RU2380370C2 - Трициклические соединения бензопирана в качестве противоаритмических агентов - Google Patents

Info

Publication number

RU2380370C2

RU2380370C2 RU2006137284/04A RU2006137284A RU2380370C2 RU 2380370 C2 RU2380370 C2 RU 2380370C2 RU 2006137284/04 A RU2006137284/04 A RU 2006137284/04A RU 2006137284 A RU2006137284 A RU 2006137284A RU 2380370 C2 RU2380370 C2 RU 2380370C2

Authority

RU

Russia

Prior art keywords

group

amino

dihydro

pyrano

trimethyl

Prior art date

2004-03-23

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 138
• KYNSBQPICQTCGU-UHFFFAOYSA-N Benzopyrane Chemical compound C1=CC=C2C=CCOC2=C1 KYNSBQPICQTCGU-UHFFFAOYSA-N 0.000 title claims 3
• 239000003416 antiarrhythmic agent Substances 0.000 title abstract description 7
• 150000003839 salts Chemical class 0.000 claims abstract description 118
• 150000001562 benzopyrans Chemical class 0.000 claims abstract description 115
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 108
• 125000003277 amino group Chemical group 0.000 claims abstract description 85
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 84
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 71
• 125000005915 C6-C14 aryl group Chemical group 0.000 claims abstract description 26
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 10
• 125000006553 (C3-C8) cycloalkenyl group Chemical group 0.000 claims abstract description 8
• -1 1,3-benzodioxol-5-yl Chemical group 0.000 claims description 843
• 125000005843 halogen group Chemical group 0.000 claims description 157
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 85
• 125000000217 alkyl group Chemical group 0.000 claims description 68
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 66
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 59
• 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 46
• 125000001072 heteroaryl group Chemical group 0.000 claims description 43
• 125000000623 heterocyclic group Chemical group 0.000 claims description 37
• 125000001424 substituent group Chemical group 0.000 claims description 37
• 125000003118 aryl group Chemical group 0.000 claims description 30
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 26
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 15
• 206010003119 arrhythmia Diseases 0.000 claims description 14
• 230000006793 arrhythmia Effects 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
• 229910052717 sulfur Inorganic materials 0.000 claims description 11
• 239000003814 drug Substances 0.000 claims description 9
• 239000004480 active ingredient Substances 0.000 claims description 8
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• CHIOVPNYOWEUJW-UHFFFAOYSA-N 2,2,7-trimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound C12=CC3=NC(C)=CC=C3C=C2OC(C)(C)C(O)C1NCCC1=CC=CC=C1 CHIOVPNYOWEUJW-UHFFFAOYSA-N 0.000 claims description 5
• ZZUSANGEAUESFL-UHFFFAOYSA-N 7-(hydroxymethyl)-2,2,9-trimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(CO)=NC3=CC=2C1NCCC1=CC=CC=C1 ZZUSANGEAUESFL-UHFFFAOYSA-N 0.000 claims description 5
• NGWVFMQMEXBFMD-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCC1=CC=CC=C1 NGWVFMQMEXBFMD-UHFFFAOYSA-N 0.000 claims description 5
• UVSBPVGBBJBIPA-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-(2-pyridin-3-ylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCC1=CC=CN=C1 UVSBPVGBBJBIPA-UHFFFAOYSA-N 0.000 claims description 5
• KCHOBYCFOXAKNM-UHFFFAOYSA-N 7-chloro-4-(2-cyclohexylethylamino)-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCC1CCCCC1 KCHOBYCFOXAKNM-UHFFFAOYSA-N 0.000 claims description 5
• HZUJFGLZSGYMQT-UHFFFAOYSA-N 8-hydroxy-7,7-dimethyl-9-(2-phenylethylamino)-8,9-dihydro-1h-pyrano[3,2-g][1,4]benzoxazin-2-one Chemical compound OC1C(C)(C)OC2=CC=3OCC(=O)NC=3C=C2C1NCCC1=CC=CC=C1 HZUJFGLZSGYMQT-UHFFFAOYSA-N 0.000 claims description 5
• 229910005965 SO 2 Inorganic materials 0.000 claims description 5
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• IDLTUNKJYAGSFN-UHFFFAOYSA-N 2,2-dimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC2=CC3=CC=CN=C3C=C2C1NCCC1=CC=CC=C1 IDLTUNKJYAGSFN-UHFFFAOYSA-N 0.000 claims description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• YFUJXCXOIXYJBA-UHFFFAOYSA-N 3-hydroxy-2,2,9-trimethyl-4-(2-phenylethylamino)-4,6-dihydro-3h-pyrano[2,3-g]quinolin-7-one Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(O)=NC3=CC=2C1NCCC1=CC=CC=C1 YFUJXCXOIXYJBA-UHFFFAOYSA-N 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
• IJBQSFCBZCLRHT-UHFFFAOYSA-N 4-[2-(4-aminophenyl)ethylamino]-7-chloro-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCC1=CC=C(N)C=C1 IJBQSFCBZCLRHT-UHFFFAOYSA-N 0.000 claims description 4
• WEPXBRHBWVVKAZ-UHFFFAOYSA-N 4-[2-(4-fluorophenyl)ethylamino]-7-(hydroxymethyl)-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(CO)=NC3=CC=2C1NCCC1=CC=C(F)C=C1 WEPXBRHBWVVKAZ-UHFFFAOYSA-N 0.000 claims description 4
• KMKAFGPNRRAYKI-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-(2-piperidin-1-ylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCN1CCCCC1 KMKAFGPNRRAYKI-UHFFFAOYSA-N 0.000 claims description 4
• ACZVHCBJCSMHIL-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-(pentylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound C1=C(Cl)N=C2C=C3C(NCCCCC)C(O)C(C)(C)OC3=CC2=C1C ACZVHCBJCSMHIL-UHFFFAOYSA-N 0.000 claims description 4
• MALZGBGSFIRJBT-UHFFFAOYSA-N 7-chloro-4-(2-cyclopentylethylamino)-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCC1CCCC1 MALZGBGSFIRJBT-UHFFFAOYSA-N 0.000 claims description 4
• OCWSNZPOQFDULI-UHFFFAOYSA-N 7-chloro-4-(2-hydroxypentylamino)-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound C1=C(Cl)N=C2C=C3C(NCC(O)CCC)C(O)C(C)(C)OC3=CC2=C1C OCWSNZPOQFDULI-UHFFFAOYSA-N 0.000 claims description 4
• KBOCOAKGVSVDNO-UHFFFAOYSA-N 7-chloro-4-[(2-hydroxy-2-phenylethyl)amino]-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCC(O)C1=CC=CC=C1 KBOCOAKGVSVDNO-UHFFFAOYSA-N 0.000 claims description 4
• KTZDNDVKDFBDHQ-UHFFFAOYSA-N 7-chloro-4-[2-(2-fluorophenyl)ethylamino]-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCC1=CC=CC=C1F KTZDNDVKDFBDHQ-UHFFFAOYSA-N 0.000 claims description 4
• SJROYWSEXZWKAM-UHFFFAOYSA-N 7-chloro-4-[2-(4-fluorophenyl)ethylamino]-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCC1=CC=C(F)C=C1 SJROYWSEXZWKAM-UHFFFAOYSA-N 0.000 claims description 4
• NFWWZVHIWDPWEY-UHFFFAOYSA-N 7-chloro-4-[2-(cyclopenten-1-yl)ethylamino]-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCC1=CCCC1 NFWWZVHIWDPWEY-UHFFFAOYSA-N 0.000 claims description 4
• KEOCMVKQQCQIJF-UHFFFAOYSA-N 8-hydroxy-4,7,7-trimethyl-9-(2-phenylethylamino)-8,9-dihydropyrano[2,3-g][1,4]benzoxazin-3-one Chemical compound OC1C(C)(C)OC=2C=C3N(C)C(=O)COC3=CC=2C1NCCC1=CC=CC=C1 KEOCMVKQQCQIJF-UHFFFAOYSA-N 0.000 claims description 4
• KOCXCSREADKFMD-UHFFFAOYSA-N 8-hydroxy-7,7-dimethyl-9-(2-phenylethylamino)-8,9-dihydro-4h-pyrano[2,3-g][1,4]benzoxazin-3-one Chemical compound OC1C(C)(C)OC2=CC=3NC(=O)COC=3C=C2C1NCCC1=CC=CC=C1 KOCXCSREADKFMD-UHFFFAOYSA-N 0.000 claims description 4
• CYRVNMMXCDNQLC-UHFFFAOYSA-N 9-(hydroxymethyl)-2,2-dimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC2=CC3=C(CO)C=CN=C3C=C2C1NCCC1=CC=CC=C1 CYRVNMMXCDNQLC-UHFFFAOYSA-N 0.000 claims description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• XEQQREZFQJPKEY-UHFFFAOYSA-N 3,3-dimethyl-1-(2-phenylethylamino)-1,2-dihydropyrano[3,2-f]quinolin-2-ol Chemical compound OC1C(C)(C)OC2=CC=C3N=CC=CC3=C2C1NCCC1=CC=CC=C1 XEQQREZFQJPKEY-UHFFFAOYSA-N 0.000 claims description 3
• AOKCDZVLSLZJQS-UHFFFAOYSA-N 7-(aminomethyl)-2,2,9-trimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(CN)=NC3=CC=2C1NCCC1=CC=CC=C1 AOKCDZVLSLZJQS-UHFFFAOYSA-N 0.000 claims description 3
• FQLGOINSFWFWGI-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-(2-pyridin-2-ylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCC1=CC=CC=N1 FQLGOINSFWFWGI-UHFFFAOYSA-N 0.000 claims description 3
• HZIDZZCZABOJDG-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-(3-methylbutylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound C1=C(Cl)N=C2C=C3C(NCCC(C)C)C(O)C(C)(C)OC3=CC2=C1C HZIDZZCZABOJDG-UHFFFAOYSA-N 0.000 claims description 3
• ODTMNOQRTBPFTK-UHFFFAOYSA-N 7-chloro-4-[2-(4-chlorophenyl)ethylamino]-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCC1=CC=C(Cl)C=C1 ODTMNOQRTBPFTK-UHFFFAOYSA-N 0.000 claims description 3
• FQNGONYRIBIZMD-UHFFFAOYSA-N 7-chloro-4-[2-(4-chloropyrazol-1-yl)ethylamino]-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCN1C=C(Cl)C=N1 FQNGONYRIBIZMD-UHFFFAOYSA-N 0.000 claims description 3
• VLOYHAHOSOHRFO-UHFFFAOYSA-N 1-[3-hydroxy-2,2,9-trimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-7-yl]ethanone Chemical compound C12=CC3=NC(C(=O)C)=CC(C)=C3C=C2OC(C)(C)C(O)C1NCCC1=CC=CC=C1 VLOYHAHOSOHRFO-UHFFFAOYSA-N 0.000 claims description 2
• LMVGPQNBHMECBB-UHFFFAOYSA-N 2,2,7,9-tetramethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound C12=CC3=NC(C)=CC(C)=C3C=C2OC(C)(C)C(O)C1NCCC1=CC=CC=C1 LMVGPQNBHMECBB-UHFFFAOYSA-N 0.000 claims description 2
• OWYYYCYHGORREH-UHFFFAOYSA-N 3-hydroxy-2,2,9-trimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinoline-7-carbonitrile Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(C#N)=NC3=CC=2C1NCCC1=CC=CC=C1 OWYYYCYHGORREH-UHFFFAOYSA-N 0.000 claims description 2
• YTPYRWAEDGCSTH-UHFFFAOYSA-N 3-hydroxy-2,2,9-trimethyl-4-(2-phenylethylamino)-3,4-dihydropyrano[2,3-g]quinoline-7-carboxylic acid Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(C(O)=O)=NC3=CC=2C1NCCC1=CC=CC=C1 YTPYRWAEDGCSTH-UHFFFAOYSA-N 0.000 claims description 2
• YHKRTDZFVQAXNA-UHFFFAOYSA-N 4-(2-anilinoethylamino)-7-chloro-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCNC1=CC=CC=C1 YHKRTDZFVQAXNA-UHFFFAOYSA-N 0.000 claims description 2
• ZVQPSPFZVMLTID-UHFFFAOYSA-N 4-(benzylamino)-7-chloro-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCC1=CC=CC=C1 ZVQPSPFZVMLTID-UHFFFAOYSA-N 0.000 claims description 2
• ILAFKBRUZSFDLN-UHFFFAOYSA-N 4-[2-(1,3-benzodioxol-5-yl)ethylamino]-7-chloro-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound C1=C2OCOC2=CC(CCNC2C=3C=C4N=C(Cl)C=C(C4=CC=3OC(C)(C)C2O)C)=C1 ILAFKBRUZSFDLN-UHFFFAOYSA-N 0.000 claims description 2
• XVQLNGKUONDIFY-UHFFFAOYSA-N 7,7-dimethyl-9-(2-phenylethylamino)-2,3,8,9-tetrahydro-1h-pyrano[3,2-g][1,4]benzoxazin-8-ol Chemical compound OC1C(C)(C)OC2=CC=3OCCNC=3C=C2C1NCCC1=CC=CC=C1 XVQLNGKUONDIFY-UHFFFAOYSA-N 0.000 claims description 2
• XBWPQJQYWLKBCY-UHFFFAOYSA-N 7,7-dimethyl-9-(2-phenylethylamino)-3,4,8,9-tetrahydro-2h-pyrano[2,3-g][1,4]benzoxazin-8-ol Chemical compound OC1C(C)(C)OC2=CC=3NCCOC=3C=C2C1NCCC1=CC=CC=C1 XBWPQJQYWLKBCY-UHFFFAOYSA-N 0.000 claims description 2
• WQZQDRKMVROFHJ-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-(2-phenylbutylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC2=CC3=C(C)C=C(Cl)N=C3C=C2C1NCC(CC)C1=CC=CC=C1 WQZQDRKMVROFHJ-UHFFFAOYSA-N 0.000 claims description 2
• MXIJWHXNCBQJHS-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-(2-pyridin-4-ylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCC1=CC=NC=C1 MXIJWHXNCBQJHS-UHFFFAOYSA-N 0.000 claims description 2
• ZRKWCAVJGJNPNW-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-(2-thiophen-3-ylethylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCC=1C=CSC=1 ZRKWCAVJGJNPNW-UHFFFAOYSA-N 0.000 claims description 2
• YMBOASLJUYMDCP-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-(5-methylhexan-2-ylamino)-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound C1=C(Cl)N=C2C=C3C(NC(C)CCC(C)C)C(O)C(C)(C)OC3=CC2=C1C YMBOASLJUYMDCP-UHFFFAOYSA-N 0.000 claims description 2
• IHFXTCWKIXGPLI-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-[2-(1-methylpyrrolidin-2-yl)ethylamino]-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound CN1CCCC1CCNC1C2=CC3=NC(Cl)=CC(C)=C3C=C2OC(C)(C)C1O IHFXTCWKIXGPLI-UHFFFAOYSA-N 0.000 claims description 2
• FPRQSHYHIOERJP-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-[2-(4-methylpyrazol-1-yl)ethylamino]-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound C1=C(C)C=NN1CCNC1C2=CC3=NC(Cl)=CC(C)=C3C=C2OC(C)(C)C1O FPRQSHYHIOERJP-UHFFFAOYSA-N 0.000 claims description 2
• NEYBDHJHQOKKJP-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-[2-(oxan-4-yl)ethylamino]-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCC1CCOCC1 NEYBDHJHQOKKJP-UHFFFAOYSA-N 0.000 claims description 2
• HSXRMLRUJJJOPX-UHFFFAOYSA-N 7-chloro-2,2,9-trimethyl-4-[2-(thian-4-yl)ethylamino]-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCCC1CCSCC1 HSXRMLRUJJJOPX-UHFFFAOYSA-N 0.000 claims description 2
• WKCNSSVKPYPGHL-UHFFFAOYSA-N 7-chloro-4-(2,2-diethoxyethylamino)-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound C1=C(Cl)N=C2C=C3C(NCC(OCC)OCC)C(O)C(C)(C)OC3=CC2=C1C WKCNSSVKPYPGHL-UHFFFAOYSA-N 0.000 claims description 2
• BKMVAQVEIIIEJD-UHFFFAOYSA-N 7-chloro-4-(cyclopropylmethylamino)-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC=2C=C3C(C)=CC(Cl)=NC3=CC=2C1NCC1CC1 BKMVAQVEIIIEJD-UHFFFAOYSA-N 0.000 claims description 2
• AHJQDTJTOLKGCR-UHFFFAOYSA-N 7-chloro-4-[2-(n-ethyl-3-methylanilino)ethylamino]-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound OC1C(C)(C)OC2=CC3=C(C)C=C(Cl)N=C3C=C2C1NCCN(CC)C1=CC=CC(C)=C1 AHJQDTJTOLKGCR-UHFFFAOYSA-N 0.000 claims description 2
• BAQBVLMAIRROTP-OZJRSANCSA-N 7-chloro-4-[[(2r)-1-ethylpyrrolidin-2-yl]methylamino]-2,2,9-trimethyl-3,4-dihydropyrano[2,3-g]quinolin-3-ol Chemical compound CCN1CCC[C@@H]1CNC1C2=CC3=NC(Cl)=CC(C)=C3C=C2OC(C)(C)C1O BAQBVLMAIRROTP-OZJRSANCSA-N 0.000 claims description 2
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
• 125000000286 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 2
• WXXVQWSDMOAHHV-UHFFFAOYSA-N quinoline-7-carboxylic acid Chemical compound C1=CC=NC2=CC(C(=O)O)=CC=C21 WXXVQWSDMOAHHV-UHFFFAOYSA-N 0.000 claims description 2
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