CA1176158A - Pharmaceutical formulations comprising human insulin and human c-peptide - Google Patents
Pharmaceutical formulations comprising human insulin and human c-peptideInfo
- Publication number
- CA1176158A CA1176158A CA000409900A CA409900A CA1176158A CA 1176158 A CA1176158 A CA 1176158A CA 000409900 A CA000409900 A CA 000409900A CA 409900 A CA409900 A CA 409900A CA 1176158 A CA1176158 A CA 1176158A
- Authority
- CA
- Canada
- Prior art keywords
- human
- insulin
- peptide
- composition
- human insulin
- 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.)
- Expired
Links
- VOUAQYXWVJDEQY-QENPJCQMSA-N 33017-11-7 Chemical compound OC(=O)CC[C@H](N)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)NCC(=O)NCC(=O)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N1[C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(O)=O)CCC1 VOUAQYXWVJDEQY-QENPJCQMSA-N 0.000 title claims abstract description 49
- PBGKTOXHQIOBKM-FHFVDXKLSA-N insulin (human) Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@H](C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3NC=NC=3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)[C@@H](C)CC)[C@@H](C)O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 PBGKTOXHQIOBKM-FHFVDXKLSA-N 0.000 title claims abstract description 38
- 101000976075 Homo sapiens Insulin Proteins 0.000 title claims abstract description 35
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 5
- 239000003937 drug carrier Substances 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 52
- 102000007327 Protamines Human genes 0.000 claims description 9
- 108010007568 Protamines Proteins 0.000 claims description 9
- 229940048914 protamine Drugs 0.000 claims description 5
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 230000003054 hormonal effect Effects 0.000 abstract description 6
- 208000002249 Diabetes Complications Diseases 0.000 abstract description 3
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- 206010012655 Diabetic complications Diseases 0.000 abstract description 2
- 230000003467 diminishing effect Effects 0.000 abstract description 2
- 230000001737 promoting effect Effects 0.000 abstract description 2
- 230000000979 retarding effect Effects 0.000 abstract description 2
- 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 description 54
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 108090001061 Insulin Proteins 0.000 description 28
- 102000004877 Insulin Human genes 0.000 description 27
- 229940125396 insulin Drugs 0.000 description 25
- 108010076181 Proinsulin Proteins 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 18
- 206010012601 diabetes mellitus Diseases 0.000 description 12
- 150000001413 amino acids Chemical class 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 235000011187 glycerol Nutrition 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 8
- 229940069330 human zinc insulin Drugs 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- 229910052725 zinc Inorganic materials 0.000 description 6
- 235000001014 amino acid Nutrition 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 239000001488 sodium phosphate Substances 0.000 description 5
- 229910000162 sodium phosphate Inorganic materials 0.000 description 5
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 5
- 108010075254 C-Peptide Proteins 0.000 description 4
- 108020004414 DNA Proteins 0.000 description 4
- 108010005991 Pork Regular Insulin Proteins 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
- 210000000496 pancreas Anatomy 0.000 description 4
- 229950008679 protamine sulfate Drugs 0.000 description 4
- 239000011787 zinc oxide Substances 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
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- 238000005755 formation reaction Methods 0.000 description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
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- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 2
- 102000003670 Carboxypeptidase B Human genes 0.000 description 2
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- 241001202975 Isophanes Species 0.000 description 2
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- 108020004511 Recombinant DNA Proteins 0.000 description 2
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- 208000032170 Congenital Abnormalities Diseases 0.000 description 1
- 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 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 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 description 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 description 1
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- 206010017553 Furuncle Diseases 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 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 description 1
- 101500025353 Homo sapiens Insulin A chain Proteins 0.000 description 1
- 101500025354 Homo sapiens Insulin B chain Proteins 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfate Natural products OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- 206010048214 Xanthoma Diseases 0.000 description 1
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- 239000002253 acid Substances 0.000 description 1
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- 235000004279 alanine Nutrition 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 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 description 1
- 230000037396 body weight Effects 0.000 description 1
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- IXIBAKNTJSCKJM-BUBXBXGNSA-N bovine insulin Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H]1CSSC[C@H]2C(=O)N[C@@H](C)C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=3C=CC(O)=CC=3)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=3NC=NC=3)NC(=O)[C@H](CO)NC(=O)CNC1=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O)=O)CSSC[C@@H](C(N2)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C(C)C)NC(=O)[C@@H](NC(=O)CN)[C@@H](C)CC)C(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CC=1C=CC=CC=1)C(C)C)C1=CN=CN1 IXIBAKNTJSCKJM-BUBXBXGNSA-N 0.000 description 1
- 230000023852 carbohydrate metabolic process Effects 0.000 description 1
- 235000021256 carbohydrate metabolism Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
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- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
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- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- -1 sodium hydroxide Chemical compound 0.000 description 1
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Classifications
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Zoology (AREA)
- Gastroenterology & Hepatology (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29671581A | 1981-08-27 | 1981-08-27 | |
| US296,715 | 1981-08-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1176158A true CA1176158A (en) | 1984-10-16 |
Family
ID=23143238
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000409900A Expired CA1176158A (en) | 1981-08-27 | 1982-08-23 | Pharmaceutical formulations comprising human insulin and human c-peptide |
Country Status (20)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6610649B2 (en) | 1996-09-27 | 2003-08-26 | Creative Peptides Sweden Ab | Insulin C-peptides |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3326473A1 (de) * | 1983-07-22 | 1985-01-31 | Hoechst Ag, 6230 Frankfurt | Pharmazeutisches mittel zur behandlung des diabetes mellitus |
| CA1296253C (en) * | 1986-10-20 | 1992-02-25 | Praveen Tyle | Stabilized growth hormone compositions |
| FI882921A7 (fi) * | 1986-10-20 | 1988-06-17 | Novo Ind A/S | Protamiinisinkki-insuliinivalmisteet. |
| WO1988006599A1 (en) * | 1987-02-25 | 1988-09-07 | Novo Industri A/S | Novel insulin derivatives |
| DE3863027D1 (de) * | 1987-08-14 | 1991-07-04 | Akzo Nv | Praeparat zur verhuetung oder bekaempfung von komplikationen bei diabetes. |
| US5212154A (en) * | 1987-08-14 | 1993-05-18 | Akzo N.V. | Preparation for treating complications in diabetes |
| GB0323979D0 (en) | 2003-10-13 | 2003-11-19 | Creative Peptides Sweden Ab | Therapeutic applications for c-peptide |
| JP4874989B2 (ja) | 2004-11-22 | 2012-02-15 | ノヴォ ノルディスク アー／エス | 可溶性で安定なインスリン含有調合物 |
| GB0511269D0 (en) | 2005-06-02 | 2005-07-13 | Creative Peptides Sweden Ab | Sustained release preparation of pro-insulin C-peptide |
| GB0601950D0 (en) * | 2006-01-31 | 2006-03-15 | Creative Peptides Sweden Ab | Compositions and methods of treating diabetes |
| AU2009292643B2 (en) | 2008-09-19 | 2016-02-18 | Nektar Therapeutics | Polymer conjugates of therapeutic peptides |
| MX2012013375A (es) * | 2010-05-17 | 2013-04-11 | Cebix Inc | Peptido c pegilado. |
| US8962553B2 (en) | 2011-11-17 | 2015-02-24 | Cebix Ab | Method of treating a diabetic subject having a microvascular impairment disorder by a pegylated C-peptide |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2789080A (en) * | 1952-08-14 | 1957-04-16 | Christensen Henry Marinus | Insulin-albumin compositions |
| CH330318A (de) * | 1953-09-08 | 1958-05-31 | British Drug Houses Ltd | Verfahren zur Herstellung eines Insulinpräparates mit verlängerter Wirkungszeit |
-
1982
- 1982-08-23 CA CA000409900A patent/CA1176158A/en not_active Expired
- 1982-08-23 ZW ZW174/82A patent/ZW17482A1/xx unknown
- 1982-08-23 CH CH5010/82A patent/CH650679A5/de not_active IP Right Cessation
- 1982-08-23 IL IL66611A patent/IL66611A0/xx unknown
- 1982-08-24 MW MW38/82A patent/MW3882A1/xx unknown
- 1982-08-24 NZ NZ201682A patent/NZ201682A/en unknown
- 1982-08-24 DZ DZ826637A patent/DZ452A1/fr active
- 1982-08-24 ZA ZA826159A patent/ZA826159B/xx unknown
- 1982-08-24 PH PH27772A patent/PH19361A/en unknown
- 1982-08-24 NL NL8203315A patent/NL192192C/nl not_active IP Right Cessation
- 1982-08-24 BE BE6/47701A patent/BE894185A/fr not_active IP Right Cessation
- 1982-08-25 FR FR8214595A patent/FR2513126B1/fr not_active Expired
- 1982-08-25 SE SE8204873A patent/SE460334B/sv not_active IP Right Cessation
- 1982-08-25 AU AU87594/82A patent/AU551879B2/en not_active Expired
- 1982-08-25 JP JP57148494A patent/JPS5846024A/ja active Pending
- 1982-08-26 GB GB08224484A patent/GB2104382B/en not_active Expired
- 1982-08-26 IE IE2064/82A patent/IE54119B1/en not_active IP Right Cessation
- 1982-08-26 LU LU84359A patent/LU84359A1/fr unknown
- 1982-08-27 DE DE19823232034 patent/DE3232034A1/de active Granted
- 1982-08-27 IT IT8223017A patent/IT1153182B/it active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6610649B2 (en) | 1996-09-27 | 2003-08-26 | Creative Peptides Sweden Ab | Insulin C-peptides |
Also Published As
| Publication number | Publication date |
|---|---|
| ZW17482A1 (en) | 1982-11-17 |
| BE894185A (fr) | 1983-02-24 |
| NL192192C (nl) | 1997-03-04 |
| PH19361A (en) | 1986-04-02 |
| AU551879B2 (en) | 1986-05-15 |
| MW3882A1 (en) | 1984-07-11 |
| ZA826159B (en) | 1984-04-25 |
| IT1153182B (it) | 1987-01-14 |
| SE8204873L (sv) | 1983-02-28 |
| SE8204873D0 (sv) | 1982-08-25 |
| IE54119B1 (en) | 1989-06-21 |
| NL8203315A (nl) | 1983-03-16 |
| SE460334B (sv) | 1989-10-02 |
| DZ452A1 (fr) | 2004-09-13 |
| IT8223017A0 (it) | 1982-08-27 |
| GB2104382B (en) | 1984-12-19 |
| FR2513126B1 (fr) | 1986-04-18 |
| AU8759482A (en) | 1983-03-03 |
| NL192192B (nl) | 1996-11-01 |
| IL66611A0 (en) | 1982-12-31 |
| IE822064L (en) | 1983-02-27 |
| GB2104382A (en) | 1983-03-09 |
| CH650679A5 (de) | 1985-08-15 |
| LU84359A1 (fr) | 1983-02-28 |
| NZ201682A (en) | 1985-08-16 |
| JPS5846024A (ja) | 1983-03-17 |
| FR2513126A1 (fr) | 1983-03-25 |
| DE3232034A1 (de) | 1983-03-10 |
| DE3232034C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-04-11 |
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