NO134372B - - Google Patents
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- Publication number
- NO134372B NO134372B NO3714/72A NO371472A NO134372B NO 134372 B NO134372 B NO 134372B NO 3714/72 A NO3714/72 A NO 3714/72A NO 371472 A NO371472 A NO 371472A NO 134372 B NO134372 B NO 134372B
- Authority
- NO
- Norway
- Prior art keywords
- water
- parts
- ether
- ethanol
- palladium
- Prior art date
Links
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 9
- -1 pivaloyloxy Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000005984 hydrogenation reaction Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 230000008018 melting Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 230000000873 masking effect Effects 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 229960003424 phenylacetic acid Drugs 0.000 description 3
- 239000003279 phenylacetic acid Substances 0.000 description 3
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- 230000002085 persistent effect Effects 0.000 description 2
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- YRCWQPVGYLYSOX-UHFFFAOYSA-N synephrine Chemical compound CNCC(O)C1=CC=C(O)C=C1 YRCWQPVGYLYSOX-UHFFFAOYSA-N 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- KWUJFMFEIDIIQI-UHFFFAOYSA-N 3-(benzylamino)-1-(4-hydroxyphenyl)propan-1-one Chemical compound C1=CC(O)=CC=C1C(=O)CCNCC1=CC=CC=C1 KWUJFMFEIDIIQI-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- 238000012404 In vitro experiment Methods 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 239000000150 Sympathomimetic Substances 0.000 description 1
- SNTGWYJPRFEDHW-UHFFFAOYSA-N [2,3-diphenyl-6-[2-(2-phenylethylamino)acetyl]phenyl] acetate Chemical compound C1(=CC=CC=C1)C=1C(=C(C=CC1C1=CC=CC=C1)C(CNCCC1=CC=CC=C1)=O)OC(C)=O SNTGWYJPRFEDHW-UHFFFAOYSA-N 0.000 description 1
- FJAHKCRRQLIPBP-UHFFFAOYSA-N [3-[3-(benzylamino)propanoyl]-5-(2,2-dimethylpropanoyloxy)phenyl] 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC1=CC(OC(=O)C(C)(C)C)=CC(C(=O)CCNCC=2C=CC=CC=2)=C1 FJAHKCRRQLIPBP-UHFFFAOYSA-N 0.000 description 1
- GNLYYQYVTORTMI-UHFFFAOYSA-N [3-[3-(benzylamino)propanoyl]phenyl] 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC1=CC=CC(C(=O)CCNCC=2C=CC=CC=2)=C1 GNLYYQYVTORTMI-UHFFFAOYSA-N 0.000 description 1
- NUHGTCXLUJRWFQ-UHFFFAOYSA-N [3-[3-(benzylamino)propanoyl]phenyl] 2-phenylacetate Chemical compound C=1C=CC(C(=O)CCNCC=2C=CC=CC=2)=CC=1OC(=O)CC1=CC=CC=C1 NUHGTCXLUJRWFQ-UHFFFAOYSA-N 0.000 description 1
- UEZDDSIYXRQSFU-UHFFFAOYSA-N [3-[4-(benzylamino)butanoyl]phenyl] 2-phenylacetate Chemical compound C=1C=CC(C(=O)CCCNCC=2C=CC=CC=2)=CC=1OC(=O)CC1=CC=CC=C1 UEZDDSIYXRQSFU-UHFFFAOYSA-N 0.000 description 1
- BJEIDEHGENHVJB-UHFFFAOYSA-N [4-[3-(benzylamino)propanoyl]phenyl] 2,2-dimethylpropanoate Chemical compound C1=CC(OC(=O)C(C)(C)C)=CC=C1C(=O)CCNCC1=CC=CC=C1 BJEIDEHGENHVJB-UHFFFAOYSA-N 0.000 description 1
- UZXKYBMHNPFNBQ-UHFFFAOYSA-N [4-[3-(benzylamino)propanoyl]phenyl] 2-phenylacetate Chemical compound C=1C=C(C(=O)CCNCC=2C=CC=CC=2)C=CC=1OC(=O)CC1=CC=CC=C1 UZXKYBMHNPFNBQ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000000058 esterolytic effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229960003684 oxedrine Drugs 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229960001802 phenylephrine Drugs 0.000 description 1
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical class NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000001975 sympathomimetic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
- C07C215/30—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/10—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide
- C07C51/14—Preparation of carboxylic acids or their salts, halides or anhydrides by reaction with carbon monoxide on a carbon-to-carbon unsaturated bond in organic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712152058 DE2152058C3 (de) | 1971-10-19 | O-Acyl-phenoläthanolamine und Verfahren zu deren Herstellung Klinge Pharma GmbH & Co, 8000 München |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134372B true NO134372B (xx) | 1976-06-21 |
| NO134372C NO134372C (xx) | 1976-09-29 |
Family
ID=5822789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3714/72A NO134372C (xx) | 1971-10-19 | 1972-10-17 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4085270A (xx) |
| AR (1) | AR196206A1 (xx) |
| AT (1) | AT317183B (xx) |
| BE (1) | BE790234A (xx) |
| BR (1) | BR7207279D0 (xx) |
| CH (1) | CH564517A5 (xx) |
| DD (1) | DD99776A1 (xx) |
| FI (1) | FI55988C (xx) |
| FR (1) | FR2158232B1 (xx) |
| GB (1) | GB1358973A (xx) |
| HU (1) | HU164582B (xx) |
| LU (1) | LU66312A1 (xx) |
| NL (1) | NL7213759A (xx) |
| NO (1) | NO134372C (xx) |
| SE (1) | SE391332B (xx) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3809714A (en) * | 1972-08-31 | 1974-05-07 | Interx Research Corp | Novel ester of ((methylamino)methyl) benzyl alcohol |
| US3868461A (en) * | 1972-11-22 | 1975-02-25 | Interx Research Corp | Ester of 3,4-dihydroxy-alpha (isopropylamino) methyl benzyl alcohol, composition and anti-asthma use thereof |
| FR2469411A1 (fr) * | 1979-11-15 | 1981-05-22 | Science Union & Cie | Nouveaux derives de la piperidylbenzimidazolinone, leurs procedes de preparation et les compositions pharmaceutiques les renfermant |
| DE3163871D1 (en) | 1980-07-09 | 1984-07-05 | Draco Ab | 1-(dihydroxyphenyl)-2-amino-ethanol derivatives; preparation, compositions and intermediates |
| GB0315929D0 (en) * | 2003-07-08 | 2003-08-13 | Koninkl Philips Electronics Nv | Display device |
| CN101921198B (zh) * | 2010-08-18 | 2013-04-24 | 潍坊幸福药业有限公司 | 一种盐酸依替福林的制备方法 |
| US20170231885A1 (en) * | 2014-10-14 | 2017-08-17 | Sculpt B.V. | Body Sculpting |
| CA3075271C (en) * | 2017-09-08 | 2021-10-12 | Insignis Therapeutics, Inc. | Methods of using dipivefrin |
-
1972
- 1972-10-11 FI FI2816/72A patent/FI55988C/fi active
- 1972-10-11 NL NL7213759A patent/NL7213759A/xx not_active Application Discontinuation
- 1972-10-12 SE SE7213184A patent/SE391332B/xx unknown
- 1972-10-13 US US05/297,416 patent/US4085270A/en not_active Expired - Lifetime
- 1972-10-17 NO NO3714/72A patent/NO134372C/no unknown
- 1972-10-17 LU LU66312A patent/LU66312A1/xx unknown
- 1972-10-17 AT AT887572A patent/AT317183B/de not_active IP Right Cessation
- 1972-10-17 DD DD166276A patent/DD99776A1/xx unknown
- 1972-10-17 HU HUCE900A patent/HU164582B/hu unknown
- 1972-10-18 BE BE790234D patent/BE790234A/xx not_active IP Right Cessation
- 1972-10-18 CH CH1521272A patent/CH564517A5/xx not_active IP Right Cessation
- 1972-10-18 GB GB4809872A patent/GB1358973A/en not_active Expired
- 1972-10-18 BR BR7279/72A patent/BR7207279D0/pt unknown
- 1972-10-18 FR FR7236899A patent/FR2158232B1/fr not_active Expired
- 1972-10-19 AR AR244726A patent/AR196206A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| NO134372C (xx) | 1976-09-29 |
| SE391332B (sv) | 1977-02-14 |
| HU164582B (xx) | 1974-03-28 |
| FR2158232A1 (xx) | 1973-06-15 |
| GB1358973A (en) | 1974-07-03 |
| DE2152058B2 (de) | 1976-03-04 |
| AT317183B (de) | 1974-08-12 |
| DD99776A1 (xx) | 1973-08-20 |
| BR7207279D0 (pt) | 1973-09-25 |
| BE790234A (fr) | 1973-02-15 |
| FI55988B (fi) | 1979-07-31 |
| CH564517A5 (xx) | 1975-07-31 |
| AR196206A1 (es) | 1973-12-10 |
| US4085270A (en) | 1978-04-18 |
| DE2152058A1 (de) | 1973-04-26 |
| NL7213759A (xx) | 1973-04-25 |
| FR2158232B1 (xx) | 1975-10-17 |
| LU66312A1 (xx) | 1973-01-23 |
| FI55988C (fi) | 1979-11-12 |
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