SK164795A3 - Benzene derivatives - Google Patents
Benzene derivatives Download PDFInfo
- Publication number
- SK164795A3 SK164795A3 SK1647-95A SK164795A SK164795A3 SK 164795 A3 SK164795 A3 SK 164795A3 SK 164795 A SK164795 A SK 164795A SK 164795 A3 SK164795 A3 SK 164795A3
- Authority
- SK
- Slovakia
- Prior art keywords
- group
- butyl
- carbon atoms
- optionally substituted
- methyl
- Prior art date
Links
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 127
- 150000003839 salts Chemical class 0.000 claims abstract description 55
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 51
- 230000003287 optical effect Effects 0.000 claims abstract description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 147
- -1 2- (3,4-methylenedioxyphenoxy) ethyl Chemical group 0.000 claims description 114
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 42
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 40
- 125000003545 alkoxy group Chemical group 0.000 claims description 35
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
- 125000003107 substituted aryl group Chemical group 0.000 claims description 35
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 239000001301 oxygen Substances 0.000 claims description 23
- 150000002431 hydrogen Chemical class 0.000 claims description 21
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 21
- 125000004434 sulfur atom Chemical group 0.000 claims description 21
- 125000004423 acyloxy group Chemical group 0.000 claims description 18
- 150000001555 benzenes Chemical class 0.000 claims description 18
- DTCZSWHPFSCCJV-UHFFFAOYSA-N 3-[3-[2-(1,3-benzodioxol-5-yloxy)ethyl-methylamino]propyl]-2-(3,5-ditert-butyl-4-hydroxyphenyl)-1,3-thiazolidin-4-one Chemical compound C=1C=C2OCOC2=CC=1OCCN(C)CCCN(C(CS1)=O)C1C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 DTCZSWHPFSCCJV-UHFFFAOYSA-N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- VSCGBVQOYASCLJ-UHFFFAOYSA-N ethyl 2-[3-[3-[2-(1,3-benzodioxol-5-yloxy)ethyl-methylamino]propyl]-2-(3,5-ditert-butyl-4-hydroxyphenyl)-4-oxo-1,3-thiazolidin-5-yl]acetate Chemical compound C=1C=C2OCOC2=CC=1OCCN(C)CCCN1C(=O)C(CC(=O)OCC)SC1C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSCGBVQOYASCLJ-UHFFFAOYSA-N 0.000 claims description 3
- PMUMJQRSTLSPIQ-UHFFFAOYSA-N n-[3-[2-(1,3-benzodioxol-5-yloxy)ethyl-methylamino]propyl]-3,5-ditert-butyl-4-hydroxybenzamide Chemical compound C=1C=C2OCOC2=CC=1OCCN(C)CCCNC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 PMUMJQRSTLSPIQ-UHFFFAOYSA-N 0.000 claims description 3
- RDNYXEDBZMOHTQ-UHFFFAOYSA-N 3-[3-[2-(1,3-benzodioxol-5-yloxy)ethyl-methylamino]propyl]-2-[4-hydroxy-3,5-di(propan-2-yl)phenyl]-1,3-thiazolidin-4-one Chemical compound CC(C)C1=C(O)C(C(C)C)=CC(C2N(C(=O)CS2)CCCN(C)CCOC=2C=C3OCOC3=CC=2)=C1 RDNYXEDBZMOHTQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 26
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 7
- 125000005936 piperidyl group Chemical group 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003003 spiro group Chemical group 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- DNGKALAOBQCDPL-UHFFFAOYSA-N 3-[4-[2-(1,3-benzodioxol-5-yloxy)ethyl-methylamino]butyl]-2-(3,5-ditert-butyl-4-hydroxyphenyl)-1,3-thiazolidin-4-one Chemical compound C=1C=C2OCOC2=CC=1OCCN(C)CCCCN(C(CS1)=O)C1C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 DNGKALAOBQCDPL-UHFFFAOYSA-N 0.000 claims 1
- 241000894242 Idyla Species 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- JORGYNDOMPQOTH-UHFFFAOYSA-N n,n-dimethyl-2-(4-oxo-1,3-thiazolidin-3-yl)acetamide Chemical compound CN(C)C(=O)CN1CSCC1=O JORGYNDOMPQOTH-UHFFFAOYSA-N 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 10
- 230000002401 inhibitory effect Effects 0.000 abstract description 6
- 230000001964 calcium overload Effects 0.000 abstract description 3
- 230000003859 lipid peroxidation Effects 0.000 abstract description 3
- 206010020772 Hypertension Diseases 0.000 abstract description 2
- 208000023589 ischemic disease Diseases 0.000 abstract description 2
- 230000003449 preventive effect Effects 0.000 abstract description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- 230000008485 antagonism Effects 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 230000001196 vasorelaxation Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 description 113
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 96
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
- 239000000203 mixture Substances 0.000 description 72
- 238000006243 chemical reaction Methods 0.000 description 64
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 238000005481 NMR spectroscopy Methods 0.000 description 49
- 239000002904 solvent Substances 0.000 description 48
- 238000002360 preparation method Methods 0.000 description 44
- 238000010992 reflux Methods 0.000 description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000003480 eluent Substances 0.000 description 24
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 22
- 230000000704 physical effect Effects 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000012442 inert solvent Substances 0.000 description 21
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 20
- 239000012044 organic layer Substances 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 19
- 238000005160 1H NMR spectroscopy Methods 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 18
- 230000035484 reaction time Effects 0.000 description 18
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
- 239000013078 crystal Substances 0.000 description 17
- 238000010898 silica gel chromatography Methods 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 150000004967 organic peroxy acids Chemical class 0.000 description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 150000007529 inorganic bases Chemical class 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 229910000029 sodium carbonate Inorganic materials 0.000 description 11
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- 239000012267 brine Substances 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000005457 ice water Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 229960003975 potassium Drugs 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 239000012230 colorless oil Substances 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 230000002140 halogenating effect Effects 0.000 description 8
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 7
- HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 description 7
- 229960004166 diltiazem Drugs 0.000 description 7
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 7
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 6
- DOZRDZLFLOODMB-UHFFFAOYSA-N 3,5-di-tert-Butyl-4-hydroxybenzaldehyde Chemical compound CC(C)(C)C1=CC(C=O)=CC(C(C)(C)C)=C1O DOZRDZLFLOODMB-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical group O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- WVFXPIQAPJNXAJ-UHFFFAOYSA-N 3-(3-bromopropyl)-2-(3,5-ditert-butyl-4-hydroxyphenyl)-1,3-thiazolidin-4-one Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C2N(C(=O)CS2)CCCBr)=C1 WVFXPIQAPJNXAJ-UHFFFAOYSA-N 0.000 description 5
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
- ICLQADWQMAOEPS-UHFFFAOYSA-N 3-(3-chloropropyl)-2-[4-hydroxy-3,5-di(propan-2-yl)phenyl]-1,3-thiazolidin-4-one Chemical compound CC(C)C1=C(O)C(C(C)C)=CC(C2N(C(=O)CS2)CCCCl)=C1 ICLQADWQMAOEPS-UHFFFAOYSA-N 0.000 description 4
- 241000755093 Gaidropsarus vulgaris Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 230000008602 contraction Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000001629 suppression Effects 0.000 description 4
- FMWKJKKEOQAJBO-UHFFFAOYSA-N 2-[2-(3,5-ditert-butyl-4-hydroxyphenyl)-3-(3-hydroxypropyl)-4-oxo-1,3-thiazolidin-5-yl]acetic acid Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C2N(C(=O)C(CC(O)=O)S2)CCCO)=C1 FMWKJKKEOQAJBO-UHFFFAOYSA-N 0.000 description 3
- XFCJHRBMIGIQSD-UHFFFAOYSA-N 3-(3-bromopropyl)-5-(3,5-ditert-butyl-4-hydroxyphenyl)-1,3,4-oxadiazol-2-one Chemical compound CC(C)(C)c1cc(cc(c1O)C(C)(C)C)-c1nn(CCCBr)c(=O)o1 XFCJHRBMIGIQSD-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- YUCGGPRNBYMGJU-UHFFFAOYSA-N n'-[2-(1,3-benzodioxol-5-yloxy)ethyl]-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCOC1=CC=C2OCOC2=C1 YUCGGPRNBYMGJU-UHFFFAOYSA-N 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000002883 vasorelaxation effect Effects 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- MSDSSBHISUDQCR-UHFFFAOYSA-N 1-[2-(3,5-ditert-butyl-4-hydroxyphenyl)-1,3-thiazolidin-3-yl]prop-2-en-1-one Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C2N(CCS2)C(=O)C=C)=C1 MSDSSBHISUDQCR-UHFFFAOYSA-N 0.000 description 2
- CYQAYKAFWNKHMI-UHFFFAOYSA-N 2,6-ditert-butyl-4-[3-(3-chloropropyl)imidazol-4-yl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C=2N(C=NC=2)CCCCl)=C1 CYQAYKAFWNKHMI-UHFFFAOYSA-N 0.000 description 2
- AZSGEIRQLYNMPS-UHFFFAOYSA-N 2,6-ditert-butyl-4-[3-(3-hydroxypropyl)imidazol-4-yl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C=2N(C=NC=2)CCCO)=C1 AZSGEIRQLYNMPS-UHFFFAOYSA-N 0.000 description 2
- PACLRQUOUFYNAF-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenyl)-3-(3-hydroxypropyl)-1,3-thiazolidin-4-one Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C2N(C(=O)CS2)CCCO)=C1 PACLRQUOUFYNAF-UHFFFAOYSA-N 0.000 description 2
- OGSCEMPGOLHCLT-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenyl)-3-[3-(methylamino)propyl]-1,3-thiazolidin-4-one;hydrobromide Chemical compound Br.S1CC(=O)N(CCCNC)C1C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 OGSCEMPGOLHCLT-UHFFFAOYSA-N 0.000 description 2
- VKJCJJYNVIYVQR-UHFFFAOYSA-N 2-(3-bromopropyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCBr)C(=O)C2=C1 VKJCJJYNVIYVQR-UHFFFAOYSA-N 0.000 description 2
- FJFKFUIBDLZKOK-UHFFFAOYSA-N 2-[4-hydroxy-3,5-di(propan-2-yl)phenyl]-3-(3-hydroxypropyl)-1,3-thiazolidin-4-one Chemical compound CC(C)C1=C(O)C(C(C)C)=CC(C2N(C(=O)CS2)CCCO)=C1 FJFKFUIBDLZKOK-UHFFFAOYSA-N 0.000 description 2
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 2
- YEXOWHQZWLCHHD-UHFFFAOYSA-N 3,5-ditert-butyl-4-hydroxybenzoic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=CC(C(C)(C)C)=C1O YEXOWHQZWLCHHD-UHFFFAOYSA-N 0.000 description 2
- DYHNAVNJQOWKCR-UHFFFAOYSA-N 3-(3-bromopropyl)-2-(3,5-ditert-butyl-4-hydroxyphenyl)-5-methoxy-1,3-thiazolidin-4-one Chemical compound BrCCCN1C(=O)C(OC)SC1C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 DYHNAVNJQOWKCR-UHFFFAOYSA-N 0.000 description 2
- RDOQTWIWKNOHBE-UHFFFAOYSA-N 3-(3-chloropropyl)-2-(3,5-ditert-butyl-4-hydroxyphenyl)-5-(2-oxo-2-pyrrolidin-1-ylethyl)-1,3-thiazolidin-4-one Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(C2N(C(=O)C(CC(=O)N3CCCC3)S2)CCCCl)=C1 RDOQTWIWKNOHBE-UHFFFAOYSA-N 0.000 description 2
- HTYISEZGGUMDOL-UHFFFAOYSA-N 3-(3-chloropropyl)-2-(3,5-ditert-butyl-4-hydroxyphenyl)-5-methyl-1,3-thiazolidin-4-one Chemical compound ClCCCN1C(=O)C(C)SC1C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 HTYISEZGGUMDOL-UHFFFAOYSA-N 0.000 description 2
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- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
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- 210000002808 connective tissue Anatomy 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 210000000107 myocyte Anatomy 0.000 description 1
- VITMIHCGONQCRB-UHFFFAOYSA-N n-[3-[2-(1,3-benzodioxol-5-yloxy)ethyl-methylamino]propyl]-3,5-ditert-butyl-4-hydroxybenzenesulfonamide Chemical compound C=1C=C2OCOC2=CC=1OCCN(C)CCCNS(=O)(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VITMIHCGONQCRB-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 108010071584 oxidized low density lipoprotein Proteins 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 210000001567 regular cardiac muscle cell of ventricle Anatomy 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 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
- C07D405/02—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 two hetero rings
- C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/14—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/82—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
-
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D417/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D417/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- C07D417/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D419/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms
- C07D419/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D419/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/10—Spiro-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP15224893 | 1993-06-23 | ||
PCT/JP1994/001009 WO1995000471A1 (fr) | 1993-06-23 | 1994-06-23 | Derive du benzene utile contre les ischemies |
Publications (1)
Publication Number | Publication Date |
---|---|
SK164795A3 true SK164795A3 (en) | 1996-10-02 |
Family
ID=15536338
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SK1647-95A SK164795A3 (en) | 1993-06-23 | 1994-06-23 | Benzene derivatives |
Country Status (18)
Country | Link |
---|---|
EP (1) | EP0705816B1 (ro) |
KR (1) | KR100262419B1 (ro) |
CN (1) | CN1038582C (ro) |
AT (1) | ATE196464T1 (ro) |
CA (1) | CA2165662A1 (ro) |
CZ (1) | CZ289716B6 (ro) |
DE (1) | DE69425970T2 (ro) |
ES (1) | ES2152319T3 (ro) |
FI (1) | FI956151A (ro) |
HU (1) | HUT75102A (ro) |
NO (1) | NO305956B1 (ro) |
PL (1) | PL176687B1 (ro) |
RO (1) | RO115518B1 (ro) |
RU (1) | RU2127254C1 (ro) |
SK (1) | SK164795A3 (ro) |
TW (1) | TW403734B (ro) |
UA (1) | UA43338C2 (ro) |
WO (1) | WO1995000471A1 (ro) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5998452A (en) * | 1993-06-23 | 1999-12-07 | Chugai Seiyaku Kabushiki Kaisha | Benzene derivatives, compositions and methods for treating ischemic diseases |
EP0799614A4 (en) * | 1994-12-22 | 2000-03-22 | Chugai Pharmaceutical Co Ltd | ISCHEMIC DISEASE MEDICINE |
WO1998021584A1 (en) * | 1996-11-12 | 1998-05-22 | Eli Lilly And Company | Combinatorial process for preparing thiazolidinone libraries |
US6174908B1 (en) | 1999-05-10 | 2001-01-16 | Icagen, Inc. | Potassium channel inhibitors |
EP1082315A1 (en) | 1998-06-05 | 2001-03-14 | Icagen, Inc. | Potassium channel inhibitors |
JP2004002206A (ja) * | 2000-07-26 | 2004-01-08 | Chugai Pharmaceut Co Ltd | 光学活性なチアゾリジノン誘導体の製造方法 |
MXPA04000411A (es) | 2001-07-16 | 2004-03-18 | Euro Celtique Sa | Tiazolidinonas arilo sustituidas y uso de las mismas. |
AU2003255843A1 (en) * | 2002-08-23 | 2004-03-11 | Ionix Pharmaceuticals Limited | 1,3-thiazolin-4-ones as therapeutic compounds in the treatment of pain |
FR3120368B1 (fr) * | 2021-03-02 | 2024-01-19 | Michelin & Cie | Monomères contenant un motif 4-thiazolidinone et leurs polycondensats polyamide, polyester et polyuréthane. |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2623048A (en) * | 1948-04-05 | 1952-12-23 | Parke Davis & Co | 4-thiazolidone derivatives and process for preparing the same |
US2520179A (en) * | 1949-02-02 | 1950-08-29 | Sterling Drug Inc | 4-thiazolidones and a method for preparation thereof |
US3309377A (en) * | 1964-10-19 | 1967-03-14 | Sterling Drug Inc | 3-[(2-oxazolidinone-3-yl)-alkyl]-4-thiazolidinones and their preparation |
FR2504528A1 (fr) * | 1981-04-23 | 1982-10-29 | Choay Sa | Dialcoxy (2,4) benzenesulfonamides n-substitues |
US4820715A (en) * | 1984-06-28 | 1989-04-11 | Bristol-Myers Company | Anti-emetic quinuclidinyl benzamides |
PT83152B (pt) * | 1985-08-09 | 1989-03-30 | Lilly Co Eli | Processo para a preparacao de compostos di-t-butilfenoicos |
GB8820442D0 (en) * | 1988-08-30 | 1988-09-28 | Usherwood P N R | Therapeutic polyamine amides |
AU7317391A (en) * | 1990-02-14 | 1991-09-03 | Chugai Seiyaku Kabushiki Kaisha | Inhibitor of denatured ldl formation |
-
1994
- 1994-06-23 CA CA002165662A patent/CA2165662A1/en not_active Abandoned
- 1994-06-23 UA UA95125450A patent/UA43338C2/uk unknown
- 1994-06-23 SK SK1647-95A patent/SK164795A3/sk unknown
- 1994-06-23 DE DE69425970T patent/DE69425970T2/de not_active Expired - Fee Related
- 1994-06-23 RO RO95-02265A patent/RO115518B1/ro unknown
- 1994-06-23 KR KR1019950705894A patent/KR100262419B1/ko not_active IP Right Cessation
- 1994-06-23 PL PL94312471A patent/PL176687B1/pl unknown
- 1994-06-23 AT AT94918559T patent/ATE196464T1/de not_active IP Right Cessation
- 1994-06-23 TW TW083105734A patent/TW403734B/zh not_active IP Right Cessation
- 1994-06-23 HU HU9503775A patent/HUT75102A/hu unknown
- 1994-06-23 CN CN94192846A patent/CN1038582C/zh not_active Expired - Fee Related
- 1994-06-23 ES ES94918559T patent/ES2152319T3/es not_active Expired - Lifetime
- 1994-06-23 CZ CZ19953450A patent/CZ289716B6/cs not_active IP Right Cessation
- 1994-06-23 EP EP94918559A patent/EP0705816B1/en not_active Expired - Lifetime
- 1994-06-23 RU RU96102006/04A patent/RU2127254C1/ru not_active IP Right Cessation
- 1994-06-23 WO PCT/JP1994/001009 patent/WO1995000471A1/ja active IP Right Grant
-
1995
- 1995-12-20 FI FI956151A patent/FI956151A/fi unknown
- 1995-12-20 NO NO955176A patent/NO305956B1/no unknown
Also Published As
Publication number | Publication date |
---|---|
CN1127502A (zh) | 1996-07-24 |
TW403734B (en) | 2000-09-01 |
EP0705816A1 (en) | 1996-04-10 |
ES2152319T3 (es) | 2001-02-01 |
AU674239B2 (en) | 1996-12-12 |
CN1038582C (zh) | 1998-06-03 |
DE69425970D1 (de) | 2000-10-26 |
RO115518B1 (ro) | 2000-03-30 |
PL176687B1 (pl) | 1999-07-30 |
AU6982994A (en) | 1995-01-17 |
ATE196464T1 (de) | 2000-10-15 |
RU2127254C1 (ru) | 1999-03-10 |
CZ345095A3 (en) | 1996-12-11 |
EP0705816A4 (en) | 1997-05-28 |
WO1995000471A1 (fr) | 1995-01-05 |
HU9503775D0 (en) | 1996-02-28 |
UA43338C2 (uk) | 2001-12-17 |
NO955176L (no) | 1996-02-23 |
CA2165662A1 (en) | 1995-01-05 |
NO305956B1 (no) | 1999-08-23 |
NO955176D0 (no) | 1995-12-20 |
HUT75102A (en) | 1997-04-28 |
DE69425970T2 (de) | 2001-01-18 |
CZ289716B6 (cs) | 2002-03-13 |
KR100262419B1 (ko) | 2000-09-01 |
EP0705816B1 (en) | 2000-09-20 |
FI956151A (fi) | 1996-02-19 |
FI956151A0 (fi) | 1995-12-20 |
PL312471A1 (en) | 1996-04-29 |
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