NO131908B - - Google Patents
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- Publication number
- NO131908B NO131908B NO3347/71A NO334771A NO131908B NO 131908 B NO131908 B NO 131908B NO 3347/71 A NO3347/71 A NO 3347/71A NO 334771 A NO334771 A NO 334771A NO 131908 B NO131908 B NO 131908B
- Authority
- NO
- Norway
- Prior art keywords
- piperazine
- benzene
- methoxyphenyl
- mixture
- analysis
- Prior art date
Links
- -1 alkoxyalkyl halide Chemical class 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 96
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- 239000000203 mixture Substances 0.000 description 24
- 239000000047 product Substances 0.000 description 24
- 229910052739 hydrogen Inorganic materials 0.000 description 22
- 229910052799 carbon Inorganic materials 0.000 description 19
- 239000002585 base Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 238000010992 reflux Methods 0.000 description 13
- 238000009835 boiling Methods 0.000 description 11
- 239000000284 extract Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 229960005141 piperazine Drugs 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- ITNSQDCAZVVFMS-UHFFFAOYSA-N 1-(2-methoxyphenyl)-4-(3-methoxypropyl)piperazine Chemical compound C1CN(CCCOC)CCN1C1=CC=CC=C1OC ITNSQDCAZVVFMS-UHFFFAOYSA-N 0.000 description 5
- VNZLQLYBRIOLFZ-UHFFFAOYSA-N 1-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCNCC1 VNZLQLYBRIOLFZ-UHFFFAOYSA-N 0.000 description 5
- 206010020772 Hypertension Diseases 0.000 description 5
- 230000036772 blood pressure Effects 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 4
- FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000001631 hypertensive effect Effects 0.000 description 3
- JHEGFJPJFFDLIB-UHFFFAOYSA-N n,n-bis(2-chloroethyl)-2-methoxyaniline Chemical compound COC1=CC=CC=C1N(CCCl)CCCl JHEGFJPJFFDLIB-UHFFFAOYSA-N 0.000 description 3
- PEVHLEAAXLKMSZ-UHFFFAOYSA-N 7-methoxyheptan-1-amine Chemical compound COCCCCCCCN PEVHLEAAXLKMSZ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 208000032140 Sleepiness Diseases 0.000 description 2
- 206010041349 Somnolence Diseases 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 229940125717 barbiturate Drugs 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 150000004885 piperazines Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- NCOMQNWYMLGJPF-UHFFFAOYSA-N 1-(2-methoxyphenyl)-4-(3-methoxypropyl)piperazine;phosphoric acid Chemical compound OP(O)(O)=O.C1CN(CCCOC)CCN1C1=CC=CC=C1OC NCOMQNWYMLGJPF-UHFFFAOYSA-N 0.000 description 1
- ZYXMVSPWOATGIW-UHFFFAOYSA-N 1-(2-methoxyphenyl)-4-methylpiperazine Chemical compound COC1=CC=CC=C1N1CCN(C)CC1 ZYXMVSPWOATGIW-UHFFFAOYSA-N 0.000 description 1
- CEVMYGZHEJSOHZ-UHFFFAOYSA-N 1-bromo-3-methoxypropane Chemical compound COCCCBr CEVMYGZHEJSOHZ-UHFFFAOYSA-N 0.000 description 1
- LPFDVSDSQQLJMA-UHFFFAOYSA-N 1-bromo-8-methoxyoctane Chemical compound COCCCCCCCCBr LPFDVSDSQQLJMA-UHFFFAOYSA-N 0.000 description 1
- OGWXTWGOYZGJTH-UHFFFAOYSA-N 1-bromo-9-methoxynonane Chemical compound COCCCCCCCCCBr OGWXTWGOYZGJTH-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- ZRJOUVOXPWNFOF-UHFFFAOYSA-N 3-dodecoxypropan-1-amine Chemical compound CCCCCCCCCCCCOCCCN ZRJOUVOXPWNFOF-UHFFFAOYSA-N 0.000 description 1
- SOYBEXQHNURCGE-UHFFFAOYSA-N 3-ethoxypropan-1-amine Chemical compound CCOCCCN SOYBEXQHNURCGE-UHFFFAOYSA-N 0.000 description 1
- NWGJTXNNXLHFSE-UHFFFAOYSA-N 3-hexoxypropan-1-amine Chemical compound CCCCCCOCCCN NWGJTXNNXLHFSE-UHFFFAOYSA-N 0.000 description 1
- HWZUQAKHJDKBOE-UHFFFAOYSA-N 3-methoxypropyl 4-methylbenzenesulfonate Chemical compound COCCCOS(=O)(=O)C1=CC=C(C)C=C1 HWZUQAKHJDKBOE-UHFFFAOYSA-N 0.000 description 1
- VHYUNSUGCNKWSO-UHFFFAOYSA-N 3-propan-2-yloxypropan-1-amine Chemical compound CC(C)OCCCN VHYUNSUGCNKWSO-UHFFFAOYSA-N 0.000 description 1
- YUUFAJOXLZUDJG-UHFFFAOYSA-N 4-methoxybutan-1-amine Chemical compound COCCCCN YUUFAJOXLZUDJG-UHFFFAOYSA-N 0.000 description 1
- DMRHQYSRQGGRCK-UHFFFAOYSA-N 5-methoxypentan-1-amine Chemical compound COCCCCCN DMRHQYSRQGGRCK-UHFFFAOYSA-N 0.000 description 1
- UVOBODVSFRKUQX-UHFFFAOYSA-N 6-methoxyhexan-1-amine Chemical compound COCCCCCCN UVOBODVSFRKUQX-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 200000000007 Arterial disease Diseases 0.000 description 1
- 206010062542 Arterial insufficiency Diseases 0.000 description 1
- 206010052895 Coronary artery insufficiency Diseases 0.000 description 1
- 206010011703 Cyanosis Diseases 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 206010039710 Scleroderma Diseases 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000037007 arousal Effects 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000003457 ganglion blocking agent Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 201000009939 hypertensive encephalopathy Diseases 0.000 description 1
- 208000015210 hypertensive heart disease Diseases 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 239000005554 hypnotics and sedatives Substances 0.000 description 1
- 229940005535 hypnotics and sedatives Drugs 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- NQQWFVUVBGSGQN-UHFFFAOYSA-N phosphoric acid;piperazine Chemical compound OP(O)(O)=O.C1CNCCN1 NQQWFVUVBGSGQN-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229940080360 rauwolfia alkaloid Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01H—ELECTRIC SWITCHES; RELAYS; SELECTORS; EMERGENCY PROTECTIVE DEVICES
- H01H33/00—High-tension or heavy-current switches with arc-extinguishing or arc-preventing means
- H01H33/70—Switches with separate means for directing, obtaining, or increasing flow of arc-extinguishing fluid
- H01H33/72—Switches with separate means for directing, obtaining, or increasing flow of arc-extinguishing fluid having stationary parts for directing the flow of arc-extinguishing fluid, e.g. arc-extinguishing chamber
- H01H33/75—Liquid-break switches, e.g. oil-break
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01H—ELECTRIC SWITCHES; RELAYS; SELECTORS; EMERGENCY PROTECTIVE DEVICES
- H01H3/00—Mechanisms for operating contacts
- H01H3/60—Mechanical arrangements for preventing or damping vibration or shock
Landscapes
- Circuit Breakers (AREA)
- Driving Mechanisms And Operating Circuits Of Arc-Extinguishing High-Tension Switches (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1347270A CH521011A (de) | 1970-09-10 | 1970-09-10 | Olarmer Leistungsschalter |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO131908B true NO131908B (pl) | 1975-05-12 |
| NO131908C NO131908C (pl) | 1975-08-20 |
Family
ID=4392731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3347/71A NO131908C (pl) | 1970-09-10 | 1971-09-08 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3742168A (pl) |
| AT (1) | AT308230B (pl) |
| AU (1) | AU456609B2 (pl) |
| BE (1) | BE772332A (pl) |
| BR (1) | BR7105893D0 (pl) |
| CA (1) | CA936199A (pl) |
| CH (1) | CH521011A (pl) |
| DE (2) | DE7037094U (pl) |
| ES (1) | ES394893A1 (pl) |
| FR (1) | FR2107418A5 (pl) |
| GB (1) | GB1316380A (pl) |
| NL (1) | NL7112340A (pl) |
| NO (1) | NO131908C (pl) |
| PL (1) | PL77828B1 (pl) |
| SE (1) | SE380129B (pl) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2548280B1 (fr) * | 1983-06-30 | 1987-08-07 | Paris & Du Rhone | Perfectionnements aux contacteurs de demarreur electrique dont l'axe est independant du noyau mobile |
| NO321080B1 (no) * | 2004-11-04 | 2006-03-13 | Bennex As | Bryter for høy spenning og/eller strøm |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE472305C (de) * | 1927-10-30 | 1929-02-26 | Siemens Schuckertwerke Akt Ges | Loeschkammer fuer Schalter |
| DE1298176B (de) * | 1961-12-23 | 1969-06-26 | Calor Emag Elektrizitaets Ag | Elektrischer Schalter mit Lichtbogenloeschung durch eine Loeschmittelstroemung |
-
1970
- 1970-09-10 CH CH1347270A patent/CH521011A/de not_active IP Right Cessation
- 1970-10-07 DE DE7037094U patent/DE7037094U/de not_active Expired
- 1970-10-07 DE DE19702049265 patent/DE2049265A1/de active Pending
-
1971
- 1971-06-14 AT AT510771A patent/AT308230B/de not_active IP Right Cessation
- 1971-07-26 AU AU31626/71A patent/AU456609B2/en not_active Expired
- 1971-08-19 US US00172970A patent/US3742168A/en not_active Expired - Lifetime
- 1971-08-25 CA CA121498A patent/CA936199A/en not_active Expired
- 1971-09-08 FR FR7132403A patent/FR2107418A5/fr not_active Expired
- 1971-09-08 PL PL1971150401A patent/PL77828B1/pl unknown
- 1971-09-08 ES ES394893A patent/ES394893A1/es not_active Expired
- 1971-09-08 BE BE772332A patent/BE772332A/xx unknown
- 1971-09-08 NO NO3347/71A patent/NO131908C/no unknown
- 1971-09-08 BR BR5893/71A patent/BR7105893D0/pt unknown
- 1971-09-08 SE SE7111399A patent/SE380129B/xx unknown
- 1971-09-08 GB GB4189971A patent/GB1316380A/en not_active Expired
- 1971-09-08 NL NL7112340A patent/NL7112340A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO131908C (pl) | 1975-08-20 |
| DE7037094U (de) | 1971-08-19 |
| AT308230B (de) | 1973-06-25 |
| SE380129B (pl) | 1975-10-27 |
| CH521011A (de) | 1972-03-31 |
| BE772332A (fr) | 1972-01-17 |
| ES394893A1 (es) | 1974-05-16 |
| US3742168A (en) | 1973-06-26 |
| CA936199A (en) | 1973-10-30 |
| BR7105893D0 (pt) | 1973-03-29 |
| AU456609B2 (en) | 1974-12-19 |
| NL7112340A (pl) | 1972-03-14 |
| AU3162671A (en) | 1973-02-01 |
| DE2049265A1 (de) | 1972-03-16 |
| FR2107418A5 (pl) | 1972-05-05 |
| GB1316380A (en) | 1973-05-09 |
| PL77828B1 (pl) | 1975-04-30 |
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