NO146548B - DEVICE FOR SPROSSE WINDOW CONSTRUCTIONS - Google Patents

DEVICE FOR SPROSSE WINDOW CONSTRUCTIONS Download PDF

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Publication number
NO146548B
NO146548B NO792682A NO792682A NO146548B NO 146548 B NO146548 B NO 146548B NO 792682 A NO792682 A NO 792682A NO 792682 A NO792682 A NO 792682A NO 146548 B NO146548 B NO 146548B
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Norway
Prior art keywords
bicyclo
salts
amino ketones
heptanone
general formula
Prior art date
Application number
NO792682A
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Norwegian (no)
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NO792682L (en
NO146548C (en
Inventor
Karsten Lian
Original Assignee
Karsten Lian
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.)
Filing date
Publication date
Application filed by Karsten Lian filed Critical Karsten Lian
Priority to NO792682A priority Critical patent/NO146548C/en
Priority to DE8080901497T priority patent/DE3067844D1/en
Priority to PCT/NO1980/000026 priority patent/WO1981000589A1/en
Priority to AT80901497T priority patent/ATE7526T1/en
Publication of NO792682L publication Critical patent/NO792682L/en
Priority to EP80901497A priority patent/EP0034593B1/en
Publication of NO146548B publication Critical patent/NO146548B/en
Publication of NO146548C publication Critical patent/NO146548C/en

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    • EFIXED CONSTRUCTIONS
    • E06DOORS, WINDOWS, SHUTTERS, OR ROLLER BLINDS IN GENERAL; LADDERS
    • E06BFIXED OR MOVABLE CLOSURES FOR OPENINGS IN BUILDINGS, VEHICLES, FENCES OR LIKE ENCLOSURES IN GENERAL, e.g. DOORS, WINDOWS, BLINDS, GATES
    • E06B3/00Window sashes, door leaves, or like elements for closing wall or like openings; Layout of fixed or moving closures, e.g. windows in wall or like openings; Features of rigidly-mounted outer frames relating to the mounting of wing frames
    • E06B3/68Window bars

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  • Engineering & Computer Science (AREA)
  • Civil Engineering (AREA)
  • Structural Engineering (AREA)
  • Securing Of Glass Panes Or The Like (AREA)
  • Window Of Vehicle (AREA)

Description

Fremgangsmåte til fremstilling av nye farmakologisk virksomme bicykliske aminoketoner og av salter av sådanne. Process for the production of new pharmacologically active bicyclic amino ketones and salts thereof.

Foreliggende oppfinnelse angår en The present invention relates to a

fremgangsmåte til fremstilling av farmakologisk virksomme bicycliske aminoketoner med nedenstående generelle formel I. method for the production of pharmacologically active bicyclic amino ketones with the following general formula I.

I denne formel betegner R, og R2 lavere In this formula R, and R2 denote lower

alkyl, cycloalkyl, aryl, aralkyl eller, sammen med nitrogenatomet en pyrrolidin-, piperidin-, morfolin- eller piperazinring, alkyl, cycloalkyl, aryl, aralkyl or, together with the nitrogen atom, a pyrrolidine, piperidine, morpholine or piperazine ring,

som dessuten kan være substituert med lavere alkylrester, mens X betegner -CH2-eller CH,-CH2-. which can also be substituted with lower alkyl residues, while X denotes -CH 2 - or CH, -CH 2 -.

Det er kjent at cycloalifatiske ketoner It is known that cycloaliphatic ketones

lar seg overføre til aminoketoner ved omsetning med formaldehyd og sekundære aminer. Blandt disse aminoketoner er der funnet farmakologisk virksomme stoffer (se sveitsisk patent nr. 347 829, Badische Anilin- und Sodafabrik AG). can be transferred to aminoketones by reaction with formaldehyde and secondary amines. Among these amino ketones, pharmacologically active substances have been found (see Swiss patent no. 347,829, Badische Anilin- und Sodafabrik AG).

Det ble nu funnet at man ved å an-vende denne reaksjon på bicyclo-[2,2,l"!-heptanon-(2) og bicyclo-[2,2,2]-octanon får forbindelser med verdifulle farmakolo-giske egenskaper. It was now found that by applying this reaction to bicyclo-[2,2,1"!-heptanone-(2) and bicyclo-[2,2,2]-octanone compounds with valuable pharmacological properties are obtained .

Fremstilling av de nye aminoketoner foregår ifølge oppfinnelsen ved omsetning av bicyclo-[2,2,l]-heptanon-(2) eller bicyclo-[2,2,2]-octanon med sekundære aminer eller salter av sådanne og formaldehyd i vandig oppløsning ved oppvarming under tilbakeløpskjøling. Ikke omsatt utgangs-materiale, altså keton, kan gjenvinnes fra reaksjonsblandingen ved å taes opp i orga-niske oppløsningsmidler eller ved avdriv-ning med vanndamp. Production of the new amino ketones takes place according to the invention by reacting bicyclo-[2,2,1]-heptanone-(2) or bicyclo-[2,2,2]-octanone with secondary amines or salts thereof and formaldehyde in aqueous solution when heating during reflux cooling. Unreacted starting material, i.e. ketone, can be recovered from the reaction mixture by being taken up in organic solvents or by stripping with steam.

De nye aminoketoner lar seg direkte isolere fra reaksjonsblandingen som hydrc-klorider, eller som frie aminoketoner etter at reaksjonsblandingen er gjort alkalisk. The new amino ketones can be directly isolated from the reaction mixture as hydric chlorides, or as free amino ketones after the reaction mixture has been made alkaline.

Disse nye bicycliske aminoketoner er bestandige forbindelser, de lar seg uten å spaltes destillere i høyt vakuum. De frie aminoketoner er lite oppløselige eller uopp-løselige i vann, men deres salter f. eks. hyd-rokloridene og methobromidene oppløsen lett i vann. These new bicyclic aminoketones are stable compounds, they can be distilled in high vacuum without splitting. The free amino ketones are poorly soluble or insoluble in water, but their salts, e.g. the hydrochlorides and methobromides dissolve easily in water.

De nye aminoketoner som fåes vec". fremgangsmåten ifølge oppfinnelsen, er relativt lite giftige. Således er f. eks. den dose som forårsaker 50 pst.'s dødelighet (DL-n) hos albinoide Swiss-Webster-mus, ca. 800 mg/kg legemsvekt for 3-dimethyl-aminomethyl- og 3-piperidino-methyl-bicyclo-[2,2,l]-heptanon-(2). Ved dyreforsøl: viser disse aminoketoner en analgetisl: virkning som tilsvarer acetylsalicylsyrenn virkning (se Arzneim.—Forsch. (Drug Re-search) 13, 414—15 (1963)). The new amino ketones obtained by the method according to the invention are relatively untoxic. Thus, for example, the dose that causes 50 percent mortality (DL-n) in albino Swiss-Webster mice is approximately 800 mg /kg body weight for 3-dimethyl-aminomethyl- and 3-piperidino-methyl-bicyclo-[2,2,1]-heptanone-(2). In animal poisoning: these aminoketones show an analgesic: action corresponding to the action of acetylsalicylic acid (see Arzneim .—Forsch. (Drug Re-search) 13, 414-15 (1963)).

Bicyclo- [2,2,1 ] -heptan-derivater opp-trer som bekjent i endo-exo-isomere for-mer: Bicyclo-[2,2,1]-heptane derivatives appear as known in endo-exo-isomeric forms:

Det ble nu funnet at gruppen It was now found that the group

-CHgNRjRj i den generelle formel I inntar exo-stillingén, da der av 3-dimethylamino-methyl-bicyclo- [ 2,2,1 ] -heptanon- (2) ved fjernelse av carbonylgruppen ved fremgangsmåte I ifølge Huang-Minlon dannes exo-3-dimethylaminomethyl-bicyclo-[2,2,l]-heptan hvis konfigurasjonen er fastslått. I -CHgNRjRj in the general formula I takes the exo-position, since from 3-dimethylamino-methyl-bicyclo- [ 2,2,1 ]-heptanone- (2) upon removal of the carbonyl group by method I according to Huang-Minlon, exo- 3-dimethylaminomethyl-bicyclo-[2,2,1]-heptane if the configuration is established. IN

I det følgende beskrives som eksempler noen utførel|sesformer for oppfinnelsen. In the following, some embodiments of the invention are described as examples.

Eksempel 1. Example 1.

110 g bicyclo-[2,2,l]-heptanon-(2) (1 mol) oppvarmes i 20 timer under tilbake-løpskjøling med 123,5 g morfolinhydroklo-rid (1 mol) ,og 120 ml 40 pst.'s formalde-hydoppløsnihg (1,6 mol) under tilsetning av 1 ml konsentrert saltsyre. Etter avkjø-ling fjernes det ikke omsatte bicyclo-[2,2,l]-heptånon-(2) ved utetring (eller avdrives direkte med vanndamp). Den vandige oppløsning gjøres derpå alkalisk med fast kaliumkarbonat og utetres påny. Etter at oppløsningen i ether er befridd for vann og etheren avdestillert, blir residuet destillert i høyt vakuum. Det erholdte 3-morf olinomethyl-bicyclo- [2,2,1 ] -hepta-non-(2) destilleres ved 102—106°C, 0,04 Torr. Utbyttet er 72 pst. av det teoretiske beregnet på omsatt bicyclo-[2,2,l]-hepta-non-(2). Den vandige oppløsning kan og-så som sådan inndampes under forminsket trykk og det J erholdte hydroklorid omkrys-talliseres fra; n-propanol, hvorved man får 110 g of bicyclo-[2,2,1]-heptanone-(2) (1 mol) are heated for 20 hours under reflux with 123.5 g of morpholine hydrochloride (1 mol) and 120 ml of 40% formaldehyde hydopplosnihg (1.6 mol) while adding 1 ml of concentrated hydrochloric acid. After cooling, the unreacted bicyclo-[2,2,1]-heptanone-(2) is removed by decantation (or stripped off directly with steam). The aqueous solution is then made alkaline with solid potassium carbonate and extracted again. After the solution in ether has been freed from water and the ether distilled off, the residue is distilled in high vacuum. The 3-morph olinomethyl-bicyclo-[2,2,1]-hepta-non-(2) obtained is distilled at 102-106°C, 0.04 Torr. The yield is 72 percent of the theoretical calculated for converted bicyclo-[2,2,1]-hepta-non-(2). The aqueous solution can also be evaporated as such under reduced pressure and the hydrochloride obtained recrystallized from; n-propanol, which gives

det i ren tilstand med smeltepunkt 194,0— 194,5°C. it in its pure state with a melting point of 194.0— 194.5°C.

I tabellene I og II i det følgende er oppført fysikalske data for frie aminoketoner så vel som smeltepunktene for hyd-roklorider og methobromider samt resul-tatene av halogenbestemmelser, av enkelte aminoketoner som fåes ved fremgangsmåten ifølge oppfinnelsen og som er avledet fra bicyclo-[2,2,l]-heptanon-(2). Fremstillingen av disse forbindelser ble utført således som angitt i eksempel 1 med unntagel-se av dimethylamino-ethyl-forbindelsen som ble fremstillet som angitt i følgende eksempel 2. Tables I and II below list physical data for free amino ketones as well as the melting points for hydrochlorides and methobromides as well as the results of halogen determinations of certain amino ketones which are obtained by the method according to the invention and which are derived from bicyclo-[2 ,2,1]-heptanone-(2). The preparation of these compounds was carried out as indicated in example 1 with the exception of the dimethylamino-ethyl compound which was prepared as indicated in the following example 2.

Eksempel 2. Example 2.

110 g bicyclo-[2,2,l]-héptanon-(2) (1 mol) oppvarmes i 20 timer under tilbake-løpskjøling med 135 ml 33 pst.'s dimethyl-amin (1 mol), 120 ml 40 pst.'s formalin (1,6 110 g of bicyclo-[2,2,1]-heptanone-(2) (1 mol) are heated for 20 hours under reflux with 135 ml of 33% dimethylamine (1 mol), 120 ml of 40% 's formalin (1.6

mol) og 100 ml konsentrert saltsyre. Opp-arbeidelsen foregår på den i eksempel 1 beskrevne måte. Det erholdte dimethyl-aminomethyl-bicyclo- [2,2,1 ] -heptanon-(2) koker ved 58—61°C/0,02 Torr. Utbyttet mol) and 100 ml concentrated hydrochloric acid. The preparation takes place in the manner described in example 1. The obtained dimethyl-aminomethyl-bicyclo-[2,2,1]-heptanone-(2) boils at 58-61°C/0.02 Torr. The dividend

er 48 pst. av det teoretiske, beregnet på omsatt bicyclo-[2,2,1]-heptanon-(2). is 48 percent of the theoretical, calculated on converted bicyclo-[2,2,1]-heptanone-(2).

I stedet for formaldehyd kan man an-vende paraformaldehyd. Instead of formaldehyde, paraformaldehyde can be used.

Fremstillingen av saltene foregår på i The production of the salts takes place at i

og for seg kjent måte. and known manner.

Omsetningen med bicyclo-[2,2,2 ]-oc-tanon kan utføres på den måte som er be-skrevet i eksemplene 1 og 2. 3-piperidino-methyl-bicyclo-[2,2,2]-octanon koker ved The reaction with bicyclo-[2,2,2]-octanone can be carried out in the manner described in examples 1 and 2. 3-piperidino-methyl-bicyclo-[2,2,2]-octanone boils at

115—120°C/0,03 Torr, nn2o 1,5060, D42o 1,0159, Mn 64,73 (MD lier <6>4,20). Metho- jo-didets sm.p. 206,5—208°C (fra ethanol-ether (2:1)). Formel: C15<H>2G<N>OJ (363,28), beregnet C 49,59 pst., H 7,21 pst. og N 3,85 pst., funnet C 49,35 pst., H 7,36 pst., N 3,97 pst. 115—120°C/0.03 Torr, nn2o 1.5060, D42o 1.0159, Mn 64.73 (MD lier <6>4.20). Metho-dide's m.p. 206.5-208°C (from ethanol-ether (2:1)). Formula: C15<H>2G<N>OJ (363.28), calculated C 49.59%, H 7.21% and N 3.85%, found C 49.35%, H 7, 36 per cent, N 3.97 per cent.

Claims (1)

Fremgangsmåte til fremstilling av farmakologisk virksomme bicycliske aminoketoner med den generelle formel: (i hvilken R, og R2 betegner lavere alkyl, cycloalkyl, aryl, aralkyl, eller sammen med nitrogenatomet betegner en pyrrolidin-, piperidin-, morfolin- eller piperazinringProcess for the preparation of pharmacologically active bicyclic amino ketones of the general formula: (in which R, and R 2 denote lower alkyl, cycloalkyl, aryl, aralkyl, or together with the nitrogen atom denote a pyrrolidine, piperidine, morpholine or piperazine ring som dessuten kan være substituert med lavmolekylære alkylrester, mens X betegner -CH2- eller -CH2-CH2-), eller salter av sådanne, karakterisert ved at man omsetter bicyclo-[2,2,l]-heptanon-(2) eller bicyclo-[2,2,2]-octanon med sekundære aminer av den generelle formel: NH(R,R2), eller med salter av sådanne, og formaldehyd, hvorpå man eventuelt overfører de erholdte fri aminoketoner til ønskede salter.which can also be substituted with low molecular weight alkyl residues, while X denotes -CH2- or -CH2-CH2-), or salts thereof, characterized by reacting bicyclo-[2,2,1]-heptanone-(2) or bicyclo -[2,2,2]-octanone with secondary amines of the general formula: NH(R,R2), or with salts thereof, and formaldehyde, whereupon the free amino ketones obtained are optionally transferred to the desired salts.
NO792682A 1979-08-16 1979-08-16 DEVICE FOR SPROSSE WINDOW CONSTRUCTIONS. NO146548C (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
NO792682A NO146548C (en) 1979-08-16 1979-08-16 DEVICE FOR SPROSSE WINDOW CONSTRUCTIONS.
DE8080901497T DE3067844D1 (en) 1979-08-16 1980-08-11 Cross bar window constructions
PCT/NO1980/000026 WO1981000589A1 (en) 1979-08-16 1980-08-11 Device for cross bar constructions
AT80901497T ATE7526T1 (en) 1979-08-16 1980-08-11 BAR WINDOW CONSTRUCTIONS.
EP80901497A EP0034593B1 (en) 1979-08-16 1981-03-09 Cross bar window constructions

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NO792682A NO146548C (en) 1979-08-16 1979-08-16 DEVICE FOR SPROSSE WINDOW CONSTRUCTIONS.

Publications (3)

Publication Number Publication Date
NO792682L NO792682L (en) 1981-02-17
NO146548B true NO146548B (en) 1982-07-12
NO146548C NO146548C (en) 1982-10-20

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NO792682A NO146548C (en) 1979-08-16 1979-08-16 DEVICE FOR SPROSSE WINDOW CONSTRUCTIONS.

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EP (1) EP0034593B1 (en)
DE (1) DE3067844D1 (en)
NO (1) NO146548C (en)
WO (1) WO1981000589A1 (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE433433B (en) * 1981-10-29 1984-05-28 Bror Goran Einar Liljemark INTERIOR ELEMENTS
DE4017608C2 (en) * 1990-05-31 1998-05-07 Hampel Zoellner Ges Fuer Klass Kit for windows

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2365954A (en) * 1942-06-17 1944-12-26 Herold H Hebestreit Window sash
FR1030758A (en) * 1951-01-08 1953-06-17 Improvements in the manufacture of windows, glass doors and the like
FR1548686A (en) * 1967-10-27 1968-12-06
SE352922B (en) * 1970-10-22 1973-01-15 Kaehrs Maskiner Ab

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DE3067844D1 (en) 1984-06-20
EP0034593B1 (en) 1984-05-16
EP0034593A1 (en) 1981-09-02
NO792682L (en) 1981-02-17
NO146548C (en) 1982-10-20
WO1981000589A1 (en) 1981-03-05

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