IL45525A - (2-hydroxy-3-amino-propoxy)benzoyl benzofuran derivatives - Google Patents

(2-hydroxy-3-amino-propoxy)benzoyl benzofuran derivatives

Info

Publication number: IL45525A
Authority: IL; Israel
Prior art keywords: benzofuran; butyl; hydroxy; compound; mol
Prior art date: 1973-09-21

Application number

IL45525A

Other languages

English (en)

Other versions

IL45525A0 (en

Original Assignee

Smithkline Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1973-09-21

Filing date

1974-08-23

Publication date

1977-08-31

1974-08-23 Application filed by Smithkline Corp filed Critical Smithkline Corp

1974-11-29 Publication of IL45525A0 publication Critical patent/IL45525A0/xx

1977-08-31 Publication of IL45525A publication Critical patent/IL45525A/en

Links

MYLJSNXLOBLDOC-UHFFFAOYSA-N [3-(3-amino-2-hydroxypropoxy)-1-benzofuran-2-yl]-phenylmethanone Chemical class OC(COC1=C(OC2=C1C=CC=C2)C(C2=CC=CC=C2)=O)CN MYLJSNXLOBLDOC-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 abstract description 87
150000001907 coumarones Chemical class 0.000 abstract description 6
230000000694 effects Effects 0.000 abstract description 6
239000003218 coronary vasodilator agent Substances 0.000 abstract description 3
230000000144 pharmacologic effect Effects 0.000 abstract description 3
206010002383 Angina Pectoris Diseases 0.000 abstract description 2
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical class C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 230
238000000034 method Methods 0.000 description 63
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 57
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 56
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
239000004593 Epoxy Substances 0.000 description 47
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
239000000243 solution Substances 0.000 description 44
239000000203 mixture Substances 0.000 description 37
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 33
239000011541 reaction mixture Substances 0.000 description 32
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 27
125000000217 alkyl group Chemical group 0.000 description 25
229910052739 hydrogen Inorganic materials 0.000 description 25
239000001257 hydrogen Substances 0.000 description 25
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 24
230000000875 corresponding effect Effects 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
150000002924 oxiranes Chemical class 0.000 description 19
150000003839 salts Chemical class 0.000 description 18
230000017858 demethylation Effects 0.000 description 17
238000010520 demethylation reaction Methods 0.000 description 17
239000000284 extract Substances 0.000 description 17
239000000047 product Substances 0.000 description 17
238000007142 ring opening reaction Methods 0.000 description 17
-1 2 -HYDROXY -3 AMINO PROPOXY Chemical class 0.000 description 15
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
230000010933 acylation Effects 0.000 description 13
238000005917 acylation reaction Methods 0.000 description 13
MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 13
238000001816 cooling Methods 0.000 description 12
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
238000006467 substitution reaction Methods 0.000 description 11
LTHMASCHPKLOPL-UHFFFAOYSA-N 1-benzofuran-2-yl-(2-hydroxyphenyl)methanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC2=CC=CC=C2O1 LTHMASCHPKLOPL-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
239000007864 aqueous solution Substances 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
239000002904 solvent Substances 0.000 description 10
OVJKFJDEVKABNF-UHFFFAOYSA-N 2-butyl-1-benzofuran Chemical compound C1=CC=C2OC(CCCC)=CC2=C1 OVJKFJDEVKABNF-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
125000001589 carboacyl group Chemical group 0.000 description 9
239000010410 layer Substances 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 8
150000002431 hydrogen Chemical class 0.000 description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
JJXPTUWJVQUHKN-UHFFFAOYSA-N 5-methoxy-1-benzofuran Chemical compound COC1=CC=C2OC=CC2=C1 JJXPTUWJVQUHKN-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
125000001309 chloro group Chemical group Cl* 0.000 description 5
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
238000001914 filtration Methods 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
HCXJFMDOHDNDCC-UHFFFAOYSA-N 5-$l^{1}-oxidanyl-3,4-dihydropyrrol-2-one Chemical group O=C1CCC(=O)[N]1 HCXJFMDOHDNDCC-UHFFFAOYSA-N 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
239000002585 base Substances 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 4
238000010561 standard procedure Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 4
ZHGKQUXXASLVQQ-UHFFFAOYSA-N (2-Butylbenzofuran-3-yl)(4-hydroxyphenyl)ketone Chemical compound CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 ZHGKQUXXASLVQQ-UHFFFAOYSA-N 0.000 description 3
VZLKQEPNZIWSFF-UHFFFAOYSA-N 1-pyrrolidin-1-ylpiperidine Chemical compound C1CCCN1N1CCCCC1 VZLKQEPNZIWSFF-UHFFFAOYSA-N 0.000 description 3
OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 3
GAPGQBDURBPRLG-UHFFFAOYSA-N 3-chloro-4-methoxybenzoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1Cl GAPGQBDURBPRLG-UHFFFAOYSA-N 0.000 description 3
CPJOPFBXUHIQQL-UHFFFAOYSA-N 5-chloro-1-benzofuran Chemical compound ClC1=CC=C2OC=CC2=C1 CPJOPFBXUHIQQL-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
235000011054 acetic acid Nutrition 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
230000017531 blood circulation Effects 0.000 description 3
XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000002002 slurry Substances 0.000 description 3
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
AQNNLGWKMDCSLD-UHFFFAOYSA-N (2-benzyl-1-benzofuran-3-yl)-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C(C1=CC=CC=C1O1)=C1CC1=CC=CC=C1 AQNNLGWKMDCSLD-UHFFFAOYSA-N 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
HJFONKSERLWIGE-DEOSSOPVSA-N (2s)-2-[[4-[4-(1-benzofuran-2-carbonylamino)phenyl]phenyl]sulfonylamino]-3-methylbutanoic acid Chemical compound C1=CC(S(=O)(=O)N[C@@H](C(C)C)C(O)=O)=CC=C1C(C=C1)=CC=C1NC(=O)C1=CC2=CC=CC=C2O1 HJFONKSERLWIGE-DEOSSOPVSA-N 0.000 description 2
ABEDUINFUWIUNI-UHFFFAOYSA-N (4-methoxyphenyl)-(3-methyl-1-benzofuran-2-yl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(C)C2=CC=CC=C2O1 ABEDUINFUWIUNI-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
XJQLOIGEZXCUND-UHFFFAOYSA-N 1-benzofuran-2-yl-(4-nitrophenyl)methanone Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)C1=CC2=CC=CC=C2O1 XJQLOIGEZXCUND-UHFFFAOYSA-N 0.000 description 2
VLLADTXGBAUFMW-UHFFFAOYSA-N 1-benzofuran-3-carbonitrile Chemical compound C1=CC=C2C(C#N)=COC2=C1 VLLADTXGBAUFMW-UHFFFAOYSA-N 0.000 description 2
VJJAGAVQYBKEPY-UHFFFAOYSA-N 1-ethynyl-3-nitrobenzene Chemical compound [O-][N+](=O)c1cccc(c1)C#[C-] VJJAGAVQYBKEPY-UHFFFAOYSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
HFGUMVYWWPOKKI-UHFFFAOYSA-N 2-[[3-(trifluoromethyl)phenyl]methyl]-1-benzofuran Chemical compound FC(F)(F)C1=CC=CC(CC=2OC3=CC=CC=C3C=2)=C1 HFGUMVYWWPOKKI-UHFFFAOYSA-N 0.000 description 2
JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical compound CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 description 2
HXMZLDUBSSPQIB-UHFFFAOYSA-N 2-phenyl-1-benzofuran Chemical compound O1C2=CC=CC=C2C=C1C1=CC=CC=C1 HXMZLDUBSSPQIB-UHFFFAOYSA-N 0.000 description 2
QGNLHMKIGMZKJX-UHFFFAOYSA-N 3-chloro-4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C(Cl)=C1 QGNLHMKIGMZKJX-UHFFFAOYSA-N 0.000 description 2
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
RTKSHBXMWCKUDQ-UHFFFAOYSA-N 4-methoxy-3-methylbenzoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1C RTKSHBXMWCKUDQ-UHFFFAOYSA-N 0.000 description 2
VFMHROFKHVJMRD-UHFFFAOYSA-N 5-chloro-2-phenyl-1-benzofuran Chemical compound C=1C2=CC(Cl)=CC=C2OC=1C1=CC=CC=C1 VFMHROFKHVJMRD-UHFFFAOYSA-N 0.000 description 2
206010002091 Anaesthesia Diseases 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
208000001871 Tachycardia Diseases 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
AKRGXGBDYAXGGW-UHFFFAOYSA-N [2-[(4-aminophenyl)methyl]-1-benzofuran-3-yl]-(4-hydroxyphenyl)methanone Chemical compound C1=CC(N)=CC=C1CC1=C(C(=O)C=2C=CC(O)=CC=2)C2=CC=CC=C2O1 AKRGXGBDYAXGGW-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
230000037005 anaesthesia Effects 0.000 description 2
230000004872 arterial blood pressure Effects 0.000 description 2
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
229920001429 chelating resin Polymers 0.000 description 2
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical class OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical class CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
150000007857 hydrazones Chemical class 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
238000005342 ion exchange Methods 0.000 description 2
229940039009 isoproterenol Drugs 0.000 description 2
ZSBIMTDWIGWJPW-UHFFFAOYSA-N methyl 3-chloro-4-hydroxybenzoate Chemical compound COC(=O)C1=CC=C(O)C(Cl)=C1 ZSBIMTDWIGWJPW-UHFFFAOYSA-N 0.000 description 2
PINQDVFQCCFACD-UHFFFAOYSA-N methyl 3-chloro-4-methoxybenzoate Chemical compound COC(=O)C1=CC=C(OC)C(Cl)=C1 PINQDVFQCCFACD-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
SATVIFGJTRRDQU-UHFFFAOYSA-N potassium hypochlorite Chemical compound [K+].Cl[O-] SATVIFGJTRRDQU-UHFFFAOYSA-N 0.000 description 2
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
230000009467 reduction Effects 0.000 description 2
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229920006395 saturated elastomer Polymers 0.000 description 2
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238000000354 decomposition reaction Methods 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
210000003191 femoral vein Anatomy 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
238000007429 general method Methods 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
230000001077 hypotensive effect Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
230000003601 intercostal effect Effects 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229960005181 morphine Drugs 0.000 description 1
229960004715 morphine sulfate Drugs 0.000 description 1
GRVOTVYEFDAHCL-RTSZDRIGSA-N morphine sulfate pentahydrate Chemical compound O.O.O.O.O.OS(O)(=O)=O.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O GRVOTVYEFDAHCL-RTSZDRIGSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
210000003516 pericardium Anatomy 0.000 description 1
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical class BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
150000003152 propanolamines Chemical class 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
238000010791 quenching Methods 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000000523 sample Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 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 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012360 testing method Methods 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000005406 washing Methods 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
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Cardiology (AREA)
General Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Furan Compounds (AREA)

IL45525A 1973-09-21 1974-08-23 (2-hydroxy-3-amino-propoxy)benzoyl benzofuran derivatives IL45525A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US399573A US3880891A (en)	1973-09-21	1973-09-21	Substituted benzofurans

Publications (2)

Publication Number	Publication Date
IL45525A0 IL45525A0 (en)	1974-11-29
IL45525A true IL45525A (en)	1977-08-31

Family

ID=23580073

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL45525A IL45525A (en)	1973-09-21	1974-08-23	(2-hydroxy-3-amino-propoxy)benzoyl benzofuran derivatives

Country Status (11)

Country	Link
US (1)	US3880891A (fr)
JP (1)	JPS5850220B2 (fr)
BE (1)	BE819675A (fr)
CA (1)	CA1043801A (fr)
DE (1)	DE2445120A1 (fr)
FR (1)	FR2244490B1 (fr)
GB (1)	GB1435261A (fr)
IE (1)	IE39854B1 (fr)
IL (1)	IL45525A (fr)
NL (1)	NL7412457A (fr)
ZA (1)	ZA744918B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3947470A (en) *	1974-06-20	1976-03-30	Smithkline Corporation	Substituted benzofurans and benzothiophenes
US4001426A (en) *	1974-10-17	1977-01-04	Smithkline Corporation	Substituted benzofurans and benzothiophenes
US4117128A (en) *	1976-08-03	1978-09-26	Smithkline Corporation	Sulfonyl benzofurans and benzothiophenes having coronary vasodilator activity
IT1154888B (it) *	1980-11-12	1987-01-21	Menarini Sas	Derivati del benzofurano 2-sostituiti e relativi metodi di preparazione
US4418068A (en)	1981-04-03	1983-11-29	Eli Lilly And Company	Antiestrogenic and antiandrugenic benzothiophenes
SE9101509D0 (sv) *	1991-05-17	1991-05-17	Karobio Ab	Receptor ligands
EP0736007A4 (fr) *	1993-12-21	1997-03-19	Lilly Co Eli	Antagonistes non peptidiques des recepteurs des tachykinines
CN117209483B (zh) *	2022-10-28	2025-10-10	扬州中宝药业股份有限公司	苯并呋喃类衍生物及其制备方法和应用

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3248401A (en) *		1966-04-26		Diethylaminoe hoxybenzoyl benzofurans

1973
- 1973-09-21 US US399573A patent/US3880891A/en not_active Expired - Lifetime
1974
- 1974-08-01 ZA ZA00744918A patent/ZA744918B/xx unknown
- 1974-08-15 CA CA207,106A patent/CA1043801A/fr not_active Expired
- 1974-08-23 IL IL45525A patent/IL45525A/en unknown
- 1974-09-09 BE BE148320A patent/BE819675A/fr not_active IP Right Cessation
- 1974-09-17 FR FR7431391A patent/FR2244490B1/fr not_active Expired
- 1974-09-19 IE IE1942/74A patent/IE39854B1/xx unknown
- 1974-09-20 NL NL7412457A patent/NL7412457A/xx not_active Application Discontinuation
- 1974-09-20 DE DE19742445120 patent/DE2445120A1/de not_active Ceased
- 1974-09-20 GB GB4100174A patent/GB1435261A/en not_active Expired
- 1974-09-20 JP JP49109434A patent/JPS5850220B2/ja not_active Expired

Also Published As

Publication number	Publication date
IE39854L (en)	1975-03-21
JPS5058055A (fr)	1975-05-20
ZA744918B (en)	1975-08-27
IL45525A0 (en)	1974-11-29
CA1043801A (fr)	1978-12-05
FR2244490B1 (fr)	1978-07-28
US3880891A (en)	1975-04-29
BE819675A (fr)	1975-03-10
FR2244490A1 (fr)	1975-04-18
GB1435261A (en)	1976-05-12
NL7412457A (nl)	1975-03-25
IE39854B1 (en)	1979-01-17
DE2445120A1 (de)	1975-03-27
JPS5850220B2 (ja)	1983-11-09
AU7269474A (en)	1976-02-26

Publication	Publication Date	Title
US3947470A (en)	1976-03-30	Substituted benzofurans and benzothiophenes
US4001426A (en)	1977-01-04	Substituted benzofurans and benzothiophenes
SU764610A3 (ru)	1980-09-15	Способ получени производных 2-ароил-3-фенилбензотиофенов или их солей
US4424231A (en)	1984-01-03	Compounds
US4996225A (en)	1991-02-26	Tri-phenyl alkane derivatives and their oestrogenic, anti-oestrogenic and progestanic uses
Schultz et al.	1978	Heteroatom directed photoarylation. Synthetic potential of the heteroatom oxygen
US3983245A (en)	1976-09-28	Certain 4-(3-azacycloalkoxy or azacycloalkylmethoxy)benzoylbenzofurans or benzothiophenes
AU2011266805A1 (en)	2013-01-10	Process for the preparation of dronedarone
Hadimani et al.	1996	Asymmetric total synthesis of (−) podophyllotoxin
US4024273A (en)	1977-05-17	Coronary vasodilator and anti-anginal compositions comprising substituted benzofurans and benzothiophenes and methods of producing coronary vasodilation and anti-anginal activity
US3880891A (en)	1975-04-29	Substituted benzofurans
Carvalho et al.	1984	Naturally occurring dibenzofurans. Part 4. Synthesis of dibenzofurandiols by annelation of benzofurans
US3975537A (en)	1976-08-17	Pharmaceutical compositions and methods of producing coronary vasodilation
Sargent et al.	1982	Naturally occurring dibenzofurans. Part 1. A synthesis of cannabifuran
Mustafa	2009	Benzofurans, Volume 29
IINUMA et al.	1984	Synthetic Studies on the Flavone Derivatives. XII. Synthesis of 2', 3', 5'-and 3', 4', 5'-Trioxygenated Flavones
US3972900A (en)	1976-08-03	7-Substituted benzofuran derivatives
Meisinger et al.	1959	The Structure of a New Product from Yeast: 2-(6-Hydroxy-2-methoxy-3, 4-methylenedioxyphenyl)-benzofuran
OHISHI et al.	1984	Reactions of salicylaldehydes with bromonitromethane
Wu et al.	1994	Preparation of 4, 4-dimethoxybutyl iodide from 1, 4-butanediol via the corresponding tosylate
US3985896A (en)	1976-10-12	Benzophenalenofurans
Dauzonne et al.	1987	A convenient route to substituted phenylalanines
Bellinger et al.	1982	Formation of some 3-aryl-3, 4-dihydroisocoumarins by thermal ring closure of stilbene-2-carboxylic acids
IE42353B1 (en)	1980-07-30	Benzofurans and benzothiophenes and compisitions comprising them
Knight et al.	1979	Total synthesis of pulvinones, 4-benzylidene-2-phenyltetronic acid pigments of fungi