CN2CCN(CC2)C=2C(=CC=CN=2)C(=O)OC(C)C)=C1 UNQPGLLTNVHTPR-UHFFFAOYSA-N 0.000 claims description 2
- KKNLBNQHOSHBQV-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[(4-methylphenoxy)methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(COC=3C=CC(C)=CC=3)C=CC=2)CC1 KKNLBNQHOSHBQV-UHFFFAOYSA-N 0.000 claims description 2
- TZQGSQFYHWQYOK-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[(4-methylphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(OCC=3C=CC(C)=CC=3)C=CC=2)CC1 TZQGSQFYHWQYOK-UHFFFAOYSA-N 0.000 claims description 2
- IFRGERMEVWPTQG-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[(4-methylsulfonylphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(OCC=3C=CC(=CC=3)S(C)(=O)=O)C=CC=2)CC1 IFRGERMEVWPTQG-UHFFFAOYSA-N 0.000 claims description 2
- FEZOTBIKVVGNCQ-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[(4-nitrophenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(OCC=3C=CC(=CC=3)[N+]([O-])=O)C=CC=2)CC1 FEZOTBIKVVGNCQ-UHFFFAOYSA-N 0.000 claims description 2
- PZZALTXGZUTWMO-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[(4-propan-2-ylphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(OCC=3C=CC(=CC=3)C(C)C)C=CC=2)CC1 PZZALTXGZUTWMO-UHFFFAOYSA-N 0.000 claims description 2
- FDLQXGIZVDJXSU-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[2-(2-chloroethoxy)ethoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(OCCOCCCl)C=CC=2)CC1 FDLQXGIZVDJXSU-UHFFFAOYSA-N 0.000 claims description 2
- WEXRFUOTKKJPNB-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[2-(trifluoromethyl)anilino]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(NC=3C(=CC=CC=3)C(F)(F)F)C=CC=2)CC1 WEXRFUOTKKJPNB-UHFFFAOYSA-N 0.000 claims description 2
- GYNCYHGSKJOVBW-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[3-(trifluoromethyl)phenoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(OC=3C=C(C=CC=3)C(F)(F)F)C=CC=2)CC1 GYNCYHGSKJOVBW-UHFFFAOYSA-N 0.000 claims description 2
- BLOUVIPRYXOGEN-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[[2-(trifluoromethyl)phenoxy]methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(COC=3C(=CC=CC=3)C(F)(F)F)C=CC=2)CC1 BLOUVIPRYXOGEN-UHFFFAOYSA-N 0.000 claims description 2
- VWSSXNFSGCXVDE-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[[3-(dimethylamino)phenyl]methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(OCC=3C=C(C=CC=3)N(C)C)C=CC=2)CC1 VWSSXNFSGCXVDE-UHFFFAOYSA-N 0.000 claims description 2
- PRQKFUJKJKKGFK-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[[3-(trifluoromethyl)phenyl]methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(OCC=3C=C(C=CC=3)C(F)(F)F)C=CC=2)CC1 PRQKFUJKJKKGFK-UHFFFAOYSA-N 0.000 claims description 2
- OWRLNCORQCYHCK-UHFFFAOYSA-N propan-2-yl 2-[4-[[3-[benzoyl(methyl)amino]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate;hydrochloride Chemical compound Cl.CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=C(C=CC=2)N(C)C(=O)C=2C=CC=CC=2)CC1 OWRLNCORQCYHCK-UHFFFAOYSA-N 0.000 claims description 2
- LYJUYGHKOBPTPL-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-(2,4-dichlorophenoxy)phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OC=3C(=CC(Cl)=CC=3)Cl)=CC=2)CC1 LYJUYGHKOBPTPL-UHFFFAOYSA-N 0.000 claims description 2
- ZBXKPTQCAHYZGK-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-(2,6-difluoroanilino)phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(NC=3C(=CC=CC=3F)F)=CC=2)CC1 ZBXKPTQCAHYZGK-UHFFFAOYSA-N 0.000 claims description 2
- NOLIHEMPCZBLNU-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-(2-chloroanilino)phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(NC=3C(=CC=CC=3)Cl)=CC=2)CC1 NOLIHEMPCZBLNU-UHFFFAOYSA-N 0.000 claims description 2
- ISKZAQWKGHCWFF-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-(2-fluoroanilino)phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(NC=3C(=CC=CC=3)F)=CC=2)CC1 ISKZAQWKGHCWFF-UHFFFAOYSA-N 0.000 claims description 2
- CVHLHCFEIGJAAL-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-(3-chlorophenoxy)phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OC=3C=C(Cl)C=CC=3)=CC=2)CC1 CVHLHCFEIGJAAL-UHFFFAOYSA-N 0.000 claims description 2
- ULNFCPYPUUTLHO-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-(3-phenylpropyl)phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate;hydrochloride Chemical compound Cl.CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(CCCC=3C=CC=CC=3)=CC=2)CC1 ULNFCPYPUUTLHO-UHFFFAOYSA-N 0.000 claims description 2
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- PGQPTOJRJRMHKS-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-(4-chlorophenoxy)phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OC=3C=CC(Cl)=CC=3)=CC=2)CC1 PGQPTOJRJRMHKS-UHFFFAOYSA-N 0.000 claims description 2
- ADDGJEQOLAENEL-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-(4-cyanophenoxy)phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OC=3C=CC(=CC=3)C#N)=CC=2)CC1 ADDGJEQOLAENEL-UHFFFAOYSA-N 0.000 claims description 2
- IYQIVNTUFMCDIS-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-(4-fluorophenoxy)phenyl]methyl]piperazin-1-yl]-4-phenylpyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=C(N2CCN(CC=3C=CC(OC=4C=CC(F)=CC=4)=CC=3)CC2)N=CC=C1C1=CC=CC=C1 IYQIVNTUFMCDIS-UHFFFAOYSA-N 0.000 claims description 2
- NEVJSYAHCYMDLC-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-(4-fluorophenoxy)phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OC=3C=CC(F)=CC=3)=CC=2)CC1 NEVJSYAHCYMDLC-UHFFFAOYSA-N 0.000 claims description 2
- QVYVUAZKGFVFIJ-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-(4-methoxyanilino)phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C1=CC(OC)=CC=C1NC(C=C1)=CC=C1CN1CCN(C=2C(=CC=CN=2)C(=O)OC(C)C)CC1 QVYVUAZKGFVFIJ-UHFFFAOYSA-N 0.000 claims description 2
- LGCUWPHHOMQPCW-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-(4-methoxyphenoxy)phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C1=CC(OC)=CC=C1OC(C=C1)=CC=C1CN1CCN(C=2C(=CC=CN=2)C(=O)OC(C)C)CC1 LGCUWPHHOMQPCW-UHFFFAOYSA-N 0.000 claims description 2
- URQSNZFLLDRULM-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-(4-methylphenoxy)phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OC=3C=CC(C)=CC=3)=CC=2)CC1 URQSNZFLLDRULM-UHFFFAOYSA-N 0.000 claims description 2
- ZMSIZUGAWCHCJY-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-(benzamidomethyl)phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical group CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(CNC(=O)C=3C=CC=CC=3)=CC=2)CC1 ZMSIZUGAWCHCJY-UHFFFAOYSA-N 0.000 claims description 2
- MFRAUEUVSJIVBD-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-(dimethylcarbamoyl)phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate;hydrochloride Chemical compound Cl.CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(=CC=2)C(=O)N(C)C)CC1 MFRAUEUVSJIVBD-UHFFFAOYSA-N 0.000 claims description 2
- VKNVYKVZWAQFAL-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-(dimethylsulfamoyl)phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(=CC=2)S(=O)(=O)N(C)C)CC1 VKNVYKVZWAQFAL-UHFFFAOYSA-N 0.000 claims description 2
- XSOGSBPFQVMFLX-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-(ethylaminomethyl)phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate;dihydrochloride Chemical compound Cl.Cl.C1=CC(CNCC)=CC=C1CN1CCN(C=2C(=CC=CN=2)C(=O)OC(C)C)CC1 XSOGSBPFQVMFLX-UHFFFAOYSA-N 0.000 claims description 2
- RXQUDCCGKKOIOC-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-(hydroxymethyl)phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate;hydrochloride Chemical compound Cl.CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(CO)=CC=2)CC1 RXQUDCCGKKOIOC-UHFFFAOYSA-N 0.000 claims description 2
- XIGUXDXADAEMQG-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-(naphthalen-1-ylmethoxy)phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C4=CC=CC=C4C=CC=3)=CC=2)CC1 XIGUXDXADAEMQG-UHFFFAOYSA-N 0.000 claims description 2
- DJWCPHGAFMLXJM-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(2,3-dichlorophenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C(=C(Cl)C=CC=3)Cl)=CC=2)CC1 DJWCPHGAFMLXJM-UHFFFAOYSA-N 0.000 claims description 2
- SUIKVWWNLADLFG-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(2,3-dimethoxyphenoxy)methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound COC1=CC=CC(OCC=2C=CC(CN3CCN(CC3)C=3C(=CC=CN=3)C(=O)OC(C)C)=CC=2)=C1OC SUIKVWWNLADLFG-UHFFFAOYSA-N 0.000 claims description 2
- UWGBAWGVYPHSPB-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(2,4,5-trifluorophenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C(=CC(F)=C(F)C=3)F)=CC=2)CC1 UWGBAWGVYPHSPB-UHFFFAOYSA-N 0.000 claims description 2
- KFHDCNYQAHDNHZ-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(2,4-dichlorophenoxy)methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(COC=3C(=CC(Cl)=CC=3)Cl)=CC=2)CC1 KFHDCNYQAHDNHZ-UHFFFAOYSA-N 0.000 claims description 2
- MFPCVCGRBJNITE-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(2,4-dichlorophenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C(=CC(Cl)=CC=3)Cl)=CC=2)CC1 MFPCVCGRBJNITE-UHFFFAOYSA-N 0.000 claims description 2
- ULOQXJWCSCILHC-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(2,4-difluorophenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C(=CC(F)=CC=3)F)=CC=2)CC1 ULOQXJWCSCILHC-UHFFFAOYSA-N 0.000 claims description 2
- LVQWSQRKDLWBLH-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(2,4-dimethoxyphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound COC1=CC(OC)=CC=C1COC(C=C1)=CC=C1CN1CCN(C=2C(=CC=CN=2)C(=O)OC(C)C)CC1 LVQWSQRKDLWBLH-UHFFFAOYSA-N 0.000 claims description 2
- FUPGKTVHFFKFON-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(2,4-dimethylphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C(=CC(C)=CC=3)C)=CC=2)CC1 FUPGKTVHFFKFON-UHFFFAOYSA-N 0.000 claims description 2
- CAZJLEBACBAEFH-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(2,6-dichlorophenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C(=CC=CC=3Cl)Cl)=CC=2)CC1 CAZJLEBACBAEFH-UHFFFAOYSA-N 0.000 claims description 2
- LSYSISINDWQMKX-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(2,6-difluorophenoxy)methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(COC=3C(=CC=CC=3F)F)=CC=2)CC1 LSYSISINDWQMKX-UHFFFAOYSA-N 0.000 claims description 2
- VIJNDSFHDLTBKH-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(2-chloro-6-fluorophenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C(=CC=CC=3F)Cl)=CC=2)CC1 VIJNDSFHDLTBKH-UHFFFAOYSA-N 0.000 claims description 2
- UVYXJINKYJFYKU-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(2-chlorophenoxy)methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(COC=3C(=CC=CC=3)Cl)=CC=2)CC1 UVYXJINKYJFYKU-UHFFFAOYSA-N 0.000 claims description 2
- SJWXDDIGCNXLGL-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(2-chlorophenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C(=CC=CC=3)Cl)=CC=2)CC1 SJWXDDIGCNXLGL-UHFFFAOYSA-N 0.000 claims description 2
- ADZMXHKEBWZVOX-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(2-ethoxyphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CCOC1=CC=CC=C1COC(C=C1)=CC=C1CN1CCN(C=2C(=CC=CN=2)C(=O)OC(C)C)CC1 ADZMXHKEBWZVOX-UHFFFAOYSA-N 0.000 claims description 2
- MXUBFRDJBJERRK-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(2-ethylphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CCC1=CC=CC=C1COC(C=C1)=CC=C1CN1CCN(C=2C(=CC=CN=2)C(=O)OC(C)C)CC1 MXUBFRDJBJERRK-UHFFFAOYSA-N 0.000 claims description 2
- VIOOPPBOPKUSNX-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(2-methoxyphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound COC1=CC=CC=C1COC(C=C1)=CC=C1CN1CCN(C=2C(=CC=CN=2)C(=O)OC(C)C)CC1 VIOOPPBOPKUSNX-UHFFFAOYSA-N 0.000 claims description 2
- XQHVYSIUTCYKAK-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(2-methylphenoxy)methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(COC=3C(=CC=CC=3)C)=CC=2)CC1 XQHVYSIUTCYKAK-UHFFFAOYSA-N 0.000 claims description 2
- XQKYDWOYFBJZBR-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(2-methylphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C(=CC=CC=3)C)=CC=2)CC1 XQKYDWOYFBJZBR-UHFFFAOYSA-N 0.000 claims description 2
- ONKAIGUFCYXSMA-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(3,4-dichlorophenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C=C(Cl)C(Cl)=CC=3)=CC=2)CC1 ONKAIGUFCYXSMA-UHFFFAOYSA-N 0.000 claims description 2
- DZVNQYYXDASGJV-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(3,4-difluorophenoxy)methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(COC=3C=C(F)C(F)=CC=3)=CC=2)CC1 DZVNQYYXDASGJV-UHFFFAOYSA-N 0.000 claims description 2
- YKZSXRFASJFPJW-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(3,4-difluorophenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C=C(F)C(F)=CC=3)=CC=2)CC1 YKZSXRFASJFPJW-UHFFFAOYSA-N 0.000 claims description 2
- LACXLTMNDHUQEE-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(3,4-dimethoxyphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C1=C(OC)C(OC)=CC=C1COC(C=C1)=CC=C1CN1CCN(C=2C(=CC=CN=2)C(=O)OC(C)C)CC1 LACXLTMNDHUQEE-UHFFFAOYSA-N 0.000 claims description 2
- NURATLGKIMCBFR-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(3,5-dichlorophenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C=C(Cl)C=C(Cl)C=3)=CC=2)CC1 NURATLGKIMCBFR-UHFFFAOYSA-N 0.000 claims description 2
- CAALGLFXCRSUDN-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(3,5-dimethoxyphenoxy)methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound COC1=CC(OC)=CC(OCC=2C=CC(CN3CCN(CC3)C=3C(=CC=CN=3)C(=O)OC(C)C)=CC=2)=C1 CAALGLFXCRSUDN-UHFFFAOYSA-N 0.000 claims description 2
- PKGFZAHCJIEICM-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(3,5-dimethoxyphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound COC1=CC(OC)=CC(COC=2C=CC(CN3CCN(CC3)C=3C(=CC=CN=3)C(=O)OC(C)C)=CC=2)=C1 PKGFZAHCJIEICM-UHFFFAOYSA-N 0.000 claims description 2
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- GGLUTQKSNYDQSD-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(3-chlorophenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C=C(Cl)C=CC=3)=CC=2)CC1 GGLUTQKSNYDQSD-UHFFFAOYSA-N 0.000 claims description 2
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- ZUQSOUHUKCRLNW-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(3-fluorophenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C=C(F)C=CC=3)=CC=2)CC1 ZUQSOUHUKCRLNW-UHFFFAOYSA-N 0.000 claims description 2
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- RUFJBIAPTAGPPY-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(3-methoxyphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound COC1=CC=CC(COC=2C=CC(CN3CCN(CC3)C=3C(=CC=CN=3)C(=O)OC(C)C)=CC=2)=C1 RUFJBIAPTAGPPY-UHFFFAOYSA-N 0.000 claims description 2
- PBOXZSFFBZIVFZ-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(3-methylphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C=C(C)C=CC=3)=CC=2)CC1 PBOXZSFFBZIVFZ-UHFFFAOYSA-N 0.000 claims description 2
- RXSQYDSYILHMPU-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(4-benzylpiperazin-1-yl)methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(CN3CCN(CC=4C=CC=CC=4)CC3)=CC=2)CC1 RXSQYDSYILHMPU-UHFFFAOYSA-N 0.000 claims description 2
- QUMSMHIXMVIAHO-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(4-bromophenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C=CC(Br)=CC=3)=CC=2)CC1 QUMSMHIXMVIAHO-UHFFFAOYSA-N 0.000 claims description 2
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- AMRNNEIVGVNGNA-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(4-cyanophenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C=CC(=CC=3)C#N)=CC=2)CC1 AMRNNEIVGVNGNA-UHFFFAOYSA-N 0.000 claims description 2
- WJCMIVBNCATQEE-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(4-ethoxyphenoxy)methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C1=CC(OCC)=CC=C1OCC(C=C1)=CC=C1CN1CCN(C=2C(=CC=CN=2)C(=O)OC(C)C)CC1 WJCMIVBNCATQEE-UHFFFAOYSA-N 0.000 claims description 2
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- DLHDANBUASFLRI-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(4-fluorophenoxy)methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(COC=3C=CC(F)=CC=3)=CC=2)CC1 DLHDANBUASFLRI-UHFFFAOYSA-N 0.000 claims description 2
- UEIFZTPTFTWFIZ-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(4-fluorophenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C=CC(F)=CC=3)=CC=2)CC1 UEIFZTPTFTWFIZ-UHFFFAOYSA-N 0.000 claims description 2
- OKFOHAOFKPTQCF-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(4-methoxycarbonylphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C1=CC(C(=O)OC)=CC=C1COC(C=C1)=CC=C1CN1CCN(C=2C(=CC=CN=2)C(=O)OC(C)C)CC1 OKFOHAOFKPTQCF-UHFFFAOYSA-N 0.000 claims description 2
- PCKMGZMQQHSEAF-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(4-methoxyphenoxy)methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C1=CC(OC)=CC=C1OCC(C=C1)=CC=C1CN1CCN(C=2C(=CC=CN=2)C(=O)OC(C)C)CC1 PCKMGZMQQHSEAF-UHFFFAOYSA-N 0.000 claims description 2
- GPUGIPQXRLRURK-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(4-methoxyphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C1=CC(OC)=CC=C1COC(C=C1)=CC=C1CN1CCN(C=2C(=CC=CN=2)C(=O)OC(C)C)CC1 GPUGIPQXRLRURK-UHFFFAOYSA-N 0.000 claims description 2
- XKBHEXKRTXZADP-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(4-methylphenoxy)methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(COC=3C=CC(C)=CC=3)=CC=2)CC1 XKBHEXKRTXZADP-UHFFFAOYSA-N 0.000 claims description 2
- LCLJQYHOZCHUGK-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(4-methylphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C=CC(C)=CC=3)=CC=2)CC1 LCLJQYHOZCHUGK-UHFFFAOYSA-N 0.000 claims description 2
- QEXLGEZWJSKSRN-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(4-methylsulfonylphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C=CC(=CC=3)S(C)(=O)=O)=CC=2)CC1 QEXLGEZWJSKSRN-UHFFFAOYSA-N 0.000 claims description 2
- XDYKHBALHWFETK-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(4-propan-2-ylphenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C=CC(=CC=3)C(C)C)=CC=2)CC1 XDYKHBALHWFETK-UHFFFAOYSA-N 0.000 claims description 2
- PIMZJEKVSKNGCO-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(5-chloro-2-fluorophenyl)methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C(=CC=C(Cl)C=3)F)=CC=2)CC1 PIMZJEKVSKNGCO-UHFFFAOYSA-N 0.000 claims description 2
- YCYFBQLJKJFNKC-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[(benzylamino)methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(CNCC=3C=CC=CC=3)=CC=2)CC1 YCYFBQLJKJFNKC-UHFFFAOYSA-N 0.000 claims description 2
- VRIUYMYZKWLSIQ-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[2-(trifluoromethoxy)anilino]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(NC=3C(=CC=CC=3)OC(F)(F)F)=CC=2)CC1 VRIUYMYZKWLSIQ-UHFFFAOYSA-N 0.000 claims description 2
- UFFSDIHABKGUMH-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[[(2-chlorophenyl)methyl-ethylamino]methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C=1C=CC=C(Cl)C=1CN(CC)CC(C=C1)=CC=C1CN(CC1)CCN1C1=NC=CC=C1C(=O)OC(C)C UFFSDIHABKGUMH-UHFFFAOYSA-N 0.000 claims description 2
- NJJUCTRCMAAPSR-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[[(2-fluorobenzoyl)amino]methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical group CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(CNC(=O)C=3C(=CC=CC=3)F)=CC=2)CC1 NJJUCTRCMAAPSR-UHFFFAOYSA-N 0.000 claims description 2
- SOQCJWUBYHRNQM-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[[(2-fluorophenyl)methylamino]methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(CNCC=3C(=CC=CC=3)F)=CC=2)CC1 SOQCJWUBYHRNQM-UHFFFAOYSA-N 0.000 claims description 2
- KDELUSPWWHLPAT-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[[(3-chlorophenyl)methyl-ethylamino]methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C=1C=CC(Cl)=CC=1CN(CC)CC(C=C1)=CC=C1CN(CC1)CCN1C1=NC=CC=C1C(=O)OC(C)C KDELUSPWWHLPAT-UHFFFAOYSA-N 0.000 claims description 2
- KXZGKGFOELZVSO-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[[(4-chlorophenyl)methyl-ethylamino]methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C=1C=C(CN2CCN(CC2)C=2C(=CC=CN=2)C(=O)OC(C)C)C=CC=1CN(CC)CC1=CC=C(Cl)C=C1 KXZGKGFOELZVSO-UHFFFAOYSA-N 0.000 claims description 2
- HFOZCSBSQFVBSX-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[[2-(trifluoromethyl)phenoxy]methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(COC=3C(=CC=CC=3)C(F)(F)F)=CC=2)CC1 HFOZCSBSQFVBSX-UHFFFAOYSA-N 0.000 claims description 2
- FOYTWLKMIYZKMI-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[[2-(trifluoromethyl)phenyl]methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C(=CC=CC=3)C(F)(F)F)=CC=2)CC1 FOYTWLKMIYZKMI-UHFFFAOYSA-N 0.000 claims description 2
- ANQQDVGTJJJFIY-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[[3-(dimethylamino)phenyl]methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C=C(C=CC=3)N(C)C)=CC=2)CC1 ANQQDVGTJJJFIY-UHFFFAOYSA-N 0.000 claims description 2
- CSKFBGZYXNBVJC-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[[3-(trifluoromethyl)phenyl]methoxy]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(OCC=3C=C(C=CC=3)C(F)(F)F)=CC=2)CC1 CSKFBGZYXNBVJC-UHFFFAOYSA-N 0.000 claims description 2
- FHLPCTACCZNKCX-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[[4-[(2-chloro-6-fluorophenyl)methyl]piperazin-1-yl]methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1N1CCN(CC=2C=CC(CN3CCN(CC=4C(=CC=CC=4F)Cl)CC3)=CC=2)CC1 FHLPCTACCZNKCX-UHFFFAOYSA-N 0.000 claims description 2
- GPIIIHBDAYYGRB-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[[benzyl(ethyl)amino]methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C=1C=C(CN2CCN(CC2)C=2C(=CC=CN=2)C(=O)OC(C)C)C=CC=1CN(CC)CC1=CC=CC=C1 GPIIIHBDAYYGRB-UHFFFAOYSA-N 0.000 claims description 2
- CQPGKNUXBJCXDC-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[[benzyl(ethyl)amino]methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate;dihydrochloride Chemical compound Cl.Cl.C=1C=C(CN2CCN(CC2)C=2C(=CC=CN=2)C(=O)OC(C)C)C=CC=1CN(CC)CC1=CC=CC=C1 CQPGKNUXBJCXDC-UHFFFAOYSA-N 0.000 claims description 2
- LGOWSFCXBRRKNH-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[[ethyl(furan-2-ylmethyl)amino]methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C=1C=C(CN2CCN(CC2)C=2C(=CC=CN=2)C(=O)OC(C)C)C=CC=1CN(CC)CC1=CC=CO1 LGOWSFCXBRRKNH-UHFFFAOYSA-N 0.000 claims description 2
- JZKLOGRZYVCHSK-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[[ethyl(furan-3-ylmethyl)amino]methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C=1C=C(CN2CCN(CC2)C=2C(=CC=CN=2)C(=O)OC(C)C)C=CC=1CN(CC)CC=1C=COC=1 JZKLOGRZYVCHSK-UHFFFAOYSA-N 0.000 claims description 2
- BIBGZBDCUKDKSA-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[[ethyl(thiophen-2-ylmethyl)amino]methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C=1C=C(CN2CCN(CC2)C=2C(=CC=CN=2)C(=O)OC(C)C)C=CC=1CN(CC)CC1=CC=CS1 BIBGZBDCUKDKSA-UHFFFAOYSA-N 0.000 claims description 2
- LSDCPMGLDJKPNK-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[[ethyl-[(2-fluorophenyl)methyl]amino]methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C=1C=CC=C(F)C=1CN(CC)CC(C=C1)=CC=C1CN(CC1)CCN1C1=NC=CC=C1C(=O)OC(C)C LSDCPMGLDJKPNK-UHFFFAOYSA-N 0.000 claims description 2
- LZGJFQAQELONPG-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[[ethyl-[(3-fluorophenyl)methyl]amino]methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C=1C=CC(F)=CC=1CN(CC)CC(C=C1)=CC=C1CN(CC1)CCN1C1=NC=CC=C1C(=O)OC(C)C LZGJFQAQELONPG-UHFFFAOYSA-N 0.000 claims description 2
- NBMQFTRDUGSLNF-UHFFFAOYSA-N propan-2-yl 2-[4-[[4-[[ethyl-[(4-fluorophenyl)methyl]amino]methyl]phenyl]methyl]piperazin-1-yl]pyridine-3-carboxylate Chemical compound C=1C=C(CN2CCN(CC2)C=2C(=CC=CN=2)C(=O)OC(C)C)C=CC=1CN(CC)CC1=CC=C(F)C=C1 NBMQFTRDUGSLNF-UHFFFAOYSA-N 0.000 claims description 2
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- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
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- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
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- MIWNRZQEZIFLSG-UHFFFAOYSA-N [2-[4-[[4-[[(2-chloro-6-fluorophenyl)methyl-ethylamino]methyl]phenyl]methyl]piperazin-1-yl]pyridin-3-yl]methyl cyclopropanecarboxylate Chemical compound FC=1C=CC=C(Cl)C=1CN(CC)CC(C=C1)=CC=C1CN(CC1)CCN1C1=NC=CC=C1COC(=O)C1CC1 MIWNRZQEZIFLSG-UHFFFAOYSA-N 0.000 claims 1
- AHRXJJXZIXUTNB-UHFFFAOYSA-N [2-[4-[[4-[[(2-chloro-6-fluorophenyl)methyl-ethylamino]methyl]phenyl]methyl]piperazin-1-yl]pyridin-3-yl]methyl propanoate Chemical class FC=1C=CC=C(Cl)C=1CN(CC)CC(C=C1)=CC=C1CN(CC1)CCN1C1=NC=CC=C1COC(=O)CC AHRXJJXZIXUTNB-UHFFFAOYSA-N 0.000 claims 1
- SGDNBFUALVARSN-FHQKDBNESA-N [O-]C(=O)\C=C/C([O-])=O.[O-]C(=O)\C=C/C([O-])=O.FC=1C=CC=C(Cl)C=1C[NH+](CC)CC(C=C1)=CC=C1C[NH+](CC1)CCN1C1=NC=CC=C1C(=O)OC(C)C.FC=1C=CC=C(Cl)C=1C[NH+](CC)CC(C=C1)=CC=C1C[NH+](CC1)CCN1C1=NC=CC=C1C(=O)OC(C)C Chemical compound [O-]C(=O)\C=C/C([O-])=O.[O-]C(=O)\C=C/C([O-])=O.FC=1C=CC=C(Cl)C=1C[NH+](CC)CC(C=C1)=CC=C1C[NH+](CC1)CCN1C1=NC=CC=C1C(=O)OC(C)C.FC=1C=CC=C(Cl)C=1C[NH+](CC)CC(C=C1)=CC=C1C[NH+](CC1)CCN1C1=NC=CC=C1C(=O)OC(C)C SGDNBFUALVARSN-FHQKDBNESA-N 0.000 claims 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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| EA201992707A1 (ru) | 2013-11-18 | 2020-06-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
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| RU2019114964A (ru) | 2016-10-17 | 2020-11-17 | Дженентек, Инк. | Терапевтические средства и способы их применения |
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| EP3774801A1 (en) | 2018-03-30 | 2021-02-17 | F. Hoffmann-La Roche AG | Fused ring hydro-pyrido compounds as sodium channel inhibitors |
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| KR102845511B1 (ko) * | 2019-02-08 | 2025-08-12 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
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- 2011-01-13 KR KR1020127021186A patent/KR20120124064A/ko not_active Withdrawn
- 2011-01-13 AU AU2011205302A patent/AU2011205302B2/en not_active Ceased
- 2011-01-13 PH PH1/2012/501421A patent/PH12012501421A1/en unknown
- 2011-01-13 US US13/522,183 patent/US20130023541A1/en not_active Abandoned
- 2011-01-13 MA MA35122A patent/MA33987B1/fr unknown
- 2011-01-13 EA EA201290644A patent/EA201290644A1/ru unknown
- 2011-01-13 SG SG2012050068A patent/SG182400A1/en unknown
- 2011-01-13 MX MX2012008285A patent/MX2012008285A/es not_active Application Discontinuation
- 2011-01-13 JP JP2012549074A patent/JP2013517283A/ja active Pending
- 2011-01-13 PE PE2012000982A patent/PE20121518A1/es not_active Application Discontinuation
- 2011-01-13 NZ NZ601126A patent/NZ601126A/en not_active IP Right Cessation
- 2011-01-13 WO PCT/US2011/021114 patent/WO2011088201A1/en not_active Ceased
- 2011-01-13 CA CA2787025A patent/CA2787025A1/en not_active Abandoned
- 2011-01-13 EP EP11733370.8A patent/EP2523665A4/en not_active Withdrawn
- 2011-01-14 UY UY33186A patent/UY33186A/es not_active Application Discontinuation
- 2011-01-14 AR ARP110100127A patent/AR079906A1/es unknown
-
2012
- 2012-07-09 IL IL220836A patent/IL220836A0/en unknown
- 2012-07-10 ZA ZA2012/05126A patent/ZA201205126B/en unknown
- 2012-07-13 CL CL2012001971A patent/CL2012001971A1/es unknown
- 2012-07-13 CO CO12118387A patent/CO6592051A2/es active IP Right Grant
- 2012-07-31 CR CR20120402A patent/CR20120402A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR079906A1 (es) | 2012-02-29 |
| PE20121518A1 (es) | 2012-12-12 |
| CA2787025A1 (en) | 2011-07-21 |
| SG182400A1 (en) | 2012-08-30 |
| MX2012008285A (es) | 2012-08-03 |
| CR20120402A (es) | 2012-09-03 |
| ZA201205126B (en) | 2013-03-27 |
| EP2523665A4 (en) | 2013-07-03 |
| AU2011205302B2 (en) | 2014-10-09 |
| NZ601126A (en) | 2014-10-31 |
| TW201139406A (en) | 2011-11-16 |
| CN102802627A (zh) | 2012-11-28 |
| EP2523665A1 (en) | 2012-11-21 |
| JP2013517283A (ja) | 2013-05-16 |
| WO2011088201A1 (en) | 2011-07-21 |
| CL2012001971A1 (es) | 2013-01-25 |
| BR112012017266A2 (pt) | 2016-04-19 |
| MA33987B1 (fr) | 2013-02-01 |
| IL220836A0 (en) | 2012-08-30 |
| EA201290644A1 (ru) | 2012-12-28 |
| US20130023541A1 (en) | 2013-01-24 |
| UY33186A (enExample) | 2011-07-29 |
| AU2011205302A1 (en) | 2012-08-02 |
| PH12012501421A1 (en) | 2017-08-09 |
| CO6592051A2 (es) | 2013-01-02 |
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| PA0105 | International application |
Patent event date: 20120813 Patent event code: PA01051R01D Comment text: International Patent Application |
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| PG1501 | Laying open of application | ||
| PC1203 | Withdrawal of no request for examination | ||
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |