SU1172449A3 - Способ получени производных фенилалкиламина или их солей - Google Patents
Способ получени производных фенилалкиламина или их солей Download PDFInfo
- Publication number
- SU1172449A3 SU1172449A3 SU813358171A SU3358171A SU1172449A3 SU 1172449 A3 SU1172449 A3 SU 1172449A3 SU 813358171 A SU813358171 A SU 813358171A SU 3358171 A SU3358171 A SU 3358171A SU 1172449 A3 SU1172449 A3 SU 1172449A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- phenyl
- ethanol
- amino
- methyl
- propyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 4
- 150000003839 salts Chemical class 0.000 title claims abstract 5
- 229940085239 selective calcium channel blockers with direct cardiac effects phenylalkylamine derivative Drugs 0.000 title claims abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 229910052987 metal hydride Inorganic materials 0.000 claims abstract description 3
- 150000004681 metal hydrides Chemical class 0.000 claims abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract 3
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract 2
- 125000003277 amino group Chemical group 0.000 claims abstract 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract 2
- 238000002955 isolation Methods 0.000 claims abstract 2
- 125000004429 atom Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 claims 1
- -1 hydroxymethylene group Chemical group 0.000 abstract description 19
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 1
- 239000002245 particle Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 76
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 239000003921 oil Substances 0.000 description 23
- 238000002211 ultraviolet spectrum Methods 0.000 description 20
- 238000002329 infrared spectrum Methods 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- 229910000033 sodium borohydride Inorganic materials 0.000 description 10
- 239000012279 sodium borohydride Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 5
- 239000012280 lithium aluminium hydride Substances 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 244000250129 Trigonella foenum graecum Species 0.000 description 2
- 235000001484 Trigonella foenum graecum Nutrition 0.000 description 2
- 229940037003 alum Drugs 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 235000014121 butter Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000011097 chromatography purification Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 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
- 239000003205 fragrance Substances 0.000 description 2
- 210000005240 left ventricle Anatomy 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 2
- 229940050176 methyl chloride Drugs 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 229960001412 pentobarbital Drugs 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000005245 sintering Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- JHCFNOAZZCOTEZ-UHFFFAOYSA-N 2-(4-amino-3,5-dichlorophenyl)-N-[3-(4-chlorophenyl)propyl]acetamide Chemical compound NC1=C(C=C(C=C1Cl)CC(=O)NCCCC1=CC=C(C=C1)Cl)Cl JHCFNOAZZCOTEZ-UHFFFAOYSA-N 0.000 description 1
- SFVMYQHQDBKOPR-UHFFFAOYSA-N 3-phenyl-n-propylpropan-1-amine;hydrochloride Chemical compound Cl.CCCNCCCC1=CC=CC=C1 SFVMYQHQDBKOPR-UHFFFAOYSA-N 0.000 description 1
- 241000009881 Aega Species 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- BMRUPLWFQDETNA-UHFFFAOYSA-N C1(=CC=CC=C1)CC(=O)NC(CCC1=CC=C(C=C1)O)C Chemical compound C1(=CC=CC=C1)CC(=O)NC(CCC1=CC=C(C=C1)O)C BMRUPLWFQDETNA-UHFFFAOYSA-N 0.000 description 1
- 101100521097 Caenorhabditis elegans pri-1 gene Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000237074 Centris Species 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- JLGQDBULZJWVGO-UHFFFAOYSA-N Cl.COC1=CC=C(C=C1)CCCNC(C)C Chemical compound Cl.COC1=CC=C(C=C1)CCCNC(C)C JLGQDBULZJWVGO-UHFFFAOYSA-N 0.000 description 1
- 101100130250 Drosophila melanogaster mfrn gene Proteins 0.000 description 1
- 244000078127 Eleusine coracana Species 0.000 description 1
- 235000013499 Eleusine coracana subsp coracana Nutrition 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 101000984710 Homo sapiens Lymphocyte-specific protein 1 Proteins 0.000 description 1
- 101150007144 Intu gene Proteins 0.000 description 1
- 102000006835 Lamins Human genes 0.000 description 1
- 108010047294 Lamins Proteins 0.000 description 1
- 102100027105 Lymphocyte-specific protein 1 Human genes 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241001585714 Nola Species 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 101150088385 SLC25A37 gene Proteins 0.000 description 1
- 241000282898 Sus scrofa Species 0.000 description 1
- MGQIWUQTCOJGJU-UHFFFAOYSA-N [AlH3].Cl Chemical compound [AlH3].Cl MGQIWUQTCOJGJU-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical compound [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 208000014797 chronic intestinal pseudoobstruction Diseases 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 101150086656 dim1 gene Proteins 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 210000005053 lamin Anatomy 0.000 description 1
- RLAWWYSOJDYHDC-BZSNNMDCSA-N lisinopril Chemical compound C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 RLAWWYSOJDYHDC-BZSNNMDCSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical group CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 235000002079 ragi Nutrition 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 101150101156 slc51a gene Proteins 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- 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
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B23/00—Record carriers not specific to the method of recording or reproducing; Accessories, e.g. containers, specially adapted for co-operation with the recording or reproducing apparatus ; Intermediate mediums; Apparatus or processes specially adapted for their manufacture
- G11B23/02—Containers; Storing means both adapted to cooperate with the recording or reproducing means
- G11B23/04—Magazines; Cassettes for webs or filaments
- G11B23/08—Magazines; Cassettes for webs or filaments for housing webs or filaments having two distinct ends
- G11B23/087—Magazines; Cassettes for webs or filaments for housing webs or filaments having two distinct ends using two different reels or cores
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B25/00—Apparatus characterised by the shape of record carrier employed but not specific to the method of recording or reproducing, e.g. dictating apparatus; Combinations of such apparatus
- G11B25/06—Apparatus characterised by the shape of record carrier employed but not specific to the method of recording or reproducing, e.g. dictating apparatus; Combinations of such apparatus using web-form record carriers, e.g. tape
- G11B25/066—Apparatus characterised by the shape of record carrier employed but not specific to the method of recording or reproducing, e.g. dictating apparatus; Combinations of such apparatus using web-form record carriers, e.g. tape adapted for use with containers of different sizes or configurations; adaptor devices therefor
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3046465 | 1980-12-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1172449A3 true SU1172449A3 (ru) | 1985-08-07 |
Family
ID=6118763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU813358171A SU1172449A3 (ru) | 1980-12-10 | 1981-11-27 | Способ получени производных фенилалкиламина или их солей |
Country Status (32)
| Country | Link |
|---|---|
| JP (1) | JPS57122048A (es) |
| KR (1) | KR870000183B1 (es) |
| AR (1) | AR227802A1 (es) |
| AT (1) | AT379378B (es) |
| AU (1) | AU547655B2 (es) |
| BE (1) | BE891416A (es) |
| CA (1) | CA1202636A (es) |
| CH (1) | CH651541A5 (es) |
| CS (1) | CS229924B2 (es) |
| DD (1) | DD202867A5 (es) |
| DE (1) | DE3146623A1 (es) |
| DK (1) | DK541981A (es) |
| ES (4) | ES8301890A1 (es) |
| FI (1) | FI813934L (es) |
| FR (1) | FR2498596B1 (es) |
| GB (1) | GB2088873B (es) |
| GR (1) | GR77323B (es) |
| HU (1) | HU185676B (es) |
| IE (1) | IE52007B1 (es) |
| IL (1) | IL64498A (es) |
| IT (1) | IT1172129B (es) |
| LU (1) | LU83830A1 (es) |
| NL (1) | NL8105170A (es) |
| NO (1) | NO152649C (es) |
| NZ (1) | NZ199215A (es) |
| PH (1) | PH21599A (es) |
| PL (1) | PL129385B1 (es) |
| PT (1) | PT74112B (es) |
| SE (1) | SE8107387L (es) |
| SU (1) | SU1172449A3 (es) |
| YU (1) | YU290381A (es) |
| ZA (1) | ZA818529B (es) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4720586A (en) * | 1983-12-06 | 1988-01-19 | Fisons, Plc | Substituted 3,4-dihydroxy-phenylethylamino compounds |
| GB8419963D0 (en) * | 1984-08-06 | 1984-09-12 | Lundbeck & Co As H | Intermediate compound and method |
| US4943591A (en) * | 1984-10-17 | 1990-07-24 | Glaxo Group Limited | Dichloroaniline derivatives |
| GB8426191D0 (en) * | 1984-10-17 | 1984-11-21 | Glaxo Holdings Ltd | Chemical compounds |
| GB8603475D0 (en) * | 1986-02-12 | 1986-03-19 | Glaxo Group Ltd | Chemical compounds |
| GB8703007D0 (en) * | 1987-02-10 | 1987-03-18 | Glaxo Group Ltd | Chemical compounds |
| JPS63290852A (ja) * | 1987-02-10 | 1988-11-28 | グラクソ、グループ、リミテッド | 化合物 |
| US4906645A (en) * | 1988-09-12 | 1990-03-06 | Merck & Co., Inc. | Pyridyl aminoethanol compounds with growth promotion and an increase in feed efficiency |
| DE4028398A1 (de) * | 1990-09-07 | 1992-03-12 | Thomae Gmbh Dr K | Phenylethanolamine, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| AU666133B2 (en) * | 1991-10-04 | 1996-02-01 | Taisho Pharmaceutical Co., Ltd. | Alkoxyphenylalkylamine derivative |
| US8349898B2 (en) * | 2008-11-18 | 2013-01-08 | Wisconsin Alumni Research Foundation | Sigma-1 receptor ligands and methods of use |
| GB201208775D0 (en) * | 2012-05-18 | 2012-07-04 | Uni I Oslo | Chemical compounds |
| US10668030B2 (en) * | 2016-04-21 | 2020-06-02 | University Of Kentucky Research Foundation | Vesicular monoamine transporter-2 ligands and their use in the treatment of psychostimulant abuse |
| WO2023235153A1 (en) * | 2022-05-31 | 2023-12-07 | Corteva Agriscience Llc | Crystalline forms of picolinamide fungicide compound |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1618007A1 (de) * | 1967-05-09 | 1970-10-29 | Thomae Gmbh Dr K | Verfahren zur Herstellung von neuen Amino-monohalogenphenylaethanolaminen |
| DE2351281C3 (de) * | 1973-10-12 | 1981-07-30 | Dr. Karl Thomae Gmbh, 7950 Biberach | Aminophenyl-äthanolamin-Derivate, deren Herstellung und Verwendung |
| NL176168C (nl) * | 1972-12-18 | 1985-03-01 | Thomae Gmbh Dr K | Werkwijze ter bereiding respectievelijk vervaardiging van een farmaceutisch preparaat en werkwijze ter bereiding van daarbij bruikbare nieuwe gesubstitueerde 1-(4-aminofenyl)-2-amino-ethanol-derivaten die, behalve een analgetische, uterusspasmolytische en anti-spastische werking op de dwarsgestreepte spieren, in het bijzonder een beta2-mimetische en/of beta1-blokkerende werking bezitten. |
| JPS51125232A (en) * | 1975-02-05 | 1976-11-01 | Yamanouchi Pharmaceut Co Ltd | Process for preparing 4-substituted amido-3,5-dihalogeno-alpha-substituted aminomethylbenzyl alcohols |
| GB1523974A (en) * | 1975-02-05 | 1978-09-06 | Yamanouchi Pharma Co Ltd | 4-substituted amino- -aminomethylbenzyl alcohol derivatives |
| EP0006961A1 (en) * | 1978-02-21 | 1980-01-23 | Sandoz Ag | New phenylethylamines, process for their preparation, and pharmaceutical compositions containing them |
| DK268579A (da) * | 1978-07-03 | 1980-01-04 | Lilly Co Eli | Fremgangsmaade til fremstilling af phenetamolaminer |
-
1981
- 1981-11-16 NL NL8105170A patent/NL8105170A/nl not_active Application Discontinuation
- 1981-11-25 DE DE19813146623 patent/DE3146623A1/de not_active Withdrawn
- 1981-11-27 SU SU813358171A patent/SU1172449A3/ru active
- 1981-11-30 AT AT0512981A patent/AT379378B/de not_active IP Right Cessation
- 1981-12-02 ES ES507635A patent/ES8301890A1/es not_active Expired
- 1981-12-07 IT IT49853/81A patent/IT1172129B/it active
- 1981-12-07 GR GR66712A patent/GR77323B/el unknown
- 1981-12-07 DD DD81235491A patent/DD202867A5/de unknown
- 1981-12-07 CH CH7800/81A patent/CH651541A5/de not_active IP Right Cessation
- 1981-12-08 DK DK541981A patent/DK541981A/da not_active Application Discontinuation
- 1981-12-08 FI FI813934A patent/FI813934L/fi not_active Application Discontinuation
- 1981-12-09 NO NO814194A patent/NO152649C/no unknown
- 1981-12-09 BE BE0/206788A patent/BE891416A/fr not_active IP Right Cessation
- 1981-12-09 IL IL64498A patent/IL64498A/xx unknown
- 1981-12-09 CA CA000391831A patent/CA1202636A/en not_active Expired
- 1981-12-09 SE SE8107387A patent/SE8107387L/xx not_active Application Discontinuation
- 1981-12-09 JP JP56198337A patent/JPS57122048A/ja active Pending
- 1981-12-09 NZ NZ199215A patent/NZ199215A/en unknown
- 1981-12-09 GB GB8137051A patent/GB2088873B/en not_active Expired
- 1981-12-09 PL PL1981234155A patent/PL129385B1/pl unknown
- 1981-12-09 IE IE2888/81A patent/IE52007B1/en unknown
- 1981-12-09 AU AU78414/81A patent/AU547655B2/en not_active Ceased
- 1981-12-09 HU HU813708A patent/HU185676B/hu unknown
- 1981-12-09 ZA ZA818529A patent/ZA818529B/xx unknown
- 1981-12-10 FR FR8123106A patent/FR2498596B1/fr not_active Expired
- 1981-12-10 AR AR287754A patent/AR227802A1/es active
- 1981-12-10 KR KR1019810004912A patent/KR870000183B1/ko active IP Right Grant
- 1981-12-10 LU LU83830A patent/LU83830A1/de unknown
- 1981-12-10 YU YU02903/81A patent/YU290381A/xx unknown
- 1981-12-10 CS CS819178A patent/CS229924B2/cs unknown
- 1981-12-10 PH PH26726A patent/PH21599A/en unknown
- 1981-12-10 PT PT74112A patent/PT74112B/pt unknown
-
1982
- 1982-06-08 ES ES512915A patent/ES512915A0/es active Granted
- 1982-06-08 ES ES512914A patent/ES8304537A1/es not_active Expired
- 1982-06-08 ES ES512913A patent/ES512913A0/es active Granted
Non-Patent Citations (1)
| Title |
|---|
| Патент US № 3536712, кл. 260-253, опублик. 27.10.70. * |
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