CH628338A5 - Process for the preparation of benzofuran derivatives - Google Patents

Process for the preparation of benzofuran derivatives Download PDF

Info

Publication number: CH628338A5
Authority: CH; Switzerland
Prior art keywords: benzofuran; hydroxy; group; formula; viii
Prior art date: 1975-10-20

Application number

CH997876A

Other languages

German (de)

English (en)

Inventor

Kiyoshi Ito

Mitsuo Hayashida

Teruo Nakanishi

Kazuhiko Kimura

Michiko Nagahara

Masahiko Ikemoto

Original Assignee

Kakenyaku Kako Kk

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.)

1975-10-20

Filing date

1976-08-05

Publication date

1982-02-26

1975-10-20 Priority claimed from JP50126534A external-priority patent/JPS5919106B2/ja

1976-01-01 Priority claimed from JP51000351A external-priority patent/JPS5951547B2/ja

1976-01-21 Priority claimed from JP51006075A external-priority patent/JPS5951549B2/ja

1976-01-21 Priority claimed from JP51006074A external-priority patent/JPS5951548B2/ja

1976-08-05 Application filed by Kakenyaku Kako Kk filed Critical Kakenyaku Kako Kk

1981-08-17 Priority to CH529981A priority Critical patent/CH633785A5/de

1982-02-26 Publication of CH628338A5 publication Critical patent/CH628338A5/de

Links

150000001907 coumarones Chemical class 0.000 title claims description 67
238000000034 method Methods 0.000 title claims description 22
238000002360 preparation method Methods 0.000 title claims description 6
150000001875 compounds Chemical class 0.000 claims description 52
150000003839 salts Chemical class 0.000 claims description 23
125000000217 alkyl group Chemical group 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 20
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 5
201000010099 disease Diseases 0.000 claims description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
210000001428 peripheral nervous system Anatomy 0.000 claims description 4
229940079593 drug Drugs 0.000 claims description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
239000000203 mixture Substances 0.000 description 22
238000000921 elemental analysis Methods 0.000 description 21
-1 Ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy Chemical group 0.000 description 19
229910052739 hydrogen Inorganic materials 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
229960004592 isopropanol Drugs 0.000 description 13
AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
238000006722 reduction reaction Methods 0.000 description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000004809 thin layer chromatography Methods 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
238000001816 cooling Methods 0.000 description 8
239000003208 petroleum Substances 0.000 description 8
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
239000012279 sodium borohydride Substances 0.000 description 8
229910000033 sodium borohydride Inorganic materials 0.000 description 8
150000003141 primary amines Chemical class 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
229960003712 propranolol Drugs 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
SOBIXRUSPZTLPQ-UHFFFAOYSA-N 1-[[2-(1-hydroxyethyl)-1-benzofuran-7-yl]oxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1OC(C(C)O)=C2 SOBIXRUSPZTLPQ-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
ZPQPDBIHYCBNIG-UHFFFAOYSA-N befunolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1OC(C(C)=O)=C2 ZPQPDBIHYCBNIG-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
230000000694 effects Effects 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
230000000144 pharmacologic effect Effects 0.000 description 5
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
239000002904 solvent Substances 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
206010020772 Hypertension Diseases 0.000 description 4
206010020850 Hyperthyroidism Diseases 0.000 description 4
159000000021 acetate salts Chemical class 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
208000019622 heart disease Diseases 0.000 description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
229940039009 isoproterenol Drugs 0.000 description 4
150000007522 mineralic acids Chemical class 0.000 description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
150000007524 organic acids Chemical class 0.000 description 4
230000002265 prevention Effects 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
229920002253 Tannate Polymers 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001242 acetic acid derivatives Chemical class 0.000 description 3
230000000903 blocking effect Effects 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000007810 chemical reaction solvent Substances 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000005457 ice water Substances 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000010410 layer Substances 0.000 description 3
150000002688 maleic acid derivatives Chemical class 0.000 description 3
150000004701 malic acid derivatives Chemical class 0.000 description 3
150000002823 nitrates Chemical class 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
150000003891 oxalate salts Chemical class 0.000 description 3
238000011946 reduction process Methods 0.000 description 3
150000003890 succinate salts Chemical class 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
150000003467 sulfuric acid derivatives Chemical class 0.000 description 3
150000003892 tartrate salts Chemical class 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
BHCNIYOYQIRWQF-UHFFFAOYSA-N 1-(butan-2-ylamino)-3-[[2-(1-hydroxyethyl)-1-benzofuran-5-yl]oxy]propan-2-ol Chemical compound OC(C)C=1OC2=C(C=1)C=C(C=C2)OCC(CNC(C)CC)O BHCNIYOYQIRWQF-UHFFFAOYSA-N 0.000 description 2
LLEQNJAWVRKGAY-UHFFFAOYSA-N 1-(butan-2-ylamino)-3-[[2-(1-hydroxyethyl)-1-benzofuran-7-yl]oxy]propan-2-ol Chemical compound OC(C)C=1OC2=C(C=1)C=CC=C2OCC(CNC(C)CC)O LLEQNJAWVRKGAY-UHFFFAOYSA-N 0.000 description 2
NKNBDCPRGYWUBQ-UHFFFAOYSA-N 1-(tert-butylamino)-3-[[2-(1-hydroxyethyl)-1-benzofuran-6-yl]oxy]propan-2-ol Chemical compound OC(C)C=1OC2=C(C=1)C=CC(=C2)OCC(CNC(C)(C)C)O NKNBDCPRGYWUBQ-UHFFFAOYSA-N 0.000 description 2
QYSHCRFKLMBRMP-UHFFFAOYSA-N 1-(tert-butylamino)-3-[[2-(1-hydroxyethyl)-1-benzofuran-7-yl]oxy]propan-2-ol Chemical compound OC(C)C=1OC2=C(C=1)C=CC=C2OCC(CNC(C)(C)C)O QYSHCRFKLMBRMP-UHFFFAOYSA-N 0.000 description 2
HXVOYLMLSQKMNS-UHFFFAOYSA-N 1-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-1-benzofuran-2-yl]ethanone Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C=C(C(C)=O)O2 HXVOYLMLSQKMNS-UHFFFAOYSA-N 0.000 description 2
WSVKFMHYFCXAPR-UHFFFAOYSA-N 1-[[2-(1-hydroxyethyl)-1-benzofuran-4-yl]oxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound OC(C)C=1OC2=C(C=1)C(=CC=C2)OCC(CNC(C)C)O WSVKFMHYFCXAPR-UHFFFAOYSA-N 0.000 description 2
KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
102000005751 Alcohol Oxidoreductases Human genes 0.000 description 2
108010031132 Alcohol Oxidoreductases Proteins 0.000 description 2
206010002383 Angina Pectoris Diseases 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
241000283973 Oryctolagus cuniculus Species 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
241000700159 Rattus Species 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
150000003934 aromatic aldehydes Chemical class 0.000 description 2
206010003119 arrhythmia Diseases 0.000 description 2
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 2
239000002876 beta blocker Substances 0.000 description 2
229940030611 beta-adrenergic blocking agent Drugs 0.000 description 2
230000036772 blood pressure Effects 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000005515 coenzyme Substances 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
150000003840 hydrochlorides Chemical class 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000010253 intravenous injection Methods 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
238000005185 salting out Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
WUKZZTBYOQERGT-UHFFFAOYSA-N 1-(ethylamino)-3-iodopropan-2-ol Chemical compound C(C)NCC(CI)O WUKZZTBYOQERGT-UHFFFAOYSA-N 0.000 description 1
TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
AXSOEJHOADEIGQ-UHFFFAOYSA-N 1-[3-[3-(butan-2-ylamino)-2-hydroxypropoxy]-1-benzofuran-2-yl]ethanone Chemical compound C(C)(=O)C=1OC2=C(C=1OCC(CNC(C)CC)O)C=CC=C2 AXSOEJHOADEIGQ-UHFFFAOYSA-N 0.000 description 1
OPYVAIPCTIMHCB-UHFFFAOYSA-N 1-[4-[3-(butan-2-ylamino)-2-hydroxypropoxy]-1-benzofuran-2-yl]-2-methylpropan-1-one Chemical compound C(C(C)C)(=O)C=1OC2=C(C=1)C(=CC=C2)OCC(CNC(C)CC)O OPYVAIPCTIMHCB-UHFFFAOYSA-N 0.000 description 1
DVVNFDVESKQFJY-UHFFFAOYSA-N 1-[5-[3-(butan-2-ylamino)-2-hydroxypropoxy]-1-benzofuran-2-yl]ethanone Chemical compound C(C)(=O)C=1OC2=C(C=1)C=C(C=C2)OCC(CNC(C)CC)O DVVNFDVESKQFJY-UHFFFAOYSA-N 0.000 description 1
GDCDYWRDIGTBMH-UHFFFAOYSA-N 1-[6-[3-(tert-butylamino)-2-hydroxypropoxy]-1-benzofuran-2-yl]ethanone Chemical compound C1=C(OCC(O)CNC(C)(C)C)C=C2OC(C(=O)C)=CC2=C1 GDCDYWRDIGTBMH-UHFFFAOYSA-N 0.000 description 1
GTROMCBCQWPZHN-UHFFFAOYSA-N 1-[7-[3-(butan-2-ylamino)-2-hydroxypropoxy]-1-benzofuran-2-yl]ethanone Chemical compound CCC(C)NCC(O)COC1=CC=CC2=C1OC(C(C)=O)=C2 GTROMCBCQWPZHN-UHFFFAOYSA-N 0.000 description 1
SRKJBWACUFBLGI-UHFFFAOYSA-N 1-[7-[3-(tert-butylamino)-2-hydroxypropoxy]-1-benzofuran-2-yl]ethanone Chemical compound C1=CC(OCC(O)CNC(C)(C)C)=C2OC(C(=O)C)=CC2=C1 SRKJBWACUFBLGI-UHFFFAOYSA-N 0.000 description 1
DLAMFTGZTLIVIW-UHFFFAOYSA-N 1-[7-[3-(tert-butylamino)-2-hydroxypropoxy]-1-benzofuran-2-yl]propan-1-one Chemical compound C(CC)(=O)C=1OC2=C(C=1)C=CC=C2OCC(CNC(C)(C)C)O DLAMFTGZTLIVIW-UHFFFAOYSA-N 0.000 description 1
XWNPPKYRNZPSGF-UHFFFAOYSA-N 1-[[2-(hydroxymethyl)-1-benzofuran-7-yl]oxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound OCC=1OC2=C(C=1)C=CC=C2OCC(CNC(C)C)O XWNPPKYRNZPSGF-UHFFFAOYSA-N 0.000 description 1
CANISNAWCFNUBB-UHFFFAOYSA-N 1-bromo-3-(2-methylpropylamino)propan-2-ol Chemical compound C(C(C)C)NCC(CBr)O CANISNAWCFNUBB-UHFFFAOYSA-N 0.000 description 1
MUBSGYWDXHKYBY-UHFFFAOYSA-N 1-bromo-3-(butan-2-ylamino)propan-2-ol Chemical compound C(C)(CC)NCC(CBr)O MUBSGYWDXHKYBY-UHFFFAOYSA-N 0.000 description 1
FXPAWSQSXNAZPR-UHFFFAOYSA-N 1-chloro-3-(methylamino)propan-2-ol Chemical compound CNCC(O)CCl FXPAWSQSXNAZPR-UHFFFAOYSA-N 0.000 description 1
RMLUHSOTPMRODI-UHFFFAOYSA-N 1-chloro-3-(propylamino)propan-2-ol Chemical compound CCCNCC(O)CCl RMLUHSOTPMRODI-UHFFFAOYSA-N 0.000 description 1
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
JYDHBEUXXRBHTK-UHFFFAOYSA-N C(C)(=O)O.OC(C)C=1OC2=C(C1)C=CC=C2OCC(CNC(C)C)O Chemical compound C(C)(=O)O.OC(C)C=1OC2=C(C1)C=CC=C2OCC(CNC(C)C)O JYDHBEUXXRBHTK-UHFFFAOYSA-N 0.000 description 1
FACDALISYRZXPA-UHFFFAOYSA-N C(CC(C)C)(=O)C=1OC2=C(C1)C=CC=C2OCC(CNC(C)CC)O Chemical compound C(CC(C)C)(=O)C=1OC2=C(C1)C=CC=C2OCC(CNC(C)CC)O FACDALISYRZXPA-UHFFFAOYSA-N 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
241000700198 Cavia Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
FNZSITAOHCJFPS-UHFFFAOYSA-N Cl.OC(C)C=1OC2=C(C1)C=CC=C2OCC(CNC(C)C)O Chemical compound Cl.OC(C)C=1OC2=C(C1)C=CC=C2OCC(CNC(C)C)O FNZSITAOHCJFPS-UHFFFAOYSA-N 0.000 description 1
241000699800 Cricetinae Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
239000001263 FEMA 3042 Substances 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
206010021143 Hypoxia Diseases 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
239000012448 Lithium borohydride Substances 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
VNYBRHDRGOJHKF-UHFFFAOYSA-N [4-[3-(butan-2-ylamino)-2-hydroxypropoxy]-1-benzofuran-2-yl]-phenylmethanone Chemical compound C=1C=2C(OCC(O)CNC(C)CC)=CC=CC=2OC=1C(=O)C1=CC=CC=C1 VNYBRHDRGOJHKF-UHFFFAOYSA-N 0.000 description 1
WHQFQRPSOBFKJC-UHFFFAOYSA-N [7-[2-hydroxy-3-(propan-2-ylamino)propoxy]-1-benzofuran-2-yl]-phenylmethanone Chemical compound O1C=2C(OCC(O)CNC(C)C)=CC=CC=2C=C1C(=O)C1=CC=CC=C1 WHQFQRPSOBFKJC-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
JPUHCPXFQIXLMW-UHFFFAOYSA-N aluminium triethoxide Chemical compound CCO[Al](OCC)OCC JPUHCPXFQIXLMW-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
230000003444 anaesthetic effect Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000004397 blinking Effects 0.000 description 1
239000002981 blocking agent Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 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
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
210000004087 cornea Anatomy 0.000 description 1
230000006806 disease prevention Effects 0.000 description 1
NUUBJYUSRWUKGF-UHFFFAOYSA-N ethyl 7-[2-hydroxy-3-(propan-2-ylamino)propoxy]-1-benzofuran-2-carboxylate Chemical compound C1=CC(OCC(O)CNC(C)C)=C2OC(C(=O)OCC)=CC2=C1 NUUBJYUSRWUKGF-UHFFFAOYSA-N 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000007954 hypoxia Effects 0.000 description 1
238000011534 incubation Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000002690 local anesthesia Methods 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
244000005700 microbiome Species 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
230000030564 negative regulation of blood pressure Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000011514 reflex Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
125000005920 sec-butoxy group Chemical group 0.000 description 1
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
235000015523 tannic acid Nutrition 0.000 description 1
229940033123 tannic acid Drugs 0.000 description 1
229920002258 tannic acid Polymers 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 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
MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000008096 xylene Substances 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
- C07D307/86—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
- 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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CH997876A 1975-10-20 1976-08-05 Process for the preparation of benzofuran derivatives CH628338A5 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CH529981A CH633785A5 (en)	1975-10-20	1981-08-17	Process for the preparation of benzofuran derivatives

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP50126534A JPS5919106B2 (ja)	1975-10-20	1975-10-20	ベンゾフラン誘導体の製造法
JP51000351A JPS5951547B2 (ja)	1976-01-01	1976-01-01	ベンゾフラン誘導体
JP51006075A JPS5951549B2 (ja)	1976-01-21	1976-01-21	ベンゾフラン誘導体の製造法
JP51006074A JPS5951548B2 (ja)	1976-01-21	1976-01-21	ベンゾフラン誘導体の製造法

Publications (1)

Publication Number	Publication Date
CH628338A5 true CH628338A5 (en)	1982-02-26

Family

ID=27453151

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH997876A CH628338A5 (en)	1975-10-20	1976-08-05	Process for the preparation of benzofuran derivatives

Country Status (7)

Country	Link
BE (1)	BE845156A (fr)
CA (1)	CA1089866A (fr)
CH (1)	CH628338A5 (fr)
DE (1)	DE2635064C2 (fr)
FR (1)	FR2328463A1 (fr)
GB (1)	GB1502248A (fr)
NL (1)	NL7610426A (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS60202872A (ja) *	1984-03-27	1985-10-14	Kaken Pharmaceut Co Ltd	ベンゾフラン誘導体、その製法およびそれを有効成分とする降圧剤
JPS61158976A (ja) *	1984-12-28	1986-07-18	Shionogi & Co Ltd	ベンゾフランおよびベンゾチオフエン誘導体
DE69916664T2 (de) *	1998-12-18	2005-03-31	Basilea Pharmaceutica Ag	4-(aminoalkoxy)benzofurane als n-myristoyltransferasehemmer

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1058822A (en) *	1963-07-30	1967-02-15	Ici Ltd	3-amino-2-hydroxypropoxy heterocyclic derivatives

1976
- 1976-07-20 CA CA257,342A patent/CA1089866A/fr not_active Expired
- 1976-07-29 GB GB3161576A patent/GB1502248A/en not_active Expired
- 1976-08-04 DE DE19762635064 patent/DE2635064C2/de not_active Expired
- 1976-08-05 CH CH997876A patent/CH628338A5/de not_active IP Right Cessation
- 1976-08-12 FR FR7624676A patent/FR2328463A1/fr active Granted
- 1976-08-13 BE BE169780A patent/BE845156A/fr not_active IP Right Cessation
- 1976-09-20 NL NL7610426A patent/NL7610426A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
FR2328463B1 (fr)	1978-12-22
GB1502248A (en)	1978-02-22
CA1089866A (fr)	1980-11-18
NL7610426A (nl)	1977-04-22
FR2328463A1 (fr)	1977-05-20
BE845156A (fr)	1976-12-01
DE2635064A1 (de)	1977-04-21
DE2635064C2 (de)	1986-07-24

Legal Events

Date	Code	Title	Description
1992-04-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
AT363096B (de)	1981-07-10	Verfahren zur herstellung von neuen phthalazinderivaten und deren salzen
DE1643224A1 (de)	1972-03-02	1-Phenyl-2-aminoaethanolderivate und Verfahren zu ihrer Herstellung und ihre Verwendung
WO1985001048A1 (fr)	1985-03-14	Esters ou amides aromatiques de l'acide carbonique et de l'acide sulfonique
CH648553A5 (de)	1985-03-29	Neue 3,4-dihydro-5h-2,3-benzodiazepin-derivate und verfahren zur herstellung derselben.
EP0464465A1 (fr)	1992-01-08	Dérivés substitués d'aminoalkylbiphenyle, compositions antimycotiques les contenant et intermédiaires pour leur préparation
DE2461604C2 (fr)	1988-10-13
DE3430284A1 (de)	1986-02-27	Neue tryptamin-derivate, ein verfahren zu ihrer herstellung und ihre verwendung
DE2223184B2 (de)	1979-08-16	Benzofuranderivate und deren pharmazeutisch verträgliche Säureadditionssalze sowie ein Verfahren zu deren Herstellung und Arzneimittel mit einem Gehalt dieser Verbindungen
EP0374756A2 (fr)	1990-06-27	Composés cycliques azotés
DE1963182A1 (de)	1970-10-15	Neue N-Phenylindolin-Derivate und deren Verwendung als Arzneimittel
AT368130B (de)	1982-09-10	Verfahren zur herstellung von neuen 9-aminoalkyl- fluorenen und von deren salzen
EP0033156B1 (fr)	1984-10-17	Dérivés de 1-phényl-2-cyclohexène-1-alkylamine, procédé pour leur préparation et médicaments les contenant
DE2044172C3 (de)	1975-11-13	Pyrrolderivate, ein Verfahren zu ihrer Herstellung und Arzneimittel
CH628338A5 (en)	1982-02-26	Process for the preparation of benzofuran derivatives
DE2605377A1 (de)	1976-08-26	0-aminooxime, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE2819458A1 (de)	1978-11-16	Benzimidazol-derivate
DE3514843C2 (fr)	1992-11-05
DE1959898A1 (de)	1970-06-18	ortho-substituierte Phenaethylamine und Verfahren zu ihrer Herstellung
DE2653147C2 (fr)	1991-09-19
DE3853958T2 (de)	1995-10-05	Substituierte Pyridin-Verbindungen, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen.
DE2526966A1 (de)	1976-01-08	Tricyclische alkylaminverbindungen, verfahren zu ihrer herstellung und sie enthaltende mittel
EP0071950B1 (fr)	1985-11-06	Hétéroarylpropanolamines, procédé pour leur fabrication et médicaments contenant ces composés
DE3884363T2 (de)	1994-01-20	Ethanolaminderivate.
DE3882613T2 (de)	1994-07-21	Chloranilin-Derivate.
DE2217329A1 (de)	1972-11-02	Benzofuranderivate