NO128798B - - Google Patents
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- Publication number
- NO128798B NO128798B NO00068/71A NO6871A NO128798B NO 128798 B NO128798 B NO 128798B NO 00068/71 A NO00068/71 A NO 00068/71A NO 6871 A NO6871 A NO 6871A NO 128798 B NO128798 B NO 128798B
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- water
- piperidine
- soluble
- ether
- Prior art date
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 11
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 8
- 239000000126 substance Substances 0.000 description 6
- QKSGIGXOKHZCQZ-UHFFFAOYSA-N 2-chloro-2-phenylacetic acid Chemical class OC(=O)C(Cl)C1=CC=CC=C1 QKSGIGXOKHZCQZ-UHFFFAOYSA-N 0.000 description 4
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000002048 spasmolytic effect Effects 0.000 description 3
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- 230000000954 anitussive effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229960004126 codeine Drugs 0.000 description 2
- 150000001875 compounds Chemical group 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003589 local anesthetic agent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 2
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 2
- 229960004919 procaine Drugs 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- XDXXBFXNXAGXIA-UHFFFAOYSA-N 1-butan-2-yloxyethanol Chemical compound CCC(C)OC(C)O XDXXBFXNXAGXIA-UHFFFAOYSA-N 0.000 description 1
- FGEAOSXMQZWHIQ-UHFFFAOYSA-N 2-chloro-2-phenylacetyl chloride Chemical compound ClC(=O)C(Cl)C1=CC=CC=C1 FGEAOSXMQZWHIQ-UHFFFAOYSA-N 0.000 description 1
- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 1
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- -1 aromatic carbon hydrogen Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 230000003170 musculotropic effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 229960001789 papaverine Drugs 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N phenyl acetate Chemical class CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K7/00—Constructional details common to different types of electric apparatus
- H05K7/02—Arrangements of circuit components or wiring on supporting structure
- H05K7/12—Resilient or clamping means for holding component to structure
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01H—ELECTRIC SWITCHES; RELAYS; SELECTORS; EMERGENCY PROTECTIVE DEVICES
- H01H50/00—Details of electromagnetic relays
- H01H50/14—Terminal arrangements
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K7/00—Constructional details common to different types of electric apparatus
- H05K7/14—Mounting supporting structure in casing or on frame or rack
- H05K7/1417—Mounting supporting structure in casing or on frame or rack having securing means for mounting boards, plates or wiring boards
Landscapes
- Engineering & Computer Science (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Coupling Device And Connection With Printed Circuit (AREA)
- Multi-Conductor Connections (AREA)
- Hydrogenated Pyridines (AREA)
- Combinations Of Printed Boards (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE00254/70A SE330399B (ja) | 1970-01-09 | 1970-01-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO128798B true NO128798B (ja) | 1974-01-07 |
Family
ID=20256268
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO00068/71A NO128798B (ja) | 1970-01-09 | 1971-01-08 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3674960A (ja) |
| JP (1) | JPS4832859B1 (ja) |
| BE (1) | BE761264A (ja) |
| DE (1) | DE2064865B2 (ja) |
| DK (1) | DK122050B (ja) |
| FI (1) | FI51645C (ja) |
| FR (1) | FR2075369A5 (ja) |
| GB (1) | GB1318683A (ja) |
| NL (1) | NL7018946A (ja) |
| NO (1) | NO128798B (ja) |
| SE (1) | SE330399B (ja) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2704671C2 (de) * | 1977-02-04 | 1984-09-13 | Standard Elektrik Lorenz Ag, 7000 Stuttgart | Leiterplatten-Halterung |
| JPS54182846U (ja) * | 1978-05-16 | 1979-12-25 | ||
| US11384684B2 (en) | 2019-08-09 | 2022-07-12 | Astron Aerospace Llc | Rotary engine, parts thereof, and methods |
| WO2022026777A2 (en) | 2020-07-29 | 2022-02-03 | Astron Aerospace Llc | Rotary engine, parts thereof, and methods |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB786959A (en) * | 1954-09-07 | 1957-11-27 | Telephone Mfg Co Ltd | Improvements in and relating to electromagnetic relays and to apparatus incorporating such relays |
| US3242285A (en) * | 1963-03-21 | 1966-03-22 | Guardian Electric Mfg Co | Relay with unitary field piece construction |
| US3560901A (en) * | 1968-03-26 | 1971-02-02 | Omron Tateisi Electronics Co | Electromagnetic relay |
| US3493903A (en) * | 1968-08-05 | 1970-02-03 | Westinghouse Air Brake Co | Electromagnetic relay with a suspended armature |
| BE754755A (fr) * | 1969-08-13 | 1971-01-18 | Western Electric Co | Dispositif de commutation electromagnetique |
-
1970
- 1970-01-09 SE SE00254/70A patent/SE330399B/xx unknown
- 1970-12-15 FI FI703379A patent/FI51645C/fi active
- 1970-12-17 US US98981A patent/US3674960A/en not_active Expired - Lifetime
- 1970-12-29 NL NL7018946A patent/NL7018946A/xx unknown
- 1970-12-29 JP JP45121889A patent/JPS4832859B1/ja active Pending
- 1970-12-31 DE DE19702064865 patent/DE2064865B2/de not_active Withdrawn
-
1971
- 1971-01-06 BE BE761264A patent/BE761264A/xx unknown
- 1971-01-07 DK DK5771AA patent/DK122050B/da unknown
- 1971-01-08 FR FR7100562A patent/FR2075369A5/fr not_active Expired
- 1971-01-08 NO NO00068/71A patent/NO128798B/no unknown
- 1971-01-08 GB GB111571A patent/GB1318683A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI51645B (ja) | 1976-11-01 |
| GB1318683A (en) | 1973-05-31 |
| DK122050B (da) | 1972-01-10 |
| FI51645C (fi) | 1977-02-10 |
| BE761264A (fr) | 1971-06-16 |
| DE2064865B2 (de) | 1971-12-23 |
| SE330399B (ja) | 1970-11-16 |
| US3674960A (en) | 1972-07-04 |
| NL7018946A (ja) | 1971-07-13 |
| DE2064865A1 (de) | 1971-07-22 |
| FR2075369A5 (ja) | 1971-10-08 |
| JPS4832859B1 (ja) | 1973-10-09 |
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