DE1900367A1 - Stabile Glucagonloesung und Verfahren zu ihrer Herstellung - Google Patents
Stabile Glucagonloesung und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1900367A1 DE1900367A1 DE19691900367 DE1900367A DE1900367A1 DE 1900367 A1 DE1900367 A1 DE 1900367A1 DE 19691900367 DE19691900367 DE 19691900367 DE 1900367 A DE1900367 A DE 1900367A DE 1900367 A1 DE1900367 A1 DE 1900367A1
- Authority
- DE
- Germany
- Prior art keywords
- glucagon
- solution
- months
- detergent
- solutions
- 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.)
- Pending
Links
- 102000051325 Glucagon Human genes 0.000 title claims description 83
- 108060003199 Glucagon Proteins 0.000 title claims description 83
- MASNOZXLGMXCHN-ZLPAWPGGSA-N glucagon Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(O)=O)C(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC=1NC=NC=1)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 MASNOZXLGMXCHN-ZLPAWPGGSA-N 0.000 title claims description 83
- 229960004666 glucagon Drugs 0.000 title claims description 83
- 238000000034 method Methods 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 2
- 239000003599 detergent Substances 0.000 claims description 35
- 229960003431 cetrimonium Drugs 0.000 claims description 17
- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 claims description 17
- 230000000087 stabilizing effect Effects 0.000 claims description 9
- 230000003381 solubilizing effect Effects 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000002091 cationic group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 116
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- 239000013078 crystal Substances 0.000 description 15
- 238000003860 storage Methods 0.000 description 14
- 230000007935 neutral effect Effects 0.000 description 11
- 238000001556 precipitation Methods 0.000 description 11
- 239000011780 sodium chloride Substances 0.000 description 7
- 238000001962 electrophoresis Methods 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005189 flocculation Methods 0.000 description 3
- 230000016615 flocculation Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000001165 hydrophobic group Chemical group 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- OBFSQMXGZIYMMN-UHFFFAOYSA-N 3-chloro-2-hexadecylpyridine Chemical compound CCCCCCCCCCCCCCCCC1=NC=CC=C1Cl OBFSQMXGZIYMMN-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- SXPWTBGAZSPLHA-UHFFFAOYSA-M cetalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SXPWTBGAZSPLHA-UHFFFAOYSA-M 0.000 description 2
- 229960000228 cetalkonium chloride Drugs 0.000 description 2
- 230000009615 deamination Effects 0.000 description 2
- 238000006481 deamination reaction Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229940048957 glucagon 1 mg Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 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 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229940027983 antiseptic and disinfectant quaternary ammonium compound Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000003505 heat denaturation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940112041 peripherally acting muscle relaxants other quaternary ammonium compound in atc Drugs 0.000 description 1
- -1 polyoxyethylene Polymers 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 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
- 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
- A61K38/26—Glucagons
-
- 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
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
- A61K47/186—Quaternary ammonium compounds, e.g. benzalkonium chloride or cetrimide
-
- 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
- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Dermatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Gastroenterology & Hepatology (AREA)
- Zoology (AREA)
- Endocrinology (AREA)
- Immunology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0536/68A GB1202607A (en) | 1968-01-10 | 1968-01-10 | Improvements in or relating to stable glucagon solutions and their preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1900367A1 true DE1900367A1 (de) | 1969-09-04 |
Family
ID=9723689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691900367 Pending DE1900367A1 (de) | 1968-01-10 | 1969-01-04 | Stabile Glucagonloesung und Verfahren zu ihrer Herstellung |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT283600B (enExample) |
| BE (1) | BE726681A (enExample) |
| DE (1) | DE1900367A1 (enExample) |
| FR (1) | FR2000114A1 (enExample) |
| GB (1) | GB1202607A (enExample) |
| IT (1) | IT974528B (enExample) |
| NL (1) | NL6900460A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995001185A1 (en) * | 1993-06-29 | 1995-01-12 | Ferring B.V. | Stabilized pharmaceutical peptide compositions |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7235627B2 (en) | 1996-08-30 | 2007-06-26 | Novo Nordisk A/S | Derivatives of GLP-1 analogs |
| US6458924B2 (en) | 1996-08-30 | 2002-10-01 | Novo Nordisk A/S | Derivatives of GLP-1 analogs |
| AU2612599A (en) * | 1998-03-13 | 1999-10-11 | Novo Nordisk A/S | Stabilized aqueous peptide solutions |
| DE69918070T2 (de) * | 1998-03-13 | 2005-08-25 | Novo Nordisk A/S | Stabilisierte, wässrige Glukagonlösungen, enthaltend Detergenzien |
| US9610329B2 (en) | 2009-10-22 | 2017-04-04 | Albireo Pharma, Inc. | Stabilized glucagon solutions |
| EP2490708B1 (en) | 2009-10-22 | 2013-03-27 | Biodel Inc. | Stabilized glucagon solutions |
| WO2012059764A1 (en) | 2010-11-03 | 2012-05-10 | Arecor Limited | Novel composition comprising glucagon |
| US9198971B2 (en) | 2012-01-09 | 2015-12-01 | Adocia | Injectable solution at pH 7 comprising at least one basal insulin the pI of which is between 5.8 and 8.5 and a substituted co-polyamino acid |
| US20150314003A2 (en) | 2012-08-09 | 2015-11-05 | Adocia | Injectable solution at ph 7 comprising at least one basal insulin the isoelectric point of which is between 5.8 and 8.5 and a hydrophobized anionic polymer |
| KR20190025905A (ko) * | 2016-06-07 | 2019-03-12 | 아도시아 | 인간 글루카곤 및 통계적 코폴리아미노산을 포함하는 주사가능한 수용액 형태의 조성물 |
| FR3052071B1 (fr) * | 2016-06-07 | 2018-09-07 | Adocia | Compositions sous forme d'une solution aqueuse injectable comprenant du glucagon et un co-polyaminoacide |
| FR3061660B1 (fr) * | 2017-01-10 | 2019-05-31 | Adocia | Compositions sous forme d'une solution aqueuse injectable comprenant du glucagon humain et un co-polyaminoacide |
| GB201611077D0 (en) | 2016-06-24 | 2016-08-10 | Arecor Ltd | Novel composition |
| FR3083087A1 (fr) | 2018-06-29 | 2020-01-03 | Adocia | Compositions sous forme d'une solution aqueuse injectable comprenant du glucagon humain et un co-polyaminoacide |
| FR3074683B1 (fr) * | 2017-12-07 | 2020-01-10 | Adocia | Compositions sous forme d'une solution aqueuse injectable comprenant du glucagon humain et un co-polyaminoacide |
| KR20240171195A (ko) | 2017-12-07 | 2024-12-06 | 아도시아 | 인간 글루카곤 및 코-폴리아미노산을 포함하는 주사용 수용액 형태의 조성물 |
| CA3084700A1 (en) | 2017-12-07 | 2019-06-13 | Adocia | Compositions in the form of an injectable aqueous solution comprising human glucagon and a copolyamino acid |
| WO2019110838A1 (fr) | 2017-12-07 | 2019-06-13 | Adocia | Compositions sous forme d'une solution aqueuse injectable comprenant du glucagon humain et un co-polyaminoacide |
| US10987426B2 (en) * | 2017-12-07 | 2021-04-27 | Adocia | Compositions in the form of an injectable aqueous solution comprising human glucagon and a co-polyamino acid |
| FR3067247A1 (fr) | 2018-06-07 | 2018-12-14 | Adocia | Compositions sous forme d'une solution aqueuse injectable comprenant du glucagon humain et un co-polyaminoacide |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2643967A (en) * | 1946-08-31 | 1953-06-30 | Wallerstein Co Inc | Concentrate of tyrothricin and its therapeutically active components |
| NL94376C (nl) * | 1958-04-28 | 1960-05-16 | Nv Organon | Werkwijze ter bereiding van injicieerbare glacagonpreparaten met verlengde werking |
-
1968
- 1968-01-10 GB GB0536/68A patent/GB1202607A/en not_active Expired
-
1969
- 1969-01-04 DE DE19691900367 patent/DE1900367A1/de active Pending
- 1969-01-09 FR FR6900222A patent/FR2000114A1/fr not_active Withdrawn
- 1969-01-09 IT IT50089/69A patent/IT974528B/it active
- 1969-01-09 BE BE726681D patent/BE726681A/xx unknown
- 1969-01-10 AT AT26769A patent/AT283600B/de not_active IP Right Cessation
- 1969-01-10 NL NL6900460A patent/NL6900460A/xx unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995001185A1 (en) * | 1993-06-29 | 1995-01-12 | Ferring B.V. | Stabilized pharmaceutical peptide compositions |
| US5482931A (en) * | 1993-06-29 | 1996-01-09 | Ferring Ab | Stabilized pharmaceutical peptide compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| AT283600B (de) | 1970-08-10 |
| FR2000114A1 (fr) | 1969-08-29 |
| GB1202607A (en) | 1970-08-19 |
| IT974528B (it) | 1974-07-10 |
| BE726681A (enExample) | 1969-07-09 |
| NL6900460A (enExample) | 1969-07-14 |
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