NO325691B1 - Benzofuranderivater, farmasoytiske preparater inneholdende disse, anvendelse av disse forbindelsene som medikamenter, anvendelse av disse for fremstilling av farmasoytiske preparater samt fremstilling av disse. - Google Patents
Benzofuranderivater, farmasoytiske preparater inneholdende disse, anvendelse av disse forbindelsene som medikamenter, anvendelse av disse for fremstilling av farmasoytiske preparater samt fremstilling av disse. Download PDFInfo
- Publication number
- NO325691B1 NO325691B1 NO20030417A NO20030417A NO325691B1 NO 325691 B1 NO325691 B1 NO 325691B1 NO 20030417 A NO20030417 A NO 20030417A NO 20030417 A NO20030417 A NO 20030417A NO 325691 B1 NO325691 B1 NO 325691B1
- Authority
- NO
- Norway
- Prior art keywords
- dimethoxy
- ylmethyl
- benzofuran
- mmol
- pyrimidin
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 59
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 7
- 239000003814 drug Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title abstract description 17
- 150000001907 coumarones Chemical class 0.000 title abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 3
- 238000000034 method Methods 0.000 claims abstract description 75
- 239000004480 active ingredient Substances 0.000 claims abstract description 5
- -1 4-fluorophenylaminomethyl Chemical group 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 6
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 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
- 125000005002 aryl methyl group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 229930192474 thiophene Natural products 0.000 claims description 5
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 4
- 239000012964 benzotriazole Substances 0.000 claims description 4
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- JKWQHCSGMTWRIQ-UHFFFAOYSA-N 2,3-dihydro-1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NCCC2=N1 JKWQHCSGMTWRIQ-UHFFFAOYSA-N 0.000 claims description 3
- WSSZYRKYQIIXCZ-UHFFFAOYSA-N 5-[(2-benzyl-6,7-dimethoxy-1-benzofuran-4-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12C=C(CC=3C=CC=CC=3)OC2=C(OC)C(OC)=CC=1CC1=CN=C(N)N=C1N WSSZYRKYQIIXCZ-UHFFFAOYSA-N 0.000 claims description 3
- YKJOLDAJQKXHQM-UHFFFAOYSA-N 5-[(6,7-dimethoxy-2-phenyl-1-benzofuran-4-yl)methyl]pyrimidine-2,4-diamine Chemical compound C=12C=C(C=3C=CC=CC=3)OC2=C(OC)C(OC)=CC=1CC1=CN=C(N)N=C1N YKJOLDAJQKXHQM-UHFFFAOYSA-N 0.000 claims description 3
- JTGBHXQSBHUNAO-UHFFFAOYSA-N 5-[[2-(cyclopropylmethyl)-6,7-dimethoxy-1-benzofuran-4-yl]methyl]pyrimidine-2,4-diamine Chemical compound C=12C=C(CC3CC3)OC2=C(OC)C(OC)=CC=1CC1=CN=C(N)N=C1N JTGBHXQSBHUNAO-UHFFFAOYSA-N 0.000 claims description 3
- HSVBBFREAYSFJX-UHFFFAOYSA-N 5-[[6,7-dimethoxy-2-[(4-methoxyphenyl)methyl]-1-benzofuran-4-yl]methyl]pyrimidine-2,4-diamine Chemical compound C1=CC(OC)=CC=C1CC(OC1=C(OC)C(OC)=C2)=CC1=C2CC1=CN=C(N)N=C1N HSVBBFREAYSFJX-UHFFFAOYSA-N 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
- XDTYTOYRQVGRPM-UHFFFAOYSA-N 5-[[2-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-1-benzofuran-4-yl]methyl]pyrimidine-2,4-diamine Chemical compound C1=C(OC)C(OC)=CC=C1CC(OC1=C(OC)C(OC)=C2)=CC1=C2CC1=CN=C(N)N=C1N XDTYTOYRQVGRPM-UHFFFAOYSA-N 0.000 claims description 2
- QVUZYVOBYZZVHI-UHFFFAOYSA-N 5-[[2-[(4-fluoroanilino)methyl]-6,7-dimethoxy-1-benzofuran-4-yl]methyl]pyrimidine-2,4-diamine Chemical compound C=12C=C(CNC=3C=CC(F)=CC=3)OC2=C(OC)C(OC)=CC=1CC1=CN=C(N)N=C1N QVUZYVOBYZZVHI-UHFFFAOYSA-N 0.000 claims description 2
- JFVUHRFMYOXBJY-UHFFFAOYSA-N 5-[[2-[(4-fluorophenyl)methyl]-6,7-dimethoxy-1-benzofuran-4-yl]methyl]pyrimidine-2,4-diamine Chemical compound C=12C=C(CC=3C=CC(F)=CC=3)OC2=C(OC)C(OC)=CC=1CC1=CN=C(N)N=C1N JFVUHRFMYOXBJY-UHFFFAOYSA-N 0.000 claims description 2
- LQSAWCOJLJFZHX-UHFFFAOYSA-N 5-[[6,7-dimethoxy-2-(pyridin-2-ylmethyl)-1-benzofuran-4-yl]methyl]pyrimidine-2,4-diamine Chemical compound C=12C=C(CC=3N=CC=CC=3)OC2=C(OC)C(OC)=CC=1CC1=CN=C(N)N=C1N LQSAWCOJLJFZHX-UHFFFAOYSA-N 0.000 claims description 2
- GATGPUDBIFJUNI-UHFFFAOYSA-N 5-[[6,7-dimethoxy-2-(pyridin-4-ylmethyl)-1-benzofuran-4-yl]methyl]pyrimidine-2,4-diamine Chemical compound C=12C=C(CC=3C=CN=CC=3)OC2=C(OC)C(OC)=CC=1CC1=CN=C(N)N=C1N GATGPUDBIFJUNI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 244000000058 gram-negative pathogen Species 0.000 claims description 2
- 244000000059 gram-positive pathogen Species 0.000 claims description 2
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 3
- MFFFCAXZWVTCEU-UHFFFAOYSA-N 5-[[6,7-dimethoxy-2-(pyridin-3-ylmethyl)-1-benzofuran-4-yl]methyl]pyrimidine-2,4-diamine Chemical compound C=12C=C(CC=3C=NC=CC=3)OC2=C(OC)C(OC)=CC=1CC1=CN=C(N)N=C1N MFFFCAXZWVTCEU-UHFFFAOYSA-N 0.000 claims 1
- 239000012876 carrier material Substances 0.000 claims 1
- 230000002924 anti-infective effect Effects 0.000 abstract description 2
- 229960005475 antiinfective agent Drugs 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 70
- 238000006243 chemical reaction Methods 0.000 description 61
- 239000013067 intermediate product Substances 0.000 description 50
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
- 239000003921 oil Substances 0.000 description 37
- 235000019198 oils Nutrition 0.000 description 37
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 36
- 239000007787 solid Substances 0.000 description 36
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 35
- 239000000243 solution Substances 0.000 description 29
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- 238000000746 purification Methods 0.000 description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
- 229910052786 argon Inorganic materials 0.000 description 18
- 235000019441 ethanol Nutrition 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000002425 crystallisation Methods 0.000 description 15
- 230000008025 crystallization Effects 0.000 description 15
- FENJKTQEFUPECW-UHFFFAOYSA-N 3-anilinopropanenitrile Chemical compound N#CCCNC1=CC=CC=C1 FENJKTQEFUPECW-UHFFFAOYSA-N 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- 229960000789 guanidine hydrochloride Drugs 0.000 description 14
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 14
- AJJVRYDRZJOQFV-UHFFFAOYSA-N 5-[[2-(chloromethyl)-6,7-dimethoxy-1-benzofuran-4-yl]methyl]pyrimidine-2,4-diamine Chemical compound C=12C=C(CCl)OC2=C(OC)C(OC)=CC=1CC1=CN=C(N)N=C1N AJJVRYDRZJOQFV-UHFFFAOYSA-N 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 150000002367 halogens Chemical group 0.000 description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 238000003818 flash chromatography Methods 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- QOOZHVOIVZHKBO-UHFFFAOYSA-N methyl 2-formyl-3-hydroxy-4,5-dimethoxybenzoate Chemical compound COC(=O)C1=CC(OC)=C(OC)C(O)=C1C=O QOOZHVOIVZHKBO-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- IEFUQBKIAHNBAY-UHFFFAOYSA-N 6,7-dimethoxy-4-methoxycarbonyl-1-benzofuran-2-carboxylic acid Chemical compound COC(=O)C1=CC(OC)=C(OC)C2=C1C=C(C(O)=O)O2 IEFUQBKIAHNBAY-UHFFFAOYSA-N 0.000 description 7
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 230000009467 reduction Effects 0.000 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 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000002252 acyl group Chemical group 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
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- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
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- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 150000003138 primary alcohols Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- MTDFEQZPSBHGRU-UHFFFAOYSA-N 2-(hydroxymethyl)-6,7-dimethoxy-1-benzofuran-4-carboxylic acid Chemical compound COC1=CC(C(O)=O)=C2C=C(CO)OC2=C1OC MTDFEQZPSBHGRU-UHFFFAOYSA-N 0.000 description 3
- XHPZVBGIPQQTQW-UHFFFAOYSA-N 5-benzylpyrimidine-2,4-diamine Chemical class NC1=NC(N)=NC=C1CC1=CC=CC=C1 XHPZVBGIPQQTQW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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- GSVULOGUGSYOJF-UHFFFAOYSA-N [4-[(2,4-diaminopyrimidin-5-yl)methyl]-6,7-dimethoxy-1-benzofuran-2-yl]methanol Chemical compound C=12C=C(CO)OC2=C(OC)C(OC)=CC=1CC1=CN=C(N)N=C1N GSVULOGUGSYOJF-UHFFFAOYSA-N 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- GRTGGSXWHGKRSB-UHFFFAOYSA-N dichloromethyl methyl ether Chemical compound COC(Cl)Cl GRTGGSXWHGKRSB-UHFFFAOYSA-N 0.000 description 3
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000007918 intramuscular administration Methods 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- ZQIFEASGJJQAHG-UHFFFAOYSA-N methyl 2-(cyclopropylmethyl)-6,7-dimethoxy-1-benzofuran-4-carboxylate Chemical compound C=1C=2C(C(=O)OC)=CC(OC)=C(OC)C=2OC=1CC1CC1 ZQIFEASGJJQAHG-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
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- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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- 125000005047 dihydroimidazolyl group Chemical group N1(CNC=C1)* 0.000 description 1
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- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
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- WKGMWOUHQRPHHZ-UHFFFAOYSA-N ethane-1,2-diol;toluene Chemical compound OCCO.CC1=CC=CC=C1 WKGMWOUHQRPHHZ-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- RDULEYWUGKOCMR-UHFFFAOYSA-N ethyl 2-chloro-3-oxobutanoate Chemical compound CCOC(=O)C(Cl)C(C)=O RDULEYWUGKOCMR-UHFFFAOYSA-N 0.000 description 1
- UIXQOBTYQBXKTQ-UHFFFAOYSA-N ethyl 4-[(2,4-diaminopyrimidin-5-yl)methyl]-6,7-dimethoxy-3-methyl-1-benzofuran-2-carboxylate Chemical compound C=12C(C)=C(C(=O)OCC)OC2=C(OC)C(OC)=CC=1CC1=CN=C(N)N=C1N UIXQOBTYQBXKTQ-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
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- 239000000945 filler Substances 0.000 description 1
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- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
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- LNTHITQWFMADLM-UHFFFAOYSA-M gallate Chemical class OC1=CC(C([O-])=O)=CC(O)=C1O LNTHITQWFMADLM-UHFFFAOYSA-M 0.000 description 1
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- 235000011187 glycerol Nutrition 0.000 description 1
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- 229960004198 guanidine Drugs 0.000 description 1
- 229940047650 haemophilus influenzae Drugs 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
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- 125000005350 hydroxycycloalkyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
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- 238000007913 intrathecal administration Methods 0.000 description 1
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- 229940045505 klebsiella pneumoniae Drugs 0.000 description 1
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- JYMWCIDKRZUEPT-UHFFFAOYSA-N methyl 2-benzyl-6,7-dimethoxy-1-benzofuran-4-carboxylate Chemical compound C=1C=2C(C(=O)OC)=CC(OC)=C(OC)C=2OC=1CC1=CC=CC=C1 JYMWCIDKRZUEPT-UHFFFAOYSA-N 0.000 description 1
- DAGLCAMSBHIRLF-UHFFFAOYSA-N methyl 2-bromo-3-hydroxy-4,5-dimethoxybenzoate Chemical compound COC(=O)C1=CC(OC)=C(OC)C(O)=C1Br DAGLCAMSBHIRLF-UHFFFAOYSA-N 0.000 description 1
- AJYHRNHPVLMABN-UHFFFAOYSA-N methyl 6,7-dimethoxy-2-(4-methoxybenzoyl)-1-benzofuran-4-carboxylate Chemical compound C=1C=2C(C(=O)OC)=CC(OC)=C(OC)C=2OC=1C(=O)C1=CC=C(OC)C=C1 AJYHRNHPVLMABN-UHFFFAOYSA-N 0.000 description 1
- KACHFMOHOPLTNX-UHFFFAOYSA-N methyl tri-O-methylgallate Natural products COC(=O)C1=CC(OC)=C(OC)C(OC)=C1 KACHFMOHOPLTNX-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- NMWMSNPYHDISHQ-UHFFFAOYSA-N n-(4-ethoxy-2-methoxyphenyl)acetamide Chemical compound CCOC1=CC=C(NC(C)=O)C(OC)=C1 NMWMSNPYHDISHQ-UHFFFAOYSA-N 0.000 description 1
- AYEQJLOHMLYKAV-UHFFFAOYSA-N n-(4-sulfanylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(S)C=C1 AYEQJLOHMLYKAV-UHFFFAOYSA-N 0.000 description 1
- MKSALCNKEBUWQS-UHFFFAOYSA-N n-[4-[[4-[(2,4-diaminopyrimidin-5-yl)methyl]-6,7-dimethoxy-1-benzofuran-2-yl]methylsulfanyl]phenyl]acetamide Chemical compound C=12C=C(CSC=3C=CC(NC(C)=O)=CC=3)OC2=C(OC)C(OC)=CC=1CC1=CN=C(N)N=C1N MKSALCNKEBUWQS-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000006259 organic additive Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
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- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- CVEDVJRENZAPPJ-UHFFFAOYSA-N potassium;ethanol;2-methylpropan-2-olate Chemical compound [K+].CCO.CC(C)(C)[O-] CVEDVJRENZAPPJ-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical class OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000007660 quinolones Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229960005404 sulfamethoxazole Drugs 0.000 description 1
- JLKIGFTWXXRPMT-UHFFFAOYSA-N sulphamethoxazole Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 JLKIGFTWXXRPMT-UHFFFAOYSA-N 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
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
-
- 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
- C07D405/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/EP2000/007357 WO2002010156A1 (en) | 2000-07-29 | 2000-07-29 | Benzofuran derivatives and their use as antibacterial agents |
| PCT/EP2001/008426 WO2002010157A1 (en) | 2000-07-29 | 2001-07-20 | Benzofuran derivatives and their use as antibacterial agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20030417L NO20030417L (no) | 2003-01-27 |
| NO20030417D0 NO20030417D0 (no) | 2003-01-27 |
| NO325691B1 true NO325691B1 (no) | 2008-07-07 |
Family
ID=8164043
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20030417A NO325691B1 (no) | 2000-07-29 | 2003-01-27 | Benzofuranderivater, farmasoytiske preparater inneholdende disse, anvendelse av disse forbindelsene som medikamenter, anvendelse av disse for fremstilling av farmasoytiske preparater samt fremstilling av disse. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US7030130B2 (zh) |
| EP (1) | EP1307445B1 (zh) |
| JP (1) | JP2004505077A (zh) |
| CN (1) | CN1317277C (zh) |
| AT (1) | ATE313541T1 (zh) |
| AU (1) | AU2001289714A1 (zh) |
| CA (1) | CA2417401C (zh) |
| DE (1) | DE60116106T2 (zh) |
| DK (1) | DK1307445T3 (zh) |
| ES (1) | ES2250474T3 (zh) |
| MX (1) | MXPA03000606A (zh) |
| NO (1) | NO325691B1 (zh) |
| TW (1) | TWI283674B (zh) |
| WO (2) | WO2002010156A1 (zh) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6969730B2 (en) | 2001-03-16 | 2005-11-29 | Abbott Laboratories | Amines as histamine-3 receptor ligands and their therapeutic applications |
| EP1370546A2 (en) * | 2001-03-16 | 2003-12-17 | Abbott Laboratories | Novel amines as histamine-3 receptor ligands and their therapeutic applications |
| HUP0600114A2 (en) * | 2003-07-11 | 2007-09-28 | Arpida Ag | Benzofuran derivatives and their use in the treatment of microbal infections |
| WO2005014586A1 (en) * | 2003-08-08 | 2005-02-17 | Arpida Ag | Novel process for the preparation of 2h-chromenes |
| DE10351315A1 (de) * | 2003-10-31 | 2005-06-16 | Aventis Pharma Deutschland Gmbh | 2-Phenyl-benzofuran-Derivate, Verfahren zur ihrer Herstellung und ihre Verwendung |
| US7148254B2 (en) | 2003-10-31 | 2006-12-12 | Sanofi-Aventis Deutschland Gmbh | 2-Phenylbenzofuran derivatives, a process for preparing them, and their use |
| CN101087779A (zh) * | 2005-01-07 | 2007-12-12 | 阿皮德公开股份有限公司 | 选择的苯并呋喃衍生物 |
| CN101115743B (zh) * | 2005-02-18 | 2011-04-13 | 阿皮德公开股份有限公司 | 用于制备2h-色烯的新方法 |
| US7737157B2 (en) * | 2008-08-29 | 2010-06-15 | Hutchison Medipharma Enterprises Limited | Pyrimidine compounds |
| KR101156666B1 (ko) | 2010-09-17 | 2012-06-15 | 대한민국(농촌진흥청장) | 신규한 항생활성 화합물 및 그 화합물을 포함하는 항생 조성물 |
| CN103288805B (zh) * | 2013-03-13 | 2016-09-14 | 天津药物研究院有限公司 | 含有苯并呋喃的嘧啶类化合物及其制备方法和用途 |
| RU2657559C2 (ru) * | 2015-12-01 | 2018-06-14 | Общество с ограниченной ответственностью "Квантум Фармасьютикалс" | Медицинское применение фармацевтических композиций на основе роданиновых производных бензотиофена, ингибиторов белка клеточного деления FtsZ |
| US11390614B2 (en) | 2017-11-10 | 2022-07-19 | Jiangsu Hengrui Medicine Co., Ltd. | Method for preparing benzofuran derivative |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB875562A (en) * | 1957-02-21 | 1961-08-23 | Wellcome Found | Improvements in and relating to pyrimidine derivatives and the preparation thereof |
| US4438267A (en) * | 1980-11-11 | 1984-03-20 | Daluge Susan M | Monoheteroring compounds and their use |
| ZA833067B (en) * | 1982-05-01 | 1984-12-24 | Wellcome Found | Antibacterial compounds |
| DK190983A (da) * | 1982-05-01 | 1983-11-02 | Wellcome Found | 2,4-diamino-5-(substituerede)pyrimidiner, fremgangsmaade til deres fremstilling og mellemprodukter derfor |
| EP0866791B1 (en) * | 1995-12-04 | 2002-01-30 | Arpida AG, | Diaminopyrimidines, pharmaceutical compositions containing them and their use as antibacterial |
-
2000
- 2000-07-29 WO PCT/EP2000/007357 patent/WO2002010156A1/en active Application Filing
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2001
- 2001-07-20 DE DE60116106T patent/DE60116106T2/de not_active Expired - Fee Related
- 2001-07-20 JP JP2002515886A patent/JP2004505077A/ja active Pending
- 2001-07-20 ES ES01969459T patent/ES2250474T3/es not_active Expired - Lifetime
- 2001-07-20 CN CNB018123325A patent/CN1317277C/zh not_active Expired - Fee Related
- 2001-07-20 US US10/333,853 patent/US7030130B2/en not_active Expired - Fee Related
- 2001-07-20 CA CA002417401A patent/CA2417401C/en not_active Expired - Fee Related
- 2001-07-20 AT AT01969459T patent/ATE313541T1/de not_active IP Right Cessation
- 2001-07-20 AU AU2001289714A patent/AU2001289714A1/en not_active Abandoned
- 2001-07-20 WO PCT/EP2001/008426 patent/WO2002010157A1/en active IP Right Grant
- 2001-07-20 DK DK01969459T patent/DK1307445T3/da active
- 2001-07-20 EP EP01969459A patent/EP1307445B1/en not_active Expired - Lifetime
- 2001-07-20 MX MXPA03000606A patent/MXPA03000606A/es active IP Right Grant
- 2001-08-08 TW TW090119335A patent/TWI283674B/zh not_active IP Right Cessation
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Also Published As
| Publication number | Publication date |
|---|---|
| ATE313541T1 (de) | 2006-01-15 |
| CN1440404A (zh) | 2003-09-03 |
| US20040034047A1 (en) | 2004-02-19 |
| CA2417401A1 (en) | 2002-02-07 |
| CA2417401C (en) | 2009-11-10 |
| CN1317277C (zh) | 2007-05-23 |
| NO20030417L (no) | 2003-01-27 |
| DE60116106D1 (de) | 2006-01-26 |
| DE60116106T2 (de) | 2006-06-29 |
| WO2002010156A1 (en) | 2002-02-07 |
| EP1307445A1 (en) | 2003-05-07 |
| MXPA03000606A (es) | 2004-04-02 |
| JP2004505077A (ja) | 2004-02-19 |
| WO2002010157A1 (en) | 2002-02-07 |
| US7030130B2 (en) | 2006-04-18 |
| EP1307445B1 (en) | 2005-12-21 |
| TWI283674B (en) | 2007-07-11 |
| DK1307445T3 (da) | 2006-04-10 |
| ES2250474T3 (es) | 2006-04-16 |
| AU2001289714A1 (en) | 2002-02-13 |
| NO20030417D0 (no) | 2003-01-27 |
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