SE447102B - NEW ALFA ACYLOXY ACETAMIDS AND PROCEDURES FOR THEIR PREPARATION - Google Patents
NEW ALFA ACYLOXY ACETAMIDS AND PROCEDURES FOR THEIR PREPARATIONInfo
- Publication number
- SE447102B SE447102B SE8000175A SE8000175A SE447102B SE 447102 B SE447102 B SE 447102B SE 8000175 A SE8000175 A SE 8000175A SE 8000175 A SE8000175 A SE 8000175A SE 447102 B SE447102 B SE 447102B
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- SE
- Sweden
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- general formula
- acyloxy
- carboxylic acid
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- carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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Description
447 102 2 OH H l / . \ a- 5 HàN R 2 som har värdefulla farmakologiska egenskaper, speciellt bronkolytiska effekter. 447 102 2 OH H l / . \ a- 5 HàN R 2 which have valuable pharmacological properties, in particular broncholytic effects.
I de ovan angivna allmänna formlerna I och II betecknar Rl en klor- eller bromatom, _ R2 en trifluormetylgrupp, en fluor- eller kloratom, R3 betecknar en grenad alkylrest eller en cykloalkylgrupp med vardera 3 - 5 kolatomer och R en aCylreSt av ên alifatisk eller aromatisk karboxylsyra. 4 Bland de vid definitionen av resterna R3 och R4 angivna bety- delserna ifrågakommer för R3 speciellt betydelsen isopropyl, isobutyl, tert.butyl, isopentyl, neopentyl, tert.pentyl, cyklopropyl, cyklobutyl eller cyklopentyl och för R4 den ena acylresten av en alifatisk eller aromatisk karboxylsyra såsom ättiksyra, propionsyra, trimetylättiksyra, valeriansyra, bensoesyra, nitrobensoesyra eller naftalin-2-karboxylsyra.In the above general formulas I and II denote Rl a chlorine or bromine atom, _ R 2 is a trifluoromethyl group, a fluorine or chlorine atom, R 3 represents a branched alkyl radical or a cycloalkyl group with each 3 - 5 carbon atoms and R is an aCylreSt of an aliphatic or aromatic carboxylic acid. 4 Among the meanings given in the definition of residues R3 and R4, the parts in question for R3 in particular the meaning isopropyl, isobutyl, tert.butyl, isopentyl, neopentyl, tert.pentyl, cyclopropyl, cyclobutyl or cyclopentyl and for R 4 one the acyl residue of an aliphatic or aromatic carboxylic acid such as acetic acid, propionic acid, trimethyl acetic acid, valeric acid, benzoic acid, nitrobenzoic acid or naphthalene-2-carboxylic acid.
Enligt uppfinningen erhåller man de nya Q-acyloxi-acetamiderna med den ovan angivna allmänna formeln I genom omsättning av en 4-aminobensaldehyd med den allmänna formeln 31 cuo ,(III) H N 447 102 vari Rl allmänna formeln och Rz har ovan angiven betydelse med en isonitril med den 3 , (IV) vari R3 har ovan angiven betydelse, och med en karboxylsyra med den allmänna formeln R ~ OH , (V) vari R4 har ovan angiven betydelse.According to the invention the new Q-acyloxy-acetamides are obtained with the above general formula I by reacting a 4-aminobenzaldehyde of the general formula 31 cuo , (III) H N 447 102 wherein Rl general formula and R 2 has the meaning given above with an isonitrile with it 3, (IV) wherein R3 has the meaning given above, and with a carboxylic acid with it general formula R ~ OH, (V) wherein R4 has the meaning given above.
För framställning av en fenyletanolamin med den allmänna for- meln II reduceras en så erhâllen Q-acyloxi-acetamid med den alhnänna formeln I vilken även kan vidareomsättas som râpro- dukt, med en hydrid, t.ex. med en metallhydrid eller en komp- lex metallhydrid såsom bor/tetrahydrofuran eller litiumalumi- niumhydrid.For the preparation of a phenylethanolamine having the general formula meln II, a Q-acyloxy-acetamide thus obtained is reduced with it the general formula I which can also be further converted as a crude duct, with a hydride, e.g. with a metal hydride or a comp- lex metal hydride such as boron / tetrahydrofuran or lithium aluminum nium hydride.
Omsättningen av en 4-aminobensaldehyd med den allmänna formeln III med en isonitril med den allmänna formeln IV och en kar- boxylsyra med den allmänna formeln V sker lämpligen i ett lämpligt lösningsmedel såsom metylenklorid eller kloroform vid lägre temperaturer, t.ex. vid temperaturer mellan -20 och 75°C, lämpligen dock vid rumstemperatur. Omsättningen genomföres dock företrädesvis på så sätt att under omrörning och vid rumstemperatur antingen samtidigt ur en dropptratt en förening med den allmänna formeln IV och en karboxylsyra med den allmänna formeln V droppas till en lösning av en aldehyd med den allmänna formeln III eller till en lösning av en isonitril med den allmänna formeln IV och en aldehyd med den allmänna formeln III av en karboxylsyra med den allmänna formeln V inom nâgra timmar, t.ex. 5 - lO timmar och att blandningen därefter omröres ytterligare lO~l65 timmar. 447 102 4 De som utgångsämnen använda föreningarna med den allmänna for- meln IV och V är kända från litteraturen.The reaction of a 4-aminobenzaldehyde of the general formula III with an isonitrile of the general formula IV and a car boxylic acid of the general formula V preferably takes place in one suitable solvent such as methylene chloride or chloroform at lower temperatures, for example at temperatures between -20 and 75 ° C, preferably at room temperature. However, sales are preferably carried out on so that while stirring and at room temperature either at the same time from a dropping funnel a compound of the general formula IV and a carboxylic acid of the general formula V are added dropwise a solution of an aldehyde of the general formula III or to a solution of an isonitrile of general formula IV and an aldehyde of the general formula III of a carboxylic acid with the general formula V within a few hours, e.g. 5 - 10 hours and that the mixture is then stirred for a further 10 ~ l65 hours. 447 102 4 The starting compounds used are the compounds of the general formula meln IV and V are known from the literature.
En som utgångsämne använd aldehyd med den allmänna formeln III erhålles exempelvis genom reduktion av en motsvarande 4- aminobensoesyrahalogenid eller -ester och efterföljande oxida- tion av en eventuellt erhållen bensylalkohol med brunsten_ De enligt det nya förfarandet enligt uppfinningen erhållna goda utbytena kunde inte förutses av en fackman, då det ur litteraturen är känt (jämför J. Amer. chem. Soc. volym 67 (1945) sid 1499 - l500) att Passerini-reaktionen inte kan genomföras med steriskt hindrande och a,B-omättade karbonyl- föreningar. Härvid förklaras inreaktiviteten för a,B-omättade karbonylföreningar, t.ex. krotonaldehyd, i jämförelse med Passerini-reaktionen genom neutralisation av det elektroniska centrumet av karbonylfunktionen på grund av den mesomera gränsstrukturen 0 ® ïo R-crwcn-g-R (---,è R-CH-CH=C-R alltså på grund av den elektronavgivande effekten av en när- belägen_grupp.An aldehyde of the general formula used as starting material III is obtained, for example, by reducing a corresponding 4- aminobenzoic acid halide or ester and subsequent oxide of a benzyl alcohol, if any, obtained with the rut_ Those obtained according to the new process according to the invention good exchanges could not be foreseen by a professional, as it out the literature is known (compare J. Amer. chem. Soc. volume 67 (1945) pp. 1499 - l500) that the Passerini reaction cannot carried out with steric hindrance and α, β-unsaturated carbonyl associations. This explains the inreactivity of α, β-unsaturated carbonyl compounds, e.g. crotonaldehyde, compared to The Passerini reaction by neutralizing the electronic the center of the carbonyl function due to the mesomer border structure 0 ® ïo R-crwcn-g-R (---, è R-CH-CH = C-R thus due to the electron-emitting effect of a located_group.
Det är ytterligare känt att aminogruppen i o- eller p-position av en fenylkärna har en stark elektronavgivande effekt.It is further known that the amino group is in the o- or p-position of a phenyl nucleus has a strong electron-releasing effect.
Fackmannen skulle därför ha väntat sig att det elektroniska centrumet i karbonylfunktionen av en 4-aminobensaldehyd med den alhnänna formeln III på grund av sin mesomera grundstruk-' tur med den allmänna formeln 447 102 5 /,H *H /c\ C) 0 H\@ ,(IIIa) a'”' R 2 desaktiveras och därmed inte lämpar sig för Passerini-reak- tionen. Detta är överraskande inte fallet.The person skilled in the art would therefore have expected the electronic the center of the carbonyl function of a 4-aminobenzaldehyde with the general formula III due to its mesomeric basic structure lucky with the general formula 447 102 5 /,HRS * H / c \ C) 0 H \ @, (IIIa) a '”' R 2 deactivated and thus not suitable for the Passerini reaction tion. This is surprisingly not the case.
Uppfinningen âskådliggöres närmare medelst följande exempel vari temperaturerna avser Celsius-grader.The invention is further illustrated by the following examples wherein the temperatures refer to degrees Celsius.
Exemgel l a-acetoxi-u-(4-amino-3,5-diklorfenyl)-N-tert.butylacetamid Till en lösning av 3,8 g (0,02 mol) 4-amino-3,5-diklorbens- aldehyd i 50 ml absolut metylenklorid tilldroppar man under omrörning vid rumtemperatur 3,32 g (0,04 mol) tert.butyliso- nitril och 4,8 g (0,08 mol) isättika ur tvâ skilda dropp- trattar med samma hastighet under 8 timmar. Därefter induns- tas den erhållna lösningen till hälften och avkyles. Den här- vid utfallande icke omsatta 4-amino-3,5-diklorbensaldehyden avsuges och filtratet indunstas ånyo till hälften. Till den erhållna blandningen sätter man samma volym diisopropyleter varvid den önskade produkten utkristalliseras, avsuges och tvättas med diisopropyleter. smä1tpunkt= 175 - 17e°. _ 447 102 Exemgel 2 d-acetoxi-a-(4-amino-3,5-diklorfenyl)-N-tert.butylacetamid Till en lösning av 30 g (0,l6 mol) 4-amino-3,5-diklorbens- aldehyd i 280 ml metylenklorid sättes 45 ml tert.butyliso- cyanid och därefter tilldroppas under omrörning och vid rums- temperatur cirka 4O ml isättika under 16 timmar. Därefter om- rör man ytterligare 4 timmar och indunstar blandningen i vakuum så länge att de första kristallerna utfälles. Efter av- kylning till 00 avsuges den utfallande icke omsatta 4-amino- 3,5-diklorbensaldehyden. Denna kan direkt omsättas på nytt.Exemgel l α-acetoxy-u- (4-amino-3,5-dichlorophenyl) -N-tert-butylacetamide To a solution of 3.8 g (0.02 mol) of 4-amino-3,5-dichlorobenzene aldehyde in 50 ml of absolute methylene chloride is added dropwise stirring at room temperature 3.32 g (0.04 mol) of tert-butyl iso- nitrile and 4.8 g (0.08 mol) of glacial acetic acid from two different droplets funnels at the same speed for 8 hours. Then evaporate take the resulting solution in half and cool. This- in the case of precipitated unreacted 4-amino-3,5-dichlorobenzaldehyde is filtered off with suction and the filtrate is evaporated again to half. To it the resulting mixture is added the same volume of diisopropyl ether whereby the desired product is crystallized, filtered off with suction and wash with diisopropyl ether. melting point = 175 - 17th °. _ 447 102 Example 2 d-acetoxy-α- (4-amino-3,5-dichlorophenyl) -N-tert-butylacetamide To a solution of 30 g (0.66 mol) of 4-amino-3,5-dichlorobenzene aldehyde in 280 ml of methylene chloride, add 45 ml of tert-butyl iso- cyanide and then added dropwise with stirring and at room temperature temperature about 40 ml of glacial acetic acid for 16 hours. Then re- stir for another 4 hours and evaporate the mixture in vacuum until the first crystals precipitate. After cooling to 00, the resulting unreacted 4-amino acid is aspirated. 3,5-dichlorobenzaldehyde. This can be immediately resold.
Filtratet försättes med n-hexan varvid den önskade produkten utfälles. Fällningen avsuges, tvättas med n-hexan och torkas. smä1tpunkt= 175 - 176°.The filtrate is added with n-hexane to give the desired product precipitates. The precipitate is filtered off with suction, washed with n-hexane and dried. melting point = 175 - 176 °.
Exemgel 3 a-acetoxi-u-(4-amino-3-klor-5-trifluormetylfenvlf-ättiksyra- tert.butylamid Till en lösning av 4,47 g (20 mmol) 4-amino-3-klor-5-trifluor- metylbensaldehyd i 50 ml metylenklorid tilldroppas vid rums- temperatur under omrörning 3,32 g (40 mmol) tert.butyliso- nitril och 4,8 g (80 mmol) isättika samtidigt under 5 timmar och omröres därefter 65 timmar vid rumstemperatur. Efter att ha avlägsnat lösningsmedlet i vakuum löses återstoden i eter, tvättas i tur och ordning med vatten och en mättad natrium- bikarbonatlösning, torkas över magnesiumsulfat och indunstas i vakuum till torrhet. Återstoden kromatograferas över en kiselgelkolonn med metylenklorid som elueringsmedel. Frak- tionerna, som innehåller dm önskade föreningen, förenas, in- dunstas och återstoden kristalliseras ur eter. smä1tpunkt= 155 - 1s6°. 447 102 Exemoel 4 d-acetoxi-a-(4-amino-3,5-diklorfenyl)-N-tert.butylacetamid Till en lösning av l4,l 9 (0,08 mol) 4-amino-3,5~diklor- bensaldehyd i 60 ml metylenklorid tillsättes vid rumstempera- tur och under omrörning 3,6 g (0,06mOl) ättiksyra och 2,5 g (0,03 mol) tert.butyl-isonotril. Därefter upphettas reaktions- blundningen 3 timmar under återflöde. När de ovan angivna förfarandena (tillsats av ättiksyra, tert.butyl-isonitril och upphettning under àterflöde) upprepats fyra gånger hällde man reaktionsblandningen i kall 2N natriumhydroxid och avskilda den organiska fasen. Efter tvättning med vatten och torkning av den organiska fasen över natriumsulfat indunstas bland- ningen i vakuum och återstoden kristalliserade ur metylen- klorid/hexan. smäitpunkt 175 - 17e°.Exemgel 3 α-acetoxy-u- (4-amino-3-chloro-5-trifluoromethylphenyl) -acetic acid tert.butylamide To a solution of 4.47 g (20 mmol) of 4-amino-3-chloro-5-trifluoro- methylbenzaldehyde in 50 ml of methylene chloride is added dropwise at room temperature. temperature with stirring 3.32 g (40 mmol) of tert-butyl iso- nitrile and 4.8 g (80 mmol) of glacial acetic acid simultaneously for 5 hours and then stirred for 65 hours at room temperature. After having removed the solvent in vacuo, the residue is dissolved in ether, washed in turn with water and a saturated sodium bicarbonate solution, dried over magnesium sulphate and evaporated in vacuum to dryness. The residue is chromatographed over one silica gel column with methylene chloride as eluent. Frak- the ions containing the desired compound are combined, evaporated and the residue crystallized from ether. melting point = 155 - 1s6 °. 447 102 Example 4 d-acetoxy-α- (4-amino-3,5-dichlorophenyl) -N-tert-butylacetamide To a solution of 14.19 (0.08 mol) of 4-amino-3,5-dichloro- benzaldehyde in 60 ml of methylene chloride is added at room temperature and with stirring 3.6 g (0.06 mol) of acetic acid and 2.5 g (0.03 mol) tert.butyl-isonotrile. Thereafter, the reaction medium is heated. the snooze 3 hours under reflux. When the above procedures (addition of acetic acid, tert-butyl isonitrile and heating under reflux) was repeated four times the reaction mixture in cold 2N sodium hydroxide and separated the organic phase. After washing with water and drying of the organic phase over sodium sulphate is evaporated in vacuo and the residue crystallized from methylene chloride / hexane. melting point 175 - 17th °.
Exemgel 5 a-(4-amino-3,5-diklorfenyl)-Q-bensoyloxi-N-tert.butylacetamid Framställd ur 4-amino-3,5-diklorbensaldehyd, tert.butyl- isonitril och bensoesyra i kloroform vid återflödes tempera- tur analogt med exempel 3. smäitpunkt 189 - 192° (sintring från 1as°).Example 5 α- (4-amino-3,5-dichlorophenyl) -Q-benzooyloxy-N-tert-butylacetamide Prepared from 4-amino-3,5-dichlorobenzaldehyde, tert-butyl isonitrile and benzoic acid in chloroform at reflux temperature turn analogous to Example 3. melting point 189 - 192 ° (sintering from 1as °).
Exemgel 6 Q-(4-amino-3,5-diklorfenyl)-a-valeroyloxi-N-tert.butylacetamid Framställd ur 4-amino-3,5-diklorbensaldehyd, tert.butyl- isonitril och valeriansyra analogt med exempel 3. smä1tpunkt= 95 - 9a°.Example 6 Q- (4-amino-3,5-dichlorophenyl) -α-valeroyloxy-N-tert-butylacetamide Prepared from 4-amino-3,5-dichlorobenzaldehyde, tert-butyl isonitrile and valeric acid analogously to Example 3. melting point = 95 - 9a °.
Claims (5)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI790067A FI59396C (en) | 1979-01-10 | 1979-01-10 | PROCEDURE FOR THE FRAMSTATION OF AV 2- (4-AMINO-3,5-DICHLOROPHENYL) -2-CARBOXY-N-TERT-BUTYL ACETAMIDER |
| DE19792942723 DE2942723A1 (en) | 1979-10-23 | 1979-10-23 | Prepn. of broncholytic phenyl-ethanolamine derivs. - via new 2-acyloxy-2-phenyl-acetamide derivs. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8000175L SE8000175L (en) | 1980-07-11 |
| SE447102B true SE447102B (en) | 1986-10-27 |
Family
ID=25781629
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8000175A SE447102B (en) | 1979-01-10 | 1980-01-09 | NEW ALFA ACYLOXY ACETAMIDS AND PROCEDURES FOR THEIR PREPARATION |
| SE8405631A SE452979B (en) | 1979-01-10 | 1984-11-09 | NEW PROCEDURE FOR THE PREPARATION OF PHENYLETANOLAMINES |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8405631A SE452979B (en) | 1979-01-10 | 1984-11-09 | NEW PROCEDURE FOR THE PREPARATION OF PHENYLETANOLAMINES |
Country Status (18)
| Country | Link |
|---|---|
| AT (1) | AT367398B (en) |
| BG (1) | BG33584A3 (en) |
| CA (1) | CA1146958A (en) |
| CH (1) | CH645611A5 (en) |
| CS (1) | CS214689B2 (en) |
| DD (2) | DD150198A5 (en) |
| DK (2) | DK159263C (en) |
| ES (1) | ES487548A0 (en) |
| GR (1) | GR74391B (en) |
| HU (2) | HU188207B (en) |
| NL (1) | NL8000126A (en) |
| NO (2) | NO148522C (en) |
| PL (2) | PL126876B1 (en) |
| PT (1) | PT70661A (en) |
| RO (1) | RO78779A (en) |
| SE (2) | SE447102B (en) |
| SU (1) | SU884563A3 (en) |
| YU (1) | YU4880A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR102020008433A2 (en) | 2020-04-28 | 2021-11-03 | Universidade Federal Do Parana | ARTHROPOD REPELLENTS OBTAINED FROM THE CHEMICAL TRANSFORMATION OF LACTIC ACID, LACTATES OR OTHER LACTIC ACID DERIVATIVES |
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1979
- 1979-12-24 BG BG7946027A patent/BG33584A3/en unknown
- 1979-12-28 NO NO794314A patent/NO148522C/en unknown
-
1980
- 1980-01-04 GR GR60893A patent/GR74391B/el unknown
- 1980-01-04 AT AT0003380A patent/AT367398B/en not_active IP Right Cessation
- 1980-01-04 SU SU802863255A patent/SU884563A3/en active
- 1980-01-07 CS CS80164A patent/CS214689B2/en unknown
- 1980-01-07 PT PT70661A patent/PT70661A/en not_active IP Right Cessation
- 1980-01-07 CH CH6680A patent/CH645611A5/en not_active IP Right Cessation
- 1980-01-08 DD DD80218350A patent/DD150198A5/en unknown
- 1980-01-08 CA CA000343261A patent/CA1146958A/en not_active Expired
- 1980-01-08 DK DK008480A patent/DK159263C/en not_active IP Right Cessation
- 1980-01-08 YU YU00048/80A patent/YU4880A/en unknown
- 1980-01-08 DD DD80227454A patent/DD156179A5/en unknown
- 1980-01-09 PL PL1980221288A patent/PL126876B1/en unknown
- 1980-01-09 SE SE8000175A patent/SE447102B/en not_active IP Right Cessation
- 1980-01-09 RO RO8099824A patent/RO78779A/en unknown
- 1980-01-09 HU HU8330A patent/HU188207B/en unknown
- 1980-01-09 PL PL1980234384A patent/PL126046B1/en unknown
- 1980-01-09 ES ES487548A patent/ES487548A0/en active Granted
- 1980-01-09 NL NL8000126A patent/NL8000126A/en not_active Application Discontinuation
- 1980-01-09 HU HU8041A patent/HU181681B/en unknown
-
1982
- 1982-09-17 NO NO823159A patent/NO148997C/en unknown
-
1984
- 1984-11-09 SE SE8405631A patent/SE452979B/en not_active IP Right Cessation
-
1989
- 1989-10-18 DK DK517289A patent/DK159262C/en not_active IP Right Cessation
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