IL118484A

IL118484A - Trifluoromethyl-biphenyl carboxylic acid amides, uses thereof and pharmaceutical compositions containing them

Trifluoromethyl-biphenyl carboxylic acid amides, uses thereof and pharmaceutical compositions containing them

Info

Publication number: IL118484A
Authority: IL; Israel
Prior art keywords: biphenyl; trifluoromethyl; amide; carboxylic acid; tetrahydroisoquinolin
Prior art date: 1995-06-07

Application number

IL11848496A

Other languages

English (en)

Other versions

IL118484A0 (en

Original Assignee

Pfizer

Priority date

1995-06-07

Filing date

1996-05-30

Publication date

2001-11-25

1995-06-07 Priority claimed from CA002223574A external-priority patent/CA2223574C/fr

1996-05-30 Application filed by Pfizer filed Critical Pfizer

1996-05-30 Priority to IL13537696A priority Critical patent/IL135376A/en

1996-05-30 Priority to IL13537596A priority patent/IL135375A/en

1996-05-30 Priority to IL13537796A priority patent/IL135377A/en

1996-09-12 Publication of IL118484A0 publication Critical patent/IL118484A0/xx

2001-11-25 Publication of IL118484A publication Critical patent/IL118484A/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 6
UKOOYMRLGQSVEU-UHFFFAOYSA-N 2-phenyl-6-(trifluoromethyl)benzamide Chemical class C1=CC=C(C(F)(F)F)C(C(=O)N)=C1C1=CC=CC=C1 UKOOYMRLGQSVEU-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 131
-1 cyano, nitro, oxo, thioxo, aminosulfonyl Chemical group 0.000 claims abstract description 110
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 32
150000003839 salts Chemical class 0.000 claims abstract description 22
125000003118 aryl group Chemical group 0.000 claims abstract description 20
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 19
125000001424 substituent group Chemical group 0.000 claims abstract description 19
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 17
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 14
229920006395 saturated elastomer Polymers 0.000 claims abstract description 13
229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract description 11
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims abstract description 10
125000002252 acyl group Chemical group 0.000 claims abstract description 10
125000004423 acyloxy group Chemical group 0.000 claims abstract description 10
229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 10
125000005842 heteroatom Chemical group 0.000 claims abstract description 10
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 8
125000006554 (C4-C8) cycloalkenyl group Chemical group 0.000 claims abstract description 8
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 8
229920002554 vinyl polymer Polymers 0.000 claims abstract description 8
125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
229910052717 sulfur Chemical group 0.000 claims abstract description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 6
125000004104 aryloxy group Chemical group 0.000 claims abstract description 6
125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 6
239000011593 sulfur Chemical group 0.000 claims abstract description 6
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 5
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
239000001301 oxygen Substances 0.000 claims abstract description 5
125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims abstract description 4
125000005110 aryl thio group Chemical group 0.000 claims abstract description 4
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 4
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
125000004465 cycloalkenyloxy group Chemical group 0.000 claims abstract description 4
125000005592 polycycloalkyl group Polymers 0.000 claims abstract description 4
125000006413 ring segment Chemical group 0.000 claims abstract description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
IQOMYCGTGFGDFN-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 IQOMYCGTGFGDFN-UHFFFAOYSA-N 0.000 claims description 41
239000002253 acid Substances 0.000 claims description 19
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 15
230000028327 secretion Effects 0.000 claims description 13
125000005647 linker group Chemical group 0.000 claims description 12
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 12
201000001320 Atherosclerosis Diseases 0.000 claims description 11
150000001408 amides Chemical group 0.000 claims description 11
208000008589 Obesity Diseases 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 9
235000020824 obesity Nutrition 0.000 claims description 9
229940124530 sulfonamide Drugs 0.000 claims description 9
101150102415 Apob gene Proteins 0.000 claims description 8
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 8
150000003456 sulfonamides Chemical group 0.000 claims description 8
206010033645 Pancreatitis Diseases 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
206010012601 diabetes mellitus Diseases 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 5
208000035150 Hypercholesterolemia Diseases 0.000 claims description 5
229920001774 Perfluoroether Polymers 0.000 claims description 5
230000003247 decreasing effect Effects 0.000 claims description 5
208000006575 hypertriglyceridemia Diseases 0.000 claims description 5
125000002883 imidazolyl group Chemical group 0.000 claims description 5
LBBXOYBEGXAARL-UHFFFAOYSA-N n-[2-(1,3-thiazol-2-ylmethyl)-3,4-dihydro-1h-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC=2SC=CN=2)CC2)C2=C1 LBBXOYBEGXAARL-UHFFFAOYSA-N 0.000 claims description 5
125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
125000000335 thiazolyl group Chemical group 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
101710095342 Apolipoprotein B Proteins 0.000 claims description 4
102100040202 Apolipoprotein B-100 Human genes 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
VBLDQJIRPICNBW-UHFFFAOYSA-N (6-amino-3,4-dihydro-1H-isoquinolin-2-yl)-pyridin-2-ylmethanone Chemical compound C1CC2=CC(N)=CC=C2CN1C(=O)C1=CC=CC=N1 VBLDQJIRPICNBW-UHFFFAOYSA-N 0.000 claims description 3
125000006664 (C1-C3) perfluoroalkyl group Chemical group 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
125000000842 isoxazolyl group Chemical group 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 claims description 2
VHYSQPXVQFAMOU-UHFFFAOYSA-N 2-[(1-methylpyrrol-2-yl)methyl]-3,4-dihydro-1H-isoquinolin-6-amine Chemical compound CN1C=CC=C1CN1CC2=CC=C(N)C=C2CC1 VHYSQPXVQFAMOU-UHFFFAOYSA-N 0.000 claims description 2
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 2
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 2
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical group NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
AVEJPRXCBCHUEY-UHFFFAOYSA-N N-(2-propan-2-ylsulfonyl-3,4-dihydro-1H-isoquinolin-6-yl)-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C=1C=C2CN(S(=O)(=O)C(C)C)CCC2=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 AVEJPRXCBCHUEY-UHFFFAOYSA-N 0.000 claims description 2
IZFQSQQGQRFVHN-UHFFFAOYSA-N N-[2-(cyclobutanecarbonyl)-3,4-dihydro-1H-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC2)C(=O)C3CCC3)C2=C1 IZFQSQQGQRFVHN-UHFFFAOYSA-N 0.000 claims description 2
ZJVMHRAFXYAOPU-UHFFFAOYSA-N N-[2-[2-(trifluoromethoxy)phenyl]sulfonyl-3,4-dihydro-1H-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound FC(F)(F)OC1=CC=CC=C1S(=O)(=O)N1CC2=CC=C(NC(=O)C=3C(=CC=CC=3)C=3C=CC(=CC=3)C(F)(F)F)C=C2CC1 ZJVMHRAFXYAOPU-UHFFFAOYSA-N 0.000 claims description 2
125000004450 alkenylene group Chemical group 0.000 claims description 2
239000003524 antilipemic agent Substances 0.000 claims description 2
125000002619 bicyclic group Chemical group 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 claims description 2
ITJYVAJPJUJZOO-UHFFFAOYSA-N n-(2-benzyl-3,4-dihydro-1h-isoquinolin-6-yl)-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC=2C=CC=CC=2)CC2)C2=C1 ITJYVAJPJUJZOO-UHFFFAOYSA-N 0.000 claims description 2
CUNBFJSOUZFOIJ-UHFFFAOYSA-N n-(2-but-3-enoyl-3,4-dihydro-1h-isoquinolin-6-yl)-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC2)C(=O)CC=C)C2=C1 CUNBFJSOUZFOIJ-UHFFFAOYSA-N 0.000 claims description 2
RONNIDMEEXKTTP-UHFFFAOYSA-N n-(2-butanoyl-3,4-dihydro-1h-isoquinolin-6-yl)-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C=1C=C2CN(C(=O)CCC)CCC2=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 RONNIDMEEXKTTP-UHFFFAOYSA-N 0.000 claims description 2
ZGWBGDZTNIPNGY-UHFFFAOYSA-N n-(2-hex-3-enoyl-3,4-dihydro-1h-isoquinolin-6-yl)-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C=1C=C2CN(C(=O)CC=CCC)CCC2=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 ZGWBGDZTNIPNGY-UHFFFAOYSA-N 0.000 claims description 2
JHWRGYDZUYBPRO-UHFFFAOYSA-N n-(2-pentanoyl-3,4-dihydro-1h-isoquinolin-6-yl)-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C=1C=C2CN(C(=O)CCCC)CCC2=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 JHWRGYDZUYBPRO-UHFFFAOYSA-N 0.000 claims description 2
YFTYDDCAGKFLQU-UHFFFAOYSA-N n-[1-(2-ethoxyacetyl)-1,2,3,4-tetrahydroisoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C=1C=C2C(C(=O)COCC)NCCC2=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 YFTYDDCAGKFLQU-UHFFFAOYSA-N 0.000 claims description 2
IPBZICXEEPVWTK-UHFFFAOYSA-N n-[1-(2-phenylacetyl)-1,2,3,4-tetrahydroisoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(C(NCC2)C(=O)CC=3C=CC=CC=3)C2=C1 IPBZICXEEPVWTK-UHFFFAOYSA-N 0.000 claims description 2
XGJYPBLLKVZMKG-UHFFFAOYSA-N n-[2-(1h-imidazol-2-ylmethyl)-3,4-dihydro-1h-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC=2NC=CN=2)CC2)C2=C1 XGJYPBLLKVZMKG-UHFFFAOYSA-N 0.000 claims description 2
UEZDQGILGUGPBI-UHFFFAOYSA-N n-[2-(2-thiophen-3-ylacetyl)-3,4-dihydro-1h-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC2)C(=O)CC3=CSC=C3)C2=C1 UEZDQGILGUGPBI-UHFFFAOYSA-N 0.000 claims description 2
OWUTUOOOSSLKAT-UHFFFAOYSA-N n-[2-(3-methylbutanoyl)-3,4-dihydro-1h-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C=1C=C2CN(C(=O)CC(C)C)CCC2=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 OWUTUOOOSSLKAT-UHFFFAOYSA-N 0.000 claims description 2
MANDBIMAUNFYAR-UHFFFAOYSA-N n-[2-(cyclopropylcarbamothioyl)-3,4-dihydro-1h-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC2)C(=S)NC3CC3)C2=C1 MANDBIMAUNFYAR-UHFFFAOYSA-N 0.000 claims description 2
OGZZFGVXDAQWFM-UHFFFAOYSA-N n-[2-(quinolin-2-ylmethyl)-3,4-dihydro-1h-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC=2N=C3C=CC=CC3=CC=2)CC2)C2=C1 OGZZFGVXDAQWFM-UHFFFAOYSA-N 0.000 claims description 2
HGSHHOKODPHGRI-UHFFFAOYSA-N n-[2-[2-(cyclopenten-1-yl)acetyl]-3,4-dihydro-1h-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC2)C(=O)CC=3CCCC=3)C2=C1 HGSHHOKODPHGRI-UHFFFAOYSA-N 0.000 claims description 2
KTKJCGKOCTXFRX-UHFFFAOYSA-N tert-butyl 6-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C=1C=C2CN(C(=O)OC(C)(C)C)CCC2=CC=1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 KTKJCGKOCTXFRX-UHFFFAOYSA-N 0.000 claims description 2
239000003814 drug Substances 0.000 claims 4
125000001475 halogen functional group Chemical group 0.000 claims 3
WXIVOQCTQSVGAQ-UHFFFAOYSA-N n-[2-(2-thiophen-2-ylacetyl)-3,4-dihydro-1h-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC2)C(=O)CC=3SC=CC=3)C2=C1 WXIVOQCTQSVGAQ-UHFFFAOYSA-N 0.000 claims 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 3
CUKAVTVGWFENTO-UHFFFAOYSA-N 2-(pyridin-2-ylmethyl)-3,4-dihydro-1H-isoquinolin-6-amine Chemical compound C1CC2=CC(N)=CC=C2CN1CC1=CC=CC=N1 CUKAVTVGWFENTO-UHFFFAOYSA-N 0.000 claims 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea group Chemical group NC(=S)N UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 2
QIXSYRICKPSRKY-UHFFFAOYSA-N 1-(6-amino-1,2,3,4-tetrahydroisoquinolin-1-yl)-2-methoxyethanone Chemical compound NC1=CC=C2C(C(=O)COC)NCCC2=C1 QIXSYRICKPSRKY-UHFFFAOYSA-N 0.000 claims 1
OVAFWEXNFPWMCA-UHFFFAOYSA-N 1-(6-amino-1,2,3,4-tetrahydroisoquinolin-1-yl)-2-phenoxyethanone Chemical compound N1CCC2=CC(N)=CC=C2C1C(=O)COC1=CC=CC=C1 OVAFWEXNFPWMCA-UHFFFAOYSA-N 0.000 claims 1
VWDHVRYTZFLPSM-UHFFFAOYSA-N 1-(6-amino-1,2,3,4-tetrahydroisoquinolin-1-yl)butane-1-thione Chemical compound NC1=CC=C2C(C(=S)CCC)NCCC2=C1 VWDHVRYTZFLPSM-UHFFFAOYSA-N 0.000 claims 1
RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 claims 1
BSRQOTSUHGLKTI-UHFFFAOYSA-N 2-(thiophen-3-ylmethyl)-3,4-dihydro-1H-isoquinolin-6-amine Chemical compound C1CC2=CC(N)=CC=C2CN1CC=1C=CSC=1 BSRQOTSUHGLKTI-UHFFFAOYSA-N 0.000 claims 1
UALJVGZBTOOZQQ-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]-n-[2-[(2,6,6-trimethylcyclohex-2-en-1-yl)methyl]-3,4-dihydro-1h-isoquinolin-6-yl]benzamide Chemical compound CC1=CCCC(C)(C)C1CN1CC2=CC=C(NC(=O)C=3C(=CC=CC=3)C=3C=CC(=CC=3)C(F)(F)F)C=C2CC1 UALJVGZBTOOZQQ-UHFFFAOYSA-N 0.000 claims 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
208000031226 Hyperlipidaemia Diseases 0.000 claims 1
CQOIDPPHPCWHIG-UHFFFAOYSA-N N-[2-(oxolane-3-carbonyl)-3,4-dihydro-1H-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC2)C(=O)C3COCC3)C2=C1 CQOIDPPHPCWHIG-UHFFFAOYSA-N 0.000 claims 1
HTQLPGBGOMIIOQ-UHFFFAOYSA-N N-[2-[(2,4-dichlorophenyl)methyl]-3,4-dihydro-1H-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC=2C(=CC(Cl)=CC=2)Cl)CC2)C2=C1 HTQLPGBGOMIIOQ-UHFFFAOYSA-N 0.000 claims 1
DJUZVMDRWXUYFJ-UHFFFAOYSA-N N-[2-[(3-nitrophenyl)methyl]-3,4-dihydro-1H-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound [O-][N+](=O)C1=CC=CC(CN2CC3=CC=C(NC(=O)C=4C(=CC=CC=4)C=4C=CC(=CC=4)C(F)(F)F)C=C3CC2)=C1 DJUZVMDRWXUYFJ-UHFFFAOYSA-N 0.000 claims 1
239000004202 carbamide Substances 0.000 claims 1
KEDZZOLFYJSFTQ-UHFFFAOYSA-N n-[2-(1h-pyrrol-2-ylmethyl)-3,4-dihydro-1h-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC=2NC=CC=2)CC2)C2=C1 KEDZZOLFYJSFTQ-UHFFFAOYSA-N 0.000 claims 1
CVHJDCYMGDFQSA-UHFFFAOYSA-N n-[2-(4,5a,6,9,9a,9b-hexahydro-1h-dibenzofuran-4a-ylmethyl)-3,4-dihydro-1h-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC23C(CC=CC2)C2C(CC=CC2)O3)CC2)C2=C1 CVHJDCYMGDFQSA-UHFFFAOYSA-N 0.000 claims 1
DDIQYNDUIFCEAY-UHFFFAOYSA-N n-[2-(furan-2-ylmethyl)-3,4-dihydro-1h-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC=2OC=CC=2)CC2)C2=C1 DDIQYNDUIFCEAY-UHFFFAOYSA-N 0.000 claims 1
DRLCIQLMMFMQGH-UHFFFAOYSA-N n-[2-(thiophen-2-ylmethyl)-3,4-dihydro-1h-isoquinolin-6-yl]-2-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC=2SC=CC=2)CC2)C2=C1 DRLCIQLMMFMQGH-UHFFFAOYSA-N 0.000 claims 1
BQBWUBKROPEBDY-UHFFFAOYSA-N n-benzyl-6-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]-3,4-dihydro-1h-isoquinoline-2-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CC=CC=C1C(=O)NC1=CC=C(CN(CC2)C(=O)NCC=3C=CC=CC=3)C2=C1 BQBWUBKROPEBDY-UHFFFAOYSA-N 0.000 claims 1
125000001391 thioamide group Chemical group 0.000 claims 1
125000005843 halogen group Chemical group 0.000 abstract description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
239000002904 solvent Substances 0.000 description 51
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 41
239000000243 solution Substances 0.000 description 41
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 40
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
238000000034 method Methods 0.000 description 38
238000006243 chemical reaction Methods 0.000 description 34
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 32
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