CH434241A - Verfahren zur Herstellung bicyclisch substituierter Aminoalkane - Google Patents

Verfahren zur Herstellung bicyclisch substituierter Aminoalkane

Info

Publication number: CH434241A
Authority: CH; Switzerland
Prior art keywords: sep; compounds; preparation; formula; aminoalkanes
Prior art date: 1962-06-09

Application number

CH1638166A

Other languages

German (de)

English (en)

Inventor

Helmut Kraft

Wilfried Klavehn

Original Assignee

Knoll Ag

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.)

1962-06-09

Filing date

1963-05-21

Publication date

1967-04-30

1963-05-21 Application filed by Knoll Ag filed Critical Knoll Ag

1967-04-30 Publication of CH434241A publication Critical patent/CH434241A/de

Links

238000000034 method Methods 0.000 title claims description 8
238000002360 preparation method Methods 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims description 9
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 4
150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
239000011230 binding agent Substances 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
229960000583 acetic acid Drugs 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000012362 glacial acetic acid Substances 0.000 description 6
239000001294 propane Substances 0.000 description 6
239000001257 hydrogen Substances 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
-1 alkylene radical Chemical class 0.000 description 2
238000001035 drying Methods 0.000 description 2
229940093915 gynecological organic acid Drugs 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
229910003446 platinum oxide Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
238000003756 stirring Methods 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical class CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 description 1
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
239000003434 antitussive agent Substances 0.000 description 1
229940124584 antitussives Drugs 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000000812 cholinergic antagonist Substances 0.000 description 1
JPWJQIKXWASNOD-UHFFFAOYSA-N cycloheptylidenecycloheptane Chemical group C1CCCCCC1=C1CCCCCC1 JPWJQIKXWASNOD-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000002048 spasmolytic effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (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)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1638166A 1962-06-09 1963-05-21 Verfahren zur Herstellung bicyclisch substituierter Aminoalkane CH434241A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEK46969A DE1284421B (de)	1962-06-09	1962-06-09	Bicyclisch substituierte Aminoalkane und Verfahren zu ihrer Herstellung

Publications (1)

Publication Number	Publication Date
CH434241A true CH434241A (de)	1967-04-30

Family

ID=7224390

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH1638166A CH434241A (de)	1962-06-09	1963-05-21	Verfahren zur Herstellung bicyclisch substituierter Aminoalkane
CH638263A CH435250A (de)	1962-06-09	1963-05-21	Verfahren zur Herstellung bicyclisch substituierter Aminoalkane

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH638263A CH435250A (de)	1962-06-09	1963-05-21	Verfahren zur Herstellung bicyclisch substituierter Aminoalkane

Country Status (3)

Country	Link
CH (2)	CH434241A (fr)
DE (1)	DE1284421B (fr)
FR (1)	FR2641M (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1130318A (fr) *	1978-10-11	1982-08-24	Peter M. Muller	Derives du cyclohexadiene

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1088484B (de) *	1958-03-10	1960-09-08	Bayer Ag	Verfahren zur Herstellung blutdruckwirksamer bicyclisch substituierter Carbinamine bzw. deren nicht toxischen Salzen
DE1110159B (de) *	1959-08-01	1961-07-06	Merck Ag E	Verfahren zur Herstellung analeptisch wirksamer N-substituierter Aminonorcamphanderivate bzw. von deren Saeureadditionssalzen und quaternaeren Ammoniumverbindungen
BE598255A (fr) *	1959-12-19	1961-06-16	Knoll Ag	Nouvelles amines et leur préparation

1962
- 1962-06-09 DE DEK46969A patent/DE1284421B/de active Pending
1963
- 1963-05-21 CH CH1638166A patent/CH434241A/de unknown
- 1963-05-21 CH CH638263A patent/CH435250A/de unknown
- 1963-06-10 FR FR937603A patent/FR2641M/fr not_active Expired

Also Published As

Publication number	Publication date
CH435250A (de)	1967-05-15
FR2641M (fr)	1964-07-06
DE1284421B (de)	1968-12-05

Publication	Publication Date	Title
DE2313258A1 (de)	1973-09-27	Verfahren zur herstellung von butyrophenonderivaten und ihren salzen neue butyrophenonderivate, ihre salze und diese verbindungen enthaltende arzneimittel
DE2351281C3 (de)	1981-07-30	Aminophenyl-äthanolamin-Derivate, deren Herstellung und Verwendung
DE1807218A1 (de)	1969-06-12	Oxotremorin-Antagonisten und Verfahren zu deren Herstellung
CH434241A (de)	1967-04-30	Verfahren zur Herstellung bicyclisch substituierter Aminoalkane
DE1795176B2 (de)	1974-03-21	N'-substituierte 5-Aminoacetyl-5,10-dihydro-l lH-dibenzo eckige Klammer auf b,e eckige Klammer zu eckige Klammer auf 1,4 eckige Klammer zu diazepin-11one und Verfahren zu ihrer Herstellung
DE2730593A1 (de)	1978-01-19	Neue aminoalkoxybenzofurane, verfahren zur herstellung derselben und diese enthaltende pharmazeutische mittel
DE945449C (de)	1956-07-12	Verfahren zur Herstellung von 2-Methyl-4-cyclohexyl-6-methyl-aminomethylphenol
AT239210B (de)	1965-03-25	Verfahren zur Herstellung von neuen bicyclisch substituierten Aminoalkanen sowie deren Salzen und quaternären Ammoniumverbindungen
DE955591C (de)	1957-01-03	Verfahren zur Herstellung von 2-Methyl-4-cyclohexyl-6-dimethylaminomethylphenol
AT239209B (de)	1965-03-25	Verfahren zur Herstellung von neuen bicyclisch substituierten Aminoalkanen sowie deren Salzen und quaternären Ammoniumverbindungen
AT235284B (de)	1964-08-25	Verfahren zur Herstellung neuer Indolderivate
AT275518B (de)	1969-10-27	Verfahren zur Herstellung von neuen in 4-Stellung substituierten 1-(4-Oxo-4-phenyl-butyl)-piperidinen sowie von deren Säureaddtionssalzen
DE1545672B2 (de)	1974-11-07	Dikarbonsäureimidderivate und Verfahren zu ihrer Herstellung
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AT262971B (de)	1968-07-10	Verfahren zur Herstellung von neuen 2-Amino-5-halogenbenzylaminen und deren Additionssalzen mit Säuren
AT204556B (de)	1959-07-25	Verfahren zur Herstellung von neuen, substituierten Piperidinderivaten
AT262989B (de)	1968-07-10	Verfahren zur Herstellung von neuen, pharmazeutisch wirksamen cyclischen Imiden und ihren Salzen
AT233577B (de)	1964-05-11	Verfahren zur Herstellung neuer, basischer Phenoxazin-Derivate und ihrer Salze
AT273149B (de)	1969-08-11	Verfahren zur Herstellung von neuen N-Aminoacyl-3,4-dihydro-(2H)-1,4-benzoxazinen und ihren Salzen
AT217024B (de)	1961-09-11	Verfahren zur Herstellung neuer basischer Äther, sowie ihrer Salze und quartären Ammoniumverbindungen
AT227707B (de)	1963-06-10	Verfahren zur Herstellung von neuen Chinazolinonderivaten
AT248433B (de)	1966-07-25	Verfahren zur Herstellung von neuen ω-Phenyl-ω-pyridyl-alkylaminderivaten
AT276353B (de)	1969-11-25	Verfahren zur Herstellung von neuen 2-Amino-chlor-benzylaminen und deren Säureadditionssalzen
AT207380B (de)	1960-01-25	Verfahren zur Herstellung von neuen, substituierten Piperidinderivaten
AT210420B (de)	1960-08-10	Verfahren zur Herstellung von neuen Azetidin-Derivaten