NO122614B - - Google Patents
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- NO122614B NO122614B NO2180/70A NO218070A NO122614B NO 122614 B NO122614 B NO 122614B NO 2180/70 A NO2180/70 A NO 2180/70A NO 218070 A NO218070 A NO 218070A NO 122614 B NO122614 B NO 122614B
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- Prior art keywords
- phenthiazine
- carboxylate
- formula
- heated
- bis
- Prior art date
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- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical class C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000003776 cleavage reaction Methods 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 230000007017 scission Effects 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000009835 boiling Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- NIXYMFJMHHIQAC-UHFFFAOYSA-N 1,1-bis(dimethylamino)propan-2-ol Chemical compound CC(O)C(N(C)C)N(C)C NIXYMFJMHHIQAC-UHFFFAOYSA-N 0.000 description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000003285 pharmacodynamic effect Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000002048 spasmolytic effect Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 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
- 239000003085 diluting agent Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000002005 ganglioplegic effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 description 1
Classifications
-
- E—FIXED CONSTRUCTIONS
- E05—LOCKS; KEYS; WINDOW OR DOOR FITTINGS; SAFES
- E05D—HINGES OR SUSPENSION DEVICES FOR DOORS, WINDOWS OR WINGS
- E05D15/00—Suspension arrangements for wings
- E05D15/40—Suspension arrangements for wings supported on arms movable in vertical planes
- E05D15/44—Suspension arrangements for wings supported on arms movable in vertical planes with pivoted arms and vertically-sliding guides
-
- E—FIXED CONSTRUCTIONS
- E05—LOCKS; KEYS; WINDOW OR DOOR FITTINGS; SAFES
- E05Y—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES E05D AND E05F, RELATING TO CONSTRUCTION ELEMENTS, ELECTRIC CONTROL, POWER SUPPLY, POWER SIGNAL OR TRANSMISSION, USER INTERFACES, MOUNTING OR COUPLING, DETAILS, ACCESSORIES, AUXILIARY OPERATIONS NOT OTHERWISE PROVIDED FOR, APPLICATION THEREOF
- E05Y2800/00—Details, accessories and auxiliary operations not otherwise provided for
- E05Y2800/74—Specific positions
- E05Y2800/742—Specific positions abnormal
- E05Y2800/744—Specific positions abnormal cleaning or service
-
- E—FIXED CONSTRUCTIONS
- E05—LOCKS; KEYS; WINDOW OR DOOR FITTINGS; SAFES
- E05Y—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES E05D AND E05F, RELATING TO CONSTRUCTION ELEMENTS, ELECTRIC CONTROL, POWER SUPPLY, POWER SIGNAL OR TRANSMISSION, USER INTERFACES, MOUNTING OR COUPLING, DETAILS, ACCESSORIES, AUXILIARY OPERATIONS NOT OTHERWISE PROVIDED FOR, APPLICATION THEREOF
- E05Y2900/00—Application of doors, windows, wings or fittings thereof
- E05Y2900/10—Application of doors, windows, wings or fittings thereof for buildings or parts thereof
- E05Y2900/13—Type of wing
- E05Y2900/148—Windows
Landscapes
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Wing Frames And Configurations (AREA)
- Window Of Vehicle (AREA)
- Hinges (AREA)
Description
Fremgangsmåte for fremstilling av terapeutisk aktive fentiazinderivater. Process for the preparation of therapeutically active phenthiazine derivatives.
Nærværende oppfinnelse angår en fremgangsmåte for fremstilling av visse terapeutisk aktive fentiazin-derivater. The present invention relates to a process for the production of certain therapeutically active phenthiazine derivatives.
I patent nr. 90.611 er der beskrevet It is described in patent no. 90,611
fentiazinderivater med den generelle formel: Phenothiazine derivatives of the general formula:
og deres salter og deres kvaternære am-moniumderivater i hvilken formel X betyr et hydrogen- eller halogenatom eller and their salts and their quaternary ammonium derivatives in which formula X represents a hydrogen or halogen atom or
en lavere alkyl-, lavere alkoksy-, eller lavere acyl-gruppe, fortrinnsvis i 3-stilling i a lower alkyl, lower alkoxy or lower acyl group, preferably in the 3-position i
fentiazinkjernen (Beilstein nummerering), the phenothiazine core (Beilstein numbering),
A betyr en treverdig alifatisk kjede inneholdende tre kullstoffatomer av hvilke A means a trivalent aliphatic chain containing three carbon atoms of which
hvert er bundet til et forskjellig nitrogen-atom og gruppene R er metyl- eller etyl-grupper, og fremgangsmåter for deres each is attached to a different nitrogen atom and the groups R are methyl or ethyl groups, and methods for their
fremstilling. Disse subsituerte fentiazinderivater har spesielt verdifulle farmakody-namiske egenskaper (ganglioplegiske, lo-kalanestetiske og spesielt spasmolytiske) manufacture. These substituted phenthiazine derivatives have particularly valuable pharmacodynamic properties (ganglioplegic, lo-calanesthetic and especially spasmolytic)
av hvilken grunn de kan brukes i medi-sinen. Av spesiell betydning er forbindel-sene 10-[2:3-bis(dimetylamino)-l-propyl] - for which reason they can be used in medicine. Of particular importance are the compounds 10-[2:3-bis(dimethylamino)-1-propyl] -
fentiazin, 3-metyl-10-[2:3-bis(dimetylamino)-l-propyl]fentiazin og l-klor-10-[2:3-bis (dimetylamino) -1 -propyl ] fentiazin og phenthiazine, 3-methyl-10-[2:3-bis(dimethylamino)-1-propyl]phenthiazine and l-chloro-10-[2:3-bis(dimethylamino)-1-propyl] phenthiazine and
deres salter og kvaternære ammonium-derivater, og isomere blandinger inneholdende disse forbindelser, og den mest betyd-ningsfulle forbindelse er 10-[2:2-bis(dimetylamino)-l-propyl]fentiazin som har en ytterst sterk spasmolytisk virkning. their salts and quaternary ammonium derivatives, and isomeric mixtures containing these compounds, and the most significant compound is 10-[2:2-bis(dimethylamino)-1-propyl]phenthiazine, which has an extremely strong spasmolytic effect.
Uttrykket «lavere» når brukt i denne beskrivelse og etterfølgende påstander an-gir at omhandlede grupper inneholder ikke mere enn fire kullstoffatomer. The term "lower" when used in this description and subsequent claims indicates that the groups in question contain no more than four carbon atoms.
Det er hensikten med nærværende oppfinnelse å fremskaffe en ny fremgangsmåte for fremstillingen av foran nevnte fentiazin forbindelser. It is the purpose of the present invention to provide a new method for the production of the above-mentioned phenthiazine compounds.
Ifølge nærværende oppfinnelse, består en fremgangsmåte for fremstilling av foran nevnte fentiazinderivater i spaltning av et fentiazin-10-karboksylat av en diaminoalkohol med den generelle formel: According to the present invention, a method for the production of the above-mentioned phenthiazine derivatives consists in the cleavage of a phenthiazine-10-carboxylate of a diamino alcohol with the general formula:
eller sure addisjonssalter av dette (X, A og R er som foran definert) ved opphet-ing til en temperatur over 100° C, og for-trinsvis mellom 150° C og 200° C. Det er ingen fordel å arbeide ved høyere tempe- or acid addition salts thereof (X, A and R are as defined above) when heated to a temperature above 100° C, and preferably between 150° C and 200° C. There is no advantage to working at higher temperatures -
raturer, som eventuelt kan forårsake mis- for dekarboksylering som for eksempel ki-farging av reaksjonsproduktene. nolin eller svake baser. rations, which may possibly cause improper decarboxylation such as ki-staining of the reaction products. noline or weak bases.
Reaksjonen kan utføres med fentiazin- Under spaltningen av fentiazin-10-10-karboksylatet alene, dvs. uten et fortyn- karboksylatet etter formel II, finner en ningsmiddel, eller i et inert medium som isomerisasjon sted og der oppnås en blan-flytende parafin, difenyl eller difenylok- ding av de to isomerer: The reaction can be carried out with phenthiazine During the cleavage of the phenthiazine 10-10-carboxylate alone, i.e. without a dilute carboxylate according to formula II, a ning agent, or in an inert medium as isomerization takes place and a mixed liquid paraffin is obtained, diphenyl or diphenyl coupling of the two isomers:
syd eller i de klassiske fortynningsmidler syd or in the classic diluents
I det tilfelle hvor R er lik OHa over-veier isomeren (a). Separering av isome-rene kan utføres ved for eksempel frak-sjonert krystallisasjon av saltene, som di-hydrokloridene, fra et egnet oppløsnings-middel, som alkohol. Det er imidlertid ikke av vesentlig betydning å utføre separasjo-nen da de to isomerer har meget like far-makodynamiske egenskaper. In the case where R is equal to OHa, the isomer (a) predominates. Separation of the isomers can be carried out by, for example, fractional crystallization of the salts, such as the dihydrochlorides, from a suitable solvent, such as alcohol. However, it is not of significant importance to carry out the separation as the two isomers have very similar pharmacodynamic properties.
Utgangsmaterialene etter formel II kan oppnås ved kjente metoder. For eksempel kan de fremstilles ved innvirknin-gen av et halogenid (eller en ester) av en fentiazin-10-karboksylsyre på den eg-nete diaminoalkohol, ved innvirkning av en halogenalkyl-fentiazin-10-karboksylat på et sekundært amin, eller ved innvirkning av et egnet fentiazin på et klorkarbonat av en diaminoalkohol. The starting materials according to formula II can be obtained by known methods. For example, they can be prepared by the action of a halide (or an ester) of a phenthiazine-10-carboxylic acid on the appropriate diamino alcohol, by the action of a haloalkyl-phenthiazine-10-carboxylate on a secondary amine, or by the action of a suitable phenthiazine on a chlorocarbonate of a diamino alcohol.
En spesielt fordelaktig metode for ut-førelse av fremgangsmåten etter oppfinnelsen som ikke krever isolering i ren til-stand av utgangsmaterialene etter formel II, består i oppvarming av et fentiazin-10-karboksylat med formelen: (hvor X er som foran definert og Z betyr residuet av en flyktig alkohol) med en diaminoalkohol med formelen: A particularly advantageous method for carrying out the method according to the invention which does not require isolation in a pure state of the starting materials according to formula II, consists in heating a phenthiazine-10-carboxylate with the formula: (where X is as defined above and Z means the residue of a volatile alcohol) with a diamino alcohol of the formula:
(hvor A og R er som foran definert). Reaksjonen foregår da i to trinn som kan finne sted samtidig og som består i elimineringen av alkohol for å gi et karboksylat av formel II, og elimineringen av kulldioksyd fra karboksylatet for å gi det ønskede fentiazin-derivat med formel I. (where A and R are as defined above). The reaction then takes place in two steps which can take place simultaneously and which consist in the elimination of alcohol to give a carboxylate of formula II, and the elimination of carbon dioxide from the carboxylate to give the desired phenthiazine derivative of formula I.
Oppfinnelsen illustreres av de følgende eksempler. The invention is illustrated by the following examples.
Eksempel 1. Example 1.
l:3-bis(dimetylamino) -propyl fentiazin-10-karboksylat (6 g.), smeltepunkt 94-95° C, oppvarmes i 30 min. fra 160 til 230°C og destilleres derpå i vakuum. Der oppnås en blekgul olje (5 g.), kokepunkt 176-177°C /0.12 mm H., bestående hovedsakelig av 10- [2:3-bis (dimetylamino) -1 -propyl ] fentiazin, hvis nøytrale fumarat smelter ved 168-169° C. 1:3-bis(dimethylamino)-propyl phenthiazine-10-carboxylate (6 g.), melting point 94-95° C., heated for 30 min. from 160 to 230°C and then distilled in vacuum. There is obtained a pale yellow oil (5 g.), boiling point 176-177°C /0.12 mm H., consisting mainly of 10-[2:3-bis(dimethylamino)-1-propyl] phenthiazine, whose neutral fumarate melts at 168 -169°C.
Begynnelsesesteren kan fremstilles ved innvirkning av fentiazin-10-karbonylklorid på l:3-bis(dimetylamino)propan-2-ol. Dens monometjodid smelter ved 168° C og dets dipikrat ved 145° C (spaltning). The starting ester can be prepared by the action of phenthiazine-10-carbonyl chloride on 1:3-bis(dimethylamino)propan-2-ol. Its monomethiodide melts at 168° C and its dipyrate at 145° C (decomposition).
Eksempel 2. Example 2.
1:3-bis(dietylamino)-2-propyl fentiazin-10-karboksylat (20 g.) behandles som i eksempel 1. Der oppnås til slutt en blekgul olje (7.4 g.), kokepunkt 200-202° C/0.17 mm Hg, fra hvilken der separeres ved krystallisasjon fra vandig isopropanol 10-[2:3-bis(dietylamino)-l-propyl]fentiazin (5.8 g) smeltepunkt 58° C. Det tilsvarende dipikrat smelter ved 162-163° C. 1:3-bis(diethylamino)-2-propyl phenthiazine-10-carboxylate (20 g.) is treated as in example 1. A pale yellow oil (7.4 g.) is finally obtained, boiling point 200-202° C/0.17 mm Hg, from which is separated by crystallization from aqueous isopropanol 10-[2:3-bis(diethylamino)-l-propyl]phenthiazine (5.8 g) melting point 58° C. The corresponding dipicrate melts at 162-163° C.
Begynnelsesesteren kan fremstilles ved kondensasjon av l:3-bis(dietylamino)pro-pan-2-ol med fentiazin-10-karbonylklorid i pyridin. The starting ester can be prepared by condensation of 1:3-bis(diethylamino)propan-2-ol with phenthiazine-10-carbonyl chloride in pyridine.
Eksempel 3. Example 3.
1:3-bis(dimetylamino)-2-propyl 3-ace-tyl-fentiazin-10-karboksylat (14.1 g), smeltepunkt Kofler 128° C, oppløst i o-diklor-bensol (25 cc) oppvarmes i en time under kokning inntil utviklingen av COi opphø-rer. De oppnådde oppløsning fortynnes med eter (50 cc), og de basiske produkter ek-straheres med fortynnet saltsyre. Det or-ganiske lag helles fra den sure oppløsning, vaskes med eter og gjøres derpå alkalisk med fortynnet natriumhydroksyd. Etter ekstrasjon med eter, tørres den eteriske oppløsning over natriumsulfat og fordam-pes. En rå oljeliknende base (11.5 g) oppnås. 1:3-bis(dimethylamino)-2-propyl 3-acetyl-phenthiazine-10-carboxylate (14.1 g), melting point Kofler 128° C., dissolved in o-dichloro-benzene (25 cc) is heated for one hour under boiling until the evolution of COi ceases. The obtained solution is diluted with ether (50 cc), and the basic products are extracted with dilute hydrochloric acid. The organic layer is poured from the acidic solution, washed with ether and then made alkaline with dilute sodium hydroxide. After extraction with ether, the ethereal solution is dried over sodium sulfate and evaporated. A crude oil-like base (11.5 g) is obtained.
Produktet kan renses ved reaksjon med fumarsyre i vandig etanol. Etter omkrystal-lisering fra metanol av det oppnådde salt, oppnås det nøytrale fumarat av 3-acetyl-10-[2:3-bis(dimetylamino)-l-propyl] fentiazin (smeltepunkt 222° C Kofler). The product can be purified by reaction with fumaric acid in aqueous ethanol. After recrystallization from methanol of the obtained salt, the neutral fumarate of 3-acetyl-10-[2:3-bis(dimethylamino)-1-propyl] phenthiazine is obtained (melting point 222° C. Kofler).
Begynnelsesesteren fremstilles ved kondensasjon i toluol av 1:3-bis (dimetylamino)propan-2-ol med 3-acetyl-fentiazin-10-karbonylklorid, smeltepunkt 123° C. (Kofler), som igjen er oppnådd ved innvirkning av fosgen på 3-acetylfentiazin i toluol, i nærvær av pyridin. The initial ester is prepared by condensation in toluene of 1:3-bis(dimethylamino)propan-2-ol with 3-acetyl-phenthiazine-10-carbonyl chloride, melting point 123° C. (Kofler), which is again obtained by the action of phosgene on 3 -acetylphenthiazine in toluene, in the presence of pyridine.
Eksempel IV. Example IV.
Ved å følge arbeidsmåte etter eksempel 1 fremstiltes fra de tilsvarende fentiazin-10-karboksylater de følgende forbindelser: 3 -metyl-10 - [ 2:3 -bis (dim etylamino) -1 - propyl] fentiazin, kokepunkt 195-200° C/0.8 mm 'Hg; 1 -klor-10- [ 2:3-bis (dimetylamino) -1 - propyl]fentiazin, kokepunkt 205-210° C/l mm Hg; By following the procedure according to example 1, the following compounds were prepared from the corresponding phenthiazine-10-carboxylates: 3-methyl-10-[2:3-bis(dimethylamino)-1-propyl] phenthiazine, boiling point 195-200° C/ 0.8 mm 'Hg; 1 -chloro-10-[2:3-bis(dimethylamino)-1-propyl]phenthiazine, boiling point 205-210° C/l mm Hg;
'3 -met oksy -10 - [ 2:2 -bis ( dimetylamino) - 1-propyl]fentiazin, kokepunkt 205-210° C/ 0.9 mm Hg, og '3-Methoxy-10-[2:2-bis(dimethylamino)-1-propyl]phenthiazine, boiling point 205-210° C/ 0.9 mm Hg, and
3-klor-10-[2:3-bis (dimetylamino)-l-propyl]fentiazin, kokepunkt 200-205° C/l mm Hg. 3-chloro-10-[2:3-bis(dimethylamino)-1-propyl]phenthiazine, boiling point 200-205° C/l mm Hg.
Claims (4)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO2180/70A NO122614B (en) | 1970-06-04 | 1970-06-04 | |
| DE2125639A DE2125639C3 (en) | 1970-06-04 | 1971-05-24 | Swivel fitting device for reversible windows |
| DK257371A DK149096C (en) | 1970-06-04 | 1971-05-27 | REVERSIBLE VIP WINDOW AND STEERING ARM SYSTEM THEREOF |
| NL7107517A NL7107517A (en) | 1970-06-04 | 1971-06-01 | |
| AT478171A AT322404B (en) | 1970-06-04 | 1971-06-02 | DEVICE FOR A TOP-HINGED WINDOW |
| FI711527A FI48629C (en) | 1970-06-04 | 1971-06-02 | Hinge device for reversible windows. |
| US00149696A US3721044A (en) | 1970-06-04 | 1971-06-03 | Hinge means for reversible windows |
| FR7120228A FR2095904A5 (en) | 1970-06-04 | 1971-06-03 | |
| SE7107194A SE380863B (en) | 1970-06-04 | 1971-06-03 | Hinged device for reversible windows |
| BE768040A BE768040A (en) | 1970-06-04 | 1971-06-03 | HINGE SYSTEM FOR REVERSIBLE WINDOWS |
| CH806771A CH542352A (en) | 1970-06-04 | 1971-06-03 | Pivoting device for pivoting windows |
| GB09039/71A GB1299154A (en) | 1970-06-04 | 1971-06-04 | A window operating assembly for reversible windows |
| NL8102603A NL8102603A (en) | 1970-06-04 | 1981-05-27 | ASSEMBLY OF A FRAME AND A REVERSIBLE TILTABLE FRAME THEREIN. |
| DK253581A DK253581A (en) | 1970-06-04 | 1981-06-11 | HANGING DEVICE FOR REVERSIBLE WINDOWS |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO2180/70A NO122614B (en) | 1970-06-04 | 1970-06-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO122614B true NO122614B (en) | 1971-07-19 |
Family
ID=19878693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2180/70A NO122614B (en) | 1970-06-04 | 1970-06-04 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3721044A (en) |
| AT (1) | AT322404B (en) |
| BE (1) | BE768040A (en) |
| CH (1) | CH542352A (en) |
| DE (1) | DE2125639C3 (en) |
| DK (1) | DK149096C (en) |
| FI (1) | FI48629C (en) |
| FR (1) | FR2095904A5 (en) |
| GB (1) | GB1299154A (en) |
| NL (2) | NL7107517A (en) |
| NO (1) | NO122614B (en) |
| SE (1) | SE380863B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0053905A1 (en) * | 1980-12-10 | 1982-06-16 | V. Kann Rasmussen Holding A/S | A tilting window |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE44554B1 (en) * | 1975-12-03 | 1982-01-13 | Interlock Ind Ltd | Timprovements in window or the like stays |
| NO137868C (en) * | 1976-11-17 | 1978-05-10 | Harald Kvasnes | DEVICE FOR REVERSE WINDOW. |
| NO150171C (en) * | 1982-01-11 | 1984-08-29 | Kva Spil Ltd | DEVICE FOR REVERSIBLE WINDOW |
| DE8202421U1 (en) * | 1982-01-30 | 1982-07-01 | August Bilstein GmbH & Co KG, 5828 Ennepetal | SIDE FITTING FOR TURN-TIP WINDOWS, DOORS OD. DGL. |
| US4480406A (en) * | 1982-08-11 | 1984-11-06 | Wilh. Frank Gmbh | Skylight |
| GB2127092A (en) * | 1982-09-16 | 1984-04-04 | Securistyle Ltd | Improvements in friction supporting stays for windows |
| DE8325105U1 (en) * | 1983-09-01 | 1984-06-28 | Fa. Walter Schüring, 5000 Köln | SWIVEL FITTING FOR WINDOW |
| NO161748C (en) * | 1985-01-22 | 1989-09-20 | Kva Spil Ltd | DEVICE FOR SWITCHING WINDOW. |
| ATA112985A (en) * | 1985-04-16 | 1991-05-15 | Grass Alfred Metallwaren | FITTING FOR A CABINET WITH DOOR ON THE FRONT |
| NZ226410A (en) * | 1988-03-09 | 1993-01-27 | Interlock Ind Ltd | Window stay with transverse retaining force on closure |
| SE464482C (en) * | 1989-08-25 | 1997-09-08 | Teknoskand Invent Ab | Swivel arm fittings fitted with latches for windows, hatches and the like |
| NO178043B (en) * | 1991-11-11 | 1995-10-02 | Ernst Lahmann | Fittings for blades in windows or the like, which are tiltable or rotatable 180 |
| SE9202552L (en) * | 1992-09-07 | 1994-03-08 | Teknoskand Invent Ab | A window, a door or the like and in particular a sliding bracket for this purpose |
| DE9406891U1 (en) * | 1994-04-26 | 1994-06-16 | Roto Frank Ag, 70771 Leinfelden-Echterdingen | Folding swing roof window with opening aid |
| US5815984A (en) * | 1996-03-27 | 1998-10-06 | Wright Products Corp. | Casement window operator |
| GB2318613A (en) * | 1996-10-22 | 1998-04-29 | Securistyle Ltd | A stay for a vent |
| NO982357A (en) * | 1998-05-25 | 1999-07-05 | Gunnar Lien | Floor-proof safety device for tilting window with child lock |
| DE10300847A1 (en) * | 2003-01-10 | 2004-07-22 | SCHÜCO International KG | Fitting unit for a window or a door |
| CH702221B1 (en) * | 2005-04-14 | 2011-05-31 | 4B Fassaden Ag | Fitting for turning window, has window leaf, whose end is displaceably mounted along window frame which is displaced from closing position of leaf into open position from end of frame |
| ATE503072T1 (en) * | 2004-10-20 | 2011-04-15 | Walch Gmbh | FITTING FOR A REVERSIBLE WINDOW AND REVERSIBLE WINDOW WITH SUCH A FITTING |
| SE530170C2 (en) * | 2005-11-25 | 2008-03-18 | Assa Ab | Swivel mechanism for reversible windows, doors and the like |
| SE529571C2 (en) * | 2006-02-22 | 2007-09-18 | Assa Ab | Suspension device for windows, doors and the like |
| SE530173C2 (en) * | 2006-02-22 | 2008-03-18 | Assa Ab | Suspension device for windows, doors and the like |
| DE102008021638A1 (en) | 2008-04-30 | 2009-11-05 | Franz Hesedenz Gmbh | Component for closing a wall opening |
| DE102011101490A1 (en) * | 2011-05-14 | 2012-11-15 | Roto Frank Ag | Holding device for a rooftop and residential roof windows with holding device |
| SE536359C2 (en) * | 2012-04-05 | 2013-09-10 | Assa Oem Ab | Suspension for windows |
| AR097994A1 (en) | 2014-10-10 | 2016-04-27 | Anselmo Antonetti Oscar | SUPERIOR OPENING WINDOW TYPE BANDEROLA AND FRAME |
-
1970
- 1970-06-04 NO NO2180/70A patent/NO122614B/no unknown
-
1971
- 1971-05-24 DE DE2125639A patent/DE2125639C3/en not_active Expired
- 1971-05-27 DK DK257371A patent/DK149096C/en not_active IP Right Cessation
- 1971-06-01 NL NL7107517A patent/NL7107517A/xx unknown
- 1971-06-02 FI FI711527A patent/FI48629C/en active
- 1971-06-02 AT AT478171A patent/AT322404B/en not_active IP Right Cessation
- 1971-06-03 SE SE7107194A patent/SE380863B/en unknown
- 1971-06-03 CH CH806771A patent/CH542352A/en not_active IP Right Cessation
- 1971-06-03 BE BE768040A patent/BE768040A/en not_active IP Right Cessation
- 1971-06-03 FR FR7120228A patent/FR2095904A5/fr not_active Expired
- 1971-06-03 US US00149696A patent/US3721044A/en not_active Expired - Lifetime
- 1971-06-04 GB GB09039/71A patent/GB1299154A/en not_active Expired
-
1981
- 1981-05-27 NL NL8102603A patent/NL8102603A/en not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0053905A1 (en) * | 1980-12-10 | 1982-06-16 | V. Kann Rasmussen Holding A/S | A tilting window |
Also Published As
| Publication number | Publication date |
|---|---|
| NL8102603A (en) | 1981-10-01 |
| DE2125639B2 (en) | 1975-03-27 |
| NL7107517A (en) | 1971-12-07 |
| AT322404B (en) | 1975-05-26 |
| BE768040A (en) | 1971-11-03 |
| US3721044A (en) | 1973-03-20 |
| DE2125639C3 (en) | 1975-11-06 |
| FI48629B (en) | 1974-07-31 |
| CH542352A (en) | 1973-09-30 |
| FI48629C (en) | 1974-11-11 |
| FR2095904A5 (en) | 1972-02-11 |
| GB1299154A (en) | 1972-12-06 |
| SE380863B (en) | 1975-11-17 |
| DK149096B (en) | 1986-01-20 |
| DE2125639A1 (en) | 1971-12-09 |
| DK149096C (en) | 1986-08-11 |
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