NO820045L - Fremgangsmaate for fremstilling av stabile opploesninger av levonantradol og n-metyllevonantradol - Google Patents
Fremgangsmaate for fremstilling av stabile opploesninger av levonantradol og n-metyllevonantradolInfo
- Publication number
- NO820045L NO820045L NO820045A NO820045A NO820045L NO 820045 L NO820045 L NO 820045L NO 820045 A NO820045 A NO 820045A NO 820045 A NO820045 A NO 820045A NO 820045 L NO820045 L NO 820045L
- Authority
- NO
- Norway
- Prior art keywords
- amphiphile
- levonantradol
- active ingredient
- present
- concentration
- Prior art date
Links
- FFVXQGMUHIJQAO-BFKQJKLPSA-N levonantradol Chemical compound C([C@@H](C)OC=1C=C(OC(C)=O)C=2[C@@H]3C[C@H](O)CC[C@H]3[C@H](C)NC=2C=1)CCC1=CC=CC=C1 FFVXQGMUHIJQAO-BFKQJKLPSA-N 0.000 title claims description 25
- 229950005812 levonantradol Drugs 0.000 title claims description 25
- 238000000034 method Methods 0.000 title claims description 21
- TYTNJHKTKQNNKL-UHFFFAOYSA-N [9-hydroxy-5,6-dimethyl-3-(5-phenylpentan-2-yloxy)-6a,7,8,9,10,10a-hexahydro-6h-phenanthridin-1-yl] acetate Chemical compound C=1C(OC(C)=O)=C2C3CC(O)CCC3C(C)N(C)C2=CC=1OC(C)CCCC1=CC=CC=C1 TYTNJHKTKQNNKL-UHFFFAOYSA-N 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 claims description 49
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 claims description 27
- 239000004480 active ingredient Substances 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- -1 fatty acid ester Chemical class 0.000 claims description 18
- 239000003963 antioxidant agent Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 229920001214 Polysorbate 60 Polymers 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 claims description 8
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims description 8
- 229920000053 polysorbate 80 Polymers 0.000 claims description 8
- 229940068968 polysorbate 80 Drugs 0.000 claims description 8
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 7
- 239000000194 fatty acid Substances 0.000 claims description 7
- 229930195729 fatty acid Natural products 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000004615 ingredient Substances 0.000 claims description 3
- 239000000693 micelle Substances 0.000 claims description 3
- 230000000087 stabilizing effect Effects 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims 4
- 239000000243 solution Substances 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 10
- 239000000126 substance Substances 0.000 description 9
- 239000000872 buffer Substances 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 230000003474 anti-emetic effect Effects 0.000 description 4
- 239000002111 antiemetic agent Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 238000004108 freeze drying Methods 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- 239000001509 sodium citrate Substances 0.000 description 4
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 229930195725 Mannitol Natural products 0.000 description 3
- 229920001213 Polysorbate 20 Polymers 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000000594 mannitol Substances 0.000 description 3
- 235000010355 mannitol Nutrition 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 3
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 3
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 3
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 3
- 229940068977 polysorbate 20 Drugs 0.000 description 3
- 229940113124 polysorbate 60 Drugs 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 229920002642 Polysorbate 65 Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- NSOGAHPJIFTUHV-YINRMENDSA-N [(6s,6ar,9r,10ar)-9-hydroxy-6-methyl-3-[(2r)-5-phenylpentan-2-yl]oxy-5,6,6a,7,8,9,10,10a-octahydrophenanthridin-1-yl] acetate;hydrochloride Chemical compound Cl.C([C@@H](C)OC=1C=C(OC(C)=O)C=2[C@@H]3C[C@H](O)CC[C@H]3[C@H](C)NC=2C=1)CCC1=CC=CC=C1 NSOGAHPJIFTUHV-YINRMENDSA-N 0.000 description 2
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 235000019799 monosodium phosphate Nutrition 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000001816 polyoxyethylene sorbitan tristearate Substances 0.000 description 2
- 235000010988 polyoxyethylene sorbitan tristearate Nutrition 0.000 description 2
- 229940099511 polysorbate 65 Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 1
- FDCJDKXCCYFOCV-UHFFFAOYSA-N 1-hexadecoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC FDCJDKXCCYFOCV-UHFFFAOYSA-N 0.000 description 1
- HBXWUCXDUUJDRB-UHFFFAOYSA-N 1-octadecoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCC HBXWUCXDUUJDRB-UHFFFAOYSA-N 0.000 description 1
- JKXYOQDLERSFPT-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-octadecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO JKXYOQDLERSFPT-UHFFFAOYSA-N 0.000 description 1
- IEQAICDLOKRSRL-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO IEQAICDLOKRSRL-UHFFFAOYSA-N 0.000 description 1
- AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 description 1
- 241000208140 Acer Species 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 229920002675 Polyoxyl Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229960005274 benzocaine Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- DTPCFIHYWYONMD-UHFFFAOYSA-N decaethylene glycol Polymers OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO DTPCFIHYWYONMD-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- RCHUVCPBWWSUMC-UHFFFAOYSA-N trichloro(octyl)silane Chemical compound CCCCCCCC[Si](Cl)(Cl)Cl RCHUVCPBWWSUMC-UHFFFAOYSA-N 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
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Biophysics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Dispersion Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Otolaryngology (AREA)
- Hospice & Palliative Care (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/223,672 US4406888A (en) | 1981-01-09 | 1981-01-09 | Aqueous micellar solutions of levonantradol and N-methyllevonantradol and lyophilic forms thereof for reconstitution |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO820045L true NO820045L (no) | 1982-07-12 |
Family
ID=22837540
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO820045A NO820045L (no) | 1981-01-09 | 1982-01-08 | Fremgangsmaate for fremstilling av stabile opploesninger av levonantradol og n-metyllevonantradol |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4406888A (es) |
| EP (1) | EP0056681A3 (es) |
| JP (1) | JPS57136512A (es) |
| AU (1) | AU528316B2 (es) |
| CA (1) | CA1172569A (es) |
| CS (1) | CS235524B2 (es) |
| DK (1) | DK4382A (es) |
| ES (1) | ES8304429A1 (es) |
| FI (1) | FI813969L (es) |
| GR (1) | GR76514B (es) |
| HU (1) | HU186462B (es) |
| IL (1) | IL64731A0 (es) |
| NO (1) | NO820045L (es) |
| NZ (1) | NZ199415A (es) |
| PH (1) | PH17593A (es) |
| PT (1) | PT74257B (es) |
| ZA (1) | ZA82118B (es) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE33239E (en) * | 1983-09-06 | 1990-06-26 | Farmaceutisk Laboratorium Ferring A/S | Packaged stable enema solution or suspension containing 5-aminosalicyclic acid |
| US4657900A (en) * | 1983-09-27 | 1987-04-14 | Rowell Laboratories | Pharmaceutical article of manufacture comprising a bisulfite stabilized aqueous solution of 5-aminosalicylic acid and method |
| GB9512854D0 (en) * | 1995-06-23 | 1995-08-23 | Wellcome Found | Novel formulation |
| US8163797B2 (en) * | 2003-12-31 | 2012-04-24 | Actavis Elizabeth Llc | Method of treating with stable pravastatin formulation |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2391552A (en) * | 1942-02-25 | 1945-12-25 | Curtis David | Stabilized aromatic compounds |
| BE786427A (fr) * | 1971-07-19 | 1973-01-18 | Pfizer | Compositions aqueuses de doxycycline |
| SE7704749L (sv) * | 1976-05-17 | 1977-12-05 | Pfizer | Kinoliner och forfarande och mellanprodukter for framstellning derav |
| HU180916B (hu) | 1976-05-17 | 1983-05-30 | Pfizer | Eljárás benzo[c]kinolin-származékok előállítására |
| US4260764A (en) * | 1976-12-22 | 1981-04-07 | Pfizer Inc. | 9-Hydroxyoctahydrobenzo [C] quinolines and intermediates therefor |
| JPS54157818A (en) * | 1978-06-02 | 1979-12-13 | Tokyo Tanabe Co | Injectionable preparation of chlorethylnitrosourea compound |
| US4320124A (en) * | 1980-10-17 | 1982-03-16 | Pfizer Inc. | Composition for enhancing binding of a benzodiazepine to central benzodiazepine receptors and use thereof |
-
1981
- 1981-01-09 US US06/223,672 patent/US4406888A/en not_active Expired - Lifetime
- 1981-12-10 FI FI813969A patent/FI813969L/fi not_active Application Discontinuation
-
1982
- 1982-01-04 HU HU8211A patent/HU186462B/hu unknown
- 1982-01-05 EP EP82300018A patent/EP0056681A3/en not_active Withdrawn
- 1982-01-06 NZ NZ199415A patent/NZ199415A/en unknown
- 1982-01-07 CA CA000393740A patent/CA1172569A/en not_active Expired
- 1982-01-07 JP JP57001342A patent/JPS57136512A/ja active Pending
- 1982-01-07 PH PH26711A patent/PH17593A/en unknown
- 1982-01-08 ES ES508609A patent/ES8304429A1/es not_active Expired
- 1982-01-08 NO NO820045A patent/NO820045L/no unknown
- 1982-01-08 ZA ZA82118A patent/ZA82118B/xx unknown
- 1982-01-08 PT PT74257A patent/PT74257B/pt unknown
- 1982-01-08 DK DK4382A patent/DK4382A/da not_active Application Discontinuation
- 1982-01-08 GR GR66964A patent/GR76514B/el unknown
- 1982-01-08 CS CS82174A patent/CS235524B2/cs unknown
- 1982-01-08 IL IL64731A patent/IL64731A0/xx unknown
- 1982-01-08 AU AU79404/82A patent/AU528316B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| AU7940482A (en) | 1982-07-22 |
| HU186462B (en) | 1985-08-28 |
| CA1172569A (en) | 1984-08-14 |
| AU528316B2 (en) | 1983-04-21 |
| FI813969L (fi) | 1982-07-10 |
| GR76514B (es) | 1984-08-10 |
| ZA82118B (en) | 1982-11-24 |
| NZ199415A (en) | 1985-04-30 |
| DK4382A (da) | 1982-07-10 |
| PT74257A (en) | 1982-02-01 |
| IL64731A0 (en) | 1982-03-31 |
| US4406888A (en) | 1983-09-27 |
| JPS57136512A (en) | 1982-08-23 |
| PT74257B (en) | 1984-05-29 |
| PH17593A (en) | 1984-10-02 |
| ES508609A0 (es) | 1983-03-01 |
| ES8304429A1 (es) | 1983-03-01 |
| EP0056681A2 (en) | 1982-07-28 |
| CS235524B2 (en) | 1985-05-15 |
| EP0056681A3 (en) | 1983-07-20 |
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