SK9492003A3 - Combinations of sterol absorption inhibitor(s) with cardiovascular agent(s) for the treatment of vascular conditions - Google Patents

Info

Publication number

SK9492003A3

SK9492003A3 SK949-2003A SK9492003A SK9492003A3 SK 9492003 A3 SK9492003 A3 SK 9492003A3 SK 9492003 A SK9492003 A SK 9492003A SK 9492003 A3 SK9492003 A3 SK 9492003A3

Authority

SK

Slovakia

Prior art keywords

alkyl

group

aryl

hydrochloride

substituted

Prior art date

2001-01-26

Links

• Espacenet
• Global Dossier
• Discuss

• 150000003432 sterols Chemical class 0.000 title claims abstract description 134
• 239000003112 inhibitor Substances 0.000 title claims abstract description 113
• 229930182558 Sterol Natural products 0.000 title claims abstract description 101
• 235000003702 sterols Nutrition 0.000 title claims abstract description 101
• 238000010521 absorption reaction Methods 0.000 title claims abstract description 80
• 239000002327 cardiovascular agent Substances 0.000 title claims abstract description 50
• 229940125692 cardiovascular agent Drugs 0.000 title claims abstract description 50
• 230000002792 vascular Effects 0.000 title claims abstract description 29
• 238000011282 treatment Methods 0.000 title claims description 42
• 239000000203 mixture Substances 0.000 claims abstract description 117
• 230000001225 therapeutic effect Effects 0.000 claims abstract description 46
• 238000000034 method Methods 0.000 claims abstract description 42
• 208000008589 Obesity Diseases 0.000 claims abstract description 19
• 235000020824 obesity Nutrition 0.000 claims abstract description 19
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 13
• 230000036470 plasma concentration Effects 0.000 claims abstract description 5
• 150000001875 compounds Chemical class 0.000 claims description 206
• 125000000217 alkyl group Chemical group 0.000 claims description 159
• -1 R-substituted benzyloxy Chemical group 0.000 claims description 157
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 126
• 229910052739 hydrogen Inorganic materials 0.000 claims description 106
• 125000003118 aryl group Chemical group 0.000 claims description 88
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 88
• 150000003839 salts Chemical class 0.000 claims description 77
• 125000001424 substituent group Chemical group 0.000 claims description 71
• 239000001257 hydrogen Substances 0.000 claims description 69
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 61
• 229910052736 halogen Inorganic materials 0.000 claims description 61
• 239000012453 solvate Substances 0.000 claims description 57
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 52
• 150000002367 halogens Chemical class 0.000 claims description 52
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 46
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 35
• 125000003545 alkoxy group Chemical group 0.000 claims description 35
• 229940002612 prodrug Drugs 0.000 claims description 35
• 239000000651 prodrug Substances 0.000 claims description 35
• 235000012000 cholesterol Nutrition 0.000 claims description 31
• 125000002947 alkylene group Chemical group 0.000 claims description 30
• 125000001072 heteroaryl group Chemical class 0.000 claims description 26
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
• 230000015572 biosynthetic process Effects 0.000 claims description 24
• 239000012190 activator Substances 0.000 claims description 22
• 241000124008 Mammalia Species 0.000 claims description 20
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 19
• MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims description 16
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 15
• 125000004432 carbon atom Chemical group C* 0.000 claims description 15
• 125000005843 halogen group Chemical group 0.000 claims description 15
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
• 125000001544 thienyl group Chemical group 0.000 claims description 13
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 12
• 125000004076 pyridyl group Chemical group 0.000 claims description 12
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 125000003003 spiro group Chemical group 0.000 claims description 11
• UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 claims description 10
• 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 claims description 10
• 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 claims description 10
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 10
• 239000000460 chlorine Substances 0.000 claims description 10
• 125000002883 imidazolyl group Chemical group 0.000 claims description 10
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 10
• IBBLRJGOOANPTQ-JKVLGAQCSA-N quinapril hydrochloride Chemical compound Cl.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)CC1=CC=CC=C1 IBBLRJGOOANPTQ-JKVLGAQCSA-N 0.000 claims description 10
• 229960003042 quinapril hydrochloride Drugs 0.000 claims description 10
• 125000000335 thiazolyl group Chemical group 0.000 claims description 10
• GHOSNRCGJFBJIB-UHFFFAOYSA-N Candesartan cilexetil Chemical compound C=12N(CC=3C=CC(=CC=3)C=3C(=CC=CC=3)C3=NNN=N3)C(OCC)=NC2=CC=CC=1C(=O)OC(C)OC(=O)OC1CCCCC1 GHOSNRCGJFBJIB-UHFFFAOYSA-N 0.000 claims description 9
• 239000002333 angiotensin II receptor antagonist Substances 0.000 claims description 9
• 125000002541 furyl group Chemical group 0.000 claims description 9
• 125000002757 morpholinyl group Chemical group 0.000 claims description 9
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
• 125000003386 piperidinyl group Chemical group 0.000 claims description 9
• 239000011734 sodium Substances 0.000 claims description 9
• 229910052708 sodium Inorganic materials 0.000 claims description 9
• RMMXLENWKUUMAY-UHFFFAOYSA-N telmisartan Chemical compound CCCC1=NC2=C(C)C=C(C=3N(C4=CC=CC=C4N=3)C)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1C(O)=O RMMXLENWKUUMAY-UHFFFAOYSA-N 0.000 claims description 9
• GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 claims description 8
• ZNIFSRGNXRYGHF-UHFFFAOYSA-N Clonidine hydrochloride Chemical compound Cl.ClC1=CC=CC(Cl)=C1NC1=NCCN1 ZNIFSRGNXRYGHF-UHFFFAOYSA-N 0.000 claims description 8
• 239000000674 adrenergic antagonist Substances 0.000 claims description 8
• 125000003282 alkyl amino group Chemical group 0.000 claims description 8
• 229940030600 antihypertensive agent Drugs 0.000 claims description 8
• 239000002220 antihypertensive agent Substances 0.000 claims description 8
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 8
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 7
• 229940127291 Calcium channel antagonist Drugs 0.000 claims description 7
• JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical group C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 claims description 7
• FDJCVHVKXFIEPJ-JCNFZFLDSA-N Delapril hydrochloride Chemical compound Cl.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N(CC(O)=O)C1CC2=CC=CC=C2C1)CC1=CC=CC=C1 FDJCVHVKXFIEPJ-JCNFZFLDSA-N 0.000 claims description 7
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
• 239000000480 calcium channel blocker Substances 0.000 claims description 7
• 150000001721 carbon Chemical group 0.000 claims description 7
• 239000011737 fluorine Substances 0.000 claims description 7
• 229910052731 fluorine Inorganic materials 0.000 claims description 7
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 7
• XLFWDASMENKTKL-UHFFFAOYSA-N molsidomine Chemical compound O1C(N=C([O-])OCC)=C[N+](N2CCOCC2)=N1 XLFWDASMENKTKL-UHFFFAOYSA-N 0.000 claims description 7
• 125000001624 naphthyl group Chemical group 0.000 claims description 7
• HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 claims description 7
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
• RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 claims description 7
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 7
• SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 claims description 6
• 239000002053 C09CA06 - Candesartan Substances 0.000 claims 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 claims description 6
• 102000000853 LDL receptors Human genes 0.000 claims description 6
• 108010001831 LDL receptors Proteins 0.000 claims description 6
• RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 claims description 6
• DOQPXTMNIUCOSY-UHFFFAOYSA-N [4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl]-[2-(3,4-dimethoxyphenyl)ethyl]-methylazanium;chloride Chemical compound [H+].[Cl-].C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 DOQPXTMNIUCOSY-UHFFFAOYSA-N 0.000 claims description 6
• 229920000080 bile acid sequestrant Polymers 0.000 claims description 6
• 229960000932 candesartan Drugs 0.000 claims description 6
• FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 claims description 6
• 229960002925 clonidine hydrochloride Drugs 0.000 claims description 6
• 239000003218 coronary vasodilator agent Substances 0.000 claims description 6
• 239000002934 diuretic Substances 0.000 claims description 6
• 125000000592 heterocycloalkyl group Chemical class 0.000 claims description 6
• YWXYYJSYQOXTPL-SLPGGIOYSA-N isosorbide mononitrate Chemical compound [O-][N+](=O)O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-SLPGGIOYSA-N 0.000 claims description 6
• RLAWWYSOJDYHDC-BZSNNMDCSA-N lisinopril Chemical compound C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 RLAWWYSOJDYHDC-BZSNNMDCSA-N 0.000 claims description 6
• 125000002971 oxazolyl group Chemical group 0.000 claims description 6
• FLSLEGPOVLMJMN-YSSFQJQWSA-N quinaprilat Chemical compound C([C@H](N[C@@H](C)C(=O)N1[C@@H](CC2=CC=CC=C2C1)C(O)=O)C(O)=O)CC1=CC=CC=C1 FLSLEGPOVLMJMN-YSSFQJQWSA-N 0.000 claims description 6
• 229920006395 saturated elastomer Polymers 0.000 claims description 6
• 229960002855 simvastatin Drugs 0.000 claims description 6
• YKFCISHFRZHKHY-NGQGLHOPSA-N (2s)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid;trihydrate Chemical compound O.O.O.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 YKFCISHFRZHKHY-NGQGLHOPSA-N 0.000 claims description 5
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
• DGFYECXYGUIODH-UHFFFAOYSA-N Guanfacine hydrochloride Chemical compound Cl.NC(N)=NC(=O)CC1=C(Cl)C=CC=C1Cl DGFYECXYGUIODH-UHFFFAOYSA-N 0.000 claims description 5
• WQVZLXWQESQGIF-UHFFFAOYSA-N Labetalol hydrochloride Chemical compound Cl.C=1C=C(O)C(C(N)=O)=CC=1C(O)CNC(C)CCC1=CC=CC=C1 WQVZLXWQESQGIF-UHFFFAOYSA-N 0.000 claims description 5
• JXRAXHBVZQZSIC-JKVLGAQCSA-N Moexipril hydrochloride Chemical compound Cl.C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CC2=CC(OC)=C(OC)C=C2C1)C(O)=O)CC1=CC=CC=C1 JXRAXHBVZQZSIC-JKVLGAQCSA-N 0.000 claims description 5
• PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 claims description 5
• 230000001800 adrenalinergic effect Effects 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• ZPBWCRDSRKPIDG-UHFFFAOYSA-N amlodipine benzenesulfonate Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl ZPBWCRDSRKPIDG-UHFFFAOYSA-N 0.000 claims description 5
• 102000012740 beta Adrenergic Receptors Human genes 0.000 claims description 5
• 108010079452 beta Adrenergic Receptors Proteins 0.000 claims description 5
• KVWNWTZZBKCOPM-UHFFFAOYSA-M bretylium tosylate Chemical group CC1=CC=C(S([O-])(=O)=O)C=C1.CC[N+](C)(C)CC1=CC=CC=C1Br KVWNWTZZBKCOPM-UHFFFAOYSA-M 0.000 claims description 5
• 229960004195 carvedilol Drugs 0.000 claims description 5
• 229940083181 centrally acting adntiadrenergic agent methyldopa Drugs 0.000 claims description 5
• 229910052801 chlorine Inorganic materials 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• WQVZLXWQESQGIF-WJKBNZMCSA-N dilevalol hydrochloride Chemical compound Cl.C([C@@H](C)NC[C@H](O)C=1C=C(C(O)=CC=1)C(N)=O)CC1=CC=CC=C1 WQVZLXWQESQGIF-WJKBNZMCSA-N 0.000 claims description 5
• 125000001475 halogen functional group Chemical group 0.000 claims description 5
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 5
• 229960003091 labetalol hydrochloride Drugs 0.000 claims description 5
• PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 claims description 5
• IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 claims description 5
• IPVQLZZIHOAWMC-QXKUPLGCSA-N perindopril Chemical compound C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H]21 IPVQLZZIHOAWMC-QXKUPLGCSA-N 0.000 claims description 5
• FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 claims description 5
• 229960003912 probucol Drugs 0.000 claims description 5
• HDACQVRGBOVJII-JBDAPHQKSA-N ramipril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](C[C@@H]2CCC[C@@H]21)C(O)=O)CC1=CC=CC=C1 HDACQVRGBOVJII-JBDAPHQKSA-N 0.000 claims description 5
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 4
• RZPZLFIUFMNCLY-WLHGVMLRSA-N (e)-but-2-enedioic acid;1-(propan-2-ylamino)-3-[4-(2-propan-2-yloxyethoxymethyl)phenoxy]propan-2-ol Chemical compound OC(=O)\C=C\C(O)=O.CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1 RZPZLFIUFMNCLY-WLHGVMLRSA-N 0.000 claims description 4
• JDZOTSLZMQDFLG-BTJKTKAUSA-N (z)-but-2-enedioic acid;2-(2,2-dicyclohexylethyl)piperidine Chemical compound OC(=O)\C=C/C(O)=O.C1CCCNC1CC(C1CCCCC1)C1CCCCC1 JDZOTSLZMQDFLG-BTJKTKAUSA-N 0.000 claims description 4
• SKQDKFOTIPJUSV-UHFFFAOYSA-N 4-[2-[[2-hydroxy-3-(2-methylphenoxy)propyl]amino]ethoxy]benzamide Chemical compound CC1=CC=CC=C1OCC(O)CNCCOC1=CC=C(C(N)=O)C=C1 SKQDKFOTIPJUSV-UHFFFAOYSA-N 0.000 claims description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 4
• RGHAZVBIOOEVQX-UHFFFAOYSA-N Metoprolol succinate Chemical compound OC(=O)CCC(O)=O.COCCC1=CC=C(OCC(O)CNC(C)C)C=C1.COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 RGHAZVBIOOEVQX-UHFFFAOYSA-N 0.000 claims description 4
• DXHWOBBGGCYHNV-UHFFFAOYSA-N [4-[3-(dibutylamino)propoxy]phenyl]-(2-ethylindolizin-3-yl)methanone;hydron;chloride Chemical compound Cl.C1=CC(OCCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CC)C=C2N1C=CC=C2 DXHWOBBGGCYHNV-UHFFFAOYSA-N 0.000 claims description 4
• GOEMGAFJFRBGGG-UHFFFAOYSA-N acebutolol Chemical compound CCCC(=O)NC1=CC=C(OCC(O)CNC(C)C)C(C(C)=O)=C1 GOEMGAFJFRBGGG-UHFFFAOYSA-N 0.000 claims description 4
• 125000004414 alkyl thio group Chemical group 0.000 claims description 4
• 125000005529 alkyleneoxy group Chemical group 0.000 claims description 4
• 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 4
• 239000004004 anti-anginal agent Substances 0.000 claims description 4
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• 239000003963 antioxidant agent Substances 0.000 claims description 4
• 125000004104 aryloxy group Chemical class 0.000 claims description 4
• 125000002047 benzodioxolyl group Chemical class O1OC(C2=C1C=CC=C2)* 0.000 claims description 4
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
• NDTSRXAMMQDVSW-UHFFFAOYSA-N benzthiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1N=C2CSCC1=CC=CC=C1 NDTSRXAMMQDVSW-UHFFFAOYSA-N 0.000 claims description 4
• VHYCDWMUTMEGQY-UHFFFAOYSA-N bisoprolol Chemical compound CC(C)NCC(O)COC1=CC=C(COCCOC(C)C)C=C1 VHYCDWMUTMEGQY-UHFFFAOYSA-N 0.000 claims description 4
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• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• VMZCXIGDNRMWGI-GEEYTBSJSA-N diethyl 2-[(dimethylamino)methyl]-6-methyl-4-[2-[(e)-3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]phenyl]-1,4-dihydropyridine-3,5-dicarboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1=C(C)NC(CN(C)C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C VMZCXIGDNRMWGI-GEEYTBSJSA-N 0.000 claims description 4
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