RU2005100959A - Кислые инсулиновые препараты с повышенной стабильностью - Google Patents
Кислые инсулиновые препараты с повышенной стабильностью Download PDFInfo
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- RU2005100959A RU2005100959A RU2005100959/15A RU2005100959A RU2005100959A RU 2005100959 A RU2005100959 A RU 2005100959A RU 2005100959/15 A RU2005100959/15 A RU 2005100959/15A RU 2005100959 A RU2005100959 A RU 2005100959A RU 2005100959 A RU2005100959 A RU 2005100959A
- Authority
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- Prior art keywords
- pharmaceutical composition
- composition according
- insulin
- human insulin
- group
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- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 title claims 17
- 102000004877 Insulin Human genes 0.000 title claims 4
- 108090001061 Insulin Proteins 0.000 title claims 4
- 229940125396 insulin Drugs 0.000 title claims 4
- 239000002253 acid Substances 0.000 title claims 2
- 229940079593 drug Drugs 0.000 title 1
- 239000003814 drug Substances 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 21
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 14
- 239000004026 insulin derivative Substances 0.000 claims 8
- 239000004094 surface-active agent Substances 0.000 claims 6
- 235000011187 glycerol Nutrition 0.000 claims 5
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 4
- 229920000136 polysorbate Polymers 0.000 claims 4
- 239000000600 sorbitol Substances 0.000 claims 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims 3
- 150000002170 ethers Chemical class 0.000 claims 3
- 229930195729 fatty acid Natural products 0.000 claims 3
- 239000000194 fatty acid Substances 0.000 claims 3
- -1 fatty acid esters Chemical class 0.000 claims 3
- 239000003755 preservative agent Substances 0.000 claims 3
- 150000005846 sugar alcohols Polymers 0.000 claims 3
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 claims 2
- 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 claims 2
- 101000976075 Homo sapiens Insulin Proteins 0.000 claims 2
- 229930195725 Mannitol Natural products 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- 239000000872 buffer Substances 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 150000004665 fatty acids Chemical class 0.000 claims 2
- YMAWOPBAYDPSLA-UHFFFAOYSA-N glycylglycine Chemical compound [NH3+]CC(=O)NCC([O-])=O YMAWOPBAYDPSLA-UHFFFAOYSA-N 0.000 claims 2
- 239000007951 isotonicity adjuster Substances 0.000 claims 2
- 239000000594 mannitol Substances 0.000 claims 2
- 235000010355 mannitol Nutrition 0.000 claims 2
- 229920005862 polyol Polymers 0.000 claims 2
- 150000003077 polyols Chemical class 0.000 claims 2
- 230000002335 preservative effect Effects 0.000 claims 2
- 239000011780 sodium chloride Substances 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 claims 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 claims 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims 1
- 241000283690 Bos taurus Species 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 1
- 108010008488 Glycylglycine Proteins 0.000 claims 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims 1
- 229930006000 Sucrose Natural products 0.000 claims 1
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 claims 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims 1
- 239000012928 buffer substance Substances 0.000 claims 1
- 229960002242 chlorocresol Drugs 0.000 claims 1
- 229930003836 cresol Natural products 0.000 claims 1
- 239000008121 dextrose Substances 0.000 claims 1
- 229940043257 glycylglycine Drugs 0.000 claims 1
- 239000008101 lactose Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 229920001983 poloxamer Polymers 0.000 claims 1
- 239000008389 polyethoxylated castor oil Substances 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 229920001184 polypeptide Polymers 0.000 claims 1
- 229920001451 polypropylene glycol Polymers 0.000 claims 1
- 229950008882 polysorbate Drugs 0.000 claims 1
- 102000004196 processed proteins & peptides Human genes 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000005720 sucrose Substances 0.000 claims 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 claims 1
Classifications
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- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7032—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a polyol, i.e. compounds having two or more free or esterified hydroxy groups, including the hydroxy group involved in the glycosidic linkage, e.g. monoglucosyldiacylglycerides, lactobionic acid, gangliosides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- A61K38/22—Hormones
- A61K38/28—Insulins
-
- 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
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Endocrinology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Immunology (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Biochemistry (AREA)
- Hematology (AREA)
- Dermatology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
Claims (20)
1. Фармацевтическая композиция, содержащая полипептид, выбранный из группы, состоящей из инсулина (крупного рогатого скота, свиньи или человека), аналога инсулина, производного инсулина, активного метаболита инсулина или их комбинаций; поверхностно-активное вещество или комбинации нескольких поверхностно-активных веществ; необязательно консервант или комбинации нескольких консервантов; и необязательно изотонизирующее средство, буферы или другие вспомогательные вещества или их комбинации, причем фармацевтическая композиция представляет собой прозрачный раствор, который имеет значение рН в кислой области (рН 1-6,8).
2. Фармацевтическая композиция по п.1 со значением рН в области рН 3,5-6,8.
3. Фармацевтическая композиция по п.1 со значением рН в области рН 3,5-4,5.
4. Фармацевтическая композиция по п.1, причем поверхностно-активное вещество выбрано из группы, состоящей из неполных и полных эфиров жирных кислот и простых эфиров многоатомных спиртов, глицерина, сорбита и сахарозы, полиолов.
5. Фармацевтическая композиция по п.4, причем неполные и полные эфиры жирных кислот и простые эфиры многоатомных спиртов, глицерина и сорбита выбраны из группы, состоящей из Span®, Tween® (полисорбат), Myrj®, Brij®, Triton®, Cremophor®.
6. Фармацевтическая композиция по п.5, причем неполные и полные эфиры жирных кислот и простые эфиры многоатомных спиртов, глицерина и сорбита выбраны из группы, состоящей из Tween®20 и Tween®80.
7. Фармацевтическая композиция по п.4, причем полиолы выбраны из группы, состоящей из полипропиленгликолей, полиэтиленгликолей, полоксамеров, плюроникса, тетроникса.
8. Фармацевтическая композиция по п.1, причем консервант выбран из группы, состоящей из фенола, крезола, хлоркрезола, бензилового спирта, парабена.
9. Фармацевтическая композиция по п.1, причем изотонизирующее средство выбрано из группы, состоящей из маннита, сорбита, лактозы, декстрозы, трегалозы, хлорида натрия, глицерина.
10. Фармацевтическая композиция по п.1, причем вспомогательные вещества выбраны из группы, состоящей из буферных веществ, как, например, ТРИС, фосфат, цитрат, ацетат, глицилглицин, или других веществ, как кислоты, щелочи, соли.
11. Фармацевтическая композиция по п.1, причем аналог инсулина выбран из группы, состоящей из Gly(A21),Arg(B31),Arg(B32)-человеческого инсулина, Lys(B3), Glu(B29)-человеческого инсулина, Asp(B28)-человеческого инсулина, Lys(B28)Pro(B29)-человеческого инсулина, Des(B30)-человеческого инсулина.
12. Фармацевтическая композиция по п.1, причем производное инсулина выбрано из группы, состоящей из В29-N-миристоил-des(B30)-человеческого инсулина, В29-N-пальмитоил-des(B30)-человеческого инсулина, B29-N-миристоил-человеческого инсулина, B29-N-пальмитоил-человеческого инсулина, В28-N-миристоил-LysB28ProB29-человеческого инсулина, В28-N-пальмитоил-LysB28ProB29-человеческого инсулина, В30-N-миристоил-ThrB29LysB30-человеческого инсулина, В30-N-пальмитоил-ThrB29LysB30-человеческого инсулина, B29-N-(N-пальмитоил-γ-глутамил)-des(B30)-человеческого инсулина, В29-N-(N-литохолил-γ-глутамил)-des(B30)-человеческого инсулина, В29-N-(ω-карбоксигептадеканоил)-des(B30)-человеческого инсулина и В29-N-(ω-карбоксигептадеканоил)-человеческого инсулина.
13. Фармацевтическая композиция по п.1, в которой инсулин, аналог инсулина и/или производное инсулина находится в концентрации 60-6000 нмоль/мл.
14. Фармацевтическая композиция по п.13, причем инсулин, аналог инсулина и/или производное инсулина находится в концентрации 240-3000 нмоль/мл.
15. Фармацевтическая композиция по п.1, в которой поверхностно-активное вещество находится в концентрации 5-200 мкг/мл.
16. Фармацевтическая композиция по п.15, в которой поверхностно-активное вещество находится в концентрации 5-120 мкг/мл.
17. Фармацевтическая композиция по п.16, в которой поверхностно-активное вещество находится в концентрации 20-75 мкг/мл.
18. Фармацевтическая композиция по по п.16, в которой глицерин и/или маннит находится в концентрации 100-250 ммоль.
19. Фармацевтическая композиция по п. 18, в которой NaCl находится в концентрации вплоть до 150 ммоль.
20. Фармацевтическая композиция по любому из пп.1-19, в которой буферное вещество находится в концентрации 5-250 ммоль.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10227232.8 | 2002-06-18 | ||
| DE10227232A DE10227232A1 (de) | 2002-06-18 | 2002-06-18 | Saure Insulinzubereitungen mit verbesserter Stabilität |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2005100959A true RU2005100959A (ru) | 2005-06-27 |
| RU2313362C2 RU2313362C2 (ru) | 2007-12-27 |
Family
ID=29723248
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2005100959/15A RU2313362C2 (ru) | 2002-06-18 | 2003-06-05 | Кислые инсулиновые препараты с повышенной стабильностью |
Country Status (38)
| Country | Link |
|---|---|
| US (4) | US20040048783A1 (ru) |
| EP (2) | EP2305288B1 (ru) |
| JP (2) | JP5237522B2 (ru) |
| KR (1) | KR101040029B1 (ru) |
| CN (2) | CN102133393B (ru) |
| AR (1) | AR039688A1 (ru) |
| AU (1) | AU2003238471B2 (ru) |
| BR (1) | BRPI0311877B8 (ru) |
| CA (1) | CA2490116C (ru) |
| CR (1) | CR7614A (ru) |
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