PL96538B1 - Sposob wytwarzania nowych aminofenyloetanoloamin - Google Patents

Sposob wytwarzania nowych aminofenyloetanoloamin Download PDF

Info

Publication number: PL96538B1
Authority: PL; Poland
Prior art keywords: hydrogen; general formula; compound; carbon atoms; amino
Prior art date: 1972-12-18

Application number

PL18240673A

Other languages

English (en)

Polish (pl)

Original Assignee

Thomae Karl (Dr) Gmbh

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.)

1972-12-18

Filing date

1973-12-17

Publication date

1977-12-31

1972-12-18 Priority claimed from DE2261914A external-priority patent/DE2261914C3/de

1973-09-08 Priority claimed from DE19732345442 external-priority patent/DE2345442C2/de

1973-10-12 Priority claimed from DE19732351281 external-priority patent/DE2351281C3/de

1973-12-17 Application filed by Thomae Karl (Dr) Gmbh filed Critical Thomae Karl (Dr) Gmbh

1977-12-31 Publication of PL96538B1 publication Critical patent/PL96538B1/pl

Links

IKNLHBCWJCVJDZ-UHFFFAOYSA-N 1,2-diamino-1-phenylethanol Chemical compound NCC(N)(O)C1=CC=CC=C1 IKNLHBCWJCVJDZ-UHFFFAOYSA-N 0.000 title claims description 4
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 27
238000000034 method Methods 0.000 claims description 22
150000002431 hydrogen Chemical group 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
239000003054 catalyst Substances 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 9
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
238000005695 dehalogenation reaction Methods 0.000 claims description 7
238000005984 hydrogenation reaction Methods 0.000 claims description 7
150000007524 organic acids Chemical class 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
-1 cyano, carboxy, carboxy Chemical group 0.000 claims description 6
229910052740 iodine Inorganic materials 0.000 claims description 6
150000007522 mineralic acids Chemical class 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
239000000203 mixture Substances 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
235000005985 organic acids Nutrition 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
125000004103 aminoalkyl group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
238000004440 column chromatography Methods 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
239000011630 iodine Substances 0.000 claims 3
238000002360 preparation method Methods 0.000 claims 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
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 claims 1
OCQAXYHNMWVLRH-ROUUACIJSA-N (2s,3s)-2,3-dibenzoyl-2,3-dihydroxybutanedioic acid Chemical compound O=C([C@](O)(C(=O)O)[C@@](O)(C(O)=O)C(=O)C=1C=CC=CC=1)C1=CC=CC=C1 OCQAXYHNMWVLRH-ROUUACIJSA-N 0.000 claims 1
DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims 1
229930007886 (R)-camphor Natural products 0.000 claims 1
235000011002 L(+)-tartaric acid Nutrition 0.000 claims 1
239000001358 L(+)-tartaric acid Substances 0.000 claims 1
FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
238000002425 crystallisation Methods 0.000 claims 1
230000008025 crystallization Effects 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
ITHPEWAHFNDNIO-UHFFFAOYSA-N triphosphane Chemical compound PPP ITHPEWAHFNDNIO-UHFFFAOYSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
238000002844 melting Methods 0.000 description 16
230000008018 melting Effects 0.000 description 16
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
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238000000354 decomposition reaction Methods 0.000 description 9
230000000694 effects Effects 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
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KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
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239000000047 product Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
NPFVNFAXZKBDCE-UHFFFAOYSA-N 1-(pentylamino)ethanol Chemical compound CCCCCNC(C)O NPFVNFAXZKBDCE-UHFFFAOYSA-N 0.000 description 4
230000000202 analgesic effect Effects 0.000 description 4
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
ZUYWFUUNQDJUKG-UHFFFAOYSA-N 1-(butylamino)ethanol Chemical compound CCCCNC(C)O ZUYWFUUNQDJUKG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
208000009079 Bronchial Spasm Diseases 0.000 description 3
208000014181 Bronchial disease Diseases 0.000 description 3
206010006482 Bronchospasm Diseases 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000001813 broncholytic effect Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
230000007017 scission Effects 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
NEPOREXZZHXGPN-UHFFFAOYSA-N 2-amino-5-[2-(cyclopropylamino)-1-hydroxyethyl]benzonitrile Chemical compound C1=C(C#N)C(N)=CC=C1C(O)CNC1CC1 NEPOREXZZHXGPN-UHFFFAOYSA-N 0.000 description 2
241000700198 Cavia Species 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
208000036029 Uterine contractions during pregnancy Diseases 0.000 description 2
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
229960004373 acetylcholine Drugs 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
230000002921 anti-spasmodic effect Effects 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229910052681 coesite Inorganic materials 0.000 description 2
229910052906 cristobalite Inorganic materials 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
238000013213 extrapolation Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
229910003445 palladium oxide Inorganic materials 0.000 description 2
JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
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229910052682 stishovite Inorganic materials 0.000 description 2
210000003699 striated muscle Anatomy 0.000 description 2
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
229910052905 tridymite Inorganic materials 0.000 description 2
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235000014655 lactic acid 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
239000000155 melt Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

PL18240673A 1972-12-18 1973-12-17 Sposob wytwarzania nowych aminofenyloetanoloamin PL96538B1 (pl)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE2261914A DE2261914C3 (de)	1972-12-18	1972-12-18	Amino-phenyl-äthanolamine und deren Säureadditionssalze, Verfahren zu deren Herstellung und Arzneimittel
DE19732345442 DE2345442C2 (de)	1973-09-08	1973-09-08	d- und l-Phenyläthanolamine und deren Salze, Herstellungsverfahren und Arzneimittel auf deren Basis
DE19732351281 DE2351281C3 (de)	1973-10-12	1973-10-12	Aminophenyl-äthanolamin-Derivate, deren Herstellung und Verwendung

Publications (1)

Publication Number	Publication Date
PL96538B1 true PL96538B1 (pl)	1977-12-31

Family

ID=27184904

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
PL18240673A PL96538B1 (pl)	1972-12-18	1973-12-17	Sposob wytwarzania nowych aminofenyloetanoloamin
PL18241073A PL96535B1 (pl)	1972-12-18	1973-12-17	Sposob wytwarzania nowych aminofenyloetanoloamin
PL16739973A PL96221B1 (pl)	1972-12-18	1973-12-17	Sposob wytwarzania nowych aminofenyloetanoloamin

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
PL18241073A PL96535B1 (pl)	1972-12-18	1973-12-17	Sposob wytwarzania nowych aminofenyloetanoloamin
PL16739973A PL96221B1 (pl)	1972-12-18	1973-12-17	Sposob wytwarzania nowych aminofenyloetanoloamin

Country Status (5)

Country	Link
AT (1)	AT333251B (de)
CH (2)	CH605656A5 (de)
ES (4)	ES421350A1 (de)
PH (2)	PH20591A (de)
PL (3)	PL96538B1 (de)

1973
- 1973-12-10 AT AT1028573A patent/AT333251B/de not_active IP Right Cessation
- 1973-12-11 ES ES421350A patent/ES421350A1/es not_active Expired
- 1973-12-14 CH CH1179077A patent/CH605656A5/xx not_active IP Right Cessation
- 1973-12-14 CH CH1178877A patent/CH605623A5/de not_active IP Right Cessation
- 1973-12-17 PL PL18240673A patent/PL96538B1/pl unknown
- 1973-12-17 PL PL18241073A patent/PL96535B1/pl unknown
- 1973-12-17 PL PL16739973A patent/PL96221B1/pl unknown
- 1973-12-18 PH PH15328A patent/PH20591A/en unknown
1974
- 1974-04-30 ES ES425792A patent/ES425792A1/es not_active Expired
- 1974-04-30 ES ES425793A patent/ES425793A1/es not_active Expired
- 1974-04-30 ES ES425791A patent/ES425791A1/es not_active Expired
1982
- 1982-03-28 PH PH27074A patent/PH19317A/en unknown

Also Published As

Publication number	Publication date
PH20591A (en)	1987-02-20
PH19317A (en)	1986-03-18
ES425791A1 (es)	1976-06-16
CH605623A5 (en)	1978-10-13
ES425793A1 (es)	1977-07-01
ES421350A1 (es)	1976-12-01
ATA1028573A (de)	1976-03-15
CH605656A5 (de)	1978-10-13
PL96535B1 (pl)	1977-12-31
PL96221B1 (pl)	1977-12-31
AT333251B (de)	1976-11-10
ES425792A1 (es)	1976-06-16

Publication	Publication Date	Title
EP0110372B1 (de)	1986-09-10	1-Phenylisochinolinderivate und Verfahren zu ihrer Herstellung, diese Verbindung enthaltende pharmazeutische Präparate und deren Anwendung
US4119710A (en)	1978-10-10	Bronchospasmolytic 1-(p-amino-phenyl)-2-amino-ethanols-(1) and salts
FI72714B (fi)	1987-03-31	Foerfarande foer framstaellning av farmakologiskt vaerdefulla 4-acylamino-fenyl-etanolaminer.
US3574211A (en)	1971-04-06	1-(amino-monohalo-phenyl)-2-amino-alkanols and salts
US4730042A (en)	1988-03-08	Compounds 1 or 3-hydroxy-4-benzyl-6-methyl-7-(4-isopropylamino-butoxy)-1,3-dihydro[3,4-C]pyridine and 2-methyl-3-(4-isopropyl-aminobutoxy)-4-(1'-morphilinomethyl)-5-hydroxymethyl-6-benzyl pyridine, useful for treating cardiac arrhythmias
DE2639718A1 (de)	1978-03-16	Neue phenylaethylamine
PL97194B1 (pl)	1978-02-28	Sposob wytwarzania nowych aminofenyloetanoloamin
US4782058A (en)	1988-11-01	1,3,4,6,7,11b-Hexahydro-6-phenyl-2H-pyrazino-(2,1-a)isoquinolines, for anti-histamine or anti-depression treatment
US4224332A (en)	1980-09-23	1-Aza-[2,2,2]-bicyclooctanes and anti-depressant and anti-parkinsonian compositions thereof
DD202867A5 (de)	1983-10-05	Verfahren zur herstellung von phenylalkylaminen
DE2333847A1 (de)	1974-01-24	Tetrahydronaphthole, ihre salze und diese verbindungen enthaltende arzneimittel
US3256289A (en)	1966-06-14	Carbocyclic substituted piperidyl dioxanes
EP0000395B1 (de)	1981-01-07	2-Piperazinotetraline, ihre Herstellung und Verwendung als Arzneimittel
NO141160B (no)	1979-10-15	Analogifremgangsmaate til fremstilling av terapeutisk virksomme 3,4-dihydro-2(1h)-isokinolinkarboksamider
SK16896A3 (en)	1996-10-02	1-£2-(substituted vinyl)\|-3,4-dihydro-5h-2,3-benzodiazepine derivatives
US3910915A (en)	1975-10-07	1-Aryl-2-{8 (substituted amino)alkanoyl{9 -1,2,3,4-tetrahydroisoquinolines
JPS6011901B2 (ja)	1985-03-28	新規の脂肪族置換された４−フエニル−ピペリジン
US3217007A (en)	1965-11-09	Halo- and nitro-substituted phenethyl-z- methyl tetrahydroisoquinolsnes
US4393226A (en)	1983-07-12	Compounds and methods for changing calcium metabolism within the cells of a mammal
Counsell et al.	1960	Esters of Bicyclic Aminoalcohols II: The Synthesis of the Hydroxyquinolizidines and Some of Their Esters as Potential Therapeutic Agents
US3998965A (en)	1976-12-21	4-Aminoalkyl-4-cyano-4-phenyl-butanoic acid esters
Kador et al.	1977	Synthesis and biological evaluation of a tetrahydroisoquinoline derivative possessing selective. beta. 2-adrenergic agonist activity
US2878254A (en)	1959-03-17	N, n'-alkylene-bis-(3-hydroxypiperidine) compounds and preparation thereof
DD251289A5 (de)	1987-11-11	Verfahren zur herstellung einer neuartigen racemischen oder optisch aktiven verbindung
FI58326C (fi)	1981-01-12	Foerfarande foer framstaellning av som beta-adrenergiskt stimulerande medel anvaendbara alfa-aminometyl-4-hydroksi-3-metylsulfonyl-metylbensylalkoholer