DE69525763T2 - 4,6-DI-t-BUTYL-2,3-DIHYDROBENZOTHIOPHENE, DIE LDL OXIDATION HEMMEN - Google Patents
4,6-DI-t-BUTYL-2,3-DIHYDROBENZOTHIOPHENE, DIE LDL OXIDATION HEMMENInfo
- Publication number
- DE69525763T2 DE69525763T2 DE69525763T DE69525763T DE69525763T2 DE 69525763 T2 DE69525763 T2 DE 69525763T2 DE 69525763 T DE69525763 T DE 69525763T DE 69525763 T DE69525763 T DE 69525763T DE 69525763 T2 DE69525763 T2 DE 69525763T2
- Authority
- DE
- Germany
- Prior art keywords
- optionally substituted
- radical
- compound
- formula
- butyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
Links
- 238000007254 oxidation reaction Methods 0.000 title description 7
- 230000003647 oxidation Effects 0.000 title description 5
- NEVKGRDCAMPEII-UHFFFAOYSA-N 4,6-ditert-butyl-2,3-dihydro-1-benzothiophene Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC2=C1CCS2 NEVKGRDCAMPEII-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 127
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 47
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 36
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 29
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- 239000001301 oxygen Substances 0.000 claims abstract description 13
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims abstract description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 125000003003 spiro group Chemical group 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 239000011593 sulfur Substances 0.000 claims abstract description 6
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 12
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 11
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 10
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 abstract description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 9
- 230000004048 modification Effects 0.000 abstract description 9
- 238000012986 modification Methods 0.000 abstract description 9
- 239000003814 drug Substances 0.000 abstract description 8
- 230000002401 inhibitory effect Effects 0.000 abstract description 7
- 230000001590 oxidative effect Effects 0.000 abstract description 7
- 206010003210 Arteriosclerosis Diseases 0.000 abstract description 4
- 208000011775 arteriosclerosis disease Diseases 0.000 abstract description 4
- 125000000547 substituted alkyl group Chemical group 0.000 abstract description 4
- 125000002252 acyl group Chemical group 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000005017 substituted alkenyl group Chemical group 0.000 abstract 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 165
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 78
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 65
- 239000000243 solution Substances 0.000 description 64
- -1 C2-C20-alkenyl radical Chemical class 0.000 description 56
- 230000015572 biosynthetic process Effects 0.000 description 53
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
- 238000003786 synthesis reaction Methods 0.000 description 48
- 239000000203 mixture Substances 0.000 description 47
- 238000005160 1H NMR spectroscopy Methods 0.000 description 39
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 39
- 239000011541 reaction mixture Substances 0.000 description 36
- 239000012141 concentrate Substances 0.000 description 33
- 229920006395 saturated elastomer Polymers 0.000 description 33
- 238000010898 silica gel chromatography Methods 0.000 description 33
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- 239000012044 organic layer Substances 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
- 238000010992 reflux Methods 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- 108010007622 LDL Lipoproteins Proteins 0.000 description 20
- 102000007330 LDL Lipoproteins Human genes 0.000 description 20
- 238000001816 cooling Methods 0.000 description 19
- 239000012299 nitrogen atmosphere Substances 0.000 description 19
- 239000011780 sodium chloride Substances 0.000 description 19
- 239000007864 aqueous solution Substances 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 16
- 238000002844 melting Methods 0.000 description 16
- 230000008018 melting Effects 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- 239000012230 colorless oil Substances 0.000 description 14
- 230000003859 lipid peroxidation Effects 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 235000019270 ammonium chloride Nutrition 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 239000012280 lithium aluminium hydride Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000003963 antioxidant agent Substances 0.000 description 7
- 230000003078 antioxidant effect Effects 0.000 description 7
- 235000006708 antioxidants Nutrition 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- SKKZEOWXZNQGGG-UHFFFAOYSA-N (2,6-ditert-butyl-4-hydroxyphenyl) acetate Chemical compound CC(=O)OC1=C(C(C)(C)C)C=C(O)C=C1C(C)(C)C SKKZEOWXZNQGGG-UHFFFAOYSA-N 0.000 description 5
- LXEKPEMOWBOYRF-QDBORUFSSA-N AAPH Chemical compound Cl.Cl.NC(=N)C(C)(C)\N=N\C(C)(C)C(N)=N LXEKPEMOWBOYRF-QDBORUFSSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000002516 radical scavenger Substances 0.000 description 5
- YOGQIUSKOWCRET-UHFFFAOYSA-N (4,6-ditert-butyl-1-benzothiophen-5-yl) acetate Chemical compound CC(=O)OC1=C(C(C)(C)C)C=C2SC=CC2=C1C(C)(C)C YOGQIUSKOWCRET-UHFFFAOYSA-N 0.000 description 4
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 4
- AGAVMBCDBACJEA-UHFFFAOYSA-N 4,6-ditert-butyl-1-benzothiophen-5-ol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC2=C1C=CS2 AGAVMBCDBACJEA-UHFFFAOYSA-N 0.000 description 4
- OXTHDDIHJBDEEW-UHFFFAOYSA-N 4,6-ditert-butyl-2,2-dimethyl-3h-1-benzothiophen-5-ol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC2=C1CC(C)(C)S2 OXTHDDIHJBDEEW-UHFFFAOYSA-N 0.000 description 4
- HSBIASAJWXDTJM-UHFFFAOYSA-N 4,6-ditert-butyl-2,3-dihydro-1-benzothiophen-5-ol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC2=C1CCS2 HSBIASAJWXDTJM-UHFFFAOYSA-N 0.000 description 4
- HYKLPZHCTSELKT-UHFFFAOYSA-N 4,6-ditert-butyl-2-(hydroxymethyl)-2-methyl-3h-1-benzothiophen-5-ol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC2=C1CC(C)(CO)S2 HYKLPZHCTSELKT-UHFFFAOYSA-N 0.000 description 4
- IOPMNBVTHGGNMS-UHFFFAOYSA-N 4,6-ditert-butyl-2-[(dimethylamino)methyl]-2-methyl-3h-1-benzothiophen-5-ol Chemical compound C1=C(C(C)(C)C)C(O)=C(C(C)(C)C)C2=C1SC(CN(C)C)(C)C2 IOPMNBVTHGGNMS-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 201000001320 Atherosclerosis Diseases 0.000 description 4
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- MNGWKFNRROGUDS-UHFFFAOYSA-N [4,6-ditert-butyl-2-(iodomethyl)-2-methyl-3h-1-benzothiophen-5-yl] acetate Chemical compound CC(=O)OC1=C(C(C)(C)C)C=C2SC(C)(CI)CC2=C1C(C)(C)C MNGWKFNRROGUDS-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000000543 intermediate Substances 0.000 description 4
- 208000023589 ischemic disease Diseases 0.000 description 4
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 4
- 235000020778 linoleic acid Nutrition 0.000 description 4
- 208000010125 myocardial infarction Diseases 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 4
- ZXLSPBINTBCOEN-UHFFFAOYSA-N (2,6-ditert-butyl-3-formyl-4-hydroxyphenyl) acetate Chemical compound CC(=O)OC1=C(C(C)(C)C)C=C(O)C(C=O)=C1C(C)(C)C ZXLSPBINTBCOEN-UHFFFAOYSA-N 0.000 description 3
- XCRRGMKOURUQBY-UHFFFAOYSA-N (2,6-ditert-butyl-4-hydroxy-3-prop-2-enylphenyl) acetate Chemical compound CC(=O)OC1=C(C(C)(C)C)C=C(O)C(CC=C)=C1C(C)(C)C XCRRGMKOURUQBY-UHFFFAOYSA-N 0.000 description 3
- GTKGUPGJCXOVIH-UHFFFAOYSA-N (2,6-ditert-butyl-4-methoxyphenyl) acetate Chemical compound COC1=CC(C(C)(C)C)=C(OC(C)=O)C(C(C)(C)C)=C1 GTKGUPGJCXOVIH-UHFFFAOYSA-N 0.000 description 3
- MVMJPOWBEAVKQJ-UHFFFAOYSA-N (2,6-ditert-butyl-4-prop-2-enoxyphenyl) acetate Chemical compound CC(=O)OC1=C(C(C)(C)C)C=C(OCC=C)C=C1C(C)(C)C MVMJPOWBEAVKQJ-UHFFFAOYSA-N 0.000 description 3
- UVOZXTWWUCUVCM-UHFFFAOYSA-N (4,6-ditert-butyl-1,1-dioxo-1-benzothiophen-5-yl) acetate Chemical compound CC(=O)OC1=C(C(C)(C)C)C=C2S(=O)(=O)C=CC2=C1C(C)(C)C UVOZXTWWUCUVCM-UHFFFAOYSA-N 0.000 description 3
- JYTUBGJBFNIIHP-UHFFFAOYSA-N (4,6-ditert-butyl-1,1-dioxo-2,3-dihydro-1-benzothiophen-5-yl) acetate Chemical compound CC(=O)OC1=C(C(C)(C)C)C=C2S(=O)(=O)CCC2=C1C(C)(C)C JYTUBGJBFNIIHP-UHFFFAOYSA-N 0.000 description 3
- XCSZBQMRQLIIDV-UHFFFAOYSA-N (5-acetyloxy-4,6-ditert-butyl-2-methyl-3h-1-benzothiophen-2-yl)methyl acetate Chemical compound C1=C(C(C)(C)C)C(OC(C)=O)=C(C(C)(C)C)C2=C1SC(COC(=O)C)(C)C2 XCSZBQMRQLIIDV-UHFFFAOYSA-N 0.000 description 3
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 3
- DCMQCQCKUAESOE-UHFFFAOYSA-N 4,6-ditert-butyl-2,2-dipentyl-3h-1-benzothiophen-5-ol Chemical compound C1=C(C(C)(C)C)C(O)=C(C(C)(C)C)C2=C1SC(CCCCC)(CCCCC)C2 DCMQCQCKUAESOE-UHFFFAOYSA-N 0.000 description 3
- QAWYGBQXMCJJJY-UHFFFAOYSA-N 4,6-ditert-butyl-2-(4,8-dimethylnonyl)-2-methyl-3h-1-benzothiophen-5-ol Chemical compound C1=C(C(C)(C)C)C(O)=C(C(C)(C)C)C2=C1SC(CCCC(C)CCCC(C)C)(C)C2 QAWYGBQXMCJJJY-UHFFFAOYSA-N 0.000 description 3
- SDVQSQWWBOZKAK-UHFFFAOYSA-N 4,6-ditert-butyl-2-methyl-2,3-dihydro-1-benzothiophen-5-ol Chemical compound C1=C(C(C)(C)C)C(O)=C(C(C)(C)C)C2=C1SC(C)C2 SDVQSQWWBOZKAK-UHFFFAOYSA-N 0.000 description 3
- VYGALKFTVWDPBT-UHFFFAOYSA-N 4h-1,2-benzoxazine Chemical compound C1=CC=C2CC=NOC2=C1 VYGALKFTVWDPBT-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 102000006991 Apolipoprotein B-100 Human genes 0.000 description 3
- 108010008150 Apolipoprotein B-100 Proteins 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
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- 208000006011 Stroke Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XZKXKIKWDQMOFZ-UHFFFAOYSA-N [2,6-ditert-butyl-3-[[(2-chloroacetyl)amino]methyl]-4-hydroxyphenyl] acetate Chemical compound CC(=O)OC1=C(C(C)(C)C)C=C(O)C(CNC(=O)CCl)=C1C(C)(C)C XZKXKIKWDQMOFZ-UHFFFAOYSA-N 0.000 description 3
- KMKKIKWBZRABCJ-UHFFFAOYSA-N [2,6-ditert-butyl-4-(2-methylprop-2-enoxy)phenyl] acetate Chemical compound CC(=C)COC1=CC(C(C)(C)C)=C(OC(C)=O)C(C(C)(C)C)=C1 KMKKIKWBZRABCJ-UHFFFAOYSA-N 0.000 description 3
- FBEUEGCWBRHLQI-UHFFFAOYSA-N [2,6-ditert-butyl-4-(dimethylcarbamoylsulfanyl)-3-(2-oxoethyl)phenyl] acetate Chemical compound CN(C)C(=O)SC1=CC(C(C)(C)C)=C(OC(C)=O)C(C(C)(C)C)=C1CC=O FBEUEGCWBRHLQI-UHFFFAOYSA-N 0.000 description 3
- PWPKMEQGSCQLQH-UHFFFAOYSA-N [2,6-ditert-butyl-4-(dimethylcarbamoylsulfanyl)-3-(2-pentylhept-1-enyl)phenyl] acetate Chemical compound CCCCCC(CCCCC)=CC1=C(SC(=O)N(C)C)C=C(C(C)(C)C)C(OC(C)=O)=C1C(C)(C)C PWPKMEQGSCQLQH-UHFFFAOYSA-N 0.000 description 3
- GMTYOINOBGLYGA-UHFFFAOYSA-N [2,6-ditert-butyl-4-(dimethylcarbamoylsulfanyl)-3-prop-2-enylphenyl] acetate Chemical compound CN(C)C(=O)SC1=CC(C(C)(C)C)=C(OC(C)=O)C(C(C)(C)C)=C1CC=C GMTYOINOBGLYGA-UHFFFAOYSA-N 0.000 description 3
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- 239000012046 mixed solvent Substances 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 108010071584 oxidized low density lipoprotein Proteins 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229940097156 peroxyl Drugs 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000010410 reperfusion Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 102000014452 scavenger receptors Human genes 0.000 description 1
- 108010078070 scavenger receptors Proteins 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/02—Monothiocarbamic acids; Derivatives thereof
- C07C333/04—Monothiocarbamic acids; Derivatives thereof having nitrogen atoms of thiocarbamic groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/58—Radicals substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10736594 | 1994-04-11 | ||
| PCT/JP1995/000706 WO1995027710A1 (en) | 1994-04-11 | 1995-04-11 | 4,6-DI-t-BUTYL-2,3-DIHYDROBENZOTHIOPHENE DERIVATIVE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69525763D1 DE69525763D1 (de) | 2002-04-11 |
| DE69525763T2 true DE69525763T2 (de) | 2002-10-02 |
Family
ID=14457243
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69525763T Expired - Fee Related DE69525763T2 (de) | 1994-04-11 | 1995-04-11 | 4,6-DI-t-BUTYL-2,3-DIHYDROBENZOTHIOPHENE, DIE LDL OXIDATION HEMMEN |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5789436A (enExample) |
| EP (1) | EP0791589B1 (enExample) |
| CN (1) | CN1073563C (enExample) |
| AT (1) | ATE214059T1 (enExample) |
| AU (1) | AU683552B2 (enExample) |
| DE (1) | DE69525763T2 (enExample) |
| ES (1) | ES2173182T3 (enExample) |
| WO (1) | WO1995027710A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW565558B (en) * | 1995-11-09 | 2003-12-11 | Chugai Pharmaceutical Co Ltd | Intimal thickening inhibitory agent |
| DE19548708A1 (de) * | 1995-12-23 | 1997-06-26 | Merck Patent Gmbh | Cyclische Sulfone |
| KR100383835B1 (ko) * | 1996-06-26 | 2003-08-27 | 쥬가이 세이야쿠 가부시키가이샤 | 신장질환치료제및장기보존제 |
| WO1998050025A1 (en) * | 1997-05-08 | 1998-11-12 | Chugai Seiyaku Kabushiki Kaisha | Preventives/remedies for arteriosclerosis |
| TW472051B (en) | 1997-05-23 | 2002-01-11 | Chugai Pharmaceutical Co Ltd | 2,3-dihydrobenzofuran derivatives |
| DK1033975T3 (da) * | 1997-11-28 | 2002-05-27 | Knoll Ag | Fremgangsmåde til fremstilling af opløsningsmiddelfrie ikke-krystallinske aktive stoffer |
| WO1999051587A1 (en) | 1998-04-01 | 1999-10-14 | Ono Pharmaceutical Co., Ltd. | Fused thiophene derivatives and drugs containing the same as the active ingredient |
| DE10038709A1 (de) * | 2000-08-09 | 2002-02-28 | Aventis Pharma Gmbh | Substituierte und unsubstituierte Benzooxathiazole sowie daraus abgeleitete Verbindungen |
| EP1792614A1 (en) * | 2001-02-22 | 2007-06-06 | Teijin Pharma Limited | Benzo[b]thiophene derivatives |
| RU2184732C1 (ru) * | 2001-04-26 | 2002-07-10 | Некоммерческое партнерство "АСГЛ-Исследовательские лаборатории" | 5,5-дизамещенные-2-метил-9,9-диоксо-9-тиабицикло[4.3.0]нонаны |
| US20050159476A1 (en) * | 2002-03-29 | 2005-07-21 | Chugai Seiyaku Kabushiki Kaisha | Pharmaceutical composition for preventing or treating respiratory disease |
| DE10260095A1 (de) * | 2002-12-19 | 2004-07-01 | Basell Polyolefine Gmbh | Verfahren zur Herstellung von heterocyclischen Ketonen |
| CN102391521B (zh) * | 2011-06-30 | 2013-08-21 | 北京林业大学 | 一种改性碱木质素及其制备方法 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3530146A (en) * | 1968-07-01 | 1970-09-22 | American Cyanamid Co | Substituted benzothiophendione compounds |
| JPS505356A (enExample) * | 1973-05-30 | 1975-01-21 | ||
| GB1456323A (en) * | 1974-06-06 | 1976-11-24 | Labaz | Benzothiophenes process for preparing them and pharmaceutical compositions containing the same |
| US4001426A (en) * | 1974-10-17 | 1977-01-04 | Smithkline Corporation | Substituted benzofurans and benzothiophenes |
| US4224330A (en) * | 1979-09-13 | 1980-09-23 | Zoecon Corporation | Esters and thiolesters of benzothienyl acids |
| JPS5646879A (en) * | 1979-09-25 | 1981-04-28 | Takeda Chem Ind Ltd | Spiro compound, its preparation, and preventive and remedy for circulatory system disorder |
| US4436748A (en) * | 1980-10-20 | 1984-03-13 | Hoechst-Roussel Pharmaceuticals Inc. | Benzo[b]thiophenes |
| US4418068A (en) * | 1981-04-03 | 1983-11-29 | Eli Lilly And Company | Antiestrogenic and antiandrugenic benzothiophenes |
| US4521320A (en) * | 1983-10-21 | 1985-06-04 | Ciba Geigy Corporation | Thiocarbamate stabilizers |
| GB8402047D0 (en) * | 1984-01-26 | 1984-02-29 | Fisons Plc | Nitrogen heterocycles |
| EP0150966B1 (en) * | 1984-01-26 | 1989-07-12 | FISONS plc | Benzopyran derivatives, compositions containing them and processes for their preparation |
| GB8406906D0 (en) * | 1984-03-16 | 1984-04-18 | Akzo Nv | Benzo-thiazole and benzothiophene derivatives |
| GB8417559D0 (en) * | 1984-07-10 | 1984-08-15 | Pfizer Ltd | Anti-diarrhoeal agents |
| US5112852A (en) * | 1986-12-23 | 1992-05-12 | Merrell Dow Pharmaceuticals Inc. | Allenyl amines |
| ATE79876T1 (de) * | 1988-03-16 | 1992-09-15 | Ciba Geigy Ag | Thioverbindungen. |
| US4963580A (en) * | 1988-10-18 | 1990-10-16 | Merck & Co., Inc. | Substituted 5-hydroxy-2,3-dihydrobenzothiophenes as inhibitors of leukotriene biosynthesis |
| GB2224028A (en) * | 1988-10-18 | 1990-04-25 | Merck & Co Inc | Substituted 5-hydroxy-2,3-dihydrobenzothiophenes as inhibitors of leukotriene biosynthesis |
| JPH02121975A (ja) * | 1988-10-28 | 1990-05-09 | Eisai Co Ltd | ２，３−ジヒドロベンゾフラン誘導体 |
| DE4115184A1 (de) * | 1991-05-09 | 1992-11-12 | Bayer Ag | Benzothiophen-2-carboxamid-s,s-dioxide |
| FR2681324B1 (fr) * | 1991-09-18 | 1993-10-29 | Adir Cie | Nouveaux derives de la trimetazidine, leur procede de preparation et les compositions pharmaceutiques les contenant. |
| DE4204969A1 (de) * | 1992-02-19 | 1993-08-26 | Basf Ag | Verfahren zur herstellung von benzo(b)thiophenen |
| EP0639573A1 (de) * | 1993-08-03 | 1995-02-22 | Hoechst Aktiengesellschaft | Benzokondensierte 5-Ringheterocyclen, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, ihre Verwendung als Diagnostikum, sowie sie enthaltendes Medikament |
-
1995
- 1995-04-11 AU AU21485/95A patent/AU683552B2/en not_active Ceased
- 1995-04-11 EP EP95914557A patent/EP0791589B1/en not_active Expired - Lifetime
- 1995-04-11 DE DE69525763T patent/DE69525763T2/de not_active Expired - Fee Related
- 1995-04-11 CN CN95193057A patent/CN1073563C/zh not_active Expired - Fee Related
- 1995-04-11 WO PCT/JP1995/000706 patent/WO1995027710A1/ja not_active Ceased
- 1995-04-11 AT AT95914557T patent/ATE214059T1/de not_active IP Right Cessation
- 1995-04-11 ES ES95914557T patent/ES2173182T3/es not_active Expired - Lifetime
- 1995-04-11 US US08/727,652 patent/US5789436A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0791589A1 (en) | 1997-08-27 |
| US5789436A (en) | 1998-08-04 |
| EP0791589A4 (enExample) | 1997-08-27 |
| ES2173182T3 (es) | 2002-10-16 |
| DE69525763D1 (de) | 2002-04-11 |
| AU2148595A (en) | 1995-10-30 |
| AU683552B2 (en) | 1997-11-13 |
| WO1995027710A1 (en) | 1995-10-19 |
| CN1148386A (zh) | 1997-04-23 |
| ATE214059T1 (de) | 2002-03-15 |
| CN1073563C (zh) | 2001-10-24 |
| EP0791589B1 (en) | 2002-03-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8339 | Ceased/non-payment of the annual fee |