HU176557B - Process for producing acetamidoxime derivatives of benzofurane - Google Patents
Process for producing acetamidoxime derivatives of benzofurane Download PDFInfo
- Publication number
- HU176557B HU176557B HU76LA901A HULA000901A HU176557B HU 176557 B HU176557 B HU 176557B HU 76LA901 A HU76LA901 A HU 76LA901A HU LA000901 A HULA000901 A HU LA000901A HU 176557 B HU176557 B HU 176557B
- Authority
- HU
- Hungary
- Prior art keywords
- ethyl
- benzofuranyl
- formula
- oxadiazol
- acetamidoxime
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 37
- 230000008569 process Effects 0.000 title claims description 7
- AEXITZJSLGALNH-UHFFFAOYSA-N n'-hydroxyethanimidamide Chemical class CC(N)=NO AEXITZJSLGALNH-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
- -1 dimethylamino, diethylamino, di-n-propylamino Chemical group 0.000 claims description 125
- 238000002360 preparation method Methods 0.000 claims description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 238000007142 ring opening reaction Methods 0.000 claims description 4
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 25
- 239000000203 mixture Substances 0.000 abstract description 12
- 230000003276 anti-hypertensive effect Effects 0.000 abstract description 8
- 239000007858 starting material Substances 0.000 abstract description 7
- 230000001225 therapeutic effect Effects 0.000 abstract description 7
- 230000001882 diuretic effect Effects 0.000 abstract description 5
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 abstract 2
- 230000005792 cardiovascular activity Effects 0.000 abstract 1
- ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical class O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 123
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 62
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- 229960004592 isopropanol Drugs 0.000 description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 24
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- 206010020772 Hypertension Diseases 0.000 description 20
- 239000000243 solution Substances 0.000 description 17
- 241000700159 Rattus Species 0.000 description 16
- 238000001953 recrystallisation Methods 0.000 description 16
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- JYXQXKHTALMLNI-UHFFFAOYSA-N 2-(2-ethyl-1-benzofuran-3-yl)-n-hydroxy-n'-(2-morpholin-4-ylethyl)ethanimidamide Chemical compound CCC=1OC2=CC=CC=C2C=1CC(NO)=NCCN1CCOCC1 JYXQXKHTALMLNI-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
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- 238000010992 reflux Methods 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 210000002700 urine Anatomy 0.000 description 7
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002220 antihypertensive agent Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 210000003734 kidney Anatomy 0.000 description 4
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VPGRYOFKCNULNK-ACXQXYJUSA-N Deoxycorticosterone acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)COC(=O)C)[C@@]1(C)CC2 VPGRYOFKCNULNK-ACXQXYJUSA-N 0.000 description 3
- 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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- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
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- 229910052708 sodium Inorganic materials 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000002889 sympathetic effect Effects 0.000 description 3
- 231100000816 toxic dose Toxicity 0.000 description 3
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- SNFAMSJEKJVIDA-UHFFFAOYSA-N 2-(2-ethyl-1-benzofuran-3-yl)-n'-hydroxy-2-methylpropanimidamide Chemical compound C1=CC=C2C(C(C)(C)C(N)=NO)=C(CC)OC2=C1 SNFAMSJEKJVIDA-UHFFFAOYSA-N 0.000 description 2
- GQDGLWUFLGHKON-UHFFFAOYSA-N 2-(2-ethyl-1-benzofuran-3-yl)-n'-hydroxyethanimidamide;hydrochloride Chemical compound Cl.C1=CC=C2C(CC(N)=NO)=C(CC)OC2=C1 GQDGLWUFLGHKON-UHFFFAOYSA-N 0.000 description 2
- PVWUVYBOLVWWHC-UHFFFAOYSA-N 2-(2-ethyl-1-benzofuran-3-yl)-n'-hydroxypropanimidamide Chemical compound C1=CC=C2C(C(C)C(N)=NO)=C(CC)OC2=C1 PVWUVYBOLVWWHC-UHFFFAOYSA-N 0.000 description 2
- RWCHGCSLPRNFRX-UHFFFAOYSA-N 2-(2-ethyl-1-benzofuran-3-yl)acetonitrile Chemical compound C1=CC=C2C(CC#N)=C(CC)OC2=C1 RWCHGCSLPRNFRX-UHFFFAOYSA-N 0.000 description 2
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- JQQKLSYCABAIJP-UHFFFAOYSA-N 2-(2-ethyl-1-benzofuran-3-yl)propanoic acid Chemical compound C1=CC=C2C(C(C)C(O)=O)=C(CC)OC2=C1 JQQKLSYCABAIJP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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- 208000007530 Essential hypertension Diseases 0.000 description 2
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- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- TVEGBGLLZMPPOI-UHFFFAOYSA-N n'-hydroxyethanimidamide;dihydrochloride Chemical compound Cl.Cl.CC(N)=NO TVEGBGLLZMPPOI-UHFFFAOYSA-N 0.000 description 2
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- PEKBDPWIKMPIIL-UHFFFAOYSA-N (2-ethyl-1-benzofuran-3-yl)methyl acetate Chemical compound C1=CC=C2C(COC(C)=O)=C(CC)OC2=C1 PEKBDPWIKMPIIL-UHFFFAOYSA-N 0.000 description 1
- LKAMWXDMKZWCAQ-UHFFFAOYSA-N 1-[3-(3-pyrrolidin-1-ylpropoxy)propyl]pyrrolidine Chemical compound C1CCCN1CCCOCCCN1CCCC1 LKAMWXDMKZWCAQ-UHFFFAOYSA-N 0.000 description 1
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- XFSLKSZBLORVIX-UHFFFAOYSA-N 2-(2-ethyl-1-benzofuran-3-yl)-n-hydroxy-2-methyl-n'-(2-morpholin-4-ylethyl)propanimidamide Chemical compound CCC=1OC2=CC=CC=C2C=1C(C)(C)C(NO)=NCCN1CCOCC1 XFSLKSZBLORVIX-UHFFFAOYSA-N 0.000 description 1
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- HOBWAPHTEJGALG-JKCMADFCSA-N [(1r,5s)-8-methyl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate;sulfate Chemical compound [O-]S([O-])(=O)=O.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1 HOBWAPHTEJGALG-JKCMADFCSA-N 0.000 description 1
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- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- XIWFQDBQMCDYJT-UHFFFAOYSA-M benzyl-dimethyl-tridecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 XIWFQDBQMCDYJT-UHFFFAOYSA-M 0.000 description 1
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- 210000004204 blood vessel Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 210000001168 carotid artery common Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical class C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- ZESRJSPZRDMNHY-UHFFFAOYSA-N de-oxy corticosterone Natural products O=C1CCC2(C)C3CCC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 ZESRJSPZRDMNHY-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940119740 deoxycorticosterone Drugs 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000000574 ganglionic effect Effects 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000026781 habituation Effects 0.000 description 1
- 229960002003 hydrochlorothiazide Drugs 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 description 1
- VPBPOXIFRZBJEU-UHFFFAOYSA-L iron(2+);dinitrite Chemical compound [Fe+2].[O-]N=O.[O-]N=O VPBPOXIFRZBJEU-UHFFFAOYSA-L 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 210000003801 laryngeal nerve Anatomy 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 208000012866 low blood pressure Diseases 0.000 description 1
- 201000005857 malignant hypertension Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- DGEYTDCFMQMLTH-UHFFFAOYSA-N methanol;propan-2-ol Chemical compound OC.CC(C)O DGEYTDCFMQMLTH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- CSXSCJPKUQRGBB-UHFFFAOYSA-N n-hydroxy-2-(2-methyl-1-benzofuran-3-yl)-n'-(2-morpholin-4-ylethyl)ethanimidamide Chemical compound CC=1OC2=CC=CC=C2C=1CC(=NO)NCCN1CCOCC1 CSXSCJPKUQRGBB-UHFFFAOYSA-N 0.000 description 1
- 210000004237 neck muscle Anatomy 0.000 description 1
- 230000002232 neuromuscular Effects 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- ZDYUUBIMAGBMPY-UHFFFAOYSA-N oxalic acid;hydrate Chemical compound O.OC(=O)C(O)=O ZDYUUBIMAGBMPY-UHFFFAOYSA-N 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000015598 salt intake Nutrition 0.000 description 1
- 210000003497 sciatic nerve Anatomy 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000003730 sympathetic denervation Effects 0.000 description 1
- 230000000194 sympathicotonic effect Effects 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 229940057613 veratrum Drugs 0.000 description 1
Classifications
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB52475/75A GB1508210A (en) | 1975-12-22 | 1975-12-22 | Benzofuran-derived amidoximes and process for preparing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU176557B true HU176557B (en) | 1981-03-28 |
Family
ID=10464059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU76LA901A HU176557B (en) | 1975-12-22 | 1976-12-21 | Process for producing acetamidoxime derivatives of benzofurane |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS52102268A (OSRAM) |
| AR (1) | AR212605A1 (OSRAM) |
| AT (1) | AT354430B (OSRAM) |
| AU (1) | AU503931B2 (OSRAM) |
| BE (1) | BE849430A (OSRAM) |
| CA (1) | CA1080723A (OSRAM) |
| CH (1) | CH617688A5 (OSRAM) |
| DD (1) | DD127762A5 (OSRAM) |
| DE (1) | DE2657902A1 (OSRAM) |
| DK (1) | DK577276A (OSRAM) |
| ES (1) | ES454421A1 (OSRAM) |
| FI (1) | FI60395C (OSRAM) |
| FR (1) | FR2336127A1 (OSRAM) |
| GB (1) | GB1508210A (OSRAM) |
| HU (1) | HU176557B (OSRAM) |
| IE (1) | IE44753B1 (OSRAM) |
| IT (1) | IT1123948B (OSRAM) |
| MX (1) | MX3927E (OSRAM) |
| NL (1) | NL7613753A (OSRAM) |
| NO (1) | NO144794C (OSRAM) |
| NZ (1) | NZ182809A (OSRAM) |
| OA (1) | OA05521A (OSRAM) |
| PL (1) | PL102695B1 (OSRAM) |
| PT (1) | PT65971B (OSRAM) |
| SE (1) | SE429233B (OSRAM) |
| SU (1) | SU598564A3 (OSRAM) |
| YU (1) | YU309376A (OSRAM) |
| ZA (1) | ZA767241B (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3398941A1 (en) * | 2017-05-03 | 2018-11-07 | AXXAM S.p.A. | Heterocyclic p2x7 antagonists |
-
1975
- 1975-12-22 GB GB52475/75A patent/GB1508210A/en not_active Expired
-
1976
- 1976-12-03 IE IE2663/76A patent/IE44753B1/en unknown
- 1976-12-06 ZA ZA767241A patent/ZA767241B/xx unknown
- 1976-12-06 NZ NZ182809A patent/NZ182809A/xx unknown
- 1976-12-10 NL NL7613753A patent/NL7613753A/xx not_active Application Discontinuation
- 1976-12-13 AR AR265814A patent/AR212605A1/es active
- 1976-12-14 AU AU20534/76A patent/AU503931B2/en not_active Expired
- 1976-12-14 FR FR7637622A patent/FR2336127A1/fr active Granted
- 1976-12-15 BE BE173280A patent/BE849430A/xx not_active IP Right Cessation
- 1976-12-15 MX MX765235U patent/MX3927E/es unknown
- 1976-12-15 CA CA267,918A patent/CA1080723A/en not_active Expired
- 1976-12-15 FI FI763604A patent/FI60395C/fi not_active IP Right Cessation
- 1976-12-15 PT PT65971A patent/PT65971B/pt unknown
- 1976-12-20 CH CH1603476A patent/CH617688A5/fr not_active IP Right Cessation
- 1976-12-20 ES ES454421A patent/ES454421A1/es not_active Expired
- 1976-12-20 YU YU03093/76A patent/YU309376A/xx unknown
- 1976-12-21 DK DK577276A patent/DK577276A/da not_active Application Discontinuation
- 1976-12-21 AT AT948476A patent/AT354430B/de not_active IP Right Cessation
- 1976-12-21 HU HU76LA901A patent/HU176557B/hu unknown
- 1976-12-21 SU SU762430683A patent/SU598564A3/ru active
- 1976-12-21 PL PL1976194589A patent/PL102695B1/pl unknown
- 1976-12-21 NO NO76764332A patent/NO144794C/no unknown
- 1976-12-21 DE DE19762657902 patent/DE2657902A1/de not_active Withdrawn
- 1976-12-21 IT IT7630679A patent/IT1123948B/it active
- 1976-12-21 SE SE7614368A patent/SE429233B/xx unknown
- 1976-12-22 JP JP15558976A patent/JPS52102268A/ja active Pending
- 1976-12-22 DD DD7600196548A patent/DD127762A5/xx unknown
- 1976-12-22 OA OA56023A patent/OA05521A/xx unknown
Also Published As
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