CH622023A5 - Process for the preparation of a water-soluble compound based on a substituted phenylaminoalcohol - Google Patents
Process for the preparation of a water-soluble compound based on a substituted phenylaminoalcohol Download PDFInfo
- Publication number
- CH622023A5 CH622023A5 CH689277A CH689277A CH622023A5 CH 622023 A5 CH622023 A5 CH 622023A5 CH 689277 A CH689277 A CH 689277A CH 689277 A CH689277 A CH 689277A CH 622023 A5 CH622023 A5 CH 622023A5
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- glucuronic acid
- substituted
- alcohol
- salt
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 21
- 150000001875 compounds Chemical class 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 7
- CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical class ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 title claims 3
- -1 phenyl -substituted amino Chemical group 0.000 claims description 21
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 claims description 14
- 229940097043 glucuronic acid Drugs 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- ZJNGCHWVIQXKRC-UHFFFAOYSA-N 1-(octylamino)propan-1-ol Chemical compound CCCCCCCCNC(O)CC ZJNGCHWVIQXKRC-UHFFFAOYSA-N 0.000 claims description 5
- AEMOLEFTQBMNLQ-WAXACMCWSA-N alpha-D-glucuronic acid Chemical compound O[C@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-WAXACMCWSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 238000004090 dissolution Methods 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 238000012216 screening Methods 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 229940097042 glucuronate Drugs 0.000 description 9
- AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 5
- 238000001990 intravenous administration Methods 0.000 description 5
- 150000001414 amino alcohols Chemical class 0.000 description 4
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical compound CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- 230000002921 anti-spasmodic effect Effects 0.000 description 2
- 230000002785 anti-thrombosis Effects 0.000 description 2
- 210000000709 aorta Anatomy 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 210000003405 ileum Anatomy 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000010412 perfusion Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 206010002660 Anoxia Diseases 0.000 description 1
- 241000976983 Anoxia Species 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 206010058667 Oral toxicity Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 239000008156 Ringer's lactate solution Substances 0.000 description 1
- 241000168254 Siro Species 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000007953 anoxia Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 230000000702 anti-platelet effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- ZEWYCNBZMPELPF-UHFFFAOYSA-J calcium;potassium;sodium;2-hydroxypropanoic acid;sodium;tetrachloride Chemical compound [Na].[Na+].[Cl-].[Cl-].[Cl-].[Cl-].[K+].[Ca+2].CC(O)C(O)=O ZEWYCNBZMPELPF-UHFFFAOYSA-J 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000037149 energy metabolism Effects 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000003170 musculotropic effect Effects 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- 230000000444 normolipidemic effect Effects 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 239000000810 peripheral vasodilating agent Substances 0.000 description 1
- 229960002116 peripheral vasodilator Drugs 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000001012 protector Effects 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 235000020354 squash Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229940125725 tranquilizer Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- UMFCIIBZHQXRCJ-NSCUHMNNSA-N trans-anol Chemical compound C\C=C\C1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-NSCUHMNNSA-N 0.000 description 1
- 239000004552 water soluble powder Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7617110A FR2353288A1 (fr) | 1976-06-04 | 1976-06-04 | Composition pharmaceutique hydrosoluble a base d'un compose amine comme produit actif |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH622023A5 true CH622023A5 (en) | 1981-03-13 |
Family
ID=9174050
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH689277A CH622023A5 (en) | 1976-06-04 | 1977-06-03 | Process for the preparation of a water-soluble compound based on a substituted phenylaminoalcohol |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5318721A (OSRAM) |
| BE (1) | BE855320A (OSRAM) |
| CA (1) | CA1095416A (OSRAM) |
| CH (1) | CH622023A5 (OSRAM) |
| DE (1) | DE2724608C2 (OSRAM) |
| FR (1) | FR2353288A1 (OSRAM) |
| GB (1) | GB1569380A (OSRAM) |
| NL (1) | NL7706177A (OSRAM) |
| SE (1) | SE441183B (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1198386B (it) * | 1982-07-06 | 1988-12-21 | Lepetit Spa | Un prodotto a rilascio protratto contenente il suloctidile |
| DE3815273A1 (de) * | 1988-05-05 | 1989-11-16 | Draegerwerk Ag | Mobile intensivbehandlungseinheit |
| AU5103898A (en) * | 1996-11-05 | 1998-05-29 | Alcon Laboratories, Inc. | Polyhydroxy monocarboxylic and dicarboxylic acids and their lactones in ophthalmic compositions |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH54A (fr) * | 1889-01-08 | Emile Mertz | Appareil à humidifier et à rafraîchir l'air des salles de filatures, des malteries, des bateaux, des salles de théâtres, etc. | |
| CH52A (de) * | 1889-01-08 | Emil Zetter | Neuer Petroleumgas-Apparat für Heizzwecke | |
| GB1390748A (en) * | 1973-04-09 | 1975-04-16 | Continental Pharma | Alkyl and cycloalkylthiophenylalkylaminoalkanols their salts and the preparation thereof |
-
1976
- 1976-06-04 FR FR7617110A patent/FR2353288A1/fr active Granted
-
1977
- 1977-06-01 DE DE2724608A patent/DE2724608C2/de not_active Expired
- 1977-06-02 BE BE178135A patent/BE855320A/xx not_active IP Right Cessation
- 1977-06-03 NL NL7706177A patent/NL7706177A/xx not_active Application Discontinuation
- 1977-06-03 CA CA279,790A patent/CA1095416A/en not_active Expired
- 1977-06-03 CH CH689277A patent/CH622023A5/fr not_active IP Right Cessation
- 1977-06-03 SE SE7706481A patent/SE441183B/xx not_active IP Right Cessation
- 1977-06-03 GB GB23697/77A patent/GB1569380A/en not_active Expired
- 1977-06-03 JP JP6490677A patent/JPS5318721A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| CA1095416A (en) | 1981-02-10 |
| SE7706481L (sv) | 1977-12-05 |
| FR2353288B1 (OSRAM) | 1978-12-15 |
| SE441183B (sv) | 1985-09-16 |
| NL7706177A (nl) | 1977-12-06 |
| BE855320A (fr) | 1977-12-02 |
| DE2724608C2 (de) | 1986-09-18 |
| DE2724608A1 (de) | 1977-12-22 |
| FR2353288A1 (fr) | 1977-12-30 |
| GB1569380A (en) | 1980-06-11 |
| JPS6126526B2 (OSRAM) | 1986-06-20 |
| JPS5318721A (en) | 1978-02-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUE | Assignment |
Owner name: CONTINENTAL PHARMA, INC. |
|
| PL | Patent ceased | ||
| PL | Patent ceased |