TWI302459B - - Google Patents
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- TWI302459B TWI302459B TW091118723A TW91118723A TWI302459B TW I302459 B TWI302459 B TW I302459B TW 091118723 A TW091118723 A TW 091118723A TW 91118723 A TW91118723 A TW 91118723A TW I302459 B TWI302459 B TW I302459B
- Authority
- TW
- Taiwan
- Prior art keywords
- lipid
- composition
- drug
- encapsulated
- fatty acid
- Prior art date
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- 150000002632 lipids Chemical class 0.000 claims description 162
- 239000000203 mixture Substances 0.000 claims description 148
- 239000000194 fatty acid Substances 0.000 claims description 78
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 77
- 229930195729 fatty acid Natural products 0.000 claims description 77
- 150000004665 fatty acids Chemical class 0.000 claims description 71
- -1 iso arene Chemical class 0.000 claims description 54
- 238000000034 method Methods 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 40
- 239000012867 bioactive agent Substances 0.000 claims description 24
- 238000005538 encapsulation Methods 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 21
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 102000004190 Enzymes Human genes 0.000 claims description 18
- 108090000790 Enzymes Proteins 0.000 claims description 18
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000002634 lipophilic molecules Chemical class 0.000 claims description 14
- 239000004215 Carbon black (E152) Substances 0.000 claims description 12
- 241000700605 Viruses Species 0.000 claims description 12
- 230000000975 bioactive effect Effects 0.000 claims description 12
- 229930195733 hydrocarbon Natural products 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 11
- 239000002775 capsule Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 8
- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 claims description 7
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- 229930182478 glucoside Natural products 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 229940117972 triolein Drugs 0.000 claims description 7
- 229930182555 Penicillin Natural products 0.000 claims description 6
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229940049954 penicillin Drugs 0.000 claims description 6
- 235000013877 carbamide Nutrition 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 5
- 229940049964 oleate Drugs 0.000 claims description 5
- 102000004169 proteins and genes Human genes 0.000 claims description 5
- 108090000623 proteins and genes Proteins 0.000 claims description 5
- 239000004575 stone Substances 0.000 claims description 5
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- 238000001035 drying Methods 0.000 claims description 4
- 239000002777 nucleoside Substances 0.000 claims description 4
- 229920001282 polysaccharide Polymers 0.000 claims description 4
- 239000005017 polysaccharide Substances 0.000 claims description 4
- 229940126586 small molecule drug Drugs 0.000 claims description 4
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- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 claims description 3
- 229920001542 oligosaccharide Polymers 0.000 claims description 2
- 150000002482 oligosaccharides Chemical class 0.000 claims description 2
- 125000005555 sulfoximide group Chemical group 0.000 claims description 2
- 230000008827 biological function Effects 0.000 claims 4
- 102000004366 Glucosidases Human genes 0.000 claims 3
- 108010056771 Glucosidases Proteins 0.000 claims 3
- 102000001708 Protein Isoforms Human genes 0.000 claims 3
- 108010029485 Protein Isoforms Proteins 0.000 claims 3
- YXHXDEBLSQQHQE-UHFFFAOYSA-N N.N.OP(O)=O Chemical class N.N.OP(O)=O YXHXDEBLSQQHQE-UHFFFAOYSA-N 0.000 claims 2
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 229940124530 sulfonamide Drugs 0.000 claims 2
- 150000003456 sulfonamides Chemical class 0.000 claims 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims 2
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims 1
- 241000555745 Sciuridae Species 0.000 claims 1
- 229910052785 arsenic Inorganic materials 0.000 claims 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims 1
- SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical compound O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 150000003672 ureas Chemical class 0.000 claims 1
- 239000003814 drug Substances 0.000 description 196
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- 238000011282 treatment Methods 0.000 description 45
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- RDXLYGJSWZYTFJ-UHFFFAOYSA-N Niridazole Chemical compound S1C([N+](=O)[O-])=CN=C1N1C(=O)NCC1 RDXLYGJSWZYTFJ-UHFFFAOYSA-N 0.000 description 24
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- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 16
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- AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 description 14
- SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 description 14
- 125000000524 functional group Chemical group 0.000 description 14
- 229960002418 ivermectin Drugs 0.000 description 14
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 13
- 229960001138 acetylsalicylic acid Drugs 0.000 description 13
- 210000004369 blood Anatomy 0.000 description 13
- 239000008280 blood Substances 0.000 description 13
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
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- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 10
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 9
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- 235000013330 chicken meat Nutrition 0.000 description 8
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
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- 125000003118 aryl group Chemical group 0.000 description 6
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- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- MIHADVKEHAFNPG-UHFFFAOYSA-N 2-Amino-5-nitrothiazole Chemical compound NC1=NC=C([N+]([O-])=O)S1 MIHADVKEHAFNPG-UHFFFAOYSA-N 0.000 description 2
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- 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
- A61K47/54—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 an organic compound
- A61K47/543—Lipids, e.g. triglycerides; Polyamines, e.g. spermine or spermidine
-
- 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
- A61K47/54—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 an organic compound
- A61K47/542—Carboxylic acids, e.g. a fatty acid or an amino acid
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31409201P | 2001-08-23 | 2001-08-23 | |
| US10/134,329 US7125568B2 (en) | 2001-08-23 | 2002-04-29 | Lipophilic drug compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI302459B true TWI302459B (enExample) | 2008-11-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091118723A TWI302459B (enExample) | 2001-08-23 | 2002-08-19 |
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| Country | Link |
|---|---|
| US (2) | US7125568B2 (enExample) |
| EP (1) | EP1420828B1 (enExample) |
| CA (1) | CA2458394C (enExample) |
| ES (1) | ES2395408T3 (enExample) |
| TW (1) | TWI302459B (enExample) |
| WO (1) | WO2003018064A2 (enExample) |
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| JP2007509981A (ja) * | 2003-10-31 | 2007-04-19 | テバ ファーマシューティカル インダストリーズ リミティド | 薬物デリバリー用ナノ粒子 |
| AU2006235490A1 (en) * | 2005-04-12 | 2006-10-19 | Romark Laboratories, L.C. | Methods for treating diseases through the function of molecular chaperones such as protein disulfide isomerases, pharmaceutical compositions comprising them, and screening methods for identifying therapeutic agents |
| EA015560B1 (ru) | 2006-01-09 | 2011-08-30 | Ромарк Лэборетериз, Эл.Си. | Способ лечения вирусного гепатита |
| WO2007134245A2 (en) * | 2006-05-12 | 2007-11-22 | Wisconsin Alumni Research Foundation | Elastin-like polymer delivery vehicles |
| US20100104625A1 (en) * | 2007-02-16 | 2010-04-29 | Cornell University | Biodegradable compositions and materials |
| US8354116B2 (en) * | 2007-06-18 | 2013-01-15 | Biochemics, Inc. | Bifunctional synthetic molecules |
| US7790401B2 (en) * | 2007-08-06 | 2010-09-07 | Siemens Healthcare Diagnostics | Methods for detection of immunosuppressant drugs |
| TW200936180A (en) * | 2007-11-27 | 2009-09-01 | Intervet Int Bv | Carrier particle for a microorganism or subunit thereof, pharmaceutical composition comprising such particles, method for preparation of this composition and its use in the treatment of animals |
| GB0724550D0 (en) * | 2007-12-18 | 2008-01-30 | Univ Hull | Formulations |
| GB0812513D0 (en) * | 2008-07-09 | 2008-08-13 | Univ Hull | Delivery vehicle |
| WO2011044136A1 (en) * | 2009-10-05 | 2011-04-14 | Catabasis Pharmaceuticals, Inc. | Fatty acid acipimox derivatives and their uses |
| CA2811931C (en) | 2010-10-20 | 2015-06-16 | Galderma S.A. | Method of treating herpes virus infection using macrocyclic lactone compound |
| WO2015069699A1 (en) * | 2013-11-05 | 2015-05-14 | Ultragenyx Pharmaceutical Inc. | Creatine analogs and the use thereof |
| EP3475442B1 (en) | 2016-06-23 | 2024-10-23 | The Regents of The University of Michigan | 12(s)-hydroxyeicosatrienoic acid compounds and their use as therapeutic agents |
| CN111417620B (zh) | 2017-12-01 | 2023-08-25 | 奥特吉尼克斯制药公司 | 肌酸前药、其组合物以及使用方法 |
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| DE2655369A1 (de) * | 1976-12-03 | 1978-06-08 | Schering Ag | 5-(subst. phenyl)-oxazolidinone und deren schwefelanaloga sowie verfahren zu deren herstellung |
| US4315018A (en) * | 1978-12-07 | 1982-02-09 | Rossignol Jean F | Specific parasiticidal use of 2-benzamido-5-nitro-thiazole derivatives |
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| MX9203808A (es) * | 1987-03-05 | 1992-07-01 | Liposome Co Inc | Formulaciones de alto contenido de medicamento: lipido, de agentes liposomicos-antineoplasticos. |
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| US5907030A (en) * | 1995-01-25 | 1999-05-25 | University Of Southern California | Method and compositions for lipidization of hydrophilic molecules |
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2002
- 2002-04-29 US US10/134,329 patent/US7125568B2/en not_active Expired - Lifetime
- 2002-08-19 TW TW091118723A patent/TWI302459B/zh active
- 2002-08-21 CA CA2458394A patent/CA2458394C/en not_active Expired - Fee Related
- 2002-08-21 ES ES02766045T patent/ES2395408T3/es not_active Expired - Lifetime
- 2002-08-21 WO PCT/US2002/026571 patent/WO2003018064A2/en not_active Ceased
- 2002-08-21 EP EP02766045A patent/EP1420828B1/en not_active Expired - Lifetime
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2006
- 2006-03-03 US US11/367,929 patent/US7390506B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003018064A3 (en) | 2003-09-25 |
| CA2458394C (en) | 2013-04-23 |
| WO2003018064A2 (en) | 2003-03-06 |
| ES2395408T3 (es) | 2013-02-12 |
| EP1420828B1 (en) | 2012-09-26 |
| EP1420828A2 (en) | 2004-05-26 |
| US20030108596A1 (en) | 2003-06-12 |
| CA2458394A1 (en) | 2003-03-06 |
| US7390506B2 (en) | 2008-06-24 |
| US20060147525A1 (en) | 2006-07-06 |
| US7125568B2 (en) | 2006-10-24 |
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