NO142101B - EXTENSION LIGHT WITH ADJUSTABLE DISC VALVE - Google Patents
EXTENSION LIGHT WITH ADJUSTABLE DISC VALVE Download PDFInfo
- Publication number
- NO142101B NO142101B NO762511A NO762511A NO142101B NO 142101 B NO142101 B NO 142101B NO 762511 A NO762511 A NO 762511A NO 762511 A NO762511 A NO 762511A NO 142101 B NO142101 B NO 142101B
- Authority
- NO
- Norway
- Prior art keywords
- carbinol
- pyridyl
- ether
- carbon atoms
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 27
- -1 2,3,5,6-tetramethyl-phenyl-(2-pyridyl)-carbinol Chemical compound 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000002170 ethers Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000000506 psychotropic effect Effects 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 229960002887 deanol Drugs 0.000 claims description 2
- 238000012546 transfer Methods 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- FPWGIABDOFXETH-UHFFFAOYSA-N 2-bromo-1,3-diethylbenzene Chemical compound CCC1=CC=CC(CC)=C1Br FPWGIABDOFXETH-UHFFFAOYSA-N 0.000 description 7
- 239000012458 free base Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- PDBXHPORMXSXKO-UHFFFAOYSA-N 8-benzyl-7-[2-[ethyl(2-hydroxyethyl)amino]ethyl]-1,3-dimethylpurine-2,6-dione;hydron;chloride Chemical class Cl.N=1C=2N(C)C(=O)N(C)C(=O)C=2N(CCN(CCO)CC)C=1CC1=CC=CC=C1 PDBXHPORMXSXKO-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical class NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 5
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 5
- 235000013922 glutamic acid Nutrition 0.000 description 5
- 239000004220 glutamic acid Substances 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 3
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000000739 antihistaminic agent Substances 0.000 description 3
- 210000005013 brain tissue Anatomy 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 230000004060 metabolic process Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- NOKBSQZILRQNJD-UHFFFAOYSA-N (2-propan-2-ylphenyl)-pyridin-2-ylmethanol Chemical compound CC(C)C1=CC=CC=C1C(O)C1=CC=CC=N1 NOKBSQZILRQNJD-UHFFFAOYSA-N 0.000 description 2
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000037354 amino acid metabolism Effects 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 230000001387 anti-histamine Effects 0.000 description 2
- 239000000043 antiallergic agent Substances 0.000 description 2
- 150000001499 aryl bromides Chemical class 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- LECYCYNAEJDSIL-UHFFFAOYSA-N 1-bromo-2-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC=C1Br LECYCYNAEJDSIL-UHFFFAOYSA-N 0.000 description 1
- RRTLQRYOJOSPEA-UHFFFAOYSA-N 2-bromo-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=C(Br)C(C)=C1 RRTLQRYOJOSPEA-UHFFFAOYSA-N 0.000 description 1
- QEOQKWIURDCGIJ-UHFFFAOYSA-N 2-bromo-1,3-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1Br QEOQKWIURDCGIJ-UHFFFAOYSA-N 0.000 description 1
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
- LQLJZSJKRYTKTP-UHFFFAOYSA-N 2-dimethylaminoethyl chloride hydrochloride Chemical compound Cl.CN(C)CCCl LQLJZSJKRYTKTP-UHFFFAOYSA-N 0.000 description 1
- SNEBKUGUQQWVOV-UHFFFAOYSA-N 3-bromo-1,2,4,5-tetraethylbenzene Chemical compound CCC1=CC(CC)=C(CC)C(Br)=C1CC SNEBKUGUQQWVOV-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 229960001076 chlorpromazine Drugs 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- AJECZOAMLZFBIN-UHFFFAOYSA-M magnesium;2h-pyridin-2-ide;bromide Chemical compound [Mg+2].[Br-].C1=CC=N[C-]=C1 AJECZOAMLZFBIN-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960004738 nicotinyl alcohol Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QVYRGXJJSLMXQH-UHFFFAOYSA-N orphenadrine Chemical compound C=1C=CC=C(C)C=1C(OCCN(C)C)C1=CC=CC=C1 QVYRGXJJSLMXQH-UHFFFAOYSA-N 0.000 description 1
- 229960003941 orphenadrine Drugs 0.000 description 1
- 230000036284 oxygen consumption Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- UYESUYBXKHPUDU-UHFFFAOYSA-N phenyl(pyridin-2-yl)methanol Chemical compound C=1C=CC=NC=1C(O)C1=CC=CC=C1 UYESUYBXKHPUDU-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Classifications
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F24—HEATING; RANGES; VENTILATING
- F24F—AIR-CONDITIONING; AIR-HUMIDIFICATION; VENTILATION; USE OF AIR CURRENTS FOR SCREENING
- F24F13/00—Details common to, or for air-conditioning, air-humidification, ventilation or use of air currents for screening
- F24F13/02—Ducting arrangements
- F24F13/06—Outlets for directing or distributing air into rooms or spaces, e.g. ceiling air diffuser
- F24F13/078—Outlets for directing or distributing air into rooms or spaces, e.g. ceiling air diffuser combined with lighting fixtures
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F24—HEATING; RANGES; VENTILATING
- F24F—AIR-CONDITIONING; AIR-HUMIDIFICATION; VENTILATION; USE OF AIR CURRENTS FOR SCREENING
- F24F13/00—Details common to, or for air-conditioning, air-humidification, ventilation or use of air currents for screening
- F24F13/08—Air-flow control members, e.g. louvres, grilles, flaps or guide plates
- F24F13/10—Air-flow control members, e.g. louvres, grilles, flaps or guide plates movable, e.g. dampers
- F24F13/16—Air-flow control members, e.g. louvres, grilles, flaps or guide plates movable, e.g. dampers built up of parallelly-movable plates
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Check Valves (AREA)
- Self-Closing Valves And Venting Or Aerating Valves (AREA)
- Temperature-Responsive Valves (AREA)
Abstract
Avtrekkslykt med stillbar tallerkenventil.Exhaust lamp with adjustable poppet valve.
Description
Fremgangsmåte til fremstilling av />' -dimethylaminoethylethere av alkylfenyl-(2-pyridyl)-carbinoler med psychotrop virkning. Process for the preparation of />'-dimethylaminoethylether of alkylphenyl-(2-pyridyl)-carbinols with psychotropic effect.
Foreliggende oppfinnelse angår en The present invention relates to a
fremgangsmåte til fremstilling av nye (3-dimethylaminoethylethere av alkylfenyl-(2-pyridyl)-carbinoler med psychotrop process for the preparation of new (3-dimethylaminoethylethers of alkylphenyl-(2-pyridyl)-carbinols with psychotropic
virkning og med den generelle formel: effect and with the general formula:
i hvilken R, betegner en alkylgruppe med in which R, denotes an alkyl group with
høyst 6 carbonatomer og symbolene fra og at most 6 carbon atoms and the symbols from and
med R2 til og med Rr, betegner hvert et with R2 through Rr, each represents one
hydrogenatom eller en alkylgruppe med hydrogen atom or an alkyl group with
høyst 4 carbonatomer, idet gruppene R,— at most 4 carbon atoms, the groups R,—
R-, tilsammen inneholder minst 3 carbonatomer. Oppfinnelsen omfatter også fremstilling av salter av sådanne forbindelser. R-, together contain at least 3 carbon atoms. The invention also encompasses the preparation of salts of such compounds.
Disse forbindelser tilhører klassen aryl-pyridylcarbinoletherne. Forskjellige repre-sentanter for denne klasse er kjent fra litteraturen. Således beskrives i U.S. patentskrift nr. 2 606 193 forbindelser som til-svarer den generelle formel: These compounds belong to the class of aryl pyridyl carbinol ethers. Various representatives of this class are known from the literature. Thus is described in the U.S. patent document no. 2 606 193 compounds corresponding to the general formula:
i hvilken Ar betegner en fenylgruppe som kan være substituert med alkylgrupper eller alkoxygrupper, n er et helt tall fra 1 til 4 og X blant annet kan være en mono- eller dialkylaminogruppe. I patentskriftets eksempel 1 nevnes som utgangsmateriale for fremstilling av ethere 2,4-dimethylfenyl-2-pyridylcarbinol. Disse ethere angis å være verdifulle antispasmodiske midler, anti-histaminmidler og antiallergiske midler. in which Ar denotes a phenyl group which may be substituted with alkyl groups or alkoxy groups, n is an integer from 1 to 4 and X may, among other things, be a mono- or dialkylamino group. In example 1 of the patent, 2,4-dimethylphenyl-2-pyridylcarbinol is mentioned as a starting material for the production of ethers. These ethers are reported to be valuable antispasmodic, antihistamine and antiallergic agents.
Engelsk patentskrift nr. 651 710 angår forbindelser med den generelle formel: English patent document no. 651 710 relates to compounds with the general formula:
s\ -r s\ -r
I II I / I H- C-0-CK.-CH..-N N I \ I II I / I H- C-0-CK.-CH..-N N I \
Ar Year
er kjent fra U.S. patentskrift nr. 2 606 195. 1 denne generelle formel er R et hydrogenatom, Ar en tolylrest, mens de fri valenser på nitrogenatomet kan betegne alkylgrupper med høyst 3 carbonatomer. I dette patentskrift angis at vedkommende forbindelser lar seg anvende til bekjempelse av og nedsettelse av fysiologiske virkninger av histamin og andre allergiske stoffer. is known from the U.S. patent document no. 2 606 195. In this general formula, R is a hydrogen atom, Ar a tolyl residue, while the free valences on the nitrogen atom can denote alkyl groups with a maximum of 3 carbon atoms. This patent document states that the compounds in question can be used to combat and reduce the physiological effects of histamine and other allergic substances.
Videre kan nevnes U.S. patentskrift nr. 2 662 891, 2 606 190 og 2 534 238 i hvilke mere eller mindre lignende forbindelser beskrives som antiallergiske midler. Furthermore, mention may be made of the U.S. patent no. 2 662 891, 2 606 190 and 2 534 238 in which more or less similar compounds are described as anti-allergic agents.
Det forholder seg slik at den i fenylkjernen ikke substituerte forbindelse av (3-dimethylaminoethyletheren av fenyl-(2-pyridyl)-carbinol har en sterk antihist-amin virkning. It is such that the unsubstituted compound of (3-dimethylaminoethylether of phenyl-(2-pyridyl)-carbinol in the phenyl nucleus has a strong antihistamine effect.
Der ble nu funnet det overraskende forhold at denne anthihistaminvirkning og til og med den spasmolytiske virkning prak-tisk talt forsvinner når alkylgrupper i fenylkjernen substitueres (hva der således står i motsetning til angivelsene i ovenfor-nevnte patentskrifter), mens andre terapeutiske virkninger i sterk grad kommer i forgrunnen. I særdeleshet har det vist seg at forbindelser fremstilt ved fremgangsmåten ifølge oppfinnelsen og som har en alkylgruppe med høyst 6 carbonatomer i fenylrestens ortho-stilling og eventuelt også inneholder ytterligere alkylgrupper med høyst 4 carbonatomer, slik at summen av carbonatomene i de i fenylkjernen substituerte alkylgrupper er minst 3, har en bestemt analgetisk virkning, forhøyer blod-trykket og/eller har en diuretisk virkning. Det er imidlertid meget viktig at disse forbindelser har en sterk innflytelse på metabolismen i hjernens vev, og at i særdeleshet amin osyrer-stof f vekselen i hjernevevet påvirkes av disse forbindelser. Ån-dedrettet hemmes, hva der fremgår av nedsettelsen av oxygenforbruket ved me-tabolisme i rotters hjerne, under aerobe betingelser, mens totalkonsentrasjonen av y-amino-smørsyrer (GABA) og/eller glutaminsyre øker. Da begge disse aminosyrer spiller en ytterst viktig rolle i sentralner-vesystemet, er en forhøyelse av deres kon-sentrasjon i hjernevevet av overordentlig stor betydning. Dette fremgår også av at andre farmasøytiske midler som har fått stor betydning i terapien, utøver en lignende innvirkning på aminosyrestoffveks-leren som forbindelser fremstilt ved fremgangsmåten ifølge oppfinnelsen. Som ek-semplér kan nevnes Orphenadrin ((3-di-methylaminoethyl-2-methyl-benzhydryl-ether) og Chlorpromazin (10-(3'-dimethyl-aminopropyl)-3-klorfenothiazin) som ifølge Nauta c.s. (The Lancet 1958, sider 591— 592) frembringer en økning på syv ganger av mengden av glutaminsyre og en økning på mere enn ti ganger av mengden av GABA i inkubasjonsmediet. Sammenhen-gen mellom innvirkningen på aminosyre-stoffvekselen og den psychotrope virkning av visse terapeutiske midler, er ennu ikke helt oppklart, men der synes ikke å være noen tvil om at der er en sammenheng. The surprising fact was now found that this antihistamine effect and even the spasmolytic effect practically disappear when alkyl groups in the phenyl nucleus are substituted (which is thus contrary to the statements in the above-mentioned patents), while other therapeutic effects to a large extent comes to the fore. In particular, it has been shown that compounds produced by the method according to the invention and which have an alkyl group with a maximum of 6 carbon atoms in the ortho-position of the phenyl residue and optionally also contain additional alkyl groups with a maximum of 4 carbon atoms, so that the sum of the carbon atoms in the alkyl groups substituted in the phenyl nucleus is at least 3, has a specific analgesic effect, increases blood pressure and/or has a diuretic effect. However, it is very important that these compounds have a strong influence on the metabolism in the brain tissue, and that in particular the amino acid metabolism in the brain tissue is affected by these compounds. Breathing is inhibited, as can be seen from the reduction in oxygen consumption during metabolism in rat brains, under aerobic conditions, while the total concentration of γ-aminobutyric acids (GABA) and/or glutamic acid increases. As both of these amino acids play an extremely important role in the central nervous system, an increase in their concentration in the brain tissue is extremely important. This is also evident from the fact that other pharmaceutical agents which have gained great importance in therapy exert a similar effect on the amino acid exchanger as compounds produced by the method according to the invention. Examples include Orphenadrine ((3-di-methylaminoethyl-2-methyl-benzhydryl-ether) and Chlorpromazine (10-(3'-dimethyl-aminopropyl)-3-chlorophenothiazine) which, according to Nauta et al. (The Lancet 1958, pages 591-592) produces a seven-fold increase in the amount of glutamic acid and a more than ten-fold increase in the amount of GABA in the incubation medium. The connection between the effect on amino acid metabolism and the psychotropic effect of certain therapeutic agents is still not completely clear, but there seems to be no doubt that there is a connection.
Den undersøkelsesmetode som ble anvendt for å prøve innvirkning av forbindelser fremstilt ved fremgangsmåten ifølge oppfinnelsen på metabolismen i rotters hjerne, og særlig på konsentrasjonen av GABA og glutaminsyre, er i det vesentlige den metode som er beskrevet av Ernsting (J. of Neurochem. 15, 121—127 (1960)). The research method that was used to test the effect of compounds produced by the method according to the invention on the metabolism in the brain of rats, and in particular on the concentration of GABA and glutamic acid, is essentially the method described by Ernsting (J. of Neurochem. 15, 121-127 (1960)).
I nedenstående tabell I ble mengdene av aminosyrer bestemt ved hjelp av spe-sielle kromatografiske metoder. Som inku-basjonsvæske ble valgt den puffer som også er beskrevet av Ernsting (på et annet sted enn i den ovenfor anførte litteratur). Som substrat ble anvendt D-glukose i en slutt-konsentrasjon på 0,02 mol. Sluttkonsentra-sjonen for forbindelser fremstilt ifølge oppfinnelsen, ble fastsatt til 0,002 mol. I nedenstående tabell er også kontrollverdier oppført. In Table I below, the amounts of amino acids were determined using special chromatographic methods. The buffer that was also described by Ernsting (in a different place than in the literature cited above) was chosen as the incubation liquid. D-glucose was used as substrate in a final concentration of 0.02 mol. The final concentration for compounds prepared according to the invention was set at 0.002 mol. In the table below, control values are also listed.
Av denne tabell fremgår at mediene ved anvendelse av forbindelser fremstilt ifølge oppfinnelsen inneholder mere GABA og glutaminsyre enn ved anvendelsen av de forskjellige monomethyl- og dimethyl-forbindelser. Både ved økning av antallet av alkylgrupper og ved å velge større alkylgrupper forbedres resultatene. I kontroll-forsøkene for medium og vev viser det seg at innholdet av GABA og glutaminsyre er omtrent lik de innhold av disse forbindelser som ble funnet umiddelbart etter obduk-sjonen. This table shows that the media when using compounds produced according to the invention contain more GABA and glutamic acid than when using the various monomethyl and dimethyl compounds. Both by increasing the number of alkyl groups and by choosing larger alkyl groups, the results are improved. In the control experiments for medium and tissue, it turns out that the content of GABA and glutamic acid is approximately equal to the content of these compounds that was found immediately after the autopsy.
Det karakteristiske hovedtrekk ved fremgangsmåten ifølge oppfinnelsen til fremstilling av ethere som definert i det foregående, er at man forethrer en carbinol med den generelle formel: The main characteristic feature of the method according to the invention for the production of ethers as defined above is that a carbinol with the general formula is etherified:
eller et funksjonelt derivat av en sådan carbinol, med (3-dimethylaminoethanol eller et funksjonelt derivat av sistnevnte forbindelse og eventuelt overfører de herved erholdte ethere i sine salter. or a functional derivative of such a carbinol, with (3-dimethylaminoethanol or a functional derivative of the latter compound and optionally transfer the ethers obtained thereby in their salts.
I en foretrukken utførelsesform for fremgangsmåten ifølge oppfinnelsen omsetter man carbinolen med den ovenstå-ende formel med |3-dimethylaminoethyl-klorid. In a preferred embodiment of the method according to the invention, the carbinol with the above formula is reacted with β-dimethylaminoethyl chloride.
I litteraturen beskrives forskjellige metoder til fremstilling av disse carbinoler. Der kan f. eks. nevnes reduksjon av de tilsvarende ketoner ifølge Tschitschibabin (Ber. 37, 1371 (1904)), omsetning av et arylaldehyd med 2-pyridylmagnesiumbro-mid ifølge Overhoff og Proost, (Ree. Trav. chim. 57, 179—189 (1938)) og omsetning av pyridin med et aromatisk aldehyd under innvirkning av en katalysator som beskrevet i Emmert og Assendorf (Ber. 72 B, 1188, (1939)). The literature describes different methods for producing these carbinols. There can e.g. mention is made of the reduction of the corresponding ketones according to Tschitschibabin (Ber. 37, 1371 (1904)), reaction of an aryl aldehyde with 2-pyridylmagnesium bromide according to Overhoff and Proost, (Ree. Trav. chim. 57, 179-189 (1938)) and reacting pyridine with an aromatic aldehyde under the action of a catalyst as described in Emmert and Assendorf (Ber. 72 B, 1188, (1939)).
Fortrinsvis anvender man følgende The following is preferably used
metode: method:
I en 2-liters trehalset kolbe med dråpetrakt, tilbakeløpskjøler og røreverk anbringes 0,55 gramatomer magnesiumspon. Derpå tilsetter man 0,05 mol arylbromid oppløst i 30 ml vannfri ether. Etterat reaksjonen er satt igang, tildryppes 0,45 mol arylbromid i 150 ml vannfri ether. 0.55 gram atoms of magnesium shavings are placed in a 2-liter three-necked flask with dropping funnel, reflux condenser and stirrer. 0.05 mol of aryl bromide dissolved in 30 ml of anhydrous ether is then added. After the reaction has been started, 0.45 mol of aryl bromide is added dropwise in 150 ml of anhydrous ether.
Reaksjonsblandingen holdes på en sådan temperatur at etheren stadig koker sterkt. Når reaksjonen er avsluttet, avkjø-les blandingen til 0° C. Derpå tilsettes i løpet av 1 time 0,5 mol nylig destillert 2-pyridinaldehyd, og reaksjonsblandingen omrøres kraftig. Etterat reaksjonen er avsluttet, koker man i ytterligere ca. 1 time The reaction mixture is kept at such a temperature that the ether constantly boils strongly. When the reaction is finished, the mixture is cooled to 0° C. 0.5 mol of freshly distilled 2-pyridinealdehyde is then added over the course of 1 hour, and the reaction mixture is stirred vigorously. After the reaction has ended, it is boiled for a further approx. 1 hour
under tilbakeløpskjøling. Derpå avkjøles during reflux cooling. Then cool
reaksjonsblandingen, og reaksjonsproduk-tet spaltes ved å helle blandingen i 200 ml vann som inneholder 60 g ammoniumklorid. Etherskiktet skilles fra det vandige skikt, og sistnevnte skikt ekstraheres to ganger med ether. Etherekstraktene blan-des og ekstraheres tre ganger med 50 ml 10 pst.'s saltsyre. Saltsyreekstraktet nøy-traliseres med natriumcarbonat og ekstraheres tre ganger med ether. Etherekstrak-tet vaskes med vann og befries derpå for vann med vannfritt kaliumcarbonat. Det inndampes derpå og man bringer carbinolen til å krystallisere. Eventuelt kan den renses ytterligere ved omkrystallisasj on fra en blanding av ether og petrolether. the reaction mixture, and the reaction product is split by pouring the mixture into 200 ml of water containing 60 g of ammonium chloride. The ether layer is separated from the aqueous layer, and the latter layer is extracted twice with ether. The ether extracts are mixed and extracted three times with 50 ml of 10% hydrochloric acid. The hydrochloric acid extract is neutralized with sodium carbonate and extracted three times with ether. The ether extract is washed with water and then freed from water with anhydrous potassium carbonate. It is then evaporated and the carbinol is brought to crystallize. If necessary, it can be further purified by recrystallization from a mixture of ether and petroleum ether.
I påfølgende tabell II er oppført data angående de på denne måte erholdte alkylfenyl-(2-pyridyl)-carbinoler som altså tjener som mellomprodukter. In subsequent Table II, data are listed regarding the alkylphenyl-(2-pyridyl)-carbinols obtained in this way, which thus serve as intermediate products.
For terapeutisk anvendelse kan forbindelser fremstilt ved fremgangsmåten ifølge oppfinnelsen på vanlige måter opp-arbeides til preparater av normal art. For therapeutic use, compounds produced by the method according to the invention can be prepared in normal ways into preparations of a normal nature.
I det nedenstående beskrives som ek-sempler fremstilling av et utvalg av slutt-produktene ved fremgangsmåten i henhold til oppfinnelsen. In the following, the production of a selection of the end products by the method according to the invention is described as examples.
Eksempel 1. Example 1.
a. Magnesiumspon i en mengde av 3,4 gram anbringes i en 2-liters trehalset flaske utstyrt med en dråpetrakt, en tilbakeløps-kondensator og en rører. Derpå tilsettes en oppløsning av 10,6 g 2,6-diethylbrom-benzen i 30 ml vannfri ether. Etter at reaksjonen er startet ved forsiktig oppvarm - ning av flasken, tilsettes 95,9 g 2,6-diethyl-brombenzen i 150 ml vannfri ether dråpe-vis, under omrøring, med en slik hastig-het at etheren fortsetter å koke under til-bakeløpskjøling. Etter at reaksjonen er avsluttet, fortsettes oppvarmningen under tilbakeløpskjøling i ytterligere 30—60 minutter på et vannbad. Vannbadet erstattes derpå med et isbad, hvorved reaksjonsblandingen kjøles til 0° C. Ved denne temperatur tilsettes der i løpet av 1 time under kraftig omrøring 53,5 g 2-pyridinalde-hyd i 200 ml vannfri ether. Herved dannes en gulbrun utfelning. Etter endt tilsetning oppvarmes reaksjonsblandingen under til-bakeløpskjøling i 30 minutter på vannbad, kjøles til 0° C og skilles med en iskold opp-løsning av 60 g ammoniumklorid i 200 ml vann. Etherskiktet separeres fra det vandige skikt, og det sistnevnte ekstraheres to ganger med ether. De sammenslåtte etherskikt vaskes derpå to ganger med vann, hvoretter de ekstraheres tre ganger med 50 ml 10 pst. saltsyre. Det rødlig-brune ekstrakt nøytraliseres med natriumbicar-bonat og ekstraheres derpå tre ganger med ether. Etter å være vasket med vann og tørket med vannfritt kaliumkarbonat inndampes ether oppløsningen, hvorved 2,6-diethylfenyl- (2-pyridyl) -carbinolen utkry-stalliserer. Smeltepunktet for den frie base er 42° C. Utbyttet: 67 pst. a. Magnesium shavings in an amount of 3.4 grams are placed in a 2-liter three-necked bottle equipped with a dropping funnel, a reflux condenser, and a stirrer. A solution of 10.6 g of 2,6-diethylbromobenzene in 30 ml of anhydrous ether is then added. After the reaction has started by carefully heating the bottle, 95.9 g of 2,6-diethyl-bromobenzene in 150 ml of anhydrous ether is added dropwise, while stirring, at such a rate that the ether continues to boil until -backflow cooling. After the reaction has ended, the heating is continued under reflux for a further 30-60 minutes in a water bath. The water bath is then replaced with an ice bath, whereby the reaction mixture is cooled to 0° C. At this temperature, 53.5 g of 2-pyridinealdehyde in 200 ml of anhydrous ether are added over the course of 1 hour with vigorous stirring. This forms a yellow-brown precipitate. After the addition is complete, the reaction mixture is heated under reflux for 30 minutes in a water bath, cooled to 0° C. and separated with an ice-cold solution of 60 g of ammonium chloride in 200 ml of water. The ether layer is separated from the aqueous layer, and the latter is extracted twice with ether. The combined ether layers are then washed twice with water, after which they are extracted three times with 50 ml of 10% hydrochloric acid. The reddish-brown extract is neutralized with sodium bicarbonate and then extracted three times with ether. After being washed with water and dried with anhydrous potassium carbonate, the ether solution is evaporated, whereby the 2,6-diethylphenyl-(2-pyridyl)-carbinol crystallizes out. The melting point of the free base is 42° C. Yield: 67 per cent.
b. I en trehalset flaske utstyrt med en rører, tilbakeløpskondensator og dråpetrakt oppløses 25,9 g 2,6-diethylfenyl-(2-pyridyl)-carbinol i 200 ml vannfritt toluen, hvoretter 15 ml toluen avdestilleres. Oppløsningen kjøles derpå til 0° C på et is-salt-bad, og 5,7 g natriumamid tilsettes. Blandingen oppvarmes deretter til 100° C under rolig omrøring. Herunder skjer en kraftig utvikling av ammoniakk. Oppløs- b. In a three-necked flask equipped with a stirrer, reflux condenser and dropping funnel, dissolve 25.9 g of 2,6-diethylphenyl-(2-pyridyl)-carbinol in 200 ml of anhydrous toluene, after which 15 ml of toluene is distilled off. The solution is then cooled to 0° C. in an ice-salt bath, and 5.7 g of sodium amide are added. The mixture is then heated to 100° C with gentle stirring. Below this, a strong development of ammonia takes place. dissolve-
ningen antar en dyp blå til rødlig-brun farve .Oppvarmningen fortsettes i ca. 4 timer inntil utviklingen av ammoniakk er opphørt. Ytterligere 5,7 g natriumamid tilsettes og derpå, ved 0° C, 20,3 g dimethyl-aminoethylklorid-hydroklorid. Det utvik-les ammoniakk. Temperaturen økes til 100° C under omrøring i ca. 1 time og reaksjonsblandingen holdes ved denne temperatur i 14—16 timer. Den kjøles deretter til romtemperatur, og 100 ml vann tilsettes. Toluenskiktet fraskilles og vaskes en gang med vann, tørkes med vannfritt kaliumkarbonat og destilleres. Etter at innholdet av (3-dimethylaminoethyl-2,6-diethylfenyl-(2-pyridyl)-carbinolether i destillatet er bestemt ved titrering, oppløses denne i vannfritt ethylacetat, og den beregnede mengde av alkoholisk saltsyreoppløsning som er nødvendig for å danne mono-HCl-saltet, tilsettes. Smeltepunktet for mono-HCl-saltet av (3-dimethylaminoethyl-2,6-diethylf enyl-(2-pyridyl)-carbinolether er 151° C. Kokepunktet for den frie base: 172—174° C/2 mm. Utbytte: 30 pst. the mixture takes on a deep blue to reddish-brown colour. The heating is continued for approx. 4 hours until the development of ammonia has ceased. A further 5.7 g of sodium amide are added and then, at 0° C, 20.3 g of dimethylaminoethyl chloride hydrochloride. Ammonia is evolved. The temperature is increased to 100° C while stirring for approx. 1 hour and the reaction mixture is kept at this temperature for 14-16 hours. It is then cooled to room temperature, and 100 ml of water is added. The toluene layer is separated and washed once with water, dried with anhydrous potassium carbonate and distilled. After the content of (3-dimethylaminoethyl-2,6-diethylphenyl-(2-pyridyl)-carbinol ether in the distillate has been determined by titration, this is dissolved in anhydrous ethyl acetate, and the calculated amount of alcoholic hydrochloric acid solution necessary to form mono- The HCl salt is added. The melting point of the mono-HCl salt of (3-dimethylaminoethyl-2,6-diethylphenyl-(2-pyridyl)-carbinol ether is 151° C. The boiling point of the free base: 172-174° C/ 2 mm Yield: 30 percent
Eksempel 2. Example 2.
Samme fremgangsmåte benyttes som den beskrevet i eksempel 1 a, men en ekvivalent mengde av 2-isopropylbrombenzen anvendes i stedet for 2,6-diethylbrombenze-net. Det erholdes 2-isopropylfenyl-(2-pyridyl)-carbinol i 62 pst. utbytte. Den frie base smelter ved 77° C. The same method is used as that described in example 1 a, but an equivalent amount of 2-isopropylbromobenzene is used instead of 2,6-diethylbromobenzene. 2-isopropylphenyl-(2-pyridyl)carbinol is obtained in 62% yield. The free base melts at 77°C.
Ved samme fremgangsmåte som den beskrevet i eksempel 1 b, men hvor der imidlertid anvendes en tilsvarende mengde av 2-isopropylf enyl- (2-pyridyl) -carbinol i stedet for 2,6-diethylfenyl-(2-pyridyl)-carbinolen, erholdes mono-HCl-saltet av p-dimethylaminoethyl-2-isopropyl-fenyl-(2-pyridyl)-carbinolether i 30 pst. utbytte. Smeltepunkt 173—174° C. By the same method as that described in example 1 b, but where, however, a corresponding amount of 2-isopropylphenyl-(2-pyridyl)-carbinol is used instead of 2,6-diethylphenyl-(2-pyridyl)-carbinol, is obtained the mono-HCl salt of p-dimethylaminoethyl-2-isopropyl-phenyl-(2-pyridyl)-carbinol ether in 30% yield. Melting point 173-174° C.
Eksempel 3. Example 3.
Samme fremgangsmåte benyttes som den beskrevet i eksempel 1 a, men en ekvivalent mengde av 2-tert.butylbrombenzen anvendes i stedet for 2,6-diethylbromben-zenet. Det erholdes 2-tert.butylfenyl-(2-pyridyl)-carbinol i 51 pst. utbytte. Den frie base smelter ved 111° C. The same method is used as that described in example 1 a, but an equivalent amount of 2-tert.butylbromobenzene is used instead of the 2,6-diethylbromobenzene. 2-tert.butylphenyl-(2-pyridyl)carbinol is obtained in 51% yield. The free base melts at 111°C.
Ved samme fremgangsmåte som den beskrevet i eksempel 1 b, men hvor der imidlertid anvendes en tilsvarende mengde 2-tert.butylf enyl- (2-pyridyl) -carbinol i stedet for 2,6-diethylfenyl- (2-pyridyl) - carbinolen, erholdes mono-HCl-saltet av p-dimethyl-aminoethyl-2-tert.butylfenyl-(2-pyridyl)-carbinolether i 41 pst. utbytte. Smeltepunkt: 186—187° C. By the same method as that described in example 1 b, but where, however, a corresponding amount of 2-tert.butylphenyl-(2-pyridyl)-carbinol is used instead of 2,6-diethylphenyl-(2-pyridyl)-carbinol, the mono-HCl salt of p-dimethyl-aminoethyl-2-tert.butylphenyl-(2-pyridyl)-carbinol ether is obtained in 41% yield. Melting point: 186-187° C.
Eksempel 4. Example 4.
Samme fremgangsmåte benyttes som den beskrevet i eksempel 1 a, men en ekvivalent mengde av 2,6-diisopropylbromben-zen anvendes i stedet for 2,6-diethylbrom-benzenet. Det erholdes 2,6-diisopropylfe-nyl-(2-pyridyl)-carbinol i 47 pst. utbytte. Den frie base smelter ved 102° C. The same method is used as that described in example 1 a, but an equivalent amount of 2,6-diisopropylbromobenzene is used instead of the 2,6-diethylbromobenzene. 2,6-diisopropylphenyl-(2-pyridyl)carbinol is obtained in 47% yield. The free base melts at 102°C.
Ved samme fremgangsmåte som den beskrevet i eksempel 1 b, men hvor der imidlertid anvendes en tilsvarende mengde 2,6-diisopropylf enyl- (2-pyridyl) -carbinol i stedet for 2,6-diethylf enyl-(2-pyridyl) - carbinolen, erholdes mono-HCl-saltet av p-dimethylaminoethyl-2,6-diisopropylfe-nyl-(2-pyridyl)-carbinolether i 46 pst. utbytte. Smeltepunkt: 156—157° C. By the same method as that described in example 1 b, but where, however, a corresponding amount of 2,6-diisopropylphenyl-(2-pyridyl)-carbinol is used instead of 2,6-diethylphenyl-(2-pyridyl)-carbinol , the mono-HCl salt of p-dimethylaminoethyl-2,6-diisopropylphenyl-(2-pyridyl)-carbinol ether is obtained in 46% yield. Melting point: 156-157° C.
Eksempel 5. Example 5.
Samme fremgangsmåte benyttes som den beskrevet i eksempel 1 a, men en ekvivalent mengde av 2,4,6-trimethylbromben-zen anvendes i stedet for 2,6-diethylbrom-benzenet. Det erholdes 2,4,6-trimethylfenyl-(2-pyridyl)-carbinol i 40 pst. utbytte. Den frie base smelter ved 65° C, hydrokloridet ved 188—190° C. The same method is used as that described in example 1 a, but an equivalent amount of 2,4,6-trimethylbromobenzene is used instead of the 2,6-diethylbromobenzene. 2,4,6-trimethylphenyl-(2-pyridyl)carbinol is obtained in 40% yield. The free base melts at 65° C, the hydrochloride at 188-190° C.
Ved samme fremgangsmåte som den beskrevet i eksempel 1 b, men hvor der imidlertid anvendes en ekvivalent mengde 2,4,6-trimethylfenyl- (2-pyridyl) -carbinol i stedet for 2,6-diethylf enyl-(2-pyridyl)-carbinolen, erholdes mono-HCl-saltet av p-dimethylaminoethyl-2,4,6-trimethylfenyl-(2-pyridyl)-carbinolether i 42 pst. utbytte. Smeltepunkt 173—174° C. By the same method as that described in example 1 b, but where, however, an equivalent amount of 2,4,6-trimethylphenyl-(2-pyridyl)-carbinol is used instead of 2,6-diethylphenyl-(2-pyridyl)- the carbinol, the mono-HCl salt of p-dimethylaminoethyl-2,4,6-trimethylphenyl-(2-pyridyl)-carbinol ether is obtained in 42% yield. Melting point 173-174° C.
Eksempel 6. Example 6.
Samme fremgangsmåte benyttes som den beskrevet i eksempel 1 a, men en ekvivalent mengde av 2,3,5,6-tetraethylbrom-benzen anvendes i stedet for 2,6-diethyl-brombenzenet. Det erholdes 2,3,5,6-tetra-methylfenyl-(2-pyridyl)-carbinol i 20 pst. utbytte. Den frie base smelter ved 104° C, hydrokloridet ved 187—188° C. The same method is used as that described in example 1 a, but an equivalent amount of 2,3,5,6-tetraethylbromobenzene is used instead of the 2,6-diethylbromobenzene. 2,3,5,6-tetramethylphenyl-(2-pyridyl)carbinol is obtained in 20% yield. The free base melts at 104° C, the hydrochloride at 187-188° C.
Ved samme fremgangsmåte som den beskrevet i eksempel 1 b, men hvor der imidlertid anvendes en tilsvarende mengde av 2,3,5,6-tetramethylf enyl- (2-pyridyl) - carbinol i stedet for 2,6-diethylfenyl-(2-pyridyl)-carbinolen, erholdes mono-HCl-saltet av p-dimethylaminoethyl-2,3,5,6-tetramethylfenyl- (pyridyl) -carbinolether i 48 pst. utbytte. Smeltepunkt 197° C. By the same method as that described in example 1 b, but where, however, a corresponding amount of 2,3,5,6-tetramethylphenyl-(2-pyridyl)-carbinol is used instead of 2,6-diethylphenyl-(2- pyridyl)-carbinol, the mono-HCl salt of p-dimethylaminoethyl-2,3,5,6-tetramethylphenyl-(pyridyl)-carbinol ether is obtained in 48% yield. Melting point 197° C.
Claims (4)
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DE7523491U DE7523491U (en) | 1975-07-23 | 1975-07-23 | EXHAUST LUMINAIRE WITH ADJUSTABLE DISC VALVE |
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NO142101C (en) | 1980-06-25 |
SE430101B (en) | 1983-10-17 |
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