NO123817B - - Google Patents
Download PDFInfo
- 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)
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 (fr) | 1972-01-17 |
Family
ID=24930296
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1966/69A NO123817B (fr) | 1968-05-15 | 1969-05-13 |
Country Status (6)
| Country | Link |
|---|---|
| DE (1) | DE1923654A1 (fr) |
| FR (1) | FR2008593A1 (fr) |
| GB (1) | GB1269080A (fr) |
| IE (1) | IE32687B1 (fr) |
| NO (1) | NO123817B (fr) |
| SE (1) | SE354344B (fr) |
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 |
|---|---|
| FR2008593A1 (fr) | 1970-01-23 |
| SE354344B (sv) | 1973-03-05 |
| IE32687L (en) | 1969-11-15 |
| GB1269080A (en) | 1972-03-29 |
| DE1923654A1 (de) | 1969-11-27 |
| IE32687B1 (en) | 1973-10-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Jones | The synthesis of some amines and amino acids containing the pyrazole nucleus | |
| US3810906A (en) | N1-heteroacylated phenylhydrazines | |
| NO164476B (no) | Analogifremgangsmaate ved fremstilling av terapeutisk virksomme 1,2,3,5-tetrahydroimidazo-(2,1-b)-kinazoliner. | |
| CH398626A (de) | Verfahren zur Herstellung neuer Pyrazolopyrimidine | |
| NO127607B (fr) | ||
| US3265692A (en) | Process for the preparation of oxadiazole derivatives | |
| DE1545925A1 (de) | Neue Pyrrolidinderivate und Verfahren zur Herstellung derselben | |
| US2416258A (en) | 3-(5-ethoxy-3-indolyl)-propyl compounds | |
| NO128157B (fr) | ||
| NO123817B (fr) | ||
| Toki | Studies on sarkomycin–optically active 2-methylenecyclopentanone-3-carboxylic acids | |
| NO127054B (fr) | ||
| US3056796A (en) | 2.8-diazaspiro(4.5)decane-1.3 diones | |
| US2793212A (en) | Substituted benzamidopiperidinopropanes | |
| NO128543B (fr) | ||
| BOSE et al. | Some Derivatives of Glycineamidine1 | |
| US2841590A (en) | Indole derivatives | |
| SU468423A3 (ru) | Способ получени 6-аза-3н-1,4-бензодиазепинов | |
| JPS5930703B2 (ja) | 血糖降下作用を有するインド−ルカルボン酸誘導体の製法 | |
| NO116314B (fr) | ||
| US2724710A (en) | 4-pyridazinecarboxylic acid and salts thereof with bases | |
| US3438976A (en) | 1-sulfonyl-3-nortropanyl-urea derivatives | |
| CH546742A (de) | Verfahren zur herstellung von methoxyamin-derivaten und ihren salzen. | |
| NO126453B (fr) | ||
| US3265696A (en) | Pyridylethylated 4 (1h)-quinazolinones and derivatives thereof |