WO2007133711B1 - Pharmaceutical compositions for vein irritating drugs - Google Patents
Pharmaceutical compositions for vein irritating drugsInfo
- Publication number
- WO2007133711B1 WO2007133711B1 PCT/US2007/011465 US2007011465W WO2007133711B1 WO 2007133711 B1 WO2007133711 B1 WO 2007133711B1 US 2007011465 W US2007011465 W US 2007011465W WO 2007133711 B1 WO2007133711 B1 WO 2007133711B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- emulsion
- oil
- weight
- concentration
- water
- Prior art date
Links
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
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/14—Peptides containing saccharide radicals; Derivatives thereof, e.g. bleomycin, phleomycin, muramylpeptides or vancomycin
-
- 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
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/19—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles lyophilised, i.e. freeze-dried, solutions or dispersions
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)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Dispersion Chemistry (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Dermatology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
Abstract
Non-vein irritating pharmaceutical formulations (e.g., oil-in-water emulsions, frozen formulations, and lyophilized formulations) of vancomycin and clarithromycin are provided. Also provided are methods for preparing and using such formulations.
Claims
1. An oil-in-water emulsion comprising:
(i) vancomycin at a concentration of about 0.1% to about 3% by weight or a pharmaceutically acceptable salt or analog of vancomycin at an equivalent concentration;
(ii) one or more liquid oils at a total concentration of about 2% to about 4% by weight;
(iii) one or more phospholipids at a total concentration of about 2% to about 5% by weight, wherein the weight ratio of the total phospholipid(s) to the total liquid oil(s) is at least 0.5:1 ;
(iv) about 5% to about 6% dextrose by weight; and
(v) water, wherein the average size of the oil droplets in the emulsion is no more than about 200 nm, and the PFAT5 of the emulsion is less than about 0.05.
2. The emulsion of claim 1 , wherein the one or more liquid oils comprise soybean oil.
3. The emulsion of claim 1 , wherein the one or more liquid oils comprise a vegetable oil and a medium chain triglyceride.
4. The emulsion of any one of claims 1 to 3, wherein the one or more phospholipids comprise lecithin.
5. The emulsion of claim 1 , comprising:
(1 ) vancomycin hydrochloride at a concentration of about 0.5% by weight,
(2) soybean oil at a concentration of about 1% to about 2% by weight,
(3) medium chain triglyceride at a concentration of about 1 % to about 2% by weight;
(4) lecithin at a concentration of about 2% to about 4% by weight; and
(5) dextrose at a concentration of about 5% to about 6% by weight.
66
6. The emulsion of claim 1 , comprising:
(1 ) vancomycin hydrochloride at a concentration of about 0.5% by weight, ,
(2) soybean oil and medium chaiiji triglyceride, wherein the total concentration of soybean oil and medium chain' triglyceride is about 2% by weight, and the weight ratio of soybean oil to medium chain triglyceride is between 2:1 to 1 :1 ;
(3) lecithin at a concentration of about 2% by weight; and
(4) dextrose at a concentration of about 5% by weight.
7. The emulsion of any one of claims 1 to 6, wherein the emulsion does not further comprise a compound that increases the amount of vancomycin in the oil droplets of the emulsion.
8. The emulsion of any one of claims 1 to 6, wherein less than about 30% of vancomycin is in the oil droplets of the emulsion.
9. A frozen composition comprising:!
(i) vancomycin at a concentration of about 0.1 % to about 3% by weight or a pharmaceutically acceptable salt or analog of vancomycin at an equivalent concentration; ,
(Ii) one or more liquid oils at a total concentration of about 2% to about 4% by weight; :
(iii) one or more phospholipids at a total concentration of about 2% to about 5% by weight, wherein the weight ratio of the total phospholipid(s) to the total liquid oil(s) is at least 0.5:1 ; .
(iv) about 5% to about 6% dextrose by weight; and
(v) water; wherein when thawed, the composition forms an oil-in-water emulsion with an average diameter of oil droplets no more than about 200 nm and a PFAT of less than about 0.05.
67
10. The composition of claim 9, corriprising vancomycin at a concentration of about 0.5% by weight or a pharmaceutically acceptable salt or analog of vancomycin at an equivalent concentration.
11. The composition of claim 9 or claim 10, wherein the one or more liquid oils comprise a vegetable oil and a medium chain triglyceride.
12. The composition of any one of claims 9 to 11 , wherein the composition does not further comprise a compound that increases the amount of vancomycin in the oil droplets of the emulsion.
13. The composition of any one of claims 9 to 11 , wherein when thawed, less than about 30% of vancomycin is present in the oil droplets of the oil-in-water emulsion.
14. A method for treating or reducing infection comprising administering to a patient in need thereof a pharmaceutically effective amount of the emulsion of any one of claims 1 to 8.
15. A method for treating or reducing infection comprising administering to a patient in need thereof a pharmaceutically effective amount of an oil-in-water emulsion formed by thawing the frozen composition of any one of claims 9 to 13.
16. An oil-in-water emulsion comprising:
(i) clarithromycin at a concentration of at least about 0.5% by weight or a pharmaceutically acceptable salt or ester of clarithromycin at an equivalent concentration;
(ii) one or more liquid oils at a total concentration of about 2% to about 4% by weight;
(iii) one or more phospholipids at a total concentration of about 1 % to about 5% by weight, wherein the weight ratio of the total phospholipid(s) to the total liquid oil(s) is at least 0.5:1;
(iv) about 5% to about 6% dextrose by weight; and
(v) water;
68 wherein the average size of the oil droplets in the emulsion is no more than about 200 nm, and the PFAT5 of the emulsion is less than about 0.05.
17. The emulsion of claim 16, wherein the one or more liquid oils comprise soybean oil.
18. The emulsion of claim 16, wherόin the one or more liquid oils comprise a vegetable oil and a medium chain triglyceride.
19. The emulsion of any one of claims 16 to 18, wherein the one or more phospholipids comprise lecithin.
20. The emulsion of any one of claims 16 to 19, wherein ,the emulsion does not further comprise a compound thai: increases the amount of clarithromycin in the oil droplets of the emulsion.
21. The emulsion of any one of claims 16 to 19, wherein less than about 30% of clarithromycin is in the oil droplets of the emulsion.
22. The emulsion of claim 16, comprising:
(1) clarithromycin at a concentration 1Of about 1% to about 5% by weight, j
(2) soybean oil and medium chain ! triglyceride, wherein the total concentration of soybean oil and medium chain triglyceride is about 2% by weight, the weight ratio of soybean oil to medium chain triglyceride is between 2:1 to 1 :1 ; i
(3) lecithin at a concentration of about 2% by weight; and
(4) dextrose at a concentration of about 5% by weight.
23. A frozen composition comprising: ,
(i) clarithromycin at a concentration of at least about 0.5% by weight or a pharmaceutically acceptable salt or este.r of clarithromycin at an equivalent concentration; :
(ii) one or more liquid oils at a total concentration of about 2% to about 4% by weight;
69 (iii) one or more phospholipids at a total: concentration of about 1% to about 5% by weight, wherein the weight ratio ofjthe total phospholipid(s) to the total liquid oil(s) is at least 0.5:1; ;
(iv) about 5% to about 6% dextrose byiweight; and
(v) water; . wherein when thawed, the compositiom forms an oiMn-water emulsion with an average diameter of oil droplets no more than about 200 nm and a PFAT5 of less than about 0.05.
24. The composition of claim 23, wherein the one or more i » liquid oils comprise a vegetable oil and a medium chain triglyceride.
25. A method for treating or reducing infection comprising administering to a patient in need thereof a pharmaceutically effective amount of the emulsion of any one of claims 16 to 22. ;
26. A method for treating or reducing infection comprising administering to a patient in need thereof a pharmaceutically effective amount of an oil-in-water emulsion formed by thawing the frozen composition of claim 23 or claim 24.
27. An oil-in-water emulsion comprising,:
(i) at least about 15 mg/ml vancomycin or a pharmaceutically acceptable salt or analog thereof at an equivalent concentration,
(ii) one or more liquid oils at a total concentration of about 2% to about 10% by weight,
(iii) one or more phospholipids at a total concentration of about 1 % to about 10% by weight, and
(iv) dextrose at a concentration of a^t least about 10% by weight.
28. The oil-in-water emulsion of claim 27 wherein the one or more liquid oils comprise soybean oil.
29. The oil-in-water emulsion of claim 27 wherein the one or more phospholipids comprise lecithin.
70
30. The oil-in-water emulsion of claim 27 comprising vancomycin hydrochloride at a concentration of about 1 % to about 3% by weight, medium chain triglyceride at a concentration όi about 1 % to about 5% by weight, vegetable oil at a concentration of about 1% to about 5% by weight, lecithin at a concentration of about 1 % to about 4% by weight, and dextrose at a concentration of about 15% to about 25% by weight.
31. The oil-in-water emulsion of claim 27 wherein the pH of the emulsion is about 3 to about 8.
32. The oil-in-water emulsion of any one of claims 27 to 31 wherein the average size of the oil droplets in the emulsion is less than 250 nm.
33. The oil-in-water emulsion of claim 32, wherein the average size of the oil droplets in the emulsion is no more than about 200 nm, and the PFAT5 of the emulsion is less than about 0.05.
34. The oil-in-water emulsion of any one of claims 27 to 33, wherein the emulsion does not further comprise a compound that increases the amount of vancomycin in the oil droplets of the emulsion.
35. The oil-in-water emulsion of any one of claims 27 to 33, wherein no more than about 30% of vancomycin is present in the oil droplets of the oil-in-water emulsion.
36. A lyophilized composition comprising vancomycin or a pharmaceutically acceptable salt or analog thereof, liquid oil(s), phospholipid(s), and dextrose, wherein the composition is prepared by removal of water from the oil-in- water emulsion of any one of claims 27 to 35, , the composition can be rehydrated with water to form an emulsion suitable for injection, and • the average diameter of the re-formed Emulsion droplets is no greater than about 1 micron.
71
37. The lyophilized composition of ; claim 36 wherein the average diameter of the reformed emulsion droplets is no greater than about 400 nm.
38. A lyophilized composition comprising:
(i) vancomycin at a concentration of about 5% to about 10% by weight or a pharmaceutically acceptable salt or analog thereof at an equivalent concentration,
(ii) one or more liquid oils at a totai concentration of about 10% to about 20% by weight,
(iii) one or more phospholipids at a total concentration of about 10% to 20% by weight, and
(iv) dextrose at a concentration about 50% to about 80% by weight.
39. The lyophilized composition of claim 38, wherein the composition forms an oil-in-water emulsion when rehydrated with water, and the average diameter of the oil droplets in the oil-ip-water emulsion is no greater than about 1 micron.
40. The lyophilized composition of claim 38 or claim 39, wherein the composition does not further comprise a compound that increases the amount of vancomycin in the oil droplets of an oil-in-water emulsion formed by rehydrating the composition with water.
41. The lyophilized composition of claim 38 or claim 39, wherein the composition forms an oil-in-water emulsion when rehydrated with water, and less than about 30% of vancomycin is in the oil droplets of the emulsion.
42. The lyophilized composition of any One of claims 38 to 41 , wherein the composition forms an oil-in-water emulsion when rehydrated with water, the average size of the oil droplets in the emulsion is no more than about 200 nm, and the PFAT5 of the emulsion is less than about 0.05.
43. A method for treating or reduci'ng infection comprising administrating to a patient in need thereof a pharmaceutically effective amount of the oil-in-water emulsion of any one of claims 27 to 3|5.
44. A method for treating or reducing infection comprising administering to a patient in need thereof a pharmaceutically effective amount of an oil-in-water emulsion formed by rehydrating the lyophilized composition of any one of claims 36 to 42.
45. An oil-in-water emulsion comprising:
(i) clarithromycin at a concentration of at least about 1% by weight or a pharmaceutically acceptable salt or ester thereof at an equivalent concentration,
(ii) one or more liquid oils at a total concentration of about 2% to about 10% by weight,
(iii) one or more phospholipids at a total concentration of about 1 % to about 10% by weight, and
(iv) dextrose at a concentration of ait least about 10% by weight.
46. The oil-in-water emulsion of claim 45 comprising clarithromycin at a concentration of about 1% to about;3% by weight, medium chain triglyceride at a concentration of about 1% to! about 5% by weight, vegetable oil at a concentration of about 1% to about 5% by weight, lecithin at a concentration of about 1% to about 10% by weight, andl dextrose of about 15% to about 25% by weight.
47. The oil-in-water emulsion of claim 45 or claim 46 wherein the average size of the oil droplets in the emulsion is less than about 250 nm. i
48. The oil-in-water emulsion of claim 47, wherein the average size of the oil droplets in the emulsion is no more than about 200 nm, and the PFAT5 of the emulsion is less than about 0.05.
49. The oil-in-water emulsion of any one of claims 45 to 48, wherein the emulsion does not further comprise a compound that increases the amount of clarithromycin in the oil droplets of the emulsion.
73
50. The oil-in-water emulsion of any one of claims 45 to 48, wherein no more than 30% of clarithromycin is in ' the oil droplets of the emulsion.
51. A lyophilized composition comprising clarithromycin or a pharmaceutically acceptable salt or ester thereof, liquid oil(s), phospholipid(s), and dextrose, wherein the composition is prepared by removal ;of water from the oil-in- water emulsion of any one of claims 45 to 50, ; the composition can be rehydrated with water to form an emulsion suitable for injection, and the average diameter of the re-formed emulsion droplets is no greater than about 1 micron.
52. The lyophilized composition of iclaim 51 wherein the average diameter of the re-formed emulsion droplets is no greater than about 200 nm.
53. A lyophilized composition comprisirig:
(i) clarithromycin at a concentration of about 2% to about 8% by weight or a pharmaceutically acceptable salt or ester thereof at an equivalent concentration,
(ii) liquid oil at a concentration of about 10% to about 20% by weight,
(iii) one or more phospholipids at a concentration of about 10% to about 20% by weight, and
(iv) dextrose at a concentration about; 50% to about 80% by weight. :
54. The lyophilized composition of Claim 53, wherein the composition forms an oil-in-water emulsion when rehydrated with water, and the average diameter of the emulsion droplets is no greater than about 200 nm.
55. The lyophilized composition of claim 54, wherein the composition forms an oil-in-water emulsion when rehydrated with water, and the PFAT5 of the emulsion is less than about 0.05.
74
56. The lyophilized composition of any one of claims 53 to 55, wherein the composition forms an oil-in-water emulsicjn when rehydrated with water, and the composition does not further comprise a compound that increases the amount of clarithromycin in the oil droplets of the emulsion.
57. The lyophilized composition of any one of claims 53 to 55, wherein the composition forms an oil-in-water emulsiqn when rehydrated with water, and less than about 30% of clarithromycin is ih the oil droplets of the emulsion.
58. A method for treating or reducing the risk of infection comprising administrating to a patient in need thereof a pharmaceutically effective amount of the oil-in-water emulsion of any one.of claims 45 to 50. i
59. A method for treating or reducing the risk of infection comprising administering to a patient in need thereof a pharmaceutically effective amount of an oil-in-water emulsion formed by rehydrating the lyophilized composition of any one of claims 51 to 57.
75
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002651988A CA2651988A1 (en) | 2006-05-12 | 2007-05-11 | Pharmaceutical compositions for vein irritating drugs |
EP07777015A EP2023895A2 (en) | 2006-05-12 | 2007-05-11 | Pharmaceutical compositions for vein irritating drugs |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US80013306P | 2006-05-12 | 2006-05-12 | |
US60/800,133 | 2006-05-12 |
Publications (3)
Publication Number | Publication Date |
---|---|
WO2007133711A2 WO2007133711A2 (en) | 2007-11-22 |
WO2007133711A3 WO2007133711A3 (en) | 2008-01-24 |
WO2007133711B1 true WO2007133711B1 (en) | 2008-03-13 |
Family
ID=38599386
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2007/011465 WO2007133711A2 (en) | 2006-05-12 | 2007-05-11 | Pharmaceutical compositions for vein irritating drugs |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP2023895A2 (en) |
CN (1) | CN101472562A (en) |
CA (1) | CA2651988A1 (en) |
TW (1) | TW200812608A (en) |
WO (1) | WO2007133711A2 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103330734A (en) * | 2013-06-21 | 2013-10-02 | 辽宁海思科制药有限公司 | Medium/long-chain fat emulsion injection pharmaceutical composition and preparation method thereof |
US20140155320A1 (en) * | 2010-10-22 | 2014-06-05 | Dr. Reddy's Laboratories, Inc. | Use of storage stable viscous phospholipid depot to treat wounds |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102026621A (en) | 2008-05-15 | 2011-04-20 | 巴克斯特国际公司 | Stable pharmaceutical formulations |
AU2015202240B2 (en) * | 2010-08-20 | 2016-09-29 | Dr. Reddy's Laboratories Sa | Phospholipid depot |
CA2809022C (en) * | 2010-08-20 | 2017-01-03 | Dr. Reddy`S Laboratories, Inc. | Phospholipid depot |
AU2015229069A1 (en) | 2014-03-14 | 2016-11-03 | CutisPharma,Inc. | Composition and method for vancomycin oral liquid |
CN107904286A (en) * | 2017-12-27 | 2018-04-13 | 苏州普瑞森基因科技有限公司 | A kind of colorectal cancer microbial markers and its application |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050049209A1 (en) * | 2003-08-06 | 2005-03-03 | Chen Andrew Xian | Pharmaceutical compositions for delivering macrolides |
US7871632B2 (en) * | 2004-07-12 | 2011-01-18 | Adventrx Pharmaceuticals, Inc. | Compositions for delivering highly water soluble drugs |
-
2007
- 2007-05-11 CA CA002651988A patent/CA2651988A1/en not_active Abandoned
- 2007-05-11 EP EP07777015A patent/EP2023895A2/en not_active Withdrawn
- 2007-05-11 TW TW96116904A patent/TW200812608A/en unknown
- 2007-05-11 WO PCT/US2007/011465 patent/WO2007133711A2/en active Application Filing
- 2007-05-11 CN CNA2007800228020A patent/CN101472562A/en active Pending
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20140155320A1 (en) * | 2010-10-22 | 2014-06-05 | Dr. Reddy's Laboratories, Inc. | Use of storage stable viscous phospholipid depot to treat wounds |
CN103330734A (en) * | 2013-06-21 | 2013-10-02 | 辽宁海思科制药有限公司 | Medium/long-chain fat emulsion injection pharmaceutical composition and preparation method thereof |
CN103330734B (en) * | 2013-06-21 | 2015-02-04 | 辽宁海思科制药有限公司 | Medium/long-chain fat emulsion injection pharmaceutical composition and preparation method thereof |
Also Published As
Publication number | Publication date |
---|---|
CA2651988A1 (en) | 2007-11-22 |
WO2007133711A2 (en) | 2007-11-22 |
TW200812608A (en) | 2008-03-16 |
CN101472562A (en) | 2009-07-01 |
EP2023895A2 (en) | 2009-02-18 |
WO2007133711A3 (en) | 2008-01-24 |
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