CH462189A - Verfahren zur Herstellung von substituierten Propylaminderivaten - Google Patents

Verfahren zur Herstellung von substituierten Propylaminderivaten

Info

Publication number: CH462189A
Authority: CH; Switzerland
Prior art keywords: group; formula; compounds; hydrogen; starting material
Prior art date: 1961-08-10

Application number

CH889162A

Other languages

German (de)

English (en)

Inventor

Harsanyi Kalman Dr Dipl-Ing

Dezso Dipl Ing Korbonits

Kalman Dipl Ing Takats

Laszlo Dr Med Tardos

Leszkovszky Gyorgy Dr Dipl-Ing

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

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.)

1961-08-10

Filing date

1962-07-24

Publication date

1968-09-15

1962-07-24 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1968-09-15 Publication of CH462189A publication Critical patent/CH462189A/de

Links

238000000034 method Methods 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title claims description 6
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical class CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 14
239000003054 catalyst Substances 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 11
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 11
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 5
150000002431 hydrogen Chemical group 0.000 claims description 5
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 4
150000001412 amines Chemical class 0.000 claims description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 3
125000004663 dialkyl amino group Chemical group 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
150000002576 ketones Chemical class 0.000 claims description 3
239000007868 Raney catalyst Substances 0.000 claims description 2
229910000564 Raney nickel Inorganic materials 0.000 claims description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
229910052763 palladium Inorganic materials 0.000 claims description 2
229910052697 platinum Inorganic materials 0.000 claims description 2
KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 claims description 2
150000003892 tartrate salts Chemical class 0.000 claims description 2
239000007858 starting material Substances 0.000 claims 4
OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical class [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 0.000 claims 1
150000000994 L-ascorbates Chemical class 0.000 claims 1
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 1
239000002253 acid Substances 0.000 claims 1
150000007513 acids Chemical class 0.000 claims 1
235000010323 ascorbic acid Nutrition 0.000 claims 1
150000001860 citric acid derivatives Chemical class 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
150000003893 lactate salts Chemical class 0.000 claims 1
150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
239000000047 product Substances 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 9
239000002585 base Substances 0.000 description 8
239000000155 melt Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
241000700159 Rattus Species 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
-1 dimethyiamino Chemical group 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000011976 maleic acid Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 5
241000282472 Canis lupus familiaris Species 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
230000036772 blood pressure Effects 0.000 description 4
230000007423 decrease Effects 0.000 description 4
230000001988 toxicity Effects 0.000 description 4
231100000419 toxicity Toxicity 0.000 description 4
241000282326 Felis catus Species 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 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
150000002689 maleic acids Chemical class 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
OJYGBLRPYBAHRT-IPQSZEQASA-N chloralose Chemical compound O1[C@H](C(Cl)(Cl)Cl)O[C@@H]2[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]21 OJYGBLRPYBAHRT-IPQSZEQASA-N 0.000 description 2
229950009941 chloralose Drugs 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000012458 free base Substances 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000000725 suspension Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
GKDLTXYXODKDEA-UHFFFAOYSA-N 1-phenylbutan-2-one Chemical compound CCC(=O)CC1=CC=CC=C1 GKDLTXYXODKDEA-UHFFFAOYSA-N 0.000 description 1
RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
ONNSYMOPMFOHHE-UHFFFAOYSA-N 4-(3-aminobutyl)-2-methoxyphenol Chemical compound COC1=CC(CCC(C)N)=CC=C1O ONNSYMOPMFOHHE-UHFFFAOYSA-N 0.000 description 1
WNTVTQIJPAFZEL-UHFFFAOYSA-N 4-(3-aminobutyl)phenol Chemical compound CC(N)CCC1=CC=C(O)C=C1 WNTVTQIJPAFZEL-UHFFFAOYSA-N 0.000 description 1
229910000761 Aluminium amalgam Inorganic materials 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
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 1
239000012448 Lithium borohydride Substances 0.000 description 1
208000007101 Muscle Cramp Diseases 0.000 description 1
208000005392 Spasm Diseases 0.000 description 1
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
229960004266 acetylcholine chloride Drugs 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000003289 ascorbyl group Chemical class [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 description 1
WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
229910001626 barium chloride Inorganic materials 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000001816 cooling Methods 0.000 description 1
210000003748 coronary sinus Anatomy 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000004744 fabric Substances 0.000 description 1
210000001105 femoral artery Anatomy 0.000 description 1
210000003191 femoral vein Anatomy 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229960002748 norepinephrine Drugs 0.000 description 1
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910001023 sodium amalgam Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
- 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
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/24—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds
- C07C209/26—Preparation of compounds containing amino groups bound to a carbon skeleton by reductive alkylation of ammonia, amines or compounds having groups reducible to amino groups, with carbonyl compounds by reduction with hydrogen
- 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
- C07C211/27—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 having amino groups linked to the six-membered aromatic ring by saturated carbon chains
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Emergency Medicine (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH889162A 1961-08-10 1962-07-24 Verfahren zur Herstellung von substituierten Propylaminderivaten CH462189A (de)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
HUCI000360		1961-08-10
HUCI000387		1962-03-10
HUCI000389		1962-03-15

Publications (1)

Publication Number	Publication Date
CH462189A true CH462189A (de)	1968-09-15

Family

ID=27270140

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH889162A CH462189A (de)	1961-08-10	1962-07-24	Verfahren zur Herstellung von substituierten Propylaminderivaten

Country Status (5)

Country	Link
CH (1)	CH462189A (da)
DK (1)	DK106438C (da)
FI (1)	FI41960C (da)
GB (1)	GB954735A (da)
SE (1)	SE300819B (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU200591B (en) *	1986-07-11	1990-07-28	Chinoin Gyogyszer Es Vegyeszet	Process for producing new diphenyl propylamine derivatives and pharmaceutical compositions comprising such compounds

1962
- 1962-07-24 CH CH889162A patent/CH462189A/de unknown
- 1962-08-03 FI FI621467A patent/FI41960C/fi active
- 1962-08-09 DK DK350562AA patent/DK106438C/da active
- 1962-08-09 SE SE8694/62A patent/SE300819B/xx unknown
- 1962-08-10 GB GB30848/62A patent/GB954735A/en not_active Expired

Also Published As

Publication number	Publication date
SE300819B (da)	1968-05-13
DK106438C (da)	1967-02-06
GB954735A (en)	1964-04-08
FI41960B (da)	1969-12-31
FI41960C (fi)	1970-04-10

Publication	Publication Date	Title
DE2461860C2 (da)	1989-10-26
DE1275069B (de)	1968-08-14	1-(3', 5'-Dihydroxyphenyl)-1-hydroxy-2-isopropylaminoalkane und Verfahren zu ihrer Herstellung
DE2305092C2 (da)	1987-10-01
DE1080563B (de)	1960-04-28	Verfahren zur Herstellung diquaternaerer Salze von Alkylendiaminen
DE2413102A1 (de)	1975-10-09	Verfahren zur herstellung von 1-(3,5dihydroxyphenyl)-1-hydroxy-2- eckige klammer auf 1-methyl-2-(4-hydroxyphenyl)-aethyl eckige klammer zu -amino-aethan
CH500983A (de)	1970-12-31	Verfahren zur Herstellung von 1-Amino-isochinolinen
DE1110159B (de)	1961-07-06	Verfahren zur Herstellung analeptisch wirksamer N-substituierter Aminonorcamphanderivate bzw. von deren Saeureadditionssalzen und quaternaeren Ammoniumverbindungen
EP0075752A2 (de)	1983-04-06	Substituierte 2-Phenyl-2-(pyridyloxy)-ethylamine und isostere Verbindungen, Verfahren zu ihrer Herstellung und Verwendung
DE1470194C3 (de)	1975-07-24	1,3,3-trisubstituierte 4-0mega-(Aminoalkyl) -2-pyrrolidinone und-2-thiopyrrolidinone
EP0086416A2 (de)	1983-08-24	Corynanthein-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DE2951247C2 (da)	1988-03-10
DE1695140A1 (de)	1970-12-17	Verfahren zur Herstellung von Phenanthridinderivaten
CH640507A5 (en)	1984-01-13	Process for preparing novel 1-aryloxy-2-hydroxy-3-aminopropanes
CH638184A5 (de)	1983-09-15	Verfahren zur herstellung neuer phenylazacycloalkane.
CH462189A (de)	1968-09-15	Verfahren zur Herstellung von substituierten Propylaminderivaten
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AT237597B (de)	1964-12-28	Verfahren zur Herstellung von neuen Propylaminderivaten und deren Salzen
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AT238180B (de)	1965-01-25	Verfahren zur Herstellung neuer Pyrrolidinverbindungen
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AT238181B (de)	1965-01-25	Verfahren zur Herstellung neuer Pyrrolidinverbindungen