ZA200502276B - Diaryl ethers as opioid receptor antagonist - Google Patents
Diaryl ethers as opioid receptor antagonist Download PDFInfo
- Publication number
- ZA200502276B ZA200502276B ZA200502276A ZA200502276A ZA200502276B ZA 200502276 B ZA200502276 B ZA 200502276B ZA 200502276 A ZA200502276 A ZA 200502276A ZA 200502276 A ZA200502276 A ZA 200502276A ZA 200502276 B ZA200502276 B ZA 200502276B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenoxy
- nicotinamide
- methyl
- ethyl
- phenyl
- Prior art date
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- 229940123257 Opioid receptor antagonist Drugs 0.000 title description 4
- 239000003401 opiate antagonist Substances 0.000 title description 4
- 150000001987 diarylethers Chemical class 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 171
- 150000001875 compounds Chemical class 0.000 claims description 93
- 229910052739 hydrogen Inorganic materials 0.000 claims description 77
- 239000001257 hydrogen Substances 0.000 claims description 76
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 73
- -1 chloro, bromo, methoxy, ethoxy, methyl Chemical group 0.000 claims description 69
- 125000003118 aryl group Chemical group 0.000 claims description 63
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 55
- 125000003342 alkenyl group Chemical group 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 47
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
- 150000002431 hydrogen Chemical class 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
- 125000000304 alkynyl group Chemical group 0.000 claims description 31
- 125000001188 haloalkyl group Chemical group 0.000 claims description 31
- 208000008589 Obesity Diseases 0.000 claims description 29
- 235000020824 obesity Nutrition 0.000 claims description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 24
- 238000011282 treatment Methods 0.000 claims description 24
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 239000012453 solvate Substances 0.000 claims description 23
- 201000010099 disease Diseases 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 17
- 125000004001 thioalkyl group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
- 125000001624 naphthyl group Chemical group 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 13
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 125000002619 bicyclic group Chemical group 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 8
- 208000024891 symptom Diseases 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 230000004580 weight loss Effects 0.000 claims description 5
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- XLSUSYVBQYFCGM-UHFFFAOYSA-N 6-[4-[2-[benzyl(2-phenylethyl)amino]ethyl]phenoxy]pyridine-3-carboxamide Chemical compound N1=CC(C(=O)N)=CC=C1OC(C=C1)=CC=C1CCN(CC=1C=CC=CC=1)CCC1=CC=CC=C1 XLSUSYVBQYFCGM-UHFFFAOYSA-N 0.000 claims description 3
- JPJZAZLTRFFPHP-UHFFFAOYSA-N 6-[4-[2-[benzyl(3-phenylpropyl)amino]ethyl]phenoxy]pyridine-3-carboxamide Chemical compound N1=CC(C(=O)N)=CC=C1OC(C=C1)=CC=C1CCN(CC=1C=CC=CC=1)CCCC1=CC=CC=C1 JPJZAZLTRFFPHP-UHFFFAOYSA-N 0.000 claims description 3
- JDWUVBTYGYRQQS-UHFFFAOYSA-N 6-[4-[2-[benzyl(heptyl)amino]ethyl]phenoxy]pyridine-3-carboxamide Chemical compound C=1C=CC=CC=1CN(CCCCCCC)CCC(C=C1)=CC=C1OC1=CC=C(C(N)=O)C=N1 JDWUVBTYGYRQQS-UHFFFAOYSA-N 0.000 claims description 3
- BKHZPPRSRAFKME-UHFFFAOYSA-N 6-[4-[2-[benzyl(hexyl)amino]ethyl]phenoxy]pyridine-3-carboxamide Chemical compound C=1C=CC=CC=1CN(CCCCCC)CCC(C=C1)=CC=C1OC1=CC=C(C(N)=O)C=N1 BKHZPPRSRAFKME-UHFFFAOYSA-N 0.000 claims description 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 description 3
- 150000003973 alkyl amines Chemical class 0.000 claims description 3
- 125000004043 oxo group Chemical group O=* 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 21
- 125000004897 3-methylbutylamino group Chemical group CC(CCN*)C 0.000 claims 19
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 claims 18
- 229960003966 nicotinamide Drugs 0.000 claims 18
- 239000011570 nicotinamide Substances 0.000 claims 18
- 239000000126 substance Substances 0.000 claims 17
- 125000004911 3,3-dimethylbutylamino group Chemical group CC(CCN*)(C)C 0.000 claims 10
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 10
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 8
- 230000000903 blocking effect Effects 0.000 claims 6
- 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims 6
- MHTPAXQXPKKCNG-UHFFFAOYSA-N 6-[4-[(2-ethylbutylamino)methyl]-2-methoxyphenoxy]pyridine-3-carboxamide Chemical compound COC1=CC(CNCC(CC)CC)=CC=C1OC1=CC=C(C(N)=O)C=N1 MHTPAXQXPKKCNG-UHFFFAOYSA-N 0.000 claims 5
- ADXBHKREPBWTDP-UHFFFAOYSA-N 6-[4-[(3-methylbutylamino)methyl]phenoxy]pyridine-3-carboxamide Chemical compound C1=CC(CNCCC(C)C)=CC=C1OC1=CC=C(C(N)=O)C=N1 ADXBHKREPBWTDP-UHFFFAOYSA-N 0.000 claims 5
- 241000124008 Mammalia Species 0.000 claims 5
- 125000004905 4-methylpentylamino group Chemical group CC(CCCN*)C 0.000 claims 4
- NICFMWRZPWQTTB-UHFFFAOYSA-N 6-[2-methoxy-4-[(3-methylbutylamino)methyl]phenoxy]pyridine-3-carboxamide Chemical compound COC1=CC(CNCCC(C)C)=CC=C1OC1=CC=C(C(N)=O)C=N1 NICFMWRZPWQTTB-UHFFFAOYSA-N 0.000 claims 4
- ZTROKUVCIXKYCV-UHFFFAOYSA-N 6-[4-[(2-phenylethylamino)methyl]phenoxy]pyridine-3-carboximidamide Chemical compound N1=CC(C(=N)N)=CC=C1OC(C=C1)=CC=C1CNCCC1=CC=CC=C1 ZTROKUVCIXKYCV-UHFFFAOYSA-N 0.000 claims 4
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 4
- 239000000833 heterodimer Substances 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- AWJPDSMGQGPILL-UHFFFAOYSA-N methanesulfonic acid;pyridine-3-carboxamide Chemical compound CS(O)(=O)=O.NC(=O)C1=CC=CN=C1 AWJPDSMGQGPILL-UHFFFAOYSA-N 0.000 claims 4
- 235000005152 nicotinamide Nutrition 0.000 claims 4
- LFBXAEHQTYUOBS-UHFFFAOYSA-N 3-fluoro-4-[2-methyl-4-[(3-methylbutylamino)methyl]phenoxy]benzamide Chemical compound CC1=CC(CNCCC(C)C)=CC=C1OC1=CC=C(C(N)=O)C=C1F LFBXAEHQTYUOBS-UHFFFAOYSA-N 0.000 claims 3
- YEKAXYJRFMIMLJ-UHFFFAOYSA-N 5-[2-chloro-4-[(pentylamino)methyl]phenoxy]pyridine-2-carboxamide Chemical compound ClC1=CC(CNCCCCC)=CC=C1OC1=CC=C(C(N)=O)N=C1 YEKAXYJRFMIMLJ-UHFFFAOYSA-N 0.000 claims 3
- XVFODPPOWNOUNK-UHFFFAOYSA-N 5-[2-fluoro-4-[(pentylamino)methyl]phenoxy]pyridine-2-carboxamide Chemical compound FC1=CC(CNCCCCC)=CC=C1OC1=CC=C(C(N)=O)N=C1 XVFODPPOWNOUNK-UHFFFAOYSA-N 0.000 claims 3
- KXIFIKGCMNZIRR-UHFFFAOYSA-N 5-[2-methoxy-4-[(pentylamino)methyl]phenoxy]pyrazine-2-carboxamide Chemical compound COC1=CC(CNCCCCC)=CC=C1OC1=CN=C(C(N)=O)C=N1 KXIFIKGCMNZIRR-UHFFFAOYSA-N 0.000 claims 3
- QVHMCEVUNFBRCJ-UHFFFAOYSA-N 5-[2-methyl-4-[(3-methylbutylamino)methyl]phenoxy]pyrazine-2-carboxamide Chemical compound CC1=CC(CNCCC(C)C)=CC=C1OC1=CN=C(C(N)=O)C=N1 QVHMCEVUNFBRCJ-UHFFFAOYSA-N 0.000 claims 3
- OUANICYGXKJINI-UHFFFAOYSA-N 6-[2-ethoxy-4-[(3-methylbutylamino)methyl]phenoxy]pyridine-3-carboxamide Chemical compound CCOC1=CC(CNCCC(C)C)=CC=C1OC1=CC=C(C(N)=O)C=N1 OUANICYGXKJINI-UHFFFAOYSA-N 0.000 claims 3
- KVOQIWDZGPBFDX-UHFFFAOYSA-N 6-[2-methyl-4-[[methyl(3-methylbutyl)amino]methyl]phenoxy]pyridine-3-carboxamide Chemical compound CC1=CC(CN(C)CCC(C)C)=CC=C1OC1=CC=C(C(N)=O)C=N1 KVOQIWDZGPBFDX-UHFFFAOYSA-N 0.000 claims 3
- OHHQIRLRDUVKEN-UHFFFAOYSA-N 6-[4-[(3,3-dimethylbutylamino)methyl]-2-methoxyphenoxy]pyridine-3-carboxamide Chemical compound COC1=CC(CNCCC(C)(C)C)=CC=C1OC1=CC=C(C(N)=O)C=N1 OHHQIRLRDUVKEN-UHFFFAOYSA-N 0.000 claims 3
- ZQRSJYJPFBTANQ-UHFFFAOYSA-N 6-[4-[(3,3-dimethylbutylamino)methyl]-2-methylphenoxy]pyridine-3-carboxamide Chemical compound CC1=CC(CNCCC(C)(C)C)=CC=C1OC1=CC=C(C(N)=O)C=N1 ZQRSJYJPFBTANQ-UHFFFAOYSA-N 0.000 claims 3
- LHWQPEJTJZBUML-UHFFFAOYSA-N 6-[4-[(hexylamino)methyl]-2-methoxyphenoxy]pyridine-3-carboxamide Chemical compound COC1=CC(CNCCCCCC)=CC=C1OC1=CC=C(C(N)=O)C=N1 LHWQPEJTJZBUML-UHFFFAOYSA-N 0.000 claims 3
- UZWDALCERDNUMM-UHFFFAOYSA-N 6-[4-[(hexylamino)methyl]-2-methoxyphenoxy]pyridine-3-carboxamide;methanesulfonic acid Chemical compound CS(O)(=O)=O.COC1=CC(CNCCCCCC)=CC=C1OC1=CC=C(C(N)=O)C=N1 UZWDALCERDNUMM-UHFFFAOYSA-N 0.000 claims 3
- MPAAEZPHTFLIIG-UHFFFAOYSA-N 6-[4-[2-(3,3-dimethylbutylamino)ethyl]-2,6-difluorophenoxy]pyridine-3-carboxamide Chemical compound FC1=CC(CCNCCC(C)(C)C)=CC(F)=C1OC1=CC=C(C(N)=O)C=N1 MPAAEZPHTFLIIG-UHFFFAOYSA-N 0.000 claims 3
- ZGCYVRNZWGUXNQ-UHFFFAOYSA-N Bevenopran Chemical compound C=1C=C(OC=2N=CC(=NC=2)C(N)=O)C(OC)=CC=1CNCCC1CCOCC1 ZGCYVRNZWGUXNQ-UHFFFAOYSA-N 0.000 claims 3
- AIYUWOOEBYTVKG-UHFFFAOYSA-N methanesulfonic acid;pyridine-2-carboxamide Chemical compound CS(O)(=O)=O.NC(=O)C1=CC=CC=N1 AIYUWOOEBYTVKG-UHFFFAOYSA-N 0.000 claims 3
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 claims 3
- YLLVGEIRKKEJEA-UHFFFAOYSA-N 2-[4-[2-(benzylamino)ethyl]phenoxy]-4-fluorobenzamide Chemical compound NC(=O)C1=CC=C(F)C=C1OC(C=C1)=CC=C1CCNCC1=CC=CC=C1 YLLVGEIRKKEJEA-UHFFFAOYSA-N 0.000 claims 2
- GVUCSVIJHDIURV-UHFFFAOYSA-N 2-[4-[2-(benzylamino)ethyl]phenoxy]pyridine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=C1OC(C=C1)=CC=C1CCNCC1=CC=CC=C1 GVUCSVIJHDIURV-UHFFFAOYSA-N 0.000 claims 2
- LYBVJRGNHGNDMJ-UHFFFAOYSA-N 2-[4-[5-(aminomethyl)pyridin-2-yl]oxyphenyl]-n-benzylethanamine Chemical compound N1=CC(CN)=CC=C1OC(C=C1)=CC=C1CCNCC1=CC=CC=C1 LYBVJRGNHGNDMJ-UHFFFAOYSA-N 0.000 claims 2
- ZSCOUZIIPQFXIM-UHFFFAOYSA-N 2-chloro-4-[4-[(2-phenylethylamino)methyl]phenoxy]benzamide Chemical compound C1=C(Cl)C(C(=O)N)=CC=C1OC(C=C1)=CC=C1CNCCC1=CC=CC=C1 ZSCOUZIIPQFXIM-UHFFFAOYSA-N 0.000 claims 2
- WQGNLWYXXDUVQL-UHFFFAOYSA-N 3-chloro-4-[4-[(2-phenylethylamino)methyl]phenoxy]benzamide Chemical compound ClC1=CC(C(=O)N)=CC=C1OC(C=C1)=CC=C1CNCCC1=CC=CC=C1 WQGNLWYXXDUVQL-UHFFFAOYSA-N 0.000 claims 2
- VMWJPJYLAHKLLC-UHFFFAOYSA-N 3-fluoro-4-[4-[(2-phenylethylamino)methyl]phenoxy]benzamide Chemical compound FC1=CC(C(=O)N)=CC=C1OC(C=C1)=CC=C1CNCCC1=CC=CC=C1 VMWJPJYLAHKLLC-UHFFFAOYSA-N 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- FWMXWDSVFAEPCC-UHFFFAOYSA-N 4-[3-chloro-5-[[2-(3-chlorophenyl)ethylamino]methyl]pyridin-2-yl]oxybenzamide Chemical compound C1=CC(C(=O)N)=CC=C1OC(C(=C1)Cl)=NC=C1CNCCC1=CC=CC(Cl)=C1 FWMXWDSVFAEPCC-UHFFFAOYSA-N 0.000 claims 2
- KTFDVGGSWFOYTI-UHFFFAOYSA-N 4-[4-(2-phenylethylamino)phenoxy]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1OC(C=C1)=CC=C1NCCC1=CC=CC=C1 KTFDVGGSWFOYTI-UHFFFAOYSA-N 0.000 claims 2
- JCCQVASQJDFTNG-UHFFFAOYSA-N 4-[4-(3-phenylpropylamino)phenoxy]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1OC(C=C1)=CC=C1NCCCC1=CC=CC=C1 JCCQVASQJDFTNG-UHFFFAOYSA-N 0.000 claims 2
- WXHVVWFXOHALKT-UHFFFAOYSA-N 4-[4-(benzylamino)phenoxy]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1OC(C=C1)=CC=C1NCC1=CC=CC=C1 WXHVVWFXOHALKT-UHFFFAOYSA-N 0.000 claims 2
- PHYGLWXCKRODAU-UHFFFAOYSA-N 4-[4-[(2-cyclopentylethylamino)methyl]phenoxy]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1OC(C=C1)=CC=C1CNCCC1CCCC1 PHYGLWXCKRODAU-UHFFFAOYSA-N 0.000 claims 2
- LQOXGQIRZIKCHV-UHFFFAOYSA-N 4-[4-[(2-phenylpropylamino)methyl]phenoxy]benzamide Chemical compound C=1C=CC=CC=1C(C)CNCC(C=C1)=CC=C1OC1=CC=C(C(N)=O)C=C1 LQOXGQIRZIKCHV-UHFFFAOYSA-N 0.000 claims 2
- RJMQAVZPAFHQLE-UHFFFAOYSA-N 4-[4-[(pentylamino)methyl]phenoxy]benzamide Chemical compound C1=CC(CNCCCCC)=CC=C1OC1=CC=C(C(N)=O)C=C1 RJMQAVZPAFHQLE-UHFFFAOYSA-N 0.000 claims 2
- QORKXQXXTQDKBS-UHFFFAOYSA-N 4-[4-[2-(benzylamino)ethyl]phenoxy]-2-chlorobenzamide Chemical compound C1=C(Cl)C(C(=O)N)=CC=C1OC(C=C1)=CC=C1CCNCC1=CC=CC=C1 QORKXQXXTQDKBS-UHFFFAOYSA-N 0.000 claims 2
- IHJVFKZLDJZZMO-UHFFFAOYSA-N 4-[4-[2-(benzylamino)ethyl]phenoxy]-2-fluorobenzamide Chemical compound C1=C(F)C(C(=O)N)=CC=C1OC(C=C1)=CC=C1CCNCC1=CC=CC=C1 IHJVFKZLDJZZMO-UHFFFAOYSA-N 0.000 claims 2
- KOXIGTOGGYUAIC-UHFFFAOYSA-N 4-[4-[[(2,6-dichlorophenyl)methylamino]methyl]phenoxy]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1OC(C=C1)=CC=C1CNCC1=C(Cl)C=CC=C1Cl KOXIGTOGGYUAIC-UHFFFAOYSA-N 0.000 claims 2
- GBNFDVFRBHKXGG-UHFFFAOYSA-N 4-[4-[[(4-fluorophenyl)methylamino]methyl]phenoxy]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1OC(C=C1)=CC=C1CNCC1=CC=C(F)C=C1 GBNFDVFRBHKXGG-UHFFFAOYSA-N 0.000 claims 2
- SAKNLICUALLOQM-UHFFFAOYSA-N 4-[4-[[2-(2,4-dichlorophenyl)ethylamino]methyl]phenoxy]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1OC(C=C1)=CC=C1CNCCC1=CC=C(Cl)C=C1Cl SAKNLICUALLOQM-UHFFFAOYSA-N 0.000 claims 2
- TYSLDLBJENZVST-UHFFFAOYSA-N 4-[4-[[2-(2,6-dichlorophenyl)ethylamino]methyl]phenoxy]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1OC(C=C1)=CC=C1CNCCC1=C(Cl)C=CC=C1Cl TYSLDLBJENZVST-UHFFFAOYSA-N 0.000 claims 2
- OHINXTVDIBEJGB-UHFFFAOYSA-N 4-[4-[[2-(2-chlorophenyl)ethylamino]methyl]phenoxy]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1OC(C=C1)=CC=C1CNCCC1=CC=CC=C1Cl OHINXTVDIBEJGB-UHFFFAOYSA-N 0.000 claims 2
- KUDORAXWVWONNR-UHFFFAOYSA-N 4-[4-[[2-(2-fluorophenyl)ethylamino]methyl]phenoxy]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1OC(C=C1)=CC=C1CNCCC1=CC=CC=C1F KUDORAXWVWONNR-UHFFFAOYSA-N 0.000 claims 2
- KJTWSAMGJMWOQE-UHFFFAOYSA-N 4-[4-[[2-(3-chlorophenyl)ethylamino]methyl]phenoxy]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1OC(C=C1)=CC=C1CNCCC1=CC=CC(Cl)=C1 KJTWSAMGJMWOQE-UHFFFAOYSA-N 0.000 claims 2
- IYEGSWKZNHZDBQ-UHFFFAOYSA-N 4-[4-[[2-(3-fluorophenyl)ethylamino]methyl]phenoxy]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1OC(C=C1)=CC=C1CNCCC1=CC=CC(F)=C1 IYEGSWKZNHZDBQ-UHFFFAOYSA-N 0.000 claims 2
- PABCCZSWGPTLTN-UHFFFAOYSA-N 4-[4-[[2-(4-fluorophenyl)ethylamino]methyl]phenoxy]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1OC(C=C1)=CC=C1CNCCC1=CC=C(F)C=C1 PABCCZSWGPTLTN-UHFFFAOYSA-N 0.000 claims 2
- SJVBRUCCVXXMKY-UHFFFAOYSA-N 4-[4-[[[4-(trifluoromethoxy)phenyl]methylamino]methyl]phenoxy]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1OC(C=C1)=CC=C1CNCC1=CC=C(OC(F)(F)F)C=C1 SJVBRUCCVXXMKY-UHFFFAOYSA-N 0.000 claims 2
- RZRPKKBCUBSAJI-UHFFFAOYSA-N 5-[2-chloro-4-[(2-pyridin-3-ylethylamino)methyl]phenoxy]pyridine-2-carboxamide Chemical compound C1=NC(C(=O)N)=CC=C1OC(C(=C1)Cl)=CC=C1CNCCC1=CC=CN=C1 RZRPKKBCUBSAJI-UHFFFAOYSA-N 0.000 claims 2
- YAMACEIRCGSTTI-UHFFFAOYSA-N 5-[2-chloro-4-[(2-thiophen-2-ylethylamino)methyl]phenoxy]pyridine-2-carboxamide Chemical compound C1=NC(C(=O)N)=CC=C1OC(C(=C1)Cl)=CC=C1CNCCC1=CC=CS1 YAMACEIRCGSTTI-UHFFFAOYSA-N 0.000 claims 2
- LVUJXCSJXGRJPH-UHFFFAOYSA-N 5-[2-fluoro-4-[(2-pyridin-3-ylethylamino)methyl]phenoxy]pyridine-2-carboxamide Chemical compound C1=NC(C(=O)N)=CC=C1OC(C(=C1)F)=CC=C1CNCCC1=CC=CN=C1 LVUJXCSJXGRJPH-UHFFFAOYSA-N 0.000 claims 2
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Classifications
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- 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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- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- C07D213/643—2-Phenoxypyridines; Derivatives thereof
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/46—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
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