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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biophysics (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 (OSRAM) | 2008-11-01 |
Family
ID=26832219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091118723A TWI302459B (OSRAM) | 2001-08-23 | 2002-08-19 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7125568B2 (OSRAM) |
| EP (1) | EP1420828B1 (OSRAM) |
| CA (1) | CA2458394C (OSRAM) |
| ES (1) | ES2395408T3 (OSRAM) |
| TW (1) | TWI302459B (OSRAM) |
| WO (1) | WO2003018064A2 (OSRAM) |
Families Citing this family (15)
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|---|---|---|---|---|
| EP1680087A1 (en) * | 2003-10-31 | 2006-07-19 | Teva Pharmaceutical Industries Limited | Nanoparticles for drug delivery |
| CA2604640A1 (en) * | 2005-04-12 | 2006-10-19 | Romark Laboratories L.C. | Methods for treating diseases through interruption of protein maturation, compounds that inhibit the function of molecular chaperones such as protein disulfide isomerases or interfere with glycosylation, pharmaceutical compositions comprising them, and screening methods for identifying therapeutic agents |
| AU2007204963B2 (en) * | 2006-01-09 | 2012-09-27 | Romark Laboratories, L.C. | Viral hepatitis treatment |
| US20100119529A1 (en) * | 2006-05-12 | 2010-05-13 | Furgeson Darin Y | Elastin-like polymer delivery vehicles |
| WO2008101173A2 (en) * | 2007-02-16 | 2008-08-21 | 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 |
| WO2012054334A1 (en) * | 2010-10-20 | 2012-04-26 | Galderma S.A. | Method of treating herpes virus infection using macrocyclic lactone compound |
| CA2929538A1 (en) * | 2013-11-05 | 2015-05-14 | Ultragenyx Pharmaceutical Inc. | Creatine analogs and the use thereof |
| WO2017223447A1 (en) * | 2016-06-23 | 2017-12-28 | The Regents Of The University Of Michigan | 12(s)-hydroxyeicosatrienoic acid compounds and their use as therapeutic agents |
| AU2018375199B2 (en) | 2017-12-01 | 2023-03-30 | Ultragenyx Pharmaceutical Inc. | Creatine prodrugs, compositions and methods of use thereof |
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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 WO PCT/US2002/026571 patent/WO2003018064A2/en not_active Ceased
- 2002-08-21 ES ES02766045T patent/ES2395408T3/es not_active Expired - Lifetime
- 2002-08-21 EP EP02766045A patent/EP1420828B1/en not_active Expired - Lifetime
- 2002-08-21 CA CA2458394A patent/CA2458394C/en not_active Expired - Fee Related
-
2006
- 2006-03-03 US US11/367,929 patent/US7390506B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1420828B1 (en) | 2012-09-26 |
| CA2458394A1 (en) | 2003-03-06 |
| US20030108596A1 (en) | 2003-06-12 |
| WO2003018064A2 (en) | 2003-03-06 |
| WO2003018064A3 (en) | 2003-09-25 |
| US7390506B2 (en) | 2008-06-24 |
| CA2458394C (en) | 2013-04-23 |
| EP1420828A2 (en) | 2004-05-26 |
| US20060147525A1 (en) | 2006-07-06 |
| ES2395408T3 (es) | 2013-02-12 |
| US7125568B2 (en) | 2006-10-24 |
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