NO133068B - - Google Patents
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- Publication number
- NO133068B NO133068B NO305370A NO305370A NO133068B NO 133068 B NO133068 B NO 133068B NO 305370 A NO305370 A NO 305370A NO 305370 A NO305370 A NO 305370A NO 133068 B NO133068 B NO 133068B
- Authority
- NO
- Norway
- Prior art keywords
- phosphoric acid
- hydroxy
- acid ester
- indole
- dibenzyl
- Prior art date
Links
- 229940054051 antipsychotic indole derivative Drugs 0.000 claims description 6
- 150000002475 indoles Chemical class 0.000 claims description 6
- NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical class OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 239000011574 phosphorus Substances 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- -1 lithium aluminum hydride Chemical compound 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- SMVXYBYTGKEHCS-UHFFFAOYSA-N [benzyl(chloro)phosphoryl]methylbenzene Chemical compound C=1C=CC=CC=1CP(=O)(Cl)CC1=CC=CC=C1 SMVXYBYTGKEHCS-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- HDFFVHSMHLDSLO-UHFFFAOYSA-N Dibenzyl phosphate Chemical compound C=1C=CC=CC=1COP(=O)(O)OCC1=CC=CC=C1 HDFFVHSMHLDSLO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- BCBIDTUKRGWHPL-UHFFFAOYSA-N 3-[2-(dimethylamino)ethyl]-1h-indol-4-ol;phosphoric acid Chemical compound OP(O)(O)=O.C1=CC(O)=C2C(CCN(C)C)=CNC2=C1 BCBIDTUKRGWHPL-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- SPCIYGNTAMCTRO-UHFFFAOYSA-N psilocin Chemical compound C1=CC(O)=C2C(CCN(C)C)=CNC2=C1 SPCIYGNTAMCTRO-UHFFFAOYSA-N 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- QTERVOZQCNPERI-UHFFFAOYSA-N 1h-indole;phosphoric acid Chemical compound OP(O)(O)=O.C1=CC=C2NC=CC2=C1 QTERVOZQCNPERI-UHFFFAOYSA-N 0.000 description 1
- KSDRYRLZDHZMDM-UHFFFAOYSA-N 2-(4-phenylmethoxy-1h-indol-3-yl)ethanamine Chemical compound C=12C(CCN)=CNC2=CC=CC=1OCC1=CC=CC=C1 KSDRYRLZDHZMDM-UHFFFAOYSA-N 0.000 description 1
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 1
- RVBHLXCWKWOISZ-UHFFFAOYSA-N 3-(2-piperidin-1-ylethyl)-1h-indol-4-ol Chemical compound C1=2C(O)=CC=CC=2NC=C1CCN1CCCCC1 RVBHLXCWKWOISZ-UHFFFAOYSA-N 0.000 description 1
- OHHYMKDBKJPILO-UHFFFAOYSA-N 3-[2-(diethylamino)ethyl]-1h-indol-4-ol Chemical compound C1=CC(O)=C2C(CCN(CC)CC)=CNC2=C1 OHHYMKDBKJPILO-UHFFFAOYSA-N 0.000 description 1
- LJFVSIDBFJPKLD-UHFFFAOYSA-N 4-phenylmethoxy-1h-indole Chemical compound C=1C=CC=2NC=CC=2C=1OCC1=CC=CC=C1 LJFVSIDBFJPKLD-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 208000006550 Mydriasis Diseases 0.000 description 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 235000005811 Viola adunca Nutrition 0.000 description 1
- 240000009038 Viola odorata Species 0.000 description 1
- 235000013487 Viola odorata Nutrition 0.000 description 1
- 235000002254 Viola papilionacea Nutrition 0.000 description 1
- 244000172533 Viola sororia Species 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000011083 clear filtration Methods 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- RQKYHDHLEMEVDR-UHFFFAOYSA-N oxo-bis(phenylmethoxy)phosphanium Chemical compound C=1C=CC=CC=1CO[P+](=O)OCC1=CC=CC=C1 RQKYHDHLEMEVDR-UHFFFAOYSA-N 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical class C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01F—PROCESSING OF HARVESTED PRODUCE; HAY OR STRAW PRESSES; DEVICES FOR STORING AGRICULTURAL OR HORTICULTURAL PRODUCE
- A01F25/00—Storing agricultural or horticultural produce; Hanging-up harvested fruit
- A01F25/04—Stacks, ricks or the like
- A01F25/045—Distributing arrangements in haystacks
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
- B65G—TRANSPORT OR STORAGE DEVICES, e.g. CONVEYORS FOR LOADING OR TIPPING, SHOP CONVEYOR SYSTEMS OR PNEUMATIC TUBE CONVEYORS
- B65G53/00—Conveying materials in bulk through troughs, pipes or tubes by floating the materials or by flow of gas, liquid or foam
- B65G53/34—Details
- B65G53/52—Adaptations of pipes or tubes
Landscapes
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental Sciences (AREA)
- Cleaning In General (AREA)
- Extrusion Moulding Of Plastics Or The Like (AREA)
- Specific Conveyance Elements (AREA)
- Indole Compounds (AREA)
- Feeding And Watering For Cattle Raising And Animal Husbandry (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1226769A CH502940A (de) | 1967-06-07 | 1969-08-11 | Heuförder- und -Verteileranlage mit Gebläse |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO133068B true NO133068B (de) | 1975-11-24 |
| NO133068C NO133068C (de) | 1976-03-03 |
Family
ID=4381425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO305370A NO133068C (de) | 1969-08-11 | 1970-08-10 |
Country Status (11)
| Country | Link |
|---|---|
| AT (1) | AT306632B (de) |
| BE (1) | BE754480A (de) |
| CH (1) | CH505743A (de) |
| DE (2) | DE6933544U (de) |
| DK (1) | DK140081B (de) |
| ES (1) | ES382503A1 (de) |
| FR (1) | FR2057910A5 (de) |
| GB (1) | GB1279164A (de) |
| NL (1) | NL7011866A (de) |
| NO (1) | NO133068C (de) |
| SE (1) | SE354835B (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3114137A1 (de) * | 1981-04-08 | 1982-11-04 | Johannes Stieve GmbH, 4520 Melle | Foerdereinrichtung, insbesondere fuer landwirtschaftliches erntegut |
| CN107810723B (zh) * | 2017-11-20 | 2020-09-15 | 安徽德鑫源食品有限公司 | 智能控制的恒压型储粮设备 |
-
1969
- 1969-08-11 CH CH1187670A patent/CH505743A/de not_active IP Right Cessation
- 1969-08-25 AT AT810869A patent/AT306632B/de not_active IP Right Cessation
- 1969-08-26 DE DE19696933544 patent/DE6933544U/de not_active Expired
- 1969-08-26 DE DE19691943334 patent/DE1943334B2/de not_active Ceased
-
1970
- 1970-07-31 FR FR7028438A patent/FR2057910A5/fr not_active Expired
- 1970-08-04 SE SE1065570A patent/SE354835B/xx unknown
- 1970-08-06 ES ES382503A patent/ES382503A1/es not_active Expired
- 1970-08-06 BE BE754480D patent/BE754480A/xx unknown
- 1970-08-07 GB GB3819470A patent/GB1279164A/en not_active Expired
- 1970-08-10 NO NO305370A patent/NO133068C/no unknown
- 1970-08-10 DK DK408870A patent/DK140081B/da unknown
- 1970-08-11 NL NL7011866A patent/NL7011866A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH505743A (de) | 1971-04-15 |
| BE754480A (fr) | 1971-01-18 |
| AT306632B (de) | 1973-04-25 |
| SE354835B (de) | 1973-03-26 |
| ES382503A1 (es) | 1972-12-01 |
| GB1279164A (en) | 1972-06-28 |
| DE6933544U (de) | 1970-12-10 |
| DK140081B (da) | 1979-06-18 |
| NL7011866A (de) | 1971-02-15 |
| DE1943334B2 (de) | 1974-07-25 |
| NO133068C (de) | 1976-03-03 |
| FR2057910A5 (de) | 1971-05-21 |
| DE1943334A1 (de) | 1971-02-25 |
| DK140081C (de) | 1979-11-19 |
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