HRP20000600A2 - Benzofurylpyrone derivatives - Google Patents
Benzofurylpyrone derivatives Download PDFInfo
- Publication number
- HRP20000600A2 HRP20000600A2 HR20000600A HRP20000600A HRP20000600A2 HR P20000600 A2 HRP20000600 A2 HR P20000600A2 HR 20000600 A HR20000600 A HR 20000600A HR P20000600 A HRP20000600 A HR P20000600A HR P20000600 A2 HRP20000600 A2 HR P20000600A2
- Authority
- HR
- Croatia
- Prior art keywords
- group
- carbon atoms
- pyran
- denotes
- dimethyl
- Prior art date
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- 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 140
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 140
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 133
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 50
- 150000003839 salts Chemical class 0.000 claims abstract description 44
- 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 29
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000003623 enhancer Substances 0.000 claims abstract description 7
- 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 5
- -1 diethylaminosulfonyl group Chemical group 0.000 claims description 545
- 125000004432 carbon atom Chemical group C* 0.000 claims description 402
- 125000000623 heterocyclic group Chemical group 0.000 claims description 186
- 150000002431 hydrogen Chemical class 0.000 claims description 108
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 79
- 125000003118 aryl group Chemical group 0.000 claims description 64
- 230000015572 biosynthetic process Effects 0.000 claims description 58
- 238000003786 synthesis reaction Methods 0.000 claims description 55
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 43
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 42
- 150000003626 triacylglycerols Chemical class 0.000 claims description 41
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- 125000001624 naphthyl group Chemical group 0.000 claims description 35
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 28
- 239000008280 blood Substances 0.000 claims description 26
- 210000004369 blood Anatomy 0.000 claims description 26
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 23
- 125000004390 alkyl sulfonyl group Chemical class 0.000 claims description 22
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 125000004104 aryloxy group Chemical group 0.000 claims description 21
- 229920006395 saturated elastomer Polymers 0.000 claims description 21
- 125000006848 alicyclic heterocyclic group Chemical group 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 201000001320 Atherosclerosis Diseases 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 15
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 13
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 11
- 239000004480 active ingredient Substances 0.000 claims description 10
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- 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
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 9
- 125000004193 piperazinyl group Chemical group 0.000 claims description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 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 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 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 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 150000001721 carbon Chemical group 0.000 claims description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 6
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
- 125000004442 acylamino group Chemical group 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000005553 heteroaryloxy group Chemical group 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
- YDBQJGWNFSPUNX-UHFFFAOYSA-N [O-][N+](=O)BrC#N Chemical compound [O-][N+](=O)BrC#N YDBQJGWNFSPUNX-UHFFFAOYSA-N 0.000 claims description 4
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 4
- 239000002131 composite material Substances 0.000 claims description 3
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 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
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 21
- 239000003814 drug Substances 0.000 abstract description 13
- 208000006575 hypertriglyceridemia Diseases 0.000 abstract description 10
- 229940124597 therapeutic agent Drugs 0.000 abstract description 6
- 230000000069 prophylactic effect Effects 0.000 abstract description 4
- 206010003210 Arteriosclerosis Diseases 0.000 abstract 1
- 208000011775 arteriosclerosis disease Diseases 0.000 abstract 1
- 238000004458 analytical method Methods 0.000 description 180
- 239000000243 solution Substances 0.000 description 117
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 83
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 83
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 70
- 239000000203 mixture Substances 0.000 description 62
- 238000006243 chemical reaction Methods 0.000 description 61
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 46
- 238000000034 method Methods 0.000 description 45
- 239000012044 organic layer Substances 0.000 description 37
- 238000010898 silica gel chromatography Methods 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 238000003756 stirring Methods 0.000 description 29
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 238000002360 preparation method Methods 0.000 description 27
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
- 239000007864 aqueous solution Substances 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
- 235000019341 magnesium sulphate Nutrition 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 238000000605 extraction Methods 0.000 description 22
- 239000003795 chemical substances by application Substances 0.000 description 21
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical class O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 239000000725 suspension Substances 0.000 description 15
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 14
- 230000000694 effects Effects 0.000 description 13
- 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 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 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
- 108010010234 HDL Lipoproteins Proteins 0.000 description 11
- 239000013543 active substance Substances 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 239000012452 mother liquor Substances 0.000 description 11
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000010410 layer Substances 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 230000002401 inhibitory effect Effects 0.000 description 9
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 238000004809 thin layer chromatography Methods 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- 239000007832 Na2SO4 Substances 0.000 description 8
- 241000700159 Rattus Species 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 235000012000 cholesterol Nutrition 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 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 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 235000015320 potassium carbonate Nutrition 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 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
- 125000003277 amino group Chemical group 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 7
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 7
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 208000031226 Hyperlipidaemia Diseases 0.000 description 6
- 108090001030 Lipoproteins Proteins 0.000 description 6
- 102000004895 Lipoproteins Human genes 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 235000019270 ammonium chloride Nutrition 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 229910052740 iodine Inorganic materials 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
- 238000004519 manufacturing process Methods 0.000 description 6
- AVNZOGNVFGETNQ-UHFFFAOYSA-N methyl 2-methyl-3-oxopentanoate Chemical compound CCC(=O)C(C)C(=O)OC AVNZOGNVFGETNQ-UHFFFAOYSA-N 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- OFFSPAZVIVZPHU-UHFFFAOYSA-N Benzofurane-2-carboxylic acid Natural products C1=CC=C2OC(C(=O)O)=CC2=C1 OFFSPAZVIVZPHU-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- FAEGTUWJBBZTBP-UHFFFAOYSA-N [3,5-dimethyl-2-oxo-6-[6-(trifluoromethylsulfonyloxy)-1-benzofuran-2-yl]pyran-4-yl] acetate Chemical compound O1C(=O)C(C)=C(OC(=O)C)C(C)=C1C1=CC2=CC=C(OS(=O)(=O)C(F)(F)F)C=C2O1 FAEGTUWJBBZTBP-UHFFFAOYSA-N 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 125000005129 aryl carbonyl group Chemical group 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 125000004851 cyclopentylmethyl group Chemical class C1(CCCC1)C* 0.000 description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
- 125000002632 imidazolidinyl group Chemical group 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 125000001786 isothiazolyl group Chemical group 0.000 description 5
- 125000000160 oxazolidinyl group Chemical group 0.000 description 5
- 125000003373 pyrazinyl group Chemical group 0.000 description 5
- 125000003226 pyrazolyl group Chemical group 0.000 description 5
- 125000000168 pyrrolyl group Chemical group 0.000 description 5
- 239000012266 salt solution Substances 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
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 5
- 125000001984 thiazolidinyl group Chemical group 0.000 description 5
- 125000001425 triazolyl group Chemical group 0.000 description 5
- 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
- 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 4
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 4
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
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- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- QHFFOIFUVFOJPE-UHFFFAOYSA-N tert-butyl 2-[[2-(4-hydroxy-3,5-dimethyl-6-oxopyran-2-yl)-1-benzofuran-5-yl]oxymethyl]piperidine-1-carboxylate Chemical compound OC1=C(C)C(=O)OC(C=2OC3=CC=C(OCC4N(CCCC4)C(=O)OC(C)(C)C)C=C3C=2)=C1C QHFFOIFUVFOJPE-UHFFFAOYSA-N 0.000 description 1
- GXKQNLXDKGTVTJ-UHFFFAOYSA-N tert-butyl 4-[[2-(4-hydroxy-3,5-dimethyl-6-oxopyran-2-yl)-1-benzofuran-5-yl]oxy]piperidine-1-carboxylate Chemical compound OC1=C(C)C(=O)OC(C=2OC3=CC=C(OC4CCN(CC4)C(=O)OC(C)(C)C)C=C3C=2)=C1C GXKQNLXDKGTVTJ-UHFFFAOYSA-N 0.000 description 1
- WUGBIRSKZYGPDM-UHFFFAOYSA-N tert-butyl n-[3-[[2-(4-hydroxy-3,5-dimethyl-6-oxopyran-2-yl)-1-benzofuran-5-yl]oxymethyl]phenyl]carbamate Chemical compound OC1=C(C)C(=O)OC(C=2OC3=CC=C(OCC=4C=C(NC(=O)OC(C)(C)C)C=CC=4)C=C3C=2)=C1C WUGBIRSKZYGPDM-UHFFFAOYSA-N 0.000 description 1
- UWSGENMKKVFGSJ-UHFFFAOYSA-N tert-butyl n-[4-[[2-(4-hydroxy-3,5-dimethyl-6-oxopyran-2-yl)-1-benzofuran-5-yl]oxy]butyl]carbamate Chemical compound OC1=C(C)C(=O)OC(C=2OC3=CC=C(OCCCCNC(=O)OC(C)(C)C)C=C3C=2)=C1C UWSGENMKKVFGSJ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- SANWDQJIWZEKOD-UHFFFAOYSA-N tributyl(furan-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CO1 SANWDQJIWZEKOD-UHFFFAOYSA-N 0.000 description 1
- UKTDFYOZPFNQOQ-UHFFFAOYSA-N tributyl(thiophen-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CS1 UKTDFYOZPFNQOQ-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (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)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Luminescent Compositions (AREA)
- External Artificial Organs (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Farming Of Fish And Shellfish (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP6135698 | 1998-03-12 | ||
PCT/JP1999/001225 WO1999046262A1 (fr) | 1998-03-12 | 1999-03-12 | Derives de benzofurylpyrone |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20000600A2 true HRP20000600A2 (en) | 2001-06-30 |
Family
ID=13168805
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20000600A HRP20000600A2 (en) | 1998-03-12 | 2000-09-12 | Benzofurylpyrone derivatives |
Country Status (25)
Country | Link |
---|---|
US (2) | US6589984B1 (ja) |
EP (1) | EP1063235B1 (ja) |
JP (1) | JP3922884B2 (ja) |
KR (1) | KR100595332B1 (ja) |
CN (1) | CN1170827C (ja) |
AT (1) | ATE266659T1 (ja) |
AU (1) | AU756965B2 (ja) |
BG (1) | BG104761A (ja) |
BR (1) | BR9908706A (ja) |
CA (1) | CA2323456A1 (ja) |
DE (1) | DE69917237T2 (ja) |
EE (1) | EE200000504A (ja) |
HR (1) | HRP20000600A2 (ja) |
HU (1) | HUP0101381A3 (ja) |
ID (1) | ID27511A (ja) |
IL (1) | IL138279A0 (ja) |
IS (1) | IS5617A (ja) |
NO (1) | NO20004517L (ja) |
NZ (1) | NZ506802A (ja) |
PL (1) | PL343419A1 (ja) |
RU (1) | RU2199536C2 (ja) |
SK (1) | SK13412000A3 (ja) |
TR (1) | TR200002642T2 (ja) |
UA (1) | UA58587C2 (ja) |
WO (1) | WO1999046262A1 (ja) |
Families Citing this family (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE266659T1 (de) * | 1998-03-12 | 2004-05-15 | Teijin Ltd | Benzofurylpyron-derivate |
US7179912B2 (en) * | 2000-09-01 | 2007-02-20 | Icos Corporation | Materials and methods to potentiate cancer treatment |
DE10115408A1 (de) * | 2001-03-29 | 2002-10-02 | Bayer Ag | Benzofuran-Derivate |
DK1485377T5 (da) * | 2002-02-25 | 2010-12-06 | Kudos Pharm Ltd | Pyranoner egnede som ATM-inhibitorer |
DE10314610A1 (de) | 2003-04-01 | 2004-11-04 | Aventis Pharma Deutschland Gmbh | Neues Diphenylazetidinon mit verbesserten physiologischen Eigenschaften, Verfahren zu dessen Herstellung, diese Verbindungen enthaltende Arzneimittel und dessen Verwendung |
KR20090047458A (ko) | 2006-08-08 | 2009-05-12 | 사노피-아벤티스 | 아릴아미노아릴-알킬-치환된 이미다졸리딘-2,4-디온, 이의 제조방법, 이들 화합물을 포함하는 약제 및 이의 용도 |
EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
DE102007054497B3 (de) * | 2007-11-13 | 2009-07-23 | Sanofi-Aventis Deutschland Gmbh | Neue kristalline Diphenylazetidinonhydrate und Verfahren zu deren Herstellung |
FR2929276B1 (fr) * | 2008-04-01 | 2010-04-23 | Servier Lab | Nouveaux derives de diosmetine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
US8470841B2 (en) | 2008-07-09 | 2013-06-25 | Sanofi | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
RU2012111354A (ru) | 2009-08-26 | 2013-10-10 | Санофи | Новые кристаллические гидраты фторгликозидов, содержащие их фармацевтические препараты и их использование |
EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
WO2012120050A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
WO2012120058A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
WO2012120057A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
US8809325B2 (en) | 2011-03-08 | 2014-08-19 | Sanofi | Benzyl-oxathiazine derivatives substituted with adamantane and noradamantane, medicaments containing said compounds and use thereof |
EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
US8901114B2 (en) | 2011-03-08 | 2014-12-02 | Sanofi | Oxathiazine derivatives substituted with carbocycles or heterocycles, method for producing same, drugs containing said compounds, and use thereof |
WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
WO2012120054A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
US8828995B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Branched oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
DE102014214016A1 (de) | 2014-07-18 | 2015-11-05 | Deutsches Zentrum für Luft- und Raumfahrt e.V. | Leichtbaustruktur und Verfahren zur Herstellung einer Leichtbaustruktur |
US11433047B2 (en) * | 2015-10-09 | 2022-09-06 | Neurotheryx Canada Ltd. | Pharmaceutical compositions comprising one or more pyrone compounds, and their use for treating inflammatory and neurodegenerative diseases |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4668803A (en) | 1984-05-10 | 1987-05-26 | Atlantic Richfield Company | Benzafuran derivatives |
DE4308451A1 (de) | 1992-09-10 | 1994-04-14 | Bayer Ag | 3-Aryl-pyron-Derivate |
ZA938019B (en) | 1992-11-13 | 1995-04-28 | Upjohn Co | Pyran-2-ones and 5,6-dihydropyran-2-ones useful for treating HIV and other retroviruses |
US5808062A (en) | 1993-11-19 | 1998-09-15 | Warner-Lambert Company | Pyrone derivatives as protease inhibitors and antiviral agents |
ATE266659T1 (de) * | 1998-03-12 | 2004-05-15 | Teijin Ltd | Benzofurylpyron-derivate |
-
1999
- 1999-03-12 AT AT99939191T patent/ATE266659T1/de not_active IP Right Cessation
- 1999-03-12 PL PL99343419A patent/PL343419A1/xx not_active Application Discontinuation
- 1999-03-12 BR BR9908706-5A patent/BR9908706A/pt not_active IP Right Cessation
- 1999-03-12 KR KR1020007010037A patent/KR100595332B1/ko not_active IP Right Cessation
- 1999-03-12 CA CA002323456A patent/CA2323456A1/en not_active Abandoned
- 1999-03-12 US US09/646,005 patent/US6589984B1/en not_active Expired - Fee Related
- 1999-03-12 DE DE69917237T patent/DE69917237T2/de not_active Expired - Fee Related
- 1999-03-12 EP EP99939191A patent/EP1063235B1/en not_active Expired - Lifetime
- 1999-03-12 ID IDW20001761A patent/ID27511A/id unknown
- 1999-03-12 NZ NZ506802A patent/NZ506802A/xx unknown
- 1999-03-12 IL IL13827999A patent/IL138279A0/xx unknown
- 1999-03-12 JP JP2000535641A patent/JP3922884B2/ja not_active Expired - Fee Related
- 1999-03-12 WO PCT/JP1999/001225 patent/WO1999046262A1/ja not_active Application Discontinuation
- 1999-03-12 CN CNB99805917XA patent/CN1170827C/zh not_active Expired - Fee Related
- 1999-03-12 HU HU0101381A patent/HUP0101381A3/hu unknown
- 1999-03-12 AU AU32773/99A patent/AU756965B2/en not_active Ceased
- 1999-03-12 RU RU2000125690/04A patent/RU2199536C2/ru not_active IP Right Cessation
- 1999-03-12 TR TR2000/02642T patent/TR200002642T2/xx unknown
- 1999-03-12 SK SK1341-2000A patent/SK13412000A3/sk unknown
- 1999-03-12 EE EEP200000504A patent/EE200000504A/xx unknown
- 1999-12-03 UA UA2000105676A patent/UA58587C2/uk unknown
-
2000
- 2000-09-08 IS IS5617A patent/IS5617A/is unknown
- 2000-09-11 NO NO20004517A patent/NO20004517L/no unknown
- 2000-09-12 BG BG104761A patent/BG104761A/xx unknown
- 2000-09-12 HR HR20000600A patent/HRP20000600A2/hr not_active Application Discontinuation
-
2003
- 2003-05-12 US US10/435,746 patent/US20030186976A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
ID27511A (id) | 2001-04-12 |
IS5617A (is) | 2000-09-08 |
KR100595332B1 (ko) | 2006-07-03 |
NO20004517D0 (no) | 2000-09-11 |
US6589984B1 (en) | 2003-07-08 |
HUP0101381A2 (hu) | 2002-05-29 |
KR20010041776A (ko) | 2001-05-25 |
UA58587C2 (uk) | 2003-08-15 |
TR200002642T2 (tr) | 2001-01-22 |
AU3277399A (en) | 1999-09-27 |
SK13412000A3 (sk) | 2001-04-09 |
PL343419A1 (en) | 2001-08-13 |
CN1299359A (zh) | 2001-06-13 |
DE69917237D1 (de) | 2004-06-17 |
EE200000504A (et) | 2002-02-15 |
EP1063235A1 (en) | 2000-12-27 |
HUP0101381A3 (en) | 2002-06-28 |
NO20004517L (no) | 2000-09-11 |
RU2199536C2 (ru) | 2003-02-27 |
BR9908706A (pt) | 2000-11-21 |
EP1063235B1 (en) | 2004-05-12 |
CA2323456A1 (en) | 1999-09-16 |
US20030186976A1 (en) | 2003-10-02 |
AU756965B2 (en) | 2003-01-30 |
IL138279A0 (en) | 2001-10-31 |
WO1999046262A1 (fr) | 1999-09-16 |
DE69917237T2 (de) | 2005-05-04 |
CN1170827C (zh) | 2004-10-13 |
EP1063235A4 (en) | 2003-01-07 |
ATE266659T1 (de) | 2004-05-15 |
JP3922884B2 (ja) | 2007-05-30 |
BG104761A (en) | 2001-08-31 |
NZ506802A (en) | 2002-11-26 |
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