NO146548B - DEVICE FOR SPROSSE WINDOW CONSTRUCTIONS - Google Patents
DEVICE FOR SPROSSE WINDOW CONSTRUCTIONS Download PDFInfo
- 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
- Authority
- NO
- Norway
- Prior art keywords
- bicyclo
- salts
- amino ketones
- heptanone
- general formula
- Prior art date
Links
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- -1 bicyclic amino ketones Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 238000006856 Wolf-Kishner-Huang Minlon reduction reaction Methods 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- JXYZHMPRERWTPM-UHFFFAOYSA-N hydron;morpholine;chloride Chemical compound Cl.C1COCCN1 JXYZHMPRERWTPM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Classifications
-
- E—FIXED CONSTRUCTIONS
- E06—DOORS, WINDOWS, SHUTTERS, OR ROLLER BLINDS IN GENERAL; LADDERS
- E06B—FIXED OR MOVABLE CLOSURES FOR OPENINGS IN BUILDINGS, VEHICLES, FENCES OR LIKE ENCLOSURES IN GENERAL, e.g. DOORS, WINDOWS, BLINDS, GATES
- E06B3/00—Window 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
- E06B3/68—Window bars
Landscapes
- 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)
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 |
Family
ID=19885011
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO792682A NO146548C (en) | 1979-08-16 | 1979-08-16 | DEVICE FOR SPROSSE WINDOW CONSTRUCTIONS. |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0034593B1 (en) |
DE (1) | DE3067844D1 (en) |
NO (1) | NO146548C (en) |
WO (1) | WO1981000589A1 (en) |
Families Citing this family (2)
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)
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 |
-
1979
- 1979-08-16 NO NO792682A patent/NO146548C/en unknown
-
1980
- 1980-08-11 DE DE8080901497T patent/DE3067844D1/en not_active Expired
- 1980-08-11 WO PCT/NO1980/000026 patent/WO1981000589A1/en active IP Right Grant
-
1981
- 1981-03-09 EP EP80901497A patent/EP0034593B1/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
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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