NO753391L - - Google Patents
Info
- Publication number
- NO753391L NO753391L NO753391A NO753391A NO753391L NO 753391 L NO753391 L NO 753391L NO 753391 A NO753391 A NO 753391A NO 753391 A NO753391 A NO 753391A NO 753391 L NO753391 L NO 753391L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- indolyloxy
- alkyl
- mixture
- hydroxy
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 3
- -1 arylsulfonyl chloride Chemical compound 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- FNZTVUHCYCHOFH-UHFFFAOYSA-N 3-(1h-indol-4-yloxy)propane-1,2-diol Chemical class OCC(O)COC1=CC=CC2=C1C=CN2 FNZTVUHCYCHOFH-UHFFFAOYSA-N 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 150000002894 organic compounds Chemical class 0.000 abstract description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000003087 receptor blocking agent Substances 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Organiske forbindelser samt fremgangsmåte for deres fremstilling.Organic compounds and methods for their production.
Description
Foreliggende oppfinnelse angår nye organiske forbindelser som er verdifulle mellomprodukter ved fremstilling av 4~(2~hydroksy-*3~ isopropylaminoprpoksy)-indol samt fremgangsmåte for fremstilling av disse som mellomprodukter frembragte nye organiske forbindelser. The present invention relates to new organic compounds which are valuable intermediates in the production of 4~(2~hydroxy-*3~ isopropylaminopropoxy)-indole as well as a method for producing these as intermediates produced new organic compounds.
Nevnte 4-(2-hydroksy-S-isopropylarainopropoksy)-indol med formelen Said 4-(2-hydroxy-S-isopropylarainopropoxy)-indole of the formula
er kjent på grunn av sine farmakologiske egenskaper. Den er en kardioselektiv Ø-reseptor-blokkerer (blocking agent) og har så-ledes funnet anvendelse ved behandling av angina pectoris og rytmeforstyrrelser i hjertet. De nye organiske forbindelser ifølge oppfinnelsen karakteriseres av att de har formelen hvor R er en alkyl- eller arylgruppe. Karakteriserende for fremgangsmåten ifølge oppfinnelsen er, at 4~(l,2-dihydroksypropoksy)-indol med formel får reagere med en alkyl- eller arylsulfonylklorid med formelen is known for its pharmacological properties. It is a cardioselective Ø-receptor blocker (blocking agent) and has thus found application in the treatment of angina pectoris and heart rhythm disturbances. The new organic compounds according to the invention are characterized by having the formula where R is an alkyl or aryl group. Characterizing the method according to the invention is that 4~(1,2-dihydroxypropoxy)-indole with the formula is allowed to react with an alkyl or arylsulfonyl chloride with the formula
hvor R har den betydning som er angitt ovenfor. Reaksjonen kan ut-føres i en basisk vannløsning eller et vannfritt organisk løsnings-middel i nærvær av en egnet aromatisk amin»så som pyridin. where R has the meaning given above. The reaction can be carried out in a basic water solution or an anhydrous organic solvent in the presence of a suitable aromatic amine such as pyridine.
Egnete organiske løsningsmidler er f.eks. kloroform og dimetylformamid. Suitable organic solvents are e.g. chloroform and dimethylformamide.
Forbindelsene ifølge oppfinnelsen byr en industriell fordelaktig og Økonomisk måte å fremstille isopropylamin ifølge den generelle formelen I, Herunder får et esterderivat ifølge den generelle formelen II reagere med en isopropylamin med formelen The compounds according to the invention offer an industrially advantageous and economical way to prepare isopropylamine according to the general formula I, Herein, an ester derivative according to the general formula II is allowed to react with an isopropylamine with the formula
Denne reaksjonen skjer lett og ved værelsestempøratur som løsningsmiddel benyttes f.eks. dimetylformamid. This reaction takes place easily and at room temperature e.g. dimethylformamide.
Oppfinnelsen beskrives nærmere i de etterfølgende eksemplene. The invention is described in more detail in the following examples.
Eksempel 1Example 1
2- Hydroksy- 3- ( 4- indolyloksy) - propylester av p- toluensulfonsyre. 2-Hydroxy-3-(4-indolyloxy)-propyl ester of p-toluenesulfonic acid.
6»2 g 4-(l,2-dihydroksypropoksy)-indol ble løst i en blanding, bestående av 15 g pyridin og 6 g diroetylforraamid. Blandingen ble kjølt til 0-5° og 6 g p-toluensulfonylklorid ble tilsatt i små porsjoner slik at blandingens temperatur holdt seg ved 0~5°C. Etter at all klorid var tilsatt ble kjølningen avbrutt og om-røringen fikk fortsette i ytterligere tre timer. Reaksjonsbland-ingen ble helt i 50 ml kaldt vann og surgjort med saltsyre. Produktet ble ekstrahert i kloroform, som ble vasket med vann og tørket med Na2SO^og inndampet. Den frembragte p-toluønsulfon-syrens 2-hydroksy~3-(4-indolyloksy)-propylester, var under disse forhold en viskøs olje og utbyttet var 10 g. 6.2 g of 4-(1,2-dihydroxypropoxy)-indole was dissolved in a mixture consisting of 15 g of pyridine and 6 g of diroethylformamide. The mixture was cooled to 0-5° and 6 g of p-toluenesulfonyl chloride was added in small portions so that the temperature of the mixture remained at 0-5°C. After all the chloride had been added, the cooling was interrupted and the stirring was allowed to continue for a further three hours. The reaction mixture was poured into 50 ml of cold water and acidified with hydrochloric acid. The product was extracted into chloroform, which was washed with water and dried with Na 2 SO 4 and evaporated. The p-toluenesulfonic acid 2-hydroxy~3-(4-indolyloxy)-propyl ester produced was, under these conditions, a viscous oil and the yield was 10 g.
Eksempel 2Example 2
4-( 2 - hydroksy- 3- i s op ropy1aminopropok sy)- indo14-( 2 - hydroxy- 3- i s op ropy1aminopropok sy)- indo1
10 g 2-hydroksy-3-(4-indolyloksy)-propylester av p-toluensulfonsyre, 12 g isopropylamin 'og 20 ml dimetylformamid ble blandet. Denne blanding ble omrørt i to døgn ved værelsestemperatur og deretter inndampet. 30 ml vann ble tilsatt og blandingen gjort sterkt basisk med natriumhydroksyd. Blandingen ble ekstrahert en rekke ganger med kloroform under oppvarming. De forente kloroform-ekstrakter ble vasket med vann og tørket med Na^SO^og inndampet. 5,5 g rå 3~isopropylaminopropoksy-indol.ble frembragt. Produktene krystalliseres av alkohol»idet deres smeltepunkt var 170-171°C. 10 g of 2-hydroxy-3-(4-indolyloxy)-propyl ester of p-toluenesulfonic acid, 12 g of isopropylamine and 20 ml of dimethylformamide were mixed. This mixture was stirred for two days at room temperature and then evaporated. 30 ml of water was added and the mixture made strongly basic with sodium hydroxide. The mixture was extracted several times with chloroform while heating. The combined chloroform extracts were washed with water and dried with Na 2 SO 4 and evaporated. 5.5 g of crude 3-isopropylaminopropoxyindole was produced. The products are crystallized from alcohol, their melting point being 170-171°C.
Claims (2)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI3807/74A FI50791B (en) | 1974-12-31 | 1974-12-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO753391L true NO753391L (en) | 1976-07-01 |
Family
ID=8508759
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO753391A NO753391L (en) | 1974-12-31 | 1975-10-08 |
Country Status (4)
| Country | Link |
|---|---|
| DK (1) | DK510675A (en) |
| FI (1) | FI50791B (en) |
| NO (1) | NO753391L (en) |
| SE (1) | SE7511194L (en) |
-
1974
- 1974-12-31 FI FI3807/74A patent/FI50791B/fi active
-
1975
- 1975-10-07 SE SE7511194A patent/SE7511194L/en unknown
- 1975-10-08 NO NO753391A patent/NO753391L/no unknown
- 1975-11-13 DK DK510675A patent/DK510675A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE7511194L (en) | 1976-07-01 |
| FI50791B (en) | 1976-03-31 |
| DK510675A (en) | 1976-07-01 |
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