SK13412000A3 - Deriváty benzofuryl-alfa-pyrónu, farmaceutické prostriedky, synergisty, inhibítory a činidlá - Google Patents

Info

Publication number

SK13412000A3

SK13412000A3 SK1341-2000A SK13412000A SK13412000A3 SK 13412000 A3 SK13412000 A3 SK 13412000A3 SK 13412000 A SK13412000 A SK 13412000A SK 13412000 A3 SK13412000 A3 SK 13412000A3

Authority

SK

Slovakia

Prior art keywords

carbon atoms

heterocycle

group

pyran

dimethyl

Prior art date

1998-03-12

Links

• Espacenet
• Global Dossier
• Discuss

• SKPOULXOGAGECM-UHFFFAOYSA-N 3-(1-benzofuran-2-yl)pyran-2-one Chemical class O=C1OC=CC=C1C1=CC2=CC=CC=C2O1 SKPOULXOGAGECM-UHFFFAOYSA-N 0.000 title 1
• 239000001257 hydrogen Substances 0.000 claims abstract description 141
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 141
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 123
• 150000003839 salts Chemical class 0.000 claims abstract description 45
• 125000001424 substituent group Chemical group 0.000 claims abstract description 40
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 36
• 208000011775 arteriosclerosis disease Diseases 0.000 claims abstract description 10
• 206010003210 Arteriosclerosis Diseases 0.000 claims abstract description 9
• 230000000069 prophylactic effect Effects 0.000 claims abstract description 9
• 230000037356 lipid metabolism Effects 0.000 claims abstract description 7
• IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims abstract description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
• -1 phenoxy, benzyloxy Chemical group 0.000 claims description 638
• 125000004432 carbon atom Chemical group C* 0.000 claims description 354
• 125000000623 heterocyclic group Chemical group 0.000 claims description 187
• 150000002431 hydrogen Chemical class 0.000 claims description 103
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 82
• 230000015572 biosynthetic process Effects 0.000 claims description 60
• 125000003118 aryl group Chemical group 0.000 claims description 58
• 125000003545 alkoxy group Chemical group 0.000 claims description 57
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 46
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
• 125000001624 naphthyl group Chemical group 0.000 claims description 37
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 36
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 30
• 239000008280 blood Substances 0.000 claims description 27
• 210000004369 blood Anatomy 0.000 claims description 27
• 229910052736 halogen Inorganic materials 0.000 claims description 25
• UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 25
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 22
• 125000004104 aryloxy group Chemical group 0.000 claims description 21
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
• 239000004480 active ingredient Substances 0.000 claims description 19
• 239000003795 chemical substances by application Substances 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 16
• 125000002252 acyl group Chemical group 0.000 claims description 15
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 15
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 15
• 125000005843 halogen group Chemical group 0.000 claims description 15
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 11
• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 11
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 11
• 125000004193 piperazinyl group Chemical group 0.000 claims description 10
• 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 9
• 125000000304 alkynyl group Chemical group 0.000 claims description 9
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 9
• 125000002541 furyl group Chemical group 0.000 claims description 9
• 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 9
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 8
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
• 125000002757 morpholinyl group Chemical group 0.000 claims description 8
• 125000001544 thienyl group Chemical group 0.000 claims description 8
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
• 125000001072 heteroaryl 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
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
• 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 6
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
• 125000004442 acylamino group Chemical group 0.000 claims description 5
• 125000004429 atom Chemical group 0.000 claims description 5
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
• 239000003112 inhibitor Substances 0.000 claims description 5
• 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 5
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 5
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• 125000004423 acyloxy group Chemical group 0.000 claims description 4
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
• 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 4
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
• 239000008194 pharmaceutical composition Substances 0.000 claims description 3
• 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 2
• 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 2
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
• YDBQJGWNFSPUNX-UHFFFAOYSA-N [O-][N+](=O)BrC#N Chemical compound [O-][N+](=O)BrC#N YDBQJGWNFSPUNX-UHFFFAOYSA-N 0.000 claims 2
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 1
• 125000005976 1-phenylethyloxy group Chemical group 0.000 claims 1
• 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims 1
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims 1
• 125000002723 alicyclic group Chemical group 0.000 claims 1
• 239000003638 chemical reducing agent Substances 0.000 claims 1
• 125000004981 cycloalkylmethyl group Chemical group 0.000 claims 1
• 150000001875 compounds Chemical class 0.000 abstract description 20
• 239000003814 drug Substances 0.000 abstract description 19
• 208000006575 hypertriglyceridemia Diseases 0.000 abstract description 9
• 229910052799 carbon Inorganic materials 0.000 abstract description 7
• 229940124597 therapeutic agent Drugs 0.000 abstract description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 3
• 239000003623 enhancer Substances 0.000 abstract 1
• 238000004458 analytical method Methods 0.000 description 181
• 239000000243 solution Substances 0.000 description 125
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 83
• VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 80
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 76
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 72
• 239000000203 mixture Substances 0.000 description 65
• 238000003786 synthesis reaction Methods 0.000 description 51
• 238000006243 chemical reaction Methods 0.000 description 45
• ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical class O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 43
• 239000012044 organic layer Substances 0.000 description 39
• 125000004244 benzofuran-2-yl group Chemical group [H]C1=C(*)OC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 36
• 238000010898 silica gel chromatography Methods 0.000 description 35
• 238000004519 manufacturing process Methods 0.000 description 33
• 238000000034 method Methods 0.000 description 29
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
• 239000011541 reaction mixture Substances 0.000 description 25
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
• 238000003756 stirring Methods 0.000 description 24
• 150000003626 triacylglycerols Chemical class 0.000 description 23
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 22
• 239000000460 chlorine Substances 0.000 description 22
• 238000000605 extraction Methods 0.000 description 22
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
• 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 description 16
• 229920006395 saturated elastomer Polymers 0.000 description 16
• KYPMTIQWDKIHOG-UHFFFAOYSA-N 6-(1-benzofuran-2-yl)-4-hydroxy-3,5-dimethylpyran-2-one Chemical compound OC1=C(C)C(=O)OC(C=2OC3=CC=CC=C3C=2)=C1C KYPMTIQWDKIHOG-UHFFFAOYSA-N 0.000 description 15
• 238000001816 cooling Methods 0.000 description 15
• 239000000725 suspension Substances 0.000 description 15
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 14
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• 108010010234 HDL Lipoproteins Proteins 0.000 description 12
• 239000002253 acid Substances 0.000 description 12
• 239000000543 intermediate Substances 0.000 description 12
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
• 239000011734 sodium Substances 0.000 description 12
• 239000007864 aqueous solution Substances 0.000 description 11
• 229940079593 drug Drugs 0.000 description 11
• 125000004076 pyridyl group Chemical group 0.000 description 11
• 239000000126 substance Substances 0.000 description 11
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• 230000002401 inhibitory effect Effects 0.000 description 10
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 10
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 10
• 238000002360 preparation method Methods 0.000 description 10
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
• 239000010410 layer Substances 0.000 description 9
• 239000012452 mother liquor Substances 0.000 description 9
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 9
• 125000000335 thiazolyl group Chemical group 0.000 description 9
• 238000004809 thin layer chromatography Methods 0.000 description 9
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 8
• 239000013078 crystal Substances 0.000 description 8
• DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 8
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 8
• 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 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
• 229910052794 bromium Inorganic materials 0.000 description 7
• 235000012000 cholesterol Nutrition 0.000 description 7
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
• AVNZOGNVFGETNQ-UHFFFAOYSA-N methyl 2-methyl-3-oxopentanoate Chemical compound CCC(=O)C(C)C(=O)OC AVNZOGNVFGETNQ-UHFFFAOYSA-N 0.000 description 7
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 7
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
• 241000700159 Rattus Species 0.000 description 6
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
• 125000002632 imidazolidinyl group Chemical group 0.000 description 6
• 230000001965 increasing effect Effects 0.000 description 6
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
• 230000008569 process Effects 0.000 description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 description 6
• 239000007787 solid Substances 0.000 description 6
• 239000007858 starting material Substances 0.000 description 6
• 238000011282 treatment Methods 0.000 description 6
• XHSRMZQYNJMYLS-UHFFFAOYSA-N 6-(5-amino-1-benzofuran-2-yl)-4-(methoxymethoxy)-3,5-dimethylpyran-2-one Chemical compound O1C(=O)C(C)=C(OCOC)C(C)=C1C1=CC2=CC(N)=CC=C2O1 XHSRMZQYNJMYLS-UHFFFAOYSA-N 0.000 description 5
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
• 208000031226 Hyperlipidaemia Diseases 0.000 description 5
• 108090001030 Lipoproteins Proteins 0.000 description 5
• 102000004895 Lipoproteins Human genes 0.000 description 5
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
• 125000005129 aryl carbonyl group Chemical group 0.000 description 5
• 239000012298 atmosphere Substances 0.000 description 5
• 210000004027 cell Anatomy 0.000 description 5
• 229910052801 chlorine Inorganic materials 0.000 description 5
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
• 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
• 125000002883 imidazolyl group Chemical group 0.000 description 5
• 229910052740 iodine Inorganic materials 0.000 description 5
• 239000011630 iodine Substances 0.000 description 5
• 125000001786 isothiazolyl group Chemical group 0.000 description 5
• 125000000842 isoxazolyl group Chemical group 0.000 description 5
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
• 229910052763 palladium Inorganic materials 0.000 description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
• 125000003373 pyrazinyl group Chemical group 0.000 description 5
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
• 238000012360 testing method Methods 0.000 description 5
• 125000001984 thiazolidinyl group Chemical group 0.000 description 5
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 4
• WZUODJNEIXSNEU-UHFFFAOYSA-N 2-Hydroxy-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(O)=C1 WZUODJNEIXSNEU-UHFFFAOYSA-N 0.000 description 4
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 4
• 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 4
• PZPVCEZVXKWRRK-UHFFFAOYSA-N 5-[[2-(4-hydroxy-3,5-dimethyl-6-oxopyran-2-yl)-1-benzofuran-5-yl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound OC1=C(C)C(=O)OC(C=2OC3=CC=C(C=C4C(NC(=O)S4)=O)C=C3C=2)=C1C PZPVCEZVXKWRRK-UHFFFAOYSA-N 0.000 description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
• OFFSPAZVIVZPHU-UHFFFAOYSA-N Benzofurane-2-carboxylic acid Natural products C1=CC=C2OC(C(=O)O)=CC2=C1 OFFSPAZVIVZPHU-UHFFFAOYSA-N 0.000 description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
• CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
• 108010013563 Lipoprotein Lipase Proteins 0.000 description 4
• 102000043296 Lipoprotein lipases Human genes 0.000 description 4
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
• UCEOLGNAHBHVCF-UHFFFAOYSA-N [2-(1-benzofuran-2-yl)-3,5-dimethyl-6-oxopyran-4-yl] acetate Chemical compound O1C(=O)C(C)=C(OC(=O)C)C(C)=C1C1=CC2=CC=CC=C2O1 UCEOLGNAHBHVCF-UHFFFAOYSA-N 0.000 description 4
• ZSLZBFCDCINBPY-ZSJPKINUSA-N acetyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 ZSLZBFCDCINBPY-ZSJPKINUSA-N 0.000 description 4
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 4
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 4
• 125000003277 amino group Chemical class 0.000 description 4
• 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
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