CA2744558A1 - Amide-based insulin prodrugs - Google Patents
Amide-based insulin prodrugs Download PDFInfo
- Publication number
- CA2744558A1 CA2744558A1 CA2744558A CA2744558A CA2744558A1 CA 2744558 A1 CA2744558 A1 CA 2744558A1 CA 2744558 A CA2744558 A CA 2744558A CA 2744558 A CA2744558 A CA 2744558A CA 2744558 A1 CA2744558 A1 CA 2744558A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- group
- seq
- amino acid
- 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.)
- Abandoned
Links
- 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 abstract description 467
- 229940002612 prodrug Drugs 0.000 title claims abstract description 259
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 221
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 156
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 85
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- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 21
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- 229920001897 terpolymer Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 150000001467 thiazolidinediones Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 229960002277 tolazamide Drugs 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 229940035266 tolinase Drugs 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
- 229960001254 vildagliptin Drugs 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/62—Insulins
- C07K14/622—Insulins at least 1 amino acid in D-form
-
- 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/62—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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/62—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being a protein, peptide or polyamino acid
- A61K47/64—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/62—Insulins
- C07K14/625—Extraction from natural sources
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Diabetes (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Endocrinology (AREA)
- Zoology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Toxicology (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13921808P | 2008-12-19 | 2008-12-19 | |
| US61/139,218 | 2008-12-19 | ||
| PCT/US2009/068716 WO2010080609A1 (en) | 2008-12-19 | 2009-12-18 | Amide-based insulin prodrugs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2744558A1 true CA2744558A1 (en) | 2010-07-15 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2744558A Abandoned CA2744558A1 (en) | 2008-12-19 | 2009-12-18 | Amide-based insulin prodrugs |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8697632B2 (enExample) |
| EP (1) | EP2376521B1 (enExample) |
| JP (1) | JP5755566B2 (enExample) |
| CN (1) | CN102245624B (enExample) |
| AU (1) | AU2009335715B2 (enExample) |
| CA (1) | CA2744558A1 (enExample) |
| WO (1) | WO2010080609A1 (enExample) |
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| US20110065633A1 (en) | 2008-01-30 | 2011-03-17 | Indiana University Research And Technology Corporation | Ester-based peptide prodrugs |
| CA2728284C (en) | 2008-06-17 | 2019-09-10 | Richard D. Dimarchi | Glucagon/glp-1 receptor co-agonists |
| MA32970B1 (fr) | 2008-12-15 | 2012-01-02 | Zealand Pharma As | Analogues du glucagon |
| AU2008365557A1 (en) | 2008-12-15 | 2011-07-21 | Zealand Pharma A/S | Glucagon analogues |
| ES2502218T3 (es) | 2008-12-15 | 2014-10-03 | Zealand Pharma A/S | Análogos de glucagón |
| US8642540B2 (en) | 2008-12-15 | 2014-02-04 | Zealand Pharma A/S | Glucagon analogues |
| EP2376097A4 (en) | 2008-12-19 | 2012-10-03 | Univ Indiana Res & Tech Corp | PEPTIDE PRODRUGS OF AMIDE-BASED GLUCAGON SUPERFAMILY |
| WO2010148089A1 (en) | 2009-06-16 | 2010-12-23 | Indiana University Research And Technology Corporation | Gip receptor-active glucagon compounds |
| JP6054742B2 (ja) | 2009-07-13 | 2016-12-27 | ジーランド ファーマ アクティーゼルスカブ | アシル化グルカゴン類似体 |
| AR081975A1 (es) | 2010-06-23 | 2012-10-31 | Zealand Pharma As | Analogos de glucagon |
| CA2803164C (en) | 2010-06-24 | 2018-08-21 | Indiana University Research And Technology Corporation | Amide-based insulin prodrugs |
| CA2802897A1 (en) | 2010-06-24 | 2011-12-29 | Zealand Pharma A/S | Glucagon analogues |
| KR20130083843A (ko) * | 2010-06-24 | 2013-07-23 | 인디애나 유니버시티 리서치 앤드 테크놀로지 코퍼레이션 | 디펩티드 연결된 약제 |
| EA201390796A1 (ru) | 2011-01-20 | 2014-07-30 | Зилэнд Фарма А/С | Применение ацилированного аналога глюкагона |
| CN103533952B (zh) * | 2011-03-15 | 2017-02-15 | 诺沃—诺迪斯克有限公司 | 包含半胱氨酸置换的人胰岛素类似物和衍生物 |
| EP2720711A1 (en) * | 2011-06-15 | 2014-04-23 | Novo Nordisk A/S | Multi substituted insulins |
| CN103857408B (zh) | 2011-06-22 | 2017-04-12 | 印第安那大学科技研究公司 | 胰高血糖素/glp‑1受体协同激动剂 |
| CN104114183A (zh) * | 2011-12-20 | 2014-10-22 | 印第安纳大学研究及科技有限公司 | 用于治疗糖尿病的基于ctp的胰岛素类似物 |
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| CN108383902A (zh) | 2012-09-26 | 2018-08-10 | 印第安纳大学研究及科技有限公司 | 胰岛素类似物二聚体 |
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| JP6538645B2 (ja) * | 2013-03-14 | 2019-07-03 | インディアナ ユニバーシティー リサーチ アンド テクノロジー コーポレーションＩｎｄｉａｎａ Ｕｎｉｖｅｒｓｉｔｙ Ｒｅｓｅａｒｃｈ Ａｎｄ Ｔｅｃｈｎｏｌｏｇｙ Ｃｏｒｐｏｒａｔｉｏｎ | インスリン‐インクレチン複合物 |
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-
2009
- 2009-12-18 US US13/130,966 patent/US8697632B2/en not_active Expired - Fee Related
- 2009-12-18 CN CN200980151543.0A patent/CN102245624B/zh not_active Expired - Fee Related
- 2009-12-18 WO PCT/US2009/068716 patent/WO2010080609A1/en not_active Ceased
- 2009-12-18 AU AU2009335715A patent/AU2009335715B2/en not_active Ceased
- 2009-12-18 EP EP09837985.2A patent/EP2376521B1/en not_active Not-in-force
- 2009-12-18 JP JP2011542484A patent/JP5755566B2/ja not_active Expired - Fee Related
- 2009-12-18 CA CA2744558A patent/CA2744558A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20110257076A1 (en) | 2011-10-20 |
| CN102245624A (zh) | 2011-11-16 |
| EP2376521A1 (en) | 2011-10-19 |
| EP2376521B1 (en) | 2016-04-13 |
| EP2376521A4 (en) | 2014-06-25 |
| CN102245624B (zh) | 2016-08-10 |
| JP2012512901A (ja) | 2012-06-07 |
| US8697632B2 (en) | 2014-04-15 |
| AU2009335715B2 (en) | 2016-09-15 |
| AU2009335715A1 (en) | 2010-07-15 |
| WO2010080609A1 (en) | 2010-07-15 |
| JP5755566B2 (ja) | 2015-07-29 |
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| FZDE | Discontinued |
Effective date: 20190910 |