CA1144480A - Stabilized parenterally administrable solutions - Google Patents
Stabilized parenterally administrable solutionsInfo
- Publication number
- CA1144480A CA1144480A CA000347973A CA347973A CA1144480A CA 1144480 A CA1144480 A CA 1144480A CA 000347973 A CA000347973 A CA 000347973A CA 347973 A CA347973 A CA 347973A CA 1144480 A CA1144480 A CA 1144480A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- phospholipid
- arylpropionic
- arylacetic
- solution
- 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
- 239000002253 acid Substances 0.000 claims abstract description 45
- 150000003904 phospholipids Chemical class 0.000 claims abstract description 29
- 239000000243 solution Substances 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 25
- 239000000126 substance Substances 0.000 claims description 18
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims description 16
- 229960001017 tolmetin Drugs 0.000 claims description 11
- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 claims description 11
- 206010061218 Inflammation Diseases 0.000 claims description 10
- 230000004054 inflammatory process Effects 0.000 claims description 10
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims description 9
- RDJGLLICXDHJDY-NSHDSACASA-N (2s)-2-(3-phenoxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](C)C1=CC=CC(OC=2C=CC=CC=2)=C1 RDJGLLICXDHJDY-NSHDSACASA-N 0.000 claims description 8
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims description 8
- 229960001419 fenoprofen Drugs 0.000 claims description 8
- 229960001680 ibuprofen Drugs 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- MDKGKXOCJGEUJW-VIFPVBQESA-N (2s)-2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid Chemical compound C1=CC([C@@H](C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 MDKGKXOCJGEUJW-VIFPVBQESA-N 0.000 claims description 7
- ARHWPKZXBHOEEE-UHFFFAOYSA-N alclofenac Chemical compound OC(=O)CC1=CC=C(OCC=C)C(Cl)=C1 ARHWPKZXBHOEEE-UHFFFAOYSA-N 0.000 claims description 7
- 229960005142 alclofenac Drugs 0.000 claims description 7
- 229960001259 diclofenac Drugs 0.000 claims description 7
- 229960002390 flurbiprofen Drugs 0.000 claims description 7
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 claims description 7
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims description 7
- 229960000991 ketoprofen Drugs 0.000 claims description 7
- 229960004492 suprofen Drugs 0.000 claims description 7
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims description 6
- 229960002009 naproxen Drugs 0.000 claims description 6
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 6
- -1 Narpoxen Chemical compound 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000000644 isotonic solution Substances 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 3
- 230000005923 long-lasting effect Effects 0.000 abstract description 3
- 238000007911 parenteral administration Methods 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 244000068988 Glycine max Species 0.000 description 5
- 235000010469 Glycine max Nutrition 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 241000700159 Rattus Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000002502 liposome Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- 208000025747 Rheumatic disease Diseases 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000011866 long-term treatment Methods 0.000 description 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 2
- 150000008105 phosphatidylcholines Chemical class 0.000 description 2
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- ASWBNKHCZGQVJV-UHFFFAOYSA-N (3-hexadecanoyloxy-2-hydroxypropyl) 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC[N+](C)(C)C ASWBNKHCZGQVJV-UHFFFAOYSA-N 0.000 description 1
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- KILNVBDSWZSGLL-KXQOOQHDSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-KXQOOQHDSA-N 0.000 description 1
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 description 1
- LEMRHTTWKDVQEI-UHFFFAOYSA-N 2-(3-phenoxyphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(OC=2C=CC=CC=2)=C1 LEMRHTTWKDVQEI-UHFFFAOYSA-N 0.000 description 1
- CFWRDBDJAOHXSH-SECBINFHSA-N 2-azaniumylethyl [(2r)-2,3-diacetyloxypropyl] phosphate Chemical compound CC(=O)OC[C@@H](OC(C)=O)COP(O)(=O)OCCN CFWRDBDJAOHXSH-SECBINFHSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000784713 Cupido Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001741 anti-phlogistic effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- KILNVBDSWZSGLL-UHFFFAOYSA-N colfosceril palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- CITHEXJVPOWHKC-UHFFFAOYSA-N dimyristoyl phosphatidylcholine Chemical compound CCCCCCCCCCCCCC(=O)OCC(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC CITHEXJVPOWHKC-UHFFFAOYSA-N 0.000 description 1
- 229960003724 dimyristoylphosphatidylcholine Drugs 0.000 description 1
- ZGSPNIOCEDOHGS-UHFFFAOYSA-L disodium [3-[2,3-di(octadeca-9,12-dienoyloxy)propoxy-oxidophosphoryl]oxy-2-hydroxypropyl] 2,3-di(octadeca-9,12-dienoyloxy)propyl phosphate Chemical compound [Na+].[Na+].CCCCCC=CCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COP([O-])(=O)OCC(O)COP([O-])(=O)OCC(OC(=O)CCCCCCCC=CCC=CCCCCC)COC(=O)CCCCCCCC=CCC=CCCCCC ZGSPNIOCEDOHGS-UHFFFAOYSA-L 0.000 description 1
- 238000011549 displacement method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000008350 hydrogenated phosphatidyl choline Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000003905 phosphatidylinositols Chemical class 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- MDKGKXOCJGEUJW-UHFFFAOYSA-N suprofen Chemical compound C1=CC(C(C(O)=O)C)=CC=C1C(=O)C1=CC=CS1 MDKGKXOCJGEUJW-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- 238000005303 weighing Methods 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- 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
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
-
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
- A61K47/543—Lipids, e.g. triglycerides; Polyamines, e.g. spermine or spermidine
- A61K47/544—Phospholipids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biophysics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dermatology (AREA)
- Organic Chemistry (AREA)
- Pain & Pain Management (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792914788 DE2914788A1 (de) | 1979-04-11 | 1979-04-11 | Parenteral applizierbare, stabile arzneimittelloesungen mit entzuendungshemmender wirkung |
| DEP2914788.4 | 1979-04-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1144480A true CA1144480A (en) | 1983-04-12 |
Family
ID=6068137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000347973A Expired CA1144480A (en) | 1979-04-11 | 1980-03-19 | Stabilized parenterally administrable solutions |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4309421A (enExample) |
| JP (1) | JPS55141407A (enExample) |
| AT (1) | AT369651B (enExample) |
| AU (1) | AU539044B2 (enExample) |
| BE (1) | BE882731A (enExample) |
| CA (1) | CA1144480A (enExample) |
| CH (1) | CH642546A5 (enExample) |
| DE (1) | DE2914788A1 (enExample) |
| FR (1) | FR2453644B1 (enExample) |
| GB (1) | GB2046094B (enExample) |
| IT (1) | IT1148790B (enExample) |
| NL (1) | NL8002097A (enExample) |
| SE (1) | SE451427B (enExample) |
| ZA (1) | ZA802157B (enExample) |
Families Citing this family (57)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3042365C2 (de) * | 1980-11-10 | 1987-01-29 | Extrakta Strauss GmbH, 2000 Hamburg | Flüssige, lecithinhaltige einphasige Mehrstoffsysteme und Verfahren zu ihrer Herstellung |
| JPS57203011A (en) * | 1981-06-05 | 1982-12-13 | Taiyo Yakuhin Kogyo Kk | Anti-inflammatory external agent |
| EP0146243A1 (en) * | 1983-10-31 | 1985-06-26 | Merck Frosst Canada Inc. | Lipoxygenase inhibitors |
| DE3346525C2 (de) * | 1983-12-22 | 1987-03-19 | A. Nattermann & Cie GmbH, 5000 Köln | Pharmazeutische Zubereitung mit speziellen 1,2-Diacyl-glycero-3-phosphocholinen zur Behandlung von Erkrankungen im Magen-Darmbereich |
| DE3346526C2 (de) * | 1983-12-22 | 1986-12-11 | A. Nattermann & Cie GmbH, 5000 Köln | Pharmazeutisches Präparat zur therapeutischen Behandlung von rheumatischen Erkrankungen |
| JPH0647533B2 (ja) * | 1984-08-10 | 1994-06-22 | 裕 水島 | ４−ビフエニリル酢酸系化合物含有脂肪乳剤 |
| US5171566A (en) * | 1986-05-16 | 1992-12-15 | The Green Cross Corporation | Flurbiprofen derivative ophthalmic preparation |
| DE3621036A1 (de) * | 1986-06-24 | 1988-01-07 | Merckle Gmbh | Fluessige ibuprofen-zubereitungen |
| US4877619A (en) * | 1986-08-25 | 1989-10-31 | Vestar, Inc. | Liposomal vesicles for intraperitoneal administration of therapeutic agents |
| US5283067A (en) * | 1987-01-30 | 1994-02-01 | Ciba-Geigy Corporation | Parenteral suspensions |
| CH673395A5 (enExample) * | 1987-01-30 | 1990-03-15 | Ciba Geigy Ag | |
| CA1319886C (en) * | 1987-02-03 | 1993-07-06 | Alberto Ferro | Mixed micelle solutions |
| US4960799A (en) * | 1988-09-13 | 1990-10-02 | Ciba-Geigy Corporation | Stabilized aqueous solutions of pharmaceutically acceptable salts of ortho-(2,6-dichlorophenyl)-aminophenylacetic acid for opthalmic use |
| IT1242642B (it) * | 1990-04-17 | 1994-05-16 | Alfa Wassermann Spa | Formulazioni iniettabili contenenti naproxen sale sodico. |
| US5091188A (en) * | 1990-04-26 | 1992-02-25 | Haynes Duncan H | Phospholipid-coated microcrystals: injectable formulations of water-insoluble drugs |
| US5246707A (en) * | 1990-04-26 | 1993-09-21 | Haynes Duncan H | Sustained release delivery of water-soluble bio-molecules and drugs using phospholipid-coated microcrystals, microdroplets and high-concentration liposomes |
| US5091187A (en) * | 1990-04-26 | 1992-02-25 | Haynes Duncan H | Phospholipid-coated microcrystals: injectable formulations of water-insoluble drugs |
| DE4124252A1 (de) * | 1991-07-22 | 1993-01-28 | Knoll Ag | Verfahren zur herstellung einer sterilfiltrierbaren wirkstoffloesung |
| US5389681A (en) * | 1992-10-22 | 1995-02-14 | Ciba-Geigy Corporation | Parenteral solutions for diclofenac salts |
| DE4305003A1 (de) * | 1993-02-18 | 1994-08-25 | Knoll Ag | Verfahren zur Herstellung kolloidaler wäßriger Lösungen schwer löslicher Wirkstoffe |
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|---|---|---|---|---|
| US3044931A (en) * | 1960-01-27 | 1962-07-17 | Geigy Chem Corp | Aryloxy acetic acid amides: process for parenteral application |
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| DE2856333C2 (de) * | 1978-12-27 | 1983-09-22 | A. Nattermann & Cie GmbH, 5000 Köln | Oral einnehmbare Arzneimittel mit entzündungshemmender Wirkung |
| JPS6320209A (ja) * | 1986-07-11 | 1988-01-27 | Mitsubishi Motors Corp | 油圧サスペンシヨン装置を備える車両の車高調整方法 |
-
1979
- 1979-04-11 DE DE19792914788 patent/DE2914788A1/de active Granted
-
1980
- 1980-03-19 CA CA000347973A patent/CA1144480A/en not_active Expired
- 1980-04-08 GB GB8011632A patent/GB2046094B/en not_active Expired
- 1980-04-09 FR FR8007937A patent/FR2453644B1/fr not_active Expired
- 1980-04-10 CH CH274480A patent/CH642546A5/de not_active IP Right Cessation
- 1980-04-10 IT IT21299/80A patent/IT1148790B/it active
- 1980-04-10 US US06/139,118 patent/US4309421A/en not_active Expired - Lifetime
- 1980-04-10 ZA ZA00802157A patent/ZA802157B/xx unknown
- 1980-04-10 SE SE8002714A patent/SE451427B/sv not_active IP Right Cessation
- 1980-04-10 BE BE0/200182A patent/BE882731A/fr not_active IP Right Cessation
- 1980-04-10 JP JP4632180A patent/JPS55141407A/ja active Granted
- 1980-04-10 NL NL8002097A patent/NL8002097A/nl not_active Application Discontinuation
- 1980-04-10 AT AT0195880A patent/AT369651B/de not_active IP Right Cessation
- 1980-04-10 AU AU57331/80A patent/AU539044B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0337524B2 (enExample) | 1991-06-05 |
| DE2914788C2 (enExample) | 1990-06-21 |
| AU5733180A (en) | 1980-10-16 |
| SE451427B (sv) | 1987-10-12 |
| NL8002097A (nl) | 1980-10-14 |
| CH642546A5 (de) | 1984-04-30 |
| FR2453644B1 (fr) | 1985-07-05 |
| DE2914788A1 (de) | 1980-10-16 |
| GB2046094B (en) | 1983-10-26 |
| ZA802157B (en) | 1981-05-27 |
| US4309421A (en) | 1982-01-05 |
| SE8002714L (sv) | 1980-10-12 |
| AU539044B2 (en) | 1984-09-06 |
| JPS55141407A (en) | 1980-11-05 |
| BE882731A (fr) | 1980-07-31 |
| ATA195880A (de) | 1982-06-15 |
| AT369651B (de) | 1983-01-25 |
| IT8021299A0 (it) | 1980-04-10 |
| FR2453644A1 (fr) | 1980-11-07 |
| IT1148790B (it) | 1986-12-03 |
| GB2046094A (en) | 1980-11-12 |
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