DD107670B3 - Verfahren zur herstellung von (3.4-dihydroxy-n-)3-(4-hydroxyphenyl)-1-methyl-n-propyl/-beta-phenethyl-amin - Google Patents

Verfahren zur herstellung von (3.4-dihydroxy-n-)3-(4-hydroxyphenyl)-1-methyl-n-propyl/-beta-phenethyl-amin Download PDF

Info

Publication number: DD107670B3
Authority: DD; German Democratic Republic
Prior art keywords: compound; amine; propyl; methyl; heart
Prior art date: 1972-04-12

Application number

DD73170118A

Other languages

German (de)

English (en)

Other versions

DD107670A5 (de

Inventor

Ronald R Tuttle

Jack Mills

Original Assignee

Lilly Co Eli

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.)

1972-04-12

Filing date

1973-04-12

Publication date

1988-04-06

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=22918877&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=DD107670(B3) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1973-04-12 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1974-08-12 Publication of DD107670A5 publication Critical patent/DD107670A5/xx

1988-04-06 Publication of DD107670B3 publication Critical patent/DD107670B3/de

Links

-1 4-HYDROXYPHENYL Chemical class 0.000 title description 8
238000004519 manufacturing process Methods 0.000 title 1
150000003839 salts Chemical class 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 18
238000000034 method Methods 0.000 claims description 13
229940117803 phenethylamine Drugs 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 8
150000007513 acids Chemical class 0.000 claims description 5
229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
239000011707 mineral Substances 0.000 claims description 5
230000008569 process Effects 0.000 claims description 3
FRJMDYSVLCJWQC-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-4-(4-methoxyphenyl)butan-2-amine Chemical compound C1=CC(OC)=CC=C1CCC(C)NCCC1=CC=C(OC)C(OC)=C1 FRJMDYSVLCJWQC-UHFFFAOYSA-N 0.000 claims description 2
150000001875 compounds Chemical class 0.000 description 87
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
230000036772 blood pressure Effects 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
230000000747 cardiac effect Effects 0.000 description 26
239000000243 solution Substances 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 16
230000010247 heart contraction Effects 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 14
230000017531 blood circulation Effects 0.000 description 14
230000000694 effects Effects 0.000 description 13
241000282472 Canis lupus familiaris Species 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 10
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 10
229960001089 dobutamine Drugs 0.000 description 10
239000000203 mixture Substances 0.000 description 10
229960002748 norepinephrine Drugs 0.000 description 10
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 10
239000002244 precipitate Substances 0.000 description 10
230000009467 reduction Effects 0.000 description 10
238000006722 reduction reaction Methods 0.000 description 10
150000003335 secondary amines Chemical class 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
150000001412 amines Chemical class 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
JRWZLRBJNMZMFE-UHFFFAOYSA-N Dobutamine Chemical compound C=1C=C(O)C(O)=CC=1CCNC(C)CCC1=CC=C(O)C=C1 JRWZLRBJNMZMFE-UHFFFAOYSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
230000002829 reductive effect Effects 0.000 description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000001257 hydrogen Substances 0.000 description 7
229910052739 hydrogen Inorganic materials 0.000 description 7
238000001802 infusion Methods 0.000 description 7
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
230000007423 decrease Effects 0.000 description 6
229960003638 dopamine Drugs 0.000 description 6
210000001105 femoral artery Anatomy 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
238000005984 hydrogenation reaction Methods 0.000 description 6
210000000056 organ Anatomy 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
238000010992 reflux Methods 0.000 description 6
210000002027 skeletal muscle Anatomy 0.000 description 6
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 5
ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 5
230000009471 action Effects 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000003814 drug Substances 0.000 description 5
238000001990 intravenous administration Methods 0.000 description 5
229940039009 isoproterenol Drugs 0.000 description 5
230000002093 peripheral effect Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
102000005962 receptors Human genes 0.000 description 5
108020003175 receptors Proteins 0.000 description 5
239000007858 starting material Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
230000008859 change Effects 0.000 description 4
238000001816 cooling Methods 0.000 description 4
231100000673 dose–response relationship Toxicity 0.000 description 4
229940079593 drug Drugs 0.000 description 4
238000000921 elemental analysis Methods 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
238000011835 investigation Methods 0.000 description 4
210000004165 myocardium Anatomy 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
229940048346 phenethylamine hydrochloride Drugs 0.000 description 4
230000002792 vascular Effects 0.000 description 4
241001465754 Metazoa Species 0.000 description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
206010003119 arrhythmia Diseases 0.000 description 3
210000004204 blood vessel Anatomy 0.000 description 3
229910000085 borane Inorganic materials 0.000 description 3
206010007625 cardiogenic shock Diseases 0.000 description 3
150000003943 catecholamines Chemical class 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
230000008602 contraction Effects 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
230000000297 inotrophic effect Effects 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 2
UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 2
229930182837 (R)-adrenaline Natural products 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
CFFZDZCDUFSOFZ-UHFFFAOYSA-N 3,4-Dihydroxy-phenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C(O)=C1 CFFZDZCDUFSOFZ-UHFFFAOYSA-N 0.000 description 2
WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
206010019280 Heart failures Diseases 0.000 description 2
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
VYWQTJWGWLKBQA-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;chloride Chemical compound Cl.NC(N)=O VYWQTJWGWLKBQA-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
230000006793 arrhythmia Effects 0.000 description 2
239000002585 base Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
230000036760 body temperature Effects 0.000 description 2
230000004087 circulation Effects 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000001035 drying Methods 0.000 description 2
229960005139 epinephrine Drugs 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000012458 free base Substances 0.000 description 2
150000003840 hydrochlorides Chemical class 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
WRLGYAWRGXKSKG-UHFFFAOYSA-M phenobarbital sodium Chemical compound [Na+].C=1C=CC=CC=1C1(CC)C(=O)NC([O-])=NC1=O WRLGYAWRGXKSKG-UHFFFAOYSA-M 0.000 description 2
238000005932 reductive alkylation reaction Methods 0.000 description 2
239000000523 sample Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
238000000926 separation method Methods 0.000 description 2
230000035939 shock Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
230000000638 stimulation Effects 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
AWLILQARPMWUHA-UHFFFAOYSA-M thiopental sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC([S-])=NC1=O AWLILQARPMWUHA-UHFFFAOYSA-M 0.000 description 2
210000001186 vagus nerve Anatomy 0.000 description 2
DXDIHODZARUBLA-IODNYQNNSA-N (2s,3s)-2,3-dibenzoyloxybutanedioic acid;hydrate Chemical compound O.O([C@H](C(=O)O)[C@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 DXDIHODZARUBLA-IODNYQNNSA-N 0.000 description 1
CSFLLVUCUISNAZ-UHFFFAOYSA-N (dimethoxyamino)oxymethane Chemical group CON(OC)OC CSFLLVUCUISNAZ-UHFFFAOYSA-N 0.000 description 1
WRRZKDVBPZBNJN-ONEGZZNKSA-N (e)-4-(4-methoxyphenyl)but-3-en-2-one Chemical compound COC1=CC=C(\C=C\C(C)=O)C=C1 WRRZKDVBPZBNJN-ONEGZZNKSA-N 0.000 description 1
IRAGENYJMTVCCV-UHFFFAOYSA-N 2-phenylethanamine;hydrobromide Chemical compound [Br-].[NH3+]CCC1=CC=CC=C1 IRAGENYJMTVCCV-UHFFFAOYSA-N 0.000 description 1
PCBSXBYCASFXTM-UHFFFAOYSA-N 4-(4-Methoxyphenyl)-2-butanone Chemical compound COC1=CC=C(CCC(C)=O)C=C1 PCBSXBYCASFXTM-UHFFFAOYSA-N 0.000 description 1
JMHAKVPFYWWNOW-UHFFFAOYSA-N 4-(4-methoxyphenyl)butan-2-amine Chemical compound COC1=CC=C(CCC(C)N)C=C1 JMHAKVPFYWWNOW-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
108060003345 Adrenergic Receptor Proteins 0.000 description 1
102000017910 Adrenergic receptor Human genes 0.000 description 1
JAJPWCFAKADKHY-UHFFFAOYSA-N COC1=CC=C(C=C1)CC=CC(=O)C=CCC1=CC=C(C=C1)OC Chemical compound COC1=CC=C(C=C1)CC=CC(=O)C=CCC1=CC=C(C=C1)OC JAJPWCFAKADKHY-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
206010028851 Necrosis Diseases 0.000 description 1
GMPKIPWJBDOURN-MICDWDOJSA-N O-(deuteriomethyl)hydroxylamine Chemical compound C(ON)[2H] GMPKIPWJBDOURN-MICDWDOJSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
239000000150 Sympathomimetic Substances 0.000 description 1
206010047139 Vasoconstriction Diseases 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
210000000709 aorta Anatomy 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
230000022900 cardiac muscle contraction Effects 0.000 description 1
229940030602 cardiac therapy drug Drugs 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
210000000038 chest Anatomy 0.000 description 1
208000035850 clinical syndrome Diseases 0.000 description 1
230000001609 comparable effect Effects 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
230000034994 death Effects 0.000 description 1
238000005661 deetherification reaction Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
229960001654 dobutamine hydrochloride Drugs 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229960002897 heparin Drugs 0.000 description 1
229920000669 heparin Polymers 0.000 description 1
XQBYLOYJNLQCLU-UHFFFAOYSA-N hepta-2,5-dien-4-one Chemical compound CC=CC(=O)C=CC XQBYLOYJNLQCLU-UHFFFAOYSA-N 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000004041 inotropic agent Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
230000017074 necrotic cell death Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000006213 oxygenation reaction Methods 0.000 description 1
210000005259 peripheral blood Anatomy 0.000 description 1
239000011886 peripheral blood Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
230000009090 positive inotropic effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
239000012264 purified product Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
210000005241 right ventricle Anatomy 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000001975 sympathomimetic effect Effects 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1
230000025033 vasoconstriction Effects 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
230000003313 weakening effect Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- 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
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Epidemiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Heart & Thoracic Surgery (AREA)
General Chemical & Material Sciences (AREA)
Hospice & Palliative Care (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD73170118A 1972-04-12 1973-04-12 Verfahren zur herstellung von (3.4-dihydroxy-n-)3-(4-hydroxyphenyl)-1-methyl-n-propyl/-beta-phenethyl-amin DD107670B3 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US24346672A	1972-04-12	1972-04-12

Publications (2)

Publication Number	Publication Date
DD107670A5 DD107670A5 (de)	1974-08-12
DD107670B3 true DD107670B3 (de)	1988-04-06

Family

ID=22918877

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD73170118A DD107670B3 (de)	1972-04-12	1973-04-12	Verfahren zur herstellung von (3.4-dihydroxy-n-)3-(4-hydroxyphenyl)-1-methyl-n-propyl/-beta-phenethyl-amin

Country Status (31)

Country	Link
JP (2)	JPS5825656B2 (fr)
KR (1)	KR790000113B1 (fr)
AR (1)	AR203822A1 (fr)
AT (1)	AT323719B (fr)
AU (1)	AU472734B2 (fr)
BE (1)	BE798051A (fr)
BG (1)	BG23001A3 (fr)
CA (1)	CA1018188A (fr)
CH (2)	CH569691A5 (fr)
CS (2)	CS190406B2 (fr)
CY (1)	CY963A (fr)
DD (1)	DD107670B3 (fr)
DE (1)	DE2317710C2 (fr)
DK (1)	DK142750C (fr)
ES (1)	ES413639A1 (fr)
FR (1)	FR2182947B1 (fr)
GB (1)	GB1392674A (fr)
HK (1)	HK50178A (fr)
HU (2)	HU167597B (fr)
IE (1)	IE37511B1 (fr)
IL (1)	IL42016A (fr)
KE (1)	KE2870A (fr)
MY (1)	MY7800381A (fr)
NL (1)	NL174459C (fr)
PH (1)	PH11041A (fr)
PL (2)	PL90695B1 (fr)
RO (2)	RO65105A (fr)
SE (1)	SE399064B (fr)
SU (1)	SU496719A3 (fr)
YU (2)	YU36483B (fr)
ZA (1)	ZA732136B (fr)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH585693A5 (fr) *	1974-02-08	1977-03-15	Ciba Geigy Ag
US4342692A (en) *	1980-10-20	1982-08-03	Usv Pharmaceutical Corporation	Pyrrolidines
ZA825227B (en) *	1981-07-22	1984-03-28	Syntex Inc	Substituted pyrrolidine cardiovascular system regulators antihypertensives
JPS6061523A (ja) *	1983-09-16	1985-04-09	Shionogi & Co Ltd	経口用ドブタミン製剤
ZA881076B (en) *	1987-02-24	1989-10-25	Lilly Co Eli	Dobutamine salts
JPH0383364U (fr) *	1989-12-18	1991-08-23
AU658188B2 (en) *	1991-05-20	1995-04-06	Tsumura & Co.	Phellodendrine analogs and allergy type IV suppressor containing the same as active ingredient
ATE155125T1 (de) *	1993-04-13	1997-07-15	Duphar Int Res	Herstellung von dobutamin verbindungen
EP0620208B1 (fr) *	1993-04-13	1997-07-09	Duphar International Research B.V	Production de composés de la dobutamine
WO2004031129A2 (fr)	2002-10-03	2004-04-15	New Era Biotech, Ltd.	Nouveaux composes destines au traitement des maladies auto-immunes, des maladies immuno-allergiques et des rejets en cas de greffes d'organes ou de tissus
CA2560922C (fr)	2004-03-26	2014-01-07	New Era Biotech, Ltd.	Ameliorations apportees a des composes destines a etre utilises dans le traitement du sida ou d'autres maladies virales et infections associees au vih et compositions contenant ces composes, methodes de traitement de ces maladies et de ces infections et methodes de fabrication de ces composes et de ces compositions
GB0804213D0 (en)	2008-03-06	2008-04-16	New Era Biotech Ltd	A method of printing or preventing pain
US9192585B2 (en)	2009-07-31	2015-11-24	Cognition Therapeutics, Inc.	Inhibitors of cognitive decline
US8802734B2 (en)	2009-09-09	2014-08-12	Novaremed Limited	Method of treating or preventing pain
EP2747759A4 (fr) *	2011-08-25	2015-05-13	Cognition Therapeutics Inc	Compositions et méthodes pour le traitement de maladies neurodégénératives
AU2015210852B2 (en)	2014-01-31	2019-01-24	Cognition Therapeutics, Inc.	Isoindoline compositions and methods for treating neurodegenerative disease
DK3634394T3 (da)	2017-05-15	2026-03-02	Cognition Therapeutics Inc	Sammensætninger til behandling af neurogenerative sygdomme
CN114524734B (zh) *	2021-12-27	2024-04-26	嘉实（湖南）医药科技有限公司	一种盐酸多巴酚丁胺的制备方法
CN117326958B (zh) *	2023-09-21	2025-07-11	锦州奥鸿药业有限责任公司	一种高纯度盐酸多巴酚丁胺的制备方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2276619A (en) *		1942-03-17		N-phentlaliphatic-dihtoroxyphentnl

1973
- 1973-03-28 ZA ZA732136A patent/ZA732136B/xx unknown
- 1973-04-09 GB GB1683573A patent/GB1392674A/en not_active Expired
- 1973-04-09 CY CY963A patent/CY963A/xx unknown
- 1973-04-09 DE DE2317710A patent/DE2317710C2/de not_active Expired
- 1973-04-10 FR FR7312845A patent/FR2182947B1/fr not_active Expired
- 1973-04-10 SE SE7305032A patent/SE399064B/xx unknown
- 1973-04-10 IE IE563/73A patent/IE37511B1/xx unknown
- 1973-04-11 SU SU1908277A patent/SU496719A3/ru active
- 1973-04-11 KR KR7300573A patent/KR790000113B1/ko not_active Expired
- 1973-04-11 AT AT318773A patent/AT323719B/de not_active IP Right Cessation
- 1973-04-11 DK DK196773A patent/DK142750C/da not_active IP Right Cessation
- 1973-04-11 CA CA168,428A patent/CA1018188A/en not_active Expired
- 1973-04-11 CH CH517473A patent/CH569691A5/xx not_active IP Right Cessation
- 1973-04-11 CH CH1112475A patent/CH580563A5/xx not_active IP Right Cessation
- 1973-04-11 BE BE1004956A patent/BE798051A/fr not_active IP Right Cessation
- 1973-04-11 AU AU54385/73A patent/AU472734B2/en not_active Expired
- 1973-04-11 YU YU00976/73A patent/YU36483B/xx unknown
- 1973-04-11 NL NLAANVRAGE7305097,A patent/NL174459C/xx not_active IP Right Cessation
- 1973-04-11 BG BG023268A patent/BG23001A3/xx unknown
- 1973-04-12 CS CS732601A patent/CS190406B2/cs unknown
- 1973-04-12 RO RO7374457A patent/RO65105A/fr unknown
- 1973-04-12 HU HUEI552A patent/HU167597B/hu unknown
- 1973-04-12 CS CS77171A patent/CS190448B2/cs unknown
- 1973-04-12 HU HUEI469A patent/HU166213B/hu unknown
- 1973-04-12 PL PL1973161874A patent/PL90695B1/pl unknown
- 1973-04-12 ES ES413639A patent/ES413639A1/es not_active Expired
- 1973-04-12 AR AR247523A patent/AR203822A1/es active
- 1973-04-12 IL IL42016A patent/IL42016A/en unknown
- 1973-04-12 DD DD73170118A patent/DD107670B3/de unknown
- 1973-04-12 RO RO7383749A patent/RO70892A/fr unknown
- 1973-04-12 PH PH14508A patent/PH11041A/en unknown
- 1973-04-12 PL PL1973183808A patent/PL94207B1/pl unknown
- 1973-04-12 JP JP48041750A patent/JPS5825656B2/ja not_active Expired
1978
- 1978-08-10 KE KE2870A patent/KE2870A/xx unknown
- 1978-09-07 HK HK501/78A patent/HK50178A/xx unknown
- 1978-12-30 MY MY381/78A patent/MY7800381A/xx unknown
1979
- 1979-12-28 YU YU3212/79A patent/YU37113B/xx unknown
1982
- 1982-08-27 JP JP57149025A patent/JPS58131945A/ja active Granted

Also Published As

Publication number	Publication date
DK142750C (da)	1981-08-17
NL174459C (nl)	1984-06-18
CA1018188A (en)	1977-09-27
PH11041A (en)	1977-10-25
BE798051A (fr)	1973-10-11
AT323719B (de)	1975-07-25
JPS497237A (fr)	1974-01-22
AU5438573A (en)	1974-10-17
IE37511B1 (en)	1977-08-03
JPS58131945A (ja)	1983-08-06
YU36483B (en)	1984-02-29
KR790000113B1 (en)	1979-03-20
HU167597B (fr)	1975-11-28
HK50178A (en)	1978-09-15
RO65105A (fr)	1980-01-15
CS190406B2 (en)	1979-05-31
MY7800381A (en)	1978-12-31
IL42016A (en)	1976-05-31
CH580563A5 (fr)	1976-10-15
CY963A (en)	1978-12-22
YU321279A (en)	1983-04-27
GB1392674A (en)	1975-04-30
HU166213B (fr)	1975-02-28
DK142750B (da)	1981-01-12
JPS6221343B2 (fr)	1987-05-12
NL7305097A (fr)	1973-10-16
ZA732136B (en)	1974-03-27
JPS5825656B2 (ja)	1983-05-28
RO70892A (fr)	1982-02-26
NL174459B (nl)	1984-01-16
AR203822A1 (es)	1975-10-31
ES413639A1 (es)	1976-01-16
CH569691A5 (fr)	1975-11-28
DE2317710C2 (de)	1983-08-04
KE2870A (en)	1978-09-01
DE2317710A1 (de)	1973-10-18
PL90695B1 (fr)	1977-01-31
YU37113B (en)	1984-08-31
BG23001A3 (bg)	1977-05-20
FR2182947A1 (fr)	1973-12-14
CS190448B2 (en)	1979-05-31
IL42016A0 (en)	1973-06-29
YU97673A (en)	1982-02-25
DD107670A5 (de)	1974-08-12
SU496719A3 (ru)	1975-12-25
SE399064B (sv)	1978-01-30
FR2182947B1 (fr)	1976-07-02
AU472734B2 (en)	1976-06-03
PL94207B1 (fr)	1977-07-30

Publication	Publication Date	Title
DE2317710C2 (de)	1983-08-04	3,4-Dihydroxy-N-[3-(4-hydroxyphenyl)-1-methyl-n-propyl]-&beta;-phenethylamin und dessen Säureadditionssalze, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE2106209C3 (de)	1980-05-29	p-substituierte Phenoxypropanolamine, Verfahren zu deren Herstellung und Arzneimittel auf deren Basis AB Hässle, Mölndal (Schweden)
DE1294955B (de)	1969-05-14	1-(o-Allylphenoxy)- und 1-(p-Allyl-phenoxy)-2-hydroxy-3-isopropylaminopropan und Verfahren zu deren Herstellung
DE1275069B (de)	1968-08-14	1-(3', 5'-Dihydroxyphenyl)-1-hydroxy-2-isopropylaminoalkane und Verfahren zu ihrer Herstellung
DE1468092B2 (de)	1976-07-22	Aminopropoxy-derivate des tetrahydronaphthalins und des indans, deren saeureadditionssalze, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische praeparate
AT321888B (de)	1975-04-25	Verfahren zur herstellung von neuen sulfamidensowie deren saeureadditionssalzen
DE1915230C3 (de)	1978-10-26	Hydroxyphenylalkylaminderivate, Verfahren zu deren Herstellung und Arzneimittel auf deren Basis
DE2501122B2 (de)	1981-05-21	Amidoximderivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2304414C3 (de)	1976-11-16	1-[3-(trifluormethyl)phenyl]-2-[(cyanoalkyl)amino]-propane, verfahren zu deren herstellung und diese enthaltende arzneimittel
DE2062055C3 (de)	1979-01-18	Propanolamin-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
DE1593924C3 (de)	1975-10-09	6-Guanidomethyl-1,4-benzodioxan und dessen pharmakologisch nichtgiftige Säureadditionssalze sowie Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
DE2754148A1 (de)	1978-06-08	Substituierte aminoaethanole, verfahren zu ihrer herstellung und ihre verwendung als arzneistoffe
DE2810482C2 (de)	1982-12-02	1-Phenyl-2- eckige Klammer auf (N-alkyl)-amino eckige Klammer zu -propan-1,3-diole, Verfahren zur Herstellung derselben und solche enthaltende Arzneimittel
AT256816B (de)	1967-09-11	Verfahren zur Herstellung von neuen substituierten 1-Phenyl-2-aminoalkanolen und deren Säureadditionssalzen
DE2738131A1 (de)	1978-03-09	Aminoketone, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
AT228786B (de)	1963-08-12	Verfahren zur Herstellung des neuen (-)-Enantiomeren des 1-(p-Hydroxyphenyl)-2-(α-methyl- γ-phenyl-propylamino)-propanols-(1) und seiner Säureadditionssalze
DE2427208A1 (de)	1975-01-09	Triazole und deren salze, verfahren zu deren herstellung und sie enthaltende arzneimittel
AT371102B (de)	1983-06-10	Verfahren zur herstellung neuer optisch aktiver phenethanolamine und der pharmazeutisch unbedenklichen salze hiervon
DE1518444C (de)	1973-07-19	erythro alpha Phenyl beta amino propanole, Verfahren zu ihrer Herstellung und solche Verbindungen enthaltende Arz neimittel
DE1812770C (de)	1972-02-03	Saureadditionssalze des Racemats des 1 (3,4 Dihydroxyphenyl) 2 tert butyl aminobutanols (1) und dessen optischem 1R,2S Isomer
AT268247B (de)	1969-02-10	Verfahren zur Herstellung von neuen 1-Isopropylamino-2-hydroxy-3-(alkenylphenoxy)-propanen und deren Salzen
AT371101B (de)	1983-06-10	Verfahren zur herstellung neuer optisch aktiver phenethanolamine und der pharmazeutisch unbedenklichen salze hiervon
AT223595B (de)	1962-09-25	Verfahren zur Herstellung der neuen optischen Antipoden desjenigen der je zwei möglichen α- und β-erythro-Razemate von 1-(4'-Hydroxyphenyl)-2-(1"-methyl-2"-phenoxyäthylamino)-propanol-(1), dessen Hydrochlorid die geringste Löslichkeit in Wasser aufweist
AT333264B (de)	1976-11-10	Verfahren zur herstellung des neuen 3-(4-biphenylyl)-3-methyl-propionsaurenitrils
DE1468092C3 (de)	1977-03-24	Aminopropoxy-Derivate des Tetrahydronaphthalins und des Indans, deren Säureadditionssalze, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Präparate