JP2005531520A5 - - Google Patents
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- JP2005531520A5 JP2005531520A5 JP2003579734A JP2003579734A JP2005531520A5 JP 2005531520 A5 JP2005531520 A5 JP 2005531520A5 JP 2003579734 A JP2003579734 A JP 2003579734A JP 2003579734 A JP2003579734 A JP 2003579734A JP 2005531520 A5 JP2005531520 A5 JP 2005531520A5
- Authority
- JP
- Japan
- Prior art keywords
- chlorophenyl
- dichlorophenyl
- alkyl
- pyridine
- nicotinonitrile
- 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.)
- Pending
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- 125000000217 alkyl group Chemical group 0.000 claims 117
- 125000001424 substituent group Chemical group 0.000 claims 64
- 125000003118 aryl group Chemical group 0.000 claims 53
- 229910052739 hydrogen Inorganic materials 0.000 claims 53
- 239000001257 hydrogen Substances 0.000 claims 53
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 45
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 43
- 229910052736 halogen Inorganic materials 0.000 claims 34
- 150000002367 halogens Chemical class 0.000 claims 34
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 34
- 125000001072 heteroaryl group Chemical group 0.000 claims 23
- -1 cyclopropylmethoxy Chemical group 0.000 claims 20
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 16
- 125000003545 alkoxy group Chemical group 0.000 claims 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
- 125000004429 atom Chemical group 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 7
- NPDLYUOYAGBHFB-WDSKDSINSA-N Asn-Arg Chemical compound NC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N NPDLYUOYAGBHFB-WDSKDSINSA-N 0.000 claims 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 6
- 239000003937 drug carrier Substances 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 6
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims 6
- 125000004043 oxo group Chemical group O=* 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000001301 oxygen Substances 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 239000011593 sulfur Substances 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 5
- 208000030814 Eating disease Diseases 0.000 claims 5
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 5
- 208000008589 Obesity Diseases 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000000304 alkynyl group Chemical group 0.000 claims 5
- 125000004104 aryloxy group Chemical group 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 235000014632 disordered eating Nutrition 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 125000006606 n-butoxy group Chemical group 0.000 claims 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 5
- 235000020824 obesity Nutrition 0.000 claims 5
- 125000000062 cyclohexylmethoxy group Chemical group [H]C([H])(O*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 4
- 230000037406 food intake Effects 0.000 claims 4
- 235000012631 food intake Nutrition 0.000 claims 4
- HQPPJTUGTUANCS-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(3,4-difluorophenoxy)pyridine-3-carboxamide Chemical compound C=1C=C(Cl)C=C(Cl)C=1C=1N=C(OC=2C=C(F)C(F)=CC=2)C(C(=O)N)=CC=1C1=CC=C(Cl)C=C1 HQPPJTUGTUANCS-UHFFFAOYSA-N 0.000 claims 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 108020003175 receptors Proteins 0.000 claims 3
- 102000005962 receptors Human genes 0.000 claims 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 claims 2
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims 2
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 claims 2
- UHNJRKVMGGJKDS-UHFFFAOYSA-N 2-(3-chlorophenoxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyridine-3-carbonitrile Chemical compound C1=CC(Cl)=CC=C1C(C(=N1)C=2C(=CC(Cl)=CC=2)Cl)=CC(C#N)=C1OC1=CC=CC(Cl)=C1 UHNJRKVMGGJKDS-UHFFFAOYSA-N 0.000 claims 2
- OMLGPXXIQYFOSM-UHFFFAOYSA-N 2-(4-chlorophenoxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyridine-3-carbonitrile Chemical compound C1=CC(Cl)=CC=C1OC1=NC(C=2C(=CC(Cl)=CC=2)Cl)=C(C=2C=CC(Cl)=CC=2)C=C1C#N OMLGPXXIQYFOSM-UHFFFAOYSA-N 0.000 claims 2
- 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 2
- VXENZXMHWSMSBB-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-6-[(3,4-difluorophenyl)methoxy]pyridine Chemical compound C1=C(F)C(F)=CC=C1COC(N=C1C=2C(=CC(Cl)=CC=2)Cl)=CC=C1C1=CC=C(Cl)C=C1 VXENZXMHWSMSBB-UHFFFAOYSA-N 0.000 claims 2
- RXTUAOJEIAWETB-UHFFFAOYSA-N 5-(4-chlorophenyl)-2-(3,5-dichlorophenoxy)-6-(2,4-dichlorophenyl)pyridine-3-carbonitrile Chemical compound C1=CC(Cl)=CC=C1C(C(=N1)C=2C(=CC(Cl)=CC=2)Cl)=CC(C#N)=C1OC1=CC(Cl)=CC(Cl)=C1 RXTUAOJEIAWETB-UHFFFAOYSA-N 0.000 claims 2
- TUQXVTIUEVMLEA-UHFFFAOYSA-N 5-(4-chlorophenyl)-2-(5-chloropyridin-3-yl)oxy-6-(2,4-dichlorophenyl)pyridine-3-carbonitrile Chemical compound C1=CC(Cl)=CC=C1C(C(=N1)C=2C(=CC(Cl)=CC=2)Cl)=CC(C#N)=C1OC1=CN=CC(Cl)=C1 TUQXVTIUEVMLEA-UHFFFAOYSA-N 0.000 claims 2
- MJPHWVJHMTWHPX-UHFFFAOYSA-N 5-(4-chlorophenyl)-2-[(3-chlorophenyl)methoxy]-6-(2,4-dichlorophenyl)pyridine-3-carbonitrile Chemical compound C1=CC(Cl)=CC=C1C(C(=N1)C=2C(=CC(Cl)=CC=2)Cl)=CC(C#N)=C1OCC1=CC=CC(Cl)=C1 MJPHWVJHMTWHPX-UHFFFAOYSA-N 0.000 claims 2
- PVSSDPWBXZUKBJ-UHFFFAOYSA-N 5-(4-chlorophenyl)-2-cyclohexyloxy-6-(2,4-dichlorophenyl)pyridine-3-carbonitrile Chemical compound C1=CC(Cl)=CC=C1C(C(=N1)C=2C(=CC(Cl)=CC=2)Cl)=CC(C#N)=C1OC1CCCCC1 PVSSDPWBXZUKBJ-UHFFFAOYSA-N 0.000 claims 2
- DTUGSOQLNBOHAQ-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(3,4-difluorophenoxy)-n-ethylpyridine-3-carboxamide Chemical compound C=1C=C(Cl)C=C(Cl)C=1C=1N=C(OC=2C=C(F)C(F)=CC=2)C(C(=O)NCC)=CC=1C1=CC=C(Cl)C=C1 DTUGSOQLNBOHAQ-UHFFFAOYSA-N 0.000 claims 2
- RJWQSFKRHOUSJO-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(3,4-difluorophenoxy)-n-methylpyridine-3-carboxamide Chemical compound C=1C=C(Cl)C=C(Cl)C=1C=1N=C(OC=2C=C(F)C(F)=CC=2)C(C(=O)NC)=CC=1C1=CC=C(Cl)C=C1 RJWQSFKRHOUSJO-UHFFFAOYSA-N 0.000 claims 2
- RWZVVBVAUPBWHG-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(3,4-difluorophenoxy)-n-propan-2-ylpyridine-3-carboxamide Chemical compound C=1C=C(Cl)C=C(Cl)C=1C=1N=C(OC=2C=C(F)C(F)=CC=2)C(C(=O)NC(C)C)=CC=1C1=CC=C(Cl)C=C1 RWZVVBVAUPBWHG-UHFFFAOYSA-N 0.000 claims 2
- SPDRNWALGCLXAG-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(3,4-difluorophenoxy)-n-pyrrolidin-1-ylpyridine-3-carboxamide Chemical compound C1=C(F)C(F)=CC=C1OC1=NC(C=2C(=CC(Cl)=CC=2)Cl)=C(C=2C=CC(Cl)=CC=2)C=C1C(=O)NN1CCCC1 SPDRNWALGCLXAG-UHFFFAOYSA-N 0.000 claims 2
- OMIHQKYKCRPXPH-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(3,4-difluorophenoxy)pyridine-3-carbonitrile Chemical compound C1=C(F)C(F)=CC=C1OC1=NC(C=2C(=CC(Cl)=CC=2)Cl)=C(C=2C=CC(Cl)=CC=2)C=C1C#N OMIHQKYKCRPXPH-UHFFFAOYSA-N 0.000 claims 2
- ANBYXDYPKJILHK-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(3-fluorophenoxy)pyridine-3-carbonitrile Chemical compound FC1=CC=CC(OC=2C(=CC(=C(C=3C(=CC(Cl)=CC=3)Cl)N=2)C=2C=CC(Cl)=CC=2)C#N)=C1 ANBYXDYPKJILHK-UHFFFAOYSA-N 0.000 claims 2
- GVMVKUDTCSWOCV-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(4-fluorophenoxy)pyridine-3-carbonitrile Chemical compound C1=CC(F)=CC=C1OC1=NC(C=2C(=CC(Cl)=CC=2)Cl)=C(C=2C=CC(Cl)=CC=2)C=C1C#N GVMVKUDTCSWOCV-UHFFFAOYSA-N 0.000 claims 2
- QIERXXZDSLXNAV-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(4-methoxyphenoxy)pyridine-3-carbonitrile Chemical compound C1=CC(OC)=CC=C1OC1=NC(C=2C(=CC(Cl)=CC=2)Cl)=C(C=2C=CC(Cl)=CC=2)C=C1C#N QIERXXZDSLXNAV-UHFFFAOYSA-N 0.000 claims 2
- PUPIRIVKMRMBDY-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-[(2,4-difluorophenyl)methoxy]pyridine-3-carbonitrile Chemical compound FC1=CC(F)=CC=C1COC1=NC(C=2C(=CC(Cl)=CC=2)Cl)=C(C=2C=CC(Cl)=CC=2)C=C1C#N PUPIRIVKMRMBDY-UHFFFAOYSA-N 0.000 claims 2
- FPBZDYQUXHBXBO-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-[(3,4-difluorophenyl)methoxy]-n-methylpyridine-3-carboxamide Chemical compound C=1C=C(Cl)C=C(Cl)C=1C=1N=C(OCC=2C=C(F)C(F)=CC=2)C(C(=O)NC)=CC=1C1=CC=C(Cl)C=C1 FPBZDYQUXHBXBO-UHFFFAOYSA-N 0.000 claims 2
- XQQYSNIMBGWIEC-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-[(3,4-difluorophenyl)methoxy]pyridine-3-carbonitrile Chemical compound C1=C(F)C(F)=CC=C1COC1=NC(C=2C(=CC(Cl)=CC=2)Cl)=C(C=2C=CC(Cl)=CC=2)C=C1C#N XQQYSNIMBGWIEC-UHFFFAOYSA-N 0.000 claims 2
- LJRDDUPQALIJGH-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-[(3,4-difluorophenyl)methyl]pyridine-3-carbonitrile Chemical compound C1=C(F)C(F)=CC=C1CC1=NC(C=2C(=CC(Cl)=CC=2)Cl)=C(C=2C=CC(Cl)=CC=2)C=C1C#N LJRDDUPQALIJGH-UHFFFAOYSA-N 0.000 claims 2
- NJTKTPGFVGYUCD-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-[(3,5-difluorophenyl)methoxy]pyridine-3-carbonitrile Chemical compound FC1=CC(F)=CC(COC=2C(=CC(=C(C=3C(=CC(Cl)=CC=3)Cl)N=2)C=2C=CC(Cl)=CC=2)C#N)=C1 NJTKTPGFVGYUCD-UHFFFAOYSA-N 0.000 claims 2
- ZZUKFXGVUSGZCV-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-[(4-fluorophenyl)methoxy]pyridine-3-carbonitrile Chemical compound C1=CC(F)=CC=C1COC1=NC(C=2C(=CC(Cl)=CC=2)Cl)=C(C=2C=CC(Cl)=CC=2)C=C1C#N ZZUKFXGVUSGZCV-UHFFFAOYSA-N 0.000 claims 2
- GTFYXEYTWAYYLT-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-[1-(4-fluorophenyl)ethoxy]pyridine-3-carbonitrile Chemical compound C=1C=C(F)C=CC=1C(C)OC(C(=CC=1C=2C=CC(Cl)=CC=2)C#N)=NC=1C1=CC=C(Cl)C=C1Cl GTFYXEYTWAYYLT-UHFFFAOYSA-N 0.000 claims 2
- MQPIPCZNBMMMNO-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-phenylmethoxy-n-piperidin-1-ylpyridine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1C(C(=N1)C=2C(=CC(Cl)=CC=2)Cl)=CC(C(=O)NN2CCCCC2)=C1OCC1=CC=CC=C1 MQPIPCZNBMMMNO-UHFFFAOYSA-N 0.000 claims 2
- QUAZWCZRNVNLQQ-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-phenylmethoxypyridine-3-carbonitrile Chemical compound C1=CC(Cl)=CC=C1C(C(=N1)C=2C(=CC(Cl)=CC=2)Cl)=CC(C#N)=C1OCC1=CC=CC=C1 QUAZWCZRNVNLQQ-UHFFFAOYSA-N 0.000 claims 2
- ONJZNBNUXSLKBK-UHFFFAOYSA-N 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-pyridin-3-yloxypyridine-3-carbonitrile Chemical compound C1=CC(Cl)=CC=C1C(C(=N1)C=2C(=CC(Cl)=CC=2)Cl)=CC(C#N)=C1OC1=CC=CN=C1 ONJZNBNUXSLKBK-UHFFFAOYSA-N 0.000 claims 2
- 229930003347 Atropine Natural products 0.000 claims 2
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 claims 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 2
- YNBADRVTZLEFNH-UHFFFAOYSA-N Methyl nicotinate Natural products COC(=O)C1=CC=CN=C1 YNBADRVTZLEFNH-UHFFFAOYSA-N 0.000 claims 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- ZZHLYYDVIOPZBE-UHFFFAOYSA-N Trimeprazine Chemical compound C1=CC=C2N(CC(CN(C)C)C)C3=CC=CC=C3SC2=C1 ZZHLYYDVIOPZBE-UHFFFAOYSA-N 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 230000001430 anti-depressive effect Effects 0.000 claims 2
- 239000000935 antidepressant agent Substances 0.000 claims 2
- 229940005513 antidepressants Drugs 0.000 claims 2
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 claims 2
- 229960000396 atropine Drugs 0.000 claims 2
- 239000003246 corticosteroid Substances 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 239000011777 magnesium Substances 0.000 claims 2
- 229910052749 magnesium Inorganic materials 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- AWZPBECDKVFELS-UHFFFAOYSA-N methyl 5-(4-chlorophenyl)-2-(5-chloropyridin-3-yl)oxy-6-(2,4-dichlorophenyl)pyridine-3-carboxylate Chemical compound C=1C=C(Cl)C=C(Cl)C=1C=1N=C(OC=2C=C(Cl)C=NC=2)C(C(=O)OC)=CC=1C1=CC=C(Cl)C=C1 AWZPBECDKVFELS-UHFFFAOYSA-N 0.000 claims 2
- CYDGBODJXMLPGY-UHFFFAOYSA-N methyl 6-(4-chlorophenyl)-2-methoxy-5-phenylpyridine-3-carboxylate Chemical compound C=1C=C(Cl)C=CC=1C=1N=C(OC)C(C(=O)OC)=CC=1C1=CC=CC=C1 CYDGBODJXMLPGY-UHFFFAOYSA-N 0.000 claims 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 2
- 229960001238 methylnicotinate Drugs 0.000 claims 2
- 239000002899 monoamine oxidase inhibitor Substances 0.000 claims 2
- GTHBLKNJWUFWAO-UHFFFAOYSA-N n-[2-[5-(4-chlorophenyl)-3-cyano-6-(2,4-dichlorophenyl)pyridin-2-yl]oxyethyl]-4-fluorobenzamide Chemical compound C1=CC(F)=CC=C1C(=O)NCCOC1=NC(C=2C(=CC(Cl)=CC=2)Cl)=C(C=2C=CC(Cl)=CC=2)C=C1C#N GTHBLKNJWUFWAO-UHFFFAOYSA-N 0.000 claims 2
- KTRFZZLLQIRRJI-UHFFFAOYSA-N n-[2-[5-(4-chlorophenyl)-3-cyano-6-(2,4-dichlorophenyl)pyridin-2-yl]oxyethyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(C(=N1)C=2C(=CC(Cl)=CC=2)Cl)=CC(C#N)=C1OCCNC(=O)C1=CC=CC=C1 KTRFZZLLQIRRJI-UHFFFAOYSA-N 0.000 claims 2
- AYYXHEXYNSQCSS-UHFFFAOYSA-N n-[2-[5-(4-chlorophenyl)-3-cyano-6-(2,4-dichlorophenyl)pyridin-2-yl]oxyethyl]cyclobutanecarboxamide Chemical compound C1=CC(Cl)=CC=C1C(C(=N1)C=2C(=CC(Cl)=CC=2)Cl)=CC(C#N)=C1OCCNC(=O)C1CCC1 AYYXHEXYNSQCSS-UHFFFAOYSA-N 0.000 claims 2
- WEXCSKKFHLUZDO-UHFFFAOYSA-N n-[2-[5-(4-chlorophenyl)-3-cyano-6-(2,4-dichlorophenyl)pyridin-2-yl]oxyethyl]cyclopentanecarboxamide Chemical compound C1=CC(Cl)=CC=C1C(C(=N1)C=2C(=CC(Cl)=CC=2)Cl)=CC(C#N)=C1OCCNC(=O)C1CCCC1 WEXCSKKFHLUZDO-UHFFFAOYSA-N 0.000 claims 2
- AIBYWAIPRHPVNS-UHFFFAOYSA-N n-[2-[5-(4-chlorophenyl)-3-cyano-6-(2,4-dichlorophenyl)pyridin-2-yl]oxyethyl]cyclopropanecarboxamide Chemical compound C1=CC(Cl)=CC=C1C(C(=N1)C=2C(=CC(Cl)=CC=2)Cl)=CC(C#N)=C1OCCNC(=O)C1CC1 AIBYWAIPRHPVNS-UHFFFAOYSA-N 0.000 claims 2
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2003
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- 2003-03-24 AU AU2003225964A patent/AU2003225964B2/en not_active Ceased
- 2003-03-24 WO PCT/US2003/009005 patent/WO2003082191A2/en not_active Ceased
- 2003-03-24 JP JP2003579734A patent/JP2005531520A/ja active Pending
- 2003-03-24 EP EP03745578A patent/EP1492784A4/en not_active Withdrawn
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