CA2664568C - Formulations comprising cyclic compounds - Google Patents
Formulations comprising cyclic compounds Download PDFInfo
- Publication number
- CA2664568C CA2664568C CA2664568A CA2664568A CA2664568C CA 2664568 C CA2664568 C CA 2664568C CA 2664568 A CA2664568 A CA 2664568A CA 2664568 A CA2664568 A CA 2664568A CA 2664568 C CA2664568 C CA 2664568C
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- CA
- Canada
- Prior art keywords
- cyclic
- protonated
- compound
- active agent
- acid
- 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.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 82
- 150000001923 cyclic compounds Chemical class 0.000 title claims abstract description 73
- 238000009472 formulation Methods 0.000 title description 20
- 239000013543 active substance Substances 0.000 claims abstract description 115
- 150000001875 compounds Chemical class 0.000 claims abstract description 105
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical group NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims abstract description 49
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 34
- 239000003125 aqueous solvent Substances 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 117
- 125000004122 cyclic group Chemical group 0.000 claims description 109
- 239000000178 monomer Substances 0.000 claims description 56
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- 108090000623 proteins and genes Proteins 0.000 claims description 47
- 102000004169 proteins and genes Human genes 0.000 claims description 46
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 41
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 38
- 229940061720 alpha hydroxy acid Drugs 0.000 claims description 29
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- 229920001184 polypeptide Polymers 0.000 claims description 29
- 150000001413 amino acids Chemical class 0.000 claims description 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000003277 amino group Chemical group 0.000 claims description 17
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
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- 125000000524 functional group Chemical group 0.000 abstract description 42
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
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- OHRURASPPZQGQM-GCCNXGTGSA-N romidepsin Chemical compound O1C(=O)[C@H](C(C)C)NC(=O)C(=C/C)/NC(=O)[C@H]2CSSCC\C=C\[C@@H]1CC(=O)N[C@H](C(C)C)C(=O)N2 OHRURASPPZQGQM-GCCNXGTGSA-N 0.000 description 15
- 125000001424 substituent group Chemical group 0.000 description 15
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
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- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 11
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- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- CIJQTPFWFXOSEO-NDMITSJXSA-J tetrasodium;(2r,3r,4s)-2-[(2r,3s,4r,5r,6s)-5-acetamido-6-[(1r,2r,3r,4r)-4-[(2r,3s,4r,5r,6r)-5-acetamido-6-[(4r,5r,6r)-2-carboxylato-4,5-dihydroxy-6-[[(1r,3r,4r,5r)-3-hydroxy-4-(sulfonatoamino)-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy]oxan-3-yl]oxy-2-(hydroxy Chemical compound [Na+].[Na+].[Na+].[Na+].O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1O)NC(C)=O)O[C@@H]1C(C[C@H]([C@@H]([C@H]1O)O)O[C@@H]1[C@@H](CO)O[C@H](OC2C(O[C@@H](OC3[C@@H]([C@@H](NS([O-])(=O)=O)[C@@H]4OC[C@H]3O4)O)[C@H](O)[C@H]2O)C([O-])=O)[C@H](NC(C)=O)[C@H]1C)C([O-])=O)[C@@H]1OC(C([O-])=O)=C[C@H](O)[C@H]1O CIJQTPFWFXOSEO-NDMITSJXSA-J 0.000 description 1
- OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 description 1
- 229960004659 ticarcillin Drugs 0.000 description 1
- AGHANLSBXUWXTB-UHFFFAOYSA-N tienilic acid Chemical compound ClC1=C(Cl)C(OCC(=O)O)=CC=C1C(=O)C1=CC=CS1 AGHANLSBXUWXTB-UHFFFAOYSA-N 0.000 description 1
- 229960000356 tienilic acid Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 229960000707 tobramycin Drugs 0.000 description 1
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- 229960001288 triamterene Drugs 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
- 229960000604 valproic acid Drugs 0.000 description 1
- 208000012137 von Willebrand disease (hereditary or acquired) Diseases 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229960003414 zomepirac Drugs 0.000 description 1
- ZXVNMYWKKDOREA-UHFFFAOYSA-N zomepirac Chemical compound C1=C(CC(O)=O)N(C)C(C(=O)C=2C=CC(Cl)=CC=2)=C1C ZXVNMYWKKDOREA-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D323/00—Heterocyclic compounds containing more than two oxygen atoms as the only ring hetero atoms
-
- 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
-
- 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
- A61K47/69—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—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 conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nanotechnology (AREA)
- Epidemiology (AREA)
- Biotechnology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Engineering & Computer Science (AREA)
- Medical Informatics (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Polyesters Or Polycarbonates (AREA)
- Peptides Or Proteins (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06020286A EP1905454A1 (en) | 2006-09-27 | 2006-09-27 | Formulations comprising cyclic compounds |
| EP06020286.8 | 2006-09-27 | ||
| PCT/EP2007/008442 WO2008037484A2 (en) | 2006-09-27 | 2007-09-27 | Formulations comprising cyclic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2664568A1 CA2664568A1 (en) | 2008-04-03 |
| CA2664568C true CA2664568C (en) | 2015-11-24 |
Family
ID=37728182
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2664568A Active CA2664568C (en) | 2006-09-27 | 2007-09-27 | Formulations comprising cyclic compounds |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8513188B2 (OSRAM) |
| EP (2) | EP1905454A1 (OSRAM) |
| JP (1) | JP5335677B2 (OSRAM) |
| CN (2) | CN101557829A (OSRAM) |
| AU (1) | AU2007302270B2 (OSRAM) |
| BR (1) | BRPI0714761B8 (OSRAM) |
| CA (1) | CA2664568C (OSRAM) |
| ES (1) | ES2691736T3 (OSRAM) |
| IL (1) | IL197760A (OSRAM) |
| WO (1) | WO2008037484A2 (OSRAM) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2010323117B2 (en) | 2009-11-25 | 2015-09-03 | Capsugel Belgium Nv | Mucosal delivery compositions comprising a peptide complexed with a crown comppound and/or a counter ion |
| EP2332929A1 (en) * | 2009-11-25 | 2011-06-15 | ArisGen SA | Orthoester derivatives of crown ethers as carriers for pharmaceutical and diagnostic compositions |
| EP2526971A1 (en) * | 2011-05-25 | 2012-11-28 | ArisGen SA | Mucosal delivery of drugs |
| CN102863358B (zh) * | 2012-09-20 | 2014-02-12 | 华中农业大学 | 具有除草活性的化合物及其制备方法 |
| EP3000811B1 (en) * | 2014-09-24 | 2017-11-08 | Friedrich-Alexander-Universität Erlangen-Nürnberg | Crown Ether Complexes and Methods for Poducing the Same |
| US9937223B2 (en) | 2015-01-30 | 2018-04-10 | Par Pharmaceutical, Inc. | Vasopressin formulations for use in treatment of hypotension |
| US9750785B2 (en) | 2015-01-30 | 2017-09-05 | Par Pharmaceutical, Inc. | Vasopressin formulations for use in treatment of hypotension |
| US9687526B2 (en) | 2015-01-30 | 2017-06-27 | Par Pharmaceutical, Inc. | Vasopressin formulations for use in treatment of hypotension |
| US9375478B1 (en) | 2015-01-30 | 2016-06-28 | Par Pharmaceutical, Inc. | Vasopressin formulations for use in treatment of hypotension |
| US9925233B2 (en) | 2015-01-30 | 2018-03-27 | Par Pharmaceutical, Inc. | Vasopressin formulations for use in treatment of hypotension |
| US9744209B2 (en) | 2015-01-30 | 2017-08-29 | Par Pharmaceutical, Inc. | Vasopressin formulations for use in treatment of hypotension |
| CN108658264B (zh) * | 2018-04-17 | 2021-05-25 | 唐山师范学院 | 多支化聚环氧琥珀酸衍生物阻垢缓蚀剂的制备及其应用方法 |
| CN113527672B (zh) * | 2020-03-30 | 2022-09-20 | 复旦大学 | 一种胍基衍生物及其基因递释系统 |
| CN116178887B (zh) * | 2023-02-16 | 2024-10-29 | 东华大学 | 一种可降解快递袋材料及其制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2923787A1 (de) * | 1979-06-12 | 1980-12-18 | Max Planck Gesellschaft | Verfahren zur selektiven bildung von disulfidbruecken in polypeptiden und die dabei erhaltenen produkte als wirkstoffe enthaltende arzneimittel |
| US4474753A (en) * | 1983-05-16 | 1984-10-02 | Merck & Co., Inc. | Topical drug delivery system utilizing thermosetting gels |
| AU6738487A (en) * | 1985-12-04 | 1987-06-30 | Hsieh, D. | Transdermal delivery of drugs |
| US5023252A (en) * | 1985-12-04 | 1991-06-11 | Conrex Pharmaceutical Corporation | Transdermal and trans-membrane delivery of drugs |
| EP2280004B1 (en) * | 1999-06-29 | 2016-04-20 | MannKind Corporation | Pharmaceutical formulations comprising insulin complexed with a diketopiperazine |
| CN1379771A (zh) * | 1999-09-20 | 2002-11-13 | 天藤制药株式会社 | 环状乳酸齐聚物的制备方法 |
| US7169814B2 (en) * | 2001-12-11 | 2007-01-30 | The Board Of Trustees Of The Leland Stanford Junior University | Guanidinium transport reagents and conjugates |
| JP2006232909A (ja) * | 2005-02-23 | 2006-09-07 | Tokai Univ | 環状オリゴ乳酸 |
-
2006
- 2006-09-27 EP EP06020286A patent/EP1905454A1/en not_active Withdrawn
-
2007
- 2007-09-26 CN CNA2007800425762A patent/CN101557829A/zh active Pending
- 2007-09-27 EP EP07818525.3A patent/EP2068934B8/en not_active Not-in-force
- 2007-09-27 JP JP2009529613A patent/JP5335677B2/ja not_active Expired - Fee Related
- 2007-09-27 WO PCT/EP2007/008442 patent/WO2008037484A2/en not_active Ceased
- 2007-09-27 CN CN200780043437.1A patent/CN101541346B/zh not_active Expired - Fee Related
- 2007-09-27 AU AU2007302270A patent/AU2007302270B2/en not_active Ceased
- 2007-09-27 BR BRPI0714761A patent/BRPI0714761B8/pt not_active IP Right Cessation
- 2007-09-27 US US12/443,327 patent/US8513188B2/en not_active Expired - Fee Related
- 2007-09-27 CA CA2664568A patent/CA2664568C/en active Active
- 2007-09-27 ES ES07818525.3T patent/ES2691736T3/es active Active
-
2009
- 2009-03-23 IL IL197760A patent/IL197760A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2007302270A1 (en) | 2008-04-03 |
| US20100137188A1 (en) | 2010-06-03 |
| CN101541346B (zh) | 2014-07-02 |
| EP2068934A2 (en) | 2009-06-17 |
| JP2010504934A (ja) | 2010-02-18 |
| BRPI0714761B1 (pt) | 2021-03-23 |
| AU2007302270B2 (en) | 2014-05-29 |
| JP5335677B2 (ja) | 2013-11-06 |
| IL197760A (en) | 2016-10-31 |
| BRPI0714761A2 (pt) | 2013-07-02 |
| CN101557829A (zh) | 2009-10-14 |
| IL197760A0 (en) | 2009-12-24 |
| ES2691736T3 (es) | 2018-11-28 |
| WO2008037484A2 (en) | 2008-04-03 |
| CA2664568A1 (en) | 2008-04-03 |
| BRPI0714761B8 (pt) | 2021-05-25 |
| US8513188B2 (en) | 2013-08-20 |
| EP2068934B8 (en) | 2018-09-05 |
| WO2008037484A3 (en) | 2008-12-18 |
| CN101541346A (zh) | 2009-09-23 |
| EP2068934B1 (en) | 2018-07-18 |
| EP1905454A1 (en) | 2008-04-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |