DE3346123A1 - Pharmazeutische praeparate von in wasser schwerloeslichen oder instabilen arzneistoffen und verfahren zu ihrer herstellung - Google Patents
Pharmazeutische praeparate von in wasser schwerloeslichen oder instabilen arzneistoffen und verfahren zu ihrer herstellungInfo
- Publication number
- DE3346123A1 DE3346123A1 DE19833346123 DE3346123A DE3346123A1 DE 3346123 A1 DE3346123 A1 DE 3346123A1 DE 19833346123 DE19833346123 DE 19833346123 DE 3346123 A DE3346123 A DE 3346123A DE 3346123 A1 DE3346123 A1 DE 3346123A1
- Authority
- DE
- Germany
- Prior art keywords
- water
- cyclodextrin
- drug
- pharmaceutical preparation
- hydroxyethyl
- 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.)
- Withdrawn
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims description 14
- 239000000126 substance Substances 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 10
- 229940079593 drug Drugs 0.000 claims abstract description 18
- 239000003814 drug Substances 0.000 claims abstract description 18
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical class OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 239000001116 FEMA 4028 Substances 0.000 claims description 15
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims description 15
- 229960004853 betadex Drugs 0.000 claims description 15
- -1 hydroxypropyl Chemical group 0.000 claims description 12
- 229920000858 Cyclodextrin Polymers 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 150000002170 ethers Chemical class 0.000 claims description 5
- 239000008363 phosphate buffer Substances 0.000 claims description 4
- 150000003431 steroids Chemical class 0.000 claims description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 3
- 229940097217 cardiac glycoside Drugs 0.000 claims description 3
- 239000002368 cardiac glycoside Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229930002534 steroid glycoside Natural products 0.000 claims description 3
- 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 claims description 2
- 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 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940124599 anti-inflammatory drug Drugs 0.000 claims 1
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 claims 1
- 230000003637 steroidlike Effects 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 19
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 11
- 239000008055 phosphate buffer solution Substances 0.000 description 7
- PCWPQSDFNIFUPO-VDQKLNDWSA-N (1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37S,38R,39S,40R,41S,42R,43S,44R,45S,46R,47S,48R,49S)-37,39,41,43,45,47,49-heptakis(2-hydroxyethoxy)-5,10,15,20,25,30,35-heptakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,38,40,42,44,46,48-heptol Chemical compound OCCO[C@H]1[C@H](O)[C@@H]2O[C@H]3O[C@H](CO)[C@@H](O[C@H]4O[C@H](CO)[C@@H](O[C@H]5O[C@H](CO)[C@@H](O[C@H]6O[C@H](CO)[C@@H](O[C@H]7O[C@H](CO)[C@@H](O[C@H]8O[C@H](CO)[C@@H](O[C@H]1O[C@@H]2CO)[C@@H](O)[C@@H]8OCCO)[C@@H](O)[C@@H]7OCCO)[C@@H](O)[C@@H]6OCCO)[C@@H](O)[C@@H]5OCCO)[C@@H](O)[C@@H]4OCCO)[C@@H](O)[C@@H]3OCCO PCWPQSDFNIFUPO-VDQKLNDWSA-N 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 229960000905 indomethacin Drugs 0.000 description 5
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 3
- 229960003529 diazepam Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012907 medicinal substance Substances 0.000 description 3
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 3
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- 150000001557 benzodiazepines Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 229960004926 chlorobutanol Drugs 0.000 description 2
- 229960003957 dexamethasone Drugs 0.000 description 2
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000006196 drop Substances 0.000 description 2
- 239000003889 eye drop Substances 0.000 description 2
- 229940012356 eye drops Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- 229960004194 lidocaine Drugs 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229960002985 medroxyprogesterone acetate Drugs 0.000 description 2
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 2
- 239000000693 micelle Substances 0.000 description 2
- 239000002504 physiological saline solution Substances 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 235000002639 sodium chloride Nutrition 0.000 description 2
- 239000007909 solid dosage form Substances 0.000 description 2
- 150000008143 steroidal glycosides Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YZOUYRAONFXZSI-SBHWVFSVSA-N (1S,3R,5R,6R,8R,10R,11R,13R,15R,16R,18R,20R,21R,23R,25R,26R,28R,30R,31S,33R,35R,36R,37S,38R,39S,40R,41S,42R,43S,44R,45S,46R,47S,48R,49S)-5,10,15,20,25,30,35-heptakis(hydroxymethyl)-37,39,40,41,42,43,44,45,46,47,48,49-dodecamethoxy-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,38-diol Chemical compound O([C@@H]([C@H]([C@@H]1OC)OC)O[C@H]2[C@@H](O)[C@@H]([C@@H](O[C@@H]3[C@@H](CO)O[C@@H]([C@H]([C@@H]3O)OC)O[C@@H]3[C@@H](CO)O[C@@H]([C@H]([C@@H]3OC)OC)O[C@@H]3[C@@H](CO)O[C@@H]([C@H]([C@@H]3OC)OC)O[C@@H]3[C@@H](CO)O[C@@H]([C@H]([C@@H]3OC)OC)O3)O[C@@H]2CO)OC)[C@H](CO)[C@H]1O[C@@H]1[C@@H](OC)[C@H](OC)[C@H]3[C@@H](CO)O1 YZOUYRAONFXZSI-SBHWVFSVSA-N 0.000 description 1
- CUJVBAPGYBSBHJ-YWBSARSQSA-N 2-[[(1R,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21R,23R,25R,26R,28R,30R,31R,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-36,38,40,42-tetrakis(carboxymethoxy)-10,15-bis(carboxymethoxymethyl)-37,39,41,43,44,45,46,47,48,49-decahydroxy-20,25,30,35-tetrakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-5-yl]methoxy]acetic acid Chemical compound OC[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCC(O)=O)O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCC(O)=O)O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCC(O)=O)O[C@@H]3[C@@H](CO)O[C@H](O[C@@H]4[C@@H](CO)O[C@H](O[C@@H]5[C@@H](CO)O[C@H](O[C@H]1[C@H](OCC(O)=O)[C@H]2O)[C@H](O)[C@H]5OCC(O)=O)[C@H](O)[C@H]4OCC(O)=O)[C@H](O)[C@H]3OCC(O)=O CUJVBAPGYBSBHJ-YWBSARSQSA-N 0.000 description 1
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- 239000011770 retinyl acetate Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
-
- 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
- A61K47/69—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
- C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Nanotechnology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Biotechnology (AREA)
- Polymers & Plastics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biophysics (AREA)
- Organic Chemistry (AREA)
- General Engineering & Computer Science (AREA)
- Medical Informatics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biochemistry (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833346123 DE3346123A1 (de) | 1983-12-21 | 1983-12-21 | Pharmazeutische praeparate von in wasser schwerloeslichen oder instabilen arzneistoffen und verfahren zu ihrer herstellung |
| AU38352/85A AU565966B2 (en) | 1983-12-21 | 1984-12-20 | Pharmaceutical compositions containing drugs which are instable or sparingly soluble in water and methods for their preparation |
| JP60500307A JPS61500788A (ja) | 1983-12-21 | 1984-12-20 | 水に不安定なまたは僅かに溶解性の薬物を含有する医薬調製物およびその製造方法 |
| HU85795D HU200943B (en) | 1983-12-21 | 1984-12-20 | Process for producing pharmaceutical compositions comprising active ingredients which are instable or badly soluble in water |
| AT84115965T ATE51145T1 (de) | 1983-12-21 | 1984-12-20 | Pharmazeutische praeparate von in wasser schwerloeslichen oder instabilen arzneistoffen und verfahren zu ihrer herstellung. |
| EP84115965A EP0149197B2 (de) | 1983-12-21 | 1984-12-20 | Pharmazeutische Präparate von in Wasser schwerlöslichen oder instabilen Arzneistoffen und Verfahren zu ihrer Herstellung |
| DE8484115965T DE3481680D1 (de) | 1983-12-21 | 1984-12-20 | Pharmazeutische praeparate von in wasser schwerloeslichen oder instabilen arzneistoffen und verfahren zu ihrer herstellung. |
| KR1019850700172A KR920008700B1 (ko) | 1983-12-21 | 1984-12-20 | 수-난용성 또는 수-불안정성 약제와 β-사이클로덱스트린 에테르의 수용성 복합체의 제조방법 |
| PCT/EP1984/000417 WO1985002767A1 (en) | 1983-12-21 | 1984-12-20 | Pharmaceutical compositions containing drugs which are instable or sparingly soluble in water and methods for their preparation |
| ZA8410042A ZA8410042B (en) | 1983-12-21 | 1984-12-21 | Pharmaceutical compositions containing drugs which are instable or sparingly soluble in water and methods for their preparation |
| CA000470876A CA1222697A (en) | 1983-12-21 | 1984-12-21 | Pharmaceutical compositions containing drugs which are instable or sparingly soluble in water and methods for their preparation |
| NO853070A NO171888C (no) | 1983-12-21 | 1985-08-02 | Fremgangsmaate for fremstilling av et farmasoeytisk preparat inneholdende medisinske stoffer som er lite opploeselige eller ustabile i vann |
| DK198503595A DK175288B1 (da) | 1983-12-21 | 1985-08-07 | Farmaceutiske midler indeholdende lægemidler, der er ustabile eller sparsomt oplöselige i vand, og fremgangsmåder til deres fremstilling |
| FI853198A FI86140C (fi) | 1983-12-21 | 1985-08-20 | Foerfarande foer framstaellning av en farmaceutisk beredning som innehaoller ett i vatten svaorloesligt eller i vatten instabilt laekemedel. |
| SG248/93A SG24893G (en) | 1983-12-21 | 1993-03-04 | Pharmaceutical compositions containing drugs which are sparingly soluble in water or instable and methods for their preparation |
| HK1312/93A HK131293A (en) | 1983-12-21 | 1993-11-25 | Pharmaceutical compositions containing drugs which are sparingly soluble in water or instable and methods for their preparation |
| CY168994A CY1689A (en) | 1983-12-21 | 1994-01-14 | Pharmaceutical compositions containing drugs wich are sparingly soluble in water or instable and methods for their preparation |
| NL980009C NL980009I1 (nl) | 1983-12-21 | 1998-02-26 | Farmaceutische preparaten van in water moeilijk oplosbare of instabiele geneesmiddelen en werkwijzenvoor het bereiden daarvan. |
| LU90283C LU90283I2 (fr) | 1983-12-21 | 1998-09-02 | Sporanox soluté buvable et ses dérivés pharmaceutiquement acceptables |
| NO2000007C NO2000007I1 (no) | 1983-12-21 | 2000-08-21 | Itraconazol inklusjonskompleks med hydroksypropyl-ß -cyklodekstriner |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833346123 DE3346123A1 (de) | 1983-12-21 | 1983-12-21 | Pharmazeutische praeparate von in wasser schwerloeslichen oder instabilen arzneistoffen und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3346123A1 true DE3346123A1 (de) | 1985-06-27 |
Family
ID=6217510
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19833346123 Withdrawn DE3346123A1 (de) | 1983-12-21 | 1983-12-21 | Pharmazeutische praeparate von in wasser schwerloeslichen oder instabilen arzneistoffen und verfahren zu ihrer herstellung |
| DE8484115965T Expired - Lifetime DE3481680D1 (de) | 1983-12-21 | 1984-12-20 | Pharmazeutische praeparate von in wasser schwerloeslichen oder instabilen arzneistoffen und verfahren zu ihrer herstellung. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8484115965T Expired - Lifetime DE3481680D1 (de) | 1983-12-21 | 1984-12-20 | Pharmazeutische praeparate von in wasser schwerloeslichen oder instabilen arzneistoffen und verfahren zu ihrer herstellung. |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0149197B2 (https=) |
| JP (1) | JPS61500788A (https=) |
| AT (1) | ATE51145T1 (https=) |
| AU (1) | AU565966B2 (https=) |
| CA (1) | CA1222697A (https=) |
| CY (1) | CY1689A (https=) |
| DE (2) | DE3346123A1 (https=) |
| DK (1) | DK175288B1 (https=) |
| FI (1) | FI86140C (https=) |
| HK (1) | HK131293A (https=) |
| HU (1) | HU200943B (https=) |
| LU (1) | LU90283I2 (https=) |
| NL (1) | NL980009I1 (https=) |
| NO (1) | NO2000007I1 (https=) |
| SG (1) | SG24893G (https=) |
| WO (1) | WO1985002767A1 (https=) |
| ZA (1) | ZA8410042B (https=) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3809808A1 (de) * | 1988-03-23 | 1989-10-05 | Hexal Pharma Gmbh & Co Kg | Feste, insbesondere festorale und rektale, etofenamat enthaltende arzneimittel |
| DE4227569C1 (de) * | 1992-08-20 | 1994-06-09 | Inst Chemo Biosensorik | Verfahren zum empfindlichen enzymatischen Nachweis von anorganischem Phosphat |
| RU2108109C1 (ru) * | 1990-10-04 | 1998-04-10 | Мадаус АГ | Способ получения комплекса силибинина с циклодекстрином, комплекс включения силибинина с циклодекстрином, фармацевтическая композиция антигепатотоксической активности и способ ее получения |
| DE19848303A1 (de) * | 1998-10-14 | 2000-04-20 | Schering Ag | Kombination aus Gestagenen und Zuckern |
| EP0780129A3 (en) * | 1995-12-11 | 2000-07-19 | CAC Corporation | Adrenal cortical steroid containing external therapeutic composition for dermatitis |
| US6194181B1 (en) | 1998-02-19 | 2001-02-27 | Novartis Ag | Fermentative preparation process for and crystal forms of cytostatics |
| US6683100B2 (en) | 1999-01-19 | 2004-01-27 | Novartis Ag | Organic compounds |
| US6962944B2 (en) | 2001-07-31 | 2005-11-08 | Arqule, Inc. | Pharmaceutical compositions containing beta-lapachone, or derivatives or analogs thereof, and methods of using same |
| US7074824B2 (en) | 2001-07-31 | 2006-07-11 | Arqule, Inc. | Pharmaceutical compositions containing beta-lapachone, or derivatives or analogs thereof, and methods of using same |
| US11925659B2 (en) | 2018-10-29 | 2024-03-12 | Cyclo Therapeutics, Inc. | Methods for treating Alzheimer's disease |
Families Citing this family (125)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4920214A (en) * | 1986-04-16 | 1990-04-24 | American Maize-Products Company | Process for producing modified cyclodextrins |
| JPH0819004B2 (ja) * | 1986-12-26 | 1996-02-28 | 日清製粉株式会社 | 徐放性医薬製剤 |
| IT1203968B (it) * | 1987-04-24 | 1989-02-23 | Bononi Ricerca | Complessi di b-ciclodestrina ad attivita' antimicotica |
| NZ224497A (en) * | 1987-05-18 | 1990-04-26 | Janssen Pharmaceutica Nv | Pharmaceutical composition comprising flunarizine |
| JP2577049B2 (ja) * | 1987-06-04 | 1997-01-29 | 三共株式会社 | シクロスポリン製剤 |
| NZ225045A (en) * | 1987-07-01 | 1990-06-26 | Janssen Pharmaceutica Nv | Antiviral pharmaceutical compositions containing cyclodextrin and an antiviral agent |
| ZA884592B (en) * | 1987-08-31 | 1989-03-29 | Warner Lambert Co | Cyclodextrin complexes of bis-biguanido hexane compounds |
| US4877774A (en) * | 1987-09-09 | 1989-10-31 | The United States Of America As Represented By The Department Of Health And Human Services | Administration of steroid hormones |
| US5256652A (en) * | 1987-11-12 | 1993-10-26 | Pharmedic Co. | Topical compositions and methods for treatment of male impotence |
| NO885689L (no) * | 1987-12-22 | 1989-06-23 | Glaxo Group Ltd | Fremgangsmaate for fremstilling av vandige preparater inneholdende et piperidinylcyklopentyl-heptensyrederivat. |
| US5221695A (en) * | 1987-12-22 | 1993-06-22 | Glaxo Group Limited | Aqueous formulation containing a piperidinylcyclopentylheptenoic acid derivative and beta-cyclodextrin |
| US5017566A (en) * | 1987-12-30 | 1991-05-21 | University Of Florida | Redox systems for brain-targeted drug delivery |
| US5002935A (en) * | 1987-12-30 | 1991-03-26 | University Of Florida | Improvements in redox systems for brain-targeted drug delivery |
| ES2037385T3 (es) * | 1988-01-14 | 1993-06-16 | Akzo N.V. | Un procedimiento de manufactura de una preparacion farmaceutica para administracion local. |
| US5658894A (en) * | 1989-04-23 | 1997-08-19 | The Trustees Of The University Of Pennsylvania | Compositions for inhibiting restenosis |
| US5637575A (en) * | 1988-01-19 | 1997-06-10 | The Trustees Of The University Of Pennsylvania | Methods of inhibiting restenosis |
| AU626538B2 (en) * | 1988-01-19 | 1992-08-06 | Moses Judah Folkman | Growth inhibiting agent and the use thereof |
| US5760015A (en) * | 1988-01-19 | 1998-06-02 | The Trustees Of The University Of Pennsylvania | Cyclodextrin compounds and methods of making and use thereof |
| US5019562A (en) * | 1988-01-19 | 1991-05-28 | The Trustees Of The University Of Pennsylvania/Childrens Hospital Corporation | Growth inhibiting agent and the use thereof |
| DE68910113T2 (de) * | 1988-01-19 | 1994-03-17 | Childrens Hospital Corp | Wachstuminhibierendes mittel und dessen verwendung. |
| US5236944A (en) * | 1988-03-28 | 1993-08-17 | Janssen Pharmaceutica N.V. | Compounds, compositions and anti-neoplastic methods |
| DE3815902A1 (de) * | 1988-05-10 | 1989-11-23 | Schwarz Pharma Gmbh | Einschlussverbindungen des 1-(4-(2-(5-chloro-2-methoxybenzamido)ethyl) -phenylsulfonyl)-3-cyclohexylharnstoffs mit (alpha)-,ss-,(gamma)-cyclodextrinen, jeweils diese enthaltendes pharmazeutisches praeparat und verfahren zu deren herstellung |
| GB8813682D0 (en) * | 1988-06-09 | 1988-07-13 | Reckitt & Colmann Prod Ltd | Pharmaceutical compositions |
| NL8801670A (nl) | 1988-07-01 | 1990-02-01 | Walter Adrianus Josephus Johan | Farmaceutisch preparaat. |
| US5229370A (en) * | 1988-08-15 | 1993-07-20 | Ammeraal Robert N | Water soluble branched beta cyclodextrin steroid complex |
| EP0381747A4 (en) * | 1988-08-15 | 1991-09-11 | American Maize-Products Company | Water soluble branched beta cyclodextrin steroid complex |
| MY106598A (en) * | 1988-08-31 | 1995-06-30 | Australian Commercial Res & Development Ltd | Compositions and methods for drug delivery and chromatography. |
| US5997856A (en) * | 1988-10-05 | 1999-12-07 | Chiron Corporation | Method and compositions for solubilization and stabilization of polypeptides, especially proteins |
| AU616571B2 (en) * | 1988-10-28 | 1991-10-31 | Shiseido Company Ltd. | Cosmetic composition containing inclusion product with hydroxyalkylated cyclodextrin |
| JP2929108B2 (ja) * | 1988-10-28 | 1999-08-03 | 株式会社資生堂 | 化粧料および粉末化粧料 |
| IT1227626B (it) * | 1988-11-28 | 1991-04-23 | Vectorpharma Int | Farmaci supportati aventi velocita' di dissoluzione aumentata e procedimento per la loro preparazione |
| US5441944A (en) * | 1989-04-23 | 1995-08-15 | The Trustees Of The University Of Pennsylvania | Substituted cyclodextrin sulfates and their uses as growth modulating agents |
| GB8910069D0 (en) * | 1989-05-03 | 1989-06-21 | Janssen Pharmaceutica Nv | Method of topically treating acne vulgaris |
| JPH0737390B2 (ja) * | 1989-08-29 | 1995-04-26 | 久光製薬株式会社 | 軟膏組成物 |
| WO1991004026A1 (en) * | 1989-09-14 | 1991-04-04 | Australian Commercial Research & Development Limited | Drug delivery compositions |
| US5053240A (en) * | 1989-10-24 | 1991-10-01 | Kalamazoo Holdings, Inc. | Norbixin adducts with water-soluble or water-dispersible proteins or branched-chain or cyclic polysaccharides |
| GB9001987D0 (en) * | 1990-01-29 | 1990-03-28 | Janssen Pharmaceutica Nv | Improved cyclodextrin based erythropietin formulation |
| EP0518930A4 (en) * | 1990-03-02 | 1993-09-15 | Australian Commercial Research & Development Limited | Cyclodextrin compositions and methods for pharmaceutical and industrial applications |
| FR2660309B1 (fr) * | 1990-03-27 | 1992-07-17 | Roussel Uclaf | Nouveaux complexes de l'acide tiaprofenique ou de ses esters insolubles ou partiellement solubles avec les cyclodextrines ou leurs derives. |
| JP2867162B2 (ja) * | 1990-03-31 | 1999-03-08 | 株式会社資生堂 | ピールオフ型パック化粧料 |
| US5124154A (en) * | 1990-06-12 | 1992-06-23 | Insite Vision Incorporated | Aminosteroids for ophthalmic use |
| US5120720A (en) * | 1990-09-20 | 1992-06-09 | The United States Of America As Represented By The Secretary Of The Department Of Health & Human Services | Preparation of lipophile:hydroxypropylcyclodextrin complexes by a method using co-solubilizers |
| LU87843A1 (fr) * | 1990-11-15 | 1992-08-25 | Cird Galderma | Gel aqueux a base d'acide retinoique et d'hydroxypropyl-beta-cyclodextrine et son utilisation en medecine humaine et en cosmetique |
| JPH04351603A (ja) * | 1991-05-29 | 1992-12-07 | Toppan Printing Co Ltd | β−シクロデキストリン誘導体 |
| EP1004318A3 (en) * | 1991-06-21 | 2002-08-07 | Takeda Chemical Industries, Ltd. | Cyclodextrin composition |
| US5446030A (en) * | 1991-09-19 | 1995-08-29 | Weisz; Paul B. | Prevention of hemolysis |
| PL170591B1 (pl) * | 1991-10-16 | 1997-01-31 | Schering Corp | Sposób wytwarzania kompozycji farmaceutycznej zawierajacej lipofilowy antybiotyk oligosacharydowy PL PL PL PL PL PL |
| IL103558A0 (en) | 1991-10-30 | 1993-03-15 | Schering Corp | Tri-substituted tetrahydrofuran antifungals |
| US5254541A (en) * | 1991-11-15 | 1993-10-19 | Merck Frosst Canada, Inc. | (Quinolin-2-ylmethoxy)indole/cyclodextrin complex |
| DE4207922A1 (de) * | 1992-03-13 | 1993-09-23 | Pharmatech Gmbh | Wasserloesliche einschlussverbindungen und verfahren zu deren herstellung |
| CA2117651C (en) * | 1992-03-18 | 2006-01-03 | Jan Heeres | Itraconazole and saperconazole stereoisomers |
| US5324718A (en) * | 1992-07-14 | 1994-06-28 | Thorsteinn Loftsson | Cyclodextrin/drug complexation |
| US5472954A (en) * | 1992-07-14 | 1995-12-05 | Cyclops H.F. | Cyclodextrin complexation |
| TW251236B (https=) * | 1992-09-10 | 1995-07-11 | Ciba Vision Ag | |
| JP2879395B2 (ja) * | 1992-10-26 | 1999-04-05 | 富士写真フイルム株式会社 | ロダシアニン化合物及びシクロデキストリンを含有する抗癌性組成物 |
| US5494901A (en) * | 1993-01-05 | 1996-02-27 | Javitt; Jonathan C. | Topical compositions for the eye comprising a β-cyclodextrin derivative and a therapeutic agent |
| EP0687174B1 (en) * | 1993-03-05 | 2001-06-13 | Hexal Ag | Crystalline cyclodextrin inclusion complexes of ranitidine hydrochloride and process for their preparation |
| EP0697874A1 (en) * | 1993-03-31 | 1996-02-28 | The Trustees Of The University Of Pennsylvania | Methods of affecting the growth of living tissue in mammals and compounds and compositions therefor |
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| PH31594A (en) * | 1993-09-30 | 1998-11-03 | Janssen Pharmaceutica Nv | Oral formulations on an antifungal. |
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| AU1716995A (en) * | 1994-03-18 | 1995-10-09 | Ciba-Geigy Ag | Aqueous solution of levocabastine for ophthalmic use |
| DE4414138A1 (de) * | 1994-04-22 | 1995-10-26 | Consortium Elektrochem Ind | Acylierte gamma-Cyclodextrine |
| JPH10500982A (ja) * | 1994-05-27 | 1998-01-27 | ファーマーク、ネダーランド、ベスローテン、フェンノートシャップ | 医薬組成物 |
| FR2726765B1 (fr) * | 1994-11-14 | 1996-12-20 | Cis Bio Int | Compositions radiopharmaceutiques comprenant un complexe d'inclusion d'une cyclodextrine et d'un acide gras radiohalogene |
| US5576311A (en) * | 1994-11-30 | 1996-11-19 | Pharmos Corporation | Cyclodextrins as suspending agents for pharmaceutical suspensions |
| FR2735136B1 (fr) * | 1995-06-08 | 1997-08-14 | Roquette Freres | Composition pulverulente d'hydroxypropyl-betacyclodextrine et son procede de preparation. |
| GB9605705D0 (en) | 1996-03-19 | 1996-05-22 | Pfizer Ltd | Therapeutic agents |
| DE69733664T3 (de) | 1996-04-19 | 2011-04-14 | Grifols Inc. (n.d. Ges.d.Staates Delaware), Los Angeles | Verfahren zur INaktivierung von Viren und Lyophilisierung von Blutproteinen |
| SE9601556D0 (sv) * | 1996-04-24 | 1996-04-24 | Astra Ab | New pharmaceutical formulation of a thrombin inhibitor for parenteral use |
| PT877600E (pt) * | 1996-08-09 | 2004-02-27 | Alcon Mfg Ltd | Sistemas conservantes para composicoes farmaceuticas contendo ciclodextrinas |
| US5942501A (en) * | 1996-08-16 | 1999-08-24 | Collaborative Laboratories, Inc. | Cyclodextrin derivative complex |
| EP0838225A3 (en) * | 1996-10-25 | 1999-03-24 | Hiji, Yasutake | Aqueous local anesthetic solution |
| JP3608800B2 (ja) * | 1997-03-26 | 2005-01-12 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 抗真菌剤およびポリマーでコートされたコアを有するペレット剤 |
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| AU9650398A (en) * | 1997-11-07 | 1999-05-31 | Daiichi Pharmaceutical Co., Ltd. | Piperazine-cyclodextrin complexes |
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| GB9906126D0 (en) * | 1999-03-18 | 1999-05-12 | Knoll Ag | Pharmaceutical formulations |
| WO2001001955A1 (en) * | 1999-07-02 | 2001-01-11 | Janssen Pharmaceutica N.V. | Nasal formulation of an antifungal |
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| JP4870314B2 (ja) | 2000-05-02 | 2012-02-08 | セラヴァンス, インコーポレーテッド | シクロデキストリンを含むグリコペプチド抗生物質組成物 |
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| US6881726B2 (en) | 2001-12-24 | 2005-04-19 | Dow Pharmaceutical Sciences | Aqueous compositions containing metronidazole |
| EP1476135A1 (en) | 2002-02-22 | 2004-11-17 | Pharmacia Corporation | Ophthalmic formulation with gum system |
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Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3459731A (en) * | 1966-12-16 | 1969-08-05 | Corn Products Co | Cyclodextrin polyethers and their production |
| US3453259A (en) * | 1967-03-22 | 1969-07-01 | Corn Products Co | Cyclodextrin polyol ethers and their oxidation products |
| HU181703B (en) * | 1980-05-09 | 1983-11-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing aqueus solutuins of water insoluble or hardly soluble vitamines, steroides, localanesthetics, prostanoides and non-steroid and antiphlogistic agents |
| US4371673A (en) * | 1980-07-21 | 1983-02-01 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Water soluble forms of retinoids |
-
1983
- 1983-12-21 DE DE19833346123 patent/DE3346123A1/de not_active Withdrawn
-
1984
- 1984-12-20 WO PCT/EP1984/000417 patent/WO1985002767A1/en not_active Ceased
- 1984-12-20 HU HU85795D patent/HU200943B/hu unknown
- 1984-12-20 AT AT84115965T patent/ATE51145T1/de active
- 1984-12-20 JP JP60500307A patent/JPS61500788A/ja active Granted
- 1984-12-20 EP EP84115965A patent/EP0149197B2/de not_active Expired - Lifetime
- 1984-12-20 DE DE8484115965T patent/DE3481680D1/de not_active Expired - Lifetime
- 1984-12-20 AU AU38352/85A patent/AU565966B2/en not_active Expired
- 1984-12-21 CA CA000470876A patent/CA1222697A/en not_active Expired
- 1984-12-21 ZA ZA8410042A patent/ZA8410042B/xx unknown
-
1985
- 1985-08-07 DK DK198503595A patent/DK175288B1/da active
- 1985-08-20 FI FI853198A patent/FI86140C/fi active IP Right Grant
-
1993
- 1993-03-04 SG SG248/93A patent/SG24893G/en unknown
- 1993-11-25 HK HK1312/93A patent/HK131293A/xx not_active IP Right Cessation
-
1994
- 1994-01-14 CY CY168994A patent/CY1689A/xx unknown
-
1998
- 1998-02-26 NL NL980009C patent/NL980009I1/nl unknown
- 1998-09-02 LU LU90283C patent/LU90283I2/fr unknown
-
2000
- 2000-08-21 NO NO2000007C patent/NO2000007I1/no unknown
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3809808A1 (de) * | 1988-03-23 | 1989-10-05 | Hexal Pharma Gmbh & Co Kg | Feste, insbesondere festorale und rektale, etofenamat enthaltende arzneimittel |
| RU2108109C1 (ru) * | 1990-10-04 | 1998-04-10 | Мадаус АГ | Способ получения комплекса силибинина с циклодекстрином, комплекс включения силибинина с циклодекстрином, фармацевтическая композиция антигепатотоксической активности и способ ее получения |
| DE4227569C1 (de) * | 1992-08-20 | 1994-06-09 | Inst Chemo Biosensorik | Verfahren zum empfindlichen enzymatischen Nachweis von anorganischem Phosphat |
| EP0780129A3 (en) * | 1995-12-11 | 2000-07-19 | CAC Corporation | Adrenal cortical steroid containing external therapeutic composition for dermatitis |
| US7101702B2 (en) | 1998-02-19 | 2006-09-05 | Novartis Ag | Fermentative preparation process for and crystal forms of cytostatics |
| US6194181B1 (en) | 1998-02-19 | 2001-02-27 | Novartis Ag | Fermentative preparation process for and crystal forms of cytostatics |
| US6380227B1 (en) | 1998-02-19 | 2002-04-30 | Novartis Ag | Fermentative preparation process for and crystal forms of cytostatics |
| US6656711B2 (en) | 1998-02-19 | 2003-12-02 | Novartis Ag | Fermentative preparation process for and crystal forms of cytostatics |
| DE19848303A1 (de) * | 1998-10-14 | 2000-04-20 | Schering Ag | Kombination aus Gestagenen und Zuckern |
| US6683100B2 (en) | 1999-01-19 | 2004-01-27 | Novartis Ag | Organic compounds |
| US6962944B2 (en) | 2001-07-31 | 2005-11-08 | Arqule, Inc. | Pharmaceutical compositions containing beta-lapachone, or derivatives or analogs thereof, and methods of using same |
| US7074824B2 (en) | 2001-07-31 | 2006-07-11 | Arqule, Inc. | Pharmaceutical compositions containing beta-lapachone, or derivatives or analogs thereof, and methods of using same |
| US11925659B2 (en) | 2018-10-29 | 2024-03-12 | Cyclo Therapeutics, Inc. | Methods for treating Alzheimer's disease |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0570612B2 (https=) | 1993-10-05 |
| EP0149197A2 (de) | 1985-07-24 |
| ZA8410042B (en) | 1985-09-25 |
| DE3481680D1 (de) | 1990-04-26 |
| FI853198L (fi) | 1985-08-20 |
| LU90283I2 (fr) | 1998-11-03 |
| HU200943B (en) | 1990-09-28 |
| HUT40561A (en) | 1987-01-28 |
| DK359585A (da) | 1985-08-07 |
| AU565966B2 (en) | 1987-10-01 |
| EP0149197A3 (en) | 1985-08-14 |
| NL980009I1 (nl) | 1998-05-06 |
| DK175288B1 (da) | 2004-08-09 |
| CY1689A (en) | 1994-01-14 |
| DK359585D0 (da) | 1985-08-07 |
| FI86140C (fi) | 1992-07-27 |
| FI86140B (fi) | 1992-04-15 |
| JPS61500788A (ja) | 1986-04-24 |
| NO2000007I1 (no) | 2000-09-21 |
| WO1985002767A1 (en) | 1985-07-04 |
| EP0149197B1 (de) | 1990-03-21 |
| SG24893G (en) | 1993-08-06 |
| ATE51145T1 (de) | 1990-04-15 |
| HK131293A (en) | 1993-12-03 |
| CA1222697A (en) | 1987-06-09 |
| AU3835285A (en) | 1985-07-12 |
| FI853198A0 (fi) | 1985-08-20 |
| EP0149197B2 (de) | 1997-01-08 |
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