SK284689B6 - Benzopyrano[3,4-f]chinolínová zlúčenina a liečivo s jej obsahom - Google Patents

Benzopyrano[3,4-f]chinolínová zlúčenina a liečivo s jej obsahom Download PDF

Info

Publication number: SK284689B6
Authority: SK; Slovakia
Prior art keywords: benzopyrano; dihydro; trimethyl; quinoline; methoxy
Prior art date: 1998-02-13

Application number

SK1197-2000A

Other languages

English (en)

Slovak (sk)

Other versions

SK11972000A3 (sk

Inventor

Michael J. Coughlan

Steven W. Elmore

Michael E. Kort

Philip R. Kym

Jimmie L. Moore

John K. Pratt

Alan X. Wang

James P. Edwards

Todd K. Jones

Original Assignee

Abbott Laboratories

Ligand Pharmaceuticals, Inc.

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-02-13

Filing date

1999-02-12

Publication date

2005-09-08

1999-02-12 Application filed by Abbott Laboratories, Ligand Pharmaceuticals, Inc. filed Critical Abbott Laboratories

2001-08-06 Publication of SK11972000A3 publication Critical patent/SK11972000A3/sk

2005-09-08 Publication of SK284689B6 publication Critical patent/SK284689B6/sk

Links

239000003814 drug Substances 0.000 title claims abstract description 17
-1 Benzopyrano[3,4-f]quinoline compound Chemical class 0.000 title claims description 332
150000001875 compounds Chemical class 0.000 claims abstract description 495
AUBMWPNTVARGGM-UHFFFAOYSA-N 5h-chromeno[3,4-f]quinoline Chemical class N1=CC=CC2=C3COC4=CC=CC=C4C3=CC=C21 AUBMWPNTVARGGM-UHFFFAOYSA-N 0.000 claims abstract description 96
102000003676 Glucocorticoid Receptors Human genes 0.000 claims abstract description 22
108090000079 Glucocorticoid Receptors Proteins 0.000 claims abstract description 22
208000023275 Autoimmune disease Diseases 0.000 claims abstract description 5
241000124008 Mammalia Species 0.000 claims abstract description 5
208000026278 immune system disease Diseases 0.000 claims abstract description 5
238000004519 manufacturing process Methods 0.000 claims abstract description 5
208000027866 inflammatory disease Diseases 0.000 claims abstract description 4
230000003042 antagnostic effect Effects 0.000 claims abstract description 3
230000001363 autoimmune Effects 0.000 claims abstract description 3
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 416
125000004432 carbon atom Chemical group C* 0.000 claims description 295
125000000217 alkyl group Chemical group 0.000 claims description 141
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 117
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 81
229910052799 carbon Inorganic materials 0.000 claims description 71
125000001424 substituent group Chemical group 0.000 claims description 64
125000003118 aryl group Chemical group 0.000 claims description 56
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 47
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 44
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 43
229910052757 nitrogen Inorganic materials 0.000 claims description 42
125000000753 cycloalkyl group Chemical group 0.000 claims description 41
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 40
150000001721 carbon Chemical group 0.000 claims description 37
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 33
229910052739 hydrogen Inorganic materials 0.000 claims description 32
150000002367 halogens Chemical class 0.000 claims description 29
229910052736 halogen Inorganic materials 0.000 claims description 28
150000002148 esters Chemical class 0.000 claims description 27
125000003342 alkenyl group Chemical group 0.000 claims description 24
125000003545 alkoxy group Chemical group 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 24
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
125000000304 alkynyl group Chemical group 0.000 claims description 19
125000000623 heterocyclic group Chemical group 0.000 claims description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 19
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 18
RVYLMCJINZTBAG-UHFFFAOYSA-N 10-methoxy-2,2,4-trimethyl-5-(1-methylcyclohex-3-en-1-yl)-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C1(C)CCC=CC1 RVYLMCJINZTBAG-UHFFFAOYSA-N 0.000 claims description 15
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
125000004438 haloalkoxy group Chemical group 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
MTUNPZRNIWKUHS-UHFFFAOYSA-N 5-cyclohex-3-en-1-yl-10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinolin-9-ol Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=C(O)C=CC=1OC2C1CCC=CC1 MTUNPZRNIWKUHS-UHFFFAOYSA-N 0.000 claims description 12
229920001774 Perfluoroether Polymers 0.000 claims description 12
125000004423 acyloxy group Chemical group 0.000 claims description 12
125000000392 cycloalkenyl group Chemical group 0.000 claims description 12
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 12
AHJZGERXBACBDO-UHFFFAOYSA-N [1-(10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinolin-5-yl)cyclohex-3-en-1-yl]methanol Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C1(CO)CCC=CC1 AHJZGERXBACBDO-UHFFFAOYSA-N 0.000 claims description 11
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
229910052717 sulfur Inorganic materials 0.000 claims description 11
UTLVNNNRCCRBDZ-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)-10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C1=CC(Cl)=CC(Cl)=C1 UTLVNNNRCCRBDZ-UHFFFAOYSA-N 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
125000001639 phenylmethylene group Chemical group [H]C(=*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 9
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
125000001589 carboacyl group Chemical group 0.000 claims description 9
125000005309 thioalkoxy group Chemical group 0.000 claims description 9
CZSDJYXNNJQXBB-UHFFFAOYSA-N 10-methoxy-2,2,4-trimethyl-5-prop-2-enyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound N1C(C)(C)C=C(C)C2=C1C=CC1=C2C(CC=C)OC2=C1C(OC)=CC=C2 CZSDJYXNNJQXBB-UHFFFAOYSA-N 0.000 claims description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 8
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 8
CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 claims description 8
125000005322 morpholin-1-yl group Chemical group 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 8
ZJDOKOYFQMUCAA-HSZRJFAPSA-N (5r)-5-cyclopent-3-en-1-yl-10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinolin-9-ol Chemical compound C1([C@H]2OC=3C=CC(O)=C(C=3C3=C2C=2C(C)=CC(C)(C)NC=2C=C3)OC)CC=CC1 ZJDOKOYFQMUCAA-HSZRJFAPSA-N 0.000 claims description 7
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 7
IOQIJULQRLQTLW-UHFFFAOYSA-N 10-methoxy-5-[1-(methoxymethyl)cyclohex-3-en-1-yl]-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound O1C2=CC=CC(OC)=C2C2=CC=C3NC(C)(C)C=C(C)C3=C2C1C1(COC)CCC=CC1 IOQIJULQRLQTLW-UHFFFAOYSA-N 0.000 claims description 6
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
BSJYFMFPTGYKFE-VOTSOKGWSA-N 5-[(e)-but-2-enyl]-10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound N1C(C)(C)C=C(C)C2=C1C=CC1=C2C(C\C=C\C)OC2=C1C(OC)=CC=C2 BSJYFMFPTGYKFE-VOTSOKGWSA-N 0.000 claims description 6
HCASQQRVVZESNK-UHFFFAOYSA-N 5-but-3-enyl-10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound N1C(C)(C)C=C(C)C2=C1C=CC1=C2C(CCC=C)OC2=C1C(OC)=CC=C2 HCASQQRVVZESNK-UHFFFAOYSA-N 0.000 claims description 6
206010061218 Inflammation Diseases 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
230000004054 inflammatory process Effects 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
125000003003 spiro group Chemical group 0.000 claims description 6
GAURXTVQCLMZDF-UHFFFAOYSA-N 10-chloro-2,2,4-trimethyl-5-(3-methylcyclohex-2-en-1-yl)-1,5-dihydrochromeno[3,4-f]quinolin-9-ol Chemical compound C1CCC(C)=CC1C1C2=C3C(C)=CC(C)(C)NC3=CC=C2C2=C(Cl)C(O)=CC=C2O1 GAURXTVQCLMZDF-UHFFFAOYSA-N 0.000 claims description 5
JLKOGSSZSBFPNY-UHFFFAOYSA-N 10-methoxy-2,2,4-trimethyl-5-phenyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C1=CC=CC=C1 JLKOGSSZSBFPNY-UHFFFAOYSA-N 0.000 claims description 5
DZJNEBDBFOHSLU-UHFFFAOYSA-N 10-methoxy-2,2,4-trimethyl-5-pyridin-2-yl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C1=CC=CC=N1 DZJNEBDBFOHSLU-UHFFFAOYSA-N 0.000 claims description 5
APCWDXUMGJRXRY-UHFFFAOYSA-N 3-(10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinolin-5-yl)phenol Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C1=CC=CC(O)=C1 APCWDXUMGJRXRY-UHFFFAOYSA-N 0.000 claims description 5
BDZQBRNZPXXVRN-UHFFFAOYSA-N 5-cyclopent-2-en-1-yl-10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C1CCC=C1 BDZQBRNZPXXVRN-UHFFFAOYSA-N 0.000 claims description 5
UNZHHWJTTNVJLH-UHFFFAOYSA-N 5H-chromeno[3,4-f]quinolin-10-ol Chemical compound N1=CC=CC2=C3C(=CC=C12)C1=C(OC3)C=CC=C1O UNZHHWJTTNVJLH-UHFFFAOYSA-N 0.000 claims description 5
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 5
HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 5
DWLVWMUCHSLGSU-UHFFFAOYSA-M n,n-dimethylcarbamate Chemical compound CN(C)C([O-])=O DWLVWMUCHSLGSU-UHFFFAOYSA-M 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
CRODFMXMGHZTCT-UHFFFAOYSA-N (2,2,4-trimethyl-5-prop-2-enyl-1,5-dihydrochromeno[3,4-f]quinolin-10-yl)methanol Chemical compound C1=CC(CO)=C2C3=CC=C4NC(C)(C)C=C(C)C4=C3C(CC=C)OC2=C1 CRODFMXMGHZTCT-UHFFFAOYSA-N 0.000 claims description 4
RIMMQBPPMWIKQL-UHFFFAOYSA-N 1-[1-(10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinolin-5-yl)cyclohex-3-en-1-yl]-n,n-dimethylmethanamine Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C1(CN(C)C)CCC=CC1 RIMMQBPPMWIKQL-UHFFFAOYSA-N 0.000 claims description 4
LAPMZMQWRPTALX-UHFFFAOYSA-N 1-amino-3-[3-(10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinolin-5-yl)propyl]urea Chemical compound N1C(C)(C)C=C(C)C2=C1C=CC1=C2C(CCCNC(=O)NN)OC2=C1C(OC)=CC=C2 LAPMZMQWRPTALX-UHFFFAOYSA-N 0.000 claims description 4
YPWZJBIPKXBVJU-UHFFFAOYSA-N 10-methoxy-2,2,4-trimethyl-5-(2-methylpropyl)-1,5-dihydrochromeno[3,4-f]quinolin-9-ol Chemical compound N1C(C)(C)C=C(C)C2=C1C=CC1=C2C(CC(C)C)OC2=C1C(OC)=C(O)C=C2 YPWZJBIPKXBVJU-UHFFFAOYSA-N 0.000 claims description 4
SKEJNSVRWWQZBJ-UHFFFAOYSA-N 10-methoxy-2,2,4-trimethyl-5-(3,4,5-trifluorophenyl)-1,5-dihydrochromeno[3,4-f]quinolin-9-ol Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=C(O)C=CC=1OC2C1=CC(F)=C(F)C(F)=C1 SKEJNSVRWWQZBJ-UHFFFAOYSA-N 0.000 claims description 4
FYTLUAPGNVPELX-UHFFFAOYSA-N 10-methoxy-2,2,4-trimethyl-5-(3,4,5-trifluorophenyl)-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C1=CC(F)=C(F)C(F)=C1 FYTLUAPGNVPELX-UHFFFAOYSA-N 0.000 claims description 4
UGAAGFLLDUNYHF-UHFFFAOYSA-N 10-methoxy-2,2,4-trimethyl-5-(3-methyl-5-prop-2-enylphenyl)-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C1=CC(C)=CC(CC=C)=C1 UGAAGFLLDUNYHF-UHFFFAOYSA-N 0.000 claims description 4
IAEZOXGQHZOTMT-UHFFFAOYSA-N 10-methoxy-2,2,4-trimethyl-5-(3-methylsulfanylphenyl)-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C1=CC=CC(SC)=C1 IAEZOXGQHZOTMT-UHFFFAOYSA-N 0.000 claims description 4
OFTFOMXOHSRDLN-UHFFFAOYSA-N 10-methoxy-2,2,4-trimethyl-5-(4-phenylmethoxyphenyl)-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C(C=C1)=CC=C1OCC1=CC=CC=C1 OFTFOMXOHSRDLN-UHFFFAOYSA-N 0.000 claims description 4
BCOHBHZHJMEMCP-UHFFFAOYSA-N 10-methoxy-2,2,4-trimethyl-5-(5-propylthiophen-2-yl)-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound S1C(CCC)=CC=C1C1C2=C3C(C)=CC(C)(C)NC3=CC=C2C2=C(OC)C=CC=C2O1 BCOHBHZHJMEMCP-UHFFFAOYSA-N 0.000 claims description 4
VJGOOMWSGKQZIC-UHFFFAOYSA-N 10-methoxy-2,2,4-trimethyl-5-(pyridin-2-ylmethylidene)-1h-chromeno[3,4-f]quinoline Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2=CC1=CC=CC=N1 VJGOOMWSGKQZIC-UHFFFAOYSA-N 0.000 claims description 4
DNPSCURCSGTQSO-UHFFFAOYSA-N 10-methoxy-2,2,4-trimethyl-5-[3-(trifluoromethyl)phenyl]-1,5-dihydrochromeno[3,4-f]quinolin-9-ol Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=C(O)C=CC=1OC2C1=CC=CC(C(F)(F)F)=C1 DNPSCURCSGTQSO-UHFFFAOYSA-N 0.000 claims description 4
YEHYAJFHTQBDDU-UHFFFAOYSA-N 10-methoxy-2,2,4-trimethyl-5-phenyl-1,5-dihydrochromeno[3,4-f]quinolin-9-ol Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=C(O)C=CC=1OC2C1=CC=CC=C1 YEHYAJFHTQBDDU-UHFFFAOYSA-N 0.000 claims description 4
LJGRIJMDQDYZEI-UHFFFAOYSA-N 10-methoxy-2,2,4-trimethyl-5-propan-2-yl-1,5-dihydrochromeno[3,4-f]quinolin-9-ol Chemical compound N1C(C)(C)C=C(C)C2=C1C=CC1=C2C(C(C)C)OC2=C1C(OC)=C(O)C=C2 LJGRIJMDQDYZEI-UHFFFAOYSA-N 0.000 claims description 4
CYWHTVAWQZZCLR-UHFFFAOYSA-N 10-methoxy-2,2,4-trimethyl-5-thiophen-2-yl-1,5-dihydrochromeno[3,4-f]quinolin-9-ol Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=C(O)C=CC=1OC2C1=CC=CS1 CYWHTVAWQZZCLR-UHFFFAOYSA-N 0.000 claims description 4
IVOXXCUEPVLBCH-UHFFFAOYSA-N 10-methoxy-2,2,4-trimethyl-5-thiophen-2-yl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C1=CC=CS1 IVOXXCUEPVLBCH-UHFFFAOYSA-N 0.000 claims description 4
CGZQTIUDWCOCRV-UHFFFAOYSA-N 10-methoxy-5-(4-methoxyphenyl)-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C1=CC(OC)=CC=C1C1C2=C3C(C)=CC(C)(C)NC3=CC=C2C2=C(OC)C=CC=C2O1 CGZQTIUDWCOCRV-UHFFFAOYSA-N 0.000 claims description 4
VJCVRQMEQRYDCN-UHFFFAOYSA-N 10-methoxy-5-(5-methoxythiophen-2-yl)-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound S1C(OC)=CC=C1C1C2=C3C(C)=CC(C)(C)NC3=CC=C2C2=C(OC)C=CC=C2O1 VJCVRQMEQRYDCN-UHFFFAOYSA-N 0.000 claims description 4
AGAKZBMODNRFPP-UHFFFAOYSA-N 10-methoxy-5-[2-(methoxymethoxy)ethyl]-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound N1C(C)(C)C=C(C)C2=C3C(CCOCOC)OC4=CC=CC(OC)=C4C3=CC=C21 AGAKZBMODNRFPP-UHFFFAOYSA-N 0.000 claims description 4
ZOPNTBMGYNZKTM-UHFFFAOYSA-N 2,2,4-trimethyl-5-phenyl-10-prop-2-enoxy-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C=12C(C)=CC(C)(C)NC2=CC=C(C2=C(OCC=C)C=CC=C2O2)C=1C2C1=CC=CC=C1 ZOPNTBMGYNZKTM-UHFFFAOYSA-N 0.000 claims description 4
FLSDPNQUUKAJMU-UHFFFAOYSA-N 2,2,4-trimethyl-5-phenyl-10-prop-2-ynoxy-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C=12C(C)=CC(C)(C)NC2=CC=C(C2=C(OCC#C)C=CC=C2O2)C=1C2C1=CC=CC=C1 FLSDPNQUUKAJMU-UHFFFAOYSA-N 0.000 claims description 4
DMSJQVOZSHWGKP-UHFFFAOYSA-N 2,2,4-trimethyl-5-prop-2-enyl-1,5-dihydrochromeno[3,4-f]quinoline-10-carboxylic acid Chemical compound C1=CC(C(O)=O)=C2C3=CC=C4NC(C)(C)C=C(C)C4=C3C(CC=C)OC2=C1 DMSJQVOZSHWGKP-UHFFFAOYSA-N 0.000 claims description 4
GWHOLYNFWRVFLD-UHFFFAOYSA-N 2-(10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinolin-5-yl)-n,n-dimethylacetamide Chemical compound N1C(C)(C)C=C(C)C2=C1C=CC1=C2C(CC(=O)N(C)C)OC2=C1C(OC)=CC=C2 GWHOLYNFWRVFLD-UHFFFAOYSA-N 0.000 claims description 4
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JKPLCNDLENZQTJ-UHFFFAOYSA-N 5-butyl-10-chloro-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinolin-9-ol Chemical compound N1C(C)(C)C=C(C)C2=C3C(CCCC)OC4=CC=C(O)C(Cl)=C4C3=CC=C21 JKPLCNDLENZQTJ-UHFFFAOYSA-N 0.000 claims description 3
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FPIHUZAABXEZHI-UHFFFAOYSA-N 5-butyl-10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound N1C(C)(C)C=C(C)C2=C3C(CCCC)OC4=CC=CC(OC)=C4C3=CC=C21 FPIHUZAABXEZHI-UHFFFAOYSA-N 0.000 claims description 3
CTXVBMCYRRTVQU-UHFFFAOYSA-N 5-cyclohept-3-en-1-yl-10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C1CCCC=CC1 CTXVBMCYRRTVQU-UHFFFAOYSA-N 0.000 claims description 3
OHJZGTKTVPXFCI-UHFFFAOYSA-N 5-cyclohex-3-en-1-yl-10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C1CCC=CC1 OHJZGTKTVPXFCI-UHFFFAOYSA-N 0.000 claims description 3
VIFBLAKPQHTSPL-UHFFFAOYSA-N 5-cyclohexyl-10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C1CCCCC1 VIFBLAKPQHTSPL-UHFFFAOYSA-N 0.000 claims description 3
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JIGSXDRQEJZDLK-UHFFFAOYSA-N 5-cyclopentyl-10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C1CCCC1 JIGSXDRQEJZDLK-UHFFFAOYSA-N 0.000 claims description 3
VAGFSACHGXYODJ-UHFFFAOYSA-N 5-cyclopropyl-10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C1CC1 VAGFSACHGXYODJ-UHFFFAOYSA-N 0.000 claims description 3
SEAIFPXFJWWJGW-UHFFFAOYSA-N 8-fluoro-10-methoxy-2,2,4-trimethyl-5-phenyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC(F)=CC=1OC2C1=CC=CC=C1 SEAIFPXFJWWJGW-UHFFFAOYSA-N 0.000 claims description 3
RLNRYNADPTVFSB-UHFFFAOYSA-N 9,10-dimethoxy-2,2,4-trimethyl-5-prop-2-enyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound N1C(C)(C)C=C(C)C2=C1C=CC1=C2C(CC=C)OC2=CC=C(OC)C(OC)=C21 RLNRYNADPTVFSB-UHFFFAOYSA-N 0.000 claims description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
YSFYGKSDPUESIT-UHFFFAOYSA-N [3-(10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinolin-5-yl)phenyl] n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC(C2C3=C4C(C)=CC(C)(C)NC4=CC=C3C3=C(OC)C=CC=C3O2)=C1 YSFYGKSDPUESIT-UHFFFAOYSA-N 0.000 claims description 3
VHWYXAQAJMTGAG-UHFFFAOYSA-N [5-(10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinolin-5-yl)cyclohexen-1-yl]methanol Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C1CCC=C(CO)C1 VHWYXAQAJMTGAG-UHFFFAOYSA-N 0.000 claims description 3
125000004419 alkynylene group Chemical group 0.000 claims description 3
RFDCXOHZVYCSJT-UHFFFAOYSA-N ethyl 10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinoline-5-carboxylate Chemical compound N1C(C)(C)C=C(C)C2=C3C(C(=O)OCC)OC4=CC=CC(OC)=C4C3=CC=C21 RFDCXOHZVYCSJT-UHFFFAOYSA-N 0.000 claims description 3
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
ATDPSUIIYYUMNQ-UHFFFAOYSA-N methyl 2,2,4-trimethyl-5-prop-2-enyl-1,5-dihydrochromeno[3,4-f]quinoline-10-carboxylate Chemical compound N1C(C)(C)C=C(C)C2=C1C=CC1=C2C(CC=C)OC2=C1C(C(=O)OC)=CC=C2 ATDPSUIIYYUMNQ-UHFFFAOYSA-N 0.000 claims description 3
LWUPMTHSGBNKFN-UHFFFAOYSA-N methyl 2-[[3-(10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinolin-5-yl)phenoxy]carbonyl-methylamino]acetate Chemical compound COC(=O)CN(C)C(=O)OC1=CC=CC(C2C3=C4C(C)=CC(C)(C)NC4=CC=C3C3=C(OC)C=CC=C3O2)=C1 LWUPMTHSGBNKFN-UHFFFAOYSA-N 0.000 claims description 3
FTXXHRFFVNCHHO-UHFFFAOYSA-N n,2,2,4-tetramethyl-5-prop-2-enyl-1,5-dihydrochromeno[3,4-f]quinolin-10-amine Chemical compound N1C(C)(C)C=C(C)C2=C1C=CC1=C2C(CC=C)OC2=C1C(NC)=CC=C2 FTXXHRFFVNCHHO-UHFFFAOYSA-N 0.000 claims description 3
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125000004043 oxo group Chemical group O=* 0.000 claims description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
WHGHSRRMRUCBSH-AZGAKELHSA-N (5s)-5-[(1s)-1-(hydroxymethyl)cyclopent-2-en-1-yl]-10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinolin-9-ol Chemical compound OC[C@]1([C@H]2OC=3C=CC(O)=C(C=3C3=C2C=2C(C)=CC(C)(C)NC=2C=C3)OC)CCC=C1 WHGHSRRMRUCBSH-AZGAKELHSA-N 0.000 claims description 2
DITDJYCJTMQGAN-QHCPKHFHSA-N (5s)-5-cyclopentyl-10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinolin-9-ol Chemical compound C1([C@@H]2OC=3C=CC(O)=C(C=3C3=C2C=2C(C)=CC(C)(C)NC=2C=C3)OC)CCCC1 DITDJYCJTMQGAN-QHCPKHFHSA-N 0.000 claims description 2
LBEMTXLBZBWMMF-RMKNXTFCSA-N (e)-3-(10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinolin-5-yl)prop-2-en-1-ol Chemical compound N1C(C)(C)C=C(C)C2=C1C=CC1=C2C(\C=C\CO)OC2=C1C(OC)=CC=C2 LBEMTXLBZBWMMF-RMKNXTFCSA-N 0.000 claims description 2
BPVBUBWHSYZREC-UHFFFAOYSA-N 10-chloro-2,2,4-trimethyl-5-(2-methylpropyl)-1,5-dihydrochromeno[3,4-f]quinolin-9-ol Chemical compound N1C(C)(C)C=C(C)C2=C3C(CC(C)C)OC4=CC=C(O)C(Cl)=C4C3=CC=C21 BPVBUBWHSYZREC-UHFFFAOYSA-N 0.000 claims description 2
NBRIKHRTCZEGES-UHFFFAOYSA-N 10-chloro-2,2,4-trimethyl-5-(3,4,5-trifluorophenyl)-1,5-dihydrochromeno[3,4-f]quinolin-9-ol Chemical compound C=12C(C)=CC(C)(C)NC2=CC=C(C2=C(Cl)C(O)=CC=C2O2)C=1C2C1=CC(F)=C(F)C(F)=C1 NBRIKHRTCZEGES-UHFFFAOYSA-N 0.000 claims description 2
SUPUFUJDXQAONV-UHFFFAOYSA-N 10-ethenyl-2,2,4-trimethyl-5-phenyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C=12C(C)=CC(C)(C)NC2=CC=C(C2=C(C=C)C=CC=C2O2)C=1C2C1=CC=CC=C1 SUPUFUJDXQAONV-UHFFFAOYSA-N 0.000 claims description 2
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XYEXCHWRSPFRSU-UHFFFAOYSA-N 5-cyclooct-3-en-1-yl-10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C1CCCCC=CC1 XYEXCHWRSPFRSU-UHFFFAOYSA-N 0.000 claims description 2
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PNNWBQRENKVGBD-UHFFFAOYSA-N C(C)(=O)O.BrC=1C=C(C=C(C1)C)C1OC2=C(C(=CC=C2)OC)C=2C1=C1C(=CC(NC1=CC2)(C)C)C Chemical compound C(C)(=O)O.BrC=1C=C(C=C(C1)C)C1OC2=C(C(=CC=C2)OC)C=2C1=C1C(=CC(NC1=CC2)(C)C)C PNNWBQRENKVGBD-UHFFFAOYSA-N 0.000 claims description 2
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CFEWSMJNCORYGX-UHFFFAOYSA-N [3-(9-hydroxy-10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinolin-5-yl)phenyl] acetate Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=C(O)C=CC=1OC2C1=CC=CC(OC(C)=O)=C1 CFEWSMJNCORYGX-UHFFFAOYSA-N 0.000 claims description 2
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HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 2
235000010233 benzoic acid Nutrition 0.000 claims description 2
125000004494 ethyl ester group Chemical group 0.000 claims description 2
FWFRSLYOSNVRNL-UHFFFAOYSA-N methyl 2,2,4-trimethyl-5-phenyl-1,5-dihydrochromeno[3,4-f]quinoline-10-carboxylate Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(C(=O)OC)=CC=CC=1OC2C1=CC=CC=C1 FWFRSLYOSNVRNL-UHFFFAOYSA-N 0.000 claims description 2
FFILGGNTUAHIFQ-UHFFFAOYSA-N methyl 2-(10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinolin-5-yl)acetate Chemical compound N1C(C)(C)C=C(C)C2=C3C(CC(=O)OC)OC4=CC=CC(OC)=C4C3=CC=C21 FFILGGNTUAHIFQ-UHFFFAOYSA-N 0.000 claims description 2
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150000003254 radicals Chemical class 0.000 claims description 2
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ZCVBMAYOOJIAPW-UHFFFAOYSA-N (2,2,4-trimethyl-5-phenyl-1,5-dihydrochromeno[3,4-f]quinolin-10-yl)methanol Chemical compound C=12C(C)=CC(C)(C)NC2=CC=C(C2=C(CO)C=CC=C2O2)C=1C2C1=CC=CC=C1 ZCVBMAYOOJIAPW-UHFFFAOYSA-N 0.000 claims 2
SQJCERRWCWFROJ-UHFFFAOYSA-N 1-(10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinolin-5-yl)propan-2-one Chemical compound N1C(C)(C)C=C(C)C2=C1C=CC1=C2C(CC(C)=O)OC2=C1C(OC)=CC=C2 SQJCERRWCWFROJ-UHFFFAOYSA-N 0.000 claims 2
CTMHWPIWNRWQEG-UHFFFAOYSA-N 1-methylcyclohexene Chemical compound CC1=CCCCC1 CTMHWPIWNRWQEG-UHFFFAOYSA-N 0.000 claims 2
ULRRSYIZPSVFCL-UHFFFAOYSA-N 10-(methoxymethyl)-2,2,4-trimethyl-5-phenyl-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(COC)=CC=CC=1OC2C1=CC=CC=C1 ULRRSYIZPSVFCL-UHFFFAOYSA-N 0.000 claims 2
YDFCZYLORDKUIZ-UHFFFAOYSA-N 10-chloro-2,2,4-trimethyl-5-propyl-1,5-dihydrochromeno[3,4-f]quinolin-9-ol Chemical compound N1C(C)(C)C=C(C)C2=C3C(CCC)OC4=CC=C(O)C(Cl)=C4C3=CC=C21 YDFCZYLORDKUIZ-UHFFFAOYSA-N 0.000 claims 2
ZIBZOWGYLKHFLW-UHFFFAOYSA-N 10-chloro-5-cyclopentyl-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinolin-9-ol Chemical compound C=12C(C)=CC(C)(C)NC2=CC=C(C2=C(Cl)C(O)=CC=C2O2)C=1C2C1CCCC1 ZIBZOWGYLKHFLW-UHFFFAOYSA-N 0.000 claims 2
JQXUMYDCGLWHAE-UHFFFAOYSA-N 10-methoxy-2,2,4-trimethyl-5-(3-methylbut-2-enyl)-1,5-dihydrochromeno[3,4-f]quinolin-9-ol Chemical compound N1C(C)(C)C=C(C)C2=C1C=CC1=C2C(CC=C(C)C)OC2=C1C(OC)=C(O)C=C2 JQXUMYDCGLWHAE-UHFFFAOYSA-N 0.000 claims 2
AZKXBAPRQCXHRZ-UHFFFAOYSA-N 10-methoxy-2,2,4-trimethyl-5-[3-(trifluoromethyl)phenyl]-1,5-dihydrochromeno[3,4-f]quinoline Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C1=CC=CC(C(F)(F)F)=C1 AZKXBAPRQCXHRZ-UHFFFAOYSA-N 0.000 claims 2
NNAGCDWUOREVAN-UHFFFAOYSA-N 2,2,4-trimethyl-5-phenyl-1,5-dihydrochromeno[3,4-f]quinoline-10-carbaldehyde Chemical compound C=12C(C)=CC(C)(C)NC2=CC=C(C2=C(C=O)C=CC=C2O2)C=1C2C1=CC=CC=C1 NNAGCDWUOREVAN-UHFFFAOYSA-N 0.000 claims 2
MDVLJEDOMYRKFS-UHFFFAOYSA-N 2-[3-(10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinolin-5-yl)phenyl]-n,n-dimethylethanamine Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C1=CC=CC(CCN(C)C)=C1 MDVLJEDOMYRKFS-UHFFFAOYSA-N 0.000 claims 2
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims 2
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YDYYTUAFGSYBGD-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)-2,2,4-trimethyl-n-prop-2-enyl-1,5-dihydrochromeno[3,4-f]quinolin-10-amine Chemical compound C=12C(C)=CC(C)(C)NC2=CC=C(C2=C(NCC=C)C=CC=C2O2)C=1C2C1=CC(Cl)=CC(Cl)=C1 YDYYTUAFGSYBGD-UHFFFAOYSA-N 0.000 claims 2
CICRBHXWMNTOFT-UHFFFAOYSA-N 5-(3,5-dichlorophenyl)-n,2,2,4-tetramethyl-1,5-dihydrochromeno[3,4-f]quinolin-10-amine Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(NC)=CC=CC=1OC2C1=CC(Cl)=CC(Cl)=C1 CICRBHXWMNTOFT-UHFFFAOYSA-N 0.000 claims 2
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KJTFKCUCRGSOQF-UHFFFAOYSA-N C(C)(=O)O.ClCC(CC1OC2=C(C(=CC=C2)OC)C=2C1=C1C(=CC(NC1=CC2)(C)C)C)=C Chemical compound C(C)(=O)O.ClCC(CC1OC2=C(C(=CC=C2)OC)C=2C1=C1C(=CC(NC1=CC2)(C)C)C)=C KJTFKCUCRGSOQF-UHFFFAOYSA-N 0.000 claims 2
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HHFIVLGVJXIPDS-VIZOYTHASA-N methyl (e)-2-(10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinolin-5-yl)but-2-enoate Chemical compound N1C(C)(C)C=C(C)C2=C3C(/C(=C\C)C(=O)OC)OC4=CC=CC(OC)=C4C3=CC=C21 HHFIVLGVJXIPDS-VIZOYTHASA-N 0.000 claims 2
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DJGBKUNGXYZODB-UHFFFAOYSA-N 1-[3-(10-methoxy-2,2,4-trimethyl-1,5-dihydrochromeno[3,4-f]quinolin-5-yl)-5-methylphenyl]ethanone Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=CC=CC=1OC2C1=CC(C)=CC(C(C)=O)=C1 DJGBKUNGXYZODB-UHFFFAOYSA-N 0.000 claims 1
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238000004809 thin layer chromatography Methods 0.000 description 1
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231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000000844 transformation Methods 0.000 description 1
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150000003624 transition metals Chemical class 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
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YLGRTLMDMVAFNI-UHFFFAOYSA-N tributyl(prop-2-enyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)CC=C YLGRTLMDMVAFNI-UHFFFAOYSA-N 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
125000006168 tricyclic group Chemical group 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
229940030010 trimethoxybenzene Drugs 0.000 description 1
AFFPCIMDERUIST-UHFFFAOYSA-N trimethyl(1-phenylethenoxy)silane Chemical group C[Si](C)(C)OC(=C)C1=CC=CC=C1 AFFPCIMDERUIST-UHFFFAOYSA-N 0.000 description 1
YKXTUAGSORHHEC-UHFFFAOYSA-N trimethyl(3-methylbut-2-enyl)silane Chemical compound CC(C)=CC[Si](C)(C)C YKXTUAGSORHHEC-UHFFFAOYSA-N 0.000 description 1
UAIFZYSPVVBOPN-UHFFFAOYSA-N trimethyl(prop-1-en-2-yloxy)silane Chemical compound CC(=C)O[Si](C)(C)C UAIFZYSPVVBOPN-UHFFFAOYSA-N 0.000 description 1
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
XMQSELBBYSAURN-UHFFFAOYSA-M triphenyl(propyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCC)C1=CC=CC=C1 XMQSELBBYSAURN-UHFFFAOYSA-M 0.000 description 1
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
241000701447 unidentified baculovirus Species 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SK1197-2000A 1998-02-13 1999-02-12 Benzopyrano[3,4-f]chinolínová zlúčenina a liečivo s jej obsahom SK284689B6 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US2394798A	1998-02-13	1998-02-13
US24783199A	1999-02-10	1999-02-10
PCT/US1999/003127 WO1999041256A1 (en)	1998-02-13	1999-02-12	Glucocorticoid-selective anti-inflammatory agents

Publications (2)

Publication Number	Publication Date
SK11972000A3 SK11972000A3 (sk)	2001-08-06
SK284689B6 true SK284689B6 (sk)	2005-09-08

Family

ID=26697833

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1197-2000A SK284689B6 (sk)	1998-02-13	1999-02-12	Benzopyrano[3,4-f]chinolínová zlúčenina a liečivo s jej obsahom

Country Status (20)

Country	Link
EP (1)	EP1053239B1 (de)
JP (1)	JP2002503665A (de)
KR (1)	KR20010040935A (de)
CN (1)	CN1119348C (de)
AT (1)	ATE230749T1 (de)
AU (1)	AU766441B2 (de)
BG (1)	BG64317B1 (de)
BR (1)	BR9907788A (de)
CA (1)	CA2320943A1 (de)
DE (1)	DE69904804T2 (de)
DK (1)	DK1053239T3 (de)
ES (1)	ES2192035T3 (de)
HU (1)	HUP0100460A3 (de)
IL (1)	IL137508A0 (de)
NO (1)	NO20004053L (de)
NZ (1)	NZ506013A (de)
PL (1)	PL193323B1 (de)
SK (1)	SK284689B6 (de)
TR (1)	TR200003094T2 (de)
WO (1)	WO1999041256A1 (de)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6506766B1 (en)	1998-02-13	2003-01-14	Abbott Laboratories	Glucocortiocoid-selective antinflammatory agents
US6329534B1 (en)	1999-09-01	2001-12-11	Abbott Laboratories	Glucocorticoid receptor antagonists for treatment of diabetes
US6593480B2 (en) *	1999-09-01	2003-07-15	Abbott Laboratories	Glucocorticoid receptor antagonists for treatment of diabetes
CO5180649A1 (es) *	1999-09-01	2002-07-30	Abbott Lab	Antagonistas de los receptores de los glucocorticoides para el tratamiento de la diabetes para el tratamiento de la diabetes
US6436986B1 (en)	1999-09-01	2002-08-20	Abbott Laboratories	Glucocorticoid receptor antagonists for treatment of diabetes
ES2246292T3 (es)	2000-10-30	2006-02-16	Pfizer Products Inc.	Moduladores de receptor glucocorticoide.
US6608216B2 (en)	2001-06-29	2003-08-19	Abbott Laboratories	Process for the preparation of chiral glucocorticoid receptor agents
WO2003002548A1 (en) *	2001-06-29	2003-01-09	Abbott Laboratories	A process for the preparation of chiral glucocorticoid receptor agents
US6518430B1 (en) *	2001-09-21	2003-02-11	Abbott Laboratories	Process for the preparation of 5-(substituted)-10-methoxy-2,2,4-trimethyl-2,5-dihydro-1H-chromeno[3,4-F]quinolines and derivatives thereof
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- 1999-02-12 AT AT99906996T patent/ATE230749T1/de active
- 1999-02-12 JP JP2000531449A patent/JP2002503665A/ja active Pending
- 1999-02-12 KR KR1020007008850A patent/KR20010040935A/ko not_active Ceased
- 1999-02-12 CN CN99804902A patent/CN1119348C/zh not_active Expired - Fee Related
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- 1999-02-12 IL IL13750899A patent/IL137508A0/xx unknown
- 1999-02-12 PL PL343018A patent/PL193323B1/pl not_active IP Right Cessation
- 1999-02-12 CA CA002320943A patent/CA2320943A1/en not_active Abandoned
- 1999-02-12 EP EP99906996A patent/EP1053239B1/de not_active Expired - Lifetime
- 1999-02-12 AU AU26773/99A patent/AU766441B2/en not_active Ceased
- 1999-02-12 WO PCT/US1999/003127 patent/WO1999041256A1/en not_active Ceased
- 1999-02-12 TR TR2000/03094T patent/TR200003094T2/xx unknown
- 1999-02-12 DK DK99906996T patent/DK1053239T3/da active
- 1999-02-12 DE DE69904804T patent/DE69904804T2/de not_active Expired - Lifetime
- 1999-02-12 HU HU0100460A patent/HUP0100460A3/hu unknown
- 1999-02-12 BR BR9907788-4A patent/BR9907788A/pt not_active Application Discontinuation
- 1999-02-12 ES ES99906996T patent/ES2192035T3/es not_active Expired - Lifetime
2000
- 2000-08-11 NO NO20004053A patent/NO20004053L/no not_active Application Discontinuation
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Also Published As

Publication number	Publication date
EP1053239B1 (de)	2003-01-08
BR9907788A (pt)	2001-10-30
PL343018A1 (en)	2001-07-30
IL137508A0 (en)	2001-07-24
NZ506013A (en)	2003-03-28
HUP0100460A3 (en)	2003-03-28
DK1053239T3 (da)	2003-04-22
CA2320943A1 (en)	1999-09-19
NO20004053L (no)	2000-09-11
SK11972000A3 (sk)	2001-08-06
WO1999041256A1 (en)	1999-08-19
NO20004053D0 (no)	2000-08-11
BG104719A (en)	2001-05-31
AU2677399A (en)	1999-08-30
CN1296486A (zh)	2001-05-23
TR200003094T2 (tr)	2001-01-22
KR20010040935A (ko)	2001-05-15
AU766441B2 (en)	2003-10-16
HUP0100460A2 (hu)	2001-09-28
DE69904804T2 (de)	2003-11-06
EP1053239A1 (de)	2000-11-22
HK1033308A1 (en)	2001-08-24
CN1119348C (zh)	2003-08-27
DE69904804D1 (de)	2003-02-13
ES2192035T3 (es)	2003-09-16
ATE230749T1 (de)	2003-01-15
PL193323B1 (pl)	2007-02-28
JP2002503665A (ja)	2002-02-05
BG64317B1 (bg)	2004-09-30

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