NO328138B1 - Benzofuran- eller benzotiofenderivater, fremgangsmate for deres fremstilling, preparater inneholdende de samme samt deres anvendelse - Google Patents
Benzofuran- eller benzotiofenderivater, fremgangsmate for deres fremstilling, preparater inneholdende de samme samt deres anvendelse Download PDFInfo
- Publication number
- NO328138B1 NO328138B1 NO20030800A NO20030800A NO328138B1 NO 328138 B1 NO328138 B1 NO 328138B1 NO 20030800 A NO20030800 A NO 20030800A NO 20030800 A NO20030800 A NO 20030800A NO 328138 B1 NO328138 B1 NO 328138B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- benzofuran
- general formula
- stated
- chain
- Prior art date
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- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 title claims description 82
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title claims description 39
- 238000000034 method Methods 0.000 title claims description 35
- 238000002360 preparation method Methods 0.000 title claims description 22
- 230000008569 process Effects 0.000 title claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 320
- 239000000203 mixture Substances 0.000 claims description 129
- 229910052721 tungsten Inorganic materials 0.000 claims description 67
- 239000001257 hydrogen Substances 0.000 claims description 58
- 229910052739 hydrogen Inorganic materials 0.000 claims description 58
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 51
- 125000002947 alkylene group Chemical group 0.000 claims description 37
- 239000012458 free base Substances 0.000 claims description 37
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
- -1 ketone compound Chemical class 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 25
- 239000003795 chemical substances by application Substances 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 150000007522 mineralic acids Chemical class 0.000 claims description 15
- 150000007524 organic acids Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 11
- 230000002140 halogenating effect Effects 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 9
- 150000001266 acyl halides Chemical class 0.000 claims description 9
- 229910052783 alkali metal Chemical group 0.000 claims description 8
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- MGQPBJVSORVILM-UHFFFAOYSA-N propan-2-yl 2-butyl-3-[4-[3-(dibutylamino)propyl]benzoyl]-6-methyl-1-benzofuran-5-carboxylate Chemical compound C1=CC(CCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCCC)OC2=CC(C)=C(C(=O)OC(C)C)C=C12 MGQPBJVSORVILM-UHFFFAOYSA-N 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- 150000001340 alkali metals Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 150000004820 halides Chemical class 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- 206010020772 Hypertension Diseases 0.000 claims description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000468 ketone group Chemical group 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000003544 oxime group Chemical group 0.000 claims description 5
- 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 claims description 4
- 206010019280 Heart failures Diseases 0.000 claims description 4
- 239000002841 Lewis acid Substances 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 210000000748 cardiovascular system Anatomy 0.000 claims description 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 150000007517 lewis acids Chemical class 0.000 claims description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims description 4
- 229960001860 salicylate Drugs 0.000 claims description 4
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 3
- 206010047281 Ventricular arrhythmia Diseases 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 235000010323 ascorbic acid Nutrition 0.000 claims description 3
- 239000011668 ascorbic acid Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 claims description 3
- 238000010511 deprotection reaction Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical group OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
- 230000001575 pathological effect Effects 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 239000012321 sodium triacetoxyborohydride Substances 0.000 claims description 3
- 208000011580 syndromic disease Diseases 0.000 claims description 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 3
- 230000002861 ventricular Effects 0.000 claims description 3
- OJGUHVXJDZPQSK-WLHGVMLRSA-N (e)-but-2-enedioic acid;propan-2-yl 2-butyl-3-[4-[3-(dibutylamino)propyl]benzoyl]-1-benzofuran-5-carboxylate Chemical compound OC(=O)\C=C\C(O)=O.C1=CC(CCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCCC)OC2=CC=C(C(=O)OC(C)C)C=C12 OJGUHVXJDZPQSK-WLHGVMLRSA-N 0.000 claims description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-M 4-aminobenzoate Chemical compound NC1=CC=C(C([O-])=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-M 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 206010002383 Angina Pectoris Diseases 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 claims description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- 206010061216 Infarction Diseases 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 206010042600 Supraventricular arrhythmias Diseases 0.000 claims description 2
- VYEYJCBEXFTGBN-UHFFFAOYSA-N acetic acid;1,3-dimethyl-7h-purine-2,6-dione Chemical class CC(O)=O.O=C1N(C)C(=O)N(C)C2=C1NC=N2 VYEYJCBEXFTGBN-UHFFFAOYSA-N 0.000 claims description 2
- 229940024606 amino acid Drugs 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 229940072107 ascorbate Drugs 0.000 claims description 2
- 229940009098 aspartate Drugs 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- 229940077388 benzenesulfonate Drugs 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 2
- ZCENNVQCOZQSGH-UHFFFAOYSA-N celivarone Chemical compound C1=CC(CCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCCC)OC2=CC=C(C(=O)OC(C)C)C=C12 ZCENNVQCOZQSGH-UHFFFAOYSA-N 0.000 claims description 2
- 230000002490 cerebral effect Effects 0.000 claims description 2
- 229940114081 cinnamate Drugs 0.000 claims description 2
- 229940018560 citraconate Drugs 0.000 claims description 2
- 229940001468 citrate Drugs 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- IRXSLJNXXZKURP-UHFFFAOYSA-N fluorenylmethyloxycarbonyl chloride Chemical compound C1=CC=C2C(COC(=O)Cl)C3=CC=CC=C3C2=C1 IRXSLJNXXZKURP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 229940050410 gluconate Drugs 0.000 claims description 2
- 229930195712 glutamate Natural products 0.000 claims description 2
- 229940049906 glutamate Drugs 0.000 claims description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 claims description 2
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 2
- 229940001447 lactate Drugs 0.000 claims description 2
- 229940049920 malate Drugs 0.000 claims description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 claims description 2
- 208000010125 myocardial infarction Diseases 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- HQALDKFFRYFTKP-UHFFFAOYSA-N 2-[4-[4-(2-benzyl-1-benzothiophen-3-yl)phenyl]-2-bromo-6-(3-methoxyphenyl)phenoxy]acetic acid Chemical compound COC1=CC=CC(C=2C(=C(Br)C=C(C=2)C=2C=CC(=CC=2)C=2C3=CC=CC=C3SC=2CC=2C=CC=CC=2)OCC(O)=O)=C1 HQALDKFFRYFTKP-UHFFFAOYSA-N 0.000 claims 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 2
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims 1
- 206010003130 Arrhythmia supraventricular Diseases 0.000 claims 1
- 206010065929 Cardiovascular insufficiency Diseases 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 claims 1
- 230000001746 atrial effect Effects 0.000 claims 1
- 125000004965 chloroalkyl group Chemical group 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 claims 1
- 125000000487 histidyl group Chemical class [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 claims 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 claims 1
- 150000002823 nitrates Chemical class 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- ZWMGKPGMHDMETC-UHFFFAOYSA-N propan-2-yl 2-butyl-3-[4-[3-(dibutylamino)propyl]benzoyl]-1-benzofuran-5-carboxylate;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC(CCCN(CCCC)CCCC)=CC=C1C(=O)C1=C(CCCC)OC2=CC=C(C(=O)OC(C)C)C=C12 ZWMGKPGMHDMETC-UHFFFAOYSA-N 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 283
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 148
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 132
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 125
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 105
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 101
- 239000000243 solution Substances 0.000 description 91
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 81
- 238000004587 chromatography analysis Methods 0.000 description 50
- 239000003480 eluent Substances 0.000 description 50
- 239000000284 extract Substances 0.000 description 50
- 239000000377 silicon dioxide Substances 0.000 description 50
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 44
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- 239000000047 product Substances 0.000 description 38
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 238000000746 purification Methods 0.000 description 36
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
- 238000000605 extraction Methods 0.000 description 32
- 239000011780 sodium chloride Substances 0.000 description 31
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 26
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- 238000010992 reflux Methods 0.000 description 19
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 18
- 239000012429 reaction media Substances 0.000 description 18
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 17
- 235000011114 ammonium hydroxide Nutrition 0.000 description 17
- 125000003118 aryl group Chemical group 0.000 description 17
- 230000000694 effects Effects 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 15
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 13
- 235000006408 oxalic acid Nutrition 0.000 description 13
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
- 235000009518 sodium iodide Nutrition 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
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- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940114926 stearate Drugs 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
- TXNWLNDDWPLCEC-UHFFFAOYSA-N tert-butyl-hex-5-ynoxy-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](OCCCCC#C)(C(C)(C)C)C1=CC=CC=C1 TXNWLNDDWPLCEC-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- UGKSITLWMZJTHC-UHFFFAOYSA-N tribromo-$l^{3}-bromane Chemical compound BrBr(Br)Br UGKSITLWMZJTHC-UHFFFAOYSA-N 0.000 description 1
- 210000001186 vagus nerve Anatomy 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans 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
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
-
- 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0010834A FR2813306B1 (fr) | 2000-08-23 | 2000-08-23 | Aminoalkybenzoyl-benzofurannes ou benzothiophenes, leur procede de preparation et les compositions les contenant |
| PCT/FR2001/002640 WO2002016339A1 (fr) | 2000-08-23 | 2001-08-21 | Aminoalkylbenzoyl-benzofuranes ou benzothiophenes, leur procede de preparation et les compositions les contenant |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20030800D0 NO20030800D0 (no) | 2003-02-20 |
| NO20030800L NO20030800L (no) | 2003-04-23 |
| NO328138B1 true NO328138B1 (no) | 2009-12-14 |
Family
ID=8853674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20030800A NO328138B1 (no) | 2000-08-23 | 2003-02-20 | Benzofuran- eller benzotiofenderivater, fremgangsmate for deres fremstilling, preparater inneholdende de samme samt deres anvendelse |
Country Status (36)
| Country | Link |
|---|---|
| US (1) | US6949583B2 (de) |
| EP (1) | EP1315709B1 (de) |
| JP (2) | JP5081363B2 (de) |
| KR (1) | KR100911280B1 (de) |
| CN (1) | CN1246315C (de) |
| AR (1) | AR032892A1 (de) |
| AT (1) | ATE469138T1 (de) |
| AU (2) | AU8414901A (de) |
| BG (1) | BG66240B1 (de) |
| BR (1) | BR0113425B1 (de) |
| CA (1) | CA2415847C (de) |
| CY (1) | CY1110738T1 (de) |
| CZ (1) | CZ304003B6 (de) |
| DE (1) | DE60142240D1 (de) |
| DK (1) | DK1315709T3 (de) |
| EA (1) | EA006237B1 (de) |
| ES (1) | ES2346291T3 (de) |
| FR (1) | FR2813306B1 (de) |
| HK (1) | HK1053113A1 (de) |
| HU (1) | HU229456B1 (de) |
| IL (2) | IL153632A0 (de) |
| IS (1) | IS2821B (de) |
| MA (1) | MA26943A1 (de) |
| ME (2) | MEP23008A (de) |
| MX (1) | MXPA03001463A (de) |
| NO (1) | NO328138B1 (de) |
| NZ (1) | NZ523446A (de) |
| OA (1) | OA12359A (de) |
| PL (1) | PL219848B1 (de) |
| PT (1) | PT1315709E (de) |
| RS (1) | RS51603B (de) |
| SI (1) | SI1315709T1 (de) |
| SK (1) | SK288126B6 (de) |
| TW (1) | TWI290920B (de) |
| WO (1) | WO2002016339A1 (de) |
| ZA (1) | ZA200300744B (de) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7401072B2 (en) * | 2003-06-10 | 2008-07-15 | Google Inc. | Named URL entry |
| KR20080015077A (ko) * | 2005-05-05 | 2008-02-18 | 사노피-아벤티스 유.에스. 엘엘씨 | 안정한 나노입자 제형 |
| FR2893616B1 (fr) * | 2005-11-23 | 2008-01-04 | Sanofi Aventis Sa | Nouveaux derives d'indolizine, leur procede de preparation et les compositions therapeutiques les comprenant |
| CN1946120B (zh) * | 2006-10-20 | 2010-05-12 | 华为技术有限公司 | 实现话单关联的方法及系统 |
| EP2308488A1 (de) | 2009-10-09 | 2011-04-13 | Sanofi-Aventis | Verwendung von Celivaron zur Herstellung eines Medikaments zur Verwendung bei der Prävention von Interventionen oder Todesfällen in Verbindung mit einem implantierbaren Defibrillator |
| US20110207811A1 (en) * | 2010-02-19 | 2011-08-25 | Sanofi-Aventis | Use of celivarone for reducing occurrences of cardiovascular hospitalization |
| FR2958290B1 (fr) | 2010-03-30 | 2012-10-19 | Sanofi Aventis | Procede de preparation de derives de sulfonamido-benzofurane |
| HUP1000330A2 (en) | 2010-06-18 | 2011-12-28 | Sanofi Sa | Process for the preparation of dronedarone and the novel intermediates |
| AU2011202542A1 (en) | 2010-07-14 | 2012-02-02 | Indian Institute Of Science | Benzothiophene carboxamide compounds, composition and applications thereof |
| FR2963006B1 (fr) | 2010-07-21 | 2013-03-15 | Sanofi Aventis | Procede de preparation de derives de nitro-benzofurane |
| FR2967067A1 (fr) | 2010-11-10 | 2012-05-11 | Sanofi Aventis | Composition pharmaceutique et forme galenique a base de dronedarone et son procede de preparation |
| HUP1100167A2 (en) | 2011-03-29 | 2012-11-28 | Sanofi Sa | Process for preparation of dronedarone by mesylation |
| HUP1100165A2 (en) | 2011-03-29 | 2012-12-28 | Sanofi Sa | Process for preparation of dronedarone by n-butylation |
| CN102757444B (zh) * | 2011-04-29 | 2016-02-10 | 南京信诺泰医药有限公司 | 具有一氧化氮供体性质的苯并呋喃类化合物 |
| FR2983198B1 (fr) | 2011-11-29 | 2013-11-15 | Sanofi Sa | Procede de preparation de derives de 5-amino-benzoyl-benzofurane |
| EP2617718A1 (de) | 2012-01-20 | 2013-07-24 | Sanofi | Verfahren zur Herstellung von Dronedaron unter Verwendung von Dibutylaminopropanolreagenz |
| US9221778B2 (en) | 2012-02-13 | 2015-12-29 | Sanofi | Process for preparation of dronedarone by removal of hydroxyl group |
| US9249119B2 (en) | 2012-02-14 | 2016-02-02 | Sanofi | Process for the preparation of dronedarone by oxidation of a sulphenyl group |
| US9382223B2 (en) | 2012-02-22 | 2016-07-05 | Sanofi | Process for preparation of dronedarone by oxidation of a hydroxyl group |
| US9238636B2 (en) | 2012-05-31 | 2016-01-19 | Sanofi | Process for preparation of dronedarone by Grignard reaction |
| CN105315245B (zh) * | 2014-06-16 | 2018-10-12 | 华润赛科药业有限责任公司 | 苯并呋喃类衍生物、其制备方法和应用 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3248401A (en) * | 1966-04-26 | Diethylaminoe hoxybenzoyl benzofurans | ||
| GB1345872A (en) * | 1970-09-03 | 1974-02-06 | Wyeth John & Brother Ltd | Amino-and acylamino-pyridine and hydropyridine derivatives |
| US4851554A (en) | 1987-04-06 | 1989-07-25 | University Of Tennessee Research Corporation | Certain 3-substituted 2-alkyl benzofuran derivatives |
| US4806663A (en) | 1987-04-06 | 1989-02-21 | The University Of Tennessee Research Corporation | Certain 3-substituted 2-alkyl benzofuran derivatives |
| US4831054A (en) * | 1988-04-18 | 1989-05-16 | Taro Pharmaceuticals, Ltd. | 2-Alkyl-3-benzoylbenzofurans useful for treating cardiac arrhythmia |
| AT391316B (de) | 1988-09-15 | 1990-09-25 | Ebewe Arzneimittel | Neue thienyloxy-alkylamin-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| FR2665444B1 (fr) * | 1990-08-06 | 1992-11-27 | Sanofi Sa | Derives d'amino-benzofuranne, benzothiophene ou indole, leur procede de preparation ainsi que les compositions les contenant. |
| JP3157882B2 (ja) * | 1991-11-15 | 2001-04-16 | 帝国臓器製薬株式会社 | 新規なベンゾチオフエン誘導体 |
| US5482949A (en) * | 1993-03-19 | 1996-01-09 | Eli Lilly And Company | Sulfonate derivatives of 3-aroylbenzo[b]thiophenes |
| US5364880A (en) * | 1993-06-16 | 1994-11-15 | Advanced Therapies, Inc. | Compound for treatment of cardiac arrhythmia, synthesis, and methods of use |
| US6756388B1 (en) * | 1993-10-12 | 2004-06-29 | Pfizer Inc. | Benzothiophenes and related compounds as estrogen agonists |
| US5482950A (en) * | 1993-10-15 | 1996-01-09 | Eli Lilly And Company | Methods for lowering serum cholesterol |
| US5523309A (en) * | 1995-03-10 | 1996-06-04 | Eli Lilly And Company | Benzofuran pharmaceutical compounds |
| CA2217373A1 (en) | 1996-10-10 | 1998-04-10 | Michael John Martin | Benzo¬b|thiophene compounds, intermediates, formulations, and methods |
-
2000
- 2000-08-23 FR FR0010834A patent/FR2813306B1/fr not_active Expired - Fee Related
-
2001
- 2001-08-21 CZ CZ20030521A patent/CZ304003B6/cs not_active IP Right Cessation
- 2001-08-21 PT PT01963113T patent/PT1315709E/pt unknown
- 2001-08-21 HU HU0302968A patent/HU229456B1/hu not_active IP Right Cessation
- 2001-08-21 PL PL362119A patent/PL219848B1/pl unknown
- 2001-08-21 EA EA200300062A patent/EA006237B1/ru not_active IP Right Cessation
- 2001-08-21 BR BRPI0113425-6A patent/BR0113425B1/pt not_active IP Right Cessation
- 2001-08-21 IL IL15363201A patent/IL153632A0/xx active IP Right Grant
- 2001-08-21 ES ES01963113T patent/ES2346291T3/es not_active Expired - Lifetime
- 2001-08-21 SI SI200130974T patent/SI1315709T1/sl unknown
- 2001-08-21 AU AU8414901A patent/AU8414901A/xx active Pending
- 2001-08-21 KR KR1020037002618A patent/KR100911280B1/ko active IP Right Grant
- 2001-08-21 NZ NZ523446A patent/NZ523446A/xx not_active IP Right Cessation
- 2001-08-21 ME MEP-230/08A patent/MEP23008A/xx unknown
- 2001-08-21 AT AT01963113T patent/ATE469138T1/de active
- 2001-08-21 DK DK01963113.4T patent/DK1315709T3/da active
- 2001-08-21 CN CNB018177670A patent/CN1246315C/zh not_active Expired - Fee Related
- 2001-08-21 ME MEP-2008-230A patent/ME00106B/me unknown
- 2001-08-21 DE DE60142240T patent/DE60142240D1/de not_active Expired - Lifetime
- 2001-08-21 AU AU2001284149A patent/AU2001284149B2/en not_active Ceased
- 2001-08-21 OA OA1200300035A patent/OA12359A/fr unknown
- 2001-08-21 EP EP01963113A patent/EP1315709B1/de not_active Expired - Lifetime
- 2001-08-21 SK SK216-2003A patent/SK288126B6/sk not_active IP Right Cessation
- 2001-08-21 JP JP2002521440A patent/JP5081363B2/ja not_active Expired - Fee Related
- 2001-08-21 RS YU12903A patent/RS51603B/sr unknown
- 2001-08-21 US US10/362,324 patent/US6949583B2/en not_active Expired - Lifetime
- 2001-08-21 MX MXPA03001463A patent/MXPA03001463A/es active IP Right Grant
- 2001-08-21 CA CA2415847A patent/CA2415847C/fr not_active Expired - Fee Related
- 2001-08-21 WO PCT/FR2001/002640 patent/WO2002016339A1/fr active IP Right Grant
- 2001-08-22 TW TW090120633A patent/TWI290920B/zh not_active IP Right Cessation
- 2001-08-23 AR ARP010104023A patent/AR032892A1/es not_active Application Discontinuation
-
2002
- 2002-12-24 IL IL153632A patent/IL153632A/en not_active IP Right Cessation
-
2003
- 2003-01-13 IS IS6677A patent/IS2821B/is unknown
- 2003-01-28 ZA ZA200300744A patent/ZA200300744B/xx unknown
- 2003-02-05 BG BG107527A patent/BG66240B1/bg unknown
- 2003-02-17 MA MA27042A patent/MA26943A1/fr unknown
- 2003-02-20 NO NO20030800A patent/NO328138B1/no not_active IP Right Cessation
- 2003-07-25 HK HK03105391.1A patent/HK1053113A1/xx not_active IP Right Cessation
-
2010
- 2010-08-17 CY CY20101100763T patent/CY1110738T1/el unknown
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2011
- 2011-12-14 JP JP2011273790A patent/JP5603849B2/ja not_active Expired - Fee Related
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