CH499490A - Verfahren zur Herstellung von Derivaten des rechtsdrehenden Propanolamins - Google Patents
Verfahren zur Herstellung von Derivaten des rechtsdrehenden PropanolaminsInfo
- Publication number
- CH499490A CH499490A CH188266A CH188266A CH499490A CH 499490 A CH499490 A CH 499490A CH 188266 A CH188266 A CH 188266A CH 188266 A CH188266 A CH 188266A CH 499490 A CH499490 A CH 499490A
- Authority
- CH
- Switzerland
- Prior art keywords
- radical
- alkyl
- formula
- alkoxy
- dextrorotatory
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 16
- 150000003839 salts Chemical class 0.000 title claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 6
- 239000002253 acid Substances 0.000 title abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 150000003152 propanolamines Chemical class 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 3
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- CKNOLMVLQUPVMU-XOMFLMSUSA-N Digitalin Natural products O(C)[C@H]1[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@H](CO)O2)[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@@](C)([C@@H]([C@H](O)C5)C5=CC(=O)OC5)CC4)CC3)CC2)[C@@H]1O CKNOLMVLQUPVMU-XOMFLMSUSA-N 0.000 abstract 1
- WDJUZGPOPHTGOT-OAXVISGBSA-N Digitoxin Natural products O([C@H]1[C@@H](C)O[C@@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@@](C)([C@H](C6=CC(=O)OC6)CC5)CC4)CC3)CC2)C[C@H]1O)[C@H]1O[C@@H](C)[C@H](O[C@H]2O[C@@H](C)[C@@H](O)[C@@H](O)C2)[C@@H](O)C1 WDJUZGPOPHTGOT-OAXVISGBSA-N 0.000 abstract 1
- CPFNIKYEDJFRAT-UHFFFAOYSA-N Strospasid Natural products OC1C(OC)C(O)C(C)OC1OC1CC(CCC2C3(CC(O)C(C3(C)CCC32)C=2COC(=O)C=2)O)C3(C)CC1 CPFNIKYEDJFRAT-UHFFFAOYSA-N 0.000 abstract 1
- CKNOLMVLQUPVMU-UHFFFAOYSA-N UNPD183315 Natural products O1C(C)C(OC2C(C(O)C(O)C(CO)O2)O)C(OC)C(O)C1OC(C1)CCC2(C)C1CCC(C1(CC3O)O)C2CCC1(C)C3C1=CC(=O)OC1 CKNOLMVLQUPVMU-UHFFFAOYSA-N 0.000 abstract 1
- 125000003435 aroyl group Chemical group 0.000 abstract 1
- 206010003119 arrhythmia Diseases 0.000 abstract 1
- 230000006793 arrhythmia Effects 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- CKNOLMVLQUPVMU-YMMLYESFSA-N digitalin Chemical compound C1([C@@H]2[C@@]3(C)CC[C@H]4[C@H]([C@]3(C[C@@H]2O)O)CC[C@H]2[C@]4(C)CC[C@@H](C2)O[C@H]2[C@H](O)[C@H]([C@H]([C@@H](C)O2)O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)OC)=CC(=O)OC1 CKNOLMVLQUPVMU-YMMLYESFSA-N 0.000 abstract 1
- 229950004590 digitalin Drugs 0.000 abstract 1
- 229930182478 glucoside Natural products 0.000 abstract 1
- 150000008131 glucosides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- -1 naphthyl radical Chemical class 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- DIJUYSHEKLLUFO-UHFFFAOYSA-N 1-[benzyl(propan-2-yl)amino]-3-naphthalen-1-yloxypropan-2-ol Chemical compound C=1C=CC2=CC=CC=C2C=1OCC(O)CN(C(C)C)CC1=CC=CC=C1 DIJUYSHEKLLUFO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229960004592 isopropanol Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- AQHHHDLHHXJYJD-CQSZACIVSA-N (R)-(+)-propranolol Chemical compound C1=CC=C2C(OC[C@H](O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-CQSZACIVSA-N 0.000 description 1
- NKGDFENDOJZTDR-UHFFFAOYSA-N 1-(tert-butylamino)-3-(4-methylnaphthalen-1-yl)oxypropan-2-ol Chemical compound C(C)(C)(C)NCC(COC1=CC=C(C2=CC=CC=C12)C)O NKGDFENDOJZTDR-UHFFFAOYSA-N 0.000 description 1
- CAHJWWNWFUPHCR-UHFFFAOYSA-N 2-[[2-hydroxy-3-(2-phenoxyphenoxy)propyl]amino]-2-methylpropan-1-ol Chemical compound OCC(C)(C)NCC(COC1=C(C=CC=C1)OC1=CC=CC=C1)O CAHJWWNWFUPHCR-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- LTMHDMANZUZIPE-UHFFFAOYSA-N 3-[3-[5-[5-(4,5-dihydroxy-6-methyloxan-2-yl)oxy-4-hydroxy-6-methyloxan-2-yl]oxy-4-hydroxy-6-methyloxan-2-yl]oxy-12,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2h-furan-5-one Chemical compound C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 description 1
- LPMXVESGRSUGHW-UHFFFAOYSA-N Acolongiflorosid K Natural products OC1C(O)C(O)C(C)OC1OC1CC2(O)CCC3C4(O)CCC(C=5COC(=O)C=5)C4(C)CC(O)C3C2(CO)C(O)C1 LPMXVESGRSUGHW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- LPMXVESGRSUGHW-GHYGWZAOSA-N Ouabain Natural products O([C@@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1)[C@H]1C[C@@H](O)[C@@]2(CO)[C@@](O)(C1)CC[C@H]1[C@]3(O)[C@@](C)([C@H](C4=CC(=O)OC4)CC3)C[C@@H](O)[C@H]21 LPMXVESGRSUGHW-GHYGWZAOSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 244000166550 Strophanthus gratus Species 0.000 description 1
- BQOWUDKEXDCGQS-UHFFFAOYSA-N [CH]1CCCC1 Chemical compound [CH]1CCCC1 BQOWUDKEXDCGQS-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229940097217 cardiac glycoside Drugs 0.000 description 1
- 239000002368 cardiac glycoside Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
- 229960003343 ouabain Drugs 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229930002534 steroid glycoside Natural products 0.000 description 1
- 150000008143 steroidal glycosides Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
Landscapes
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1318169A CH512435A (de) | 1966-02-10 | 1966-02-10 | Verfahren zur Herstellung von Säureadditionssalzen des rechtsdrehenden Propanolamins |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB25473/65A GB1136919A (en) | 1965-06-16 | 1965-06-16 | Amines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH499490A true CH499490A (de) | 1970-11-30 |
Family
ID=10228288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH188266A CH499490A (de) | 1965-06-16 | 1966-02-10 | Verfahren zur Herstellung von Derivaten des rechtsdrehenden Propanolamins |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS4842629B1 (enrdf_load_stackoverflow) |
| BE (1) | BE675967A (enrdf_load_stackoverflow) |
| CH (1) | CH499490A (enrdf_load_stackoverflow) |
| DE (1) | DE1543684A1 (enrdf_load_stackoverflow) |
| DK (1) | DK116062B (enrdf_load_stackoverflow) |
| FR (1) | FR5800M (enrdf_load_stackoverflow) |
| GB (1) | GB1136919A (enrdf_load_stackoverflow) |
| NL (1) | NL6601430A (enrdf_load_stackoverflow) |
| SE (1) | SE353317B (enrdf_load_stackoverflow) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5051722U (enrdf_load_stackoverflow) * | 1973-09-10 | 1975-05-19 | ||
| GB1458392A (en) * | 1973-11-09 | 1976-12-15 | Ici Ltd | Optically-active 1-aryloxy-2,3-epoxypropane derivatives |
| CH585693A5 (enrdf_load_stackoverflow) * | 1974-02-08 | 1977-03-15 | Ciba Geigy Ag | |
| US4210653A (en) * | 1978-06-27 | 1980-07-01 | Merck & Co., Inc. | Pyridyloxypropanolamines |
| US4294966A (en) * | 1978-07-28 | 1981-10-13 | Ciba-Geigy Corporation | Process for inverting the configuration in optically active compounds |
| US5013761A (en) * | 1988-06-03 | 1991-05-07 | Eli Lilly And Company | Serotonin antagonists |
| JP2801768B2 (ja) * | 1990-11-17 | 1998-09-21 | 日東電工株式会社 | 新規な光学活性メトプロロール・酒石酸誘導体塩及びその製法、並びにこの塩を用いる光学活性メトプロロールの製法 |
-
1965
- 1965-06-16 GB GB25473/65A patent/GB1136919A/en not_active Expired
-
1966
- 1966-01-26 SE SE01018/66A patent/SE353317B/xx unknown
- 1966-02-02 BE BE675967D patent/BE675967A/xx not_active IP Right Cessation
- 1966-02-04 DE DE19661543684 patent/DE1543684A1/de active Pending
- 1966-02-04 NL NL6601430A patent/NL6601430A/xx unknown
- 1966-02-10 CH CH188266A patent/CH499490A/de not_active IP Right Cessation
- 1966-02-25 JP JP41011499A patent/JPS4842629B1/ja active Pending
- 1966-06-17 FR FR65901A patent/FR5800M/fr not_active Expired
- 1966-12-01 DK DK623566AA patent/DK116062B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK116062B (da) | 1969-12-08 |
| JPS4842629B1 (enrdf_load_stackoverflow) | 1973-12-13 |
| BE675967A (enrdf_load_stackoverflow) | 1966-08-02 |
| DE1543684A1 (de) | 1969-10-09 |
| SE353317B (enrdf_load_stackoverflow) | 1973-01-29 |
| FR5800M (enrdf_load_stackoverflow) | 1968-02-19 |
| NL6601430A (enrdf_load_stackoverflow) | 1966-12-19 |
| GB1136919A (en) | 1968-12-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |