CH539607A - Verfahren zur Herstellung neuer 1-Aryloxy-2-hydroxy-3-isopropylamino-propane und ihrer Salze - Google Patents
Verfahren zur Herstellung neuer 1-Aryloxy-2-hydroxy-3-isopropylamino-propane und ihrer SalzeInfo
- Publication number
- CH539607A CH539607A CH765073A CH765073A CH539607A CH 539607 A CH539607 A CH 539607A CH 765073 A CH765073 A CH 765073A CH 765073 A CH765073 A CH 765073A CH 539607 A CH539607 A CH 539607A
- Authority
- CH
- Switzerland
- Prior art keywords
- hydroxy
- alkyl
- phenoxy
- adrenolytics
- hypotensives
- Prior art date
Links
- -1 phenoxy hydroxy Chemical group 0.000 title claims description 6
- 208000001953 Hypotension Diseases 0.000 title abstract 3
- 230000003288 anthiarrhythmic effect Effects 0.000 title abstract 3
- 239000003416 antiarrhythmic agent Substances 0.000 title abstract 3
- 208000021822 hypotensive Diseases 0.000 title abstract 3
- 230000002959 anti-hypotensive effect Effects 0.000 title abstract 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 title description 2
- 230000001077 hypotensive effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 4
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000000059 bradycardiac effect Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 206010003119 arrhythmia Diseases 0.000 description 2
- 230000036471 bradycardia Effects 0.000 description 2
- 208000006218 bradycardia Diseases 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- NXQMNKUGGYNLBY-UHFFFAOYSA-N toliprolol Chemical compound CC(C)NCC(O)COC1=CC=CC(C)=C1 NXQMNKUGGYNLBY-UHFFFAOYSA-N 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- YDNBUDLNDAAOEH-UHFFFAOYSA-N 1-(2,3-dimethylphenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC(C)=C1C YDNBUDLNDAAOEH-UHFFFAOYSA-N 0.000 description 1
- CKXVUQMSIUHNFE-UHFFFAOYSA-N 1-(2,4-dichlorophenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=C(Cl)C=C1Cl CKXVUQMSIUHNFE-UHFFFAOYSA-N 0.000 description 1
- NAOVAEUCWSXGAZ-UHFFFAOYSA-N 1-(2,5-dichlorophenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC(Cl)=CC=C1Cl NAOVAEUCWSXGAZ-UHFFFAOYSA-N 0.000 description 1
- MCHKWZKCDSOXGD-UHFFFAOYSA-N 1-(2,5-dimethylphenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC(C)=CC=C1C MCHKWZKCDSOXGD-UHFFFAOYSA-N 0.000 description 1
- MMFAMLTXBOVZAJ-UHFFFAOYSA-N 1-(2-aminophenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1N MMFAMLTXBOVZAJ-UHFFFAOYSA-N 0.000 description 1
- UXPPUNYWLDXKEG-UHFFFAOYSA-N 1-(2-chlorophenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1Cl UXPPUNYWLDXKEG-UHFFFAOYSA-N 0.000 description 1
- QQGBBQFTLXYBOS-UHFFFAOYSA-N 1-(3,4-dimethylphenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=C(C)C(C)=C1 QQGBBQFTLXYBOS-UHFFFAOYSA-N 0.000 description 1
- ZEQHCHRGGOXXLH-UHFFFAOYSA-N 1-(3,5-dimethylphenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC(C)=CC(C)=C1 ZEQHCHRGGOXXLH-UHFFFAOYSA-N 0.000 description 1
- NPHCEXNMYYMJDL-UHFFFAOYSA-N 1-(3-chlorophenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC(Cl)=C1 NPHCEXNMYYMJDL-UHFFFAOYSA-N 0.000 description 1
- NNXODRVFWIOCGZ-UHFFFAOYSA-N 1-(propan-2-ylamino)-3-(2,4,5-trichlorophenoxy)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC(Cl)=C(Cl)C=C1Cl NNXODRVFWIOCGZ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- PYCBXTOMXDPDRC-UHFFFAOYSA-N CC1=C(OC(C(CC(C)C)O)N)C=CC=C1 Chemical compound CC1=C(OC(C(CC(C)C)O)N)C=CC=C1 PYCBXTOMXDPDRC-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 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
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- VKMGSWIFEHZQRS-UHFFFAOYSA-N dichloroisoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(Cl)C(Cl)=C1 VKMGSWIFEHZQRS-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1963B0073262 DE1493454C3 (de) | 1963-08-26 | 1963-08-26 | 1 -Aryloxy^-hydroxy-S-isopropylaminopropane und deren Salze sowie deren Herstellung und darauf basierende Arzneimittel |
| CH1109264A CH539606A (de) | 1963-08-26 | 1964-08-25 | Verfahren zur Herstellung neuer 1-Aryloxy-2-hydroxy-3-isopropylamino-propane und ihrer Salze |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH539607A true CH539607A (de) | 1973-07-31 |
Family
ID=6977785
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH765073A CH539607A (de) | 1963-08-26 | 1964-08-25 | Verfahren zur Herstellung neuer 1-Aryloxy-2-hydroxy-3-isopropylamino-propane und ihrer Salze |
| CH765173A CH539608A (de) | 1963-08-26 | 1964-08-25 | Verfahren zur Herstellung neuer 1-Aryloxy-2-hydroxy-3-isopropylamino-propane und ihrer Salze |
| CH764973A CH540225A (de) | 1963-08-26 | 1964-08-25 | Verfahren zur Herstellung neuer 1-Aryloxy-2-hydroxy-3-isopropylamino-propane und ihrer Salze |
| CH765273A CH539609A (de) | 1963-08-26 | 1964-08-25 | Verfahren zur Herstellung neuer 1-Aryloxy-2-hydroxy-3-isopropylamino-propane und ihrer Salze |
| CH1109264A CH539606A (de) | 1963-08-26 | 1964-08-25 | Verfahren zur Herstellung neuer 1-Aryloxy-2-hydroxy-3-isopropylamino-propane und ihrer Salze |
| CH765373A CH539610A (de) | 1963-08-26 | 1964-08-25 | Verfahren zur Herstellung neuer 1-Aryloxy-2-hydroxy-3-isopropylamino-propane und ihrer Salze |
Family Applications After (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH765173A CH539608A (de) | 1963-08-26 | 1964-08-25 | Verfahren zur Herstellung neuer 1-Aryloxy-2-hydroxy-3-isopropylamino-propane und ihrer Salze |
| CH764973A CH540225A (de) | 1963-08-26 | 1964-08-25 | Verfahren zur Herstellung neuer 1-Aryloxy-2-hydroxy-3-isopropylamino-propane und ihrer Salze |
| CH765273A CH539609A (de) | 1963-08-26 | 1964-08-25 | Verfahren zur Herstellung neuer 1-Aryloxy-2-hydroxy-3-isopropylamino-propane und ihrer Salze |
| CH1109264A CH539606A (de) | 1963-08-26 | 1964-08-25 | Verfahren zur Herstellung neuer 1-Aryloxy-2-hydroxy-3-isopropylamino-propane und ihrer Salze |
| CH765373A CH539610A (de) | 1963-08-26 | 1964-08-25 | Verfahren zur Herstellung neuer 1-Aryloxy-2-hydroxy-3-isopropylamino-propane und ihrer Salze |
Country Status (13)
| Country | Link |
|---|---|
| JP (5) | JPS509780B1 (cs) |
| BE (1) | BE652336A (cs) |
| BR (1) | BR6462130D0 (cs) |
| CH (6) | CH539607A (cs) |
| CY (1) | CY572A (cs) |
| DE (1) | DE1493454C3 (cs) |
| DK (4) | DK129411B (cs) |
| FI (2) | FI43881C (cs) |
| FR (2) | FR3647M (cs) |
| GB (1) | GB1084793A (cs) |
| IL (1) | IL21978A (cs) |
| NL (2) | NL142950B (cs) |
| SE (6) | SE318891B (cs) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE881436C (de) * | 1938-12-04 | 1953-06-29 | Ind G M B H | Einrichtung zum Abfuehren des von Schlauchfiltern abgeworfenen Staubes |
| US3466325A (en) * | 1965-04-30 | 1969-09-09 | Haessle Ab | 1-(ortho-alkenyl phenoxy) - 2-hydroxy-3-isopropylaminopropanes and the salts thereof |
| US3868460A (en) * | 1967-02-06 | 1975-02-25 | Boehringer Sohn Ingelheim | Therapeutic compositions and method |
| US3541130A (en) * | 1967-02-06 | 1970-11-17 | Boehringer Sohn Ingelheim | 1-(cyanophenoxy)-2-hydroxy-3-tert.-butylamine propanes |
| GB1501632A (en) * | 1974-06-28 | 1978-02-22 | Cm Ind | Aromatic ketones having cardiovascular activity |
| JPS5418240U (cs) * | 1977-07-07 | 1979-02-06 | ||
| JPS54133863U (cs) * | 1978-03-08 | 1979-09-17 | ||
| DE2839475A1 (de) * | 1978-09-11 | 1980-03-20 | Dolorgiet Arzneimittelfabrik | Isopropylamin-verbindungen, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
-
1963
- 1963-08-26 DE DE1963B0073262 patent/DE1493454C3/de not_active Expired
-
1964
- 1964-08-25 CH CH765073A patent/CH539607A/de not_active IP Right Cessation
- 1964-08-25 CH CH765173A patent/CH539608A/de not_active IP Right Cessation
- 1964-08-25 CH CH764973A patent/CH540225A/de not_active IP Right Cessation
- 1964-08-25 CH CH765273A patent/CH539609A/de not_active IP Right Cessation
- 1964-08-25 CH CH1109264A patent/CH539606A/de not_active IP Right Cessation
- 1964-08-25 CH CH765373A patent/CH539610A/de not_active IP Right Cessation
- 1964-08-26 FI FI182164A patent/FI43881C/fi active
- 1964-08-26 NL NL6409883A patent/NL142950B/xx not_active IP Right Cessation
- 1964-08-26 GB GB3495264A patent/GB1084793A/en not_active Expired
- 1964-08-26 BE BE652336A patent/BE652336A/xx unknown
- 1964-08-26 JP JP4838064A patent/JPS509780B1/ja active Pending
- 1964-08-26 FR FR986265A patent/FR3647M/fr not_active Expired
- 1964-08-26 IL IL2197864A patent/IL21978A/xx unknown
- 1964-08-26 SE SE10240/64A patent/SE318891B/xx unknown
- 1964-08-26 DK DK421664A patent/DK129411B/da unknown
- 1964-08-26 SE SE129268A patent/SE346775B/xx unknown
- 1964-08-26 BR BR16213064A patent/BR6462130D0/pt unknown
- 1964-08-26 FR FR1555463D patent/FR1555463A/fr not_active Expired
-
1967
- 1967-03-31 DK DK185167A patent/DK112739B/da unknown
- 1967-07-07 JP JP4341567A patent/JPS507047B1/ja active Pending
- 1967-07-07 JP JP4341467A patent/JPS5021454B1/ja active Pending
- 1967-07-07 JP JP4341167A patent/JPS509781B1/ja active Pending
- 1967-07-07 JP JP4341367A patent/JPS509782B1/ja active Pending
-
1968
- 1968-01-31 SE SE01294/68A patent/SE346778B/xx unknown
- 1968-01-31 SE SE01295/68A patent/SE346779B/xx unknown
- 1968-01-31 SE SE01293/68A patent/SE346776B/xx unknown
- 1968-01-31 SE SE01296/68A patent/SE346777B/xx unknown
-
1969
- 1969-09-22 FI FI269869A patent/FI52974C/fi active
-
1970
- 1970-12-07 NL NL7017830A patent/NL7017830A/xx unknown
-
1971
- 1971-01-16 CY CY57271A patent/CY572A/xx unknown
- 1971-06-01 DK DK267371A patent/DK129032B/da unknown
-
1972
- 1972-11-29 DK DK596872A patent/DK131988C/da active
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |