SK280143B6 - Heterobicyklické zlúčeniny, spôsoby ich prípravy a - Google Patents

Info

Publication number

SK280143B6

SK280143B6 SK1007-94A SK100794A SK280143B6 SK 280143 B6 SK280143 B6 SK 280143B6 SK 100794 A SK100794 A SK 100794A SK 280143 B6 SK280143 B6 SK 280143B6

Authority

SK

Slovakia

Prior art keywords

phenyl

methyl

benzopyran

oxo

piperazinyl

Prior art date

1992-02-25

Links

• Espacenet
• Global Dossier
• Discuss

• 238000000034 method Methods 0.000 title claims description 125
• 125000002618 bicyclic heterocycle group Chemical group 0.000 title claims description 14
• 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
• 150000001875 compounds Chemical class 0.000 claims abstract description 429
• -1 but also C=S Chemical group 0.000 claims abstract description 89
• 125000001424 substituent group Chemical group 0.000 claims abstract description 26
• 150000003839 salts Chemical class 0.000 claims abstract description 23
• 239000000651 prodrug Substances 0.000 claims abstract description 14
• 229940002612 prodrug Drugs 0.000 claims abstract description 14
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 13
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 10
• 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 8
• 239000001301 oxygen Substances 0.000 claims abstract description 7
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
• 206010020772 Hypertension Diseases 0.000 claims abstract description 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 319
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 298
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 192
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 165
• 239000002904 solvent Substances 0.000 claims description 135
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 119
• 238000006243 chemical reaction Methods 0.000 claims description 117
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 59
• 229910052739 hydrogen Inorganic materials 0.000 claims description 58
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 58
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 55
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 51
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
• 229910000027 potassium carbonate Inorganic materials 0.000 claims description 29
• 239000001257 hydrogen Substances 0.000 claims description 28
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
• 239000002253 acid Substances 0.000 claims description 22
• 239000002798 polar solvent Substances 0.000 claims description 20
• 125000000217 alkyl group Chemical group 0.000 claims description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
• 229910052799 carbon Inorganic materials 0.000 claims description 16
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 16
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
• 238000002360 preparation method Methods 0.000 claims description 14
• 229910052717 sulfur Inorganic materials 0.000 claims description 14
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 13
• 230000008569 process Effects 0.000 claims description 13
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 11
• 125000005843 halogen group Chemical group 0.000 claims description 10
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
• 125000006239 protecting group Chemical group 0.000 claims description 7
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
• 239000000460 chlorine Substances 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
• 150000002367 halogens Chemical class 0.000 claims description 5
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 5
• 125000004434 sulfur atom Chemical group 0.000 claims description 5
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000004432 carbon atom Chemical group C* 0.000 claims description 4
• DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 claims description 4
• 150000002431 hydrogen Chemical class 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
• 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 3
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
• 229910052801 chlorine Inorganic materials 0.000 claims description 3
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
• DUCNHKDCVVSJLG-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 DUCNHKDCVVSJLG-UHFFFAOYSA-N 0.000 claims description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 3
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
• XMPPERZAQRJCQQ-UHFFFAOYSA-N 3-methyl-4-oxo-2-phenyl-n-[3-(4-phenylpiperazin-1-yl)propyl]chromene-8-carboxamide Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)NCCCN(CC1)CCN1C1=CC=CC=C1 XMPPERZAQRJCQQ-UHFFFAOYSA-N 0.000 claims description 2
• JUXHWXSCFVJNBO-UHFFFAOYSA-N 3-methyl-4-oxo-n-[3-[4-(2-oxo-3h-benzimidazol-1-yl)piperidin-1-yl]propyl]-2-phenylchromene-8-carboxamide Chemical compound O1C2=C(C(=O)NCCCN3CCC(CC3)N3C(NC4=CC=CC=C43)=O)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 JUXHWXSCFVJNBO-UHFFFAOYSA-N 0.000 claims description 2
• JDAUINVSCGMHMP-UHFFFAOYSA-N 4-[4-(2-methoxyphenyl)piperazin-1-yl]-n-(3-methyl-4-oxo-2-phenylchromen-8-yl)butanamide Chemical compound COC1=CC=CC=C1N1CCN(CCCC(=O)NC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 JDAUINVSCGMHMP-UHFFFAOYSA-N 0.000 claims description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
• 208000019901 Anxiety disease Diseases 0.000 claims description 2
• 125000003282 alkyl amino group Chemical group 0.000 claims description 2
• 230000036506 anxiety Effects 0.000 claims description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 239000003085 diluting agent Substances 0.000 claims description 2
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
• 208000035475 disorder Diseases 0.000 claims description 2
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
• FWSZQMLRAZLIOL-UHFFFAOYSA-N n-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 FWSZQMLRAZLIOL-UHFFFAOYSA-N 0.000 claims description 2
• NUFZAKVXJKBCKH-UHFFFAOYSA-N n-[3-[4-(2-hydroxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)NCCCN(CC1)CCN1C1=CC=CC=C1O NUFZAKVXJKBCKH-UHFFFAOYSA-N 0.000 claims description 2
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
• 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
• 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
• 230000002485 urinary effect Effects 0.000 claims description 2
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 6
• 125000001309 chloro group Chemical group Cl* 0.000 claims 3
• PLUMFQNYUVGHER-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound COC1=CC=CC=C1N1CCN(CCCOC(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 PLUMFQNYUVGHER-UHFFFAOYSA-N 0.000 claims 2
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 2
• 125000003545 alkoxy group Chemical group 0.000 claims 2
• 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims 2
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
• 229910052731 fluorine Inorganic materials 0.000 claims 2
• 125000001153 fluoro group Chemical group F* 0.000 claims 2
• BUGZODXDBBCPKQ-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-(4-phenylphenyl)chromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC(=CC=3)C=3C=CC=CC=3)=O)C=CC=2)CC1 BUGZODXDBBCPKQ-UHFFFAOYSA-N 0.000 claims 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 1
• VKFKZXYBWCJYEL-UHFFFAOYSA-N 2-(4-acetamidophenyl)-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4h-chromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C=3OC(=C(C)CC=3C=CC=2)C=2C=CC(NC(C)=O)=CC=2)CC1 VKFKZXYBWCJYEL-UHFFFAOYSA-N 0.000 claims 1
• YUPSOPFUCAUEBD-UHFFFAOYSA-N 2-(4-aminophenyl)-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxochromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC(N)=CC=3)=O)C=CC=2)CC1 YUPSOPFUCAUEBD-UHFFFAOYSA-N 0.000 claims 1
• ZSRGFRKPAWJRFS-UHFFFAOYSA-N 2-(4-benzoylphenyl)-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxochromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC(=CC=3)C(=O)C=3C=CC=CC=3)=O)C=CC=2)CC1 ZSRGFRKPAWJRFS-UHFFFAOYSA-N 0.000 claims 1
• XUECUOBWPJVEDM-UHFFFAOYSA-N 2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound COC1=CC=CC=C1N1CCN(CCOC(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 XUECUOBWPJVEDM-UHFFFAOYSA-N 0.000 claims 1
• WDCJTOYZECAXFV-UHFFFAOYSA-N 2-benzoyl-3-ethyl-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-1-benzofuran-7-carboxamide Chemical compound C1=CC=C2C(CC)=C(C(=O)C=3C=CC=CC=3)OC2=C1C(=O)NCCCN(CC1)CCN1C1=CC=CC=C1OC WDCJTOYZECAXFV-UHFFFAOYSA-N 0.000 claims 1
• YGDSUOONUHSVLM-UHFFFAOYSA-N 3-(4-phenylpiperazin-1-yl)propyl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)OCCCN(CC1)CCN1C1=CC=CC=C1 YGDSUOONUHSVLM-UHFFFAOYSA-N 0.000 claims 1
• NCIOCKHTDZICDA-UHFFFAOYSA-N 3-(hydroxymethyl)-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(CO)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 NCIOCKHTDZICDA-UHFFFAOYSA-N 0.000 claims 1
• ONWDJAVBRVVPJB-UHFFFAOYSA-N 3-[4-(2-chlorophenyl)piperazin-1-yl]propyl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)OCCCN(CC1)CCN1C1=CC=CC=C1Cl ONWDJAVBRVVPJB-UHFFFAOYSA-N 0.000 claims 1
• JSVHNOKUGUAUJG-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]-n-methyl-n-(3-methyl-4-oxo-2-phenylchromen-8-yl)propanamide Chemical compound COC1=CC=CC=C1N1CCN(CCC(=O)N(C)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 JSVHNOKUGUAUJG-UHFFFAOYSA-N 0.000 claims 1
• PITPWFZWDVXSRM-UHFFFAOYSA-N 3-methyl-4-oxo-2-phenyl-n-[3-(4-phenylpiperidin-1-yl)propyl]chromene-8-carboxamide Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)NCCCN(CC1)CCC1C1=CC=CC=C1 PITPWFZWDVXSRM-UHFFFAOYSA-N 0.000 claims 1
• VQMKJJVRCUJKEZ-UHFFFAOYSA-N 3-methyl-4-oxo-2-phenyl-n-[3-(4-pyrimidin-2-ylpiperazin-1-yl)propyl]chromene-8-carboxamide Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)NCCCN(CC1)CCN1C1=NC=CC=N1 VQMKJJVRCUJKEZ-UHFFFAOYSA-N 0.000 claims 1
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
• LVCAOLJGEFYZDO-UHFFFAOYSA-N 6-(ethylamino)-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound C=12OC(C=3C=CC=CC=3)=C(C)C(=O)C2=CC(NCC)=CC=1C(=O)NCCCN(CC1)CCN1C1=CC=CC=C1OC LVCAOLJGEFYZDO-UHFFFAOYSA-N 0.000 claims 1
• QDNHGZLDPJIVMR-UHFFFAOYSA-N 6-(methanesulfonamido)-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=C(NS(C)(=O)=O)C=2)CC1 QDNHGZLDPJIVMR-UHFFFAOYSA-N 0.000 claims 1
• SYEJJGSUNDDJNN-UHFFFAOYSA-N 6-amino-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=C(N)C=2)CC1 SYEJJGSUNDDJNN-UHFFFAOYSA-N 0.000 claims 1
• IJNREAGEYUEUGU-UHFFFAOYSA-N 6-bromo-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=C(Br)C=2)CC1 IJNREAGEYUEUGU-UHFFFAOYSA-N 0.000 claims 1
• MFARXKMBBGGEBW-UHFFFAOYSA-N 6-hydroxy-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=C(O)C=2)CC1 MFARXKMBBGGEBW-UHFFFAOYSA-N 0.000 claims 1
• STXXGVGIPQLGJW-UHFFFAOYSA-N 6-methoxy-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound C=12OC(C=3C=CC=CC=3)=C(C)C(=O)C2=CC(OC)=CC=1C(=O)NCCCN(CC1)CCN1C1=CC=CC=C1OC STXXGVGIPQLGJW-UHFFFAOYSA-N 0.000 claims 1
• FZCYCHSLXKNZEO-UHFFFAOYSA-N 7-methoxy-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2OC)CC1 FZCYCHSLXKNZEO-UHFFFAOYSA-N 0.000 claims 1
• BUXSCFIFZNLZAN-NJZRLIGZSA-N 8-[(e)-2-[4-(2-methoxyphenyl)piperazin-1-yl]ethoxyiminomethyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCO\N=C\C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 BUXSCFIFZNLZAN-NJZRLIGZSA-N 0.000 claims 1
• XIRPNHGMMUAPCN-MDWZMJQESA-N 8-[(e)-4-[4-(2-methoxyphenyl)piperazin-1-yl]but-1-enyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CC\C=C\C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 XIRPNHGMMUAPCN-MDWZMJQESA-N 0.000 claims 1
• NUXJIGIXAYKHLS-UHFFFAOYSA-N 8-[1-hydroxy-2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CC(O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 NUXJIGIXAYKHLS-UHFFFAOYSA-N 0.000 claims 1
• DIINRQCXLCEVHL-UHFFFAOYSA-N 8-[1-hydroxy-2-[4-(2-methylphenyl)piperazin-1-yl]ethyl]-3-methyl-2-phenylchromen-4-one Chemical compound CC1=CC=CC=C1N1CCN(CC(O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 DIINRQCXLCEVHL-UHFFFAOYSA-N 0.000 claims 1
• SVSKMWIABCVAAN-UHFFFAOYSA-N 8-[1-hydroxy-3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCC(O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 SVSKMWIABCVAAN-UHFFFAOYSA-N 0.000 claims 1
• SYQQRFMQEMZAII-UHFFFAOYSA-N 8-[1-hydroxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCCC(O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 SYQQRFMQEMZAII-UHFFFAOYSA-N 0.000 claims 1
• JOKODPSBEBBYKU-UHFFFAOYSA-N 8-[2-[2-(2,6-dimethoxyphenoxy)ethylamino]ethoxy]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC(OC)=C1OCCNCCOC1=CC=CC2=C1OC(C=1C=CC=CC=1)=C(C)C2=O JOKODPSBEBBYKU-UHFFFAOYSA-N 0.000 claims 1
• QZQDOXYNXHKXMZ-UHFFFAOYSA-N 8-[2-[4-(2-ethoxyphenyl)piperazin-1-yl]-1-hydroxyethyl]-3-methyl-2-phenylchromen-4-one Chemical compound CCOC1=CC=CC=C1N1CCN(CC(O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 QZQDOXYNXHKXMZ-UHFFFAOYSA-N 0.000 claims 1
• HZJHNFOSGZTPOE-UHFFFAOYSA-N 8-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethylamino]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCNC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 HZJHNFOSGZTPOE-UHFFFAOYSA-N 0.000 claims 1
• TWVXROHAQOEUQA-UHFFFAOYSA-N 8-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethylsulfonylmethyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCS(=O)(=O)CC=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 TWVXROHAQOEUQA-UHFFFAOYSA-N 0.000 claims 1
• XSIMYVIHHSVTML-UHFFFAOYSA-N 8-[2-hydroxy-3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CC(O)COC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 XSIMYVIHHSVTML-UHFFFAOYSA-N 0.000 claims 1
• CVIYJJLZWPEVRU-UHFFFAOYSA-N 8-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propanoyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCC(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 CVIYJJLZWPEVRU-UHFFFAOYSA-N 0.000 claims 1
• FMYFHINQACBOCS-UHFFFAOYSA-N 8-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCCOC=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 FMYFHINQACBOCS-UHFFFAOYSA-N 0.000 claims 1
• GEHDMIHNCABTQT-UHFFFAOYSA-N 8-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propylsulfanyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCCSC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 GEHDMIHNCABTQT-UHFFFAOYSA-N 0.000 claims 1
• TTWAZPUHJYFZBE-UHFFFAOYSA-N 8-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propylsulfonyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCCS(=O)(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 TTWAZPUHJYFZBE-UHFFFAOYSA-N 0.000 claims 1
• XFALKYFMNKMBHS-UHFFFAOYSA-N 8-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butoxy]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCCCOC=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 XFALKYFMNKMBHS-UHFFFAOYSA-N 0.000 claims 1
• BNZGJYFMZJHEKO-UHFFFAOYSA-N 8-[5-[4-(2-methoxyphenyl)piperazin-1-yl]pentoxy]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCCCCOC=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 BNZGJYFMZJHEKO-UHFFFAOYSA-N 0.000 claims 1
• UASGDBYXFRMWIK-UHFFFAOYSA-N CC1=C(SCCNCCCNC(=O)C2=CC=CC=3C(C(=C(OC32)C3=CC=CC=C3)C)=O)C=CC=C1 Chemical compound CC1=C(SCCNCCCNC(=O)C2=CC=CC=3C(C(=C(OC32)C3=CC=CC=C3)C)=O)C=CC=C1 UASGDBYXFRMWIK-UHFFFAOYSA-N 0.000 claims 1
• DWMFBOPKPQUICB-UHFFFAOYSA-N [1-[4-(2-methoxyphenyl)piperazin-1-yl]-2-methylpropan-2-yl] 3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound COC1=CC=CC=C1N1CCN(CC(C)(C)OC(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 DWMFBOPKPQUICB-UHFFFAOYSA-N 0.000 claims 1
• OFJQVZWDPUFURL-UHFFFAOYSA-N [2-[4-[3-[(3-methyl-4-oxo-2-phenylchromene-8-carbonyl)amino]propyl]piperazin-1-yl]phenyl] acetate Chemical compound CC(=O)OC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 OFJQVZWDPUFURL-UHFFFAOYSA-N 0.000 claims 1
• UFFGPEFBPWDTPG-UHFFFAOYSA-N [2-[4-[3-[(3-methyl-4-oxo-2-phenylchromene-8-carbonyl)amino]propyl]piperazin-1-yl]phenyl] n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 UFFGPEFBPWDTPG-UHFFFAOYSA-N 0.000 claims 1
• AJLQOIWTUULSNB-UHFFFAOYSA-N [8-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propylcarbamoyl]-3-methyl-4-oxo-2-phenylchromen-6-yl] acetate Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=C(OC(C)=O)C=2)CC1 AJLQOIWTUULSNB-UHFFFAOYSA-N 0.000 claims 1
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
• 125000006309 butyl amino group Chemical group 0.000 claims 1
• 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims 1
• 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 claims 1
• UUBJKHVFGWGJKX-UHFFFAOYSA-N hydrate tetrahydrochloride Chemical compound O.Cl.Cl.Cl.Cl UUBJKHVFGWGJKX-UHFFFAOYSA-N 0.000 claims 1
• 238000004519 manufacturing process Methods 0.000 claims 1
• YPDGPJDAJSYIFA-UHFFFAOYSA-N n-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-3-methyl-4-oxo-2-phenylchromene-8-sulfonamide Chemical compound COC1=CC=CC=C1N1CCN(CCNS(=O)(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 YPDGPJDAJSYIFA-UHFFFAOYSA-N 0.000 claims 1
• MCLOMZZRMDQNQC-UHFFFAOYSA-N n-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-n,3-dimethyl-4-oxo-2-phenylchromene-8-sulfonamide Chemical compound COC1=CC=CC=C1N1CCN(CCN(C)S(=O)(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 MCLOMZZRMDQNQC-UHFFFAOYSA-N 0.000 claims 1
• NIMDSPINUAFMMC-UHFFFAOYSA-N n-[3-(4,4-diphenylpiperidin-1-yl)propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)NCCCN(CC1)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 NIMDSPINUAFMMC-UHFFFAOYSA-N 0.000 claims 1
• KOSMADHBKLXGHG-UHFFFAOYSA-N n-[3-[2-(2-methoxyphenoxy)ethyl-methylamino]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1OCCN(C)CCCNC(=O)C1=CC=CC2=C1OC(C=1C=CC=CC=1)=C(C)C2=O KOSMADHBKLXGHG-UHFFFAOYSA-N 0.000 claims 1
• KDLDDFQFOSUQGH-UHFFFAOYSA-N n-[3-[2-(2-methoxyphenoxy)ethylamino]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1OCCNCCCNC(=O)C1=CC=CC2=C1OC(C=1C=CC=CC=1)=C(C)C2=O KDLDDFQFOSUQGH-UHFFFAOYSA-N 0.000 claims 1
• KSBGCFBIJRSOLC-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-2-(3-methyl-4-oxothiophen-2-yl)-4h-chromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C=3OC(=CCC=3C=CC=2)C=2SCC(=O)C=2C)CC1 KSBGCFBIJRSOLC-UHFFFAOYSA-N 0.000 claims 1
• BZJYCSXPKYJDOC-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3,6-dimethyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=C(C)C=2)CC1 BZJYCSXPKYJDOC-UHFFFAOYSA-N 0.000 claims 1
• PBSDQNKLWORARF-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-2-(4-methylphenyl)-4-oxochromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC(C)=CC=3)=O)C=CC=2)CC1 PBSDQNKLWORARF-UHFFFAOYSA-N 0.000 claims 1
• YCAOYABUUCKMON-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-2-(4-nitrophenyl)-4-oxochromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC(=CC=3)[N+]([O-])=O)=O)C=CC=2)CC1 YCAOYABUUCKMON-UHFFFAOYSA-N 0.000 claims 1
• WMPKEDKQVRWTAP-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-[4-(trifluoromethyl)phenyl]chromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC(=CC=3)C(F)(F)F)=O)C=CC=2)CC1 WMPKEDKQVRWTAP-UHFFFAOYSA-N 0.000 claims 1
• CRDHCIIFWPLAMU-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-sulfonamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNS(=O)(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 CRDHCIIFWPLAMU-UHFFFAOYSA-N 0.000 claims 1
• KXLPEPDVRPPMRV-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-pyridin-3-ylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=NC=CC=3)=O)C=CC=2)CC1 KXLPEPDVRPPMRV-UHFFFAOYSA-N 0.000 claims 1
• OUTKNWJZTFUTJQ-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-6-nitro-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=C(C=2)[N+]([O-])=O)CC1 OUTKNWJZTFUTJQ-UHFFFAOYSA-N 0.000 claims 1
• OJXGVCMQMVZHBR-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-4-oxo-2,3-dihydrochromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C=3OCCC(=O)C=3C=CC=2)CC1 OJXGVCMQMVZHBR-UHFFFAOYSA-N 0.000 claims 1
• YWSUCLWWSZFZMG-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-4-oxo-3-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C=4C=CC=CC=4)=CO3)=O)C=CC=2)CC1 YWSUCLWWSZFZMG-UHFFFAOYSA-N 0.000 claims 1
• NPJCJQQKGMFUDQ-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-4-oxochromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C=CO3)=O)C=CC=2)CC1 NPJCJQQKGMFUDQ-UHFFFAOYSA-N 0.000 claims 1
• VCAOCJITXXCABH-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-n,3-dimethyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCN(C)C(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 VCAOCJITXXCABH-UHFFFAOYSA-N 0.000 claims 1
• IQTMRJWHZXBCTB-UHFFFAOYSA-N n-[3-[4-(4-fluorobenzoyl)piperidin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)NCCCN(CC1)CCC1C(=O)C1=CC=C(F)C=C1 IQTMRJWHZXBCTB-UHFFFAOYSA-N 0.000 claims 1
• UAWUUKBOXDSXPL-UHFFFAOYSA-N n-[3-[4-(5-chloro-2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=C(Cl)C=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 UAWUUKBOXDSXPL-UHFFFAOYSA-N 0.000 claims 1
• WYUJYNXKIBXCJO-UHFFFAOYSA-N n-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-3-methyl-4-oxo-2-phenylchromene-8-sulfonamide Chemical compound COC1=CC=CC=C1N1CCN(CCCCNS(=O)(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 WYUJYNXKIBXCJO-UHFFFAOYSA-N 0.000 claims 1
• OIYIVORGVLZTJV-UHFFFAOYSA-N n-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-n,3-dimethyl-4-oxo-2-phenylchromene-8-sulfonamide Chemical compound COC1=CC=CC=C1N1CCN(CCCCN(C)S(=O)(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 OIYIVORGVLZTJV-UHFFFAOYSA-N 0.000 claims 1
• GHZOJONNTRFRRA-UHFFFAOYSA-N n-hydroxy-n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCN(O)C(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 GHZOJONNTRFRRA-UHFFFAOYSA-N 0.000 claims 1
• 125000004193 piperazinyl group Chemical group 0.000 claims 1
• 150000001412 amines Chemical class 0.000 abstract description 5
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 4
• 125000000623 heterocyclic group Chemical group 0.000 abstract description 3
• 210000001635 urinary tract Anatomy 0.000 abstract description 3
• 125000005842 heteroatom Chemical group 0.000 abstract description 2
• 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 abstract 1
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 abstract 1
• 208000004403 Prostatic Hyperplasia Diseases 0.000 abstract 1
• 239000005864 Sulphur Chemical group 0.000 abstract 1
• OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical group C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 abstract 1
• 125000005647 linker group Chemical group 0.000 abstract 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 434
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 313
• 239000000543 intermediate Substances 0.000 description 249
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 232
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 186
• 239000000243 solution Substances 0.000 description 185
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 164
• 239000000203 mixture Substances 0.000 description 136
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 132
• 235000019439 ethyl acetate Nutrition 0.000 description 105
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 94
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 84
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 84
• 239000011541 reaction mixture Substances 0.000 description 77
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 72
• 238000010992 reflux Methods 0.000 description 71
• 238000003756 stirring Methods 0.000 description 68
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 62
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 62
• 239000002585 base Substances 0.000 description 59
• 239000000741 silica gel Substances 0.000 description 54
• 229910002027 silica gel Inorganic materials 0.000 description 54
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
• 238000003818 flash chromatography Methods 0.000 description 46
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 38
• 238000001816 cooling Methods 0.000 description 38
• 238000002425 crystallisation Methods 0.000 description 38
• 230000008025 crystallization Effects 0.000 description 38
• 238000002844 melting Methods 0.000 description 38
• 230000008018 melting Effects 0.000 description 37
• VNZLQLYBRIOLFZ-UHFFFAOYSA-N 1-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCNCC1 VNZLQLYBRIOLFZ-UHFFFAOYSA-N 0.000 description 36
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 36
• 239000003208 petroleum Substances 0.000 description 34
• 238000000746 purification Methods 0.000 description 34
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 32
• 229960000583 acetic acid Drugs 0.000 description 32
• 238000001704 evaporation Methods 0.000 description 31
• 239000012044 organic layer Substances 0.000 description 30
• 230000008020 evaporation Effects 0.000 description 29
• AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 28
• 125000000896 monocarboxylic acid group Chemical group 0.000 description 27
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 27
• 239000003586 protic polar solvent Substances 0.000 description 26
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
• 239000012074 organic phase Substances 0.000 description 23
• 239000000047 product Substances 0.000 description 23
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
• 239000000284 extract Substances 0.000 description 21
• 239000007858 starting material Substances 0.000 description 21
• 239000003054 catalyst Substances 0.000 description 20
• 239000012043 crude product Substances 0.000 description 20
• 239000007787 solid Substances 0.000 description 20
• KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 description 19
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 19
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 19
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 19
• NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical class OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 19
• GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 18
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 18
• 238000001914 filtration Methods 0.000 description 18
• 238000010438 heat treatment Methods 0.000 description 18
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 18
• 239000002244 precipitate Substances 0.000 description 18
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 16
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
• 238000009835 boiling Methods 0.000 description 16
• 239000000725 suspension Substances 0.000 description 16
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 15
• 239000000010 aprotic solvent Substances 0.000 description 15
• 238000000967 suction filtration Methods 0.000 description 15
• 238000003786 synthesis reaction Methods 0.000 description 15
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
• 125000003118 aryl group Chemical group 0.000 description 14
• 230000015572 biosynthetic process Effects 0.000 description 14
• 238000004440 column chromatography Methods 0.000 description 14
• 229910000104 sodium hydride Inorganic materials 0.000 description 14
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 14
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 13
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
• 230000009467 reduction Effects 0.000 description 12
• 238000010898 silica gel chromatography Methods 0.000 description 12
• GPFVBEXADULZAD-UHFFFAOYSA-N 3-methyl-4-oxo-2-phenylchromene-8-carbonyl chloride Chemical compound O1C2=C(C(Cl)=O)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 GPFVBEXADULZAD-UHFFFAOYSA-N 0.000 description 11
• 239000012267 brine Substances 0.000 description 11
• 239000005457 ice water Substances 0.000 description 11
• 229940098779 methanesulfonic acid Drugs 0.000 description 11
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 11
• 238000007363 ring formation reaction Methods 0.000 description 11
• 239000011780 sodium chloride Substances 0.000 description 11
• 229910052938 sodium sulfate Inorganic materials 0.000 description 11
• 235000011152 sodium sulphate Nutrition 0.000 description 11
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
• IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 10
• 239000002841 Lewis acid Substances 0.000 description 10
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
• 244000309464 bull Species 0.000 description 10
• 150000007517 lewis acids Chemical class 0.000 description 10
• 239000000155 melt Substances 0.000 description 10
• 239000012279 sodium borohydride Substances 0.000 description 10
• 229910000033 sodium borohydride Inorganic materials 0.000 description 10
• 238000000605 extraction Methods 0.000 description 9
• 239000010410 layer Substances 0.000 description 9
• WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
• 229920000137 polyphosphoric acid Polymers 0.000 description 9
• 102000005962 receptors Human genes 0.000 description 9
• 108020003175 receptors Proteins 0.000 description 9
• 235000017557 sodium bicarbonate Nutrition 0.000 description 9
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
• 238000005406 washing Methods 0.000 description 9
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 8
• AECRGCYUBPXQBU-UHFFFAOYSA-N 8-amino-3-methyl-2-phenylchromen-4-one Chemical compound O1C2=C(N)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 AECRGCYUBPXQBU-UHFFFAOYSA-N 0.000 description 8
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
• 230000002378 acidificating effect Effects 0.000 description 8
• 239000008346 aqueous phase Substances 0.000 description 8
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
• 230000000694 effects Effects 0.000 description 8
• 239000003480 eluent Substances 0.000 description 8
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
• LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
• 239000003921 oil Substances 0.000 description 8
• 239000012258 stirred mixture Substances 0.000 description 8
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 8
• OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 7
• 238000005481 NMR spectroscopy Methods 0.000 description 7
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
• 239000003153 chemical reaction reagent Substances 0.000 description 7
• 238000009833 condensation Methods 0.000 description 7
• 230000005494 condensation Effects 0.000 description 7
• 235000011949 flavones Nutrition 0.000 description 7
• 239000011734 sodium Substances 0.000 description 7
• 229910000029 sodium carbonate Inorganic materials 0.000 description 7
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 7
• VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 7
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
• 238000001035 drying Methods 0.000 description 6
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
• 229910052757 nitrogen Inorganic materials 0.000 description 6
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 6
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 6
• 229910052708 sodium Inorganic materials 0.000 description 6
• 239000012312 sodium hydride Substances 0.000 description 6
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
• JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 6
• PFFBVVXRQFBACM-UHFFFAOYSA-N 3-methyl-4-oxo-2-phenylchromene-8-carbaldehyde Chemical compound O1C2=C(C=O)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 PFFBVVXRQFBACM-UHFFFAOYSA-N 0.000 description 5
• 101150065749 Churc1 gene Proteins 0.000 description 5
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 5
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
• 239000007864 aqueous solution Substances 0.000 description 5
• CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 5
• 239000003795 chemical substances by application Substances 0.000 description 5
• 239000012065 filter cake Substances 0.000 description 5
• 238000005984 hydrogenation reaction Methods 0.000 description 5
• 230000007062 hydrolysis Effects 0.000 description 5
• 238000006460 hydrolysis reaction Methods 0.000 description 5
• 230000001965 increasing effect Effects 0.000 description 5
• 230000003647 oxidation Effects 0.000 description 5
• 238000007254 oxidation reaction Methods 0.000 description 5
• 238000001953 recrystallisation Methods 0.000 description 5
• 229920006395 saturated elastomer Polymers 0.000 description 5
• 239000008096 xylene Substances 0.000 description 5
• 239000011701 zinc Substances 0.000 description 5
• RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
• MUSOMUXTQGJZKD-UHFFFAOYSA-N 1-(2-chloroethyl)-4-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCN(CCCl)CC1 MUSOMUXTQGJZKD-UHFFFAOYSA-N 0.000 description 4
• OIZBMQFOSPOOIS-UHFFFAOYSA-N 1-(3-chloropropyl)-4-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCN(CCCCl)CC1 OIZBMQFOSPOOIS-UHFFFAOYSA-N 0.000 description 4
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 4
• HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
• ONJRTQUWKRDCTA-UHFFFAOYSA-N 2h-thiochromene Chemical compound C1=CC=C2C=CCSC2=C1 ONJRTQUWKRDCTA-UHFFFAOYSA-N 0.000 description 4
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
• MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 4
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
• OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
• WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
• 102100038239 Protein Churchill Human genes 0.000 description 4
• NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
• 125000003277 amino group Chemical group 0.000 description 4
• 239000013078 crystal Substances 0.000 description 4
• 238000010511 deprotection reaction Methods 0.000 description 4
• GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 4
• SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 4
• WEMCZZDLULONHY-UHFFFAOYSA-N ethyl 2-hydroxy-3-propanoylbenzoate Chemical compound CCOC(=O)C1=CC=CC(C(=O)CC)=C1O WEMCZZDLULONHY-UHFFFAOYSA-N 0.000 description 4
• 150000002212 flavone derivatives Chemical class 0.000 description 4
• SPIUTQOUKAMGCX-UHFFFAOYSA-N flavoxate Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)OCCN1CCCCC1 SPIUTQOUKAMGCX-UHFFFAOYSA-N 0.000 description 4
• 239000012362 glacial acetic acid Substances 0.000 description 4
• 150000002391 heterocyclic compounds Chemical class 0.000 description 4
• 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
• 238000002955 isolation Methods 0.000 description 4
• 239000002480 mineral oil Substances 0.000 description 4
• 235000010446 mineral oil Nutrition 0.000 description 4
• 239000012454 non-polar solvent Substances 0.000 description 4
• 230000020477 pH reduction Effects 0.000 description 4
• 239000012071 phase Substances 0.000 description 4
• 229910052700 potassium Inorganic materials 0.000 description 4
• 239000011591 potassium Substances 0.000 description 4
• 230000002829 reductive effect Effects 0.000 description 4
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
• 230000009466 transformation Effects 0.000 description 4
• 238000010626 work up procedure Methods 0.000 description 4
• ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 3
• GUTWDZXWTKMXPI-UHFFFAOYSA-N 1-(2-chlorophenyl)piperazin-4-ium;chloride Chemical compound Cl.ClC1=CC=CC=C1N1CCNCC1 GUTWDZXWTKMXPI-UHFFFAOYSA-N 0.000 description 3
• 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 3
• OXZYBOLWRXENKT-UHFFFAOYSA-N 4-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=C(C(Cl)=O)C=C1 OXZYBOLWRXENKT-UHFFFAOYSA-N 0.000 description 3
• KUHLPDFFVKSOLQ-UHFFFAOYSA-N 8-hydroxy-3-methyl-2-phenylchromen-4-one Chemical compound O1C2=C(O)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 KUHLPDFFVKSOLQ-UHFFFAOYSA-N 0.000 description 3
• 239000004342 Benzoyl peroxide Substances 0.000 description 3
• OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
• 239000007868 Raney catalyst Substances 0.000 description 3
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
• GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 3
• 239000000370 acceptor Substances 0.000 description 3
• 230000003042 antagnostic effect Effects 0.000 description 3
• 239000003125 aqueous solvent Substances 0.000 description 3
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
• 150000001562 benzopyrans Chemical group 0.000 description 3
• 235000019400 benzoyl peroxide Nutrition 0.000 description 3
• HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 3
• 230000027455 binding Effects 0.000 description 3
• 229910002091 carbon monoxide Inorganic materials 0.000 description 3
• 239000003638 chemical reducing agent Substances 0.000 description 3
• 230000008602 contraction Effects 0.000 description 3
• 238000000354 decomposition reaction Methods 0.000 description 3
• 238000004090 dissolution Methods 0.000 description 3
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
• 239000000706 filtrate Substances 0.000 description 3
• 229930003944 flavone Natural products 0.000 description 3
• 229960000855 flavoxate Drugs 0.000 description 3
• 235000019253 formic acid Nutrition 0.000 description 3
• 239000007789 gas Substances 0.000 description 3
• VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylene tetramine Natural products C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 3
• 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
• 239000012280 lithium aluminium hydride Substances 0.000 description 3
• GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 3
• 231100000053 low toxicity Toxicity 0.000 description 3
• 239000002808 molecular sieve Substances 0.000 description 3
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Substances ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 3
• MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
• 229910052763 palladium Inorganic materials 0.000 description 3
• 229910003446 platinum oxide Inorganic materials 0.000 description 3
• 239000012286 potassium permanganate Substances 0.000 description 3
• 235000017281 sodium acetate Nutrition 0.000 description 3
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
• 239000000126 substance Substances 0.000 description 3
• 239000011593 sulfur Substances 0.000 description 3
• 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 3
• 239000011592 zinc chloride Substances 0.000 description 3
• 235000005074 zinc chloride Nutrition 0.000 description 3
• OTXJEUQUKNCKPS-UHFFFAOYSA-N (3-methyl-4-oxo-2-phenylchromen-8-yl)methyl carbamimidothioate Chemical compound O1C2=C(CSC(N)=N)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 OTXJEUQUKNCKPS-UHFFFAOYSA-N 0.000 description 2
• VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 2
• JZJRVFQLQMGBTI-UHFFFAOYSA-N 1-[4-(2-methoxyphenyl)piperazin-1-yl]propan-1-amine Chemical compound C1CN(C(N)CC)CCN1C1=CC=CC=C1OC JZJRVFQLQMGBTI-UHFFFAOYSA-N 0.000 description 2
• IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
• JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 2
• OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
• 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
• BNKPFZVIJZNDLZ-UHFFFAOYSA-N 2-hydroxy-3-propanoylbenzoic acid Chemical compound CCC(=O)C1=CC=CC(C(O)=O)=C1O BNKPFZVIJZNDLZ-UHFFFAOYSA-N 0.000 description 2
• SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
• OVGGXHMQXIQOBR-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propan-1-amine Chemical compound COC1=CC=CC=C1N1CCN(CCCN)CC1 OVGGXHMQXIQOBR-UHFFFAOYSA-N 0.000 description 2
• RSRUCDFWUAEYEU-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate;dihydrochloride Chemical compound Cl.Cl.COC1=CC=CC=C1N1CCN(CCCOC(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 RSRUCDFWUAEYEU-UHFFFAOYSA-N 0.000 description 2
• LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
• KMMBBZOSQNLLMN-UHFFFAOYSA-N 3-methylflavone-8-carboxylic acid Chemical compound O1C2=C(C(O)=O)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 KMMBBZOSQNLLMN-UHFFFAOYSA-N 0.000 description 2
• UFJPFLDFMPVGRW-UHFFFAOYSA-N 4-[4-(2-methoxyphenyl)piperazin-1-yl]butan-1-amine Chemical compound COC1=CC=CC=C1N1CCN(CCCCN)CC1 UFJPFLDFMPVGRW-UHFFFAOYSA-N 0.000 description 2
• NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 2
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
• ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
• 229940127291 Calcium channel antagonist Drugs 0.000 description 2
• UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
• VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
• 239000005977 Ethylene Substances 0.000 description 2
• AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
• 229910010082 LiAlH Inorganic materials 0.000 description 2
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
• RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
• 208000026723 Urinary tract disease Diseases 0.000 description 2
• HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
• 230000001476 alcoholic effect Effects 0.000 description 2
• 150000001298 alcohols Chemical class 0.000 description 2
• 238000005904 alkaline hydrolysis reaction Methods 0.000 description 2
• 125000005277 alkyl imino group Chemical group 0.000 description 2
• 229940030600 antihypertensive agent Drugs 0.000 description 2
• 239000002220 antihypertensive agent Substances 0.000 description 2
• 239000003849 aromatic solvent Substances 0.000 description 2
• 125000003710 aryl alkyl group Chemical group 0.000 description 2
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
• 229910052796 boron Inorganic materials 0.000 description 2
• 229910052794 bromium Inorganic materials 0.000 description 2
• 239000000480 calcium channel blocker Substances 0.000 description 2
• 239000001110 calcium chloride Substances 0.000 description 2
• 229910001628 calcium chloride Inorganic materials 0.000 description 2
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
• 150000007942 carboxylates Chemical group 0.000 description 2
• 230000003197 catalytic effect Effects 0.000 description 2
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
• 210000003169 central nervous system Anatomy 0.000 description 2
• DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 2
• KTRFZWJCHOQHMN-UHFFFAOYSA-N chloromethanethioic s-acid Chemical compound SC(Cl)=O KTRFZWJCHOQHMN-UHFFFAOYSA-N 0.000 description 2
• MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 description 2
• 239000007822 coupling agent Substances 0.000 description 2
• 239000013058 crude material Substances 0.000 description 2
• 238000001212 derivatisation Methods 0.000 description 2
• 238000006193 diazotization reaction Methods 0.000 description 2
• 238000004821 distillation Methods 0.000 description 2
• 239000003814 drug Substances 0.000 description 2
• 238000000921 elemental analysis Methods 0.000 description 2
• 238000005886 esterification reaction Methods 0.000 description 2
• 150000002148 esters Chemical class 0.000 description 2
• WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
• 125000001072 heteroaryl group Chemical group 0.000 description 2
• 239000004312 hexamethylene tetramine Substances 0.000 description 2
• 235000010299 hexamethylene tetramine Nutrition 0.000 description 2
• 150000002466 imines Chemical class 0.000 description 2
• 150000002475 indoles Chemical class 0.000 description 2
• 239000002198 insoluble material Substances 0.000 description 2
• QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 2
• 229910052740 iodine Inorganic materials 0.000 description 2
• 239000011630 iodine Substances 0.000 description 2
• INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
• 229910052751 metal Inorganic materials 0.000 description 2
• 239000002184 metal Substances 0.000 description 2
• YUIMWZDRXNUGMO-UHFFFAOYSA-N methyl 4-oxo-2-phenylthiochromene-8-carboxylate Chemical compound COC(=O)C1=CC=CC(C(C=2)=O)=C1SC=2C1=CC=CC=C1 YUIMWZDRXNUGMO-UHFFFAOYSA-N 0.000 description 2
• XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
• 239000003960 organic solvent Substances 0.000 description 2
• 239000007800 oxidant agent Substances 0.000 description 2
• 230000001590 oxidative effect Effects 0.000 description 2
• 239000003444 phase transfer catalyst Substances 0.000 description 2
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
• 150000002989 phenols Chemical class 0.000 description 2
• YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 2
• 235000011007 phosphoric acid Nutrition 0.000 description 2
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
• 239000001103 potassium chloride Substances 0.000 description 2
• 235000011164 potassium chloride Nutrition 0.000 description 2
• GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 2
• IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 2
• 210000002307 prostate Anatomy 0.000 description 2
• 238000000926 separation method Methods 0.000 description 2
• 229940076279 serotonin Drugs 0.000 description 2
• NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
• SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
• 239000001632 sodium acetate Substances 0.000 description 2
• ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
• 235000009518 sodium iodide Nutrition 0.000 description 2
• 235000010288 sodium nitrite Nutrition 0.000 description 2
• JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
• 238000006467 substitution reaction Methods 0.000 description 2
• KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
• DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
• 229940124597 therapeutic agent Drugs 0.000 description 2
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
• FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
• 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 2
• 238000000844 transformation Methods 0.000 description 2
• AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
• 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 2
• 229910052721 tungsten Inorganic materials 0.000 description 2
• 208000014001 urinary system disease Diseases 0.000 description 2
• 229910052725 zinc Inorganic materials 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
• TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
• VQTYZZPDAFGNCK-UHFFFAOYSA-N (2-methyl-1-piperidin-1-ylpropan-2-yl) 3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)OC(C)(C)CN1CCCCC1 VQTYZZPDAFGNCK-UHFFFAOYSA-N 0.000 description 1
• MKYPNZBEBRPWDQ-UHFFFAOYSA-N (2-methyl-1-piperidin-1-ylpropan-2-yl) 3-methyl-4-oxo-2-phenylchromene-8-carboxylate;hydrochloride Chemical compound Cl.C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)OC(C)(C)CN1CCCCC1 MKYPNZBEBRPWDQ-UHFFFAOYSA-N 0.000 description 1
• NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
• QCSZDAARWAAPHR-UHFFFAOYSA-N (3-methyl-4-oxo-2-phenylchromen-8-yl)methanesulfonyl chloride Chemical compound O1C2=C(CS(Cl)(=O)=O)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 QCSZDAARWAAPHR-UHFFFAOYSA-N 0.000 description 1
• ABERUOJGWHYBJL-UHFFFAOYSA-N (4-fluorophenyl)-piperidin-4-ylmethanone Chemical compound C1=CC(F)=CC=C1C(=O)C1CCNCC1 ABERUOJGWHYBJL-UHFFFAOYSA-N 0.000 description 1
• HIFPBFTYXVCJGH-ZHACJKMWSA-N (e)-3-(3-methyl-4-oxo-2-phenylchromen-8-yl)prop-2-enoyl chloride Chemical compound O1C2=C(\C=C\C(Cl)=O)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 HIFPBFTYXVCJGH-ZHACJKMWSA-N 0.000 description 1
• WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 1
• VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 1
• IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 description 1
• 125000005877 1,4-benzodioxanyl group Chemical group 0.000 description 1
• OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
• RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
• IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 1
• CFTRKGCBMZSAED-UHFFFAOYSA-N 1-(2,2-diethoxyethylsulfanyl)-2-methylbenzene Chemical compound CCOC(OCC)CSC1=CC=CC=C1C CFTRKGCBMZSAED-UHFFFAOYSA-N 0.000 description 1
• MRBFGEHILMYPTF-UHFFFAOYSA-N 1-(2-Pyrimidyl)piperazine Chemical compound C1CNCCN1C1=NC=CC=N1 MRBFGEHILMYPTF-UHFFFAOYSA-N 0.000 description 1
• UBCOUCLJQAJMMO-UHFFFAOYSA-N 1-(2-chloroethyl)-3-[(3-methyl-4-oxo-2-phenylchromen-8-yl)methyl]urea Chemical compound O1C2=C(CNC(=O)NCCCl)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 UBCOUCLJQAJMMO-UHFFFAOYSA-N 0.000 description 1
• FBQIUSDQWOLCNY-UHFFFAOYSA-N 1-(2-ethoxyphenyl)piperazine Chemical compound CCOC1=CC=CC=C1N1CCNCC1 FBQIUSDQWOLCNY-UHFFFAOYSA-N 0.000 description 1
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
• QABBSGYZBFHJIW-UHFFFAOYSA-N 1-[4-(2-methoxyphenyl)piperazin-1-yl]-2-methylpropan-2-ol Chemical compound COC1=CC=CC=C1N1CCN(CC(C)(C)O)CC1 QABBSGYZBFHJIW-UHFFFAOYSA-N 0.000 description 1
• WXMQDCRVBPMUBV-UHFFFAOYSA-N 1-anilinopropan-1-ol Chemical class CCC(O)NC1=CC=CC=C1 WXMQDCRVBPMUBV-UHFFFAOYSA-N 0.000 description 1
• NIDSRGCVYOEDFW-UHFFFAOYSA-N 1-bromo-4-chlorobutane Chemical compound ClCCCCBr NIDSRGCVYOEDFW-UHFFFAOYSA-N 0.000 description 1
• BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 1
• JNOZGFXJZQXOSU-UHFFFAOYSA-N 1-chloro-2-methylpropan-2-ol Chemical compound CC(C)(O)CCl JNOZGFXJZQXOSU-UHFFFAOYSA-N 0.000 description 1
• XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
• 238000005160 1H NMR spectroscopy Methods 0.000 description 1
• WXOCMYPFQNKWMB-UHFFFAOYSA-N 2,2,2-trifluoro-n-(3-methyl-4-oxo-2-phenylchromen-8-yl)acetamide Chemical compound O1C2=C(NC(=O)C(F)(F)F)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 WXOCMYPFQNKWMB-UHFFFAOYSA-N 0.000 description 1
• PZFILRCPUYXADH-UHFFFAOYSA-N 2,2,2-trifluoro-n-[(3-methyl-4-oxo-2-phenylchromen-8-yl)methyl]acetamide Chemical compound O1C2=C(CNC(=O)C(F)(F)F)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 PZFILRCPUYXADH-UHFFFAOYSA-N 0.000 description 1
• DVDHFUKIABYMND-UHFFFAOYSA-N 2,2,2-trifluoro-n-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-n-methylacetamide Chemical compound COC1=CC=CC=C1N1CCN(CCCCN(C)C(=O)C(F)(F)F)CC1 DVDHFUKIABYMND-UHFFFAOYSA-N 0.000 description 1
• NDBBSDFKFGLWIL-UHFFFAOYSA-N 2,2,2-trifluoro-n-methyl-n-(3-methyl-4-oxo-2-phenylchromen-8-yl)acetamide Chemical compound FC(F)(F)C(=O)N(C)C1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=CC=C1 NDBBSDFKFGLWIL-UHFFFAOYSA-N 0.000 description 1
• LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
• UOBSJOUJKBGJMU-UHFFFAOYSA-N 2-(2,6-dimethoxyphenoxy)acetaldehyde Chemical compound COC1=CC=CC(OC)=C1OCC=O UOBSJOUJKBGJMU-UHFFFAOYSA-N 0.000 description 1
• OOKCBENPEIHOJG-UHFFFAOYSA-N 2-(2-ethoxyphenoxy)ethanamine Chemical compound CCOC1=CC=CC=C1OCCN OOKCBENPEIHOJG-UHFFFAOYSA-N 0.000 description 1
• CKJRKLKVCHMWLV-UHFFFAOYSA-N 2-(2-methoxyphenoxy)ethanamine Chemical compound COC1=CC=CC=C1OCCN CKJRKLKVCHMWLV-UHFFFAOYSA-N 0.000 description 1
• RZNHYZIKLBDXFL-UHFFFAOYSA-N 2-(2-methylphenyl)sulfanylacetaldehyde Chemical compound CC1=CC=CC=C1SCC=O RZNHYZIKLBDXFL-UHFFFAOYSA-N 0.000 description 1
• BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
• QMOBUFLQLKJJOE-UHFFFAOYSA-N 2-(3-methyl-4-oxo-2-phenylchromen-8-yl)-2-morpholin-4-ylacetonitrile Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(C#N)N1CCOCC1 QMOBUFLQLKJJOE-UHFFFAOYSA-N 0.000 description 1
• LVEAVEPHDCWUKJ-UHFFFAOYSA-N 2-(3-methyl-4-oxo-2-phenylchromen-8-yl)-2-morpholin-4-ylpentanedinitrile Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(CCC#N)(C#N)N1CCOCC1 LVEAVEPHDCWUKJ-UHFFFAOYSA-N 0.000 description 1
• KYDJUPYKCCFBTB-UHFFFAOYSA-N 2-(3-methyl-4-oxo-2-phenylchromen-8-yl)acetic acid Chemical compound O1C2=C(CC(O)=O)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 KYDJUPYKCCFBTB-UHFFFAOYSA-N 0.000 description 1
• OLUBPSFSFRZWGK-UHFFFAOYSA-N 2-(4-benzoylphenyl)-3-methyl-4-oxochromene-8-carboxylic acid Chemical compound O1C2=C(C(O)=O)C=CC=C2C(=O)C(C)=C1C(C=C1)=CC=C1C(=O)C1=CC=CC=C1 OLUBPSFSFRZWGK-UHFFFAOYSA-N 0.000 description 1
• DCNPRASTLOYJDV-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-methyl-4-oxochromene-8-carboxylic acid Chemical compound O1C2=C(C(O)=O)C=CC=C2C(=O)C(C)=C1C1=CC=C(F)C=C1 DCNPRASTLOYJDV-UHFFFAOYSA-N 0.000 description 1
• RIAFRDBEMVUDGW-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-3-methyl-4-oxochromene-8-carboxylic acid Chemical compound O1C2=C(C(O)=O)C=CC=C2C(=O)C(C)=C1C1=CC=C(O)C=C1 RIAFRDBEMVUDGW-UHFFFAOYSA-N 0.000 description 1
• XEOVRAFBAQWWAE-UHFFFAOYSA-N 2-(furan-2-yl)-3-methyl-4-oxochromene-8-carboxylic acid Chemical compound O1C2=C(C(O)=O)C=CC=C2C(=O)C(C)=C1C1=CC=CO1 XEOVRAFBAQWWAE-UHFFFAOYSA-N 0.000 description 1
• XWKAVQKJQBISOL-UHFFFAOYSA-N 2-(phenylazaniumyl)propanoate Chemical class OC(=O)C(C)NC1=CC=CC=C1 XWKAVQKJQBISOL-UHFFFAOYSA-N 0.000 description 1
• XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
• CQVKMVQRSNNAGO-UHFFFAOYSA-N 2-[4-formyl-3-methyl-n-(2-methylsulfonyloxyethyl)anilino]ethyl methanesulfonate Chemical compound CC1=CC(N(CCOS(C)(=O)=O)CCOS(C)(=O)=O)=CC=C1C=O CQVKMVQRSNNAGO-UHFFFAOYSA-N 0.000 description 1
• GIPINPBJQMOFDA-UHFFFAOYSA-N 2-benzoyl-3-ethyl-1-benzofuran-7-carboxylic acid Chemical compound O1C2=C(C(O)=O)C=CC=C2C(CC)=C1C(=O)C1=CC=CC=C1 GIPINPBJQMOFDA-UHFFFAOYSA-N 0.000 description 1
• LILXDMFJXYAKMK-UHFFFAOYSA-N 2-bromo-1,1-diethoxyethane Chemical compound CCOC(CBr)OCC LILXDMFJXYAKMK-UHFFFAOYSA-N 0.000 description 1
• RCZVJASMLCGXQO-UHFFFAOYSA-N 2-chloro-n-methyl-n-[(3-methyl-4-oxo-2-phenylchromen-8-yl)methyl]acetamide Chemical compound ClCC(=O)N(C)CC1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=CC=C1 RCZVJASMLCGXQO-UHFFFAOYSA-N 0.000 description 1
• VHCSBTPOPKFYIU-UHFFFAOYSA-N 2-chloroethanesulfonyl chloride Chemical compound ClCCS(Cl)(=O)=O VHCSBTPOPKFYIU-UHFFFAOYSA-N 0.000 description 1
• 125000006012 2-chloroethoxy group Chemical group 0.000 description 1
• MXBICIPZCUTERU-UHFFFAOYSA-N 2-cyclohexyl-3-methyl-4-oxochromene-8-carboxylic acid Chemical compound O1C2=C(C(O)=O)C=CC=C2C(=O)C(C)=C1C1CCCCC1 MXBICIPZCUTERU-UHFFFAOYSA-N 0.000 description 1
• NCXQTNBHJRSRJD-UHFFFAOYSA-N 2-hydroxy-5-nitro-3-propanoylbenzoic acid Chemical compound CCC(=O)C1=CC([N+]([O-])=O)=CC(C(O)=O)=C1O NCXQTNBHJRSRJD-UHFFFAOYSA-N 0.000 description 1
• CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 1
• SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
• UORNTHBBLYBAJJ-UHFFFAOYSA-N 2-piperazin-1-ylphenol Chemical compound OC1=CC=CC=C1N1CCNCC1 UORNTHBBLYBAJJ-UHFFFAOYSA-N 0.000 description 1
• MDRKZASMSSBJBO-UHFFFAOYSA-N 2-tert-butyl-3-methyl-4-oxochromene-8-carboxylic acid Chemical compound C1=CC=C2C(=O)C(C)=C(C(C)(C)C)OC2=C1C(O)=O MDRKZASMSSBJBO-UHFFFAOYSA-N 0.000 description 1
• HMXJOWDZAJWLTF-UHFFFAOYSA-N 2h-chromene-2-carboxylic acid Chemical class C1=CC=C2C=CC(C(=O)O)OC2=C1 HMXJOWDZAJWLTF-UHFFFAOYSA-N 0.000 description 1
• DKFROYPQEDVABD-UHFFFAOYSA-N 3-(hydroxymethyl)-4-oxo-2-phenylchromene-8-carboxylic acid Chemical compound O1C2=C(C(O)=O)C=CC=C2C(=O)C(CO)=C1C1=CC=CC=C1 DKFROYPQEDVABD-UHFFFAOYSA-N 0.000 description 1
• WBSJEDOPYRUTDF-UHFFFAOYSA-N 3-[4-(2-chlorophenyl)piperazin-1-yl]propyl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate;dihydrochloride Chemical compound Cl.Cl.C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)OCCCN(CC1)CCN1C1=CC=CC=C1Cl WBSJEDOPYRUTDF-UHFFFAOYSA-N 0.000 description 1
• IYXMMOVSDUHPKI-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]-n-(oxan-2-yloxy)propan-1-amine Chemical compound COC1=CC=CC=C1N1CCN(CCCNOC2OCCCC2)CC1 IYXMMOVSDUHPKI-UHFFFAOYSA-N 0.000 description 1
• SGJVKKPHPYTNHR-UHFFFAOYSA-N 3-[4-(2-methoxyphenyl)piperazin-1-yl]-n-methylpropan-1-amine Chemical compound C1CN(CCCNC)CCN1C1=CC=CC=C1OC SGJVKKPHPYTNHR-UHFFFAOYSA-N 0.000 description 1
• TVYRJQXMQNZLNO-UHFFFAOYSA-N 3-acetyl-2-hydroxybenzoic acid Chemical compound CC(=O)C1=CC=CC(C(O)=O)=C1O TVYRJQXMQNZLNO-UHFFFAOYSA-N 0.000 description 1
• BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
• GIAXIYZWZIDTPK-UHFFFAOYSA-N 3-bromopropyl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound O1C2=C(C(=O)OCCCBr)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 GIAXIYZWZIDTPK-UHFFFAOYSA-N 0.000 description 1
• PCDJHJZQHWVTQD-UHFFFAOYSA-N 3-methyl-2-(4-methylphenyl)-4-oxochromene-8-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=C(C)C(=O)C2=CC=CC(C(O)=O)=C2O1 PCDJHJZQHWVTQD-UHFFFAOYSA-N 0.000 description 1
• UUQRMWIJWUBHGE-UHFFFAOYSA-N 3-methyl-2-(4-nitrophenyl)-4-oxochromene-8-carboxylic acid Chemical compound O1C2=C(C(O)=O)C=CC=C2C(=O)C(C)=C1C1=CC=C([N+]([O-])=O)C=C1 UUQRMWIJWUBHGE-UHFFFAOYSA-N 0.000 description 1
• CPMKAFLZWFEHBO-UHFFFAOYSA-N 3-methyl-2-phenyl-8-prop-2-enylchromen-4-one Chemical compound O1C2=C(CC=C)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 CPMKAFLZWFEHBO-UHFFFAOYSA-N 0.000 description 1
• LEOYTYBMBCHUEH-UHFFFAOYSA-N 3-methyl-2-phenyl-8-sulfanylchromen-4-one Chemical compound O1C2=C(S)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 LEOYTYBMBCHUEH-UHFFFAOYSA-N 0.000 description 1
• GJZUZCGURONHAJ-UHFFFAOYSA-N 3-methyl-4-oxo-2-(4-phenoxyphenyl)chromene-8-carboxylic acid Chemical compound O1C2=C(C(O)=O)C=CC=C2C(=O)C(C)=C1C(C=C1)=CC=C1OC1=CC=CC=C1 GJZUZCGURONHAJ-UHFFFAOYSA-N 0.000 description 1
• KJVFYFCDYCXAPH-UHFFFAOYSA-N 3-methyl-4-oxo-2-(4-phenylphenyl)chromene-8-carboxylic acid Chemical compound O1C2=C(C(O)=O)C=CC=C2C(=O)C(C)=C1C(C=C1)=CC=C1C1=CC=CC=C1 KJVFYFCDYCXAPH-UHFFFAOYSA-N 0.000 description 1
• WXGGUSZOQVTNNI-UHFFFAOYSA-N 3-methyl-4-oxo-2-(trifluoromethyl)chromene-8-carboxylic acid Chemical compound C1=CC=C2C(=O)C(C)=C(C(F)(F)F)OC2=C1C(O)=O WXGGUSZOQVTNNI-UHFFFAOYSA-N 0.000 description 1
• XIBYEFNFXSXHJP-ZHACJKMWSA-N 3-methyl-4-oxo-2-[(e)-2-phenylethenyl]chromene-8-carboxylic acid Chemical compound O1C2=C(C(O)=O)C=CC=C2C(=O)C(C)=C1\C=C\C1=CC=CC=C1 XIBYEFNFXSXHJP-ZHACJKMWSA-N 0.000 description 1
• AOWOKBFRDIQJQZ-UHFFFAOYSA-N 3-methyl-4-oxo-2-[4-(trifluoromethyl)phenyl]chromene-8-carboxylic acid Chemical compound O1C2=C(C(O)=O)C=CC=C2C(=O)C(C)=C1C1=CC=C(C(F)(F)F)C=C1 AOWOKBFRDIQJQZ-UHFFFAOYSA-N 0.000 description 1
• MKBUTOMQYDNUON-UHFFFAOYSA-N 3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound O1C2=C(C(N)=O)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 MKBUTOMQYDNUON-UHFFFAOYSA-N 0.000 description 1
• HNSPZGPQEAIHNV-UHFFFAOYSA-N 3-methyl-4-oxo-2-thiophen-2-ylchromene-8-carboxylic acid Chemical compound O1C2=C(C(O)=O)C=CC=C2C(=O)C(C)=C1C1=CC=CS1 HNSPZGPQEAIHNV-UHFFFAOYSA-N 0.000 description 1
• CXEKXNFFOPQONM-UHFFFAOYSA-N 3-methyl-5-[4-[(2-methylpropan-2-yl)oxyamino]-4-oxobutyl]-4-oxo-2-phenylchromene-8-carboxamide Chemical compound CC(C)(C)ONC(=O)CCCC1=CC=C(C2=C1C(C(=C(O2)C1=CC=CC=C1)C)=O)C(=O)N CXEKXNFFOPQONM-UHFFFAOYSA-N 0.000 description 1
• JSTJHPZLFGAHJW-UHFFFAOYSA-N 3-methyl-6-nitro-4-oxo-2-phenylchromene-8-carbonyl chloride Chemical compound O1C2=C(C(Cl)=O)C=C([N+]([O-])=O)C=C2C(=O)C(C)=C1C1=CC=CC=C1 JSTJHPZLFGAHJW-UHFFFAOYSA-N 0.000 description 1
• XZRASZGEMDJHPL-UHFFFAOYSA-N 3-methyl-6-nitro-4-oxo-2-phenylchromene-8-carboxylic acid Chemical compound O1C2=C(C(O)=O)C=C([N+]([O-])=O)C=C2C(=O)C(C)=C1C1=CC=CC=C1 XZRASZGEMDJHPL-UHFFFAOYSA-N 0.000 description 1
• VEJXEPSOOWFEQF-UHFFFAOYSA-N 3-methyl-8-(methylamino)-2-phenylchromen-4-one Chemical compound CNC1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=CC=C1 VEJXEPSOOWFEQF-UHFFFAOYSA-N 0.000 description 1
• SCPIAZNQDNSMJP-UHFFFAOYSA-N 3-methyl-8-(methylaminomethyl)-2-phenylchromen-4-one Chemical compound CNCC1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=CC=C1 SCPIAZNQDNSMJP-UHFFFAOYSA-N 0.000 description 1
• PJLSGSKVDWCDFL-UHFFFAOYSA-N 3-methyl-8-(oxiran-2-ylmethoxy)-2-phenylchromen-4-one Chemical compound C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1OCC1CO1 PJLSGSKVDWCDFL-UHFFFAOYSA-N 0.000 description 1
• CXWSANLKPOWREJ-UHFFFAOYSA-N 3-methyl-8-[2-[4-(2-methylphenyl)piperazin-1-yl]acetyl]-2-phenylchromen-4-one;hydrochloride Chemical compound Cl.CC1=CC=CC=C1N1CCN(CC(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 CXWSANLKPOWREJ-UHFFFAOYSA-N 0.000 description 1
• BTVVEKSXUOEVAY-UHFFFAOYSA-N 4,4-diphenylpiperidine Chemical compound C1CNCCC1(C=1C=CC=CC=1)C1=CC=CC=C1 BTVVEKSXUOEVAY-UHFFFAOYSA-N 0.000 description 1
• LJZBGFOFUHTZMH-UHFFFAOYSA-N 4-(3-methyl-4-oxo-2-phenylchromen-8-yl)-4-oxobutanoic acid Chemical compound O1C2=C(C(=O)CCC(O)=O)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 LJZBGFOFUHTZMH-UHFFFAOYSA-N 0.000 description 1
• RLPUCOGGXWIZIW-UHFFFAOYSA-N 4-(3-methyl-4-oxo-2-phenylchromen-8-yl)butanal Chemical compound O1C2=C(CCCC=O)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 RLPUCOGGXWIZIW-UHFFFAOYSA-N 0.000 description 1
• ZYHAYJMLLUJQSN-UHFFFAOYSA-N 4-[4-(2-methoxyphenyl)piperazin-1-yl]-n-methylbutan-1-amine Chemical compound C1CN(CCCCNC)CCN1C1=CC=CC=C1OC ZYHAYJMLLUJQSN-UHFFFAOYSA-N 0.000 description 1
• IKTNWWVLKHUQGL-UHFFFAOYSA-N 4-chloro-n-(3-methyl-4-oxo-2-phenylchromen-8-yl)butanamide Chemical compound O1C2=C(NC(=O)CCCCl)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 IKTNWWVLKHUQGL-UHFFFAOYSA-N 0.000 description 1
• CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 1
• SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
• UWWFTNNDTBZWRD-UHFFFAOYSA-N 4-oxo-2-phenylthiochromene-8-carboxylic acid Chemical compound OC(=O)C1=CC=CC(C(C=2)=O)=C1SC=2C1=CC=CC=C1 UWWFTNNDTBZWRD-UHFFFAOYSA-N 0.000 description 1
• WRXPTTJYUOVFEY-UHFFFAOYSA-N 4-oxo-3-phenylchromene-2-carbaldehyde Chemical compound C1(=CC=CC=C1)C1=C(OC2=C(C1=O)C=CC=C2)C=O WRXPTTJYUOVFEY-UHFFFAOYSA-N 0.000 description 1
• VZTQNMQYYOIJAB-UHFFFAOYSA-N 4-oxo-3-phenylchromene-8-carbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C2=O)=C1OC=C2C1=CC=CC=C1 VZTQNMQYYOIJAB-UHFFFAOYSA-N 0.000 description 1
• OLJXMAJPVRIDNZ-UHFFFAOYSA-N 4-oxo-3-phenylchromene-8-carboxylic acid Chemical compound OC(=O)C1=CC=CC(C2=O)=C1OC=C2C1=CC=CC=C1 OLJXMAJPVRIDNZ-UHFFFAOYSA-N 0.000 description 1
• SGOLZFYWLCQQEW-UHFFFAOYSA-N 4-oxochromene-8-carboxylic acid Chemical compound O1C=CC(=O)C2=C1C(C(=O)O)=CC=C2 SGOLZFYWLCQQEW-UHFFFAOYSA-N 0.000 description 1
• AOOZVQGGMFGGEE-UHFFFAOYSA-N 4-phenoxybenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1OC1=CC=CC=C1 AOOZVQGGMFGGEE-UHFFFAOYSA-N 0.000 description 1
• JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 description 1
• UTBULQCHEUWJNV-UHFFFAOYSA-N 4-phenylpiperidine Chemical compound C1CNCCC1C1=CC=CC=C1 UTBULQCHEUWJNV-UHFFFAOYSA-N 0.000 description 1
• ZSGATUFGSJXVOU-UHFFFAOYSA-N 5-amino-3-methyl-2-phenylchromen-4-one Chemical compound O1C2=CC=CC(N)=C2C(=O)C(C)=C1C1=CC=CC=C1 ZSGATUFGSJXVOU-UHFFFAOYSA-N 0.000 description 1
• XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
• JSNWZIONBZGCQB-UHFFFAOYSA-N 6-hydroxy-3-methyl-4-oxo-2-phenylchromene-8-carboxylic acid Chemical compound O1C2=C(C(O)=O)C=C(O)C=C2C(=O)C(C)=C1C1=CC=CC=C1 JSNWZIONBZGCQB-UHFFFAOYSA-N 0.000 description 1
• KLBMQTSRUOUVOW-UHFFFAOYSA-N 6-methoxy-3-methyl-4-oxo-2-phenylchromene-8-carboxylic acid Chemical compound CC=1C(=O)C2=CC(OC)=CC(C(O)=O)=C2OC=1C1=CC=CC=C1 KLBMQTSRUOUVOW-UHFFFAOYSA-N 0.000 description 1
• ZMPRIFFHZKYWRG-UHFFFAOYSA-N 7-methoxy-3-methyl-4-oxo-2-phenylchromene-8-carbaldehyde Chemical compound O=CC=1C(OC)=CC=C(C(C=2C)=O)C=1OC=2C1=CC=CC=C1 ZMPRIFFHZKYWRG-UHFFFAOYSA-N 0.000 description 1
• UTQVGSBXGWOWIE-UHFFFAOYSA-N 7-methoxy-3-methyl-4-oxo-2-phenylchromene-8-carboxylic acid Chemical compound OC(=O)C=1C(OC)=CC=C(C(C=2C)=O)C=1OC=2C1=CC=CC=C1 UTQVGSBXGWOWIE-UHFFFAOYSA-N 0.000 description 1
• OVEILYAHWHKZFD-UHFFFAOYSA-N 8-(2-azidoethoxy)-3-methyl-2-phenylchromen-4-one Chemical compound O1C2=C(OCCN=[N+]=[N-])C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 OVEILYAHWHKZFD-UHFFFAOYSA-N 0.000 description 1
• AQANSGZENKMQNT-UHFFFAOYSA-N 8-(2-bromoacetyl)-3-methyl-2-phenylchromen-4-one Chemical compound O1C2=C(C(=O)CBr)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 AQANSGZENKMQNT-UHFFFAOYSA-N 0.000 description 1
• KEYVDSDWLDIYKS-UHFFFAOYSA-N 8-(2-chloroethoxymethyl)-3-methyl-2-phenylchromen-4-one Chemical compound O1C2=C(COCCCl)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 KEYVDSDWLDIYKS-UHFFFAOYSA-N 0.000 description 1
• ZAGRFIUFTGGJIJ-UHFFFAOYSA-N 8-(2-chloroethylsulfanylmethyl)-3-methyl-2-phenylchromen-4-one Chemical compound O1C2=C(CSCCCl)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 ZAGRFIUFTGGJIJ-UHFFFAOYSA-N 0.000 description 1
• BYDPDLJDCRXHRI-UHFFFAOYSA-N 8-(2-chloroethylsulfonylmethyl)-3-methyl-2-phenylchromen-4-one Chemical compound O1C2=C(CS(=O)(=O)CCCl)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 BYDPDLJDCRXHRI-UHFFFAOYSA-N 0.000 description 1
• MXEFLTNOJZYEMA-UHFFFAOYSA-N 8-(2-hydroxyethoxymethyl)-3-methyl-2-phenylchromen-4-one Chemical compound O1C2=C(COCCO)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 MXEFLTNOJZYEMA-UHFFFAOYSA-N 0.000 description 1
• NNFAXBSULGQQNZ-UHFFFAOYSA-N 8-(3-chloropropoxy)-3-methyl-2-phenylchromen-4-one Chemical compound O1C2=C(OCCCCl)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 NNFAXBSULGQQNZ-UHFFFAOYSA-N 0.000 description 1
• QKKCOKDDGITZCB-UHFFFAOYSA-N 8-(3-chloropropyl)-3-methyl-2-phenylchromen-4-one Chemical compound CC1=C(OC2=C(C=CC=C2C1=O)CCCCl)C3=CC=CC=C3 QKKCOKDDGITZCB-UHFFFAOYSA-N 0.000 description 1
• ODXHBPOSVIDZLL-UHFFFAOYSA-N 8-(3-chloropropylsulfonyl)-3-methyl-2-phenylchromen-4-one Chemical compound O1C2=C(S(=O)(=O)CCCCl)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 ODXHBPOSVIDZLL-UHFFFAOYSA-N 0.000 description 1
• JRBYQSOISKCWIQ-UHFFFAOYSA-N 8-(4,4-dimethoxybutyl)-3-methyl-2-phenylchromen-4-one Chemical compound COC(OC)CCCC1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=CC=C1 JRBYQSOISKCWIQ-UHFFFAOYSA-N 0.000 description 1
• WMMOPONOBXFYNV-UHFFFAOYSA-N 8-(4-bromobutoxy)-3-methyl-2-phenylchromen-4-one Chemical compound O1C2=C(OCCCCBr)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 WMMOPONOBXFYNV-UHFFFAOYSA-N 0.000 description 1
• FBPJFOJRWGXVBF-UHFFFAOYSA-N 8-(4-chlorobutylsulfanyl)-3-methyl-2-phenylchromen-4-one Chemical compound O1C2=C(SCCCCCl)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 FBPJFOJRWGXVBF-UHFFFAOYSA-N 0.000 description 1
• LBFRNMMTAISPJT-UHFFFAOYSA-N 8-(4-chlorobutylsulfinyl)-3-methyl-2-phenylchromen-4-one Chemical compound O1C2=C(S(=O)CCCCCl)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 LBFRNMMTAISPJT-UHFFFAOYSA-N 0.000 description 1
• XEEWBQOUXXOAIX-UHFFFAOYSA-N 8-(4-chlorobutylsulfonyl)-3-methyl-2-phenylchromen-4-one Chemical compound O1C2=C(S(=O)(=O)CCCCCl)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 XEEWBQOUXXOAIX-UHFFFAOYSA-N 0.000 description 1
• ZPEYJHHUJVERNB-UHFFFAOYSA-N 8-(5-bromopentoxy)-3-methyl-2-phenylchromen-4-one Chemical compound O1C2=C(OCCCCCBr)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 ZPEYJHHUJVERNB-UHFFFAOYSA-N 0.000 description 1
• FLZSFGAYXHJKQH-UHFFFAOYSA-N 8-(aminomethyl)-3-methyl-2-phenylchromen-4-one Chemical compound O1C2=C(CN)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 FLZSFGAYXHJKQH-UHFFFAOYSA-N 0.000 description 1
• FCAGDICYOQTQNU-UHFFFAOYSA-N 8-(azidomethyl)-3-methyl-2-phenylchromen-4-one Chemical compound O1C2=C(CN=[N+]=[N-])C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 FCAGDICYOQTQNU-UHFFFAOYSA-N 0.000 description 1
• HORAOKMGKDQDED-UHFFFAOYSA-N 8-(chloromethyl)-3-methyl-2-phenylchromen-4-one Chemical compound O1C2=C(CCl)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 HORAOKMGKDQDED-UHFFFAOYSA-N 0.000 description 1
• IQBKHKVKJGFNCN-UHFFFAOYSA-N 8-(hydroxymethyl)-3-methyl-2-phenylchromen-4-one Chemical compound O1C2=C(CO)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 IQBKHKVKJGFNCN-UHFFFAOYSA-N 0.000 description 1
• QPJNKIXGCFVHAS-UHFFFAOYSA-N 8-[(2-hydroxyethylamino)methyl]-3-methyl-2-phenylchromen-4-one Chemical compound O1C2=C(CNCCO)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 QPJNKIXGCFVHAS-UHFFFAOYSA-N 0.000 description 1
• JEXDLZFCLORCJJ-UHFFFAOYSA-N 8-[1-ethoxy-2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-3-methyl-2-phenylchromen-4-one;hydrochloride Chemical compound Cl.C=1C=CC(C(C(C)=C(C=2C=CC=CC=2)O2)=O)=C2C=1C(OCC)CN(CC1)CCN1C1=CC=CC=C1OC JEXDLZFCLORCJJ-UHFFFAOYSA-N 0.000 description 1
• HBPLAZAJFLRFBR-UHFFFAOYSA-N 8-[1-hydroxy-2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-3-methyl-2-phenylchromen-4-one;hydrochloride Chemical compound Cl.COC1=CC=CC=C1N1CCN(CC(O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 HBPLAZAJFLRFBR-UHFFFAOYSA-N 0.000 description 1
• NTLZYQDLRGLDTE-UHFFFAOYSA-N 8-[1-hydroxy-2-[4-(2-methylphenyl)piperazin-1-yl]ethyl]-3-methyl-2-phenylchromen-4-one;hydrochloride Chemical compound Cl.CC1=CC=CC=C1N1CCN(CC(O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 NTLZYQDLRGLDTE-UHFFFAOYSA-N 0.000 description 1
• DWBUPKMHVQXYLV-UHFFFAOYSA-N 8-[1-hydroxy-4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-3-methyl-2-phenylchromen-4-one;hydrate;hydrochloride Chemical compound O.Cl.COC1=CC=CC=C1N1CCN(CCCC(O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 DWBUPKMHVQXYLV-UHFFFAOYSA-N 0.000 description 1
• VMNOFNVEELOTIA-UHFFFAOYSA-N 8-[2-[2-(2,6-dimethoxyphenoxy)ethylamino]ethoxy]-3-methyl-2-phenylchromen-4-one;hydrochloride Chemical compound Cl.COC1=CC=CC(OC)=C1OCCNCCOC1=CC=CC2=C1OC(C=1C=CC=CC=1)=C(C)C2=O VMNOFNVEELOTIA-UHFFFAOYSA-N 0.000 description 1
• KTBWSUHGVISLDE-UHFFFAOYSA-N 8-[2-[4-(2-ethoxyphenyl)piperazin-1-yl]-1-hydroxyethyl]-3-methyl-2-phenylchromen-4-one;hydrochloride Chemical compound Cl.CCOC1=CC=CC=C1N1CCN(CC(O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 KTBWSUHGVISLDE-UHFFFAOYSA-N 0.000 description 1
• BWNRKYORONVLQP-UHFFFAOYSA-N 8-[2-[4-(2-ethoxyphenyl)piperazin-1-yl]acetyl]-3-methyl-2-phenylchromen-4-one;hydrochloride Chemical compound Cl.CCOC1=CC=CC=C1N1CCN(CC(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 BWNRKYORONVLQP-UHFFFAOYSA-N 0.000 description 1
• FXFXMKCEDVBSCK-UHFFFAOYSA-N 8-[2-[4-(2-methoxyphenyl)piperazin-1-yl]acetyl]-3-methyl-2-phenylchromen-4-one;hydrochloride Chemical compound Cl.COC1=CC=CC=C1N1CCN(CC(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 FXFXMKCEDVBSCK-UHFFFAOYSA-N 0.000 description 1
• CNEKREHSMPAMOT-UHFFFAOYSA-N 8-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethoxy]-3-methyl-2-phenylchromen-4-one;hydrate;hydrochloride Chemical compound O.Cl.COC1=CC=CC=C1N1CCN(CCOC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 CNEKREHSMPAMOT-UHFFFAOYSA-N 0.000 description 1
• LQUBPSPGBAYDQX-UHFFFAOYSA-N 8-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethoxymethyl]-3-methyl-2-phenylchromen-4-one;dihydrochloride Chemical compound Cl.Cl.COC1=CC=CC=C1N1CCN(CCOCC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 LQUBPSPGBAYDQX-UHFFFAOYSA-N 0.000 description 1
• PCZYLYPTNAIDIF-UHFFFAOYSA-N 8-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethylamino]-3-methyl-2-phenylchromen-4-one;dihydrochloride Chemical compound Cl.Cl.COC1=CC=CC=C1N1CCN(CCNC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 PCZYLYPTNAIDIF-UHFFFAOYSA-N 0.000 description 1
• PFSGMIQTZYGVAX-UHFFFAOYSA-N 8-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethylsulfanylmethyl]-3-methyl-2-phenylchromen-4-one;hydrochloride Chemical compound Cl.COC1=CC=CC=C1N1CCN(CCSCC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 PFSGMIQTZYGVAX-UHFFFAOYSA-N 0.000 description 1
• UEVUYQDBNPGDNB-UHFFFAOYSA-N 8-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethylsulfinylmethyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCS(=O)CC=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 UEVUYQDBNPGDNB-UHFFFAOYSA-N 0.000 description 1
• IASVBHWDCMHBTQ-UHFFFAOYSA-N 8-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethylsulfonylmethyl]-3-methyl-2-phenylchromen-4-one;hydrochloride Chemical compound Cl.COC1=CC=CC=C1N1CCN(CCS(=O)(=O)CC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 IASVBHWDCMHBTQ-UHFFFAOYSA-N 0.000 description 1
• XXRIILODNJVAMT-UHFFFAOYSA-N 8-[2-hydroxy-3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy]-3-methyl-2-phenylchromen-4-one;hydrochloride Chemical compound Cl.COC1=CC=CC=C1N1CCN(CC(O)COC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 XXRIILODNJVAMT-UHFFFAOYSA-N 0.000 description 1
• WZSLGOHWOMQGBJ-UHFFFAOYSA-N 8-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propanoyl]-3-methyl-2-phenylchromen-4-one;hydrochloride Chemical compound Cl.COC1=CC=CC=C1N1CCN(CCC(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 WZSLGOHWOMQGBJ-UHFFFAOYSA-N 0.000 description 1
• FOQUKURSTSTWCQ-UHFFFAOYSA-N 8-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propylsulfonyl]-3-methyl-2-phenylchromen-4-one;hydrochloride Chemical compound Cl.COC1=CC=CC=C1N1CCN(CCCS(=O)(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 FOQUKURSTSTWCQ-UHFFFAOYSA-N 0.000 description 1
• JNMSQZLCYSVUBX-UHFFFAOYSA-N 8-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butylamino]-3-methyl-2-phenylchromen-4-one;hydrochloride Chemical compound Cl.COC1=CC=CC=C1N1CCN(CCCCNC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 JNMSQZLCYSVUBX-UHFFFAOYSA-N 0.000 description 1
• AQGTZNUGGNTJTH-UHFFFAOYSA-N 8-[5-[4-(2-methoxyphenyl)piperazin-1-yl]pentoxy]-3-methyl-2-phenylchromen-4-one;hydrochloride Chemical compound Cl.COC1=CC=CC=C1N1CCN(CCCCCOC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 AQGTZNUGGNTJTH-UHFFFAOYSA-N 0.000 description 1
• WBWMQLSFKCZZKH-UHFFFAOYSA-N 8-[[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl-methylamino]methyl]-3-methyl-2-phenylchromen-4-one Chemical compound COC1=CC=CC=C1N1CCN(CCN(C)CC=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 WBWMQLSFKCZZKH-UHFFFAOYSA-N 0.000 description 1
• ULMUPCSUXPMXKI-UHFFFAOYSA-N 8-[[2-chloroethyl(methyl)amino]methyl]-3-methyl-2-phenylchromen-4-one Chemical compound ClCCN(C)CC1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=CC=C1 ULMUPCSUXPMXKI-UHFFFAOYSA-N 0.000 description 1
• VZDFEEUHCAQOBQ-UHFFFAOYSA-N 8-acetyl-3-methyl-2-phenylchromen-4-one Chemical compound CC(=O)C1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=CC=C1 VZDFEEUHCAQOBQ-UHFFFAOYSA-N 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
• 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
• 229910000497 Amalgam Inorganic materials 0.000 description 1
• DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
• FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 1
• YTYNJTXPWPEDGC-UHFFFAOYSA-N C1CCN(C(=O)C1)N2C3=CC=CC=C3NC2=O Chemical compound C1CCN(C(=O)C1)N2C3=CC=CC=C3NC2=O YTYNJTXPWPEDGC-UHFFFAOYSA-N 0.000 description 1
• XDGHQLHTSSFROF-UHFFFAOYSA-N CC1=C(OC2=C(C1=O)C=CC=C2C(CCN3CCN(CC3)C4=CC=CC=C4OC)N)C5=CC=CC=C5 Chemical compound CC1=C(OC2=C(C1=O)C=CC=C2C(CCN3CCN(CC3)C4=CC=CC=C4OC)N)C5=CC=CC=C5 XDGHQLHTSSFROF-UHFFFAOYSA-N 0.000 description 1
• SALSCDVVELEJAC-UHFFFAOYSA-N CC1=C(OC2=C(C1=O)C=CC=C2SCCCC3CN(CCN3)C4=CC=CC=C4OC)C5=CC=CC=C5 Chemical compound CC1=C(OC2=C(C1=O)C=CC=C2SCCCC3CN(CCN3)C4=CC=CC=C4OC)C5=CC=CC=C5 SALSCDVVELEJAC-UHFFFAOYSA-N 0.000 description 1
• XVMKOHGCLNZBTG-UHFFFAOYSA-N CC1C=C(C=CC1=O)C2=C(CC3=CC=CC=C3O2)C(=O)NCCCl Chemical compound CC1C=C(C=CC1=O)C2=C(CC3=CC=CC=C3O2)C(=O)NCCCl XVMKOHGCLNZBTG-UHFFFAOYSA-N 0.000 description 1
• XYAGDRZEVXLKDE-UHFFFAOYSA-N CCC(CC1=C2C(=CC=C1)OC(=C(C2=O)C)C3=CC=CC=C3)C4OCCCO4 Chemical compound CCC(CC1=C2C(=CC=C1)OC(=C(C2=O)C)C3=CC=CC=C3)C4OCCCO4 XYAGDRZEVXLKDE-UHFFFAOYSA-N 0.000 description 1
• LQTQXAXJIABTNK-UHFFFAOYSA-N COC1=CC=CC=C1N2CCN(CC2)C(CCCN)C(=O)C(F)(F)F Chemical compound COC1=CC=CC=C1N2CCN(CC2)C(CCCN)C(=O)C(F)(F)F LQTQXAXJIABTNK-UHFFFAOYSA-N 0.000 description 1
• QONVEYXOPKREFC-UHFFFAOYSA-N CS(=O)(=O)O.C(C)NC(NC1=CC=CC2=C1C(C(=C(O2)C2=CC=CC=C2)C)=O)=O Chemical compound CS(=O)(=O)O.C(C)NC(NC1=CC=CC2=C1C(C(=C(O2)C2=CC=CC=C2)C)=O)=O QONVEYXOPKREFC-UHFFFAOYSA-N 0.000 description 1
• RZDCMOVESXCHBM-UHFFFAOYSA-N Cc1ccc(cc1)S(=O)(=O)OC1COc2ccccc2O1 Chemical compound Cc1ccc(cc1)S(=O)(=O)OC1COc2ccccc2O1 RZDCMOVESXCHBM-UHFFFAOYSA-N 0.000 description 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
• XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
• SVGZHXKLYSCJRE-UHFFFAOYSA-N ClCCCN(C(=O)C1=CC=CC=2C(C(=C(OC21)C2=CC=CC=C2)C)=O)CCC Chemical compound ClCCCN(C(=O)C1=CC=CC=2C(C(=C(OC21)C2=CC=CC=C2)C)=O)CCC SVGZHXKLYSCJRE-UHFFFAOYSA-N 0.000 description 1
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
• 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
• FVIGODVHAVLZOO-UHFFFAOYSA-N Dixanthogen Chemical compound CCOC(=S)SSC(=S)OCC FVIGODVHAVLZOO-UHFFFAOYSA-N 0.000 description 1
• BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
• GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 1
• 206010020880 Hypertrophy Diseases 0.000 description 1
• 208000001953 Hypotension Diseases 0.000 description 1
• 206010022998 Irritability Diseases 0.000 description 1
• 229910010084 LiAlH4 Inorganic materials 0.000 description 1
• 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
• 238000006683 Mannich reaction Methods 0.000 description 1
• 238000007126 N-alkylation reaction Methods 0.000 description 1
• 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• 101150003085 Pdcl gene Proteins 0.000 description 1
• WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
• 229910000564 Raney nickel Inorganic materials 0.000 description 1
• 101000650578 Salmonella phage P22 Regulatory protein C3 Proteins 0.000 description 1
• 239000002262 Schiff base Substances 0.000 description 1
• 150000004753 Schiff bases Chemical class 0.000 description 1
• 229910020346 SiS 2 Inorganic materials 0.000 description 1
• BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
• 239000004133 Sodium thiosulphate Substances 0.000 description 1
• 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
• 101001040920 Triticum aestivum Alpha-amylase inhibitor 0.28 Proteins 0.000 description 1
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
• 206010046543 Urinary incontinence Diseases 0.000 description 1
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
• XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
• VCNNRCZHTSSCCH-UHFFFAOYSA-N [1-[4-(2-methoxyphenyl)piperazin-1-yl]-2-methylpropan-2-yl] 3-methyl-4-oxo-2-phenylchromene-8-carboxylate;dihydrochloride Chemical compound Cl.Cl.COC1=CC=CC=C1N1CCN(CC(C)(C)OC(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 VCNNRCZHTSSCCH-UHFFFAOYSA-N 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-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
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
• 238000005903 acid hydrolysis reaction Methods 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• 150000001263 acyl chlorides Chemical class 0.000 description 1
• 230000010933 acylation Effects 0.000 description 1
• 238000005917 acylation reaction Methods 0.000 description 1
• 230000001800 adrenalinergic effect Effects 0.000 description 1
• 150000001335 aliphatic alkanes Chemical class 0.000 description 1
• 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
• 150000008041 alkali metal carbonates Chemical class 0.000 description 1
• 239000012670 alkaline solution Substances 0.000 description 1
• 150000008051 alkyl sulfates Chemical class 0.000 description 1
• 230000029936 alkylation Effects 0.000 description 1
• 238000005804 alkylation reaction Methods 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 150000001413 amino acids Chemical class 0.000 description 1
• 125000004103 aminoalkyl group Chemical group 0.000 description 1
• 229910021529 ammonia Inorganic materials 0.000 description 1
• 229960003116 amyl nitrite Drugs 0.000 description 1
• 150000008064 anhydrides Chemical class 0.000 description 1
• 239000005557 antagonist Substances 0.000 description 1
• 230000001466 anti-adreneric effect Effects 0.000 description 1
• 239000002246 antineoplastic agent Substances 0.000 description 1
• 229940041181 antineoplastic drug Drugs 0.000 description 1
• 229940000488 arsenic acid Drugs 0.000 description 1
• UIJGNTRUPZPVNG-UHFFFAOYSA-N benzenecarbothioic s-acid Chemical compound SC(=O)C1=CC=CC=C1 UIJGNTRUPZPVNG-UHFFFAOYSA-N 0.000 description 1
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
• CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 1
• FKPSBYZGRQJIMO-UHFFFAOYSA-M benzyl(triethyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC1=CC=CC=C1 FKPSBYZGRQJIMO-UHFFFAOYSA-M 0.000 description 1
• 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
• 108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
• 230000004071 biological effect Effects 0.000 description 1
• AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 1
• 230000000903 blocking effect Effects 0.000 description 1
• 230000036772 blood pressure Effects 0.000 description 1
• 210000004204 blood vessel Anatomy 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
• HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
• 150000001718 carbodiimides Chemical class 0.000 description 1
• 150000001722 carbon compounds Chemical class 0.000 description 1
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
• KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
• 239000007810 chemical reaction solvent Substances 0.000 description 1
• FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
• 229940061627 chloromethyl methyl ether Drugs 0.000 description 1
• IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
• 238000004587 chromatography analysis Methods 0.000 description 1
• 239000010941 cobalt Substances 0.000 description 1
• 229910017052 cobalt Inorganic materials 0.000 description 1
• GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
• 229910052802 copper Inorganic materials 0.000 description 1
• 239000010949 copper Substances 0.000 description 1
• 150000001879 copper Chemical class 0.000 description 1
• JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
• OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
• 125000004093 cyano group Chemical group *C#N 0.000 description 1
• UCDHYFZYUGDETN-UHFFFAOYSA-N cyanophosphonic acid Chemical compound OP(O)(=O)C#N UCDHYFZYUGDETN-UHFFFAOYSA-N 0.000 description 1
• RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
• 238000006114 decarboxylation reaction Methods 0.000 description 1
• 230000018044 dehydration Effects 0.000 description 1
• 238000006297 dehydration reaction Methods 0.000 description 1
• 238000006356 dehydrogenation reaction Methods 0.000 description 1
• 230000003111 delayed effect Effects 0.000 description 1
• RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 1
• 239000012954 diazonium Substances 0.000 description 1
• 150000001989 diazonium salts Chemical class 0.000 description 1
• 229940117389 dichlorobenzene Drugs 0.000 description 1
• 238000007865 diluting Methods 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• OAGOUCJGXNLJNL-UHFFFAOYSA-N dimethylcyanamide Chemical compound CN(C)C#N OAGOUCJGXNLJNL-UHFFFAOYSA-N 0.000 description 1
• VDCSGNNYCFPWFK-UHFFFAOYSA-N diphenylsilane Chemical compound C=1C=CC=CC=1[SiH2]C1=CC=CC=C1 VDCSGNNYCFPWFK-UHFFFAOYSA-N 0.000 description 1
• 230000008034 disappearance Effects 0.000 description 1
• 238000009826 distribution Methods 0.000 description 1
• 239000000428 dust Substances 0.000 description 1
• 238000003379 elimination reaction Methods 0.000 description 1
• 125000003700 epoxy group Chemical group 0.000 description 1
• 230000032050 esterification Effects 0.000 description 1
• 238000006266 etherification reaction Methods 0.000 description 1
• 150000002170 ethers Chemical class 0.000 description 1
• DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
• NYKYMICIVFDUCX-UHFFFAOYSA-N ethyl 2-(2,2-dimethylpropanoyloxy)-3-propanoylbenzoate Chemical compound CCOC(=O)C1=CC=CC(C(=O)CC)=C1OC(=O)C(C)(C)C NYKYMICIVFDUCX-UHFFFAOYSA-N 0.000 description 1
• VHMNHMSQLODNNN-UHFFFAOYSA-N ethyl 2-(4-benzoylphenyl)-3-methyl-4-oxochromene-8-carboxylate Chemical compound CCOC(=O)C1=CC=CC(C(C=2C)=O)=C1OC=2C(C=C1)=CC=C1C(=O)C1=CC=CC=C1 VHMNHMSQLODNNN-UHFFFAOYSA-N 0.000 description 1
• YFCKNQKBASOTEI-UHFFFAOYSA-N ethyl 2-(4-fluorophenyl)-3-methyl-4-oxochromene-8-carboxylate Chemical compound CCOC(=O)C1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=C(F)C=C1 YFCKNQKBASOTEI-UHFFFAOYSA-N 0.000 description 1
• OSXMYHFVVNIXNF-UHFFFAOYSA-N ethyl 2-(furan-2-yl)-3-methyl-4-oxochromene-8-carboxylate Chemical compound CCOC(=O)C1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=CO1 OSXMYHFVVNIXNF-UHFFFAOYSA-N 0.000 description 1
• WXGXCZKSPVWVGY-UHFFFAOYSA-N ethyl 2-benzoyl-3-ethyl-1-benzofuran-7-carboxylate Chemical compound O1C=2C(C(=O)OCC)=CC=CC=2C(CC)=C1C(=O)C1=CC=CC=C1 WXGXCZKSPVWVGY-UHFFFAOYSA-N 0.000 description 1
• BAOBBAUWUCLYIS-UHFFFAOYSA-N ethyl 2-cyclohexyl-3-methyl-4-oxochromene-8-carboxylate Chemical compound CCOC(=O)C1=CC=CC(C(C=2C)=O)=C1OC=2C1CCCCC1 BAOBBAUWUCLYIS-UHFFFAOYSA-N 0.000 description 1
• KGHJIPKLQZWGQO-OUKQBFOZSA-N ethyl 2-hydroxy-3-[(e)-2-methyl-4-phenylbut-3-enoyl]benzoate Chemical compound CCOC(=O)C1=CC=CC(C(=O)C(C)\C=C\C=2C=CC=CC=2)=C1O KGHJIPKLQZWGQO-OUKQBFOZSA-N 0.000 description 1
• NARWPOACABXCRU-UHFFFAOYSA-N ethyl 2-tert-butyl-3-methyl-4-oxochromene-8-carboxylate Chemical compound O1C(C(C)(C)C)=C(C)C(=O)C2=C1C(C(=O)OCC)=CC=C2 NARWPOACABXCRU-UHFFFAOYSA-N 0.000 description 1
• XBRLIAGHHNZULX-UHFFFAOYSA-N ethyl 3-(acetyloxymethyl)-4-oxo-2-phenylchromene-8-carboxylate Chemical compound CCOC(=O)C1=CC=CC(C(C=2COC(C)=O)=O)=C1OC=2C1=CC=CC=C1 XBRLIAGHHNZULX-UHFFFAOYSA-N 0.000 description 1
• COUUOUUKFWJVDR-UHFFFAOYSA-N ethyl 3-[4-(furan-2-yl)-4-oxobutanoyl]-2-hydroxybenzoate Chemical compound CCOC(=O)C1=CC=CC(C(=O)CCC(=O)C=2OC=CC=2)=C1O COUUOUUKFWJVDR-UHFFFAOYSA-N 0.000 description 1
• FQELDVYCJBSHDQ-UHFFFAOYSA-N ethyl 3-acetyl-2-hydroxybenzoate Chemical compound CCOC(=O)C1=CC=CC(C(C)=O)=C1O FQELDVYCJBSHDQ-UHFFFAOYSA-N 0.000 description 1
• UPXUJDRBSBNGJB-UHFFFAOYSA-N ethyl 3-methyl-2-(4-nitrophenyl)-4-oxochromene-8-carboxylate Chemical compound CCOC(=O)C1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=C([N+]([O-])=O)C=C1 UPXUJDRBSBNGJB-UHFFFAOYSA-N 0.000 description 1
• PSRHCZBTKVLUPX-UHFFFAOYSA-N ethyl 3-methyl-4-oxo-2-(4-phenylphenyl)chromene-8-carboxylate Chemical compound CCOC(=O)C1=CC=CC(C(C=2C)=O)=C1OC=2C(C=C1)=CC=C1C1=CC=CC=C1 PSRHCZBTKVLUPX-UHFFFAOYSA-N 0.000 description 1
• CUWBHENXTOASMK-UHFFFAOYSA-N ethyl 3-methyl-4-oxo-2-[4-(trifluoromethyl)phenyl]chromene-8-carboxylate Chemical compound CCOC(=O)C1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=C(C(F)(F)F)C=C1 CUWBHENXTOASMK-UHFFFAOYSA-N 0.000 description 1
• NFRGNMIIGIZYDL-UHFFFAOYSA-N ethyl 3-methyl-4-oxo-2-phenylchromene-8-carboxylate Chemical compound CCOC(=O)C1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=CC=C1 NFRGNMIIGIZYDL-UHFFFAOYSA-N 0.000 description 1
• OFERXBKVJATDJS-UHFFFAOYSA-N ethyl 3-methyl-4-oxo-2-thiophen-2-ylchromene-8-carboxylate Chemical compound CCOC(=O)C1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=CS1 OFERXBKVJATDJS-UHFFFAOYSA-N 0.000 description 1
• CBJKVHPSDMKKGL-UHFFFAOYSA-N ethyl 4-oxochromene-8-carboxylate Chemical compound O1C=CC(=O)C2=C1C(C(=O)OCC)=CC=C2 CBJKVHPSDMKKGL-UHFFFAOYSA-N 0.000 description 1
• 125000004494 ethyl ester group Chemical group 0.000 description 1
• PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
• 238000007429 general method Methods 0.000 description 1
• GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
• 150000004678 hydrides Chemical class 0.000 description 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
• 229940071870 hydroiodic acid Drugs 0.000 description 1
• 230000002209 hydrophobic effect Effects 0.000 description 1
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 1
• 150000002440 hydroxy compounds Chemical class 0.000 description 1
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
• QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
• 230000036543 hypotension Effects 0.000 description 1
• 239000012442 inert solvent Substances 0.000 description 1
• 229910010272 inorganic material Inorganic materials 0.000 description 1
• 239000011147 inorganic material Substances 0.000 description 1
• 229910052500 inorganic mineral Inorganic materials 0.000 description 1
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
• 229910052742 iron Inorganic materials 0.000 description 1
• 239000012948 isocyanate Substances 0.000 description 1
• 150000002513 isocyanates Chemical class 0.000 description 1
• 150000002540 isothiocyanates Chemical class 0.000 description 1
• 150000002576 ketones Chemical class 0.000 description 1
• CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
• 239000003446 ligand Substances 0.000 description 1
• 230000000670 limiting effect Effects 0.000 description 1
• YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
• 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
• 239000011777 magnesium Substances 0.000 description 1
• 229910052749 magnesium Inorganic materials 0.000 description 1
• USSBDBZGEDUBHE-UHFFFAOYSA-L magnesium;2-oxidooxycarbonylbenzoate Chemical compound [Mg+2].[O-]OC(=O)C1=CC=CC=C1C([O-])=O USSBDBZGEDUBHE-UHFFFAOYSA-L 0.000 description 1
• 239000000463 material Substances 0.000 description 1
• 230000004060 metabolic process Effects 0.000 description 1
• 229910052987 metal hydride Inorganic materials 0.000 description 1
• 150000004681 metal hydrides Chemical class 0.000 description 1
• 229910044991 metal oxide Inorganic materials 0.000 description 1
• 150000004706 metal oxides Chemical class 0.000 description 1
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
• BOWRWIGIDPOMQH-UHFFFAOYSA-N methanesulfonic acid;3-[4-(2-methoxyphenyl)piperazin-1-yl]-n-methyl-n-(3-methyl-4-oxo-2-phenylchromen-8-yl)propanamide Chemical compound CS(O)(=O)=O.COC1=CC=CC=C1N1CCN(CCC(=O)N(C)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 BOWRWIGIDPOMQH-UHFFFAOYSA-N 0.000 description 1
• MJVCLNSBBDXFMT-UHFFFAOYSA-N methanesulfonic acid;8-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butanoyl]-3-methyl-2-phenylchromen-4-one Chemical compound CS(O)(=O)=O.COC1=CC=CC=C1N1CCN(CCCC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 MJVCLNSBBDXFMT-UHFFFAOYSA-N 0.000 description 1
• WYXXOFSNWPXNLP-UHFFFAOYSA-N methanesulfonic acid;8-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-3-methyl-2-phenylchromen-4-one Chemical compound CS(O)(=O)=O.COC1=CC=CC=C1N1CCN(CCCCC=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 WYXXOFSNWPXNLP-UHFFFAOYSA-N 0.000 description 1
• NZBUQWLFUNKDGI-UHFFFAOYSA-N methanesulfonic acid;n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-4-oxo-3-phenylchromene-8-carboxamide Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.COC1=CC=CC=C1N1CCN(CCCNC(=O)C=2C3=C(C(C(C=4C=CC=CC=4)=CO3)=O)C=CC=2)CC1 NZBUQWLFUNKDGI-UHFFFAOYSA-N 0.000 description 1
• YMHYWBXWJCEHIP-UHFFFAOYSA-N methanesulfonic acid;n-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound CS(O)(=O)=O.COC1=CC=CC=C1N1CCN(CCCCNC(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 YMHYWBXWJCEHIP-UHFFFAOYSA-N 0.000 description 1
• KLKJSLJQSMTJBV-UHFFFAOYSA-N methanesulfonic acid;n-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-3-methyl-4-oxo-2-phenylchromene-8-sulfonamide Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.COC1=CC=CC=C1N1CCN(CCCCNS(=O)(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 KLKJSLJQSMTJBV-UHFFFAOYSA-N 0.000 description 1
• BDPIZWCNTCVHAJ-UHFFFAOYSA-N methyl 2-(4-methylbenzoyl)oxy-3-propanoylbenzoate Chemical compound CCC(=O)C1=CC=CC(C(=O)OC)=C1OC(=O)C1=CC=C(C)C=C1 BDPIZWCNTCVHAJ-UHFFFAOYSA-N 0.000 description 1
• UFGVWANOISVHGQ-UHFFFAOYSA-N methyl 2-hydroxy-3-propanoylbenzoate Chemical compound CCC(=O)C1=CC=CC(C(=O)OC)=C1O UFGVWANOISVHGQ-UHFFFAOYSA-N 0.000 description 1
• BAQGCWNPCFABAY-UHFFFAOYSA-N methyl 2-sulfanylbenzoate Chemical compound COC(=O)C1=CC=CC=C1S BAQGCWNPCFABAY-UHFFFAOYSA-N 0.000 description 1
• ZTIFDLYMYBXRLT-UHFFFAOYSA-N methyl 3-methyl-2-(4-methylphenyl)-4-oxochromene-8-carboxylate Chemical compound COC(=O)C1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=C(C)C=C1 ZTIFDLYMYBXRLT-UHFFFAOYSA-N 0.000 description 1
• MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 1
• NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
• 238000007069 methylation reaction Methods 0.000 description 1
• 230000027939 micturition Effects 0.000 description 1
• 235000010755 mineral Nutrition 0.000 description 1
• 239000011707 mineral Substances 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
• 235000019799 monosodium phosphate Nutrition 0.000 description 1
• 239000012452 mother liquor Substances 0.000 description 1
• QAXZWHGWYSJAEI-UHFFFAOYSA-N n,n-dimethylformamide;ethanol Chemical compound CCO.CN(C)C=O QAXZWHGWYSJAEI-UHFFFAOYSA-N 0.000 description 1
• WMEXLJWQUOXKOU-UHFFFAOYSA-N n-(2-chloroethyl)-n,3-dimethyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound ClCCN(C)C(=O)C1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=CC=C1 WMEXLJWQUOXKOU-UHFFFAOYSA-N 0.000 description 1
• GOLLEUIGUXTIQM-UHFFFAOYSA-N n-(2-chloroethyl)-n-[(3-methyl-4-oxo-2-phenylchromen-8-yl)methyl]acetamide Chemical compound ClCCN(C(=O)C)CC1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=CC=C1 GOLLEUIGUXTIQM-UHFFFAOYSA-N 0.000 description 1
• PMIXTRZLOQRROF-UHFFFAOYSA-N n-(2-hydroxyethyl)-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound O1C2=C(C(=O)NCCO)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 PMIXTRZLOQRROF-UHFFFAOYSA-N 0.000 description 1
• XLZOIXODTOCDJA-UHFFFAOYSA-N n-(2-hydroxyethyl)-n,3-dimethyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound OCCN(C)C(=O)C1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=CC=C1 XLZOIXODTOCDJA-UHFFFAOYSA-N 0.000 description 1
• MTMHCUYAIGMXDZ-UHFFFAOYSA-N n-(2-hydroxyethyl)-n,3-dimethyl-4-oxo-2-phenylchromene-8-sulfonamide Chemical compound OCCN(C)S(=O)(=O)C1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=CC=C1 MTMHCUYAIGMXDZ-UHFFFAOYSA-N 0.000 description 1
• ZPUWOEPNUWNPHN-UHFFFAOYSA-N n-(2-hydroxyethyl)-n-[(3-methyl-4-oxo-2-phenylchromen-8-yl)methyl]acetamide Chemical compound OCCN(C(=O)C)CC1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=CC=C1 ZPUWOEPNUWNPHN-UHFFFAOYSA-N 0.000 description 1
• JICPGKVAZANWHF-UHFFFAOYSA-N n-(3-aminopropyl)-3-methyl-4-oxo-2-phenylchromene-8-carboxamide;hydrochloride Chemical compound Cl.O1C2=C(C(=O)NCCCN)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 JICPGKVAZANWHF-UHFFFAOYSA-N 0.000 description 1
• FYMVNVJQSHEMLP-UHFFFAOYSA-N n-(3-hydroxypropyl)-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound O1C2=C(C(=O)NCCCO)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 FYMVNVJQSHEMLP-UHFFFAOYSA-N 0.000 description 1
• ARIWQLAPCTWAQV-UHFFFAOYSA-N n-(3-methyl-4-oxo-2-phenylchromen-8-yl)prop-2-enamide Chemical compound O1C2=C(NC(=O)C=C)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 ARIWQLAPCTWAQV-UHFFFAOYSA-N 0.000 description 1
• QHADQZZLTAUQAF-UHFFFAOYSA-N n-[(3-methyl-4-oxo-2-phenylchromen-8-yl)methyl]ethenesulfonamide Chemical compound O1C2=C(CNS(=O)(=O)C=C)C=CC=C2C(=O)C(C)=C1C1=CC=CC=C1 QHADQZZLTAUQAF-UHFFFAOYSA-N 0.000 description 1
• DDFYCVRUAGUKHQ-UHFFFAOYSA-N n-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-3-methyl-4-oxo-2-phenylchromene-8-sulfonamide;hydrochloride Chemical compound Cl.COC1=CC=CC=C1N1CCN(CCNS(=O)(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 DDFYCVRUAGUKHQ-UHFFFAOYSA-N 0.000 description 1
• LDIDRTUDRVHVFR-UHFFFAOYSA-N n-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-n,3-dimethyl-4-oxo-2-phenylchromene-8-carboxamide;hydrochloride Chemical compound Cl.COC1=CC=CC=C1N1CCN(CCN(C)C(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 LDIDRTUDRVHVFR-UHFFFAOYSA-N 0.000 description 1
• GCYKLJGANUUQML-UHFFFAOYSA-N n-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-n,3-dimethyl-4-oxo-2-phenylchromene-8-sulfonamide;hydrochloride Chemical compound Cl.COC1=CC=CC=C1N1CCN(CCN(C)S(=O)(=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 GCYKLJGANUUQML-UHFFFAOYSA-N 0.000 description 1
• XWPVUNQTLDQLFZ-UHFFFAOYSA-N n-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-n-[(3-methyl-4-oxo-2-phenylchromen-8-yl)methyl]acetamide;hydrochloride Chemical compound Cl.COC1=CC=CC=C1N1CCN(CCN(CC=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)C(C)=O)CC1 XWPVUNQTLDQLFZ-UHFFFAOYSA-N 0.000 description 1
• VPBUPEOPJDZGJV-UHFFFAOYSA-N n-[3-(4,4-diphenylpiperidin-1-yl)propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide;methanesulfonic acid Chemical compound CS(O)(=O)=O.C1=CC=C2C(=O)C(C)=C(C=3C=CC=CC=3)OC2=C1C(=O)NCCCN(CC1)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 VPBUPEOPJDZGJV-UHFFFAOYSA-N 0.000 description 1
• KFZGEMWKOVXMEE-UHFFFAOYSA-N n-[3-[2-(2-methoxyphenoxy)ethyl-methylamino]propyl]-3-methyl-4-oxo-2-phenylchromene-8-carboxamide;hydrochloride Chemical compound Cl.COC1=CC=CC=C1OCCN(C)CCCNC(=O)C1=CC=CC2=C1OC(C=1C=CC=CC=1)=C(C)C2=O KFZGEMWKOVXMEE-UHFFFAOYSA-N 0.000 description 1
• HZYUSLIEQZRMOS-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-3-methyl-n-(oxan-2-yloxy)-4-oxo-2-phenylchromene-8-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(CCCN(OC2OCCCC2)C(=O)C=2C3=C(C(C(C)=C(O3)C=3C=CC=CC=3)=O)C=CC=2)CC1 HZYUSLIEQZRMOS-UHFFFAOYSA-N 0.000 description 1
• PRBDIUDXSSGNFR-UHFFFAOYSA-N n-[3-[4-(2-methoxyphenyl)piperazin-1-yl]propyl]-n-(3-methyl-4-oxo-2-phenylchromen-8-yl)acetamide;hydrate;hydrochloride Chemical compound O.Cl.COC1=CC=CC=C1N1CCN(CCCN(C(C)=O)C=2C3=C(C(C(C)=C(C=4C=CC=CC=4)O3)=O)C=CC=2)CC1 PRBDIUDXSSGNFR-UHFFFAOYSA-N 0.000 description 1
• QZFOKLPWYHXGFN-UHFFFAOYSA-N n-acetyl-3-methyl-4-oxo-2-phenylchromene-8-carboxamide Chemical compound CC(=O)NC(=O)C1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=CC=C1 QZFOKLPWYHXGFN-UHFFFAOYSA-N 0.000 description 1
• MXBFSAYTTZBUBY-UHFFFAOYSA-N n-chlorohydroxylamine Chemical compound ONCl MXBFSAYTTZBUBY-UHFFFAOYSA-N 0.000 description 1
• LKPFBGKZCCBZDK-UHFFFAOYSA-N n-hydroxypiperidine Chemical compound ON1CCCCC1 LKPFBGKZCCBZDK-UHFFFAOYSA-N 0.000 description 1
• MTOBMVSFIUMGHO-UHFFFAOYSA-N n-methyl-n-(3-methyl-4-oxo-2-phenylchromen-8-yl)prop-2-enamide Chemical compound C=CC(=O)N(C)C1=CC=CC(C(C=2C)=O)=C1OC=2C1=CC=CC=C1 MTOBMVSFIUMGHO-UHFFFAOYSA-N 0.000 description 1
• QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
• 230000000269 nucleophilic effect Effects 0.000 description 1
• NLXXVSKHVGDQAT-UHFFFAOYSA-N o-(oxan-2-yl)hydroxylamine Chemical compound NOC1CCCCO1 NLXXVSKHVGDQAT-UHFFFAOYSA-N 0.000 description 1
• WDBXHQTZERVTGM-UHFFFAOYSA-N o-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]hydroxylamine;hydrochloride Chemical compound Cl.COC1=CC=CC=C1N1CCN(CCON)CC1 WDBXHQTZERVTGM-UHFFFAOYSA-N 0.000 description 1
• 230000000414 obstructive effect Effects 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 150000002894 organic compounds Chemical class 0.000 description 1
• 238000006053 organic reaction Methods 0.000 description 1
• 239000012285 osmium tetroxide Substances 0.000 description 1
• 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
• MMKQSIQNDMIVIN-UHFFFAOYSA-N oxido-(oxido(dioxo)chromio)oxy-dioxochromium;tetrabutylazanium Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC.CCCC[N+](CCCC)(CCCC)CCCC MMKQSIQNDMIVIN-UHFFFAOYSA-N 0.000 description 1
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
• 235000011837 pasties Nutrition 0.000 description 1
• 230000037361 pathway Effects 0.000 description 1
• 239000008177 pharmaceutical agent Substances 0.000 description 1
• 230000000144 pharmacologic effect Effects 0.000 description 1
• LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
• 150000004714 phosphonium salts Chemical class 0.000 description 1
• 229910052698 phosphorus Inorganic materials 0.000 description 1
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl chloride Substances ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
• 238000006303 photolysis reaction Methods 0.000 description 1
• 230000015843 photosynthesis, light reaction Effects 0.000 description 1
• 125000003386 piperidinyl group Chemical group 0.000 description 1
• 239000003880 polar aprotic solvent Substances 0.000 description 1
• 230000001242 postsynaptic effect Effects 0.000 description 1
• 235000011056 potassium acetate Nutrition 0.000 description 1
• JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
• 239000000843 powder Substances 0.000 description 1
• 229960001289 prazosin Drugs 0.000 description 1
• 230000001376 precipitating effect Effects 0.000 description 1
• 230000003518 presynaptic effect Effects 0.000 description 1
• 238000012545 processing Methods 0.000 description 1
• ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 1
• KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
• PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical group C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 1
• 239000000376 reactant Substances 0.000 description 1
• 239000012048 reactive intermediate Substances 0.000 description 1
• 230000004648 relaxation of smooth muscle Effects 0.000 description 1
• 238000007157 ring contraction reaction Methods 0.000 description 1
• 230000002295 serotoninergic effect Effects 0.000 description 1
• 238000007086 side reaction Methods 0.000 description 1
• 229910000077 silane Inorganic materials 0.000 description 1
• 229940071536 silver acetate Drugs 0.000 description 1
• 229910001961 silver nitrate Inorganic materials 0.000 description 1
• 229910001923 silver oxide Inorganic materials 0.000 description 1
• 210000002460 smooth muscle Anatomy 0.000 description 1
• 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
• WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
• 239000004299 sodium benzoate Substances 0.000 description 1
• 235000010234 sodium benzoate Nutrition 0.000 description 1
• AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
• HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
• JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
• 229940001584 sodium metabisulfite Drugs 0.000 description 1
• 235000010262 sodium metabisulphite Nutrition 0.000 description 1
• AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
• 235000019345 sodium thiosulphate Nutrition 0.000 description 1
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
• GNCGTEQGBYYYBX-UHFFFAOYSA-M sodium;4-methylbenzoate Chemical compound [Na+].CC1=CC=C(C([O-])=O)C=C1 GNCGTEQGBYYYBX-UHFFFAOYSA-M 0.000 description 1
• 239000011877 solvent mixture Substances 0.000 description 1
• 230000002048 spasmolytic effect Effects 0.000 description 1
• 239000001119 stannous chloride Substances 0.000 description 1
• 235000011150 stannous chloride Nutrition 0.000 description 1
• 239000000758 substrate Substances 0.000 description 1
• 229960002317 succinimide Drugs 0.000 description 1
• HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
• 239000012730 sustained-release form Substances 0.000 description 1
• 208000011580 syndromic disease Diseases 0.000 description 1
• 238000010189 synthetic method Methods 0.000 description 1
• 229950003559 terflavoxate Drugs 0.000 description 1
• 150000003512 tertiary amines Chemical class 0.000 description 1
• 238000004809 thin layer chromatography Methods 0.000 description 1
• 150000003568 thioethers Chemical class 0.000 description 1
• 150000003573 thiols Chemical group 0.000 description 1
• QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
• 210000001519 tissue Anatomy 0.000 description 1
• DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
• WORJEOGGNQDSOE-ASTXPPQBSA-N trichloro(deuterio)methane;trideuterio(deuteriooxy)methane Chemical compound [2H]C(Cl)(Cl)Cl.[2H]OC([2H])([2H])[2H] WORJEOGGNQDSOE-ASTXPPQBSA-N 0.000 description 1
• KPZSTOVTJYRDIO-UHFFFAOYSA-K trichlorocerium;heptahydrate Chemical compound O.O.O.O.O.O.O.Cl[Ce](Cl)Cl KPZSTOVTJYRDIO-UHFFFAOYSA-K 0.000 description 1
• CPRPKIMXLHBUGA-UHFFFAOYSA-N triethyltin Chemical compound CC[Sn](CC)CC CPRPKIMXLHBUGA-UHFFFAOYSA-N 0.000 description 1
• JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
• SCHZCUMIENIQMY-UHFFFAOYSA-N tris(trimethylsilyl)silicon Chemical compound C[Si](C)(C)[Si]([Si](C)(C)C)[Si](C)(C)C SCHZCUMIENIQMY-UHFFFAOYSA-N 0.000 description 1
• FUCBQMFTYFQCOB-UHFFFAOYSA-N trityl perchlorate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCl(=O)(=O)=O)C1=CC=CC=C1 FUCBQMFTYFQCOB-UHFFFAOYSA-N 0.000 description 1
• 210000003708 urethra Anatomy 0.000 description 1
• 210000002700 urine Anatomy 0.000 description 1
• 238000003828 vacuum filtration Methods 0.000 description 1
• HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
• 238000010792 warming Methods 0.000 description 1
• 239000011787 zinc oxide Substances 0.000 description 1