CA1095416A - Pharmaceutical compositions comprising substituted phenyl-amino-alcohol and process for preparing these compositions - Google Patents
Pharmaceutical compositions comprising substituted phenyl-amino-alcohol and process for preparing these compositionsInfo
- Publication number
- CA1095416A CA1095416A CA279,790A CA279790A CA1095416A CA 1095416 A CA1095416 A CA 1095416A CA 279790 A CA279790 A CA 279790A CA 1095416 A CA1095416 A CA 1095416A
- Authority
- CA
- Canada
- Prior art keywords
- amino
- alcohol
- pharmaceutical composition
- substituted phenyl
- glucuronic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical class ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 22
- 239000000203 mixture Substances 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 4
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 claims abstract description 26
- 229940097043 glucuronic acid Drugs 0.000 claims abstract description 19
- 239000004480 active ingredient Substances 0.000 claims abstract 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 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 18
- 239000000243 solution Substances 0.000 claims description 14
- 239000007864 aqueous solution Substances 0.000 claims description 9
- -1 alkyl radical Chemical group 0.000 claims description 8
- 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 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- BFCDFTHTSVTWOG-UHFFFAOYSA-N 2-(octylamino)-1-[4-(propan-2-ylthio)phenyl]-1-propanol Chemical compound CCCCCCCCNC(C)C(O)C1=CC=C(SC(C)C)C=C1 BFCDFTHTSVTWOG-UHFFFAOYSA-N 0.000 claims description 6
- 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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 group 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
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 11
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- 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 abstract description 6
- 239000003814 drug Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 5
- 229940097042 glucuronate Drugs 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 229940044613 1-propanol Drugs 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 241000700159 Rattus Species 0.000 description 3
- 208000007536 Thrombosis Diseases 0.000 description 3
- 150000001414 amino alcohols Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 230000010412 perfusion Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229960005335 propanol Drugs 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
- GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 2
- 229940089206 anhydrous dextrose Drugs 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
- 230000008901 benefit Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 210000003405 ileum Anatomy 0.000 description 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- WMCWCAHHSHKERX-UHFFFAOYSA-N 1-(4-propan-2-ylsulfanylphenyl)-2-(tetradecylamino)propan-1-ol Chemical compound CCCCCCCCCCCCCCNC(C)C(O)C1=CC=C(SC(C)C)C=C1 WMCWCAHHSHKERX-UHFFFAOYSA-N 0.000 description 1
- SKRMSEQRBCTDLN-UHFFFAOYSA-N 2-(hexylamino)-1-(4-propan-2-ylsulfanylphenyl)propan-1-ol Chemical compound CCCCCCNC(C)C(O)C1=CC=C(SC(C)C)C=C1 SKRMSEQRBCTDLN-UHFFFAOYSA-N 0.000 description 1
- WNIZRYVYKRFBIU-UHFFFAOYSA-N 2-(octylamino)-1-(4-propan-2-ylthiophen-2-yl)propan-1-ol Chemical compound CCCCCCCCNC(C)C(O)C1=CC(C(C)C)=CS1 WNIZRYVYKRFBIU-UHFFFAOYSA-N 0.000 description 1
- BHLLNXPVJAALHN-UHFFFAOYSA-N 2-(octylamino)propan-1-ol Chemical compound CCCCCCCCNC(C)CO BHLLNXPVJAALHN-UHFFFAOYSA-N 0.000 description 1
- 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-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
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007953 anoxia Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000000702 anti-platelet effect Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 229940124575 antispasmodic agent Drugs 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000003465 bronchodilatator Substances 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
- 229910052799 carbon Inorganic materials 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
- 230000008602 contraction Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 1
- 229960002768 dipyridamole Drugs 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 210000003975 mesenteric artery Anatomy 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 231100000418 oral toxicity Toxicity 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000004224 protection Effects 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 238000012216 screening Methods 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
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 239000003071 vasodilator agent Substances 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR76.17.110 | 1976-06-04 | ||
| 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 |
|---|---|
| CA1095416A true CA1095416A (en) | 1981-02-10 |
Family
ID=9174050
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA279,790A Expired CA1095416A (en) | 1976-06-04 | 1977-06-03 | Pharmaceutical compositions comprising substituted phenyl-amino-alcohol and process for preparing these compositions |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5318721A (cg-RX-API-DMAC10.html) |
| BE (1) | BE855320A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1095416A (cg-RX-API-DMAC10.html) |
| CH (1) | CH622023A5 (cg-RX-API-DMAC10.html) |
| DE (1) | DE2724608C2 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2353288A1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1569380A (cg-RX-API-DMAC10.html) |
| NL (1) | NL7706177A (cg-RX-API-DMAC10.html) |
| SE (1) | SE441183B (cg-RX-API-DMAC10.html) |
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 |
|---|---|
| SE7706481L (sv) | 1977-12-05 |
| FR2353288B1 (cg-RX-API-DMAC10.html) | 1978-12-15 |
| SE441183B (sv) | 1985-09-16 |
| CH622023A5 (en) | 1981-03-13 |
| 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 (cg-RX-API-DMAC10.html) | 1986-06-20 |
| JPS5318721A (en) | 1978-02-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |