NO324932B1 - 1,2,3,4-Tetrahydroisokinolin-derivater, fremgangsmate for fremstilling av slike, farmasoytiske preparater inneholdende slike samt slike forbindelser anvendt til fremstilling av medikament for behandling av sykdommer - Google Patents

Info

Publication number

NO324932B1

NO324932B1 NO20024339A NO20024339A NO324932B1 NO 324932 B1 NO324932 B1 NO 324932B1 NO 20024339 A NO20024339 A NO 20024339A NO 20024339 A NO20024339 A NO 20024339A NO 324932 B1 NO324932 B1 NO 324932B1

Authority

NO

Norway

Prior art keywords

benzyl

dimethoxy

acetamide

dihydro

isoquinolin

Prior art date

2000-03-14

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 title claims abstract description 66
• 238000000034 method Methods 0.000 title claims abstract description 26
• 238000002360 preparation method Methods 0.000 title claims abstract description 15
• 230000008569 process Effects 0.000 title claims abstract description 7
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 11
• 238000011282 treatment Methods 0.000 title claims description 11
• 239000003814 drug Substances 0.000 title claims description 9
• 239000000825 pharmaceutical preparation Substances 0.000 title claims description 7
• 238000004519 manufacturing process Methods 0.000 title claims description 5
• UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical class C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 title abstract description 16
• 201000010099 disease Diseases 0.000 title description 5
• 239000004480 active ingredient Substances 0.000 claims abstract 4
• 238000006243 chemical reaction Methods 0.000 claims description 157
• 239000000203 mixture Substances 0.000 claims description 34
• -1 lower-alkenyl Chemical group 0.000 claims description 33
• 125000003118 aryl group Chemical group 0.000 claims description 29
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
• 125000000623 heterocyclic group Chemical group 0.000 claims description 28
• 150000003839 salts Chemical class 0.000 claims description 22
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 21
• 239000001257 hydrogen Substances 0.000 claims description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 20
• 125000000217 alkyl group Chemical group 0.000 claims description 19
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 19
• 102000002512 Orexin Human genes 0.000 claims description 17
• 108060005714 orexin Proteins 0.000 claims description 17
• 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 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 12
• 125000001424 substituent group Chemical group 0.000 claims description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• 229910052736 halogen Inorganic materials 0.000 claims description 8
• 150000002367 halogens Chemical class 0.000 claims description 8
• 208000008589 Obesity Diseases 0.000 claims description 7
• 239000000654 additive Substances 0.000 claims description 7
• 235000020824 obesity Nutrition 0.000 claims description 7
• 208000019116 sleep disease Diseases 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• 208000035475 disorder Diseases 0.000 claims description 6
• UZJLYRRDVFWSGA-UHFFFAOYSA-N n-benzylacetamide Chemical compound CC(=O)NCC1=CC=CC=C1 UZJLYRRDVFWSGA-UHFFFAOYSA-N 0.000 claims description 5
• 239000002253 acid Substances 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 229910052757 nitrogen Inorganic materials 0.000 claims description 4
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
• 229920006395 saturated elastomer Polymers 0.000 claims description 4
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
• 125000002619 bicyclic group Chemical group 0.000 claims description 3
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
• 125000005842 heteroatom Chemical group 0.000 claims description 3
• 125000002950 monocyclic group Chemical group 0.000 claims description 3
• 125000001624 naphthyl group Chemical group 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 239000001301 oxygen Substances 0.000 claims description 3
• 229910052717 sulfur Chemical group 0.000 claims description 3
• 239000011593 sulfur Chemical group 0.000 claims description 3
• GEYCZKOLGCILBP-UHFFFAOYSA-N 2-[1-[(3,4-dichlorophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(pyridin-3-ylmethyl)acetamide Chemical compound C=1C=C(Cl)C(Cl)=CC=1CC1C=2C=C(OC)C(OC)=CC=2CCN1CC(=O)NCC1=CC=CN=C1 GEYCZKOLGCILBP-UHFFFAOYSA-N 0.000 claims description 2
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
• 125000004104 aryloxy group Chemical group 0.000 claims description 2
• 238000003776 cleavage reaction Methods 0.000 claims description 2
• 238000006482 condensation reaction Methods 0.000 claims description 2
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
• 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 2
• 238000005580 one pot reaction Methods 0.000 claims description 2
• 230000007017 scission Effects 0.000 claims description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
• BFYOCLKGJYHCMY-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(naphthalen-1-ylmethyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)NCC1=CC=CC2=CC=CC=C12 BFYOCLKGJYHCMY-UHFFFAOYSA-N 0.000 claims 1
• ASOAAMJIFYSJEV-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-8-ethoxy-5-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(pyridin-2-ylmethyl)acetamide Chemical compound C=1C=C(OC)C(OC)=CC=1CC1C=2C(OCC)=CC=C(OC)C=2CCN1CC(=O)NCC1=CC=CC=N1 ASOAAMJIFYSJEV-UHFFFAOYSA-N 0.000 claims 1
• 239000012876 carrier material Substances 0.000 claims 1
• 150000002148 esters Chemical class 0.000 claims 1
• 238000002955 isolation Methods 0.000 claims 1
• 238000002156 mixing Methods 0.000 claims 1
• ACOHAEBNFWGQCL-UHFFFAOYSA-N n-(pyridin-2-ylmethyl)acetamide Chemical compound CC(=O)NCC1=CC=CC=N1 ACOHAEBNFWGQCL-UHFFFAOYSA-N 0.000 claims 1
• FYSUZYYFUUADES-UHFFFAOYSA-N n-benzyl-2-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)NCC1=CC=CC=C1 FYSUZYYFUUADES-UHFFFAOYSA-N 0.000 claims 1
• 229940123730 Orexin receptor antagonist Drugs 0.000 abstract description 3
• 239000008194 pharmaceutical composition Substances 0.000 abstract 2
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 252
• LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 151
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 50
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 46
• 238000007363 ring formation reaction Methods 0.000 description 31
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
• 239000000243 solution Substances 0.000 description 23
• YXWQTVWJNHKSCC-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1 YXWQTVWJNHKSCC-UHFFFAOYSA-N 0.000 description 21
• WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 19
• ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 18
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
• PXJACNDVRNAFHD-UHFFFAOYSA-N (2-methoxyphenyl)methanamine Chemical compound COC1=CC=CC=C1CN PXJACNDVRNAFHD-UHFFFAOYSA-N 0.000 description 14
• LAUPTNYHVCVPFH-UHFFFAOYSA-N (2-ethoxyphenyl)methanamine Chemical compound CCOC1=CC=CC=C1CN LAUPTNYHVCVPFH-UHFFFAOYSA-N 0.000 description 13
• BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 13
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• 239000000460 chlorine Substances 0.000 description 12
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 12
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
• 239000008346 aqueous phase Substances 0.000 description 11
• AKEYUWUEAXIBTF-UHFFFAOYSA-N n-methylnaphthalen-1-amine Chemical compound C1=CC=C2C(NC)=CC=CC2=C1 AKEYUWUEAXIBTF-UHFFFAOYSA-N 0.000 description 11
• XASGBYOFEJTAPK-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-5,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound N1CCC=2C(OC)=CC=C(OC)C=2C1CC1=CC=C(OC)C(OC)=C1 XASGBYOFEJTAPK-UHFFFAOYSA-N 0.000 description 10
• QBJIMTPENIGDOG-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)acetyl chloride Chemical compound COC1=CC=C(CC(Cl)=O)C=C1OC QBJIMTPENIGDOG-UHFFFAOYSA-N 0.000 description 10
• 108091003079 Bovine Serum Albumin Proteins 0.000 description 10
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 10
• KPWTVVBDJMLSJG-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound N1CCC2=CC(OC)=CC=C2C1CC1=CC=C(OC)C(OC)=C1 KPWTVVBDJMLSJG-UHFFFAOYSA-N 0.000 description 9
• 208000002193 Pain Diseases 0.000 description 9
• 239000012074 organic phase Substances 0.000 description 9
• 239000012981 Hank's balanced salt solution Substances 0.000 description 8
• 238000003818 flash chromatography Methods 0.000 description 8
• 239000012071 phase Substances 0.000 description 8
• 239000011541 reaction mixture Substances 0.000 description 8
• 150000003526 tetrahydroisoquinolines Chemical class 0.000 description 8
• YXWQTVWJNHKSCC-INIZCTEOSA-N (1s)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=C(OC)C(OC)=CC=C1C[C@H]1C2=CC(OC)=C(OC)C=C2CCN1 YXWQTVWJNHKSCC-INIZCTEOSA-N 0.000 description 7
• ZWXFFJWOZVUYKB-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=C(OC)C(OC)=C(OC)C=C2CCN1 ZWXFFJWOZVUYKB-UHFFFAOYSA-N 0.000 description 7
• WMWYGDZKGRHADI-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-7-propan-2-yloxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC(C)C)=C(OC)C=C2CCN1 WMWYGDZKGRHADI-UHFFFAOYSA-N 0.000 description 7
• NRJCAOCPBSXOGP-UHFFFAOYSA-N 6,7-dimethoxy-1-[(3-methoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline Chemical compound COC1=CC=CC(CC2C3=CC(OC)=C(OC)C=C3CCN2)=C1 NRJCAOCPBSXOGP-UHFFFAOYSA-N 0.000 description 7
• 239000005557 antagonist Substances 0.000 description 7
• LRFWYBZWRQWZIM-UHFFFAOYSA-N (2-fluorophenyl)methanamine Chemical compound NCC1=CC=CC=C1F LRFWYBZWRQWZIM-UHFFFAOYSA-N 0.000 description 6
• ANWKSRMTENFMAJ-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-5,6,7-trimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=C(OC)C(OC)=CC=C1CC1C(C=C(OC)C(OC)=C2OC)=C2CCN1 ANWKSRMTENFMAJ-UHFFFAOYSA-N 0.000 description 6
• CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 6
• JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 6
• BGXHKISGQNWFOY-UHFFFAOYSA-N 4-[(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]-n,n-dimethylaniline Chemical compound C1=2C=C(OC)C(OC)=CC=2CCNC1CC1=CC=C(N(C)C)C=C1 BGXHKISGQNWFOY-UHFFFAOYSA-N 0.000 description 6
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
• 102000008834 Orexin receptor Human genes 0.000 description 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
• BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 6
• 238000010511 deprotection reaction Methods 0.000 description 6
• HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 6
• 239000003921 oil Substances 0.000 description 6
• 235000019198 oils Nutrition 0.000 description 6
• 150000002989 phenols Chemical class 0.000 description 6
• HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 6
• 239000002904 solvent Substances 0.000 description 6
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
• PFYXGKHVNOPDHU-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-ylmethyl)-5,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=C2OCOC2=CC(CC2C=3C(OC)=CC=C(C=3CCN2)OC)=C1 PFYXGKHVNOPDHU-UHFFFAOYSA-N 0.000 description 5
• SRKDGMYMABXBMA-UHFFFAOYSA-N 1-[(2,5-dimethoxyphenyl)methyl]-5,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound COC1=CC=C(OC)C(CC2C3=C(OC)C=CC(OC)=C3CCN2)=C1 SRKDGMYMABXBMA-UHFFFAOYSA-N 0.000 description 5
• DQLMJULGOGAQCH-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-6,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=2C(OC)=CC(OC)=CC=2CCNC1CC1=CC=C(OC)C(OC)=C1 DQLMJULGOGAQCH-UHFFFAOYSA-N 0.000 description 5
• HWNSTGWDEVWFNH-UHFFFAOYSA-N 1-benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=2C=C(OC)C(OC)=CC=2CCNC1CC1=CC=CC=C1 HWNSTGWDEVWFNH-UHFFFAOYSA-N 0.000 description 5
• MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 5
• FPWLTKFZPJGKSX-UHFFFAOYSA-N 2-methoxy-2-(3-methoxyphenyl)ethanamine Chemical compound COC(CN)C1=CC=CC(OC)=C1 FPWLTKFZPJGKSX-UHFFFAOYSA-N 0.000 description 5
• HSNRSHBFNHIQQL-UHFFFAOYSA-N 6,7-dimethoxy-1-(naphthalen-2-ylmethyl)-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=CC2=CC(CC3NCCC=4C=C(C(=CC=43)OC)OC)=CC=C21 HSNRSHBFNHIQQL-UHFFFAOYSA-N 0.000 description 5
• NCBLMBAELRCUHD-UHFFFAOYSA-N 6,7-dimethoxy-1-[(2,3,4-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=2C=C(OC)C(OC)=CC=2CCNC1CC1=CC=C(OC)C(OC)=C1OC NCBLMBAELRCUHD-UHFFFAOYSA-N 0.000 description 5
• 239000007995 HEPES buffer Substances 0.000 description 5
• 230000015572 biosynthetic process Effects 0.000 description 5
• 229940098773 bovine serum albumin Drugs 0.000 description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
• 230000008878 coupling Effects 0.000 description 5
• 238000010168 coupling process Methods 0.000 description 5
• 238000005859 coupling reaction Methods 0.000 description 5
• OFNHNCAUVYOTPM-IIIOAANCSA-N orexin-a Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H](C)NC(=O)CNC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H]1NC(=O)[C@H](CO)NC(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@H](C(N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N2)[C@@H](C)O)=O)CSSC1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(C)C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H]1NC(=O)CC1)C1=CNC=N1 OFNHNCAUVYOTPM-IIIOAANCSA-N 0.000 description 5
• 102000005962 receptors Human genes 0.000 description 5
• 108020003175 receptors Proteins 0.000 description 5
• 239000000725 suspension Substances 0.000 description 5
• 238000003786 synthesis reaction Methods 0.000 description 5
• YRYCIFUZSUMAAY-UHFFFAOYSA-N (RS)-1-benzyl-1,2,3,4-tetrahydroisoquinoline Chemical group N1CCC2=CC=CC=C2C1CC1=CC=CC=C1 YRYCIFUZSUMAAY-UHFFFAOYSA-N 0.000 description 4
• YSOCJYPSQCCGNA-UHFFFAOYSA-N 1-[(3-bromo-4-methoxyphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=C(Br)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1 YSOCJYPSQCCGNA-UHFFFAOYSA-N 0.000 description 4
• NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 4
• ZSTCPHVBMNDKEB-UHFFFAOYSA-N 6,7-dimethoxy-1-(2-phenylethyl)-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=2C=C(OC)C(OC)=CC=2CCNC1CCC1=CC=CC=C1 ZSTCPHVBMNDKEB-UHFFFAOYSA-N 0.000 description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
• 108050000742 Orexin Receptor Proteins 0.000 description 4
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• 125000003545 alkoxy group Chemical group 0.000 description 4
• 150000001347 alkyl bromides Chemical class 0.000 description 4
• 150000001412 amines Chemical class 0.000 description 4
• 229910052801 chlorine Inorganic materials 0.000 description 4
• 238000001816 cooling Methods 0.000 description 4
• 229940079593 drug Drugs 0.000 description 4
• 239000007903 gelatin capsule Substances 0.000 description 4
• 150000002527 isonitriles Chemical class 0.000 description 4
• 239000010502 orange oil Substances 0.000 description 4
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
• 229920005862 polyol Polymers 0.000 description 4
• 150000003077 polyols Chemical class 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• 108090000765 processed proteins & peptides Proteins 0.000 description 4
• 238000010992 reflux Methods 0.000 description 4
• 239000007858 starting material Substances 0.000 description 4
• KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 description 3
• CJAAPVQEZPAQNI-UHFFFAOYSA-N (2-methylphenyl)methanamine Chemical compound CC1=CC=CC=C1CN CJAAPVQEZPAQNI-UHFFFAOYSA-N 0.000 description 3
• RGXUCUWVGKLACF-UHFFFAOYSA-N (3-methylphenyl)methanamine Chemical compound CC1=CC=CC(CN)=C1 RGXUCUWVGKLACF-UHFFFAOYSA-N 0.000 description 3
• IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 3
• JPQWLBDPQWBRPV-UHFFFAOYSA-N 1-[(3,4-dichlorophenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=2C=C(OC)C(OC)=CC=2CCNC1CC1=CC=C(Cl)C(Cl)=C1 JPQWLBDPQWBRPV-UHFFFAOYSA-N 0.000 description 3
• FEBIPJYPQVUYPH-UHFFFAOYSA-N 1-[(3,4-diethylphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=C(CC)C(CC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1 FEBIPJYPQVUYPH-UHFFFAOYSA-N 0.000 description 3
• FNSGPTFLDDASLF-UHFFFAOYSA-N 1-[(3,4-dimethylphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=2C=C(OC)C(OC)=CC=2CCNC1CC1=CC=C(C)C(C)=C1 FNSGPTFLDDASLF-UHFFFAOYSA-N 0.000 description 3
• MOOMGAOQWHKDSC-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=2C=C(OC)C(OC)=CC=2CCNC1CC1=CC=C(Cl)C=C1 MOOMGAOQWHKDSC-UHFFFAOYSA-N 0.000 description 3
• IGWXUFJDUPHOHK-UHFFFAOYSA-N 1-[(4-fluorophenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=2C=C(OC)C(OC)=CC=2CCNC1CC1=CC=C(F)C=C1 IGWXUFJDUPHOHK-UHFFFAOYSA-N 0.000 description 3
• HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 3
• UPSXAPQYNGXVBF-UHFFFAOYSA-N 2-bromobutane Chemical compound CCC(C)Br UPSXAPQYNGXVBF-UHFFFAOYSA-N 0.000 description 3
• RUJHATQMIMUYKD-UHFFFAOYSA-N 2-naphthalen-1-ylethanamine Chemical compound C1=CC=C2C(CCN)=CC=CC2=C1 RUJHATQMIMUYKD-UHFFFAOYSA-N 0.000 description 3
• IGPYNHMMDJOIQN-UHFFFAOYSA-N 6,7-dimethoxy-1-(1-phenylpropyl)-1,2,3,4-tetrahydroisoquinoline Chemical compound N1CCC2=CC(OC)=C(OC)C=C2C1C(CC)C1=CC=CC=C1 IGPYNHMMDJOIQN-UHFFFAOYSA-N 0.000 description 3
• GXTUEUWFEKEQHJ-UHFFFAOYSA-N 6,7-dimethoxy-1-[(4-methoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1 GXTUEUWFEKEQHJ-UHFFFAOYSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• 208000019901 Anxiety disease Diseases 0.000 description 3
• CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 3
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
• 208000004454 Hyperalgesia Diseases 0.000 description 3
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 150000001408 amides Chemical group 0.000 description 3
• 229910052786 argon Inorganic materials 0.000 description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
• 239000000872 buffer Substances 0.000 description 3
• 239000011575 calcium Substances 0.000 description 3
• 229910052791 calcium Inorganic materials 0.000 description 3
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
• 239000013078 crystal Substances 0.000 description 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 description 3
• 239000008298 dragée Substances 0.000 description 3
• 238000002474 experimental method Methods 0.000 description 3
• 239000012894 fetal calf serum Substances 0.000 description 3
• 239000012458 free base Substances 0.000 description 3
• 230000002267 hypothalamic effect Effects 0.000 description 3
• RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 3
• 208000004296 neuralgia Diseases 0.000 description 3
• OHOWSYIKESXDMN-WMQZXSDYSA-N orexin-b Chemical compound C([C@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)CNC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@@H](N)CCSC)[C@@H](C)O)[C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CCCN=C(N)N)C(N)=O)C1=CNC=N1 OHOWSYIKESXDMN-WMQZXSDYSA-N 0.000 description 3
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
• 229940044551 receptor antagonist Drugs 0.000 description 3
• 239000002464 receptor antagonist Substances 0.000 description 3
• 239000011550 stock solution Substances 0.000 description 3
• 239000000126 substance Substances 0.000 description 3
• GDFBHCMFIUBEQT-UHFFFAOYSA-N (2,5-difluorophenyl)methanamine Chemical compound NCC1=CC(F)=CC=C1F GDFBHCMFIUBEQT-UHFFFAOYSA-N 0.000 description 2
• IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 description 2
• QUKGLNCXGVWCJX-UHFFFAOYSA-N 1,3,4-thiadiazol-2-amine Chemical compound NC1=NN=CS1 QUKGLNCXGVWCJX-UHFFFAOYSA-N 0.000 description 2
• HOFWLPPBIBQUCV-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-ylmethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=C2OCOC2=CC(CC2NCCC=3C=C(C(=CC=32)OC)OC)=C1 HOFWLPPBIBQUCV-UHFFFAOYSA-N 0.000 description 2
• LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
• HYHOBLFHBFTVGR-UHFFFAOYSA-N 1-[(2,5-dimethoxyphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound COC1=CC=C(OC)C(CC2C3=CC(OC)=C(OC)C=C3CCN2)=C1 HYHOBLFHBFTVGR-UHFFFAOYSA-N 0.000 description 2
• XUGXVRXTSBIUON-UHFFFAOYSA-N 1-[(3,4-difluorophenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=2C=C(OC)C(OC)=CC=2CCNC1CC1=CC=C(F)C(F)=C1 XUGXVRXTSBIUON-UHFFFAOYSA-N 0.000 description 2
• WKMNJFHMNUVFSX-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-5-methoxy-8-phenylmethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=2C(CC=3C=C(OC)C(OC)=CC=3)NCCC=2C(OC)=CC=C1OCC1=CC=CC=C1 WKMNJFHMNUVFSX-UHFFFAOYSA-N 0.000 description 2
• RZUZZVWHTNDQOV-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-7-phenylmethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OCC=3C=CC=CC=3)=C(OC)C=C2CCN1 RZUZZVWHTNDQOV-UHFFFAOYSA-N 0.000 description 2
• HLIQXYYZPCEECQ-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-7-methoxy-6-phenylmethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OCC=3C=CC=CC=3)C=C2CCN1 HLIQXYYZPCEECQ-UHFFFAOYSA-N 0.000 description 2
• XMKIJBZKRPJLGX-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-8-methoxy-5-phenylmethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=C(OC)C=CC(OCC=3C=CC=CC=3)=C2CCN1 XMKIJBZKRPJLGX-UHFFFAOYSA-N 0.000 description 2
• UCOSRTUSVXHIMK-UHFFFAOYSA-N 1h-benzimidazol-2-ylmethanamine Chemical compound C1=CC=C2NC(CN)=NC2=C1 UCOSRTUSVXHIMK-UHFFFAOYSA-N 0.000 description 2
• CZOZLTKKYXGUOF-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-n-[2-(2,5-dimethoxyphenyl)ethyl]acetamide Chemical compound COC1=CC=C(OC)C(CCNC(=O)CC=2C=C3OCOC3=CC=2)=C1 CZOZLTKKYXGUOF-UHFFFAOYSA-N 0.000 description 2
• RPDXVMBCIRAVCV-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)-n-[2-(3,4-dimethoxyphenyl)ethyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)CC1=CC=C(OCO2)C2=C1 RPDXVMBCIRAVCV-UHFFFAOYSA-N 0.000 description 2
• ODVLMCWNGKLROU-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-yl)acetic acid Chemical compound OC(=O)CC1=CC=C2OCOC2=C1 ODVLMCWNGKLROU-UHFFFAOYSA-N 0.000 description 2
• GJBVKWQIHCHNBO-UHFFFAOYSA-N 2-(2,5-dimethoxyphenyl)-n-[2-(2,5-dimethoxyphenyl)ethyl]acetamide Chemical compound COC1=CC=C(OC)C(CCNC(=O)CC=2C(=CC=C(OC)C=2)OC)=C1 GJBVKWQIHCHNBO-UHFFFAOYSA-N 0.000 description 2
• YSSRPZDIPQMYDW-UHFFFAOYSA-N 2-(2,5-dimethoxyphenyl)-n-[2-(3,4-dimethoxyphenyl)ethyl]acetamide Chemical compound COC1=CC=C(OC)C(CC(=O)NCCC=2C=C(OC)C(OC)=CC=2)=C1 YSSRPZDIPQMYDW-UHFFFAOYSA-N 0.000 description 2
• RAPIPBRHRYSAHQ-UHFFFAOYSA-N 2-(2,5-dimethoxyphenyl)acetyl chloride Chemical compound COC1=CC=C(OC)C(CC(Cl)=O)=C1 RAPIPBRHRYSAHQ-UHFFFAOYSA-N 0.000 description 2
• AAQIRQUMPMWERW-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-n-[2-(3,4-dimethoxyphenyl)ethyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)CC1=CC=C(F)C(F)=C1 AAQIRQUMPMWERW-UHFFFAOYSA-N 0.000 description 2
• LMBCEKZJBDMWCI-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-[2-(2,5-dimethoxyphenyl)ethyl]acetamide Chemical compound COC1=CC=C(OC)C(CCNC(=O)CC=2C=C(OC)C(OC)=CC=2)=C1 LMBCEKZJBDMWCI-UHFFFAOYSA-N 0.000 description 2
• WKMPNMHAVRYZFG-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-[2-(3-methoxyphenyl)ethyl]acetamide Chemical compound COC1=CC=CC(CCNC(=O)CC=2C=C(OC)C(OC)=CC=2)=C1 WKMPNMHAVRYZFG-UHFFFAOYSA-N 0.000 description 2
• LPBNXHIAXFOGEN-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-[2-(5-methoxy-2-phenylmethoxyphenyl)ethyl]acetamide Chemical compound C=1C=C(OC)C(OC)=CC=1CC(=O)NCCC1=CC(OC)=CC=C1OCC1=CC=CC=C1 LPBNXHIAXFOGEN-UHFFFAOYSA-N 0.000 description 2
• XPHIFDXVOGTFLO-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-[2-(3,4-dimethoxyphenyl)ethyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)CC1=CC=C(Cl)C=C1 XPHIFDXVOGTFLO-UHFFFAOYSA-N 0.000 description 2
• NBICEVBGTVHJCK-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-[(3-methylphenyl)methyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)NCC1=CC=CC(C)=C1 NBICEVBGTVHJCK-UHFFFAOYSA-N 0.000 description 2
• JOFJQVWIZBJLIW-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-[(4-fluorophenyl)methyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)NCC1=CC=C(F)C=C1 JOFJQVWIZBJLIW-UHFFFAOYSA-N 0.000 description 2
• JUIKUQOUMZUFQT-UHFFFAOYSA-N 2-bromoacetamide Chemical class NC(=O)CBr JUIKUQOUMZUFQT-UHFFFAOYSA-N 0.000 description 2
• UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 2
• VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 2
• KYHMEWQGAKQCIM-UHFFFAOYSA-N 3-naphthalen-1-ylpropanamide Chemical compound C1=CC=C2C(CCC(=O)N)=CC=CC2=C1 KYHMEWQGAKQCIM-UHFFFAOYSA-N 0.000 description 2
• FUTZESSLBXJDFG-UHFFFAOYSA-N 4-[(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)methyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(CC2C3=CC(OC)=C(OC)C=C3CCN2)=C1 FUTZESSLBXJDFG-UHFFFAOYSA-N 0.000 description 2
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
• WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 2
• 206010002383 Angina Pectoris Diseases 0.000 description 2
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
• 206010002653 Anosmia Diseases 0.000 description 2
• KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
• 241000699802 Cricetulus griseus Species 0.000 description 2
• 206010012289 Dementia Diseases 0.000 description 2
• 206010012335 Dependence Diseases 0.000 description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 2
• 208000012661 Dyskinesia Diseases 0.000 description 2
• 201000011240 Frontotemporal dementia Diseases 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• 101000598921 Homo sapiens Orexin Proteins 0.000 description 2
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
• 208000035154 Hyperesthesia Diseases 0.000 description 2
• 206010021067 Hypopituitarism Diseases 0.000 description 2
• 208000028482 Hypothalamic disease Diseases 0.000 description 2
• 208000019695 Migraine disease Diseases 0.000 description 2
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
• 208000006199 Parasomnias Diseases 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• 208000007913 Pituitary Neoplasms Diseases 0.000 description 2
• 206010036832 Prolactinoma Diseases 0.000 description 2
• 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
• 239000000556 agonist Substances 0.000 description 2
• 230000029936 alkylation Effects 0.000 description 2
• 238000005804 alkylation reaction Methods 0.000 description 2
• 150000001413 amino acids Chemical class 0.000 description 2
• 230000036506 anxiety Effects 0.000 description 2
• 239000002585 base Substances 0.000 description 2
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
• 229910052794 bromium Inorganic materials 0.000 description 2
• AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 208000014439 complex regional pain syndrome type 2 Diseases 0.000 description 2
• PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
• 206010012601 diabetes mellitus Diseases 0.000 description 2
• 208000024732 dysthymic disease Diseases 0.000 description 2
• 230000000694 effects Effects 0.000 description 2
• WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
• 239000003925 fat Substances 0.000 description 2
• 238000012632 fluorescent imaging Methods 0.000 description 2
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• QRMZSPFSDQBLIX-UHFFFAOYSA-N homovanillic acid Chemical compound COC1=CC(CC(O)=O)=CC=C1O QRMZSPFSDQBLIX-UHFFFAOYSA-N 0.000 description 2
• 208000031424 hyperprolactinemia Diseases 0.000 description 2
• 238000002347 injection Methods 0.000 description 2
• 239000007924 injection Substances 0.000 description 2
• 206010022437 insomnia Diseases 0.000 description 2
• 229910052740 iodine Inorganic materials 0.000 description 2
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• 230000014759 maintenance of location Effects 0.000 description 2
• 238000005259 measurement Methods 0.000 description 2
• RHCSKNNOAZULRK-UHFFFAOYSA-N mescaline Chemical compound COC1=CC(CCN)=CC(OC)=C1OC RHCSKNNOAZULRK-UHFFFAOYSA-N 0.000 description 2
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
• GCYIIFMWMWWCQR-UHFFFAOYSA-N methyl 2-[1-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]cyclohexa-2,4-dien-1-yl]acetate Chemical compound C1CC2=CC(OC)=C(OC)C=C2C(CC=2C=C(OC)C(OC)=CC=2)C1C1(CC(=O)OC)CC=CC=C1 GCYIIFMWMWWCQR-UHFFFAOYSA-N 0.000 description 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
• 206010027599 migraine Diseases 0.000 description 2
• JEMCXCMZAJPLLR-UHFFFAOYSA-N n-[2-(2,5-dimethoxyphenyl)ethyl]-2,2-diphenylacetamide Chemical compound COC1=CC=C(OC)C(CCNC(=O)C(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 JEMCXCMZAJPLLR-UHFFFAOYSA-N 0.000 description 2
• MDDIUSXQWPNOCY-UHFFFAOYSA-N n-[2-(2,5-dimethoxyphenyl)ethyl]-2-phenylacetamide Chemical compound COC1=CC=C(OC)C(CCNC(=O)CC=2C=CC=CC=2)=C1 MDDIUSXQWPNOCY-UHFFFAOYSA-N 0.000 description 2
• HQDGRCBVDVPNBF-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-2-(2,3,4-trimethoxyphenyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)CC1=CC=C(OC)C(OC)=C1OC HQDGRCBVDVPNBF-UHFFFAOYSA-N 0.000 description 2
• FGPUFQRNZGCKQV-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-2-(3,4,5-trimethoxyphenyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)CC1=CC(OC)=C(OC)C(OC)=C1 FGPUFQRNZGCKQV-UHFFFAOYSA-N 0.000 description 2
• JXUNQKVJRZBSER-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-2-(3-methoxyphenyl)acetamide Chemical compound COC1=CC=CC(CC(=O)NCCC=2C=C(OC)C(OC)=CC=2)=C1 JXUNQKVJRZBSER-UHFFFAOYSA-N 0.000 description 2
• FAMYMMVKOXQHTC-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-2-(4-fluorophenyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)CC1=CC=C(F)C=C1 FAMYMMVKOXQHTC-UHFFFAOYSA-N 0.000 description 2
• FBMGZFDOFQXQKX-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-2-(4-hydroxy-3-methoxyphenyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)CC1=CC=C(O)C(OC)=C1 FBMGZFDOFQXQKX-UHFFFAOYSA-N 0.000 description 2
• WZZFLNQCSFTAQT-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-2-(4-methoxy-3-phenylmethoxyphenyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)CC1=CC=C(OC)C(OCC=2C=CC=CC=2)=C1 WZZFLNQCSFTAQT-UHFFFAOYSA-N 0.000 description 2
• VXBDJWHXZMSPEZ-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-2-(4-methoxyphenyl)acetamide Chemical compound C1=CC(OC)=CC=C1CC(=O)NCCC1=CC=C(OC)C(OC)=C1 VXBDJWHXZMSPEZ-UHFFFAOYSA-N 0.000 description 2
• HVABELWWEQMYIB-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-2-phenylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)CC1=CC=CC=C1 HVABELWWEQMYIB-UHFFFAOYSA-N 0.000 description 2
• NEFROOCEKFXOJH-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-2-phenylbutanamide Chemical compound C=1C=CC=CC=1C(CC)C(=O)NCCC1=CC=C(OC)C(OC)=C1 NEFROOCEKFXOJH-UHFFFAOYSA-N 0.000 description 2
• NKTXVHNEQLENPU-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-2-phenylmethoxyacetamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)COCC1=CC=CC=C1 NKTXVHNEQLENPU-UHFFFAOYSA-N 0.000 description 2
• XZQORMQJAFYPRT-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-3-phenylpropanamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)CCC1=CC=CC=C1 XZQORMQJAFYPRT-UHFFFAOYSA-N 0.000 description 2
• GQMVLTNYCPDBLP-UHFFFAOYSA-N n-benzyl-2-[1-[(3,4-dimethoxyphenyl)methyl]-6-hydroxy-7-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C=1C=CC=CC=1CNC(=O)CN1CCC=2C=C(O)C(OC)=CC=2C1CC1=CC=C(OC)C(OC)=C1 GQMVLTNYCPDBLP-UHFFFAOYSA-N 0.000 description 2
• ZJLMETHEORLUCQ-UHFFFAOYSA-N n-benzyl-2-[1-[(3-hydroxy-4-methoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(O)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)NCC1=CC=CC=C1 ZJLMETHEORLUCQ-UHFFFAOYSA-N 0.000 description 2
• YNDQAFGFNLWXQB-UHFFFAOYSA-N n-benzyl-2-[1-[(4-hydroxy-3-methoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(O)C(OC)=CC(CC2C3=CC(OC)=C(OC)C=C3CCN2CC(=O)NCC=2C=CC=CC=2)=C1 YNDQAFGFNLWXQB-UHFFFAOYSA-N 0.000 description 2
• NVSYANRBXPURRQ-UHFFFAOYSA-N naphthalen-1-ylmethanamine Chemical compound C1=CC=C2C(CN)=CC=CC2=C1 NVSYANRBXPURRQ-UHFFFAOYSA-N 0.000 description 2
• 201000003631 narcolepsy Diseases 0.000 description 2
• 208000021722 neuropathic pain Diseases 0.000 description 2
• 208000015238 neurotic disease Diseases 0.000 description 2
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 210000001672 ovary Anatomy 0.000 description 2
• WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
• 229910000027 potassium carbonate Inorganic materials 0.000 description 2
• 235000015320 potassium carbonate Nutrition 0.000 description 2
• DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 2
• 229960003081 probenecid Drugs 0.000 description 2
• 208000030153 prolactin-producing pituitary gland adenoma Diseases 0.000 description 2
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• 201000000980 schizophrenia Diseases 0.000 description 2
• 201000002859 sleep apnea Diseases 0.000 description 2
• 150000003384 small molecules Chemical class 0.000 description 2
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
• 235000017557 sodium bicarbonate Nutrition 0.000 description 2
• 239000012279 sodium borohydride Substances 0.000 description 2
• 229910000033 sodium borohydride Inorganic materials 0.000 description 2
• 239000007787 solid Substances 0.000 description 2
• 238000003756 stirring Methods 0.000 description 2
• UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
• KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
• 239000000829 suppository Substances 0.000 description 2
• CQXDYHPBXDZWBA-UHFFFAOYSA-N tert-butyl 2,2,2-trichloroethanimidate Chemical compound CC(C)(C)OC(=N)C(Cl)(Cl)Cl CQXDYHPBXDZWBA-UHFFFAOYSA-N 0.000 description 2
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
• 235000015112 vegetable and seed oil Nutrition 0.000 description 2
• 239000008158 vegetable oil Substances 0.000 description 2
• 239000001993 wax Substances 0.000 description 2
• VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
• QOWBXWFYRXSBAS-UHFFFAOYSA-N (2,4-dimethoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C(OC)=C1 QOWBXWFYRXSBAS-UHFFFAOYSA-N 0.000 description 1
• DOMQFIFVDIAOOT-ROUUACIJSA-N (2S,3R)-N-[4-(2,6-dimethoxyphenyl)-5-(5-methylpyridin-3-yl)-1,2,4-triazol-3-yl]-3-(5-methylpyrimidin-2-yl)butane-2-sulfonamide Chemical compound COC1=C(C(=CC=C1)OC)N1C(=NN=C1C=1C=NC=C(C=1)C)NS(=O)(=O)[C@@H](C)[C@H](C)C1=NC=C(C=N1)C DOMQFIFVDIAOOT-ROUUACIJSA-N 0.000 description 1
• HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 description 1
• MCCAWZYURZFQOX-UHFFFAOYSA-N (6-methoxynaphthalen-2-yl)methanamine Chemical compound C1=C(CN)C=CC2=CC(OC)=CC=C21 MCCAWZYURZFQOX-UHFFFAOYSA-N 0.000 description 1
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
• UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 description 1
• ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
• MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
• MJUVRTYWUMPBTR-MRXNPFEDSA-N 1-(2,2-difluoro-1,3-benzodioxol-5-yl)-n-[1-[(2r)-2,3-dihydroxypropyl]-6-fluoro-2-(1-hydroxy-2-methylpropan-2-yl)indol-5-yl]cyclopropane-1-carboxamide Chemical compound FC=1C=C2N(C[C@@H](O)CO)C(C(C)(CO)C)=CC2=CC=1NC(=O)C1(C=2C=C3OC(F)(F)OC3=CC=2)CC1 MJUVRTYWUMPBTR-MRXNPFEDSA-N 0.000 description 1
• VMPLLPIDRGXFTQ-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline;hydrochloride Chemical compound [Cl-].C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CC[NH2+]1 VMPLLPIDRGXFTQ-UHFFFAOYSA-N 0.000 description 1
• FWIDZCMQCGNXCP-UHFFFAOYSA-N 1-[(4-bromo-3-methoxyphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=C(Br)C(OC)=CC(CC2C3=CC(OC)=C(OC)C=C3CCN2)=C1 FWIDZCMQCGNXCP-UHFFFAOYSA-N 0.000 description 1
• ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
• VXRWKBITZHUSQW-UHFFFAOYSA-N 1-benzhydryl-5,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound N1CCC=2C(OC)=CC=C(OC)C=2C1C(C=1C=CC=CC=1)C1=CC=CC=C1 VXRWKBITZHUSQW-UHFFFAOYSA-N 0.000 description 1
• JXBGBNUEKURSRY-UHFFFAOYSA-N 1-benzyl-5,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline Chemical compound N1CCC=2C(OC)=CC=C(OC)C=2C1CC1=CC=CC=C1 JXBGBNUEKURSRY-UHFFFAOYSA-N 0.000 description 1
• VNHWPVLQRKKKRY-UHFFFAOYSA-N 1-bromo-3-fluoropropane Chemical compound FCCCBr VNHWPVLQRKKKRY-UHFFFAOYSA-N 0.000 description 1
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
• RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
• KEJFADGISRFLFO-UHFFFAOYSA-N 1H-indazol-6-amine Chemical compound NC1=CC=C2C=NNC2=C1 KEJFADGISRFLFO-UHFFFAOYSA-N 0.000 description 1
• MSYLETHDEIJMAF-UHFFFAOYSA-N 2,2-diphenylacetyl chloride Chemical compound C=1C=CC=CC=1C(C(=O)Cl)C1=CC=CC=C1 MSYLETHDEIJMAF-UHFFFAOYSA-N 0.000 description 1
• JUOJVMYJTALTKH-UHFFFAOYSA-N 2-(1-benzyl-3,4-dihydro-1h-isoquinolin-2-yl)-n-[(2-methylphenyl)methyl]acetamide Chemical compound CC1=CC=CC=C1CNC(=O)CN1C(CC=2C=CC=CC=2)C2=CC=CC=C2CC1 JUOJVMYJTALTKH-UHFFFAOYSA-N 0.000 description 1
• YSOLKWJQSARACF-UHFFFAOYSA-N 2-(1-benzyl-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)-n-[(2-methylphenyl)methyl]acetamide Chemical compound C=1C=CC=CC=1CC1C=2C=C(OC)C(OC)=CC=2CCN1CC(=O)NCC1=CC=CC=C1C YSOLKWJQSARACF-UHFFFAOYSA-N 0.000 description 1
• RJUGHGUBIPEVPE-UHFFFAOYSA-N 2-(1-benzyl-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)-n-[(4-fluorophenyl)methyl]acetamide Chemical compound C=1C=CC=CC=1CC1C=2C=C(OC)C(OC)=CC=2CCN1CC(=O)NCC1=CC=C(F)C=C1 RJUGHGUBIPEVPE-UHFFFAOYSA-N 0.000 description 1
• ZMWCKCLDAQWIDA-UHFFFAOYSA-N 2-(2,3,4-trimethoxyphenyl)acetic acid Chemical compound COC1=CC=C(CC(O)=O)C(OC)=C1OC ZMWCKCLDAQWIDA-UHFFFAOYSA-N 0.000 description 1
• LPXOPDKFARVIQB-UHFFFAOYSA-N 2-(2-methoxy-5-phenylmethoxyphenyl)ethanamine Chemical compound C1=C(CCN)C(OC)=CC=C1OCC1=CC=CC=C1 LPXOPDKFARVIQB-UHFFFAOYSA-N 0.000 description 1
• DDSJXCGGOXKGSJ-UHFFFAOYSA-N 2-(3,4,5-trimethoxyphenyl)acetic acid Chemical compound COC1=CC(CC(O)=O)=CC(OC)=C1OC DDSJXCGGOXKGSJ-UHFFFAOYSA-N 0.000 description 1
• YCAKYFIYUHHCKW-UHFFFAOYSA-N 2-(3,4-difluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(F)C(F)=C1 YCAKYFIYUHHCKW-UHFFFAOYSA-N 0.000 description 1
• CFEHWNSMGUKJEU-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-2-methoxyethanamine Chemical compound COC(CN)C1=CC=C(OC)C(OC)=C1 CFEHWNSMGUKJEU-UHFFFAOYSA-N 0.000 description 1
• NFCIDYJGAZFATM-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-[2-(2,3,4-trimethoxyphenyl)ethyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC(=O)NCCC1=CC=C(OC)C(OC)=C1OC NFCIDYJGAZFATM-UHFFFAOYSA-N 0.000 description 1
• GYUWZWIKKACQSZ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-[2-(2-methoxy-5-phenylmethoxyphenyl)ethyl]acetamide Chemical compound C1=C(CCNC(=O)CC=2C=C(OC)C(OC)=CC=2)C(OC)=CC=C1OCC1=CC=CC=C1 GYUWZWIKKACQSZ-UHFFFAOYSA-N 0.000 description 1
• BXUQYJBJJMBZDJ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-[2-(3,4,5-trimethoxyphenyl)ethyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC(=O)NCCC1=CC(OC)=C(OC)C(OC)=C1 BXUQYJBJJMBZDJ-UHFFFAOYSA-N 0.000 description 1
• KEOYZVLRUGFKRP-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-[2-(3,5-dimethoxyphenyl)ethyl]acetamide Chemical compound COC1=CC(OC)=CC(CCNC(=O)CC=2C=C(OC)C(OC)=CC=2)=C1 KEOYZVLRUGFKRP-UHFFFAOYSA-N 0.000 description 1
• DSWVDOQADLXFFE-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-[2-(3-methoxy-4-phenylmethoxyphenyl)ethyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC(=O)NCCC(C=C1OC)=CC=C1OCC1=CC=CC=C1 DSWVDOQADLXFFE-UHFFFAOYSA-N 0.000 description 1
• UXKKZRKCHFAQGX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-[2-(3-methoxy-4-propan-2-yloxyphenyl)ethyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC(=O)NCCC1=CC=C(OC(C)C)C(OC)=C1 UXKKZRKCHFAQGX-UHFFFAOYSA-N 0.000 description 1
• UFDMCHIAXSZQGN-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-[2-(4-methoxy-3-phenylmethoxyphenyl)ethyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC(=O)NCCC1=CC=C(OC)C(OCC=2C=CC=CC=2)=C1 UFDMCHIAXSZQGN-UHFFFAOYSA-N 0.000 description 1
• GLMWLELOJCRYRI-UHFFFAOYSA-N 2-(3-methoxy-4-phenylmethoxyphenyl)ethanamine Chemical compound COC1=CC(CCN)=CC=C1OCC1=CC=CC=C1 GLMWLELOJCRYRI-UHFFFAOYSA-N 0.000 description 1
• HJGNAXXDNNYRNN-UHFFFAOYSA-N 2-(3-methoxy-4-propan-2-yloxyphenyl)ethanamine Chemical compound COC1=CC(CCN)=CC=C1OC(C)C HJGNAXXDNNYRNN-UHFFFAOYSA-N 0.000 description 1
• UZUYKYNVSJTWEH-UHFFFAOYSA-N 2-(3-methoxyphenyl)acetyl chloride Chemical compound COC1=CC=CC(CC(Cl)=O)=C1 UZUYKYNVSJTWEH-UHFFFAOYSA-N 0.000 description 1
• WJBMRZAHTUFBGE-UHFFFAOYSA-N 2-(3-methoxyphenyl)ethanamine Chemical compound COC1=CC=CC(CCN)=C1 WJBMRZAHTUFBGE-UHFFFAOYSA-N 0.000 description 1
• UMQUIRYNOVNYPA-UHFFFAOYSA-N 2-(4-chlorophenyl)acetyl chloride Chemical compound ClC(=O)CC1=CC=C(Cl)C=C1 UMQUIRYNOVNYPA-UHFFFAOYSA-N 0.000 description 1
• MGKPFALCNDRSQD-UHFFFAOYSA-N 2-(4-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(F)C=C1 MGKPFALCNDRSQD-UHFFFAOYSA-N 0.000 description 1
• WXWWJUKMWNYILA-UHFFFAOYSA-N 2-(4-methoxy-3-phenylmethoxyphenyl)acetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1OCC1=CC=CC=C1 WXWWJUKMWNYILA-UHFFFAOYSA-N 0.000 description 1
• HGPYIHOTQGSJAJ-UHFFFAOYSA-N 2-(4-methoxy-3-phenylmethoxyphenyl)ethanamine Chemical compound COC1=CC=C(CCN)C=C1OCC1=CC=CC=C1 HGPYIHOTQGSJAJ-UHFFFAOYSA-N 0.000 description 1
• CXJOONIFSVSFAD-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetyl chloride Chemical compound COC1=CC=C(CC(Cl)=O)C=C1 CXJOONIFSVSFAD-UHFFFAOYSA-N 0.000 description 1
• UPPFDZBHJOPNAI-UHFFFAOYSA-N 2-(5-methoxy-2-phenylmethoxyphenyl)ethanamine Chemical compound NCCC1=CC(OC)=CC=C1OCC1=CC=CC=C1 UPPFDZBHJOPNAI-UHFFFAOYSA-N 0.000 description 1
• YVHFWLYZVUCPFZ-VWLOTQADSA-N 2-[(1s)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(2-phenylethyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1C[C@H]1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)NCCC1=CC=CC=C1 YVHFWLYZVUCPFZ-VWLOTQADSA-N 0.000 description 1
• BFYOCLKGJYHCMY-NDEPHWFRSA-N 2-[(1s)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(naphthalen-1-ylmethyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1C[C@H]1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)NCC1=CC=CC2=CC=CC=C12 BFYOCLKGJYHCMY-NDEPHWFRSA-N 0.000 description 1
• KEWALFLCFJBWCO-QHCPKHFHSA-N 2-[(1s)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(pyridin-2-ylmethyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1C[C@H]1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)NCC1=CC=CC=N1 KEWALFLCFJBWCO-QHCPKHFHSA-N 0.000 description 1
• NNLPZVSBJHQYHC-UHFFFAOYSA-N 2-[1-(1,3-benzodioxol-5-ylmethyl)-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-[(2-ethoxyphenyl)methyl]acetamide Chemical compound CCOC1=CC=CC=C1CNC(=O)CN1C(CC=2C=C3OCOC3=CC=2)C2=CC(OC)=C(OC)C=C2CC1 NNLPZVSBJHQYHC-UHFFFAOYSA-N 0.000 description 1
• NXBHJXJJEGBLBZ-UHFFFAOYSA-N 2-[1-[(2,5-dimethoxyphenyl)methyl]-5,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-[(2-ethoxyphenyl)methyl]acetamide Chemical compound CCOC1=CC=CC=C1CNC(=O)CN1C(CC=2C(=CC=C(OC)C=2)OC)C2=C(OC)C=CC(OC)=C2CC1 NXBHJXJJEGBLBZ-UHFFFAOYSA-N 0.000 description 1
• NMIADDOCHFQYMI-UHFFFAOYSA-N 2-[1-[(3,4-diethylphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(pyridin-2-ylmethyl)acetamide Chemical compound C1=C(CC)C(CC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)NCC1=CC=CC=N1 NMIADDOCHFQYMI-UHFFFAOYSA-N 0.000 description 1
• YHOZFZRJFBWWMD-UHFFFAOYSA-N 2-[1-[(3,4-diethylphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(pyridin-4-ylmethyl)acetamide Chemical compound C1=C(CC)C(CC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)NCC1=CC=NC=C1 YHOZFZRJFBWWMD-UHFFFAOYSA-N 0.000 description 1
• GCQCVZZGKIKVTL-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-5,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(pyridin-2-ylmethyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=C(OC)C=CC(OC)=C2CCN1CC(=O)NCC1=CC=CC=N1 GCQCVZZGKIKVTL-UHFFFAOYSA-N 0.000 description 1
• UAXSWNJARCKBRP-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-5,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-[(2-methoxyphenyl)methyl]acetamide Chemical compound COC1=CC=CC=C1CNC(=O)CN1C(CC=2C=C(OC)C(OC)=CC=2)C2=C(OC)C=CC(OC)=C2CC1 UAXSWNJARCKBRP-UHFFFAOYSA-N 0.000 description 1
• MSTFIEWGGMZKOZ-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-5-methoxy-8-phenylmethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(pyridin-2-ylmethyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=C(OCC=3C=CC=CC=3)C=CC(OC)=C2CCN1CC(=O)NCC1=CC=CC=N1 MSTFIEWGGMZKOZ-UHFFFAOYSA-N 0.000 description 1
• ZPAUIZYCDVBPDX-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-6,7,8-trimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(2-phenylethyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=C(OC)C(OC)=C(OC)C=C2CCN1CC(=O)NCCC1=CC=CC=C1 ZPAUIZYCDVBPDX-UHFFFAOYSA-N 0.000 description 1
• BVIGMQYJRVBMEM-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-6,7,8-trimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(pyridin-2-ylmethyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=C(OC)C(OC)=C(OC)C=C2CCN1CC(=O)NCC1=CC=CC=N1 BVIGMQYJRVBMEM-UHFFFAOYSA-N 0.000 description 1
• BPPYYMZLRANARW-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(1-phenylethyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)NC(C)C1=CC=CC=C1 BPPYYMZLRANARW-UHFFFAOYSA-N 0.000 description 1
• WIERBVPMWIMPQC-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-[(2-fluorophenyl)methyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)NCC1=CC=CC=C1F WIERBVPMWIMPQC-UHFFFAOYSA-N 0.000 description 1
• LHFABXXKENNWII-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-[(2-methoxyphenyl)methyl]acetamide Chemical compound COC1=CC=CC=C1CNC(=O)CN1C(CC=2C=C(OC)C(OC)=CC=2)C2=CC(OC)=C(OC)C=C2CC1 LHFABXXKENNWII-UHFFFAOYSA-N 0.000 description 1
• ZQXGAZFIRYBSJF-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-[(4-methoxyphenyl)methyl]acetamide Chemical compound C1=CC(OC)=CC=C1CNC(=O)CN1C(CC=2C=C(OC)C(OC)=CC=2)C2=CC(OC)=C(OC)C=C2CC1 ZQXGAZFIRYBSJF-UHFFFAOYSA-N 0.000 description 1
• NPBJMBYFVMURHZ-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-[(4-methylphenyl)methyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)NCC1=CC=C(C)C=C1 NPBJMBYFVMURHZ-UHFFFAOYSA-N 0.000 description 1
• VOOAWEFAVCKUTD-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-[(6-methoxynaphthalen-2-yl)methyl]acetamide Chemical compound C1=CC2=CC(OC)=CC=C2C=C1CNC(=O)CN1CCC2=CC(OC)=C(OC)C=C2C1CC1=CC=C(OC)C(OC)=C1 VOOAWEFAVCKUTD-UHFFFAOYSA-N 0.000 description 1
• RLFWDBHTXGQMCU-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-phenylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)NC1=CC=CC=C1 RLFWDBHTXGQMCU-UHFFFAOYSA-N 0.000 description 1
• QBEYTWHWIXHQJE-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-6,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-[(2-ethoxyphenyl)methyl]acetamide Chemical compound CCOC1=CC=CC=C1CNC(=O)CN1C(CC=2C=C(OC)C(OC)=CC=2)C2=C(OC)C=C(OC)C=C2CC1 QBEYTWHWIXHQJE-UHFFFAOYSA-N 0.000 description 1
• CVNYSFJBKISKQS-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-6,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-[(2-methoxyphenyl)methyl]acetamide Chemical compound C=1C=C(OC)C(OC)=CC=1CC1C=2C(OC)=CC(OC)=CC=2CCN1CC(=O)NCC1=CC=CC=C1OC CVNYSFJBKISKQS-UHFFFAOYSA-N 0.000 description 1
• MJCLZUWOLGLTJO-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(pyridin-4-ylmethyl)acetamide Chemical compound C=1C=NC=CC=1CNC(=O)CN1CCC2=CC(OC)=CC=C2C1CC1=CC=C(OC)C(OC)=C1 MJCLZUWOLGLTJO-UHFFFAOYSA-N 0.000 description 1
• KEGPKYXRXFQHPW-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-[(2-methoxyphenyl)methyl]acetamide Chemical compound C=1C=CC=C(OC)C=1CNC(=O)CN1CCC2=CC(OC)=CC=C2C1CC1=CC=C(OC)C(OC)=C1 KEGPKYXRXFQHPW-UHFFFAOYSA-N 0.000 description 1
• IQTLSYMDRYQNTO-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-[(3-methylphenyl)methyl]acetamide Chemical compound C=1C=CC(C)=CC=1CNC(=O)CN1CCC2=CC(OC)=CC=C2C1CC1=CC=C(OC)C(OC)=C1 IQTLSYMDRYQNTO-UHFFFAOYSA-N 0.000 description 1
• HXNZSKZUCVPTLT-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-7-propan-2-yloxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-[(2-ethoxyphenyl)methyl]acetamide Chemical compound CCOC1=CC=CC=C1CNC(=O)CN1C(CC=2C=C(OC)C(OC)=CC=2)C2=CC(OC(C)C)=C(OC)C=C2CC1 HXNZSKZUCVPTLT-UHFFFAOYSA-N 0.000 description 1
• YHQXJDDOBCLKSE-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-7-propan-2-yloxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-[(2-methoxyphenyl)methyl]acetamide Chemical compound COC1=CC=CC=C1CNC(=O)CN1C(CC=2C=C(OC)C(OC)=CC=2)C2=CC(OC(C)C)=C(OC)C=C2CC1 YHQXJDDOBCLKSE-UHFFFAOYSA-N 0.000 description 1
• MOHOMFSWMZYMPG-UHFFFAOYSA-N 2-[1-[(3,4-dimethoxyphenyl)methyl]-8-hydroxy-5-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(pyridin-2-ylmethyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=C(O)C=CC(OC)=C2CCN1CC(=O)NCC1=CC=CC=N1 MOHOMFSWMZYMPG-UHFFFAOYSA-N 0.000 description 1
• IGIXENPZYHUOEF-UHFFFAOYSA-N 2-[1-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]cyclohexa-2,4-dien-1-yl]acetic acid Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCC1C1(CC(O)=O)C=CC=CC1 IGIXENPZYHUOEF-UHFFFAOYSA-N 0.000 description 1
• HMTMDNMTEIWDEK-UHFFFAOYSA-N 2-[1-[[4-(dimethylamino)phenyl]methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-[(2-methoxyphenyl)methyl]acetamide Chemical compound COC1=CC=CC=C1CNC(=O)CN1C(CC=2C=CC(=CC=2)N(C)C)C2=CC(OC)=C(OC)C=C2CC1 HMTMDNMTEIWDEK-UHFFFAOYSA-N 0.000 description 1
• KQGHTOZUPICELS-UHFFFAOYSA-N 2-[4-(dimethylamino)phenyl]acetic acid Chemical compound CN(C)C1=CC=C(CC(O)=O)C=C1 KQGHTOZUPICELS-UHFFFAOYSA-N 0.000 description 1
• YKYNGHKFRYUMJA-UHFFFAOYSA-N 2-[5-butoxy-1-[(3,4-dimethoxyphenyl)methyl]-8-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-(pyridin-2-ylmethyl)acetamide Chemical compound C=1C=CC=NC=1CNC(=O)CN1CCC=2C(OCCCC)=CC=C(OC)C=2C1CC1=CC=C(OC)C(OC)=C1 YKYNGHKFRYUMJA-UHFFFAOYSA-N 0.000 description 1
• XZZHDKSKEYPZIG-UHFFFAOYSA-N 2-[6,7-dimethoxy-1-(1-phenylpropyl)-3,4-dihydro-1h-isoquinolin-2-yl]-n-(pyridin-2-ylmethyl)acetamide Chemical compound C=1C=CC=CC=1C(CC)C(C1=CC(OC)=C(OC)C=C1CC1)N1CC(=O)NCC1=CC=CC=N1 XZZHDKSKEYPZIG-UHFFFAOYSA-N 0.000 description 1
• MZLWVWSSAXTNOG-UHFFFAOYSA-N 2-[6,7-dimethoxy-1-[(2,3,4-trimethoxyphenyl)methyl]-3,4-dihydro-1h-isoquinolin-2-yl]-n-(2-phenylethyl)acetamide Chemical compound C=1C=C(OC)C(OC)=C(OC)C=1CC1C=2C=C(OC)C(OC)=CC=2CCN1CC(=O)NCCC1=CC=CC=C1 MZLWVWSSAXTNOG-UHFFFAOYSA-N 0.000 description 1
• LRRYWDRLFAGGED-UHFFFAOYSA-N 2-[6,7-dimethoxy-1-[(2,3,4-trimethoxyphenyl)methyl]-3,4-dihydro-1h-isoquinolin-2-yl]-n-[(2-ethoxyphenyl)methyl]acetamide Chemical compound CCOC1=CC=CC=C1CNC(=O)CN1C(CC=2C(=C(OC)C(OC)=CC=2)OC)C2=CC(OC)=C(OC)C=C2CC1 LRRYWDRLFAGGED-UHFFFAOYSA-N 0.000 description 1
• YOFNGHNWEITSRA-UHFFFAOYSA-N 2-[6,7-dimethoxy-1-[(3-methoxyphenyl)methyl]-3,4-dihydro-1h-isoquinolin-2-yl]-n-(pyridin-3-ylmethyl)acetamide Chemical compound COC1=CC=CC(CC2C3=CC(OC)=C(OC)C=C3CCN2CC(=O)NCC=2C=NC=CC=2)=C1 YOFNGHNWEITSRA-UHFFFAOYSA-N 0.000 description 1
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
• VIBOGIYPPWLDTI-UHFFFAOYSA-N 2-naphthylacetic acid Chemical compound C1=CC=CC2=CC(CC(=O)O)=CC=C21 VIBOGIYPPWLDTI-UHFFFAOYSA-N 0.000 description 1
• QGXMHCMPIAYMGT-UHFFFAOYSA-N 2-phenylbutanoyl chloride Chemical compound CCC(C(Cl)=O)C1=CC=CC=C1 QGXMHCMPIAYMGT-UHFFFAOYSA-N 0.000 description 1
• QISAUDWTBBNJIR-UHFFFAOYSA-N 2-phenylmethoxyacetyl chloride Chemical compound ClC(=O)COCC1=CC=CC=C1 QISAUDWTBBNJIR-UHFFFAOYSA-N 0.000 description 1
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
• HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
• YGYGASJNJTYNOL-CQSZACIVSA-N 3-[(4r)-2,2-dimethyl-1,1-dioxothian-4-yl]-5-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound C1CS(=O)(=O)C(C)(C)C[C@@H]1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(F)=CC=3)C=C12 YGYGASJNJTYNOL-CQSZACIVSA-N 0.000 description 1
• SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
• MFEILWXBDBCWKF-UHFFFAOYSA-N 3-phenylpropanoyl chloride Chemical compound ClC(=O)CCC1=CC=CC=C1 MFEILWXBDBCWKF-UHFFFAOYSA-N 0.000 description 1
• AHZYDHMFNHSEHU-UHFFFAOYSA-N 3-pyridin-3-ylpropanamide Chemical compound NC(=O)CCC1=CC=CN=C1 AHZYDHMFNHSEHU-UHFFFAOYSA-N 0.000 description 1
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
• YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 1
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
• LTPVSOCPYWDIFU-UHFFFAOYSA-N 4-methoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1 LTPVSOCPYWDIFU-UHFFFAOYSA-N 0.000 description 1
• YQTZICLOPZEECN-UHFFFAOYSA-N 6,7-dimethoxy-1-(phenylmethoxymethyl)-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=2C=C(OC)C(OC)=CC=2CCNC1COCC1=CC=CC=C1 YQTZICLOPZEECN-UHFFFAOYSA-N 0.000 description 1
• IYDXQGNUXUOZOC-UHFFFAOYSA-N 6,7-dimethoxy-1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline Chemical compound C1=2C=C(OC)C(OC)=CC=2CCNC1CC1=CC(OC)=C(OC)C(OC)=C1 IYDXQGNUXUOZOC-UHFFFAOYSA-N 0.000 description 1
• OIMFNCWZUMIHMJ-UHFFFAOYSA-N 6,7-dimethoxy-1-[(4-methoxy-3-phenylmethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline Chemical compound COC1=CC=C(CC2C3=CC(OC)=C(OC)C=C3CCN2)C=C1OCC1=CC=CC=C1 OIMFNCWZUMIHMJ-UHFFFAOYSA-N 0.000 description 1
• KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
• UNQYAAAWKOOBFQ-UHFFFAOYSA-N 7-[(4-chlorophenyl)methyl]-8-[4-chloro-3-(trifluoromethoxy)phenoxy]-1-(3-hydroxypropyl)-3-methylpurine-2,6-dione Chemical compound C=1C=C(Cl)C=CC=1CN1C=2C(=O)N(CCCO)C(=O)N(C)C=2N=C1OC1=CC=C(Cl)C(OC(F)(F)F)=C1 UNQYAAAWKOOBFQ-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
• ZRPZPNYZFSJUPA-UHFFFAOYSA-N ARS-1620 Chemical compound Oc1cccc(F)c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C ZRPZPNYZFSJUPA-UHFFFAOYSA-N 0.000 description 1
• 206010000599 Acromegaly Diseases 0.000 description 1
• 201000000736 Amenorrhea Diseases 0.000 description 1
• 206010001928 Amenorrhoea Diseases 0.000 description 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
• 208000025978 Athletic injury Diseases 0.000 description 1
• 208000008035 Back Pain Diseases 0.000 description 1
• 201000009586 Basophil Adenoma Diseases 0.000 description 1
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 1
• 208000020925 Bipolar disease Diseases 0.000 description 1
• 238000006407 Bischler-Napieralski reaction Methods 0.000 description 1
• 208000032841 Bulimia Diseases 0.000 description 1
• 206010006550 Bulimia nervosa Diseases 0.000 description 1
• 206010006895 Cachexia Diseases 0.000 description 1
• 206010007556 Cardiac failure acute Diseases 0.000 description 1
• 206010007559 Cardiac failure congestive Diseases 0.000 description 1
• 208000001387 Causalgia Diseases 0.000 description 1
• 208000023890 Complex Regional Pain Syndromes Diseases 0.000 description 1
• 208000013586 Complex regional pain syndrome type 1 Diseases 0.000 description 1
• 208000027691 Conduct disease Diseases 0.000 description 1
• 229920002261 Corn starch Polymers 0.000 description 1
• 208000014311 Cushing syndrome Diseases 0.000 description 1
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
• 206010012218 Delirium Diseases 0.000 description 1
• 208000020401 Depressive disease Diseases 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• 206010052804 Drug tolerance Diseases 0.000 description 1
• 206010013883 Dwarfism Diseases 0.000 description 1
• 206010013911 Dysgeusia Diseases 0.000 description 1
• 208000030814 Eating disease Diseases 0.000 description 1
• 208000019454 Feeding and Eating disease Diseases 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• 201000001498 Froelich syndrome Diseases 0.000 description 1
• 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
• 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
• 108010010803 Gelatin Proteins 0.000 description 1
• 208000004230 Gender Dysphoria Diseases 0.000 description 1
• 206010018265 Gigantism Diseases 0.000 description 1
• 201000004311 Gilles de la Tourette syndrome Diseases 0.000 description 1
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
• 208000002705 Glucose Intolerance Diseases 0.000 description 1
• 102000018997 Growth Hormone Human genes 0.000 description 1
• 108010051696 Growth Hormone Proteins 0.000 description 1
• 206010056438 Growth hormone deficiency Diseases 0.000 description 1
• 206010019280 Heart failures Diseases 0.000 description 1
• 208000016988 Hemorrhagic Stroke Diseases 0.000 description 1
• 101500025902 Homo sapiens Orexin-A Proteins 0.000 description 1
• 208000023105 Huntington disease Diseases 0.000 description 1
• 206010020751 Hypersensitivity Diseases 0.000 description 1
• 206010020772 Hypertension Diseases 0.000 description 1
• 206010058359 Hypogonadism Diseases 0.000 description 1
• 206010050515 Hyposmia Diseases 0.000 description 1
• 208000001953 Hypotension Diseases 0.000 description 1
• 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
• 208000032382 Ischaemic stroke Diseases 0.000 description 1
• 208000001456 Jet Lag Syndrome Diseases 0.000 description 1
• 201000007493 Kallmann syndrome Diseases 0.000 description 1
• ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
• 229930182816 L-glutamine Natural products 0.000 description 1
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
• 208000019693 Lung disease Diseases 0.000 description 1
• 241000124008 Mammalia Species 0.000 description 1
• 208000019022 Mood disease Diseases 0.000 description 1
• AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
• FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical class NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 description 1
• 206010028813 Nausea Diseases 0.000 description 1
• 206010028980 Neoplasm Diseases 0.000 description 1
• 208000012902 Nervous system disease Diseases 0.000 description 1
• 208000025966 Neurological disease Diseases 0.000 description 1
• 108090000189 Neuropeptides Proteins 0.000 description 1
• 206010029333 Neurosis Diseases 0.000 description 1
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
• 206010053142 Olfacto genital dysplasia Diseases 0.000 description 1
• 208000001132 Osteoporosis Diseases 0.000 description 1
• 229910019213 POCl3 Inorganic materials 0.000 description 1
• 208000018737 Parkinson disease Diseases 0.000 description 1
• 229930182555 Penicillin Natural products 0.000 description 1
• JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
• 208000010067 Pituitary ACTH Hypersecretion Diseases 0.000 description 1
• 201000005746 Pituitary adenoma Diseases 0.000 description 1
• 208000014993 Pituitary disease Diseases 0.000 description 1
• 206010061538 Pituitary tumour benign Diseases 0.000 description 1
• 208000020627 Pituitary-dependent Cushing syndrome Diseases 0.000 description 1
• 206010062519 Poor quality sleep Diseases 0.000 description 1
• 208000004550 Postoperative Pain Diseases 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
• 208000004403 Prostatic Hyperplasia Diseases 0.000 description 1
• 208000006262 Psychological Sexual Dysfunctions Diseases 0.000 description 1
• 241000700159 Rattus Species 0.000 description 1
• 208000005793 Restless legs syndrome Diseases 0.000 description 1
• 208000036623 Severe mental retardation Diseases 0.000 description 1
• 201000001880 Sexual dysfunction Diseases 0.000 description 1
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
• 206010041738 Sports injury Diseases 0.000 description 1
• 235000021355 Stearic acid Nutrition 0.000 description 1
• 208000007107 Stomach Ulcer Diseases 0.000 description 1
• 208000006011 Stroke Diseases 0.000 description 1
• 208000032851 Subarachnoid Hemorrhage Diseases 0.000 description 1
• 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
• 229930006000 Sucrose Natural products 0.000 description 1
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
• 208000000323 Tourette Syndrome Diseases 0.000 description 1
• 208000016620 Tourette disease Diseases 0.000 description 1
• 208000025865 Ulcer Diseases 0.000 description 1
• 208000000921 Urge Urinary Incontinence Diseases 0.000 description 1
• 206010046543 Urinary incontinence Diseases 0.000 description 1
• 206010046555 Urinary retention Diseases 0.000 description 1
• 206010047700 Vomiting Diseases 0.000 description 1
• PNJSUNGZWIXPBG-UHFFFAOYSA-N [4-[[2-[2-(benzylamino)-2-oxoethyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-1-yl]methyl]-2-methoxyphenyl] n,n-dimethylcarbamate Chemical compound C=1C=C(OC(=O)N(C)C)C(OC)=CC=1CC1C=2C=C(OC)C(OC)=CC=2CCN1CC(=O)NCC1=CC=CC=C1 PNJSUNGZWIXPBG-UHFFFAOYSA-N 0.000 description 1
• SUPZGQZIGFKYJW-UHFFFAOYSA-N [chloro(phenyl)methyl] acetate Chemical compound CC(=O)OC(Cl)C1=CC=CC=C1 SUPZGQZIGFKYJW-UHFFFAOYSA-N 0.000 description 1
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
• 239000012346 acetyl chloride Substances 0.000 description 1
• AMJRSUWJSRKGNO-UHFFFAOYSA-N acetyloxymethyl 2-[n-[2-(acetyloxymethoxy)-2-oxoethyl]-2-[2-[2-[bis[2-(acetyloxymethoxy)-2-oxoethyl]amino]-5-(2,7-dichloro-3-hydroxy-6-oxoxanthen-9-yl)phenoxy]ethoxy]-4-methylanilino]acetate Chemical compound CC(=O)OCOC(=O)CN(CC(=O)OCOC(C)=O)C1=CC=C(C)C=C1OCCOC1=CC(C2=C3C=C(Cl)C(=O)C=C3OC3=CC(O)=C(Cl)C=C32)=CC=C1N(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O AMJRSUWJSRKGNO-UHFFFAOYSA-N 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 230000001154 acute effect Effects 0.000 description 1
• 208000005298 acute pain Diseases 0.000 description 1
• 230000001270 agonistic effect Effects 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 150000001299 aldehydes Chemical class 0.000 description 1
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• 150000001340 alkali metals Chemical class 0.000 description 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
• 150000001342 alkaline earth metals Chemical class 0.000 description 1
• 125000003302 alkenyloxy group Chemical group 0.000 description 1
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
• 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
• 125000005210 alkyl ammonium group Chemical group 0.000 description 1
• 230000007815 allergy Effects 0.000 description 1
• 206010053552 allodynia Diseases 0.000 description 1
• 125000005336 allyloxy group Chemical group 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 231100000540 amenorrhea Toxicity 0.000 description 1
• 208000022531 anorexia Diseases 0.000 description 1
• 235000019558 anosmia Nutrition 0.000 description 1
• 230000008485 antagonism Effects 0.000 description 1
• 239000003963 antioxidant agent Substances 0.000 description 1
• 230000036528 appetite Effects 0.000 description 1
• 235000019789 appetite Nutrition 0.000 description 1
• 230000002917 arthritic effect Effects 0.000 description 1
• 208000006673 asthma Diseases 0.000 description 1
• 230000008827 biological function Effects 0.000 description 1
• 208000028683 bipolar I disease Diseases 0.000 description 1
• AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
• HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
• 201000011510 cancer Diseases 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• 239000003153 chemical reaction reagent Substances 0.000 description 1
• 239000003795 chemical substances by application Substances 0.000 description 1
• 238000002512 chemotherapy Methods 0.000 description 1
• 208000020832 chronic kidney disease Diseases 0.000 description 1
• 208000022831 chronic renal failure syndrome Diseases 0.000 description 1
• 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
• 230000027288 circadian rhythm Effects 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 239000008120 corn starch Substances 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
• 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
• 206010061428 decreased appetite Diseases 0.000 description 1
• 230000007812 deficiency Effects 0.000 description 1
• MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
• 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
• 125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 description 1
• UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
• 235000014632 disordered eating Nutrition 0.000 description 1
• CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
• 230000004064 dysfunction Effects 0.000 description 1
• 230000002996 emotional effect Effects 0.000 description 1
• 239000003995 emulsifying agent Substances 0.000 description 1
• 239000000839 emulsion Substances 0.000 description 1
• 206010015037 epilepsy Diseases 0.000 description 1
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
• TYHRJHFMHFZOPQ-UHFFFAOYSA-N ethyl 2-[4-[[2-[2-(benzylamino)-2-oxoethyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-1-yl]methyl]-2-methoxyphenoxy]acetate Chemical compound C1=C(OC)C(OCC(=O)OCC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)NCC1=CC=CC=C1 TYHRJHFMHFZOPQ-UHFFFAOYSA-N 0.000 description 1
• PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
• 239000000284 extract Substances 0.000 description 1
• 230000008713 feedback mechanism Effects 0.000 description 1
• 230000004634 feeding behavior Effects 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 229910052731 fluorine Inorganic materials 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• 230000037406 food intake Effects 0.000 description 1
• 235000012631 food intake Nutrition 0.000 description 1
• 235000003599 food sweetener Nutrition 0.000 description 1
• 235000019253 formic acid Nutrition 0.000 description 1
• 238000006170 formylation reaction Methods 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 230000002496 gastric effect Effects 0.000 description 1
• 201000005917 gastric ulcer Diseases 0.000 description 1
• 229920000159 gelatin Polymers 0.000 description 1
• 239000008273 gelatin Substances 0.000 description 1
• 235000019322 gelatine Nutrition 0.000 description 1
• 235000011852 gelatine desserts Nutrition 0.000 description 1
• 239000008103 glucose Substances 0.000 description 1
• 239000000122 growth hormone Substances 0.000 description 1
• 239000001963 growth medium Substances 0.000 description 1
• 125000005553 heteroaryloxy group Chemical group 0.000 description 1
• 150000003840 hydrochlorides Chemical class 0.000 description 1
• 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
• 235000019559 hyposmia Nutrition 0.000 description 1
• 230000036543 hypotension Effects 0.000 description 1
• 210000003016 hypothalamus Anatomy 0.000 description 1
• 208000003532 hypothyroidism Diseases 0.000 description 1
• 230000002989 hypothyroidism Effects 0.000 description 1
• 238000003384 imaging method Methods 0.000 description 1
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 208000015181 infectious disease Diseases 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• 230000003834 intracellular effect Effects 0.000 description 1
• 208000020658 intracerebral hemorrhage Diseases 0.000 description 1
• 229960004903 invert sugar Drugs 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• 208000002551 irritable bowel syndrome Diseases 0.000 description 1
• 230000000302 ischemic effect Effects 0.000 description 1
• 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
• 125000005956 isoquinolyl group Chemical group 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 125000000842 isoxazolyl group Chemical group 0.000 description 1
• 208000017169 kidney disease Diseases 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 238000004811 liquid chromatography Methods 0.000 description 1
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
• 239000011976 maleic acid Substances 0.000 description 1
• 230000000873 masking effect Effects 0.000 description 1
• 238000004949 mass spectrometry Methods 0.000 description 1
• 239000002609 medium Substances 0.000 description 1
• COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• NHFBYYMNJUMVOT-UHFFFAOYSA-N methyl 2-bromo-2-phenylacetate Chemical compound COC(=O)C(Br)C1=CC=CC=C1 NHFBYYMNJUMVOT-UHFFFAOYSA-N 0.000 description 1
• 125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 239000003068 molecular probe Substances 0.000 description 1
• XMWFMEYDRNJSOO-UHFFFAOYSA-N morpholine-4-carbonyl chloride Chemical compound ClC(=O)N1CCOCC1 XMWFMEYDRNJSOO-UHFFFAOYSA-N 0.000 description 1
• 125000002757 morpholinyl group Chemical group 0.000 description 1
• 208000010125 myocardial infarction Diseases 0.000 description 1
• FMASTMURQSHELY-UHFFFAOYSA-N n-(4-fluoro-2-methylphenyl)-3-methyl-n-[(2-methyl-1h-indol-4-yl)methyl]pyridine-4-carboxamide Chemical compound C1=CC=C2NC(C)=CC2=C1CN(C=1C(=CC(F)=CC=1)C)C(=O)C1=CC=NC=C1C FMASTMURQSHELY-UHFFFAOYSA-N 0.000 description 1
• SODGOGUDPVAERC-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-2-[1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)NCC1=CC=CC=C1Cl SODGOGUDPVAERC-UHFFFAOYSA-N 0.000 description 1
• TZBRNIWZOAPBHV-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]acetamide Chemical compound CC(=O)NCC1=CC=CC=C1Cl TZBRNIWZOAPBHV-UHFFFAOYSA-N 0.000 description 1
• DYSXPJXIDRWVOA-UHFFFAOYSA-N n-[(2-ethoxyphenyl)methyl]-2-[1-[(4-fluorophenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound CCOC1=CC=CC=C1CNC(=O)CN1C(CC=2C=CC(F)=CC=2)C2=CC(OC)=C(OC)C=C2CC1 DYSXPJXIDRWVOA-UHFFFAOYSA-N 0.000 description 1
• ZOUCHBXJUPPSRN-UHFFFAOYSA-N n-[(2-fluorophenyl)methyl]acetamide Chemical compound CC(=O)NCC1=CC=CC=C1F ZOUCHBXJUPPSRN-UHFFFAOYSA-N 0.000 description 1
• HRQJIGPCAHFWBT-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-2-(3,4-dimethylphenyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)CC1=CC=C(C)C(C)=C1 HRQJIGPCAHFWBT-UHFFFAOYSA-N 0.000 description 1
• DWKCRQVVSFBILN-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-2-[4-(dimethylamino)phenyl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)CC1=CC=C(N(C)C)C=C1 DWKCRQVVSFBILN-UHFFFAOYSA-N 0.000 description 1
• OQSLRUAUSVKVBL-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-2-naphthalen-2-ylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)CC1=CC=C(C=CC=C2)C2=C1 OQSLRUAUSVKVBL-UHFFFAOYSA-N 0.000 description 1
• WYRVNRWVHSLADF-VWLOTQADSA-N n-benzyl-2-[(1s)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-methylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1C[C@H]1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)N(C)CC1=CC=CC=C1 WYRVNRWVHSLADF-VWLOTQADSA-N 0.000 description 1
• FYSUZYYFUUADES-DEOSSOPVSA-N n-benzyl-2-[(1s)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1C[C@H]1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)NCC1=CC=CC=C1 FYSUZYYFUUADES-DEOSSOPVSA-N 0.000 description 1
• IJHZXBWMUGHAPB-UHFFFAOYSA-N n-benzyl-2-[1-[(2,5-dimethoxyphenyl)methyl]-5,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound COC1=CC=C(OC)C(CC2C3=C(OC)C=CC(OC)=C3CCN2CC(=O)NCC=2C=CC=CC=2)=C1 IJHZXBWMUGHAPB-UHFFFAOYSA-N 0.000 description 1
• GXEWUQQANRBOSY-UHFFFAOYSA-N n-benzyl-2-[1-[(3,4-dimethoxyphenyl)methyl]-5,6,7-trimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-methylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C(C=C(OC)C(OC)=C2OC)=C2CCN1CC(=O)N(C)CC1=CC=CC=C1 GXEWUQQANRBOSY-UHFFFAOYSA-N 0.000 description 1
• RIFKIUVCVLNLNX-UHFFFAOYSA-N n-benzyl-2-[1-[(3,4-dimethoxyphenyl)methyl]-6,8-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C=1C=C(OC)C(OC)=CC=1CC1C=2C(OC)=CC(OC)=CC=2CCN1CC(=O)NCC1=CC=CC=C1 RIFKIUVCVLNLNX-UHFFFAOYSA-N 0.000 description 1
• UWLWEDNGFORSNG-UHFFFAOYSA-N n-benzyl-2-[1-[(3,4-dimethoxyphenyl)methyl]-6-ethoxy-7-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C=1C=C(OC)C(OC)=CC=1CC1C=2C=C(OC)C(OCC)=CC=2CCN1CC(=O)NCC1=CC=CC=C1 UWLWEDNGFORSNG-UHFFFAOYSA-N 0.000 description 1
• FTSPPCVUJGHARL-UHFFFAOYSA-N n-benzyl-2-[1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C=1C=CC=CC=1CNC(=O)CN1CCC2=CC(OC)=CC=C2C1CC1=CC=C(OC)C(OC)=C1 FTSPPCVUJGHARL-UHFFFAOYSA-N 0.000 description 1
• HFXHCZBJZUJSCZ-UHFFFAOYSA-N n-benzyl-2-[1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-7-phenylmethoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OCC=3C=CC=CC=3)=C(OC)C=C2CCN1CC(=O)NCC1=CC=CC=C1 HFXHCZBJZUJSCZ-UHFFFAOYSA-N 0.000 description 1
• QDVAKWOYMQNGGI-UHFFFAOYSA-N n-benzyl-2-[1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-7-propan-2-yloxy-3,4-dihydro-1h-isoquinolin-2-yl]-n-methylacetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC(C)C)=C(OC)C=C2CCN1CC(=O)N(C)CC1=CC=CC=C1 QDVAKWOYMQNGGI-UHFFFAOYSA-N 0.000 description 1
• DLZVDBYNJQVSNK-UHFFFAOYSA-N n-benzyl-2-[1-[(3,4-dimethoxyphenyl)methyl]-6-methoxy-7-propan-2-yloxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC(C)C)=C(OC)C=C2CCN1CC(=O)NCC1=CC=CC=C1 DLZVDBYNJQVSNK-UHFFFAOYSA-N 0.000 description 1
• HSGSJIIJCGUGLY-UHFFFAOYSA-N n-benzyl-2-[1-[(3,4-dimethoxyphenyl)methyl]-7-hydroxy-6-methoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C=1C=C(OC)C(OC)=CC=1CC1C=2C=C(O)C(OC)=CC=2CCN1CC(=O)NCC1=CC=CC=C1 HSGSJIIJCGUGLY-UHFFFAOYSA-N 0.000 description 1
• JCMWNICXFYUVHB-UHFFFAOYSA-N n-benzyl-2-[1-[(3,4-dimethoxyphenyl)methyl]-7-methoxy-6-phenylmethoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OCC=3C=CC=CC=3)C=C2CCN1CC(=O)NCC1=CC=CC=C1 JCMWNICXFYUVHB-UHFFFAOYSA-N 0.000 description 1
• YJNWEXBIPHHTSL-UHFFFAOYSA-N n-benzyl-2-[1-[(3-bromo-4-methoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(Br)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)NCC1=CC=CC=C1 YJNWEXBIPHHTSL-UHFFFAOYSA-N 0.000 description 1
• KUUWMXNYUJXCJE-UHFFFAOYSA-N n-benzyl-2-[1-[(3-butoxy-4-methoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(OC)C(OCCCC)=CC(CC2C3=CC(OC)=C(OC)C=C3CCN2CC(=O)NCC=2C=CC=CC=2)=C1 KUUWMXNYUJXCJE-UHFFFAOYSA-N 0.000 description 1
• XYHISTDQFPBNAJ-UHFFFAOYSA-N n-benzyl-2-[1-[(3-ethoxy-4-methoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(OC)C(OCC)=CC(CC2C3=CC(OC)=C(OC)C=C3CCN2CC(=O)NCC=2C=CC=CC=2)=C1 XYHISTDQFPBNAJ-UHFFFAOYSA-N 0.000 description 1
• MQFIVYZEVJOKJT-UHFFFAOYSA-N n-benzyl-2-[1-[(4-ethoxy-3-methoxyphenyl)methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(OC)C(OCC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1CC(=O)NCC1=CC=CC=C1 MQFIVYZEVJOKJT-UHFFFAOYSA-N 0.000 description 1
• CSASHICNZSIRNV-UHFFFAOYSA-N n-benzyl-2-[1-[[3-(cyclopropylmethoxy)-4-methoxyphenyl]methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(OCC2CC2)C(OC)=CC=C1CC(C1=CC(OC)=C(OC)C=C1CC1)N1CC(=O)NCC1=CC=CC=C1 CSASHICNZSIRNV-UHFFFAOYSA-N 0.000 description 1
• ZWPWVNIEQXBUHH-UHFFFAOYSA-N n-benzyl-2-[1-[[4-(cyclopropylmethoxy)-3-methoxyphenyl]methyl]-6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C=1C=C(OCC2CC2)C(OC)=CC=1CC(C1=CC(OC)=C(OC)C=C1CC1)N1CC(=O)NCC1=CC=CC=C1 ZWPWVNIEQXBUHH-UHFFFAOYSA-N 0.000 description 1
• LEMFUGXOSANTBO-UHFFFAOYSA-N n-benzyl-2-[6,7-dimethoxy-1-[(3-methoxy-4-propan-2-yloxyphenyl)methyl]-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C=1C=C(OC(C)C)C(OC)=CC=1CC1C=2C=C(OC)C(OC)=CC=2CCN1CC(=O)NCC1=CC=CC=C1 LEMFUGXOSANTBO-UHFFFAOYSA-N 0.000 description 1
• RRBYCHHICVPEJB-UHFFFAOYSA-N n-benzyl-2-[6,7-dimethoxy-1-[(3-methoxy-4-pyrimidin-2-yloxyphenyl)methyl]-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C=1C=C(OC=2N=CC=CN=2)C(OC)=CC=1CC1C=2C=C(OC)C(OC)=CC=2CCN1CC(=O)NCC1=CC=CC=C1 RRBYCHHICVPEJB-UHFFFAOYSA-N 0.000 description 1
• RSIFYMWHCQCEJN-UHFFFAOYSA-N n-benzyl-2-[6,7-dimethoxy-1-[(4-methoxy-3-propoxyphenyl)methyl]-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(OC)C(OCCC)=CC(CC2C3=CC(OC)=C(OC)C=C3CCN2CC(=O)NCC=2C=CC=CC=2)=C1 RSIFYMWHCQCEJN-UHFFFAOYSA-N 0.000 description 1
• CEUYUUKQQOETJF-UHFFFAOYSA-N n-benzyl-2-[6,7-dimethoxy-1-[(4-methoxy-3-pyrimidin-2-yloxyphenyl)methyl]-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(OC=2N=CC=CN=2)C(OC)=CC=C1CC(C1=CC(OC)=C(OC)C=C1CC1)N1CC(=O)NCC1=CC=CC=C1 CEUYUUKQQOETJF-UHFFFAOYSA-N 0.000 description 1
• QFHFJDFMLQDNNR-UHFFFAOYSA-N n-benzyl-2-[6,7-dimethoxy-1-[[3-methoxy-4-(2-methylpropoxy)phenyl]methyl]-3,4-dihydro-1h-isoquinolin-2-yl]acetamide Chemical compound C1=C(OCC(C)C)C(OC)=CC(CC2C3=CC(OC)=C(OC)C=C3CCN2CC(=O)NCC=2C=CC=CC=2)=C1 QFHFJDFMLQDNNR-UHFFFAOYSA-N 0.000 description 1
• NQXVNLHPEJBZAT-UHFFFAOYSA-N n-benzyl-n-methylacetamide Chemical compound CC(=O)N(C)CC1=CC=CC=C1 NQXVNLHPEJBZAT-UHFFFAOYSA-N 0.000 description 1
• 239000007922 nasal spray Substances 0.000 description 1
• 229940097496 nasal spray Drugs 0.000 description 1
• 230000008693 nausea Effects 0.000 description 1
• 208000015122 neurodegenerative disease Diseases 0.000 description 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
• 239000012038 nucleophile Substances 0.000 description 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 235000005985 organic acids Nutrition 0.000 description 1
• 239000006259 organic additive Substances 0.000 description 1
• 230000003204 osmotic effect Effects 0.000 description 1
• 125000002971 oxazolyl group Chemical group 0.000 description 1
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
• 229910052763 palladium Inorganic materials 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• 230000007170 pathology Effects 0.000 description 1
• 229940049954 penicillin Drugs 0.000 description 1
• 208000030062 persistent idiopathic facial pain Diseases 0.000 description 1
• 229960003424 phenylacetic acid Drugs 0.000 description 1
• 239000003279 phenylacetic acid Substances 0.000 description 1
• 150000007925 phenylethylamine derivatives Chemical class 0.000 description 1
• RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 125000003386 piperidinyl group Chemical group 0.000 description 1
• 208000021310 pituitary gland adenoma Diseases 0.000 description 1
• 208000020351 pituitary gland basophil adenoma Diseases 0.000 description 1
• 208000017402 pituitary gland disease Diseases 0.000 description 1
• 208000010916 pituitary tumor Diseases 0.000 description 1
• 229920001983 poloxamer Polymers 0.000 description 1
• LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
• 229910052700 potassium Inorganic materials 0.000 description 1
• 201000009104 prediabetes syndrome Diseases 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
• 201000009395 primary hyperaldosteronism Diseases 0.000 description 1
• 102000004196 processed proteins & peptides Human genes 0.000 description 1
• 230000001107 psychogenic effect Effects 0.000 description 1
• 208000026961 psychosexual disease Diseases 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000003226 pyrazolyl group Chemical group 0.000 description 1
• 125000002098 pyridazinyl group Chemical group 0.000 description 1
• TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
• 125000004076 pyridyl group Chemical group 0.000 description 1
• 125000000714 pyrimidinyl group Chemical group 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 125000005493 quinolyl group Chemical group 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• 230000004044 response Effects 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• 239000012047 saturated solution Substances 0.000 description 1
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
• 230000035945 sensitivity Effects 0.000 description 1
• 231100000872 sexual dysfunction Toxicity 0.000 description 1
• XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
• 230000007958 sleep Effects 0.000 description 1
• 229910052708 sodium Inorganic materials 0.000 description 1
• 239000003381 stabilizer Substances 0.000 description 1
• 238000010561 standard procedure Methods 0.000 description 1
• 239000008117 stearic acid Substances 0.000 description 1
• 229960005322 streptomycin Drugs 0.000 description 1
• 208000023516 stroke disease Diseases 0.000 description 1
• 238000006467 substitution reaction Methods 0.000 description 1
• 239000001384 succinic acid Substances 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
• 239000003765 sweetening agent Substances 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
• WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• 231100000397 ulcer Toxicity 0.000 description 1
• 206010046494 urge incontinence Diseases 0.000 description 1
• 210000003932 urinary bladder Anatomy 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• 208000009935 visceral pain Diseases 0.000 description 1
• 230000008673 vomiting Effects 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1