JP2005532371A - レニン阻害剤としての新規なテトラヒドロピリジン誘導体 - Google Patents

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Publication number

JP2005532371A

JP2005532371A JP2004516551A JP2004516551A JP2005532371A JP 2005532371 A JP2005532371 A JP 2005532371A JP 2004516551 A JP2004516551 A JP 2004516551A JP 2004516551 A JP2004516551 A JP 2004516551A JP 2005532371 A JP2005532371 A JP 2005532371A

Authority

JP

Japan

Prior art keywords

phenyl

tetrahydropyridine

carboxylic acid

ethoxy

amide

Prior art date

2002-06-27

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.)

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• 239000002461 renin inhibitor Substances 0.000 title abstract description 12
• 229940086526 renin-inhibitors Drugs 0.000 title abstract description 12
• VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical class C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 367
• 238000000034 method Methods 0.000 claims abstract description 41
• 238000011282 treatment Methods 0.000 claims abstract description 14
• 208000001647 Renal Insufficiency Diseases 0.000 claims abstract description 9
• 201000006370 kidney failure Diseases 0.000 claims abstract description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
• -1 tri-substituted phenyl Chemical group 0.000 claims description 211
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
• 239000000203 mixture Substances 0.000 claims description 52
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 48
• 239000002904 solvent Chemical class 0.000 claims description 36
• 125000003118 aryl group Chemical group 0.000 claims description 22
• 150000001408 amides Chemical class 0.000 claims description 21
• HEQDIKZGBQQWFK-UHFFFAOYSA-N 4-[4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxylic acid Chemical compound ClC1=CC(C)=CC(Cl)=C1OCCOC1=CC=C(C=2CCNCC=2C(O)=O)C=C1 HEQDIKZGBQQWFK-UHFFFAOYSA-N 0.000 claims description 20
• 125000000217 alkyl group Chemical group 0.000 claims description 19
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
• RWENEHDSAPYDKP-UHFFFAOYSA-N 4-[4-[2-(2,6-dichloro-4-fluorophenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxylic acid Chemical compound C1CNCC(C(=O)O)=C1C(C=C1)=CC=C1OCCOC1=C(Cl)C=C(F)C=C1Cl RWENEHDSAPYDKP-UHFFFAOYSA-N 0.000 claims description 16
• 150000003839 salts Chemical class 0.000 claims description 16
• UKLRWOHZBISUMI-UHFFFAOYSA-N (2,3-dimethylphenyl)methanamine Chemical compound CC1=CC=CC(CN)=C1C UKLRWOHZBISUMI-UHFFFAOYSA-N 0.000 claims description 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
• MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 14
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 150000002367 halogens Chemical class 0.000 claims description 13
• 230000036454 renin-angiotensin system Effects 0.000 claims description 13
• JHBVZGONNIVXFJ-UHFFFAOYSA-N (2,3-dichlorophenyl)methanamine Chemical compound NCC1=CC=CC(Cl)=C1Cl JHBVZGONNIVXFJ-UHFFFAOYSA-N 0.000 claims description 12
• 206010020772 Hypertension Diseases 0.000 claims description 12
• HWDVTQAXQJQROO-UHFFFAOYSA-N cyclopropylazanide Chemical compound [NH-]C1CC1 HWDVTQAXQJQROO-UHFFFAOYSA-N 0.000 claims description 12
• 201000010099 disease Diseases 0.000 claims description 12
• 206010019280 Heart failures Diseases 0.000 claims description 11
• 125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 10
• LXYQIBRUJZBFFC-UHFFFAOYSA-N 4-[4-[2-(2-chloro-4,5-dimethylphenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxylic acid Chemical compound C1=C(C)C(C)=CC(Cl)=C1OCCOC1=CC=C(C=2CCNCC=2C(O)=O)C=C1 LXYQIBRUJZBFFC-UHFFFAOYSA-N 0.000 claims description 10
• OUZFDZJXZYVMMY-UHFFFAOYSA-N 4-[4-[2-[2-chloro-4-(trifluoromethyl)phenoxy]ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxylic acid Chemical compound C1CNCC(C(=O)O)=C1C(C=C1)=CC=C1OCCOC1=CC=C(C(F)(F)F)C=C1Cl OUZFDZJXZYVMMY-UHFFFAOYSA-N 0.000 claims description 10
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000001072 heteroaryl group Chemical group 0.000 claims description 10
• GCJYLAWVUWEHLW-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]cyclopropanamine Chemical compound ClC1=CC=CC=C1CNC1CC1 GCJYLAWVUWEHLW-UHFFFAOYSA-N 0.000 claims description 10
• 229910052757 nitrogen Inorganic materials 0.000 claims description 10
• 239000000126 substance Substances 0.000 claims description 10
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• 229910052720 vanadium Inorganic materials 0.000 claims description 9
• YGZJTYCCONJJGZ-UHFFFAOYSA-N (3,5-dimethoxyphenyl)methanamine Chemical compound COC1=CC(CN)=CC(OC)=C1 YGZJTYCCONJJGZ-UHFFFAOYSA-N 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 8
• 125000002947 alkylene group Chemical group 0.000 claims description 8
• 229910052739 hydrogen Inorganic materials 0.000 claims description 8
• 239000001257 hydrogen Substances 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• FZHYIKABBMEJMA-UHFFFAOYSA-N 4-[4-[2-(2,6-difluoro-3-methylphenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxylic acid Chemical compound CC1=CC=C(F)C(OCCOC=2C=CC(=CC=2)C=2CCNCC=2C(O)=O)=C1F FZHYIKABBMEJMA-UHFFFAOYSA-N 0.000 claims description 7
• 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 7
• 239000005541 ACE inhibitor Substances 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 206010063897 Renal ischaemia Diseases 0.000 claims description 7
• 229910052770 Uranium Inorganic materials 0.000 claims description 7
• 125000004450 alkenylene group Chemical group 0.000 claims description 7
• 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 7
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
• 208000031225 myocardial ischemia Diseases 0.000 claims description 7
• IEBLAFHYIWKOCK-UHFFFAOYSA-N 4-[4-[2-(3-chloro-2,6-difluorophenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxylic acid Chemical compound C1CNCC(C(=O)O)=C1C(C=C1)=CC=C1OCCOC1=C(F)C=CC(Cl)=C1F IEBLAFHYIWKOCK-UHFFFAOYSA-N 0.000 claims description 6
• 125000000304 alkynyl group Chemical group 0.000 claims description 6
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
• 125000000623 heterocyclic group Chemical group 0.000 claims description 6
• 230000000877 morphologic effect Effects 0.000 claims description 6
• XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 claims description 6
• 230000002792 vascular Effects 0.000 claims description 6
• 239000002253 acid Substances 0.000 claims description 5
• 210000003734 kidney Anatomy 0.000 claims description 5
• KJYVKUQRRKDPAX-UHFFFAOYSA-N n-[(2,3-dichlorophenyl)methyl]cyclopropanamine Chemical compound ClC1=CC=CC(CNC2CC2)=C1Cl KJYVKUQRRKDPAX-UHFFFAOYSA-N 0.000 claims description 5
• NUPAMNLYORQZRV-UHFFFAOYSA-N n-[(3-methoxyphenyl)methyl]cyclopropanamine Chemical compound COC1=CC=CC(CNC2CC2)=C1 NUPAMNLYORQZRV-UHFFFAOYSA-N 0.000 claims description 5
• POYWLSASJPZKQR-UHFFFAOYSA-N n-[2-(2-methylphenyl)ethyl]cyclopropanamine Chemical compound CC1=CC=CC=C1CCNC1CC1 POYWLSASJPZKQR-UHFFFAOYSA-N 0.000 claims description 5
• 208000037803 restenosis Diseases 0.000 claims description 5
• 125000001424 substituent group Chemical group 0.000 claims description 5
• 206010007559 Cardiac failure congestive Diseases 0.000 claims description 4
• 208000002249 Diabetes Complications Diseases 0.000 claims description 4
• 206010012655 Diabetic complications Diseases 0.000 claims description 4
• 208000010228 Erectile Dysfunction Diseases 0.000 claims description 4
• 208000010412 Glaucoma Diseases 0.000 claims description 4
• 206010018364 Glomerulonephritis Diseases 0.000 claims description 4
• 206010038419 Renal colic Diseases 0.000 claims description 4
• TUPUHSXMDIWJQT-UHFFFAOYSA-N [3-(trifluoromethoxy)phenyl]methanamine Chemical compound NCC1=CC=CC(OC(F)(F)F)=C1 TUPUHSXMDIWJQT-UHFFFAOYSA-N 0.000 claims description 4
• 238000007675 cardiac surgery Methods 0.000 claims description 4
• 201000001881 impotence Diseases 0.000 claims description 4
• 210000000056 organ Anatomy 0.000 claims description 4
• 238000002054 transplantation Methods 0.000 claims description 4
• 229910052721 tungsten Inorganic materials 0.000 claims description 4
• 238000007631 vascular surgery Methods 0.000 claims description 4
• VJNGGOMRUHYAMC-UHFFFAOYSA-N (3,5-difluorophenyl)methanamine Chemical compound NCC1=CC(F)=CC(F)=C1 VJNGGOMRUHYAMC-UHFFFAOYSA-N 0.000 claims description 3
• IHMWNGLGFOAQIL-UHFFFAOYSA-N 4-[4-[3-(2-bromo-5-fluorophenoxy)propyl]phenyl]-n-cyclopropyl-n-[(2-methylphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound CC1=CC=CC=C1CN(C(=O)C=1CNCCC=1C=1C=CC(CCCOC=2C(=CC=C(F)C=2)Br)=CC=1)C1CC1 IHMWNGLGFOAQIL-UHFFFAOYSA-N 0.000 claims description 3
• XQYYULLHWJYZAL-UHFFFAOYSA-N 4-[4-[3-(2-bromo-5-fluorophenoxy)propyl]phenyl]-n-cyclopropyl-n-[2-(2-methylphenyl)ethyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound CC1=CC=CC=C1CCN(C(=O)C=1CNCCC=1C=1C=CC(CCCOC=2C(=CC=C(F)C=2)Br)=CC=1)C1CC1 XQYYULLHWJYZAL-UHFFFAOYSA-N 0.000 claims description 3
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
• 239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 3
• VDYXNMDTCPOGGV-UHFFFAOYSA-N n-cyclopropyl-n-[(2-fluoro-5-methoxyphenyl)methyl]-4-[4-[2-(2,4,6-trifluorophenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC=C(F)C(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC(F)=CC=3F)F)=CC=2)=C1 VDYXNMDTCPOGGV-UHFFFAOYSA-N 0.000 claims description 3
• YDSLMDXEOLXWOR-UHFFFAOYSA-N n-cyclopropyl-n-[(2-methylphenyl)methyl]-4-[4-[2-(2,3,5-trimethylphenoxy)ethyl]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound CC1=CC(C)=C(C)C(OCCC=2C=CC(=CC=2)C=2CCNCC=2C(=O)N(CC=2C(=CC=CC=2)C)C2CC2)=C1 YDSLMDXEOLXWOR-UHFFFAOYSA-N 0.000 claims description 3
• DIVNUTGTTIRPQA-UHFFFAOYSA-N (3,4-dimethoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1OC DIVNUTGTTIRPQA-UHFFFAOYSA-N 0.000 claims description 2
• 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 2
• 125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims description 2
• JBIOASAGZWOVGH-UHFFFAOYSA-N 4-[4-[2-(2-bromo-5-fluorophenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxylic acid Chemical compound C1CNCC(C(=O)O)=C1C(C=C1)=CC=C1OCCOC1=CC(F)=CC=C1Br JBIOASAGZWOVGH-UHFFFAOYSA-N 0.000 claims description 2
• OLHHRXWVIGFHIL-UHFFFAOYSA-N 4-[4-[2-(2-bromo-5-fluorophenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxylic acid N-[[2-chloro-3-(trifluoromethyl)phenyl]methyl]cyclopropanamine Chemical compound OC(C(CNCC1)=C1C(C=C1)=CC=C1OCCOC(C=C(C=C1)F)=C1Br)=O.FC(C1=CC=CC(CNC2CC2)=C1Cl)(F)F OLHHRXWVIGFHIL-UHFFFAOYSA-N 0.000 claims description 2
• FIKPVBOZTALOIJ-UHFFFAOYSA-N 4-[4-[2-(2-bromo-5-fluorophenoxy)ethoxy]phenyl]-n-cyclopropyl-n-[(2,3-dimethylphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound CC1=CC=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC=C(F)C=3)Br)=CC=2)=C1C FIKPVBOZTALOIJ-UHFFFAOYSA-N 0.000 claims description 2
• CZUCEGQMRLRKTB-UHFFFAOYSA-N 4-[4-[2-(2-chloro-4,5-dimethylphenoxy)ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxylic acid N-[[2-chloro-3-(trifluoromethyl)phenyl]methyl]cyclopropanamine Chemical compound CC(C(C)=C1)=CC(OCCOC(C=C2)=CC=C2C(CCNC2)=C2C(O)=O)=C1Cl.FC(C1=CC=CC(CNC2CC2)=C1Cl)(F)F CZUCEGQMRLRKTB-UHFFFAOYSA-N 0.000 claims description 2
• WHTCWJJUDHYVSP-UHFFFAOYSA-N 4-[4-[2-(2-chloro-4,5-dimethylphenoxy)ethoxy]phenyl]-n-cyclopropyl-n-[(2-fluoro-5-methoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC=C(F)C(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC(C)=C(C)C=3)Cl)=CC=2)=C1 WHTCWJJUDHYVSP-UHFFFAOYSA-N 0.000 claims description 2
• JMUJGIPCNDMYNG-UHFFFAOYSA-N 4-[4-[2-(2-chloro-4,5-dimethylphenoxy)ethoxy]phenyl]-n-cyclopropyl-n-[(3-methoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC(C)=C(C)C=3)Cl)=CC=2)=C1 JMUJGIPCNDMYNG-UHFFFAOYSA-N 0.000 claims description 2
• WZOOWBZCJFOLAU-UHFFFAOYSA-N 4-[4-[2-(3-chloro-2,6-difluorophenoxy)ethoxy]phenyl]-n-cyclopropyl-n-[(2-fluoro-5-methoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC=C(F)C(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=C(Cl)C=CC=3F)F)=CC=2)=C1 WZOOWBZCJFOLAU-UHFFFAOYSA-N 0.000 claims description 2
• DGIHJKQEJKQGFD-UHFFFAOYSA-N 4-[4-[2-(3-chloro-2,6-difluorophenoxy)ethoxy]phenyl]-n-cyclopropyl-n-[(3-methoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=C(Cl)C=CC=3F)F)=CC=2)=C1 DGIHJKQEJKQGFD-UHFFFAOYSA-N 0.000 claims description 2
• MPZVIMKAJUUMSX-UHFFFAOYSA-N 4-[4-[2-(4-chloro-2-methoxyphenoxy)ethoxy]phenyl]-n-cyclopropyl-n-[(2,3-dichlorophenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC(Cl)=CC=C1OCCOC1=CC=C(C=2CCNCC=2C(=O)N(CC=2C(=C(Cl)C=CC=2)Cl)C2CC2)C=C1 MPZVIMKAJUUMSX-UHFFFAOYSA-N 0.000 claims description 2
• OZEMDWYPAFICGO-UHFFFAOYSA-N 4-[4-[2-(4-chloro-2-methoxyphenoxy)ethoxy]phenyl]-n-cyclopropyl-n-[(2,3-dimethylphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC(Cl)=CC=C1OCCOC1=CC=C(C=2CCNCC=2C(=O)N(CC=2C(=C(C)C=CC=2)C)C2CC2)C=C1 OZEMDWYPAFICGO-UHFFFAOYSA-N 0.000 claims description 2
• CTAYAKNXEZEAIV-UHFFFAOYSA-N 4-[4-[2-(4-chloro-2-methoxyphenoxy)ethoxy]phenyl]-n-cyclopropyl-n-[(3-methoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC(Cl)=CC=3)OC)=CC=2)=C1 CTAYAKNXEZEAIV-UHFFFAOYSA-N 0.000 claims description 2
• HZYJQIWTYIOFAJ-UHFFFAOYSA-N 4-[4-[2-(4-chloro-2-methylphenoxy)ethoxy]phenyl]-n-cyclopropyl-n-[(2,3-dichlorophenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound CC1=CC(Cl)=CC=C1OCCOC1=CC=C(C=2CCNCC=2C(=O)N(CC=2C(=C(Cl)C=CC=2)Cl)C2CC2)C=C1 HZYJQIWTYIOFAJ-UHFFFAOYSA-N 0.000 claims description 2
• QXPZBKGYFZEZEL-UHFFFAOYSA-N 4-[4-[2-(4-chloro-2-methylphenoxy)ethoxy]phenyl]-n-cyclopropyl-n-[(2,3-dimethylphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound CC1=CC=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC(Cl)=CC=3)C)=CC=2)=C1C QXPZBKGYFZEZEL-UHFFFAOYSA-N 0.000 claims description 2
• BJHAITPBNSBYQP-UHFFFAOYSA-N 4-[4-[2-[2-chloro-4-(trifluoromethyl)phenoxy]ethoxy]phenyl]-1,2,3,6-tetrahydropyridine-5-carboxylic acid N-[[2-chloro-3-(trifluoromethyl)phenyl]methyl]cyclopropanamine Chemical compound OC(C(CNCC1)=C1C(C=C1)=CC=C1OCCOC(C=CC(C(F)(F)F)=C1)=C1Cl)=O.FC(C1=CC=CC(CNC2CC2)=C1Cl)(F)F BJHAITPBNSBYQP-UHFFFAOYSA-N 0.000 claims description 2
• OFJPCRUQKSZFFI-UHFFFAOYSA-N 4-[4-[2-[2-chloro-4-(trifluoromethyl)phenoxy]ethoxy]phenyl]-n-cyclopropyl-n-[(2-fluoro-5-methoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC=C(F)C(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC(=CC=3)C(F)(F)F)Cl)=CC=2)=C1 OFJPCRUQKSZFFI-UHFFFAOYSA-N 0.000 claims description 2
• POUMYTOBNJHZMG-UHFFFAOYSA-N 4-[4-[2-[2-chloro-4-(trifluoromethyl)phenoxy]ethoxy]phenyl]-n-cyclopropyl-n-[(3-methoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(OCCOC=3C(=CC(=CC=3)C(F)(F)F)Cl)=CC=2)=C1 POUMYTOBNJHZMG-UHFFFAOYSA-N 0.000 claims description 2
• ZUESJUDDPXQLMZ-UHFFFAOYSA-N 4-[4-[3-(2-bromo-5-fluorophenoxy)propyl]phenyl]-n-cyclopropyl-n-(2-phenylethyl)-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound FC1=CC=C(Br)C(OCCCC=2C=CC(=CC=2)C=2CCNCC=2C(=O)N(CCC=2C=CC=CC=2)C2CC2)=C1 ZUESJUDDPXQLMZ-UHFFFAOYSA-N 0.000 claims description 2
• NJOFHEKRDZOEQT-UHFFFAOYSA-N 4-[4-[3-(2-bromo-5-fluorophenoxy)propyl]phenyl]-n-cyclopropyl-n-[(3,5-dimethoxyphenyl)methyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound COC1=CC(OC)=CC(CN(C2CC2)C(=O)C=2CNCCC=2C=2C=CC(CCCOC=3C(=CC=C(F)C=3)Br)=CC=2)=C1 NJOFHEKRDZOEQT-UHFFFAOYSA-N 0.000 claims description 2
• WFVATWGXIDKWIS-UHFFFAOYSA-N 4-[4-[3-(2-bromo-5-fluorophenoxy)propyl]phenyl]-n-cyclopropyl-n-[2-(4-methoxyphenoxy)ethyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound C1=CC(OC)=CC=C1OCCN(C(=O)C=1CNCCC=1C=1C=CC(CCCOC=2C(=CC=C(F)C=2)Br)=CC=1)C1CC1 WFVATWGXIDKWIS-UHFFFAOYSA-N 0.000 claims description 2
• VIODYOKNCDHZFQ-UHFFFAOYSA-N 4-[4-[3-(2-bromo-5-fluorophenoxy)propyl]phenyl]-n-cyclopropyl-n-[2-(4-methylphenyl)ethyl]-1,2,3,6-tetrahydropyridine-5-carboxamide Chemical compound C1=CC(C)=CC=C1CCN(C(=O)C=1CNCCC=1C=1C=CC(CCCOC=2C(=CC=C(F)C=2)Br)=CC=1)C1CC1 VIODYOKNCDHZFQ-UHFFFAOYSA-N 0.000 claims description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
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