CA2530983C - Compounds, methods and formulations for the oral delivery of a glucagon like peptide (glp)-1 compound or an melanocortin 4 receptor (mc4) agonist peptide - Google Patents
Compounds, methods and formulations for the oral delivery of a glucagon like peptide (glp)-1 compound or an melanocortin 4 receptor (mc4) agonist peptide Download PDFInfo
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- CA2530983C CA2530983C CA2530983A CA2530983A CA2530983C CA 2530983 C CA2530983 C CA 2530983C CA 2530983 A CA2530983 A CA 2530983A CA 2530983 A CA2530983 A CA 2530983A CA 2530983 C CA2530983 C CA 2530983C
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- Canada
- Prior art keywords
- compound
- glp
- alkyl
- peptide
- pharmaceutical salt
- Prior art date
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- 238000009472 formulation Methods 0.000 title abstract description 18
- 238000000034 method Methods 0.000 title abstract description 8
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- -1 GLP-1 compound Chemical class 0.000 claims abstract description 18
- 101710198884 GATA-type zinc finger protein 1 Proteins 0.000 claims abstract description 10
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- 150000003839 salts Chemical class 0.000 claims description 20
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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- 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
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
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- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49653703P | 2003-08-20 | 2003-08-20 | |
| US60/496,537 | 2003-08-20 | ||
| PCT/US2004/024387 WO2005019212A1 (en) | 2003-08-20 | 2004-08-18 | Compounds, methods and formulations for the oral delivery of a glucagon like peptide (glp)-1 compound or an melanocortin 4 receptor (mc4) agonist peptide |
Publications (2)
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| HUE037147T2 (hu) | 2005-07-08 | 2018-08-28 | Ipsen Pharma | Melanokortin-receptor ligandumai |
| WO2008027958A2 (en) * | 2006-08-31 | 2008-03-06 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
| CA2689016C (en) * | 2007-05-25 | 2014-08-12 | Ipsen Pharma S.A.S. | Melanocortin receptor ligands modified with hydantoin |
| BRPI0909947A2 (pt) | 2008-06-09 | 2017-06-27 | Palatin Technologies Inc | '' peptídeo cíclico, composição farmacêutica, método de tratamento de uma doença, indicação, condição ou síndrome mediada por receptor de melanocortina em seres humanos ou mamíferos não humanos, e, método de tratamento de condição que reage a alterações da função de receptor de melanocortina em seres humanos ou mamíferos não humanos'' |
| CN102458436B (zh) | 2009-06-08 | 2015-06-03 | 帕拉丁科技公司 | 黑皮质素受体特异性肽 |
| UY32690A (es) | 2009-06-08 | 2011-01-31 | Astrazeneca Ab | Péptidos específicos para receptores de melanocortina |
| EP2440572B1 (en) | 2009-06-08 | 2017-04-05 | Palatin Technologies, Inc. | Lactam-bridged melanocortin receptor-specific peptides |
| BR112012011780A2 (pt) | 2009-11-23 | 2019-09-24 | Palatin Technologies, Inc | peptídeo linear,composição farmacêutica,métodopara tratamento de umadoença,indicação,condição ou sídrome mediadsa por receptor de melanocortina emum mamífero humano ou não humano e método para tratamento de uma condição responsiva ás alterações em função de receptor de melanocortina em um mamifero humano ou não humano |
| MX2012005862A (es) | 2009-11-23 | 2012-09-07 | Palatin Technologies Inc | Peptidos ciclicos especificos del receptor de melanocortina-1. |
| US10357348B2 (en) * | 2013-08-19 | 2019-07-23 | Warren Matthew Leevy | Fluid manifold |
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| CN105017136A (zh) * | 2015-07-24 | 2015-11-04 | 陈吉美 | 一种2-溴-3-甲氧基吡啶的制备方法 |
| BR112019016241A2 (pt) | 2017-02-08 | 2020-04-07 | Bayer Cropscience Ag | derivados de triazol e seu uso como fungicidas |
| EP3580218A1 (en) | 2017-02-08 | 2019-12-18 | Bayer CropScience Aktiengesellschaft | Novel triazole derivatives |
| CN110267952A (zh) | 2017-02-08 | 2019-09-20 | 拜耳公司 | 三唑硫酮衍生物 |
| AU2018217749A1 (en) | 2017-02-10 | 2019-08-01 | Bayer Aktiengesellschaft | Composition for controlling harmful microorganisms comprising 1 -(phenoxy-pyridinyl)-2-(1,2,4-triazol-1 -yl)-ethanol derivatives |
| WO2020020816A1 (en) | 2018-07-26 | 2020-01-30 | Bayer Aktiengesellschaft | Novel triazole derivatives |
| CN111793038B (zh) * | 2019-04-08 | 2022-08-12 | 新发药业有限公司 | 一种取代噁唑化合物的环保制备方法 |
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2004
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- 2004-08-18 JP JP2006523866A patent/JP4754487B2/ja not_active Expired - Fee Related
- 2004-08-18 AT AT04779447T patent/ATE361294T1/de not_active IP Right Cessation
- 2004-08-18 US US10/566,012 patent/US20070293423A1/en not_active Abandoned
- 2004-08-18 CN CNB2004800227912A patent/CN100398536C/zh not_active Expired - Fee Related
- 2004-08-18 EP EP04779447A patent/EP1658285B1/en not_active Expired - Lifetime
- 2004-08-18 DE DE602004006279T patent/DE602004006279T2/de not_active Expired - Lifetime
- 2004-08-18 BR BRPI0413676A patent/BRPI0413676B8/pt not_active IP Right Cessation
- 2004-08-18 CA CA2530983A patent/CA2530983C/en not_active Expired - Fee Related
- 2004-08-18 AU AU2004267044A patent/AU2004267044B8/en not_active Ceased
- 2004-08-18 WO PCT/US2004/024387 patent/WO2005019212A1/en not_active Ceased
- 2004-08-18 MX MXPA06001916A patent/MXPA06001916A/es active IP Right Grant
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2008
- 2008-11-03 US US12/263,722 patent/US7947841B2/en not_active Expired - Fee Related
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2011
- 2011-04-14 US US13/087,255 patent/US8546581B2/en not_active Expired - Fee Related
- 2011-05-09 JP JP2011104435A patent/JP2011207886A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU2004267044B8 (en) | 2009-12-17 |
| BRPI0413676A (pt) | 2006-10-24 |
| US20110190205A1 (en) | 2011-08-04 |
| CA2530983A1 (en) | 2005-03-03 |
| WO2005019212A1 (en) | 2005-03-03 |
| BRPI0413676B1 (pt) | 2018-07-24 |
| US8546581B2 (en) | 2013-10-01 |
| US20090239798A1 (en) | 2009-09-24 |
| DE602004006279T2 (de) | 2007-12-27 |
| BRPI0413676B8 (pt) | 2021-05-25 |
| US7947841B2 (en) | 2011-05-24 |
| EP1658285B1 (en) | 2007-05-02 |
| ES2286679T3 (es) | 2007-12-01 |
| JP2011207886A (ja) | 2011-10-20 |
| DE602004006279D1 (de) | 2007-06-14 |
| CN100398536C (zh) | 2008-07-02 |
| ATE361294T1 (de) | 2007-05-15 |
| JP4754487B2 (ja) | 2011-08-24 |
| CN1832944A (zh) | 2006-09-13 |
| JP2007502817A (ja) | 2007-02-15 |
| MXPA06001916A (es) | 2006-05-17 |
| US20070293423A1 (en) | 2007-12-20 |
| EP1658285A1 (en) | 2006-05-24 |
| AU2004267044A1 (en) | 2005-03-03 |
| AU2004267044B2 (en) | 2009-12-03 |
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