NO123817B - - Google Patents
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- Publication number
- NO123817B NO123817B NO1966/69A NO196669A NO123817B NO 123817 B NO123817 B NO 123817B NO 1966/69 A NO1966/69 A NO 1966/69A NO 196669 A NO196669 A NO 196669A NO 123817 B NO123817 B NO 123817B
- Authority
- NO
- Norway
- Prior art keywords
- carboxylic acid
- ethylindole
- solution
- indole derivatives
- dimethylamine
- Prior art date
Links
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 229940054051 antipsychotic indole derivative Drugs 0.000 claims description 5
- 150000002475 indoles Chemical class 0.000 claims description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- XOALTXJYIZPUCD-UHFFFAOYSA-N 3-ethyl-1h-indole-2-carboxylic acid Chemical compound C1=CC=C2C(CC)=C(C(O)=O)NC2=C1 XOALTXJYIZPUCD-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- -1 for example Chemical compound 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- HZLHZWIVSRYPEV-UHFFFAOYSA-N 3-ethyl-1H-indole-2-carboxamide Chemical compound C(C)C1=C(NC2=CC=CC=C12)C(=O)N HZLHZWIVSRYPEV-UHFFFAOYSA-N 0.000 description 2
- HYGCGTNJRRNCGP-UHFFFAOYSA-N 3-ethyl-n-methyl-1h-indole-2-carboxamide Chemical compound C1=CC=C2C(CC)=C(C(=O)NC)NC2=C1 HYGCGTNJRRNCGP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000004519 manufacturing process Methods 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
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- IPCFRNXNJNVMTM-UHFFFAOYSA-N 3-ethyl-1H-indole-2-carbonyl azide Chemical compound C(C)C1=C(NC2=CC=CC=C12)C(=O)N=[N+]=[N-] IPCFRNXNJNVMTM-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241001279009 Strychnos toxifera Species 0.000 description 1
- 208000010513 Stupor Diseases 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- CLRSZXHOSMKUIB-UHFFFAOYSA-M benzenediazonium chloride Chemical compound [Cl-].N#[N+]C1=CC=CC=C1 CLRSZXHOSMKUIB-UHFFFAOYSA-M 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- PUTGRHQJZXLFEJ-UHFFFAOYSA-N ethyl 3-ethyl-1h-indole-2-carboxylate Chemical compound C1=CC=C2C(CC)=C(C(=O)OCC)NC2=C1 PUTGRHQJZXLFEJ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229940070710 valerate Drugs 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
- E06B7/00—Special arrangements or measures in connection with doors or windows
- E06B7/02—Special arrangements or measures in connection with doors or windows for providing ventilation, e.g. through double windows; Arrangement of ventilation roses
- E06B7/04—Special arrangements or measures in connection with doors or windows for providing ventilation, e.g. through double windows; Arrangement of ventilation roses with ventilation wings
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F24—HEATING; RANGES; VENTILATING
- F24F—AIR-CONDITIONING; AIR-HUMIDIFICATION; VENTILATION; USE OF AIR CURRENTS FOR SCREENING
- F24F7/00—Ventilation
-
- 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
- E06B7/00—Special arrangements or measures in connection with doors or windows
- E06B7/02—Special arrangements or measures in connection with doors or windows for providing ventilation, e.g. through double windows; Arrangement of ventilation roses
- E06B7/04—Special arrangements or measures in connection with doors or windows for providing ventilation, e.g. through double windows; Arrangement of ventilation roses with ventilation wings
- E06B7/06—Special arrangements or measures in connection with doors or windows for providing ventilation, e.g. through double windows; Arrangement of ventilation roses with ventilation wings with one ventilation wing only
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F24—HEATING; RANGES; VENTILATING
- F24F—AIR-CONDITIONING; AIR-HUMIDIFICATION; VENTILATION; USE OF AIR CURRENTS FOR SCREENING
- F24F13/00—Details common to, or for air-conditioning, air-humidification, ventilation or use of air currents for screening
- F24F13/08—Air-flow control members, e.g. louvres, grilles, flaps or guide plates
Landscapes
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Civil Engineering (AREA)
- Structural Engineering (AREA)
- Hinges (AREA)
- Specific Sealing Or Ventilating Devices For Doors And Windows (AREA)
- Indole Compounds (AREA)
Description
Fremgangsmåte for fremstilling av terapeutisk virksomme indolderivater.
Nærværende oppfinnelse vedrører en
fremgangsmåte for fremstilling av nye indolderivater, som har verdifulle terapeu-tiske egenskaper.
De nye indolderivater etter nærværende oppfinnelse består av forbindelsene med
følgende generelle formel I:
i hvilken A betyr en enkel binding eller en
-NH-gruppe, og Ri og Ra er samme eller forskjellige og betyr vannstof f atomer eller
metylgrupper.
Ifølge nærværende oppfinnelse fremstilles nevnte indolderivater ved innvirkning av ammoniakk, et hydrazin eller mo-no- eller dimetylamin på et egnet derivat
av 3-etylindol-2-karboksylsyre som, f. eks.,
syrekloridet, azidet eller en ester. Reaksjo-nen utføres under betingelser normalt an-vendt for omdannelsen av et karboksyl-syrederivat til det tilsvarende amid eller
hydrazid.
Forbindelsene etter oppfinnelsen er
særlig virksomme som antikonvulsante og
medullære undertrykkere. Den siste egen-skap kan demonstreres f. eks. som antago-nistisk virkning mot stryknin [se f. eks.
F. M. Berger, Pharmaceutical Reviews 2,
274 (1949)]. De er også effektive når brukt
i tilstrekkelig høy dosering som potentiato-rer for narkose. De kan brukes som ikke hypnotiske sedativer, særlig ved behand-ling av angstfornemmelser og nervøse li-delser. På grunn av sine sedative egenskaper har de også en gunstig effekt ved be-handling av forhøyd blodtrykk. Spesielle forbindelser av særlig betydning er: 3-etylindol-2-karboksylsyre-hydrazid, 3-etylindol-2-karboksylsyre-dimetylamid, 3-etylindol-2-karboksylsyre-monometyl-amid og 3-etylindol-2-karboksylsyre-amid. Oppfinnelsen kan illustreres ved føl-gende eksempler; de angitte smeltepunk-ter er bestemt med Koflerapparatet.
Eksempel 1: Etyl-3-etylidol-2-karboksylat (51 g) og-hydrazinhydrat (120 cm<3>) oppvarmes under tilbakeløp i 3 timer. Ved avkjøling skilles det faste fra, vaskes med vann (4 x 125 cm<3>) og tørres i vakuum. 3-etylindol-2-karbok sylsyrehydrazid (46,5 g) oppnås, sm.p. 183° C.
Etyl-3-etylindol-2-karboksylat (sm.p. 124° C) oppnås ved innvirkning av ben-zendiazoniumklorid på et etyl-a-acetyl-va-lerat i alkoholisk kalium (Burton, Am. Chem. Journ. 3, 385 (1881).
Eksempel 2:
En oppløsning i eter av 3-etylindol-2-karboksylsyre-azid fremstilles ved innvirkning på 3-etylindol-2-karboksylsyrehydra-zid (34 g) (oppnådd som i eksempel 1) i dioksan (750 cm<3>) av natriumnitrit (12 g) oppløst i vann (150 cm<3>) fulgt av n-saltsyre (20 cm<3>), idet temperaturen holdes ved ca. +4° C, fulgt av fortynning med vann (1500 cm<3>) og gjenoppløsning av det faste stoff i eter (300 cm<3>). Til den slik oppnådde oppløsning tilsettes derpå en oppløsning av dimetylamin (150 g) i eter (500 cm<3>) under omrøring, idet temperaturen holdes ved ca. 0° C. Blandingen røres i en time og tillates å stå over natten ved 0° C. Eteroppløsnin-gen rystes med en mettet vandig oppløsning av natrium-bikarbonat (300 cm<3>), kloro-form (300 cm<3>) tilsettes, og det organiske lag skilles fra, vaskes med vann og tørres over kaliumkarbonat. Etter fordampning av oppløsningsmidlet oppløses resten i ko-kende benzol (100 cm<3>) varm n-heptan (100 cm<3>) tilsettes, og oppløsningen las krystallisere. Krystallene skilles fra, vaskes med heptan og tørkes i vakuum. 3-etyl-indol-2-karboksylsyre-dimetylamid (22,5
g) oppnås således, sm.p. 154° C.
Eksempel 3: Ved å gå frem som i eksempel 2, men gå ut fra 3-etylindol-2-karboksylsyrehydra-zid (12,2 g) og monometylamin (50 g) oppnås 3-etylindol-2-karboksylsyre-monome-tylamid (8,5 g), sm. p. 186° C.
Eksempel 4: 3-etylindol-2-karboksylsyre (18,9 g) tilsettes i små porsjoner ved vanlig temperatur til en oppløsning av tionylklorid (13,1
g) i toluol (50 cm<3>). Blandingen røres ved 25° C i 30 minutter og oppvarmes derpå
langsomt til en temperatur på 76° C. En klar oppløsning oppnås, som kjøles til ca. + 5° C. Flytende dimetylamin (27 g) tilsettes derpå dråpevis, idet temperaturen holdes ved +5° C. Blandingen las henstå over
natt i kjøleskap. Det krystallinske produkt skilles fra, vaskes først med toluol og derpå med en stor mengde vann. Produktet tør-res, og 3-etylindol-2-karboksylsyre-dime-tylamid (16 g), sm. p. 152—153° C, oppnås således. Ved fordampning av toluoloppløs-ningene oppnås en annen felling (4 g), sm. p. 150—151° C. Etter omkrystallisering fra benzol oppnås et rent produkt (17 g), sm. p. 154° C.
Eksempel 5: Ved å gå frem som i eksempel 3, men erstatte monometylamin med ammoniakk (20 g), oppnås der 3-etylindol-2-karboksyl-syre-amid (5,6 g), sm. p. 134° C, fulgt av gjenstørkning og et annet smeltepunkt ved 140° C.
Claims (1)
- Fremgangsmåte for fremstilling av terapeutisk virksomme indolderivater, karakterisert ved at ammoniakk, et hydrazin eller mono- eller dimetylamin reageres med et syrehalogenid eller en ester eller azidet av 3-etylindol-2-karboksylsyre for å danne en forbindelse med formelen:i hvilken A betyr en enkelt binding eller en -NH-gruppe, og Ri og R2 er samme eller forskjellige og betyr vannstof f atomer eller metylgrupper.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72926968A | 1968-05-15 | 1968-05-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO123817B true NO123817B (no) | 1972-01-17 |
Family
ID=24930296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1966/69A NO123817B (no) | 1968-05-15 | 1969-05-13 |
Country Status (6)
| Country | Link |
|---|---|
| DE (1) | DE1923654A1 (no) |
| FR (1) | FR2008593A1 (no) |
| GB (1) | GB1269080A (no) |
| IE (1) | IE32687B1 (no) |
| NO (1) | NO123817B (no) |
| SE (1) | SE354344B (no) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL8901594A (nl) * | 1989-06-23 | 1991-01-16 | Giemeta Luvema Bv | Ventilatie-inrichting. |
| BE1013930A3 (nl) * | 2001-01-24 | 2002-12-03 | Aralco Nv | Verbeterd verluchtingsrooster. |
-
1969
- 1969-04-18 GB GB09987/69A patent/GB1269080A/en not_active Expired
- 1969-04-25 IE IE571/69A patent/IE32687B1/xx unknown
- 1969-05-09 DE DE19691923654 patent/DE1923654A1/de active Pending
- 1969-05-13 NO NO1966/69A patent/NO123817B/no unknown
- 1969-05-14 SE SE06875/69A patent/SE354344B/xx unknown
- 1969-05-14 FR FR6915717A patent/FR2008593A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| GB1269080A (en) | 1972-03-29 |
| IE32687L (en) | 1969-11-15 |
| DE1923654A1 (de) | 1969-11-27 |
| SE354344B (sv) | 1973-03-05 |
| FR2008593A1 (fr) | 1970-01-23 |
| IE32687B1 (en) | 1973-10-31 |
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