CH495949A - Verfahren zur Herstellung von neuen basischen Äthern - Google Patents

Verfahren zur Herstellung von neuen basischen Äthern

Info

Publication number: CH495949A
Authority: CH; Switzerland
Prior art keywords: reaction; defined above; diphenyl; compounds; carbonates
Prior art date: 1967-03-09

Application number

CH66168A

Other languages

German (de)

English (en)

Inventor

Roderich Dr Hoellinger

Wolf Dr Wendtlandt

Original Assignee

Chemie Linz 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.)

1967-03-09

Filing date

1968-01-16

Publication date

1970-09-15

1968-01-16 Application filed by Chemie Linz Ag filed Critical Chemie Linz Ag

1970-09-15 Publication of CH495949A publication Critical patent/CH495949A/de

Links

150000002170 ethers Chemical class 0.000 title claims description 9
230000000202 analgesic effect Effects 0.000 title abstract description 4
230000000954 anitussive effect Effects 0.000 title abstract 2
230000002082 anti-convulsion Effects 0.000 title abstract 2
229940124584 antitussives Drugs 0.000 title abstract 2
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 title 1
239000002253 acid Substances 0.000 claims abstract description 18
-1 quat ammonium salts Chemical class 0.000 claims abstract description 16
125000000217 alkyl group Chemical group 0.000 claims abstract description 12
125000005843 halogen group Chemical group 0.000 claims abstract description 7
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 29
238000006243 chemical reaction Methods 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 21
150000001875 compounds Chemical class 0.000 claims description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
150000004649 carbonic acid derivatives Chemical class 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
238000000354 decomposition reaction Methods 0.000 claims description 6
238000002844 melting Methods 0.000 claims description 6
230000008018 melting Effects 0.000 claims description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
150000007513 acids Chemical class 0.000 claims description 4
230000001419 dependent effect Effects 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 3
229910052791 calcium Inorganic materials 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
150000002431 hydrogen Chemical group 0.000 claims description 3
239000000155 melt Substances 0.000 claims description 3
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 3
230000000737 periodic effect Effects 0.000 claims description 3
150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 3
230000000694 effects Effects 0.000 abstract description 4
230000000648 anti-parkinson Effects 0.000 abstract description 2
239000000939 antiparkinson agent Substances 0.000 abstract description 2
231100000053 low toxicity Toxicity 0.000 abstract description 2
208000002193 Pain Diseases 0.000 abstract 1
PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 abstract 1
230000003203 everyday effect Effects 0.000 abstract 1
229910052736 halogen Inorganic materials 0.000 abstract 1
230000036407 pain Effects 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
229940035676 analgesics Drugs 0.000 description 3
239000000730 antalgic agent Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
239000011575 calcium Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000000126 substance Substances 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
KIGWGNUATSOTSK-UHFFFAOYSA-N C1(=CC=CC=C1)C(C(CN(C)C)(C)C)(O)C1=CC=CC=C1 Chemical compound C1(=CC=CC=C1)C(C(CN(C)C)(C)C)(O)C1=CC=CC=C1 KIGWGNUATSOTSK-UHFFFAOYSA-N 0.000 description 1
AENNDRDBYISOAC-UHFFFAOYSA-N CCOC(C1=CC=CC=C1)(C2=CC=CC=C2)C(C)CN(C)C Chemical compound CCOC(C1=CC=CC=C1)(C2=CC=CC=C2)C(C)CN(C)C AENNDRDBYISOAC-UHFFFAOYSA-N 0.000 description 1
206010011224 Cough Diseases 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical class OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical class C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
150000004820 halides Chemical group 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
125000005528 methosulfate group Chemical group 0.000 description 1
229960005181 morphine Drugs 0.000 description 1
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
238000010626 work up procedure 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
- 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
- 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
- C07D295/08—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 bound oxygen or sulfur atoms
- C07D295/084—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/092—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH66168A 1967-03-09 1968-01-16 Verfahren zur Herstellung von neuen basischen Äthern CH495949A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
AT222867A AT270617B (de)	1967-03-09	1967-03-09	Verfahren zur Herstellung von neuen basischen Äthern und deren Salzen oder quartären Ammoniumverbindungen

Publications (1)

Publication Number	Publication Date
CH495949A true CH495949A (de)	1970-09-15

Family

ID=3530408

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH66168A CH495949A (de)	1967-03-09	1968-01-16	Verfahren zur Herstellung von neuen basischen Äthern

Country Status (7)

Country	Link
AT (1)	AT270617B (cs)
CH (1)	CH495949A (cs)
CS (1)	CS150566B2 (cs)
DK (1)	DK125085B (cs)
ES (1)	ES351435A1 (cs)
FI (1)	FI48070B (cs)
SE (1)	SE352338B (cs)

1967
- 1967-03-09 AT AT222867A patent/AT270617B/de active
1968
- 1968-01-16 CH CH66168A patent/CH495949A/de not_active IP Right Cessation
- 1968-02-05 CS CS871A patent/CS150566B2/cs unknown
- 1968-02-23 SE SE02369/68A patent/SE352338B/xx unknown
- 1968-03-07 FI FI00614/68A patent/FI48070B/fi active
- 1968-03-07 DK DK93168AA patent/DK125085B/da unknown
- 1968-03-09 ES ES351435A patent/ES351435A1/es not_active Expired

Also Published As

Publication number	Publication date
CS150566B2 (cs)	1973-09-04
DK125085B (da)	1972-12-27
ES351435A1 (es)	1969-06-16
SE352338B (cs)	1972-12-27
FI48070B (cs)	1974-02-28
AT270617B (de)	1969-05-12

Legal Events

Date	Code	Title	Description
1975-08-29	PL	Patent ceased

Publication	Publication Date	Title
DE2501957C2 (de)	1982-06-09	Verfahren zur Gewinnung von optisch aktivem p-Hydroxyphenylglycin
DE2741386C3 (de)	1982-04-08	Verfahren zur Isomerisierung von cis,cis- und cis, trans-Isomeren des Di-(p-aminocyclohexyl)-methans und dabei als Zwischenprodukte gebildete Bis-benzaldimine
EP0812821B1 (de)	2000-11-29	Kohlensäureesterbetaine und deren Herstellung und Verwendung
DD140041B1 (de)	1986-05-07	Verfahren zur herstellung von langkettigen n-alkyldimethylmorpholinen
DE1227914B (de)	1966-11-03	Verfahren zur Herstellung von 3-(1, 2-Dithia-cyclopentyl)-5-pentansaeure
DE1543729B2 (de)	1973-04-05	Verfahren zur herstellung von basischen benzhydrylaethern
DE2000030C3 (de)	1974-08-01	3-Alkoxy-und 3-Phenoxy-2-(diphenylhydroxy)methyl-propylamine und diese enthaltende Arzneimittel
DE883901C (de)	1953-07-23	Verfahren zur Herstellung von Chinolyl-3-dialkylphosphaten und deren Salzen
DE2166270C3 (de)	1975-10-09	Nicotinoylaminoäthansulfonyl-2amino-thiazol
CH495949A (de)	1970-09-15	Verfahren zur Herstellung von neuen basischen Äthern
DE2538095A1 (de)	1976-03-25	Neue organische verbindungen, ihre herstellung und verwendung
DE2651984C2 (de)	1983-01-27	Verfahren zur Herstellung von N,N-Dimethylpiperidiniumchlorid oder N,N-Dimethylmorpholiniumchlorid
DE2721265C2 (de)	1982-05-19	Verfahren zur Herstellung von Di- n-propylacetonitril
DE2519315C2 (de)	1986-10-30	Verfahren zur Herstellung von 3-Trichlormethyl-5-chlor-1,2,4-thiadiazol
DE2558508A1 (de)	1976-09-02	Verfahren zur racematspaltung von dl-pantolacton
DE2527157C2 (de)	1984-01-12	Verfahren zur Herstellung von 2-Formylchinoxalin-N&uarr;1&uarr;,N&uarr;4&uarr;-dioxyddimethylacetal
DE2331665A1 (de)	1974-01-17	Dialkylaminoalkylester von arylaliphatischen saeuren und ihre saeureadditionssalze und verfahren zu deren herstellung
DE3104785A1 (de)	1982-02-25	Basische ether der 4-hydroxy-benzophenone, die als (beta)-blocker wirksam sind, und verfahren zu ihrer herstellung
DE1593927A1 (de)	1970-12-10	Verfahren zur Herstellung von neuen basischen AEthern
DE2518516C3 (de)	1978-06-01	2-(3,45-Trimethoxybenzyl)-3,4-dimethylpyridin
DE2224240A1 (de)	1972-12-07	Verfahren zur Herstellung von 1- eckige Klammer auf p-(beta-Diäthylaminoäthoxy)-phenyl eckige Klammer zu -l^-diphenyl^-chloräthylen beziehungsweise therapeutisch brauchbaren Salzen desselben
DE2236005C3 (de)	1976-07-08	Dibenzo- eckige Klammer auf d,f eckige Klammer zu -dioxepin- eckige Klammer auf 1,3 eckige Klammer zu -derivate und deren pharmakologisch verträgliche Salze, sowie Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
DE1470197C (de)	1973-05-03	alpha.alpha Diphenyl alpha eckige Klammer auf 1 methylpyrrohdyl (3) eckige Klammer zu N,N dimethylace tamid und seine pharmakologisch ge eigneten Saureanlagerungssalze sowie Verfahren zur Herstellung dieser Ver bindungen
AT201584B (de)	1959-01-10	Verfahren zur Herstellung neuer Anilide und deren Salze
DE2042320C3 (de)	1980-02-07	Verfahren zur Herstellung von N,N'-Bis-(3-hydroxypropyl)-athylendiaimn-(U)