AU758989B2 - Cosolvent formulations - Google Patents
Cosolvent formulations Download PDFInfo
- Publication number
- AU758989B2 AU758989B2 AU33598/99A AU3359899A AU758989B2 AU 758989 B2 AU758989 B2 AU 758989B2 AU 33598/99 A AU33598/99 A AU 33598/99A AU 3359899 A AU3359899 A AU 3359899A AU 758989 B2 AU758989 B2 AU 758989B2
- Authority
- AU
- Australia
- Prior art keywords
- composition
- ethanol
- propylene glycol
- self
- preserved
- 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.)
- Ceased, expires
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 84
- 238000009472 formulation Methods 0.000 title claims abstract description 57
- 239000006184 cosolvent Substances 0.000 title description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 84
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- 150000002334 glycols Chemical class 0.000 claims abstract description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- -1 vitamin D compound Chemical class 0.000 claims description 15
- 229930003316 Vitamin D Natural products 0.000 claims description 14
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 claims description 14
- 235000019166 vitamin D Nutrition 0.000 claims description 14
- 239000011710 vitamin D Substances 0.000 claims description 14
- 229940046008 vitamin d Drugs 0.000 claims description 14
- 238000007911 parenteral administration Methods 0.000 claims description 12
- 230000001954 sterilising effect Effects 0.000 claims description 11
- 238000004659 sterilization and disinfection Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- GMRQFYUYWCNGIN-NKMMMXOESA-N calcitriol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C GMRQFYUYWCNGIN-NKMMMXOESA-N 0.000 claims description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- 235000020964 calcitriol Nutrition 0.000 claims description 4
- 239000011612 calcitriol Substances 0.000 claims description 4
- 229960005084 calcitriol Drugs 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- 239000003814 drug Substances 0.000 abstract description 16
- 229940124597 therapeutic agent Drugs 0.000 abstract description 15
- BPKAHTKRCLCHEA-FOPGHSPUSA-N 19-Nor-1-α,25-dihydroxyvitamin D2 Chemical compound C1([C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](C=C[C@H](C)C(C)(C)O)C)=CC=C1C[C@@H](O)C[C@H](O)C1 BPKAHTKRCLCHEA-FOPGHSPUSA-N 0.000 description 21
- 230000002335 preservative effect Effects 0.000 description 21
- 239000000243 solution Substances 0.000 description 17
- 239000003755 preservative agent Substances 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 8
- 230000002195 synergetic effect Effects 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 239000003708 ampul Substances 0.000 description 5
- 239000000872 buffer Substances 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 4
- 229940124274 edetate disodium Drugs 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 241000228245 Aspergillus niger Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 239000002738 chelating agent Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000002054 inoculum Substances 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 239000008215 water for injection Substances 0.000 description 3
- 238000012371 Aseptic Filling Methods 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 235000021472 generally recognized as safe Nutrition 0.000 description 2
- 230000036512 infertility Effects 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- 238000011287 therapeutic dose Methods 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000222122 Candida albicans Species 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
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 206010029155 Nephropathy toxic Diseases 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 206010038540 Renal tubular necrosis Diseases 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- NSTORIOUDCABGP-UHFFFAOYSA-N ethanol;prop-1-ene Chemical group CCO.CC=C NSTORIOUDCABGP-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000005308 flint glass Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 230000000415 inactivating effect Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 231100000225 lethality Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000013048 microbiological method Methods 0.000 description 1
- 230000007694 nephrotoxicity Effects 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 208000005368 osteomalacia Diseases 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000012487 rinsing solution Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000012430 stability testing Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 150000003710 vitamin D derivatives Chemical class 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
- 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
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Nutrition Science (AREA)
- Hematology (AREA)
- Physical Education & Sports Medicine (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/057143 | 1998-04-08 | ||
| US09/057,143 US6136799A (en) | 1998-04-08 | 1998-04-08 | Cosolvent formulations |
| PCT/US1999/006196 WO1999051271A2 (en) | 1998-04-08 | 1999-03-22 | Compositions comprising glycol derivatives and alcohols |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU3359899A AU3359899A (en) | 1999-10-25 |
| AU758989B2 true AU758989B2 (en) | 2003-04-03 |
Family
ID=22008769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU33598/99A Ceased AU758989B2 (en) | 1998-04-08 | 1999-03-22 | Cosolvent formulations |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US6136799A (enExample) |
| EP (1) | EP1073467B1 (enExample) |
| JP (4) | JP4664499B2 (enExample) |
| AT (1) | ATE275974T1 (enExample) |
| AU (1) | AU758989B2 (enExample) |
| CA (1) | CA2326198C (enExample) |
| DE (1) | DE69920201T2 (enExample) |
| DK (1) | DK1073467T3 (enExample) |
| ES (1) | ES2229693T3 (enExample) |
| PT (1) | PT1073467E (enExample) |
| WO (1) | WO1999051271A2 (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6586661B1 (en) | 1997-06-12 | 2003-07-01 | North Carolina State University | Regulation of quinolate phosphoribosyl transferase expression by transformation with a tobacco quinolate phosphoribosyl transferase nucleic acid |
| US6136799A (en) * | 1998-04-08 | 2000-10-24 | Abbott Laboratories | Cosolvent formulations |
| JP2004533807A (ja) * | 2000-11-07 | 2004-11-11 | ノース・キャロライナ・ステイト・ユニヴァーシティ | プトレッシン−ｎ−メチルトランスフェラーゼプロモーター |
| EA008072B1 (ru) * | 2001-12-03 | 2007-02-27 | Новацея, Инк. | Фармацевтические составы, содержащие соединения активного витамина d |
| DE60325459D1 (de) | 2002-02-19 | 2009-02-05 | Resolution Chemicals Ltd | Auf lösungsmitteln basierende sterilisation von steroiden |
| US20040053895A1 (en) * | 2002-09-18 | 2004-03-18 | Bone Care International, Inc. | Multi-use vessels for vitamin D formulations |
| US20040058895A1 (en) * | 2002-09-18 | 2004-03-25 | Bone Care International, Inc. | Multi-use vessels for vitamin D formulations |
| US7148211B2 (en) * | 2002-09-18 | 2006-12-12 | Genzyme Corporation | Formulation for lipophilic agents |
| US20050026877A1 (en) * | 2002-12-03 | 2005-02-03 | Novacea, Inc. | Pharmaceutical compositions comprising active vitamin D compounds |
| US20060189586A1 (en) * | 2003-06-11 | 2006-08-24 | Cleland Jeffrey L | Pharmaceutical compositions comprising active vitamin D compounds |
| US20050020546A1 (en) * | 2003-06-11 | 2005-01-27 | Novacea, Inc. | Pharmaceutical compositions comprising active vitamin D compounds |
| US20050148557A1 (en) * | 2003-07-29 | 2005-07-07 | Jin Tian | Use of Vitamin Ds to treat kidney disease |
| US20060009425A1 (en) * | 2004-05-28 | 2006-01-12 | Leticia Delgado-Herrera | Oral formulations of paricalcitol |
| CN101223135A (zh) * | 2005-07-18 | 2008-07-16 | 特瓦制药工业有限公司 | 帕立骨化醇的制备 |
| US20070166187A1 (en) * | 2006-01-18 | 2007-07-19 | Song Jing F | Stabilization of paricalcitol using chlorobutyl or chlorinated butyl stoppers |
| MX2008014418A (es) * | 2006-05-15 | 2008-11-27 | Wisconsin Alumni Res Found | Administracion pulmonar de la 1 alfa, 25-dihidroxivitamina d3 y co-administracion de la homona paratiroidea o calcitonina. |
| US20100075933A1 (en) * | 2008-07-28 | 2010-03-25 | Sunita Vijay Shelke | Injectable compositions of vitamin d compounds |
| US20110033529A1 (en) * | 2009-08-06 | 2011-02-10 | Durga Prasad Samantaray | Oral pharmaceutical paricalcitol formulations |
| EP2545940A1 (de) * | 2011-07-14 | 2013-01-16 | hameln rds gmbh | Parenterale Zusammensetzungen |
| MY172886A (en) | 2012-06-29 | 2019-12-13 | Wisconsin Alumni Res Found | Use of 2-methylene-19-nor-(20s)-1?25-dihydroxyvitamin d3 to treat secondary hyperparathyroidism |
| ES2698403T3 (es) * | 2012-12-27 | 2019-02-04 | Pharmathen Sa | Composición farmacéutica inyectable estable de agonista de receptor de vitamina D y proceso para su preparación |
| US9539264B2 (en) | 2014-12-30 | 2017-01-10 | Wisconsin Alumni Research Foundation | Use of 2-methylene-19-nor-(20S)-1-alpha,25-dihydroxyvitamin D3 to treat secondary hyperparathyroidism in patients previously treated with calcimimetics |
| US10369161B2 (en) | 2014-12-30 | 2019-08-06 | Wisconsin Alumni Research Foundation | Use of 2-methylene-19-NOR-(20S)-1-alpha,25-dihydroxyvitamin D3 to treat primary hyperparathyroidism |
| CN106265492B (zh) * | 2015-06-04 | 2020-12-11 | 成都国为生物医药有限公司 | 一种含有帕立骨化醇的药物组合物及其制备方法 |
| US10105375B2 (en) | 2016-08-30 | 2018-10-23 | Wisconsin Alumni Research Foundation | Combination of low dose 2-methylene-19-nor-(20S)1α, 25-dihydroxyvitamin D3 and calcimimetics to treat secondary hyperparathyroidism |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4855294A (en) * | 1988-09-06 | 1989-08-08 | Theratech, Inc. | Method for reducing skin irritation associated with drug/penetration enhancer compositions |
| US5098899A (en) * | 1989-03-06 | 1992-03-24 | Trustees Of Boston University | Method for therapeutically treating psoriatic arthritis using vitamin D analogues and metabolites |
| WO1993000079A1 (en) * | 1991-06-28 | 1993-01-07 | University Of Miami | Method of preventing and treating chemotherapy-induced alopecia |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4198391A (en) * | 1973-07-20 | 1980-04-15 | R. P. Scherer Ltd. | Pharmaceutical compositions |
| US4212886A (en) * | 1978-11-01 | 1980-07-15 | Survival Technology, Inc. | Stabilized benactyzine hydrochloride |
| US4308264A (en) * | 1981-01-28 | 1981-12-29 | Abbott Laboratories | Stabilized, dilute aqueous preparation of 1α,25-dihydroxycholecalciferol for neonatal administration |
| DE3316510A1 (de) * | 1983-05-06 | 1984-11-08 | Bayer Ag | Parenterale formulierung von nimodipin, ein verfahren zu ihrer herstellung sowie ihre verwendung bei der bekaempfung von erkrankungen |
| US4588528A (en) * | 1984-05-31 | 1986-05-13 | Wisconsin Alumni Research Foundation | 1,24-dihydroxy-Δ22 -vitamin D3 and process for preparing same |
| DE3437232A1 (de) * | 1984-10-10 | 1986-04-17 | Mack Chem Pharm | Stabilisierte injektionsloesungen von piroxicam |
| US4594340A (en) * | 1984-11-29 | 1986-06-10 | Hoffmann-La Roche Inc. | 25,26-dehydro-1α,24R-dihydroxycholecalciferol and 25,26-dehydro-1α,24S-dihydroxycholecalciferol and the epimeric mixture |
| DK191889D0 (da) * | 1989-04-20 | 1989-04-20 | Bukh Meditec | Kosmetisk middel |
| AU649057B2 (en) * | 1990-08-24 | 1994-05-12 | Wisconsin Alumni Research Foundation | Methods and compositions containing vitamin D compounds for improvement of skin conditions |
| US5502224A (en) * | 1991-06-04 | 1996-03-26 | Marigen, S.A. | Biotenside esters and phosphatides with vitamin-D and vitamin-E compounds |
| FR2677884B1 (fr) * | 1991-06-20 | 1993-07-09 | Oreal | Composition pour freiner la chute des cheveux a base de pyrimidines n-oxyde trisubstitues ou leurs derives sulfoconjugues, nouveaux composes pyrimidines n-oxyde ou leurs derives sulfoconjugues. |
| GB9201920D0 (en) * | 1992-01-29 | 1992-03-18 | Leo Pharm Prod Ltd | Novel treatment i |
| JPH05246891A (ja) * | 1992-03-09 | 1993-09-24 | Kobayashi Seiyaku Kogyo Kk | 安定な抗膵炎用注射液 |
| KR960013798B1 (ko) * | 1992-04-24 | 1996-10-10 | 재단법인 한국전자통신연구소 | 평면 도파로형 공간 스위치 |
| WO1996036340A1 (en) * | 1995-05-19 | 1996-11-21 | Abbott Laboratories | STABLE AQUEOUS FORMULATIONS OF 1α,25-DIHYDROXYCHOLECALCIFEROL FOR PARENTERAL ADMINISTRATION |
| US5597815A (en) * | 1995-07-13 | 1997-01-28 | Wisconsin Alumni Research Foundation | Prevention of hyperphosphatemia in kidney disorder patients |
| ES2188932T3 (es) * | 1996-04-04 | 2003-07-01 | Cilag Ag | Formulacion topica de vitamina d a base de liposomas. |
| DK0893121T3 (da) * | 1997-06-27 | 2002-06-17 | Akzo Nobel Nv | Flydende oral medicinopløsning |
| CA2211949A1 (en) * | 1997-07-21 | 1999-01-29 | David Farley Johnson | Nonaqueous compositions for parenteral administration |
| US6136799A (en) * | 1998-04-08 | 2000-10-24 | Abbott Laboratories | Cosolvent formulations |
-
1998
- 1998-04-08 US US09/057,143 patent/US6136799A/en not_active Expired - Lifetime
-
1999
- 1999-03-22 EP EP99914970A patent/EP1073467B1/en not_active Expired - Lifetime
- 1999-03-22 CA CA002326198A patent/CA2326198C/en not_active Expired - Lifetime
- 1999-03-22 DE DE69920201T patent/DE69920201T2/de not_active Expired - Lifetime
- 1999-03-22 DK DK99914970T patent/DK1073467T3/da active
- 1999-03-22 AU AU33598/99A patent/AU758989B2/en not_active Ceased
- 1999-03-22 WO PCT/US1999/006196 patent/WO1999051271A2/en not_active Ceased
- 1999-03-22 ES ES99914970T patent/ES2229693T3/es not_active Expired - Lifetime
- 1999-03-22 PT PT99914970T patent/PT1073467E/pt unknown
- 1999-03-22 AT AT99914970T patent/ATE275974T1/de active
- 1999-03-22 JP JP2000542041A patent/JP4664499B2/ja not_active Expired - Lifetime
-
2000
- 2000-10-12 US US09/689,507 patent/US6361758B1/en not_active Expired - Lifetime
-
2010
- 2010-09-16 JP JP2010207684A patent/JP5548079B2/ja not_active Expired - Lifetime
-
2014
- 2014-01-31 JP JP2014016658A patent/JP5887368B2/ja not_active Expired - Lifetime
-
2015
- 2015-10-16 JP JP2015204318A patent/JP2016053046A/ja active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4855294A (en) * | 1988-09-06 | 1989-08-08 | Theratech, Inc. | Method for reducing skin irritation associated with drug/penetration enhancer compositions |
| US5098899A (en) * | 1989-03-06 | 1992-03-24 | Trustees Of Boston University | Method for therapeutically treating psoriatic arthritis using vitamin D analogues and metabolites |
| WO1993000079A1 (en) * | 1991-06-28 | 1993-01-07 | University Of Miami | Method of preventing and treating chemotherapy-induced alopecia |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2011037860A (ja) | 2011-02-24 |
| DE69920201D1 (de) | 2004-10-21 |
| JP2014129360A (ja) | 2014-07-10 |
| JP4664499B2 (ja) | 2011-04-06 |
| DE69920201T2 (de) | 2005-09-29 |
| WO1999051271A3 (en) | 1999-11-18 |
| WO1999051271A2 (en) | 1999-10-14 |
| US6361758B1 (en) | 2002-03-26 |
| ATE275974T1 (de) | 2004-10-15 |
| DK1073467T3 (da) | 2005-01-03 |
| JP5887368B2 (ja) | 2016-03-16 |
| CA2326198A1 (en) | 1999-10-14 |
| PT1073467E (pt) | 2004-12-31 |
| JP2002510652A (ja) | 2002-04-09 |
| JP2016053046A (ja) | 2016-04-14 |
| EP1073467B1 (en) | 2004-09-15 |
| US6136799A (en) | 2000-10-24 |
| JP5548079B2 (ja) | 2014-07-16 |
| EP1073467A2 (en) | 2001-02-07 |
| ES2229693T3 (es) | 2005-04-16 |
| CA2326198C (en) | 2009-06-09 |
| AU3359899A (en) | 1999-10-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |